JP7705124B2 - Polycyclic aromatic compounds - Google Patents

Description

Article 30, paragraph 2 of the Patent Act applies 1. Program (posted via telecommunications lines) (1) Name of the conference: Society of Basic Organic Chemistry, Young Researchers Online Symposium No. 0 http://www.chembio.nagoya-u.ac.jp/poc-online2020/index. html (2) Posting date: November 12, 2020 (3) Publication: List of oral presentation titles (4) Disclosure authors: Susumu Oda, Wataru Kumano, Toshiki Hama, Ryosuke Kawazumi, Kazuki Yoshiura, Takuji Hatakeyama (5) Publication content: "Carbazole-Based DABNA Analogs as Highly Efficient Thermally Activated Delayed Fluorescence Materials for Narrowband Organic Light-Emitting Diodes" 2. Proceedings (posted via telecommunications lines) (1) Name of conference: 0th Online Symposium for Young Researchers of the Society of Physical Organic Chemistry (2) Posting date: November 12, 2020 (3) Published material: Proceedings of the Online Symposium for Young Researchers of the Society of Physical Organic Chemistry (4) Publisher: Susumu Oda, Wataru Kumano, Toshiteru Hama, Ryosuke Kawazumi, Kazuki Yoshiura, Takuji Hatakeyama (5) Publication content: "Carbazole-Based DABNA Analogs as Highly Efficient Thermally Activated Delayed Fluorescence Materials for Narrowband Organic Light-Emitting Diodes" 3. Conference presentation (publication by oral presentation via telecommunication line) (1) Name of conference: The Society of Physical Organic Chemistry, Young Researchers Online Symposium No. 0 (2) Date held: November 20, 2020 (3) Disclosure by: Susumu Oda, Wataru Kumano, Toshiki Hama, Ryosuke Kawazumi, Kazuki Yoshiura, Takuji Hatakeyama (4) Disclosure content: "Carbazole-Based DABNA Analogs as Highly Efficient Thermally Activated Delayed Fluorescence Materials for Narrowband Organic Light-Emitting Diodes"

Application of Article 30, Paragraph 2 of the Patent Act (1) Publication date: November 12, 2020 (2) Publication: Angewandte Chemie International Edition, 2020, 59, pp. 1-6 (3) Disclosed by: Susumu Oda, Wataru Kumano, Toshiki Hama, Ryosuke Kawazumi, Kazuki Yoshiura, and Takuji Hatakeyama (4) Disclosed content of the invention: Susumu Oda, Wataru Kumano, Toshiki Hama, Ryosuke Kawazumi, Kazuki Yoshiura, and Takuji Hatakeyama disclosed the polycyclic aromatic compound invented by Takuji Hatakeyama and Ryosuke Kawazumi in Angewandte Chemie International Edition, 2020, 59, pp. 1-6.

Article 30, paragraph 2 of the Patent Act applies 1. Program (posted via telecommunications line) (1) Name of the conference: The Chemical Society of Japan 101st Annual Meeting of Spring (2021) https://confit.atlas.jp/guide/event/csj101st/top (2) Posting date: January 18, 2021 (3) Publication: List of titles of oral presentations [A17-2pm-09] (4) Disclosure by: Toshiki Niiya, Susumu Oda, Takuji Hatakeyama (5) Publication content: "Synthesis of BN-containing nonacene analogues by one-shot multiple boronation" 2. Abstract (posted via telecommunication line) (1) Name of the society: The 101st Annual Meeting of the Chemical Society of Japan (2021) https://confit.atlas.jp/guide/event/csj101st/top (2) Posting date: March 4, 2021 (3) Publication: Abstract of the 101st Annual Meeting of the Chemical Society of Japan [A17-2pm-09] (4) Publisher: Toshiki Shintani, Susumu Oda, Takuji Hatakeyama (5) Publication content: "Synthesis of BN-containing nonacene analogues by one-shot multiple boronation"

Article 30, paragraph 2 of the Patent Act applies 1. Program (posted via telecommunications line) (1) Name of the conference: The Chemical Society of Japan 101st Annual Meeting of Spring (2021) https://confit.atlas.jp/guide/event/csj101st/top (2) Posting date: January 18, 2021 (3) Publication: List of titles of oral presentations [A17-2pm-07] (4) Disclosure by: Akio Aoyama, Susumu Oda, Takuji Hatakeyama (5) Publication content: "Synthesis of BN-containing polycyclic aromatic compounds with seven-membered rings by one-shot boronization" 2. Abstract (posted via telecommunication line) (1) Name of the society: The Chemical Society of Japan 101st Annual Meeting of Spring (2021) https://confit.atlas.jp/guide/event/csj101st/top (2) Posting date: March 4, 2021 (3) Publication: Abstract of the 101st Annual Meeting of Spring [A17-2pm-07] (4) Disclosure by: Akio Aoyama, Susumu Oda, Takuji Hatakeyama (5) Publication content: "Synthesis of BN-containing polycyclic aromatic compounds with seven-membered rings by one-shot boronization"

The present invention relates to a polycyclic aromatic compound, and an organic electroluminescent element, an organic field effect transistor, an organic thin-film solar cell, and a wavelength conversion filter, as well as a display device and a lighting device, which use the same. In this specification, the term "organic electroluminescent element" may be referred to as "organic EL element" or simply as "element."

Display devices using electroluminescent light-emitting elements have been extensively studied because they can be made thin and energy-efficient, and organic electroluminescent devices made from organic materials have been actively studied because they can be easily made large and lightweight. In particular, there has been active research into the development of organic materials that have the luminescence properties of blue, one of the three primary colors of light, and organic materials that have the ability to transport charges such as holes and electrons (potential to become semiconductors or superconductors), regardless of whether they are polymeric or low-molecular-weight compounds.

An organic EL element has a structure consisting of a pair of electrodes consisting of an anode and a cathode, and one or more layers containing organic compounds that are disposed between the pair of electrodes. The layers containing organic compounds include a light-emitting layer and a charge transport/injection layer that transports or injects charges such as holes and electrons, and various organic materials suitable for these layers have been developed.

As materials for the light-emitting layer, for example, benzofluorene-based compounds have been developed (WO 2004/061047). As hole-transporting materials, for example, triphenylamine-based compounds have been developed (JP 2001-172232 A). As electron-transporting materials, for example, anthracene-based compounds have been developed (JP 2005-170911 A).

In recent years, a material that improves triphenylamine derivatives has also been reported for use in organic electroluminescence devices and organic thin-film solar cells (WO 2012/118164). This material is based on N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), which has already been put to practical use, and is characterized by its improved planarity while placing nitrogen at the center of the ring structure by linking the aromatic rings that make up the triphenylamine. For example, this document evaluates the charge transport properties of an NO-linked compound (compound 1 on page 63), but does not describe how to manufacture materials other than NO-linked compounds, and since the electronic state of the entire compound differs depending on the linked element, the properties obtained from materials other than NO-linked compounds are not yet known. There are other examples of such compounds (WO 2011/107186). For example, compounds having a conjugated structure with a large triplet exciton energy (T1) are useful as materials for blue light-emitting layers because they can emit phosphorescence with a shorter wavelength. In addition, compounds having a novel conjugated structure with a large T1 are also required as electron transport materials and hole transport materials sandwiching the light-emitting layer.

The host material of an organic EL element is generally a molecule in which a plurality of existing aromatic rings such as benzene or carbazole are linked by single bonds, phosphorus atoms, or silicon atoms. This is because a large HOMO-LUMO gap (band gap Eg in a thin film) required for a host material is guaranteed by linking a large number of relatively small conjugated aromatic rings. Furthermore, a high triplet excitation energy (E _T ) is also required for a host material of an organic EL element using a phosphorescent material or a thermally activated delayed fluorescent material, but by linking a donor or acceptor aromatic ring or a substituent to the molecule, SOMO1 and SOMO2 in the triplet excited state (T1) are localized, and the exchange interaction between the two orbitals is reduced, thereby making it possible to improve the triplet excitation energy (E _T ). However, the redox stability of small conjugated aromatic rings is insufficient, and an element using a molecule in which existing aromatic rings are linked as a host material does not have a sufficient life. On the other hand, polycyclic aromatic compounds having an extended π-conjugated system generally have excellent redox stability, but have been considered unsuitable as host materials due to their low HOMO-LUMO gap (band gap Eg in a thin film) and triplet excitation energy (E _T ).

In recent years, compounds in which multiple aromatic rings are condensed with a central atom such as boron have also been reported (WO 2015/102118). In this document, an evaluation of an organic EL device was carried out using the compound in which multiple aromatic rings are condensed as a dopant material in the light-emitting layer.

International Publication No. 2004/061047 JP 2001-172232 A JP 2005-170911 A International Publication No. 2012/118164 International Publication No. 2011/107186 International Publication No. 2015/102118

As reported in Patent Documents 1 to 5, various materials have been developed for use in organic EL elements, but in order to increase the options for materials for organic EL elements, there is a need to develop materials made of compounds that are different from conventional ones. In particular, it would be beneficial to explore organic EL characteristics and manufacturing methods that can be obtained from materials other than NO-linked compounds in which nitrogen is located at the center of the ring structure.

Furthermore, Patent Document 6 reports on a polycyclic aromatic compound containing boron and an organic EL device using the same, but this document discloses an extremely large number of compounds, and it would be beneficial to explore light-emitting layer materials, particularly dopant materials, that can improve organic EL characteristics such as luminous efficiency and device life, in order to further improve device characteristics.

In addition, in addition to vacuum deposition, wet film-forming methods are currently used as a method for forming the organic layers that make up organic EL elements. Therefore, active development of ink materials for wet film-forming, particularly for forming hole injection layers, hole transport layers, and light-emitting layers, is underway, and it is also beneficial to explore such ink materials.

As a result of intensive research to solve the above problems, the present inventors discovered that an excellent organic EL element can be obtained by, for example, constructing an organic EL element by disposing a layer containing a polycyclic aromatic compound having a novel structure between a pair of electrodes, and thus completed the present invention. That is, the present invention provides the following polycyclic aromatic compounds, and further provides materials for organic devices, such as materials for organic EL elements, containing the following polycyclic aromatic compounds:

In this specification, the chemical structure or the substituent may be expressed by the number of carbon atoms, but the number of carbon atoms in the case where a chemical structure is substituted with a substituent or where a substituent is further substituted with a substituent means the number of carbon atoms in each of the chemical structure and the substituent, and does not mean the total number of carbon atoms in the chemical structure and the substituent, or the total number of carbon atoms in the substituent and the substituent. For example, "substituent B of carbon number Y substituted with substituent A of carbon number X" means that "substituent B of carbon number Y" is substituted with "substituent A of carbon number X", and the carbon number Y is not the total number of carbon atoms of the substituent A and the substituent B. Also, for example, "substituent B of carbon number Y substituted with substituent A" means that "substituent B of carbon number Y" is substituted with "substituent A (with no carbon number limit)", and the carbon number Y is not the total number of carbon atoms of the substituent A and the substituent B.

［φ１］ｎの部分は、上記式（φ１－ｍ１）で表される単位構造、上記式（φ１－ｍ２）で表される単位構造、上記式（φ１－ｐ１）で表される単位構造、および上記式（φ１－ｐ２）で表される単位構造からなる群から選択される少なくとも１種の単位構造が合計でｎ個連結して構成される部分であり、
ｎは１以上の整数であり、
Ｂ１環、Ｂ２環、およびＣ環は、それぞれ独立して、アリール環またはヘテロアリール環であり、これらの環における少なくとも１つの水素は置換されていてもよく、
Ｒ^ａは、それぞれ独立して、水素または置換基であり、
ａ環における「－Ｃ（－Ｒ^ａ）＝」は「－Ｎ＝」に置き換わっていてもよく、
Ｙは、それぞれ独立して、Ｂ、Ｐ、Ｐ＝Ｏ、Ｐ＝Ｓ、Ａｌ、Ｇａ、Ａｓ、Ｓｉ－Ｒ、またはＧｅ－Ｒであり、前記Ｓｉ－ＲのＲおよびＧｅ－ＲのＲは、アリール、ヘテロアリール、アルキル、またはシクロアルキルであり、
Ｘ^１は、それぞれ独立して、＞Ｎ－Ｒ、＞Ｏ、＞Ｓ、＞Ｃ（－Ｒ）_２、＞Ｓｉ（－Ｒ）_２、または＞Ｓｅであり、前記＞Ｎ－ＲのＲ、＞Ｃ（－Ｒ）_２のＲ、および＞Ｓｉ（－Ｒ）_２のＲは、それぞれ独立して、置換されていてもよいアリール、置換されていてもよいヘテロアリール、置換されていてもよいアルキル、または置換されていてもよいシクロアルキルであり、
また、前記Ｘ^１としての、＞Ｃ（－Ｒ）_２の２つのＲ同士および＞Ｓｉ（－Ｒ）_２の２つのＲ同士は、それぞれ独立して、単結合または連結基により結合していてもよく、
また、前記Ｘ^１としての＞Ｎ－ＲのＲ、＞Ｃ（－Ｒ）_２のＲ、および＞Ｓｉ（－Ｒ）_２のＲの少なくとも１つは、単結合または連結基により、前記Ｂ１環、Ｂ２環、Ｃ環、およびａ環の少なくとも１つと結合していてもよく、
Ｘ^２は、それぞれ独立して、ＮまたはＣ－Ｒであり、前記Ｃ－ＲのＲは、それぞれ独立して、置換されていてもよいアリール、置換されていてもよいヘテロアリール、置換されていてもよいアルキル、または置換されていてもよいシクロアルキルであり、
上記式（１Ａ）、式（φ１－ｍ１）、および式（φ１－ｍ２）における隣接するＣ環同士は、それぞれ独立して、単結合または連結基により結合していてもよく、
上記式（１Ａ）または式（１Ｂ）で表される化合物における、Ｂ１環、Ｂ２環、Ｃ環、アリール、およびヘテロアリールの少なくとも１つは、少なくとも１つのシクロアルカンで縮合されていてもよく、当該シクロアルカンにおける少なくとも１つの水素は置換されていてもよく、当該シクロアルカンにおける少なくとも１つの－ＣＨ_２－は－Ｏ－で置換されていてもよく、
上記式（１Ａ）または式（１Ｂ）で表される化合物における少なくとも１つの水素は、重水素、シアノ、またはハロゲンで置換されていてもよい。 Item 1.
A polycyclic aromatic compound represented by the following general formula (1A) or (1B):

the portion [φ1]n is a portion constituted by n units of at least one type of unit structure selected from the group consisting of the unit structure represented by the above formula (φ1-m1), the unit structure represented by the above formula (φ1-m2), the unit structure represented by the above formula (φ1-p1), and the unit structure represented by the above formula (φ1-p2),
n is an integer of 1 or more,
ring B1, ring B2, and ring C are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen atom in these rings may be substituted;
Each R ^a is independently hydrogen or a substituent;
"-C(-R ^a )=" in ring a may be replaced with "-N=";
Y is each independently B, P, P═O, P═S, Al, Ga, As, Si—R, or Ge—R, wherein R of Si—R and R of Ge—R are aryl, heteroaryl, alkyl, or cycloalkyl;
^X1 is each independently >N-R, >O, >S, >C(-R) ₂ , >Si(-R) ₂ , or >Se, and R of >N-R, R of >C(-R) ₂ , and R of >Si(-R) ₂ are each independently an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl, or an optionally substituted cycloalkyl;
In addition, the two Rs in >C(-R) ₂ and the two Rs in >Si(-R) ₂ as ^X1 may each be independently bonded to each other via a single bond or a linking group,
At least one of R of >N-R, R of >C(-R) ₂ , and R of >Si(-R) ₂ as ^X1 may be bonded to at least one of ring B1, ring B2, ring C, and ring a via a single bond or a linking group;
^X2 is independently N or C-R, and R in C-R is independently an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl, or an optionally substituted cycloalkyl;
adjacent C rings in the above formula (1A), formula (φ1-m1), and formula (φ1-m2) may each independently be bonded to each other via a single bond or a linking group;
In the compound represented by the above formula (1A) or (1B), at least one of ring B1, ring B2, ring C, aryl, and heteroaryl may be condensed with at least one cycloalkane, at least one hydrogen in the cycloalkane may be substituted, and at least one -CH ₂ - in the cycloalkane may be substituted with -O-;
At least one hydrogen atom in the compound represented by the above formula (1A) or (1B) may be substituted with deuterium, cyano, or halogen.

Item 2.
the portion [φ1]n is a portion constituted by n units of at least one type of unit structure selected from the group consisting of the unit structure represented by the above formula (φ1-m1), the unit structure represented by the above formula (φ1-m2), the unit structure represented by the above formula (φ1-p1), and the unit structure represented by the above formula (φ1-p2),
n is an integer from 1 to 5;
ring B1, ring B2, and ring C are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen atom in these rings may be substituted by a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted diarylamino, a substituted or unsubstituted diheteroarylamino, a substituted or unsubstituted arylheteroarylamino, a substituted or unsubstituted diarylboryl (two aryls may be bonded via a single bond or a linking group), a substituted or unsubstituted alkyl, a substituted or unsubstituted cycloalkyl, a substituted or unsubstituted alkoxy, a substituted or unsubstituted aryloxy, or a substituted silyl;
R ^a is each independently hydrogen, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted diarylamino, a substituted or unsubstituted diheteroarylamino, a substituted or unsubstituted arylheteroarylamino, a substituted or unsubstituted diarylboryl (two aryls may be bonded via a single bond or a linking group), a substituted or unsubstituted alkyl, a substituted or unsubstituted cycloalkyl, a substituted or unsubstituted alkoxy, a substituted or unsubstituted aryloxy, or a substituted silyl;
"-C(-R ^a )=" in ring a may be replaced with "-N=";
Y is each independently B, P, P═O, P═S, Al, Ga, As, Si—R, or Ge—R, wherein R of Si—R and R of Ge—R are aryl, heteroaryl, alkyl, or cycloalkyl;
X ¹ is each independently >N-R, >O, >S, >C(-R) ₂ , >Si(-R) ₂ , or >Se, and R of >N-R, R of >C(-R) ₂ , and R of >Si(-R) ₂ are each independently aryl optionally substituted with alkyl or cycloalkyl, heteroaryl optionally substituted with alkyl or cycloalkyl, alkyl, or cycloalkyl;
In addition, the two Rs of >C(-R) ₂ and the two Rs of >Si(-R) ₂ as X ¹ may each independently be bonded to each other by a single bond, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R) ₂ -, -Si(-R) ₂ -, or -Se-; the R of -CR=CR-, the R of -N(-R)-, the R of -C(-R) ₂ -, and the R of -Si(-R) ₂ - are each independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, at least one hydrogen in the R may be substituted with an alkyl or cycloalkyl, and adjacent two Rs may form a ring to form a cycloalkylene, arylene, or heteroarylene;
At least one of R of >N-R, R of >C(-R) ₂ , and R of >Si(-R) ₂ as X ¹ may be bonded to at least one of ring B1, ring B2, ring C, and ring a via a single bond, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R) ₂ -, -Si(-R) ₂ -, or -Se-; and R of -CR=CR-, R of -N(-R)-, R of -C(-R) ₂ -, and -Si(-R) ₂ - may be bonded to at least one of ring B1, ring B2, ring C, and ring a via a single bond, R in - is each independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, at least one hydrogen in the R may be substituted with alkyl or cycloalkyl, and two adjacent R may form a ring to form cycloalkylene, arylene, or heteroarylene;
^X2 each independently represents N or C-R, and R in said C-R each independently represents aryl optionally substituted with alkyl or cycloalkyl, heteroaryl optionally substituted with alkyl or cycloalkyl, alkyl, or cycloalkyl;
When X ² is N, adjacent C rings in the above formula (1A), formula (φ1-m1), and formula (φ1-m2) may each independently be bonded to each other by a single bond, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R) ₂ -, -Si(-R) ₂ -, or -Se-, R of -CR=CR-, R of -N(-R)-, R of -C(-R) ₂ -, and R of -Si(-R) ₂ - are each independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, at least one hydrogen in the R may be substituted by alkyl or cycloalkyl, two adjacent Rs may form a ring to form a cycloalkylene, arylene, or heteroarylene,
In the compound represented by the above formula (1A) or (1B), at least one of ring B1, ring B2, ring C, aryl, and heteroaryl may be condensed with at least one cycloalkane, at least one hydrogen in the cycloalkane may be substituted, and at least one -CH ₂ - in the cycloalkane may be substituted with -O-;
At least one hydrogen atom in the compound represented by the above formula (1A) or formula (1B) may be substituted with deuterium, cyano, or halogen.
Item 2. The polycyclic aromatic compound according to item 1.

［φ２］ｎの部分は、上記式（φ２－ｍ１）で表される単位構造、上記式（φ２－ｍ２）で表される単位構造、上記式（φ２－ｐ１）で表される単位構造、および上記式（φ２－ｐ２）で表される単位構造からなる群から選択される少なくとも１種の単位構造が合計でｎ個連結して構成される部分であり、
ｎは１～３の整数であり、
Ｒ^ａ、Ｒ^ｂ、およびＲ^ｃは、それぞれ独立して、水素、アリール、ヘテロアリール、ジアリールアミノ、ジヘテロアリールアミノ、アリールヘテロアリールアミノ、ジアリールボリル（２つのアリールは単結合または連結基を介して結合していてもよい）、アルキル、シクロアルキル、アルコキシ、アリールオキシ、トリアリールシリル、トリアルキルシリル、トリシクロアルキルシリル、ジアルキルシクロアルキルシリル、またはアルキルジシクロアルキルシリルであり、当該Ｒ^ａ、Ｒ^ｂ、およびＲ^ｃにおける少なくとも１つの水素は、アリール、ヘテロアリール、アルキル、またはシクロアルキルで置換されていてもよく、また、Ｒ^ｂおよびＲ^ｃのうちの隣接する基同士が結合して、ｂ１環およびｃ環と共に、アリール環またはヘテロアリール環を形成していてもよく、形成された環における少なくとも１つの水素は、アリール、ヘテロアリール、ジアリールアミノ、ジヘテロアリールアミノ、アリールヘテロアリールアミノ、ジアリールボリル（２つのアリールは単結合または連結基を介して結合していてもよい）、アルキル、シクロアルキル、アルコキシ、アリールオキシ、トリアリールシリル、トリアルキルシリル、トリシクロアルキルシリル、ジアルキルシクロアルキルシリル、またはアルキルジシクロアルキルシリルで置換されていてもよく、これらの置換基における少なくとも１つの水素は、アリール、ヘテロアリール、アルキル、またはシクロアルキルで置換されていてもよく、
ａ環における「－Ｃ（－Ｒ^ａ）＝」は「－Ｎ＝」に置き換わっていてもよく、
ｂ１環およびｃ環における、任意の「－Ｃ（－Ｒ）＝」（ここでＲはＲ^ｂまたはＲ^ｃである）は「－Ｎ＝」に置き換わっていてもよく、任意の「－Ｃ（－Ｒ）＝Ｃ（－Ｒ）－」（ここでＲはＲ^ｂまたはＲ^ｃである）は、「－Ｎ（－Ｒ）－」、「－Ｏ－」、「－Ｓ－」、「－Ｃ（－Ｒ）_２－」、「－Ｓｉ（－Ｒ）_２－」、または「－Ｓｅ－」に置き換わっていてもよく、前記「－Ｎ（－Ｒ）－」のＲ、「－Ｃ（－Ｒ）_２－」のＲ、および「－Ｓｉ（－Ｒ）_２－」のＲは、アリール、ヘテロアリール、アルキル、またはシクロアルキルであり、
ｂ２環における、任意の「－Ｃ（－Ｒ^ｂ）＝」は「－Ｎ＝」に置き換わっていてもよく、また、一方の「－Ｃ（－Ｒ^ｂ）＝」が単結合であって、かつ他方の「－Ｃ（－Ｒ^ｂ）＝」が、「－Ｎ（－Ｒ）－」、「－Ｏ－」、「－Ｓ－」、「－Ｃ（－Ｒ）_２－」、「－Ｓｉ（－Ｒ）_２－」、または「－Ｓｅ－」に置き換わっていてもよく、前記「－Ｎ（－Ｒ）－」のＲ、「－Ｃ（－Ｒ）_２－」のＲ、および「－Ｓｉ（－Ｒ）_２－」のＲは、アリール、ヘテロアリール、アルキル、またはシクロアルキルであり、
Ｙは、それぞれ独立して、Ｂ、Ｐ、Ｐ＝Ｏ、Ｐ＝Ｓ、Ａｌ、Ｇａ、Ａｓ、Ｓｉ－Ｒ、またはＧｅ－Ｒであり、前記Ｓｉ－ＲのＲおよびＧｅ－ＲのＲは、アリール、ヘテロアリール、アルキル、またはシクロアルキルであり、
Ｘ^１は、それぞれ独立して、＞Ｎ－Ｒ、＞Ｏ、＞Ｓ、＞Ｃ（－Ｒ）_２、＞Ｓｉ（－Ｒ）_２、または＞Ｓｅであり、前記＞Ｎ－ＲのＲ、＞Ｃ（－Ｒ）_２のＲ、および＞Ｓｉ（－Ｒ）_２のＲは、それぞれ独立して、炭素数１～６のアルキルもしくは炭素数３～１４のシクロアルキルで置換されていてもよい炭素数６～１２のアリール、炭素数１～６のアルキルもしくは炭素数３～１４のシクロアルキルで置換されていてもよい炭素数２～１５のヘテロアリール、炭素数１～６のアルキル、または炭素数３～１４のシクロアルキルであり、
また、前記Ｘ^１としての、＞Ｃ（－Ｒ）_２の２つのＲ同士および＞Ｓｉ（－Ｒ）_２の２つのＲ同士は、それぞれ独立して、単結合、－ＣＨ＝ＣＨ－、－ＣＲ＝ＣＲ－、－Ｃ≡Ｃ－、－Ｎ（－Ｒ）－、－Ｏ－、－Ｓ－、－Ｃ（－Ｒ）_２－、－Ｓｉ（－Ｒ）_２－、または－Ｓｅ－により結合していてもよく、前記－ＣＲ＝ＣＲ－のＲ、－Ｎ（－Ｒ）－のＲ、－Ｃ（－Ｒ）_２－のＲ、および－Ｓｉ（－Ｒ）_２－のＲは、それぞれ独立して、水素、炭素数６～１２のアリール、炭素数２～１５のヘテロアリール、炭素数１～６のアルキル、炭素数１～６のアルケニル、炭素数１～６のアルキニル、または炭素数３～１４のシクロアルキルであり、当該Ｒにおける少なくとも１つの水素は炭素数１～６のアルキルまたは炭素数３～１４のシクロアルキルで置換されていてもよく、隣接する２つのＲ同士が環を形成し、炭素数３～１４のシクロアルキレン、炭素数６～１２のアリーレン、または炭素数２～１５のヘテロアリーレンを形成していてもよく、
また、前記Ｘ^１としての＞Ｎ－ＲのＲ、＞Ｃ（－Ｒ）_２のＲ、および＞Ｓｉ（－Ｒ）_２のＲの少なくとも１つは、単結合、－ＣＨ＝ＣＨ－、－ＣＲ＝ＣＲ－、－Ｃ≡Ｃ－、－Ｎ（－Ｒ）－、－Ｏ－、－Ｓ－、－Ｃ（－Ｒ）_２－、－Ｓｉ（－Ｒ）_２－、または－Ｓｅ－により、前記ａ環、ｂ１環、ｂ２環、およびｃ環の少なくとも１つと結合していてもよく、前記－ＣＲ＝ＣＲ－のＲ、－Ｎ（－Ｒ）－のＲ、－Ｃ（－Ｒ）_２－のＲ、および－Ｓｉ（－Ｒ）_２－のＲは、それぞれ独立して、水素、炭素数６～１２のアリール、炭素数２～１５のヘテロアリール、炭素数１～６のアルキル、炭素数１～６のアルケニル、炭素数１～６のアルキニル、または炭素数３～１４のシクロアルキルであり、当該Ｒにおける少なくとも１つの水素は炭素数１～６のアルキルまたは炭素数３～１４のシクロアルキルで置換されていてもよく、隣接する２つのＲ同士が環を形成し、炭素数３～１４のシクロアルキレン、炭素数６～１２のアリーレン、または炭素数２～１５のヘテロアリーレンを形成していてもよく、
Ｘ^２は、それぞれ独立して、ＮまたはＣ－Ｒであり、前記Ｃ－ＲのＲは、それぞれ独立して、炭素数６～１２のアリール、炭素数２～１５のヘテロアリール、炭素数１～６のアルキル、または炭素数３～１４のシクロアルキルであり、
Ｘ^２がＮのとき、上記式（２Ａ）、式（φ２－ｍ１）、および式（φ２－ｍ２）における、隣接するｃ環における隣接するＲ^ｃ同士は、結合して、単結合、－ＣＨ＝ＣＨ－、－ＣＲ＝ＣＲ－、－Ｃ≡Ｃ－、－Ｎ（－Ｒ）－、－Ｏ－、－Ｓ－、－Ｃ（－Ｒ）_２－、－Ｓｉ（－Ｒ）_２－、または－Ｓｅ－になっていてもよく、前記－ＣＲ＝ＣＲ－のＲ、－Ｎ（－Ｒ）－のＲ、－Ｃ（－Ｒ）_２－のＲ、および－Ｓｉ（－Ｒ）_２－のＲは、それぞれ独立して、水素、炭素数６～１２のアリール、炭素数２～１５のヘテロアリール、炭素数１～６のアルキル、炭素数１～６のアルケニル、炭素数１～６のアルキニル、または炭素数３～１４のシクロアルキルであり、当該Ｒにおける少なくとも１つの水素は炭素数１～６のアルキルまたは炭素数３～１４のシクロアルキルで置換されていてもよく、隣接する２つのＲ同士が環を形成し、炭素数３～１４のシクロアルキレン、炭素数６～１２のアリーレン、または炭素数２～１５のヘテロアリーレンを形成していてもよく、
上記式（２Ａ）または式（２Ｂ）で表される化合物における、前記ｂ１環、前記ｃ環、前記形成された環、前記アリール、および前記ヘテロアリールの少なくとも１つは、炭素数３～２４の少なくとも１つのシクロアルカンで縮合されていてもよく、当該シクロアルカンにおける少なくとも１つの水素は、炭素数６～３０のアリール、炭素数２～３０のヘテロアリール、炭素数１～２４のアルキル、または炭素数３～２４のシクロアルキルで置換されていてもよく、当該シクロアルカンにおける少なくとも１つの－ＣＨ_２－は－Ｏ－で置換されていてもよく、
上記式（２Ａ）または式（２Ｂ）で表される化合物における少なくとも１つの水素は、重水素、シアノ、またはハロゲンで置換されていてもよい。 Item 3.
Item 3. The polycyclic aromatic compound according to item 1, which is represented by the following general formula (2A) or (2B):

the portion [φ2]n is a portion constituted by n units of at least one type of unit structure selected from the group consisting of the unit structure represented by the above formula (φ2-m1), the unit structure represented by the above formula (φ2-m2), the unit structure represented by the above formula (φ2-p1), and the unit structure represented by the above formula (φ2-p2),
n is an integer from 1 to 3;
R ^a , R ^b , and R ^c are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl, and at least one hydrogen in ^{R a} , R ^b , and R ^c may be substituted with an aryl, heteroaryl, ^alkyl , or cycloalkyl. Adjacent groups among ^c may be bonded to each other to form an aryl ring or a heteroaryl ring together with ring b1 and ring c, and at least one hydrogen atom in the formed ring may be substituted with aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl, and at least one hydrogen atom in these substituents may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl;
"-C(-R ^a )=" in ring a may be replaced with "-N=";
In the b1 ring and the c ring, any "-C(-R)=" (wherein R is R ^b or R ^c ) may be replaced with "-N=", any "-C(-R)=C(-R)-" (wherein R is R ^b or R ^c ) may be replaced with "-N(-R)-", "-O-", "-S-", "-C(-R) ₂ -", "-Si(-R) ₂ -" or "-Se-", and R of "-N(-R)-", R of "-C(-R) ₂ -" and R of "-Si(-R) ₂ -" are aryl, heteroaryl, alkyl or cycloalkyl,
any "-C(-R ^b )=" in ring b2 may be replaced with "-N=", and one "-C(-R ^b )=" may be a single bond and the other "-C(-R ^b )=" may be replaced with "-N(-R)-", "-O-", "-S-", "-C(-R) ₂ -", "-Si(-R) ₂ -" or "-Se-", and R of "-N(-R)-", R of "-C(-R) ₂ -" and R of "-Si(-R) ₂ -" are aryl, heteroaryl, alkyl or cycloalkyl,
Y is each independently B, P, P═O, P═S, Al, Ga, As, Si—R, or Ge—R, wherein R of Si—R and R of Ge—R are aryl, heteroaryl, alkyl, or cycloalkyl;
^X1 is each independently >N-R, >O, >S, >C(-R) ₂ , >Si(-R) ₂ , or >Se, and R of >N-R, R of >C(-R) ₂ , and R of >Si(-R) ₂ are each independently an aryl having 6 to 12 carbon atoms which may be substituted with an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms, a heteroaryl having 2 to 15 carbon atoms which may be substituted with an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms, an alkyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 14 carbon atoms;
In addition, the two Rs in >C(-R) ₂ and the two Rs in >Si(-R) ₂ as X ¹ may be bonded independently to each other via a single bond, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R) ₂ -, -Si(-R) ₂ -, or -Se-, and the R in -CR=CR-, the R in -N(-R)-, the R in -C(-R) ₂ -, and the -Si(-R) ₂ R's in - are each independently a hydrogen atom, an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 6 carbon atoms, an alkenyl having 1 to 6 carbon atoms, an alkynyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 14 carbon atoms, in which at least one hydrogen atom in the R's is optionally substituted with an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms, and two adjacent R's may form a ring to form a cycloalkylene having 3 to 14 carbon atoms, an arylene having 6 to 12 carbon atoms, or a heteroarylene having 2 to 15 carbon atoms;
At least one of R of >N-R, R of >C(-R) ₂ , and R of >Si(-R) ₂ as X ¹ may be bonded to at least one of the ring a, ring b1, ring b2, and ring c via a single bond, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R) _{2 -} , -Si(-R) ₂ -, or -Se- _. R's in - are each independently a hydrogen atom, an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 6 carbon atoms, an alkenyl having 1 to 6 carbon atoms, an alkynyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 14 carbon atoms, in which at least one hydrogen atom in the R's is optionally substituted with an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms, and two adjacent R's may form a ring to form a cycloalkylene having 3 to 14 carbon atoms, an arylene having 6 to 12 carbon atoms, or a heteroarylene having 2 to 15 carbon atoms;
^X2 each independently represents N or C-R, and R in the C-R each independently represents an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 14 carbon atoms;
When X ² is N, adjacent R ^c in adjacent c rings in the above formula (2A), formula (φ2-m1), and formula (φ2-m2) may be bonded to each other to form a single bond, -CH═CH-, -CR═CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R) 2 -, -Si(-R) 2 -, or -Se-, and the R of -CR═CR-, the R of -N(-R)-, the R of -C(-R) ₂ -, and the -Si(-R) ₂ - may be bonded to each other to form a single bond, -CH═CH-, -CR═CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R) ₂ - _, R's in - are each independently a hydrogen atom, an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 6 carbon atoms, an alkenyl having 1 to 6 carbon atoms, an alkynyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 14 carbon atoms, in which at least one hydrogen atom in the R's is optionally substituted with an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms, and two adjacent R's may form a ring to form a cycloalkylene having 3 to 14 carbon atoms, an arylene having 6 to 12 carbon atoms, or a heteroarylene having 2 to 15 carbon atoms;
In the compound represented by the above formula (2A) or (2B), at least one of the ring b1, the ring c, the formed ring, the aryl, and the heteroaryl may be condensed with at least one cycloalkane having 3 to 24 carbon atoms, at least one hydrogen in the cycloalkane may be substituted with an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms, an alkyl having 1 to 24 carbon atoms, or a cycloalkyl having 3 to 24 carbon atoms, and at least one -CH ₂ - in the cycloalkane may be substituted with -O-;
At least one hydrogen atom in the compound represented by the above formula (2A) or (2B) may be substituted with deuterium, cyano, or halogen.

Item 4.
the portion [φ2]n is a portion constituted by n units of at least one type of unit structure selected from the group consisting of the unit structure represented by the above formula (φ2-m1), the unit structure represented by the above formula (φ2-m2), the unit structure represented by the above formula (φ2-p1), and the unit structure represented by the above formula (φ2-p2),
n is an integer from 1 to 3;
R ^a , R ^b , and R ^c each independently represent a hydrogen atom, an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms, a diarylamino (wherein the aryl is an aryl having 6 to 12 carbon atoms), a diarylboryl (wherein the aryl is an aryl having 6 to 12 carbon atoms, and the two aryls may be bonded via a single bond or a linking group), an alkyl having 1 to 24 carbon atoms, or a cycloalkyl having 3 to 24 carbon atoms, and at least one hydrogen atom in R ^a , R ^b , and R ^c may be substituted with an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 6 carbon atoms, or a ^cycloalkyl having 3 to 14 carbon atoms. adjacent groups among ^c may be bonded to each other to form, together with ring b1 and ring c, an aryl ring having 9 to 16 carbon atoms or a heteroaryl ring having 6 to 15 carbon atoms, in which at least one hydrogen atom in the formed ring may be substituted with an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms, a diarylamino (wherein the aryl is an aryl having 6 to 12 carbon atoms), a diarylboryl (wherein the aryl is an aryl having 6 to 12 carbon atoms, and the two aryls may be bonded via a single bond or a linking group), an alkyl having 1 to 24 carbon atoms, or a cycloalkyl having 3 to 24 carbon atoms, in which at least one hydrogen atom in these substituents may be substituted with an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 14 carbon atoms;
"-C(-R ^a )=" in ring a may be replaced with "-N=";
In ring b1 and ring c, any "-C(-R)=" (wherein R is R ^b or R ^c ) may be replaced with "-N=", any "-C(-R)=C(-R)-" (wherein R is R ^b or R ^c ) may be replaced with "-N(-R)-", "-O-", "-S-", "-C(-R) ₂ -", "-Si(-R) ₂ -" or "-Se-", and R of "-N(-R)-", R of "-C(-R) ₂ -" and R of "-Si(-R) ₂ -" are aryl having 6 to 12 carbon atoms, heteroaryl having 2 to 15 carbon atoms, alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms,
In ring b2, any "-C(-R ^b )=" may be replaced with "-N=", and one "-C(-R ^b )=" may be a single bond and the other "-C(-R ^b )=" may be replaced with "-N(-R)-", "-O-", "-S-", "-C(-R) ₂ -", "-Si(-R) ₂ -" or "-Se-", and R of "-N(-R)-", R of "-C(-R) ₂ -" and R of "-Si(-R) ₂ -" are aryl having 6 to 12 carbon atoms, heteroaryl having 2 to 15 carbon atoms, alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms,
Y's are each independently B, P, P=O, P=S, Al, Ga, As, Si-R, or Ge-R, and R of the Si-R and R of the Ge-R are an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 14 carbon atoms;
X ¹ is each independently >N-R, >O, >S, >C(-R) ₂ , >Si(-R) ₂ , or >Se, and R of >N-R, R of >C(-R) ₂ , and R of >Si(-R) ₂ are each independently an aryl having 6 to 10 carbon atoms which may be substituted with an alkyl having 1 to 5 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms, a heteroaryl having 2 to 10 carbon atoms which may be substituted with an alkyl having 1 to 5 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms;
In addition, the two Rs in >C(-R) ₂ and the two Rs in >Si(-R) ₂ as X ¹ may be bonded independently to each other via a single bond, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R) ₂ -, -Si(-R) ₂ -, or -Se-, and the R in -CR=CR-, the R in -N(-R)-, the R in -C(-R) ₂ -, and the -Si(-R) ₂ R's in - are each independently hydrogen, an aryl having 6 to 10 carbon atoms, a heteroaryl having 2 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms, an alkenyl having 1 to 5 carbon atoms, an alkynyl having 1 to 5 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms, in which at least one hydrogen atom in the R's may be substituted with an alkyl having 1 to 5 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms, and two adjacent R's may form a ring to form a cycloalkylene having 5 to 10 carbon atoms, an arylene having 6 to 10 carbon atoms, or a heteroarylene having 2 to 10 carbon atoms;
At least one of R of >N-R, R of >C(-R) ₂ , and R of >Si(-R) ₂ as X ¹ may be bonded to at least one of the ring a, ring b1, ring b2, and ring c via a single bond, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R) _{2 -} , -Si(-R) ₂ -, or -Se- _. R's in - are each independently hydrogen, an aryl having 6 to 10 carbon atoms, a heteroaryl having 2 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms, an alkenyl having 1 to 5 carbon atoms, an alkynyl having 1 to 5 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms, in which at least one hydrogen atom in the R's may be substituted with an alkyl having 1 to 5 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms, and two adjacent R's may form a ring to form a cycloalkylene having 5 to 10 carbon atoms, an arylene having 6 to 10 carbon atoms, or a heteroarylene having 2 to 10 carbon atoms;
^X2 each independently represents N or C-R, and R in the C-R each independently represents an aryl having 6 to 10 carbon atoms, a heteroaryl having 2 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms;
When X ² is N, adjacent R ^c in all adjacent c rings in the above formula (2A), formula (φ2-m1), and formula (φ2-m2) may be bonded to each other to form a single bond, -CH═CH-, -CR═CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R) 2 -, -Si(-R) 2 -, or -Se-, and the R of -CR═CR-, the R of -N(-R)-, the R of -C(-R) ₂ -, and the -Si(-R) ₂ - may be bonded to each other to form a single bond, -CH═CH-, -CR═CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R) ₂ - _, R's in - are each independently hydrogen, an aryl having 6 to 10 carbon atoms, a heteroaryl having 2 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms, an alkenyl having 1 to 5 carbon atoms, an alkynyl having 1 to 5 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms, in which at least one hydrogen atom in the R's may be substituted with an alkyl having 1 to 5 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms, and two adjacent R's may form a ring to form a cycloalkylene having 5 to 10 carbon atoms, an arylene having 6 to 10 carbon atoms, or a heteroarylene having 2 to 10 carbon atoms;
In the compound represented by the above formula (2A) or formula (2B), at least one of the ring b1, the ring c, the formed ring, the aryl, and the heteroaryl may be condensed with at least one cycloalkane having 3 to 20 carbon atoms, and at least one hydrogen in the cycloalkane may be substituted with an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, an alkyl having 1 to 12 carbon atoms, or a cycloalkyl having 3 to 16 carbon atoms;
At least one hydrogen atom in the compound represented by the above formula (2A) or formula (2B) may be substituted with deuterium, cyano, or halogen.
Item 4. The polycyclic aromatic compound according to item 3.

