KR20220124097A - Polycyclic aromatic compound - Google Patents

Abstract

The present invention relates to a polycyclic aromatic compound. The polycyclic aromatic compound of the present invention is represented by Chemical Formula (1A-1) and has a structure composed of one or two or more structural units, wherein, in Chemical Formula (1A-1), A2 ring, A3 ring, and A4 ring are each a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring. Therefore, the polycyclic aromatic compound of the present invention can be used for manufacturing organic devices such as organic electroluminescent devices.

Description

Polycyclic aromatic compound {POLYCYCLIC AROMATIC COMPOUND}

The present invention relates to polycyclic aromatic compounds. The present invention relates in particular to polycyclic aromatic compounds comprising nitrogen and boron. The present invention also relates to a material for an organic device, an organic electroluminescent device, and a display device and a lighting device comprising the polycyclic aromatic compound.

Conventionally, a display device using an electroluminescent light emitting element has been studied in various ways because it can be reduced in power and thin. Furthermore, an organic electroluminescent element made of an organic material has been actively studied because it is easy to reduce the weight and increase the size. In particular, with respect to the development of organic materials having luminescent properties such as blue, which is one of the three primary colors of light, and the development of organic materials having charge transport capability of holes and electrons (possible to become semiconductors and superconductors), high molecular weight compounds , and low molecular weight compounds have been actively studied so far.

The organic electroluminescent element has a structure consisting of a pair of electrodes comprising an anode and a cathode, and one or more layers including an organic compound and disposed between the pair of electrodes. The layer containing the organic compound includes 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.

Among them, Patent Document 1 discloses that a polycyclic aromatic compound containing boron is useful as a material for an organic electroluminescent device or the like. It has been reported that the organic electroluminescent device containing this polycyclic aromatic compound has good external quantum efficiency.

Patent Document 1: International Publication 2015/102118

As described above, various materials have been developed as materials for use in organic EL devices. However, in order to increase the selection of materials for organic EL devices, development of materials made of compounds different from those in the prior art is expected.

An object of the present invention is to provide a novel compound useful as a material for an organic device such as an organic EL device.

MEANS TO SOLVE THE PROBLEM The present inventors earnestly studied in order to solve the said subject, and succeeded in manufacture of the novel polycyclic aromatic compound which is more excellent in luminescent property in the polycyclic aromatic compound which has a structure similar to the compound described in patent document 1.

Specifically, the present invention has the following structures.

<1>

A polycyclic aromatic compound represented by the following formula (1A-1) and having a structure comprising one or two or more structural units.

In formula (1A-1),

A2 ring, A3 ring, and A4 ring are each independently a substituted or unsubstituted aryl ring, or a substituted or unsubstituted heteroaryl ring,

ring A1 and ring A5 are each independently a substituted or unsubstituted aryl ring, a substituted or unsubstituted heteroaryl ring, a substituted or unsubstituted cycloalkyl ring, or a cycloheteroalkyl ring;

Y ¹ is B, P, P=O, P=S, Al, Ga, As, Si-R, or Ge-R, wherein R of Si-R and Ge-R is substituted or unsubstituted aryl , substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl;

L ¹ , L ² , L ³ , and L ⁴ are each independently a single bond, substituted or unsubstituted arylene, substituted or unsubstituted heteroarylene, substituted or unsubstituted alkylene, substituted or unsubstituted cycloalkylene, substituted or unsubstituted alkenylene, >O, >NR, >C(-R) ₂ , >Si(-R) ₂ , >S, or >Se, wherein R of >NR, said R of >Si(-R) ₂ and R of >C(-R) ₂ are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, wherein two R of >Si(-R) ₂ and two R of >C(-R) ₂ are not bonded to each other to form a ring, or , R of >NR, R of >C(-R) ₂ , and at least one R of >Si(-R) ₂ Each independently represents an A1 ring, A2 ring, A3 ring, A4 ring, and At least one of the A5 rings is not bonded to, or is bonded to, through a single bond or a linking group;

n, m, q, and r are each independently 0 or 1, and in the case of 0, each independently means that hydrogen or a substituent is present instead of L ¹ , L ² , L ³ or L ⁴ , provided that , n+m=1 and not q+r=0;

The polycyclic aromatic compound having a structure consisting of one or two or more of the structural units represented by the formula (1A-1) is not condensed with at least one cycloalkane or is condensed with at least one cycloalkane one hydrogen is unsubstituted or substituted, and at least one -CH ₂ - in the corresponding cycloalkane is unsubstituted or substituted with -O- or -S-, and;

At least one hydrogen in the structure represented by formula (1A-1) is unsubstituted or substituted with cyano, halogen, or deuterium.

<2>

The polycyclic aromatic compound according to <1>, wherein the structural unit is a structural unit represented by the following formula (1a-1).

In formula (1a-1),

Y ¹ is B, P, P=O, P=S, Al, Ga, As, Si-R, or Ge-R, wherein R of Si-R and Ge-R is substituted or unsubstituted aryl , substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl;

L ¹ , L ² , L ³ , and L ⁴ are each independently a single bond, substituted or unsubstituted arylene, substituted or unsubstituted heteroarylene, substituted or unsubstituted alkylene, substituted or unsubstituted cycloalkylene, substituted or unsubstituted alkenylene, >O, >NR, >C(-R) ₂ , >Si(-R) ₂ , >S, or >Se, wherein R of >NR, said R of >Si(-R) ₂ and R of >C(-R) ₂ are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, wherein two R of >Si(-R) ₂ and two R of >C(-R) ₂ are not bonded to each other to form a ring, or , R of >NR, R of >C(-R) ₂ , and at least one R of >Si(-R) ₂ are each independently at least one of R ^Z in Z that is CR ^Z and -O-, -S-, -C(-R) ₂ - or not bonded by a single bond or bonded;

n, m, q, and r are each independently 0 or 1, the case of 0 means that each independently R ¹ is present instead of L ¹ , L ² , L ³ or L ⁴ , provided that n+m=1 and not q+r=0;

each Z is, independently, N or CR ¹ , or Z=Z is each independently >O, >NR, >C(-R) ₂ , >Si(-R) ₂ , >S, or >Se , wherein R ¹ of CR ¹ is each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio or substituted silyl, wherein at least one hydrogen is unsubstituted or substituted with aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, The two aryls are not bonded to each other or are bonded through a linking group, and the two heteroaryls of the diheteroarylamino are not bonded to each other or are bonded through a linking group, and the aryl and heteroaryl of the arylheteroarylamino are hetero Aryl is not bonded to each other or is bonded through a linking group, and the two aryls of the diarylboryl are not bonded to each other, or are bonded to each other through a single bond or a linking group;

Two adjacent R ¹ are bonded to each other, do not form or form an aryl ring or a heteroaryl ring, and at least one hydrogen of the formed aryl ring and the formed aryl heteroaryl ring is, respectively, aryl, hetero unsubstituted or substituted with aryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or substituted silyl; At least one hydrogen in is unsubstituted or substituted with aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, and the two aryls of the diarylamino are not bonded to each other, Or they are bonded through a linking group, and the two heteroaryls of the diheteroarylamino are not bonded to each other, or are bonded through a linking group, and the aryl and heteroaryl of the arylheteroarylamino are not bonded to each other, or a linking group are bonded through, and the two aryls of the diarylboryl are not bonded to each other, or are bonded through a single bond or a linking group, and the >NR, the >C(-R) ₂ and the >Si(-R) ) ₂ R is each independently hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, wherein at least one hydrogen is aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl unsubstituted or substituted, and two R of >C(-R) ₂ and >Si(-R) ₂ are not bonded to each other to form a ring;

The polycyclic aromatic compound having a structure comprising one or two or more of the structural units represented by the formula (1a-1) is not condensed with at least one cycloalkane or is condensed with at least one cycloalkane one hydrogen is unsubstituted or substituted, and at least one -CH ₂ in the cycloalkane is unsubstituted or substituted with -O- or -S-, and;

At least one hydrogen in the structure represented by formula (1a-1) is unsubstituted or substituted with cyano, halogen, or deuterium.

<3>

The polycyclic aromatic compound according to <1>, wherein the structural unit is a structural unit represented by the following formula (1b-1) or (1b-2), respectively.

In formulas (1b-1) and (1b-2),

L ³ , L ⁴ are each independently a single bond, arylene, heteroarylene or alkenylene, at least one of which hydrogen is not substituted with alkyl, cycloalkyl, diarylamino, or substituted silyl, or is substituted, and the two aryls of the diarylamino are not bonded or bonded through a linking group;

q, and r are each independently 0 or 1, the case of 0 means that each independently R ¹ is present instead of L ³ or L ⁴ , provided that q+r=0;

Y ¹ is B, P, P=O, P=S, Al, Ga, As, Si-R, or Ge-R, wherein R of Si-R and Ge-R is substituted or unsubstituted aryl , substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl;

each Z is, independently, N or CR ¹ , or Z=Z is each independently >O, >NR, >C(-R) ₂ , >Si(-R) ₂ , >S, or >Se , wherein R ¹ of CR ¹ is each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio or substituted silyl, wherein at least one hydrogen is unsubstituted or substituted with aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, The two aryls are not bonded to each other or are bonded through a linking group, and the two heteroaryls of the diheteroarylamino are not bonded to each other or are bonded through a linking group, and the aryl and heteroaryl of the arylheteroarylamino are hetero Aryl is not bonded to each other or is bonded through a linking group, and the two aryls of the diarylboryl are not bonded to each other, or are bonded to each other through a single bond or a linking group;

Two adjacent R ¹ are bonded to each other, do not form or form an aryl ring or a heteroaryl ring, and at least one hydrogen of the formed aryl ring and the formed aryl heteroaryl ring is, respectively, aryl, hetero unsubstituted or substituted with aryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or substituted silyl; At least one hydrogen in is unsubstituted or substituted with aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, and the two aryls of the diarylamino are not bonded to each other, Or they are bonded through a linking group, and the two heteroaryls of the diheteroarylamino are not bonded to each other, or are bonded through a linking group, and the aryl and heteroaryl of the arylheteroarylamino are not bonded to each other, or a linking group are bonded through, and the two aryls of the diarylboryl are not bonded to each other, or are bonded through a single bond or a linking group, and the >NR, the >C(-R) ₂ and the >Si(-R) ) ₂ R is each independently hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, wherein at least one hydrogen is aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl unsubstituted or substituted, and two R of >C(-R)2 and >Si(-R)2 are not bonded to each other to form a ring;

The polycyclic aromatic compound having a structure comprising one or two or more of the structural units represented by formula (1b-1) or formula (1b-2) is not condensed with at least one cycloalkane or is condensed; At least one hydrogen in the cycloalkane is unsubstituted or substituted, and at least one -CH ₂ - in the cycloalkane is unsubstituted or substituted with -O- or -S-, , and;

At least one hydrogen in the structure represented by the formula (1b-1) or (1b-2) is unsubstituted or substituted with cyano, halogen, or deuterium.

<4>

The polycyclic aromatic compound according to <1>, wherein the structural unit is a structural unit represented by the following formula (1c-1), (1c-2), (1c-3), or (1c-4).

In formula (1c-1), formula (1c-2), formula (1c-3) and formula (1c-4),

each Z is, independently, N or CR ¹ , or Z=Z is each independently >O, >NR, >C(-R) ₂ , >Si(-R) ₂ , >S, or >Se , wherein R ¹ of CR ¹ is each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio or substituted silyl, wherein at least one hydrogen is unsubstituted or substituted with aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, The two aryls are not bonded to each other or are bonded through a linking group, and the two heteroaryls of the diheteroarylamino are not bonded to each other or are bonded through a linking group, and the aryl and heteroaryl of the arylheteroarylamino are hetero Aryl is not bonded to each other or is bonded through a linking group, and the two aryls of the diarylboryl are not bonded to each other, or are bonded to each other through a single bond or a linking group;

Two adjacent R ¹ are bonded to each other, do not form or form an aryl ring or a heteroaryl ring, and at least one hydrogen of the formed aryl ring and the formed aryl heteroaryl ring is, respectively, aryl, hetero unsubstituted or substituted with aryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or substituted silyl; At least one hydrogen in is unsubstituted or substituted with aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, and the two aryls of the diarylamino are not bonded to each other, Or they are bonded through a linking group, and the two heteroaryls of the diheteroarylamino are not bonded to each other, or are bonded through a linking group, and the aryl and heteroaryl of the arylheteroarylamino are not bonded to each other, or a linking group are bonded through, and the two aryls of the diarylboryl are not bonded to each other, or are bonded through a single bond or a linking group, and the >NR, the >C(-R) ₂ and the >Si(-R) ) ₂ R is each independently hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, wherein at least one hydrogen is aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl unsubstituted or substituted, and two R of >C(-R) ₂ and >Si(-R) ₂ are not bonded to each other to form a ring;

A polycyclic aromatic compound having a structure comprising one or two or more of the structural units represented by formula (1c-1), formula (1c-2), formula (1c-3), or formula (1c-4) is uncondensed or condensed with at least one cycloalkane, at least one hydrogen in the cycloalkane is unsubstituted or substituted, and at least one -CH ₂ - in the cycloalkane is - unsubstituted or substituted with O- or -S-, and;

At least one hydrogen in the structure represented by formula (1c-1), formula (1c-2), formula (1c-3), or formula (1c-4) is not substituted with cyano, halogen, or deuterium or is substituted.

<5>

The polycyclic aromatic compound according to <1>, wherein the structural unit is a structural unit represented by the formula (1d-1) or (1d-2).

In formulas (1d-1) and (1d-2),

L ³ , L ⁴ are each independently a single bond, arylene, heteroarylene or alkenylene, at least one of which hydrogen is not substituted with alkyl, cycloalkyl, diarylamino, or substituted silyl, or is substituted, and the two aryls of the diarylamino are not bonded or bonded through a linking group;

q, and r are each independently 0 or 1, the case of 0 means that each independently R ¹ is present instead of L ³ or L ⁴ with the proviso that q+r=0;

Y ¹ is B, P, P=O, P=S, Al, Ga, As, Si-R, or Ge-R, wherein R of Si-R and Ge-R is substituted or unsubstituted aryl , substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl;

each Z is, independently, N or CR ¹ , or Z=Z is each independently >O, >NR, >C(-R) ₂ , >Si(-R) ₂ , >S, or >Se , wherein R ¹ of CR ¹ is each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio or substituted silyl, wherein at least one hydrogen is unsubstituted or substituted with aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, The two aryls are not bonded to each other or are bonded through a linking group, and the two heteroaryls of the diheteroarylamino are not bonded to each other or are bonded through a linking group, and the aryl and heteroaryl of the arylheteroarylamino are hetero Aryl is not bonded to each other or is bonded through a linking group, and the two aryls of the diarylboryl are not bonded to each other, or are bonded to each other through a single bond or a linking group;

Two adjacent R ¹ are bonded to each other, do not form or form an aryl ring or a heteroaryl ring, and at least one hydrogen of the formed aryl ring and the formed aryl heteroaryl ring is, respectively, aryl, hetero unsubstituted or substituted with aryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or substituted silyl; At least one hydrogen in is unsubstituted or substituted with aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, and the two aryls of the diarylamino are not bonded to each other, Or they are bonded through a linking group, and the two heteroaryls of the diheteroarylamino are not bonded to each other, or are bonded through a linking group, and the aryl and heteroaryl of the arylheteroarylamino are not bonded to each other, or a linking group are bonded through, and the two aryls of the diarylboryl are not bonded to each other, or are bonded through a single bond or a linking group, and the >NR, the >C(-R) ₂ and the >Si(-R) ) ₂ R is each independently hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, wherein at least one hydrogen is aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl unsubstituted or substituted, and two R of >C(-R) ₂ and >Si(-R) ₂ are not bonded to each other to form a ring;

each R ^d is independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or substituted silyl, wherein at least one hydrogen is unsubstituted or substituted with aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, wherein the two aryls of the diarylamino are not bonded to each other or is bonded through a linking group, the two heteroaryls of the diheteroarylamino are not bonded to each other, or are bonded through a linking group, and the aryl and heteroaryl of the arylheteroarylamino are not bonded to each other, Or they are bonded through a linking group, and the two aryls of the diarylboryl are not bonded to each other, or are bonded through a single bond or a linking group;

The polycyclic aromatic compound having a structure consisting of one or two or more of the structural units represented by formula (1d-1) or formula (1d-2) is not condensed with at least one cycloalkane or is condensed; At least one hydrogen in the cycloalkane is unsubstituted or substituted, and at least one -CH ₂ - in the cycloalkane is unsubstituted or substituted with -O- or -S-, , and;

At least one hydrogen in the structure represented by the formula (1d-1) or (1d-2) is unsubstituted or substituted with cyano, halogen, or deuterium.

<6>

The polycyclic aromatic compound according to <1>, wherein the structural unit is a structural unit represented by Formula (1e-1), Formula (1e-2), Formula (1e-3) or Formula (1e-4).

In formula (1e-1), formula (1e-2), formula (1e-3) and formula (1e-4),

each Z is, independently, N or CR ¹ , or Z=Z is each independently >O, >NR, >C(-R) ₂ , >Si(-R) ₂ , >S, or >Se , wherein R ¹ of CR ¹ is each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio or substituted silyl, wherein at least one hydrogen is unsubstituted or substituted with aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, The two aryls are not bonded to each other or are bonded through a linking group, and the two heteroaryls of the diheteroarylamino are not bonded to each other or are bonded through a linking group, and the aryl and heteroaryl of the arylheteroarylamino are hetero Aryl is not bonded to each other or is bonded through a linking group, and the two aryls of the diarylboryl are not bonded to each other, or are bonded to each other through a single bond or a linking group;

Two adjacent R ¹ are bonded to each other, do not form or form an aryl ring or a heteroaryl ring, and at least one hydrogen of the formed aryl ring and the formed aryl heteroaryl ring is, respectively, aryl, hetero unsubstituted or substituted with aryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or substituted silyl; At least one hydrogen in is unsubstituted or substituted with aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, and the two aryls of the diarylamino are not bonded to each other, Or they are bonded through a linking group, and the two heteroaryls of the diheteroarylamino are not bonded to each other, or are bonded through a linking group, and the aryl and heteroaryl of the arylheteroarylamino are not bonded to each other, or a linking group are bonded through, and the two aryls of the diarylboryl are not bonded to each other, or are bonded through a single bond or a linking group, and the >NR, the >C(-R) ₂ and the >Si(-R) ) ₂ R is each independently hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, wherein at least one hydrogen is aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl unsubstituted or substituted, and two R of >C(-R) ₂ and >Si(-R) ₂ are not bonded to each other to form a ring;

each R ^d is independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or substituted silyl, wherein at least one hydrogen is unsubstituted or substituted with aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, wherein the two aryls of the diarylamino are not bonded to each other or is bonded through a linking group, the two heteroaryls of the diheteroarylamino are not bonded to each other, or are bonded through a linking group, and the aryl and heteroaryl of the arylheteroarylamino are not bonded to each other, Or they are bonded through a linking group, and the two aryls of the diarylboryl are not bonded to each other, or are bonded through a single bond or a linking group;

A polycyclic aromatic compound having a structure comprising one or two or more of the structural units represented by formula (1e-1), formula (1e-2), formula (1e-3) or formula (1e-4) is at least uncondensed or condensed with one cycloalkane, at least one hydrogen in the cycloalkane is unsubstituted or substituted, and at least one -CH ₂ - in the cycloalkane is -O unsubstituted or substituted with - or -S-, and;

At least one hydrogen in the structure represented by formula (1e-1), formula (1e-2), formula (1e-3) or formula (1e-4) is not substituted with cyano, halogen, or deuterium or is substituted.

<7>

The polycyclic aromatic compound according to <1>, wherein the structural unit is a structural unit represented by the formula (1f-1) or (1f-2).

In formulas (1f-1) and (1f-2),

x is an integer from 1 to 3;

Y ¹ is B, P, P=O, P=S, Al, Ga, As, Si-R, or Ge-R, wherein R of Si-R and Ge-R is substituted or unsubstituted aryl , substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl;

L ¹ , L ² , L ³ , and L ⁴ are each independently a single bond, substituted or unsubstituted arylene, substituted or unsubstituted heteroarylene, substituted or unsubstituted alkylene, substituted or unsubstituted cycloalkylene, substituted or unsubstituted alkenylene, >O, >NR, >C(-R)2, >Si(-R)2, >S, or >Se, wherein R of >NR, wherein R of >Si(-R) ₂ and R of >C(-R) ₂ are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, wherein two R of >Si(-R) ₂ and two R of >C(-R) ₂ are not bonded to each other to form a ring, or wherein R of >NR, R of >C(-R) ₂ , and at least one R of >Si(-R) ₂ are each independently at least one of R ^Z in Z that is CR ^Z One and -O-, -S-, -C(-R) ₂ - or not bonded by a single bond, or bonded;

n, m, q, and r are each independently 0 or 1, the case of 0 means that each independently hydrogen or a substituent is present instead of L ¹ , L ² , L ³ or L ⁴ , provided that , n+m=1 and not q+r=0;

A is each independently >(CR)-, wherein R of >(CR)- is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl;

each E is, independently, >O, >NR, >C(-R) ₂ , >Si(-R) ₂ , >S, or >Se, wherein R of >NR, the >Si(-R) R of ₂ and R of >C(-R) ₂ are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, wherein two R of >Si(-R) ₂ and two R of >C(-R) ₂ are not bonded to each other to form a ring;

each Z is, independently, N or CR ¹ , or Z=Z is each independently >O, >NR, >C(-R) ₂ , >Si(-R) ₂ , >S, or >Se , wherein R ¹ of CR ¹ is each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio or substituted silyl, wherein at least one hydrogen is unsubstituted or substituted with aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, The two aryls are not bonded to each other or are bonded through a linking group, and the two heteroaryls of the diheteroarylamino are not bonded to each other or are bonded through a linking group, and the aryl and heteroaryl of the arylheteroarylamino are hetero Aryl is not bonded to each other or is bonded through a linking group, and the two aryls of the diarylboryl are not bonded to each other, or are bonded to each other through a single bond or a linking group;

Two adjacent R ¹ are bonded to each other, do not form or form an aryl ring or a heteroaryl ring, and at least one hydrogen of the formed aryl ring and the formed aryl heteroaryl ring is, respectively, aryl, hetero unsubstituted or substituted with aryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or substituted silyl; At least one hydrogen in is unsubstituted or substituted with aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, and the two aryls of the diarylamino are not bonded to each other, Or they are bonded through a linking group, and the two heteroaryls of the diheteroarylamino are not bonded to each other, or are bonded through a linking group, and the aryl and heteroaryl of the arylheteroarylamino are not bonded to each other, or a linking group are bonded through, and the two aryls of the diarylboryl are not bonded to each other, or are bonded through a single bond or a linking group, and the >NR, the >C(-R) ₂ and the >Si(-R) ) ₂ R is each independently hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, wherein at least one hydrogen is aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl unsubstituted or substituted, and two R of >C(-R) ₂ and >Si(-R) ₂ are not bonded to each other to form a ring;

The polycyclic aromatic compound having a structure consisting of one or two or more of the structural units represented by the formulas (1f-1) and (1f-2) is not condensed with at least one cycloalkane or is condensed; At least one hydrogen in the cycloalkane is unsubstituted or substituted, and at least one -CH ₂ - in the cycloalkane is unsubstituted or substituted with -O- or -S-, , and;

At least one hydrogen in the structures represented by formulas (1f-1) and (1f-2) is unsubstituted or substituted with cyano, halogen, or deuterium.

<8>

The polycyclic aromatic compound according to <1>, wherein the structural unit is a structural unit represented by the following formula (1g-1) or (1g-2), respectively.

In formulas (1g-1) and (1g-2),

x is an integer from 1 to 3;

L ³ , L ⁴ are each independently a single bond, arylene, heteroarylene or alkenylene, and at least one hydrogen of these is not substituted with alkyl, cycloalkyl, diarylamino, or substituted silyl, or is substituted, and the two aryls of the diarylamino are not bonded through a linking group or are bonded;

q, and r are each independently 0 or 1, the case of 0 means that each independently R ¹ is present instead of L ³ or L ⁴ , provided that q+r=0;

Y ¹ is B, P, P=O, P=S, Al, Ga, As, Si-R, or Ge-R, wherein R of Si-R and Ge-R is substituted or unsubstituted aryl , substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl;

A is each independently >(CR)-, wherein R of >(CR)- is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl;

each E is, independently, >O, >NR, >C(-R) ₂ , >Si(-R) ₂ , >S, or >Se, wherein R of >NR, the >Si(-R) R of ₂ and R of >C(-R) ₂ are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, wherein two R of >Si(-R) ₂ and two R of >C(-R) ₂ are not bonded to each other to form a ring;

each Z is, independently, N or CR ¹ , or Z=Z is each independently >O, >NR, >C(-R) ₂ , >Si(-R) ₂ , >S, or >Se , wherein R ¹ of CR ¹ is each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio or substituted silyl, wherein at least one hydrogen is unsubstituted or substituted with aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, The two aryls are not bonded to each other or are bonded through a linking group, and the two heteroaryls of the diheteroarylamino are not bonded to each other or are bonded through a linking group, and the aryl and heteroaryl of the arylheteroarylamino are hetero Aryl is not bonded to each other or is bonded through a linking group, and the two aryls of the diarylboryl are not bonded to each other, or are bonded to each other through a single bond or a linking group;

Two adjacent R ¹ are bonded to each other, do not form or form an aryl ring or a heteroaryl ring, and at least one hydrogen of the formed aryl ring and the formed aryl heteroaryl ring is, respectively, aryl, hetero unsubstituted or substituted with aryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or substituted silyl; At least one hydrogen in is unsubstituted or substituted with aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, and the two aryls of the diarylamino are not bonded to each other, Or they are bonded through a linking group, and the two heteroaryls of the diheteroarylamino are not bonded to each other, or are bonded through a linking group, and the aryl and heteroaryl of the arylheteroarylamino are not bonded to each other, or a linking group are bonded through, and the two aryls of the diarylboryl are not bonded to each other, or are bonded through a single bond or a linking group, and the >NR, the >C(-R) ₂ and the >Si(-R) ) ₂ R is each independently hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, wherein at least one hydrogen is aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl unsubstituted or substituted, and two R of >C(-R) ₂ and >Si(-R) ₂ are not bonded to each other to form a ring;

The polycyclic aromatic compound having a structure consisting of one or two or more of the structural units represented by the formula (1g-1) or (1g-2) is not condensed with at least one cycloalkane or is condensed, At least one hydrogen in the cycloalkane is unsubstituted or substituted, and at least one -CH ₂ - in the cycloalkane is unsubstituted or substituted with -O- or -S-, , and;

At least one hydrogen in the structure represented by the formula (1g-1) or (1g-2) is unsubstituted or substituted with cyano, halogen, or deuterium.

