JP7538596B2 - Polycyclic aromatic compounds - Google Patents

Description

The present invention relates to polycyclic aromatic compounds and polymers thereof (hereinafter collectively referred to as "polycyclic aromatic compounds"), and to organic electroluminescent devices, organic field-effect transistors, organic thin-film solar cells, and display devices and lighting devices using the same. Note that in this specification, "organic electroluminescent devices" may be referred to as "organic EL devices" or simply "devices."

Display devices using electroluminescent light-emitting elements have been extensively studied because they can be made thin and energy-efficient. Furthermore, organic electroluminescent elements 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 an organic compound that are disposed between the pair of electrodes. 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 transport materials, for example, triphenylamine-based compounds have been developed (JP 2001-172232 A). As electron transport 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 as a material for use in organic electroluminescence devices and organic thin-film solar cells (WO 2012/118164). This material is characterized by its improved planarity, which is achieved by linking the aromatic rings that make up the triphenylamine, 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. This document evaluates the charge transport properties of, for example, NO-linked compounds (compound 1 on page 63), but does not describe how to manufacture materials other than NO-linked compounds. Furthermore, 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 with a conjugated structure that has a large triplet exciton energy (T1) can emit phosphorescence with a shorter wavelength, making them useful as materials for blue light-emitting layers. Additionally, compounds with new conjugated structures with large T1 are also required as electron transport materials and hole transport materials that sandwich 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, 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 ).

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 US Patent Application Publication No. 2019/67577

As mentioned above, 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, the organic EL characteristics obtained from materials other than the NO-linked compounds reported in Patent Documents 1 to 4, and the methods for producing such materials, are not yet known.

In addition, Patent Documents 6 and 7 report polycyclic aromatic compounds containing boron and organic EL devices using the same, but in order to further improve device characteristics, there is a demand for light-emitting layer materials, particularly dopant materials, that can improve the luminous efficiency and device life.

As a result of intensive research to solve the above problems, the present inventors have found 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 have completed the present invention. That is, the present invention provides a polycyclic aromatic compound or a multimer thereof as shown below, and further provides a material for an organic device, such as a material for an organic EL element containing a polycyclic aromatic compound or a multimer thereof as shown below.

In this specification, the chemical structure or the substituent may be expressed by the number of carbon atoms, but in the case where a substituent is substituted on the chemical structure or where a substituent is further substituted on the substituent, the number of carbon atoms 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 in the substituents A and 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 in the substituents A and B.

上記式（１）中、
Ａ環、Ｂ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、
Ｙ^１は、Ｂ、Ｐ、Ｐ＝Ｏ、Ｐ＝Ｓ、Ａｌ、Ｇａ、Ａｓ、Ｓｉ－Ｒ、またはＧｅ－Ｒであり、前記Ｓｉ－ＲおよびＧｅ－ＲのＲは、アリール、アルキル、またはシクロアルキルであり、
Ｘ^１は、＞Ｏ、＞Ｎ－Ｒ、＞Ｃ（－Ｒ）_２、＞Ｓｉ（－Ｒ）_２、＞Ｐ－Ｒ、＞Ｓ、または＞Ｓｅであり、前記＞Ｎ－Ｒ、＞Ｃ（－Ｒ）_２、＞Ｓｉ（－Ｒ）_２、および＞Ｐ－ＲのＲは、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＞Ｎ－Ｒ、＞Ｃ（－Ｒ）_２、＞Ｓｉ（－Ｒ）_２、および＞Ｐ－ＲのＲは、単結合または連結基により、前記Ａ環およびＢ環の少なくとも１つの環と結合していてもよく、
Ｘ^２は、＞Ｏ、＞Ｎ－Ｒ、＞Ｃ（－Ｒ）_２、＞Ｓｉ（－Ｒ）_２、＞Ｐ－Ｒ、＞Ｓ、または＞Ｓｅであり、前記＞Ｎ－Ｒ、＞Ｃ（－Ｒ）_２、＞Ｓｉ（－Ｒ）_２、または＞Ｐ－ＲのＲは、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＞Ｎ－Ｒ、＞Ｃ（－Ｒ）_２、＞Ｓｉ（－Ｒ）_２、および＞Ｐ－ＲのＲは、単結合または連結基により、前記Ｂ環およびＣ環の少なくとも１つの環と結合していてもよく（ただし、前記Ｘ^１が、＞Ｏ、＞Ｎ－Ｒ、＞Ｐ－Ｒ、＞Ｓ、または＞Ｓｅである場合は、Ｘ^２としての＞Ｎ－Ｒ、＞Ｃ（－Ｒ）_２、＞Ｓｉ（－Ｒ）_２、および＞Ｐ－ＲのＲは前記Ｂ環と結合しない）、そして、
式（１）で表される化合物または単位構造における少なくとも１つの水素は、ハロゲン、シアノ、または重水素で置換されていてもよい。 Item 1.
A polycyclic aromatic compound represented by the following general formula (1), or a multimer of a polycyclic aromatic compound having a plurality of unit structures represented by the following general formula (1).

In the above formula (1),
ring A, ring B, 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;
^Y1 is B, P, P=O, P=S, Al, Ga, As, Si-R, or Ge-R, wherein R in the Si-R and Ge-R is aryl, alkyl, or cycloalkyl;
^X1 is >O, >N-R, >C(-R) ₂ , >Si(-R) ₂ , >P-R, >S, or >Se, and R in the >N-R, >C(-R) ₂ , >Si(-R) ₂ , and >P-R is an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl, or an optionally substituted cycloalkyl, and R in the >N-R, >C(-R) ₂ , >Si(-R) ₂ , and >P-R may be bonded to at least one of the rings A and B by a single bond or a linking group;
X ² is >O, >N-R, >C(-R) ₂ , >Si(-R) ₂ , >P-R, >S, or >Se, and R of >N-R, >C(-R) ₂ , >Si(-R) ₂ , or >P-R is an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl, or an optionally substituted cycloalkyl, and R of >N-R, >C(-R) ₂ , >Si(-R) ₂ , and >P-R may be bonded to at least one of the rings B and C via a single bond or a linking group (however, when X ¹ is >O, >N-R, >P-R, >S, or >Se, R of >N-R, >C(-R) ₂ , >Si(-R) ₂ , and >P-R as X ² is not bonded to the ring B), and
At least one hydrogen atom in the compound or unit structure represented by formula (1) may be substituted with a halogen atom, a cyano atom, or a deuterium atom.

Item 2.
In the above formula (1),
ring A, ring B, and ring C are each independently an aryl ring or a heteroaryl ring, at least one hydrogen atom in these rings may be substituted with 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, and these rings have a 5- or 6-membered ring that shares a bond with the central fused bicyclic structure of the above formula (1) composed of Y ¹ , X ¹ , and X ² ,
^Y1 is B, P, P=O, P=S, Al, Ga, As, Si-R, or Ge-R, wherein R in the Si-R and Ge-R is aryl, alkyl, or cycloalkyl;
X ¹ is >O, >N-R, >C(-R) ₂ , >Si(-R) ₂ , >P-R, >S, or >Se, R of the >N-R, >C(-R) ₂ , >Si(-R) ₂ , and >P-R is aryl which may be substituted with alkyl or cycloalkyl, heteroaryl which may be substituted with alkyl or cycloalkyl, alkyl, or cycloalkyl, and R of the >N-R, >C(-R) ₂ , >Si(-R) ₂ , and >P-R may be bonded to at least one of the rings A and B by a single bond, -O-, -S-, -C(-R) ₂ -, or -N(-R)-, R of the -C(-R) ₂ - and -N(-R)- is aryl, alkyl, or cycloalkyl,
X ² is >O, >N-R, >C(-R) ₂ , >Si(-R) ₂ , >P-R, >S, or >Se, and R of the >N-R, >C(-R) ₂ , >Si(-R) ₂ , or >P-R is aryl which may be substituted with alkyl or cycloalkyl, heteroaryl which may be substituted with alkyl or cycloalkyl, alkyl, or cycloalkyl, and R of the >N-R, >C(-R) ₂ , >Si(-R) ₂ , and >P-R may be bonded to at least one of the rings B and C by a single bond, -O-, -S-, -C(-R) ₂ -, or -N(-R)- (however, when the X ¹ is >O, >N-R, >P-R, >S, or >Se, >N-R, >C(-R) 2 as X 2 may be bonded to at least one of the rings B and C by a single bond, -O-, -S-, -C(-R) ₂ -, or -N(-R)- ⁾ . R in >Si(-R) ₂ and >P-R is not bonded to the ring B), R in -C(-R) ₂ - and -N(-R)- is aryl, alkyl or cycloalkyl, and
At least one hydrogen atom in the compound or unit structure represented by formula (1) may be substituted with halogen, cyano, or deuterium.
Item 2. A polycyclic aromatic compound or a multimer thereof according to item 1.

上記式（２）中、
ａ環、ｂ環、およびｃ環における、任意の「－Ｃ（－Ｒ）＝」（ここでＲは式（２）中のＲ^１～Ｒ^１１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は式（２）中のＲ^１～Ｒ^１１である）は、「－Ｎ（－Ｒ）－」、「－Ｏ－」、または「－Ｓ－」に置き換わっていてもよく、前記「－Ｎ（－Ｒ）－」のＲは、アリール、アルキル、またはシクロアルキルであり、
Ｒ^１～Ｒ^１１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、これら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^１～Ｒ^１１のうちの隣接する基同士が結合して、ａ環、ｂ環、または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、
Ｙ^１は、Ｂ、Ｐ、Ｐ＝Ｏ、Ｐ＝Ｓ、Ａｌ、Ｇａ、Ａｓ、Ｓｉ－Ｒ、またはＧｅ－Ｒであり、前記Ｓｉ－ＲおよびＧｅ－ＲのＲは、炭素数６～１２のアリール、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^１は、＞Ｏ、＞Ｎ－Ｒ、＞Ｃ（－Ｒ）_２、＞Ｓｉ（－Ｒ）_２、＞Ｐ－Ｒ、＞Ｓ、または＞Ｓｅであり、前記＞Ｎ－Ｒ、＞Ｃ（－Ｒ）_２、＞Ｓｉ（－Ｒ）_２、および＞Ｐ－ＲのＲは、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、また、前記＞Ｎ－Ｒ、＞Ｃ（－Ｒ）_２、＞Ｓｉ（－Ｒ）_２、および＞Ｐ－ＲのＲは、単結合、－Ｏ－、－Ｓ－、－Ｃ（－Ｒ）_２－、または－Ｎ（－Ｒ）－により、前記ａ環およびｂ環の少なくとも１つの環と結合していてもよく、前記－Ｃ（－Ｒ）_２－および－Ｎ（－Ｒ）－のＲは、炭素数６～１２のアリール、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は、＞Ｏ、＞Ｎ－Ｒ、＞Ｃ（－Ｒ）_２、＞Ｓｉ（－Ｒ）_２、＞Ｐ－Ｒ、＞Ｓ、または＞Ｓｅであり、前記＞Ｎ－Ｒ、＞Ｃ（－Ｒ）_２、＞Ｓｉ（－Ｒ）_２、および＞Ｐ－ＲのＲは、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、また、前記＞Ｎ－Ｒ、＞Ｃ（－Ｒ）_２、＞Ｓｉ（－Ｒ）_２、および＞Ｐ－ＲのＲは、単結合、－Ｏ－、－Ｓ－、－Ｃ（－Ｒ）_２－、または－Ｎ（－Ｒ）－により、前記ｃ環と結合していてもよく、前記－Ｃ（－Ｒ）_２－および－Ｎ（－Ｒ）－のＲは、炭素数６～１２のアリール、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、そして、
式（２）で表される化合物または単位構造における少なくとも１つの水素は、ハロゲン、シアノ、または重水素で置換されていてもよい。 Item 3.
Item 2. The polycyclic aromatic compound or a multimer thereof according to item 1, wherein the general formula (1) is represented by the following general formula (2):

In the above formula (2),
In the ring a, ring b, and ring c, any "-C(-R)=" (wherein R is R ¹ to R ¹¹ in formula (2)) may be replaced with "-N=", any "-C(-R)=C(-R)-" (wherein R is R ¹ to R ¹¹ in formula (2)) may be replaced with "-N(-R)-", "-O-", or "-S-", and R in the "-N(-R)-" is aryl, alkyl, or cycloalkyl,
R ¹ to R ¹¹ 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, in which at least ^one hydrogen may be substituted with an aryl, heteroaryl, alkyl, or cycloalkyl. Adjacent groups among ¹¹ may be bonded to each other to form an aryl ring or a heteroaryl ring together with the a ring, the b ring, or the c ring, and at least one hydrogen atom in the formed ring may be replaced 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 may be replaced with an aryl, a heteroaryl, an alkyl, or a cycloalkyl;
^Y1 is B, P, P=O, P=S, Al, Ga, As, Si-R, or Ge-R, and R of the Si-R and Ge-R is an aryl having 6 to 12 carbon atoms, an alkyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 14 carbon atoms;
X ¹ is >O, >N-R, >C(-R) ₂ , >Si(-R) ₂ , >P-R, >S, or >Se, and R in the >N-R, >C(-R) ₂ , >Si(-R) ₂ , and >P-R is 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, and R in the >N-R, >C(-R) ₂ , >Si(-R) ₂ , and >P-R may be bonded to at least one of the ring a and ring b via a single bond, -O-, -S-, -C(-R) ₂ -, or -N(-R) _- , and R in - and -N(-R)- is an aryl having 6 to 12 carbon atoms, an alkyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 14 carbon atoms;
X ² is >O, >N-R, >C(-R) ₂ , >Si(-R) ₂ , >P-R, >S, or >Se, and R in the >N-R, >C(-R) ₂ , >Si(-R) ₂ , and >P-R is 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, and R in the >N-R, >C(-R) ₂ , >Si(-R) ₂ , and >P-R may be bonded to the ring c via a single bond, -O-, -S-, -C(-R) ₂ -, or -N(-R)-, and -C(-R) ₂ R in - and -N(-R)- is an aryl having 6 to 12 carbon atoms, an alkyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 14 carbon atoms; and
At least one hydrogen atom in the compound or unit structure represented by formula (2) may be substituted with a halogen atom, a cyano atom, or a deuterium atom.