Item 5.
The portion [φ2]n in the above formula (2A) is a portion constituted by n units of at least one type of unit structure selected from the group consisting of the unit structure represented by the above formula (φ2-m1) and the unit structure represented by the above formula (φ2-m2),
The portion [φ2]n in the above formula (2B) is a portion constituted by n units of at least one type of unit structure selected from the group consisting of the unit structure represented by the above formula (φ2-p1) and the unit structure represented by the above formula (φ2-p2),
n is an integer from 1 to 3;
R ^a , R ^b , and R ^c each independently represent a hydrogen atom, an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 20 carbon atoms, a diarylamino (wherein the aryl is an aryl having 6 to 10 carbon atoms), a diarylboryl (wherein the aryl is an aryl having 6 to 10 carbon atoms, and two aryls may be bonded via a single bond or a linking group), an alkyl having 1 to 12 carbon atoms, or a cycloalkyl having 3 to 16 carbon atoms, and at least one hydrogen atom in the R ^a , R ^b , and R ^c may be substituted by an aryl having 6 to 10 carbon atoms, a heteroaryl having 2 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms;
"-C(-R ^a )=" in ring a may be replaced with "-N=";
In ring b1 and ring c, any "-C(-R)=" (wherein R is R ^b or R ^c ) may be replaced with "-N=", any "-C(-R)=C(-R)-" (wherein R is R ^b or R ^c ) may be replaced with "-N(-R)-", "-O-", "-S-" or "-C(-R) ₂ -", and R of the "-N(-R)-" and R of "-C(-R) ₂ -" are aryl having 6 to 10 carbon atoms, heteroaryl having 2 to 10 carbon atoms, alkyl having 1 to 5 carbon atoms or cycloalkyl having 5 to 10 carbon atoms,
In ring b2, any "-C(-R ^b )=" may be replaced with "-N=", or one "-C(-R ^b )=" may be a single bond and the other "-C(-R ^b )=" may be replaced with "-N(-R)-", "-O-", "-S-" or "-C(-R) ₂ -", and R of the "-N(-R)-" and R of "-C(-R) ₂ -" are aryl having 6 to 10 carbon atoms, heteroaryl having 2 to 10 carbon atoms, alkyl having 1 to 5 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms,
Each Y is independently B, P, P=O, or P=S;
^X1 is each independently >N-R, >O, >S, or >C(-R) ₂ , and R of the >N-R and R of the >C(-R) ₂ are each independently an aryl having 6 to 10 carbon atoms which may be substituted with an alkyl having 1 to 5 carbon atoms, a heteroaryl having 2 to 10 carbon atoms which may be substituted with an alkyl having 1 to 5 carbon atoms, an alkyl having 1 to 5 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms;
In addition, the two Rs in >C(-R) ₂ and the two Rs in >Si(-R) ₂ as X ¹ may each independently be bonded to each other via a single bond, -CH=CH-, -CR=CR-, -N(-R)-, -O-, -S-, or -C(-R) ₂ -, the R in -CR=CR-, the R in -N(-R)-, and the R in -C(-R) ₂ - each independently represent a hydrogen atom, an aryl having 6 to 10 carbon atoms, a heteroaryl having 2 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms, an alkenyl having 1 to 5 carbon atoms, an alkynyl having 1 to 5 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms, and two adjacent Rs may each form a ring to form a cycloalkylene having 5 to 10 carbon atoms, an arylene having 6 to 10 carbon atoms, or a heteroarylene having 2 to 10 carbon atoms,
At least one of R of >N-R, R of >C(-R) ₂ , and R of >Si(-R) ₂ as X ¹ may be bonded to at least one of the ring a, ring b1, ring b2, and ring c via a single bond, -CH=CH-, -CR=CR-, -N(-R)-, -O-, -S-, or -C(-R) ₂ -, and R of -CR=CR-, R of -N(-R)-, and -C(-R) _{2 -} may be bonded to at least one of the ring a, ring b1, ring b2, and ring c via a single bond, R's in - are each independently hydrogen, an aryl having 6 to 10 carbon atoms, a heteroaryl having 2 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms, an alkenyl having 1 to 5 carbon atoms, an alkynyl having 1 to 5 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms, and two adjacent R's may be bonded to form a ring to form a cycloalkylene having 5 to 10 carbon atoms, an arylene having 6 to 10 carbon atoms, or a heteroarylene having 2 to 10 carbon atoms;
^X2 is N;
In the above formula (2A), formula (φ2-m1), and formula (φ2-m2), adjacent R ^c in all adjacent c rings may be bonded to each other to form a single bond, -CH═CH-, -CR═CR-, -N(-R)-, -O-, -S-, or -C(-R) ₂ -, R of the -CR═CR-, R of -N(-R)-, and R of -C(-R) ₂ - are each independently an aryl having 6 to 10 carbon atoms, a heteroaryl having 2 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms, an alkenyl having 1 to 5 carbon atoms, an alkynyl having 1 to 5 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms, and two adjacent R may be bonded to each other to form a ring, which is a cycloalkylene having 5 to 10 carbon atoms, an arylene having 6 to 10 carbon atoms, or a heteroarylene having 2 to 10 carbon atoms;
In the compound represented by the above formula (2A) or formula (2B), at least one of the ring b1, the ring c, the aryl, and the heteroaryl may be condensed with at least one cycloalkane having 3 to 16 carbon atoms, and at least one hydrogen in the cycloalkane may be substituted with an aryl having 6 to 10 carbon atoms, a heteroaryl having 2 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms;
At least one hydrogen atom in the compound represented by the above formula (2A) or formula (2B) may be substituted with deuterium, cyano, or halogen.
Item 4. The polycyclic aromatic compound according to item 3.

Item 6.
The portion [φ2]n in the above formula (2A) is a portion constituted by n units of at least one type of unit structure selected from the group consisting of the unit structure represented by the above formula (φ2-m1) and the unit structure represented by the above formula (φ2-m2),
The portion [φ2]n in the above formula (2B) is a portion constituted by n units of at least one type of unit structure selected from the group consisting of the unit structure represented by the above formula (φ2-p1) and the unit structure represented by the above formula (φ2-p2),
n is 1 or 2;
R ^a , R ^b , and R ^c each independently represent a hydrogen atom, an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 20 carbon atoms, a diarylamino (wherein the aryl is an aryl having 6 to 10 carbon atoms), a diarylboryl (wherein the aryl is an aryl having 6 to 10 carbon atoms, and two aryls may be bonded via a single bond or a linking group), an alkyl having 1 to 12 carbon atoms, or a cycloalkyl having 3 to 16 carbon atoms, and at least one hydrogen atom in the R ^a , R ^b , and R ^c may be substituted with an alkyl having 1 to 5 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms;
"-C(-R ^a )=" in ring a may be replaced with "-N=";
In ring b1 and ring c, any "-C(-R)=" (wherein R is ^Rb or ^Rc ) may be replaced with "-N=", any "-C(-R)=C(-R)-" (wherein R is ^Rb or ^Rc ) may be replaced with "-N(-R)-", "-O-" or "-S-", and R of the "-N(-R)-" is an aryl having 6 to 10 carbon atoms, a heteroaryl having 2 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms;
In ring b2, any "-C(-R ^b )=" may be replaced with "-N=", or one "-C(-R ^b )=" may be a single bond and the other "-C(-R ^b )=" may be replaced with "-N(-R)-", "-O-" or "-S-", and R of the "-N(-R)-" is an aryl having 6 to 10 carbon atoms, a heteroaryl having 2 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms;
Each Y is independently B;
^X1 's are each independently >N-R or >O, and each R in the >N-R is independently an aryl having 6 to 10 carbon atoms which may be substituted with an alkyl having 1 to 5 carbon atoms, an alkyl having 1 to 5 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms;
R in >N-R as ^X1 may be bonded to at least one of the ring a, ring b1, ring b2, and ring c via a single bond;
^X2 is N;
In the above formula (2A), formula (φ2-m1), and formula (φ2-m2), adjacent R ^c in all adjacent c rings may be bonded to each other to form a single bond,
In the compound represented by the above formula (2A) or formula (2B), at least one of the ring b1, the ring c, and the aryl having 6 to 10 carbon atoms as R in the >N-R may be condensed with a cycloalkane having 3 to 14 carbon atoms, and at least one hydrogen in the cycloalkane may be substituted with an alkyl having 1 to 5 carbon atoms;
At least one hydrogen atom in the compound represented by the above formula (2A) or formula (2B) may be substituted with deuterium, cyano, or halogen.
Item 4. The polycyclic aromatic compound according to item 3.

（構造式中の「Ｍｅ」はメチル基を示す。） Section 7.
Item 2. The polycyclic aromatic compound according to item 1, which is represented by the following structural formula:

("Me" in the structural formula represents a methyl group.)

（構造式中の「Ｍｅ」はメチル基、「ｔＢｕ」はｔ－ブチル基を示す。） Section 8.
Item 2. The polycyclic aromatic compound according to item 1, which is represented by any one of the following structural formulas:

(In the structural formula, "Me" represents a methyl group and "tBu" represents a t-butyl group.)

（構造式中の「Ｍｅ」はメチル基、「ｔＢｕ」はｔ－ブチル基を示す。） Item 9.
Item 2. The polycyclic aromatic compound according to item 1, which is represented by any one of the following structural formulas:

(In the structural formula, "Me" represents a methyl group and "tBu" represents a t-butyl group.)

Item 10.
Item 10. A reactive compound in which the polycyclic aromatic compound according to any one of items 1 to 9 is substituted with a reactive substituent.

Item 11.
Item 11. A polymer compound obtained by polymerizing the reactive compound according to item 10 as a monomer, or a crosslinked polymer obtained by further crosslinking the polymer compound.

Item 12.
Item 11. A pendant polymer compound in which a reactive compound as described in item 10 is substituted on a main chain polymer, or a pendant polymer crosslinked product in which the pendant polymer compound is further crosslinked.

Section 13.
Item 10. A material for an organic device, comprising the polycyclic aromatic compound according to any one of items 1 to 9.

Section 14.
Item 11. A material for an organic device, comprising the reactive compound according to item 10.

Item 15.
Item 12. A material for an organic device, comprising the polymer compound or crosslinked polymer according to item 11.

Section 16.
Item 13. A material for an organic device, comprising the pendant polymer compound or the pendant polymer crosslinked product according to item 12.

Section 17.
Item 17. The material for an organic device according to any one of Items 13 to 16, wherein the material for an organic device is a material for an organic electroluminescent element, a material for an organic field effect transistor, a material for an organic thin-film solar cell, or a material for a wavelength conversion filter.

Section 18.
Item 18. The material for an organic device according to item 17, wherein the material for an organic electroluminescent element is a material for a light-emitting layer.

Section 19.
10. An ink composition comprising the polycyclic aromatic compound according to any one of items 1 to 9 and an organic solvent.

Section 20.
Item 11. An ink composition comprising the reactive compound according to item 10 and an organic solvent.

Section 21.
Item 11. An ink composition comprising a main chain polymer, the reactive compound according to item 10, and an organic solvent.

Section 22.
Item 12. An ink composition comprising the polymer compound or crosslinked polymer according to item 11 and an organic solvent.

Section 23.
Item 13. An ink composition comprising the pendant polymer compound or the pendant polymer crosslinked product according to item 12 and an organic solvent.

Section 24.
Item 17. An organic electroluminescence device comprising a pair of electrodes consisting of an anode and a cathode, and an organic layer disposed between the pair of electrodes and containing the polycyclic aromatic compound according to any one of items 1 to 9, the reactive compound according to item 10, the polymer compound or crosslinked polymer according to item 11, or the pendant polymer compound or crosslinked polymer according to item 12.

Section 25.
Item 25. The organic electroluminescent device according to item 24, wherein the organic layer is a light-emitting layer.

Section 26.
Item 26. The organic electroluminescent device according to item 25, wherein the light-emitting layer contains a host and the polycyclic aromatic compound, reactive compound, polymer compound, crosslinked polymer, pendant polymer compound, or pendant crosslinked polymer as a dopant.

Section 27.
Item 27. The organic electroluminescent device according to item 26, wherein the host is an anthracene-based compound, a fluorene-based compound or a dibenzochrysene-based compound.

Section 28.
Item 28. The organic electroluminescence device according to any one of Items 25 to 27, further comprising at least one of an electron transport layer and an electron injection layer disposed between the cathode and the light emitting layer, and at least one of the electron transport layer and the electron injection layer contains at least one selected from the group consisting of borane derivatives, pyridine derivatives, fluoranthene derivatives, BO-based derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, carbazole derivatives, triazine derivatives, benzimidazole derivatives, phenanthroline derivatives, quinolinol-based metal complexes, thiazole derivatives, benzothiazole derivatives, silole derivatives, and azoline derivatives.

Section 29.
Item 29. The organic electroluminescent device according to item 28, wherein at least one of the electron transport layer and the electron injection layer further contains at least one selected from the group consisting of alkali metals, alkaline earth metals, rare earth metals, oxides of alkali metals, halides of alkali metals, oxides of alkaline earth metals, halides of alkaline earth metals, oxides of rare earth metals, halides of rare earth metals, organic complexes of alkali metals, organic complexes of alkaline earth metals, and organic complexes of rare earth metals.

Section 30.
Item 30. The organic electroluminescence device according to any one of Items 24 to 29, wherein at least one layer of the hole injection layer, the hole transport layer, the light emitting layer, the electron transport layer, and the electron injection layer comprises a polymer compound obtained by polymerizing a low molecular weight compound capable of forming each layer as a monomer, or a crosslinked polymer obtained by further crosslinking the polymer compound, or a pendant type polymer compound obtained by reacting a low molecular weight compound capable of forming each layer with a main chain polymer, or a pendant type crosslinked polymer obtained by further crosslinking the pendant type polymer compound.

Section 31.
Item 31. A display device or lighting device comprising the organic electroluminescent device according to any one of Items 24 to 30.

Section 32.
Item 18. A wavelength conversion filter comprising the material for wavelength conversion filters according to Item 17.

According to a preferred embodiment of the present invention, it is possible to provide a polycyclic aromatic compound having a novel structure that can be used as a material for organic devices, such as a material for an organic electroluminescence (EL) element, and by using this polycyclic aromatic compound, it is possible to provide an excellent organic device, such as an organic electroluminescence (EL) element.

Specifically, the inventors have found that polycyclic aromatic compounds in which aromatic rings are linked by heteroelements such as boron, phosphorus, oxygen, nitrogen, and sulfur have large or small HOMO-LUMO gaps (band gaps in thin films, Eg) depending on the method of linking the heteroelements. This is thought to be because the six-membered rings containing heteroelements have low aromaticity, which suppresses or promotes the reduction in the HOMO-LUMO gap associated with the expansion of the conjugated system and the localization or delocalization of each orbital. These polycyclic aromatic compounds have a robust skeleton in which five- or six-membered rings are condensed or linked, so that the half-width of the fluorescent emission peak is narrow, and light emission with high color purity can be obtained when used as an emitter for an organic EL device. In addition, by selecting the method of linking the heteroelements, they can exhibit thermally activated delayed fluorescence, and can obtain high efficiency when used as an emitter for an organic EL device. Furthermore, since the HOMO and LUMO energies can be arbitrarily shifted by introducing a substituent, it is possible to optimize the ionization potential and electron affinity depending on the surrounding materials. However, the present invention is not particularly limited to these principles.

1 is a schematic cross-sectional view showing an organic EL element according to an embodiment of the present invention. 1 shows the results of fluorescence lifetime measurement of the compound of the invention (1A-92). 4 shows the results of fluorescence lifetime measurement of the compound of the invention (1A-142). 4 shows the results of fluorescence lifetime measurement of the compound of the invention (1A-195). 4 shows the results of fluorescence lifetime measurement of the compound of the invention (1A-197).

上記式（１Ａ）または式（１Ｂ）中の［φ１］ｎの部分は、上記式（φ１－ｍ１）で表される単位構造、上記式（φ１－ｍ２）で表される単位構造、上記式（φ１－ｐ１）で表される単位構造、および上記式（φ１－ｐ２）で表される単位構造からなる群から選択される少なくとも１種の単位構造が合計でｎ個連結して構成される部分である。 1. Polycyclic aromatic compounds
<Explanation of the overall structure of the compound>
The present invention relates to a polycyclic aromatic compound represented by the following general formula (1A) or general formula (1B): The symbols in each structural formula are defined as above, and the symbols in all structural formulas shown in this paragraph and thereafter are also defined as above.

The portion of [φ1]n in the above formula (1A) or formula (1B) is a portion constituted by n units of at least one type of unit structure selected from the group consisting of the unit structure represented by the above formula (φ1-m1), the unit structure represented by the above formula (φ1-m2), the unit structure represented by the above formula (φ1-p1), and the unit structure represented by the above formula (φ1-p2).

上記式（２Ａ）または式（２Ｂ）中の［φ２］ｎの部分は、上記式（φ２－ｍ１）で表される単位構造、上記式（φ２－ｍ２）で表される単位構造、上記式（φ２－ｐ１）で表される単位構造、および上記式（φ２－ｐ２）で表される単位構造からなる群から選択される少なくとも１種の単位構造が合計でｎ個連結して構成される部分である。 The present invention is preferably a polycyclic aromatic compound represented by the following general formula (2A) or general formula (2B): The symbols in each structural formula are defined as above, and the symbols in all structural formulas shown in this paragraph and thereafter are also defined as above.

The portion of [φ2]n in the above formula (2A) or (2B) is a portion constituted by n units of at least one type of unit structure selected from the group consisting of the unit structure represented by the above formula (φ2-m1), the unit structure represented by the above formula (φ2-m2), the unit structure represented by the above formula (φ2-p1), and the unit structure represented by the above formula (φ2-p2).

The above n is an integer of 1 or more, and preferably an integer from 1 to 5, an integer from 1 to 3, or 1 or 2. When dissolved in a solution and used as an ink composition for application, n is preferably an integer from 1 to 20, an integer from 2 to 7, or an integer from 3 to 5.

<Explanation of the unit structure that constitutes the compound>
The polycyclic aromatic compound is a compound in which (n+1) (where n is an integer of 1 or more) unit structures of at least one type selected from the meta type unit structure and the para type unit structure shown below are fused and linked so as to share a B1 ring or a b1 ring. The ring portion formed by condensing so as to share the B1 ring is represented by a B2 ring in the above formulae (φ1-m1), (φ1-m2), (φ1-p1), and (φ1-p2), and the ring portion formed by condensing so as to share the b1 ring is represented by a b2 ring in the above formulae (φ2-m1), (φ2-m2), (φ2-p1), and (φ2-p2).

The meta-type unit structure has a structure in which two Ys are located at the meta position of the a-ring, and the para-type unit structure has a structure in which two Ys are located at the para position of the a-ring. Both unit structures contain two condensed bicyclic structures. The condensed bicyclic structure is a structure in which two 6-membered saturated hydrocarbon rings are condensed together in the meta-type unit structure (a decahydronaphthalene structure comprising Y, ^X1 and ^X2 ), and the two condensed bicyclic structures are arranged (condensed) around the a-ring so as to be condensed together. The para-type unit structure is a structure in which two 6-membered saturated hydrocarbon rings are condensed together (a decahydronaphthalene structure comprising Y and two ^X1 ), and the two condensed bicyclic structures are arranged (condensed) around the a-ring so as to be located at the para position of the a-ring.

<Description of the connection form of unit structures>
The polycyclic aromatic compound of the above formula (1A) contains at least one meta-type unit structure 1 as a unit structure φ1, and the other unit structures φ1 may be only meta-type unit structures 1, only para-type unit structures 1, or a mixture of meta-type unit structures 1 and para-type unit structures 1. A preferred embodiment is a compound in which a total of (n+1) meta-type unit structures 1 are linked as unit structures φ1.

The polycyclic aromatic compound of the above formula (1B) contains at least one para-type unit structure 1 as a unit structure φ1, and the other unit structures φ1 may be only para-type unit structures 1, only meta-type unit structures 1, or a mixture of para-type unit structures 1 and meta-type unit structures 1. However, the preferred form is a compound in which a total of (n+1) para-type unit structures 1 are linked as unit structures φ1.

The polycyclic aromatic compound of the above formula (2A) contains at least one meta-type unit structure 2 as a unit structure φ2, and the other unit structures φ2 may be only meta-type unit structures 2, only para-type unit structures 2, or a mixture of meta-type unit structures 2 and para-type unit structures 2. However, the preferred form is a compound in which a total of (n+1) meta-type unit structures 2 are linked as unit structures φ2.

The polycyclic aromatic compound of the above formula (2B) contains at least one para-type unit structure 2 as a unit structure φ2, and the other unit structures φ2 may be only para-type unit structures 2, only meta-type unit structures 2, or a mixture of para-type unit structures 2 and meta-type unit structures 2. However, the preferred form is a compound in which a total of (n+1) para-type unit structures 2 are linked as unit structures φ2.

In terms of the form in which each unit structure is linked, meta unit structure 1 comes in two forms, the form of the above formula (φ1-m1) and the form of the above formula (φ1-m2) (upside-down form), para unit structure 1 comes in two forms, the form of the above formula (φ1-p1) and the form of the above formula (φ1-p2) (upside-down form), meta unit structure 2 comes in two forms, the form of the above formula (φ2-m1) and the form of the above formula (φ2-m2) (upside-down form), and para unit structure 2 comes in two forms, the form of the above formula (φ2-p1) and the form of the above formula (φ2-p2) (upside-down form).

The polycyclic aromatic compounds of the above formula (1A), (1B), (2A) or (2B) may be linked in a mixture of upside-down inverted forms, but compounds in which only non-upside-down inverted forms are linked are preferred.

In formula (1A), an embodiment in which at least one kind selected from the group consisting of formula (φ1-m1) and formula (φ1-m2) is selected in a total of n pieces as φ1 is preferred, and an embodiment in which only n pieces of formula (φ1-m1) are selected is more preferred.
In formula (1B), an embodiment in which at least one kind selected from the group consisting of formula (φ1-p1) and formula (φ1-p2) is selected in a total of n pieces as φ1 is preferable, and an embodiment in which only n pieces of formula (φ1-p1) are selected is more preferable.
In formula (2A), an embodiment in which at least one kind selected from the group consisting of formula (φ2-m1) and formula (φ2-m2) is selected in a total of n pieces as φ2 is preferable, and an embodiment in which only n pieces of formula (φ2-m1) are selected is more preferable.
In formula (2B), an embodiment in which at least one kind selected from the group consisting of formula (φ2-p1) and formula (φ2-p2) is selected in a total of n pieces as φ2 is preferable, and an embodiment in which only n pieces of formula (φ2-p1) are selected is more preferable.

The B1 ring and the b1 ring in the meta type unit structure and the para type unit structure are fused to the fused 2-ring structure at one position, but when the unit structures are fused and linked to each other so as to share the B1 ring or the b1 ring as described above, the B1 ring and the b1 ring are transformed into a structure in which they are fused to the fused 2-ring structure at two positions (a structure sandwiched between two fused 2-ring structures), so the notations have been changed to B2 ring and b2 ring, respectively, as shown in the above formulas (φ1-m1), (φ1-m2), (φ1-p1), (φ1-p2), (φ2-m1), (φ2-m2), (φ2-p1), and (φ2-p2). The notations of the B1 ring and the b1 ring that are not involved in the linkage are left as they are.

<Description of each part of the compound and unit structure>
Next, each part of the compound and the unit structure will be described. As described above, the polycyclic aromatic compound of formula (1A), formula (1B), formula (2A), or formula (2B) is a compound formed by repeatedly linking the meta-type unit structure and the para-type unit structure, so the description of each part of the compound and the description of each part of the unit structure (the meta-type unit structure, the para-type unit structure, the unit structure of formula (φ1-m1), formula (φ1-m2), formula (φ1-p1), formula (φ1-p2), formula (φ2-m1), formula (φ2-m2), formula (φ2-p1), or formula (φ2-p2)) constituting it are basically the same. However, as described above, the B1 ring and b1 ring whose structure is deformed when the unit structures are linked to each other, and the B2 ring and b2 ring after the deformation will be described separately as necessary.

<Explanation of Ring Structure and Its Substituents>
The B1 ring, B2 ring, and C ring in each formula are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen atom in these rings may be substituted with a substituent. The substituent is preferably a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted diarylamino, a substituted or unsubstituted diheteroarylamino, a substituted or unsubstituted arylheteroarylamino (an amino group having an aryl and a heteroaryl), a substituted or unsubstituted diarylboryl (two aryls may be bonded via a single bond or a linking group), a substituted or unsubstituted alkyl, a substituted or unsubstituted cycloalkyl, a substituted or unsubstituted alkoxy, a substituted or unsubstituted aryloxy, or a substituted silyl. When these groups have a substituent, examples of the substituent include aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls may be bonded via a single bond or a linking group), an alkyl, a cycloalkyl, an alkoxy, an aryloxy, or a substituted silyl. Details of the rings and substituents listed here will be described below.

R ^a in each formula is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino (amino group having aryl and heteroaryl), substituted or unsubstituted diarylboryl (two aryls may be bonded via a single bond or a linking group), substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, or substituted silyl. When these groups have a substituent, examples of the substituent include aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyl. Details of the rings and substituents listed here will be described below.

Specific examples of R ^b and R ^c in each formula, and more specific examples of R ^a are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl, and at least one hydrogen in the R ^a , R ^b , and R ^c may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl. Details of the substituents listed here will be described below.

The aryl or heteroaryl ring as ring B1, ring B2, and ring C preferably has a 5- or 6-membered ring sharing a bond with the above-mentioned fused bicyclic structure.
Here, "a six-membered ring sharing a bond with a fused two-ring structure" means, for example, ring b1, ring b2, and ring c (benzene ring (six-membered ring)) fused to a fused two-ring structure as shown in formula (2A), formula (2B), and their unit structural formulas. In addition, "an aryl ring or heteroaryl ring (which is ring B1, ring B2, and ring C) has this six-membered ring" means that ring B1, ring B2, and ring C are formed only from this six-membered ring, or that ring B1, ring B2, and ring C are formed so as to include this six-membered ring by further condensing other rings to this six-membered ring. In other words, "an aryl ring or heteroaryl ring (which is ring B1, ring B2, and ring C) having a six-membered ring" means that the six-membered ring constituting all or part of ring B1, ring B2, and ring C is fused to a fused two-ring structure. In addition, the same explanation applies to "five-membered ring".

B1 ring, B2 ring and C ring correspond to b1 ring and its substituent R ^b , b2 ring and its substituent R ^b , and c ring and its substituent R ^c , respectively. That is, formula (2A), formula (2B) and their unit structural formulas correspond to the structure in which "B1 ring, B2 ring and C ring having 6-membered ring (benzene ring)" are selected as B1 ring, B2 ring and C ring of formula (1A), formula (1B) and their unit structural formulas. In this sense, each ring in formula (2A), formula (2B) and their unit structural formulas is represented by lowercase "b1", "b2" and "c".

<Explanation of changes in ring structure due to bonding between substituents>
Adjacent groups among the substituents R ^b and R ^c of the b1 ring and the c ring may be bonded to each other to form an aryl ring or a heteroaryl ring together with the b1 ring or the c ring, and at least one hydrogen atom in the formed ring may be substituted with an aryl, a heteroaryl, a diarylamino, a diheteroarylamino, an arylheteroarylamino, a diarylboryl (two aryls may be bonded via a single bond or a linking group), an alkyl, a cycloalkyl, an alkoxy, an aryloxy, a triarylsilyl, a trialkylsilyl, a tricycloalkylsilyl, a dialkylcycloalkylsilyl, or an alkyldicycloalkylsilyl, and at least one hydrogen atom in these substituents may be substituted with an aryl, a heteroaryl, an alkyl, or a cycloalkyl.The details of the rings and substituents listed here will be described below.

Therefore, in the polycyclic aromatic compound of formula (2A) or formula (2B), the ring structure constituting the compound changes depending on the mutual bonding form of the substituents in ring b1 and ring c, as shown in the following formulas (2A-fr1) to (2A-fr7) and (2B-fr1) to (2B-fr7). Ring B1' and ring C' in each formula correspond to ring B1 and ring C in formulas (1A) and (1B), respectively. Note that the display of φ1 and ring B1 on the right side in each formula is omitted. In addition, the structural change of ring c shown in each formula below also applies to the unit structural formula, but since there is no adjacent group in ring b2 in the unit structural formula, no new ring is formed.

The B1' ring and C' ring in the above formula (2A-fr1) to formula (2A-fr7) and formula (2B-fr1) to formula (2B-fr7) are, when explained in formula (2A) and formula (2B), aryl rings or heteroaryl rings formed together with the b1 ring and the c ring by bonding adjacent groups among the multiple substituents R ^b and R ^c (they can also be said to be fused rings formed by condensing other ring structures to the b1 ring or the c ring). Also, as can be seen from the above formula, for example, R b of the b1 ring and R ^c of the c ring, and R ^c of different c rings do not fall under "adjacent groups", and basically they do not bond together. In other words, "adjacent groups" means groups adjacent on the same ring.

The above formulae (2A-fr1) to (2A-fr7) and formulae (2B-fr1) to (2B-fr7) have a B1' ring or C' ring formed by condensing, for example, a benzene ring, an indole ring, a pyrrole ring, a benzofuran ring, or a benzothiophene ring to a benzene ring which is a b1 ring or a c ring, and the formed condensed ring B1' or condensed ring C' is, for example, a naphthalene ring, a carbazole ring, an indole ring, a dibenzofuran ring, or a dibenzothiophene ring, respectively.

For example, more specific examples of formulae (2A-fr1) to (2A-fr3) and formulae (2B-fr1) to (2B-fr3) are shown below.

The above formula (2A-fr1-ex) is a specific example of formula (2A-fr1), and is an example in which two adjacent R ^b in ring b1 of formula (2A) are bonded to form an aryl ring (naphthalene ring) represented by B1' together with ring b1 (benzene ring). The formed aryl ring has a six-membered ring (benzene ring b1) that shares a bond with the above-mentioned fused two-ring structure. Note that optional substituents on the aryl ring B1' (ring B1 of formula (1A)) are represented by n Rs in addition to R ^b , and the upper limit of n is the maximum number of possible substitutions.

The above formulae (2A-fr2-ex) and (2A-fr3-ex) are specific examples of formulae (2A-fr2) and (2A-fr3), respectively, and are examples in which two adjacent R ^c in ring c of formula (2A) are bonded to form a heteroaryl ring represented by C' (a carbazole ring and a dibenzofuran ring, respectively) together with ring c (a benzene ring). The formed heteroaryl ring has a six-membered ring (a benzene ring c) that shares a bond with the above-mentioned fused two-ring structure. Note that optional substituents on the heteroaryl ring C' (ring C of formula (1A)) are represented by n Rs in addition to R ^c , and the upper limit of n is the maximum number that can be substituted.

The above formula (2B-fr1-ex) is a specific example of formula (2B-fr1), and is an example in which two adjacent R ^b in ring b1 of formula (2B) are bonded to form an aryl ring (naphthalene ring) represented by B1' together with ring b1 (benzene ring). The formed aryl ring has a six-membered ring (benzene ring b1) that shares a bond with the above-mentioned fused two-ring structure. Note that optional substituents on the aryl ring B1' (ring B1 of formula (1B)) are represented by n Rs in addition to R ^b , and the upper limit of n is the maximum number of possible substitutions.

The above formulae (2B-fr2-ex) and (2B-fr3-ex) are specific examples of formulae (2B-fr2) and (2B-fr3), respectively, and are examples in which two adjacent R ^c in ring c of formula (2B) are bonded to form a heteroaryl ring represented by C' (a carbazole ring and a dibenzofuran ring, respectively) together with ring c (a benzene ring). The formed heteroaryl ring has a six-membered ring (a benzene ring c) that shares a bond with the above-mentioned fused two-ring structure. Note that optional substituents on the heteroaryl ring C' (ring C of formula (1B)) are represented by n Rs in addition to R ^c , and the upper limit of n is the maximum number that can be substituted.

In the above explanation, formula (2A) and formula (2B) are used, but this explanation can be applied to their partial structural formulas as well. In addition, the above explanation can be applied to any form other than the specific examples described above.

Examples of changes in the ring structure constituting the compound will be described more specifically below.
For the purpose of this explanation, the formulae representing the entire compounds of formula (2A) and formula (2B) above, and the formulae representing partial structures of formula (φ2-m1), formula (φ2-m2), formula (φ2-p1), and formula (φ2-p2) are simplified (substituents R ^a , R ^b , and R ^c are not shown but actually exist) and are represented by the following overall formula (Y2X3-A), overall formula (Y2X4-B), partial formula (φ2-Y2X3-m1), partial formula (φ2-Y2X3-m2), partial formula (φ2-Y2X4-p1), and partial formula (φ2-Y2X4-p2), respectively.

For example, the case where a 5-membered ring structure is condensed to ring b1 in the overall formula (Y2X3-A) is shown below.

Here, each Q is independently >N-R, >O, >S, >C(-R) ₂ , >Si(-R) ₂ , or >Se, and R in >N-R, R in >C(-R) ₂ , and R in >Si(-R) ₂ are each independently an optionally substituted aryl or an optionally substituted heteroaryl, and the same applies below. Details of the substituents listed here will be described below.
When Q is meta-positioned with respect to ^X1 , the TADF property tends to be high. In addition, in order to shorten the emission wavelength, it is preferable that Q is >O. Furthermore, when Q is >S, >Si(-R) ₂ , or >Se, which is an atom heavier than B atom, C atom, N atom, and O atom, the TADF property tends to be high due to the heavy atom effect.

When Q is >O, ring b1 is a dibenzofuran ring, as shown below.

Similarly, a five-membered ring structure can be condensed to the partial structure φ2. For example, the case where a five-membered ring structure is condensed to the ring c in the partial formula (φ2-Y2X3-m1) is shown below.

When Q is >O, ring c is a dibenzofuran ring, as shown below.

<Explanation of the central element Y in the compound>
Y in each formula is B, P, P=O, P=S, Al, Ga, As, Si-R, or Ge-R, and R in the Si-R and Ge-R is aryl, heteroaryl, alkyl, or cycloalkyl. In the case of P=O, P=S, Si-R, or Ge-R, the atom bonded to the ring a, the ring B1 (ring b1), the ring B2 (ring b2), and the ring C (ring c) is P, Si, or Ge. Y is preferably B, P, P=O, P=S, or Si-R, more preferably B, P, P=O, or P=S, and particularly preferably B. Details of the substituents listed here will be described below.

Next, examples of Y are explained in more detail using the overall and partial formulas described above.

By disposing Y at the meta position, the multiple resonance effect is strengthened, and light emission with high TADF and narrow half width tends to be obtained. When Y is P, P=O or P=S, light emission with shorter wavelength and large ΔEST tends to be obtained, and when Y is B, light emission with longer wavelength and small ΔEST tends to be obtained.

By arranging Y in the para position, the multiple resonance effect is weakened, and light emission with a large ΔEST and a narrow half-width tends to be obtained. When Y is P, P=O, or P=S, light emission with a shorter wavelength and a large ΔEST tends to be obtained, and when Y is B, light emission with a longer wavelength and a small ΔEST tends to be obtained.

The partial structure φ2 can be considered in a similar manner.

<Explanation of Linking Elements ^X1 and X2 ⁱⁿ Compound >
X ¹ in each formula is independently >N-R, >O, >S, >C(-R) ₂ , >Si(-R) ₂ , or >Se, and R of >N-R, R of >C(-R) ₂ , and R of >Si(-R) ₂ are independently optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl, or optionally substituted cycloalkyl.
From the viewpoint of stability, ^X1 is preferably >N-R, >O, >S, or >C(-R) ₂ , and more preferably >N-R or >O. From the viewpoint of short wavelength emission, >N-R, >O, or >C(-R) ₂ is preferable, and more preferably >O or >C(-R) ₂ .
^X2 in each formula is independently N or C-R, and R in C-R is independently an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl, or an optionally substituted cycloalkyl. N is preferable as ^X2 .
The details of the substituents listed here will be described later.

Next, examples of ^X1 and ^X2 will be described more specifically using the overall formula and partial formulae described above.

By arranging X at the meta position, the multiple resonance effect tends to be strengthened and a small ΔEST tends to be obtained. On the other hand, by arranging X at the para position, the multiple resonance effect tends to be weakened and a large ΔEST tends to be obtained. When Y is P, P=O, or P=S, emission of a shorter wavelength and a large ΔEST tend to be obtained, and when Y is B, emission of a longer wavelength and a small ΔEST tend to be obtained. In addition, since X is always arranged at the meta position or the para position in the polycyclic aromatic compound of the present invention, it has a robust skeleton and tends to emit light with a narrow half width.

The partial structure φ2 can be considered in a similar manner.