<9>

The polycyclic aromatic compound according to <1>, wherein the structural unit is a structural unit represented by the following formula (1h-1), (1h-2), (1h-3), or (1h-4).

In formula (1h-1), formula (1h-2), formula (1h-3) and formula (1h-4),

x is an integer from 1 to 3;

A is, each independently, >(CR)-, wherein R of >(CR)- is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl;

E is, each independently, >O, >NR, >C(-R) ₂ , >Si(-R) ₂ , >S, or >Se, wherein R of >NR, >Si(-R) R of ₂ and R of >C(-R) ₂ are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, wherein the two Rs of >Si(-R) ₂ and the two Rs of >C(-R) ₂ are not bonded to each other to form a ring;

each Z is, independently, N or CR ¹ , or each Z=Z is independently >O, >NR, >C(-R) ₂ , >Si(-R) ₂ , >S, or >Se , wherein R ¹ of CR ¹ is each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio or substituted silyl, wherein at least one hydrogen is unsubstituted or substituted with aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, The two aryls are not bonded to each other or are bonded through a linking group, and the two heteroaryls of the diheteroarylamino are not bonded to each other or are bonded through a linking group, and the aryl and heteroaryl of the arylheteroarylamino are hetero Aryl is not bonded to each other or is bonded through a linking group, and the two aryls of the diarylboryl are not bonded to each other, or are bonded to each other through a single bond or a linking group;

Two adjacent R ¹ are bonded to each other, do not form or form an aryl ring or a heteroaryl ring, and at least one hydrogen of the formed aryl ring and the formed aryl heteroaryl ring is, respectively, aryl, hetero unsubstituted or substituted with aryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or substituted silyl; At least one hydrogen in is unsubstituted or substituted with aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, and the two aryls of the diarylamino are not bonded to each other, Or they are bonded through a linking group, and the two heteroaryls of the diheteroarylamino are not bonded to each other, or are bonded through a linking group, and the aryl and heteroaryl of the arylheteroarylamino are not bonded to each other, or a linking group are bonded through, and the two aryls of the diarylboryl are not bonded to each other, or are bonded through a single bond or a linking group, and the >NR, the >C(-R) ₂ and the >Si(-R) ) ₂ R is each independently hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, wherein at least one hydrogen is aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl unsubstituted or substituted, and two R of >C(-R) ₂ and >Si(-R) ₂ are not bonded to each other to form a ring;

A polycyclic aromatic compound having a structure comprising one or two or more of the structural units represented by formula (1h-1), formula (1h-2), formula (1h-3), or formula (1h-4) is uncondensed or condensed with at least one cycloalkane, at least one hydrogen in the cycloalkane is unsubstituted or substituted, and at least one -CH ₂ - in the cycloalkane is - unsubstituted or substituted with O- or -S-, and;

At least one hydrogen in the structure represented by formula (1h-1), formula (1h-2), formula (1h-3), or formula (1h-4) is not substituted with cyano, halogen, or deuterium or is substituted.

<10>

The polycyclic aromatic compound according to <1>, wherein the structural unit is a structural unit represented by formula (1i-1) or (1i-2).

In formulas (1i-1) and (1i-2),

x is an integer from 1 to 3;

L ³ , L ⁴ are each independently a single bond, arylene, heteroarylene or alkenylene, and at least one hydrogen of these is not substituted with alkyl, cycloalkyl, diarylamino, or substituted silyl, or is substituted, and the two aryls of the diarylamino are not bonded through a linking group or are bonded;

q, and r are each independently 0 or 1, the case of 0 means that each independently R ¹ is present instead of L ³ or L ⁴ , provided that q+r=0;

Y ¹ is B, P, P=O, P=S, Al, Ga, As, Si-R, or Ge-R, wherein R of Si-R and Ge-R is substituted or unsubstituted aryl , substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl;

A is each independently >(CR)-, wherein R of >(CR)- is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl;

each E is, independently, >O, >NR, >C(-R) ₂ , >Si(-R) ₂ , >S, or >Se, wherein R of >NR, the >Si(-R) R of ₂ and R of >C(-R) ₂ are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, wherein two R of >Si(-R) ₂ and two R of >C(-R) ₂ are not bonded to each other to form a ring;

each Z is, independently, N or CR ¹ , or Z=Z is each independently >O, >NR, >C(-R) ₂ , >Si(-R) ₂ , >S, or > Se , wherein R ¹ of CR ¹ is each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio or substituted silyl, wherein at least one hydrogen is unsubstituted or substituted with aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, The two aryls are not bonded to each other or are bonded through a linking group, and the two heteroaryls of the diheteroarylamino are not bonded to each other or are bonded through a linking group, and the aryl and heteroaryl of the arylheteroarylamino are hetero Aryl is not bonded to each other or is bonded through a linking group, and the two aryls of the diarylboryl are not bonded to each other, or are bonded to each other through a single bond or a linking group;

Adjacent two R ¹ are bonded to each other and do not form or form an aryl ring or a heteroaryl ring, and at least one hydrogen of the formed aryl ring and the formed aryl heteroaryl ring is, respectively, aryl, hetero unsubstituted or substituted with aryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or substituted silyl; At least one hydrogen in is unsubstituted or substituted with aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, and the two aryls of the diarylamino are not bonded to each other, Or it is bonded through a linking group, the two heteroaryls of the diheteroarylamino are not bonded to each other, or are bonded through a linking group, and the aryl and heteroaryl of the arylheteroarylamino are not bonded to each other, or a linking group are bonded through, and the two aryls of the diarylboryl are not bonded to each other, or are bonded through a single bond or a linking group, and the >NR, the >C(-R) ₂ and the >Si(-R) ) ₂ R is each independently hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, wherein at least one hydrogen is aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl unsubstituted or substituted, and two R of >C(-R) ₂ and >Si(-R) ₂ are not bonded to each other to form a ring;

each R ^d is independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or substituted silyl, wherein at least one hydrogen is unsubstituted or substituted with aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, wherein the two aryls of the diarylamino are not bonded to each other or is bonded through a linking group, the two heteroaryls of the diheteroarylamino are not bonded to each other, or are bonded through a linking group, and the aryl and heteroaryl of the arylheteroarylamino are not bonded to each other, or they are bonded through a linking group, and the two aryls of the diarylboryl are not bonded to each other, or are bonded through a single bond or a linking group;

The polycyclic aromatic compound having a structure consisting of one or two or more of the structural units represented by formula (1i-1) or formula (1i-2) is not condensed with at least one cycloalkane or is condensed; At least one hydrogen in the cycloalkane is unsubstituted or substituted, and at least one -CH ₂ - in the cycloalkane is unsubstituted or substituted with -O- or -S-, , and;

At least one hydrogen in the structure represented by the formula (1i-1) or (1i-2) is unsubstituted or substituted with cyano, halogen, or deuterium.

<11>

The polycyclic aromatic compound according to <1>, wherein the structural unit is a structural unit represented by the formula (1k-1), the formula (1k-2), the formula (1k-3), or the formula (1k-4).

In formula (1k-1), formula (1k-2), formula (1k-3), and formula (1k-4),

x is an integer from 1 to 3;

A is, each independently, >(CR)-, wherein R of >(CR)- is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl;

E is, each independently, >O, >NR, >C(-R) ₂ , >Si(-R) ₂ , >S, or >Se, wherein R of >NR, >Si(-R) R of ₂ and R of >C(-R) ₂ are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted and cycloalkyl, wherein two R of >Si(-R) ₂ and two R of >C(-R) ₂ are not bonded to each other to form a ring,

each Z is, independently, N or CR ¹ , or each Z=Z is independently >O, >NR, >C(-R) ₂ , >Si(-R) ₂ , >S, or >Se , wherein R ¹ of CR ¹ is each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio or substituted silyl, wherein at least one hydrogen is unsubstituted or substituted with aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, The two aryls are not bonded to each other or are bonded through a linking group, and the two heteroaryls of the diheteroarylamino are not bonded to each other or are bonded through a linking group, and the aryl and heteroaryl of the arylheteroarylamino are hetero Aryl is not bonded to each other or is bonded through a linking group, and the two aryls of the diarylboryl are not bonded to each other, or are bonded to each other through a single bond or a linking group;

Two adjacent R ¹ are bonded to each other, do not form or form an aryl ring or a heteroaryl ring, and at least one hydrogen of the formed aryl ring and the formed aryl heteroaryl ring is, respectively, aryl, hetero unsubstituted or substituted with aryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or substituted silyl; At least one hydrogen in is unsubstituted or substituted with aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, and the two aryls of the diarylamino are not bonded to each other, Or they are bonded through a linking group, the two heteroaryls of the diheteroarylamino are not bonded to each other, or are bonded through a linking group, and the aryl and heteroaryl of arylheteroarylamino are not bonded to each other, or a linking group and the two aryls of the diarylboryl are not bonded to each other, or are bonded through a single bond or a linking group, and the >NR, the >C(-R) ₂ and the >Si(-R) R of ₂ is each independently hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, wherein at least one hydrogen is substituted with aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl unsubstituted or substituted, and two R of >C(-R) ₂ and >Si(-R) ₂ are not bonded to each other to form a ring;

each R ^d is independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or substituted silyl, wherein at least one hydrogen is unsubstituted or substituted with aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, wherein the two aryls of the diarylamino are not bonded to each other or is bonded through a linking group, the two heteroaryls of the diheteroarylamino are not bonded to each other, or are bonded through a linking group, and the aryl and heteroaryl of the arylheteroarylamino are not bonded to each other, Or they are bonded through a linking group, and the two aryls of the diarylboryl are not bonded to each other, or are bonded through a single bond or a linking group;

A polycyclic aromatic compound having a structure comprising one or two or more of the structural units represented by formula (1k-1), formula (1k-2), formula (1k-3) or formula (1k-4) is at least uncondensed or condensed with one cycloalkane, at least one hydrogen in the cycloalkane is unsubstituted or substituted, and at least one -CH ₂ - in the cycloalkane is -O unsubstituted or substituted with - or -S-, and;

At least one hydrogen in the structure represented by formula (1k-1), formula (1k-2), formula (1k-3) or formula (1k-4) is not substituted with cyano, halogen, or deuterium or is substituted.

<12>

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

In the above formula, tBu is t-butyl.

<13>

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

<14>

A material for an organic device containing the polycyclic aromatic compound according to any one of <1> to <13>.

<15>

An organic electroluminescence comprising a pair of electrodes comprising an anode and a cathode, and a light emitting layer disposed between the pair of electrodes, wherein the light emitting layer contains the polycyclic aromatic compound according to any one of <1> to <13>. device.

<16>

The organic electroluminescent device according to <15>, wherein the light emitting layer includes a host and the polycyclic aromatic compound as a dopant.

<17>

A display device or a lighting device provided with the organic electroluminescent element according to any one of <15> or <16>.

ADVANTAGE OF THE INVENTION According to this invention, the novel polycyclic aromatic compound useful as a material for organic devices, such as an organic electroluminescent element, is provided. The polycyclic aromatic compound of this invention can be used for manufacture of organic devices, such as an organic electroluminescent element.

1 is a schematic cross-sectional view showing an example of an organic electroluminescent device.
2 is an energy level diagram showing the energy relationship between a host, an assisting dopant, and an emitting dopant of a TAF device using a general fluorescent dopant.
3 is an energy level diagram showing an example of an energy relationship between a host, an assisting dopant, and an emitting dopant in an organic electroluminescent device of an embodiment of the present invention.

Hereinafter, the present invention will be described in detail. Although description of the structural requirements described below may be made based on typical embodiment and specific example, this invention is not limited to such embodiment. In addition, the numerical range shown using "-" in this specification means the range which includes the numerical value described before and after "-" as a lower limit and an upper limit. In addition, in this specification, "hydrogen" in description of a structural formula means a "hydrogen atom (H)."

In this specification, an organic electroluminescent element may be called organic electroluminescent element.

In this specification, a chemical structure or a substituent is sometimes expressed by the number of carbon atoms, and the number of carbon atoms in the case where a substituent is substituted in the chemical structure or when a substituent is further substituted in the chemical structure means the number of carbon atoms in each of the chemical structure and the substituent, It does not mean the total carbon number of a structure and a substituent, or the total carbon number of a substituent and a substituent. For example, "substituent B of carbon number Y substituted by substituent A of carbon number X" means that "substituent B of carbon number Y" is substituted with "substituent A of carbon number X", and carbon number Y is substituent A and substituent It is not the number of carbons in the sum of B. Also, for example, "substituent B of carbon number Y substituted with substituent A" means that "substituent A (with no limitation on number of carbon atoms)" is substituted for "substituent B of carbon number Y", and carbon number Y is substituent A and It is not the number of carbon atoms in the total of the substituents B.

Since the chemical structural formulas described in this specification (including the general formulas drawn by Markush structural formulas) are planar structural formulas, in reality, various isomeric structures such as enantiomers, diastereoisomers, and rotational isomers may exist. . In the present specification, unless specifically limited, the compound described may have any isomeric structure conceivable from its planar structural formula, or may be a mixture in any ratio constituted from possible isomers.

In the present specification, a number of structural formulas of aromatic compounds are described. Although aromatic compounds are described by combining a double bond and a single bond, in reality, π electrons resonate, so even for a single substance, there are a plurality of equivalent resonance structures, such as alternating double bonds and single bonds. . In the present specification, only one resonance structural formula is described for one substance, but unless otherwise limited, other resonance structural formulas that are organically and chemically equivalent are also included. This is referred to in the description of "Z=Z" etc. which will be mentioned later. That is, for example, when an example is shown about "Z=Z" in Formula (1a-1) mentioned later, it is as follows. However, the present invention is not limited thereto, and it is naturally applied not only to the one described resonance structural formula, but also to other equivalent resonance structural formulas that can be considered.

In addition, in this specification, although the expression "it may be" and the expression "it is not - or it is -" are used, both of these expressions have the same meaning.

<Polycyclic aromatic compound>

The polycyclic aromatic compound of the present invention is a polycyclic aromatic compound having a structure composed of one or two or more structural units represented by formula (1A-1). The polycyclic aromatic compound of the present invention has a high emission quantum yield (PLQY), a narrow emission half maximum width, and excellent color purity.

In formula (1A-1), A2 ring, A3 ring, and A4 ring are each independently a substituted or unsubstituted aryl ring, or a substituted or unsubstituted heteroaryl ring, A1 ring and A5 ring are each independently, a substituted or unsubstituted aryl ring, a substituted or unsubstituted heteroaryl ring, a substituted or unsubstituted cycloalkyl ring, or a cycloheteroalkyl ring.

In the formula (1A-1), examples of the "aryl ring" in the A1 ring, the A2 ring, the A3 ring, the A4 ring, and the A5 ring include, for example, an aryl ring having 6 to 30 carbon atoms, and an aryl ring having 6 to 6 carbon atoms. A 16 aryl ring is preferable, a C6-C12 aryl ring is more preferable, and a C6-C10 aryl ring is especially preferable.

Specific examples of the “aryl ring” include a monocyclic benzene ring, a bicyclic biphenyl ring, a condensed bicyclic naphthalene ring, an indene ring, and a tricyclic terphenyl ring (m-terphenyl, o-terphenyl, p-terphenyl). ), a condensed tricyclic ring, an acenaphthylene ring, a fluorene ring, a phenalene ring, a phenanthrene ring, an anthracene ring, a condensed tetracyclic triphenylene ring, a pyrene ring, a naphthacene ring, a chrysene ring, a condensed pentacyclic perylene ring, A pentacene ring etc. are mentioned. The fluorene ring, the benzofluorene ring and the indene ring also include structures in which a fluorene ring, a benzofluorene ring, a cyclopentane ring and the like are spiro bonded. In the fluorene ring, the benzofluorene ring and the indene ring, two of the two hydrogens of methylene are substituted with alkyl such as methyl as a first substituent described later, respectively, and are dimethylfluorene ring, dimethylbenzofluorene ring and dimethyl Also included are those made of den ring or the like.

In the formula (1A-1), examples of the "heteroaryl ring" in the A1 ring, the A2 ring, the A3 ring, the A4 ring and the A5 ring include, for example, a C2-C30 heteroaryl ring, A 2-25 heteroaryl ring is preferable, a C2-C20 heteroaryl ring is more preferable, a C2-C15 heteroaryl ring is still more preferable, A C2-C10 heteroaryl ring is especially preferable. Examples of the "heteroaryl ring" include a heterocyclic ring containing 1 to 5 heteroatoms selected from oxygen, sulfur and nitrogen in addition to carbon as ring-constituting atoms.

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, Pyridine ring, pyrimidine ring, pyridazine ring, pyrazine ring, triazine ring, indole ring, isoindole ring, 1H-indazole ring, benzoimidazole ring, benzoxazole ring, benzothiazole ring, 1H-benzotriazole ring, quinoline ring , isoquinoline ring, cinnoline ring, quinazoline ring, quinoxaline ring, phthalazine ring, naphthridine ring, purine ring, pteridine ring, carbazole ring, carboline ring, acridine ring, phenoxatiin ring, phenoxatiin ring Noxazine ring, phenothiazine ring, phenazine ring, phenazacillin ring, indolizine ring, furan ring, benzofuran ring, isobenzofuran ring, dibenzofuran ring, thiophene ring, benzothiophene ring, dibenzothiophene ring , furazan ring, thiantrene ring, indolocarbazole ring, benzoindolocarbazole ring, dibenzoindolocarbazole ring, naphthobenzofuran ring, dioxin ring, dihydroacridine ring, xanthene ring, thioxanthene ring , a dibenzodioxin ring, etc. are mentioned. Further, two of the two hydrogens of the dihydroacridine ring, the xanthene ring, the thioxanthene ring, silver and methylene are substituted with alkyl such as methyl as a first substituent described later, respectively, and the dimethyldihydroacridine ring, the dimethylxanthene ring, and the dimethyl It is also preferable to have a thioxanthene ring or the like. Moreover, a bipyridine ring, a phenylpyridine ring, a pyridylphenyl ring, a tricyclic system terpyridine ring, a bispyridylphenyl ring, and a pyridyl biphenyl ring are mentioned as a "heteroaryl ring". In addition, the "heteroaryl ring" shall also include a pyran ring.

In addition, the following formula (BO) is also included in the heteroaryl ring.

In the formula (1A-1), examples of the "cycloalkyl ring" in the A1 ring and the A5 ring include a cycloalkyl ring having 6 to 30 carbon atoms, and a cycloalkyl ring having 6 to 16 carbon atoms is preferable. , a C6-C12 cycloalkyl ring is more preferable, and a C6-C10 cycloalkyl ring is especially preferable.

Specific examples of the cycloalkyl ring include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclononane, cyclodecane, norborneine, 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, decahydroazulene, and alkyl (especially methyl) substituents having 1 to 4 carbon atoms.

In the formula (1A-1), examples of the "cycloheteroalkyl ring" in the A1 ring and the A5 ring include a C4-C30 cycloheteroalkyl ring, and a C4-C16 cycloheteroalkyl ring. A ring is preferable, a C4-C12 cycloheteroalkyl ring is more preferable, A C4-C10 cycloheteroalkyl ring is especially preferable.

The cycloheteroalkyl ring means that at least one carbon atom of the cycloalkyl ring is substituted with a hetero atom (oxygen, nitrogen, sulfur, etc.). Specific examples of the cycloheteroalkyl ring include a tetrahydropyrrole ring, a tetrahydrofuran ring, a tetrahydrothiophene ring, a piperidine ring, a pyrrolizine ring, a tetrahydropyran ring, a tetrahydrothiopyran ring, a dioxane ring, an oxathian ring, A dithiane ring, a morpholine ring, a piperazine ring, etc. are mentioned.

At least one hydrogen in the "aryl ring", "heteroaryl ring", "cycloalkyl ring" or "cycloheteroalkyl ring" is a first substituent, substituted or unsubstituted "aryl", substituted or unsubstituted Substituted "heteroaryl", substituted or unsubstituted "diarylamino", substituted or unsubstituted "diheteroarylamino", substituted or unsubstituted "arylheteroarylamino", substituted or unsubstituted "diaryl" Boryl", substituted or unsubstituted "alkyl", substituted or unsubstituted "cycloalkyl", substituted or unsubstituted "alkenyl", substituted or unsubstituted "alkoxy", substituted or unsubstituted "aryloxy" , a substituted or unsubstituted "arylthio", or a substituted "silyl" may be substituted. In addition, the two aryls of “diarylamino” are not bonded to each other or are bonded through a linking group, and the two heteroaryls of “diheteroarylamino” are not bonded to each other or are bonded through a linking group, and the aryl and heteroaryl of "arylheteroarylamino" are not bonded to each other or are bonded through a linking group, and the two aryls of "diarylboryl" are not bonded to each other, or a single bond or It is connected through a connector. Regarding these terms and their preferred ranges, the description in the specification can be referred to unless otherwise specified.

Specific examples of "aryl" include aryl having 6 to 30 carbon atoms, preferably aryl having 6 to 24 carbon atoms, more preferably aryl having 6 to 20 carbon atoms, and aryl having 6 to 16 carbon atoms. Even more preferred, aryl having 6 to 12 carbon atoms is particularly preferred, and aryl having 6 to 10 carbon atoms is most preferred.

Specific examples of aryl include phenyl which is monocyclic aryl, (2-,3-,4-)biphenylyl which is bicyclic aryl, (1-,2-)naphthyl which is condensed bicyclic aryl, and (2- ,3-,4-,5-,6-,7-) indenyl, tricyclic aryl terphenylyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-ter Phenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl -3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), condensed tricyclic aryl, acenaphthylene-(1-,3-,4-,5-)yl, fluorene-(1- ,2-,3-,4-,9-)yl, phenalen-(1-,2-)yl, (1-,2-,3-,4-,9-)phenanthryl, tetracyclic aryl Quarterphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenyl aryl), condensed tetracyclic aryl triphenylene-(1-,2-)yl, pyren-(1-,2-,4-)yl, naphthacen-(1-,2-,5-)yl, and perylene-(1-,2-,3-)yl and pentacene-(1-,2-,5-,6-)yl which are condensed pentacyclic aryl.

Moreover, as "heteroaryl", for example, heteroaryl having 2 to 30 carbon atoms is mentioned, heteroaryl having 2 to 25 carbon atoms is preferable, heteroaryl having 2 to 20 carbon atoms is more preferable, and heteroaryl having 2 to 20 carbon atoms is more preferable. Heteroaryl of 15 is more preferable, and heteroaryl of 2-10 carbon atoms is especially preferable. Examples of the heteroaryl include a heterocyclic ring containing 1 to 5 heteroatoms selected from oxygen, sulfur and nitrogen in addition to carbon as ring-constituting atoms.

Specific examples of heteroaryl include furyl, thienyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, furazanyl, thiadiazolyl, tria Zolyl, tetrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, benzo[b]thienyl, dibenzothienyl, indolyl , isoindolyl, 1H-indazolyl, benzoimidazolyl, benzooxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, cinnolyl, quinazolyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, carboryl, acridinyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenoxathinyl, thiantrenyl, indolizinyl, etc. are mentioned. .

Moreover, as "alkyl" as a 1st substituent, either a linear or branched chain may be sufficient, For example, C1-C24 linear alkyl or C3-C24 branched alkyl is mentioned. alkyl having 1 to 18 carbon atoms (branched chain alkyl having 3 to 18 carbon atoms) is preferable, alkyl having 1 to 12 carbon atoms (branched chain alkyl having 3 to 12 carbon atoms) is more preferable, and alkyl having 1 to 8 carbon atoms (branched chain alkyl having 3 carbon atoms) is more preferable. ∼8 branched chain alkyl) is more preferred, alkyl having 1 to 6 carbon atoms (branched chain alkyl having 3 to 6 carbon atoms) is particularly preferred, and alkyl having 1 to 5 carbon atoms (branched chain alkyl having 3 to 5 carbon atoms) is particularly preferred. This is most preferable.