上記式（２－Ｍ１）および式（２－Ｍ２）中、
ａ環、ｂ環、およびｃ環における、任意の「－Ｃ（－Ｒ）＝」（ここでＲは式（２－Ｍ１）または式（２－Ｍ２）中のＲ^１～Ｒ^７、Ｒ^１０、およびＲ^１１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は式（２－Ｍ１）または式（２－Ｍ２）中のＲ^１～Ｒ^７、Ｒ^１０、およびＲ^１１である）は、「－Ｎ（－Ｒ）－」、「－Ｏ－」、または「－Ｓ－」に置き換わっていてもよく、前記「－Ｎ（－Ｒ）－」のＲは、アリール、アルキル、またはシクロアルキルであり、
Ｒ^１～Ｒ^７、Ｒ^１０、およびＲ^１１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、これら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^１～Ｒ^７、Ｒ^１０、およびＲ^１１のうちの隣接する基同士が結合して、ａ環、ｂ環、または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、
Ｙ^１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およびＧｅ－ＲのＲは、炭素数６～１２のアリール、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^１は、それぞれ独立して、＞Ｏ、＞Ｎ－Ｒ、＞Ｃ（－Ｒ）_２、＞Ｓｉ（－Ｒ）_２、＞Ｐ－Ｒ、＞Ｓ、または＞Ｓｅであり、前記＞Ｎ－Ｒ、＞Ｃ（－Ｒ）_２、＞Ｓｉ（－Ｒ）_２、および＞Ｐ－ＲのＲは、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、また、前記＞Ｎ－Ｒ、＞Ｃ（－Ｒ）_２、＞Ｓｉ（－Ｒ）_２、および＞Ｐ－ＲのＲは、単結合、－Ｏ－、－Ｓ－、－Ｃ（－Ｒ）_２－、または－Ｎ（－Ｒ）－により、前記ａ環およびｂ環の少なくとも１つの環と結合していてもよく、前記－Ｃ（－Ｒ）_２－および－Ｎ（－Ｒ）－のＲは、炭素数６～１２のアリール、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は、それぞれ独立して、ＮまたはＰであり、そして、
式（２－Ｍ１）または式（２－Ｍ２）で表される多量体における少なくとも１つの水素は、ハロゲン、シアノ、または重水素で置換されていてもよい。 Item 4.
Item 4. A multimer of the polycyclic aromatic compound according to item 3, represented by the following general formula (2-M1) or (2-M2):

In the above formula (2-M1) and formula (2-M2),
Any "-C(-R)=" in the ring a, ring b, and ring c (wherein R is R ¹ to R ⁷ , R ¹⁰ , and R ¹¹ in the formula (2-M1) or the formula (2-M2)) may be replaced with "-N=", any "-C(-R)=C(-R)-" (wherein R is R ¹ to R ⁷ , R ¹⁰ , and R ¹¹ in the formula (2-M1) or the formula (2-M2)) may be replaced with "-N(-R)-", "-O-", or "-S-", and R in the "-N(-R)-" is an aryl, an alkyl, or a cycloalkyl,
R ¹ to R ⁷ , R ¹⁰ , and R ¹¹ 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, in which at least one hydrogen may be replaced by an aryl, heteroaryl, alkyl, or cycloalkyl, and R ¹ to R ⁷ , R ¹⁰ , and R Adjacent groups among ¹¹ may be bonded to each other to form an aryl ring or a heteroaryl ring together with the a ring, the b ring, or the c ring, and at least one hydrogen atom in the formed ring may be replaced 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 may be replaced with an aryl, a heteroaryl, an alkyl, or a cycloalkyl;
^Y1 is each independently B, P, P=O, P=S, Al, Ga, As, Si-R, or Ge-R, and R of Si-R and Ge-R is an aryl having 6 to 12 carbon atoms, an alkyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 14 carbon atoms;
X ¹ is each independently >O, >N-R, >C(-R) ₂ , >Si(-R) ₂ , >P-R, >S, or >Se, and R in the >N-R, >C(-R) ₂ , >Si(-R) ₂ , and >P-R is 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, and R in the >N-R, >C(-R) ₂ , >Si(-R) ₂ , and >P-R may be bonded to at least one of the ring a and ring b via a single bond, -O-, -S-, -C(-R) ₂ -, or -N(-R) _- , and R in - and -N(-R)- is an aryl having 6 to 12 carbon atoms, an alkyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 14 carbon atoms;
Each ^X2 is independently N or P; and
At least one hydrogen atom in the multimer represented by formula (2-M1) or formula (2-M2) may be substituted with halogen, cyano, or deuterium.

Item 5.
In the above formula (2), formula (2-M1), and formula (2-M2),
In the ring a, the ring b, and the ring c, any "-C(-R)=" (wherein R is R ¹ to R ¹¹ in the formula (2), the formula (2-M1), or the formula (2-M2)) may be replaced with "-N=", any "-C(-R)=C(-R)-" (wherein R is R ¹ to R ¹¹ in the formula (2), the formula (2-M1), or the formula (2-M2)) may be replaced with "-N(-R)-", "-O-", or "-S-", and R in the "-N(-R)-" is an aryl having 6 to 12 carbon atoms, an alkyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 14 carbon atoms,
R ¹ to R ¹¹ are each independently hydrogen, an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms, diarylamino (wherein the aryl is an aryl having 6 to 12 carbon atoms), diarylboryl (wherein the aryl is an aryl having 6 to 12 carbon atoms, and two aryls may be bonded via a single bond or a linking group), an alkyl having 1 to 24 carbon atoms, a cycloalkyl having 3 to 24 carbon atoms, an alkoxy having 1 to 24 carbon atoms, or an aryloxy having 6 to 30 carbon atoms, in which at least one hydrogen may be substituted by 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 ¹¹ may be bonded to each other to form an aryl ring having 9 to 16 carbon atoms or a heteroaryl ring having 6 to 15 carbon atoms together with the a ring, the b ring, or the c ring, and 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, a cycloalkyl having 3 to 24 carbon atoms, an alkoxy having 1 to 24 carbon atoms, or an aryloxy having 6 to 30 carbon atoms, and at least one hydrogen atom in these 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;
^Each Y1 is independently B, P, P=O, P=S, or Si-R, wherein R in the Si-R is an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms;
^X1 is each independently >O, >N-R, or >S, and R of the >N-R is an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms;
In formula (2), ^X2 is >O, >N-R, or >S, and R of the >N-R is an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms;
In formula (2-M1) or formula (2-M2), ^X2 is N, and
At least one hydrogen atom in the compound or unit structure represented by formula (2), or the multimer represented by formula (2-M1) or formula (2-M2) may be substituted with halogen, cyano, or deuterium.
Item 5. The polycyclic aromatic compound or a multimer thereof according to Item 3 or 4.

Item 6.
In the above formula (2), formula (2-M1), and formula (2-M2),
In the ring a, the ring b, and the ring c, any "-C(-R)=" (wherein R is R ¹ to R ¹¹ in the formula (2), the formula (2-M1), or the formula (2-M2)) may be replaced with "-N=", any "-C(-R)=C(-R)-" (wherein R is R ¹ to R ¹¹ in the formula (2), the formula (2-M1), or the formula (2-M2)) may be replaced with "-N(-R)-", "-O-", or "-S-", and R in the "-N(-R)-" is an aryl having 6 to 12 carbon atoms, an alkyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 14 carbon atoms,
R ¹ to R ¹¹ are each independently 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, in which at least one hydrogen atom 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;
^Each Y1 is independently B, P, P=O, or P=S;
Each ^X1 is independently >O or >N-R, and R in the >N-R is an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms;
In formula (2), ^X2 is >O or >N-R, and R of the >N-R is an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms, and
In formula (2-M1) or formula (2-M2), ^X2 is N.
Item 5. The polycyclic aromatic compound or a multimer thereof according to Item 3 or 4.

Item 7.
In the above formula (2), formula (2-M1), and formula (2-M2),
R ¹ to R ¹¹ are each independently hydrogen, 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 the 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;
^Y1 is B;
Each ^X1 is independently >O or >N-R, and R in the >N-R is an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms;
In formula (2), ^X2 is >O or >N-R, and R of the >N-R is an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms, and
In formula (2-M1) or formula (2-M2), ^X2 is N.
Item 5. The polycyclic aromatic compound or a multimer thereof according to Item 3 or 4.

Item 8.
Item 2. The polycyclic aromatic compound or a multimer thereof according to item 1, which is represented by any one of the following structural formulas:

Item 9.
Item 9. A reactive compound in which the polycyclic aromatic compound or a multimer thereof according to any one of Items 1 to 8 is substituted with a reactive substituent.

Item 10.
Item 10. A polymer compound obtained by polymerizing the reactive compound according to item 9 as a monomer, or a crosslinked polymer obtained by further crosslinking the polymer compound.

Item 11.
Item 10. A pendant polymer compound in which a reactive compound as described in item 9 is substituted on a main chain polymer, or a pendant polymer crosslinked product in which the pendant polymer compound is further crosslinked.

Item 12.
Item 12. The polymer compound or crosslinked polymer according to item 10, or the pendant polymer compound or crosslinked pendant polymer according to item 11, comprising, as a repeating unit, 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.

Item 13.
Item 9. A material for an organic device, comprising the polycyclic aromatic compound or a multimer thereof according to any one of Items 1 to 8.

Item 14.
Item 10. A material for an organic device, comprising the reactive compound according to item 9.

Item 15.
Item 11. A material for an organic device, comprising the polymer compound or crosslinked polymer according to item 10.

Item 16.
Item 12. A material for an organic device, comprising the pendant polymer compound or the pendant polymer crosslinked product according to item 11.

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

Item 18.
Item 18. The material for an organic device according to item 17, which is a material for a light-emitting layer of an organic electroluminescent device.

Item 19.
9. An ink composition comprising the polycyclic aromatic compound or a multimer thereof according to any one of items 1 to 8, and an organic solvent.

Item 20.
10. An ink composition comprising the reactive compound according to item 9 and an organic solvent.

Item 21.
Item 10. An ink composition comprising a main chain polymer, the reactive compound according to item 9, and an organic solvent.

Item 22.
Item 11. An ink composition comprising the polymer compound or crosslinked polymer according to item 10 and an organic solvent.

Item 23.
Item 12. An ink composition comprising the pendant polymer compound or the pendant polymer crosslinked product according to item 11 and an organic solvent.

Item 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 or a polymer thereof according to any one of items 1 to 8, the reactive compound according to item 9, the polymer compound or crosslinked polymer according to item 10, or the pendant polymer compound or crosslinked polymer according to item 11.

Item 25.
24. 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 formed from the ink composition according to any one of items 19 to 23.

Item 26.
Item 26. The organic electroluminescent device according to item 24 or 25, wherein the organic layer is a light-emitting layer.

Item 27.
Item 27. The organic electroluminescent device according to item 26, wherein the light-emitting layer comprises the polycyclic aromatic compound or a multimer thereof, a reactive compound, a polymer compound, a crosslinked polymer, a pendant polymer compound, or a pendant crosslinked polymer as a host, and a dopant.

Item 28.
Item 28. The organic electroluminescent device according to item 27, wherein the host further contains an anthracene-based compound, a fluorene-based compound, or a dibenzochrysene-based compound.

Item 29.
Item 29. The organic electroluminescence device according to any one of Items 24 to 28, 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 the 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, and quinolinol-based metal complexes.

Item 30.
Item 30. The organic electroluminescent device according to item 29, 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.

Item 31.
Item 31. The organic electroluminescence device according to any one of Items 24 to 30, 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.

Item 32.
Item 32. A display device or lighting device comprising the organic electroluminescent device according to any one of Items 24 to 31.

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 hetero elements such as boron, phosphorus, oxygen, nitrogen, and sulfur have a large HOMO-LUMO gap (band gap Eg in a thin film). This is thought to be because six-membered rings containing hetero elements have low aromaticity, which suppresses the decrease in the HOMO-LUMO gap associated with the expansion of the conjugated system. These polycyclic aromatic compounds can arbitrarily change the HOMO and LUMO energies by introducing substituents, making it possible to optimize the ionization potential and electron affinity according to 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.

なお、上記の各構造式中の符号の定義は上述した定義と同じであり、さらに、この段落以降で示すすべての構造式中の符号の定義も上述した定義と同じである。 1. Polycyclic aromatic compound and multimer thereof The present invention relates to a polycyclic aromatic compound represented by the following general formula (1) or a multimer of a polycyclic aromatic compound having a plurality of unit structures represented by the following general formula (1), and is preferably a polycyclic aromatic compound represented by the following general formula (2) or a multimer of a polycyclic aromatic compound having a plurality of unit structures represented by the following general formula (2).