Furthermore, the two Rs in >C(-R) ₂ and the two Rs in >Si(-R) ₂ as X ¹ may each be independently bonded to each other via a single bond or a linking group. Examples of this linking group include -CH ₂ -CH ₂ -, -CHR-CHR-, -CR ₂ -CR ₂ -, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R) ₂ -, -Si(-R) ₂ -, or -Se-, and examples of the structure include the following: The R of -CHR-CHR-, the R of -CR ₂ -CR ₂ -, the R of -CR═CR-, the R of -N(-R)-, the R of -C(-R) ₂ -, and the R of -Si(-R) ₂ - are each independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, and at least one hydrogen in the R may be substituted with an alkyl or cycloalkyl. Two adjacent Rs may form a ring to form a cycloalkylene, arylene, or heteroarylene. Details of the substituents listed here will be described below.

Among these, a single bond and the linking groups -CR=CR-, -N(-R)-, -O-, -S-, -C(-R) ₂ -, -Si(-R) ₂ -, and -Se- are preferred, a single bond and the linking groups -CR=CR-, -N(-R)-, -O-, -S-, and -C(-R) ₂ - are more preferred, a single bond and the linking groups -CR=CR-, -N(-R)-, -O-, and -S- are even more preferred, and a single bond is most preferred.

The position at which two R's are bonded by a single bond or a linking group is not particularly limited as long as it is a position where bonding is possible, but it is preferable for them to be bonded at the most adjacent positions. For example, if two R's are phenyl groups, it is preferable for them to be bonded at the ortho (2nd) positions based on the bonding position (1st position) of "C" or "Si" in the phenyl group (see the structural formula above).

< Explanation of Change in Ring Structure Due to Bonding of X1 to the Ring ^>
At least one of ^X1 , R of >N-R, R of >C(-R) ₂ , and R of >Si(-R) ₂ may be bonded to at least one of ring B1 (ring b1), ring B2 (ring b2), ring C (ring c), and ring a in each formula through a single bond or a linking group.
As X ¹ which may participate in a bond, >N--R and >C(--R) ₂ are preferred, and >N--R is more preferred.
The ring to be bonded is preferably ring B1 (ring b1) or ring C (ring c).
Examples of the linking group connecting R to the ring include -CH2 _{- CH2-} , -CHR-CHR-, _{-CR2- CR2-} , -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R) _2- , -Si(-R) _2- and -Se-, with -CR=CR-, -N(-R)-, -O-, -S- and -C(-R) _2- being preferred, and -CR=CR-, -N(-R)-, -O- and -S- being more preferred. In addition, R in the above "-CHR-CHR-", "-CR ₂ -CR ₂ -", "-CR═CR-", "-N(-R)-", "-C(-R) ₂ -" and "-Si(-R) ₂ -" is each independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, and at least one hydrogen in the R may be substituted with alkyl or cycloalkyl. In addition, two adjacent Rs may form a ring to form a cycloalkylene, arylene, or heteroarylene.
The details of the substituents listed here will be described later.

The provision in formula (1A) and formula (1B) that "at least one of R of >N-R as ^X1 , R of >C(-R) ₂ , and R of >Si(-R) ₂ is bonded to at least one of the ring B1, ring B2, ring C, and ring a through a single bond or a linking group" corresponds to the provision in formula (2A) and formula (2B) that "at least one of R of >N-R as ^X1 , R of >C(-R) ₂ , and R of >Si(-R) ₂ is bonded to at least one of the ring a, ring b1, ring b2, and ring c through a single bond, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R) _{2- ,} -Si(-R)2-, or -Se-".

左の構造式では、Ｘ^１の選択肢（＞Ｎ－Ｒ、＞Ｃ（－Ｒ）_２、および＞Ｓｉ（－Ｒ）_２）におけるＲがｂ１環、ｂ２環、およびａ環と結合した例であり、式（２Ａ）および式（φ２－ｍ１）におけるｂ１環（ベンゼン環）、ｂ２環（ベンゼン環）、およびａ環（ベンゼン環）に対してＸ^１を取り込むようにして他の環が縮合して形成されたＢ１’環、Ｂ２’環、およびａ’環を有する化合物を表している。形成された縮合環Ｂ１’、縮合環Ｂ２’、および縮合環ａ’は、例えば、フェノキサジン環、フェノチアジン環、カルバゾール環、またはアクリジン環などである。
右の構造式は、左の構造式のより具体的な例を表しており、
Ｘ^１である＞Ｎ－ＲのＲ（フェニル基）が、連結基である－Ｏ－によりｂ１環（ベンゼン環）と結合して、破線で囲んだフェノキサジン環Ｂ１’が形成され、
Ｘ^１である＞Ｎ－ＲのＲ（フェニル基）が、連結基である－Ｓ－によりｂ２環（ベンゼン環）と結合して、破線で囲んだフェノチアジン環Ｂ２’が形成され、
Ｘ^１である＞Ｎ－ＲのＲ（フェニル基）が、単結合によりａ環（ベンゼン環）と結合して、破線で囲んだカルバゾール環ａ’が形成された例である。 This definition can be expressed, for example, by the following structural formula, which is a combination (n=1) of formula (2A) and formula (φ2-m1) where φ2 is a group. Note that although the substituents R ^a , R ^b and R ^c in the structural formula are not shown, they actually exist.

The structural formula on the left is an example in which R in the options for ^X1 (>N-R, >C(-R) ₂ , and >Si(-R) ₂ ) is bonded to ring b1, ring b2, and ring a, and represents a compound having ring B1', ring B2', and ring a' formed by condensing other rings to ring b1 (benzene ring), ring b2 (benzene ring), and ring a (benzene ring) in formula (2A) and formula (φ2-m1) so as to incorporate ^X1 . The formed condensed ring B1', condensed ring B2', and condensed ring a' are, for example, a phenoxazine ring, a phenothiazine ring, a carbazole ring, or an acridine ring.
The structural formula on the right shows a more specific example of the structural formula on the left.
R (phenyl group) of >N-R which is ^X1 is bonded to the b1 ring (benzene ring) via the linking group -O- to form a phenoxazine ring B1' surrounded by a dashed line,
R (phenyl group) of >N-R which is ^X1 is bonded to ring b2 (benzene ring) via a linking group -S- to form a phenothiazine ring B2' surrounded by a dashed line,
This is an example in which R (phenyl group) of >N--R, which is ^X1 , is bonded to a ring (benzene ring) via a single bond to form a carbazole ring a' surrounded by a dashed line.

左の構造式では、Ｘ^１の選択肢（＞Ｎ－Ｒ、＞Ｃ（－Ｒ）_２、および＞Ｓｉ（－Ｒ）_２）におけるＲがｃ環、ｂ２環、およびｂ１環と結合した例であり、式（２Ｂ）および式（φ２－ｐ１）におけるｃ環（ベンゼン環）、ｂ２環（ベンゼン環）、およびｂ１環（ベンゼン環）に対してＸ^１を取り込むようにして他の環が縮合して形成されたＣ’環、Ｂ２’環、およびＢ１’環を有する化合物を表している。形成された縮合環Ｃ’、縮合環Ｂ２’、および縮合環Ｂ１’は、例えば、フェノキサジン環、フェノチアジン環、カルバゾール環、またはアクリジン環などである。
右の構造式は、左の構造式のより具体的な例を表しており、
Ｘ^１である＞Ｎ－ＲのＲ（フェニル基）が、連結基である－Ｏ－によりｃ環（ベンゼン環）と結合して、破線で囲んだフェノキサジン環Ｃ’が形成され、
Ｘ^１である＞Ｎ－ＲのＲ（フェニル基）が、単結合によりｂ２環（ベンゼン環）と結合して、破線で囲んだカルバゾール環Ｂ２’が形成され、
Ｘ^１である＞Ｎ－ＲのＲ（フェニル基）が、連結基である－Ｓ－によりｂ１環（ベンゼン環）と結合して、破線で囲んだフェノチアジン環Ｂ１’が形成された例である。 This rule can be expressed, for example, by the following structural formula, which is a combination (n=1) of formula (2B) and formula (φ2-p1) where φ2 is a group. Note that although the substituents R ^a , R ^b and R ^c are not shown in the structural formula, they actually exist.

The structural formula on the left is an example in which R in the options for ^X1 (>N-R, >C(-R) ₂ , and >Si(-R) ₂ ) is bonded to ring c, ring b2, and ring b1, and represents a compound having rings C', B2', and B1' formed by condensing other rings to ring c (benzene ring), ring b2 (benzene ring), and ring b1 (benzene ring) in formula (2B) and formula (φ2-p1) so as to incorporate ^X1 . The condensed ring C', condensed ring B2', and condensed ring B1' formed are, for example, a phenoxazine ring, a phenothiazine ring, a carbazole ring, or an acridine ring.
The structural formula on the right shows a more specific example of the structural formula on the left.
R (phenyl group) of >N-R which is ^X1 is bonded to ring c (benzene ring) via the linking group -O- to form a phenoxazine ring C' surrounded by a dashed line;
R (phenyl group) of >N-R which is ^X1 is bonded to ring b2 (benzene ring) via a single bond to form a carbazole ring B2' surrounded by a dashed line;
This is an example in which R (phenyl group) of >N--R, which is ^X1 , is bonded to the b1 ring (benzene ring) via the linking group --S-- to form a phenothiazine ring B1' surrounded by a dashed line.

The explanations of the specific examples above can be equally applied to any form other than these specific examples.

<Explanation of the form in which adjacent C rings or c rings are bonded to each other>
Adjacent C rings in the above formula (1A), formula (φ1-m1), and formula (φ1-m2) may each independently be bonded to each other via a single bond or a linking group. In addition, adjacent R ^c in adjacent c rings in the above formula (2A), formula (φ2-m1), and formula (φ2-m2) (R ^c at the ortho position relative to X ² linking the two c rings) may each independently be bonded to each other via a single bond or a linking group.
Such a bond is preferred when ^X2 between two C rings or two c rings is N. In addition, in the case of bonding, it is preferred that all adjacent C rings or c rings are bonded to each other.

Examples of the linking group include -CH ₂ -CH ₂ -, -CHR-CHR-, -CR ₂ -CR ₂ -, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R) ₂ -, -Si(-R) ₂ - and -Se-, with -CR=CR-, -N(-R)-, -O-, -S- and -C(-R) ₂ - being preferred, and -CR=CR-, -N(-R)-, -O- and -S- being more preferred. In addition, R in the above "-CHR-CHR-", "-CR ₂ -CR ₂ -", "-CR═CR-", "-N(-R)-", "-C(-R) ₂ -" and "-Si(-R) ₂ -" is each independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, and at least one hydrogen in the R may be substituted with alkyl or cycloalkyl. In addition, two adjacent Rs may form a ring to form a cycloalkylene, arylene, or heteroarylene.
The details of the substituents listed here will be described later.

Next, examples in which adjacent C rings or C rings are bonded together will be explained in more detail using the overall and partial formulae described above.

As the group connecting the two rings, from the viewpoint of high TADF property, a single bond, >O and >C(-R) ₂ are preferred, and a single bond is more preferred.

The partial structure φ2 can be considered in a similar manner.

<Explanation of structural changes of ring a, ring b1, ring c, and ring b2>

In the above explanation, the rings a, b1, c, and b2 are benzene rings, but below, we will explain examples in which the rings a, b1, c, and b2 are structurally changed to 5- or 6-membered aryl or heteroaryl rings that are not benzene rings. The above explanation can be understood in the same way when these rings undergo the following structural changes.

<Structural change of ring a>
"-C(-R ^a )=" in the a ring may be replaced with "-N=" to form a pyridine ring. The a ring having "-C(-R ^a )=" is included only in formula (1A), (φ1-m1), (φ1-m2), (2A), (φ2-m1), and (φ2-m2), and is not included in formula (1B), (φ1-p1), (φ1-p2), (2B), (φ2-p1), and (φ2-p2). The structural diagram below shows only the a ring and a portion of its surrounding structure.

以上に示すように、例えばｃ環における「－Ｃ（－Ｒ^ｃ）＝」の箇所が「－Ｎ＝」に置き換わってもよく、このようにして、各式中でベンゼン環として表示されるｃ環は、ピリジン環、ピリミジン環、ピリダジン環、ピラジン環、その他の含窒素ヘテロアリール環に変化してもよい。また、ｃ環上に隣接する基が存在する場合（上記式中では残りの２つの隣接するＲ^ｃ）には、これらが結合してｃ環と共にヘテロアリール環（上記式中ではキノリン環）を形成し、形成された環がさらに置換されていてもよい（ｎ個のＲで示す）ことは、上述したとおりである。 <Structural changes in ring b1 and ring c>
In ring b1 and ring c, any "-C(-R)=" (wherein R is ^Rb or ^Rc ) may be replaced with "-N=".

As shown above, for example, "-C(-R ^c )=" in ring c may be replaced with "-N=", and thus ring c shown as a benzene ring in each formula may be changed to a pyridine ring, a pyrimidine ring, a pyridazine ring, a pyrazine ring, or other nitrogen-containing heteroaryl ring. In addition, when adjacent groups are present on ring c (the remaining two adjacent R ^c in the above formula), they are bonded to form a heteroaryl ring (a quinoline ring in the above formula) together with ring c, and the ring formed may be further substituted (represented by n Rs), as described above.

In addition, there are the following variations:

The same applies when other parts are replaced with "-N=" or when the b1 ring changes.

以上に示すように、例えばｃ環における「－Ｃ（－Ｒ^ｃ）＝Ｃ（－Ｒ^ｃ）－」の箇所が「－Ｎ（－Ｒ）－」、「－Ｏ－」、「－Ｓ－」、「－Ｃ（－Ｒ）_２－」、「－Ｓｉ（－Ｒ）_２－」、または「－Ｓｅ－」に置き換わってもよく、このようにして、各式中でベンゼン環として表示されるｃ環は、Ｒ置換のピロール環、フラン環、チオフェン環、その他の含窒素・酸素・硫黄ヘテロアリール環（５員環）やアリール環（５員環）に変化してもよい。また、ｃ環上に隣接する基が存在する場合（上記式中では残りの２つの隣接するＲ^ｃ）には、これらが結合してｃ環と共にヘテロアリール環（上記式中ではＲ置換のインドール環、ベンゾフラン環、またはベンゾチオフェン環などの環）やアリール環を形成し、形成された環がさらに置換されていてもよい（ｎ個のＲで示す）ことは、上述したとおりである。 Furthermore, any "-C(-R)=C(-R)-" (wherein R is R ^b or R ^c ) in ring b1 and ring c may be replaced with "-N(-R)-", "-O-", "-S-", "-C(-R) ₂ -", "-Si(-R) ₂ -" or "-Se-", and R of "-N(-R)-", R of "-C(-R) ₂ -" and R of "-Si(-R) ₂ -" are aryl, heteroaryl, alkyl or cycloalkyl. Details of the substituents listed here will be described below.

As shown above, for example, "-C(-R ^c )=C(-R ^c )-" in ring c may be replaced with "-N(-R)-", "-O-", "-S-", "-C(-R) ₂ -", "-Si(-R) ₂ -" or "-Se-", and thus ring c shown as a benzene ring in each formula may be changed to an R-substituted pyrrole ring, furan ring, thiophene ring, other nitrogen-, oxygen- or sulfur-containing heteroaryl ring (5-membered ring) or aryl ring (5-membered ring). In addition, when adjacent groups are present on ring c (the remaining two adjacent R ^c in the above formula), these are bonded together with ring c to form a heteroaryl ring (a ring such as an R-substituted indole ring, benzofuran ring, or benzothiophene ring in the above formula) or an aryl ring, and the formed ring may be further substituted (indicated by n Rs), as described above.

In addition, there are the following variations:

The same applies when other positions are replaced with "-N(-R)-", "-O-", "-S-", "-C(-R) ₂ -", "-Si(-R) ₂ -" or "-Se-" or when the b1 ring is changed.

The two Rs in the "-C(-R) ₂ -" and the two Rs in the "-Si(-R) ₂ -" may each be independently bonded to each other via a single bond or a linking group. Examples of this linking group include -CH ₂ -CH ₂ -, -CHR-CHR-, -CR ₂ -CR ₂ -, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R) ₂ -, -Si(-R) ₂ -, or -Se-, and examples of the structure include the following: The R of -CHR-CHR-, the R of -CR ₂ -CR ₂ -, the R of -CR═CR-, the R of -N(-R)-, the R of -C(-R) ₂ -, and the R of -Si(-R) ₂ - are each independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, and at least one hydrogen in the R may be substituted with an alkyl or cycloalkyl. Two adjacent Rs may form a ring to form a cycloalkylene, arylene, or heteroarylene. Details of the substituents listed here will be described below.

Among these, a single bond and the linking groups -CR=CR-, -N(-R)-, -O-, -S-, -C(-R) ₂ -, -Si(-R) ₂ -, and -Se- are preferred, a single bond and the linking groups -CR=CR-, -N(-R)-, -O-, -S-, and -C(-R) ₂ - are more preferred, a single bond and the linking groups -CR=CR-, -N(-R)-, -O-, and -S- are even more preferred, and a single bond is most preferred.

The position at which two R's are bonded by a single bond or a linking group is not particularly limited as long as it is a position where bonding is possible, but it is preferable for them to be bonded at the most adjacent positions. For example, if two R's are phenyl groups, it is preferable for them to be bonded at the ortho (2nd) positions based on the bonding position (1st position) of "C" or "Si" in the phenyl group (see the structural formula above).

<Structural change of b2 ring>
Any "-C(-R ^b )=" in the b2 ring may be replaced with "-N=." Note that the following structural diagram shows only the b2 ring and a part of its peripheral structure.

In addition, in ring b2, one "-C(-R ^b )=" may be a single bond and the other "-C(-R ^b )=" may be replaced with "-N(-R)-", "-O-", "-S-", "-C(-R) ₂ -", "-Si(-R) ₂ -" or "-Se-", and R of "-N(-R)-", R of "-C(-R) ₂ -" and R of "-Si(-R) ₂ -" are aryl, heteroaryl, alkyl or cycloalkyl. Details of the substituents listed here will be described below.
The other "-C(-R ^b )=" is preferably replaced with "-N(-R)-", "-O-", "-S-" or "-C(-R) ₂ -", more preferably replaced with "-N(-R)-", "-O-" or "-S-".
The following structural diagram shows only the b2 ring and a part of its surrounding structure.

The same applies when one "-C(-R ^b )=" and the other "-C(-R ^b )=" are swapped.

The two Rs in the "-C(-R) ₂ -" and the two Rs in the "-Si(-R) ₂ -" may each be independently bonded to each other via a single bond or a linking group. Examples of this linking group include -CH ₂ -CH ₂ -, -CHR-CHR-, -CR ₂ -CR ₂ -, -CH=CH-, -CR=CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R) ₂ -, -Si(-R) ₂ -, or -Se-, and examples of the structure include the following: The R of -CHR-CHR-, the R of -CR ₂ -CR ₂ -, the R of -CR═CR-, the R of -N(-R)-, the R of -C(-R) ₂ -, and the R of -Si(-R) ₂ - are each independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, and at least one hydrogen in the R may be substituted with an alkyl or cycloalkyl. Two adjacent Rs may form a ring to form a cycloalkylene, arylene, or heteroarylene. Details of the substituents listed here will be described below.

Among these, a single bond and the linking groups -CR=CR-, -N(-R)-, -O-, -S-, -C(-R) ₂ -, -Si(-R) ₂ -, and -Se- are preferred, a single bond and the linking groups -CR=CR-, -N(-R)-, -O-, -S-, and -C(-R) ₂ - are more preferred, a single bond and the linking groups -CR=CR-, -N(-R)-, -O-, and -S- are even more preferred, and a single bond is most preferred.

The position at which two R's are bonded by a single bond or a linking group is not particularly limited as long as it is a position where bonding is possible, but it is preferable for them to be bonded at the most adjacent positions. For example, if two R's are phenyl groups, it is preferable for them to be bonded at the ortho (2nd) positions based on the bonding position (1st position) of "C" or "Si" in the phenyl group (see the structural formula above).

<Explanation of specific structural changes of ring a, ring b1, ring c, and ring b2>
Next, examples in which the ring a, ring b1, ring c, and ring b2 have been structurally changed will be described in more detail using the overall formula and partial formulae given above.

When the ring a, ring b1, ring c, and ring b2 form a nitrogen-containing (N) aromatic ring, when N is in the ortho or para position relative to ^X1 or ^X2 in each formula, the multiple resonance effect is strengthened, and emission of shorter wavelengths and a small ΔEST tend to be obtained. When N is in the meta position relative to ^X1 or ^X2 in each formula, the multiple resonance effect is weakened, and emission of longer wavelengths and a large ΔEST tend to be obtained. However, this applies to the case of a 6-membered ring. For example, the case where the carbons of the ring a, ring b1, and ring c in the overall formula (Y2X3-A) are replaced with N is shown below.

The same can be said about the b2 ring in the partial structure φ2.

The ring b1, ring c, and ring b2 can be structurally changed to a 5- or 6-membered aryl or heteroaryl ring other than a benzene ring. For example, in the overall formula (Y2X3-A), the case where ring b1 and ring c are substituted with a 5-membered ring structure having a benzene ring is shown below.

Here, each Q is independently >N-R, >O, >S, >C(-R) ₂ , >Si(-R) ₂ , or >Se, and R in >N-R, R in >C(-R) ₂ , and R in >Si(-R) ₂ are each independently an optionally substituted aryl or an optionally substituted heteroaryl, and the same applies below. Details of the substituents listed here will be described below.
From the viewpoint of stability, Q is preferably >C(-R) ₂ , >S or >N-R, and more preferably >S. Furthermore, when Q has a five-membered ring structure, the TADF property decreases.

More specifically, when Q is >S, ring b1 and ring c are benzothiophene rings.

The partial structure φ2 can be considered in the same manner. For example, in the partial formula (φ2-Y2X3-m1), the case where the ring c is substituted with a five-membered ring structure having a benzene ring is shown below.

More specifically, when Q is >S, the c ring is a benzothiophene ring.

<Specific explanation of rings and substituents>
Next, details of the rings and substituents (including the second substituent which further substitutes the first substituent) enumerated in the above description will be collectively described.

The "aryl ring" is, for example, an aryl ring having 6 to 30 carbon atoms, preferably an aryl ring having 6 to 20 carbon atoms, an aryl ring having 6 to 16 carbon atoms, an aryl ring having 6 to 12 carbon atoms, or an aryl ring having 6 to 10 carbon atoms.
The "aryl ring" as ring B1 and ring C in formula (1A) and formula (1B) corresponds to "an aryl ring formed together with ring b1 and ring c by bonding adjacent groups of R ^b and R ^c to each other" defined in formula (2A) and formula (2B). However, for this "formed aryl ring", ring b1 or ring c is already composed of a benzene ring having 6 carbon atoms, and therefore the lower limit of the carbon number is the total carbon number of the fused ring formed by condensing this benzene ring with a minimum 5-membered ring, which is 9.

Specific examples of "aryl rings" include a monocyclic benzene ring, a fused bicyclic naphthalene ring, a fused tricyclic acenaphthylene ring, a fluorene ring, a phenalene ring, a phenanthrene ring, an anthracene ring, a fused tetracyclic tricyclic triphenylene ring, a pyrene ring, or a naphthacene ring, or a fused pentacyclic perylene ring or a pentacene ring.

The "heteroaryl ring" is, for example, a heteroaryl ring having 2 to 30 carbon atoms, and preferably a heteroaryl ring having 2 to 25 carbon atoms, a heteroaryl ring having 2 to 20 carbon atoms, a heteroaryl ring having 2 to 15 carbon atoms, or a heteroaryl ring having 2 to 10 carbon atoms. In addition, the "heteroaryl ring" is, for example, a heterocycle containing, as ring-constituting atoms other than carbon, 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen.
The "heteroaryl ring" as the ring B1 and ring C in formula (1A) and formula (1B) corresponds to the "heteroaryl ring formed together with the ring b1 and ring c by bonding adjacent groups among R ^b and R ^c" defined in formula (2A) and formula (2B), but for this "formed aryl ring", since the ring b1 or ring c is already composed of a benzene ring having 6 carbon atoms, the total carbon number of the fused ring in which the smallest 5-membered ring is fused to this benzene ring is 6. However, since the ring b1 and ring c, which are the benzene rings, may be changed to a nitrogen-containing heteroaryl ring (6-membered or 5-membered ring) or an oxygen-sulfur-containing heteroaryl ring (5-membered ring) as described above, in this case, the lower limit of the carbon number changes accordingly.

Specific examples of the "heteroaryl ring" include a pyrrole ring, an oxazole ring, an isoxazole ring, a thiazole ring, an isothiazole ring, an imidazole ring, an oxadiazole ring, a thiadiazole ring, a triazole ring, a tetrazole ring, a pyrazole ring, a pyridine ring, a pyrimidine ring, a pyridazine ring, a pyrazine ring, a triazine ring, an indole ring, an isoindole ring, a 1H-indazole ring, a benzimidazole ring, a benzoxazole ring, a benzothiazole ring, a 1H-benzotriazole ring, a quinoline ring, an isoquinoline ring, a cinnoline ring, a quinazoline ring, a quinoxaline ring, a phenanthroline ring, a phthalazine ring, a naphthyridine ring, a purine ring, a pteridine ring, a carba Examples of the ring include a zole ring, an acridine ring, a phenoxathiin ring, a phenoxazine ring, a phenothiazine ring, a phenazine ring, a phenazasiline ring, an indolizine ring, a furan ring, a benzofuran ring, an isobenzofuran ring, a dibenzofuran ring, a naphthobenzofuran ring, a thiophene ring, a benzothiophene ring, an isobenzothiophene ring, a dibenzothiophene ring, a naphthobenzothiophene ring, a benzophosphole ring, a dibenzophosphole ring, a benzophosphole oxide ring, a dibenzophosphole oxide ring, a furazan ring, a thianthrene ring, an indolocarbazole ring, a benzoindolocarbazole ring, a benzobenzoindolocarbazole ring, an imidazoline ring, and an oxazoline ring.

"Aryl" is, for example, an aryl having 6 to 30 carbon atoms, and preferably an aryl having 6 to 20 carbon atoms, an aryl having 6 to 16 carbon atoms, an aryl having 6 to 12 carbon atoms, or an aryl having 6 to 10 carbon atoms.

Specific examples of "aryl" include phenyl, which is a monocyclic ring; biphenylyl (2-biphenylyl, 3-biphenylyl, or 4-biphenylyl) which is a bicyclic ring; naphthyl (1-naphthyl or 2-naphthyl) which is a condensed bicyclic ring; terphenylyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, or p-terphenyl-4-yl) which is a condensed tricyclic ring; acenaphthyl, which is a condensed tricyclic ring; m-terphenylyl, a tetracyclic ring system (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, or m-quaterphenyl), a fused tetracyclic ring system (triphenylene-(1- or 2-)yl, pyrene-(1-, 2-, or 4-)yl, or naphthacene-(1-, 2-, or 5-)yl), or a fused pentacyclic ring system (perylene-(1-, 2-, or 3-)yl, or pentacene-(1-, 2-, 5-, or 6-)yl).

The aryl as the second substituent, i.e., the aryl as the substituent (second substituent) that further substitutes the substituent (first substituent), also includes a structure in which at least one hydrogen in the aryl is substituted with an aryl such as phenyl (specific examples are the groups described above), an alkyl such as methyl (specific examples are groups described later), or a cycloalkyl such as cyclohexyl or adamantyl (specific examples are groups described later).
As an example, when the second substituent is a fluorenyl group, at least one hydrogen atom at the 9-position is substituted with an aryl group such as phenyl, an alkyl group such as methyl, or a cycloalkyl group such as cyclohexyl or adamantyl, and such groups are also included in the aryl group as the second substituent.

The "arylene" is, for example, an arylene having 6 to 30 carbon atoms, and preferably an arylene having 6 to 20 carbon atoms, an arylene having 6 to 16 carbon atoms, an arylene having 6 to 12 carbon atoms, or an arylene having 6 to 10 carbon atoms.
Specific examples of "arylene" include structures in which one hydrogen is removed from the above-mentioned "aryl" (monovalent group) to form a divalent group.

"Heteroaryl" is, for example, a heteroaryl having 2 to 30 carbon atoms, and preferably a heteroaryl having 2 to 25 carbon atoms, a heteroaryl having 2 to 20 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, or a heteroaryl having 2 to 10 carbon atoms. In addition, "heteroaryl" is, for example, a monovalent group such as a heterocycle containing, in addition to carbon, 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen as ring-constituting atoms.

Specific examples of "heteroaryl" include pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, phenanthrolinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, and phenoxathiinyl. phenyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenazasilinyl, indolizinyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, naphthobenzofuranyl, thiophenyl, benzothiophenyl, isobenzothiophenyl, dibenzothiophenyl, naphthobenzothiophenyl, benzophosphoryl, dibenzophosphoryl, a monovalent group of a benzophosphole oxide ring, a monovalent group of a dibenzophosphole oxide ring, furazanyl, thianthrenyl, indolocarbazolyl, benzoindolocarbazolyl, benzobenzoindolocarbazolyl, imidazolinyl, oxazolinyl, or dibenzosilacyclopentadienyl.

In addition, the heteroaryl as the second substituent, i.e., the heteroaryl as the substituent (second substituent) that further substitutes the substituent (first substituent), also includes a structure in which at least one hydrogen in the heteroaryl is replaced by an aryl such as phenyl (specific examples are the groups described above), an alkyl such as methyl (specific examples are groups described later), or a cycloalkyl such as cyclohexyl or adamantyl (specific examples are groups described later).
An example of such a case is when the second substituent is a carbazolyl group, at least one hydrogen atom at the 9-position is substituted with an aryl group such as phenyl, an alkyl group such as methyl, or a cycloalkyl group such as cyclohexyl or adamantyl, and such a group is also included in the heteroaryl group as the second substituent.

The "heteroarylene" is, for example, a heteroarylene having 2 to 30 carbon atoms, and preferably a heteroarylene having 2 to 25 carbon atoms, a heteroarylene having 2 to 20 carbon atoms, a heteroarylene having 2 to 15 carbon atoms, or a heteroarylene having 2 to 10 carbon atoms. In addition, the "heteroarylene" is, for example, a divalent group such as a heterocycle containing, in addition to carbon, 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen as ring-constituting atoms.
Specific examples of "heteroarylene" include structures in which one hydrogen atom is removed from the above-mentioned "heteroaryl" (monovalent group) to form a divalent group.

The term "diarylamino" refers to an amino group substituted with two aryl groups. For details of the aryl group, see the above description of the "aryl".
The term "diheteroarylamino" refers to an amino group substituted with two heteroaryls. For details of the heteroaryl, the above description of the "heteroaryl" can be cited.
The "arylheteroarylamino" is an amino group substituted with an aryl and a heteroaryl, and the details of the aryl and the heteroaryl can be found in the above descriptions of the "aryl" and the "heteroaryl".

"Diarylboryl" is a boryl group substituted with two aryls, and the above description of "aryl" can be cited for details of the aryl. The two aryls may be bonded via a single bond or a linking group (e.g., -CH ₂ -CH ₂ -, -CHR-CHR-, -CR ₂ -CR ₂ -, -CH═CH-, -CR═CR-, -C≡C-, >N-R, >O, >S, >C(-R) ₂ , >Si(-R) ₂ , or >Se). Here, R of -CHR-CHR-, R of -CR ₂ -CR ₂ -, R of -CR=CR-, R of >N-R, R of >C(-R) ₂ , and R of >Si(-R) are aryl, heteroaryl, diarylamino, alkyl, alkenyl, alkynyl, cycloalkyl, alkoxy, or aryloxy, and at least one hydrogen in the R may be further substituted with aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl. In addition, two adjacent R may form a ring to form a cycloalkylene, arylene, or heteroarylene. For details of the substituents listed here, the explanations of "aryl", "arylene", "heteroaryl", "heteroarylene", and "diarylamino" above, and the explanations of "alkyl", "alkenyl", "alkynyl", "cycloalkyl", "cycloalkylene", "alkoxy", and "aryloxy" below can be cited.

"Alkyl" may be either straight-chain or branched-chain, for example straight-chain alkyl having 1 to 24 carbon atoms or branched-chain alkyl having 3 to 24 carbon atoms, and preferably alkyl having 1 to 18 carbon atoms (branched-chain alkyl having 3 to 18 carbon atoms), alkyl having 1 to 12 carbon atoms (branched-chain alkyl having 3 to 12 carbon atoms), alkyl having 1 to 6 carbon atoms (branched-chain alkyl having 3 to 6 carbon atoms), alkyl having 1 to 5 carbon atoms (branched-chain alkyl having 3 to 5 carbon atoms), alkyl having 1 to 4 carbon atoms (branched-chain alkyl having 3 to 4 carbon atoms), etc.

Specific examples of "alkyl" include methyl, ethyl, n-propyl, isopropyl, 1-ethyl-1-methylpropyl, 1,1-diethylpropyl, 1,1,2-trimethylpropyl, 1,1,2,2-tetramethylpropyl, 1-ethyl-1,2,2-trimethylpropyl, n-butyl, isobutyl, s-butyl, t-butyl, 2-ethylbutyl, 1,1-dimethylbutyl, 3,3-dimethylbutyl, 1,1-diethylbutyl, 1-ethyl-1-methylbutyl, 1-propyl-1-methylbutyl, 1,1,3-trimethylbutyl, 1-ethyl-1,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, t-pentyl (t-amyl), 1-methylpentyl, 2-propylpentyl, 1,1-dimethylpentyl, 1-ethyl-1-methylpentyl, 1-propyl-1 -methylpentyl, 1-butyl-1-methylpentyl, 1,1,4-trimethylpentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 1,1-dimethylhexyl, 1-ethyl-1-methylhexyl, 1,1,5-trimethylhexyl, 3,5,5-trimethylhexyl, n-heptyl, 1-methylheptyl, 1-hexylheptyl, 1,1-dimethylheptyl, 2,2-dimethylhexyl, Examples of the alkyl radical include methylheptyl, 2,6-dimethyl-4-heptyl, n-octyl, t-octyl (1,1,3,3-tetramethylbutyl), 1,1-dimethyloctyl, n-nonyl, n-decyl, 1-methyldecyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, and n-eicosyl.

For "alkenyl," please refer to the explanation of "alkyl" above. It is a group in which the C-C single bond in the "alkyl" structure is replaced with a C=C double bond, and also includes groups in which not only one but two or more single bonds are replaced with double bonds (also called alkadiene-yl or alkanetriene-yl).

For "alkynyl," please refer to the explanation of "alkyl" above, and it is a group in which the C-C single bond in the "alkyl" structure is replaced with a C≡C triple bond, including groups in which not only one but two or more single bonds are replaced with triple bonds (also called alkadiyn-yl or alkanetriyn-yl).

"Cycloalkyl" is, for example, cycloalkyl having 3 to 24 carbon atoms, and preferably cycloalkyl having 3 to 20 carbon atoms, cycloalkyl having 3 to 16 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, cycloalkyl having 3 to 12 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, cycloalkyl having 5 to 8 carbon atoms, cycloalkyl having 5 to 6 carbon atoms, or cycloalkyl having 5 carbon atoms.

Specific examples of "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, or alkyl (especially methyl) substituted derivatives of these having 1 to 5 or 1 to 4 carbon atoms, norbornenyl, bicyclo[1.1.0]butyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.0]pentyl, bicyclo[2.1.1]hexyl, bicyclo[3.1.0]hexyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl, adamantyl, diamantyl, decahydronaphthalenyl, and decahydroazulenyl.

The "cycloalkylene" is, for example, a cycloalkylene having 3 to 24 carbon atoms, and preferably a cycloalkylene having 3 to 20 carbon atoms, a cycloalkylene having 3 to 16 carbon atoms, a cycloalkylene having 3 to 14 carbon atoms, a cycloalkylene having 3 to 12 carbon atoms, a cycloalkylene having 5 to 10 carbon atoms, a cycloalkylene having 5 to 8 carbon atoms, a cycloalkylene having 5 to 6 carbon atoms, or a cycloalkylene having 5 carbon atoms.
Specific examples of "cycloalkylene" include structures obtained by removing one hydrogen from the above-mentioned "cycloalkyl" (monovalent group) to form a divalent group.

"Alkoxy" may be either straight chain or branched chain, for example straight chain alkoxy having 1 to 24 carbon atoms or branched chain alkoxy having 3 to 24 carbon atoms, and preferably alkoxy having 1 to 18 carbon atoms (branched chain alkoxy having 3 to 18 carbon atoms), alkoxy having 1 to 12 carbon atoms (branched chain alkoxy having 3 to 12 carbon atoms), alkoxy having 1 to 6 carbon atoms (branched chain alkoxy having 3 to 6 carbon atoms), alkoxy having 1 to 5 carbon atoms (branched chain alkoxy having 3 to 5 carbon atoms), alkoxy having 1 to 4 carbon atoms (branched chain alkoxy having 3 to 4 carbon atoms), etc.

Specific examples of "alkoxy" include methoxy, ethoxy, n-propoxy, isopropoxy, 1-ethyl-1-methylpropoxy, 1,1-diethylpropoxy, 1,1,2-trimethylpropoxy, 1,1,2,2-tetramethylpropoxy, 1-ethyl-1,2,2-trimethylpropoxy, n-butoxy, isobutoxy, s-butoxy, t-butoxy, 2-ethylbutoxy, 1,1-dimethylbutoxy, 3,3-dimethylbutoxy, 1,1-diethylbutoxy, 1-ethyl-1-methylbutoxy, 1-propyl-1-methylbutoxy, 1,1,3-trimethylbutoxy, 1-ethyl-1,3-dimethylbutoxy, n-pentyloxy, isopentyloxy, neopentyloxy, t-pentyloxy (t-amyloxy), 1-methylpentyloxy, 2-propylpentyloxy, 1,1-dimethylpentyloxy, 1-ethyl-1-methylpentyloxy, 1-propyl-1-methylpentyloxy, 1-butyl-1-methyl Pentyloxy, 1,1,4-trimethylpentyloxy, n-hexyloxy, 1-methylhexyloxy, 2-ethylhexyloxy, 1,1-dimethylhexyloxy, 1-ethyl-1-methylhexyloxy, 1,1,5-trimethylhexyloxy, 3,5,5-trimethylhexyloxy, n-heptyloxy, 1-methylheptyloxy, 1-hexylheptyloxy, 1,1-dimethylheptyloxy, 2,2-dimethylheptyloxy, 2,6-dimethyl Examples of the aryloxy group include n-tyl-4-heptyloxy, n-octyloxy, t-octyloxy (1,1,3,3-tetramethylbutyloxy), 1,1-dimethyloctyloxy, n-nonyloxy, n-decyloxy, 1-methyldecyloxy, n-undecyloxy, n-dodecyloxy, n-tridecyloxy, n-tetradecyloxy, n-pentadecyloxy, n-hexadecyloxy, n-heptadecyloxy, n-octadecyloxy, and n-eicosyloxy.

"Aryloxy" is a group represented by "Ar-O- (Ar is an aryl group)" and for details on the aryl, the explanation of "aryl" above can be cited.

"Substituted silyl" is, for example, a silyl substituted with at least one of aryl, alkyl, and cycloalkyl, and is preferably triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl.

The "triarylsilyl" is a silyl group substituted with three aryl groups. For details of the aryl groups, see the above description of the "aryl".
Specific "triarylsilyl" includes, for example, triphenylsilyl, diphenylmononaphthylsilyl, monophenyldinaphthylsilyl, trinaphthylsilyl, and the like.

The term "trialkylsilyl" refers to a silyl group substituted with three alkyl groups. For details of this alkyl group, see the above description of "alkyl."
Specific examples of "trialkylsilyl" include trimethylsilyl, triethylsilyl, tri-n-propylsilyl, triisopropylsilyl, tri-n-butylsilyl, triisobutylsilyl, tri-s-butylsilyl, tri-t-butylsilyl, ethyldimethylsilyl, n-propyldimethylsilyl, isopropyldimethylsilyl, n-butyldimethylsilyl, isobutyldimethylsilyl, s-butyldimethylsilyl, t-butyldimethylsilyl, methyldiethylsilyl, n-propyldiethylsilyl, isopropyldiethylsilyl, n-butyldiethylsilyl, s-butyldiethylsilyl, t-butyldiethylsilyl, methyldi-n-propylsilyl, ethyldi-n-propylsilyl, n-butyldi-n-propylsilyl, s-butyldi-n-propylsilyl, t-butyldi-n-propylsilyl, methyldiisopropylsilyl, ethyldiisopropylsilyl, n-butyldiisopropylsilyl, s-butyldiisopropylsilyl, and t-butyldiisopropylsilyl.