Specific examples of alkyl include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl (t-amyl), n -Hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 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-hepta and decyl, n-octadecyl, and n-eicosyl. Also, for example, 1-ethyl-1-methylpropyl, 1,1-diethylpropyl, 1,1-dimethylbutyl, 1-ethyl-1-methylbutyl, 1,1,4-trimethylpentyl, 1, 1,2-Trimethylpropyl, 1,1-dimethyloctyl, 1,1-dimethylpentyl, 1,1-dimethylheptyl, 1,1,5-trimethylhexyl, 1-ethyl-1-methylhexyl, 1-ethyl- 1,3-dimethylbutyl, 1,1,2,2-tetramethylpropyl, 1-butyl-1-methylpentyl, 1,1-diethylbutyl, 1-ethyl-1-methylpentyl, 1,1,3 -Trimethylbutyl, 1-propyl-1-methylpentyl, 1,1,2-trimethylpropyl, 1-ethyl-1,2,2-trimethylpropyl, 1-propyl-1-methylbutyl, 1,1-dimethylhexyl and the like.

As a substituent containing the above "alkyl", tertiaryalkyl represented by the following formula (tR) is a substituent to the aryl ring or heteroaryl ring in the A ring, the B ring and the C ring, among those particularly preferred. one This is because the luminescence quantum yield (PLQY) is improved because the intermolecular distance is increased by such bulky substituents. Moreover, the substituent in which the tertiary alkyl represented by Formula (tR) is substituted by the other substituent as a 2nd substituent is also preferable. Specifically, diarylamino substituted with tertiaryalkyl represented by (tR), carbazolyl substituted with tertiaryalkyl represented by (tR) (preferably N-carbazolyl) or (tR) and benzocarbazolyl (preferably N-benzocarbazolyl) substituted with tertiaryalkyl represented by . In addition, the two aryls of the diarylamino are not bonded to each other or are bonded through a linking group. The group described as the following "first substituent" is mentioned about "diarylamino". Examples of the substitution form of the group of the formula (tR) for diarylamino, carbazolyl and benzocarbazolyl include examples in which some or all of the hydrogens of the aryl ring or benzene ring in these groups are substituted with the group of the formula (tR) can

In formula (tR), R ^a , R ^b , and R ^c are each independently an alkyl having 1 to 24 carbon atoms, and any -CH ₂ - in the alkyl is unsubstituted or substituted with -O- and the group represented by the formula (tR) is substituted with at least one hydrogen in the structure including the structural unit represented by the formula (1) in *.

The "C1-C24 alkyl" of R ^a , R ^b and R ^c 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; 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 4 carbon atoms (branched chain alkyl having 3 to 4 carbon atoms).

C3-C20 is preferable and, as for the sum total of carbon number of R ^<a> , Rb, and R< ^c > in Formula (tR) of Formula (1 ⁾ , C3-C10 is especially preferable.

Specific examples of alkyl for R ^a , R ^b , and R ^c include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n -Undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n -Eicosil, etc. are mentioned.

Examples of the group represented by the formula (tR) include t-butyl, t-amyl, 1-ethyl-1-methylpropyl, 1,1-diethylpropyl, 1,1-dimethylbutyl, 1-ethyl-1 -Methylbutyl, 1,1,3,3-tetramethylbutyl, 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, 1,1-dimethylhexyl, etc. are mentioned. Of these, t-butyl and t-amyl are preferred.

Further, as "cycloalkyl" as the first substituent, 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, cycloalkyl having 5 carbon atoms, and the like. Cyclohexyl in the present specification includes polycyclic ones such as adamantyl in addition to monocyclic cyclohexyl and the like, as listed below.

Specific examples of cycloalkyl include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, 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, and decahydronaphthalenyl, decahydroazulenyl, and alkyl (especially methyl) substituents having 1 to 5 carbon atoms.

Moreover, as "alkoxy" as a 1st substituent, C1-C24 linear or C3-C24 branched chain alkoxy is mentioned, for example. Alkoxy having 1 to 18 carbon atoms (branched alkoxy having 3 to 18 carbon atoms) is preferable, alkoxy having 1 to 12 carbon atoms (branched alkoxy having 3 to 12 carbon atoms) is more preferable, and alkoxy having 1 to 6 carbon atoms (branched alkoxy having 3 to 12 carbon atoms) is more preferable. -6 branched-chain alkoxy) is more preferable, and C1-C5 alkoxy (C3-C5 branched-chain alkoxy) is especially preferable.

Specific examples of alkoxy include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, s-butoxy, t-butoxy, t-amyloxy, pentyloxy, hexyloxy, heptyloxy, octyloxy and the like.

Further, examples of the “substituted silyl” as the first substituent include silyl substituted with three substituents selected from the group consisting of alkyl, cycloalkyl, and aryl. Examples include trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, triarylsilyl, dialkylarylsilyl, and alkyldiarylsilyl.

As "trialkylsilyl", a group in which three hydrogens in silyl are each independently substituted with alkyl can be exemplified. Preferred alkyl for substitution is alkyl having 1 to 5 carbon atoms, and specific examples thereof include methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, t-butyl and t-amyl.

Specific examples of trialkylsilyl include trimethylsilyl, triethylsilyl, tripropylsilyl, triisopropylsilyl, tributylsilyl, trisec-butylsilyl, trit-butylsilyl, trit-amylsilyl, ethyldimethylsilyl, and propyldimethyl Silyl, isopropyldimethylsilyl, butyldimethylsilyl, sec-butyldimethylsilyl, t-butyldimethylsilyl, t-amyldimethylsilyl, methyldiethylsilyl, propyldiethylsilyl, isopropyldiethylsilyl, butyldiethylsilyl, sec-butyldiethylsilyl, t-butyldiethylsilyl, t-amyldiethylsilyl, methyldipropylsilyl, ethyldipropylsilyl, butyldipropylsilyl, sec-butyldipropylsilyl, t-butyldipropylsilyl, t-amyldipropylsilyl, methylisopropylsilyl, ethyldiisopropylsilyl, butyldiisopropylsilyl, sec-butyldiisopropylsilyl, t-butyldiisopropylsilyl, t-amyldiisopropylsilyl, etc. can

Examples of "tricycloalkylsilyl" include a group in which three hydrogens in the silyl group are each independently substituted with cycloalkyl. can Cycloalkyl preferred for substitution is cycloalkyl having 5 to 10 carbon atoms, and specifically, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, bicyclo[1.1.1]pentyl, and 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, decahydronaphtharenyl, Decahydroazulenyl, etc. are mentioned.

Specific examples of tricycloalkylsilyl include tricyclopentylsilyl and tricyclohexylsilyl.

As specific examples of dialkylcycloalkylsilyl in which two alkyls and one cycloalkyl are substituted and alkyldicycloalkylsilyl in which one alkyl and two cycloalkyls are substituted, a group selected from the above specific alkyl and cycloalkyl is substituted and silyl.

Specific examples of dialkylarylsilyl in which two alkyls and one aryl are substituted, alkyldiarylsilyl in which one alkyl and two aryls are substituted, and triarylsilyl in which three aryls are substituted include the specific alkyl and aryl and silyl substituted with a group selected from . Specific examples of triarylsilyl include triphenylsilyl.

The "aryloxy" as the first substituent is a group in which the hydrogen of the -OH group is substituted with aryl, and the aryl described above as "aryl" can be cited.

The "arylthio" as the first substituent is a group in which the hydrogen of the -SH group is substituted with aryl, and the aryl described above can be cited.

Examples of the "alkenyl" as the first substituent include 2-24 straight-chain alkenyl or C4-C24 branched-chain alkenyl. C2-C18 alkenyl is preferable, C2-C12 alkenyl is more preferable, C2-C6 alkenyl is still more preferable, C2-C4 alkenyl is especially preferable.

Specific examples of "alkenyl" include vinyl, allyl, butadienyl.

In addition, as "aryl" in "diarylboryl" of the first substituent, the description of aryl described above can be cited. In addition, these two aryls may be couple|bonded via a single bond or a coupling group (for example, >C(-R) ₂ , >O, >S, or >NR). wherein R of >C(-R) ₂ and >NR is aryl, heteroaryl, alkyl, cycloalkyl, alkoxy or aryloxy (or more, the first substituent), and at least one hydrogen of the first substituent is aryl , heteroaryl, alkyl or cycloalkyl (above, the second substituent) is further unsubstituted or substituted, as specific examples of these groups, the description of the above-described first substituent can be cited. In addition, the two aryls of the diarylboryl are not bonded to each other, or are bonded through a single bond or a linking group.

As the aryl and heteroaryl in each of "diarylamino which may be substituted", "diheteroarylamino which may be substituted", and "arylheteroarylamino which may be substituted" as the first substituent, the above-mentioned "aryl" However, what has been described as "heteroaryl" can be cited. In addition, although at least one hydrogen of aryl and heteroaryl is unsubstituted or substituted, as a substituent, the description regarding "substituted or unsubstituted" mentioned later can be referred to, and the tertiaryalkyl mentioned later is preferable. In addition, the two aryls of the diarylamino are not bonded to each other or are bonded through a linking group, and the two heteroaryls of the diheteroarylamino are not bonded to each other or are bonded through a linking group, and the aryl The aryl and heteroaryl of heteroarylamino are not bonded to each other or are bonded through a linking group.

Diarylamino, diheteroarylamino, and arylheteroarylamino as the first substituent are "two aryls are bonded through a linking group or not", "two heteroaryls are bonded through a linking group, or or not bonded" or "heteroaryl is bonded or not bonded through a linking group", this description, as shown below, for example, two phenyl groups indicates that a bond is formed. This description also applies to diheteroarylamino and arylheteroarylamino formed from aryl or heteroaryl.

Specifically as a linking group, >O, >NR ^X , >C(-R ^X ) ₂ , >Si(-R ^X ) ₂ , >S, >CO, >CS, >SO, >SO ₂ , and >Se and R ^X are each independently alkyl, cycloalkyl, aryl or heteroaryl, which are unsubstituted or substituted with alkyl, cycloalkyl, aryl or heteroaryl, and also >C(-R ^X ) R ^X in ₂ , >Si(-R ^X ) ₂ , may be bonded to each other via a single bond or a linking group ^XY to form a ring. X ^Y includes >O, >N-RY, >C(-R ^Y ) ₂ , >Si(-R ^Y ) ₂ , >S, >CO, >CS, >SO, >SO ₂ , and >Se and R ^Y is each independently alkyl, cycloalkyl, aryl or heteroaryl, which may be substituted with alkyl, cycloalkyl, aryl or heteroaryl. with the proviso that when X ^Y is >C(-R ^Y ) ₂ and >Si(-R ^Y ) ₂ , two R ^Y are joined to form no further ring. Furthermore, alkenylene is also mentioned as a coupling group. Any at least one hydrogen of alkenylene is each independently unsubstituted or substituted with R ^X , each R ^X is independently alkyl, cycloalkyl, substituted silyl, aryl, and heteroaryl, at least one of which Hydrogen is unsubstituted or substituted with alkyl (especially tertiaryalkyl described later), cycloalkyl, substituted silyl, or aryl.

In addition, when it is simply described as "diarylamino", "diheteroarylamino" or "arylheteroarylamino" in this specification, unless otherwise specifically limited, each "two aryls are bonded through a linking group, or , or not bonded”, “two heteroaryls are bonded through a linking group or are not bonded” and “aryl and heteroaryl are bonded through a linking group or are not bonded” It is said that this has been added.

The first substituent, substituted or unsubstituted "aryl", substituted or unsubstituted "heteroaryl", substituted or unsubstituted "diarylamino", substituted or unsubstituted "diheteroarylamino", substituted or unsubstituted Substituted “arylheteroarylamino”, substituted or unsubstituted “diarylboryl”, substituted or unsubstituted “alkyl”, substituted or unsubstituted “alkenyl”, substituted or unsubstituted “cycloalkyl”, substituted or unsubstituted "alkoxy", substituted or unsubstituted "aryloxy", substituted or unsubstituted "arylthio", or "substituted silyl" as described as substituted or unsubstituted, At least one hydrogen may be substituted with a second substituent. As this 2nd substituent, Preferably, aryl, heteroaryl, alkyl, cycloalkyl, or substituted silyl is mentioned, For those specific examples, the description in this specification can be referred. Unless otherwise limited, this description can also be referred to in other phrases of "substituted or unsubstituted" in this specification. In addition, in aryl or heteroaryl as the second substituent, at least one hydrogen in them is aryl such as phenyl (specific examples are the groups described above), and alkyl such as methyl and t-butyl (specific examples are the groups described above) ) or a structure substituted with cycloalkyl such as cyclohexyl (specific examples are the groups described above) is also included in aryl and heteroaryl as the second substituent. As an example, when the second substituent is carbazolyl, carbazolyl in which at least one hydrogen in position 9 is substituted with aryl such as phenyl, alkyl such as methyl, or cycloalkyl such as cyclohexyl is also a second substituent included in heteroaryl as In addition, the two aryls of “diarylamino” are not bonded to each other or are bonded through a linking group, and the two heteroaryls of “diheteroarylamino” are not bonded to each other or are bonded through a linking group, and the aryl and heteroaryl of "arylheteroarylamino" are not bonded to each other or are bonded through a linking group, and the two aryls of the "diarylboryl" are not bonded to each other or are bonded through a linking group, have.

The emission wavelength can be adjusted by the structural steric hindrance property, electron donating property, and electron withdrawing property of the first substituent. Preferably, it is a group represented by the following structural formula, More preferably, 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, carbazolyl, 3,6-dimethylcarbazolyl, 3,6-di-t-butylcarbazolyl and phenoxy, even more preferably 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 easiness of synthesis, the one with larger steric hindrance is preferable 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 formula, "Me" represents methyl, "tBu" represents t-butyl, "tAm" represents t-amyl, "tOct" represents t-octyl, and * represents a bonding position.

The polycyclic aromatic compound having a structure comprising one or two or more of the structural units represented by the formula (1A-1) is a tertiaryalkyl (such as t-butyl or t-amyl) represented by the aforementioned formula (tR). , neopentyl or adamantyl is preferable, and it is more preferable to include a tertiary alkyl (such as t-butyl or t-amyl) represented by the formula (tR). This is because the luminescence quantum yield (PLQY) is improved because the intermolecular distance is increased by such bulky substituents. Moreover, as a substituent, diarylamino is more preferable. Further, diarylamino substituted with a group of formula (tR), carbazolyl (preferably N-carbazolyl) substituted with a group of formula (tR) or benzocarbazolyl substituted with a group of formula (tR) ( Preferably, N-benzocarbazolyl) is also preferred. Examples of the substitution form of the group of the formula (tR) for diarylamino, carbazolyl and benzocarbazolyl include examples in which some or all of the hydrogens of the aryl ring or benzene ring in these groups are substituted with the group of the formula (tR) can In addition, the two aryls of the diarylamino are not bonded to each other or are bonded through a linking group.

Y ¹ is B, P, P=O, P=S, Al, Ga, As, Si-R, or Ge-R, wherein R of Si-R and Ge-R is substituted or unsubstituted aryl , substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl. As Y< ¹ >, B, P, P=O, and P=S are preferable, B and P=O are more preferable, and B is the most preferable.

n, m, q, and r are each independently 0 or 1, and in the case of 0, the carbon atom bonded to L ¹ , L ² , L ³ or L ⁴ in parentheses is hydrogen or a substituent (or R to be described later) Although it is substituted with ¹ ), it is preferable that all are substituted with hydrogen. And in the case of ¹ , it means that L1, L2, ^L3 , and ^L4 are ^couple |bonding as it is. Specifically, a case where n, q, and r are 1 and m is 0 will be described by taking Formula (1A-1) as an example. This description also applies to the preferable form of Formula (1A-1) unless it specifically limits. And, although n+m=1 and q+r=0 is not, it is preferable that q+r=1.

L ¹ , L ² , L ³ , and L ⁴ are each independently a single bond, substituted or unsubstituted arylene, substituted or unsubstituted heteroarylene, substituted or unsubstituted alkylene, substituted or unsubstituted cycloalkylene, substituted or unsubstituted alkenylene, >O, >NR, >C(-R) ₂ , >Si(-R) ₂ , >S, or >Se, wherein R of >NR, said R of >Si(-R) ₂ and R of >C(-R) ₂ are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, wherein >Si(-R) ₂ , and two R of >C(-R) ₂ are not bonded to each other to form a ring, and the >NR At least one R of R, >C(-R) ₂ R, and >Si(-R) ₂ At least one R is each independently from at least one of ring A1 to ring A5 through a single bond or a linking group bound or unbound. "Arylene", "heteroarylene", "alkylene", "cycloalkylene" and "alkenylene" are respectively "aryl", "heteroaryl", "alkyl", "cycloalkyl" and "alkenyl" Rather, it is a divalent group excluding one hydrogen, and the preferable range can be referred to in accordance with them.

L ¹ and L ² are preferably substituted or unsubstituted arylene, substituted or unsubstituted heteroarylene, or substituted or unsubstituted alkenylene, substituted or unsubstituted arylene, or substituted or unsubstituted of alkenylene is more preferable. As arylene, phenylene or naphthylene is preferable, and as hetero arylene, benzothiophenylene, benzofuranylene, indolylene, dibenzothiophenylene, dibenzofuranylene, or carbazolylene is preferable. As a substituent, the description of "substituted or unsubstituted" in this specification can be referred to, but arylene and heteroarylene are unsubstituted, or at least one hydrogen is alkyl (especially t-butyl or t-amyl and tertiaryalkyl), cycloalkyl, diarylamino, or substituted silyl, preferably unsubstituted, or at least one hydrogen is alkyl (especially tertiaryalkyl such as t-butyl or t-amyl); It is preferably substituted with cycloalkyl or diarylamino. Also, alkenylene is preferably unsubstituted or in a form in which at least one hydrogen is substituted with alkyl or aryl. In addition, although the two aryls of the said diarylamino are couple|bonded through a coupling group, or it is not couple|bonded, at least one hydrogen of two aryl may be substituted with tertiaryalkyl.

A single bond is more preferable as L ³ and L ⁴ .

The polycyclic aromatic compound of the present invention is a polycyclic aromatic compound having a structure composed of one or two or more structural units represented by formula (1A-1). As the polycyclic aromatic compound having a structure consisting of one of the structural units, a polycyclic aromatic compound represented by the formula described above as the structural unit represented by the formula (1A-1) can be given. As the polycyclic aromatic compound having a structure comprising two or more of the structural units represented by the formula (1A-1), a multimer of the polycyclic aromatic compound represented by the formula described above as the structural unit represented by the formula (1A-1) compounds corresponding to As for a multimer, a 2-hexamer is preferable, A 2-3-mer is more preferable, A dimer is especially preferable. The multimer may be a form having a plurality of the above-mentioned unit structures in one compound, and any ring contained in the above-mentioned structural unit (when described with the formula (1A-1), A1 ring, A2 ring, A3 ring, A4 ring, and A5 ring) may be combined so as to be shared by a plurality of unit structures, and when any ring (formula (1A-1)) included in the unit structure is described, A1 ring, A2 ring, A3 ring, A4 The ring and the A5 ring) may be in a form in which they are combined so as to be condensed. Moreover, the form in which the said unit structure couple|bonded with linking groups, such as a single bond, C1-C3 alkylene, phenylene, and naphthylene, may be sufficient. Among these, the form combined so as to share a ring is more preferable. This description is also applicable to a preferred embodiment of a polycyclic aromatic compound having a structure consisting of one or two or more structural units represented by formula (1A-1) described later.

In a polycyclic aromatic compound having a structure consisting of one or two or more of the structural units represented by the formula (1A-1), and in its preferred embodiment described later, it may be condensed with at least one cycloalkane.

The cycloalkane may be a cycloalkane having 3 to 24 carbon atoms. At this time, at least one hydrogen in the cycloalkane is unsubstituted or substituted with aryl having 6 to 30 carbon atoms, heteroaryl having 2 to 30 carbon atoms, alkyl having 1 to 24 carbon atoms or cycloalkyl having 3 to 24 carbon atoms. and at least one -CH ₂ - in the cycloalkane may be substituted with -O- or -S-.

When at least one selected from the group consisting of an aryl ring and a heteroaryl ring in a structure consisting of one or two or more of the structural units represented by formula (1A-1) is condensed with at least one cycloalkane, At least one cycloalkane is a cycloalkane having 3 to 20 carbon atoms, and at least one hydrogen in the cycloalkane is aryl having 6 to 16 carbon atoms, heteroaryl having 2 to 22 carbon atoms, alkyl having 1 to 12 carbon atoms, or It is preferable that it is a cycloalkane which may be substituted with C3-C16 cycloalkyl.

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

Specific examples of the cycloalkane include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclononane, cyclodecane, 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, and decahydronaphthalene and decahydroazulene, and alkyl (especially methyl) substituents having 1 to 5 carbon atoms, halogen (especially fluorine) substituents and deuterium substituents.

Among these, for example, at least one at the α-position carbon of the cycloalkane (the carbon in the position adjacent to the carbon of the condensation site in the cycloalkyl condensed to an aryl ring or a heteroaryl ring) as shown in the following structural formula A structure in which hydrogen is substituted is preferable, a structure in which two hydrogens at the carbons at the α-position are substituted is more preferable, and a structure in which a total of four hydrogens at the carbons at the two α-positions is substituted is even more preferable. do. As this substituent, a C1-C5 alkyl (especially methyl) substituent, a halogen (especially fluorine) substituent, a deuterium substituent, etc. are mentioned. In particular, it is preferable to have a structure in which a partial structure represented by the following formula (Z) is bonded to an adjacent carbon atom in an aryl ring or a heteroaryl ring.

In formula (Z), Me represents methyl, and * represents a bonding position.

1-3 pieces are preferable, as for the number of the cycloalkanes condensed to one aryl ring or heteroaryl ring, 1 piece or 2 pieces are more preferable, and 1 piece is still more preferable. For example, the example in which one or several cycloalkanes condensed to one benzene ring (phenyl) is shown below. * indicates a bonding position, and the position may be any of carbon constituting the benzene ring and not constituting the cycloalkane. Cycloalkanes condensed as shown in formulas (Cy-1-4) and (Cy-2-4) may be condensed. The same applies even if the condensed ring (group) is an aryl ring or heteroaryl ring other than the benzene ring (phenyl), or the cycloalkane to be condensed is a cycloalkane other than cyclopentane or cyclohexane.

At least one -CH ₂ - in the cycloalkane may be substituted with -O- or -S-. For example, an example in which one or more -CH ₂ - in a cycloalkane condensed on one benzene ring (phenyl) is substituted with -O- is shown below. The same applies when the ring (group) to be condensed is an aromatic ring or a heteroaromatic ring other than the benzene ring (phenyl), or when the cycloalkane to be condensed is a cycloalkane other than cyclopentane or cyclohexane.

At least one hydrogen in the cycloalkane is unsubstituted or substituted, and examples of the substituent include aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, alkenyl, cycloalkyl, alkoxy, aryloxy, arylthio, substituted silyl, deuterium, cyano or halogen, details of which may be cited in the description of the first substituent described above. In addition, the two aryls of the diarylamino are not bonded to each other or are bonded through a linking group, and the two heteroaryls of the diheteroarylamino are not bonded to each other or are bonded through a linking group, and the aryl The aryl and heteroaryl of heteroarylamino are not bonded to each other or are bonded through a linking group, and the two aryls of the diarylboryl are not bonded to each other or are bonded through a linking group.

Among these substituents, alkyl (for example, alkyl having 1 to 6 carbon atoms), cycloalkyl (for example, cycloalkyl having 3 to 14 carbon atoms), halogen (for example, fluorine) and deuterium are preferable. In addition, when substituted with cycloalkyl, the substituted form which forms a spiro structure may be sufficient, and this example is shown below.

As the form of the cycloalkane condensation, first, an aryl ring in each of rings A1 to A5 in a polycyclic aromatic compound having a structure consisting of one or two or more of the structural units represented by formula (1A-1); A form in which a heteroaryl ring is condensed with a cycloalkane is mentioned.

As another form of cycloalkane condensation, a polycyclic aromatic compound having a structure consisting of one or two or more structural units represented by formula (1A-1) is condensed with a cycloalkane, and diarylamino is attached to the aryl moiety. Examples having condensation, carbazolyl condensed with a cycloalkane (condensed on a benzene ring moiety), or benzocarbazolyl condensed with a cycloalkane (condensed with a benzene ring moiety) can be given. Moreover, the form in which the arylene, heteroarylene, or alkenylene etc. which are L ¹ , L ² , L ³ , and L ⁴ are condensed with a cycloalkane is also mentioned, Furthermore, NR, >C(-R) ₂ , or >Si Examples in which at least one R of (-R) ₂ is aryl condensed with a cycloalkane or heteroaryl condensed with a cycloalkane are also exemplified. As for "diarylamino", the group described as the said "first substituent" is mentioned. In addition, the two aryls of the diarylamino are not bonded to each other or are bonded through a linking group.

