JP7622941B2 - Polycyclic aromatic compounds - Google Patents

Description

The present invention relates to polycyclic aromatic compounds, organic devices using the same, such as organic field-effect transistors and organic thin-film solar cells, as well as display devices and lighting devices. In this specification, "organic electroluminescent devices" may be referred to as "organic EL elements" or simply as "elements."

Display devices using electroluminescent light-emitting elements have been extensively studied because they can be made thin and energy-efficient. Furthermore, organic electroluminescent devices made from organic materials have been actively studied because they can be easily made large and lightweight. In particular, there has been active research into the development of organic materials that have the luminescence properties of blue and green, which are 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.

Currently, three types of materials are used for the light-emitting layer: fluorescent materials, phosphorescent materials, and thermally activated delayed fluorescence (TADF) materials. For example, benzofluorene-based compounds have been developed as fluorescent materials (WO 2004/061047), and noble metal complexes with multidentate ligands have been developed as phosphorescent materials (JP 2014-239225).

In addition, in recent years, materials that improve azaborine derivatives have also been reported (WO 2015/102118). Compounds having a conjugated structure with a narrow emission half-width at a single peak and a small energy difference (ΔS ¹ T ¹ ) between singlet energy (S ¹ ) and triplet energy (T ¹ ) are useful as materials for blue and green light-emitting layers because they provide high color purity and high efficiency due to thermally activated delayed fluorescence (TADF). In addition, compounds having a new conjugated structure with a large triplet energy (T ¹ ) are also required as electron transport materials and hole transport materials that sandwich the light-emitting layer.

However, fluorescent materials have the problem of low luminous efficiency, while phosphorescent and TADF materials have the problem of high luminous efficiency but a wide half-width of the emission spectrum and low color purity of the emitted light. Furthermore, phosphorescent materials are expensive because they contain precious metals (Nature Vol. 492 13 December 2012, Applied Physics Letters 75, 4 (1999)).

International Publication No. 2004/061047 JP 2014-239225 A International Publication No. 2015/102118

Nature Vol.492 13 December 2012 Applied Physics Letters 75, 4 (1999)

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, it is desirable to develop materials made of compounds different from conventional ones. In addition, Patent Document 3 reports a polycyclic aromatic compound containing boron and an organic EL element using the same, but in order to further improve the device characteristics, there is a demand for materials for the light-emitting layer, particularly dopant materials, that can improve the color purity, luminous efficiency, and device life. In addition, as shown in Non-Patent Documents 1 and 2, thermally activated delayed fluorescent materials and phosphorescent materials utilizing the heavy atom effect have a wide half-width of the emission spectrum, which is a problem in terms of improving color purity.

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

As a result of intensive research to solve the above problems, the present inventors have succeeded in producing a novel polycyclic aromatic compound, and further discovered that this compound is effective as a material with a small difference between the singlet energy and triplet energy required for thermally activated delayed fluorescence. They have also discovered that an excellent thermally activated delayed fluorescence type organic EL element can be obtained by, for example, using such a polycyclic aromatic compound as a dopant material and disposing an emission layer in which a compound having a larger triplet energy than the dopant material is used as a host material between a pair of electrodes to form an organic EL element, and have thus completed the present invention.

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

The chemical structural formulae described herein (including general formulae depicted in Markush structural formulae) are planar structural formulae, and therefore may in fact exist in various isomeric structures such as enantiomers, diastereoisomers, and rotational isomers. In this specification, unless otherwise specified, the compounds described may be any isomeric structure conceivable from their planar structural formulae, or may be mixtures of possible isomers in any ratio.

In this specification, many structural formulas of aromatic compounds are described. Although aromatic compounds are described by combining double bonds and single bonds, in reality, since π electrons resonate, even a single substance has multiple equivalent resonance structures in which double bonds and single bonds alternate. In this specification, only one resonance structural formula is described for each substance, but other resonance structural formulas that are organically equivalent are also included unless otherwise specified. This is referred to in the description below, such as "any "-C(-R)=" may be replaced with "-N=" (R is defined as R ^a , R ^b , R ^c , R ^d , R ^e , R ^f , or R ^g in each case). That is, for example, the following is an example of "-C(-R)=" in formula (2A) described below. However, this is not limited to this, and it naturally applies not only to the one resonance structural formula described, but also to other possible equivalent resonance structural formulas.

The statement that "any '-C(-R)=' may be replaced with '-N='" applies to all structural formulas in this specification unless otherwise specified. In addition, the R in the above-mentioned -C(-R)= is to be interpreted as a substituent defined for the ring structure in each case.

Note that in this specification, the two expressions "may be" and "is not, or has been" are used, but both have the same meaning.

上記式（１Ａ）または式（１Ｂ）中、
Ｒ^ａは水素または置換基であり、ａ環における「－Ｃ（－Ｒ^ａ）＝」は「－Ｎ＝」に置き換わっていないか、または置き換わっており、
Ｂ環、Ｃ環、Ｄ環、Ｅ環、Ｆ環、およびＧ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いないか、または置換されており、
Ｙ^１、Ｙ^２、およびＹ^３は、それぞれ独立して、＞Ｂ－、＞Ｐ－、＞Ｐ（＝Ｏ）－、＞Ｐ（＝Ｓ）－、＞Ａｌ－、＞Ｇａ－、＞Ａｓ－、＞Ｃ（－Ｒ）－、＞Ｓｉ（－Ｒ）－、または＞Ｇｅ（－Ｒ）－であり、前記＞Ｃ（－Ｒ）－のＲ、＞Ｓｉ（－Ｒ）－のＲ、および＞Ｇｅ（－Ｒ）－のＲは、それぞれ独立して、置換もしくは無置換のアリール、置換もしくは無置換のヘテロアリール、置換もしくは無置換のアルキル、または置換もしくは無置換のシクロアルキルであり、
式（１Ａ）中、
Ｘ^１およびＸ^２は、それぞれ独立して、＞Ｎ－Ｒ、＞Ｏ、＞Ｓ、＞Ｃ（－Ｒ）_２、＞Ｓｉ（－Ｒ）_２、または＞Ｓｅであり、前記＞Ｎ－ＲのＲ、＞Ｃ（－Ｒ）_２のＲ、および＞Ｓｉ（－Ｒ）_２のＲは、それぞれ独立して、水素、もしくは無置換のアリール、置換もしくは無置換のヘテロアリール、置換もしくは無置換のアルキル、または置換もしくは無置換のシクロアルキルであり、前記＞Ｃ（－Ｒ）_２の２つのＲ同士および＞Ｓｉ（－Ｒ）_２の２つのＲ同士の少なくとも１つは、単結合または連結基により結合していていないか、または結合しており、
Ｘ^１としての前記＞Ｎ－ＲのＲ、＞Ｃ（－Ｒ）_２のＲ、または＞Ｓｉ（－Ｒ）_２のＲは、単結合または連結基により、ａ環およびＢ環の少なくとも１つと結合しており、Ｘ^２としての前記＞Ｎ－ＲのＲ、＞Ｃ（－Ｒ）_２のＲ、または＞Ｓｉ（－Ｒ）_２のＲは、単結合または連結基により、ａ環およびＥ環の少なくとも１つと結合しており、ただし複数の連結基はそれぞれ同一であるか、または異なっており、
上記式（１Ａ）または式（１Ｂ）中、
Ｌはそれぞれ独立して、単結合または連結基であり、ただしＬの少なくとも１つは、置換もしくは無置換のアルキレン、置換もしくは無置換のシクロアルキレン、置換もしくは無置換のアルケニレン、置換もしくは無置換のアルキニレン、置換もしくは無置換のアリーレンまたは置換もしくは無置換のヘテロアリーレンであり、上記式（１Ａ）または式（１Ｂ）で表される化合物における、Ｂ環、Ｃ環、Ｄ環、Ｅ環、Ｆ環、Ｇ環、アリール、およびヘテロアリールの少なくとも１つは、少なくとも１つのシクロアルカンで縮合されていないか、または縮合されており、当該シクロアルカンにおける少なくとも１つの水素は置換されていないか、または置換されており、当該シクロアルカンにおける少なくとも１つの－ＣＨ_２－は－Ｏ－で置換されていないか、または置換されており、
上記式（１Ａ）または式（１Ｂ）で表される化合物における少なくとも１つの水素は、重水素、シアノ、またはハロゲンで置換されていていないか、または置換されている。 <1> A polycyclic aromatic compound represented by the following general formula (1A) or general formula (1B):

In the above formula (1A) or (1B),
R ^a is hydrogen or a substituent, and "-C(-R ^a )=" in the a ring is not replaced or is replaced with "-N=";
ring B, ring C, ring D, ring E, ring F, and ring G are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen atom in these rings is unsubstituted or substituted;
Y ¹ , Y ² , and Y ³ are each independently >B-, >P-, >P(═O)-, >P(═S)-, >Al-, >Ga-, >As-, >C(-R)-, >Si(-R)-, or >Ge(-R)-, and R of >C(-R)-, R of >Si(-R)-, and R of >Ge(-R)- are each independently a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted alkyl, or a substituted or unsubstituted cycloalkyl;
In formula (1A),
^X1 and ^X2 are each independently >N-R, >O, >S, >C(-R) _2, >Si(-R) ₂ , or >Se, R of the >N-R, R of the >C(-R) ₂ , and R of the >Si(-R) ₂ are each independently hydrogen, or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, and at least one of the two Rs of the >C(-R) ₂ and the two Rs of the >Si(-R) ₂ are not bonded together or are bonded together by a single bond or a linking group,
R of the >N-R, R of the >C(-R) ₂ , or R of the >Si(-R) ₂ as X ¹ is bonded to at least one of the ring a and the ring B by a single bond or a linking group, and R of the >N-R, R of the >C(-R) ₂ , or R of the >Si(-R) ₂ as X ² is bonded to at least one of the ring a and the ring E by a single bond or a linking group, with the proviso that each of the multiple linking groups is the same or different;
In the above formula (1A) or (1B),
L's are each independently a single bond or a linking group, with the proviso that at least one of L's is a substituted or unsubstituted alkylene, a substituted or unsubstituted cycloalkylene, a substituted or unsubstituted alkenylene, a substituted or unsubstituted alkynylene, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene, at least one of ring B, ring C, ring D, ring E, ring F, ring G, aryl, and heteroaryl in the compound represented by formula (1A) or formula (1B) is not condensed with or is condensed with at least one cycloalkane, at least one hydrogen in the cycloalkane is not substituted or is substituted, and at least one -CH ₂ - in the cycloalkane is not substituted or is substituted with -O-,
At least one hydrogen atom in the compound represented by the above formula (1A) or formula (1B) is not substituted or is substituted with deuterium, cyano, or halogen.

<2> In the above formula (1A) or formula (1B),
R ^a is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino, substituted or unsubstituted diarylboryl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted arylthio, or substituted silyl, wherein the two aryls of the diarylamino are not bonded to each other or are bonded to each other via a linking group, the two heteroaryls of the diheteroarylamino are not bonded to each other or are bonded to each other via a linking group, the aryl and heteroaryl of the arylheteroarylamino are not bonded to each other or are bonded to each other via a linking group, and the two aryls of the diarylboryl are not bonded to each other or are bonded to each other via a single bond or a linking group;
"-C(-R ^a )=" in ring a is not replaced or is replaced with "-N=";
ring B, ring C, ring D, ring E, ring F, and ring G are each independently an aryl ring or a heteroaryl ring, at least one hydrogen atom in these rings may be replaced by a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted diarylamino, a substituted or unsubstituted diheteroarylamino, a substituted or unsubstituted arylheteroarylamino, a substituted or unsubstituted diarylboryl, a substituted or unsubstituted alkyl, a substituted or unsubstituted cycloalkyl, a substituted or unsubstituted alkenyl, a substituted or unsubstituted alkoxy, a substituted or unsubstituted aryloxy, a substituted or unsubstituted arylthio, or a substituted silyl, the two aryls in the diarylamino are not bonded to each other or are bonded to each other via a linking group, the two heteroaryls in the diheteroarylamino are not bonded to each other or are bonded to each other via a linking group, the aryl and heteroaryl in the arylheteroarylamino are not bonded to each other or are bonded to each other via a linking group, and the two aryls in the diarylboryl are not bonded to each other or are bonded to each other via a single bond or a linking group;
Y ¹ , Y ² and Y ³ are each independently >B-, >P-, >P(═O)-, >P(═S)-, >Al-, >Ga-, >As-, >C(—R)-, >Si(—R)- or >Ge(—R)-, wherein R of >C(—R)-, R of >Si(—R)- and R of >Ge(—R)- are each independently aryl, heteroaryl, alkyl or cycloalkyl, and at least one hydrogen atom in these may be substituted by alkyl or cycloalkyl;
In formula (1A),
^X1 and ^X2 are each independently >N-R, >O, >S, >C(-R) _2, >Si(-R) ₂ , or >Se, R of the >N-R, R of the >C(-R) ₂ , and R of the >Si(-R) ₂ are each independently hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, at least one hydrogen atom of which is not substituted or is substituted by alkyl or cycloalkyl, two R of the >C(-R) ₂ and two R of the >Si(-R) ₂ are not bonded together or are bonded together by a single bond or a linking group, and the multiple linking groups are the same or different,
R of the >N-R, R of the >C(-R) ₂ , or R of the >Si(-R) ₂ as X ¹ is bonded to at least one of the ring a and the ring B by a single bond or a linking group, and R of the >N-R, R of the >C(-R) ₂ , or R of the >Si(-R) ₂ as X ² is bonded to at least one of the ring a and the ring E by a single bond or a linking group, with the proviso that each of the multiple linking groups is the same or different;
In the above formula (1A) or (1B),
L's are each independently a single bond or a linking group, with the proviso that at least one L is a substituted or unsubstituted alkylene, a substituted or unsubstituted cycloalkylene, a substituted or unsubstituted alkenylene, a substituted or unsubstituted alkynylene, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene;
the linking group is -N(-R)-, -O-, -S-, -C(-R) ₂ -, -Si(-R) ₂ -, -Se-, a substituted or unsubstituted cycloalkylene, a substituted or unsubstituted alkylene, a substituted or unsubstituted alkenylene, a substituted or unsubstituted alkynylene, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene, R of -N(-R)-, R of -C(-R) ₂ -, and R of -Si(-R) ₂ - are each independently hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, and at least one hydrogen atom in these is not substituted or is substituted by alkyl or cycloalkyl;
In the compound represented by the above formula (1A) or (1B), at least one of ring B, ring C, ring D, ring E, ring F, ring G, aryl, and heteroaryl is not condensed with or is condensed with at least one cycloalkane, at least one hydrogen in the cycloalkane is not substituted or is substituted, and at least one -CH ₂ - in the cycloalkane is not substituted or is substituted with -O-,
At least one hydrogen atom in the compound represented by the above formula (1A) or formula (1B) is not substituted or is substituted with deuterium, cyano, or halogen.
The polycyclic aromatic compound according to <1>.

上記式（２Ａ）または式（２Ｂ）中、
Ｒ^ａは、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、アルキル、シクロアルキル、アルケニル、アルコキシ、アリールオキシ、アリールチオ、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いないか、または置換されており、前記ジアリールアミノの２つのアリールは互いに結合していないか、または連結基を介して結合しており、前記ジヘテロアリールアミノの２つのヘテロアリールは互いに結合していないか、または連結基を介して結合しており、前記アリールヘテロアリールアミノのアリールとヘテロアリールは互いに結合していないか、または連結基を介して結合しており、前記ジアリールボリルの２つのアリールは互いに結合していないか、または単結合または連結基を介して結合しており、
ａ環における「－Ｃ（－Ｒ^ａ）＝」は「－Ｎ＝」に置き換わっていてもよく、
Ｒ^ｂ、Ｒ^ｃ、Ｒ^ｄ、Ｒ^ｅ、Ｒ^ｆ、およびＲ^ｇ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、アルキル、シクロアルキル、アルケニル、アルコキシ、アリールオキシ、アリールチオ、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いないか、または置換されており、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ないか、または置換されており、前記ジアリールアミノの２つのアリールは互いに結合していないか、または連結基を介して結合しており、前記ジヘテロアリールアミノの２つのヘテロアリールは互いに結合していないか、または連結基を介して結合しており、前記アリールヘテロアリールアミノのアリールとヘテロアリールは互いに結合していないか、または連結基を介して結合しており、前記ジアリールボリルの２つのアリールは互いに結合していないか、または単結合または連結基を介して結合しており、
また、Ｒ^ｂ、Ｒ^ｃ、Ｒ^ｄ、Ｒ^ｅ、Ｒ^ｆ、およびＲ^ｇのうちの隣接する基同士が結合して、それぞれｂ環、ｃ環、ｄ環、ｅ環、ｆ環、およびｇ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、アルキル、シクロアルキル、アルケニル、アルコキシ、アリールオキシ、アリールチオ、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ないか、または置換されており、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ないか、または置換されており、前記ジアリールアミノの２つのアリールは互いに結合していないか、または連結基を介して結合しており、前記ジヘテロアリールアミノの２つのヘテロアリールは互いに結合していないか、または連結基を介して結合しており、前記アリールヘテロアリールアミノのアリールとヘテロアリールは互いに結合していないか、または連結基を介して結合しており、前記ジアリールボリルの２つのアリールは互いに結合していないか、または単結合または連結基を介して結合しており、
ｂ環、ｃ環、ｄ環、ｅ環、ｆ環、およびｇ環における、任意の「－Ｃ（－Ｒ）＝」（ここでＲは、Ｒ^ｂ、Ｒ^ｃ、Ｒ^ｄ、Ｒ^ｅ、Ｒ^ｆ、またはＲ^ｇである）は「－Ｎ＝」に置き換わっていないか、または置き換わっており、任意の「－Ｃ（－Ｒ）＝Ｃ（－Ｒ）－」（ここでＲは、Ｒ^ｂ、Ｒ^ｃ、Ｒ^ｄ、Ｒ^ｅ、Ｒ^ｆ、またはＲ^ｇである）は、「－Ｎ（－Ｒ）－」、「－Ｏ－」、「－Ｓ－」、「－Ｃ（－Ｒ）_２－」、「－Ｓｉ（－Ｒ）_２－」、または「－Ｓｅ－」に置き換わっていないか、または置き換わっており、前記「－Ｎ（－Ｒ）－」のＲ、「－Ｃ（－Ｒ）_２－」のＲ、および「－Ｓｉ（－Ｒ）_２－」のＲは、水素、アリール、ヘテロアリール、アルキル、またはシクロアルキルであり、これらにおける少なくとも１つの水素は、アルキルまたはシクロアルキルで置換されていないか、または置換されており、前記「－Ｃ（－Ｒ）_２－」の２つのＲ同士および「－Ｓｉ（－Ｒ）_２－」の２つのＲは、単結合または連結基で結合していてもよく、
Ｌは、それぞれ独立して、単結合または連結基であり、ただし、少なくとも１つのＬは、アルキレン、シクロアルキレン、アルキレン、アルケニレン、アルキニレン、アリーレンヘテロアリーレンであり、前記シクロアルキレン、前記アルケニレン、前記アルキニレン、前記アリーレン、および前記ヘテロアリーレンの少なくとも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、アルキル、シクロアルキル、アルケニル、アルコキシ、アリールオキシ、アリールチオ、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ないか、または置換されており、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いないか、または置換されており、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ないか、または置換されており、前記ジアリールアミノの２つのアリールは互いに結合していないか、または連結基を介して結合しており、前記ジヘテロアリールアミノの２つのヘテロアリールは互いに結合していないか、または連結基を介して結合しており、前記アリールヘテロアリールアミノのアリールとヘテロアリールは互いに結合していないか、または連結基を介して結合しており、前記ジアリールボリルの２つのアリールは互いに結合していないか、または単結合または連結基を介して結合しており、
連結基は、－Ｎ（－Ｒ）－、－Ｏ－、－Ｓ－、－Ｃ（－Ｒ）_２－、－Ｓｉ（－Ｒ）_２－、－Ｓｅ－、シクロアルキレン、アルキレン、アルケニレン、アルキニレン、アリーレン、ヘテロアリーレンであり、前記－Ｎ（－Ｒ）－のＲ、前記－Ｃ（－Ｒ）_２－のＲ、および前記－Ｓｉ（－Ｒ）_２－のＲは、それぞれ独立して、水素、アリール、ヘテロアリール、アルキル、またはシクロアルキルであり、これらにおける少なくとも１つの水素は、アルキルまたはシクロアルキルで置換されていていないか、または置換されており、前記シクロアルキレン、前記アルキレン、前記アルケニレン、前記アルキニレン、前記アリーレン、および前記ヘテロアリーレンの少なくとも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、アルキル、シクロアルキル、アルケニル、アルコキシ、アリールオキシ、アリールチオ、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ないか、または置換されており、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いないか、または置換されており、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ないか、または置換されており、前記ジアリールアミノの２つのアリールは互いに結合していないか、または連結基を介して結合しており、前記ジヘテロアリールアミノの２つのヘテロアリールは互いに結合していないか、または連結基を介して結合しており、前記アリールヘテロアリールアミノのアリールとヘテロアリールは互いに結合していないか、または連結基を介して結合しており、前記ジアリールボリルの２つのアリールは互いに結合していないか、または単結合または連結基を介して結合しており、
Ｙ^１、Ｙ^２、およびＹ^３は、それぞれ独立して、＞Ｂ－、＞Ｐ－、＞Ｐ（＝Ｏ）－、＞Ｐ（＝Ｓ）－、＞Ａｌ－、＞Ｇａ－、＞Ａｓ－、＞Ｃ（－Ｒ）－、＞Ｓｉ（－Ｒ）－、または＞Ｇｅ（－Ｒ）－であり、前記＞Ｃ（－Ｒ）－のＲ、＞Ｓｉ（－Ｒ）－のＲ、および＞Ｇｅ（－Ｒ）－のＲは、それぞれ独立して、アリール、ヘテロアリール、アルキル、またはシクロアルキルであり、これらにおける少なくとも１つの水素は、アルキルもしくはシクロアルキルで置換されていてもよく、
式（２Ａ）中
Ｘ^１およびＸ^２は、それぞれ独立して、＞Ｎ－Ｒ、＞Ｏ、＞Ｓ、＞Ｃ（－Ｒ）_２、＞Ｓｉ（－Ｒ）_２、または＞Ｓｅであり、前記＞Ｎ－ＲのＲ、＞Ｃ（－Ｒ）_２のＲ、および＞Ｓｉ（－Ｒ）_２のＲは、それぞれ独立して、水素、アリール、ヘテロアリール、アルキル、またはシクロアルキルであり、これらにおける少なくとも１つの水素は、アルキルまたはシクロアルキルで置換されていていないか、または置換されており、前記＞Ｃ（－Ｒ）_２の２つのＲ同士および＞Ｓｉ（－Ｒ）_２の２つのＲ同士は、単結合、連結基で結合していないか、または結合しており、ただし複数の前記連結基は異なっているか、または同一であり、
Ｘ^１としての前記＞Ｎ－ＲのＲ、＞Ｃ（－Ｒ）_２のＲ、または＞Ｓｉ（－Ｒ）_２のＲは、単結合または連結基により、ａ環およびｂ環の少なくとも１つと結合しており、Ｘ^２としての前記＞Ｎ－ＲのＲ、＞Ｃ（－Ｒ）_２のＲ、または＞Ｓｉ（－Ｒ）_２のＲは、単結合または連結基により、ａ環およびｅ環の少なくとも１つと結合しており、複数の前記連結基は異なっているか、または同一であり、
上記式（２Ａ）または式（２Ｂ）で表される化合物における、前記ｂ環、前記ｃ環、前記ｄ環、前記ｅ環、前記ｆ環、前記ｇ環、前記形成された環、前記アリール、および前記ヘテロアリールの少なくとも１つは、炭素数３～２４の少なくとも１つのシクロアルカンで縮合されていないか、または縮合されており、当該シクロアルカンにおける少なくとも１つの水素は、炭素数６～３０のアリール、炭素数２～３０のヘテロアリール、炭素数１～２４のアルキル、または炭素数３～２４のシクロアルキルで置換されていていないか、または置換されており、当該シクロアルカンにおける少なくとも１つの－ＣＨ_２－は－Ｏ－で置換されていないか、または置換されており、
上記式（２Ａ）または式（２Ｂ）で表される化合物における少なくとも１つの水素は、重水素、シアノ、またはハロゲンで置換されていないか、または置換されている。 <3> The polycyclic aromatic compound according to <1>, represented by the following general formula (2A) or the following general formula (2B):