The term "tricycloalkylsilyl" refers to a silyl group substituted with three cycloalkyl groups. For details of this cycloalkyl, see the above description of the "cycloalkyl".
Specific "tricycloalkylsilyl" includes, for example, tricyclopentylsilyl or tricyclohexylsilyl.

"Dialkylcycloalkylsilyl" is a silyl group substituted with two alkyls and one cycloalkyl; for details of the alkyl and cycloalkyl, see the explanations of "alkyl" and "cycloalkyl" above.

"Alkyldicycloalkylsilyl" is a silyl group substituted with one alkyl and two cycloalkyl groups; for details on the alkyl and cycloalkyl groups, see the explanations of "alkyl" and "cycloalkyl" above.

The substituents (including the first and second substituents) affect the emission wavelength of the polycyclic aromatic compound due to the steric hindrance, electron donating property, and electron withdrawing property of the structure, so the emission wavelength can be adjusted by selecting the substituents. The groups represented by the following structural formulas are preferred, and more preferred are methyl, t-butyl, bicyclooctyl, cyclohexyl, adamantyl, phenyl, o-tolyl, p-tolyl, 2,4-xylyl, 2,5-xylyl, 2,6-xylyl, 2,4,6-mesityl, diphenylamino, di-p-tolylamino, bis(p-(t-butyl)phenyl)amino, diphenylboryl, dimesitylboryl, dibenzoxaborinyl, phenyldibenzyl, and phenyldibenzyl. Preferred are phenyldiboroninyl, carbazolyl, 3,6-dimethylcarbazolyl, 3,6-di-t-butylcarbazolyl and phenoxy, and more preferred are methyl, t-butyl, phenyl, o-tolyl, 2,6-xylyl, 2,4,6-mesityl, diphenylamino, di-p-tolylamino, bis(p-(t-butyl)phenyl)amino, carbazolyl, 3,6-dimethylcarbazolyl and 3,6-di-t-butylcarbazolyl. From the viewpoint of ease of synthesis, a larger steric hindrance is preferred for selective synthesis, and specifically, t-butyl, o-tolyl, p-tolyl, 2,4-xylyl, 2,5-xylyl, 2,6-xylyl, 2,4,6-mesityl, di-p-tolylamino, bis(p-(t-butyl)phenyl)amino, 3,6-dimethylcarbazolyl and 3,6-di-t-butylcarbazolyl are preferred.

In the following structural formulas, "Me" represents methyl, "tBu" represents t-butyl, "tAm" represents t-amyl, "tOct" represents t-octyl, and * represents the bonding position.

<Explanation of Cycloalkane Condensation>
In addition, at least one of the aromatic rings and heteroaromatic rings in the chemical structure of the polycyclic aromatic compound of the present invention may be condensed with at least one cycloalkane.

For example, at least one of the aryl and heteroaryl rings which are ring B1, ring B2, ring C, ring b1, and ring c, the aryl group (aryl group moiety in aryl, diarylamino, arylheteroarylamino, diarylboryl, aryloxy, or triarylsilyl) and the heteroaryl group (heteroaryl moiety in heteroaryl, diheteroarylamino, or arylheteroarylamino) as the first and second substituents on these rings, the aryl ring or the heteroaryl ring formed by bonding adjacent substituents on ring b1 and ring c, the aryl group (similar to the above) and the heteroaryl group (similar to the above) as the first and second substituents on ring a and ring ^b2 , and the aryl group or the heteroaryl group as R of >N-R, R of >C(-R) ₂ , and R of >Si(-R) ₂ which is X1 may be fused with at least one cycloalkane.

Preferably, at least one of the aryl and heteroaryl rings which are ring B1, ring B2, ring C, ring b1, and ring c, the aryl group (aryl group moiety in aryl, diarylamino, diarylboryl, or aryloxy) and the heteroaryl group (heteroaryl moiety in heteroaryl or diheteroarylamino) as the first substituent on these rings, the aryl ring or the heteroaryl ring formed by bonding adjacent substituents on ring b1 and ring c, the aryl group (similar to the above) and the heteroaryl group (similar to the above) as the first substituent on ring a and ring ^b2 , and the aryl group or the heteroaryl group as X1, R of >N-R, R of >C(-R) ₂ , and R of >Si(-R) ₂ may be fused with at least one cycloalkane.

More preferably, at least one of the aryl rings which are ring B1, ring B2, ring C, ring b1, and ring c, the aryl group (aryl group moiety in aryl or diarylamino) and heteroaryl group (heteroaryl moiety in heteroaryl) as first substituents on these rings, the aryl ring formed by bonding adjacent substituents on ring b1 and ring c, the aryl group (similar to above) and heteroaryl group (similar to above) as first substituents on ring a and ring b2, and the aryl group as R of >N-R which is ^X1 may be fused with at least one cycloalkane.

More preferably, at least one of the aryl rings which are ring B1, ring B2, ring C, ring b1, and ring c, the aryl group as the first substituent on these rings (the aryl group moiety in aryl or diarylamino), the aryl group as the first substituent on ring a and ring b2 (similar to the above), and the aryl group as R of >N-R which is ^X1 may be condensed with at least one cycloalkane.

Examples of "cycloalkanes" include cycloalkanes having 3 to 24 carbon atoms, cycloalkanes having 3 to 20 carbon atoms, cycloalkanes having 3 to 16 carbon atoms, cycloalkanes having 3 to 14 carbon atoms, cycloalkanes having 5 to 10 carbon atoms, cycloalkanes having 5 to 8 carbon atoms, cycloalkanes having 5 to 6 carbon atoms, and cycloalkanes having 5 carbon atoms.

Specific examples of cycloalkanes include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclononane, cyclodecane, norbornene, bicyclo[1.1.0]butane, bicyclo[1.1.1]pentane, bicyclo[2.1.0]pentane, bicyclo[2.1.1]hexane, bicyclo[3.1.0]hexane, bicyclo[2.2.1]heptane, bicyclo[2.2.2]octane, adamantane, diamantane, decahydronaphthalene, and decahydroazulene, as well as alkyl (especially methyl) substituted, halogen (especially fluorine) substituted, and deuterium substituted derivatives of these having 1 to 5 carbon atoms.

Among these, for example, as shown in the following structural formula, a structure in which at least one hydrogen atom is substituted on the carbon atom at the α-position of a cycloalkane (a carbon atom at a position adjacent to the carbon atom at the condensation site in a cycloalkyl fused to an aromatic ring or heteroaromatic ring) is preferred, a structure in which two hydrogen atoms are substituted on the carbon atom at the α-position is more preferred, and a structure in which a total of four hydrogen atoms are substituted on the two carbon atoms at the α-position is even more preferred. Examples of this substituent include an alkyl (particularly methyl) substituent having 1 to 5 carbon atoms, a halogen (particularly fluorine) substituent, and a deuterium substituent.

The number of cycloalkanes fused to one aromatic ring or heteroaromatic ring is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1. For example, an example in which one or more cycloalkanes are fused to one benzene ring (phenyl group) is shown below. In each structural formula, * means a benzene ring contained in the skeletal structure of the compound when it is a benzene ring, and means a bond substituting the skeletal structure of the compound when it is a phenyl group. Cycloalkanes fused as in formula (Cy-1-4) and formula (Cy-2-4) may be condensed together. The same applies even if the condensed ring (group) is an aromatic ring or heteroaromatic ring other than a benzene ring (phenyl group), or even if the condensed cycloalkane is a cycloalkane other than cyclopentane or cyclohexane.

At least one -CH ₂ - in a cycloalkane may be substituted with -O-. However, when multiple -CH ₂ - are substituted with -O-, adjacent -CH ₂ - are not substituted with -O-. For example, examples in which one or multiple -CH ₂ - in a cycloalkane fused to one benzene ring (phenyl group) are substituted with -O- are shown below. In each structural formula, * means a benzene ring contained in the skeletal structure of the compound when it is a benzene ring, and means a bond substituting the skeletal structure of the compound when it is a phenyl group. The same applies when the fused ring (group) is an aromatic ring or heteroaromatic ring other than a benzene ring (phenyl group) or when the fused cycloalkane is a cycloalkane other than cyclopentane or cyclohexane.

At least one hydrogen atom in the cycloalkane may be substituted. Examples of the substituent include aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, substituted silyl, deuterium, cyano, or halogen. For details of these, the description of the first substituent can be cited. Among these substituents, alkyl (e.g., alkyl having 1 to 6 carbon atoms), cycloalkyl (e.g., cycloalkyl having 3 to 14 carbon atoms), halogen (e.g., fluorine), and deuterium are preferred. In addition, when cycloalkyl is substituted, it may be a substitution form that forms a spiro structure. For example, an example in which a spiro structure is formed in a cycloalkane condensed to one benzene ring (phenyl group) is shown below. In each structural formula, * means that in the case of a benzene ring, it is a benzene ring included in the skeletal structure of the compound, and in the case of a phenyl group, it means a bond that substitutes in the skeletal structure of the compound.

Other forms of cycloalkane condensation include polycyclic aromatic compounds represented by formula (1A), (1B), (2A), or (2B) substituted with, for example, a diarylamino group condensed with a cycloalkane (condensed to the aryl group portion), a carbazolyl group condensed with a cycloalkane (condensed to the benzene ring portion), or a benzocarbazolyl group condensed with a cycloalkane (condensed to the benzene ring portion). Examples of the "diarylamino group" include the groups described above as the "first substituent."

Further, as a more specific example, there can be mentioned an example in which R ^a in the polycyclic aromatic compound represented by formula (1A) or formula (2A) is a diarylamino group condensed with a cycloalkane (condensed to the aryl group portion) or a carbazolyl group condensed with a cycloalkane (condensed to the benzene ring portion).

Explanation of substitution by deuterium, cyano, or halogen
At least one hydrogen atom in the polycyclic aromatic compound of the present invention may be substituted with deuterium, cyano, or a halogen atom. The halogen atom is fluorine, chlorine, bromine, or iodine, preferably fluorine, chlorine, or bromine, and more preferably fluorine or chlorine.

<Explanation of specific examples of polycyclic aromatic compounds of the present invention>
More specific examples of polycyclic aromatic compounds include compounds represented by the following structural formulas: In the structural formulas, "Me" represents a methyl group and "tBu" represents a t-butyl group.

<Explanation of the increase in molecular weight of polycyclic aromatic compounds>
The polycyclic aromatic compound represented by the above general formula (1A) or general formula (1B) can also be used as a material for organic devices, for example, a material for organic electroluminescent elements, a material for organic field effect transistors, a material for organic thin-film solar cells, or a wavelength conversion filter, in the form of a polymer compound obtained by polymerizing a reactive compound substituted with the compound as a monomer (the monomer for obtaining this polymer compound has a polymerizable substituent), or a crosslinked polymer obtained by further crosslinking the polymer compound (the polymer compound for obtaining this crosslinked polymer has a crosslinkable substituent), or a pendant polymer compound obtained by reacting a main-chain polymer with the reactive compound (the reactive compound for obtaining this pendant polymer compound has a reactive substituent), or a pendant polymer crosslinked polymer obtained by further crosslinking the pendant polymer compound (the pendant polymer compound for obtaining this pendant polymer crosslinked polymer has a crosslinkable substituent).

The reactive substituents mentioned above (including the polymerizable substituents, the crosslinkable substituents, and the reactive substituents for obtaining a pendant polymer, hereinafter also referred to simply as "reactive substituents") are not particularly limited as long as they are substituents capable of increasing the molecular weight of the polycyclic aromatic compound, substituents capable of further crosslinking the polymer compound thus obtained, and substituents capable of pendant reaction with the main chain polymer, but are preferably those having the following structures: * in each structural formula indicates a bond position.

Each L is independently a single bond, -O-, -S-, >C=O, -O-C(=O)-, an alkylene having 1 to 12 carbon atoms, an oxyalkylene having 1 to 12 carbon atoms, or a polyoxyalkylene having 1 to 12 carbon atoms. Among the above substituents, a group represented by formula (XLS-1), formula (XLS-2), formula (XLS-3), formula (XLS-9), formula (XLS-10) or formula (XLS-17) is preferred, and a group represented by formula (XLS-1), formula (XLS-3) or formula (XLS-17) is more preferred.

Such a polymer compound, crosslinked polymer, pendant type polymer compound, and pendant type crosslinked polymer may contain, in addition to the repeating unit of the polycyclic aromatic compound represented by formula (1A) or formula (1B), at least one selected from the group consisting of substituted or unsubstituted triarylamine, substituted or unsubstituted fluorene, substituted or unsubstituted anthracene, substituted or unsubstituted tetracene, substituted or unsubstituted triazine, substituted or unsubstituted carbazole, substituted or unsubstituted tetraphenylsilane, substituted or unsubstituted spirofluorene, substituted or unsubstituted triphenylphosphine, substituted or unsubstituted dibenzothiophene, and substituted or unsubstituted dibenzofuran, as a repeating unit.
Examples of the substituents in these repeating units include aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl. For details of the "aryl" in triarylamine and these substituents, the explanation in the polycyclic aromatic compound represented by formula (1A) or formula (1B) can be cited.

The uses of such polymer compounds, crosslinked polymers, pendant polymer compounds and pendant polymer crosslinked polymers (hereinafter simply referred to as "polymer compounds and crosslinked polymers") will be described in detail below.

2. Method for producing polycyclic aromatic compounds The polycyclic aromatic compounds of the present invention are basically produced by first bonding the a ring with the B1 ring (b1 ring), the B2 ring (b2 ring) and the C ring (c ring) with a bonding group (a group containing ^X1 or ^X2 ) to produce an intermediate (first reaction), and then bonding the a ring with the B1 ring (b1 ring), the B2 ring (b2 ring) and the C ring (c ring) with a bonding group (a group containing Y) to produce a final product (second reaction). The production method described in International Publication No. WO 2015/102118 can be used as a reference.

In the first reaction, for example, if it is an etherification reaction, a common reaction such as a nucleophilic substitution reaction or the Ullmann reaction can be used, and if it is an amination reaction, a common reaction such as the Buchwald-Hartwig reaction can be used. In addition, in the second reaction, a tandem hetero Friedel-Crafts reaction (sequential aromatic electrophilic substitution reaction, the same applies below) can be used.

The second reaction is a reaction of introducing Y that bonds ring a, ring B1 (ring b1), ring B2 (ring b2) and ring C (ring c) as shown in the following schemes (1) and (2). First, the hydrogen atom between X ¹ and X ² is orthometalated with n-butyllithium, sec-butyllithium, t-butyllithium or the like. Next, a halide of Y such as boron trichloride or boron tribromide is added, and after performing lithium-boron metal exchange, a tandem boron-Friedel-Crafts reaction is carried out by adding a Bronsted base such as N,N-diisopropylethylamine to obtain the target product. In the second reaction, a Lewis acid such as aluminum trichloride may be added to promote the reaction. The definitions of the symbols in the structural formulae in the following schemes (1) and (2) and in the subsequent schemes are the same as those described above.

In the above scheme (1), the unit structure φ1 is not shown, but since the compound of the present invention is a compound composed of the above-mentioned "meta type unit structure" and "para type unit structure" repeatedly linked together, the same reaction occurs in all unit structures, and the compound of the present invention can be produced. The above scheme (2) is a method for producing a compound having a representative structure, and shows a method for producing a compound in which n (n=1) unit structures of formula (φ1-m1) are selected as φ1 in formula (1A).

In the above scheme, lithium was introduced to the desired position by ortho-metallation, but as shown in the following scheme (3), lithium can also be introduced to the desired position by introducing a bromine atom or the like to the position where lithium is to be introduced and then by halogen-metal exchange. This method is useful because it allows the production of the target product even in cases where ortho-metallation is not possible due to the influence of a substituent.

The above schemes (1) to (3) are typical production methods when Y is boron (B), etc.

Next, as an example, the case where Y is phosphorus sulfide, phosphorus oxide, or phosphorus atom is shown in the following schemes (4) and (5). As in the above, first, the hydrogen atom between ^X1 and ^X2 is orthometalated with n-butyllithium or the like. Next, phosphorus trichloride and sulfur are added in this order, and finally, a Lewis acid such as aluminum trichloride and a Bronsted base such as N,N-diisopropylethylamine are added to carry out a tandem phospha Friedel-Crafts reaction, thereby obtaining a compound in which Y is phosphorus sulfide. In addition, a compound in which Y is phosphorus oxide can be obtained by treating the obtained phosphorus sulfide compound with m-chloroperbenzoic acid (m-CPBA), and a compound in which Y is a phosphorus atom can be obtained by treating with triethylphosphine.

In the above scheme, examples where Y is B, P, P=O or P=S are mainly described, but other compounds can also be produced by appropriately changing the raw materials.

In the above scheme, an example is shown in which a tandem hetero Friedel-Crafts reaction is carried out by ortho-metalating a hydrogen atom (or a halogen atom) between ^X1 and ^X2 with butyllithium or the like before adding a halide of Y such as boron trichloride or boron tribromide. However, the reaction can also be carried out by adding a halide of Y such as boron trichloride or boron tribromide without ortho-metalating using butyllithium or the like.

Solvents used in the above scheme include t-butylbenzene and xylene.

Orthometalation reagents used in the above scheme include alkyllithiums such as methyllithium, n-butyllithium, sec-butyllithium, and t-butyllithium; organic alkali compounds such as lithium diisopropylamide, lithium tetramethylpiperidide, lithium hexamethyldisilazide, and potassium hexamethyldisilazide; and dispersed alkali metals such as Na dispersed in an organic solvent.

The metal exchange reagent of metal-Y used in the above scheme includes halides of Y such as trifluoride of Y, trichloride of Y, tribromide of Y, triiodide of Y, etc., aminated halides of Y such as CIPN(NEt ₂ ) ₂ , alkoxylated Y, aryloxylated Y, etc.

Examples of Bronsted bases used in the above scheme include N,N-diisopropylethylamine, triethylamine, 2,2,6,6-tetramethylpiperidine, 1,2,2,6,6-pentamethylpiperidine, N,N-dimethylaniline, N,N-dimethyltoluidine, 2,6-lutidine, sodium tetraphenylborate, potassium tetraphenylborate, triphenylborane, tetraphenylsilane, Ar ₄ BNa, Ar ₄ BK, Ar ₃ B, and Ar ₄ Si (wherein Ar is an aryl such as phenyl).

Lewis acids used in the above scheme include _AlCl3 , AlBr3, _AlF3 , _BF3.OEt2 , _BCl3 , _BBr3 , _GaCl3 , _GaBr3 , _InCl3 , _InBr3 , In(OTf)3, SnCl4, _SnBr4 , AgOTf, _ScCl3 , Sc(OTf) ₃ , _ZnCl2 , _ZnBr2 , Zn(OTf) ₂ , _MgCl2 , _MgBr2 , Mg(OTf) ₂ , LiOTf, NaOTf _, KOTf, Me3SiOTf _, Cu(OTf) _{2 , CuCl2} , _YCl3 , Y ₍ OTf) _{3 , TiCl4} , _TiBr4 , _ZrCl4 , _ZrBr4 , _FeCl3 , _FeBr3 , _CoCl3 , _CoBr3 , etc.

In the above scheme, a Brönsted base or Lewis acid may be used to promote the tandem hetero Friedel-Crafts reaction. However, when a halide of Y such as trifluoride of Y, trichloride of Y, tribromide of Y, or triiodide of Y is used, acids such as hydrogen fluoride, hydrogen chloride, hydrogen bromide, and hydrogen iodide are generated as the aromatic electrophilic substitution reaction proceeds, so it is effective to use a Brönsted base to capture the acid. On the other hand, when an amino halide of Y or an alkoxylated product of Y is used, amines and alcohols are generated as the aromatic electrophilic substitution reaction proceeds, so it is not necessary to use a Brönsted base in many cases, but since the elimination ability of amino groups and alkoxy groups is low, it is effective to use a Lewis acid to promote the elimination.

The polycyclic aromatic compounds of the present invention also include compounds in which at least some of the hydrogen atoms are replaced by deuterium, cyano, or halogen. Such compounds can be produced in the same manner as described above by using raw materials in which the desired positions are halogenated, such as deuterated, cyanated, fluorinated, or chlorinated.

3. Organic Devices In the chemical structural formulas exemplified below, "Me" represents a methyl group and "tBu" represents a t-butyl group.
The polycyclic aromatic compound according to the present invention can be used as a material for an organic device, such as an organic electroluminescent element, an organic field effect transistor, an organic thin-film solar cell, or a wavelength conversion filter.

3-1. Organic electroluminescence element The polycyclic aromatic compound according to the present invention can be used, for example, as a material for an organic electroluminescence element. The organic EL element according to this embodiment will be described in detail below with reference to the drawings. Figure 1 is a schematic cross-sectional view showing an organic EL element according to this embodiment.

<Structure of Organic Electroluminescent Device>
The organic EL element 100 shown in FIG. 1 has a substrate 101, an anode 102 provided on the substrate 101, a hole injection layer 103 provided on the anode 102, a hole transport layer 104 provided on the hole injection layer 103, a light emitting layer 105 provided on the hole transport layer 104, an electron transport layer 106 provided on the light emitting layer 105, an electron injection layer 107 provided on the electron transport layer 106, and a cathode 108 provided on the electron injection layer 107.

In addition, the organic EL element 100 may be fabricated in the reverse order, for example, to have a substrate 101, a cathode 108 provided on the substrate 101, an electron injection layer 107 provided on the cathode 108, an electron transport layer 106 provided on the electron injection layer 107, an emitting layer 105 provided on the electron transport layer 106, a hole transport layer 104 provided on the emitting layer 105, a hole injection layer 103 provided on the hole transport layer 104, and an anode 102 provided on the hole injection layer 103.

Not all of the above layers are essential, and the minimum structural unit is the anode 102, the light-emitting layer 105, and the cathode 108. The hole injection layer 103, the hole transport layer 104, the electron transport layer 106, and the electron injection layer 107 are layers that are optionally provided. Each of the above layers may be a single layer or multiple layers.

In addition to the above-mentioned "substrate/anode/hole injection layer/hole transport layer/light-emitting layer/electron transport layer/electron injection layer/cathode" configuration, the layers constituting the organic EL element may be "substrate/anode/hole transport layer/light-emitting layer/electron transport layer/electron injection layer/cathode", "substrate/anode/hole injection layer/light-emitting layer/electron transport layer/electron injection layer/cathode", "substrate/anode/hole injection layer/light-emitting layer/electron transport layer/electron injection layer/cathode", "substrate/anode/hole injection layer/hole transport layer/light-emitting ... transport", The configuration may be, for example, "substrate/anode/light-emitting layer/electron transport layer/electron injection layer/cathode", "substrate/anode/hole transport layer/light-emitting layer/electron injection layer/cathode", "substrate/anode/hole transport layer/light-emitting layer/electron transport layer/cathode", "substrate/anode/hole transport layer/light-emitting layer/electron transport layer/cathode", "substrate/anode/hole injection layer/light-emitting layer/electron injection layer/cathode", "substrate/anode/hole injection layer/light-emitting layer/electron transport layer/cathode", "substrate/anode/hole injection layer/light-emitting layer/electron transport layer/cathode", "substrate/anode/light-emitting layer/electron transport layer/cathode", or "substrate/anode/light-emitting layer/electron injection layer/cathode".

<Substrate in Organic Electroluminescent Device>
The substrate 101 is a support for the organic EL element 100, and is usually made of quartz, glass, metal, plastic, or the like. The substrate 101 is formed into a plate, film, or sheet shape depending on the purpose, and for example, a glass plate, a metal plate, a metal foil, a plastic film, a plastic sheet, or the like is used. Among them, a glass plate and a plate made of a transparent synthetic resin such as polyester, polymethacrylate, polycarbonate, or polysulfone are preferable. For a glass substrate, soda-lime glass or alkali-free glass is used, and the thickness is sufficient to maintain mechanical strength, so that it may be, for example, 0.2 mm or more. The upper limit of the thickness is, for example, 2 mm or less, preferably 1 mm or less. As for the material of the glass, it is better to have fewer ions eluted from the glass, so alkali-free glass is preferable, but soda-lime glass with a barrier coat such as SiO ₂ is also commercially available, and this can be used. In addition, in order to improve the gas barrier properties, the substrate 101 may be provided with a gas barrier film such as a dense silicon oxide film on at least one side, and it is preferable to provide a gas barrier film, especially when a synthetic resin plate, film or sheet with poor gas barrier properties is used as the substrate 101.

<Anode in Organic Electroluminescent Device>
The anode 102 plays a role in injecting holes into the light-emitting layer 105. When at least one layer of the hole injection layer 103 and the hole transport layer 104 is provided between the anode 102 and the light-emitting layer 105, holes are injected into the light-emitting layer 105 via these layers.

Materials for forming the anode 102 include inorganic and organic compounds. Inorganic compounds include, for example, metals (aluminum, gold, silver, nickel, palladium, chromium, etc.), metal oxides (indium oxide, tin oxide, indium-tin oxide (ITO), indium-zinc oxide (IZO), etc.), metal halides (copper iodide, etc.), copper sulfide, carbon black, ITO glass, and Nesa glass. Organic compounds include, for example, polythiophenes such as poly(3-methylthiophene), polypyrrole, polyaniline, and other conductive polymers. In addition, materials that are used as anodes in organic EL elements can be appropriately selected and used.

The resistance of the transparent electrode is not limited as long as it can supply sufficient current to light the light-emitting element, but a low resistance is desirable from the viewpoint of the power consumption of the light-emitting element. For example, an ITO substrate of 300 Ω/□ or less will function as an element electrode, but since it is now possible to supply substrates of around 10 Ω/□, it is particularly desirable to use a low resistance product of, for example, 100 to 5 Ω/□, preferably 50 to 5 Ω/□. The thickness of the ITO can be selected arbitrarily according to the resistance value, but it is usually used in the range of 50 to 300 nm.

<Hole injection layer and hole transport layer in organic electroluminescence device>
The hole injection layer 103 plays a role of efficiently injecting holes moving from the anode 102 into the light emitting layer 105 or the hole transport layer 104. The hole transport layer 104 plays a role of efficiently transporting holes injected from the anode 102 or holes injected from the anode 102 through the hole injection layer 103 to the light emitting layer 105. The hole injection layer 103 and the hole transport layer 104 are each formed by laminating and mixing one or more types of hole injection/transport materials, or by a mixture of a hole injection/transport material and a polymer binder. Alternatively, a layer may be formed by adding an inorganic salt such as iron (III) chloride to the hole injection/transport material.

A hole injection/transport material needs to be able to efficiently inject and transport holes from the positive electrode between electrodes to which an electric field is applied, and it is desirable for the material to have high hole injection efficiency and efficiently transport the injected holes. To achieve this, it is preferable for the material to have a low ionization potential, high hole mobility, and excellent stability, and to be one that is unlikely to generate impurities that act as traps during manufacture and use.

The polycyclic aromatic compound represented by the above general formula (1A) or general formula (1B) can be used as a material for forming the hole injection layer 103 and the hole transport layer 104. In addition, any compound can be selected and used from compounds that have been conventionally used as charge transport materials for holes in photoconductive materials, p-type semiconductors, and known compounds used in the hole injection layer and hole transport layer of organic EL elements.

Specific examples thereof include carbazole derivatives (N-phenylcarbazole, polyvinylcarbazole, etc.), biscarbazole derivatives such as bis(N-arylcarbazole) or bis(N-alkylcarbazole), triarylamine derivatives (polymers having an aromatic tertiary amino in the main chain or side chain, 1,1-bis(4-di-p-tolylaminophenyl)cyclohexane, N,N'-diphenyl-N,N'-di(3-methylphenyl)-4,4'-diaminobiphenyl, N,N'-diphenyl-N,N'-dinaphthyl-4,4'-diaminobiphenyl, N,N'-diphenyl-N,N'-di(3-methylphenyl)-4,4'-diphenyl-1,1'-diamine, N,N'-dinaphthyl-N,N'-diphenyl-4,4'-diphenyl-1,1'-diamine, N ⁴ ,N ^{4 '} -diphenyl-N ⁴ ,N ^{4 '} -Bis(9-phenyl-9H-carbazol-3-yl)-[1,1'-biphenyl]-4,4'-diamine, N ⁴ , N ⁴ , N ^{4 '} , N ^{4 '} -tetra[1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine, triphenylamine derivatives such as 4,4',4"-tris(3-methylphenyl(phenyl)amino)triphenylamine, starburst amine derivatives, etc.), stilbene derivatives, phthalocyanine derivatives (metal-free, copper phthalocyanine, etc.), pyrazoline derivatives, hydrazone compounds, benzofuran derivatives, thiophene derivatives, oxadiazole derivatives, quinoxaline derivatives (for example, 1,4,5,8,9,12-hexaazatriphenylene-2,3,6,7,10,11-hexacarbonitrile, etc.), heterocyclic compounds such as porphyrin derivatives, polysilanes, etc. As for polymers, polycarbonates and styrene derivatives having the above-mentioned monomers in the side chains, polyvinylcarbazole, polysilane, etc. are preferable, but there is no particular limitation as long as they are compounds that can form a thin film required for producing a light-emitting element, can inject holes from the anode, and can transport holes.

It is also known that the electrical conductivity of organic semiconductors is strongly influenced by their doping. Such organic semiconductor matrix substances consist of compounds with good electron donating or accepting properties. For doping with electron donating substances, strong electron acceptors such as tetracyanoquinone dimethane (TCNQ) or 2,3,5,6-tetrafluorotetracyano-1,4-benzoquinone dimethane (F4TCNQ) are known (see, for example, the literature "M. Pfeiffer, A. Beyer, T. Fritz, K. Leo, Appl. Phys. Lett., 73(22), 3202-3204 (1998)" and the literature "J. Blochwitz, M. Pheiffer, T. Fritz, K. Leo, Appl. Phys. Lett., 73(6), 729-731 (1998)"). These generate so-called holes by an electron transfer process in an electron-donating base material (hole transport material). The conductivity of the base material varies considerably depending on the number and mobility of the holes. Matrix materials with hole transport properties are known, for example, benzidine derivatives (such as TPD) or starburst amine derivatives (such as TDATA), or certain metal phthalocyanines (especially zinc phthalocyanine (ZnPc)) (JP 2005-167175 A).

The hole injection layer material and the hole transport layer material described above can also be used as hole layer materials in the form of a polymer compound obtained by polymerizing a reactive compound substituted with a reactive substituent as a monomer, or a crosslinked polymer thereof, or a pendant polymer compound obtained by reacting a main chain polymer with the reactive compound, or a crosslinked pendant polymer thereof. In this case, the reactive substituent can be quoted from the description of the polycyclic aromatic compound represented by formula (1A) or formula (1B).
The applications of such polymer compounds and crosslinked polymers will be described in detail below.

<Light-emitting layer in organic electroluminescent device>
The light-emitting layer 105 is a layer that emits light by recombining holes injected from the anode 102 and electrons injected from the cathode 108 between electrodes to which an electric field is applied. The material for the light-emitting layer 105 may be a polycyclic aromatic compound represented by the above general formula (1A) or general formula (1B). Any compound (light-emitting compound) that is excited by the recombination of holes and electrons to emit light may be used, and it is preferable that the compound is capable of forming a stable thin film shape and exhibits strong light-emitting (fluorescence) efficiency in a solid state.

The light-emitting layer may be a single layer or multiple layers, each of which is formed from light-emitting layer materials (host material, dopant material). The host material and the dopant material may each be one type or a combination of multiple types. The host material may be mixed with a hole transport layer material or an electron transport layer material, or a combination of these. The dopant material may be contained in the entire host material or may be contained partially in the host material. As a doping method, the dopant material may be formed by co-evaporation with the host material, but it may also be mixed with the host material in advance and then simultaneously evaporated, or mixed with the host material in advance with an organic solvent and then formed into a film by a wet film-forming method.

The amount of the host material used varies depending on the type of host material and can be determined according to the characteristics of the host material. The amount of the host material used is preferably 50 to 99.999% by weight, more preferably 80 to 99.95% by weight, and even more preferably 90 to 99.9% by weight, of the total light-emitting layer material.

The amount of dopant material used varies depending on the type of dopant material, and may be determined according to the characteristics of the dopant material. The amount of dopant used is preferably 0.001 to 50% by weight of the total material for the light-emitting layer, more preferably 0.05 to 20% by weight, and even more preferably 0.1 to 10% by weight. The above ranges are preferable in that, for example, concentration quenching can be prevented. In addition, from the viewpoint of durability, it is also preferable that some or all of the hydrogen atoms of the dopant material are deuterated.

On the other hand, in an organic EL element using a thermally activated delayed fluorescence dopant material, a low concentration of the dopant material is preferable in terms of preventing concentration quenching, but a high concentration of the dopant material is preferable in terms of the efficiency of the thermally activated delayed fluorescence mechanism. Furthermore, in an organic EL element using a thermally activated delayed fluorescence assist dopant material, a low concentration of the dopant material is preferable compared to the amount of the assist dopant material in terms of the efficiency of the thermally activated delayed fluorescence mechanism of the assist dopant material.

When an assist dopant material is used, the approximate amounts of the host material, assist dopant material, and dopant material used are 40 to 99.999% by weight, 59 to 1% by weight, and 20 to 0.001% by weight, respectively, of the total light-emitting layer material, preferably 60 to 99.99% by weight, 39 to 5% by weight, and 10 to 0.01% by weight, respectively, and more preferably 70 to 99.95% by weight, 29 to 10% by weight, and 5 to 0.05% by weight. The polycyclic aromatic compound represented by the above general formula (1A) or general formula (1B) can also be used as an assist dopant material.

Examples of host materials include condensed ring derivatives such as anthracene, pyrene, dibenzochrysene, or fluorene, which have long been known as light emitters, bisstyryl derivatives such as bisstyryl anthracene derivatives and distyrylbenzene derivatives, tetraphenylbutadiene derivatives, and cyclopentadiene derivatives. In particular, anthracene-based compounds, fluorene-based compounds, or dibenzochrysene-based compounds are preferred. From the viewpoint of durability, it is also preferred that some or all of the hydrogen atoms in the host material are deuterated. Furthermore, it is also preferred to form an emission layer by combining a host compound in which some or all of the hydrogen atoms are deuterated with a dopant compound in which some or all of the hydrogen atoms are deuterated.

<Anthracene-based compounds>
The anthracene compound serving as the host is, for example, a compound represented by the following general formula (3).

In formula (3),
X and Ar ⁴ are each independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted diarylamino, optionally substituted diheteroarylamino, optionally substituted arylheteroarylamino, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted arylthio or optionally substituted silyl, and all of X and Ar ⁴ are not hydrogen at the same time;
At least one hydrogen atom in the compound represented by formula (3) may be substituted with halogen, cyano, deuterium or an optionally substituted heteroaryl.

In addition, a polymer (preferably a dimer) may be formed using the structure represented by formula (3) as a unit structure. In this case, for example, the unit structures represented by formula (3) may be bonded to each other via X, where X may be a single bond, an arylene (phenylene, biphenylene, naphthylene, etc.), or a heteroarylene (a pyridine ring, a dibenzofuran ring, a dibenzothiophene ring, a carbazole ring, a benzocarbazole ring, a phenyl-substituted carbazole ring, etc., having a divalent bond).

The details of the above aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or silyl are described in the preferred embodiments section below. In addition, the substituents on these groups include aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or silyl, and the details of these are also described in the preferred embodiments section below.

Preferred embodiments of the above anthracene-based compounds are described below. The symbols in the structures below are defined as above.

In general formula (3), X is each independently a group represented by the above formula (3-X1), formula (3-X2) or formula (3-X3), and the group represented by formula (3-X1), formula (3-X2) or formula (3-X3) is bonded to the anthracene ring of formula (3) at *. Preferably, two Xs are not simultaneously a group represented by formula (3-X3). More preferably, two Xs are not simultaneously a group represented by formula (3-X2).

In addition, a polymer (preferably a dimer) may be formed using the structure represented by formula (3) as a unit structure. In this case, for example, the unit structures represented by formula (3) may be bonded to each other via X, where X may be a single bond, an arylene (phenylene, biphenylene, naphthylene, etc.), or a heteroarylene (a pyridine ring, a dibenzofuran ring, a dibenzothiophene ring, a carbazole ring, a benzocarbazole ring, a phenyl-substituted carbazole ring, etc., having a divalent bond).

The naphthylene moieties in formula (3-X1) and formula (3-X2) may be condensed with one benzene ring. The condensed structures are as follows:

Ar ¹ and Ar ² are each independently hydrogen, phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenylyl, or a group represented by the above formula (A) (including a carbazolyl group, a benzocarbazolyl group, and a phenyl-substituted carbazolyl group). When Ar ¹ or Ar ² is a group represented by formula (A), the group represented by formula (A) is bonded to the naphthalene ring in formula (3-X1) or formula (3-X2) at the *.

Ar ³ is phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenylyl, or a group represented by the above formula (A) (including a carbazolyl group, a benzocarbazolyl group, and a phenyl-substituted carbazolyl group). When Ar ³ is a group represented by formula (A), the group represented by formula (A) is bonded to the single bond represented by a straight line in formula (3-X3) at the *. That is, the anthracene ring of formula (3) and the group represented by formula (A) are directly bonded.

In addition, Ar ³ may have a substituent, and at least one hydrogen atom in Ar ³ may be further substituted with an alkyl having 1 to 4 carbon atoms, a cycloalkyl having 5 to 10 carbon atoms, phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, chrysenyl, triphenylenyl, pyrenylyl, or a group represented by the above formula (A) (including a carbazolyl group and a phenyl-substituted carbazolyl group). When the substituent in Ar ³ is a group represented by formula (A), the group represented by formula (A) bonds to Ar ³ in formula (3-X3) at the *.

Each ^Ar4 is independently hydrogen, phenyl, biphenylyl, terphenylyl, naphthyl, or silyl substituted with alkyl having 1 to 4 carbon atoms (eg, methyl, ethyl, t-butyl) and/or cycloalkyl having 5 to 10 carbon atoms.

Examples of alkyl groups having 1 to 4 carbon atoms that can be substituted for silyl include methyl, ethyl, propyl, i-propyl, butyl, sec-butyl, t-butyl, and cyclobutyl, and each of the three hydrogen atoms in the silyl is independently substituted with one of these alkyl groups.

Specific examples of "silyl substituted with alkyl having 1 to 4 carbon atoms" include trimethylsilyl, triethylsilyl, tripropylsilyl, tri-i-propylsilyl, tributylsilyl, trisec-butylsilyl, tri-t-butylsilyl, ethyldimethylsilyl, propyldimethylsilyl, i-propyldimethylsilyl, butyldimethylsilyl, sec-butyldimethylsilyl, t-butyldimethylsilyl, methyldiethylsilyl, propyldiethylsilyl, i-propyldiethylsilyl, butyldiethylsilyl, sec-butyldiethylsilyl, t-butyldiethylsilyl, methyldipropylsilyl, ethyldipropylsilyl, butyldipropylsilyl, sec-butyldipropylsilyl, t-butyldipropylsilyl, methyldi-i-propylsilyl, ethyldi-i-propylsilyl, butyldi-i-propylsilyl, sec-butyldi-i-propylsilyl, and t-butyldi-i-propylsilyl.

Examples of cycloalkyls having 5 to 10 carbon atoms that can be substituted for silyl include cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, norbornenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.0]pentyl, bicyclo[2.1.1]hexyl, bicyclo[3.1.0]hexyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl, adamantyl, decahydronaphthalenyl, and decahydroazulenyl, and each of the three hydrogen atoms in the silyl is independently substituted with one of these cycloalkyls.

Specific examples of "silyl substituted with cycloalkyl having 5 to 10 carbon atoms" include tricyclopentylsilyl, tricyclohexylsilyl, etc.