In addition, by introducing a cycloalkane structure into the polycyclic aromatic compound of the present invention, a decrease in melting point or sublimation temperature can be expected. This means that in sublimation refining, which is almost indispensable as a method for refining materials for organic devices such as organic EL devices that require high purity, it can be purified at a relatively low temperature, so that thermal decomposition of the material and the like can be avoided. The same applies to the vacuum deposition process, which is a powerful means for producing organic devices such as organic EL elements, and since the process can be carried out at a relatively low temperature, thermal decomposition of materials can be avoided, and as a result, high-performance organic devices can be obtained. can Moreover, since the solubility to an organic solvent improves by introduction of a cycloalkane structure, it becomes possible to apply also to device fabrication using the application|coating process. However, the present invention is not particularly limited to these principles.

All or part of hydrogen in the polycyclic aromatic compound which consists of one or two or more structural units represented by Formula (1A-1) and its preferable form mentioned later may be deuterium, cyano, or halogen. Halogen is fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine, or bromine, more preferably fluorine or chlorine, and still more preferably fluorine. In addition, from the viewpoint of durability, it is preferable that all or part of hydrogen in the aromatic ring portion in the structure consisting of one or two or more of the structural units represented by the formula (1A-1) is deuterated, and the aromatic ring portion It is more preferable that all are deuterated, and the hydrogen substituted with alkenylene which is L ¹ , L ² , L ³ or L ⁴ , and all of the aromatic ring moieties are most preferably deuterated.

For example, in a structure comprising one or two or more of the structural units represented by the formula (1A-1), the aryl ring and heteroaryl ring as the A1 ring, the A2 ring, the A3 ring, the A4 ring, and the A5 ring , a cycloalkyl ring, or a cycloheteroalkyl ring, or a substituent on the A1 ring, the A2 ring, the A3 ring, the A4 ring, and the A5 ring, or L ¹ , L ² , L ³ , and L ⁴ ; unsubstituted arylene, substituted or unsubstituted heteroarylene, substituted or unsubstituted alkylene, substituted or unsubstituted cycloalkylene, substituted or unsubstituted alkenylene, >NR, >C(-R) ₂ , >Si(-R) ₂ arylene, heteroarylene, alkylene, cycloalkylene, alkenylene, >NR R , >Si(-R) ₂ R , and >C(-R) ₂ above Although hydrogen in R may be substituted with deuterium, cyano or halogen, among these, all or part of hydrogen in the aromatic ring moiety of aryl, heteroaryl, arylene, and heteroarylene is deuterium, cyano, Or an embodiment substituted with halogen is preferably mentioned.

Preferred examples of the structural unit represented by the formula (1A-1) include a structural unit represented by the following formula (1a-1). In addition, for the structure of the substituent in Formula (1a-1), the ring contained, and preferable range, each description of the corresponding Formula (1a-1) can be referred.

In the formula (1a-1), Y ¹ , L ¹ , L ² , L ³ , L ⁴ , n, m, q and r are defined and their preferred ranges, respectively, and The same is true.

In the formula (1a-1), Z is each independently N or CR ¹ , wherein R ¹ of CR ¹ is each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, aryl heteroarylamino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or substituted silyl, preferably hydrogen, aryl, heteroaryl, alkyl, cycloalkyl, or diarylamino. At least one hydrogen in these is unsubstituted or substituted with aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl. It is even more preferred that R ¹ is hydrogen, alkyl, cycloalkyl, or diarylamino, wherein diarylamino is unsubstituted or substituted with alkyl or cycloalkyl. In addition, the two aryls of the diarylamino are not bonded to each other or are bonded through a linking group, and the two heteroaryls of the diheteroarylamino are not bonded to each other or are bonded through a linking group, and the aryl The aryl and heteroaryl of heteroarylamino are not bonded to each other or are bonded through a linking group, and the two aryls of the diarylboryl are not bonded to each other or are bonded through a linking group. For details of the substituents enumerated here and their preferred ranges, reference can be made to the description in the present specification.

In the formula (1a-1), two adjacent R ¹ are bonded to each other to form, or not form an aryl ring or a heteroaryl ring, at least one of the formed aryl ring and the formed arylheteroaryl ring each hydrogen is substituted with aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or substituted silyl; may be, but preferably hydrogen, aryl, heteroaryl, alkyl, cycloalkyl, or diarylamino, wherein at least one hydrogen is aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl may be substituted with In addition, the two aryls of the diarylamino are not bonded to each other or are bonded through a linking group, and the two heteroaryls of the diheteroarylamino are not bonded to each other or are bonded through a linking group, and the aryl The aryl and heteroaryl of heteroarylamino are not bonded to each other or are bonded through a linking group, and the two aryls of the diarylboryl are not bonded to each other or are bonded through a linking group. For details of the substituents enumerated here and their preferred ranges, reference can be made to the description in the present specification.

each Z is, independently, N or CR ¹ , or Z=Z is each independently >O, >NR, >C(-R) ₂ , >Si(-R) ₂ , >S, or >Se, , all independently are preferably CR ¹ . R of >NR, >C(-R) ₂ , and >Si(-R) ₂ are each independently hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, wherein at least one hydrogen When is substituted, it is preferably aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl. Two R of >C(-R) ₂ and >Si(-R) 2 may or may not be bonded to each other to form a ring. For details of the substituents enumerated here and their preferred ranges, reference can be made to the description in the present specification.

For example, in ring a2 in formula (1a-1), the position of "Z=Z" is >O, >NR, >C(-R) ₂ , >Si(-R) ₂ , >S, or Examples of the ring obtained by substituting for >Se include a cyclopentadiene ring, a pyrrole ring, a furan ring, and a thiophene ring. In the a2 ring, etc., one Z=Z is >NR, >O, >S, >C(-R) ₂ , and the remaining Z is CH. However, it is not limited to the following example as a form which a2 ring etc. can take. As described above, since the organic chemically completely equivalent resonance structural formula exists in the aromatic compound, it may be based on any possible resonance structural formula.

R in at least one of >NR, >Si(-R) ₂ and >C(-R) ₂ in L ¹ , L ² , L ³ , and L ⁴ in Formula (1A-1) is , the above-described description of whether or not bonded to the A1 ring to the A5 ring by a linking group or a single bond is, in the formula (1a-1), "R of >NR, and >C(-R) ) ₂ R, and at least one R of >Si(-R) ₂ are each independently at least one of R ^Z for CR ^Z , -O-, -S-, -C( -R) ₂ - or bonded by a single bond, or not bonded". Specifically, the above R is bonded to the a1 ring to the a5 ring, or to Z which is the spatially closest CR ^Z in each ring, or is not.

Formula (1a-1) and its preferable form WHEREIN: The number of rings (monocyclic) containing Z which is N is 0-4, It is preferable that it is 0-3, It is more preferable that it is 0-2, It is 0- It is especially preferable that it is one. In the formula (1a-1) and its preferred form, it is also preferable that all of Z are CR ^Z .

In formula (1a-1) and in the ring (monocyclic) containing Z which is N in its preferable form, it is preferable that one or two of several Z are N, and when two are N, 2 It is preferable that the number of N are not adjacent to each other. When the 6-membered ring is a ring containing N which is N, a pyridine ring, a pyrimidine ring, a pyridazine ring, or a 1,2,3-triazine ring is preferable, and a pyridine ring or a pyrimidine ring is more preferable. When a 5-membered ring is a ring containing Z which is N, a thiazole ring and an oxazole ring are preferable.

As a preferable example of the structural unit represented by Formula (1A-1), the structural unit represented by Formula (1b-1) or Formula (1b-2) is mentioned. In addition, for the structure of the substituent in Formula (1b-1) and Formula (1b-2), the structure of the ring contained, and preferable range, each description of the corresponding Formula (1a-1) can be referred.

In formulas (1b-1) and (1b-2), q and r are each independently 0 or 1, and in the case of 0, the carbon atom bonded to the divalent group in parentheses is substituted with R ¹ , However, although q+r=0 is not, q+r=1 is preferable.

L ³ , L ⁴ are each independently a single bond, arylene, heteroarylene or alkenylene, at least one hydrogen of which is substituted with alkyl, cycloalkyl, diarylamino, or substituted silyl, or It is not substituted, and the two aryls of the diarylamino are bonded through a linking group or are not bonded. L ³ and L ⁴ are preferably a single bond. In addition, for definitions of Z and Y1 and their preferred ranges, reference can be made to the respective descriptions of the formula (1a-1).

As a preferable example of the structural unit represented by Formula (1A-1), the structural unit represented by Formula (1c-1), Formula (1c-2), Formula (1c-3), or Formula (1c-4) is can be heard In addition, about the definition of Z in Formula (1c-1), Formula (1c-2), Formula (1c-3), and Formula (1c-4), and its preferable range, the corresponding Formula (1a-1) ) can be referred to for each description.

As a preferable example of the structural unit represented by Formula (1A-1), the structural unit represented by Formula (1d-1) or Formula (1d-2) is mentioned.

In formulas (1d-1) and (1d-2), R ^d is each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cyclo alkyl, alkenyl, alkoxy, aryloxy, arylthio, or substituted silyl, preferably hydrogen, aryl, heteroaryl, alkyl, cycloalkyl, or diarylamino, or substituted silyl, hydrogen, alkyl, cycloalkyl, It is more preferred that they are aryl or heteroaryl, and most preferably all are hydrogen. In addition, at least one hydrogen in these is unsubstituted or substituted with aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl. In addition, the two aryls of the diarylamino are not bonded to each other or are bonded through a linking group, and the two heteroaryls of the diheteroarylamino are not bonded to each other or are bonded through a linking group, and the aryl The aryl and heteroaryl of heteroarylamino are not bonded to each other or are bonded through a linking group, and the two aryls of the diarylboryl are not bonded to each other, or are bonded to each other through a single bond or a linking group. For details of the substituents enumerated here and their preferred ranges, reference can be made to the description in the present specification. In addition, for definitions of other symbols in formulas (1d-1) and formulas (1d-2) and preferred ranges, refer to explanations of formulas (1b-1) and (1b-2) can do.

Preferred examples of the structural unit represented by the formula (1A-1) include a structural unit represented by the formula (1e-1), (1e-2), (1e-3) or (1e-4). can For the definition of each code and the preferred range, reference can be made to the descriptions of the formulas (1d-1) and (1d-2).

Preferred examples of the structural unit represented by the formula (1A-1) include a structural unit represented by the formula (1f-1) or (1f-2).

In the formula (1f-1) or (1f-2), x is an integer from 1 to 3. Taking Formula (1f-1) as an example, the case where x is 1 or 2 is shown.

Also, when x is 2 or 3, two or three E's are continuous, but as they are defined as "independently" as will be described later, two or three E's are the same or different. Moreover, when x is 3, two E may be the same, and one E may differ. This description also applies to the preferable form of Formula (1f-1) or Formula (1f-2), which will be described later, unless specifically limited.

In formula (1f-1) or formula (1f-2), A is each independently >(CR)-, wherein R in >(CR)- is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted It is substituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, and it is more preferable that it is hydrogen or alkyl. In addition, it is preferable that R of >(CR)- of A bonded to N and L ¹ to L ⁴ when the subscripts (n, m, q, and r) in parentheses are 1 is alkyl. For details of the substituents enumerated here and their preferred ranges, reference can be made to the description in the present specification.

In addition, in Formula (1f-1) or Formula (1f-2), when the parenthesis subscript of L ³ or L ⁴ adjacent to A is 1, L ³ or L ⁴ is bonded, and when 0, A carbon atom of >(CR)- which is A, and a carbon atom of the f3 ring or f4 ring bonded to L ³ or L ⁴ are each independently substituted with R ¹ . When this is expressed by Formula (1f-1), for example, it becomes as follows. Moreover, in the following, R represents R of >(CR)- which is A. This description also applies to the preferable form of Formula (1f-1) or Formula (1f-2), which will be described later, unless specifically limited. For details of the substituents enumerated here and their preferred ranges, reference can be made to the description in the present specification.

In formula (1f-1) or formula (1f-2), E is each independently >O, >NR, >C(-R) ₂ , >Si(-R) ₂ , >S, or >Se and R of >NR, R of >Si(-R) ₂ , and R of >C(-R) ₂ are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted hetero aryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, wherein two R of >Si(-R) ₂ and two R of >C(-R) ₂ are bonded to each other to form a ring It does not form or forms, but each E is preferably >O, >NR, >S, or >C(-R) ₂ , and all E are each independently >C(-R) ) ₂ is most preferred. And it is more preferable that all R of >C(-R) ₂ are hydrogen. This description also applies to the preferable form of Formula (1f-1) or Formula (1f-2), which will be described later, unless specifically limited.

For other symbols in the formula (1f-1) or (1f-2) and their preferred ranges, reference may be made to the description in the formula (1a-1). In addition, for the detail of the substituent enumerated here and its preferable range, the description in this specification can be referred to.

Preferred examples of the structural unit represented by the formula (1f-1) or (1f-2) include a structural unit represented by the formula (1g-1) or (1g-2).

For the definitions of A, E and x in the formula (1g-1) or (1g-2) and their preferred ranges, reference is made to the explanations in the formulas (1f-1) and (1f-2). can Further, for definitions of Z, Y ¹ , L ³ , L ⁴ , r and q and their preferred ranges, reference may be made to the descriptions of formulas (1b-1) and (1b-2).

Preferred examples of the structural unit represented by formula (1f-1) or formula (1f-2) include formula (1h-1), formula (1h-2), formula (1h-3), or formula (1h-4) The structural unit represented by ) is mentioned.

In formulas (1h-1), (1h-2), (1h-3), and (1h-4), the definitions of A, E, and x and their preferred ranges are described in formula (1f-1) ) and the description in the formula (1f-2) can be referred to. Further, for the definition of Z and their preferred ranges, reference may be made to the descriptions of the formulas (1b-1) and (1b-2).

Preferred examples of the structural unit represented by the formula (1f-1) or (1f-2) include the structural unit represented by the formula (1i-1) or (1i-2).

For the definition of R ^d in the formula (1i-1) or (1i-2) and a preferable range thereof, reference may be made to the description of the formula (1d-1) or (1d-2). In addition, for other code|symbols and their preferable range, the description in Formula (1b-1) or Formula (1b-2) can be referred.

Preferred examples of the structural unit represented by formula (1f-1) or formula (1f-2) include formula (1k-1), formula (1k-2), formula (1k-3) or formula (1k-4) and structural units represented by

In formula (1k-1), formula (1k-2), formula (1k-3) or formula (1k-4), regarding the definition of R ^d and their preferred ranges, formula (1d-1) or formula See the description of (1d-2). Moreover, regarding the definition of Z and their preferable range, the description in Formula (1b-1) and Formula (1b-2) can be referred to.

Preferred examples of the polycyclic aromatic compound having a structure consisting of two structural units represented by formula (1a-1) include formulas (1a-d-1), formulas (1a-d-2), and formulas (1a-d). -3) and formulas (1a-d-4). Each of these structures is a dimer structure sharing an a8 ring.

In formulas (1a-d-1), (1a-d-2), (1a-d-3), and (1a-d-4), L ⁵ , L ⁶ , L ⁷ , L ⁸ , L ⁹ , L ¹⁰ , L ¹¹ and L ¹² are each independently a single bond, substituted or unsubstituted arylene, substituted or unsubstituted heteroarylene, substituted or unsubstituted alkylene, substituted or unsubstituted cycloalkyl ren, substituted or unsubstituted alkenylene, >O, >NR, >C(-R) ₂ , >Si(-R) ₂ , >S, or >Se, wherein R of >NR, >Si( R of -R) ₂ and R of >C(-R) ₂ are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or It is unsubstituted cycloalkyl, and two R of the said >Si(-R) ₂ and two R of the said >C(-R) ₂ may combine with each other and may form a ring. Among these, single bond, substituted or unsubstituted arylene (preferably phenylene or naphthylene), or substituted or unsubstituted heteroarylene (preferably benzothiophenylene, benzofuranylene, indolylene) , dibenzothiophenylene, dibenzofuranylene, or carbazolylene) is preferred, and at least one of L ⁵ to L ¹² is substituted or unsubstituted arylene, substituted or unsubstituted heteroarylene, or substituted or unsubstituted alkenylene (in each case the parenthetical subscript is 1). Moreover, d+e+f+h+s+t+w+w=0 does not become. Y ¹ and Z may apply the definition and preferred ranges of formula (1a-1), but preferably all of Z are CR ¹ , and Y ¹ is preferably B. For details of the substituents enumerated here and their preferred ranges, reference can be made to the description in the present specification.

Preferred examples of the polycyclic aromatic compound having a structure consisting of two structural units represented by formulas (1c-1) to (1c-4) include, for example, formulas (1c-d-1) and formula (1c). -d-2), formula (1c-d-3), formula (1c-d-4), formula (1c-d-5), formula (1c-d-6), formula (1c-d-7) , formula (1c-d-8), formula (1c-d-9), formula (1c-d-10), formula (1c-d-11), formula (1c-d-12), formula (1c- d-13), formula (1c-d-14), formula (1c-d-15), formula (1c-d-16), formula (1c-d-17), formula (1c-d-18), or formula (1c-d-19),

Preferred examples of the polycyclic aromatic compound having a structure consisting of two structural units represented by formulas (1e-1) to (1e-4) include, for example, formulas (1e-d-1) and formula (1e). -d-2), formula (1e-d-3), formula (1e-d-4), formula (1e-d-5), formula (1e-d-6), formula (1e-d-7) , formula (1e-d-8), formula (1e-d-9), formula (1e-d-10), formula (1e-d-11), formula (1e-d-12), (1e-d -13), formula (1e-d-14), formula (1e-d-15), formula (1e-d-16), formula (1e-d-17), formula (1e-d-18), or Formula (1e-d-19) is mentioned.

These structures are dimer structures each sharing a c11 ring or an e11 ring. Z is each applicable to the definitions and preferred ranges of formulas (1c-1) to (1c-4) and (1e-1) to (1e-4).

Further specific examples of the polycyclic aromatic compound having a structure comprising one or two or more of the structural units represented by formula (1A-1) of the present invention include the following compounds. In the following structural formula, "Me" represents methyl, "tBu" represents t-butyl, and "D" represents deuterium. In addition, the following structure is an example.

The polycyclic aromatic compound of the present invention can be produced by the following procedure.

<Method for producing polycyclic aromatic compound>

A polycyclic aromatic compound having a structure composed of one or two or more of the structural units represented by the formula (1A-1) is basically, first, a bonding group (L ¹ to L ⁴ , and a nitrogen atom in rings A1 to A5) A final product can be prepared by combining the intermediates ( ^first reaction) by bonding with a group including ). In the first reaction, for example, if it is an etherification reaction, a general reaction such as a nucleophilic substitution reaction or a Ullman reaction may be used, and if it is an amination reaction, a general reaction such as a Birchwald-Hartwick reaction may be used. In addition, in the second reaction, a tandem hetero Friedel Crafts reaction (continuous aromatic sphere substitution reaction, the same hereinafter) can be used. A condensed ring compound can be produced by using a raw material having a desired condensed ring or adding a ring condensing step in any of the reaction steps. In addition, the polycyclic aromatic compound having a structure composed of two or more structural units may be bound by a bonding group (group including Y ¹ ) in the second reaction by preparing the corresponding intermediate in the first reaction. In this case, what is necessary is just to adjust the reagent (boron tribromide etc.) necessary for introduction|transduction of the group containing Y< ¹ > according to the number of Y< ¹ > to be introduced.

<Production method via intermediate-1>

The polycyclic aromatic compound of the present invention can be produced by a production method including the following steps. For each process below, reference may be made to the description of International Publication No. 2015/102118.

A reaction step of metallizing a halogen atom (Hal) between nitrogen atoms in the following intermediate-1 using an organic alkali compound, a halide of Y ¹ , an amination halide of Y ¹ , and alkoxide of Y ¹ And Y ¹ by a reaction step of exchanging the metal and Y ¹ using a reagent selected from the group consisting of an aryloxide of Y 1, and a continuous aromatic sphere substitution reaction using a Bronsted base to Y ¹ to B A reaction including a reaction step for bonding a ring and a C ring is recorded below.

<Production method via intermediate-2>

The polycyclic aromatic compound of the present invention can also be produced by a production method including the following steps. For each process below, reference may be made to the description of International Publication No. 2015/102118.

A reaction step of metallizing a hydrogen atom (H) between nitrogen atoms in the following intermediate-2 using an organic alkali compound, a halide of Y ¹ , an amination halide of Y ¹ , and alkoxide of Y ¹ And Y ¹ by a reaction step of exchanging the metal and Y ¹ using a reagent selected from the group consisting of an aryloxide of Y 1, and a continuous aromatic sphere substitution reaction using a Bronsted base to Y ¹ to B A reaction including a reaction step for bonding a ring and a C ring is recorded below. Also described in Journal of The American Chemistry, 2018, 140, 1195-1198, Angewandte Chemie International Edition 2021, 60, 2882-2886, or Nature Photonics 2019, 13, 678. A method of directly reacting with a halide of Y ¹ (such as boron tribromide) may be used (one-shot method) by omitting the reaction step of metallizing the atom (H). In this case, after making it react with the halide (boron tribromide etc.) of Y< ¹ >, or simultaneously, you may use bases, such as an amine.

Examples of the metallizing reagent used in the halogen-metal exchange reaction in the scheme described so far include alkyl lithium such as methyl lithium, n-butyl lithium, sec-butyl lithium and t-butyl lithium, isopropyl magnesium chloride, and isobromide. propylmagnesium, phenylmagnesium chloride, phenylmagnesium bromide, and a lithium chloride complex of isopropylmagnesium chloride known as a turbogrignard reagent.

In addition to the above reagents, lithium diisopropylamide, lithium tetramethylpiperidide, lithium hexamethyldisilazide, potassium hexa and organic alkali compounds such as methyldisilazide, lithium chloride tetramethylpiperidinyl magnesium/lithium chloride complex, and lithium tri-n-butylmagnesium acid.

In addition, as an additive for accelerating the reaction when alkyllithium is used as a metallization reagent, N,N,N',N'-tetramethylethylenediamine, 1,4-diazabicyclo[2.2.2]octane, N, and N-dimethylpropylene urea.

In addition, as Lewis acids used in the schemes described so far, AlCl ₃ , AlBr ₃ , AlF ₃ , BF ₃ ·OEt ₂ , BCl ₃ , BBr ₃ , GaCl ₃ , GaBr ₃ , InCl ₃ , InBr ₃ , In(OTf) ) ₃ , SnCl ₄ , SnBr ₄ , AgOTf, ScCl ₃ , Sc(OTf) ₃ , ZnCl ₂ , ZnBr ₂ , Zn(OTf) ₂ , MgCl ₂ , MgBr ₂ , Mg(OTf) ₂ , LiOTf, NaOTf, KOTf, Me ₃ SiOTf, Cu(OTf) ₂ , CuCl ₂ , YCl ₃ , Y(OTf) ₃ , TiCl ₄ , TiBr ₄ , ZrCl ₄ , ZrBr ₄ , FeCl ₃ , FeBr ₃ , CoCl ₃ , CoBr ₃ and the like. . In addition, those in which these Lewis acids are supported on a solid can be used similarly.

In addition, as the Bronsted acid used in the scheme described so far, p-toluenesulfonic acid, methanesulfonic acid, trifluoromethanesulfonic acid, fluorosulfonic acid, carboric acid, trifluoroacetic acid, (trifluoromethanesulfonyl ) imide, tris(trifluoromethanesulfonyl)methane, hydrogen chloride, hydrogen bromide, hydrogen fluoride, and the like. Examples of the solid Bronsted acid include Amberlyst (trade name: Dow Chemical), Nafion (trade name: DuPont), zeolite, and Teikacure (trade name: Teika Corporation).

In addition, as an amine which may be added in the scheme demonstrated so far, diisopropylethylamine, triethylamine, tributylamine, 1, 4- diazabicyclo [2.2.2] octane, N, N- dimethyl-p- toluidine, N,N-dimethylaniline, pyridine, 2,6-lutidine, 2,6-di-t-butylamine, and the like.

In addition, as solvents used in the schemes described so far, o-dichlorobenzene, chlorobenzene, toluene, benzene, methylene chloride, chloroform, dichloroethylene, benzotrifluoride, decalin, cyclohexane, hexane, heptane, 1,2 and 4-trimethylbenzene, xylene, diphenyl ether, anisole, cyclopentyl methyl ether, tetrahydrofuran, dioxane, methyl-t-butyl ether, and the like.

Here, an example in which Y ¹ is B is described, but by appropriately changing the raw material, compounds in which Y ¹ is P, P=O, P=S, Al, Ga, As, Si-R or Ge-R are also synthesized. can do.

As ^a halide of Y1 to be used, as Y1 is ^B , boron trichloride, boron tribromide, and boron trioxide are mentioned.

In the above scheme, a Bronsted base or a Lewis acid may be used to promote the tandem hetero Friedel Crafts reaction. However, when using the halide ^of Y1, such as the trifluoride ^of Y1, the trichloride ^of Y1, ^the tribromide ^of Y1, and the trioxide of Y1, hydrogen fluoride with progress of an aromatic sphere substitution reaction Since acids such as , hydrogen chloride, hydrogen bromide, and hydrogen iodide are formed, the use of a Bronsted base to trap acids is effective. On the other hand, when an amination halide of Y ¹ or an alkoxide of Y ¹ is used, amines and alcohols are generated along with the progress of the aromatic ball substitution reaction, so in many cases, it is not necessary to use a Bronsted base , since the desorption ability of amino or alkoxy is low, it is effective to use a Lewis acid that promotes the desorption.