The symbols in the structural formulae above are defined as above, and the symbols in all structural formulae shown in this paragraph and thereafter are defined as above.

In formula (1), the A ring, the B ring, and the C ring 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. In the case where these groups have a substituent, examples of the substituent include an aryl, a heteroaryl, an alkyl, or a cycloalkyl. Details of the rings and the substituents listed here will be described below.

In formula (2), R ¹ to R ¹¹ 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 atom in these may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl. Details of the substituents listed here will be described below.

The aryl or heteroaryl ring in formula (1) preferably has a 5- or 6-membered ring which shares a bond with the central fused two-ring structure of formula (1) composed of Y ¹ , X ¹ , and X ² .
Here, the term "fused bicyclic structure" refers to a structure in which two saturated hydrocarbon rings, which are composed of Y ¹ , X ¹ , and X ² as shown in the center of formula (1), are fused together. In addition, the term "six-membered ring sharing a bond with the fused bicyclic structure" refers to a ring (benzene ring (six-membered ring)) fused to the fused bicyclic structure, as shown in formula (2), for example. In addition, "an aryl ring or heteroaryl ring (which is the A ring) has this six-membered ring" means that the A ring is formed only from this six-membered ring, or that the A ring is formed by further condensing other rings to this six-membered ring so as to include this six-membered ring. In other words, the term "an aryl ring or heteroaryl ring (which is the A ring) having a six-membered ring" refers to the six-membered ring constituting all or a part of the A ring being fused to the fused bicyclic structure. The same explanation applies to "B ring (b ring)", "C ring (c ring)", and "five-membered ring".

Ring A (or ring B or ring C) in formula (1) corresponds to ring a and its substituents R ¹ to R ³ (or ring b and its substituents R ⁴ to R ⁷ , or ring c and its substituents R ⁸ to R ¹¹ ) in formula (2). That is, formula (2) corresponds to a structure in which "rings A to C having 6-membered rings" are selected as rings A to C in formula (1). In that sense, each ring in formula (2) is represented by lowercase letters a to c.

In formula (2), adjacent groups among the substituents R ¹ to R ¹¹ of the ring a, ring b, and ring c 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 (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 may be substituted with an aryl, heteroaryl, alkyl, or cycloalkyl. Details of the rings and substituents listed here will be described below.
Therefore, in the polycyclic aromatic compound represented by formula (2), the ring structure constituting the compound changes depending on the mutual bonding form of the substituents in ring a, ring b, and ring c, as shown in the following formulas (2-a) to (2-abc). Ring A', ring B', and ring C' in each formula correspond to ring A, ring B, and ring C in formula (1), respectively.

In the above formulas (2-a) to (2-abc), the ring A', ring B', and ring C' are aryl or heteroaryl rings formed by bonding adjacent groups among the substituents R ¹ to R ¹¹ together with the ring a, ring b, and ring c, respectively, when explained in formula (2). (They can also be said to be condensed rings formed by condensing other ring structures to the ring a, ring b, or ring c). As can be seen from the above formulas (2-a) to (2-abc), for example, R ³ of the ring a and R ⁴ of the ring b, R ⁷ of the ring b and R ⁸ of the ring c, R ¹¹ of the ring c and R ¹ of the ring a are not "adjacent groups" and are not bonded to each other. In other words, "adjacent groups" means groups adjacent on the same ring.

The compounds represented by any of the above formulas (2-a) to (2-abc) are compounds having ring A' (or ring B' or ring C') formed by condensing a benzene ring, which is ring a (or ring b or ring c), with a benzene ring, an indole ring, a pyrrole ring, a benzofuran ring, or a benzothiophene ring, etc., and the condensed ring A' (or condensed ring B' or condensed ring C') formed is a naphthalene ring, a carbazole ring, an indole ring, a dibenzofuran ring, or a dibenzothiophene ring, etc., respectively.

上記式（２－ａ－ｅｘ）は、式（２－ａ）の具体例であり、式（２）のａ環におけるＲ^２とＲ^３が結合して、ａ環（ベンゼン環）と共に、Ａ’で示すアリール環（ナフタレン環）が形成された例である。形成されたアリール環は上述した「縮合２環構造」と結合を共有する６員環（ベンゼン環ａ）を有している。なお、アリール環Ａ’（式（１）のＡ環）への任意の置換基をＲ^１の他にｎ個のＲで示しており、ｎの上限は置換可能な最大数である。
上記式（２－ｂ－ｅｘ）は、式（２－ｂ）の具体例であり、式（２）のｂ環におけるＲ^５とＲ^６が結合して、ｂ環（ベンゼン環）と共に、Ｂ’で示すヘテロアリール環（カルバゾール環）が形成された例である。形成されたヘテロアリール環は上述した「縮合２環構造」と結合を共有する６員環（ベンゼン環ｂ）を有している。なお、ヘテロアリール環Ｂ’（式（１）のＢ環）への任意の置換基をＲ^４およびＲ^７の他にｎ個のＲで示しており、ｎの上限は置換可能な最大数である。
上記式（２－ｃ－ｅｘ）は、式（２－ｃ）の具体例であり、式（２）のｃ環におけるＲ^８とＲ^９が結合して、ｃ環（ベンゼン環）と共に、Ｃ’で示すヘテロアリール環（ジベンゾフラン環）が形成された例である。形成されたヘテロアリール環は上述した「縮合２環構造」と結合を共有する６員環（ベンゼン環ｃ）を有している。なお、ヘテロアリール環Ｃ’（式（１）のＣ環）への任意の置換基をＲ^１０およびＲ^１１の他にｎ個のＲで示しており、ｎの上限は置換可能な最大数である。
これらの具体例の説明は、上述した具体例以外のあらゆる形態にも同様に適用できる。 For example, more specific examples of formula (2-a), formula (2-b), and formula (2-c) are shown below.

The above formula (2-a-ex) is a specific example of formula (2-a), and is an example in which ^R2 and ^R3 in the ring a of formula (2) are bonded to form an aryl ring (naphthalene ring) represented by A' together with the ring a (benzene ring). The formed aryl ring has a six-membered ring (benzene ring a) that shares a bond with the above-mentioned "condensed two-ring structure". Note that optional substituents on the aryl ring A' (ring A of formula (1)) are represented by n Rs in addition to ^R1 , and the upper limit of n is the maximum number that can be substituted.
The above formula (2-b-ex) is a specific example of formula (2-b), and is an example in which ^R5 and ^R6 in ring b of formula (2) are bonded to form a heteroaryl ring (carbazole ring) represented by B' together with ring b (benzene ring). The formed heteroaryl ring has a 6-membered ring (benzene ring b) that shares a bond with the above-mentioned "fused 2-ring structure". In addition to ^R4 and ^R7 , optional substituents on the heteroaryl ring B' (ring B in formula (1)) are represented by n Rs, and the upper limit of n is the maximum number of possible substitutions.
The above formula (2-c-ex) is a specific example of formula (2-c), and is an example in which R ⁸ and R ⁹ in the ring c of formula (2) are bonded to form a heteroaryl ring (dibenzofuran ring) represented by C' together with the ring c (benzene ring). The formed heteroaryl ring has a 6-membered ring (benzene ring c) that shares a bond with the above-mentioned "fused 2-ring structure". In addition to R ¹⁰ and R ¹¹ , optional substituents on the heteroaryl ring C' (ring C of formula (1)) are represented by n Rs, and the upper limit of n is the maximum number that can be substituted.
The description of these specific examples can be similarly applied to any form other than the specific examples described above.

Y ¹ in formula (1) 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, alkyl, or cycloalkyl. In the case of P=O, P=S, Si-R, or Ge-R, the atom bonded to the A ring, the B ring, or X ² is P, Si, or Ge. Y ¹ is preferably B, P, P=O, P=S, or Si-R, more preferably B, P, P=O, or P=S, and particularly preferably B. This explanation is the same for Y ¹ in formula (2). Details of the substituents listed here will be described below.

In formula (1), ^X1 and ^X2 are each independently >O, >N-R, >C(-R) ₂ , >Si(-R) ₂ , >P-R, >S, or >Se, and R in >N-R, >C(-R) ₂ , >Si(-R) ₂ , and >P-R is optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl, or optionally substituted cycloalkyl.
Here, R in >N-R, >C(-R) ₂ , >Si(-R) ₂ , and >P-R may be bonded to a nearby ring via a single bond or a linking group. Specifically, R in >N-R, >C(-R) ₂ , >Si(-R) ₂ , or >P-R as X ¹ may be bonded to at least one of the rings A and B. R in >N-R, >C(-R) ₂ , >Si(-R) ₂ , or >P-R as X ² may be bonded to at least one of the rings B and C, except that when X ¹ is >O, >N-R, >P-R, >S, or >Se, R in >N-R, >C(-R) ₂ , >Si(-R) ₂ , or >P-R as X ² does not bond to the ring B.
As ^X1 and ^X2 which can be involved in a bond, among >N-R, >C(-R) ₂ , >Si(-R) ₂ , and >P-R, >N-R, >C(-R) ₂ , and >P-R are preferred, >N-R or >P-R are more preferred, and >N-R is particularly preferred.
The linking group connecting R to the ring in >N-R, >C(-R) ₂ , >Si(-R) ₂ or >P-R is preferably -O-, -S-, -C(-R) ₂ - or -N(-R)-. In addition, R in "-C(-R) ₂ -" and "-N(-R)-" is aryl, alkyl or cycloalkyl.
The above explanation also applies to ^X1 and ^X2 in formula (2).
The details of the substituents listed here will be described later.

The provision in formula (1) that "R of the >N-R, >C(-R) ₂ , >Si(-R) ₂ , and >P-R is bonded to at least one of the ring A and ring B (or the ring B and ring C) via a single bond or a linking group" corresponds to the provision in formula ( ₂ ) that "R of the >N-R, >C(-R) ₂ , >Si(-R) ₂ , and >P-R is bonded to at least one of the ring a and ring b (or the ring b and ring c) via a single bond, -O-, -S-, -C(-R) 2 -, or -N(-R)-".

This definition can be expressed, for example, by the structure of the following formula (2-aX1), formula (2-bX1), formula (2-bX2Y1), or formula (2-cX2), in which ^X1 or ^X2 , and in some cases ^Y1 , have a ring structure incorporated into fused ring A', fused ring B', or fused ring C'. The formed fused ring A', fused ring B', and fused ring C are, for example, a phenoxazine ring, a phenothiazine ring, or an acridine ring.

上記式（２－ａＸ１）は、Ｘ^１の選択肢におけるＲがａ環と結合した例であり、式（２）における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るＡ’環を有する化合物を表している。上記式（２－ａＸ１－ｅｘ）は、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、ａ環（ベンゼン環）と結合しており、形成された縮合環Ａ’はフェノキサジン環である。なお、縮合環Ａ’への任意の置換基をＲ^１およびＲ^２の他にｎ個のＲで示しており、ＲはＡ環への置換基と同じであり、ｎの上限は置換可能な最大数である。

The above formula (2-aX1) is an example in which R in the options for ^X1 is bonded to the ring a, and represents a compound having a ring A' formed by condensing another ring to the ring a (benzene ring) in formula (2) so as to incorporate ^X1 . The above formula (2-aX1-ex) represents a more specific example, in which R (phenyl group) of >N-R which is ^X1 is bonded to the ring a (benzene ring) via the linking group -O-, and the formed condensed ring A' is a phenoxazine ring. Note that optional substituents on the condensed ring A' are represented by n R in addition to ^R1 and ^R2 , R is the same as the substituent on the ring A, and the upper limit of n is the maximum number that can be substituted.

上記式（２－ｂＸ１）は、Ｘ^１の選択肢におけるＲがｂ環と結合した例であり、式（２）におけるｂ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るＢ’環を有する化合物を表している。上記式（２－ｂＸ１－ｅｘ）は、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－Ｓ－により、ｂ環（ベンゼン環）と結合しており、形成された縮合環Ｂ’はフェノチアジン環である。なお、縮合環Ｂ’への任意の置換基をＲ^５～Ｒ^７の他にｎ個のＲで示しており、ＲはＢ環への置換基と同じであり、ｎの上限は置換可能な最大数である。

The above formula (2-bX1) is an example in which R in the options for ^X1 is bonded to ring b, and represents a compound having ring B' formed by condensing another ring to ring b (benzene ring) in formula (2) so as to incorporate ^X1 . The above formula (2-bX1-ex) represents a more specific example, in which R (phenyl group) of >N-R which is ^X1 is bonded to ring b (benzene ring) via -S- which is a linking group, and the formed condensed ring B' is a phenothiazine ring. Note that optional substituents on condensed ring B' are represented by n R in addition to R ⁵ to R ⁷ , R is the same as the substituent on ring B, and the upper limit of n is the maximum number that can be substituted.