In the above formula (2A) or (2B),
R ^a is hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl, in which at least one hydrogen is unsubstituted or substituted with aryl, heteroaryl, alkyl, or cycloalkyl; the two aryls of the diarylamino are not bonded to each other or are bonded via a linking group; the two heteroaryls of the diheteroarylamino are not bonded to each other or are bonded via a linking group; the aryl and heteroaryl of the arylheteroarylamino are not bonded to each other or are bonded via a linking group; the two aryls of the diarylboryl are not bonded to each other or are bonded via a single bond or a linking group;
"-C(-R ^a )=" in ring a may be replaced with "-N=";
^Rb , ^Rc , ^Rd , ^Re , ^Rf , and R ^g 's are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl, in which at least one hydrogen is unsubstituted or substituted with an aryl, heteroaryl, alkyl, or cycloalkyl, and in which at least one hydrogen is unsubstituted or substituted with an aryl, heteroaryl, alkyl, or cycloalkyl, the two aryls of the diarylamino are not bonded to each other or are bonded via a linking group, the two heteroaryls of the diheteroarylamino are not bonded to each other or are bonded via a linking group, the aryl and heteroaryl of the arylheteroarylamino are not bonded to each other or are bonded via a linking group, and the two aryls of the diarylboryl are not bonded to each other or are bonded via a single bond or a linking group;
Adjacent groups among R ^b , R ^c , R ^d , R ^e , R ^f and R ^g may be bonded to each other to form an aryl ring or a heteroaryl ring together with the b ring, the c ring, the d ring, the e ring, the f ring and the g ring, respectively, and at least one hydrogen atom in the formed ring is not substituted or is substituted with an aryl, a heteroaryl, a diarylamino, a diheteroarylamino, an arylheteroarylamino, a diarylboryl, an alkyl, a cycloalkyl, an alkenyl, an alkoxy, an aryloxy, an arylthio, a triarylsilyl, a trialkylsilyl, a tricycloalkylsilyl, a dialkylcycloalkylsilyl or an alkyldicycloalkylsilyl, at least one hydrogen atom in each of these is unsubstituted or substituted with an aryl, heteroaryl, alkyl, or cycloalkyl; the two aryls in the diarylamino are not bonded to each other or are bonded to each other via a linking group; the two heteroaryls in the diheteroarylamino are not bonded to each other or are bonded to each other via a linking group; the aryl and heteroaryl in the arylheteroarylamino are not bonded to each other or are bonded to each other via a linking group; the two aryls in the diarylboryl are not bonded to each other or are bonded to each other via a single bond or a linking group;
In rings b, c, d, e, f and g, any "-C(-R)=" (wherein R is R ^b , R ^c , R ^d , R ^e , R ^f or R ^g ) is not replaced or is replaced with "-N=", any "-C(-R)=C(-R)-" (wherein R is R b , R ^c , R ^d , R ^e , R ^f or R ^g ) is not replaced or is replaced with "-N(-R)-", "-O-", "-S-", "-C(-R) 2 -", "-Si(-R) 2 -" or "-Se-", and R of "-N(-R)- ^" , R of "-C(-R) ₂ -" and "-Si(-R) ₂ -" are not replaced or are replaced with "-N(-R)-", "-O-", "-S-", "-C(-R) ₂ -", "-Si(-R) ₂ -" or "-Se-". R in "-" is hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, and at least one hydrogen in these is unsubstituted or substituted with alkyl or cycloalkyl, and the two R in "-C(-R) ₂ -" and the two R in "-Si(-R) ₂ -" may be bonded to each other via a single bond or a linking group;
L is each independently a single bond or a linking group, provided that at least one L is alkylene, cycloalkylene, alkylene, alkenylene, alkynylene, aryleneheteroarylene, and at least one hydrogen atom of the cycloalkylene, the alkenylene, the alkynylene, the arylene, and the heteroarylene is unsubstituted or substituted with an aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl, and at least one hydrogen atom in each of the above is unsubstituted or substituted with an aryl, heteroaryl, alkyl, or cycloalkyl, at least one hydrogen atom in each of the above is unsubstituted or substituted with an aryl, heteroaryl, alkyl, or cycloalkyl, the two aryls in the diarylamino are not bonded to each other or are bonded via a linking group, the two heteroaryls in the diheteroarylamino are not bonded to each other or are bonded via a linking group, the aryl and heteroaryl in the arylheteroarylamino are not bonded to each other or are bonded via a linking group, and the two aryls in the diarylboryl are not bonded to each other or are bonded via a single bond or a linking group;
The linking group is -N(-R)-, -O-, -S-, -C(-R) ₂ -, -Si(-R) ₂ -, -Se-, cycloalkylene, alkylene, alkenylene, alkynylene, arylene, or heteroarylene, and R of -N(-R)-, R of -C(-R) ₂ -, and -Si(-R) ₂ R in - is each independently hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, in which at least one hydrogen is not substituted or is substituted with alkyl or cycloalkyl, and at least one hydrogen of the cycloalkylene, the alkylene, the alkenylene, the alkynylene, the arylene, and the heteroarylene is not substituted or is substituted with aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyldicycloalkylsilyl. wherein at least one hydrogen atom is unsubstituted or substituted with an aryl, heteroaryl, alkyl, or cycloalkyl, wherein at least one hydrogen atom is unsubstituted or substituted with an aryl, heteroaryl, alkyl, or cycloalkyl, wherein the two aryls of the diarylamino are not bonded to each other or are bonded via a linking group, wherein the two heteroaryls of the diheteroarylamino are not bonded to each other or are bonded via a linking group, wherein the aryl and heteroaryl of the arylheteroarylamino are not bonded to each other or are bonded via a linking group, wherein the two aryls of the diarylboryl are not bonded to each other or are bonded via a single bond or a linking group,
Y ¹ , Y ² and Y ³ are each independently >B-, >P-, >P(═O)-, >P(═S)-, >Al-, >Ga-, >As-, >C(—R)-, >Si(—R)- or >Ge(—R)-, R of >C(—R)-, R of >Si(—R)- and R of >Ge(—R)- are each independently aryl, heteroaryl, alkyl or cycloalkyl, at least one hydrogen of which may be substituted by alkyl or cycloalkyl;
In formula (2A), ^X1 and ^X2 are each independently >N-R, >O, >S, >C(-R) _2, >Si(-R) ₂ , or >Se, R of the >N-R, R of the >C(-R) ₂ , and R of the >Si(-R) ₂ are each independently hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, at least one hydrogen atom of which is not substituted or is substituted by alkyl or cycloalkyl, two R of the >C(-R) ₂ and two R of the >Si(-R) ₂ are not bonded together by a single bond or a linking group or are bonded together, and a plurality of the linking groups are different or the same,
R of the >N-R, R of the >C(-R) ₂ , or R of the >Si(-R) ₂ as X ¹ is bonded to at least one of the ring a and the ring b by a single bond or a linking group, and R of the >N-R, R of the >C(-R) ₂ , or R of the >Si(-R) ₂ as X ² is bonded to at least one of the ring a and the ring e by a single bond or a linking group, and a plurality of the linking groups are different or the same;
In the compound represented by the above formula (2A) or (2B), at least one of the ring b, the ring c, the ring d, the ring e, the ring f, the ring g, the formed ring, the aryl, and the heteroaryl is not condensed with or is condensed with at least one cycloalkane having 3 to 24 carbon atoms, at least one hydrogen atom in the cycloalkane is not substituted with or is substituted with an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms, an alkyl having 1 to 24 carbon atoms, or a cycloalkyl having 3 to 24 carbon atoms, and at least one -CH ₂ - in the cycloalkane is not substituted with or is substituted with -O-,
At least one hydrogen atom in the compound represented by the above formula (2A) or formula (2B) is not substituted or is substituted with deuterium, cyano, or halogen.

各式中、
Ｒは、それぞれ独立して、水素、炭素数６～１６のアリール、炭素数２～２０のヘテロアリール、ジアリールアミノ（ただしアリールは炭素数６～１０のアリール）、ジアリールボリル（ただしアリールは炭素数６～１０のアリール）、炭素数１～１２のアルキル、または炭素数３～１６のシクロアルキルであり、これらにおける少なくとも１つの水素は、炭素数１～５のアルキルまたは炭素数５～１０のシクロアルキルで置換されていてもよく、前記ジアリールアミノの２つのアリールは互いに結合していないか、または連結基を介して結合しており、前記ジアリールボリルの２つのアリールは互いに結合していないか、単結合または連結基を介して結合しており
ｏはそれぞれ独立して１～３の整数であり、
ｐはそれぞれ独立して１～４の整数であり、
ｑはそれぞれ独立して１～５の整数であり、
上記各式で表される化合物における少なくとも１つの水素は、重水素、シアノ、またはハロゲンで置換されていてもよい。 <4> The polycyclic aromatic compound according to any one of <1> to <3>, which is represented by any one of the following structural formulas:

In each formula,
R's 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), 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 alkyl having 1 to 5 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms, the two aryls of the diarylamino are not bonded to each other or are bonded to each other via a linking group, and the two aryls of the diarylboryl are not bonded to each other or are bonded to each other via a single bond or a linking group, and each o is independently an integer of 1 to 3,
Each p is independently an integer from 1 to 4;
Each q is independently an integer from 1 to 5;
At least one hydrogen in the compounds represented by the above formulas may be substituted with deuterium, cyano, or halogen.

<5> The polycyclic aromatic compound according to <1>, represented by any one of the following structural formulas:

<6> A reactive compound in which a polycyclic aromatic compound described in any one of <1> to <5> is substituted with a reactive substituent.

<7> A polymer compound obtained by polymerizing the reactive compound described in <6> as a monomer, or a polymer crosslinked body obtained by further crosslinking the polymer compound.

<8> A pendant polymer compound in which the reactive compound described in <6> is substituted on a main chain polymer, or a pendant polymer crosslinked body in which the pendant polymer compound is further crosslinked.

<9> A material for organic devices, containing a polycyclic aromatic compound according to any one of <1> to <5>.

<10> A material for organic devices containing the reactive compound described in <6>.

<11> A material for organic devices containing the polymer compound or crosslinked polymer described in <7>.

<12> A material for organic devices containing the pendant polymer compound or pendant polymer crosslinker described in <8>.

<13> The material for an organic device according to any one of <9> to <12>, wherein the material for an organic device 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.

<14> The material for an organic device according to <13>, wherein the material for an organic electroluminescent element is a material for a light-emitting layer.

<15> An ink composition comprising the polycyclic aromatic compound described in any one of <1> to <5> and an organic solvent.

<16> An ink composition comprising the reactive compound described in <6> and an organic solvent.

<17> An ink composition comprising a main chain polymer, the reactive compound described in <6>, and an organic solvent.

<18> An ink composition comprising the polymer compound or crosslinked polymer described in <7> and an organic solvent.

<19> An ink composition comprising the pendant polymer compound or the pendant polymer crosslinker described in <8> and an organic solvent.

<20> An organic electroluminescence device having a pair of electrodes consisting of an anode and a cathode, and an organic layer disposed between the pair of electrodes and containing a polycyclic aromatic compound described in any one of <1> to <5>, a reactive compound described in <6>, a polymer compound or crosslinked polymer described in <7>, or a pendant polymer compound or pendant polymer crosslinked polymer described in <8>.

<21> The organic electroluminescent element according to <20>, wherein the organic layer is a light-emitting layer.

<22> The organic electroluminescent device according to <21>, wherein the light-emitting layer contains a host and the polycyclic aromatic compound, reactive compound, polymer compound, crosslinked polymer, pendant polymer compound, or pendant polymer crosslinked polymer as a dopant.

上記一般式（Ｈ１）中、Ｌ^１は炭素数６～３０のアリーレンまたは炭素数２～３０のヘテロアリーレンであり、
上記一般式（Ｈ２）中、Ｌ^２およびＬ^３は、それぞれ独立して、炭素数６～３０のアリールまたは炭素数２～３０のヘテロアリールであり、
上記一般式（Ｈ３）中、ＭＵはそれぞれ独立して芳香族化合物から任意の２つの水素原子を除いて表される２価の基、ＥＣはそれぞれ独立して芳香族化合物から任意の１つの水素原子を除いて表される１価の基であり、ＭＵ中の２つの水素がＥＣまたはＭＵと置換され、ｋは２～５００００の整数であり、
上記一般式（Ｈ４）中、Ｇはそれぞれ独立して＝Ｃ（－Ｈ）－または＝Ｎ－であり、前記＝Ｃ（－Ｈ）－中のＨは置換基または他の式（Ｈ４）で表される構造で置換されていてもよく、
上記一般式（Ｈ５）中、
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、アリールへテロアリールアミノ、アルキルまたはシクロアルキルであり、これらにおける少なくとも１つの水素はさらにアリール、ヘテロアリール、ジアリールアミノ、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、前記ジアリールアミノの２つのアリールは互いに結合していないか、または連結基を介して結合しており、前記ジヘテロアリールアミノの２つのヘテロアリールは互いに結合していないか、または連結基を介して結合しており、前記アリールヘテロアリールアミノのアリールとヘテロアリールは互いに結合していないか、または連結基を介して結合しており、
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、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、これらにおける少なくとも１つの水素はさらにアリール、ヘテロアリール、ジアリールアミノ、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、前記ジアリールアミノの２つのアリールは互いに結合していないか、または連結基を介して結合しており、前記ジヘテロアリールアミノの２つのヘテロアリールは互いに結合していないか、または連結基を介して結合しており、前記アリールヘテロアリールアミノのアリールとヘテロアリールは互いに結合していないか、または連結基を介して結合しており、
ａ環、ｂ環、およびｃ環における、任意の「－Ｃ（－Ｒ）＝」（ここでＲはＲ^１～Ｒ^１１である）は「－Ｎ＝」に置き換わっていてもよく、
上記一般式（Ｈ６）中、
Ｒ^１～Ｒ^１６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、アリールへテロアリールアミノ、アルキルまたはシクロアルキルであり、これらにおける少なくとも１つの水素はさらにアリール、ヘテロアリール、ジアリールアミノ、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、前記ジアリールアミノの２つのアリールは互いに結合していないか、または連結基を介して結合しており、前記ジヘテロアリールアミノの２つのヘテロアリールは互いに結合していないか、または連結基を介して結合しており、前記アリールヘテロアリールアミノのアリールとヘテロアリールは互いに結合していないか、または連結基を介して結合しており、
Ｒ^１～Ｒ^１６のうちの隣接する基同士が結合してａ環、ｂ環、ｃ環またはｄ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、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、これらにおける少なくとも１つの水素はさらにアリール、ヘテロアリール、ジアリールアミノ、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、前記ジアリールアミノの２つのアリールは互いに結合していないか、または連結基を介して結合しており、前記ジヘテロアリールアミノの２つのヘテロアリールは互いに結合していないか、または連結基を介して結合しており、前記アリールヘテロアリールアミノのアリールとヘテロアリールは互いに結合していないか、または連結基を介して結合しており、そして、
上記各式で表される化合物または構造における少なくとも１つの水素は、炭素数１～６のアルキル、炭素数３～１４のシクロアルキル、シアノ、ハロゲンまたは重水素で置換されていてもよい。 <23> The organic electroluminescent device according to <22>, in which the light-emitting layer further contains at least one selected from the group consisting of a compound represented by the following general formula (H1), a compound represented by the following general formula (H2), a compound represented by the following general formula (H3), a compound having a structure represented by the following general formula (H4), a compound represented by the following general formula (H5), a compound represented by the following general formula (H6), and a TADF material:

In the above general formula (H1), L ¹ is an arylene having 6 to 30 carbon atoms or a heteroarylene having 2 to 30 carbon atoms,
In the above general formula (H2), L ² and L ³ each independently represent an aryl having 6 to 30 carbon atoms or a heteroaryl having 2 to 30 carbon atoms;
In the above general formula (H3), 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 by EC or MU, and k is an integer of 2 to 50,000,
In the above general formula (H4), each G is independently =C(-H)- or =N-, and H in the =C(-H)- may be substituted with a substituent or a structure represented by another formula (H4),
In the above general formula (H5),
R ¹ to R ¹¹ are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl or cycloalkyl, at least one hydrogen of which may be further substituted with aryl, heteroaryl, diarylamino, alkyl or cycloalkyl, the two aryls of the diarylamino are not bonded to each other or are bonded via a linking group, the two heteroaryls of the diheteroarylamino are not bonded to each other or are bonded via a linking group, the aryl and heteroaryl of the arylheteroarylamino are not bonded to each other or are bonded via a linking group,
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 a ring, the b ring or the c ring, at least one hydrogen atom in the formed ring may be substituted with an aryl, a heteroaryl, a diarylamino, a diheteroarylamino, an arylheteroarylamino, an alkyl or a cycloalkyl, at least one hydrogen atom in these rings may be further substituted with an aryl, a heteroaryl, a diarylamino, an alkyl or a cycloalkyl, the two aryls in the diarylamino are not bonded to each other or are bonded to each other via a linking group, the two heteroaryls in the diheteroarylamino are not bonded to each other or are bonded to each other via a linking group, the aryl and heteroaryl in the arylheteroarylamino are not bonded to each other or are bonded to each other via a linking group,
Any "-C(-R)=" (wherein R is R ¹ to R ¹¹ ) in the a, b and c rings may be replaced with "-N=";
In the above general formula (H6),
R ¹ to R ¹⁶ are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl or cycloalkyl, at least one hydrogen of which may be further substituted with aryl, heteroaryl, diarylamino, alkyl or cycloalkyl, the two aryls of the diarylamino are not bonded to each other or are bonded via a linking group, the two heteroaryls of the diheteroarylamino are not bonded to each other or are bonded via a linking group, the aryl and heteroaryl of the arylheteroarylamino are not bonded to each other or are bonded via a linking group,
adjacent groups among R ¹ to R ¹⁶ may be bonded to each other to form an aryl ring or a heteroaryl ring together with the a ring, the b ring, the c ring or the d ring, at least one hydrogen atom in the formed ring may be substituted with an aryl, a heteroaryl, a diarylamino, a diheteroarylamino, an arylheteroarylamino, an alkyl or a cycloalkyl, at least one hydrogen atom in these rings may be further substituted with an aryl, a heteroaryl, a diarylamino, an alkyl or a cycloalkyl, the two aryls in the diarylamino are not bonded to each other or are bonded to each other via a linking group, the two heteroaryls in the diheteroarylamino are not bonded to each other or are bonded to each other via a linking group, the aryl and heteroaryl in the arylheteroarylamino are not bonded to each other or are bonded to each other via a linking group, and
At least one hydrogen atom in the compound or structure represented by each of the above formulas may be substituted with alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, cyano, halogen or deuterium.

<24> A display device or lighting device equipped with an organic electroluminescent element according to any one of <20> to <23>.