In addition, the polycyclic aromatic compound of the present invention includes a compound in which at least a part of hydrogen atoms are substituted with deuterium or cyano, or a compound substituted with halogen such as fluorine or chlorine. By using a cyanoated, fluorinated or chlorinated raw material, it can be synthesized in the same manner as above. Further, the deuterated compound and the halogen compound can also be obtained by halogenating and deuterating the target halogenated compound or the precursor of the deuterated compound, respectively.

<Organic device>

The polycyclic aromatic compound of the present invention can be used as a material for an organic device. As an organic device, although an organic electroluminescent element, an organic field effect transistor, an organic thin film solar cell, etc. are mentioned, for example, It is preferable that it is a material for organic electroluminescent elements.

<Organic electroluminescent device>

<Structure of organic electroluminescent device>

1 is a schematic cross-sectional view showing an example of an organic EL device.

The organic EL device 100 shown in FIG. 1 includes a substrate 101 , an anode 102 provided on the substrate 101 , a hole injection layer 103 provided on the anode 102 , and a hole injection layer The hole transport layer 104 provided on (103), the light emitting layer 105 provided on the hole transport layer 104, the electron transport layer 106 provided on the light emitting layer 105, and the electrons provided on the electron transport layer 106 It has an injection layer 107 and a cathode 108 provided on the electron injection layer 107 .

In the organic EL device 100 , for example, the substrate 101 , the cathode 108 provided on the substrate 101 , and the electron injection layer ( 107 , 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 , and a hole transport layer It is good also as a structure which has the hole injection layer 103 provided on (104), and the anode 102 provided on the hole injection layer 103. As shown in FIG.

All of the above layers are not indispensable, and the minimum structural unit is a configuration consisting of the anode 102, the light emitting layer 105, and the cathode 108, and the hole injection layer 103, the hole transport layer 104, and the electron transport layer 106 ), the electron injection layer 107 is an arbitrarily provided layer. In addition, each said layer may consist of a single layer, respectively, and may consist of multiple layers.

As the aspect of the layer constituting the organic EL element, in addition to the configuration aspect of "substrate / anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode" described above, "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/hole transport layer/light emitting layer/electron injection layer/ Cathode", "substrate / anode / hole injection layer / hole transport layer / light emitting layer / electron 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 injection layer/light-emitting layer/electron injection layer/cathode", "substrate/anode/hole injection layer/ The structural aspect of "substrate/anode/light-emitting layer/electron transport layer/cathode" and "substrate/anode/light-emitting layer/electron injection layer/cathode" may be sufficient.

<Light emitting layer in organic electroluminescent element>

The polycyclic aromatic compound of the present invention is preferably used as a material for forming any one or more organic layers in an organic electroluminescent device, and more preferably used as a material for forming a light emitting layer. The light emitting layer 105 is a layer that emits light by recombination between the electrodes to which the electric field is applied, and the holes injected from the anode 102 and the electrons injected from the cathode 108 . The material for forming the light emitting layer 105 may be a compound that emits light by being excited by recombination of holes and electrons (a light emitting compound), and can form a stable thin film, and exhibit strong light emission (fluorescence) efficiency in a solid state. It is preferable that it is a compound represented. The polycyclic aromatic compound of the present invention may be used as a material for a light emitting layer, may be used as a dopant material, or may be used as a host material, but is preferably used as a material for a light emitting layer, more preferably used as a dopant material .

In addition, as a dopant, there is an example in which an assisting dopant and an emitting dopant are used together as described later, but in the present specification, only when "dopant" is described, the emitting dopant, that is, the emitting dopant itself emits light. refers to the dopant.

A single layer may be sufficient as it, or it may consist of multiple layers, either may be sufficient as it, and a light emitting layer is formed with the material for light emitting layers (host material, dopant material), respectively. The number of each of a host material and a dopant material may be one, or a plurality of combinations may be sufficient, and any may be sufficient as them. The dopant material may be contained in the whole host material, may be contained partially, and any may be sufficient as it. As a doping method, although it can form by the co-evaporation method with a host material, you may vapor-deposit simultaneously after mixing with a host material beforehand.

The usage-amount of a host material changes with the kind of host material, and what is necessary is just to determine according to the characteristic of the host material. The standard of the usage-amount of a host material becomes like this. Preferably it is 50-99.999 mass % of the whole material for light emitting layers, More preferably, it is 80-99.95 mass %, More preferably, it is 90-99.9 mass %.

The usage-amount of a dopant material changes with the kind of dopant material, and what is necessary is just to determine it according to the characteristic of the dopant material. The standard of the usage-amount of a dopant becomes like this. Preferably it is 0.001-50 mass % of the whole material for light emitting layer, More preferably, it is 0.05-20 mass %, More preferably, it is 0.1-10 mass %. If it is the said range, for example, it is preferable at the point that a density|concentration quenching phenomenon can be prevented.

<Host Material>

Examples of the host material include condensed ring derivatives such as anthracene, pyrene, dibenzochrysene or fluorene, bisstyryl derivatives such as bisstyrylanthracene derivatives and distyrylbenzene derivatives, tetraphenylbutadiene derivatives, and cyclones, which have been previously known as light emitters. A pentadiene derivative, a fluorene derivative, a benzofluorene derivative, a dibenzochrysene type compound, etc. are mentioned.

In addition, as a host material, the compound represented by any one of following formula (H1), (H2), and (H3) can be used, for example.

In formulas (H1), (H2) and (H3), L ¹ is arylene having 6 to 24 carbon atoms, heteroarylene having 2 to 24 carbon atoms, heteroarylene arylene having 6 to 24 carbon atoms, and heteroarylene arylene having 6 to 24 carbon atoms. It is an arylene heteroarylene arylene, C6-C16 arylene is preferable, C6-C12 arylene is more preferable, C6-C10 arylene is especially preferable, Specifically, a benzene ring and divalent groups such as a biphenyl ring, a terphenyl ring and a fluorene ring. As the heteroarylene, heteroarylene having 2 to 24 carbon atoms is preferable, heteroarylene having 2 to 20 carbon atoms is more preferable, heteroarylene having 2 to 15 carbon atoms is even more preferable, and heteroarylene having 2 to 10 carbon atoms is more preferable. Arylene is particularly preferable, and specifically, 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 Ring, pyrimidine ring, pyridazine ring, pyrazine ring, triazine ring, indole ring, isoindole ring, 1H-indazole ring, benzoimidazole ring, benzoxazole ring, benzothiazole ring, 1H-benzotriazole ring, quinoline ring, Isoquinoline ring, cinnoline ring, quinazoline ring, quinoxaline ring, phthalazine ring, naphthridine ring, purine ring, pteridine ring, carbazole ring, acridine ring, phenoxatiin ring, phenoxazine ring, phenothia Jin ring, phenazine ring, indolizine ring, furan ring, benzofuran ring, isobenzofuran ring, dibenzofuran ring, thiophene ring, benzothiophene ring, dibenzothiophene ring, furazan ring, oxadiazole ring and thiant Bivalent groups, such as a ren ring, are mentioned.

At least one hydrogen in the compound represented by the above formulas may be substituted with alkyl, cyano, halogen or deuterium having 1 to 6 carbon atoms.

Preferred specific examples include compounds represented by any one of the structural formulas listed below. In the structural formulas listed below, at least one hydrogen may be substituted with halogen, cyano, alkyl having 1 to 4 carbon atoms (eg, methyl or t-butyl), phenyl or naphthyl.

(mCP)

<Anthracene-based compound>

Examples of the anthracene-based compound as the host material include a compound represented by formula (3-H) and a compound represented by formula (3-H2).

In formula (3-H),

X and Ar ⁴ are each independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted diarylamino, optionally substituted diheteroarylamino, or optionally substituted arylheteroarylamino , optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted arylthio or optionally substituted silyl, and all X And Ar ⁴ is not hydrogen at the same time,

At least one hydrogen in the compound represented by formula (3-H) may be substituted with halogen, cyano, deuterium or optionally substituted heteroaryl. In addition, the two aryls of the diarylamino are not bonded to each other or are bonded through a linking group, and the two heteroaryls of the diheteroarylamino are not bonded to each other or are bonded through a linking group, and the aryl The aryl and heteroaryl of heteroarylamino are not bonded to each other or are bonded through a linking group.

Moreover, you may form a multimer (preferably a double body) by making the structure represented by Formula (3-H) as a unit structure. In this case, for example, a form in which the unit structures represented by the formula (3-H) are bonded to each other through X, where X is a single bond, arylene (phenylene, biphenylene, naphthylene, etc.) and heteroarylene (groups in which a pyridine ring, a dibenzofuran ring, a dibenzothiophene ring, a carbazole ring, a benzocarbazole ring, and a phenyl-substituted carbazole ring have a divalent bonding value), and the like.

For the details of each group in the compound represented by the formula (3-H), the description in the formula (1) can be cited, and further, the following describes in the column of the preferred embodiment.

Preferred embodiments of the anthracene-based compound will be described below. The definition of the code|symbol in the following structure is the same as that of the definition mentioned above.

In formula (3-H), each X independently represents a group represented by formula (3-X1), formula (3-X2) or formula (3-X3), formula (3-X1), formula (3-X3) X2) or the group represented by the formula (3-X3) is bonded to the anthracene ring of the formula (3-H) in *. Preferably, two X's do not become a group represented by formula (3-X3) at the same time. More preferably, two Xs do not become a group represented by the formula (3-X2) at the same time.

Moreover, you may form a multimer (preferably a double body) by making the structure represented by Formula (3-H) as a unit structure. In this case, for example, a form in which the unit structures represented by the formula (3-H) are bonded to each other through X, where X is a single bond, arylene (phenylene, biphenylene, naphthylene, etc.) and heteroarylene (groups in which a pyridine ring, a dibenzofuran ring, a dibenzothiophene ring, a carbazole ring, a benzocarbazole ring, and a phenyl-substituted carbazole ring have a divalent bonding value), and the like.

The naphthylene moiety in formulas (3-X1) and (3-X2) may be condensed with one benzene ring. The structure condensed in this way is as follows.

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

Ar ³ is phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenyl, or, formula (A) is a group represented by (including carbazolyl, benzocarbazolyl and phenyl-substituted carbazolyl). In addition, when Ar ³ is a group represented by the formula (A), the group represented by the formula (A) is bonded to a single bond represented by a straight line in the formula (3-X3) in the *. That is, the anthracene ring of Formula (3-H) and the group represented by Formula (A) couple|bond directly.

In addition, Ar ³ may have a substituent, and at least one hydrogen in Ar ³ is alkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, phenyl, biphenylyl, terphenylyl, naphthyl, phenane. It may be further substituted with triyl, fluorenyl, chrysenyl, triphenylenyl, pyrenyl, or a group represented by the formula (A) (including carbazolyl and phenyl-substituted carbazolyl). In addition, when the substituent which Ar ³ has is a group represented by the formula (A), the group represented by the formula (A) is bonded to Ar ³ in the formula (3-X3) in *.

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

Examples of the alkyl having 1 to 4 carbon atoms substituted for silyl include methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, t-butyl and cyclobutyl, and three hydrogens in silyl are each independently , which is substituted with these alkyls.

Specific examples of “silyl substituted with alkyl having 1 to 4 carbon atoms” include trimethylsilyl, triethylsilyl, tripropylsilyl, triisopropylsilyl, tributylsilyl, trisec-butylsilyl, trit-butylsilyl, and ethyldimethyl Silyl, propyldimethylsilyl, isopropyldimethylsilyl, butyldimethylsilyl, sec-butyldimethylsilyl, t-butyldimethylsilyl, methyldiethylsilyl, propyldiethylsilyl, isopropyldiethylsilyl, butyldiethylsilyl, sec- Butyldiethylsilyl, t-butyldiethylsilyl, methyldipropylsilyl, ethyldipropylsilyl, butyldipropylsilyl, sec-butyldipropylsilyl, t-butyldipropylsilyl, methylisopropylsilyl, ethyldiisopropyl and silyl, butyldiisopropylsilyl, sec-butyldiisopropylsilyl, and t-butyldiisopropylsilyl.

Cycloalkyl having 5 to 10 carbon atoms substituted for silyl is cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.0]pentyl, bi Cyclo[2.1.1]hexyl, bicyclo[3.1.0]hexyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl, adamantyl, decahydronaphthalenyl, decahydroazulenyl, etc. and three hydrogens in silyl are each independently substituted with these cycloalkyls.

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

Examples of the substituted silyl include dialkylcycloalkylsilyl in which two alkyls and one cycloalkyl are substituted, and alkyldicycloalkylsilyl in which one alkyl and two cycloalkyls are substituted. As a specific example, the group mentioned above is mentioned.

In addition, hydrogen in the chemical structure of the anthracene type compound represented by Formula (3-H) may be substituted by the group represented by Formula (A). When substituted with the group represented by the formula (A), the group represented by the formula (A) is substituted with at least one hydrogen in the compound represented by the formula (3-H) in the *.

The group represented by the formula (A) is one of the substituents that the anthracene-based compound represented by the formula (3-H) may have.

In formula (A), Y is -O-, -S-, or >NR ²⁹ , and R ²¹ to R ²⁸ are each independently hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, or optionally substituted aryl. , optionally substituted heteroaryl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, substituted optionally amino, halogen, hydroxy or cyano, and adjacent groups among R ²¹ to R ²⁸ do not form or form a hydrocarbon ring, an aryl ring or a heteroaryl ring by combining with each other, R ²⁹ is hydrogen or It is aryl which may be substituted.

It is preferable that Y in a formula (A) is -O-.

The "alkyl" of the "optionally substituted alkyl" in R ²¹ to R ²⁸ may be either a straight chain or a branched chain, for example, a straight chain alkyl having 1 to 24 carbon atoms or a branched chain having 3 to 24 carbon atoms. alkyl; Alkyl having 1 to 18 carbon atoms (branched chain alkyl having 3 to 18 carbon atoms) is preferable, alkyl having 1 to 12 carbon atoms (branched chain alkyl having 3 to 12 carbon atoms) is more preferable, and alkyl having 1 to 6 carbon atoms (branched chain alkyl having 3 carbon atoms) is more preferable. -6 branched chain alkyl) is more preferable, and C1-C4 alkyl (C3-C4 branched chain alkyl) is especially preferable.

Specific examples of "alkyl" include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl, 1-methylheptyl, 2-ethyl Hexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl , n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-eicosyl, etc. are mentioned. .

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

Specific examples of "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and these alkyl (especially methyl) substituents having 1 to 4 carbon atoms, and 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, and bicyclo[2.2.2]octyl, adamantyl, diamantyl, decahydronaphthalenyl, and decahydroazulenyl.

Examples of the “aryl” of the “optionally substituted aryl” in R ²¹ to R ²⁸ include aryl having 6 to 30 carbon atoms, and aryl having 6 to 16 carbon atoms is preferable, and aryl having 6 to 12 carbon atoms is preferable. aryl is more preferable, and aryl having 6 to 10 carbon atoms is particularly preferable.

Specific examples of "aryl" include monocyclic phenyl, bicyclic biphenylyl, condensed bicyclic naphthyl, tricyclic terphenylyl (m-terphenylyl, o-terphenylyl, p-terphenylyl), Condensed tricyclic acenaphthyrenyl, fluorenyl, phenalenyl, phenanthrenyl, fused tetracyclic triphenylenyl, pyrenyl, naphthacenyl, condensed pentacyclic perylenyl, pentacenyl, etc. are mentioned. .

Examples of the "heteroaryl" of "heteroaryl which may be substituted" in R ²¹ to R ²⁸ include heteroaryl having 2 to 30 carbon atoms, and heteroaryl having 2 to 25 carbon atoms is preferable; Heteroaryl having 2 to 20 carbon atoms is more preferable, heteroaryl having 2 to 15 carbon atoms is still more preferable, and heteroaryl having 2 to 10 carbon atoms is particularly preferable. Examples of the heteroaryl include a heterocyclic ring containing 1 to 5 heteroatoms selected from oxygen, sulfur and nitrogen in addition to carbon as ring-constituting atoms.

Specific examples of "heteroaryl" include pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyrazolyl Dill, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzoimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, Isoquinolyl, cinnolyl, quinazolyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxathinyl, phenoxazinyl, phenothiazinyl, Phenazinyl, indolizinyl, furyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thienyl, benzo[b]thienyl, dibenzothienyl, furazanyl, thianthrenyl, naphthobenzofuranyl , and naphthobenzothienyl.

Examples of the “alkoxy” of the “optionally substituted alkoxy” in R ²¹ to R ²⁸ include straight-chain or branched-chain alkoxy having 1 to 24 carbon atoms or branched chain alkoxy having 3 to 24 carbon atoms. Alkoxy having 1 to 18 carbon atoms (branched alkoxy having 3 to 18 carbon atoms) is preferable, alkoxy having 1 to 12 carbon atoms (branched alkoxy having 3 to 12 carbon atoms) is more preferable, and alkoxy having 1 to 6 carbon atoms (branched alkoxy having 3 to 12 carbon atoms) is more preferable. -6 branched chain alkoxy) is more preferable, and C1-C4 alkoxy (C3-C4 branched chain alkoxy) is especially preferable.

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

The "aryloxy" of the "optionally substituted aryloxy" in R ²¹ to R ²⁸ is a group in which the hydrogen of the -OH group is substituted with aryl, and this aryl is the "aryloxy which may be substituted" in R ²¹ to R ²⁸ described above. The group described as "aryl" can be cited.

The "arylthio" of the "optionally substituted arylthio" in R ²¹ to R ²⁸ is a group in which the hydrogen of the -SH group is substituted with aryl, and this aryl is the "arylthio" in R ²¹ to R ²⁸ described above. The group described as "aryl" can be cited.

Examples of the "trialkylsilyl" for R ²¹ to R ²⁸ include a group in which three hydrogens in the silyl group are each independently substituted with alkyl, and this alkyl is the above-mentioned "alkyl silyl" for R ²¹ to R ²⁸ The group described as ' can be cited. Preferred alkyl for substitution is alkyl having 1 to 4 carbon atoms, and specific examples thereof include methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, t-butyl and cyclobutyl.

Specific examples of "trialkylsilyl" include trimethylsilyl, triethylsilyl, tripropylsilyl, triisopropylsilyl, tributylsilyl, trisec-butylsilyl, trit-butylsilyl, ethyldimethylsilyl, propyldimethylsilyl, isopropyl Dimethylsilyl, butyldimethylsilyl, sec-butyldimethylsilyl, t-butyldimethylsilyl, methyldiethylsilyl, propyldiethylsilyl, isopropyldiethylsilyl, butyldiethylsilyl, sec-butyldiethylsilyl, t-butyl Diethylsilyl, methyldipropylsilyl, ethyldipropylsilyl, butyldipropylsilyl, sec-butyldipropylsilyl, t-butyldipropylsilyl, methylisopropylsilyl, ethyldiisopropylsilyl, butyldiisopropylsilyl, and sec-butyldiisopropylsilyl and t-butyldiisopropylsilyl.

Examples of "tricycloalkylsilyl" for R ²¹ to R ²⁸ include a group in which three hydrogens in the silyl group are each independently substituted with cycloalkyl, and this cycloalkyl is represented by R ²¹ to R ²⁸ as described above. The group described as "cycloalkyl" of can be cited. Cycloalkyl preferred for substitution is cycloalkyl having 5 to 10 carbon atoms, and specifically, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, bicyclo[1.1.1]pentyl, and bicyclo[2.0 .1]pentyl, bicyclo[1.2.1]hexyl, bicyclo[3.0.1]hexyl, bicyclo[2.1.2]heptyl, bicyclo[2.2.2]octyl, adamantyl, decahydronaphtharenyl, Decahydroazulenyl, etc. are mentioned.

Specific examples of "tricycloalkylsilyl" include tricyclopentylsilyl and tricyclohexylsilyl.

As specific examples of dialkylcycloalkylsilyl substituted by two alkyls and one cycloalkyl, and alkyldicycloalkylsilyl substituted by one alkyl and two cycloalkyls, a group selected from the above specific alkyl and cycloalkyl is substituted One silyl can be mentioned.

Examples of the "substituted amino" of the "optionally substituted amino" in R ²¹ to R ²⁸ include amino in which two hydrogens are substituted with aryl or heteroaryl. Amino in which two hydrogens are substituted by aryl is diaryl substituted amino, amino in which two hydrogens are substituted by heteroaryl is diheteroaryl substituted amino, and amino in which two hydrogens are substituted by aryl and heteroaryl is arylheteroaryl substituted amino. As the aryl or heteroaryl, the groups described as “aryl” or “heteroaryl” for R ²¹ to R ²⁸ described above can be cited. In addition, the two aryls of the diaryl substituted amino are not bonded to each other or are bonded through a linking group, and the two heteroaryls of the diheteroaryl substituted amino are not bonded to each other or are bonded through a linking group, The aryl and heteroaryl of the aryl heteroaryl substituted amino are not bonded to each other or are bonded to each other through a linking group.

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

Examples of "halogen" in R ²¹ to R ²⁸ include fluorine, chlorine, bromine and iodine.

Some of the groups described as R ²¹ to R ²⁸ may be substituted as described above, and examples of the substituent in this case include alkyl, cycloalkyl, aryl and heteroaryl. For the alkyl, cycloalkyl, aryl or heteroaryl, the groups described as “alkyl”, “cycloalkyl”, “aryl” or “heteroaryl” for R ²¹ to R ²⁸ described above can be cited.

R ²⁹ in “>NR ²⁹ ” as Y is hydrogen or optionally substituted aryl, and as this aryl, the group described as “aryl” for R ²¹ to R ²⁸ described above can be cited, and as the substituent, The groups described as substituents for R ²¹ to R ²⁸ can be cited.

Adjacent groups among R ²¹ to R ²⁸ may be bonded to each other to form a hydrocarbon ring, an aryl ring or a heteroaryl ring. A case in which a ring is not formed is a group represented by the following formula (A-1), and examples of a case in which a ring is formed include groups represented by the following formulas (A-2) to (A-14). . In addition, at least one hydrogen in the group represented by any one of formulas (A-1) to (A-14) is alkyl, cycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, arylthio, trialkylsilyl, It may be substituted with tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, diaryl substituted amino, diheteroaryl substituted amino, arylheteroaryl substituted amino, halogen, hydroxy or cyano. In addition, the two aryls of the diaryl substituted amino are not bonded to each other or are bonded through a linking group, and the two heteroaryls of the diheteroaryl substituted amino are not bonded to each other or are bonded through a linking group, The aryl and heteroaryl of the aryl heteroaryl substituted amino are not bonded to each other or are bonded to each other through a linking group.

Examples of the ring formed by bonding adjacent groups to each other include a cyclohexane ring as long as it is a hydrocarbon ring, and as an aryl ring or heteroaryl ring, in "aryl" or "heteroaryl" for R ²¹ to R ²⁸ described above. The described ring structure is mentioned, These rings are formed so that it may condense with the 1 or 2 benzene ring in Formula (A-1).

The group represented by the formula (A) is a group obtained by removing one hydrogen at any one position of the formula (A), and * indicates the position. That is, the group represented by Formula (A) may make any one position into a bonding position. For example, any one carbon atom on two benzene rings in the structure of formula (A), any one cyclic atom formed by bonding adjacent groups among R ²¹ to R ²⁸ in the structure of formula (A), or Directly with any position of R ²⁹ in “>NR ²⁹ ” as Y in the structure of formula (A), or N in “>NR ²⁹ ” (R ²⁹ is a bond) It may be a binding group. The same applies to the group represented by any one of formulas (A-1) to (A-14).

Examples of the group represented by the formula (A) include groups represented by any one of formulas (A-1) to (A-14), formulas (A-1) to (A-5) and The group represented by any one of the formulas (A-12) to (A-14) is preferable, and the group represented by any one of the formulas (A-1) to (A-4) is more preferable, and the group represented by the formula (A-1) is more preferable. ), the group represented by any one of the formulas (A-3) and (A-4) is still more preferable, and the group represented by the formula (A-1) is particularly preferable.

As group represented by Formula (A), the following groups are mentioned, for example. Y and * in the formula have the same definitions as above.

In the compound represented by the formula (3-H), the group represented by the formula (A) is a naphthalene ring in the formula (3-X1) or (3-X2), a single bond in the formula (3-X3), and/ Alternatively, a form bonded to Ar ³ in formula (3-X3) is preferable.

In addition, all or part of hydrogen in the chemical structure of the anthracene type compound represented by Formula (3-H) may be deuterium.

The anthracene-based compound as the host may be, for example, a compound represented by the following formula (3-H2).

In formula (3-H2), Ar ^c is optionally substituted aryl or optionally substituted heteroaryl, R ^c is hydrogen, alkyl, or cycloalkyl, Ar ¹¹ , Ar ¹² , Ar ¹³ , Ar ¹⁴ , Ar ¹⁵ , Ar ¹⁶ , Ar ¹⁷ , and Ar ¹⁸ are each independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted diarylamino, or optionally substituted diheteroarylamino , optionally substituted arylheteroarylamino, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted arylthio, Or it is silyl which may be substituted, and at least 1 hydrogen in the compound represented by Formula (1) may be substituted by halogen, cyano, or deuterium. In addition, the two aryls of the optionally substituted diarylamino are not bonded to each other or are bonded through a linking group, and the two heteroaryls of the optionally substituted diheteroarylamino are not bonded to each other, or a linking group. The aryl and heteroaryl of the optionally substituted arylheteroarylamino are not bonded to each other or are bonded through a linking group.