上記式（２－ｂＸ２Ｙ１）は、Ｘ^２の選択肢におけるＲがｂ環と結合した例であり、式（２）におけるｂ環（ベンゼン環）に対してＸ^２およびＹ^１を取り込むようにして他の環が縮合して形成されるＢ’環を有する化合物を表している。上記式（２－ｂＸ２Ｙ１－ｅｘ）は、より具体的な例を表しており、Ｘ^２である＞Ｎ－ＲのＲ（フェニル基）が、単結合により、ｂ環（ベンゼン環）と結合しており、形成された縮合環Ｂ’はＮとＹ^１を含む縮合三環系ヘテロアリール環である。なお、縮合環Ｂ’への任意の置換基をＲ^４～Ｒ^６の他にｎ個のＲで示しており、ＲはＢ環への置換基と同じであり、ｎの上限は置換可能な最大数である。

The above formula (2-bX2Y1) is an example where R in the options for ^X2 is bonded to ring b, and represents a compound having ring B' formed by condensing another ring to ring b (benzene ring) in formula (2) so as to incorporate ^X2 and ^Y1 . The above formula (2-bX2Y1-ex) represents a more specific example, in which R (phenyl group) of >N-R which is ^X2 is bonded to ring b (benzene ring) by a single bond, and the formed condensed ring B' is a condensed tricyclic heteroaryl ring containing N and ^Y1 . Note that optional substituents on condensed ring B' are represented by n R in addition to ^R4 to ^R6 , R is the same as the substituent on ring B, and the upper limit of n is the maximum number that can be substituted.

上記式（２－ｃＸ２）は、Ｘ^２の選択肢におけるＲがｃ環と結合した例であり、式（２）におけるｃ環（ベンゼン環）に対してＸ^２を取り込むようにして他の環が縮合して形成されるＣ’環を有する化合物を表している。上記式（２－ｃＸ２－ｅｘ）は、より具体的な例を表しており、Ｘ^２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）と結合しており、形成された縮合環Ｃ’はフェノキサジン環である。なお、縮合環Ｃ’への任意の置換基をＲ^９～Ｒ^１１の他にｎ個のＲで示しており、ＲはＣ環への置換基と同じであり、ｎの上限は置換可能な最大数である。

The above formula (2-cX2) is an example in which R in the options for ^X2 is bonded to the c ring (benzene ring) in formula (2), and represents a compound having a C' ring formed by condensing another ring to incorporate ^X2 to the c ring (benzene ring) in formula ( ² ). The above formula (2-cX2-ex) represents a more specific example, in which R (phenyl group) of >N-R which is X2 is bonded to the c ring (benzene ring) via the linking group -O-, and the formed condensed ring C' is a phenoxazine ring. Note that optional substituents on the condensed ring C' are represented by n R in addition to R ⁹ to R ¹¹ , R is the same as the substituent on the C ring, and the upper limit of n is the maximum number that can be substituted.

In addition to the structures of the above-mentioned formula (2-aX1), formula (2-bX1), formula (2-bX2Y1), or formula (2-cX2), a structure in which the above-mentioned formula (2-aX1) and formula (2-bX1) are combined, that is, a structure having ring A′ and ring B′ incorporating ^X1 may be used, and similarly, the following combined structures may be used.
Formula (2-aX1) and Formula (2-bX2Y1)
Formula (2-aX1) and Formula (2-cX2)
Formula (2-bX1) and Formula (2-bX2Y1)
Formula (2-bX1) and Formula (2-cX2)
Formula (2-bX2Y1) and Formula (2-cX2)
Formula (2-aX1), Formula (2-bX1), and Formula (2-bX2Y1)
Formula (2-aX1), Formula (2-bX1), and Formula (2-cX2)
Formula (2-aX1), Formula (2-bX2Y1), and Formula (2-cX2)
Formula (2-bX1), Formula (2-bX2Y1), and Formula (2-cX2)
Formula (2-aX1), Formula (2-bX1), Formula (2-bX2Y1) and Formula (2-cX2)
In addition, the explanation of the specific examples of formula (2-aX1-ex), formula (2-bX1-ex), formula (2-bX2Y1-ex), or formula (2-cX2-ex) described above can be similarly applied to any forms other than these specific examples.

以上に示すように、例えばｂ環における「－Ｃ（－Ｒ^５）＝」の箇所が「－Ｎ＝」に置き換わってもよく、このようにして、式（２）でベンゼン環として表示されるｂ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、ｂ環上に隣接する基が存在する場合（上記式中ではＲ^６およびＲ^７）には、これらが結合してｂ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。
その他、以下のような変形例もある。

その他の箇所が「－Ｎ＝」に置き換わった場合や、ａ環またはｃ環が変化した場合についても同じである。 In formula (2), any "-C(-R)=" (wherein R is R ¹ to R ¹¹ in formula (2)) in ring a, ring b, and ring c may be replaced with "-N=".

As shown above, for example, "-C(-R ⁵ )=" in ring b may be replaced with "-N=", and thus ring b shown as a benzene ring in formula (2) may be changed to a pyridine ring, pyrimidine ring, pyridazine ring, pyrazine ring, or other nitrogen-containing heteroaryl ring. Furthermore, when adjacent groups are present on ring b (R ⁶ and R ⁷ in the above formula), they are bonded to form a heteroaryl ring (a quinoline ring in the above formula) together with ring b, 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 positions are replaced with "-N=" or when the a-ring or c-ring is changed.

Also, as an example, a structure in which all "-C(-R)=" are replaced with "-N=" is shown below.

以上に示すように、例えばｂ環における「－Ｃ（－Ｒ^７）＝Ｃ（－Ｒ^６）－」の箇所が「－Ｎ（－Ｒ）－」、「－Ｏ－」、または「－Ｓ－」に置き換わってもよく、このようにして、式（２）でベンゼン環として表示されるｂ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に変化してもよい。また、ｂ環上に隣接する基が存在する場合（上記式中ではＲ^４およびＲ^５）には、これらが結合してｂ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）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。
その他、以下のような変形例もある。

その他の箇所が「－Ｎ（－Ｒ）－」、「－Ｏ－」、または「－Ｓ－」に置き換わった場合や、ａ環またはｃ環が変化した場合についても同じである。 In formula (2), any "-C(-R)=C(-R)-" (wherein R is R ¹ to R ¹¹ in formula (2)) in ring a, ring b, and ring c may be replaced with "-N(-R)-", "-O-", or "-S-", and R in the "-N(-R)-" is aryl, alkyl, or cycloalkyl. Details of the substituents listed here will be described below.

As shown above, for example, "-C(-R ⁷ )=C(-R ⁶ )-" in ring b may be replaced with "-N(-R)-", "-O-" or "-S-", and thus ring b shown as a benzene ring in formula (2) may be changed to an R-substituted pyrrole ring, furan ring, thiophene ring or other nitrogen-, oxygen- or sulfur-containing heteroaryl ring. Furthermore, when adjacent groups are present on ring b (R ⁴ and R ⁵ in the above formula), they are bonded together with ring b to form a heteroaryl ring (an R-substituted indole ring, benzofuran ring or benzothiophene ring in the above formula), 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-" or "-S-" or when ring a or ring c is changed.

In the above explanations of formulas (2-a) to (2-abc), (2-a-ex) to (2-c-ex), (2-aX1) to (2-cX2), and (2-aX1-ex) to (2-cX2-ex), rings a, b, and c are described as benzene rings, but the same applies when rings a to c are changed to nitrogen-containing heteroaryl rings (six- or five-membered rings) or oxygen- and sulfur-containing heteroaryl rings (five-membered rings).

Next, we will explain the details of the rings and substituents (including the second substituent that further substitutes the first substituent) listed in the explanation so far.

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 rings A to C in formula (1) corresponds to the "aryl ring formed together with ring a, ring b, or ring c by bonding adjacent groups among R ¹ to R ¹¹ " defined in formula (2). However, for this "formed aryl ring", ring a, ring b, or ring c is already composed of a benzene ring having 6 carbon atoms, so the lower limit of the carbon number is the total carbon number of 9 in the fused ring formed by condensing the smallest 5-membered ring to this benzene ring.

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, or a phenanthrene 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 rings A to C in formula (1) corresponds to the "heteroaryl ring formed together with ring a, ring b, or ring c by bonding adjacent groups among R ¹ to R ¹¹ " defined in formula (2), but for this "formed aryl ring", ring a, ring b, or ring c is already composed of a benzene ring having 6 carbon atoms, so the lower limit of the carbon number is the total carbon number of the fused ring formed by condensing this benzene ring with the smallest 5-membered ring, which is 6. However, rings a to c, which are benzene rings, may be changed to nitrogen-containing heteroaryl rings (6- or 5-membered rings) or oxygen-sulfur-containing heteroaryl rings (5-membered rings) as described above, and in this case, the lower limit of the carbon number will change 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 phthalazine ring, a naphthyridine ring, a purine ring, a pteridine ring, a kaolin ... These include a carbazole 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, or a benzobenzoindolocarbazole 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 (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, etc.

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.

"Heteroaryl" is, for example, a heteroaryl having 2 to 30 carbon atoms, and is 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, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, nyl, phenoxathiinyl, 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, or benzobenzoindolocarbazolyl.

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 such as phenyl, an alkyl such as methyl, or a cycloalkyl such as cyclohexyl or adamantyl, and such a group is also included in the heteroaryl as the second substituent.

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, and the details of this heteroaryl can be found in the above description of the "heteroaryl".
The term "arylheteroarylamino" refers to an amino group substituted with an aryl and a heteroaryl. For details of the aryl and the heteroaryl, the above descriptions of "aryl" and "heteroaryl" can be cited.

"Diarylboryl" is a boryl group substituted with two aryls, and the above-mentioned explanation of "aryl" can be cited for details of this aryl. In addition, the two aryls may be bonded via a single bond or a linking group (e.g., >C(-R) ₂ , >O, >S, or >N-R). Here, R in >C(-R) ₂ and >N-R is aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, or aryloxy, and at least one hydrogen in these groups may be further substituted with aryl, heteroaryl, alkyl, or cycloalkyl. For details of the substituents listed here, the above-mentioned explanations of "aryl", "heteroaryl", and "diarylamino", as well as the explanations of "alkyl", "cycloalkyl", "alkoxy", and "aryloxy" can be cited for details.

"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, 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, or n-eicosyl.

"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 carbon atoms, norbornenyl, bicyclo[1.0.1]butyl, bicyclo[1.1.1]pentyl, bicyclo[2.0.1]pentyl, bicyclo[1.2.1]hexyl, bicyclo[3.0.1]hexyl, bicyclo[2.1.2]heptyl, bicyclo[2.2.2]octyl, adamantyl, diamantyl, decahydronaphthalenyl, and decahydroazulenyl.

"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, 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-methylpentyloxy butyloxy, 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 n-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, or n-eicosyloxy.

"Aryloxy" is a group represented by "Ar-O- (Ar is an aryl group)" and the details of this aryl can be found in the explanation of "aryl" above.

"Substituted silyl" refers to a silyl substituted with at least one of, for example, 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 on the alkyl and cycloalkyl, see the explanations of "alkyl" and "cycloalkyl" above.

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

Substituents (including the first and second substituents) affect the emission wavelength of the polycyclic aromatic compound due to the steric hindrance, electron donating, and electron withdrawing properties of the structure, so the emission wavelength can be adjusted by selecting the substituent. Preferred substituents are groups represented by the following structural formula. In the structural formula, "Me" represents methyl, "tBu" represents t-butyl, "tAm" represents t-amyl, "tOct" represents t-octyl, and * represents the bond position.

Among these substituents, methyl, t-butyl, t-amyl, t-octyl, 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, carbazolyl, 3,6-dimethylcarbazolyl, 3,6-di-t-butylcarbazolyl, trimethylsilyl, t- Butyldimethylsilyl, triphenylsilyl, and phenoxy are more preferred, and methyl, t-butyl, t-amyl, t-octyl, adamantyl, 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 are even more preferred.
From the viewpoint of ease of synthesis, larger steric hindrance is preferred for selective synthesis. For example, t-butyl, t-amyl, t-octyl, adamantyl, o-tolyl, p-tolyl, 2,4-xylyl, 2,5-xylyl, 2,6-xylyl, 2,4,6-mesityl, di-p-tolylamino, diphenylamino, bis(p-(t-butyl)phenyl)amino, carbazolyl, 3,6-dimethylcarbazolyl, and 3,6-di-t-butylcarbazolyl are preferred, and t-butyl, t-amyl, adamantyl, diphenylamino, bis(p-(t-butyl)phenyl)amino, carbazolyl, and 3,6-di-t-butylcarbazolyl are more preferred.

The present invention also relates to a multimer of a polycyclic aromatic compound having a plurality of unit structures represented by general formula (1), preferably a multimer of a polycyclic aromatic compound having a plurality of unit structures represented by general formula (2). The multimer is preferably a dimer to a hexamer, more preferably a dimer to a trimer, and particularly preferably a dimer. The multimer may have a plurality of the unit structures in one compound. For example, the unit structures may be linked by a linking group such as a single bond, an alkylene group having 1 to 3 carbon atoms, a phenylene group, or a naphthylene group (linked multimer), or may be linked so that any ring (ring A, ring B, or ring C, ring a, ring b, or ring c) contained in the unit structure is shared by multiple unit structures (ring-shared multimer), or may be linked so that any ring (ring A, ring B, or ring C, ring a, ring b, or ring c) contained in the unit structure is condensed (ring-condensed multimer), or may be linked so that some rings are shared and some rings are condensed (combined ring-shared and ring-condensed multimer). Ring-shared multimers, ring-condensed multimers, and composite multimers are preferred, and ring-shared multimers and composite multimers are more preferred.