According to a preferred embodiment of the present invention, by producing an organic EL element using a novel polycyclic aromatic compound, for example as a dopant material, it is possible to provide an organic EL element having a narrow half-width of the emission spectrum and excellent color purity, as well as an organic EL element having excellent quantum efficiency and device life. In addition, since the novel polycyclic aromatic compound of the present invention has a rigid structure, many of the compounds have a sharper emission spectrum, a narrow half-width of the emission spectrum, and emit light with high color purity.

Specifically, the inventors have found that polycyclic aromatic compounds in which aromatic rings are linked by heteroelements such as boron, phosphorus, oxygen, nitrogen, and sulfur have a large HOMO-LUMO gap (band gap Eg in thin films) and high triplet energy. This is thought to be because the six-membered rings containing heteroelements have low aromaticity, which suppresses the decrease in the HOMO-LUMO gap associated with the expansion of the conjugated system, and because electronic perturbation of the heteroelements causes localization of the triplet excited states SOMO1 and SOMO2.

The heteroelement-containing polycyclic aromatic compounds according to the present invention have a small energy difference between the triplet excited state and the singlet excited state, and further have a large spin-orbit interaction and exhibit thermally activated delayed fluorescence, making them useful as fluorescent materials for organic EL devices. Materials with high triplet energy are also useful as electron transport layers and hole transport layers for phosphorescent organic EL devices and organic EL devices that utilize thermally activated delayed fluorescence. Furthermore, the HOMO and LUMO energies of these polycyclic aromatic compounds can be freely moved by introducing substituents, making it possible to optimize the ionization potential and electron affinity according to the surrounding materials.

1 is a schematic cross-sectional view showing an organic EL element according to an embodiment of the present invention.

<Polycyclic aromatic compound of the present invention>
<Explanation of the overall structure of the compound>
The present invention relates to a polycyclic aromatic compound represented by the following general formula (1A) or general formula (1B), and preferably to a polycyclic aromatic compound represented by the following general formula (2A) or general formula (2B). In each of the above formulas, "B" to "G" in a circle are symbols indicating the ring structure represented by the circle, "a" to "g" in the 6-membered aromatic ring are benzene rings or rings modified therefrom in some cases (such as 6- or 5-membered heteroaromatic rings), and the other symbols are the same as defined above. Furthermore, the symbols in all structural formulas shown in this paragraph and subsequent paragraphs are also defined as above.

The compound of the present invention is characterized in that it has a linking group Q as L in the molecule, or a linking group Q as a link to R in ^X1 or ^X2 , and at least one linking group Q is alkylene, cycloalkylene, alkenylene, alkynylene, arylene or heteroarylene. At least one hydrogen of the linking group Q is unsubstituted or substituted.

The linking group Q may be independently formed as L selected from a single bond and a linking group Q, or may be a linking group Q with R in ^X1 or ^X2 , or may be referred to as other linking groups. For example, as will be described in detail later, the linking group Q is, for example, L linking ring C and ring D in formula (1A), and is formed as a linking group when R is linked to ring B or ring E when ^X1 or ^X2 is >N-R. In formula (2A), for example, L linking ring c and ring d, and is a linking group when R is linked to ring b or ring e when ^X1 or ^X2 is >N-R. In formula (1B), similarly, it is formed as L linking ring C and ring D, and is also L linking ring G and ring B, and is also L linking ring F and ring E. Similarly, in formula (2B), for example, L connects ring c and ring d, and also L is a linking group connecting ring g and ring b, and also L connects ring f and ring e.

<Explanation of Ring Structure and Its Substituents>
R ^a is hydrogen or a substituent. The substituents include substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino (two aryls are not bonded to each other or are bonded via a linking group), substituted or unsubstituted diheteroarylamino (two heteroaryls of diheteroarylamino are not bonded to each other or are bonded via a linking group), substituted or unsubstituted arylheteroarylamino (aryl and heteroaryl are not bonded to each other or are bonded via a linking group), substituted or unsubstituted diarylboryl (two aryls are not bonded to each other or are bonded via a single bond or a linking group), substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted arylthio, or substituted silyl. Examples of the substituents when these groups have a substituent include aryl, heteroaryl, alkyl, or cycloalkyl. Details of the substituents listed here will be described below.

Ring B, ring C, ring D, ring E, ring F, and ring G are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen atom in these rings is not substituted or is substituted with a substituent. As the substituent, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted diarylamino (two aryls are not bonded to each other or are bonded via a linking group), a substituted or unsubstituted diheteroarylamino (two heteroaryls of diheteroarylamino are not bonded to each other or are bonded via a linking group), a substituted or unsubstituted arylheteroarylamino (aryls and heteroaryls are not bonded to each other or are bonded via a linking group), a substituted or unsubstituted diarylboryl (two aryls are not bonded to each other or are bonded via a single bond or a linking group), a substituted or unsubstituted alkyl, a substituted or unsubstituted cycloalkyl, a substituted or unsubstituted alkenyl, a substituted or unsubstituted alkoxy, a substituted or unsubstituted aryloxy, a substituted or unsubstituted arylthio, or a substituted silyl is preferable. When these groups have a substituent, the substituent can be aryl, heteroaryl, alkyl, or cycloalkyl. Details of the rings and substituents listed here will be described later.

R ^b , R ^c , R ^d , R ^e , R ^f , and R ^g are each independently hydrogen, aryl, heteroaryl, diarylamino (two aryls are not bonded to each other or are bonded via a linking group), diheteroarylamino (two heteroaryls of diheteroarylamino are not bonded to each other or are bonded via a linking group), arylheteroarylamino (aryl and heteroaryl are not bonded to each other or are bonded via a linking group), diarylboryl (two aryls are not bonded to each other or are bonded via a single bond or a linking group), alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, 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 (1A) and formula (1B) (i.e., rings B to G) preferably has a 5- or 6-membered ring that shares a bond with the fused bicyclic structure contained in each formula.

Here, the "fused bicyclic structure" means, in formula (1A), a structure in which two saturated hydrocarbon rings comprising Y ¹ , X ¹ , and N are fused (the first fused bicyclic structure on the left side of the formula), and a structure in which two saturated hydrocarbon rings comprising Y ² , X ² , and N are fused (the second fused bicyclic structure on the right side of the formula). Similarly, in formula (1B), a structure in which two saturated hydrocarbon rings comprising Y ¹ and two N are fused (the first fused bicyclic structure on the left side of the formula), a structure in which two saturated hydrocarbon rings comprising Y ² and two N are fused (the second fused bicyclic structure on the right side of the formula), and a structure in which two saturated hydrocarbon rings comprising Y ³ and two N are fused (the third fused bicyclic structure on the lower side of the formula). Although not shown in formula (2A) and formula (2B), fused bicyclic structures are present at similar positions.

In addition, the term "six-membered ring sharing a bond with a fused bicyclic structure" means ring b (a benzene ring (six-membered ring)) fused to a fused bicyclic structure, for example, as shown in formula (2A) or formula (2B). In addition, "an aryl ring or heteroaryl ring (which is ring B) has this six-membered ring" means that ring B is formed by this six-membered ring alone, or that ring B is formed by further condensing this six-membered ring to this six-membered ring so as to include this six-membered ring. In other words, the term "aryl ring or heteroaryl ring (which is ring B) having a six-membered ring" means that the six-membered ring constituting all or part of ring B is fused to a fused bicyclic structure. The same explanation applies to "ring C (ring c)", "ring D (ring d)", "ring E (ring e)", "ring F (ring f)", and "ring G (ring g)", and also to "five-membered ring".

The rings B, C, D, and E in formula (1A) correspond to the ring b and its substituent R ^b , the ring c and its substituent R ^c , the ring d and its substituent R ^d , and the ring e and its substituent R ^e in formula (2A), respectively. That is, formula (2A) corresponds to a structure in which "rings B to E having 6-membered rings" are selected as rings B to E in formula (1A). The reason for "having" a 6-membered ring is that, as described later, for example, adjacent groups among the four substituents R ^b for the 6-membered ring b are bonded to form a ring, and the ring b is further condensed with another ring, which corresponds to ring B. In this sense, while the rings in formula (1A) are represented by capital letters B to E, the rings in formula (2A) are represented by lowercase letters b to e.

The rings B, C, D, E, F, and G in formula (1B) correspond to the ring b and its substituent R ^b , the ring c and its substituent R ^c , the ring d and its substituent R ^d , the ring e and its substituent R ^e , the ring f and its substituent R ^f , and the ring g and its substituent R ^g in formula (2B), respectively. That is, formula (2B) corresponds to a structure in which "rings B to G having 6-membered rings" are selected as rings B to G in formula (1B). The reason for "having" a 6-membered ring is that, as described later, adjacent groups among the four substituents R ^b are bonded to form a ring for the 6-membered ring b, and the ring B is further condensed to the 6-membered ring b. In this sense, while the rings in formula (1B) are represented by capital letters B to G, the rings in formula (2B) are represented by lowercase letters b to g.

<Explanation of changes in ring structure due to bonding between substituents>
The substituents R ^b , R ^c , R ^d , R ^e , R ^f , and R Adjacent groups in ^g may be bonded to each other to form an aryl ring or a heteroaryl ring together with ring b, ring c, ring d, ring e, ring f, and ring g, respectively, and at least one hydrogen atom in the formed ring may be substituted with aryl, heteroaryl, diarylamino (two aryls are not bonded to each other or bonded via a linking group), diheteroarylamino (two heteroaryls in diheteroarylamino are not bonded to each other or bonded via a linking group), arylheteroarylamino (aryl and heteroaryl are not bonded to each other or bonded via a linking group), diarylboryl (two aryls are not bonded to each other or bonded via a single bond or a linking group), alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, 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 rings and substituents listed here will be described below.

Therefore, in the polycyclic aromatic compound of formula (2A) or formula (2B), the ring structure constituting the compound changes depending on the mutual bonding form of the substituents in rings b to g, for example, as shown in formulas (2A-fr) and (2B-fr) below. Rings B' and C' in the following formulas correspond to rings B and C in formulas (1A) and (1B), respectively. Rings d to g may also change in the same manner.

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

The above formula (2A-fr) and formula (2B-fr) have a ring B' or C' formed by condensing, for example, a benzene ring, an indole ring, a pyrrole ring, a benzofuran ring, or a benzothiophene ring to a ring b or ring c of the benzene ring, and the condensed ring B' or condensed ring C' formed is, for example, a naphthalene ring, a carbazole ring, an indole ring, a dibenzofuran ring, or a dibenzothiophene ring, respectively.

More specific examples of formula (2A-fr) and formula (2B-fr) are shown below.

The above formulae (2A-fr-ex) and (2B-fr-ex) are specific examples of formulae (2A-fr) and (2B-fr), respectively, in which two adjacent R ^b in the ring b of formulae (2A) and (2B) are bonded to form an aryl ring (naphthalene ring) represented by B' together with the ring b (benzene ring), and two adjacent R ^c in the ring c are bonded to form an aryl ring (dibenzofuran ring) represented by C' together with the ring b (benzene ring). The formed aryl ring has a six-membered ring (benzene ring b or c) that shares a bond with the above-mentioned fused two-ring structure. The optional substituents on the aryl rings B' and C' (rings B and C of formulae (1A) and (1B)) are represented by n Rs in addition to R ^b and R ^c , and the upper limit of n is the maximum number that can be substituted. These explanations can be similarly applied to any form other than the specific examples described above, for example, when rings d to g are changed or when other aryl rings or heteroaryl rings are formed.

<Explanation of central elements Y ¹ to Y ³ in the compound>
Y ¹ , Y ² , and Y ³ are each independently >B-, >P-, >P(═O)-, >P(═S)-, >Al-, >Ga-, >As-, >C(-R)-, >Si(-R)-, or >Ge(-R)-, and the R of >C(-R)-, the R of >Si(-R)-, and the R of >Ge(-R)- are each independently an aryl which may be substituted, a heteroaryl which may be substituted, an alkyl which may be substituted, or a cycloalkyl which may be substituted. ^{Y 1} , Y ² , and Y ³ are preferably >B-, >P-, >P(═O)-, or >P(═S)-, and more preferably >B-. Details of the substituents listed here will be described below.

<Explanation of Change in Ring Structure Due to Linking Group L Between Rings>
The rings C and D in formula (1A) and formula (1B) are bonded via L. The rings G and B, and the rings F and E in formula (1B) are also each independently bonded via L. The bond between the rings C and D via L is also called a CLD bond, the bond between the rings G and B via GLB bond, and the bond between the rings F and E via L via FLE bond.

<Explanation of Linking Group>
The linking group is an atom or a functional group that links two carbon atoms, and is preferably the linking group Q.
The linking group Q is -N(-R)-, -O-, -S-, -C(-R) ₂ -, -Si(-R) ₂ -, -Se-, a substituted or unsubstituted cycloalkylene, a substituted or unsubstituted alkylene, a substituted or unsubstituted alkenylene, a substituted or unsubstituted alkynylene, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene, and R of -N(-R)-, R of -C(-R) ₂ -, and R of -Si(-R) ₂ - are each independently hydrogen, an aryl, a heteroaryl, an alkyl, or a cycloalkyl, and preferably hydrogen, 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. At least one hydrogen atom in these is unsubstituted or substituted with alkyl (preferably alkyl having 1 to 6 carbon atoms, more preferably alkyl having 2 to 4 carbon atoms) or cycloalkyl (preferably cycloalkyl having 3 to 14 carbon atoms, more preferably cycloalkyl having 3 to 10 carbon atoms).
Furthermore, the cycloalkylene, alkenylene, alkynylene, arylene, and heteroarylene are preferably alkenylene having 2 to 6 carbon atoms, alkylene having 2 to 6 carbon atoms, cycloalkylene having 3 to 14 carbon atoms, arylene having 6 to 12 carbon atoms, or heteroarylene having 2 to 15 carbon atoms, and more preferably alkenylene having 2 to 6 carbon atoms, alkylene having 2 to 4 carbon atoms, cycloalkylene having 3 to 10 carbon atoms, arylene having 6 to 10 carbon atoms, or heteroarylene having 2 to 12 carbon atoms. At least one hydrogen atom in these is not substituted or is substituted with alkyl (preferably alkyl having 1 to 6 carbon atoms, more preferably alkyl having 2 to 4 carbon atoms) or cycloalkyl (preferably cycloalkyl having 3 to 14 carbon atoms, more preferably cycloalkyl having 3 to 10 carbon atoms).
As the alkenylene, the form -CR=CR- is most preferable, and as the alkylene, the form -CR ₂ -CR ₂ - is most preferable, where R is hydrogen or a substituent, and the preferred range of the substituent can be found in the above description of alkenylene and alkylene.
The details of the substituents listed here will be described later.

Examples of L include a single bond and a linking group Q, and are preferably a single bond, -N(-R)-, -O-, -S-, -C(-R) ₂ -, alkenylene, arylene, and heteroarylene, more preferably a single bond, arylene, -N(-R)-, -O-, and -S-, and most preferably a single bond and arylene. The above description can be referred to for the preferred ranges of these. Phenylene is most preferred as the arylene. At least one hydrogen of these is unsubstituted or substituted, and the above description can be referred to for the preferred range of the substituent.

At least one L is alkylene, cycloalkylene, alkenylene, alkynylene, arylene, or heteroarylene, preferably alkenylene or arylene, and most preferably phenylene. The above description can be referred to for the preferred ranges. At least one hydrogen is unsubstituted or substituted, and the above description can be referred to for the preferred ranges.

The position at which the two rings are bonded by the bonding group is not particularly limited as long as it is a position where bonding is possible, but it is preferable for them to be bonded at the most adjacent positions, for example, it is preferable for them to be bonded at the ortho (2nd) positions based on the bonding position (1st position) of the "N" in each ring (see the structural formulas of formula (1A) and formula (1B)).

In the lower formulas, the c and d rings in formula (2A) and formula (2B) are also bonded by L in the same manner as in the higher formula. In the lower formula, the g and b rings and the f and e rings in formula (2B) are also bonded independently by L in the same manner as in the higher formula. They may be bonded by a single bond or a linking group (collectively also referred to as a linking group). The bond between the c and d rings via L consisting of a single bond or a linking group Q is also referred to as a cLd bond, the bond between the g and b rings is also referred to as a gLb bond, and the bond between the f and e rings is also referred to as an fLe bond. The type and bonding position of the linking group Q can be found in the explanation of the higher formulas.

<Explanation of Bond L (1)>
In the compound of the present invention, as described above, the C and D rings (c and d rings), the G and B rings (g and b rings), and the F and E rings (f and e rings) can be bonded by L, so that the first bridged structure can be formed in formula (1A) and formula (2A), and the first, second, and third bridged structures can be formed in formula (1B) and formula (2B). L in the following structural formula means a bonding group (single bond and linking group). However, the compound of the present invention is characterized in that one or two of the three bridged structures that can be formed in the molecule are formed.

As described above, L includes single bonds and linking groups as bonding groups, and the bonding positions between rings are not limited. In addition, as described elsewhere, the ring structure of each ring, such as ring c, changes due to bonding between adjacent substituents.

The position at which the two rings are bonded by L is not particularly limited as long as it is a bondable position, but it is preferable that they are bonded at the most adjacent positions, and for example, it is preferable that they are bonded at ortho (2-position) positions based on the bonding position (1-position) of "N" in each ring (see the structural formulas of formula (1A), formula (1B), formula (2A), and formula (2B)).
When L is formed, the two rings which it bonds to are both preferably benzene rings.

<Explanation of Linking Elements ^X1 and ^X2 in Compound>
^X1 and ^X2 in formula (1A) and formula (2A) are each independently >N-R, >O, >S, >C(-R) ₂ , >Si(-R) ₂ , or >Se, and R of >N-R, R of >C(-R) ₂ , and R of >Si(-R) ₂ are each independently hydrogen, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl, or an optionally substituted cycloalkyl. Details of the substituents listed here will be described below.

^X1 and ^X2 are preferably >N-R, >O, >S, or >C(-R) ₂ , more preferably >N-R or >O, and even more preferably >N-R. From the viewpoint of good TADF properties, >N-R, >O, and >S are preferred, and more specifically, from the viewpoint of orbital localization due to multiple resonance effect, >N-R is preferred, and from the viewpoint of heavy atom effect, >S is preferred. From the viewpoint of emission wavelength, >O is preferred for short wavelength emission, and >N-R or >S is preferred for long wavelength emission.

Preferred embodiments of formula (1A) and formula (1B) include formula (1A-a), formula (1A-b), formula (1A-c), formula (1B-a), formula (1B-b), or formula (1B-c) as shown below. This is based on the description that "R of >N-R, R of >C(-R) ₂ , or R of >Si(-R) ₂ as X ¹ is bonded to at least one of ring a and ring B via a single bond or a linking group, and R of >N-R, R of >C(-R) ₂ , or R of >Si(-R) ₂ as X ² is bonded to at least one of ring a and ring E via a single bond or a linking group", and corresponds to the form in formula (1A) and formula (1B) where X ¹ or X ² is >N-R and R is bonded to ring B or ring E (ring b or ring e) via a single bond or a linking group (L ^Q ). For each symbol and its preferred range, the explanation of formula (1A) and formula (1B) can be referred to, but in formula (1A-a), formula (1A-b), formula (1A-c), formula (1B-a), formula (1B-b), or formula (1B-c), ^X1 or ^X2 is not >N-R. In addition, for ^LQ, the description of L can be referred to as it is.

At least one of the two Rs in >C(-R) ₂ and at least one of the two Rs in >Si(-R) ₂ may be bonded to each other via a single bond or a linking group (collectively referred to as a linking group). An example of this linking group is the linking group Q. Details of the substituents listed here will be described below.

As the bonding group, a single bond, alkenylene as a linking group, -N(-R)-, -O-, -S-, -C(-R) ₂ -, -Si(-R) ₂ -, and -Se- are preferred, a single bond, alkenylene (particularly, -CR=CR-), -N(-R)-, -O-, -S-, and -C(-R) ₂ - are more preferred, a single bond, and -CR=CR-, -N(-R)-, -O-, and -S- as a linking group are further preferred, and a single bond is most preferred.

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

<Explanation of Change in Ring Structure due to Bonding of ^X1 or ^X2 to a Ring>
In formula (1A) and formula (2A), R of >N-R, R of >C(-R) ₂ , or R of >Si(-R) ₂ as ^X1 is not bonded to at least one of ring a and ring B (ring b) through a single bond or a linking group (preferably a linking group Q, which are also collectively referred to as a linking group).
In formula (1A) and formula (2A), R of >N-R, R of >C(-R) ₂ , or R of >Si(-R) ₂ as ^X2 is not bonded to or is bonded to at least one of ring a and ring E (ring e) via a single bond or a linking group (collectively also referred to as a bonding group).

As ^X1 or ^X2 involved in the bond, >N--R and >C(--R) ₂ are preferred, and >N--R is more preferred.

As the bonding group, a single bond, and -CR=CR-, -N(-R)-, -O-, -S-, -C(-R) ₂ -, -Si(-R) ₂ -, and -Se- are preferred as the linking group Q, a single bond and -CR=CR-, -N(-R)-, -O-, -S-, and -C(-R) ₂ - are more preferred, a single bond, and -CR=CR-, -N(-R)-, -O-, and -S- are further preferred as the linking group Q, and a single bond and -CR=CR- as the linking group Q are most preferred.

As the ring to be bonded, ^X1 is preferably ring B (ring b), and ^X2 is preferably ring E (ring e).