In formula (3-H2), "optionally substituted aryl", "optionally substituted heteroaryl", "optionally substituted diarylamino", "optionally substituted diheteroarylamino", "even substituted "Arylheteroarylamino which may be substituted", "Alkyl which may be substituted", "Cycloalkyl which may be substituted", "Alkenyl which may be substituted", "Alkoxy which may be substituted", "Aryloxy which may be substituted", The definition of "optionally substituted arylthio" or "optionally substituted silyl" is the same as that in the above formula (3-H), and the description in formula (1) can be cited. In addition, the two aryls of the "diarylamino which may be substituted" are not bonded to each other or are bonded through a linking group, and the two heteroaryls of the "diheteroarylamino which may be substituted" are not bonded to each other. Or, they are bonded through a linking group, and the aryl and heteroaryl of the above “arylheteroarylamino which may be substituted” are not bonded to each other or are bonded through a linking group.

The "optionally substituted aryl" is also preferably a group represented by any of the following formulas (3-H2-X1) to (3-H2-X7).

In formulas (3-H2-X1) to (3-H2-X7), * represents a bonding position. In the formulas (3-H2-X1) to (3-H2-X3), Ar ²¹ , Ar ²² , and Ar ²³ are each independently hydrogen, phenyl, biphenylyl, terphenylyl, quaterphenylyl , naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenyl, anthracenyl, or a group represented by the formula (A). In addition, in the description of the formula (3-H2), the group represented by the formula (A) is the same as that described for the anthracene-based compound represented by the formula (3-H).

In formulas (3-H2-X4) to (3-H2-X7), Ar ²⁴ , Ar ²⁵ , Ar ²⁶ , Ar ²⁷ and Ar ²⁸ are each independently hydrogen, phenyl, biphenylyl, or terphenyl lyl, naphthyl, phenanthryl, fluorenyl, chrysenyl, triphenylenyl, pyrenyl, or a group represented by the formula (A). In addition, any one or two or more hydrogens in each of the groups represented by the formulas (3-H2-X1) to (3-H2-X7) is an alkyl having 1 to 6 carbon atoms (preferably methyl or t-butyl) may be substituted.

Furthermore, as a preferable example of "optionally substituted aryl", it is represented by phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, chrysenyl, triphenylenyl, pyrenyl, and formula (A) terphenylyl (particularly, m-terphenyl-5'-yl) which may be substituted with one or more substituents selected from the group consisting of groups is mentioned.

As "heteroaryl which may be substituted", the group represented by Formula (A) is mentioned. In addition, as a specific example of "the aryl which may be substituted" and the "heteroaryl which may be substituted", dibenzofuryl, naphthobenzofuryl, phenyl-substituted dibenzofuryl, etc. are mentioned.

At least one hydrogen in the compound represented by Formula (1) may be substituted with halogen, cyano, or deuterium. Examples of "halogen" in this case include fluorine, chlorine, bromine, and iodine. In particular, a compound in which all hydrogens in the compound represented by formula (3-H2) are substituted with deuterium is preferable.

In formula (3-H2), R ^c is hydrogen, alkyl, or cycloalkyl, preferably hydrogen, methyl, or t-butyl, more preferably hydrogen.

In formula (3-H2), it is preferable that at least two of Ar ¹¹ to Ar ¹⁸ are optionally substituted aryl or optionally substituted heteroaryl. That is, the anthracene-based compound represented by the formula (3-H2) preferably has a structure in which at least three substituents selected from the group consisting of optionally substituted aryl and optionally substituted heteroaryl are bonded to an anthracene ring. .

The anthracene-based compound represented by the formula (3-H2) is aryl or optionally substituted heteroaryl in which two of Ar ¹¹ to Ar ¹⁸ are hydrogen, optionally substituted alkyl, or substituted It is more preferable that it is cycloalkyl which is used, optionally substituted alkenyl, or optionally substituted alkoxy. That is, the anthracene-based compound represented by the formula (3-H2) more preferably has a structure in which three substituents selected from the group consisting of optionally substituted aryl and optionally substituted heteroaryl are bonded to an anthracene ring. .

The anthracene-based compound represented by the formula (3-H2) is aryl or optionally substituted heteroaryl in which any two of Ar ¹¹ to Ar ¹⁸ are substituted, and the other six are hydrogen, methyl, or t-butyl. more preferably.

Furthermore, in formula (3-H2), it is preferable that R ^c is hydrogen, and that any six of Ar ¹¹ to Ar ¹⁸ are hydrogen.

The anthracene compound represented by the formula (3-H2) has the following formula (3-H2-A), (3-H2-B), (3-H2-C), (3-H2-D), or (3 It is preferable that it is an anthracene type compound represented by -H2-E).

In formula (3-H2-A), (3-H2-B), (3-H2-C), (3-H2-D) or (3-H2-E), Ar ^c ', Ar ¹¹ ', Ar ¹² ', Ar ¹³ ', Ar ¹⁴ ', Ar ¹⁵ ', Ar ¹⁷ ', and Ar18' are each independently phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, fluorenyl , benzofluorenyl, chrysenyl, triphenylenyl, pyrenyl, or a group represented by the formula (A), wherein at least one hydrogen in this group is phenyl, biphenylyl, terphenylyl, quaterphenyl It may be substituted with the group represented by reyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenyl, or Formula (A). Here, when all the hydrogens of methylene in fluorenyl and benzofluorenyl are substituted with phenyl, these phenyls may be mutually couple|bonded with a single bond. In the carbon atom of the anthracene ring to which Ar ^c ', Ar ¹¹ ', Ar ¹² ', Ar ¹³ ', Ar ¹⁴ ', Ar ¹⁵ ', Ar ¹⁷ ', and Ar ¹⁸ ' are not bonded, methyl or t-butyl is You may combine.

When Ar ^c ', Ar ¹¹ ', Ar ¹² ', Ar ¹³ ', Ar ¹⁴ ', Ar ¹⁵ ', Ar ¹⁷ ', and Ar ¹⁸ ' are substituted or unsubstituted phenyl or substituted or unsubstituted naphthyl, respectively , is preferably a group represented by any one of the above formulas (3-H2-X1) to (3-H2-X7).

Ar ^c ', Ar ¹¹ ', Ar ¹² ', Ar ¹³ ', Ar ¹⁴ ', Ar ¹⁵ ', Ar ¹⁷ ', and Ar ¹⁸ ' are each independently phenyl, biphenylyl (especially biphenyl-2-yl or biphenyl-4-yl), terphenylyl (particularly m-terphenyl-5'-yl), naphthyl, phenanthryl, fluorenyl, or the above formulas (A-1) to (A-1) It is more preferable that it is a group represented by any one of -4), and in this case, at least one hydrogen in this group is phenyl, biphenylyl, naphthyl, phenanthryl, fluorenyl, or the above formula (A -1) to the group represented by any one of formulas (A-4) may be substituted.

In addition, in the compound represented by formula (3-H2-A), (3-H2-B), (3-H2-C), (3-H2-D), or (3-H2-E) At least one hydrogen may be substituted with halogen, cyano, or deuterium. In addition, the deuterated form is preferable, and the form in which all anthracene rings are deuterated, or the form in which all hydrogen atoms are deuterated is preferable.

Particularly preferred examples of the anthracene-based compound represented by the formula (3-H2) include an anthracene-based compound represented by the following formula (3-H2-Aa).

In formula (3-H2-Aa), Ar ^c ', Ar ¹⁴ ', and Ar ¹⁵ ' are each independently phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorene nyl, chrysenyl, triphenylenyl, pyrenyl, or a group represented by any one of the above formulas (A-1) to (A-11), wherein at least one hydrogen in this group is phenyl, biphenylyl , terphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenyl, or a group represented by any one of formulas (A-1) to (A-11); It may be substituted. Here, when all the hydrogens of methylene in fluorenyl and benzofluorenyl are substituted with phenyl, these phenyls may be mutually couple|bonded with a single bond. In addition, methyl or t-butyl may be substituted for the carbon atom on the anthracene ring to which Ar ^c ', Ar ¹⁴ ', and Ar ¹⁵ ' are not bonded. At least one hydrogen in the compound represented by the formula (3-H2-Aa) is unsubstituted or substituted with halogen or cyano, and at least one hydrogen in the compound represented by the formula (3-H2-Aa) One hydrogen is substituted with deuterium.

In formula (3-H2-Aa), Ar ^c ', Ar ¹⁴ ', and Ar ¹⁵ ' are each independently phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, or the formula ( It is preferably a group represented by any one of A-1) to formula (A-4), and at least one hydrogen in this group is phenyl, naphthyl, phenanthryl, fluorenyl, or formula (A-1) You may be substituted by the group represented by any one of - formula (A-4).

In the compound represented by the formula (3-H2-Aa), it is preferable that at least the hydrogen bonded to the 10-position carbon (the carbon to which Ar ^c ' is bonded is the 9-position) to the anthracene ring is substituted with deuterium. . That is, the compound represented by the formula (3-H2-Aa) is preferably a compound represented by the following formula (3-H2-Ab). In the formula (3-H2-Ab), D is deuterium, and Ar ^c ′, Ar ¹⁴ ′, and Ar ¹⁵ ′ have the same definitions as in the formula (1Aa). D in the formula (1Ab) represents at least that this position is deuterium, and any one or more hydrogens among others in the formula (3-H2-Aa) may be deuterium at the same time, and in the formula (3-H2-Aa) It is also preferable that all the hydrogens in this are deuterium.

Specific examples of the anthracene-based compound include compounds represented by the following formulas. In addition, in the following structural formula, "Me" represents methyl, "D" represents deuterium, and "tBu" represents t-butyl.

Further, as another specific example of the anthracene-based compound, for example, a compound represented by the following formulas (3-131-Y) to (3-179-Y), and a compound represented by the following formulas (3-180-Y) to (3) -182-Y), the following formula (3-183-N), the following formula (3-184-Y) - the formula (3-254-Y), the formula (3-255-Y) - the formula ( 3-269-Y) and compounds represented by the following formulas (3-500) to (3-557) and (3-600) to (3-620). The compound represented by the following formula (3-131-Y) - the formula (3-179-Y), the compound represented by the following formula (3-180-Y) - the formula (3-182-Y), the following formula (3) -183-N), the following formula (3-184-Y) - the formula (3-254-Y), the formula (3-255-Y) - the formula (3-269-Y), and the following formula (3-500) ) to (3-557) and (3-600) to (3-620), hydrogen atoms may be partially or all substituted with deuterium. Y in the formula is -O-, -S-, >NR ²⁹ (R ²⁹ is as defined above) or >C(-R ³⁰ ) ₂ (R ³⁰ is optionally linked aryl or alkyl) and R ²⁹ is, for example, phenyl, and R ³⁰ is, for example, methyl. The formula number is, for example, when Y is O, the formula (3-131-Y) is the formula (3-131-O), and when Y is -S- or >NR ²⁹ , the formula (3-131-Y) 131-S) or formula (3-131-N).

Among these compounds, formula (3-131-Y) to formula (3-134-Y), formula (3-138-Y), formula (3-140-Y) to formula (3-143-Y), formula (3-150-Y), formula (3-153-Y) to formula (3-156-Y), formula (3-166-Y), formula (3-168-Y), formula (3-173- Y), formula (3-177-Y), formula (3-180-Y) to formula (3-183-N), formula (3-185-Y), formula (3-190-Y), formula ( 3-223-Y), formula (3-241-Y), formula (3-250-Y), formula (3-252-Y) to formula (3-254-Y), formula (3-501), Equation (3-507), Equation (3-508), Equation (3-509), Equation (3-513), Equation (3-514), Equation (3-519), Equation (3-521), Equation Compounds represented by (3-538) to (3-547) or (3-600) to (3-620) are preferable. Moreover, it is preferable that Y is -O-.

The anthracene-based compound described above includes a compound having a reactive group at a desired position in the anthracene skeleton, and an anthracene ^- based compound represented by formula (3-H). It can manufacture by applying a Suzuki coupling, a Negishi coupling, and other well-known coupling reaction using the compound which has it as a starting material. Halogen, boronic acid, etc. are mentioned as a reactive group of these reactive compounds. As a specific manufacturing method, the synthesis method in paragraphs [0089] - [0175] of International Publication No. 2014/141725 can be referred to, for example.

<Fluorene-based compound>

The compound represented by the formula (4-H) basically functions as a host.

In formula (4-H),

R ¹ to R ¹⁰ are each independently hydrogen, aryl, heteroaryl (the heteroaryl may be bonded to the fluorene skeleton in formula (4-H) through a linking group), diarylamino (two Aryl is not bonded to each other or may be bonded through a linking group), diheteroarylamino (two heteroaryls may not be bonded to each other or may be bonded to each other via a single bond or a linking group), arylheteroarylamino (aryl and Heteroaryl is not bonded to each other or may be bonded through a single bond or a linking group), alkyl, cycloalkyl, alkenyl, alkoxy or aryloxy, and at least one hydrogen in these is aryl, heteroaryl, alkyl or unsubstituted or substituted with cycloalkyl and furthermore, R ¹ and R ² , R ² and R ³ , R ³ and R ⁴ , R ⁵ and R ⁶ , R ⁶ and R ⁷ , R ⁷ and R ⁸ or R ⁹ and R ¹⁰ are each independently combined to form a condensed ring or a spiro ring, or at least one hydrogen in the formed ring is aryl, heteroaryl (the heteroaryl is the corresponding formed through a linking group) may be bonded to a ring), diarylamino (two aryls may not be bonded to each other or may be bonded via a linking group), diheteroarylamino (two heteroaryls may not be bonded to each other or via a single bond or linking group) may be bonded), arylheteroarylamino (aryl and heteroaryl may not be bonded to each other or may be bonded through a single bond or a linking group), alkyl, cycloalkyl, alkenyl, alkoxy or aryloxy, or substituted, wherein at least one hydrogen in these is unsubstituted or substituted with aryl, heteroaryl, alkyl or cycloalkyl, and at least one hydrogen in the compound represented by formula (4-H) may be substituted with halogen, cyano or deuterium.

For details of each group in the definition of the formula (4-H), the description of the polycyclic aromatic compound of the formula (1) described above can be cited.

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

In addition, as a specific example of heteroaryl, any one of the compounds of formula (4-Ar1), formula (4-Ar2), formula (4-Ar3), formula (4-Ar4) or formula (4-Ar5) and a monovalent group represented by removing a hydrogen atom of

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

These heteroaryl may couple|bond with the fluorene skeleton in Formula (4-H) via a coupling group. That is, not only the fluorene skeleton in Formula (4-H) and the said heteroaryl couple|bond directly, but you may couple|bond together via a coupling group between them. Examples of the linking group include phenylene, biphenylene, naphthylene, anthracenylene, methylene, ethylene, -OCH ₂ CH ₂ -, -CH ₂ CH ₂ O-, or -OCH ₂ CH ₂ O-. have.

In addition, in Formula (4-H), R ¹ and R ² , R ² and R ³ , R ³ and R ⁴ , R ⁵ and R ⁶ , R ⁶ and R ⁷ or R ⁷ and R ⁸ are each independently bonded to each other, In the condensed ring, R ⁹ and R ¹⁰ may combine to form a spiro ring. The condensed ring formed by R ¹ to R ⁸ is a ring condensed on the benzene ring in the formula (4-H), and is an aliphatic ring or an aromatic ring. Preferably, it is an aromatic ring, and a naphthalene ring, a phenanthrene ring, etc. are mentioned as a structure which included the benzene ring in Formula (4-H). The spiro ring formed by R ⁹ and R ¹⁰ is a ring spiro-coupled to the 5-membered ring in formula (4-H), and is an aliphatic ring or an aromatic ring. Preferably, it is an aromatic ring, and a fluorene ring etc. are mentioned.

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

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

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

The definitions of R ² to R ⁷ in the formulas (4-H-1A), (4-H-2A) and (4-H-3A) are the formulas (4-H-1) and (4-H-3A). It is the same as the corresponding R ² to R ⁷ in the formulas (H-2) and (4-H-3), and R ¹¹ to R in the formulas (4-H-1A) and (4-H-2A). The definition of ¹⁴ is also the same as that of R ¹¹ to R ¹⁴ in formulas (4-H-1) and (4-H-2).

In addition, all or part of hydrogen in the compound represented by Formula (4-H) may be substituted by halogen, cyano, or deuterium.

As a more specific example of the fluorene type compound as a host of this invention, the compound represented by the following structural formula is mentioned. In addition, "Me" represents methyl.

<Dibenzochrysene-based compound>

The dibenzochrysene-based compound as a host is, for example, a compound represented by the following formula (5-H).

In formula (5-H), R ¹ to R ¹⁶ are each independently hydrogen, aryl, heteroaryl (the heteroaryl is bonded to the dibenzochrysene skeleton in formula (5-H) through a linking group, and may be), diarylamino (two aryls may not be bonded to each other or may be bonded through a linking group), diheteroarylamino (two heteroaryls may not be bonded to each other or may be bonded to each other via a single bond or a linking group) ), arylheteroarylamino (aryl and heteroaryl may not be bonded to each other or may be bonded through a single bond or a linking group), alkyl, cycloalkyl, alkenyl, alkoxy or aryloxy, and at least one of them hydrogen is not substituted with aryl, heteroaryl, alkyl or cycloalkyl, or is substituted, and adjacent groups of R ¹ to R ¹⁶ are bonded to each other to form a condensed ring, or are formed At least one hydrogen in the ring is aryl, heteroaryl (the heteroaryl may be bonded to the ring formed through a linking group), diarylamino (two aryls may not be bonded to each other or may be bonded to each other via a linking group) ), diheteroarylamino (two heteroaryls are not bonded to each other or may be bonded through a single bond or a linking group), arylheteroarylamino (aryl and heteroaryl are not bonded to each other, or through a single bond or a linking group) may be bonded), unsubstituted or substituted with alkyl, cycloalkyl, alkenyl, alkoxy or aryloxy, and at least one hydrogen in these is not substituted with aryl, heteroaryl, alkyl or cycloalkyl or is substituted, and at least one hydrogen in the compound represented by formula (5-H) may be substituted with halogen, cyano or deuterium.

For the details of each group in the definition of the formula (5-H), the description of the polycyclic aromatic compound of the formula (1) described above can be cited.

As alkenyl in the definition of formula (5-H), a C2-C30 alkenyl is mentioned, for example, C2-C20 alkenyl is preferable, C2-C10 alkenyl is More preferably, alkenyl having 2 to 6 carbon atoms is still more preferable, and alkenyl having 2 to 4 carbon atoms is particularly preferable. Preferred alkenyls are vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pen tenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, or 5-hexenyl.

In addition, as a specific example of heteroaryl, any one of the compounds of formula (5-Ar1), formula (5-Ar2), formula (5-Ar3), formula (5-Ar4) or formula (5-Ar5) and a monovalent group represented by removing a hydrogen atom of

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

These heteroaryl may be couple|bonded with the dibenzochrysene skeleton in Formula (5-H) via a coupling group. That is, not only the dibenzochrysene skeleton in Formula (5-H) and the said heteroaryl couple|bond directly, but you may couple|bond via a coupling group between them. Examples of the linking group include phenylene, biphenylene, naphthylene, anthracenylene, methylene, ethylene, -OCH ₂ CH ₂ -, -CH ₂ CH ₂ O-, or -OCH ₂ CH ₂ O-. have.

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

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

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

As a more specific example of the dibenzochrysene type compound as a host of this invention, the compound represented by the following structural formula is mentioned. In addition, "tBu" represents t-butyl.

The material for the light emitting layer (host material and dopant material) described above is a polymer compound obtained by polymerizing a reactive compound substituted with a reactive substituent as a monomer, or a polymer crosslinked product thereof, or a main chain polymer and the reactive compound. The reacted pendant polymer compound or the pendant polymer crosslinked product can also be used as a material for a light emitting layer. As a reactive substituent in this case, the description in the polycyclic aromatic compound represented by Formula (1) can be cited.

<Emissive Layer Containing Assisting Dopant and Emitting Dopant>

The light emitting layer in an organic electroluminescent element may contain a host compound as a 1st component, an assisting dopant (compound) as a 2nd component, and an emitting dopant (compound) as a 3rd component. The polycyclic aromatic compound of the present invention is also preferably used as an emitting dopant. As the assisting dopant (compound), a thermally activated delayed phosphor can be used.

In the following description, an organic electroluminescent device using a thermally activated delayed phosphor as an assisting dopant may be referred to as a "TAF element" (TADF Assisting Fluorescence element). The "host compound" in the TAF element means that the lowest singlet excitation energy level obtained from the shoulder on the short wavelength side of the peak of the fluorescence spectrum is higher than that of the thermally activated delayed phosphor as the second component and the emitting dopant as the third component. high compound.

"Thermal-activated delayed phosphor" means that it absorbs thermal energy, causes an inverse crossover from the lowest triplet excitation state to the lowest singlet excitation state, and causes radiation deactivation from the lowest singlet state to emit delayed fluorescence. means a compound. However, "thermal-activated delayed fluorescence" also includes passing through a higher-order triplet in the excitation process from the lowest triplet excited state to the lowest singlet excited state. For example, a paper by Durham University Monkmans (NATURE COMMUNICATIONS, 7:13680, DOI:10.1038/ncomms13680), a paper by Hosokai et al., Sci.Adv.2017;3: e1603282), a paper by Kyoto University Satos (Scientific Reports, 7:4820, DOI:10.1038/s41598-017-05007-7), and similarly presented at a conference by Kyoto University Satos (the 98th Spring Banquet of the Japanese Chemical Society, Publication No.: 2I4-15, a high-efficiency luminescence mechanism in organic electroluminescence using DABNA as a luminescent molecule, Kyoto University Graduate School of Engineering) and the like. In the present invention, when the fluorescence lifetime of a sample containing the target compound is measured at 300 K, a slow fluorescence component is observed, and it is determined that the target compound is a "thermally activated delayed phosphor". Here, the slow fluorescence component means that the fluorescence lifetime is 0.1 µsec or more. The fluorescence lifetime can be measured using, for example, a fluorescence lifetime measuring device (manufactured by Hamamatsu Photonics, C11367-01).

The polycyclic aromatic compound of the present invention can function as an emitting dopant, and the "thermal activated delayed phosphor" can function as an assisting dopant that assists light emission of the polycyclic aromatic compound of the present invention.

FIG. 2 shows an energy level diagram of a light emitting layer of a TAF device using a general fluorescent dopant as an emitting dopant (ED). In the figure, the energy level of the ground state of the host is E(1, G), the lowest singlet excitation energy level obtained from the shoulder on the short-wavelength side of the host fluorescence spectrum is E(1, S, Sh), and the phosphorescence spectrum of the host is short-wavelength. The lowest triplet excitation energy level obtained from the shoulder of the side is E(1, T, Sh), the ground state energy level of the assisting dopant as the second component is E(2, G), and that of the assisting dopant as the second component. E(2, S, Sh) is the lowest singlet excitation energy level obtained from the shoulder on the short wavelength side of the fluorescence spectrum, and E is the lowest triplet excitation energy level obtained from the shoulder on the short wavelength side of the phosphorescence spectrum of the second component, an assisting dopant. (2, T, Sh), the ground state energy level of the emitting dopant as the third component is E(3, G), and the lowest singlet excitation energy obtained from the shoulder on the short wavelength side of the fluorescence spectrum of the emitting dopant as the third component. The level is E(3, S, Sh); e-, fluorescence resonance energy transfer is referred to as FRET (Fluorescence Resonance Energy Transfer). In the TAF device, when a general fluorescent dopant is used as the emitting dopant (ED), the energy upconverted from the assisting dopant moves to the lowest singlet excitation energy level E(3, S, Sh) of the emitting dopant and emits light. do. However, the lowest triplet excitation energy E(2, T, Sh) of some on the assisting dopant shifts to the lowest triplet excitation energy level E(3, T, Sh) of the emitting dopant, or the lowest excitation on the emitting dopant. Interterminal crossover from singlet energy level E(3, S, Sh) to lowest excited triplet energy level E(3, T, Sh) occurs, and then thermally to ground state E(3, G) come alive A part of energy is not used for light emission by this path, and energy is wasted.

In contrast, in the organic electroluminescent device of the present embodiment, the energy transferred from the assisting dopant to the emitting dopant can be efficiently used for light emission, thereby realizing high light emission efficiency. This is presumed to be due to the following light emission mechanism.

A preferable energy relationship in the organic electroluminescent device of this embodiment is shown in FIG. 3 . In the organic electroluminescent device of this embodiment, a compound having a boron atom as an emitting dopant has a high lowest triplet excitation energy level E(3, T, Sh). For this reason, even when the lowest singlet excitation energy upconverted in the assisting dopant intersects with the lowest triplet excitation energy level E(3, T, Sh) in the emitting dopant, upconversion on the emitting dopant or the lowest excitation triplet energy level E(2, T, Sh) on the assisting dopant (thermally activated delayed phosphor). Therefore, the generated excitation energy can be used for light emission without wasting. Further, by dividing the upconversion and luminescence functions into two types of molecules each capable of good functions, it is expected that the residence time of high energy is reduced and the burden on the compound is reduced.