Substituted silyls include dialkylcycloalkylsilyls, which are substituted with two alkyls and one cycloalkyl, and alkyldicycloalkylsilyls, which are substituted with one alkyl and two cycloalkyls. Specific examples of the alkyl and cycloalkyl substituents include the groups mentioned above.

In addition, hydrogen in the chemical structure of the anthracene compound represented by general formula (3) may be substituted with a group represented by formula (A) above. When substituted with a group represented by formula (A), the group represented by formula (A) replaces at least one hydrogen in the compound represented by formula (3) at the *.

The group represented by formula (A) is one of the substituents that the anthracene compound represented by formula (3) can have.

In the above formula (A), Y is -O-, -S- or >N-R ²⁹ , R ²¹ to R ²⁸ are each independently hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, optionally substituted amino, halogen, hydroxy or cyano, adjacent groups among R ²¹ to R ²⁸ may be bonded to each other to form a hydrocarbon ring, an aryl ring or a heteroaryl ring, and R ²⁹ is hydrogen or optionally substituted aryl.

The "alkyl" in the "optionally substituted alkyl" in R ²¹ to R ²⁸ may be either linear or branched, and examples thereof include linear alkyl having 1 to 24 carbon atoms or branched alkyl having 3 to 24 carbon atoms. An alkyl having 1 to 18 carbon atoms (branched alkyl having 3 to 18 carbon atoms) is preferred, an alkyl having 1 to 12 carbon atoms (branched alkyl having 3 to 12 carbon atoms) is more preferred, an alkyl having 1 to 6 carbon atoms (branched alkyl having 3 to 6 carbon atoms) is even more preferred, and an alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms) is particularly preferred.

Specific examples of "alkyl" include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl (t-amyl), n-hexyl, 1-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl (1,1,3,3-tetramethylbutyl), 1-methyl Examples of the aryl ether include arylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, and n-eicosyl.

Examples of the "cycloalkyl" in the "optionally substituted cycloalkyl" in R ²¹ to R ²⁸ include cycloalkyl having 3 to 24 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, cycloalkyl having 3 to 16 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, cycloalkyl having 5 to 8 carbon atoms, cycloalkyl having 5 to 6 carbon atoms, and cycloalkyl having 5 carbon atoms.

Specific examples of "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and alkyl (especially methyl) substituted derivatives of these having 1 to 4 carbon atoms, as well as norbornenyl, bicyclo[1.1.0]butyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.0]pentyl, bicyclo[2.1.1]hexyl, bicyclo[3.1.0]hexyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl, adamantyl, diamantyl, decahydronaphthalenyl, and decahydroazulenyl.

The "aryl" in the "optionally substituted aryl" in R ^{to R} is, for example, an aryl having 6 to 30 carbon atoms, preferably an aryl having 6 to 16 carbon atoms, more preferably an aryl having 6 to 12 carbon atoms, and particularly preferably an aryl having 6 to 10 carbon atoms.

Specific examples of "aryl" include monocyclic phenyl, bicyclic ...

Examples of the "heteroaryl" in the "optionally substituted heteroaryl" in R ^{to R} include heteroaryl having 2 to 30 carbon atoms, preferably heteroaryl having 2 to 25 carbon atoms, more preferably heteroaryl having 2 to 20 carbon atoms, still more preferably heteroaryl having 2 to 15 carbon atoms, and particularly preferably heteroaryl having 2 to 10 carbon atoms. Examples of the heteroaryl include heterocycles containing, as ring-constituting atoms other than carbon, 1 to 5 heteroatoms selected from oxygen, sulfur and nitrogen.

Specific examples of "heteroaryl" include pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, and carbazolyl. , acridinyl, phenoxathiinyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenazasilinyl, indolizinyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, naphthobenzofuranyl, thiophenyl, benzothiophenyl, dibenzothiophenyl, naphthobenzothiophenyl, benzophosphoryl, dibenzophosphoryl, a monovalent group of a benzophosphole oxide ring, a monovalent group of a dibenzophosphole oxide ring, furazanyl, thianthrenyl, indolocarbazolyl, benzoindolocarbazolyl, and benzobenzoindolocarbazolyl.

Examples of the "alkoxy" in the "optionally substituted alkoxy" in R ²¹ to R ²⁸ include linear alkoxy having 1 to 24 carbon atoms or branched alkoxy having 3 to 24 carbon atoms. An alkoxy having 1 to 18 carbon atoms (branched alkoxy having 3 to 18 carbon atoms) is preferred, an alkoxy having 1 to 12 carbon atoms (branched alkoxy having 3 to 12 carbon atoms) is more preferred, an alkoxy having 1 to 6 carbon atoms (branched alkoxy having 3 to 6 carbon atoms) is even more preferred, and an alkoxy having 1 to 4 carbon atoms (branched alkoxy having 3 to 4 carbon atoms) is particularly preferred.

Specific examples of "alkoxy" include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, s-butoxy, t-butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, etc.

The "aryloxy" in the "optionally substituted aryloxy" in R ²¹ to R ²⁸ is a group in which the hydrogen of the -OH group is substituted with an aryl, and the aryl can be any of the groups explained above as the "aryl" in R ²¹ to R ²⁸ .

The "arylthio" in the "optionally substituted arylthio" in R ²¹ to R ²⁸ is a group in which the hydrogen of the -SH group is replaced by an aryl, and the aryl can be any of the groups explained as the "aryl" in R ²¹ to R ²⁸ above.

The "trialkylsilyl" in R ²¹ to R ²⁸ includes a group in which three hydrogen atoms in a silyl group are each independently substituted with an alkyl, and this alkyl can be cited from the groups explained above as the "alkyl" in R ²¹ to R ^28. The alkyl to be substituted is preferably an alkyl having 1 to 4 carbon atoms, and specific examples thereof include methyl, ethyl, propyl, i-propyl, butyl, sec-butyl, t-butyl, cyclobutyl, etc.

Specific examples of "trialkylsilyl" include trimethylsilyl, triethylsilyl, tripropylsilyl, tri-i-propylsilyl, tributylsilyl, trisec-butylsilyl, tri-t-butylsilyl, ethyldimethylsilyl, propyldimethylsilyl, i-propyldimethylsilyl, butyldimethylsilyl, sec-butyldimethylsilyl, t-butyldimethylsilyl, methyldiethylsilyl, propyldiethylsilyl, i-propyldiethylsilyl, butyldiethylsilyl, sec-butyldiethylsilyl, t-butyldiethylsilyl, methyldipropylsilyl, ethyldipropylsilyl, butyldipropylsilyl, sec-butyldipropylsilyl, t-butyldipropylsilyl, methyldi-i-propylsilyl, ethyldi-i-propylsilyl, butyldi-i-propylsilyl, sec-butyldi-i-propylsilyl, and t-butyldi-i-propylsilyl.

The "tricycloalkylsilyl" in R ²¹ to R ²⁸ includes a group in which three hydrogen atoms in a silyl group are each independently replaced with a cycloalkyl, and this cycloalkyl can be cited from the groups described above as the "cycloalkyl" in R ²¹ to R ^28. Preferred cycloalkyl for substitution is a cycloalkyl having 5 to 10 carbon atoms, and specific examples thereof include cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.0]pentyl, bicyclo[2.1.1]hexyl, bicyclo[3.1.0]hexyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl, adamantyl, decahydronaphthalenyl, and decahydroazulenyl.

Specific examples of "tricycloalkylsilyl" include tricyclopentylsilyl, tricyclohexylsilyl, etc.

Specific examples of dialkylcycloalkylsilyl substituted with two alkyls and one cycloalkyl, and alkyldicycloalkylsilyl substituted with one alkyl and two cycloalkyls include silyl substituted with groups selected from the specific alkyls and cycloalkyls mentioned above.

The "substituted amino" in the "optionally substituted amino" in R ²¹ to R ²⁸ includes, for example, an amino group in which two hydrogen atoms are substituted with aryl or heteroaryl. An amino group in which two hydrogen atoms are substituted with aryl atoms is a diaryl-substituted amino, an amino group in which two hydrogen atoms are substituted with heteroaryl atoms is a diheteroaryl-substituted amino, and an amino group in which two hydrogen atoms are substituted with an aryl and a heteroaryl atom is an arylheteroaryl-substituted amino. The aryl and heteroaryl groups can be cited from the groups explained as "aryl" and "heteroaryl" in R ²¹ to R ²⁸ above.

Specific examples of "substituted amino" include diphenylamino, dinaphthylamino, phenylnaphthylamino, dipyridylamino, phenylpyridylamino, naphthylpyridylamino, and the like.

The "halogen" in R ²¹ to R ²⁸ includes fluorine, chlorine, bromine and iodine.

Some of the groups described as R ²¹ to R ²⁸ may be substituted as described above, and in this case, the substituents include alkyl, cycloalkyl, aryl, or heteroaryl. The alkyl, cycloalkyl, aryl, or heteroaryl can refer to the groups described as "alkyl", "cycloalkyl", "aryl", or "heteroaryl" in R ²¹ to R ²⁸ above.

R ²⁹ in ">N-R ²⁹ " as Y is hydrogen or an optionally substituted aryl, and examples of this aryl include the groups described above as the "aryl" in R ²¹ to R ²⁸ , and examples of the substituents thereof include the groups described above as the substituents for R ²¹ to R ²⁸ .

Adjacent groups among R ²¹ to R ²⁸ may be bonded to each other to form a hydrocarbon ring, an aryl ring, or a heteroaryl ring. The group represented by the following formula (A-1) does not form a ring, and examples of the group represented by any of the following formulas (A-2) to (A-14) include groups represented by the following formulas (A-1) to (A-14). At least one hydrogen atom in the group represented by any of formulas (A-1) to (A-14) may be substituted with alkyl, cycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, diaryl-substituted amino, diheteroaryl-substituted amino, arylheteroaryl-substituted amino, halogen, hydroxy, or cyano. * in each structural formula represents a bonding position, and Y is defined as above.

Examples of the ring formed by bonding adjacent groups to each other include a hydrocarbon ring such as a cyclohexane ring, and examples of the aryl ring and heteroaryl ring include the ring structures explained in relation to "aryl" and "heteroaryl" in R ^to R ^above . These rings are formed so as to be condensed with one or two benzene rings in the above formula (A-1).

Examples of the group represented by formula (A) include groups represented by any of the above formulas (A-1) to (A-14), preferably any of the above formulas (A-1) to (A-5) and (A-12) to (A-14), more preferably any of the above formulas (A-1) to (A-4), even more preferably any of the above formulas (A-1), (A-3) and (A-4), and particularly preferably any of the above formulas (A-1).

As described above, the group represented by formula (A) is bonded to the naphthalene ring in formula (3-X1) or formula (3-X2), the single bond in formula (3-X3), or Ar ³ in formula (3-X3) at * in formula (A), and is substituted for at least one hydrogen in the compound represented by formula (3). Among these bonding forms, a bonding form to at least one of the naphthalene ring in formula (3-X1) or formula (3-X2), the single bond in formula (3-X3), and Ar ³ in formula (3-X3) is preferred.

In addition, in the structure of the group represented by formula (A), the naphthalene ring in formula (3-X1) or formula (3-X2), the single bond in formula (3-X3), and the position at which Ar ³ in formula (3-X3) is bonded, and in the structure of the group represented by formula (A), the position at which at least one hydrogen atom in the compound represented by formula (3) is substituted, may be any position in the structure of formula (A), and may be bonded, for example, to any of the two benzene rings in the structure of formula (A), to any ring formed by bonding adjacent groups among R ²¹ to R ²⁸ in the structure of formula (A), or to any position in R ²⁹ in “>N-R ²⁹ ” as Y in the structure of formula (A).

Examples of the group represented by formula (A) include the following groups: In the formula, Y and * are defined as above.

In addition, all or some of the hydrogen atoms in the chemical structure of the anthracene compound represented by general formula (3) may be deuterium atoms.

Specific examples of anthracene-based compounds include compounds represented by any of the following formulas (3-1) to (3-142). In the structural formulas below, "Me" represents a methyl group, "D" represents deuterium, and "tBu" represents a t-butyl group.

The anthracene compound represented by formula (3) can be produced by applying Suzuki coupling, Negishi ^coupling , or other known coupling reactions using a compound having a reactive group at a desired position of the anthracene skeleton and a compound having a reactive group in a partial structure such as X, Ar4, and the structure of formula (A) as starting materials. Examples of reactive groups in these reactive compounds include halogens and boronic acids. As a specific production method, for example, the synthesis method in paragraphs [0089] to [0175] of WO 2014/141725 A can be referred to.

<Fluorene-based compounds>
The compound represented by formula (4) basically functions as a host.

In the above formula (4),
R ¹ to R ¹⁰ are each independently hydrogen, aryl, heteroaryl (the heteroaryl may be bonded to the fluorene skeleton in the above formula (4) via a linking group), diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkenyl, alkoxy or aryloxy, and at least one hydrogen in R ¹ to R ¹⁰ may be substituted with an aryl, heteroaryl, alkyl or cycloalkyl;
In addition, ^R1 and ^R2 , ^R2 and ^R3 , ^R3 and ^R4 , ^R5 and ^R6 , ^R6 and ^R7 , ^R7 and ^R8 , or ^R9 and ^R10 may each independently bond to form a fused ring or a spiro ring, and at least one hydrogen atom in the formed ring may be substituted with an aryl, a heteroaryl (the heteroaryl may be bonded to the formed ring via a linking group), a diarylamino, a diheteroarylamino, an arylheteroarylamino, an alkyl, a cycloalkyl, an alkenyl, an alkoxy, or an aryloxy, and at least one hydrogen atom in these substituents may be substituted with an aryl, a heteroaryl, an alkyl, or a cycloalkyl, and
At least one hydrogen in the compound represented by formula (4) may be substituted with halogen, cyano or deuterium.

For details of each group in the definition of the above formula (4), the explanation for the polycyclic aromatic compound represented by the above formula (1A) or formula (1B) can be cited.

Examples of the alkenyl in R ¹ to R ¹⁰ include alkenyl having 2 to 30 carbon atoms, preferably alkenyl having 2 to 20 carbon atoms, more preferably alkenyl having 2 to 10 carbon atoms, further preferably alkenyl having 2 to 6 carbon atoms, and particularly preferably alkenyl having 2 to 4 carbon atoms. Preferred alkenyls are vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, or 5-hexenyl.

式（４－Ａｒ１）から式（４－Ａｒ５）中、Ｙ^１は、それぞれ独立して、Ｏ、ＳまたはＮ－Ｒであり、Ｒはフェニル、ビフェニリル、ナフチル、アントラセニルまたは水素であり、
上記式（４－Ａｒ１）から式（４－Ａｒ５）の構造における少なくとも１つの水素はフェニル、ビフェニリル、ナフチル、アントラセニル、フェナントレニル、メチル、エチル、プロピル、または、ブチルで置換されていてもよい。 Specific examples of heteroaryl include monovalent groups represented by removing any one hydrogen atom from a compound of the following formula (4-Ar1), formula (4-Ar2), formula (4-Ar3), formula (4-Ar4), or formula (4-Ar5).

In formula (4-Ar1) to formula (4-Ar5), each Y ¹ is independently O, S or N—R, and R is phenyl, biphenylyl, naphthyl, anthracenyl or hydrogen;
At least one hydrogen atom in the structures of the above formulae (4-Ar1) to (4-Ar5) may be substituted with phenyl, biphenylyl, naphthyl, anthracenyl, phenanthrenyl, methyl, ethyl, propyl, or butyl.

These heteroaryls may be bonded to the fluorene skeleton in formula (4) via a linking group. That is, the fluorene skeleton in formula (4) and the heteroaryl may be bonded directly or via a linking group. Examples of the linking group include phenylene, biphenylene, naphthylene, anthracenylene, methylene, ethylene, -OCH ₂ CH ₂ -, -CH ₂ CH ₂ O-, and -OCH ₂ CH ₂ O-.

In addition, R ¹ and R ² , R ² and R ³ , ^{R 3} and R ⁴ , R ⁵ and R ⁶ , R 6 and R ⁷ or R ⁷ and R ⁸ in formula (4) may be independently bonded to form a fused ring, and R ⁹ and R ¹⁰ may be bonded to form a spiro ring. The fused ring formed by R ¹ to R ⁸ is a ring fused to the benzene ring in formula (4), and is an aliphatic ring or an aromatic ring. It is preferably an aromatic ring, and examples of the structure including the benzene ring in formula (4) include a naphthalene ring and a phenanthrene ring. The spiro ring formed by R ⁹ and R ¹⁰ is a ring spiro-bonded to the 5-membered ring in formula (4), and is an aliphatic ring or an aromatic ring. It is preferably an aromatic ring, and examples of the structure including the benzene ring in formula (4) include a fluorene ring.

The compound represented by general formula (4) is preferably a compound represented by the following formula (4-1), formula (4-2) or formula (4-3), which is a compound in which a benzene ring formed by bonding R ¹ and R ² in general formula (4) is condensed, a compound in which a benzene ring formed by bonding R ³ and R ⁴ in general formula (4) is condensed, and a compound in which none of R ¹ to R ⁸ is bonded in general formula (4), respectively.

The definitions of R ¹ to R ¹⁰ in formulas (4-1), (4-2) and (4-3) are the same as the corresponding R ¹ to R ¹⁰ in formula (4), and the definitions of R ¹¹ to R ¹⁴ in formulas (4-1) and (4-2) are the same as the corresponding R ¹ to R ¹⁰ in formula (4).

The compound represented by general formula (4) is more preferably a compound represented by the following formula (4-1A), formula (4-2A) or formula (4-3A), which is a compound in which R ⁹ and R ¹⁰ are bonded to form a spiro-fluorene ring in formula (4-1), formula (4-1) or formula (4-3), respectively.

The definitions of R ² to R ⁷ in formulae (4-1A), (4-2A) and (4-3A) are the same as the corresponding R ² to R ⁷ in formulae (4-1), (4-2) and (4-3), and the definitions of R ¹¹ to R ¹⁴ in formulae (4-1A) and (4-2A) are the same as R ¹¹ to R ¹⁴ in formulae (4-1) and (4-2).

In addition, all or some of the hydrogen atoms in the compound represented by formula (4) may be replaced by halogen, cyano or deuterium.

Specific examples of the fluorene-based compound include compounds represented by any one of the following formulas (4-4) to (4-22): In the following structural formulas, "Me" represents a methyl group.

<Dibenzochrysene compounds>
The dibenzochrysene compound as the host is, for example, a compound represented by the following general formula (5).

In the above formula (5),
R ¹ to R ¹⁶ are each independently hydrogen, aryl, heteroaryl (the heteroaryl may be bonded to the dibenzochrysene skeleton in the above formula (5) via a linking group), diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkenyl, alkoxy or aryloxy, and at least one hydrogen in R ¹ to R ¹⁶ may be substituted with an aryl, heteroaryl, alkyl or cycloalkyl;
In addition, adjacent groups among R ¹ to R ¹⁶ may be bonded to each other to form a fused ring, and at least one hydrogen atom in the formed ring may be substituted with an aryl, a heteroaryl (the heteroaryl may be bonded to the formed ring via a linking group), a diarylamino, a diheteroarylamino, an arylheteroarylamino, an alkyl, a cycloalkyl, an alkenyl, an alkoxy, or an aryloxy, and at least one hydrogen atom in these substituents may be substituted with an aryl, a heteroaryl, an alkyl, or a cycloalkyl, and
At least one hydrogen in the compound represented by formula (5) may be substituted with halogen, cyano or deuterium.

For details of each group in the definition of the above formula (5), the explanation for the polycyclic aromatic compound represented by formula (1A) or formula (1B) described above can be cited.

In the definition of the above formula (5), the alkenyl may, for example, be an alkenyl having 2 to 30 carbon atoms, preferably an alkenyl having 2 to 20 carbon atoms, more preferably an alkenyl having 2 to 10 carbon atoms, even more preferably an alkenyl having 2 to 6 carbon atoms, and particularly preferably an alkenyl having 2 to 4 carbon atoms. Preferred alkenyls are vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, or 5-hexenyl.

式（５－Ａｒ１）から式（５－Ａｒ５）中、Ｙ^１は、それぞれ独立して、Ｏ、ＳまたはＮ－Ｒであり、Ｒはフェニル、ビフェニリル、ナフチル、アントラセニルまたは水素であり、
上記式（５－Ａｒ１）から式（５－Ａｒ５）の構造における少なくとも１つの水素はフェニル、ビフェニリル、ナフチル、アントラセニル、フェナントレニル、メチル、エチル、プロピル、または、ブチルで置換されていてもよい。 Specific examples of heteroaryl include monovalent groups represented by removing any one hydrogen atom from a compound of the following formula (5-Ar1), formula (5-Ar2), formula (5-Ar3), formula (5-Ar4), or formula (5-Ar5).

In formula (5-Ar1) to formula (5-Ar5), each Y ¹ is independently O, S or N—R, and R is phenyl, biphenylyl, naphthyl, anthracenyl or hydrogen;
At least one hydrogen atom in the structures of the above formulae (5-Ar1) to (5-Ar5) may be substituted with phenyl, biphenylyl, naphthyl, anthracenyl, phenanthrenyl, methyl, ethyl, propyl, or butyl.

These heteroaryls may be bonded to the dibenzochrysene skeleton in formula (5) via a linking group. That is, the dibenzochrysene skeleton and the heteroaryl in formula (5) may be bonded directly or via a linking group. Examples of the linking group include phenylene, biphenylene, naphthylene, anthracenylene, methylene, ethylene, -OCH ₂ CH ₂ -, -CH ₂ CH ₂ O-, and -OCH ₂ CH ₂ O-.

In the compound represented by formula (5), R ¹ , R ⁴ , R ⁵ , R ⁸ , R ⁹ , R ¹² , R ¹³ and R ¹⁶ are preferably hydrogen. In this case, it is preferable that R ² , R ³ , R ⁶ , R ⁷ , R ¹⁰ , R ¹¹ , R ¹⁴ and R ¹⁵ in formula (5) are each independently hydrogen, phenyl, biphenylyl, naphthyl, anthracenyl, phenanthrenyl, a monovalent group having the structure of the above formula (5-Ar1), (5-Ar2), (5-Ar3), (5-Ar4) or (5-Ar5) (the monovalent group having the structure may be bonded to the dibenzochrysene skeleton in formula (5)) via phenylene, biphenylene, naphthylene, anthracenylene, methylene, ethylene, -OCH ₂ CH ₂ -, -CH ₂ CH ₂ O- or -OCH ₂ CH ₂ O-), methyl, ethyl, propyl or butyl.

In the compound represented by formula (5), R ¹ , R ² , R ⁴ , R ⁵ , R 7 , R ⁸ , R ⁹ , R ¹⁰ , R ¹² , R ¹³ , R ^{15 and R 16 are} more preferably hydrogen. In this case, at least one (preferably one or two, more preferably one) of R ³ , R ⁶ , R ¹¹ and R ¹⁴ in formula (5) is a single bond, phenylene, biphenylene, naphthylene, anthracenylene, methylene, ethylene, -OCH ₂ CH ₂ -, -CH ₂ CH ₂ O-, or a monovalent group having the structure of formula (5-Ar1), formula (5-Ar2), formula (5-Ar3), formula (5-Ar4) or formula (5-Ar5) via -OCH ₂ CH ₂ O-;
The other than the at least one (i.e., other than the position substituted by the monovalent group having the structure) is hydrogen, phenyl, biphenylyl, naphthyl, anthracenyl, methyl, ethyl, propyl, or butyl, and at least one hydrogen in these groups may be substituted with phenyl, biphenylyl, naphthyl, anthracenyl, methyl, ethyl, propyl, or butyl.

In addition, when a monovalent group having a structure represented by any of formulas (5-Ar1) to (5-Ar5) is selected as R ² , R ³ , R ⁶ , R ⁷ , R ¹⁰ , R ¹¹ , R ¹⁴ and R ¹⁵ in formula (5), at least one hydrogen atom in the structure may be bonded to any of R ¹ to R ¹⁶ in formula (5) to form a single bond.

Specific examples of the dibenzochrysene compound include compounds represented by any of the following formulas (5-1) to (5-39): In the following structural formulas, "tBu" represents a t-butyl group.

The above-mentioned light-emitting layer materials (host material and dopant material) can be used as light-emitting layer materials in the form of polymer compounds obtained by polymerizing a reactive compound substituted with a reactive substituent as a monomer, or a crosslinked polymer thereof, or a pendant-type polymer compound obtained by reacting a main-chain polymer with the reactive compound, or a crosslinked pendant polymer thereof. In this case, the reactive substituent can be quoted from the description of the polycyclic aromatic compound represented by formula (1A) or formula (1B).
The applications of such polymer compounds and crosslinked polymers will be described in detail below.

<Examples of polymer host materials>

In formula (SPH-1),
Each MU is independently a divalent group represented by removing any two hydrogen atoms from an aromatic compound, each EC is independently a monovalent group represented by removing any one hydrogen atom from an aromatic compound, two hydrogen atoms in MU are replaced with EC or MU, and k is an integer from 2 to 50,000.

More specifically,
Each MU is independently arylene, heteroarylene, diarylenarylamino, diarylenarylboryl, oxaborine-diyl, or azaborine-diyl;
each E C is independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, or aryloxy;
At least one hydrogen in MU and EC may be further substituted with aryl, heteroaryl, diarylamino, alkyl, and cycloalkyl;
k is an integer from 2 to 50,000.
k is preferably an integer from 20 to 50,000, and more preferably an integer from 100 to 50,000.

At least one hydrogen atom in MU and EC in formula (SPH-1) may be substituted with an alkyl group having 1 to 24 carbon atoms, a cycloalkyl group having 3 to 24 carbon atoms, a halogen atom or deuterium atom; further, any —CH ₂ — group in the alkyl group may be substituted with —O— or —Si(CH ₃ ) ₂ —; any —CH ₂ — group in the alkyl group except for the —CH ₂ — group directly bonded to EC in formula (SPH-1) may be substituted with an arylene group having 6 to 24 carbon atoms; and any hydrogen atom in the alkyl group may be substituted with fluorine.

Examples of MU include a divalent group represented by removing any two hydrogen atoms from any of the following compounds:

More specifically, examples include divalent groups represented by any of the following structures: In these, MU is bonded to another MU or EC at *.

EC may be, for example, a monovalent group represented by any of the following structures. In these, EC is bonded to MU at *.

From the viewpoint of solubility and coating film-forming properties, the compound represented by formula (SPH-1) is preferably such that 10 to 100% of the total number of MUs (k) in the molecule have an alkyl having 1 to 24 carbon atoms, more preferably 30 to 100% of the total number of MUs (k) in the molecule have an alkyl having 1 to 18 carbon atoms (branched chain alkyl having 3 to 18 carbon atoms), and even more preferably 50 to 100% of the total number of MUs (k) in the molecule have an alkyl having 1 to 12 carbon atoms (branched chain alkyl having 3 to 12 carbon atoms). On the other hand, from the viewpoint of in-plane orientation and charge transport, it is preferable that 10 to 100% of the total number of MUs (k) in the molecule have an alkyl having 7 to 24 carbon atoms, and more preferably 30 to 100% of the total number of MUs (k) in the molecule have an alkyl having 7 to 24 carbon atoms (branched chain alkyl having 7 to 24 carbon atoms).

The uses of such polymer compounds and crosslinked polymers will be described in detail later.

<Electron Injection Layer and Electron Transport Layer in Organic Electroluminescent Device>
The electron injection layer 107 plays a role of efficiently injecting electrons moving from the cathode 108 into the light emitting layer 105 or the electron transport layer 106. The electron transport layer 106 plays a role of efficiently transporting electrons injected from the cathode 108 or electrons injected from the cathode 108 via the electron injection layer 107 to the light emitting layer 105. The electron transport layer 106 and the electron injection layer 107 are each formed by laminating or mixing one or more types of electron transport/injection materials, or by a mixture of an electron transport/injection material and a polymer binder.

The electron injection/transport layer is a layer that is responsible for injecting electrons from the cathode and transporting the electrons. It is desirable that the electron injection efficiency is high and that the injected electrons are transported efficiently. For this purpose, it is preferable that the material has a large electron affinity, a large electron mobility, excellent stability, and is unlikely to generate impurities that become traps during manufacture and use. However, when considering the balance of hole and electron transport, if the material mainly plays a role of efficiently preventing holes from the anode from flowing to the cathode without recombining, even if the electron transport ability is not so high, it has the effect of improving the luminous efficiency equivalent to a material with a high electron transport ability. Therefore, the electron injection/transport layer in this embodiment may also include the function of a layer that can efficiently block the movement of holes.

The material (electron transport material) forming the electron transport layer 106 or the electron injection layer 107 can be a polycyclic aromatic compound represented by the above general formula (1A) or general formula (1B). In addition, any compound that has been conventionally used as an electron transport compound in photoconductive materials and known compounds used in the electron injection layer and electron transport layer of an organic EL element can be selected and used.

Materials used in the electron transport layer or electron injection layer preferably contain at least one selected from compounds consisting of aromatic rings or heteroaromatic rings composed of one or more atoms selected from carbon, hydrogen, oxygen, sulfur, silicon, and phosphorus, pyrrole derivatives and their condensed ring derivatives, and metal complexes having electron-accepting nitrogen. Specific examples include condensed ring aromatic ring derivatives such as naphthalene and anthracene, styryl aromatic ring derivatives such as 4,4'-bis(diphenylethenyl)biphenyl, perinone derivatives, coumarin derivatives, naphthalimide derivatives, quinone derivatives such as anthraquinone and diphenoquinone, phosphorus oxide derivatives, carbazole derivatives, and indole derivatives. Metal complexes having electron-accepting nitrogen include, for example, hydroxyazole complexes such as hydroxyphenyloxazole complexes, azomethine complexes, tropolone metal complexes, flavonol metal complexes, and benzoquinoline metal complexes. These materials can be used alone or in combination with different materials.

Specific examples of other electron transport compounds include pyridine derivatives, naphthalene derivatives, anthracene derivatives, phenanthroline derivatives, perinone derivatives, coumarin derivatives, naphthalimide derivatives, anthraquinone derivatives, diphenoquinone derivatives, diphenylquinone derivatives, perylene derivatives, oxadiazole derivatives (such as 1,3-bis[(4-t-butylphenyl)1,3,4-oxadiazolyl]phenylene), thiophene derivatives, triazole derivatives (such as N-naphthyl-2,5-diphenyl-1,3,4-triazole), thiadiazole derivatives, metal complexes of oxine derivatives, quinolinol-based metal complexes, quinoxaline derivatives, polymers of quinoxaline derivatives, benzazole compounds, gallium complexes, pyrazole derivatives, perfluorinated phenylene derivatives, triazine derivatives, and pyridine derivatives. Examples of the compound include arylazine derivatives, benzoquinoline derivatives (such as 2,2'-bis(benzo[h]quinolin-2-yl)-9,9'-spirobifluorene), imidazopyridine derivatives, borane derivatives, benzimidazole derivatives (such as tris(N-phenylbenzimidazol-2-yl)benzene), benzoxazole derivatives, benzothiazole derivatives, quinoline derivatives, oligopyridine derivatives such as terpyridine, bipyridine derivatives, terpyridine derivatives (such as 1,3-bis(4'-(2,2':6'2"-terpyridinyl))benzene), naphthyridine derivatives (such as bis(1-naphthyl)-4-(1,8-naphthyridin-2-yl)phenylphosphine oxide), aldazine derivatives, carbazole derivatives, indole derivatives, phosphorus oxide derivatives, and bisstyryl derivatives.

Metal complexes having electron-accepting nitrogen can also be used, such as hydroxyazole complexes such as quinolinol metal complexes and hydroxyphenyloxazole complexes, azomethine complexes, tropolone metal complexes, flavonol metal complexes, and benzoquinoline metal complexes.

The above-mentioned materials can be used alone or in combination with different materials.

Among the above-mentioned materials, borane derivatives, pyridine derivatives, fluoranthene derivatives, BO-based derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, carbazole derivatives, triazine derivatives, benzimidazole derivatives, phenanthroline derivatives, and quinolinol-based metal complexes are preferred.

上記式（ＥＴＭ－１）中、Ｒ^１１およびＲ^１２は、それぞれ独立して、水素、アルキル、シクロアルキル、置換されていてもよいアリール、置換されているシリル、置換されていてもよい窒素含有複素環、またはシアノの少なくとも１つであり、Ｒ^１３～Ｒ^１６は、それぞれ独立して、置換されていてもよいアルキル、置換されていてもよいシクロアルキルまたは置換されていてもよいアリールであり、Ｘは、置換されていてもよいアリーレンであり、Ｙは、置換されていてもよい炭素数１６以下のアリール、置換されているボリル、または置換されていてもよいカルバゾリルであり、そして、ｎはそれぞれ独立して０～３の整数である。また、「置換されていてもよい」または「置換されている」場合の置換基としては、アリール、ヘテロアリール、アルキルまたはシクロアルキルなどが挙げられる。 <Borane derivatives>
The borane derivative is, for example, a compound represented by the following general formula (ETM-1), and is disclosed in detail in JP-A-2007-27587.

In the above formula (ETM-1), R ¹¹ and R ¹² are each independently at least one of hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, or cyano, R ¹³ to R ¹⁶ are each independently optionally substituted alkyl, optionally substituted cycloalkyl, or optionally substituted aryl, X is optionally substituted arylene, Y is optionally substituted aryl having 16 or less carbon atoms, substituted boryl, or optionally substituted carbazolyl, and n is each independently an integer of 0 to 3. In addition, examples of the substituent in the case of "optionally substituted" or "substituted" include aryl, heteroaryl, alkyl, and cycloalkyl.

式（ＥＴＭ－１－１）中、Ｒ^１１およびＲ^１２は、それぞれ独立して、水素、アルキル、シクロアルキル、置換されていてもよいアリール、置換されているシリル、置換されていてもよい窒素含有複素環、またはシアノの少なくとも１つであり、Ｒ^１３～Ｒ^１６は、それぞれ独立して、置換されていてもよいアルキル、置換されていてもよいシクロアルキルまたは置換されていてもよいアリールであり、Ｒ^２１およびＲ^２２は、それぞれ独立して、水素、アルキル、シクロアルキル、置換されていてもよいアリール、置換されているシリル、置換されていてもよい窒素含有複素環、またはシアノの少なくとも１つであり、Ｘ^１は、置換されていてもよい炭素数２０以下のアリーレンであり、ｎはそれぞれ独立して０～３の整数であり、そして、ｍはそれぞれ独立して０～４の整数である。また、「置換されていてもよい」または「置換されている」場合の置換基としては、アリール、ヘテロアリール、アルキルまたはシクロアルキルなどが挙げられる。

式（ＥＴＭ－１－２）中、Ｒ^１１およびＲ^１２は、それぞれ独立して、水素、アルキル、シクロアルキル、置換されていてもよいアリール、置換されているシリル、置換されていてもよい窒素含有複素環、またはシアノの少なくとも１つであり、Ｒ^１３～Ｒ^１６は、それぞれ独立して、置換されていてもよいアルキル、置換されていてもよいシクロアルキルまたは置換されていてもよいアリールであり、Ｘ^１は、置換されていてもよい炭素数２０以下のアリーレンであり、そして、ｎはそれぞれ独立して０～３の整数である。また、「置換されていてもよい」または「置換されている」場合の置換基としては、アリール、ヘテロアリール、アルキルまたはシクロアルキルなどが挙げられる。 Among the compounds represented by the above general formula (ETM-1), compounds represented by the following general formula (ETM-1-1) and compounds represented by the following general formula (ETM-1-2) are preferred.

In formula (ETM-1-1), R ¹¹ and R ¹² are each independently at least one of hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, or cyano, R ¹³ to R ¹⁶ are each independently at least one of optionally substituted alkyl, optionally substituted cycloalkyl, or optionally substituted aryl, R ²¹ and R ²² are each independently at least one of hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, or cyano, X ¹ is an optionally substituted arylene having 20 or less carbon atoms, n is each independently an integer of 0 to 3, and m is each independently an integer of 0 to 4. In addition, examples of the substituent in the case of "optionally substituted" or "substituted" include aryl, heteroaryl, alkyl, and cycloalkyl.

In formula (ETM-1-2), R ¹¹ and R ¹² each independently represent at least one of hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, or cyano, R ¹³ to R ¹⁶ each independently represent optionally substituted alkyl, optionally substituted cycloalkyl, or optionally substituted aryl, X ¹ represents an optionally substituted arylene having 20 or less carbon atoms, and each n represents independently an integer of 0 to 3. In addition, examples of the substituent in the case of "optionally substituted" or "substituted" include aryl, heteroaryl, alkyl, and cycloalkyl.

（各式中、Ｒ^ａは、それぞれ独立してアルキル基、シクロアルキル基または置換されていてもよいフェニル基である。） Specific examples of ^X1 include divalent groups represented by any of the following formulae (X-1) to (X-9). In each structural formula, * represents a bonding position.

(In each formula, R ^a is independently an alkyl group, a cycloalkyl group, or an optionally substituted phenyl group.)

Specific examples of the borane derivative include the following compounds:

This borane derivative can be produced using known raw materials and known synthesis methods.

<Pyridine derivatives>
The pyridine derivative is, for example, a compound represented by the following formula (ETM-2), and is preferably a compound represented by formula (ETM-2-1) or (ETM-2-2).

φ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring or triphenylene ring), and n is an integer from 1 to 4.

In the above formula (ETM-2-1), R ¹¹ to R ¹⁸ are each independently hydrogen, alkyl (preferably alkyl having 1 to 24 carbon atoms), cycloalkyl (preferably cycloalkyl having 3 to 12 carbon atoms) or aryl (preferably aryl having 6 to 30 carbon atoms).

In the above formula (ETM-2-2), R ¹¹ and R ¹² are each independently hydrogen, alkyl (preferably alkyl having 1 to 24 carbon atoms), cycloalkyl (preferably cycloalkyl having 3 to 12 carbon atoms) or aryl (preferably aryl having 6 to 30 carbon atoms), and R ¹¹ and R ¹² may be bonded to form a ring.

In each formula, the "pyridine-based substituent" is any one of the following formulae (Py-1) to (Py-15), and each pyridine-based substituent may be independently substituted with an alkyl having 1 to 4 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms. In addition, the pyridine-based substituent may be bonded to the φ, anthracene ring, or fluorene ring in each formula via a phenylene group or naphthylene group. * in each structural formula indicates a bonding position.

The pyridine-based substituent is any one of the above formulae (Py-1) to (Py-15), and among these, any one of the following formulae (Py-21) to (Py-44) is preferable. In each structural formula, * indicates a bonding position.

At least one hydrogen in each pyridine derivative may be replaced with deuterium, and one of the two "pyridine-based substituents" in the above formulas (ETM-2-1) and (ETM-2-2) may be replaced with an aryl.

The "alkyl" in R ¹¹ to R ¹⁸ may be either linear or branched, and examples thereof include linear alkyl having 1 to 24 carbon atoms or branched alkyl having 3 to 24 carbon atoms. A preferred "alkyl" is an alkyl having 1 to 18 carbon atoms (branched alkyl having 3 to 18 carbon atoms). A more preferred "alkyl" is an alkyl having 1 to 12 carbon atoms (branched alkyl having 3 to 12 carbon atoms). An even more preferred "alkyl" is an alkyl having 1 to 6 carbon atoms (branched alkyl having 3 to 6 carbon atoms). An especially preferred "alkyl" is an alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms).

Specific examples of "alkyl" include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl (t-amyl), n-hexyl, 1-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl (1,1,3,3-tetramethylbutyl), 1-methyl Examples of the aryl ether include arylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, and n-eicosyl.
Further, for example, 1-ethyl-1-methylpropyl, 1,1-diethylpropyl, 1,1-dimethylbutyl, 1-ethyl-1-methylbutyl, 1,1,4-trimethylpentyl, 1,1,2-trimethylpropyl, 1,1-dimethyloctyl, 1,1-dimethylpentyl, 1,1-dimethylheptyl, 1,1,5-trimethylhexyl, 1-ethyl-1-methylhexyl, 1-ethyl-1,3-dimethylbutyl, 1,1,2,2-tetramethylpropyl, 1-butyl-1-methylpentyl, 1,1-diethylbutyl, 1-ethyl-1-methylpentyl, 1,1,3-trimethylbutyl, 1-propyl-1-methylpentyl, 1,1,2-trimethylpropyl, 1-ethyl-1,2,2-trimethylpropyl, 1-propyl-1-methylbutyl, and 1,1-dimethylhexyl.