The provision in the higher-level formula (1A) that "R of >N-R, R of >C(-R) ₂ , or R of >Si(-R) ₂ is bonded to at least one of ring a and ring B (or ring E) through a single bond or a linking group Q" corresponds to the provision in the lower-level formula (2A) that "R of >N-R, R of >C(-R) ₂ , or R of >Si(-R) ₂ is bonded to at least one of ring a and ring b (or ring e) through a single bond or a linking group Q that is -CR=CR-, -C≡C-, -N(-R)-, -O-, -S-, -C(-R) ₂ -, -Si(-R) ₂ -, or -Se-."

This definition can be expressed, for example, by the following structural formula: In the structural formula, the substituents R ^a , R ^b , R ^c , R ^d and R ^e are not shown, but actually exist.

In the structural formula on the left, R in the options for ^X1 and ^X2 (>N-R, >C(-R) ₂ , and >Si(-R) ₂ ) is an example where R is bonded to ring b and ring e, respectively, and represents a compound having rings B' and E' formed by condensing other rings to ring b (benzene ring) and ring e (benzene ring) so as to incorporate ^X1 or ^X2 . The condensed rings B' and E' formed are, for example, dihydrodibenzoazepine rings, dibenzoazepine rings, tribenzoazepines, phenoxazine rings, phenothiazine rings, carbazole rings, or acridine rings.

The structural formula in the center represents a more specific example of the structural formula on the left, in which R (phenyl group) of >N-R, which are ^X1 and ^X2 , is bonded to ring b (benzene ring) via o-phenylene, which is the linking group Q, to form a tribenzoazepine ring B', and is bonded to ring e (benzene ring) via a single bond to form a carbazole ring E' surrounded by a dashed line.

The structural formula on the right shows a more specific example of the structural formula on the left, in which R (phenyl group) of >N-R which are ^X1 and ^X2 is bonded to ring b (benzene ring) via the linking group -O- to form a phenoxazine ring B' surrounded by a dashed line, and R is bonded to ring e (benzene ring) via the linking group -S- to form a phenothiazine ring E' surrounded by a dashed line.

The position at which R in the options for ^X1 and ^X2 (>N-R, >C(-R) ₂ , and >Si(-R) ₂ ) is bonded to the ring (ring B, ring E, ring b, and ring e) via a bonding group is not particularly limited as long as it is a bondable position, but it is preferable for it to be bonded at the most adjacent position, and for example, when R is a phenyl group, it is preferable for it to be bonded at the ortho (2nd position) positions based on the bonding positions (1st position) of "X ¹ " and "X ² " in the ring and phenyl group to be bonded (see the above structural formula).

The above-mentioned explanation of the specific examples can be similarly applied to any other forms than these specific examples, for example, when either one of ^X1 and ^X2 is bonded to a ring, when they are bonded to ring a, when they are bonded via another linking group, and the like.

<Explanation regarding the number of bridge structures via single bonds or linking group Q in the carbazole-like structure>
As described above, in formula (1A) and formula (2A), the first bridge structure is formed from the C ring and D ring bond bridged by a single bond or a linking group, or the c ring d bond and d ring bridged by L consisting of a single bond and a linking group Q, the second bridge structure is formed from the X ¹ B bond, X ¹ QB bond, X ¹ b bond or X ¹ Qb bond, and the third bridge structure is formed from the X ² E bond, X ² QE bond, X ² e bond or X ² Qe bond. In addition, in formula (1B) and formula (2B), the first bridge-like structure is formed from the CLD bond or cLd bond, the second structure is formed from the GL ^Q B bond or gL ^Q b bond, and the third structure is formed from the FL ^Q E bond or fL ^Q e bond. The compound of the present invention is characterized in that at least one of these three bridge-like structures that can be formed within a molecule is formed, and at least one of the linking groups Q is an alkylene, cycloalkylene, alkenylene, alkynylene, arylene, or heteroarylene.

<Explanation of structural changes in ring a and rings b to g>
In the above explanation, ring a, ring b, ring c, ring d, ring e, ring f, and ring g have been illustrated and explained as benzene rings, but hereinafter, examples will be explained in which ring a and rings b to g are structurally changed to 5- or 6-membered aryl or heteroaryl rings other than benzene rings. Note that the above explanation can be similarly understood for the cases in which these rings undergo the following structural changes.

<Structural change of ring a>
In formula (1A) and formula (2A), "-C(-R ^a )=" in the ring a may be replaced with "-N=" to form a pyridine ring. Note that the following structural diagram shows only the ring a and a part of its surrounding structure.

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

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

In addition, there are the following variations:

It is preferred that "-C(-R ^d )=" at the ortho or para position relative to the carbon to which X ¹ , X ² or >N- is bonded is replaced with "-N=".

The same applies when other parts are replaced with "-N=", or when rings b, c, e, f, and g other than ring d are changed.

In addition, all of "-C(-R)=" (including the cases where R is R ^a , R ^b , R ^c , R ^d , R ^e , R ^f or R ^g , and all of the cases where R is a substituent defined by the ring structure) are preferably not "-N=".

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

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

In addition, there are the following variations:

The same applies when other positions are replaced with "-N(-R)-", "-O-", "-S-", "-C(-R) ₂ -", "-Si(-R) ₂ -" or "-Se-" or when rings b, c, e, f and g other than ring d are changed.

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

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

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

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

The "aryl ring" is, for example, an aryl ring having 6 to 30 carbon atoms, preferably an aryl ring having 6 to 20 carbon atoms, an aryl ring having 6 to 16 carbon atoms, an aryl ring having 6 to 12 carbon atoms, or an aryl ring having 6 to 10 carbon atoms.
The "aryl rings" as rings B to G in formulae (1A) and (1B) correspond to "aryl rings formed by bonding adjacent groups among R ^b , R ^c , R ^d , R ^e , R ^f , and R ^g together to form rings b, c, d, e, f, and g, respectively" defined in formulae (2A) and (2B). However, for this "formed aryl ring", rings b to g are already composed of a benzene ring having 6 carbon atoms, and therefore the lower limit of the carbon number is the total carbon number of the fused ring formed by condensing the smallest 5-membered ring to this benzene ring, which is 9.
However, rings b to g, which are benzene rings, may be changed to nitrogen-containing heteroaryl rings (six- or five-membered rings) or oxygen- and sulfur-containing heteroaryl rings (five-membered rings) as described above, and in this case, the lower limit of the number of carbon atoms changes accordingly.

Specific examples of "aryl rings" include a monocyclic benzene ring, a fused bicyclic naphthalene ring, a fused tricyclic acenaphthylene ring, a fluorene ring, a phenalene ring, a phenanthrene ring, an anthracene ring, a fused tetracyclic tricyclic triphenylene ring, a pyrene ring, or a naphthacene ring, or a fused pentacyclic perylene ring or 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 ring B to ring G in formula (1A) and formula (1B) corresponds to the "heteroaryl ring formed by bonding adjacent groups among R ^b , R ^c , R ^d , R ^e , R ^f , and R ^g together to form ring b, ring c, ring d, ring e, ring f, and ring g, respectively" defined in formula (2A) and formula (2B). However, for this "formed heteroaryl ring", ring b to ring g are already composed of a benzene ring having 6 carbon atoms, and therefore the lower limit of the carbon number is the total carbon number of the fused ring formed by condensing the smallest 5-membered ring to this benzene ring, which is 6.
However, rings b to g, which are benzene rings, may be changed to nitrogen-containing heteroaryl rings (six- or five-membered rings) or oxygen- and sulfur-containing heteroaryl rings (five-membered rings) as described above, and in this case, the lower limit of the number of carbon atoms changes accordingly.

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

The heteroaryl ring also includes the following formula (BO):

"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; acenaphthylene-(1-, 3-, 4- , or 5-)yl, fluoren-(1-, 2-, 3-, 4-, or 9-)yl, phenalen-(1- or 2-)yl, phenanthrene-(1-, 2-, 3-, 4-, or 9-)yl, or anthracene-(1-, 2-, or 9-)yl, the tetracyclic ring system quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-furanyl, m-terphenyl-4-yl, or m-quaterphenyl), fused tetracyclic ring systems, triphenylene-(1- or 2-)yl, pyrene-(1-, 2-, or 4-)yl, or naphthacene-(1-, 2-, or 5-)yl, or fused pentacyclic ring systems, 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.

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

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

Specific examples of "heteroaryl" include pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, phenanthrolinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, carbolyl, 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, benzobenzoindolocarbazolyl, imidazolinyl, or oxazolinyl.

Furthermore, a monovalent group obtained by removing one hydrogen from the following formula (BO) is also included in the heteroaryl.

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

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

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

The description "two heteroaryls are bonded through a linking group or are not bonded" in diarylamino (two aryls are bonded through a linking group or are not bonded), diheteroarylamino (two heteroaryls are bonded through a linking group or are not bonded), and arylheteroarylamino (aryl and heteroaryl are bonded through a linking group or are not bonded) means that, for example, two phenyl groups of a diphenylamino group form a bond with a linking group as shown below. This explanation also applies to diheteroarylamino and arylheteroarylamino formed by aryls and heteroaryls. As the linking group, a linking group Q is preferred, and the description in the specification can be referred to for its preferred range (including the preferred range of the substituent).

In addition, in this specification, when it is simply described as "diarylamino", "diheteroarylamino" or "arylheteroarylamino", unless otherwise specified, it is assumed that the explanation that "two aryls are bonded via a linking group or are not bonded", "two heteroaryls are bonded via a linking group or are not bonded", and "aryl and heteroaryl are bonded via a linking group or are not bonded", respectively, is added.

"Diarylboryl" is a boryl group substituted with two aryls, and the above description of "aryl" can be cited for details of this aryl. In addition, these two aryls are not bonded or are bonded via a single bond or a linking group (preferably linking group Q). Here, the definition of linking group Q and its preferred range can be referred to the description in this specification.

"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.

"Alkylene" refers to a divalent group in which one hydrogen atom has been removed from the above-mentioned "alkyl". For example, it is a straight chain alkylene having 1 to 24 carbon atoms or a branched chain alkylene having 3 to 24 carbon atoms, and preferably, it is an alkylene having 1 to 18 carbon atoms (branched chain alkylene having 3 to 18 carbon atoms), an alkylene having 1 to 12 carbon atoms (branched chain alkylene having 3 to 12 carbon atoms), an alkylene having 1 to 6 carbon atoms (branched chain alkylene having 3 to 6 carbon atoms), an alkylene having 1 to 5 carbon atoms (branched chain alkylene having 3 to 5 carbon atoms), an alkylene having 1 to 4 carbon atoms (branched chain alkylene having 3 to 4 carbon atoms), etc.

For "alkenyl", the above explanation of "alkyl" can be referred to, and it is a group in which the C-C single bond in the "alkyl" structure is replaced with a C=C double bond, including groups in which not only one but two or more single bonds are replaced with double bonds (also called alkadiene-yl or alkanetriene-yl). "Alkenyl" includes linear alkenyl with 2 to 24 carbon atoms or branched alkenyl with 4 to 24 carbon atoms. Alkenyl with 2 to 18 carbon atoms is preferred, alkenyl with 2 to 12 carbon atoms is more preferred, alkenyl with 2 to 6 carbon atoms is even more preferred, and alkenyl with 2 to 4 carbon atoms is particularly preferred. Specific examples of "alkenyl" include vinyl, allyl, butadienyl, etc.

"Alkenylene" refers to a divalent group obtained by removing one hydrogen from the above-mentioned "alkenyl".

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

"Alkynylene" refers to a divalent group obtained by removing one hydrogen from the above-mentioned "alkynyl".

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

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

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

"Alkoxy" may be either straight chain or branched chain, for example straight chain alkoxy having 1 to 24 carbon atoms or branched chain alkoxy having 3 to 24 carbon atoms, 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.

"Arylthio" is a group represented by "Ar-S- (Ar is an aryl group)" and for details on this aryl, please refer to the explanation of "aryl" above.

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

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

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

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

"Dialkylcycloalkylsilyl" is a silyl group substituted with two alkyls and one cycloalkyl. For details 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.

Specifically, the emission wavelength can be adjusted by the steric hindrance, electron donating property and electron withdrawing property of the structure of the first and second substituents, and the groups represented by the following structural formulas are preferred, and more preferred are methyl, t-butyl, t-amyl, t-octyl, neopentyl, 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, Preferred are methyl, t-butyl, t-amyl, t-octyl, neopentyl, 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. From the viewpoint of ease of synthesis, a larger steric hindrance is preferred for selective synthesis, and specifically, 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, bis(p-(t-butyl)phenyl)amino, 3,6-dimethylcarbazolyl, and 3,6-di-t-butylcarbazolyl are preferred.

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

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

For example, in the compound represented by formula (1A) or formula (1B), ring B, ring C, ring D, ring E, ring F, ring G, aryl, and heteroaryl, and in the compound represented by formula (2A) or formula (2B), ring b, ring c, ring d, ring e, ring f, ring g, the "formed ring", aryl, and heteroaryl (including aryl and heteroaryl as part of each of the substituents listed above) may be condensed with at least one cycloalkane.

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

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

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

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

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

At least one hydrogen atom in the cycloalkane may be substituted. Examples of the substituent include aryl, heteroaryl, diarylamino (two aryls are not bonded to each other or are bonded via a linking group), diheteroarylamino (two heteroaryls in diheteroarylamino are not bonded to each other or are bonded via a linking group), arylheteroarylamino (aryl and heteroaryl are not bonded to each other or are bonded via a linking group), diarylboryl (two aryls are not bonded to each other or are bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, substituted silyl, deuterium, cyano, and halogen. For details of these, the description of the first substituent described above can be cited. Among these substituents, alkyl (e.g., alkyl having 1 to 6 carbon atoms), cycloalkyl (e.g., cycloalkyl having 3 to 14 carbon atoms), halogen (e.g., fluorine), and deuterium are preferred. In addition, when cycloalkyl is substituted, it may be a substitution form that forms a spiro structure. For example, an example in which a spiro structure is formed in a cycloalkane condensed to one benzene ring (phenyl group) is shown below. In each structural formula, * means a benzene ring included in the skeletal structure of the compound when it is a benzene ring, and means a bond substituting the skeletal structure of the compound when it is a phenyl group.

Other forms of cycloalkane condensation include those in which the polycyclic aromatic compound of the present invention is substituted with, for example, a diarylamino group condensed with a cycloalkane (condensed to the aryl group portion), a carbazolyl group condensed with a cycloalkane (condensed to the benzene ring portion), or a benzocarbazolyl group condensed with a cycloalkane (condensed to the benzene ring portion). The above explanation of the "diarylamino group" can be cited.

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

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

各式中、
Ｒは、それぞれ独立して、水素、炭素数６～１６のアリール、炭素数２～２０のヘテロアリール、ジアリールアミノ（ただしアリールは炭素数６～１０のアリール）、ジアリールボリル（ただしアリールは炭素数６～１０のアリールであり、２つのアリールは単結合または連結基により結合していてもよい）、炭素数１～１２のアルキル、または炭素数３～１６のシクロアルキルであり、これらにおける少なくとも１つの水素は、炭素数１～５のアルキルまたは炭素数５～１０のシクロアルキルで置換されていてもよく、
ｏはそれぞれ独立して１～３の整数であり、
ｐはそれぞれ独立して１～４の整数であり、
ｑはそれぞれ独立して１～５の整数であり、
上記各式で表される化合物における少なくとも１つの水素は、重水素、シアノ、またはハロゲンで置換されていてもよい。 <Explanation of specific examples of polycyclic aromatic compounds of the present invention>
For example, a compound represented by any one of the following structural formulas is preferred.

In each formula,
R's 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 two aryls may be bonded to each other 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 may be substituted by an alkyl having 1 to 5 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms;
Each o is independently an integer from 1 to 3;
Each p is independently an integer from 1 to 4;
Each q is independently an integer from 1 to 5;
At least one hydrogen in the compounds represented by the above formulas may be substituted with deuterium, cyano, or halogen.

For a more specific description of R, the above description of aryl and the like can be cited. In addition, o, p, and q are preferably 1 or 2, more preferably 1, and even more preferably 0.

<Use as a thermally activated delayed fluorescence (TADF) material>
The compound of the present invention can also be used as a TADF material. In particular, the compounds represented by formulae (1A) and (2A) are more preferable than the compounds represented by formulae (1B) and (2B), and the rings sharing a bond with the fused bicyclic structure in rings B to G and rings b to g are preferably six-membered rings, and more preferably six-membered aryl rings including ring a.

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

The polycyclic aromatic compound according to the present invention can 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.

These polymer compounds, crosslinked polymers, pendant polymer compounds, and pendant crosslinked polymers may contain, in addition to the repeating units of the polycyclic aromatic compound according to the present invention, at least one repeating unit 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.

Examples of the substituents in these repeating units include aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (the two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, and alkyldicycloalkylsilyl. For details on the "aryl" in triarylamine and these substituents, see the explanation in the polycyclic aromatic compound of the present invention.

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 Compound According to the Present Invention The polycyclic aromatic compound according to the present invention can be basically produced by first producing an intermediate by bonding ring a to rings B to G or rings b to g with a bonding group (a group containing "N" or ^X1 or ^X2 ) (first reaction), and then producing a final product by bonding ring a to rings B to G or rings b to g with a bonding group (a group containing ^Y1 to ^Y3 ) (second reaction). The production method described in International Publication WO 2015/102118 can be used as a reference.

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

The second reaction is a reaction for introducing Y ¹ to Y ³ which bond the ring a to the rings B to G or the rings b to g as shown in the following schemes (1) and (2). First, the hydrogen atoms between "N" and X ¹ and X ² , and the hydrogen atoms between "N"s are orthometalated with n-butyllithium, sec-butyllithium, t-butyllithium, or the like. Next, a halide of Y ¹ to Y ³ such as boron trichloride or boron tribromide is added to carry out lithium-boron metal exchange, and then a Bronsted base such as N,N-diisopropylethylamine is added to carry out a tandem boron-Friedel-Crafts reaction to obtain the target product. In the second reaction, a Lewis acid such as aluminum trichloride may be added to promote the reaction. The symbols in the structural formulae in the following schemes (1) and (2) and the subsequent schemes are defined as above. In addition, it is also possible to omit the reaction step of metalating a hydrogen atom (H) using an organic alkali compound, as described in Journal of the American Chemistry, 2018, 140, 1195-1198, and directly react ^Y1 with a halide (such as boron tribromide).

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

The above schemes (1) to (3) are representative methods for producing a compound in which Y ¹ to Y ³ are boron (B) atoms.

Next, as an example, the following schemes (4) and (5) show cases where Y ¹ to Y ³ are phosphorus sulfide, phosphorus oxide, or phosphorus atom. As in the above, first, the hydrogen atoms between "N" and X ¹ and X ² , and the hydrogen atoms between "N"s are orthometalated with n-butyl lithium or the like. Next, phosphorus trichloride and sulfur are added in this order, and finally, a Lewis acid such as aluminum trichloride and a Bronsted base such as N,N-diisopropylethylamine are added to carry out a tandem phospha Friedel-Crafts reaction, thereby obtaining a compound in which Y ¹ to Y ³ are phosphorus sulfide. In addition, a compound in which Y ¹ to Y ³ are phosphorus oxide can be obtained by treating the obtained phosphorus sulfide compound with m-chloroperbenzoic acid (m-CPBA), and a compound in which Y ¹ to Y ³ are phosphorus atoms can be obtained by treating with triethylphosphine.

In the above scheme, examples where Y ¹ to Y ³ are B, P, P═O or P═S are mainly described, but other compounds can also be produced by appropriately changing the raw materials.

In the above scheme, an example ^is shown in which a tandem hetero Friedel-Crafts reaction is carried out by ortho-metalating the hydrogen atoms (or halogen atoms) between "N" and ^X1 and ^X2 , or the hydrogen atoms (or halogen atoms) between "N"s with butyllithium or the like before adding halides of Y 1 to Y ³ such as boron trichloride or boron tribromide. However, the reaction can also be carried out by adding halides of Y ¹ to Y ³ such as boron trichloride or boron tribromide without ortho-metalating using butyllithium or the like.

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

The orthometalation reagents used in the above scheme include alkyl lithiums such as methyl lithium, n-butyl lithium, sec-butyl lithium, and t-butyl lithium, organic alkali compounds such as lithium diisopropylamide, lithium tetramethylpiperidide, lithium hexamethyldisilazide, and potassium hexamethyldisilazide, and dispersed alkali metals such as organic solvent-dispersed Na.

Examples of the metal exchange reagent of metal-(Y ¹ to Y ³ ) used in the above scheme include halides of Y ¹ to Y ³ such as trifluorides of Y ¹ to Y ³ , trichlorides of Y ¹ to Y ³ , tribromides of Y ¹ to Y ³ , and triiodides of Y ¹ to Y ³ , aminated halides of Y ¹ to Y ³ such as CIPN(NEt ₂ ) ₂ , alkoxylated compounds of Y ¹ to Y ³ , and aryloxylated compounds of Y ¹ to Y ³ .

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

Lewis acids used in the above scheme include _AlCl3 , AlBr3, _AlF3 , _BF3.OEt2 , _BCl3 , _BBr3 , _GaCl3 , _GaBr3 , _InCl3 , _InBr3 , In(OTf) ₃ , SnCl4, _SnBr4 , AgOTf, _ScCl3 , Sc(OTf) ₃ , _ZnCl2 , _ZnBr2 , Zn(OTf) ₂ , _{MgCl2 , MgBr2} , Mg(OTf) ₂ , LiOTf _, NaOTf _, KOTf, Me3SiOTf, Cu(OTf) ₂ , _CuCl2 , _YCl3 , Y( _OTf ) ₃ , _TiCl4 , _TiBr4 , _ZrCl4 , _ZrBr4 , _FeCl3 , _FeBr3 , _CoCl3 , _CoBr3 , etc.