In this aspect, a well-known thing can be used as a host compound, For example, the compound which has at least one of a carbazole ring and a furan ring is mentioned, Especially, at least one of furanyl and carbazolyl, and aryl It is preferable to use a compound in which at least one of ene and heteroarylene is bonded. As a specific example, mCP, mCBP, etc. are mentioned.

The lowest triplet excitation energy level E (1, T, Sh) obtained from the shoulder on the short wavelength side of the peak of the phosphorescence spectrum of the host compound is the highest in the light emitting layer from the viewpoint of accelerating the generation of TADF in the light emitting layer without inhibiting it. Higher than the lowest triplet excitation energy levels E(2, T, Sh), E(3, T, Sh) of the emitting dopant or assisting dopant having a high lowest triplet excitation energy level is preferable, and specifically As, the lowest triplet excitation energy level E(1, T, Sh) of the host compound is preferably 0.01 eV or more, compared with E(2, T, Sh), E(3, T, Sh), and 0.03 eV or more is more preferable, and 0.1 eV or more is still more preferable. Moreover, you may use the compound which is TADF active for a host compound.

As the host compound, for example, a compound represented by any one of the formulas (H1), (H2) and (H3) can be used.

<Heat-activated delayed phosphor (assisting dopant)>

The thermally activated delayed phosphor (TADF compound) used in the TAF device uses an electron-donating substituent called a donor and an electron-accepting substituent called an acceptor to form a Highest Occupied Molecular Orbital (HOMO) and Lowest Unoccupied Molecular Orbital (LUMO) in a molecule. It is preferable that it is a donor-acceptor type thermally activated delayed fluorescent substance (D-A type TADF compound) designed to localize Molecular Orbital so that efficient reverse intersystem crossing occurs. Here, in the present specification, "electron-donating substituent" (donor) means a substituent and partial structure in which the HOMO orbital is localized in a thermally activated delayed phosphor molecule, and "electron-accepting substituent" (acceptor) is, It shall mean the substituent and partial structure in which the LUMO orbital is localized among thermally activated delayed fluorescent substance molecules.

In general, a thermally activated delayed phosphor using a donor or acceptor has a large spin orbit coupling (SOC) due to its structure, while at the same time an exchange interaction between HOMO and LUMO is small and ΔE(ST) is small. Therefore, a very fast inter-inverse crossover speed is obtained. On the other hand, in thermally activated delayed phosphors using donors or acceptors, the structural relaxation in the excited state is large (for some molecules, the stable structure is different between the ground state and the excited state, When conversion occurs, the structure changes to a stable structure in the excited state after that), providing a broad emission spectrum, so that when used as a light emitting material, there is a possibility that the color purity may be lowered.

As the thermally activated delayed phosphor in the TAF device, for example, a compound in which a donor and an acceptor are directly or via a spacer can be used. As the electron-donating group (donor-like structure) and electron-accepting group (acceptor-like structure) used in the thermally activated delayed phosphor of the present invention, for example, the structure described in Chemistry of Materials, 2017, 29, 1946-1963 Can be used. Examples of the donor structure include carbazole, dimethylcarbazole, di-tert-butylcarbazole, dimethoxycarbazole, tetramethylcarbazole, benzofluorocarbazole, benzothienocarbazole, phenyldihydroindolocarbazole, Phenylbicarbazole, bicarbazole, tercarbazole, diphenylcarbazolylamine, tetraphenylcarbazolyldiamine, phenoxazine, dihydrophenazine, phenothiazine, dimethyldihydroacridine, diphenylamine, bis (tert-butyl phenyl)amine, N1-(4-(diphenylamino)phenyl)-N4,N4-diphenylbenzene-1,4-diamine, dimethyltetraphenyldihydroacridinediamine, tetramethyl-dihydro Noacridine, diphenyl dihydrodibenzoazacilline, etc. are mentioned. Examples of the acceptor structure include sulfonyldibenzene, benzophenone, phenylenebis(phenylmethanone), benzonitrile, isonicotinonitrile, phthalonitrile, isophthalonitrile, paraphthalonitrile, benzenetricarbonitrile, and triazole. , oxazole, thiadiazole, benzothiazole, benzobis (thiazole), benzoxazole, benzobis (oxazole), quinoline, benzoimidazole, dibenzoquinoxaline, heptaazaphenalene, thioxanthone dioxide , Dimethylanthracenone, anthracenedione, 5H-cyclopenta[1,2-b:5,4-b']dipyridine, fluorenedicarbonitrile, triephenyltriazine, pyrazinedicarbonitrile, pyrimidine, phenyl pyrimidine, methylpyrimidine, pyridinedicarbonitrile, dibenzoquinoxaline dicarbonitrile, bis(phenylsulfonyl)benzene, dimethylthioxanthene dioxide, thianthrenetetraoxide and tris(dimethylphenyl)borane. In particular, the compound having thermally activated delayed fluorescence in the TAF device has, as a partial structure, carbazole, phenoxazine, acridine, triazine, pyrimidine, pyrazine, thioxanthene, benzonitrile, phthalonitrile, and isop. It is preferably a compound having at least one selected from talonitrile, diphenylsulfone, triazole, oxadiazole, thiadiazole and benzophenone.

It is preferable that the compound used as the second component of the light emitting layer in the TAF element is a thermally activated delayed phosphor, and is a compound whose emission spectrum overlaps at least partially with the absorption peak of the emitting dopant. Below, the compound which can be used as a 2nd component (thermally activated delayed fluorescent substance) of the light emitting layer in a TAF element is illustrated. However, compounds that can be used as thermally activated delayed phosphors in the TAF device are not limitedly interpreted by the following exemplary compounds. In the following formula, Me represents methyl, t-Bu represents t-butyl, and the broken line represents the bonding position.

Further, as the thermally activated delayed phosphor, a compound represented by any one of the following formulas (AD1), (AD2) and (AD3) can also be used.

In the formulas (AD1), (AD2) and (AD3), M is each independently a single bond, -O-, >N-Ar or >CAr ₂ , and the depth and lowest excitation of the HOMO of the partial structure to be formed. In view of the height of the singlet energy level and the lowest triplet excited energy level, it is preferably a single bond, -O- or >N-Ar. J is a spacer structure dividing the partial structure of the donor property and the partial structure of the acceptor property, each independently an arylene having 6 to 18 carbon atoms, from the viewpoint of the size of the conjugate exuding from the partial structure of the donor property and the partial structure of the acceptor property, Arylene having 6 to 12 carbon atoms is preferable. More specifically, phenylene, methylphenylene, and dimethylphenylene are mentioned. Q is, each independently, =C(-H)- or =N-, from the viewpoint of the shallowness of the LUMO of the forming partial structure and the height of the lowest singlet excitation energy level and the lowest triplet excitation energy level, preferably , =N-. Ar is each independently hydrogen, aryl having 6 to 24 carbon atoms, heteroaryl having 2 to 24 carbon atoms, alkyl having 1 to 12 carbon atoms, or cycloalkyl having 3 to 18 carbon atoms, the depth and minimum of the HOMO of the partial structure to be formed From the viewpoint of the height of the singlet excitation energy level and the lowest triplet excitation energy level, preferably hydrogen, aryl having 6 to 12 carbon atoms, heteroaryl having 2 to 14 carbon atoms, alkyl having 1 to 4 carbon atoms or 6 to 10 carbon atoms Cycloalkyl, more preferably hydrogen, phenyl, tolyl, xylyl, mesityl, biphenyl, pyridyl, bipyridyl, triazyl, carbazolyl, dimethylcarbazolyl, di-tert-butylcarba zolyl, benzoimidazole or phenyl benzoimidazole, even more preferably hydrogen, phenyl or carbazolyl. m is 1 or 2. n is an integer of - (6-m), and preferably an integer of 4 - (6-m) from the viewpoint of steric hindrance. In addition, at least 1 hydrogen in the compound represented by said each formula may be substituted by halogen or deuterium.

The compound used as the second component of this embodiment is, more specifically, 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 are preferred.

The compound used as the second component of this embodiment may be a donor-acceptor-type TADF compound represented by D-A in which one donor D and one acceptor A are directly bonded or bonded through a linking group, but one acceptor A It is preferable to have a structure represented by the following formula (DAD1) in which a plurality of donors D are bonded to each other through a direct bond or a linking group, since the characteristics of the organic electroluminescent device are more excellent.

(D ¹ -L ¹ )nA ¹ (DAD1)

The compound represented by a following formula (DAD2) is contained in Formula (DAD1).

D ² -L ² -A ² -L ³ -D ³ (DAD2)

In formulas (DAD1) and (DAD2), D ¹ , D ² , and D ³ each independently represent a donor group. As a donor group, the said donor structure is employable. A ¹ and A ² each independently represent an acceptor group. As the acceptor group, the above acceptor structure can be adopted. L ¹ , L ² , and L ³ each independently represent a single bond or a conjugated linking group. The conjugated linking group is a spacer structure that separates the donor group and the acceptor group, and is preferably arylene having 6 to 18 carbon atoms, more preferably arylene having 6 to 12 carbon atoms. It is even more preferable that L ¹ , L ² and L ³ are each independently phenylene, methylphenylene or dimethylphenylene. n in formula (DAD1) is 2 or more, and A< ¹ > represents the integer less than the maximum number which can be substituted. n may be selected, for example, within the range of 2 to 10, or may be selected within the range of 2 to 6. When n is 2, it becomes a compound represented by Formula (DAD2). n pieces of D ¹ may be the same or different, and n pieces of L ¹ may be the same or different. Preferred specific examples of the compounds represented by the formulas (DAD1) and (DAD2) include 2PXZ-TAZ and the following compounds, but the second component that can be employed in the present invention is not limited to these compounds.

In this aspect, a single layer may be sufficient as a light emitting layer, or even if it consists of multiple layers, either may be sufficient as it. In addition, the host compound, the thermally activated delayed fluorescent substance, and the polycyclic aromatic compound of this invention may be contained in the same layer, and at least one component may be contained in multiple layers at a time. The number of each of the host compound, the thermally activated delayed fluorescent substance, and the polycyclic aromatic compound of the present invention included in the light emitting layer may be one, a plurality of combinations, or any may be sufficient. The assisting dopant and the emitting dopant may be contained entirely or partially contained in the host compound as a matrix. The light emitting layer doped with the assisting dopant and the emitting dopant is deposited at the same time after mixing the host compound, the assisting dopant, and the emitting dopant in advance, a method of forming a film of the host compound, the assisting dopant, and the emitting dopant by a ternary co-evaporation method. It can be formed by a wet film forming method or the like in which a composition (paint) for forming a light emitting layer prepared by dissolving a host compound, an assisting dopant, and an emitting dopant in an organic solvent is applied.

The amount of the host compound used varies depending on the type of the host compound, and may be determined according to the characteristics of the host compound. The standard of the usage-amount of a host compound becomes like this. Preferably it is 40-99.999 mass % of the whole material for light emitting layers, More preferably, it is 50-99.99 mass %, More preferably, it is 60-99.9 mass %. If it is the above range, for example, it is preferable from the point of efficient electric charge transport and efficient energy transfer to a dopant.

The amount of the assisting dopant (thermally activated delayed phosphor) to be used varies depending on the type of the assisting dopant, and may be determined according to the characteristics of the assisting dopant. The standard of the usage-amount of an assisting dopant becomes like this. Preferably it is 1-60 mass % of the whole light emitting layer material, More preferably, it is 2-50 mass %, More preferably, it is 5-30 mass %. If it is the above range, for example, it is preferable at the point of efficiently transferring energy to an emitting dopant.

The amount of the emitting dopant (compound having a boron atom) to be used varies depending on the type of the emitting dopant, and may be determined according to the characteristics of the emitting dopant. The standard of the amount of the emitting dopant to be used is preferably 0.001 to 30 mass%, more preferably 0.01 to 20 mass%, still more preferably 0.1 to 10 mass%, based on the total amount of the light emitting layer material. If it is the above-mentioned range, it is preferable at the point that a density|concentration quenching phenomenon can be prevented, for example.

The amount of the emitting dopant to be used is preferably at a low concentration in that it is possible to prevent the concentration quenching phenomenon. A high concentration of the assisting dopant used is preferable from the viewpoint of the efficiency of the thermally activated delayed fluorescence mechanism. In addition, from the viewpoint of the efficiency of the thermally activated delayed fluorescence mechanism of the assisting dopant, it is preferable that the amount of the emitting dopant used is lower than that of the assisting dopant.

2-1-3. Substrate in organic electroluminescent device

The substrate 101 is a support body of the organic EL element 100, and usually quartz, glass, metal, plastic, or the like is used. The substrate 101 is formed in a plate shape, a film shape, or a 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. In the case of a glass substrate, soda-lime glass, an alkali-free glass, etc. are used, and since thickness also just needs to have sufficient thickness in order to maintain mechanical strength, what is necessary is just 0.2 mm or more, for example. As an upper limit of thickness, it is 2 mm or less, for example, Preferably it is 1 mm or less. About the material of glass, since it is good that there are few ions eluted from glass, although alkali-free glass is preferable, since soda _- lime glass which gave barrier coating, such as SiO2, is also marketed, it can be used. In addition, in order to improve gas barrier properties, a gas barrier film such as a dense silicon oxide film may be formed on at least one surface of the substrate 101, and a synthetic resin plate, film or sheet having particularly low gas barrier properties is applied to the substrate. When using (101), it is preferable to form a gas barrier film.

2-1-4. Anode in organic electroluminescent element

The anode 102 serves to inject holes into the light emitting layer 105 . Further, when the hole injection layer 103 and/or 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 through these.

Examples of the material for forming the anode 102 include inorganic compounds and organic compounds. Examples of the inorganic compound include metals (aluminum, gold, silver, nickel, palladium, chromium, etc.), metal oxides (indium oxide, tin oxide, indium-tin oxide (ITO), indium-zinc oxide (IZO)) etc.), a metal halide (copper iodide etc.), copper sulfide, carbon black, ITO glass, Nessa glass, etc. are mentioned. Examples of the organic compound include polythiophene such as poly(3-methylthiophene), and conductive polymers such as polypyrrole and polyaniline. In addition, it can be used by selecting suitably from the materials used as an anode of an organic electroluminescent element.

The resistance of the transparent electrode is not limited as long as it can supply a sufficient current for light emission of the light emitting element, but is preferably low resistance from the viewpoint of power consumption of the light emitting element. For example, an ITO substrate of 300 Ω/square or less functions as an element electrode, but now it is possible to supply a substrate of about 10 Ω/square, for example, 100 to 5 Ω/square, preferably 50 to 5Ω/square It is particularly preferable to use a low-resistance product of Although the thickness of ITO can be arbitrarily selected according to a resistance value, Usually, it is used between 50-300 nm in many cases.

2-1-5. A hole injection layer and a hole transport layer in an organic electroluminescent device

The hole injection layer 103 serves to efficiently inject holes moving from the anode 102 into the light emitting layer 105 or the hole transport layer 104 . The hole transport layer 104 serves to efficiently transport 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 . Each of the hole injection layer 103 and the hole transport layer 104 is formed by laminating and mixing one or two or more of the hole injection/transport material, or a mixture of the hole injection/transport material and the polymer binder. In addition, an inorganic salt such as iron (III) chloride may be added to the hole injection/transport material to form a layer.

As the hole injection/transport material, it is necessary to efficiently inject and transport holes from the positive electrode between the electrodes to which an electric field is applied, and it is preferable that the hole injection efficiency is high and the injected holes are efficiently transported. For this purpose, it is preferable that the ionization potential is small, the hole mobility is large, and furthermore, the material is excellent in stability, and the impurity that becomes a trap is difficult to generate during manufacture and use.

As a material for forming the hole injection layer 103 and the hole transport layer 104, a compound conventionally used as a charge transport material for holes in a photoconductive material, a p-type semiconductor, a hole injection layer and a hole of an organic EL device. Any compound can be selected and used from known compounds used for the transport layer. Specific examples of these include carbazole derivatives (N-phenylcarbazole, polyvinylcarbazole, etc.), biscarbazole derivatives such as bis(N-arylcarbazole) or bis(N-alkylcarbazole), triarylamine Derivatives (4,4',4"-tris(N-carbazolyl)triphenylamine, polymers having aromatic tertiary amino in the main chain or side chains, 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, N4,N4'-diphenyl-N4,N4'-bis(9-phenyl-9H-carbox bazol-3-yl)-[1,1'-biphenyl]-4,4'-diamine, N4,N4,N4',N4'-tetra[1,1'-biphenyl]-4-yl)- Triphenylamine derivatives such as [1,1'-biphenyl]-4,4'-diamine, 4,4',4"-tris(3-methylphenyl(phenyl)amino)triphenylamine, starburstamine derivatives, etc. ), stilbene derivatives, phthalocyanine derivatives (metal-free, copper phthalocyanine, etc.), pyrazoline derivatives, hydrazone compounds, benzofuran derivatives or thiophene derivatives, oxadiazole derivatives, quinoxaline derivatives (e.g., 1,4, 5,8,9,12-hexaazatriphenylene-2,3,6,7,10,11-hexacarbonitrile, etc.), heterocyclic compounds such as porphyrin derivatives, polysilane, and the like. Polycarbonate, styrene derivatives, polyvinylcarbazole, polysilane, etc. having the above monomers in the side chain are preferable in the polymer system. It will not specifically limit if it is a compound which can transport.

Moreover, it is also known that the electroconductivity of an organic semiconductor is strongly influenced by the doping. Such an organic semiconductor matrix material is composed of a compound having good electron donating property or a compound having good electron acceptability. For doping of the electron donor material, a strong electron acceptor such as tetracyanoquinonedimethane (TCNQ) or 2,3,5,6-tetrafluorotetracyano-1,4-benzoquinonedimethane (F4TCNQ) is used. known (eg, M. Pfeiffer, A. Beyer, T. Fritz, K. Leo, Appl. Phys. Lett., 73 (22), 3202-3204 (1998) and J. Blochwitz , M. Pfeiffer, 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 type base material (hole-transporting material). Depending on the number and mobility of holes, the conductivity of the base material changes significantly. As a matrix material having hole transport properties, for example, benzidine derivatives (TPD, etc.) or starburstamine derivatives (TDATA, etc.), or specific metal phthalocyanines (especially zinc phthalocyanine (ZnPc) etc.) are known (Japanese Patent Laid-Open No. Publication No. 2005-167175). The polycyclic aromatic compound of the present invention may be used as a material for forming a hole injection layer or a material for forming a hole transport layer.

2-1-6. Electron blocking layer in organic electroluminescent device

An electron blocking layer for preventing diffusion of electrons from the light emitting layer may be formed between the hole injecting/transporting layer and the light emitting layer. The compound represented by any one of Formula (H1), (H2) and (H3) mentioned above can be used for formation of an electron blocking layer. The polycyclic aromatic compound of the present invention may be used as a material for forming an electron blocking layer.

<Electron injection layer and electron transport layer in organic electroluminescent element>

The electron injection layer 107 serves to efficiently inject electrons moving from the cathode 108 into the light emitting layer 105 or the electron transport layer 106 . The electron transport layer 106 serves to efficiently transport electrons injected from the cathode 108 or electrons injected from the cathode 108 through 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 one or two or more types of electron transporting/injecting materials, or by mixing the electron transporting/injecting materials with a polymer binder.

The electron injection/transport layer is a layer in which electrons are injected from the cathode and is responsible for transporting electrons, and it is preferable that the electron injection efficiency is high and the injected electrons are transported efficiently. For this purpose, it is preferable that the material is a material having high electron affinity, high electron mobility, excellent stability, and difficult to generate trap impurities during manufacture and use. However, in the case of considering the transport balance of holes and electrons, if the main role is to effectively block the flow of holes from the anode to the cathode without recombination, the luminous efficiency is improved even if the electron transport ability is not very high. The effect is equivalent to that of a material having a high electron transport ability. Therefore, the electron injection/transport layer in this embodiment may also contain the function of the layer which can block|block the movement of a hole efficiently.

As a material (electron transport material) forming the electron transport layer 106 or the electron injection layer 107, a compound conventionally used as an electron transport compound in a photoconductive material, an electron injection layer and an electron transport layer of an organic EL device It can be used arbitrarily selected from known compounds used.

Examples of the material used for the electron transport layer or the electron injection layer include compounds comprising an aromatic ring or heteroaromatic ring composed of one or more atoms selected from carbon, hydrogen, oxygen, sulfur, silicon and phosphorus, pyrrole derivatives and condensed ring derivatives thereof; It is preferable to contain at least 1 sort(s) chosen from the metal complex which has electron-accepting nitrogen. Specifically, condensed ring derivatives such as naphthalene and anthracene, styryl aromatic ring derivatives typified by 4,4'-bis(diphenylethenyl)biphenyl, perinone derivatives, coumarin derivatives, and naphthalimide derivatives and quinone derivatives such as anthraquinone and diphenoquinone, phosphine oxide derivatives, arylnitrile derivatives, and indole derivatives. Examples of the metal complex having electron-accepting nitrogen include hydroxyazole complexes such as hydroxyphenyloxazole complex, azomethine complex, tropolone metal complex, flavonol metal complex, and benzoquinoline metal complex. These materials may be used alone, but may be used in combination with other materials.

Further, as specific examples of other electron transport compounds, pyridine derivatives, naphthalene derivatives, fluoranthene derivatives, BO derivatives, anthracene derivatives, phenanthroline derivatives, perinone derivatives, coumarin derivatives, naphthalimide derivatives, anthraquinone derivatives , diphenoquinone derivatives, diphenylquinone derivatives, perylene derivatives, oxadiazole derivatives (1,3-bis[(4-t-butylphenyl)1,3,4-oxadiazolyl]phenylene, etc.), thi Offene derivatives, triazole derivatives (N-naphthyl-2,5-diphenyl-1,3,4-triazole, etc.), thiadiazole derivatives, metal complexes of auxin derivatives, quinolinol-based metal complexes, quinoxaline derivatives , quinoxaline derivative polymer, benzazole compound, gallium complex, pyrazole derivative, perfluorinated phenylene derivative, triazine derivative, pyrazine derivative, benzoquinoline derivative (2,2'-bis(benzo[h]quinoline- 2-yl)-9,9'-spirofluorene etc.), imidazopyridine derivatives, borane derivatives, benzimidazole derivatives (tris(N-phenyl benzoimidazol-2-yl)benzene, etc.), benzoxazole derivatives , thiazole derivatives, benzothiazole derivatives, quinoline derivatives, oligopyridine derivatives such as terpyridine, bipyridine derivatives, terpyridine derivatives (1,3-bis(2,2':6',2"-terpyridine-4) '-yl)benzene, etc.), naphthyridine derivatives (bis(1-naphthyl)-4-(1,8-naphthyridin-2-yl)phenyl phosphine oxide, etc.), ardazine derivatives, pyrimidine derivatives, aryl and nitrile derivatives, indole derivatives, phosphine oxide derivatives, bisstyryl derivatives, silol derivatives and azoline derivatives.

Metal complexes having electron-accepting nitrogen may also be used, for example, hydroxyazole complexes such as quinolinol-based metal complexes and hydroxyphenyloxazole complexes, azomethine complexes, tropolone metal complexes, and flavonol metal complexes. and a benzoquinoline metal complex.

The above-mentioned materials may be used alone, but may be used in combination with other materials.

Among the above materials, borane derivatives, pyridine derivatives, fluoranthene derivatives, BO derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, arylnitrile derivatives, triazine derivatives, benzoimidazole derivatives, Phenanthroline derivatives, quinolinol-based metal complexes, thiazole derivatives, benzothiazole derivatives, silol derivatives and azoline derivatives are preferable.

The polycyclic aromatic compound of the present invention may be used as a material for forming an electron injection layer or a material for forming an electron transport layer.

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. Various substances are used as the reducing substance as long as it has a certain reducing property, for example, alkali metals, alkaline earth metals, rare earth metals, alkali metal oxides, alkali metal halides, alkaline earth metal oxides, alkaline earth metals. At least one selected from the group consisting of metal halides, rare earth metal oxides, rare earth metal halides, alkali metal organic complexes, alkaline earth metal organic complexes and rare earth metal organic complexes can be preferably used.

Preferred reducing substances include alkali metals such as Na (work function 2.36 eV), K (2.28 eV copper), Rb ( 2.16 eV copper) or Cs (1.95 eV copper), Ca (2.9 eV copper), Sr (2.0 copper) to 2.5 eV) or an alkaline earth metal such as Ba (2.52 eV copper), and a material having a work function of 2.9 eV or less is particularly preferable. Among these, a more preferable reducing substance is an alkali metal of K, Rb, or Cs, More preferably, it is Rb or Cs, Most preferably, it is Cs. These alkali metals have particularly high reducing ability, and by adding a relatively small amount to a material for forming the electron transport layer or the electron injection layer, the luminance of light emission in the organic EL device and the lifespan of the organic EL device are improved. 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 preferable, and in particular, a combination containing Cs, for example, Cs and Na, Cs and K, Cs and Rb, or Cs and a combination of Na and K is preferred. By containing Cs, the reducing ability can be exhibited efficiently, and the improvement of the light emission luminance in an organic electroluminescent element and life extension are attained by addition to the material which forms an electron carrying layer or an electron injection layer.

In addition, one or a plurality of organic layers such as a capping layer having various functions according to the characteristics of the organic electroluminescent device may be further included.