上記式（２－Ｍ１）で表される多量体化合物は、式（２）の単位構造におけるｃ環であるベンゼン環を共有し、かつ式（２）の単位構造におけるｂ環であるベンゼン環同士が縮合するようにして、二つの式（２）で表される単位構造を一つの化合物中に有する多量体化合物（複合型多量体）である。また、上記式（２－Ｍ２）で表される多量体化合物は、式（２）の単位構造におけるｃ環であるベンゼン環を共有するようにして、二つの式（２）で表される単位構造を一つの化合物中に有する多量体化合物（環共有型多量体）である。 Examples of such multimers include multimer compounds represented by the following formula (2-M1) or formula (2-M2).

The multimeric compound represented by the formula (2-M1) is a multimeric compound (complex multimer) having two unit structures represented by formula (2) in one compound, in such a way that the benzene ring that is the c-ring in the unit structure of formula (2) is shared and the benzene rings that are the b-ring in the unit structure of formula (2) are condensed together. The multimeric compound represented by the formula (2-M2) is a multimeric compound (ring-sharing multimer) having two unit structures represented by formula (2) in one compound, in such a way that the benzene ring that is the c-ring in the unit structure of formula (2) is shared.

上記式（２－Ｍ３）で表される多量体化合物は、二つの式（２）で表される単位構造が単結合により連結された多量体化合物（連結型多量体）である。上記式（２－Ｍ４）で表される多量体化合物は、二つの式（２）で表される単位構造がエーテル結合（連結基「－Ｏ－」）により連結された多量体化合物（連結型多量体）である。上記式（２－Ｍ５）で表される多量体化合物は、式（２）の単位構造におけるｂ環であるベンゼン環を共有するようにして、二つの式（２）で表される単位構造を一つの化合物中に有する多量体化合物（環共有型多量体）である。上記式（２－Ｍ６）で表される多量体化合物は、式（２）の単位構造におけるａ環であるベンゼン環同士が縮合するようにして、二つの式（２）で表される単位構造を一つの化合物中に有する多量体化合物（環縮合型多量体）である。 Further, examples thereof include multimeric compounds represented by any one of the following formulae (2-M3) to (2-M6).

The multimeric compound represented by the formula (2-M3) is a multimeric compound (linked multimer) in which two unit structures represented by the formula (2) are linked by a single bond. The multimeric compound represented by the formula (2-M4) is a multimeric compound (linked multimer) in which two unit structures represented by the formula (2) are linked by an ether bond (linking group "-O-"). The multimeric compound represented by the formula (2-M5) is a multimeric compound (ring-sharing multimer) in which two unit structures represented by the formula (2) are included in one compound by sharing a benzene ring that is a b ring in the unit structure of the formula (2). The multimeric compound represented by the formula (2-M6) is a multimeric compound (ring-condensed multimer) in which two unit structures represented by the formula (2) are included in one compound by condensing a benzene ring that is an a ring in the unit structure of the formula (2).

Since the multimers represented by formulae (2-M1) to (2-M6) are composed of a plurality of unit structures represented by formula (2), the definitions of the symbols in formulae (2-M1) to (2-M6) and changes in the ring structure can be directly referred to the explanation in formula (2). However, ^X2 in formulae (2-M1) and (2-M2) is limited to N or P, and N is preferable.

At least one hydrogen atom in the polycyclic aromatic compound represented by formula (1) or formula (2) and its multimer may be substituted with a halogen atom, cyano, or deuterium. The halogen atom is fluorine, chlorine, bromine, or iodine, preferably fluorine, chlorine, or bromine, and more preferably fluorine or chlorine.

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

The polycyclic aromatic compound represented by the above general formula (1) and its multimer 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, or a material for organic thin-film solar cells, as a polymer compound obtained by polymerizing a reactive compound substituted with a reactive substituent as a monomer (the monomer for obtaining this polymer compound has a polymerizable substituent), or as a crosslinked polymer obtained by further crosslinking the polymer compound (the polymer compound for obtaining this crosslinked polymer has a crosslinkable substituent), or as 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 as 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, groups represented by formula (XLS-1), (XLS-2), (XLS-3), (XLS-9), (XLS-10) or (XLS-17) are preferred, and groups represented by formula (XLS-1), (XLS-3) or (XLS-17) are more preferred.

Such a polymer compound, crosslinked polymer, pendant-type polymer compound, and pendant-type crosslinked polymer may contain, in addition to the repeating units of the polycyclic aromatic compound represented by formula (1) and its multimer, 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 (1) 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 and Multimers Thereof Polycyclic aromatic compounds and multimers thereof represented by general formula (1) or (2) can basically be produced by first producing an intermediate by bonding ring A (ring a) to ring B (ring b) and ring C (ring c) via bonding groups (groups containing ^X1 or ^X2 ) (first reaction), and then bonding ring A (ring a), ring B (ring b), and ring C (ring c) via bonding groups (groups containing ^Y1 ) to produce a final product (second reaction).

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

まず、Ｘ^１とＸ^２の間の水素原子（Ａ環またはａ環上の「Ｈ」）をｎ－ブチルリチウム、ｓ－ブチルリチウムまたはｔ－ブチルリチウム等でオルトメタル化する。次いで、三塩化ホウ素や三臭化ホウ素等を加え、リチウム－ホウ素の金属交換を行った後、Ｎ，Ｎ－ジイソプロピルエチルアミン等のブレンステッド塩基を加えることで、タンデムボラフリーデルクラフツ反応させ、目的物を得ることができる。第２反応においては反応を促進させるために三塩化アルミニウム等のルイス酸を加えてもよい。 The second reaction is a reaction for introducing ^Y1 which bonds ring A (ring a), ring B (ring b), and ring C (ring c) as shown in the following schemes (1) and (2), and an example in which ^Y1 is a boron atom and ^X1 and ^X2 are >N-R is shown below. Note that the definitions of the symbols in the structural formulae in the following schemes (1) and (2) are the same as those described above, and furthermore, the definitions of the symbols in the structural formulae in all schemes shown in this paragraph and thereafter are the same as those described above.

First, the hydrogen atom between ^X1 and ^X2 ("H" on ring A or ring a) is ortho-metallated with n-butyllithium, s-butyllithium, t-butyllithium, or the like. Next, boron trichloride, boron tribromide, or the like is added to carry out lithium-boron metal exchange, and then a Brønsted base such as N,N-diisopropylethylamine is added to carry out a tandem boron-Friedel-Crafts reaction to obtain the target compound. In the second reaction, a Lewis acid such as aluminum trichloride may be added to promote the reaction.

The above schemes (1) and (2) mainly show the method for producing the polycyclic aromatic compound represented by the general formula (1) or (2), but the multimers thereof can be produced by using intermediates having multiple A rings (a rings), B rings (b rings) and C rings (c rings). Details are explained in the following schemes (3) and (4). In this case, the desired dimers and trimers can be obtained by doubling or tripling the amount of the reagent such as n-butyllithium used.

In the above schemes (1) to (4), lithium is introduced to the desired position by ortho-metallation, but lithium can also be introduced to the desired position by introducing a bromine atom or the like to the desired position and then performing halogen-metal exchange. This method is useful because it allows the synthesis of the target compound even in cases where ortho-metallation is not possible due to the influence of substituents.

By appropriately selecting the above-mentioned synthesis method and the raw materials to be used, it is possible to synthesize polycyclic aromatic compounds and multimers thereof having substituents at desired positions, Y ¹ being a boron atom, and X ¹ and X ² being >N-R. Furthermore, when synthesizing an intermediate, these polycyclic aromatic compounds can also be synthesized by setting X ¹ and X ² to a group other than >N-R, >O, >C(-R) ₂ , >Si(-R) ₂ , >P-R, >S, or >Se.

スキーム（１）～（４）と同様に、まずＸ^１とＸ^２の間の水素原子（Ａ環上の「Ｈ」）をｎ－ブチルリチウム等でオルトメタル化する。次いで、三塩化リン、硫黄の順に添加し、最後に三塩化アルミニウム等のルイス酸およびＮ，Ｎ－ジイソプロピルエチルアミン等のブレンステッド塩基を加えることで、タンデムホスファフリーデルクラフツ反応させ、Ｙ^１がリンスルフィド（Ｐ＝Ｓ）である化合物を得ることができる。また、得られたリンスルフィド化合物をｍ－クロロ過安息香酸（ｍ－ＣＰＢＡ）で処理することでＹ^１がリンオキサイド（Ｐ＝Ｏ）である化合物を得ることができ、トリエチルホスフィンで処理することでＹ^１がリン原子である化合物を得ることができる。 Next, the cases where Y ¹ is phosphorus sulfide (P═S), phosphorus oxide (P═O), or a phosphorus atom, and X ¹ and X ² are >N—R are shown in the following schemes (5) to (7).

As in schemes (1) to (4), first, the hydrogen atom between ^X1 and ^X2 ("H" on the A ring) 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 perform a tandem phospha Friedel-Crafts reaction, thereby obtaining a compound in which ^Y1 is a phosphorus sulfide (P=S). In addition, a compound in which ^Y1 is a phosphorus oxide (P=O) can be obtained by treating the obtained phosphorus sulfide compound with m-chloroperbenzoic acid (m-CPBA), and a compound in which ^Y1 is a phosphorus atom can be obtained by treating with triethylphosphine.

In the above scheme, an example has been described in which Y ¹ is B, P, P═O, or P═S, and X ¹ and X ² are >N—R. However, by appropriately changing the raw materials, it is also possible to synthesize a compound in which Y ¹ is Al, Ga, As, Si—R, or Ge—R, or in which X ¹ and X ² are >O, >C(—R) ₂ , >Si(—R) ₂ , >P—R, >S, or >Se.

Specific examples of solvents used in the above reactions include t-butylbenzene and xylene.

In addition, in the above synthesis schemes (1) to (5), examples have been shown in which a tandem hetero Friedel-Crafts reaction was carried out by ortho-metalating the hydrogen atom (or halogen atom) between ^X1 and ^X2 with n-butyllithium or the like before adding boron trichloride, boron tribromide, or the like, but the reaction can also be allowed to proceed by adding boron trichloride, boron tribromide, or the like without carrying out ortho-metalating using n-butyllithium or the like.

When ^Y1 is a phosphorus-based compound, as shown in the following scheme (8), the hydrogen atom ("H" on the A ring) between ^X1 and ^X2 (>N-R in the following formula) is orthometalated with n-butyllithium, s-butyllithium, t-butyllithium, or the like, and then bisdiethylaminochlorophosphine is added to carry out lithium-phosphorus metal exchange, followed by the addition of a Lewis acid such as aluminum trichloride to carry out a tandem phospha Friedel-Crafts reaction to obtain the target compound. This reaction method is also described in WO 2010/104047 (e.g., page 27).

In the above scheme (8), a polymeric compound can be synthesized by using an orthometalation reagent such as n-butyllithium in a molar amount two or three times that of intermediate 1. In addition, a halogen such as a bromine atom or a chlorine atom can be introduced in advance to the position where a metal such as lithium is to be introduced, and then the metal can be introduced to the desired position by halogen-metal exchange.

The orthometalation reagents used in the above schemes (1) to (8) include alkyllithiums such as methyllithium, n-butyllithium, s-butyllithium, and t-butyllithium, and organic alkali compounds such as lithium diisopropylamide, lithium tetramethylpiperidide, lithium hexamethyldisilazide, and potassium hexamethyldisilazide.

Examples of the metal exchange reagent for metal- ^Y1 used in the above schemes (1) to (8) include halides of ^Y1 such as trifluoride of Y1, trichloride of ^Y1 , tribromide of ^Y1 , and triiodide of ^Y1 , amidohalides of ^Y1 such as CIPN( _NEt2 ) ₂ , alkoxylates of ^Y1 , and aryloxylates ^{of Y1} .

Examples of the Bronsted base used in the above schemes (1) to (8) 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 (Ar is an aryl such as phenyl).

Examples of Lewis acids used in the above schemes (1) to (8) 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 , and} Y(OTf) ₃ . , _TiCl4 , _TiBr4 , _ZrCl4 , _ZrBr4 , _FeCl3 , _FeBr3 , _CoCl3 , _CoBr3 , and the like.

In the above schemes (1) to (8), a Bronsted base or Lewis acid may be used to promote the tandem hetero Friedel-Crafts reaction. However, when a halide of Y ¹ such as trifluoride of Y ¹ , trichloride of Y ¹ , tribromide of Y ¹ , or triiodide of Y ¹ 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 Bronsted base to capture the acid. On the other hand, when an amino halide of Y ¹ or an alkoxylated product of Y ¹ is used, amines and alcohols are generated as the aromatic electrophilic substitution reaction proceeds, so in many cases it is not necessary to use a Bronsted base, 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 and their multimers of the present invention also include structures in which at least one hydrogen atom is replaced by a halogen atom such as fluorine, chlorine, bromine, or iodine, cyano, or deuterium. These can be synthesized in the same manner as above by using raw materials in which the desired position is halogenated, cyanated, or deuterated, or by halogenating, cyanating, or deuterating at an intermediate or final stage of the synthesis.

The polycyclic aromatic compound and its multimer according to the present invention can be used as a material for an organic device, such as an organic electroluminescent device, an organic field effect transistor, or an organic thin-film solar cell.

3-1. Organic Electroluminescence Device The organic EL device according to this embodiment will now be described in detail with reference to the drawings. Fig. 1 is a schematic cross-sectional view showing the organic EL device 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.