In the above scheme, a Bronsted base or Lewis acid may be used to promote the tandem hetero Friedel-Crafts reaction. However, when a halide of Y ¹ to Y ³ such as trifluoride of Y ¹ to Y ³ , trichloride of Y ¹ to Y ³ , tribromide of Y ¹ to Y ³ , or triiodide of Y ¹ to Y ³ 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 to Y ³ or an alkoxylated product of Y ¹ to Y ³ is used, amines and alcohols are generated as the aromatic electrophilic substitution reaction proceeds, so it is not necessary to use a Bronsted base in many cases, but since the leaving ability of amino groups and alkoxy groups is low, it is effective to use a Lewis acid to promote the leaving thereof.

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

3. Organic Devices The polycyclic aromatic compound according to the present invention can be used as a material for organic devices, such as organic electroluminescent devices, organic field effect transistors, and organic thin-film solar cells.

3-1 Organic Electroluminescent Device The organic EL device according to this embodiment will be described in detail below 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 be a single layer or multiple layers.

In addition to the above-mentioned "substrate/anode/hole injection layer/hole transport layer/light-emitting layer/electron transport layer/electron injection layer/cathode" configuration, the layers constituting the organic EL element may be "substrate/anode/hole transport layer/light-emitting layer/electron transport layer/electron injection layer/cathode", "substrate/anode/hole injection layer/light-emitting layer/electron transport layer/electron injection layer/cathode", "substrate/anode/hole injection layer/light-emitting layer/electron transport layer/electron injection layer/cathode", "substrate/anode/hole injection layer/hole transport layer/light-emitting ... transport", The configuration may be "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 transport layer/cathode", "substrate/anode/hole injection layer/light-emitting layer/electron injection layer/cathode", "substrate/anode/hole injection layer/light-emitting layer/electron transport layer/cathode", "substrate/anode/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 of the substrate 101, a gas barrier film such as a dense silicon oxide film may be provided on at least one side thereof. It is particularly preferable to provide a gas barrier film when a synthetic resin plate, film or sheet having poor gas barrier properties is used as the substrate 101.

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

Materials for forming the anode 102 include inorganic and organic compounds. Examples of inorganic compounds include 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. Examples of organic compounds include 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 become traps during manufacture and use. In the present invention, the polycyclic aromatic compound represented by the above general formula (1A) or general formula (1B) can be used as a material for the hole injection layer and hole transport layer.

As the material for forming the hole injection layer 103 and the hole transport layer 104, any compound can be selected 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 above-mentioned hole injection layer material and hole transport layer material can 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 reactive substituent can be quoted from the description of the polycyclic aromatic compound represented by the above general formula (1A) or (1B).
The applications of such polymer compounds and crosslinked polymers will be described in detail below.

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

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 in the entire host material, or may be contained partially in the host material. As a doping method, the dopant material may be formed by co-evaporation with the host material, but it may also be mixed with the host material in advance and then simultaneously evaporated, or mixed with the host material together with an organic solvent in advance and then formed into a film by a wet film-forming method.

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

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

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

Host materials include condensed ring derivatives such as anthracene and pyrene, which have long been known as light emitters, bisstyryl derivatives such as bisstyrylanthracene derivatives and distyrylbenzene derivatives, tetraphenylbutadiene derivatives, cyclopentadiene derivatives, fluorene derivatives, and benzofluorene derivatives.

From the viewpoint of promoting rather than inhibiting the generation of TADF in the light-emitting layer, the triplet energy of the host material is preferably higher than the triplet energy of the dopant or assist dopant having the highest triplet energy in the light-emitting layer. Specifically, the triplet energy of the host material is preferably 0.01 eV or more, more preferably 0.03 eV or more, and even more preferably 0.1 eV or more. A TADF-active compound may also be used as the host material.

Examples of the host material include a compound represented by the following general formula (H1), a compound represented by the following general formula (H2), a compound represented by the following general formula (H3), a compound including a structure represented by the following general formula (H4), a compound represented by the following general formula (H5), a compound represented by the following general formula (H6), and a TADF material. The compound represented by the general formula (H1) is preferred.

上記式（Ｈ１）中、Ｌ^１は炭素数６～３０のアリーレンまたは炭素数２～３０のヘテロアリーレンであり、炭素数６～２４のアリーレンが好ましく、炭素数６～１６のアリーレンがより好ましく、炭素数６～１２のアリーレンがさらに好ましく、炭素数６～１０のアリーレンが特に好ましく、また、炭素数２～２５のヘテロアリーレンが好ましく、炭素数２～２０のヘテロアリーレンがより好ましく、炭素数２～１５のヘテロアリーレンがさらに好ましく、炭素数２～１０のヘテロアリーレンが特に好ましい。アリーレンとして具体的には、ベンゼン環、ビフェニル環、ナフタレン環、テルフェニル環、アセナフチレン環、フルオレン環、フェナレン環、フェナントレン環、トリフェニレン環、ピレン環、ナフタセン環、ペリレン環およびペンタセン環などの二価の基が挙げられる。また、ヘテロアリーレンとして具体的には、ピロール環、オキサゾール環、イソオキサゾール環、チアゾール環、イソチアゾール環、イミダゾール環、オキサジアゾール環、チアジアゾール環、トリアゾール環、テトラゾール環、ピラゾール環、ピリジン環、ピリミジン環、ピリダジン環、ピラジン環、トリアジン環、インドール環、イソインドール環、１Ｈ－インダゾール環、ベンゾイミダゾール環、ベンゾオキサゾール環、ベンゾチアゾール環、１Ｈ－ベンゾトリアゾール環、キノリン環、イソキノリン環、シンノリン環、キナゾリン環、キノキサリン環、フタラジン環、ナフチリジン環、プリン環、プテリジン環、カルバゾール環、アクリジン環、フェノキサチイン環、フェノキサジン環、フェノチアジン環、フェナジン環、フェナザシリン環、インドリジン環、フラン環、ベンゾフラン環、イソベンゾフラン環、ジベンゾフラン環、チオフェン環、ベンゾチオフェン環、ジベンゾチオフェン環、フラザン環、オキサジアゾール環、チアントレン環、インドロカルバゾール環、ベンゾインドロカルバゾール環、ベンゾベンゾインドロカルバゾール環およびナフトベンゾフラン環などの二価の基が挙げられる。
式（Ｈ１）で表される化合物における少なくとも１つの水素は、炭素数１～６のアルキル、炭素数３～１４のシクロアルキル、シアノ、ハロゲンまたは重水素で置換されていてもよい。 <Compound represented by general formula (H1)>

In the above formula (H1), L ¹ is an arylene having 6 to 30 carbon atoms or a heteroarylene having 2 to 30 carbon atoms, preferably an arylene having 6 to 24 carbon atoms, more preferably an arylene having 6 to 16 carbon atoms, even more preferably an arylene having 6 to 12 carbon atoms, particularly preferably an arylene having 6 to 10 carbon atoms, and also preferably a heteroarylene having 2 to 25 carbon atoms, more preferably a heteroarylene having 2 to 20 carbon atoms, even more preferably a heteroarylene having 2 to 15 carbon atoms, particularly preferably a heteroarylene having 2 to 10 carbon atoms. Specific examples of the arylene include divalent groups such as a benzene ring, a biphenyl ring, a naphthalene ring, a terphenyl ring, an acenaphthylene ring, a fluorene ring, a phenalene ring, a phenanthrene ring, a triphenylene ring, a pyrene ring, a naphthacene ring, a perylene ring, and a pentacene ring. Specific examples of heteroarylene 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, and a quinoxaline ring. Examples of divalent groups include a phthalazine ring, a naphthyridine ring, a purine ring, a pteridine ring, 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 thiophene ring, a benzothiophene ring, a dibenzothiophene ring, a furazan ring, an oxadiazole ring, a thianthrene ring, an indolocarbazole ring, a benzoindolocarbazole ring, a benzobenzoindolocarbazole ring, and a naphthobenzofuran ring.
At least one hydrogen atom in the compound represented by formula (H1) may be substituted with alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, cyano, halogen or deuterium.

上記式（Ｈ２）中、Ｌ^２およびＬ^３は、それぞれ独立して、炭素数６～３０のアリールまたは炭素数２～３０のヘテロアリールである。アリールとしては、炭素数６～２４のアリールが好ましく、炭素数６～１６のアリールがより好ましく、炭素数６～１２のアリールがさらに好ましく、炭素数６～１０のアリールが特に好ましく、具体的には、ベンゼン環、ビフェニル環、ナフタレン環、テルフェニル環、アセナフチレン環、フルオレン環、フェナレン環、フェナントレン環、トリフェニレン環、ピレン環、ナフタセン環、ペリレン環およびペンタセン環などの一価の基が挙げられる。ヘテロアリールとしては、炭素数２～２５のヘテロアリールが好ましく、炭素数２～２０のヘテロアリールがより好ましく、炭素数２～１５のヘテロアリールがさらに好ましく、炭素数２～１０のヘテロアリールが特に好ましく、具体的には、ピロール環、オキサゾール環、イソオキサゾール環、チアゾール環、イソチアゾール環、イミダゾール環、オキサジアゾール環、チアジアゾール環、トリアゾール環、テトラゾール環、ピラゾール環、ピリジン環、ピリミジン環、ピリダジン環、ピラジン環、トリアジン環、インドール環、イソインドール環、１Ｈ－インダゾール環、ベンゾイミダゾール環、ベンゾオキサゾール環、ベンゾチアゾール環、１Ｈ－ベンゾトリアゾール環、キノリン環、イソキノリン環、シンノリン環、キナゾリン環、キノキサリン環、フタラジン環、ナフチリジン環、プリン環、プテリジン環、カルバゾール環、アクリジン環、フェノキサチイン環、フェノキサジン環、フェノチアジン環、フェナジン環、フェナザシリン環、インドリジン環、フラン環、ベンゾフラン環、イソベンゾフラン環、ジベンゾフラン環、チオフェン環、ベンゾチオフェン環、ジベンゾチオフェン環、フラザン環、オキサジアゾール環、チアントレン環、インドロカルバゾール環、ベンゾインドロカルバゾール環、ベンゾベンゾインドロカルバゾール環およびナフトベンゾフラン環などの一価の基が挙げられる。
式（Ｈ２）で表される化合物における少なくとも１つの水素は、炭素数１～６のアルキル、炭素数３～１４のシクロアルキル、シアノ、ハロゲンまたは重水素で置換されていてもよい。 <Compound represented by general formula (H2)>

In the above formula (H2), ^L2 and ^L3 are each independently an aryl having 6 to 30 carbon atoms or a heteroaryl having 2 to 30 carbon atoms. The aryl is preferably an aryl having 6 to 24 carbon atoms, more preferably an aryl having 6 to 16 carbon atoms, still more preferably an aryl having 6 to 12 carbon atoms, and particularly preferably an aryl having 6 to 10 carbon atoms. Specific examples of the aryl include monovalent groups such as a benzene ring, a biphenyl ring, a naphthalene ring, a terphenyl ring, an acenaphthylene ring, a fluorene ring, a phenalene ring, a phenanthrene ring, a triphenylene ring, a pyrene ring, a naphthacene ring, a perylene ring, and a pentacene ring. The heteroaryl is preferably a heteroaryl having 2 to 25 carbon atoms, more preferably a heteroaryl having 2 to 20 carbon atoms, still more preferably a heteroaryl having 2 to 15 carbon atoms, and particularly preferably a heteroaryl having 2 to 10 carbon atoms. Specific examples thereof 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-benzyl ring, a benzophenyl ... and monovalent groups such as a 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 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 thiophene ring, a benzothiophene ring, a dibenzothiophene ring, a furazan ring, an oxadiazole ring, a thianthrene ring, an indolocarbazole ring, a benzoindolocarbazole ring, a benzobenzoindolocarbazole ring, and a naphthobenzofuran ring.
At least one hydrogen atom in the compound represented by formula (H2) may be substituted with alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, cyano, halogen or deuterium.

<Compound represented by formula (H3) (an example of a polymer host material)>

In formula (H3),
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 (H3) 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 a 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 (H3) 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 a fluorine atom.

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 the *.

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 (H3) 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 orientation and charge transport, it is preferable that 10 to 100% of the total number of MUs (k) in the molecule have an alkyl having 7 to 24 carbon atoms, and more preferably 30 to 100% of the total number of MUs (k) in the molecule have an alkyl having 7 to 24 carbon atoms (branched chain alkyl having 7 to 24 carbon atoms).

<Compound containing a structure represented by general formula (H4)>
The compound is a compound containing a structure represented by the following formula (H4), and contains a plurality of such structures, preferably 1 to 5, more preferably 1 to 3, even more preferably 1 or 2, and most preferably 1. When the compound contains a plurality of such structures, the structures are directly bonded to each other via a single bond or bonded to each other via a specific linking group.

In the above general formula (H4), each G is independently "=C(-H)-" or "=N-", and the H in the "=C(-H)-" may be substituted with a substituent or a structure represented by another formula (H4).

Compounds containing the structure represented by general formula (H4) can be, for example, compounds described in WO 2012/153780 and WO 2013/038650, and can be produced according to the methods described in the aforementioned documents.

Examples of substituents when the H in "=C(-H)-" which is G is substituted include, but are not limited to, the following:

Specific examples of the "aryl group" which is a substituent include phenyl, tolyl, xylyl, naphthyl, phenanthryl, pyrenyl, chrysenyl, benzo[c]phenanthryl, benzo[g]chrysenyl, benzanthryl, triphenylenyl, fluorenyl, 9,9-dimethylfluorenyl, benzofluorenyl, dibenzofluorenyl, biphenylyl, terphenylyl, quaterphenylyl, fluoranthenyl, etc., and preferably phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, triphenylenyl, and fluorenyl. Examples of aryl groups having a substituent include tolyl, xylyl, and 9,9-dimethylfluorenyl. As shown in the specific examples, the aryl group includes both fused and non-fused aryl groups.

Specific examples of the "heteroaryl group" substituent include pyrrolyl, pyrazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, pyridyl, triazinyl, indolyl, isoindolyl, imidazolyl, benzimidazolyl, indazolyl, imidazo[1,2-a]pyridinyl, furyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, azadibenzofuranyl, thiophenyl, benzothienyl, dibenzothienyl, azadibenzothienyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, and naphthyridinyl. , carbazolyl, azacarbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, phenothiazinyl, phenoxazinyl, oxazolyl, oxadiazolyl, furazanyl, benzoxazolyl, thienyl, thiazolyl, thiadiazolyl, benzthiazolyl, triazolyl, tetrazolyl, etc., and preferably dibenzofuranyl, dibenzothienyl, carbazolyl, pyridyl, pyrimidinyl, triazinyl, azadibenzofuranyl, and azadibenzothienyl, etc. Dibenzofuranyl, dibenzothienyl, azadibenzofuranyl, or azadibenzothienyl is more preferred.

It is also preferable that the "substituted silyl group" which is a substituent is a group selected from the group consisting of a substituted or unsubstituted trialkylsilyl group, a substituted or unsubstituted arylalkylsilyl group, and a substituted or unsubstituted triarylsilyl group.

Specific examples of substituted or unsubstituted trialkylsilyl groups include trimethylsilyl and triethylsilyl. Specific examples of substituted or unsubstituted arylalkylsilyl groups include diphenylmethylsilyl, ditolylmethylsilyl, and phenyldimethylsilyl. Specific examples of substituted or unsubstituted triarylsilyl groups include triphenylsilyl and tritolylsilyl.

The "substituted phosphine oxide group" which is a substituent is also preferably a substituted or unsubstituted diarylphosphine oxide group. Specific examples of substituted or unsubstituted diarylphosphine oxide groups include diphenylphosphine oxide and ditolylphosphine oxide.

Examples of the "substituted carboxy group" that is a substituent include benzoyloxy.

Examples of linking groups that bond multiple structures represented by formula (H4) include divalent to tetravalent, divalent to trivalent, or divalent derivatives of the above-mentioned aryl or heteroaryl.

Specific examples of the compound containing the structure represented by general formula (H4) are shown below.

上記式（Ｈ５）において、
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（２つのアリールは互いに結合していないか、または連結基を介して結合している）、ジヘテロアリールアミノ（ジヘテロアリールアミノの２つのヘテロアリールは互いに結合していないか、または連結基を介して結合している）、アリールへテロアリールアミノ（アリールとヘテロアリールは互いに結合していないか、または連結基を介して結合している）、アルキルまたはシクロアルキル（以上、第１置換基）であり、これらにおける少なくとも１つの水素はさらにアリール、ヘテロアリール、ジアリールアミノ、アルキルまたはシクロアルキル（以上、第２置換基）で置換されていてもよく、
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（２つのアリールは互いに結合していないか、または連結基を介して結合している）、ジヘテロアリールアミノ（ジヘテロアリールアミノの２つのヘテロアリールは互いに結合していないか、または連結基を介して結合している）、アリールヘテロアリールアミノ（アリールとヘテロアリールは互いに結合していないか、または連結基を介して結合している）、アルキルまたはシクロアルキル（以上、第１置換基）で置換されていてもよく、これらにおける少なくとも１つの水素はさらにアリール、ヘテロアリール、ジアリールアミノ、アルキルまたはシクロアルキル（以上、第２置換基）で置換されていてもよく、
ａ環、ｂ環、およびｃ環における、任意の「－Ｃ（－Ｒ）＝」（ここでＲはＲ^１～Ｒ^１１である）は「－Ｎ＝」に置き換わっていてもよく、
式（Ｈ５）で表される化合物における少なくとも１つの水素は、それぞれ独立して、ハロゲンまたは重水素で置換されてもよい。 <Compound represented by general formula (H5)>

In the above formula (H5),
R ¹ to R ¹¹ are each independently hydrogen, aryl, heteroaryl, diarylamino (two aryls are not bonded to each other or are bonded via a linking group), diheteroarylamino (two heteroaryls of diheteroarylamino are not bonded to each other or are bonded via a linking group), arylheteroarylamino (aryl and heteroaryl are not bonded to each other or are bonded via a linking group), alkyl or cycloalkyl (all of the above are first substituents), in which at least one hydrogen may be further substituted with aryl, heteroaryl, diarylamino, alkyl or cycloalkyl (all of the above are second substituents);
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 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, a heteroaryl, a diarylamino (two aryls are not bonded to each other or are bonded via a linking group), a diheteroarylamino (two heteroaryls of the diheteroarylamino are not bonded to each other or are bonded via a linking group), an arylheteroarylamino (aryls and heteroaryls are not bonded to each other or are bonded via a linking group), an alkyl or a cycloalkyl (all of these are first substituents), and at least one hydrogen atom in these may be further substituted with an aryl, a heteroaryl, a diarylamino, an alkyl or a cycloalkyl (all of these are second substituents);
Any "-C(-R)=" (wherein R is R ¹ to R ¹¹ ) in ring a, ring b, and ring c may be replaced with "-N=";
At least one hydrogen in the compound represented by formula (H5) may be independently replaced with a halogen or deuterium.

Any "-C(-R)=" in the rings a, b, and c in formula (H5) (where R is R ¹ to R ¹¹ ) may be replaced with "-N=" and changed to a pyridine ring, a pyrimidine ring, a pyridazine ring, a pyrazine ring, or other nitrogen-containing heteroaryl ring. For details of this explanation, refer to the explanations in the above general formula (2A) and formula (2B).

Preferably, in the above formula (H5),
R ¹ to R ¹¹ are each independently a hydrogen atom, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, a diarylamino group (wherein the two aryl groups are not bonded to each other or are bonded via a linking group, and the aryl group is an aryl group having 6 to 12 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 further substituted by an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, a diarylamino group (wherein the aryl group is an aryl group having 6 to 12 carbon atoms), an alkyl group having 1 to 12 carbon atoms, or a cycloalkyl group having 3 to 16 carbon atoms;
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 ring a, ring b or ring c, and at least one hydrogen atom in the formed ring may be substituted with an aryl ring having 6 to 30 carbon atoms, a heteroaryl ring having 2 to 30 carbon atoms, a diarylamino (wherein the two aryls are not bonded to each other or are bonded via a linking group, and the aryls are aryls having 6 to 12 carbon atoms), an alkyl ring having 1 to 12 carbon atoms or a cycloalkyl ring having 3 to 16 carbon atoms, and at least one hydrogen atom in these rings may be further substituted with an aryl ring having 6 to 30 carbon atoms, a heteroaryl ring having 2 to 30 carbon atoms, a diarylamino (wherein the aryls are aryls having 6 to 12 carbon atoms), an alkyl ring having 1 to 12 carbon atoms or a cycloalkyl ring having 3 to 16 carbon atoms.

More preferably, in the above formula (H5),
R ¹ to R ¹¹ are each independently a hydrogen atom, an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, a diarylamino (wherein the two aryl groups are not bonded to each other or are bonded via a linking group, and the aryl group is an aryl group having 6 to 10 carbon atoms), an alkyl group having 1 to 6 carbon atoms, or a cycloalkyl group having 3 to 14 carbon atoms, in which at least one hydrogen atom may be further substituted by an aryl having 6 to 16 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, a diarylamino (wherein the two aryl groups are not bonded to each other or are bonded via a linking group, and the aryl group is an aryl group having 6 to 10 carbon atoms), an alkyl group having 1 to 6 carbon atoms, or a cycloalkyl group having 3 to 14 carbon atoms;
Adjacent groups among R ¹ to R ¹¹ may be bonded to each other to form an aryl ring having 9 to 12 carbon atoms or a heteroaryl ring having 6 to 12 carbon atoms together with ring a, ring b or ring c, and at least one hydrogen atom in the formed ring may be substituted with an aryl ring having 6 to 16 carbon atoms, a heteroaryl ring having 2 to 15 carbon atoms, diarylamino (wherein the two aryls are not bonded to each other or are bonded via a linking group, and the aryl is an aryl ring having 6 to 10 carbon atoms), an alkyl ring having 1 to 6 carbon atoms or a cycloalkyl ring having 3 to 14 carbon atoms, and at least one hydrogen atom in these rings may be further substituted with an aryl ring having 6 to 16 carbon atoms, a heteroaryl ring having 2 to 15 carbon atoms, diarylamino (wherein the two aryls are not bonded to each other or are bonded via a linking group, and the aryl is an aryl ring having 6 to 10 carbon atoms), an alkyl ring having 1 to 6 carbon atoms or a cycloalkyl ring having 3 to 14 carbon atoms.