For the alkyl having 1 to 4 carbon atoms to be substituted on the pyridine-based substituent, the above description of alkyl can be cited.

The "cycloalkyl" in R ¹¹ to R ¹⁸ includes, for example, cycloalkyl having 3 to 12 carbon atoms. A preferred "cycloalkyl" is cycloalkyl having 3 to 10 carbon atoms. A more preferred "cycloalkyl" is cycloalkyl having 3 to 8 carbon atoms. An even more preferred "cycloalkyl" is cycloalkyl having 3 to 6 carbon atoms.
Specific examples of "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, and dimethylcyclohexyl.

For the cycloalkyl having 5 to 10 carbon atoms to be substituted on the pyridine-based substituent, the above description of cycloalkyl can be cited.

As the "aryl" in R ¹¹ to R ¹⁸ , the preferred aryl is an aryl having 6 to 30 carbon atoms, the more preferred aryl is an aryl having 6 to 18 carbon atoms, the further more preferred aryl is an aryl having 6 to 14 carbon atoms, and the most preferred aryl is an aryl having 6 to 12 carbon atoms.

Specific examples of "aryls having 6 to 30 carbon atoms" include monocyclic aryls such as phenyl, fused bicyclic aryls such as (1-, 2-)naphthyl, fused tricyclic aryls such as acenaphthylene-(1-, 3-, 4-, 5-)yl, fluorene-(1-, 2-, 3-, 4-, 9-)yl, phenalene-(1-, 2-)yl, and (1-, 2-, 3-, 4-, 9-)phenanthryl, fused tetracyclic aryls such as triphenylene-(1-, 2-)yl, pyrene-(1-, 2-, 4-)yl, and naphthacene-(1-, 2-, 5-)yl, and fused pentacyclic aryls such as perylene-(1-, 2-, 3-)yl and pentacene-(1-, 2-, 5-, 6-)yl.

Preferred "aryl having 6 to 30 carbon atoms" include phenyl, naphthyl, phenanthryl, chrysenyl, or triphenylenyl, more preferably phenyl, 1-naphthyl, 2-naphthyl, or phenanthryl, and particularly preferably phenyl, 1-naphthyl, or 2-naphthyl.

In the above formula (ETM-2-2), R ¹¹ and R ¹² may be bonded to form a ring, and as a result, cyclobutane, cyclopentane, cyclopentene, cyclopentadiene, cyclohexane, fluorene, indene, or the like may be spiro-bonded to the five-membered ring of the fluorene skeleton.

Specific examples of the pyridine derivative include the following compounds:

This pyridine derivative can be produced using known raw materials and known synthesis methods.

<Fluoranthene Derivatives>
The fluoranthene derivative is, for example, a compound represented by the following general formula (ETM-3), and is disclosed in detail in WO 2010/134352.

In the above formula (ETM-3), X ¹² to X ²¹ each represent hydrogen, halogen, linear, branched or cyclic alkyl, linear, branched or cyclic alkoxy, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl. In the case where a group is substituted, examples of the substituent include aryl, heteroaryl, alkyl, and cycloalkyl.

Specific examples of the fluoranthene derivative include the following compounds.

<BO derivatives>
The BO derivative is, for example, a polycyclic aromatic compound represented by the following formula (ETM-4) or a polymer of a polycyclic aromatic compound having a plurality of structures represented by the following formula (ETM-4).

R ¹ to R ¹¹ are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (the two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, or aryloxy, and at least one hydrogen in R ¹ to R ¹¹ may be substituted with an aryl, heteroaryl, alkyl, or cycloalkyl.

Adjacent groups among R ¹ to R ¹¹ may be bonded to each other to form an aryl ring or a heteroaryl ring together with the ring a, ring b, or ring c, and at least one hydrogen atom in the formed ring may be substituted with an aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (the two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, or aryloxy, and at least one hydrogen atom in these substituents may be substituted with an aryl, heteroaryl, alkyl, or cycloalkyl.

Additionally, at least one hydrogen in the compound or structure represented by formula (ETM-4) may be replaced with a halogen or deuterium.

For an explanation of the substituents and ring formation form in formula (ETM-4), as well as the multimer formed by combining multiple structures of formula (ETM-4), the explanations in International Publication No. 2015/102118 and the explanation of the polycyclic aromatic compounds represented by formula (1A) or formula (1B) above may be cited.

Specific examples of the BO derivative include the following compounds.

This BO derivative can be produced using known raw materials and known synthesis methods.

<Anthracene derivatives>
One of the anthracene derivatives is, for example, a compound represented by the following formula (ETM-5-1).

Each Ar is independently a divalent benzene or naphthalene, and each of R ¹ to R ⁴ is independently a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or an aryl group having 6 to 20 carbon atoms.

Each Ar can be independently selected from divalent benzene or naphthalene, and the two Ar may be different or the same, but it is preferable that they are the same from the viewpoint of ease of synthesis of the anthracene derivative. Ar is bonded to pyridine to form a "moiety consisting of Ar and pyridine", and this moiety is bonded to anthracene as a group represented by any one of the following formulas (Py-1) to (Py-12). * in each structural formula indicates a bonding position.

Among these groups, a group represented by any one of the above formulas (Py-1) to (Py-9) is preferred, and a group represented by any one of the above formulas (Py-1) to (Py-6) is more preferred. The two "sites consisting of Ar and pyridine" bonded to anthracene may have the same or different structures, but from the viewpoint of ease of synthesis of anthracene derivatives, it is preferable that they have the same structure. However, from the viewpoint of element characteristics, it is preferable that the structures of the two "sites consisting of Ar and pyridine" are the same or different.

The alkyl having 1 to 6 carbon atoms in R ¹ to R ⁴ may be either linear or branched. That is, it is a linear alkyl having 1 to 6 carbon atoms or a branched alkyl having 3 to 6 carbon atoms. It is more preferably an alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms). Specific examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl (t-amyl), n-hexyl, 1-methylpentyl, 3,3-dimethylbutyl, and 2-ethylbutyl, and methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, or t-butyl is preferred, and methyl, ethyl, or t-butyl is more preferred.

Specific examples of the cycloalkyl having 3 to 6 carbon atoms for R ¹ to R ⁴ include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, and dimethylcyclohexyl.

The aryl having 6 to 20 carbon atoms for R ¹ to R ⁴ is preferably an aryl having 6 to 16 carbon atoms, more preferably an aryl having 6 to 12 carbon atoms, and particularly preferably an aryl having 6 to 10 carbon atoms.

Specific examples of "aryl having 6 to 20 carbon atoms" include monocyclic aryls such as phenyl, (o-, m-, p-) tolyl, (2,3-, 2,4-, 2,5-, 2,6-, 3,4-, 3,5-) xylyl, mesityl (2,4,6-trimethylphenyl), (o-, m-, p-) cumenyl, bicyclic aryls such as (2-, 3-, 4-) biphenylyl, condensed bicyclic aryls such as (1-, 2-) naphthyl, tricyclic aryls such as terphenylyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m ...4'-yl, p-terphenyl-2-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4'-yl, p-terphenyl-2-yl, m-terphenyl-4'-yl, p-terphenyl-2-yl, m-terphenyl-2-yl, m-terphenyl-3-yl aryl, o-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl); fused tricyclic aryls, anthracene-(1-,2-,9-)yl, acenaphthylene-(1-,3-,4-,5-)yl, fluorene-(1-,2-,3-,4-,9-)yl, phenalene-(1-,2-)yl, (1-,2-,3-,4-,9-)phenanthryl; fused tetracyclic aryls, triphenylene-(1-,2-)yl, pyrene-(1-,2-,4-)yl, tetracene-(1-,2-,5-)yl; fused pentacyclic aryls, perylene-(1-,2-,3-)yl, and the like.

Preferred "aryl having 6 to 20 carbon atoms" are phenyl, biphenylyl, terphenylyl, or naphthyl, more preferably phenyl, biphenylyl, 1-naphthyl, 2-naphthyl, or m-terphenyl-5'-yl, even more preferably phenyl, biphenylyl, 1-naphthyl, or 2-naphthyl, and most preferably phenyl.

One of the anthracene derivatives is, for example, a compound represented by the following formula (ETM-5-2).

Each Ar ¹ is independently a single bond, or a divalent benzene, naphthalene, anthracene, fluorene, or phenalene.

Each Ar ² is independently an aryl having 6 to 20 carbon atoms, and the same explanation as for "aryl having 6 to 20 carbon atoms" in the above formula (ETM-5-1) can be cited. An aryl having 6 to 16 carbon atoms is preferable, an aryl having 6 to 12 carbon atoms is more preferable, and an aryl having 6 to 10 carbon atoms is particularly preferable. Specific examples include phenyl, biphenylyl, naphthyl, terphenylyl, anthracenyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, etc.

R ¹ to R ⁴ each independently represent hydrogen, alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, or aryl having 6 to 20 carbon atoms, and the explanation in the above formula (ETM-5-1) can be cited.

Specific examples of these anthracene derivatives include the following compounds.

These anthracene derivatives can be produced using known raw materials and known synthesis methods.

<Benzofluorene derivatives>
The benzofluorene derivative is, for example, a compound represented by the following formula (ETM-6).

Each Ar ¹ is independently an aryl having 6 to 20 carbon atoms, and the same explanation as for "aryl having 6 to 20 carbon atoms" in the above formula (ETM-5-1) can be cited. An aryl having 6 to 16 carbon atoms is preferable, an aryl having 6 to 12 carbon atoms is more preferable, and an aryl having 6 to 10 carbon atoms is particularly preferable. Specific examples include phenyl, biphenylyl, naphthyl, terphenylyl, anthracenyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, etc.

Each Ar ² is independently hydrogen, an alkyl (preferably an alkyl having 1 to 24 carbon atoms), a cycloalkyl (preferably a cycloalkyl having 3 to 12 carbon atoms) or an aryl (preferably an aryl having 6 to 30 carbon atoms), and two Ar ² may be bonded to form a ring.

The "alkyl" in ^Ar2 may be either linear or branched, and examples thereof include linear alkyl having 1 to 24 carbon atoms or branched alkyl having 3 to 24 carbon atoms. A preferred "alkyl" is an alkyl having 1 to 18 carbon atoms (branched alkyl having 3 to 18 carbon atoms). A more preferred "alkyl" is an alkyl having 1 to 12 carbon atoms (branched alkyl having 3 to 12 carbon atoms). An even more preferred "alkyl" is an alkyl having 1 to 6 carbon atoms (branched alkyl having 3 to 6 carbon atoms). An especially preferred "alkyl" is an alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms). Specific examples of "alkyl" include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl (t-amyl), n-hexyl, 1-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, and the like.

The "cycloalkyl" in ^Ar2 includes, for example, cycloalkyl having 3 to 12 carbon atoms. A preferred "cycloalkyl" is cycloalkyl having 3 to 10 carbon atoms. A more preferred "cycloalkyl" is cycloalkyl having 3 to 8 carbon atoms. An even more preferred "cycloalkyl" is cycloalkyl having 3 to 6 carbon atoms. Specific examples of "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, and dimethylcyclohexyl.

As the "aryl" in ^Ar2 , a preferable aryl is an aryl having 6 to 30 carbon atoms, a more preferable aryl is an aryl having 6 to 18 carbon atoms, an even more preferable aryl is an aryl having 6 to 14 carbon atoms, and an especially preferable aryl is an aryl having 6 to 12 carbon atoms.

Specific examples of "aryl having 6 to 30 carbon atoms" include phenyl, naphthyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, naphthacenyl, perylenyl, pentacenyl, etc.

Two ^Ar2 may be bonded to form a ring, and as a result, cyclobutane, cyclopentane, cyclopentene, cyclopentadiene, cyclohexane, fluorene, indene, or the like may be spiro-bonded to the five-membered ring of the fluorene skeleton.

Specific examples of the benzofluorene derivative include the following compounds.

This benzofluorene derivative can be produced using known raw materials and known synthesis methods.

Ｒ^５は、置換または無置換の、炭素数１～２０のアルキル、炭素数３～２０のシクロアルキル、炭素数６～２０のアリールまたは炭素数５～２０のヘテロアリールであり、
Ｒ^６は、ＣＮ、置換または無置換の、炭素数１～２０のアルキル、炭素数３～２０のシクロアルキル、炭素数１～２０のヘテロアルキル、炭素数６～２０のアリール、炭素数５～２０のヘテロアリール、炭素数１～２０のアルコキシまたは炭素数６～２０のアリールオキシであり、
Ｒ^７およびＲ^８は、それぞれ独立して、置換または無置換の、炭素数６～２０のアリールまたは炭素数５～２０のヘテロアリールであり、
Ｒ^９は酸素または硫黄であり、
ｊは０または１であり、ｋは０または１であり、ｒは０～４の整数であり、ｑは１～３の整数である。
ここで、置換されている場合の置換基としては、アリール、ヘテロアリール、アルキルまたはシクロアルキルなどが挙げられる。 <Phosphine oxide derivatives>
The phosphine oxide derivative is, for example, a compound represented by the following formula (ETM-7-1). Details are also described in WO 2013/079217.

^R5 is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 5 to 20 carbon atoms;
R ⁶ is CN, a substituted or unsubstituted alkyl having 1 to 20 carbon atoms, a cycloalkyl having 3 to 20 carbon atoms, a heteroalkyl having 1 to 20 carbon atoms, an aryl having 6 to 20 carbon atoms, a heteroaryl having 5 to 20 carbon atoms, an alkoxy having 1 to 20 carbon atoms, or an aryloxy having 6 to 20 carbon atoms;
R ⁷ and R ⁸ are each independently a substituted or unsubstituted aryl having 6 to 20 carbon atoms or a heteroaryl having 5 to 20 carbon atoms;
^R9 is oxygen or sulfur;
j is 0 or 1, k is 0 or 1, r is an integer of 0 to 4, and q is an integer of 1 to 3.
When substituted, the substituent may be an aryl, heteroaryl, alkyl, or cycloalkyl.

The phosphine oxide derivative may be, for example, a compound represented by the following formula (ETM-7-2).

R ¹ to R ³ may be the same or different and are selected from hydrogen, an alkyl group, a cycloalkyl group, an aralkyl group, an alkenyl group, a cycloalkenyl group, an alkynyl group, an alkoxy group, an alkylthio group, a cycloalkylthio group, an aryl ether group, an aryl thioether group, an aryl group, a heterocyclic group, a halogen, a cyano group, an aldehyde group, a carbonyl group, a carboxyl group, an amino group, a nitro group, a silyl group, and a condensed ring formed between adjacent substituents.

Ar ¹ may be the same or different and is an arylene group or a heteroarylene group. Ar ² may be the same or different and is an aryl group or a heteroaryl group. However, at least one of Ar ¹ and Ar ² has a substituent or forms a condensed ring with the adjacent substituent. n is an integer of 0 to 3, when n is 0, there is no unsaturated structural portion, and when n is 3, R ¹ does not exist.

Of these substituents, the alkyl group refers to a saturated aliphatic hydrocarbon group such as a methyl group, an ethyl group, a propyl group, or a butyl group, which may be unsubstituted or substituted. If the group is substituted, there is no particular limit to the type of substituent, and examples of the substituent include an alkyl group, an aryl group, and a heterocyclic group, which is also the case in the following descriptions. The number of carbon atoms in the alkyl group is not particularly limited, but is usually in the range of 1 to 20 from the standpoint of availability and cost.

A cycloalkyl group refers to a saturated alicyclic hydrocarbon group such as cyclopropyl, cyclohexyl, norbornyl, or adamantyl, which may be unsubstituted or substituted. The number of carbon atoms in the alkyl group is not particularly limited, but is usually in the range of 3 to 20.

The term "aralkyl group" refers to an aromatic hydrocarbon group linked via an aliphatic hydrocarbon, such as a benzyl group or a phenylethyl group, and both the aliphatic and aromatic hydrocarbons may be unsubstituted or substituted. The number of carbon atoms in the aliphatic portion is not particularly limited, but is usually in the range of 1 to 20.

Alkenyl groups refer to unsaturated aliphatic hydrocarbon groups containing a double bond, such as vinyl groups, allyl groups, and butadienyl groups, which may be unsubstituted or substituted. The number of carbon atoms in an alkenyl group is not particularly limited, but is usually in the range of 2 to 20.

Furthermore, a cycloalkenyl group refers to an unsaturated alicyclic hydrocarbon group containing a double bond, such as a cyclopentenyl group, a cyclopentadienyl group, or a cyclohexene group, which may be unsubstituted or substituted.

Alkynyl groups refer to unsaturated aliphatic hydrocarbon groups containing a triple bond, such as acetylenyl groups, which may be unsubstituted or substituted. The number of carbon atoms in an alkynyl group is not particularly limited, but is usually in the range of 2 to 20.

Alkoxy groups refer to aliphatic hydrocarbon groups, such as methoxy groups, which are linked via an ether bond, and the aliphatic hydrocarbon groups may be unsubstituted or substituted. The number of carbon atoms in the alkoxy group is not particularly limited, but is usually in the range of 1 to 20.

An alkylthio group is a group in which the oxygen atom of the ether bond of an alkoxy group is replaced with a sulfur atom.

A cycloalkylthio group is a group in which the oxygen atom of the ether bond of a cycloalkoxy group is replaced with a sulfur atom.

The aryl ether group refers to an aromatic hydrocarbon group, such as a phenoxy group, that is linked via an ether bond, and the aromatic hydrocarbon group may be unsubstituted or substituted. The number of carbon atoms in the aryl ether group is not particularly limited, but is usually in the range of 6 to 40.

An aryl thioether group is a group in which the oxygen atom of the ether bond of an aryl ether group is replaced with a sulfur atom.

An aryl group refers to an aromatic hydrocarbon group such as a phenyl group, a naphthyl group, a biphenyl group, a phenanthryl group, a terphenyl group, or a pyrenyl group. The aryl group may be unsubstituted or substituted. The number of carbon atoms in the aryl group is not particularly limited, but is usually in the range of 6 to 40.

The heterocyclic group refers to a cyclic structural group having atoms other than carbon, such as a furanyl group, a thiophenyl group, an oxazolyl group, a pyridyl group, a quinolinyl group, or a carbazolyl group, which may be unsubstituted or substituted. The number of carbon atoms in the heterocyclic group is not particularly limited, but is usually in the range of 2 to 30.

Halogen refers to fluorine, chlorine, bromine, and iodine.

The aldehyde group, carbonyl group, and amino group may also include groups substituted with aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons, heterocycles, etc.

In addition, the aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons, and heterocycles may be unsubstituted or substituted.

The silyl group refers to a silicon compound group such as a trimethylsilyl group, which may be unsubstituted or substituted. The number of carbon atoms in the silyl group is not particularly limited, but is usually in the range of 3 to 20. The number of silicon atoms is usually 1 to 6.

The fused ring formed between adjacent substituents is, for example, a conjugated or non-conjugated fused ring formed between Ar ¹ and R ² , Ar ¹ and R ³ , Ar ² and R ² , Ar ² and R ³ , R ² and R ³ , Ar ¹ and Ar ^2, etc. Here, when n is 1, two R ^1s may form a conjugated or non-conjugated fused ring. These fused rings may contain a nitrogen, oxygen, or sulfur atom in the ring structure, or may be fused with another ring.

Specific examples of the phosphine oxide derivative include the following compounds:

This phosphine oxide derivative can be produced using known raw materials and known synthesis methods.

<Pyrimidine derivatives>
The pyrimidine derivative is, for example, a compound represented by the following formula (ETM-8), preferably a compound represented by the following formula (ETM-8-1). Details are also described in WO 2011/021689.

Each Ar is independently an optionally substituted aryl or an optionally substituted heteroaryl. n is an integer from 1 to 4, preferably an integer from 1 to 3, and more preferably 2 or 3.

The "aryl" in "optionally substituted aryl" includes, for example, aryl having 6 to 30 carbon atoms, preferably aryl having 6 to 24 carbon atoms, more preferably aryl having 6 to 20 carbon atoms, and even more preferably aryl having 6 to 12 carbon atoms.

Specific examples of "aryl" include monocyclic aryl phenyl, bicyclic aryl (2-, 3-, 4-) biphenylyl, condensed bicyclic aryl (1-, 2-) naphthyl, tricyclic aryl terphenylyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), condensed tricyclic aryl Examples of the aryl include acenaphthylene-(1-,3-,4-,5-)yl, fluorene-(1-,2-,3-,4-,9-)yl, phenalene-(1-,2-)yl, and (1-,2-,3-,4-,9-)phenanthryl; the tetracyclic aryl is quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, and m-quaterphenylyl); the condensed tetracyclic aryl is triphenylene-(1-,2-)yl, pyrene-(1-,2-,4-)yl, and naphthacene-(1-,2-,5-)yl; and the condensed pentacyclic aryl is perylene-(1-,2-,3-)yl and pentacene-(1-,2-,5-,6-)yl.

Examples of the "heteroaryl" in "optionally substituted heteroaryl" include heteroaryls having 2 to 30 carbon atoms, preferably heteroaryls having 2 to 25 carbon atoms, more preferably heteroaryls having 2 to 20 carbon atoms, even more preferably heteroaryls having 2 to 15 carbon atoms, and particularly preferably heteroaryls having 2 to 10 carbon atoms. Examples of heteroaryls include heterocycles containing, in addition to carbon, 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen as ring-constituting atoms.

Specific examples of heteroaryl include pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, Examples of such alkyl groups include acridinyl, phenoxathiinyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenazasilinyl, indolizinyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, naphthobenzofuranyl, thiophenyl, benzothiophenyl, dibenzothiophenyl, naphthobenzothiophenyl, benzophosphoryl, dibenzophosphoryl, a monovalent group of a benzophosphole oxide ring, a monovalent group of a dibenzophosphole oxide ring, furazanyl, thianthrenyl, indolocarbazolyl, benzoindolocarbazolyl, and benzobenzoindolocarbazolyl.

In addition, at least one hydrogen atom in the above aryl and heteroaryl may be substituted, for example, by the above aryl or heteroaryl.

Specific examples of the pyrimidine derivative include the following compounds:

This pyrimidine derivative can be produced using known raw materials and known synthesis methods.

<Carbazole derivatives>
The carbazole derivative is, for example, a compound represented by the following formula (ETM-9), or a multimer in which a plurality of such compounds are bonded together via single bonds, etc. Details are described in U.S. Patent Publication No. 2014/0197386.

Each Ar is independently an optionally substituted aryl or an optionally substituted heteroaryl. Each n is independently an integer from 0 to 4, preferably an integer from 0 to 3, and more preferably 0 or 1.

The "aryl" in "optionally substituted aryl" includes, for example, aryl having 6 to 30 carbon atoms, preferably aryl having 6 to 24 carbon atoms, more preferably aryl having 6 to 20 carbon atoms, and even more preferably aryl having 6 to 12 carbon atoms.

Specific examples of "aryl" include monocyclic aryl phenyl, bicyclic aryl (2-, 3-, 4-) biphenylyl, condensed bicyclic aryl (1-, 2-) naphthyl, tricyclic aryl terphenylyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), condensed tricyclic aryl Examples of the aryl include acenaphthylene-(1-,3-,4-,5-)yl, fluorene-(1-,2-,3-,4-,9-)yl, phenalene-(1-,2-)yl, and (1-,2-,3-,4-,9-)phenanthryl; the tetracyclic aryl is quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, and m-quaterphenylyl); the condensed tetracyclic aryl is triphenylene-(1-,2-)yl, pyrene-(1-,2-,4-)yl, and naphthacene-(1-,2-,5-)yl; and the condensed pentacyclic aryl is perylene-(1-,2-,3-)yl and pentacene-(1-,2-,5-,6-)yl.

Examples of the "heteroaryl" in "optionally substituted heteroaryl" include heteroaryls having 2 to 30 carbon atoms, preferably heteroaryls having 2 to 25 carbon atoms, more preferably heteroaryls having 2 to 20 carbon atoms, even more preferably heteroaryls having 2 to 15 carbon atoms, and particularly preferably heteroaryls having 2 to 10 carbon atoms. Examples of heteroaryls include heterocycles containing, in addition to carbon, 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen as ring-constituting atoms.

Specific examples of heteroaryl include pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, Examples of such alkyl groups include acridinyl, phenoxathiinyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenazasilinyl, indolizinyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, naphthobenzofuranyl, thiophenyl, benzothiophenyl, dibenzothiophenyl, naphthobenzothiophenyl, benzophosphoryl, dibenzophosphoryl, a monovalent group of a benzophosphole oxide ring, a monovalent group of a dibenzophosphole oxide ring, furazanyl, thianthrenyl, indolocarbazolyl, benzoindolocarbazolyl, and benzobenzoindolocarbazolyl.

In addition, at least one hydrogen atom in the above aryl and heteroaryl may be substituted, for example, by the above aryl or heteroaryl.

The carbazole derivative may be a polymer in which a plurality of compounds represented by the above formula (ETM-9) are bonded together by single bonds or the like. In this case, in addition to single bonds, they may be bonded together by aryl rings (preferably polyvalent benzene rings, naphthalene rings, anthracene rings, fluorene rings, benzofluorene rings, phenalene rings, phenanthrene rings, or triphenylene rings).

Specific examples of the carbazole derivative include the following compounds.

This carbazole derivative can be produced using known raw materials and known synthesis methods.

<Triazine derivatives>
The triazine derivative is, for example, a compound represented by the following formula (ETM-10), preferably a compound represented by the following formula (ETM-10-1), the details of which are described in U.S. Patent Publication No. 2011/0156013.

Each Ar is independently an optionally substituted aryl or an optionally substituted heteroaryl. n is an integer from 1 to 3, preferably 2 or 3.

The "aryl" in "optionally substituted aryl" includes, for example, aryl having 6 to 30 carbon atoms, preferably aryl having 6 to 24 carbon atoms, more preferably aryl having 6 to 20 carbon atoms, and even more preferably aryl having 6 to 12 carbon atoms.

Specific examples of "aryl" include monocyclic aryl phenyl, bicyclic aryl (2-, 3-, 4-) biphenylyl, condensed bicyclic aryl (1-, 2-) naphthyl, tricyclic aryl terphenylyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), condensed tricyclic aryl Examples of the aryl include acenaphthylene-(1-,3-,4-,5-)yl, fluorene-(1-,2-,3-,4-,9-)yl, phenalene-(1-,2-)yl, and (1-,2-,3-,4-,9-)phenanthryl; the tetracyclic aryl is quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, and m-quaterphenylyl); the condensed tetracyclic aryl is triphenylene-(1-,2-)yl, pyrene-(1-,2-,4-)yl, and naphthacene-(1-,2-,5-)yl; and the condensed pentacyclic aryl is perylene-(1-,2-,3-)yl and pentacene-(1-,2-,5-,6-)yl.

Examples of the "heteroaryl" in "optionally substituted heteroaryl" include heteroaryls having 2 to 30 carbon atoms, preferably heteroaryls having 2 to 25 carbon atoms, more preferably heteroaryls having 2 to 20 carbon atoms, even more preferably heteroaryls having 2 to 15 carbon atoms, and particularly preferably heteroaryls having 2 to 10 carbon atoms. Examples of heteroaryls include heterocycles containing, in addition to carbon, 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen as ring-constituting atoms.

Specific examples of heteroaryl include pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, Examples of such alkyl groups include acridinyl, phenoxathiinyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenazasilinyl, indolizinyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, naphthobenzofuranyl, thiophenyl, benzothiophenyl, dibenzothiophenyl, naphthobenzothiophenyl, benzophosphoryl, dibenzophosphoryl, a monovalent group of a benzophosphole oxide ring, a monovalent group of a dibenzophosphole oxide ring, furazanyl, thianthrenyl, indolocarbazolyl, benzoindolocarbazolyl, and benzobenzoindolocarbazolyl.

In addition, at least one hydrogen atom in the above aryl and heteroaryl may be substituted, for example, by the above aryl or heteroaryl.

Specific examples of the triazine derivative include the following compounds:

This triazine derivative can be produced using known raw materials and known synthesis methods.

<Benzimidazole Derivatives>
The benzimidazole derivative is, for example, a compound represented by the following formula (ETM-11).

φ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring or triphenylene ring), n is an integer from 1 to 4, and the "benzoimidazole-based substituent" is a substituent in which the pyridyl group in the "pyridine-based substituent" in the above formulas (ETM-2), (ETM-2-1) and (ETM-2-2) is replaced with a benzimidazole group, and at least one hydrogen in the benzimidazole derivative may be replaced with deuterium. * in the following structural formula indicates a bonding position.

R ¹¹ in the benzimidazole group is hydrogen, alkyl having 1 to 24 carbon atoms, cycloalkyl having 3 to 12 carbon atoms, or aryl having 6 to 30 carbon atoms, and the explanation of R ¹¹ in the above formulae (ETM-2-1) and (ETM-2-2) can be cited.

It is further preferred that φ is an anthracene ring or a fluorene ring, and in this case, the structure can be as described in the above formula (ETM-2-1) or formula (ETM-2-2), and R ¹¹ to R ¹⁸ in each formula can be as described in the above formula (ETM-2-1) or formula (ETM-2-2). In addition, in the above formula (ETM-2-1) or formula (ETM-2-2), two pyridine-based substituents are described as being bonded together, but when these are replaced with benzimidazole-based substituents, both pyridine-based substituents may be replaced with benzimidazole-based substituents (i.e., n=2), or one of the pyridine-based substituents may be replaced with a benzimidazole-based substituent and the other pyridine-based substituent may be replaced with R ¹¹ to R ¹⁸ (i.e., n=1). Furthermore, for example, at least one of R ¹¹ to R ¹⁸ in the above formula (ETM-2-1) may be replaced with a benzimidazole-based substituent, and the "pyridine-based substituent" may be replaced with R ¹¹ to R ¹⁸ .

Specific examples of the benzimidazole derivative include 1-phenyl-2-(4-(10-phenylanthracen-9-yl)phenyl)-1H-benzo[d]imidazole, 2-(4-(10-(naphthalen-2-yl)anthracen-9-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole, 2-(3-(10-(naphthalen-2-yl)anthracen-9-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole, and 5-(10-(naphthalen-2-yl)anthracen-9-yl)-1,2-diphenyl-1H-benzo[d]imidazole. , 1-(4-(10-(naphthalene-2-yl)anthracen-9-yl)phenyl)-2-phenyl-1H-benzo[d]imidazole, 2-(4-(9,10-di(naphthalene-2-yl)anthracen-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole, 1-(4-(9,10-di(naphthalene-2-yl)anthracen-2-yl)phenyl)-2-phenyl-1H-benzo[d]imidazole, 5-(9,10-di(naphthalene-2-yl)anthracen-2-yl)-1,2-diphenyl-1H-benzo[d]imidazole, and the like.

This benzimidazole derivative can be produced using known raw materials and known synthesis methods.

<Phenanthroline derivatives>
The phenanthroline derivative is, for example, a compound represented by the following formula (ETM-12) or formula (ETM-12-1), the details of which are described in WO 2006/021982.

φ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring or triphenylene ring), and n is an integer from 1 to 4.

R ¹¹ to R ¹⁸ in each formula are each independently hydrogen, alkyl (preferably alkyl having 1 to 24 carbon atoms), cycloalkyl (preferably cycloalkyl having 3 to 12 carbon atoms), or aryl (preferably aryl having 6 to 30 carbon atoms). In addition, in the above formula (ETM-12-1), any of R ¹¹ to R ¹⁸ is bonded to φ which is an aryl ring.

At least one hydrogen in each phenanthroline derivative may be replaced with deuterium.

The alkyl, cycloalkyl and aryl in R ¹¹ to R ¹⁸ can be the same as those described for R ¹¹ to R ¹⁸ in formula (ETM-2). In addition to the above examples, φ can have the following structural formulae. Each R in the structural formulae is independently hydrogen, methyl, ethyl, isopropyl, cyclohexyl, phenyl, 1-naphthyl, 2-naphthyl, biphenylyl or terphenylyl. In each structural formula, * indicates a bond position.

Specific examples of the phenanthroline derivative include 4,7-diphenyl-1,10-phenanthroline, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline, 9,10-di(1,10-phenanthroline-2-yl)anthracene, 2,6-di(1,10-phenanthroline-5-yl)pyridine, 1,3,5-tri(1,10-phenanthroline-5-yl)benzene, 9,9'-difluoro-bi(1,10-phenanthroline-5-yl), bathocuproine, 1,3-bis(2-phenyl-1,10-phenanthroline-9-yl)benzene, and compounds represented by the following structural formula:

This phenanthroline derivative can be produced using known raw materials and known synthesis methods.

式中、Ｒ^１～Ｒ^６は、それぞれ独立して、水素、フッ素、アルキル、シクロアルキル、アラルキル、アルケニル、シアノ、アルコキシまたはアリールであり、ＭはＬｉ、Ａｌ、Ｇａ、ＢｅまたはＺｎであり、ｎは１～３の整数である。 <Quinolinol metal complexes>
The quinolinol metal complex is, for example, a compound represented by the following general formula (ETM-13).

In the formula, R ¹ to R ⁶ are each independently hydrogen, fluorine, alkyl, cycloalkyl, aralkyl, alkenyl, cyano, alkoxy or aryl; M is Li, Al, Ga, Be or Zn; and n is an integer of 1 to 3.

Specific examples of quinolinol-based metal complexes include 8-quinolinol lithium, tris(8-quinolinolato)aluminum, tris(4-methyl-8-quinolinolato)aluminum, tris(5-methyl-8-quinolinolato)aluminum, tris(3,4-dimethyl-8-quinolinolato)aluminum, tris(4,5-dimethyl-8-quinolinolato)aluminum, tris(4,6-dimethyl-8-quinolinolato)aluminum, and bis( 2-methyl-8-quinolinolate)(phenolate)aluminum, bis(2-methyl-8-quinolinolate)(2-methylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(3-methylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(4-methylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(2-phenylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(phenolate)aluminum linolinate)(3-phenylphenolate)aluminum, bis(2-methyl-8-quinolinate)(4-phenylphenolate)aluminum, bis(2-methyl-8-quinolinate)(2,3-dimethylphenolate)aluminum, bis(2-methyl-8-quinolinate)(2,6-dimethylphenolate)aluminum, bis(2-methyl-8-quinolinate)(3,4-dimethylphenolate)aluminum, bis(2-methyl bis(2-methyl-8-quinolinolate)(3,5-dimethylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(3,5-di-t-butylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(2,6-diphenylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(2,4,6-triphenylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(2,4,6-trimethylphenolate)aluminum bis(2-methyl-8-quinolinolate)(2,4,5,6-tetramethylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(1-naphtholate)aluminum, bis(2-methyl-8-quinolinolate)(2-naphtholate)aluminum, bis(2,4-dimethyl-8-quinolinolate)(2-phenylphenolate)aluminum, bis(2,4-dimethyl-8-quinolinolate)(3-phenylphenolate)aluminum bis(2,4-dimethyl-8-quinolinolate)(4-phenylphenolate)aluminum, bis(2,4-dimethyl-8-quinolinolate)(3,5-dimethylphenolate)aluminum, bis(2,4-dimethyl-8-quinolinolate)(3,5-di-t-butylphenolate)aluminum, bis(2-methyl-8-quinolinolate)aluminum-μ-oxo-bis(2-methyl-8-quinolinolate)aluminum quinolinolate)aluminum, bis(2,4-dimethyl-8-quinolinolate)aluminum-μ-oxo-bis(2,4-dimethyl-8-quinolinolate)aluminum, bis(2-methyl-4-ethyl-8-quinolinolate)aluminum-μ-oxo-bis(2-methyl-4-ethyl-8-quinolinolate)aluminum, bis(2-methyl-4-methoxy-8-quinolinolate)aluminum-μ-oxo-bis(2-methyl-4-methoxy-8-quinolinolate)aluminum quinolinolate)aluminum, bis(2-methyl-5-cyano-8-quinolinolate)aluminum-μ-oxo-bis(2-methyl-5-cyano-8-quinolinolate)aluminum, bis(2-methyl-5-trifluoromethyl-8-quinolinolate)aluminum-μ-oxo-bis(2-methyl-5-trifluoromethyl-8-quinolinolate)aluminum, and bis(10-hydroxybenzo[h]quinoline)beryllium.

This quinolinol metal complex can be produced using known raw materials and known synthesis methods.

ベンゾチアゾール誘導体は、例えば下記式（ＥＴＭ－１４－２）で表される化合物である。

<Thiazole Derivatives and Benzothiazole Derivatives>
The thiazole derivative is, for example, a compound represented by the following formula (ETM-14-1).

The benzothiazole derivative is, for example, a compound represented by the following formula (ETM-14-2).

In each formula, φ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring or triphenylene ring), and n is an integer from 1 to 4. The "thiazole-based substituent" and "benzothiazole-based substituent" are substituents in which the pyridyl group in the "pyridine-based substituent" in the above formulae (ETM-2), (ETM-2-1) and (ETM-2-2) is replaced with the below-mentioned thiazole group or benzothiazole group, and at least one hydrogen atom in the thiazole derivative and benzothiazole derivative may be replaced with a deuterium atom. * in the following structural formulas indicates a bond position.

It is further preferred that φ is an anthracene ring or a fluorene ring, and in this case, the structure can be explained with reference to the above formula (ETM-2-1) or formula (ETM-2-2), and R ¹¹ to R ¹⁸ in each formula can be explained with reference to the above formula (ETM-2-1) or formula (ETM-2-2). In addition, in the above formula (ETM-2-1) or formula (ETM-2-2), two pyridine-based substituents are explained as being bonded together, but when these are replaced with a thiazole-based substituent (or a benzothiazole-based substituent), both pyridine-based substituents may be replaced with a thiazole-based substituent (or a benzothiazole-based substituent) (i.e., n=2), or one of the pyridine-based substituents may be replaced with a thiazole-based substituent (or a benzothiazole-based substituent) and the other pyridine-based substituent may be replaced with R ¹¹ to R ¹⁸ (i.e., n=1). Furthermore, for example, at least one of R ¹¹ to R ¹⁸ in the above formula (ETM-2-1) may be replaced with a thiazole-based substituent (or a benzothiazole-based substituent) to replace the "pyridine-based substituent" with R ¹¹ to R ¹⁸ .

These thiazole or benzothiazole derivatives can be produced using known raw materials and known synthesis methods.

The electron transport layer or the electron injection layer may further contain a substance capable of reducing the material forming the electron transport layer or the electron injection layer. As the reducing substance, various substances can be used as long as they have a certain degree of reducing ability. For example, at least one selected from the group consisting of alkali metals, alkaline earth metals, rare earth metals, oxides of alkali metals, halides of alkali metals, oxides of alkaline earth metals, halides of alkaline earth metals, oxides of rare earth metals, halides of rare earth metals, organic complexes of alkali metals, organic complexes of alkaline earth metals, and organic complexes of rare earth metals can be preferably used.

Preferred reducing substances include alkali metals such as Na (work function 2.36 eV), K (2.28 eV), Rb (2.16 eV), or Cs (1.95 eV), and alkaline earth metals such as Ca (2.9 eV), Sr (2.0-2.5 eV), or Ba (2.52 eV), with substances with a work function of 2.9 eV or less being particularly preferred. Of these, more preferred reducing substances are alkali metals such as K, Rb, or Cs, more preferably Rb or Cs, and most preferably Cs. These alkali metals have particularly high reducing ability, and by adding a relatively small amount to the material forming the electron transport layer or electron injection layer, the luminance of the organic EL element can be improved and the lifespan can be extended. Furthermore, as a reducing substance having a work function of 2.9 eV or less, a combination of two or more of these alkali metals is also preferred, and in particular, a combination containing Cs is preferred, for example, a combination of Cs and Na, Cs and K, Cs and Rb, or a combination of Cs, Na and K. By containing Cs, the reducing ability can be efficiently exhibited, and by adding it to a material forming an electron transport layer or an electron injection layer, the luminance of the organic EL element can be improved and the life can be extended.