The organic EL element 100 may be fabricated in the reverse order, for example, with 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, a light-emitting layer 105 provided on the electron transport layer 106, a hole transport layer 104 provided on the light-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, with the hole injection layer 103, the hole transport layer 104, the electron transport layer 106, and the electron injection layer 107 being layers that may be provided optionally. Each of the above layers may consist of 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 "transport layer/cathode", "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 injection 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/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 the hole injection layer 103 and/or the hole transport layer 104 are 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.

The hole injection/transport material must 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 hole injection efficiency to be high and for the injected holes to be efficiently transported. For this purpose, it is preferable for the material to have a small ionization potential, a large hole mobility, and excellent stability, and to be unlikely to generate impurities that act as traps during manufacture and use.

The polycyclic aromatic compound represented by the above general formula (1) and its polymer can be used as the 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 conventionally used as charge transport materials for holes in photoconductive materials, p-type semiconductors, and known compounds used in hole injection layers and hole transport layers 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-transporting material). The conductivity of the base material varies considerably depending on the number and mobility of the holes. Matrix materials with hole-transporting properties are known, for example, as benzidine derivatives (such as TPD) or starburst amine derivatives (such as TDATA), or as 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 a hole 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 explanation of the polycyclic aromatic compound represented by formula (1) can be cited as the reactive substituent.
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 forming the light-emitting layer 105 may be a polycyclic aromatic compound represented by the above general formula (1) or a polymer thereof. In addition, any compound that emits light when excited by the recombination of holes and electrons (light-emitting compound) 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 dopant material may be contained entirely in the host material, or may be contained partially in the host material. As a doping method, the dopant material can be formed by co-evaporation with the host material, but it may also be mixed with the host material in advance and then vapor-deposited simultaneously.

The amount of the host material used varies depending on the type of host material, and may 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 light-emitting layer material, 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.

Examples of host materials include condensed ring derivatives such as anthracene, pyrene, dibenzochrysene, and fluorene, which have long been known as light emitters, bisstyryl derivatives such as bisstyrylanthracene derivatives and distyrylbenzene derivatives, tetraphenylbutadiene derivatives, and cyclopentadiene derivatives. In particular, anthracene-based compounds, fluorene-based compounds, and dibenzochrysene-based compounds are preferred.

<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, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted diarylamino, an optionally substituted diheteroarylamino, an optionally substituted arylheteroarylamino, an optionally substituted alkyl, an optionally substituted cycloalkyl, an optionally substituted alkenyl, an optionally substituted alkoxy, an optionally substituted aryloxy, an optionally substituted arylthio or an 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).

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, examples of substituents for these include aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or silyl, and 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) is bonded 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 substitute 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 replaced by 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 substitute for silyl include cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, norbornenyl, bicyclo[1.1.1]pentyl, bicyclo[2.0.1]pentyl, bicyclo[1.2.1]hexyl, bicyclo[3.0.1]hexyl, bicyclo[2.1.2]heptyl, bicyclo[2.2.2]octyl, adamantyl, decahydronaphthalenyl, and decahydroazulenyl, and each of the three hydrogen atoms in the silyl is independently replaced by one of these cycloalkyls.

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

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-based compound represented by general formula (3) may be substituted with a group represented by the above formula (A). 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, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl, 1-methylheptyl, 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, n-eicosyl, etc.

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[1.0.1]butyl, bicyclo[1.1.1]pentyl, bicyclo[2.0.1]pentyl, bicyclo[1.2.1]hexyl, bicyclo[3.0.1]hexyl, bicyclo[2.1.2]heptyl, bicyclo[2.2.2]octyl, adamantyl, diamantyl, decahydronaphthalenyl, and decahydroazulenyl.

The "aryl" in ^the "optionally substituted aryl" in R to ^R includes, 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, carbazolyl, Examples of such groups include acridinyl, phenoxathiinyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenazasilinyl, indolizinyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, naphthobenzofuranyl, thiophenyl, benzothiophenyl, dibenzothiophenyl, naphthobenzothiophenyl, benzophosphoryl, dibenzophosphoryl, monovalent groups of benzophosphole oxide rings, monovalent groups of dibenzophosphole oxide rings, 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, and octyloxy.

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 as the "aryl" in R ²¹ to R ²⁸ above.

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 explained as the "cycloalkyl" in R ²¹ to R ²⁸ above. 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[2.0.1]pentyl, bicyclo[1.2.1]hexyl, bicyclo[3.0.1]hexyl, bicyclo[2.1.2]heptyl, bicyclo[2.2.2]octyl, adamantyl, decahydronaphthalenyl, and decahydroazulenyl.

Specific examples of "tricycloalkylsilyl" include tricyclopentylsilyl and tricyclohexylsilyl.

Specific examples of dialkylcycloalkylsilyl substituted with two alkyls and one cycloalkyl, and alkyldicycloalkylsilyl substituted with one alkyl and two cycloalkyls include silyl substituted with a group 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, etc.

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 the following formulas (A-2) to (A-14) include groups represented by the following formulas. 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), with groups represented by any of the above formulas (A-1) to (A-5) and (A-12) to (A-14) being preferred, groups represented by any of the above formulas (A-1) to (A-4) being more preferred, groups represented by any of the above formulas (A-1), (A-3) and (A-4) being even more preferred, and groups represented by the above formula (A-1) being particularly preferred.

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 also substituted for at least one hydrogen in the compound represented by formula (3). Among these bonding forms, the bonding form to the naphthalene ring in formula (3-X1) or formula (3-X2), the single bond in formula (3-X3), and/or 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.

Specific examples of anthracene-based compounds include compounds represented by the following formulas (3-1) to (3-72). 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, in which at least one hydrogen 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, in which 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, in which at least one hydrogen atom in the formed ring 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 of formula (1) 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 may be bonded to each other 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 with halogen, cyano, or deuterium.

<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),
^R1 to ^R16 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, in which at least one hydrogen 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 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 of formula (1) can be cited.

The alkenyl in the definition of the above formula (5) 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 with the monovalent group having the structure) is hydrogen, phenyl, biphenylyl, naphthyl, anthracenyl, methyl, ethyl, propyl, or butyl, and at least one hydrogen in these may be substituted with phenyl, biphenylyl, naphthyl, anthracenyl, methyl, ethyl, propyl, or butyl.

In addition, when a monovalent group having a structure represented by formula (5-Ar1) to formula (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 one of R ¹ to R ¹⁶ in formula (5) to form a single bond.

The above-mentioned light-emitting layer materials (host material and dopant material) can also 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 crosslinked polymers thereof, or pendant-type polymer compounds obtained by reacting a main-chain polymer with the reactive compound, or crosslinked pendant polymers thereof. In this case, the explanation of the polycyclic aromatic compound represented by formula (1) can be cited as the reactive substituent.
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 viewpoints 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 viewpoints of in-plane alignment 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 for the electron injection layer to have a high electron injection efficiency and efficiently transport the injected electrons. For this purpose, it is preferable for the material to have a large electron affinity, a large electron mobility, and excellent stability, and to be a material that is unlikely to generate impurities that become traps during manufacture and use. However, when considering the balance between the transport of holes and electrons, if the material mainly plays a role in efficiently preventing holes from the anode from flowing to the cathode without recombining, even if the electron transport ability is not that 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.

As a material (electron transport material) for forming the electron transport layer 106 or the electron injection layer 107, a polycyclic aromatic compound represented by the above general formula (1) and a polymer thereof can be used. 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. Examples of metal complexes having electron-accepting nitrogen include 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, pyrazoles, etc. Examples of suitable amine derivatives include benzoquinolin 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 an electron-accepting nitrogen can also be used, such as quinolinol metal complexes, hydroxyazole complexes such as hydroxyphenyloxazole complexes, azomethine complexes, tropolone metal complexes, flavonol metal complexes, and benzoquinoline metal complexes.

The above materials can be used alone or in combination with other 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 is an optionally substituted arylene having 20 or less carbon atoms, and each n is 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, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl, 1-methylheptyl, 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, n-eicosyl, etc.

The above description of alkyl can be used for the alkyl having 1 to 4 carbon atoms that substitutes the pyridine-based substituent.

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.

The above description of cycloalkyl can be used as the cycloalkyl with 5 to 10 carbon atoms to be substituted on the pyridine-based substituent.

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, and triphenylenyl, more preferably phenyl, 1-naphthyl, 2-naphthyl, and phenanthryl, and particularly preferably phenyl, 1-naphthyl, and 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, where examples of the substituent in the case of substitution 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, in which at least one hydrogen 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 (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 rings may be substituted with an aryl, heteroaryl, alkyl, or cycloalkyl.

In addition, 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 explanation of the polycyclic aromatic compound represented by the above general formula (1) can 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 "parts 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 "parts 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 a straight chain or a branched chain. That is, it is a straight chain alkyl having 1 to 6 carbon atoms or a branched chain alkyl having 3 to 6 carbon atoms. It is more preferably an alkyl having 1 to 4 carbon atoms (branched chain 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, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 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 in 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 ... 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, etc.

Preferred "aryl having 6 to 20 carbon atoms" is 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 example of the anthracene derivative is 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, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 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, and pentacenyl.

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.

Among 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 substituent is substituted, there is no particular limit to the type of the 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 description. In addition, 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.

The cycloalkyl group refers to a saturated alicyclic hydrocarbon group such as cyclopropyl, cyclohexyl, norbornyl, adamantyl, etc., 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 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.

The 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, that 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.

Alkylthio groups are groups 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.

The 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.

Heterocyclic groups refer to cyclic structural groups having atoms other than carbon, such as furanyl groups, thiophenyl groups, oxazolyl groups, pyridyl groups, quinolinyl groups, and carbazolyl groups, 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 can 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, and may be further 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 aryl include acenaphthylene-(1-,3-,4-,5-)yl, fluorene-(1-,2-,3-,4-,9-)yl, phenalene-(1-,2-)yl, (1-,2-,3-,4-,9-)phenanthryl, tetracyclic aryl quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl), condensed tetracyclic aryl triphenylene-(1-,2-)yl, pyrene-(1-,2-,4-)yl, naphthacene-(1-,2-,5-)yl, condensed pentacyclic aryl perylene-(1-,2-,3-)yl, pentacene-(1-,2-,5-,6-)yl, etc.

The "heteroaryl" in "optionally substituted heteroaryl" includes, for example, 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. In addition, examples of heteroaryl 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, and azolyl. Examples of such groups include clidinyl, phenoxathiinyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenazasilinyl, indolizinyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, naphthobenzofuranyl, thiophenyl, benzothiophenyl, dibenzothiophenyl, naphthobenzothiophenyl, benzophosphoryl, dibenzophosphoryl, monovalent groups of benzophosphole oxide rings, monovalent groups of dibenzophosphole oxide rings, 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, respectively.

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. 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 aryl include acenaphthylene-(1-,3-,4-,5-)yl, fluorene-(1-,2-,3-,4-,9-)yl, phenalene-(1-,2-)yl, (1-,2-,3-,4-,9-)phenanthryl, tetracyclic aryl quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl), condensed tetracyclic aryl triphenylene-(1-,2-)yl, pyrene-(1-,2-,4-)yl, naphthacene-(1-,2-,5-)yl, condensed pentacyclic aryl perylene-(1-,2-,3-)yl, pentacene-(1-,2-,5-,6-)yl, etc.

The "heteroaryl" in "optionally substituted heteroaryl" includes, for example, 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. In addition, examples of heteroaryl 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, and azolyl. Examples of such groups include clidinyl, phenoxathiinyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenazasilinyl, indolizinyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, naphthobenzofuranyl, thiophenyl, benzothiophenyl, dibenzothiophenyl, naphthobenzothiophenyl, benzophosphoryl, dibenzophosphoryl, monovalent groups of benzophosphole oxide rings, monovalent groups of dibenzophosphole oxide rings, 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, respectively.

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 aryl include acenaphthylene-(1-,3-,4-,5-)yl, fluorene-(1-,2-,3-,4-,9-)yl, phenalene-(1-,2-)yl, (1-,2-,3-,4-,9-)phenanthryl, tetracyclic aryl quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl), condensed tetracyclic aryl triphenylene-(1-,2-)yl, pyrene-(1-,2-,4-)yl, naphthacene-(1-,2-,5-)yl, condensed pentacyclic aryl perylene-(1-,2-,3-)yl, pentacene-(1-,2-,5-,6-)yl, etc.

The "heteroaryl" in "optionally substituted heteroaryl" includes, for example, 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. In addition, examples of heteroaryl 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, and azolyl. Examples of such groups include clidinyl, phenoxathiinyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenazasilinyl, indolizinyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, naphthobenzofuranyl, thiophenyl, benzothiophenyl, dibenzothiophenyl, naphthobenzothiophenyl, benzophosphoryl, dibenzophosphoryl, monovalent groups of benzophosphole oxide rings, monovalent groups of dibenzophosphole oxide rings, 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, respectively.

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 bond 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 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 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.