In the above first and second substituents, examples of the "aryl" and "heteroaryl" in aryl, heteroaryl, diarylamino, diheteroarylamino, and arylheteroarylamino include the following.

Specific examples of "aryl" include aryls having 6 to 30 carbon atoms, preferably aryls having 6 to 24 carbon atoms, more preferably aryls having 6 to 20 carbon atoms, even more preferably aryls having 6 to 16 carbon atoms, particularly preferably aryls having 6 to 12 carbon atoms, and most preferably aryls having 6 to 10 carbon atoms. For example, phenyl is a monocyclic aryl, (2-, 3-, 4-)biphenylyl is a bicyclic aryl, (1-, 2-)naphthyl is a condensed bicyclic 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) is a tricyclic aryl, Examples of the fused tetracyclic aryls include acenaphthylene-(1-,3-,4-,5-)yl, fluorene-(1-,2-,3-,4-,9-)yl, phenalene-(1-,2-)yl, (1-,2-,3-,4-,9-)phenanthryl, quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl), triphenylene-(1-,2-)yl, pyrene-(1-,2-,4-)yl, naphthacene-(1-,2-,5-)yl, and perylene-(1-,2-,3-)yl and pentacene-(1-,2-,5-,6-)yl, which are fused pentacyclic aryls.

Specific examples of "heteroaryl" include heteroaryls having 2 to 30 carbon atoms, preferably heteroaryls having 2 to 25 carbon atoms, more preferably heteroaryls having 2 to 20 carbon atoms, even more preferably heteroaryls having 2 to 15 carbon atoms, and particularly preferably heteroaryls having 2 to 10 carbon atoms. For example, 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, phenoxathiyl, nyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenazasilinyl, indolizinyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, naphthobenzofuranyl, thiophenyl, benzothiophenyl, isobenzothiophenyl, dibenzothiophenyl, naphthobenzothiophenyl, benzophosphoryl, dibenzophosphoryl, monovalent groups of benzophosphole oxide rings, monovalent groups of dibenzophosphole oxide rings, furazanyl, thianthrenyl, indolocarbazolyl, benzoindolocarbazolyl, and benzobenzoindolocarbazolyl.

In the above first and second substituents, the "alkyl" 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, an alkyl having 1 to 5 carbon atoms (branched alkyl having 3 to 5 carbon atoms) or an alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms) is particularly preferred, and methyl is the most preferred. For example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl (t-amyl), n-hexyl, 1-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl (1,1,3,3-tetramethylbutyl), 1-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, and n-eicosyl. Other examples include 1-ethyl-1-methylpropyl, 1,1-diethylpropyl, 1,1-dimethylbutyl, 1-ethyl-1-methylbutyl, 1,1,4-trimethylpentyl, 1,1,2-trimethylpropyl, 1,1-dimethyloctyl, 1,1-dimethylpentyl, 1,1-dimethylheptyl, 1,1,5-trimethylhexyl, 1-ethyl-1-methylhexyl, 1-ethyl-1,3-dimethylbutyl, 1,1,2,2-tetramethylpropyl, 1-butyl-1-methylpentyl, 1,1-diethylbutyl, 1-ethyl-1-methylpentyl, 1,1,3-trimethylbutyl, 1-propyl-1-methylpentyl, 1,1,2-trimethylpropyl, 1-ethyl-1,2,2-trimethylpropyl, 1-propyl-1-methylbutyl, and 1,1-dimethylhexyl.

In the above first and second substituents, examples of "cycloalkyl" 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. Examples 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 bicyclo[1.1.0]butyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.0]pentyl, bicyclo[2.1.1]hexyl, bicyclo[3.1.0]hexyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl, adamantyl, diamantyl, decahydronaphthalenyl, and decahydroazulenyl.

When the first substituent is an aryl, the substitution positions are preferably R ¹ , R ³ , R ⁴ , R ⁵ , R ¹⁰ and R ¹¹ , and for example, substitution at R ¹ and R ³ , substitution at R ⁵ and R ¹⁰ , or substitution at R ⁴ and R ¹¹ is more preferable, and the aryl is preferably a phenyl group.

When the first substituent is a heteroaryl, the substitution positions are preferably R ¹ , R ² , R ³ , R 4 , R ⁵ , R ⁶ , R ⁹ , R ¹⁰ and R ¹¹ , and more preferably R ¹ , R ² , R ³ , R ¹ and R ³ , R ⁴ and R ¹¹ , R ⁵ and R ¹⁰ , and R ⁶ and R ^{9 ,} and the heteroaryl is preferably a carbazolyl group. This heteroaryl (e.g., carbazolyl) may be substituted at the above positions via a phenylene group.

Specific examples of compounds represented by formula (H5) include compounds represented by the following structural formula. In the formula, "Me" is a methyl group.

The compound represented by formula (H5) can be produced by first bonding rings a to c with a bonding group (-O-) to produce an intermediate (first reaction), and then bonding rings a to c with B (boron) to produce a final product (second reaction). In the first reaction, for example, a general etherification reaction such as a nucleophilic substitution reaction or an Ullmann reaction can be used. In the second reaction, a tandem hetero Friedel-Crafts reaction (sequential aromatic electrophilic substitution reaction) can be used. For details of the first and second reactions, refer to the explanations in WO 2015/102118.

上記式（Ｈ６）において、
Ｒ^１～Ｒ^１６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、アリールへテロアリールアミノ、アルキルまたはシクロアルキル（以上、第１置換基）であり、これらにおける少なくとも１つの水素はさらにアリール、ヘテロアリール、ジアリールアミノ、アルキルまたはシクロアルキル（以上、第２置換基）で置換されていてもよく、
Ｒ^１～Ｒ^１６のうちの隣接する基同士が結合してａ環、ｂ環、ｃ環、またはｄ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、アルキルまたはシクロアルキル（以上、第１置換基）で置換されていてもよく、これらにおける少なくとも１つの水素はさらにアリール、ヘテロアリール、ジアリールアミノ、アルキルまたはシクロアルキル（以上、第２置換基）で置換されていてもよく、
式（Ｈ６）で表される化合物における少なくとも１つの水素は、それぞれ独立して、ハロゲンまたは重水素で置換されてもよい。 <Compound represented by general formula (H6)>

In the above formula (H6),
R ¹ to R ¹⁶ are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, or cycloalkyl (these are all first substituents), in which at least one hydrogen may be further substituted with aryl, heteroaryl, diarylamino, alkyl, or cycloalkyl (these are all second substituents);
Adjacent groups among R ¹ to R ¹⁶ may be bonded to each other to form an aryl ring or a heteroaryl ring together with the a-ring, the b-ring, the c-ring, or the d-ring, and at least one hydrogen atom in the formed ring may be substituted with an aryl, a heteroaryl, a diarylamino, a diheteroarylamino, an arylheteroarylamino, an alkyl, or a cycloalkyl (all of which are first substituents), and at least one hydrogen atom in these rings may be further substituted with an aryl, a heteroaryl, a diarylamino, an alkyl, or a cycloalkyl (all of which are second substituents);
At least one hydrogen in the compound represented by formula (H6) may be independently replaced with a halogen or deuterium.

Preferably, in the above formula (H6),
R ¹ to R ¹⁶ are each independently a hydrogen atom, an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms, a diarylamino (wherein the two aryl groups are not bonded to each other or are bonded via a linking group, and the aryl group is an aryl group having 6 to 12 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 further substituted by an aryl having 6 to 30 carbon atoms, a heteroaryl having 2 to 30 carbon atoms, a diarylamino (wherein the two aryl groups are not bonded to each other or are bonded via a linking group, and the aryl group is an aryl group having 6 to 12 carbon atoms), an alkyl group having 1 to 12 carbon atoms, or a cycloalkyl group having 3 to 16 carbon atoms;
Adjacent groups among R ¹ to R ¹⁶ 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 ring a, ring b, ring c, or ring d, and at least one hydrogen atom in the formed ring may be substituted with an aryl ring having 6 to 30 carbon atoms, a heteroaryl ring having 2 to 30 carbon atoms, a diarylamino (wherein the two aryls are not bonded to each other or are bonded via a linking group, and the aryl is an aryl ring having 6 to 12 carbon atoms), an alkyl ring having 1 to 12 carbon atoms, or a cycloalkyl ring having 3 to 16 carbon atoms, and at least one hydrogen atom in these rings may be further substituted with an aryl ring having 6 to 30 carbon atoms, a heteroaryl ring having 2 to 30 carbon atoms, a diarylamino (wherein the two aryls are not bonded to each other or are bonded via a linking group, and the aryl is an aryl ring having 6 to 12 carbon atoms), an alkyl ring having 1 to 12 carbon atoms, or a cycloalkyl ring having 3 to 16 carbon atoms.

More preferably, in the above formula (H6),
R ¹ to R ¹⁶ are each independently a hydrogen atom, an aryl group having 6 to 16 carbon atoms, a heteroaryl group having 2 to 15 carbon atoms, a diarylamino group (wherein the two aryl groups are not bonded to each other or are bonded via a linking group, and the aryl group is an aryl group having 6 to 10 carbon atoms), an alkyl group having 1 to 6 carbon atoms, or a cycloalkyl group having 3 to 14 carbon atoms, in which at least one hydrogen atom may be further substituted by an aryl group having 6 to 16 carbon atoms, a heteroaryl group having 2 to 15 carbon atoms, a diarylamino group (wherein the aryl group is an aryl group having 6 to 10 carbon atoms), an alkyl group having 1 to 6 carbon atoms, or a cycloalkyl group having 3 to 14 carbon atoms;
Adjacent groups among R ¹ to R ¹⁶ may be bonded to each other to form an aryl ring having 9 to 12 carbon atoms or a heteroaryl ring having 6 to 12 carbon atoms together with ring a, ring b, ring c, or ring d, and at least one hydrogen atom in the formed ring may be substituted with an aryl ring having 6 to 16 carbon atoms, a heteroaryl ring having 2 to 15 carbon atoms, diarylamino (wherein the two aryls are not bonded to each other or are bonded via a linking group, and the aryl is an aryl ring having 6 to 10 carbon atoms), an alkyl ring having 1 to 6 carbon atoms, or a cycloalkyl ring having 3 to 14 carbon atoms, and at least one hydrogen atom in these rings may be further substituted with an aryl ring having 6 to 16 carbon atoms, a heteroaryl ring having 2 to 15 carbon atoms, diarylamino (wherein the two aryls are not bonded to each other or are bonded via a linking group, and the aryl is an aryl ring having 6 to 10 carbon atoms), an alkyl ring having 1 to 6 carbon atoms, or a cycloalkyl ring having 3 to 14 carbon atoms.

In the above first and second substituents, examples of "aryl" and "heteroaryl" in aryl, heteroaryl, diarylamino (wherein the two aryls are not bonded to each other or are bonded via a linking group), diheteroarylamino (wherein the two heteroaryls of diheteroarylamino are not bonded to each other or are bonded via a linking group), and arylheteroarylamino (wherein the aryl and heteroaryl are not bonded to each other or are bonded via a linking group) include the following.

Specific examples of "aryl" include aryls having 6 to 30 carbon atoms, preferably aryls having 6 to 24 carbon atoms, more preferably aryls having 6 to 20 carbon atoms, even more preferably aryls having 6 to 16 carbon atoms, particularly preferably aryls having 6 to 12 carbon atoms, and most preferably aryls having 6 to 10 carbon atoms. For example, phenyl is a monocyclic aryl, (2-, 3-, 4-)biphenylyl is a bicyclic aryl, (1-, 2-)naphthyl is a condensed bicyclic 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) is a tricyclic aryl, Examples of the fused tetracyclic aryls include acenaphthylene-(1-,3-,4-,5-)yl, fluorene-(1-,2-,3-,4-,9-)yl, phenalene-(1-,2-)yl, (1-,2-,3-,4-,9-)phenanthryl, quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl), triphenylene-(1-,2-)yl, pyrene-(1-,2-,4-)yl, naphthacene-(1-,2-,5-)yl, and perylene-(1-,2-,3-)yl and pentacene-(1-,2-,5-,6-)yl, which are fused pentacyclic aryls.

Specific examples of "heteroaryl" include heteroaryls having 2 to 30 carbon atoms, preferably heteroaryls having 2 to 25 carbon atoms, more preferably heteroaryls having 2 to 20 carbon atoms, even more preferably heteroaryls having 2 to 15 carbon atoms, and particularly preferably heteroaryls having 2 to 10 carbon atoms. For example, 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, phenoxathiyl, nyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenazasilinyl, indolizinyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, naphthobenzofuranyl, thiophenyl, benzothiophenyl, isobenzothiophenyl, dibenzothiophenyl, naphthobenzothiophenyl, benzophosphoryl, dibenzophosphoryl, monovalent groups of benzophosphole oxide rings, monovalent groups of dibenzophosphole oxide rings, furazanyl, thianthrenyl, indolocarbazolyl, benzoindolocarbazolyl, and benzobenzoindolocarbazolyl.

In the above first and second substituents, the "alkyl" 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, an alkyl having 1 to 5 carbon atoms (branched alkyl having 3 to 5 carbon atoms) or an alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms) is particularly preferred, and methyl is the most preferred. For example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl (t-amyl), n-hexyl, 1-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl (1,1,3,3-tetramethylbutyl), 1-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, and n-eicosyl. Other examples include 1-ethyl-1-methylpropyl, 1,1-diethylpropyl, 1,1-dimethylbutyl, 1-ethyl-1-methylbutyl, 1,1,4-trimethylpentyl, 1,1,2-trimethylpropyl, 1,1-dimethyloctyl, 1,1-dimethylpentyl, 1,1-dimethylheptyl, 1,1,5-trimethylhexyl, 1-ethyl-1-methylhexyl, 1-ethyl-1,3-dimethylbutyl, 1,1,2,2-tetramethylpropyl, 1-butyl-1-methylpentyl, 1,1-diethylbutyl, 1-ethyl-1-methylpentyl, 1,1,3-trimethylbutyl, 1-propyl-1-methylpentyl, 1,1,2-trimethylpropyl, 1-ethyl-1,2,2-trimethylpropyl, 1-propyl-1-methylbutyl, and 1,1-dimethylhexyl.

In the above first and second substituents, examples of "cycloalkyl" 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. Examples 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 bicyclo[1.1.0]butyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.0]pentyl, bicyclo[2.1.1]hexyl, bicyclo[3.1.0]hexyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl, adamantyl, diamantyl, decahydronaphthalenyl, and decahydroazulenyl.

The compound represented by formula (H6) can be produced by referring to the description in WO 2014/042197.

<TADF material>
By reducing the energy difference between the excited singlet state and the excited triplet state, the reverse energy transfer from the excited triplet state, which usually has a low transition probability, to the excited singlet state occurs with high efficiency, and light emission from the singlet state (thermally activated delayed fluorescence, TADF) occurs. In normal fluorescent light emission, 75% of the triplet excitons generated by current excitation pass through a thermal deactivation pathway and cannot be taken as fluorescence. On the other hand, in TADF, all excitons can be used for fluorescent light emission, and a highly efficient organic EL element can be realized.

式（Ｈ７）において、ＥＤは電子供与性基であり、Ｌｎは結合基であり、ＥＡは電子受容性基であり、式（Ｈ７）で表される化合物の一重項エネルギー（Ｓ^１）と三重項エネルギー（Ｔ^１）のエネルギー差（ΔＳ^１Ｔ^１）は０．２ｅＶ以下である（Hiroki Uoyama, Kenichi Goushi, Katsuyuki Shizu, Hiroko Nomura, Chihaya Adachi, Nature, 492, 234-238 (2012)）。エネルギー差（ΔＳ^１Ｔ^１）は、好ましくは０．１５ｅＶ以下であり、より好ましくは０．１０ｅＶ以下であり、さらに好ましくは０．０８ｅＶ以下である。 Examples of TADF materials that can be used for such purposes include compounds represented by the following general formula (H7) or compounds having the following general formula (H7) as a partial structure.

In formula (H7), ED is an electron donating group, Ln is a bonding group, EA is an electron accepting group, and the energy difference (ΔS ¹ T ¹ ) between the singlet energy (S ¹ ) and triplet energy (T ¹ ) of the compound represented by formula (H7) is 0.2 eV or less (Hiroki Uoyama, Kenichi Goushi, Katsuyuki Shizu, Hiroko Nomura, Chihaya Adachi, Nature, 492, 234-238 (2012)). The energy difference (ΔS ¹ T ¹ ) is preferably 0.15 eV or less, more preferably 0.10 eV or less, and even more preferably 0.08 eV or less.

The TADF material is preferably a donor-acceptor type TADF compound (D-A type TADF compound) designed to localize the HOMO and LUMO within the molecule using electron-donating substituents called donors and electron-accepting substituents called acceptors, thereby allowing efficient reverse intersystem crossing to occur.

Here, in this specification, "electron-donating substituent" (donor) means a substituent or partial structure in which the LUMO orbital is localized in the TADF compound molecule, and "electron-accepting substituent" (acceptor) means a substituent or partial structure in which the HOMO orbital is localized in the TADF compound molecule.

In general, TADF compounds using donors or acceptors have a large spin orbit coupling (SOC) due to their structure, and the exchange interaction between the HOMO and LUMO is small, resulting in a small ΔE(ST), resulting in a very fast reverse intersystem crossing rate. On the other hand, TADF compounds using donors or acceptors have a large structural relaxation in the excited state (in some molecules, the stable structure differs between the ground state and the excited state, so when an external stimulus causes a transition from the ground state to the excited state, the structure then changes to the stable structure in the excited state), giving a wide emission spectrum, which may reduce the color purity when used as a light-emitting material.

If the color purity is reduced by the TADF material, a fluorescent compound can be added as another component to the light-emitting layer or a layer adjacent to the light-emitting layer. The TADF material acts as an assisting dopant, and the other component acts as an emitting dopant. The other component may be a compound whose absorption spectrum at least partially overlaps with the emission peak of the assisting dopant.

As the donor and acceptor structures used in the TADF material, for example, the structures described in Chemistry of Materials, 2017, 29, 1946-1963 can be used. Examples of ED include functional groups containing sp ³ nitrogen, and more specifically, groups derived from carbazole, dimethylcarbazole, di-t-butylcarbazole, dimethoxycarbazole, tetramethylcarbazole, benzofluorocarbazole, benzothienocarbazole, phenyldihydroindolocarbazole, phenylbicarbazole, bicarbazole, tercarbazole, diphenylcarbazolylamine, tetraphenylcarbazolyldiamine, phenoxazine, dihydrophenazine, phenothiazine, dimethyldihydroacridine, diphenylamine, bis(t-butyl)phenyl)amine, (diphenylamino)phenyl)diphenylbenzenediamine, dimethyltetraphenyldihydroacridinediamine, tetramethyl-dihydro-indenoacridine, and diphenyl-dihydrodibenzoazasiline. Examples of EA include groups derived from sp ² Nitrogen-containing aromatic rings, CN-substituted aromatic rings, rings having ketones and cyano groups, more specifically sulfonyldibenzene, benzophenone, phenylenebis(phenylmethanone), benzonitrile, isonicotinonitrile, phthalonitrile, isophthalonitrile, paraphthalonitrile, triazole, oxazole, thiadiazole, benzothiazole, benzobis(thiazole), benzoxazole, benzobis(oxazole), quinoline, benzimidazole, dibenzoquinoxaline, heptaazaphenalene, thioxanthone diamine Examples of the group derived from bis(phenylsulfonyl)benzene, dimethylthioxanthene dioxide, thianthrene tetraoxide, tris(dimethylphenyl)borane, etc. are mentioned. Examples of Ln include single bonds and arylenes, more specifically, phenylene, biphenylene, naphthylene, etc. In addition, in any of the structures, hydrogen may be substituted with alkyl, cycloalkyl, and aryl. In particular, it is preferable that the compound has at least one partial structure selected from carbazole, phenoxazine, acridine, triazine, pyrimidine, pyrazine, thioxanthene, benzonitrile, phthalonitrile, isophthalonitrile, diphenylsulfone, triazole, oxadiazole, thiadiazole, and benzophenone.

The compound represented by general formula (H7) is, more specifically, a compound represented by any one of the following general formulas (H7-1), (H7-2) and (H7-3).