The above-mentioned electron injection layer material and electron transport layer material can be used as an electron layer material in the form of a polymer compound obtained by polymerizing a reactive compound substituted with a reactive substituent as a monomer, or a crosslinked polymer thereof, or a pendant polymer compound obtained by reacting a main chain polymer with the reactive compound, or a crosslinked pendant polymer thereof. In this case, the reactive substituent can be quoted from the description of the polycyclic aromatic compound represented by formula (1A) or formula (1B).
The applications of such polymer compounds and crosslinked polymers will be described in detail below.

<Cathode in Organic Electroluminescent Device>
The cathode 108 serves to inject electrons into the light-emitting layer 105 via the electron injection layer 107 and the electron transport layer 106 .

The material for forming the cathode 108 is not particularly limited as long as it can efficiently inject electrons into the organic layer, but the same material as the material for forming the anode 102 can be used. Among them, metals such as tin, indium, calcium, aluminum, silver, copper, nickel, chromium, gold, platinum, iron, zinc, lithium, sodium, potassium, cesium, and magnesium, or alloys thereof (magnesium-silver alloy, magnesium-indium alloy, aluminum-lithium alloy such as lithium fluoride/aluminum, etc.), etc. are preferred. In order to increase the electron injection efficiency and improve the device characteristics, lithium, sodium, potassium, cesium, calcium, magnesium, or alloys containing these low work function metals are effective. However, these low work function metals are generally unstable in the air. To improve this point, for example, a method is known in which a trace amount of lithium, cesium, or magnesium is doped into the organic layer to use a highly stable electrode. Other dopants that can be used include inorganic salts such as lithium fluoride, cesium fluoride, lithium oxide, and cesium oxide. However, they are not limited to these.

In addition, preferred examples of electrode protection include lamination of metals such as platinum, gold, silver, copper, iron, tin, aluminum, and indium, or alloys using these metals, as well as inorganic materials such as silica, titania, and silicon nitride, polyvinyl alcohol, vinyl chloride, and hydrocarbon polymer compounds. There are no particular limitations on the method of producing these electrodes, and they can be produced by resistance heating, electron beam deposition, sputtering, ion plating, coating, and other methods as long as they can provide electrical conductivity.

<Binder that may be used in each layer>
The materials used for the hole injection layer, hole transport layer, light emitting layer, electron transport layer and electron injection layer can form each layer alone, but they can also be used as a polymer binder by being dispersed in a solvent-soluble resin such as polyvinyl chloride, polycarbonate, polystyrene, poly(N-vinylcarbazole), polymethyl methacrylate, polybutyl methacrylate, polyester, polysulfone, polyphenylene oxide, polybutadiene, hydrocarbon resin, ketone resin, phenoxy resin, polyamide, ethyl cellulose, vinyl acetate resin, ABS resin, polyurethane resin, or a curable resin such as phenol resin, xylene resin, petroleum resin, urea resin, melamine resin, unsaturated polyester resin, alkyd resin, epoxy resin, silicone resin, or the like.

<Method for Producing Organic Electroluminescent Device>
Each layer constituting an organic EL element can be formed by forming the material to be formed into a thin film by a method such as vapor deposition, resistance heating vapor deposition, electron beam vapor deposition, sputtering, molecular lamination, printing, spin coating or casting, coating, etc. The thickness of each layer thus formed is not particularly limited and can be set appropriately according to the properties of the material, but is usually in the range of 2 nm to 5000 nm. The thickness can usually be measured with a quartz crystal oscillation type film thickness measuring device, etc. When forming a thin film by vapor deposition, the vapor deposition conditions vary depending on the type of material, the intended crystal structure and association structure of the film, etc. The vapor deposition conditions are generally preferably set appropriately in the range of boat heating temperature +50 to +400°C, vacuum degree 10 ^-6 to 10 ^-3 Pa, vapor deposition rate 0.01 to 50 nm/sec, substrate temperature -150 to +300°C, and film thickness 2 nm to 5 μm.

When applying a DC voltage to the organic EL element obtained in this way, the anode should be set to + and the cathode to -. When a voltage of about 2 to 40 V is applied, light emission can be observed from the transparent or semi-transparent electrode side (anode or cathode, or both). This organic EL element also emits light when a pulsed current or AC current is applied. The waveform of the applied AC current can be any waveform.

Next, as an example of a method for producing an organic EL element, we will explain a method for producing an organic EL element consisting of an anode, a hole injection layer, a hole transport layer, an emitting layer made of a host material and a dopant material, an electron transport layer, an electron injection layer, and a cathode.

<Vapor deposition method>
A thin film of an anode material is formed on a suitable substrate by vapor deposition or the like to prepare an anode, and then a thin film of a hole injection layer and a hole transport layer is formed on the anode. A host material and a dopant material are co-deposited on the anode to form a thin film as a light-emitting layer, an electron transport layer and an electron injection layer are formed on the light-emitting layer, and a thin film of a cathode material is further formed by vapor deposition or the like to prepare a cathode, thereby obtaining a desired organic EL element. Note that in the preparation of the above-mentioned organic EL element, the order of preparation can be reversed, and the elements can be prepared in the order of cathode, electron injection layer, electron transport layer, light-emitting layer, hole transport layer, hole injection layer, and anode.

<Wet film formation method>
The wet film formation method is carried out by preparing a low molecular weight compound capable of forming each organic layer of an organic EL element as a liquid composition for forming an organic layer, and using this. If there is no suitable organic solvent for dissolving this low molecular weight compound, the composition for forming an organic layer may be prepared from a polymer compound polymerized together with other monomers having a solubility function as a reactive compound in which the low molecular weight compound is substituted with a reactive substituent, or a main chain polymer.

In the wet film formation method, a coating film is generally formed through a coating process in which an organic layer forming composition is applied to a substrate and a drying process in which the solvent is removed from the applied organic layer forming composition. When the polymer compound has a crosslinkable substituent (also called a crosslinkable polymer compound), the polymer is further crosslinked by the drying process to form a crosslinked polymer. Depending on the difference in the coating process, the method using a spin coater is called the spin coat method, the method using a slit coater is called the slit coat method, the method using a plate is called the gravure, offset, reverse offset, or flexographic printing method, the method using an inkjet printer is called the inkjet method, and the method spraying in a mist form is called the spray method. The drying process includes air drying, heating, and drying under reduced pressure. The drying process may be performed only once, or may be performed multiple times using different methods and conditions. In addition, different methods may be used in combination, such as baking under reduced pressure.

A wet film formation method is a film formation method that uses a solution, and examples of this include some printing methods (inkjet methods), spin coating methods or casting methods, and coating methods. Unlike vacuum deposition methods, wet film formation does not require expensive vacuum deposition equipment, and films can be formed under atmospheric pressure. In addition, wet film formation allows for large area production and continuous production, which leads to reduced manufacturing costs.

On the other hand, compared to vacuum deposition, wet deposition methods can be difficult to use for layering. When using wet deposition methods to create layered films, it is necessary to prevent the lower layer from being dissolved by the composition of the upper layer, and so compositions with controlled solubility, crosslinking of the lower layer, and orthogonal solvents (solvents that are not mutually soluble) are used. However, even with these techniques, it can be difficult to use wet deposition methods to apply all films.

Therefore, a method is generally adopted for producing organic EL elements in which only a few layers are formed using wet film formation methods and the rest are formed using vacuum deposition methods.

For example, the procedure for producing an organic EL element by partially applying a wet film formation method will be described below.
(Step 1) Formation of an anode by vacuum deposition (Step 2) Formation of a hole injection layer-forming composition containing a hole injection layer material by wet deposition (Step 3) Formation of a hole transport layer-forming composition containing a hole transport layer material by wet deposition (Step 4) Formation of an emitting layer-forming composition containing a host material and a dopant material by wet deposition (Step 5) Formation of an electron transport layer by vacuum deposition (Step 6) Formation of an electron injection layer by vacuum deposition (Step 7) Formation of a cathode by vacuum deposition By going through these steps, an organic EL element consisting of an anode/hole injection layer/hole transport layer/emitting layer consisting of a host material and a dopant material/electron transport layer/electron injection layer/cathode is obtained.
Of course, if there is a means for preventing dissolution of the lower light-emitting layer, or if a means for forming a film from the cathode side is used in the opposite procedure to the above, a layer-forming composition containing a material for the electron transport layer and a material for the electron injection layer can be prepared and then the layer can be formed by a wet film formation method.

<Other film formation methods>
The composition for forming an organic layer can be formed into a film by laser thermal imaging (LITI). LITI is a method in which a compound attached to a substrate is heated and vapor-deposited by a laser, and the composition for forming an organic layer can be used as a material to be applied to the substrate.

<Optional Step>
Before and after each film-forming step, appropriate treatment steps, cleaning steps, and drying steps may be appropriately inserted. Examples of treatment steps include exposure treatment, plasma surface treatment, ultrasonic treatment, ozone treatment, cleaning treatment using an appropriate solvent, and heat treatment. Furthermore, a series of steps for preparing a bank may also be included.

Photolithography techniques can be used to fabricate the bank. Positive and negative resist materials can be used as bank materials for photolithography. In addition, patternable printing methods such as inkjet printing, gravure offset printing, reverse offset printing, and screen printing can also be used. In this case, permanent resist materials can also be used.

Materials used for banks include, but are not limited to, polysaccharides and their derivatives, homopolymers and copolymers of hydroxyl-containing ethylenic monomers, biopolymers, polyacryloyl compounds, polyesters, polystyrenes, polyimides, polyamideimides, polyetherimides, polysulfides, polysulfones, polyphenylenes, polyphenyl ethers, polyurethanes, epoxy (meth)acrylates, melamine (meth)acrylates, polyolefins, cyclic polyolefins, acrylonitrile-butadiene-styrene copolymers (ABS), silicone resins, polyvinyl chloride, chlorinated polyethylene, chlorinated polypropylene, polyacetate, polynorbornene, synthetic rubber, fluorinated polymers such as polyfluorovinylidene, polytetrafluoroethylene, and polyhexafluoropropylene, fluoroolefin-hydrocarbonolefin copolymers, and fluorocarbon polymers.

<Organic layer forming composition used in wet film formation method>
The composition for forming an organic layer is obtained by dissolving a low molecular weight compound capable of forming each organic layer of an organic EL element, or a polymer compound obtained by polymerizing the low molecular weight compound, in an organic solvent. For example, the composition for forming an emitting layer contains at least one polycyclic aromatic compound (or a polymer compound thereof) as a first component, which is a dopant material, at least one host material as a second component, and at least one organic solvent as a third component. The first component functions as a dopant component of the emitting layer obtained from the composition, and the second component functions as a host component of the emitting layer. The third component functions as a solvent that dissolves the first and second components in the composition, and gives a smooth and uniform surface shape due to the controlled evaporation rate of the third component itself during application.

<Organic solvent>
The composition for forming an organic layer contains at least one organic solvent. By controlling the evaporation rate of the organic solvent during film formation, it is possible to control and improve the film formability, the presence or absence of defects in the coating film, the surface roughness, and the smoothness. In addition, during film formation using the inkjet method, it is possible to control the meniscus stability at the pinhole of the inkjet head, and to control and improve the ejection properties. In addition, by controlling the drying rate of the film and the orientation of the derivative molecules, it is possible to improve the electrical properties, light emitting properties, efficiency, and life of an organic EL element having an organic layer obtained from the composition for forming an organic layer.

(1) Physical properties of organic solvent The boiling point of at least one organic solvent is 130°C to 300°C, more preferably 140°C to 270°C, and even more preferably 150°C to 250°C. When the boiling point is higher than 130°C, it is preferable from the viewpoint of inkjet dischargeability. Also, when the boiling point is lower than 300°C, it is preferable from the viewpoint of defects, surface roughness, residual solvent, and smoothness of the coating film. From the viewpoint of good inkjet dischargeability, film-forming property, smoothness, and low residual solvent, it is more preferable that the organic solvent contains two or more organic solvents. On the other hand, in some cases, the composition may be a solid state composition obtained by removing the solvent from the composition for forming the organic layer, taking into consideration transportability and the like.

Furthermore, it is particularly preferable that the organic solvent contains a good solvent (GS) and a poor solvent (PS) for at least one type of solute, and the boiling point (BP _GS ) of the good solvent (GS) is lower than the boiling point (BP _PS ) of the poor solvent (PS).
By adding a poor solvent with a high boiling point, the good solvent with a low boiling point volatilizes first during film formation, increasing the concentration of the components in the composition and the concentration of the poor solvent, promoting rapid film formation. This results in a coating film with few defects, small surface roughness, and high smoothness.

The difference in solubility (S _GS -S _PS ) is preferably 1% or more, more preferably 3% or more, and even more preferably 5% or more. The difference in boiling point (BP _PS -BP _GS ) is preferably 10°C or more, more preferably 30°C or more, and even more preferably 50°C or more.

After film formation, the organic solvent is removed from the coating film by a drying process such as vacuum, reduced pressure, or heating. When heating is performed, from the viewpoint of improving the coating film formation properties, it is preferable to perform the heating at a temperature of at least one of the solutes' glass transition temperature (Tg) +30°C or lower. From the viewpoint of reducing residual solvent, it is preferable to heat at at least one of the solutes' glass transition temperature (Tg) -30°C or higher. Even if the heating temperature is lower than the boiling point of the organic solvent, the organic solvent is sufficiently removed because the film is thin. Also, drying may be performed multiple times at different temperatures, and multiple drying methods may be used in combination.

(2) Specific examples of organic solvents Examples of organic solvents used in the composition for forming an organic layer include alkylbenzene solvents, phenyl ether solvents, alkyl ether solvents, cyclic ketone solvents, aliphatic ketone solvents, monocyclic ketone solvents, solvents having a diester skeleton, and fluorine-containing solvents. Specific examples include pentanol, hexanol, heptanol, octanol, nonanol, decanol, undecanol, dodecanol, tetradecanol, hexane-2-ol, heptan-2-ol, octan-2-ol, decan-2-ol, dodecan-2-ol, cyclohexanol, α-terpineol, β-terpineol, γ-terpineol, δ-terpineol, terpineol (mixture), ethylene glycol monomethyl ether acetate, propylene glycol monomethyl ether acetate, diethylene glycol dimethyl ether, dipropylene glycol dimethyl ether, diethylene glycol ethyl methyl ether, ethylene glycol ethyl ... ether, diethylene glycol isopropyl methyl ether, dipropylene glycol monomethyl ether, diethylene glycol diethyl ether, diethylene glycol monomethyl ether, diethylene glycol butyl methyl ether, tripropylene glycol dimethyl ether, triethylene glycol dimethyl ether, diethylene glycol monobutyl ether, ethylene glycol monophenyl ether, triethylene glycol monomethyl ether, diethylene glycol dibutyl ether, triethylene glycol butyl methyl ether, polyethylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, p-xylene, m-xylene, o-xylene, 2,6-lutidine, 2-fluoro-m-xylene, 3-fluoro-o-xylene, 2-chlorobenzotrifluoride, cumene, toluene, 2-chloro-6-fluorotoluene, 2-fluoroanisole, anisole, 2,3-Dimethylpyrazine, Bromobenzene, 4-Fluoroanisole, 3-Fluoroanisole, 3-Trifluoromethylanisole, Mesitylene, 1,2,4-Trimethylbenzene, t-Butylbenzene, 2-Methylanisole, Phenetole, Benzodioxole, 4-Methylanisole, s-Butylbenzene, 3-Methylanisole, 4-Fluoro-3-methylanisole, Cymene, 1,2,3-Trimethylbenzene, 1,2-Dichlorobenzene, 2-Fluorobenzonitrile, 4-Fluoroveratrol, 2,6-Dimethylanisole, n-Butylbenzene, 3-Fluorobenzonitrile, Decalin (Decahydronaphthalene), Neopentylbenzene, 2,5-Dimethylanisole, 2,4-Dimethylanisole, Benzonitrile, 3,5-Dimethylanisole, Diphenyl ether, 1-Fluoro-3,5-dimethoxybenzene, Methyl benzoate, Isopentylbenzene, 3,4-Dimethylanisole , o-tolunitrile, n-amylbenzene, veratrole, 1,2,3,4-tetrahydronaphthalene, ethyl benzoate, n-hexylbenzene, propyl benzoate, cyclohexylbenzene, 1-methylnaphthalene, butyl benzoate, 2-methylbiphenyl, 3-phenoxytoluene, 2,2'-bitolyl, dodecylbenzene, dipentylbenzene, tetramethylbenzene, trimethoxybenzene, trimethoxytoluene, 2,3-dihydrobenzofuran, 1-methyl-4-(propoxymethyl)benzene, 1-methyl-4-(butyloxymethyl)benzene, 1-methyl-4-(pentyloxymethyl)benzene, 1-methyl-4-(hexyloxymethyl)benzene, 1-methyl-4-(heptyloxymethyl)benzene, benzyl butyl ether, benzyl pentyl ether, benzyl hexyl ether, benzyl heptyl ether, benzyl octyl ether, etc., but are not limited thereto. In addition, the solvent may be used alone or may be mixed.

<Optional ingredients>
The composition for forming the organic layer may contain optional components, such as a binder and a surfactant, to the extent that the properties of the composition are not impaired.

(1) Binder The composition for forming an organic layer may contain a binder. The binder forms a film during film formation and bonds the resulting film to a substrate. The binder also plays a role in dissolving, dispersing, and binding other components in the composition for forming an organic layer.

Examples of binders used in the organic layer forming composition include, but are not limited to, acrylic resins, polyethylene terephthalate, ethylene-vinyl acetate copolymers, ethylene-vinyl alcohol copolymers, acrylonitrile-ethylene-styrene copolymer (AES) resins, ionomers, chlorinated polyethers, diallyl phthalate resins, unsaturated polyester resins, polyethylene, polypropylene, polyvinyl chloride, polyvinylidene chloride, polystyrene, polyvinyl acetate, Teflon, acrylonitrile-butadiene-styrene copolymer (ABS) resins, acrylonitrile-styrene copolymer (AS) resins, phenolic resins, epoxy resins, melamine resins, urea resins, alkyd resins, polyurethanes, and copolymers of the above resins and polymers.

The binder used in the composition for forming the organic layer may be of one type only or a mixture of multiple types.

(2) Surfactant The organic layer forming composition may contain a surfactant, for example, to control the film surface uniformity, solvent affinity and liquid repellency of the organic layer forming composition. Surfactants are classified into ionic and nonionic based on the structure of the hydrophilic group, and further classified into alkyl, silicon and fluorine based based on the structure of the hydrophobic group. In addition, based on the molecular structure, they are classified into monomolecular systems with relatively small molecular weight and simple structure, and polymer systems with large molecular weight and side chains or branches. In addition, based on the composition, they are classified into single systems and mixed systems in which two or more types of surfactants and base materials are mixed. All types of surfactants can be used as surfactants that can be used in the organic layer forming composition.

Examples of surfactants include Polyflow No. 45, Polyflow KL-245, Polyflow No. 75, Polyflow No. 90, Polyflow No. 95 (trade names, manufactured by Kyoeisha Chemical Industry Co., Ltd.), Disperbake 161, Disperbake 162, Disperbake 163, Disperbake 164, Disperbake 166, Disperbake 170, Disperbake 180, Disperbake 181, Disperbake 182, BYK300, BYK306, BYK310, BYK320, BYK330, BYK342, B YK344, BYK346 (product names, manufactured by BYK Japan Co., Ltd.), KP-341, KP-358, KP-368, KF-96-50CS, KF-50-100CS (product names, manufactured by Shin-Etsu Chemical Co., Ltd.), Surflon SC-101, Surflon KH-40 (product names, manufactured by Seimi Chemical Co., Ltd.), Ftergent 222F, Ftergent 251, FTX-218 (product names, manufactured by Neos Co., Ltd.), EFTOP EF-351, EFTOP EF-352, EFTOP EF-601, EFTOP EF-801, EFTOP EF-802 (product name, manufactured by Mitsubishi Materials Corporation), Megafac F-470, Megafac F-471, Megafac F-475, Megafac R-08, Megafac F-477, Megafac F-479, Megafac F-553, Megafac F-554 (product name, manufactured by DIC Corporation), fluoroalkylbenzenesulfonates, fluoroalkylcarboxylates, fluoroalkylpolyoxyethyleneethers, fluoroalkylammonium iodides, fluoroalkylbetaines, fluoroalkylsulfonates, diglycerol tetrakis (fluoroalkylpolyoxyethyleneether), fluoroalkyltrimethylammonium salts, fluoroalkylaminosulfonates, polyoxyethylene nonyl Examples of the alkyl ethers include polyoxyethylene octylphenyl ether, polyoxyethylene alkyl ethers, polyoxyethylene laurate, polyoxyethylene oleate, polyoxyethylene stearate, polyoxyethylene laurylamine, sorbitan laurate, sorbitan palmitate, sorbitan stearate, sorbitan oleate, sorbitan fatty acid esters, polyoxyethylene sorbitan laurate, polyoxyethylene sorbitan palmitate, polyoxyethylene sorbitan stearate, polyoxyethylene sorbitan oleate, polyoxyethylene naphthyl ether, alkyl benzene sulfonates, and alkyl diphenyl ether disulfonates.

In addition, surfactants may be used alone or in combination of two or more types.

<Composition and Properties of Organic Layer-Forming Composition>
The content of each component in the composition for forming an organic layer is determined in consideration of the good solubility, storage stability and film-forming property of each component in the composition for forming an organic layer, the good film quality of the coating film obtained from the composition for forming an organic layer, the good discharge property when using an ink jet method, and the good electrical properties, light-emitting properties, efficiency and life of an organic EL element having an organic layer produced using the composition. For example, in the case of a composition for forming an emitting layer, it is preferable that the first component is 0.0001% by weight to 2.0% by weight, the second component is 0.0999% by weight to 8.0% by weight, and the third component is 90.0% by weight to 99.9% by weight, based on the total weight of the composition for forming an emitting layer.

More preferably, the first component is 0.005% by weight to 1.0% by weight, the second component is 0.095% by weight to 4.0% by weight, and the third component is 95.0% by weight to 99.9% by weight, based on the total weight of the composition for forming the light-emitting layer. Even more preferably, the first component is 0.05% by weight to 0.5% by weight, the second component is 0.25% by weight to 2.5% by weight, and the third component is 97.0% by weight to 99.7% by weight, based on the total weight of the composition for forming the light-emitting layer.

The composition for forming the organic layer can be produced by appropriately selecting and carrying out stirring, mixing, heating, cooling, dissolving, dispersing, etc. of the above-mentioned components by known methods. In addition, after preparation, filtration, degassing (also called degassing), ion exchange treatment, and inert gas replacement/filling treatment, etc. may be appropriately selected and carried out.

The higher the viscosity of the composition for forming the organic layer, the better the film-forming properties and the better the ejection properties when using the inkjet method. On the other hand, the lower the viscosity, the easier it is to form a thin film. For this reason, the viscosity of the composition for forming the organic layer at 25°C is preferably 0.3 to 3 mPa·s, and more preferably 1 to 3 mPa·s. In the present invention, the viscosity is a value measured using a cone-plate type rotational viscometer (cone-plate type).

The lower the surface tension of the composition for forming the organic layer, the better the film-forming properties and the more defect-free the coating film will be. On the other hand, the higher the surface tension, the better the ink-jet ejection properties will be. For this reason, the viscosity of the composition for forming the organic layer is preferably such that the surface tension at 25°C is 20 to 40 mN/m, and more preferably 20 to 30 mN/m. In the present invention, the surface tension is a value measured using the hanging drop method.

式（ＸＬＰ－１）において、
ＭＵｘ、ＥＣｘおよびｋは上記式（ＳＰＨ－１）におけるＭＵ、ＥＣおよびｋと同定義であり、ただし、式（ＸＬＰ－１）で表される化合物は少なくとも１つの架橋性置換基（ＸＬＳ）を有し、好ましくは架橋性置換基を有する１価または２価の芳香族化合物の含有量は、分子中０．１～８０重量％である。 <Crosslinkable polymer compound: compound represented by general formula (XLP-1)>
Next, the case where the above-mentioned polymer compound has a crosslinkable substituent will be described. Such a crosslinkable polymer compound is, for example, a compound represented by the following general formula (XLP-1).

In formula (XLP-1),
MUx, ECx and k are defined the same as MU, EC and k in the above formula (SPH-1), with the proviso that the compound represented by formula (XLP-1) has at least one crosslinkable substituent (XLS), and preferably the content of the monovalent or divalent aromatic compound having a crosslinkable substituent is 0.1 to 80% by weight in the molecule.

The content of the monovalent or divalent aromatic compound having a crosslinkable substituent is preferably 0.5 to 50% by weight, more preferably 1 to 20% by weight.

The crosslinkable substituent (XLS) is not particularly limited as long as it is a group that can further crosslink the above-mentioned polymer compound, but substituents having the following structures are preferred: In each structural formula, * indicates a bond position.

Each L is independently a single bond, -O-, -S-, >C=O, -O-C(=O)-, an alkylene having 1 to 12 carbon atoms, an oxyalkylene having 1 to 12 carbon atoms, or a polyoxyalkylene having 1 to 12 carbon atoms. Among the above substituents, a group represented by formula (XLS-1), formula (XLS-2), formula (XLS-3), formula (XLS-9), formula (XLS-10) or formula (XLS-17) is preferred, and a group represented by formula (XLS-1), formula (XLS-3) or formula (XLS-17) is more preferred.

Examples of the divalent aromatic compound having a crosslinkable substituent include compounds having the following partial structures: In the following structural formula, * indicates a bonding position.

<Method of producing polymer compound and crosslinkable polymer compound>
The methods for producing the polymer compound and the crosslinkable polymer compound will be described below with reference to the compound represented by the above formula (SPH-1) and the compound represented by the above formula (XLP-1). These compounds can be synthesized by appropriately combining known production methods.

Solvents used in the reaction include aromatic solvents, saturated/unsaturated hydrocarbon solvents, alcohol solvents, ether solvents, etc., such as dimethoxyethane, 2-(2-methoxyethoxy)ethane, 2-(2-ethoxyethoxy)ethane, etc.

The reaction may also be carried out in a two-phase system. When carrying out the reaction in a two-phase system, a phase transfer catalyst such as a quaternary ammonium salt may be added as necessary.

The compounds of formula (SPH-1) and (XLP-1) may be produced in one step or in multiple steps. The compounds may be produced by a batch polymerization method in which all the raw materials are put into a reaction vessel and then the reaction is started, a dropwise polymerization method in which the raw materials are added dropwise to a reaction vessel, or a precipitation polymerization method in which the product precipitates as the reaction proceeds. These methods can be combined appropriately to synthesize the compounds. For example, when the compound represented by formula (SPH-1) is synthesized in one step, the target product is obtained by carrying out a reaction in a state in which the monomer unit (MU) and the end cap unit (EC) are added to a reaction vessel. When the compound represented by general formula (SPH-1) is synthesized in multiple steps, the target product is obtained by polymerizing the monomer unit (MU) to the target molecular weight, and then adding and reacting the end cap unit (EC). If different types of monomer units (MU) are added in multiple steps and the reaction is carried out, a polymer having a concentration gradient in the structure of the monomer unit can be produced. After preparing a precursor polymer, the target polymer can be obtained by a subsequent reaction.

In addition, the primary structure of the polymer can be controlled by selecting the polymerizable group of the monomer unit (MU). For example, as shown in synthesis schemes 1 to 3, it is possible to synthesize a polymer having a random primary structure (synthetic scheme 1), a polymer having a regular primary structure (synthetic schemes 2 and 3), etc., and these can be used in appropriate combination depending on the target object. Furthermore, if a monomer unit having three or more polymerizable groups is used, a hyperbranched polymer or a dendrimer can be synthesized.

The monomer units that can be used in the present invention include those described in JP 2010-189630 A, WO 2012/086671 A, WO 2013/191088 A, WO 2002/045184 A, WO 2011/049241 A, WO 2013/146806 A, WO 2005/049546 A, WO 2015/14 It can be synthesized in accordance with the methods described in JP-A-2002/045184, JP-A-2010-215886, JP-A-2008-106241, JP-A-2010-215886, WO 2016/031639, JP-A-2011-174062, WO 2016/031639, WO 2016/031639, and WO 2002/045184.

Specific polymer synthesis procedures are described in JP 2012-036388 A, WO 2015/008851 A, JP 2012-36381 A, JP 2012-144722 A, WO 2015/194448 A, WO 2013/146806 A, WO 2015/145871 A, WO 2016/ It can be synthesized in accordance with the methods described in WO 2016/031639, WO 2016/125560, WO 2016/031639, WO 2016/031639, WO 2016/125560, WO 2015/145871, WO 2011/049241, and JP 2012-144722 A.

<Application examples of organic electroluminescent devices>
The present invention can also be applied to a display device having an organic EL element or a lighting device having an organic EL element.
A display device or lighting device including an organic EL element can be manufactured by a known method, for example by connecting the organic EL element according to this embodiment to a known driving device, and can be driven appropriately using a known driving method such as DC driving, pulse driving, or AC driving.

Examples of display devices include panel displays such as color flat panel displays, and flexible displays such as flexible color organic electroluminescent (EL) displays (see, for example, JP-A-10-335066, JP-A-2003-321546, JP-A-2004-281086, etc.). Display methods include, for example, matrix and/or segment methods. Note that matrix display and segment display may coexist in the same panel.

In a matrix, the pixels for display are arranged two-dimensionally, such as in a grid or mosaic pattern, and a collection of pixels displays characters and images. The shape and size of the pixels are determined by the application. For example, square pixels with sides of 300 μm or less are usually used to display images and characters on computers, monitors, and televisions, and pixels with sides of mm order are used for large displays such as display panels. For monochrome display, pixels of the same color can be arranged, but for color display, red, green, and blue pixels are displayed side by side. In this case, there are typically delta types and stripe types. The driving method for this matrix can be either line sequential driving method or active matrix. Line sequential driving has the advantage of being simpler in structure, but when considering operating characteristics, active matrix may be superior, so it is necessary to use it according to the application.

In the segment type, a pattern is formed to display predetermined information, and a specific area is illuminated. Examples include the time and temperature displays on digital clocks and thermometers, the operating status displays on audio equipment and induction cookers, and panel displays on automobiles.

Examples of lighting devices include lighting devices for indoor lighting, backlights for liquid crystal display devices, etc. (see, for example, JP 2003-257621 A, JP 2003-277741 A, JP 2004-119211 A, etc.). Backlights are mainly used for the purpose of improving the visibility of non-self-luminous display devices, and are used in liquid crystal display devices, clocks, audio devices, automobile panels, display boards, signs, etc. In particular, for backlights for liquid crystal display devices, especially for personal computers, where thinning is an issue, it is difficult to make them thin because conventional methods are made of fluorescent lamps and light guide plates, so the backlights using the light-emitting elements according to this embodiment are characterized by their thinness and light weight.

3-2. Other Organic Devices The polycyclic aromatic compound according to the present invention can be used to prepare organic field effect transistors, organic thin-film solar cells, wavelength conversion filters, and the like, in addition to the organic electroluminescent devices described above.

An organic field-effect transistor is a transistor that controls current by generating an electric field through voltage input, and has a gate electrode in addition to source and drain electrodes. When a voltage is applied to the gate electrode, an electric field is generated, and the flow of electrons (or holes) between the source and drain electrodes can be blocked at will to control the current. Field-effect transistors are easier to miniaturize than simple transistors (bipolar transistors), and are often used as elements in integrated circuits.

The structure of an organic field effect transistor may be such that a source electrode and a drain electrode are provided in contact with an organic semiconductor active layer formed using the polycyclic aromatic compound according to the present invention, and a gate electrode is provided sandwiching an insulating layer (dielectric layer) in contact with the organic semiconductor active layer. Examples of the element structure include the following structure.
(1) Substrate/gate electrode/insulator layer/source electrode/drain electrode/organic semiconductor active layer (2) Substrate/gate electrode/insulator layer/organic semiconductor active layer/source electrode/drain electrode (3) Substrate/organic semiconductor active layer/source electrode/drain electrode/insulator layer/gate electrode (4) Substrate/source electrode/drain electrode/organic semiconductor active layer/insulator layer/gate electrode An organic field effect transistor configured in this manner can be used as a pixel driving switching element for active matrix driving liquid crystal displays and organic electroluminescence displays.

An organic thin-film solar cell has a structure in which an anode such as ITO, a hole transport layer, a photoelectric conversion layer, an electron transport layer, and a cathode are laminated on a transparent substrate such as glass. The photoelectric conversion layer has a p-type semiconductor layer on the anode side and an n-type semiconductor layer on the cathode side. The polycyclic aromatic compound according to the present invention can be used as a material for a hole transport layer, a p-type semiconductor layer, an n-type semiconductor layer, and an electron transport layer depending on its physical properties. The polycyclic aromatic compound according to the present invention can function as a hole transport material or an electron transport material in an organic thin-film solar cell. In addition to the above, the organic thin-film solar cell may appropriately include a hole blocking layer, an electron blocking layer, an electron injection layer, a hole injection layer, a smoothing layer, and the like. For the organic thin-film solar cell, known materials used in organic thin-film solar cells can be appropriately selected and combined and used.

Quantum dots with narrow emission half-widths are used as phosphors in wavelength conversion filters to widen the color gamut of displays. However, they have problems such as instability to oxidation, high coagulation due to the nano-sized particles, and the metals used are regulated as pollutants. The polycyclic aromatic compound of the present invention can be used as a phosphor in wavelength conversion filters. As a matrix for dispersing this polycyclic aromatic compound, a polymer material having high transparency, low water vapor permeability, low oxygen permeability, and high thermal stability is preferable, and examples of such materials include (meth)acrylic polymers such as polymethyl (meth)acrylate and cycloolefin polymers such as Zeonex.

The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these. First, a synthesis example of a polycyclic aromatic compound will be described below.

Synthesis Example (1)
Synthesis of Compound (1A-92): 8,10,12,14-tetrakis(3,5-dimethylphenyl)-1,6,16,21,22,28-hexamethyl-3a ² ,3b,8,10,12,14,18b,18c ² ,24b,25b-decahydro-3a ² ,8,10,12,14,18c ² -hexaaza-3b,18b,24b,25b-tetraborane-deno[4',3',2',1':3,4,5]phenanthro[2,1,10,9-g ₁ h ₁ i ₁ j ₁ ]indeno[4',3',2',1':3,4,5]phenanthro[2,1,10,9-yza ₁ b ₁ ]nonacene

Under a nitrogen atmosphere, a flask containing N ¹ ,N ³ -bis(3,5-dimethylphenyl)benzene-1,3-diamine (0.158 g, 0.50 mmol), 3-chloro-5-(4,5-dimethyl-9H-carbazol-9-yl)-N-(3,5-dimethylphenyl)-N-(m-tolyl)aniline (0.541 g, 1.1 mmol), Pd ₂ (dba) ₃ (22.9 mg, 0.025 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (SPhos: 20.5 mg, 0.050 mmol), NaOtBu (0.144 g, 1.5 mmol) and o-xylene (2.5 ml) was heated to 110° C. and stirred for 16 hours. The reaction solution was cooled to room temperature and filtered using a Florisil short-path column (eluent: toluene/heptane = 1/10 (volume ratio)), and the obtained crude product was purified by reprecipitation using hexane and dichloromethane to obtain N ¹ ,N ¹ '-(1,3-phenylene)bis(5-(4,5-dimethyl-9H-carbazol-9-yl)-N ¹ ,N ³ -bis(3,5-dimethylphenyl)-N ³ -(m-tolyl)benzene-1,3-diamine) as a white solid (0.474 g, yield 74%).

The structure of the obtained compound was confirmed by NMR measurement.
¹ H-NMR (400 MHz, CDCl ₃ ): δ = 2.09 (s, 12H), 2.16 (s, 12H), 2.20 (s, 6H), 2.98 (s, 12H), 6.50 (s, 2H), 6.56 (s, 2H), 6.60 (s, 2H), 6.62-6.64 (m, 6H), 6.69-6 .72 (m, 6H), 6.75 (d, 2H), 6.79 (s, 2H), 6.86-6.88 (m, 3H), 6.91 (s, 2H), 6.96 (d, 4H), 7.02 (t, 2H), 7.09 (t, 1H), 7.19-7.20 (m, 8H).

To a flask containing N ¹ ,N ¹ '-(1,3-phenylene)bis(5-(4,5-dimethyl-9H-carbazol-9-yl)-N ¹ ,N ³ -bis(3,5-dimethylphenyl)-N ³ -(m-tolyl)benzene-1,3-diamine) (0.127 g, 0.10 mmol) and o-dichlorobenzene (1.0 ml), boron tribromide (0.15 ml, 1.6 mmol) was added at room temperature under a nitrogen atmosphere. After the dropwise addition was completed, the mixture was heated to 200°C and stirred for 20 hours. The reaction solution was cooled to room temperature, and hydrogen bromide in the reaction solution was distilled off under reduced pressure. Dichloromethane (500 ml) was added to dilute the reaction solution, and then a phosphate buffer solution (pH = 7, 100 ml) was added at room temperature. The aqueous layer was extracted three times with dichloromethane, and the solvent was distilled off under reduced pressure. The obtained crude product was washed with toluene to obtain compound (1A-92) as a yellow solid (34.6 mg, yield 27%).

The structure of the obtained compound was confirmed by NMR measurement.
¹ H-NMR (500 MHz, (CDCl ₂ ) ₂ ): δ = 2.26 (s, 12H), 2.34 (s, 12H), 2.39 (s, 6H), 3.34 (s, 6H), 3.45 (s, 6H), 5.48 (s, 1H), 6.07 (s, 2H), 6.64 (s, 4H), 6.77 (s, 2H) , 6.84 (s, 4H), 6.97 (s, 2H), 7.06 (s, 2H), 7.19 (d, 2H), 7.64 (d, 2H), 7.87 (d, 2H), 9.01-9.05 (m, 4H), 9.49 (d, 2H), 10.9 (s, 1H).

Synthesis Example (2)
Compound (1A-142): 8,10,12,14-tetrakis(3,5-di-t-butylphenyl)-6,16-di-t-butyl-1,21,22,28-tetramethyl-3a ² ,3b,8,10,12,14,18b,18c ² ,24b,25b-decahydro-3a ² ,8,10,12,14,18c ² -hexaaza-3b,18b,24b,25b-tetraborane indeno[4',3',2',1':3,4,5]phenanthro[2,1,10,9-g ₁ h ₁ i ₁ j ₁ ]indeno[4',3',2',1':3,4,5]phenanthro[2,1,10,9-yza ₁ b ₁ Synthesis of ]nonacene

To a flask containing N ¹ ,N ^1' -(1,3-phenylene)bis(5-(4,5-dimethyl-9H-carbazol-9-yl)-N ¹ ,N ³ -bis(3,5-di-t-butylphenyl)-N ³ -(3-(t-butyl)phenyl)benzene-1,3-diamine) (0.171 g, 0.10 mmol) and o-dichlorobenzene (1.0 ml), boron tribromide (0.15 ml, 1.6 mmol) was added at room temperature under a nitrogen atmosphere. After completion of the dropwise addition, the mixture was heated to 200°C and stirred for 20 hours. The reaction solution was cooled to room temperature, and hydrogen bromide in the reaction solution was distilled off under reduced pressure. Acetonitrile (15 ml) and triethylamine (1.0 ml) were added to the reaction solution, which was then subjected to ultrasonic cleaning and suction filtration. The resulting crude product was purified using a silica gel column (eluent: hexane/dichloromethane=7/3) and washed with acetonitrile to obtain compound (1A-142) as a yellow solid (50.9 mg, yield 29%).