For the alkyl, cycloalkyl and aryl in R ¹¹ to R ¹⁸ , the explanation for R ¹¹ to R ¹⁸ in the above formula (ETM-2) can be cited. In addition to the above examples, φ can also have the following structural formulas. In the structural formulas below, R is each independently hydrogen, methyl, ethyl, isopropyl, cyclohexyl, phenyl, 1-naphthyl, 2-naphthyl, biphenylyl or terphenylyl. In each structural formula, * indicates a bonding 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 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, bis(2,4-dimethyl-8-quinolinolato)aluminum-μ-oxo-bis(2,4-dimethyl-8-quinolinolato)aluminum, bis(2-methyl-4-ethyl-8-quinolinolato)aluminum-μ-oxo-bis(2-methyl-4-ethyl-8-quinolinolato)aluminum, bis(2-methyl-4-methoxy-8-quinolinolato)aluminum-μ-oxo-bis(2-methyl-4-methoxy-8-quinolinolato)aluminum linolinate) aluminum, bis(2-methyl-5-cyano-8-quinolinate) aluminum-μ-oxo-bis(2-methyl-5-cyano-8-quinolinate) aluminum, bis(2-methyl-5-trifluoromethyl-8-quinolinate) aluminum-μ-oxo-bis(2-methyl-5-trifluoromethyl-8-quinolinate) aluminum, bis(10-hydroxybenzo[h]quinoline) beryllium, etc.

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 formulae, * 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. In addition, 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, such as a combination of Cs and Na, Cs and K, Cs and Rb, or Cs, Na and K, is preferred. By containing Cs, the reducing ability can be efficiently exerted, and by adding it to the material forming the electron transport layer or electron injection layer, the luminance of the light emitted by the organic EL element can be improved and the life span 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 monomer containing a reactive compound substituted with a reactive substituent, 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 (1).
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 is a material that 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 preferable. 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 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.

Furthermore, preferred examples include laminating 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, in order to protect the electrodes. 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, or the like, as long as electrical conductivity can be obtained.

<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 dispersing them 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, a light 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 layers 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 a reactive substituent is substituted on the low molecular weight compound, 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 methods do not require expensive vacuum deposition equipment, and can form films under atmospheric pressure. In addition, wet film formation methods allow for large area production and continuous production, which leads to reduced manufacturing costs.

On the other hand, compared to the vacuum deposition method, wet deposition methods can be difficult to layer. 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 therefore 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 common method for producing organic EL elements is to use wet deposition methods for only a few layers and vacuum deposition for the rest.

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 the electron transport layer material and the electron injection layer material 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 resist materials and negative resist materials can be used as bank materials that can be used with 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 the bank 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, polyacetates, polynorbornenes, synthetic rubbers, fluorinated polymers such as polyfluorovinylidene, polytetrafluoroethylene, and polyhexafluoropropylene, copolymers of fluoroolefins and hydrocarbon olefins, 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 organic layer forming composition 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 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 organic layer forming composition.

(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 ingredients in the composition and the concentration of the poor solvent, promoting rapid film formation. This results in a coating film with fewer defects, less 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 the film is formed, 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-forming 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 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), fluoroalkylbenzenesulfonate, fluoroalkylcarboxylate, fluoroalkylpolyoxyethyleneether, fluoroalkylammonium iodide, fluoroalkylbetaine, fluoroalkylsulfonate, diglycerol tetrakis (fluoroalkylpolyoxyethyleneether), fluoroalkyltrimethylammonium salt, fluoroalkylaminosulfonate, polyoxyethylenenonyl Examples of the alkyl ethers include phenyl ether, polyoxyethylene octylphenyl ether, polyoxyethylene alkyl ether, 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 sulfonate, and alkyl diphenyl ether disulfonate.

The surfactant may be used alone or in combination with 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 based on the total weight of the composition for forming an emitting layer, the second component is 0.0999% by weight to 8.0% by weight based on the total weight of the composition for forming an emitting layer, 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% to 1.0% by weight relative to the total weight of the composition for forming the light-emitting layer, the second component is 0.095% to 4.0% by weight relative to the total weight of the composition for forming the light-emitting layer, and the third component is 95.0% to 99.9% by weight relative to the total weight of the composition for forming the light-emitting layer. Even more preferably, the first component is 0.05% to 0.5% by weight relative to the total weight of the composition for forming the light-emitting layer, the second component is 0.25% to 2.5% by weight relative to the total weight of the composition for forming the light-emitting layer, and the third component is 97.0% to 99.7% by weight relative to 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, groups represented by formula (XLS-1), (XLS-2), (XLS-3), (XLS-9), (XLS-10) or (XLS-17) are preferred, and groups represented by formula (XLS-1), (XLS-3) or (XLS-17) are 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, and ether solvents, such as dimethoxyethane, 2-(2-methoxyethoxy)ethane, and 2-(2-ethoxyethoxy)ethane.

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 placed in 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 as appropriate. For example, when synthesizing a compound represented by formula (SPH-1) in one step, the target product is obtained by carrying out a reaction in a state in which a monomer unit (MU) and an end cap unit (EC) are added to a reaction vessel. When synthesizing a compound represented by general formula (SPH-1) 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. The target polymer can be obtained by a reaction after preparing a precursor polymer.

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 2015/145 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 International Publication No. 2016/031639, International Publication No. 2016/125560, International Publication No. 2016/031639, International Publication No. 2016/031639, International Publication No. 2016/125560, International Publication No. 2015/145871, International Publication No. 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 on the order of mm 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 method, 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-A-2003-257621, JP-A-2003-277741, JP-A-2004-119211, 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 liquid crystal display devices, particularly backlights for personal computers, where thinning is an issue, it is difficult to make them thin because conventional methods use 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 for producing organic field effect transistors or organic thin-film solar cells, 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 a source electrode and a drain electrode. When a voltage is applied to the gate electrode, an electric field is generated, and the flow of electrons (or holes) between the source electrode and drain electrode can be arbitrarily blocked 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 structures.
(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 for use.

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 (1-1): 8,13-diphenyl-8H,13H'-8,13-diaza-12b-borabenzo[gh]tetraphene

A flask containing 2,3-dichloroaniline (25 g), iodobenzene (70 g), sodium 2-methyl-2-butoxide (34 g), dichlorobis[di-t-butyl(para-dimethylaminophenyl)phosphino]palladium(II) (1.1 g) and toluene (250 ml) was heated to reflux under a nitrogen atmosphere for 4 hours. After the reaction was completed, the reaction solution was cooled to room temperature and the organic layer was separated. The organic layer was concentrated under reduced pressure, and the resulting crude was dissolved in heptane and passed through a silica gel short-path column (eluent: heptane) to obtain 2,3-dichloro-N,N-diphenylaniline (30 g) as a colorless oil.

A flask containing 2,3-dichloro-N,N-diphenylaniline (6.8 g), 2-(4,4,5,5-1,3,2-dioxaborolan-2-yl)aniline (5 g), potassium carbonate (6 g), tetrabutylammonium bromide (2.1 g), palladium(II) acetate (0.05 g), dicyclohexyl(2',6'-dimethoxy-[1,1'-biphenyl]-2-yl)phosphine (0.18 g), toluene (70 ml), Solmix A-11 (manufactured by Japan Alcohol Sales Co., Ltd., solmix, 35 ml) and water (15 ml) was heated to reflux under a nitrogen atmosphere for 2 hours. After completion of the reaction, the reaction solution was cooled to room temperature and the organic layer was separated. The organic layer was concentrated under reduced pressure, and the resulting crude product was dissolved in toluene and passed through a silica gel short-path column (eluent: toluene). The solvent of the fraction containing the target substance was distilled off under reduced pressure to obtain 2'-chloro- ^N ,N ^- diphenyl-[1,1'-biphenyl]-2,3'-diamine (8.6 g) as a pale yellow solid.

A flask containing 2'-chloro-N ^{3 '} ,N ^{3 '} -diphenyl-[1,1'-biphenyl]-2,3'-diamine (8.6 g), iodobenzene (4.7 g), sodium 2-methyl-2-butoxide (5 g), dichlorobis[di-t-butyl(para-dimethylaminophenyl)phosphino]palladium(II) (0.16 g) and toluene (90 ml) was heated to reflux under a nitrogen atmosphere for 2 hours. After the reaction was completed, the reaction solution was cooled to room temperature and the organic layer was separated. The organic layer was concentrated under reduced pressure, and the resulting crude was dissolved in heptane and passed through a silica gel short-path column (eluent: heptane) to obtain 2'-chloro-N ² ,N ^{3 '} ,N ^{3 '} -triphenyl-[1,1'-biphenyl]-2,3'-diamine (9.4 g) as a light brown oil.

A cyclohexane and n-hexane mixed solution (5 ml) of 1.0 M sec-butyllithium was dropped into a flask containing 2'-chloro-N ² ,N ^{3 '} ,N ^{3 '} -triphenyl-[1,1'-biphenyl]-2,3'-diamine (1 g) and toluene (10 ml) under a nitrogen atmosphere and ice bath. After the dropwise addition, the mixture was heated and stirred at 50°C for 1 hour. The reaction solution was cooled to room temperature again, and boron tribromide and N,N-diisopropylethylamine were added. After stirring at 0°C for 30 minutes, the mixture was heated and stirred at 120°C for 1 hour. After the reaction was completed, the reaction solution was cooled to room temperature, and water and ethyl acetate were added to separate the organic layer. The organic layer was concentrated under reduced pressure, and the resulting crude product was dissolved in toluene and passed through a silica gel pass column (eluent: toluene, heptane). The solvent of the fraction containing the target substance was distilled off under reduced pressure, and the residue was recrystallized with cyclopentyl methyl ether and Solmix A-11 (Solmix, manufactured by Japan Alcohol Sales Co., Ltd.) to obtain compound (1-1) (0.2 g) as a pale yellow solid.

The structure of the obtained compound was confirmed by liquid chromatography-mass spectrometry (LC-MS).
MS (ACPI): m/z=421 (M+)

Synthesis Example (2)
Synthesis of compound (1-101): 13-phenyl-13H-8-oxa-13-aza-12b-borabenzo[gh]tetraphene

A flask containing 1-bromo-3-phenoxybenzene (14.8 g), bis(pinacolato)diboron (18.1 g), potassium acetate (11.7 g), potassium carbonate (8.2 g), dichloromethane adduct of [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride (1.5 g), and cyclopentyl methyl ether (150 ml) was heated under reflux for 2 hours under a nitrogen atmosphere. After the reaction was completed, the insoluble matter was filtered off, and the solvent of the filtrate was distilled off under reduced pressure. The obtained crude was dissolved in heptane and passed through a silica gel short-path column (eluent: heptane), and the solvent of the fraction containing the target product was distilled off under reduced pressure to obtain 4,4,5,5-tetramethyl-2-(3-phenoxyphenyl)-1,3,2-dioxaborolane (14.2 g) as a colorless oil.

A flask containing 2-bromo-N-phenylaniline (10 g), 4,4,5,5-tetramethyl-2-(3-phenoxyphenyl)-1,3,2-dioxaborolane (13.1 g), potassium carbonate (11.1 g), tetrabutylammonium bromide (3.9 g), dichlorobis[di-t-butyl(para-dimethylaminophenyl)phosphino]palladium(II) (0.3 g), toluene (100 ml), Solmix A-11 (manufactured by Japan Alcohol Sales Co., Ltd., solmix, 50 ml) and water (25 ml) was heated under reflux for 2 hours under a nitrogen atmosphere. After the reaction was completed, the reaction solution was cooled to room temperature and the organic layer was separated. The organic layer was concentrated under reduced pressure to obtain a crude product, which was dissolved in toluene and passed through a silica gel pass column (eluent: toluene, heptane). The solvent of the fraction containing the target product was distilled off under reduced pressure to obtain 3'-phenoxy-N-phenyl-1,1'-biphenyl-2-amine (13.3 g) as a colorless oil.

A flask containing 3'-phenoxy-N-phenyl-1,1'-biphenyl-2-amine (13.3 g), boron triiodide (25 g) and dichlorobenzene (130 ml) was heated and stirred at 200°C for 8 hours under a nitrogen atmosphere. After the reaction was completed, ethyl acetate and water were added to the reaction mixture cooled to room temperature to extract the organic layer. The organic layer solvent was distilled off under reduced pressure to obtain a solid, which was dissolved in toluene (100 ml), and acetic acid (10 ml) was added. The mixture was heated and stirred at 95°C for 8 hours under a nitrogen atmosphere. After the acetic acid treatment was completed, water was added to the reaction mixture cooled to room temperature to extract the organic layer. The solid obtained by distilling off the organic layer solvent under reduced pressure was passed through an amino silica gel pass column (eluent: ethyl acetate, heptane). The solvent of the fraction containing the target product was distilled off under reduced pressure to obtain compound (1-101) (3.2 g) as a white solid.

The structure of the obtained compound was confirmed by liquid chromatography-mass spectrometry (LC-MS).
MS (ACPI): m/z=346 (M+)

Synthesis Example (3)
Synthesis of compound (1-231): 5,15-diphenyl-5,15-dihydro-5,15,19c-triaza-19b,19d-diboraanthra[9,1-ab]benzo[o]perylene

A flask containing 1-bromo-3-iodobenzene (50 g), diphenylamine (31.4 g), sodium 2-methyl-2-butoxide (38.9 g), dichlorobis[di-t-butyl(para-dimethylaminophenyl)phosphino]palladium(II) (2.5 g) and toluene (500 ml) was heated to reflux for 2 hours under a nitrogen atmosphere. After the reaction was completed, the reaction solution was cooled to room temperature and the organic layer was separated. The organic layer was concentrated under reduced pressure, and the resulting crude was dissolved in heptane and passed through a silica gel short-path column (eluent: heptane). The solvent of the fraction containing the target product was distilled off under reduced pressure, and the fraction was recrystallized with heptane to obtain 3-bromo-N,N-diphenylaniline (50 g) as a white solid.