In the above general formulas (H7-1), (H7-2) and (H7-3),
M is each independently a single bond, -O-, >N-Ar or >C(-Ar) ₂ , and is preferably a single bond, -O- or >N-Ar from the viewpoint of the HOMO depth and the height of the excited singlet energy level and the excited triplet energy level of the partial structure to be formed;
J is a spacer structure separating the donor partial structure and the acceptor partial structure, and each J is independently an arylene having 6 to 18 carbon atoms. From the viewpoint of the magnitude of conjugation exuded from the donor partial structure and the acceptor partial structure, an arylene having 6 to 12 carbon atoms is preferable, and more specific examples thereof include phenylene, methylphenylene, and dimethylphenylene.
Q is each independently ═C(—H)— or ═N—, and is preferably ═N— from the viewpoint of the shallowness of the LUMO and the height of the excited singlet energy level and the excited triplet energy level of the partial structure to be formed,
Ar are each independently hydrogen, an aryl having 6 to 24 carbon atoms, a heteroaryl having 2 to 24 carbon atoms, an alkyl having 1 to 12 carbon atoms, or a cycloalkyl having 3 to 18 carbon atoms; from the viewpoint of the HOMO depth and the height of the excited singlet energy level and the excited triplet energy level of the partial structure to be formed, preferably hydrogen, an aryl having 6 to 12 carbon atoms, a heteroaryl having 2 to 14 carbon atoms, an alkyl having 1 to 4 carbon atoms, or a cycloalkyl having 6 to 10 carbon atoms, more preferably hydrogen, phenyl, tolyl, xylyl, mesityl, biphenyl, pyridyl, bipyridyl, triazyl, carbazolyl, dimethylcarbazolyl, di-t-butylcarbazolyl, benzimidazole, or phenylbenzimidazole, and further preferably hydrogen, phenyl, or carbazolyl;
m is 1 or 2;
n is an integer of 2 to (6-m), and from the viewpoint of steric hindrance, is preferably an integer of 4 to (6-m).
Furthermore, at least one hydrogen atom in the compounds represented by the above formulas may be substituted with a halogen or deuterium.

Examples of compounds represented by formula (H7) include compounds represented by the following structures. In the structural formula, * indicates a bond position, "Me" indicates a methyl group, and "tBu" indicates a t-butyl group.

Of the above specific compounds, the following are particularly preferred as compounds represented by general formula (H7): 4CzBN, 4CzBN-Ph, 5CzBN, 3Cz2DPhCzBN, 4CzIPN, 2PXZ-TAZ, Cz-TRZ3, BDPCC-TPTA, MA-TA, PA-TA, FA-TA, PXZ-TRZ, DMAC-TRZ, BCzT, DCzTrz, DDCzTrz, spiroAC-TRZ, Ac-HPM, Ac-PPM, Ac-MPM, TCzTrz, TmCzTrz, and DCzmCzTrz.

In addition to the polycyclic aromatic compounds represented by the above general formula (1A) or general formula (1B), known compounds can be used as dopant materials, and can be selected from a variety of materials according to the desired emission color. Specifically, for example, condensed ring derivatives such as phenanthrene, anthracene, pyrene, tetracene, pentacene, perylene, naphthopyrene, dibenzopyrene, rubrene, and chrysene, benzoxazole derivatives, benzothiazole derivatives, benzimidazole derivatives, benzotriazole derivatives, oxazole derivatives, oxadiazole derivatives, thiazole derivatives, imidazole derivatives, thiadiazole derivatives, triazole derivatives, pyrazoline derivatives, stilbene derivatives, thiophene derivatives, tetraphenylbutadiene derivatives, and tetraphenylbutadiene derivatives can be used. conductors, cyclopentadiene derivatives, bisstyryl derivatives such as bisstyrylanthracene derivatives and distyrylbenzene derivatives (JP Patent Publication No. 245087/1999), bisstyrylarylene derivatives (JP Patent Publication No. 247278/1990), diazaindacene derivatives, furan derivatives, benzofuran derivatives, isobenzofuran derivatives such as phenylisobenzofuran, dimesitylisobenzofuran, di(2-methylphenyl)isobenzofuran, di(2-trifluoromethylphenyl)isobenzofuran, and phenylisobenzofuran, Coumarin derivatives such as dibenzofuran derivatives, 7-dialkylaminocoumarin derivatives, 7-piperidinocoumarin derivatives, 7-hydroxycoumarin derivatives, 7-methoxycoumarin derivatives, 7-acetoxycoumarin derivatives, 3-benzothiazolylcoumarin derivatives, 3-benzimidazolylcoumarin derivatives, and 3-benzoxazolylcoumarin derivatives, dicyanomethylenepyran derivatives, dicyanomethylenethiopyran derivatives, polymethine derivatives, cyanine derivatives, oxobenzoanthracene derivatives, xanthene derivatives, and rhodamine derivatives These include fluorescein derivatives, pyrylium derivatives, carbostyril derivatives, acridine derivatives, oxazine derivatives, phenylene oxide derivatives, quinacridone derivatives, quinazoline derivatives, pyrrolopyridine derivatives, furopyridine derivatives, 1,2,5-thiadiazolopyrene derivatives, pyrromethene derivatives, perinone derivatives, pyrrolopyrrole derivatives, squarylium derivatives, violanthrone derivatives, phenazine derivatives, acridone derivatives, deazaflavin derivatives, fluorene derivatives, and benzofluorene derivatives.

As examples of dopant materials for each color of light emitted, blue to blue-green dopant materials include aromatic hydrocarbon compounds such as naphthalene, anthracene, phenanthrene, pyrene, triphenylene, perylene, fluorene, indene, and chrysene, and their derivatives, as well as furan, pyrrole, thiophene, silole, 9-silafluorene, 9,9'-spirobisilafluorene, benzothiophene, benzofuran, indole, dibenzothiophene, dibenzofuran, imidazopyridine, phenanthroline, pyrazine, naphthyridine, quinoxaline, pyrrolopyridine, and pyrrolopyridine. Examples include aromatic heterocyclic compounds and derivatives thereof such as lysine and thioxanthene, distyrylbenzene derivatives, tetraphenylbutadiene derivatives, stilbene derivatives, aldazine derivatives, coumarin derivatives, azole derivatives such as imidazole, thiazole, thiadiazole, carbazole, oxazole, oxadiazole, and triazole, and metal complexes thereof, and aromatic amine derivatives such as N,N'-diphenyl-N,N'-di(3-methylphenyl)-4,4'-diphenyl-1,1'-diamine.

In addition, examples of green to yellow dopant materials include coumarin derivatives, phthalimide derivatives, naphthalimide derivatives, perinone derivatives, pyrrolopyrrole derivatives, cyclopentadiene derivatives, acridone derivatives, quinacridone derivatives, and naphthacene derivatives such as rubrene. Further, suitable examples include compounds in which a substituent that enables longer wavelengths, such as aryl, heteroaryl, arylvinyl, amino, or cyano, has been introduced into the compounds exemplified as the blue to blue-green dopant materials above.

Further, examples of orange to red dopant materials include naphthalimide derivatives such as bis(diisopropylphenyl)perylenetetracarboxylic acid imide, perinone derivatives, rare earth complexes such as Eu complexes with ligands such as acetylacetone, benzoylacetone and phenanthroline, 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran and its analogues, metal phthalocyanine derivatives such as magnesium phthalocyanine and aluminum chlorophthalocyanine, rhodamine compounds, deazaflavin derivatives, coumarin derivatives, quinacridone derivatives, phenoxazine derivatives, oxazine derivatives, quinazoline derivatives, pyrrolopyridine derivatives, squarylium derivatives, violanthrone derivatives, phenazine derivatives, phenoxazone derivatives and thiadiazolopyrene derivatives. Further, compounds in which a substituent that enables longer wavelengths, such as aryl, heteroaryl, arylvinyl, amino and cyano, is introduced into the compounds exemplified above as blue to blue-green and green to yellow dopant materials, are also suitable examples.

As other dopants, compounds described on page 13 of the June 2004 issue of Chemical Industry and the references cited therein can be appropriately selected and used.

Among the dopant materials described above, amines having a stilbene structure, perylene derivatives, borane derivatives, aromatic amine derivatives, coumarin derivatives, pyran derivatives, or pyrene derivatives are particularly preferred.

当該式中、Ａｒ^１は炭素数６～３０のアリールに由来するｍ価の基であり、Ａｒ^２およびＡｒ^３は、それぞれ独立して炭素数６～３０のアリールであるが、Ａｒ^１～Ａｒ^３の少なくとも１つはスチルベン構造を有し、Ａｒ^１～Ａｒ^３は、アリール、ヘテロアリール、アルキル、シクロアルキル、トリ置換シリル（アリール、アルキルおよびシクロアルキルの少なくとも１つでトリ置換されたシリル）またはシアノで置換されていてもよく、そして、ｍは１～４の整数である。 The amine having a stilbene structure is represented, for example, by the following formula.

In the formula, Ar ¹ is an m-valent group derived from an aryl having 6 to 30 carbon atoms, Ar ² and Ar ³ are each independently an aryl having 6 to 30 carbon atoms, at least one of Ar ¹ to Ar ³ has a stilbene structure, Ar ¹ to Ar ³ may be substituted with an aryl, heteroaryl, alkyl, cycloalkyl, tri-substituted silyl (silyl tri-substituted with at least one of aryl, alkyl, and cycloalkyl) or cyano, and m is an integer of 1 to 4.

当該式中、Ａｒ^２およびＡｒ^３は、それぞれ独立して炭素数６～３０のアリールであり、Ａｒ^２およびＡｒ^３は、アリール、ヘテロアリール、アルキル、シクロアルキル、トリ置換シリル（アリール、アルキルおよびシクロアルキルの少なくとも１つでトリ置換されたシリル）またはシアノで置換されていてもよい。 The amine having a stilbene structure is more preferably a diaminostilbene represented by the following formula.

In the formula, Ar ² and Ar ³ are each independently an aryl having 6 to 30 carbon atoms, and Ar ² and Ar ³ may be substituted with an aryl, heteroaryl, alkyl, cycloalkyl, tri-substituted silyl (silyl tri-substituted with at least one of aryl, alkyl, and cycloalkyl) or cyano.

Specific examples of aryls having 6 to 30 carbon atoms include phenyl, naphthyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthrenyl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphthacenyl, perylenyl, stilbenyl, distyrylphenyl, distyrylbiphenylyl, and distyrylfluorenyl.

Specific examples of the amine having a stilbene structure include N,N,N',N'-tetra(4-biphenylyl)-4,4'-diaminostilbene, N,N,N',N'-tetra(1-naphthyl)-4,4'-diaminostilbene, N,N,N',N'-tetra(2-naphthyl)-4,4'-diaminostilbene, N,N'-di(2-naphthyl)-N,N'-diphenyl-4,4'-diaminostilbene, and N,N'-di(9-phenanthryl)-N,N'-diphenyl-4,4'-diaminostilbene. nyl-4,4'-diaminostilbene, 4,4'-bis[4"-bis(diphenylamino)styryl]-biphenyl, 1,4-bis[4'-bis(diphenylamino)styryl]-benzene, 2,7-bis[4'-bis(diphenylamino)styryl]-9,9-dimethylfluorene, 4,4'-bis(9-ethyl-3-carbazovinylene)-biphenyl, 4,4'-bis(9-phenyl-3-carbazovinylene)-biphenyl, and the like.
Furthermore, amines having a stilbene structure, such as those described in JP-A Nos. 2003-347056 and 2001-307884, may also be used.

Examples of perylene derivatives include 3,10-bis(2,6-dimethylphenyl)perylene, 3,10-bis(2,4,6-trimethylphenyl)perylene, 3,10-diphenylperylene, 3,4-diphenylperylene, 2,5,8,11-tetra-t-butylperylene, 3,4,9,10-tetraphenylperylene, 3-(1'-pyrenyl)-8,11-di(t-butyl)perylene, 3-(9'-anthryl)-8,11-di(t-butyl)perylene, and 3,3'-bis(8,11-di(t-butyl)perylenyl).
Also usable are perylene derivatives described in JP-A-11-97178, JP-A-2000-133457, JP-A-2000-26324, JP-A-2001-267079, JP-A-2001-267078, JP-A-2001-267076, JP-A-2000-34234, JP-A-2001-267075, and JP-A-2001-217077.

Examples of the borane derivatives include 1,8-diphenyl-10-(dimesitylboryl)anthracene, 9-phenyl-10-(dimesitylboryl)anthracene, 4-(9'-anthryl)dimesitylborylnaphthalene, 4-(10'-phenyl-9'-anthryl)dimesitylborylnaphthalene, 9-(dimesitylboryl)anthracene, 9-(4'-biphenylyl)-10-(dimesitylboryl)anthracene, and 9-(4'-(N-carbazolyl)phenyl)-10-(dimesitylboryl)anthracene.
Also, borane derivatives described in, for example, International Publication No. 2000/40586 may be used.

当該式中、Ａｒ^４は炭素数６～３０のアリールに由来するｎ価の基であり、Ａｒ^５およびＡｒ^６はそれぞれ独立して炭素数６～３０のアリールであり、Ａｒ^４～Ａｒ^６は、アリール、ヘテロアリール、アルキル、シクロアルキル、トリ置換シリル（アリール、アルキルおよびシクロアルキルの少なくとも１つでトリ置換されたシリル）またはシアノで置換されていてもよく、そして、ｎは１～４の整数である。 The aromatic amine derivative is represented, for example, by the following formula:

In the formula, Ar ⁴ is an n-valent group derived from an aryl having 6 to 30 carbon atoms, Ar ⁵ and Ar ⁶ are each independently an aryl having 6 to 30 carbon atoms, Ar ⁴ to Ar ⁶ may be substituted with an aryl, heteroaryl, alkyl, cycloalkyl, tri-substituted silyl (silyl tri-substituted with at least one of aryl, alkyl, and cycloalkyl) or cyano, and n is an integer of 1 to 4.

In particular, an aromatic amine derivative in which Ar ⁴ is a divalent group derived from anthracene, chrysene, fluorene, benzofluorene or pyrene, Ar ⁵ and Ar ⁶ are each independently an aryl having 6 to 30 carbon atoms, Ar ⁴ to Ar ⁶ may be substituted with an aryl, heteroaryl, alkyl, cycloalkyl, tri-substituted silyl (silyl tri-substituted with at least one of aryl, alkyl and cycloalkyl) or cyano, and n is 2 is more preferable.

Specific examples of aryls having 6 to 30 carbon atoms include phenyl, naphthyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthrenyl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphthacenyl, perylenyl, and pentacenyl.

As aromatic amine derivatives, examples of chrysene derivatives include N,N,N',N'-tetraphenylchrysene-6,12-diamine, N,N,N',N'-tetra(p-tolyl)chrysene-6,12-diamine, N,N,N',N'-tetra(m-tolyl)chrysene-6,12-diamine, N,N,N',N'-tetrakis(4-isopropylphenyl)chrysene-6,12-diamine, N,N,N',N'-tetra(naphthalene-2-yl)chrysene-6,12-diamine, N,N'-diphenyl Examples include -N,N'-di(p-tolyl)chrysene-6,12-diamine, N,N'-diphenyl-N,N'-bis(4-ethylphenyl)chrysene-6,12-diamine, N,N'-diphenyl-N,N'-bis(4-isopropylphenyl)chrysene-6,12-diamine, N,N'-diphenyl-N,N'-bis(4-t-butylphenyl)chrysene-6,12-diamine, and N,N'-bis(4-isopropylphenyl)-N,N'-di(p-tolyl)chrysene-6,12-diamine.

Examples of pyrene-based compounds include N,N,N',N'-tetraphenylpyrene-1,6-diamine, N,N,N',N'-tetra(p-tolyl)pyrene-1,6-diamine, N,N,N',N'-tetra(m-tolyl)pyrene-1,6-diamine, N,N,N',N'-tetrakis(4-isopropylphenyl)pyrene-1,6-diamine, N,N,N',N'-tetrakis(3,4-dimethylphenyl)pyrene-1,6-diamine, N,N'-diphenyl-N,N'-di(p-tolyl)pyrene-1,6-diamine, and N,N'-diphenyl-N,N'-bis(4-ethylphenyl)pyrene-1, 6-diamine, N,N'-diphenyl-N,N'-bis(4-isopropylphenyl)pyrene-1,6-diamine, N,N'-diphenyl-N,N'-bis(4-t-butylphenyl)pyrene-1,6-diamine, N,N'-bis(4-isopropylphenyl)-N,N'-di(p-tolyl)pyrene-1,6-diamine, N,N,N',N'-tetrakis(3,4-dimethylphenyl)-3,8-diphenylpyrene-1,6-diamine, N,N,N,N-tetraphenylpyrene-1,8-diamine, N,N'-bis(biphenyl-4-yl)-N,N'-diphenylpyrene-1,8-diamine, N ¹ ,N ⁶ -diphenyl- ^{N 1} ,N ⁶ -bis-(4-trimethylsilanyl-phenyl)-1H,8H-pyrene-1,6-diamine and the like.

Examples of anthracene-based compounds include N,N,N,N-tetraphenylanthracene-9,10-diamine, N,N,N',N'-tetra(p-tolyl)anthracene-9,10-diamine, N,N,N',N'-tetra(m-tolyl)anthracene-9,10-diamine, N,N,N',N'-tetrakis(4-isopropylphenyl)anthracene-9,10-diamine, N,N'-diphenyl-N,N'-di(p-tolyl)anthracene-9,10-diamine, N,N'-diphenyl-N,N'-di(m-tolyl)anthracene-9,10 -diamine, N,N'-diphenyl-N,N'-bis(4-ethylphenyl)anthracene-9,10-diamine, N,N'-diphenyl-N,N'-bis(4-isopropylphenyl)anthracene-9,10-diamine, N,N'-diphenyl-N,N'-bis(4-t-butylphenyl)anthracene-9,10-diamine, N,N'-bis(4-isopropylphenyl)-N,N'-di(p-tolyl)anthracene-9,10-diamine, 2,6-di-t-butyl-N,N,N',N'-tetra(p-tolyl)anthracene-9,10-diamine 2,6-di-t-butyl-N,N'-diphenyl-N,N'-bis(4-isopropylphenyl)anthracene-9,10-diamine, 2,6-di-t-butyl-N,N'-bis(4-isopropylphenyl)-N,N'-di(p-tolyl)anthracene-9,10-diamine, 2,6-dicyclohexyl-N,N'-bis(4-isopropylphenyl)-N,N'-di(p-tolyl)anthracene-9,10-diamine, 2,6-dicyclohexyl-N,N'-bis(4-isopropylphenyl)-N,N'-bis(4-t-butylphenyl)anthracene Examples include anthracene-9,10-diamine, 9,10-bis(4-diphenylamino-phenyl)anthracene, 9,10-bis(4-di(1-naphthylamino)phenyl)anthracene, 9,10-bis(4-di(2-naphthylamino)phenyl)anthracene, 10-di-p-tolylamino-9-(4-di-p-tolylamino-1-naphthyl)anthracene, 10-diphenylamino-9-(4-diphenylamino-1-naphthyl)anthracene, and 10-diphenylamino-9-(6-diphenylamino-2-naphthyl)anthracene.

Other examples include [4-(4-diphenylamino-phenyl)naphthalen-1-yl]-diphenylamine, [6-(4-diphenylamino-phenyl)naphthalen-2-yl]-diphenylamine, 4,4'-bis[4-diphenylaminonaphthalen-1-yl]biphenyl, 4,4'-bis[6-diphenylaminonaphthalen-2-yl]biphenyl, 4,4"-bis[4-diphenylaminonaphthalen-1-yl]-p-terphenyl, and 4,4"-bis[6-diphenylaminonaphthalen-2-yl]-p-terphenyl.
Furthermore, aromatic amine derivatives described in, for example, JP-A-2006-156888 may also be used.

The coumarin derivatives include coumarin-6, coumarin-334, and the like.
Furthermore, coumarin derivatives described in JP-A-2004-43646, JP-A-2001-76876, JP-A-6-298758, and the like may also be used.

また、特開2005-126399号公報、特開2005-097283号公報、特開2002-234892号公報、特開2001-220577号公報、特開2001-081090号公報、および特開2001-052869号公報などに記載されたピラン誘導体を用いてもよい。 Examples of the pyran derivative include the following DCM and DCJTB.

Furthermore, pyran derivatives described in JP-A-2005-126399, JP-A-2005-097283, JP-A-2002-234892, JP-A-2001-220577, JP-A-2001-081090, JP-A-2001-052869, and the like may also be used.

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

<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.

The material (electron transport material) forming the electron transport layer 106 or the electron injection layer 107 can be arbitrarily selected from compounds conventionally used as electron transport compounds in photoconductive materials and known compounds used in the electron injection layer and electron transport layer of organic EL elements. In the present invention, the polycyclic aromatic compound represented by the above general formula (1A) or general formula (1B) can be used as the electron transport material.

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

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

Metal complexes having 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.

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, even more preferred are Rb or Cs, and most preferred is 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 organic EL element can be improved and the life can be extended.

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

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

The material for forming the cathode 108 is not particularly limited as long as it 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 being dispersed in a solvent-soluble resin such as polyvinyl chloride, polycarbonate, polystyrene, poly(N-vinylcarbazole), polymethyl methacrylate, polybutyl methacrylate, polyester, polysulfone, polyphenylene oxide, polybutadiene, hydrocarbon resin, ketone resin, phenoxy resin, polyamide, ethyl cellulose, vinyl acetate resin, ABS resin, polyurethane resin, or a curable resin such as phenol resin, xylene resin, petroleum resin, urea resin, melamine resin, unsaturated polyester resin, alkyd resin, epoxy resin, silicone resin, or the like.

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

When applying a DC voltage to the organic EL element obtained in this way, the anode should be set to + and the cathode to -. When a voltage of about 2 to 40 V is applied, light emission can be observed from the transparent or semi-transparent electrode side (anode or cathode, or both). This organic EL element also emits light when a pulsed current or AC current is applied. The waveform of the AC current applied 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 device. In the preparation of the above-mentioned organic EL device, it is also possible to reverse the preparation order and prepare the cathode, electron injection layer, electron transport layer, light-emitting layer, hole transport layer, hole injection layer, and anode in that order. In addition to the method of simultaneously evaporating a plurality of materials from separate vapor deposition sources, the above-mentioned co-evaporation method includes a method of putting a mixture of materials to be co-evaporated into one vapor deposition source and evaporating them at once (premix method).