The structure of the obtained compound was confirmed by NMR measurement.
¹ H-NMR (400 MHz, CDCl ₃ ): δ=1.12 (s, 18H), 1.15 (s, 36H), 1.30 (s, 36H), 3.18 (s, 6H), 3.29 (s, 6H), 5.94 (s, 2H), 6.04 (s, 2H), 6.24 (s, 1H), 6.93 (s, 4H), 7. 01 (s, 4H), 7.22 (s, 2H), 7.32 (d, 2H), 7.43 (d, 2H), 7.52 (s, 2H), 7.60 (d, 2H), 8.86 (d, 2H), 8.97 (d, 2H), 9.31 (d, 2H), 10.8 (s, 1H).

Synthesis Example (3)
Synthesis of compound (1A-149)

To a flask containing the compound (Int-1A-149) (0.10 g) and o-dichlorobenzene (1.0 ml), boron tribromide (0.20 ml) was added at room temperature under a nitrogen atmosphere. After the dropwise addition, the mixture was heated to 200° C. and stirred for 20 hours. The reaction solution was cooled to room temperature, and hydrogen bromide in the reaction solution was distilled off under reduced pressure. Acetonitrile (15 ml) and triethylamine (1.0 ml) were added to the reaction solution, which was then subjected to ultrasonic cleaning and suction filtration. The obtained crude product was purified using a silica gel column (eluent: toluene) and washed with acetonitrile to obtain compound (1A-149) as a yellow solid (10 mg).
The target compound (1A-149) was identified at m/z=2493.56 by MALDI-MS.

Synthesis Example (4)
Synthesis of compound (1A-151)

To a flask containing the compound (Int-1A-151) (0.10 g) and o-dichlorobenzene (1.0 ml), boron tribromide (0.20 ml) was added at room temperature under a nitrogen atmosphere. After the dropwise addition, the mixture was heated to 200° C. and stirred for 20 hours. The reaction solution was cooled to room temperature, and hydrogen bromide in the reaction solution was distilled off under reduced pressure. Acetonitrile (15 ml) and triethylamine (1.0 ml) were added to the reaction solution, which was then subjected to ultrasonic cleaning and suction filtration. The obtained crude product was purified using a silica gel column (eluent: toluene) and washed with acetonitrile to obtain compound (1A-151) as a yellow solid (4 mg).
The target compound (1A-151) was identified at m/z=3260.01 by MALDI-MS.

Synthesis Example (5)
Synthesis of compound (1A-195)

To a flask containing the compound (Int-1A-195) (0.175 g, 0.10 mmol) and o-dichlorobenzene (1.0 ml), boron tribromide (0.15 ml, 1.6 mmol) was added at room temperature under a nitrogen atmosphere. After the dropwise addition was completed, the mixture was heated to 200° C. and stirred for 20 hours. The reaction solution was cooled to room temperature, and hydrogen bromide in the reaction solution was distilled off under reduced pressure. After dichloromethane (500 ml) was added to dilute the reaction solution, a phosphate buffer solution (pH = 7, 100 ml) was added at room temperature, and the aqueous layer was extracted three times with dichloromethane, and the solvent was distilled off under reduced pressure. The obtained crude product was purified using a silica gel column (eluent: hexane/toluene = 2/1) to obtain the compound (1A-195) as a yellow solid (76.8 mg, yield 43%).

The structure of the obtained compound was confirmed by NMR measurement.
¹ H-NMR (400 MHz, CDCl ₃ ): δ = 0.78 (t, 6H), 0.93 (t, 6H), 0.94 (t, 6H), 1.03 (t, 6H), 1.25 (s, 18H), 1.42 (m, 16H), 1 .48 (m, 16H), 1.91 (m, 4H), 2.22 (s, 12H), 2.30 (s, 12H), 3.05 (m, 4H), 3.31 (m, 4H), 5.32 (s , 2H), 6.02 (s, 1H), 6.59 (s, 4H), 6.81 (s, 4H), 6.93 (s, 2H), 6.95 (s, 2H), 7.04 (s, 2H), 7.4 4 (d, 2H), 8.33 (s, 2H), 8.40 (s, 2H), 8.85 (s, 2H), 9.10 (d, 2H), 9.23 (s, 2H), 10.8 (s, 1H).

Synthesis Example (6)
Synthesis of compound (1A-197)

Compound (1A-197) (0.01 g) was obtained by synthesizing in the same manner as in Synthesis Example (2) except that N ¹ ,N ^{1 '} -(1,3-phenylene)bis( ^5- (4,5-dimethyl-9H-carbazol-9-yl)-N 1 ,N 3 -bis(3,5-di-t-butylphenyl)-N ³ -(3-(t-butyl)phenyl)benzene-1,3-diamine) was changed to compound (Int-1A-197).

The target compound (1A-197) was identified at m/z = 1890.011 using MALDI-TOF/MS.

The structure of the obtained compound (1A-197) was confirmed by NMR measurement.
¹ H-NMR (500 MHz, CDCl ₃ ): δ = 1.12 (s, 36H), 1.28 (s, 36H), 2.24 (s, 12H), 2.47 (s, 6H), 3.19 (s, 6H), 5.97 (s, 4H), 6.22 (s, 1H), 6.89 (s, 4H), 6.96 (s, 4H) , 7.15-7.17 (m, 6H), 7.20 (s, 2H), 7.51 (s, 2H), 7.88 (d, 2H), 8.40 (s, 2H), 8.81 (s, 2H), 8.96 (d, 2H), 9.53 (d, 2H), 11.1 (s, 1H).

Synthesis Example (7)
Synthesis of compound (1A-201)

Compound (1A-201) (0.01 g) was obtained by synthesizing in the same manner as in Synthesis Example (2) except that N ¹ ,N ^{1 '} -(1,3-phenylene)bis( ^5- (4,5-dimethyl-9H-carbazol-9-yl)-N 1 ,N 3 -bis(3,5-di-t-butylphenyl)-N ³ -(3-(t-butyl)phenyl)benzene-1,3-diamine) was changed to compound (Int-1A-201).

The target compound (1A-201) was identified at m/z = 1429.650 using MALDI-TOF/MS.

Synthesis Example (8)
Synthesis of compound (1A-203)

Compound (1A-203) was obtained (0.01 g) by synthesizing in the same manner as in Synthesis Example (3), except that compound (Int-1A-149) was changed to compound (Int-1A-203).

The target compound (1A-203) was identified at m/z = 3082.212 using MALDI-TOF/MS.

Synthesis Example (9)
Synthesis of compound (1A-204)

Compound (1A-204) was obtained (0.01 g) by synthesizing in the same manner as in Synthesis Example (4), except that compound (Int-1A-151) was changed to compound (Int-1A-204).

The target compound (1A-204) was identified at m/z = 4045.89 using MALDI-TOF/MS.

Synthesis Example (10)
Synthesis of compound (1A-212)

Compound (1A-212) (0.04 g) was obtained by synthesizing in the same manner as in Synthesis Example (2) except that N ¹ ,N ^{1 '} -(1,3-phenylene)bis( ^5- (4,5-dimethyl-9H-carbazol-9-yl)-N 1 ,N 3 -bis(3,5-di-t-butylphenyl)-N ³ -(3-(t-butyl)phenyl)benzene-1,3-diamine) was changed to compound (Int-1A-212).

The target compound (1A-212) was identified at m/z = 1875.93 using MALDI-TOF/MS.

Synthesis Example (11)
Synthesis of compound (1A-221)

Compound (1A-221) (0.20 g) was obtained by synthesizing in the same manner as in Synthesis Example (2) except that N ¹ ,N ^{1 '} -(1,3-phenylene)bis( ^5- (4,5-dimethyl-9H-carbazol-9-yl)-N 1 ,N 3 -bis(3,5-di-t-butylphenyl)-N ³ -(3-(t-butyl)phenyl)benzene-1,3-diamine) was changed to compound (Int-1A-221).

The target compound (1A-221) was identified at m/z = 1850.1244 by MALDI-MS.

Synthesis Example (12)
Synthesis of compound (1A-222)

Compound (1A-222) (0.18 g) was obtained by synthesizing in the same manner as in Synthesis Example (2) except that N ¹ ,N ^{1 '} -(1,3-phenylene)bis( ^5- (4,5-dimethyl-9H-carbazol-9-yl)-N 1 ,N 3 -bis(3,5-di-t-butylphenyl)-N ³ -(3-(t-butyl)phenyl)benzene-1,3-diamine) was changed to compound (Int-1A-222).

The target compound (1A-222) was identified at m/z = 1974.1549 by MALDI-MS.

Synthesis Example (13)
Synthesis of compound (1B-13)

Compound (1B-13) (0.02 g) was obtained by synthesizing in the same manner as in Synthesis Example (2) except that N ¹ ,N ^{1 '} -(1,3-phenylene)bis( ^5- (4,5-dimethyl-9H-carbazol-9-yl)-N ¹ ,N 3 -bis(3,5-di-t-butylphenyl)-N 3 -(3-(t-butyl)phenyl)benzene-1,3-diamine) was changed to compound (Int-1B-13).

The target compound (1B-13) was identified at m/z = 1595.8949 by MALDI-MS.

Synthesis Example (14)
Synthesis of compound (1B-15)

Compound (1B-15) (0.01 g) was obtained by synthesizing in the same manner as in Synthesis Example (2) except that N ¹ ,N ^{1 '} -(1,3-phenylene)bis( ^5- (4,5-dimethyl-9H-carbazol-9-yl)-N 1 ,N 3 -bis(3,5-di-t-butylphenyl)-N ³ -(3-(t-butyl)phenyl)benzene-1,3-diamine) was changed to compound (Int-1B-15).

The target compound (1B-15) was identified at m/z = 1595.8940 by MALDI-MS.

By appropriately changing the raw material compounds, other polycyclic aromatic compounds of the present invention can be synthesized in a manner similar to the synthesis examples described above.

Next, in order to explain the present invention in more detail, examples of organic EL elements using the compounds of the present invention are shown, but the present invention is not limited to these.

<Evaluation of basic physical properties>
Preparation of Samples When evaluating the absorption and emission characteristics (fluorescence and phosphorescence) of a compound to be evaluated, the compound to be evaluated may be dissolved in a solvent and evaluated in the solvent, or in a thin film state. Furthermore, when evaluating in a thin film state, depending on the mode of use of the compound to be evaluated in an organic EL device, the compound to be evaluated may be evaluated by forming only a thin film, or the compound to be evaluated may be dispersed in an appropriate matrix material and formed into a thin film.

As the matrix material, commercially available PMMA (polymethyl methacrylate) can be used. In this example, PMMA and the compound to be evaluated were dissolved in toluene, and then a thin film was formed on a transparent support substrate (10 mm x 10 mm) made of quartz by spin coating to prepare a thin film sample.

Furthermore, a thin film sample in the case where the matrix material was a host compound was prepared as follows. A transparent support substrate made of quartz (10 mm×10 mm×1.0 mm) was fixed to a substrate holder of a commercially available deposition apparatus (manufactured by Choshu Sangyo Co., Ltd.), and a molybdenum deposition boat containing the host compound and a molybdenum deposition boat containing the dopant compound were attached, and then the vacuum chamber was depressurized to 5×10 ⁻⁴ Pa. Next, the two deposition boats were heated simultaneously, and both compounds were co-deposited to an appropriate film thickness to form a mixed thin film (sample) of the host compound and the dopant compound. Here, the deposition rate was controlled according to the set mass ratio of the host compound and the dopant compound.

Evaluation of Absorption and Emission Characteristics The absorption spectrum of the sample was measured using an ultraviolet-visible-near infrared spectrophotometer (Shimadzu Corporation, UV-2600). The fluorescence spectrum or phosphorescence spectrum of the sample was measured using a spectrofluorophotometer (Hitachi High-Tech Corporation, F-7000).

For measuring the fluorescence spectrum, the sample was excited at an appropriate excitation wavelength at room temperature and photoluminescence was measured. For measuring the phosphorescence spectrum, the sample was immersed in liquid nitrogen (temperature 77 K) using an attached cooling unit. To observe the phosphorescence spectrum, an optical chopper was used to adjust the delay time between irradiation with excitation light and the start of measurement. The sample was excited at an appropriate excitation wavelength and photoluminescence was measured.

In addition, the fluorescence quantum yield (PLQY) was measured using an absolute PL quantum yield measurement device (Hamamatsu Photonics K.K., C9920-02G).

Evaluation of Fluorescence Lifetime (Delayed Fluorescence) The fluorescence lifetime was measured at 300K using a fluorescence lifetime measuring device (Hamamatsu Photonics Co., Ltd., C11367-01). Specifically, light-emitting components with fast and slow fluorescence lifetimes were observed at the maximum emission wavelength measured at an appropriate excitation wavelength. In the measurement of the fluorescence lifetime of a typical organic EL material that emits fluorescence at room temperature, slow emission components involving triplet components derived from phosphorescence are rarely observed due to the deactivation of triplet components by heat. If a slow emission component is observed in the compound to be evaluated, it indicates that triplet energy with a long excitation lifetime has been transferred to singlet energy by thermal activation and observed as delayed fluorescence.

Calculation of Energy Gap (Eg) The energy gap (Eg) was calculated from the long wavelength end A (nm) of the absorption spectrum obtained by the above-mentioned method as Eg = 1240/A.

Calculation of E(S,Sh), E(T,Sh) and ΔE(ST) The singlet excitation energy level E(S,Sh) was calculated from the wavelength B _Sh (nm) at the intersection of the tangent passing through the inflection point on the short wavelength side of the peak of the fluorescence spectrum and the baseline by E(S,Sh)=1240/B _Sh . The triplet excitation energy level E(T,Sh) was calculated from the wavelength C _Sh (nm) at the intersection of the tangent passing through the inflection point on the short wavelength side of the peak of the phosphorescence spectrum and the baseline by E(T,Sh)=1240/C _Sh .

ΔE(ST) is defined as ΔE(ST)=E(S,Sh)-E(T,Sh), which is the energy difference between E(S,Sh) and E(T,Sh). ΔE(ST) can also be calculated by the method described in, for example, "Purely organic electroluminescent material realizing 100% conversion from electricity to light", H. Kaji, H. Suzuki, T. Fukushima, K. Shizu, K. Katsuaki, S. Kubo, T. Komino, H. Oiwa, F. Suzuki, A. Wakamiya, Y. Murata, C. Adachi, Nat. Commun. 2015, 6, 8476.

<Example A1>
Evaluation of basic physical properties of compound (1A-92)
[Absorption characteristics]
A thin film formed on a glass substrate was prepared by dispersing compound (1A-92) in PMMA at a concentration of 1% by mass, and the absorption spectrum was measured. Due to the low solubility, no absorption peak was obtained in the visible light region.

[Light Emitting Characteristics]
A thin film substrate (made of glass) was prepared by dispersing compound (1A-92) in PMMA at a concentration of 1% by mass, and the fluorescence spectrum was observed by excitation at an excitation wavelength of 360 nm at room temperature and 77 K. As a result, the maximum emission wavelength was 477 nm and the half width was 24 nm at room temperature, and the maximum emission wavelength was 478 nm at 77 K. E(S,Sh) calculated from the intersection of the tangent passing through the inflection point on the short wavelength side of the optical peak at 77 K and the baseline was 2.73 eV.

In addition, a thin film substrate (made of quartz) was prepared in which compound (1A-92) was dispersed in PMMA at a concentration of 1% by mass, and the fluorescence quantum yield was measured by exciting the compound at an excitation wavelength of 360 nm. The result was a low value of 20%. This was because the low solubility of compound (1A-92) led to an underestimation. Although no clear absorption spectrum was obtained, clear luminescence was obtained, and therefore compound (1A-92) is expected to inherently exhibit strong luminescence.

Furthermore, a thin film substrate (made of glass) was prepared in which compound (1A-92) was dispersed in PMMA at a concentration of 1% by mass, and the phosphorescence spectrum was observed by exciting the substrate at 77 K with an excitation wavelength of 360 nm. As a result, the maximum emission wavelength was 480 nm. E(T,Sh), calculated from the intersection of the tangent passing through the inflection point on the short wavelength side of the phosphorescence peak and the baseline, was 2.67 eV.

ΔE(ST) was calculated to be 0.06 eV.

When a thin film substrate (made of quartz) in which compound (1A-92) was dispersed in PMMA at a concentration of 1% by mass was used, the lifetime of the delayed fluorescent component was measured with a fluorescence lifetime measurement device, and was found to be 3.6 μsec (Figure 2). In the fluorescence lifetime measurement, fluorescence with an emission lifetime of 100 ns or less was determined to be instantaneous fluorescence, and fluorescence with an emission lifetime of 0.1 μs or more was determined to be delayed fluorescence, and data from 3.5 to 9.5 μsec was used to calculate the fluorescence lifetime.

<Example A2>
Evaluation of basic physical properties of compound (1A-142)
[Absorption characteristics]
A thin film formed on a substrate (made of glass) in which the compound (1A-142) was dispersed in PMMA at a concentration of 1% by mass was prepared, and the absorption spectrum was measured. The longest wavelength absorption peak was at 464 nm.

[Light Emitting Characteristics]
A thin film substrate (made of glass) was prepared by dispersing compound (1A-142) in PMMA at a concentration of 1% by mass, and the fluorescence spectrum was observed by excitation at an excitation wavelength of 360 nm at room temperature and 77 K. As a result, the maximum emission wavelength was 474 nm and the half width was 23 nm at room temperature, and the maximum emission wavelength was 484 nm at 77 K. E(S,Sh) calculated from the intersection of the tangent passing through the inflection point on the short wavelength side of the optical peak at 77 K and the baseline was 2.71 eV.

In addition, a thin film substrate (made of quartz) was prepared in which compound (1A-142) was dispersed in PMMA at a concentration of 1% by mass, and the fluorescence quantum yield was measured by exciting the compound at an excitation wavelength of 360 nm. The result was a low value of 29%. This was because the low solubility of compound (1A-142) led to an underestimation. Since clear luminescence was obtained, compound (1A-142) is expected to inherently exhibit strong luminescence.

Furthermore, a thin film substrate (made of glass) was prepared in which compound (1A-142) was dispersed in PMMA at a concentration of 1% by mass, and the phosphorescence spectrum was observed by exciting the substrate at 77 K with an excitation wavelength of 360 nm. As a result, the maximum emission wavelength was 483 nm. E(T,Sh), calculated from the intersection of the tangent passing through the inflection point on the short wavelength side of the phosphorescence peak and the baseline, was 2.67 eV.

ΔE(ST) was calculated to be 0.04 eV.

When a thin film substrate (made of quartz) in which compound (1A-142) was dispersed in PMMA at a concentration of 1% by mass was used, the lifetime of the delayed fluorescent component was measured using a fluorescence lifetime measurement device, and was found to be 8.3 μsec (Figure 3). In the fluorescence lifetime measurement, fluorescence with an emission lifetime of 100 ns or less was determined to be instantaneous fluorescence, and fluorescence with an emission lifetime of 0.1 μs or more was determined to be delayed fluorescence, and data from 4.0 to 10.0 μsec was used to calculate the fluorescence lifetime.

<Example A3>
Evaluation of basic physical properties of compound (1A-195)
[Absorption characteristics]
A thin film formed on a substrate (made of glass) in which the compound (1A-195) was dispersed in PMMA at a concentration of 1% by mass was prepared, and the absorption spectrum was measured. The longest wavelength absorption peak was at 481 nm.

[Light Emitting Characteristics]
A thin film substrate (made of glass) was prepared by dispersing compound (1A-195) in PMMA at a concentration of 1% by mass, and the fluorescence spectrum was observed by excitation at an excitation wavelength of 360 nm at room temperature and 77 K. As a result, the maximum emission wavelength was 492 nm and the half width was 21 nm at room temperature, and the maximum emission wavelength was 500 nm at 77 K. E(S,Sh) calculated from the intersection of the tangent passing through the inflection point on the short wavelength side of the optical peak at 77 K and the baseline was 2.57 eV.

In addition, a thin film substrate (made of quartz) was prepared in which compound (1A-195) was dispersed in PMMA at a concentration of 1% by mass, and the fluorescence quantum yield was measured by exciting the substrate at an excitation wavelength of 360 nm, resulting in a value of 69%, indicating strong luminescence.

Furthermore, a thin film substrate (made of glass) was prepared in which compound (1A-195) was dispersed in PMMA at a concentration of 1% by mass, and the phosphorescence spectrum was observed by exciting the substrate at 77 K with an excitation wavelength of 360 nm. As a result, the maximum emission wavelength was 502 nm. E(T,Sh), calculated from the intersection of the tangent passing through the inflection point on the short wavelength side of the phosphorescence peak and the baseline, was 2.57 eV.

The calculated ΔE(ST) was 0.008 eV.

When a thin film substrate (made of quartz) in which compound (1A-195) was dispersed in PMMA at a concentration of 1% by mass was used, the lifetime of the delayed fluorescent component was measured with a fluorescence lifetime measurement device, and was found to be 5.2 μsec (Figure 4). In the fluorescence lifetime measurement, fluorescence with an emission lifetime of 100 ns or less was determined to be instantaneous fluorescence, and fluorescence with an emission lifetime of 0.1 μs or more was determined to be delayed fluorescence, and data from 4.0 to 10.0 μsec was used to calculate the fluorescence lifetime.

<Example A4>
Evaluation of basic physical properties of compound (1A-197)
[Absorption characteristics]
A thin film formed on a substrate (made of glass) in which the compound (1A-197) was dispersed in PMMA at a concentration of 1% by mass was prepared, and the absorption spectrum was measured. The longest wavelength absorption peak was at 461 nm.

[Light Emitting Characteristics]
A thin film substrate (made of glass) was prepared by dispersing compound (1A-197) in PMMA at a concentration of 1% by mass, and the fluorescence spectrum was observed by excitation at an excitation wavelength of 340 nm at room temperature and 77 K. As a result, the maximum emission wavelength was 475 nm and the half width was 31 nm at room temperature, and the maximum emission wavelength was 478 nm at 77 K. E(S,Sh) calculated from the intersection of the tangent passing through the inflection point on the short wavelength side of the optical peak at 77 K and the baseline was 2.66 eV.

In addition, a thin film substrate (made of quartz) was prepared in which compound (1A-197) was dispersed in PMMA at a concentration of 1% by mass, and the fluorescence quantum yield was measured by exciting the substrate at an excitation wavelength of 340 nm, resulting in a value of 76%, indicating strong luminescence.

Furthermore, a thin film substrate (made of glass) was prepared in which compound (1A-197) was dispersed in PMMA at a concentration of 1% by mass, and the phosphorescence spectrum was observed by exciting the substrate at 77 K with an excitation wavelength of 340 nm. As a result, the maximum emission wavelength was 479 nm. E(T,Sh), calculated from the intersection of the tangent passing through the inflection point on the short wavelength side of the phosphorescence peak and the baseline, was 2.63 V.

ΔE(ST) was calculated to be 0.03 eV.

When a thin film substrate (made of quartz) in which compound (1A-197) was dispersed in PMMA at a concentration of 1% by mass was used, the lifetime of the delayed fluorescence component was measured with a fluorescence lifetime measurement device, and was found to be 9.3 μsec (Figure 5). In the fluorescence lifetime measurement, fluorescence with an emission lifetime of 100 ns or less was determined to be instantaneous fluorescence, and fluorescence with an emission lifetime of 0.1 μs or more was determined to be delayed fluorescence, and data from 4.0 to 40.0 μsec was used to calculate the fluorescence lifetime.

<Evaluation of deposition type organic EL elements>
<Example B1>
Each thin film is laminated by vacuum deposition at a vacuum degree of 5×10 ⁻⁴ Pa on a glass substrate (26 mm×28 mm×0.7 mm) on which an anode made of ITO (indium tin oxide) with a thickness of 50 nm is formed.
First, NPD is evaporated on ITO to a thickness of 40 nm, and TcTa is evaporated on the NPD to a thickness of 15 nm to form a hole layer consisting of two layers. Then, mCP is evaporated to a thickness of 15 nm to form an electron blocking layer. Next, compound DOBNA1 as a host and compound (1A-92) as a dopant are co-evaporated from different evaporation sources to form an emitting layer having a thickness of 20 nm. At this time, the mass ratio of the host and the emitting dopant is 99:1. Next, 2CzBN is evaporated to a thickness of 10 nm, and then BPy-TP2 is evaporated to a thickness of 20 nm to form an electron transport layer consisting of two layers. Next, LiF is evaporated to a thickness of 1 nm, and aluminum is evaporated on the LiF to a thickness of 100 nm to form a cathode, and an organic EL device is obtained.

In the above Table 1, "NPD" is N,N'-diphenyl-N,N'-dinaphthyl-4,4'-diaminobiphenyl, "TcTa" is 4,4',4"-tris(N-carbazolyl)triphenylamine, "mCP" is 1,3-bis(N-carbazolyl)benzene, "DOBNA" is 3,11-di-o-tolyl-5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene, "2CzBN" is 3,4-di(9H-carbazol-9-yl)benzonitrile, and "BPy-TP2" is 2,7-di([2,2'-bipyridine]-5-yl)triphenylene. The chemical structures are shown below.

<Evaluation of Coating-Type Organic EL Device>
Next, an organic EL element obtained by forming an organic layer by coating will be described.

<Synthesis of polymer host compound: SPH-101>
SPH-101 was synthesized according to the method described in International Publication No. 2015/008851. A copolymer in which M2 or M3 was bonded next to M1 was obtained, and the ratio of each unit was estimated to be 50:26:24 (molar ratio) based on the feed ratio.

<Synthesis of polymer hole transport compound: XLP-101>
XLP-101 was synthesized according to the method described in JP 2018-61028 A. A copolymer in which M5 or M6 was bonded next to M4 was obtained, and it is estimated from the feed ratio that each unit is 40:10:50 (molar ratio).

<Examples C1 to C9>
A coating solution of the material for forming each layer is prepared to prepare a coating type organic EL element.

<Preparation of Organic EL Elements of Examples C1 to C3>
Table 2 shows the material composition of each layer in the organic EL element.

The structure of "ET1" in Table 2 is shown below.

<Preparation of Light-Emitting Layer-Forming Composition (1)>
The following components are stirred until a homogeneous solution is obtained to prepare a composition (1) for forming a light-emitting layer. The prepared composition for forming a light-emitting layer is spin-coated on a glass substrate and dried by heating under reduced pressure to obtain a coating film with no film defects and excellent smoothness.
SPH-101 1.96 weight%
Compound (X) 0.04% by weight
Xylene 69.00% by weight
Decalin 29.00% by weight

Compound (X) is a polycyclic aromatic compound represented by the above general formula (1A) or general formula (1B), a polymer compound obtained by polymerizing the polycyclic aromatic compound as a monomer (i.e., the monomer has a reactive substituent), a polymer crosslinked product obtained by further crosslinking the polymer compound, a pendant polymer compound obtained by substituting the monomer in a main chain polymer, or a pendant polymer crosslinked product obtained by further crosslinking the pendant polymer compound. The polymer compound or pendant polymer compound for obtaining the polymer crosslinked product or the pendant polymer crosslinked product has a crosslinkable substituent.

<PEDOT:PSS solution>
A commercially available PEDOT:PSS solution (Clevios™ P VP AI4083, an aqueous dispersion of PEDOT:PSS, manufactured by Heraeus Holdings) is used.

<Preparation of OTPD solution>
OTPD (LT-N159, manufactured by Luminescence Technology Corp.) and IK-2 (a photocationic polymerization initiator, manufactured by San-Apro Co., Ltd.) are dissolved in toluene to prepare an OTPD solution having an OTPD concentration of 0.7% by weight and an IK-2 concentration of 0.007% by weight.

<Preparation of XLP-101 solution>
XLP-101 is dissolved in xylene to a concentration of 0.6% by weight to prepare a 0.7% by weight XLP-101 solution.

<Preparation of PCz solution>
PCz (polyvinylcarbazole) is dissolved in dichlorobenzene to prepare a 0.7 wt % PCz solution.

<Example C1>
A PEDOT:PSS solution is spin-coated on a glass substrate on which ITO has been evaporated to a thickness of 150 nm, and baked on a hot plate at 200 ° C. for 1 hour to form a PEDOT:PSS film with a thickness of 40 nm (hole injection layer). Next, an OTPD solution is spin-coated, dried on a hot plate at 80 ° C. for 10 minutes, exposed to an exposure intensity of 100 mJ/cm ² with an exposure machine, and baked on a hot plate at 100 ° C. for 1 hour to form a solution-insoluble OTPD film with a thickness of 30 nm (hole transport layer). Next, a composition for forming an emitting layer (1) is spin-coated, and baked on a hot plate at 120 ° C. for 1 hour to form a emitting layer with a thickness of 20 nm.

The prepared multilayer film is fixed to a substrate holder of a commercially available deposition apparatus (manufactured by Showa Vacuum Co., Ltd.), and a molybdenum deposition boat containing ET1, a molybdenum deposition boat containing LiF, and a tungsten deposition boat containing aluminum are attached. After reducing the pressure of the vacuum chamber to 5×10 ⁻⁴ Pa, ET1 is heated and deposited to a thickness of 30 nm to form an electron transport layer. The deposition rate when forming the electron transport layer is 1 nm/sec. Thereafter, LiF is heated and deposited at a deposition rate of 0.01 to 0.1 nm/sec to a thickness of 1 nm. Next, aluminum is heated and deposited to a thickness of 100 nm to form a cathode. In this manner, an organic EL device is obtained.

<Example C2>
An organic EL element is obtained in the same manner as in Example C1. The hole transport layer is formed by spin-coating an XLP-101 solution and baking it on a hot plate at 200° C. for 1 hour to form a film with a thickness of 30 nm.

<Example C3>
An organic EL element is obtained in the same manner as in Example C1. The hole transport layer is formed by spin-coating a PCz solution and baking it on a hot plate at 120° C. for 1 hour to form a film with a thickness of 30 nm.

<Preparation of Organic EL Elements of Examples C4 to C6>
Table 3 shows the material composition of each layer in the organic EL element.

<Preparation of compositions (2) to (4) for forming light-emitting layer>
A composition for forming a light-emitting layer (2) is prepared by stirring the following components until a homogeneous solution is obtained.
mCBP 1.98% by weight
Compound (X) 0.02% by weight
Toluene 98.00% by weight

A composition for forming a light-emitting layer (3) is prepared by stirring the following components until a homogeneous solution is obtained.
SPH-101 1.98% by weight
Compound (X) 0.02% by weight
Xylene 98.00% by weight

A composition for forming a light-emitting layer (4) is prepared by stirring the following components until a homogeneous solution is obtained.
DOBNA 1.98% by weight
Compound (X) 0.02% by weight
Toluene 98.00% by weight

In Table 3, "mCBP" is 3,3'-bis(N-carbazolyl)-1,1'-biphenyl, "DOBNA" is 3,11-di-o-tolyl-5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene, and "TSPO1" is diphenyl[4-(triphenylsilyl)phenyl]phosphine oxide. The chemical structures are shown below.

<Example C4>
A glass substrate on which an ITO film was formed to a thickness of 45 nm was spin-coated with an ND-3202 (Nissan Chemical Industries) solution, and then heated in an air atmosphere at 50°C for 3 minutes, and then heated at 230°C for 15 minutes to form an ND-3202 film with a thickness of 50 nm (hole injection layer). Next, an XLP-101 solution was spin-coated, and heated on a hot plate in a nitrogen gas atmosphere at 200°C for 30 minutes to form an XLP-101 film with a thickness of 20 nm (hole transport layer). Next, a composition for forming an emitting layer (2) was spin-coated, and heated in a nitrogen gas atmosphere at 130°C for 10 minutes to form a emitting layer with a thickness of 20 nm.

The prepared multilayer film is fixed to a substrate holder of a commercially available deposition apparatus (manufactured by Showa Vacuum Co., Ltd.), and a molybdenum deposition boat containing TSPO1, a molybdenum deposition boat containing LiF, and a tungsten deposition boat containing aluminum are attached. After reducing the pressure of the vacuum chamber to 5×10 ⁻⁴ Pa, TSPO1 is heated and deposited to a thickness of 30 nm to form an electron transport layer. The deposition rate when forming the electron transport layer is 1 nm/sec. Thereafter, LiF is heated and deposited at a deposition rate of 0.01 to 0.1 nm/sec to a thickness of 1 nm. Next, aluminum is heated and deposited to a thickness of 100 nm to form a cathode. In this manner, an organic EL device is obtained.

<Examples C5 and C6>
An organic EL element is obtained by using the composition for forming a light-emitting layer (3) or (4) in the same manner as in Example C4.

<Preparation of Organic EL Elements of Examples C7 to C9>
Table 4 shows the material composition of each layer in the organic EL element.

<Preparation of compositions (5) to (7) for forming light-emitting layer>
A composition for forming a light-emitting layer (5) is prepared by stirring the following components until a homogeneous solution is obtained.
mCBP 1.80% by weight
2PXZ-TAZ 0.18 weight%
Compound (X) 0.02% by weight
Toluene 98.00% by weight

A composition for forming a light-emitting layer (6) is prepared by stirring the following components until a homogeneous solution is obtained.
SPH-101 1.80% by weight
2PXZ-TAZ 0.18 weight%
Compound (X) 0.02% by weight
Xylene 98.00% by weight

A composition for forming a light-emitting layer (7) is prepared by stirring the following components until a homogeneous solution is obtained.
DOBNA 1.80% by weight
2PXZ-TAZ 0.18 weight%
Compound (X) 0.02% by weight
Toluene 98.00% by weight

In Table 4, "2PXZ-TAZ" is 10,10'-((4-phenyl-4H-1,2,4-triazole-3,5-diyl)bis(4,1-phenyl))bis(10H-phenoxazine). The chemical structure is shown below.

<Example C7>
A glass substrate on which an ITO film was formed to a thickness of 45 nm was spin-coated with an ND-3202 (manufactured by Nissan Chemical Industries, Ltd.) solution, and then heated in an air atmosphere at 50° C. for 3 minutes, and then heated at 230° C. for 15 minutes to form an ND-3202 film with a thickness of 50 nm (hole injection layer). Next, an XLP-101 solution was spin-coated, and heated on a hot plate in a nitrogen gas atmosphere at 200° C. for 30 minutes to form an XLP-101 film with a thickness of 20 nm (hole transport layer). Next, a composition for forming an emitting layer (5) was spin-coated, and heated in a nitrogen gas atmosphere at 130° C. for 10 minutes to form an emitting layer with a thickness of 20 nm.

The prepared multilayer film is fixed to a substrate holder of a commercially available deposition apparatus (manufactured by Showa Vacuum Co., Ltd.), and a molybdenum deposition boat containing TSPO1, a molybdenum deposition boat containing LiF, and a tungsten deposition boat containing aluminum are attached. After reducing the pressure of the vacuum chamber to 5×10 ⁻⁴ Pa, TSPO1 is heated and deposited to a thickness of 30 nm to form an electron transport layer. The deposition rate when forming the electron transport layer is 1 nm/sec. Thereafter, LiF is heated and deposited at a deposition rate of 0.01 to 0.1 nm/sec to a thickness of 1 nm. Next, aluminum is heated and deposited to a thickness of 100 nm to form a cathode. In this manner, an organic EL device is obtained.

<Examples C8 and C9>
An organic EL element is obtained by using the composition for forming a light-emitting layer (6) or (7) in the same manner as in Example C7.

As described above, some of the compounds according to the present invention have been evaluated as materials for organic EL devices and shown to be excellent materials, but other compounds that have not been evaluated also have the same basic skeleton and have a similar structure overall, and those skilled in the art will understand that they are similarly excellent materials for organic EL devices.

According to a preferred embodiment of the present invention, it is possible to provide a polycyclic aromatic compound having a novel structure that can be used as a material for organic devices, such as a material for an organic electroluminescence (EL) element, and by using this polycyclic aromatic compound, it is possible to provide an excellent organic device, such as an organic electroluminescence (EL) element.

REFERENCE SIGNS LIST 100 Organic electroluminescent element 101 Substrate 102 Anode 103 Hole injection layer 104 Hole transport layer 105 Light-emitting layer 106 Electron transport layer 107 Electron injection layer 108 Cathode

Claims (16)

A polycyclic aromatic compound represented by the following general formula (2A) :

the portion [φ2]n is a portion constituted by n units of at least one type of unit structure selected from the group consisting of the unit structure represented by the above formula (φ2-m1) and the unit structure represented by the above formula (φ2-m2),
n is an integer from 1 to 3;
Each R ^a is independently hydrogen or alkyl having 1 to 4 carbon atoms ;
R ^b and R ^c each independently represent a hydrogen atom, an aryl having 6 to 10 carbon atoms, a diarylamino (wherein the aryl has 6 to 10 carbon atoms), or an alkyl having 1 to 12 carbon atoms , and at least one hydrogen atom in R ^b and R ^c may be substituted with an alkyl having 1 to 4 carbon atoms ;
Y is B ;
^X1 is >N-R , and each R in the >N-R is independently an aryl having 6 to 10 carbon atoms which may be substituted by an alkyl having 1 to 4 carbon atoms ;
^X2 is N ;
In the above formula (2A), formula (φ2-m1), and formula (φ2-m2), at least one pair of adjacent R ^c in adjacent c rings are bonded to each other to form a single bond or an arylene having 6 to 10 carbon atoms ,
At least one hydrogen atom in the compound represented by the above formula (2A) may be substituted with deuterium, cyano, or halogen. The polycyclic aromatic compound according to claim 1, which is represented by the following structural formula:

("Me" in the structural formula represents a methyl group.) The polycyclic aromatic compound according to claim 1 , which is represented by any one of the following structural formulas:

(In the structural formula, "Me" represents a methyl group and "tBu" represents a t-butyl group.) The polycyclic aromatic compound according to claim 1 , which is represented by any one of the following structural formulas:

(In the structural formula, "Me" represents a methyl group and "tBu" represents a t-butyl group.) A material for an organic device, comprising the polycyclic aromatic compound according to any one of claims 1 to 4 . The material for an organic device according to claim 5 , which is a material for an organic electroluminescent element, a material for an organic field effect transistor, a material for an organic thin-film solar cell, or a material for a wavelength conversion filter. The material for an organic device according to claim 6 , wherein the material for an organic electroluminescent device is a material for a light-emitting layer. An ink composition comprising the polycyclic aromatic compound according to any one of claims 1 to 4 and an organic solvent. 13. An organic electroluminescence device comprising a pair of electrodes consisting of an anode and a cathode, and an organic layer disposed between the pair of electrodes and containing the polycyclic aromatic compound according to claim 1 . The organic electroluminescent device according to claim 9 , wherein the organic layer is a light-emitting layer. The organic electroluminescent device according to claim 10 , wherein the light-emitting layer contains a host and the polycyclic aromatic compound as a dopant. 12. The organic electroluminescent device according to claim 11 , wherein the host is an anthracene-based compound, a fluorene-based compound, or a dibenzochrysene-based compound. 13. The organic electroluminescence device according to claim 10, further comprising at least one of an electron transport layer and an electron injection layer disposed between the cathode and the light emitting layer, wherein at least one of the electron transport layer and the electron injection layer contains at least one selected from the group consisting of borane derivatives, pyridine derivatives, fluoranthene derivatives, BO-based derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, carbazole derivatives, triazine derivatives, benzimidazole derivatives, phenanthroline derivatives, quinolinol-based metal complexes, thiazole derivatives, benzothiazole derivatives, silole derivatives and azoline derivatives. 14. The organic electroluminescent device according to claim 13, wherein at least one of the electron transport layer and the electron injection layer further contains at least one selected from the group consisting of alkali metals, alkaline earth metals, rare earth metals, oxides of alkali metals, halides of alkali metals, oxides of alkaline earth metals, halides of alkaline earth metals, oxides of rare earth metals, halides of rare earth metals, organic complexes of alkali metals , organic complexes of alkaline earth metals, and organic complexes of rare earth metals. A display device or a lighting device comprising the organic electroluminescent device according to any one of claims 9 to 14 . A wavelength conversion filter comprising the material for wavelength conversion filters according to claim 6 .

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