A flask containing 3-bromo-N,N-diphenylaniline (50 g), bis(pinacolato)diboron (43 g), potassium acetate (30.3 g), potassium carbonate (10.7 g), dichloromethane adduct of [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride (1.3 g), and cyclopentyl methyl ether (500 ml) was heated under reflux for 4 hours under a nitrogen atmosphere. After the reaction was completed, the reaction solution was cooled to room temperature and the organic layer was separated. The organic layer was concentrated under reduced pressure to obtain a crude product, which was dissolved in heptane and passed through a silica gel short-pass column (eluent: heptane). The solvent of the fraction containing the target product was distilled off under reduced pressure, and the product was recrystallized from heptane and Solmix A-11 (manufactured by Japan Alcohol Sales Co., Ltd.) to obtain N,N-diphenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (36 g) as a white solid.

A flask containing 2,6-dibromoaniline (8.5 g), N,N-diphenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (27.7 g), potassium carbonate (18.7 g), tetrabutylammonium bromide (3.3 g), palladium(II) acetate (0.15 g), dicyclohexyl(2',6'-dimethoxy-[1,1'-biphenyl]-2-yl)phosphine (0.56 g), toluene (85 ml), Solmix A-11 (manufactured by Japan Alcohol Sales Co., Ltd., solmix, 40 ml) and water (20 ml) was heated under reflux for 2 hours under a nitrogen atmosphere. After the reaction was completed, the mixture was cooled to room temperature, and the organic layer was distilled off under reduced pressure to obtain a solid, which was dissolved in toluene and passed through a silica gel pass column (eluent: toluene, heptane). The solvent of the fraction containing the target product was removed under reduced pressure, and the product was recrystallized from toluene and heptane to obtain N ³ ,N ³ ,N ^3″ ,N ^3″ -tetraphenyl-[1,1':3',1″-terphenyl]-2'3,3″-triamine (17.5 g) as a white solid.

A flask containing N ³ ,N ³ ,N ^{3 "} ,N ^{3 "} -tetraphenyl-[1,1':3',1"-terphenyl]-2'3,3"-triamine (6 g), boron triiodide (25 g) and dichlorobenzene (60 ml) was heated and stirred at 160°C for 8 hours under a nitrogen atmosphere. After the reaction was completed, the reaction mixture was cooled to room temperature, and ethyl acetate and water were added to extract the organic layer. The organic layer solvent was distilled off under reduced pressure to obtain a solid, which was dissolved in toluene (60 ml), and acetic acid (6 ml) was added and the mixture was heated and stirred at 95°C for 8 hours under a nitrogen atmosphere. After the acetic acid treatment was completed, water was added to the reaction mixture cooled to room temperature to extract the organic layer. The organic layer solvent was distilled off under reduced pressure to obtain a solid, which was passed through an amino silica gel pass column (eluent: ethyl acetate, heptane). The solvent of the fraction containing the target product was distilled off under reduced pressure to obtain compound (1-231) (0.8 g) as a pale yellow solid.

The structure of the obtained compound was confirmed by liquid chromatography-mass spectrometry (LC-MS).
MS (ACPI): m/z=596 (M+)

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

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

<Evaluation of deposition-type organic EL elements>
The organic EL elements of Examples 1-1 to 1-3 and Comparative Example 1 were produced, and the driving voltage (V) and external quantum efficiency (%), which are the characteristics at 100 cd/ ^m2 emission, were measured.

The quantum efficiency of a light-emitting element can be classified into internal quantum efficiency and external quantum efficiency. The internal quantum efficiency indicates the proportion of external energy injected as electrons (or holes) into the light-emitting layer of the light-emitting element that is converted purely into photons. On the other hand, the external quantum efficiency is calculated based on the amount of these photons that are emitted to the outside of the light-emitting element. Some of the photons generated in the light-emitting layer are absorbed or continue to be reflected inside the light-emitting element, and are not emitted to the outside of the light-emitting element, so the external quantum efficiency is lower than the internal quantum efficiency.

The method for measuring the external quantum efficiency is as follows. Using an Advantest voltage/current generator R6144, a voltage was applied so that the luminance of the element was 1000 cd/ ^m2 , and the element was made to emit light. Using a TOPCON spectroradiometer SR-3AR, the spectral radiance of the visible light region was measured from a direction perpendicular to the light-emitting surface. Assuming that the light-emitting surface is a completely diffusing surface, the measured spectral radiance value of each wavelength component was divided by the wavelength energy and multiplied by π to obtain the number of photons at each wavelength. Next, the number of photons was integrated over the entire wavelength range observed to obtain the total number of photons emitted from the element. The value obtained by dividing the applied current value by the elementary charge was taken as the number of carriers injected into the element, and the value obtained by dividing the total number of photons emitted from the element by the number of carriers injected into the element was taken as the external quantum efficiency.

<Examples 1-1 to 1-3 and Comparative Example 1-1>
The layer structures of the organic EL devices produced in Examples 1-1 to 1-3 and Comparative Example 1-1 are shown in Table 1.

The chemical structures of the materials indicated by the abbreviations in Table 1 are as follows:

A 26 mm x 28 mm x 0.7 mm glass substrate (manufactured by Optoscience Co., Ltd.) on which ITO was formed to a thickness of 180 nm by sputtering and polished to 50 nm was used as a transparent support substrate. This transparent support substrate was fixed to the substrate holder of a commercially available deposition device (manufactured by Choshu Sangyo Co., Ltd.), and molybdenum deposition boats containing NPD, TcTa, mCP, compound (1-1), and TSPO1, as well as tungsten deposition boats containing LiF and Al, were attached.

The following layers were formed in sequence on the ITO film of the transparent support substrate. The vacuum chamber was depressurized to 5.0×10 ⁻⁴ Pa, and first, NPD was heated and evaporated to a thickness of 50 nm, TcTa was heated and evaporated to a thickness of 15 nm, and mCP was heated and evaporated to a thickness of 15 nm to form a hole layer consisting of three layers. Next, compound (1-1) and 4Cz-IPN were heated simultaneously and evaporated to a thickness of 20 nm to form a light-emitting layer. The evaporation rate was adjusted so that the weight ratio of compound (1-1) and 4Cz-IPN was approximately 98:2. Next, TSPO1 was heated and evaporated to a thickness of 50 nm to form an electron transport layer. The evaporation rate of each layer was 0.01 to 1 nm/sec. Then, LiF was heated and evaporated to a thickness of 1 nm at an evaporation rate of 0.01 to 0.1 nm/sec. Next, aluminum was heated and evaporated at a deposition rate of 0.1 nm to 2 nm/sec to a thickness of 100 nm to form a cathode. In this way, the organic EL element of Example 1-1 was obtained.

In addition, the organic EL elements of Examples 1-2, 1-3 and Comparative Example 1-1 were obtained by replacing compound (1-1) with compound (1-101), compound (1-231) or comparative compound (mCBP).

The EL characteristics obtained from each device are shown in Table 2. It can be confirmed that the organic EL device using the compound according to the present invention has a lower driving voltage and a higher external quantum efficiency than the device using the comparative compound.

<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 2-1 to 2-8>
A coating solution of the material for forming each layer is prepared to fabricate a coating type organic EL element.

<Preparation of Organic EL Elements of Examples 2-1 to 2-3>
Table 3 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.
Compound (A) 0.04% by weight
SPH-101 1.96 weight%
Xylene 69.00% by weight
Decalin 29.00% by weight

The compound (A) is a polycyclic aromatic compound represented by the above general formula (1), a multimer thereof, a polymer compound obtained by polymerizing the polycyclic aromatic compound or the multimer thereof as a monomer (i.e., the monomer has a reactive substituent), a crosslinked polymer obtained by further crosslinking the polymer compound, a pendant polymer compound obtained by substituting the monomer in a main chain polymer, or a pendant crosslinked polymer obtained by further crosslinking the pendant polymer compound. The polymer compound for obtaining the crosslinked polymer or the pendant crosslinked polymer or the pendant polymer compound 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>
Polyvinylcarbazole (PCz) is dissolved in dichlorobenzene to prepare a 0.7 wt % PCz solution.

<Example 2-1>
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 2-2>
An organic EL element is obtained in the same manner as in Example 2-1. 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 2-3>
An organic EL element is obtained in the same manner as in Example 2-1. 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 2-4 to 2-6>
Table 4 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.
Compound (A) 0.02% by weight
mCBP 1.98% 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.
Compound (A) 0.02% by weight
SPH-101 1.98% 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.
Compound (A) 0.02% by weight
DOBNA 1.98% by weight
Toluene 98.00% by weight

In Table 4, "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 2-4>
A glass substrate on which an ITO film is formed to a thickness of 45 nm is 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 is 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) is 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 2-5 and 2-6>
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 2-4.

<Preparation of Organic EL Elements of Examples 2-7 to 2-9>
Table 5 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.
Compound (A) 0.02% by weight
2PXZ-TAZ 0.18 weight%
mCBP 1.80% 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.
Compound (A) 0.02% by weight
2PXZ-TAZ 0.18 weight%
SPH-101 1.80% 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.
Compound (A) 0.02% by weight
2PXZ-TAZ 0.18 weight%
DOBNA 1.80% by weight
Toluene 98.00% by weight

In Table 5, "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 2-7>
A glass substrate on which an ITO film is formed to a thickness of 45 nm is 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 a 50 nm thick ND-3202 film (hole injection layer). Next, an XLP-101 solution is spin-coated, and heated on a hot plate in a nitrogen gas atmosphere at 200° C. for 30 minutes to form a 20 nm thick XLP-101 film (hole transport layer). Next, a light-emitting layer forming composition (5) is spin-coated, and heated in a nitrogen gas atmosphere at 130° C. for 10 minutes to form a 20 nm thick light-emitting layer.

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 2-8 and 2-9>
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 2-7.

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 (13)

A polycyclic aromatic compound represented by the following general formula (2), or a multimer represented by the following general formula (2-M2) :

In the above formula (2) and formula (2-M2) ,
R ¹ to R ¹¹ are each independently a hydrogen atom, an aryl having 6 to 16 carbon atoms , a diarylamino (wherein aryl is an aryl having 6 to 10 carbon atoms) , an alkyl having 1 to 12 carbon atoms , or a cycloalkyl having 3 to 16 carbon atoms , in which at least one hydrogen atom may be substituted with an aryl having 6 to 10 carbon atoms , an alkyl having 1 to 5 carbon atoms , or a cycloalkyl having 5 to 10 carbon atoms , and adjacent groups among R ¹ to R ¹¹ may be bonded to each other to form an aryl ring having 9 to 16 carbon atoms or a heteroaryl ring having 6 to 15 carbon atoms together with the a, b, or c ring, and at least one hydrogen atom in the formed ring is substituted with an aryl ring having 6 to 16 carbon atoms , a diarylamino (wherein aryl is an aryl having 6 to 10 carbon atoms), , an alkyl group having 1 to 12 carbon atoms , or a cycloalkyl group having 3 to 16 carbon atoms , in which at least one hydrogen atom may be substituted by an aryl group having 6 to 10 carbon atoms , an alkyl group having 1 to 5 carbon atoms , or a cycloalkyl group having 5 to 10 carbon atoms ;
^Y1 is B ;
^X1 is >O, >N-R, >S, or >Se , and R of the >N-R is an aryl having 6 to 12 carbon atoms, an alkyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 14 carbon atoms;
In formula (2), X2 ^is >O or >N-R , and R in the >N-R is an aryl having 6 to 12 carbon atoms, an alkyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 14 carbon atoms;
In formula (2-M2), X2 ^is N, and
At least one hydrogen atom in the compound represented by formula (2) or the multimer represented by formula (2-M2) may be substituted with halogen, cyano, or deuterium. In the above formula (2) and formula (2-M2),
R ¹ to R ¹¹ each independently represent a hydrogen atom, an aryl group having 6 to 16 carbon atoms, a diarylamino group (wherein the aryl group has 6 to 10 carbon atoms), an alkyl group having 1 to 12 carbon atoms, or a cycloalkyl group having 3 to 16 carbon atoms;
^Y1 is B;
Each ^X1 is independently >O or >N-R, and R in the >N-R is an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms;
In formula (2), ^X2 is >O or >N-R, and R of the >N-R is an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 5 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms, and
In formula (2-M2) , ^X2 is N.
The polycyclic aromatic compound or a multimer thereof according to claim 1 . 2. The polycyclic aromatic compound or a multimer thereof according to claim 1, which is represented by any one of the following structural formulas:

A material for an organic device, comprising the polycyclic aromatic compound or a multimer thereof according to any one of claims 1 to 3 . The material for an organic device according to claim 4 , which is a material for an organic electroluminescent element, a material for an organic field effect transistor, or a material for an organic thin-film solar cell. The material for an organic device according to claim 5 , which is a material for a light-emitting layer of an organic electroluminescent device. 4. 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 or a polymer thereof according to claim 1 . The organic electroluminescent device according to claim 7 , wherein the organic layer is a light-emitting layer. The organic electroluminescent device according to claim 8 , wherein the light-emitting layer comprises the polycyclic aromatic compound or a polymer thereof as a host, and a dopant. The organic electroluminescent device according to claim 9 , wherein the host further comprises an anthracene-based compound, a fluorene-based compound, or a dibenzochrysene-based compound. 11. The organic electroluminescence device according to claim 7, 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 the 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, and quinolinol-based metal complexes. 12. The organic electroluminescent device according to claim 11, 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 7 to 12 .

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