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

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

A wet film formation method is a film formation method that uses a solution, and examples of this include some printing methods (inkjet methods), spin coating methods or casting methods, and coating methods. Unlike vacuum deposition methods, wet film formation 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 a material for the electron transport layer and a material for the electron injection layer can be prepared and then the layer can be formed by a wet film formation method.

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

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

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

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

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

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

After 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, Examples of the solvent include, but are not limited to, 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, and benzyl octyl ether. The solvent may be used alone or in admixture.

<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 using a known method. 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（Ｈ３）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 (H3), 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 (H3) 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 compound of formula (H3) and the compound of formula (XLP-1) may be produced in one step or in multiple steps. In addition, the reaction may be started after all the raw materials are placed in a reaction vessel by a batch polymerization method, or may be performed by a dropwise polymerization method in which the raw materials are added dropwise to a reaction vessel, or may be performed by a precipitation polymerization method in which the product precipitates as the reaction proceeds, and these methods can be combined appropriately to synthesize the compound. For example, when synthesizing the compound represented by formula (H3) in one step, the target product is obtained by carrying out a reaction in a state in which the monomer unit (MU) and the end cap unit (EC) are added to a reaction vessel. In addition, when synthesizing the compound represented by general formula (H3) in multiple steps, the monomer unit (MU) is polymerized to the target molecular weight, and then the end cap unit (EC) is added and reacted to obtain the target product. 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. In addition, after preparing a precursor polymer, the target polymer can be obtained by a subsequent reaction.

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

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-A-2012-144722.

<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 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 2003-257621 A, JP 2003-277741 A, JP 2004-119211 A, etc.). Backlights are mainly used for the purpose of improving the visibility of non-self-luminous display devices, and are used in liquid crystal display devices, clocks, audio devices, automobile panels, display boards, signs, etc. In particular, for liquid crystal display devices, and especially for 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 device 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 structure.
(1) Substrate/gate electrode/insulator layer/source electrode/drain electrode/organic semiconductor active layer (2) Substrate/gate electrode/insulator layer/organic semiconductor active layer/source electrode/drain electrode (3) Substrate/organic semiconductor active layer/source electrode/drain electrode/insulator layer/gate electrode (4) Substrate/source electrode/drain electrode/organic semiconductor active layer/insulator layer/gate electrode An organic field effect transistor configured in this manner can be used as a pixel driving switching element for active matrix driving liquid crystal displays and organic electroluminescence displays.

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

<Wavelength conversion material>
The polycyclic aromatic compound of the present invention can be used as a wavelength converting material.
Currently, the application of multi-coloring technology using color conversion methods to liquid crystal displays, organic EL displays, lighting, and the like is being actively studied. Color conversion refers to wavelength conversion of light emitted from a light emitter to light with a longer wavelength, for example, converting ultraviolet light or blue light to green light or red light emission. By forming a wavelength conversion material having this color conversion function into a film and combining it with, for example, a blue light source, it becomes possible to extract the three primary colors of blue, green, and red from the blue light source, that is, to extract white light. By combining such a white light source, which is a combination of a blue light source and a wavelength conversion film having a color conversion function, with a liquid crystal driving part and a color filter as a light source unit, it becomes possible to manufacture a full-color display. Furthermore, if there is no liquid crystal driving part, it can be used as a white light source as it is, and can be applied as a white light source such as LED lighting. Furthermore, by using a blue organic EL element as a light source in combination with a wavelength conversion film that converts blue light into green light and red light, it becomes possible to manufacture a full-color organic EL display without using a metal mask. Furthermore, by using blue micro-LEDs as a light source in combination with wavelength conversion films that convert blue light into green and red light, it becomes possible to create low-cost full-color micro-LED displays.

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 (2A-szs-0004) Compound (Int-2A-szs-0004) (2.95 g, 3.0 mmol, 1 eq.) and o-dichlorobenzene (400 ml) were added to a flask at room temperature under a nitrogen atmosphere to boron tribromide (1.13 ml, 12 mmol, 4 eq.). After the dropwise addition was completed, the temperature was raised to 180° C. and the mixture was stirred for 20 hours. Then, the mixture was cooled again to room temperature, and N,N-diisopropylethylamine (7.70 ml, 45 mmol, 15 eq.) was added and the mixture was stirred until the heat generation subsided. Then, the reaction solution was distilled off under reduced pressure at 60° C. to obtain a crude product. The obtained crude product was washed with acetonitrile, methanol, and toluene in this order, and purified with a silica gel column (eluent: toluene). The crude product was then recrystallized twice with o-dichlorobenzene to obtain compound (2A-szs-0004) (0.22 g).
The compound (2A-szs-0004) was identified as the target product with an m/z (M+H) of 998.388 by MS.

Synthesis Example (2): Synthesis of compound (2A-zsz-0004) Compound (2A-zsz-0004) (0.25 g) was obtained in the same manner as in Synthesis Example 1, except that compound (Int-2A-szs-0004) (2.95 g, 3.0 mmol, 1 eq.) was changed to compound (Int-2A-zsz-0004) (2.80 g, 3.0 mmol, 1 eq.).
The compound (2A-zsz-0004) was identified as the target product by MS with m/z (M+H) = 950.388949.380.

Synthesis Example (3): Synthesis of compound (2A-zzz-0002) Compound (2A-zzz-0002) was obtained (0.19 g) in the same manner as in Synthesis Example 1, except that compound (Int-2A-szs-0004) (2.95 g, 3.0 mmol, 1 eq.) was changed to compound (Int-2A-zzz-0002) (2.66 g, 3.0 mmol, 1 eq.).
The compound (2A-zzz-0002) was identified as the target product with m/z (M+H) = 902.388 by MS.

Synthesis Example (4): Synthesis of Compound (2B-szs-0001) To a flask containing the compound (Int-2A-szs-0004) (2.95 g, 3.0 mmol, 1 eq.) and o-dichlorobenzene (400 ml), boron tribromide (1.70 ml, 18 mmol, 6 eq.) was added at room temperature under a nitrogen atmosphere. After the dropwise addition was completed, the temperature was raised to 180° C. and the mixture was stirred for 20 hours. Then, the mixture was cooled again to room temperature, and N,N-diisopropylethylamine (11.6 ml, 68 mmol, 23 eq.) was added and the mixture was stirred until the heat generation subsided. Then, the reaction solution was distilled off under reduced pressure at 60° C. to obtain a crude product. The obtained crude product was washed with acetonitrile, methanol, and toluene in this order, and purified with a silica gel column (eluent: toluene). The crude product was then recrystallized twice with o-dichlorobenzene to obtain compound (2B-szs-0001) (0.24 g).
The compound (2B-szs-0001) was identified as the target product with m/z (M+H) = 1006.374 by MS.

Synthesis Example (5): Synthesis of compound (2B-zsz-0001) Compound (2B-zsz-0001) was obtained (0.21 g) in the same manner as in Synthesis Example 4, except that compound (Int-2A-szs-0004) (2.95 g, 3.0 mmol, 1 eq.) was changed to compound (Int-2A-zsz-0004) (2.80 g, 3.0 mmol, 1 eq.).
The compound (2B-zsz-0001) was identified as the target product with m/z (M+H) = 958.374 by MS.

Synthesis Example (6): Synthesis of compound (2B-zzz-0001) Compound (2B-zzz-0001) was obtained (0.20 g) in the same manner as in Synthesis Example 4, except that compound (Int-2A-szs-0004) (2.95 g, 3.0 mmol, 1 eq.) was changed to compound (Int-2A-zzz-0002) (2.66 g, 3.0 mmol, 1 eq.).
MS confirmed that the compound was the target (2B-zzz-0001) with m/z (M+H) = 910.374.

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, we will describe the evaluation of the basic physical properties of the compound of the present invention and the preparation and evaluation of an organic EL device using the compound of the present invention. However, the application of the compound of the present invention is not limited to the examples shown below, and the film thickness and constituent materials of each layer can be appropriately changed depending on the basic physical properties of the compound of the present invention.

<Evaluation of deposition type organic EL elements>
Organic EL elements according to Examples 1-1 to 1-6 and Comparative Examples 1-1 to 1-4 were prepared, and the emission wavelength, half-width, driving voltage, external quantum efficiency, and LT50 (the time during which a luminance of 250 cd/m2 or ^more is maintained when continuously driven at a current density at an initial luminance of 500 cd/ ^m2 ) at a luminance of 500 cd/ ^m2 were measured.

In Table 1, the chemical structures of "NPD,""TcTa,""mCP,""Ir(ppy) ₃ ,""2CzBN,""BPy-TP2," and "GH-1" are shown below.

The chemical structures of RGD-1, RGD-2, and RGD-3 in Table 1 are shown below.

<Example 1-1>
A 26 mm × 28 mm × 0.7 mm glass substrate (manufactured by Optoscience Co., Ltd.) on which an ITO film having a thickness of 200 nm was formed by sputtering and polished to 50 nm was used as a transparent support substrate. This transparent support substrate was fixed to a substrate holder of a commercially available deposition apparatus (manufactured by Showa Vacuum Co., Ltd.), and a molybdenum deposition boat containing NPD, TcTa, mCP, GH-1, compound (2A-szs-0004), 2CzBN, and BPy-TP2, and a tungsten deposition boat containing LiF and aluminum were attached.

The following layers were formed in sequence on the ITO film of the transparent support substrate. The vacuum chamber was depressurized to 5×10 ⁻⁴ Pa, and first, NPD was heated and evaporated to a thickness of 40 nm to form a hole injection layer. Next, TcTa was heated and evaporated to a thickness of 15 nm, and mCP was further heated and evaporated to a thickness of 15 nm to form a hole transport layer consisting of two layers. Next, GH-1 and the compound (2A-szs-0004) were simultaneously heated 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 GH-1 to the compound (2A-szs-0004) was approximately 99:1. Next, 2CzBN was heated and evaporated to a thickness of 10 nm, and BPy-TP2 was further heated and evaporated to a thickness of 20 nm to form an electron transport layer consisting of two layers. The evaporation rate of each layer was 0.01 to 1 nm/sec. Thereafter, LiF was heated and evaporated at a deposition rate of 0.01 to 0.1 nm/sec to a thickness of 1 nm, and then aluminum was heated and evaporated to a thickness of 100 nm to form a cathode, thereby obtaining an organic EL device. At this time, the deposition rate of aluminum was adjusted to 1 to 10 nm/sec.

<Examples 1-2 to 1-6>
The compound (2A-szs-0004) used as the dopant in Example 1 was changed to each dopant and each mixing ratio shown in Table 1 to fabricate each device.

<Comparative Examples 1-1 to 1-4>
The compound (2A-szs-0004) used as the dopant in Example 1 was changed to each of the dopants shown in Table 1 to fabricate each device.

The evaluation results of each element are shown in Table 2.

In Examples 1-1 to 1-6, the external quantum efficiency was higher and the element life was longer than in Comparative Examples 1-1 to 1-4.

<Evaluation of deposition type organic EL elements>
Organic EL elements according to Examples G2-1 to G2-6, Comparative Example G2-1, Examples G3-1 to G3-6, and Comparative Example G3-1 were prepared, and the emission wavelength, half-width, driving voltage, external quantum efficiency, and ^LT50 (the time during which a luminance of 250 cd/ ^m2 or more is maintained when continuously driven at a current density at an initial luminance of 500 cd/ ^m2 ) at a luminance of 500 cd/m2 were measured.

In Table 3, the chemical structures of "HATCN", "TBB", "CBP", "TPBi" and "GH-2" are shown below.

<Example G2-1>
A 26 mm x 28 mm x 0.7 mm glass substrate (manufactured by Optoscience Co., Ltd.) on which an ITO film having a thickness of 200 nm was formed by sputtering and polished to 50 nm was used as a transparent support substrate. This transparent support substrate was fixed to a substrate holder of a commercially available deposition apparatus (manufactured by Showa Vacuum Co., Ltd.), and a molybdenum deposition boat containing HATCN, TBB, TcTa, CBP, compound (2A-szs-0004), and TPBi, and a tungsten deposition boat containing LiF and aluminum were attached.

The following layers were formed in sequence on the ITO film of the transparent support substrate. The vacuum chamber was depressurized to 5×10 ⁻⁴ Pa, and first, HATCN was heated and evaporated to a thickness of 5 nm to form a hole injection layer. Next, TBB was heated and evaporated to a thickness of 65 nm, and further, TcTa was heated and evaporated to a thickness of 10 nm to form a two-layer hole transport layer. Next, CBP and the compound (2A-szs-0004) were heated simultaneously and evaporated to a thickness of 30 nm to form a light-emitting layer. The evaporation rate was adjusted so that the weight ratio of CBP to the compound (2A-szs-0004) was approximately 99:1. Next, TPBi 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. Thereafter, LiF was heated and evaporated at a deposition rate of 0.01 to 0.1 nm/sec to a thickness of 1 nm, and then aluminum was heated and evaporated to a thickness of 100 nm to form a cathode, thereby obtaining an organic EL device. At this time, the deposition rate of aluminum was adjusted to 1 to 10 nm/sec.

<Examples G2-2 to G2-6, Comparative Example G2-1, Examples G3-1 to G3-6, and Comparative Example G3-1>
The host CBP, the dopant compound (2A-szs-0004), and the mixing ratio in Example G2-1 were changed to each host, each dopant, and each mixing ratio shown in Table 3 to prepare each device.

The evaluation results of each element are shown in Table 4.

In Examples G2-1 to G2-6 and Examples G3-1 to G3-6, higher efficiency and longer element life were obtained as compared with Comparative Example G2-1 and Comparative Example G3-1.

<Evaluation of deposition type organic EL elements>
Organic EL elements according to Examples G4-1 to G4-4 and Comparative Example G4-1 were prepared, and the emission wavelength, half-width, driving voltage, external quantum efficiency, and LT50 (the time during which a luminance of 250 cd/ ^m2 or more is maintained when continuously driven at a current density at an initial luminance of 500 cd/ ^m2 ) at a luminance of 500 cd/ ^m2 were measured.

In Table 5, the chemical structures of "T2T", "4CzIPN", "BCC-TPTA" and "Liq" are shown below.

<Example G4-1>
A 26 mm x 28 mm x 0.7 mm glass substrate (manufactured by Optoscience Co., Ltd.) on which an ITO film formed to a thickness of 200 nm by sputtering was polished to 50 nm was used as a transparent support substrate. This transparent support substrate was fixed to a substrate holder of a commercially available deposition apparatus (manufactured by Showa Vacuum Co., Ltd.), and a molybdenum deposition boat containing HATCN, TBB, TcTa, 4CzIPN, compound (2A-szs-0004), T2T, Liq, and TPBi, and a tungsten deposition boat containing LiF and aluminum were attached.

The following layers were formed in sequence on the ITO film of the transparent support substrate. The vacuum chamber was depressurized to 5×10 ⁻⁴ Pa, and first, HATCN was heated and evaporated to a thickness of 5 nm to form a hole injection layer. Next, TBB was heated and evaporated to a thickness of 65 nm, and further, TcTa was heated and evaporated to a thickness of 10 nm to form a hole transport layer consisting of two layers. Next, TcTa, 4CzIPN, and the compound (2A-szs-0004) were heated simultaneously and evaporated to a thickness of 30 nm to form a light-emitting layer. The evaporation rate was adjusted so that the weight ratio of CBP, 4CzIPN, and the compound (2A-szs-0004) was approximately 85:14:1. Next, T2T was heated and evaporated to a thickness of 10 nm, and then TPBi and Liq were heated and evaporated to a thickness of 40 nm to form an electron transport layer consisting of two layers. The deposition rate was adjusted so that the weight ratio of TPBi to Liq was approximately 70:30. The deposition rate of each layer was 0.01 to 1 nm/sec. Thereafter, LiF was heated and deposited at a deposition rate of 0.01 to 0.1 nm/sec so as to have a film thickness of 1 nm, and then aluminum was heated and deposited to have a film thickness of 100 nm to form a cathode, thereby obtaining an organic EL device. At this time, the deposition rate of aluminum was adjusted to be 1 to 10 nm/sec.

<Examples G4-2 to G4-4 and Comparative Example G4-1>
The assisting dopant 4CzIPN and the dopant compound (2A-szs-0004) and their mixing ratios in Example G4-1 were changed to the assisting dopants, dopants, and mixing ratios shown in Table 5 to fabricate each element.

The evaluation results of each element are shown in Table 6.

In comparison with Comparative Example G4-1, Examples G4-1 to G4-4 exhibited higher efficiency and longer device life. As in Examples G4-3 and G4-4, devices using an exciplex and an assisting dopant can be realized.

<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 was obtained in which M2 or M3 was bonded next to M1, and it is estimated from the feed ratio that each unit is 50:26:24 (molar ratio). In the following structural formula, Me is a methyl group, Bpin is a pinacolatoboryl group, and * is the linking point of each unit.

<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). In the following structural formula, Me is a methyl group, Bpin is a pinacolatoboryl group, and * is the linking point of each unit.

<Examples 2-1 to 2-9>
A coating solution of the material for forming each layer is prepared to prepare a coating type organic EL element.

<Preparation of Organic EL Elements of Examples 2-1 to 2-3>
Table 7 shows the material composition of each layer in the organic EL element.

The structure of "ET1" in Table 7 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 general formula (1A) or general formula (1B) (e.g., compound (1A-32)), a polymer compound obtained by polymerizing the polycyclic aromatic compound as a monomer (i.e., the monomer has a reactive substituent), or a crosslinked polymer obtained by further crosslinking the polymer compound. The polymer compound for obtaining the crosslinked polymer 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 0.6% by weight XLP-101 solution.

<Preparation of PCz solution>
PCz (polyvinylcarbazole) 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.

<Evaluation of Organic EL Elements of Examples 2-1 to 2-3>
The coating type organic EL element obtained as described above is expected to have excellent driving voltage and external quantum efficiency, similar to the deposition type organic EL element.

<Preparation of Organic EL Elements of Examples 2-4 to 2-6>
Table 8 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 8, "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 was formed to a thickness of 45 nm was spin-coated with an ND-3202 (Nissan Chemical Industries) solution, and then heated in an air atmosphere at 50°C for 3 minutes, and then heated at 230°C for 15 minutes to form an ND-3202 film with a thickness of 50 nm (hole injection layer). Next, an XLP-101 solution was spin-coated, and heated on a hot plate in a nitrogen gas atmosphere at 200°C for 30 minutes to form an XLP-101 film with a thickness of 20 nm (hole transport layer). Next, a composition for forming an emitting layer (2) was spin-coated, and heated in a nitrogen gas atmosphere at 130°C for 10 minutes to form a emitting layer with a thickness of 20 nm.

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

<Examples 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.

<Evaluation of Organic EL Elements of Examples 2-4 to 2-6>
The coating type organic EL element obtained as described above is expected to have excellent driving voltage and external quantum efficiency, similar to the deposition type organic EL element.

<Preparation of Organic EL Elements of Examples 2-7 to 2-9>
Table 9 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 9, "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 was formed to a thickness of 45 nm was spin-coated with an ND-3202 (manufactured by Nissan Chemical Industries, Ltd.) solution, and then heated in an air atmosphere at 50° C. for 3 minutes, and then heated at 230° C. for 15 minutes to form an ND-3202 film with a thickness of 50 nm (hole injection layer). Next, an XLP-101 solution was spin-coated, and heated on a hot plate in a nitrogen gas atmosphere at 200° C. for 30 minutes to form an XLP-101 film with a thickness of 20 nm (hole transport layer). Next, a composition for forming an emitting layer (5) was spin-coated, and heated in a nitrogen gas atmosphere at 130° C. for 10 minutes to form an emitting layer with a thickness of 20 nm.

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

<Examples 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.

<Evaluation of Organic EL Elements of Examples 2-7 to 2-9>
The coating type organic EL element obtained as described above is expected to have excellent driving voltage and external quantum efficiency, similar to the deposition type organic EL element.

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, by producing an organic EL element using a novel polycyclic aromatic compound, for example as a dopant material, it is possible to provide an organic EL element having a narrow half-width of the emission spectrum and excellent color purity, as well as an organic EL element having excellent quantum efficiency and device life. In addition, since the novel polycyclic aromatic compound of the present invention has a rigid structure, many of the compounds have a sharper emission spectrum, a narrow half-width of the emission spectrum, and emit light with high color purity.

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 (10)

A polycyclic aromatic compound represented by any one of the following structural formulas.
In each formula,
R's are each independently a hydrogen atom, an aryl group having 6 to 16 carbon atoms, a heteroaryl group having 2 to 20 carbon atoms, a diarylamino group (wherein the aryl group is an aryl group having 6 to 10 carbon atoms), a diarylboryl group (wherein the aryl group is an aryl group 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 is optionally substituted by an alkyl group having 1 to 5 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms;
Each o is independently an integer from 1 to 3;
Each p is independently an integer from 1 to 4;
Each q is independently an integer from 1 to 5;
At least one hydrogen in the compounds represented by the above formulas may be substituted with deuterium, cyano, or halogen. The polycyclic aromatic compound 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 according to claim 1 or 2 . The material for an organic device according to claim 3 , 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 4 , wherein the material for an organic electroluminescent element is a material for a light-emitting layer. An ink composition comprising the polycyclic aromatic compound according to claim 1 or 2 and an organic solvent. 3. An organic electroluminescence device comprising a pair of electrodes consisting of an anode and a cathode, and an organic layer disposed between the pair of electrodes and containing the polycyclic aromatic compound according to claim 1 . The organic electroluminescent device according to claim 7 , wherein the organic layer is a light-emitting layer. The organic electroluminescent device according to claim 8 , wherein the light-emitting layer contains a host and the polycyclic aromatic compound as a dopant. A display device or a lighting device comprising the organic electroluminescent device according to any one of claims 7 to 9 .

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