<Cathode in organic electroluminescent element>

The cathode 108 serves to inject electrons into the light emitting layer 105 through 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 capable of efficiently injecting 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 electron injection efficiency and improve device characteristics, lithium, sodium, potassium, cesium, calcium, magnesium, or an alloy containing these low work function metals is effective. However, these low work function metals are generally unstable in the atmosphere in many cases. In order to improve this point, for example, a method of using an electrode with high stability by doping a trace amount of lithium, cesium, or magnesium into an organic layer is known. As other dopants, inorganic salts such as lithium fluoride, cesium fluoride, lithium oxide and cesium oxide can also be used. However, it is not limited to these.

In addition, for electrode protection, metals such as platinum, gold, silver, copper, iron, tin, aluminum and indium, or alloys using these metals, and inorganic substances such as silica, titania and silicon nitride, polyvinyl alcohol, vinyl chloride, hydrocarbon A preferred example of laminating a high molecular compound or the like is exemplified. The manufacturing method of these electrodes is also not restrict|limited in particular as long as conduction|electrical_connection, such as resistance heating, electron beam vapor deposition, sputtering, ion plating, and coating, can be taken.

<Binder that can be used in each layer>

The materials used for the above hole injection layer, hole transport layer, light emitting layer, electron transport layer, and electron injection layer can form each layer alone, but as a polymer binder, polyvinyl chloride, polycarbonate, polystyrene, poly(N-vinylcartide) Bazole), polymethyl methacrylate, polybutyl methacrylate, polyester, polysulfone, polyphenylene oxide, polybutadiene, hydrocarbon resin, ketone resin, phenoxy resin, polyamide, ethyl cellulose, vinyl acetate resin, ABS Solvent-soluble resins such as resins and polyurethane resins, phenol resins, xylene resins, petroleum resins, urea resins, melamine resins, unsaturated polyester resins, alkyd resins, epoxy resins, silicone resins, etc. It is also possible

<Composition for forming organic layer used in wet film forming method>

The composition for forming an organic layer is obtained by dissolving a low-molecular compound capable of forming each organic layer of an organic EL device, or a high-molecular compound obtained by polymerizing the low-molecular compound in an organic solvent. For example, the composition for forming a light emitting layer includes a polycyclic aromatic compound (or a polymer compound thereof) as at least one dopant material as a first component, at least one host material as a second component, and at least one as a third component. contains organic solvents of the species. The first component functions as a dopant component of the light emitting layer obtained from the composition, and the second component functions as a host component of the light emitting layer. The third component functions as a solvent for dissolving the first and second components in the composition and upon application imparts a smooth and uniform surface shape by the controlled evaporation rate of the third component itself.

<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 film formability, the presence or absence of defects in the coating film, surface roughness, and smoothness. In addition, at the time of film formation using the inkjet method, the ejection property can be controlled and improved by controlling the meniscus stability in the pinhole of the inkjet head. Furthermore, by controlling the drying rate of the film and the orientation of the derivative molecules, it is possible to improve the electrical properties, luminescent properties, efficiency, and lifespan of an organic EL device having an organic layer obtained from the composition for forming an organic layer.

(1) Physical properties of organic solvents

The boiling point of at least 1 sort(s) of organic solvent is 130 degreeC - 300 degreeC, 140 degreeC - 270 degreeC are more preferable, and 150 degreeC - 250 degreeC are still more preferable. When a boiling point is higher than 130 degreeC, it is preferable from a viewpoint of the ejection property of an inkjet. Moreover, when a boiling point is lower than 300 degreeC, it is preferable from a viewpoint of the defect of a coating film, surface roughness, a residual solvent, and smoothness. The organic solvent has a more preferable configuration including two or more organic solvents from the viewpoints of good inkjet ejection properties, film formability, smoothness, and low residual solvent. In addition, depending on the case, the composition made into the solid state by removing a solvent from the composition for organic layer formation in consideration of transportability etc. may be sufficient.

Further, the organic solvent includes a good solvent (GS) and a poor solvent (PS) for at least one kind of solute, and the boiling point (BP _GS ) of the good solvent (GS) is the boiling point (BP _PS ) of the poor solvent (PS) A lower configuration is particularly preferred.

By adding the poor solvent of high boiling point, the good solvent of low boiling point volatilizes first at the time of film-forming, and the density|concentration of the content in a composition and the density|concentration of a poor solvent increase, and rapid film-forming is accelerated|stimulated. Thereby, there are few defects, the surface roughness is small, and the coating film with high smoothness is obtained.

The difference in solubility (S _GS -S _PS ) is preferably 1% or more, more preferably 3% or more, and still more preferably 5% or more. It is preferable that it is 10 degreeC or more, and, as for the difference (BP _PS -BP _GS ) of boiling points, it is more preferable that it is 30 degreeC or more, and it is still more preferable that it is 50 degreeC or more.

The organic solvent is removed from the coating film by a drying step such as vacuum, reduced pressure, or heating after film formation. When heating, it is preferable to carry out at least 1 sort(s) of glass transition temperature (Tg) of a solute +30 degreeC or less from a viewpoint of coating film-forming property improvement. Moreover, from a viewpoint of reducing a residual solvent, it is preferable to heat to -30 degreeC or more of the glass transition point (Tg) of at least 1 sort(s) of a solute. Even if the heating temperature is lower than the boiling point of the organic solvent, since the film is thin, the organic solvent is sufficiently removed. Moreover, you may dry several times at different temperatures, and may use several drying method together.

(2) Specific examples of organic solvents

Examples of the organic solvent used in the composition for forming an organic layer include an alkylbenzene-based solvent, a phenylether-based solvent, an alkylether-based solvent, a cyclic ketone-based solvent, an aliphatic ketone-based solvent, a monocyclic ketone-based solvent, a solvent having a diester skeleton, and fluorine-based solvents and the like, and specific examples thereof include pentanol, hexanol, heptanol, octanol, nonanol, decanol, undecanol, dodecanol, tetradecanol, hexan-2-ol, heptane-2- Ol, octan-2-ol, decan-2-ol, dodecan-2-ol, cyclohexanol, α-terpineol, β-terpineol, γ-terpineol, δ-terpineol, ter Pineol (mixture), ethylene glycol monomethyl ether acetate, propylene glycol monomethyl ether acetate, diethylene glycol dimethyl ether, dipropylene glycol dimethyl ether, diethylene glycol ethyl methyl 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-luti Dean, 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-butyl Benzene, 2-methylanisole, phenetol, benzodioxole, 4-methylanisole, s-butylbenzene, 3-methylanisole, 4-fluoro-3-methylanisole, cymene, 1,2,3 -Trimethylbenzene, 1,2-dichlorobenzene, 2-fluorobenzonitrile, 4-fluoroveratrol, 2,6-dimethylanisole, n-butylbenzene, 3-fluorobenzonitrile, decalin (decahydronaphthalene) ), neopentylbenzene, 2,5-dimethylanisole, 2,4-dimethylanisole, benzonitrile , 3,5-dimethylanisole, diphenyl ether, 1-fluoro-3,5-dimethoxybenzene, methyl benzoate, isopentylbenzene, 3,4-dimethylanisole, o-tolunitrile, n-amyl Benzene, veratrol, 1,2,3,4-tetrahydronaphthalene, ethyl benzoate, n-hexylbenzene, propyl benzoate, cyclohexylbenzene, 1-methylnaphthalene, butyl benzoate, 2-methylbiphenyl, 3-phenoxy Toluene, 2,2'-bitolyl, dodecylbenzene, dipentylbenzene, tetramethylbenzene, trimethoxybenzene, trimethoxytoluene, 2,3-dihydrobenzofuran, 1-methyl-4- (propoxy Methyl) benzene, 1-methyl-4- (butyloxymethyl) benzene, 1-methyl-4- (pentyloxymethyl) benzene, 1-methyl-4- (hexyloxymethyl) benzene, 1-methyl-4- ( Heptyloxymethyl) benzene, benzyl butyl ether, benzyl pentyl ether, benzyl hexyl ether, benzyl heptyl ether, benzyl octyl ether, etc. are mentioned, However, It is not limited only to them. In addition, a solvent may be used individually and may be mixed.

<Optional ingredients>

The composition for organic layer formation may contain the arbitrary component in the range which does not impair the property. As an optional component, a binder, surfactant, etc. are mentioned.

(1) Binder

The composition for organic layer formation may contain the binder. A binder forms a film|membrane at the time of film-forming, and joins the obtained film|membrane with a board|substrate. In addition, it serves to dissolve, disperse, and bind other components in the composition for forming the organic layer.

Examples of the binder used in the composition for forming the organic layer include acrylic resin, polyethylene terephthalate, ethylene-vinyl acetate copolymer, ethylene-vinyl alcohol copolymer, acrylonitrile-ethylene-styrene copolymer (AES) resin, Ionomer, chlorinated polyether, diarylphthalate resin, unsaturated polyester resin, polyethylene, polypropylene, polyvinyl chloride, polyvinylidene chloride, polystyrene, polyvinyl acetate, Teflon, acrylonitrile-butadiene-styrene copolymer (ABS) resins, acrylonitrile-styrene copolymer (AS) resins, phenol resins, epoxy resins, melamine resins, urea resins, alkyd resins, polyurethanes, and copolymers of the above resins and polymers, but limited thereto doesn't happen

One type may be sufficient as the binder used for the composition for organic layer formation, and multiple types may be mixed and used for it.

(2) Surfactant

The composition for organic layer formation may contain surfactant for control of the film surface uniformity of the composition for organic layer formation, the solvent-philicity of a film|membrane surface, and liquid repellency, for example. Surfactants are classified into ionic and nonionic according to the structure of the hydrophilic group, and further classified into alkyl-based and silicone-based and fluorine-based according to the structure of the hydrophobic group. Further, according to the molecular structure, it is classified into a monomolecular system having a relatively small molecular weight and a simple structure, and a high molecular weight system having a large molecular weight and side chains or branches. In addition, according to the composition, it is classified into a single system and a mixed system in which two or more types of surfactants and a substrate are mixed. As the surfactant that can be used in the composition for forming an organic layer, all kinds of surfactants can be used.

As surfactant, Polyflow No.45, Polyflow KL-245, Polyflow No.75, Polyflow No.90, Polyflow No.95 (trade name, Kyoeisha Chemical Industry Co., Ltd. product) are, for example, polyflow No.45, for example. , Disperbake 161, Disperbake 162, Disperbake 163, Disperbake 164, Disperbake 166, Disperbake 170, Disperbake 180, Disperbake 181, Disperbake 182, BYK300 , BYK306, BYK310, BYK320, BYK330, BYK342, BYK344, BYK346 (brand name, made by Big Chemie Japan), KP-341, KP-358, KP-368, KF-96-50CS, KF-50-100CS (trade name, manufactured by Shin-Etsu Chemical Co., Ltd.), Suffreon SC-101, Suffreon KH-40 (trade name, manufactured by Semi Chemical Co., Ltd.), Ftagent 222F, Ftagent 251, FTX-218 (trade name, ( Neos Co., Ltd.), EFTOP EF-351, EFTOP EF-352, EFTOP EF-601, EFTOP EF-801, EFTOP EF-802 (trade name, manufactured by Mitsubishi Materials), Megapack F-470, Megapack F -471, Megapack F-475, Megapack R-08, Megapack F-477, Megapack F-479, Megapack F-553, Megapack F-554 (trade name, manufactured by DIC Corporation), Fluoro Alkylbenzenesulfonate, fluoroalkylcarboxylate, fluoroalkylpolyoxyethylene ether, fluoroalkylammonium iodide, fluoroalkylbetaine, fluoroalkylsulfonate, diglycerin tetrakis(fluoroalkylpolyoxyethylene) ether), fluoroalkyltrimethylammonium salt, fluoroalkylaminosulfonate, polyoxyethylene nonylphenyl ether, polyoxyethylene octylphenyl ether, polyoxyethylene alkyl ether, polyoxyethylene laurate, polyoxyethylene oleate, polyoxy Ethylene stearate, polyoxyethylene laurylamine, sorbitan laurate, sorbitan palmitate, sorbitan stearate, sorbitanolate, sorbitan fatty acid ester, polyoxyethylene sorbitan laurate, polyoxyethylene sorbitan palmitate Tate, polyoxyethylene sorbitan steare yt, polyoxyethylene sorbitanolate, polyoxyethylene naphthyl ether, alkylbenzenesulfonate, and alkyldiphenyletherdisulfonate.

In addition, surfactant may be used by 1 type and may use 2 or more types together.

<Composition and physical properties of the composition for forming an organic layer>

Content of each component in the composition for organic layer formation is, each component in the composition for organic layer formation has good solubility, storage stability and film-forming property, and the film quality of the coating film obtained from the said composition for organic layer formation is good, In addition, the inkjet method was used It is determined in consideration of the favorable discharge property in the case of the case and the viewpoint of favorable electrical properties, light emission properties, efficiency, and lifetime of an organic EL device having an organic layer fabricated using the composition. For example, in the case of the composition for forming a light emitting layer, the first component is 0.0001 mass % to 2.0 mass % with respect to the total mass of the composition for forming the light emitting layer, and the second component is 0.0999 mass % with respect to the total mass of the composition for forming the light emitting layer. % - 8.0 mass % and 90.0 mass % - 99.9 mass % of 3rd component are preferable with respect to the total mass of the composition for light emitting layer formation.

More preferably, the first component is 0.005 mass % to 1.0 mass % with respect to the total mass of the composition for forming a light emitting layer, the second component is 0.095 mass % to 4.0 mass % with respect to the total mass of the composition for forming the light emitting layer, the second component Three components are 95.0 mass % - 99.9 mass % with respect to the total mass of the composition for light emitting layer formation. Even more preferably, the first component is 0.05 mass% to 0.5 mass% with respect to the total mass of the composition for forming a light emitting layer, the second component is 0.25 mass% to 2.5 mass% with respect to the total mass of the composition for forming the light emitting layer, A 3rd component is 97.0 mass % - 99.7 mass % with respect to the total mass of the composition for light emitting layer formation.

The composition for organic layer formation can be manufactured by selecting suitably stirring, mixing, heating, cooling, dissolution, dispersion, etc. for the above-mentioned component by a well-known method and performing it. In addition, after preparation, filtration, degassing (also referred to as degas), ion exchange treatment, inert gas replacement/encapsulation treatment, etc. may be appropriately selected and performed.

As a viscosity of the composition for organic layer formation, the favorable discharge property at the time of using the favorable film-forming property and the inkjet method that the one with high viscosity is acquired. On the other hand, the one with a low viscosity is easy to make a thin film|membrane. From this point, it is preferable that the viscosity in 25 degreeC is 0.3-3 mPa*s, and, as for the viscosity of this composition for organic layer formation, it is more preferable that it is 1-3 mPa*s. In the present invention, the viscosity is a value measured using a conical plate rotational viscometer (corn plate type).

As the surface tension of the composition for forming an organic layer, a coating film having good film formability and no defects is obtained with a lower one. On the other hand, the higher one can obtain favorable inkjet discharge property. From this point, it is preferable that the surface tension in 25 degreeC is 20-40 mN/m, and, as for this composition for organic layer formation, it is more preferable that it is 20-30 mN/m. In the present invention, the surface tension is a value measured using the drop method.

<Crosslinkable high molecular compound: compound represented by formula (XLP-1)>

Next, the case where the above-mentioned polymer compound has a crosslinkable substituent will be described. Such a crosslinkable high molecular compound is a compound represented by a following formula (XLP-1), for example.

In the formula (XLP-1),

MUx, ECx and k have the same definitions as MU, EC and k in formula (SPH-1), provided that the compound represented by formula (XLP-1) has at least one crosslinkable substituent (XLS), Preferably, the content of the monovalent or divalent aromatic group having a crosslinkable substituent is 0.1 to 80 mass% in the molecule.

0.5-50 mass % is preferable and, as for content of the monovalent|monohydric or bivalent aromatic compound which has a crosslinkable substituent, 1-20 mass % is more preferable.

The crosslinkable substituent (XLS) is not particularly limited as long as it is a group capable of further crosslinking the above-described polymer compound, but a substituent having the following structure is preferable. * in each structural formula represents a bonding position.

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

As a divalent aromatic compound which has a crosslinkable substituent, the compound which has the following partial structure is mentioned, for example.

<Method for producing polymer compound and cross-linkable polymer compound>

The polymer compound and the method for producing the crosslinkable polymer compound will be described by taking the compound represented by the above formula (SPH-1) and the compound represented by (XLP-1) as examples. These compounds can be synthesized by appropriately combining known production methods.

Examples of the solvent used in the reaction include an aromatic solvent, a saturated/unsaturated hydrocarbon solvent, an alcohol solvent, and an ether-based solvent. For example, dimethoxyethane, 2-(2-methoxyethoxy)ethane, 2- (2-ethoxyethoxy)ethane etc. are mentioned.

In addition, you may perform reaction in a two-phase system. When making it react in a two-phase system, you may add phase transfer catalysts, such as a quaternary ammonium salt, as needed.

When manufacturing the compound of formula (SPH-1) and the compound of (XLP-1), you may manufacture in one step, and you may manufacture through multiple steps. In addition, it may be carried out by a batch polymerization method in which the reaction starts after all the raw materials are put into the reaction vessel, or it may be carried out by a dropping polymerization method in which the raw materials are added dropwise into the reaction vessel, or precipitation in which the product precipitates as the reaction proceeds. You may carry out by the polymerization method, and these can be combined suitably and can be synthesize|combined. For example, when synthesizing the compound represented by the formula (SPH-1) in one step, a monomer in which a polymerizable group is bonded to the monomer unit (MU) and a monomer in which a polymerizable group is bonded to the end cap unit (EC) are added to the reaction vessel. The target product is obtained by performing the reaction in the added state. In addition, when synthesizing the compound represented by the formula (SPH-1) in multiple steps, a monomer in which a polymerizable group is bonded to the monomer unit (MU) is polymerized to a desired molecular weight, and then a monomer in which a polymerizable group is bonded to the end cap unit (EC). By adding and reacting, the target product is obtained. By adding a monomer to which a polymerizable group is bonded to a different type of monomer unit (MU) in multiple steps and performing the reaction, a polymer having a concentration gradient with respect to the structure of the monomer unit can be prepared. Further, after preparing the precursor polymer, the target polymer can be obtained by a post-reaction.

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

As a monomer usable in the present invention, Japanese Patent Application Laid-Open No. 2010-189630, International Publication No. 2012/086671, International Publication No. 2013/191088, International Publication No. 2002/045184, International Publication No. 2011/049241, International Publication No. 2013/146806, International Publication No. 2005/049546, International Publication No. 2015/145871, Japanese Patent Laid-Open No. 2010-215886, Japanese Patent Laid-Open No. 2008-106241, Japanese Patent Laid-Open No. 2010-215886, It can be synthesized according to the method described in International Publication No. 2016/031639, Japanese Patent Application Laid-Open No. 2011-174062, and International Publication No. 2002/045184.

In addition, for specific polymer synthesis procedures, Japanese Patent Application Laid-Open No. 2012-036388, International Publication No. 2015/008851, Japanese Patent Application Laid-Open No. 2012-36381, Japanese Patent Application Laid-Open No. 2012-144722, International Publication No. 2015/194448 International Publication No. 2013/146806, International Publication No. 2015/145871, International Publication No. 2016/031639, International Publication No. 2016/125560, International Publication No. 2015/145871, International Publication No. 2011/049241 It can be synthesized according to the described method.

<Method for manufacturing organic electroluminescent device>

Each layer constituting the organic EL element is formed by applying the material constituting each layer to a vapor deposition method, resistance heating vapor deposition, electron beam vapor deposition, sputtering, molecular lamination method, printing method, inkjet method, spin coating method or casting method, coating method, etc. It can be formed by setting it as a thin film. There is no limitation in particular about the film thickness of each layer formed in this way, Although it can set suitably according to the property of a material, Usually, it is the range of 2 nm - 5000 nm. The film thickness can be usually measured with a crystal oscillation type film thickness measuring device or the like. In the case of thin film formation using the vapor deposition method, the deposition conditions differ depending on the type of material, the target crystal structure and association structure of the film, and the like. The deposition conditions are generally: boat heating temperature of +50 to +400°C, vacuum degree of 10 ^-6 to 10 ^-3 Pa, deposition rate of 0.01 to 50 nm/sec, substrate temperature of -150 to +300°C, and film thickness of 2 nm to 5 µm. It is preferable to set it appropriately in the range.

Next, as an example of a method of manufacturing an organic EL device, an organic EL device comprising an anode/hole injection layer/hole transport layer/a light emitting layer/electron transport layer/electron injection layer/cathode made of a host material and a dopant material. Explain. On a suitable substrate, a thin film of an anode material is formed by a vapor deposition method 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 this to form a thin film to form a light emitting layer, an electron transport layer and an electron injection layer are formed on the light emitting layer, and a thin film made of a material for a cathode is formed by vapor deposition or the like to form a cathode. An EL element is obtained. In the production of the organic EL device described above, it is also possible to produce the cathode, the electron injection layer, the electron transport layer, the light emitting layer, the hole transport layer, the hole injection layer, and the anode in this order by reversing the production order.

When a DC voltage is applied to the organic EL device obtained in this way, the anode may be applied with the positive polarity of + and the cathode with negative polarity. , and both) can be observed. In addition, this organic EL element emits light even when a pulse current or an alternating current is applied. In addition, the waveform of the alternating current to be applied may be arbitrary.

<Application example of organic electroluminescent device>

The organic EL element can also be applied to a display device, a lighting device, or the like.

The display device or lighting device provided with the organic EL element can be manufactured by a known method such as connecting the organic EL element and a known driving device, and a known driving method such as direct current driving, pulse driving, and alternating current driving is suitably used. It can be driven using

As a display apparatus, flexible displays, such as panel displays, such as a color flat panel display, and flexible color organic electroluminescence (EL) display, etc. are mentioned, for example (For example, Unexamined-Japanese-Patent No. 10-335066, Japanese Patent Laid-Open No. 2003-321546, Japanese Patent Application Laid-Open No. 2004-281086, etc.). Moreover, as a display method of a display, a matrix and/or a segment method etc. are mentioned, for example. In addition, the matrix display and the segment display may coexist in the same panel.

In the matrix, pixels for display are arranged two-dimensionally, such as a grid shape or a mosaic shape, and a character or an image is displayed by a set of pixels. The shape or size of the pixel is determined depending on the application. For example, a square pixel of 300 µm or less on one side is usually used for displaying images and characters on computers, monitors, and televisions, and in the case of a large display such as a display panel, pixels with a side on the order of mm are used. will do In the case of black and white display, pixels of the same color may be arranged, but in the case of color display, pixels of red, green, and blue are arranged and displayed. In this case, there are typically a delta type and a stripe type. Incidentally, as a driving method of this matrix, either a linear driving method or an active matrix may be used. Although line-sequential driving has an advantage in that it has a simple structure, the active matrix method may be excellent when the operating characteristics are taken into consideration.

In the segment method (type), a pattern is formed to display predetermined information, and a predetermined area is made to emit light. For example, time and temperature display in a digital watch or thermometer, operation state display of an audio device, an electronic cooker, etc., and a panel display of an automobile, etc. are mentioned.

Examples of the lighting device include lighting devices such as indoor lighting, backlights of liquid crystal display devices, and the like (for example, Japanese Patent Laid-Open Nos. 2003-257621, 2003-277741, Japanese Patents See Publication No. 2004-119211, etc.). The backlight is mainly used for the purpose of improving the visibility of a display device that does not emit light by itself, and is used in a liquid crystal display device, a watch, an audio device, an automobile panel, a display panel, a cover, and the like. In particular, as a backlight for a liquid crystal display device, in particular, a backlight using an organic EL element is a backlight using an organic EL element, considering that it is difficult to reduce the thickness because the conventional method consists of a fluorescent lamp or a light guide plate as a backlight for computer use, in which thickness reduction is a problem. become a characteristic

<Other organic devices>

The polycyclic aromatic compound according to the present invention can be used for production of organic field effect transistors or organic thin film solar cells in addition to the organic electroluminescent devices described above.

An organic field-effect transistor is a transistor that controls a current by an electric field generated by voltage input, and a gate electrode is provided 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 current can be controlled by blocking the flow of electrons (or holes) flowing between the source electrode and the drain electrode. BACKGROUND ART Field effect transistors are easily downsized compared to simple transistors (bipolar transistors), and are often used as elements constituting integrated circuits and the like.

In the structure of an organic field effect transistor, 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 further, an insulating layer (dielectric layer) in contact with the organic semiconductor active layer is interposed and the gate electrode is installed. As the element structure, the following structures are mentioned, for example.

(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

The organic field effect transistor constituted in this way can be applied as an active matrix driving type liquid crystal monitor, a pixel driving switching element of an organic light emitting element display, or the like.

The 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 the physical properties thereof. The polycyclic aromatic compound according to the present invention can function as a hole transporting material or an electron transporting material in an organic thin film solar cell. The organic thin film solar cell may be suitably provided with a hole blocking layer, an electron blocking layer, an electron injection layer, a hole injection layer, a smoothing layer, etc. in addition to the above. The organic thin film solar cell can be used in combination by appropriately selecting a known material used for the organic thin film solar cell.

<Wavelength conversion material>

The polycyclic aromatic compound of the present invention can be used as a wavelength conversion material.

At present, the application of the multi-colorization technology by the color conversion method to a liquid crystal monitor, an organic EL display, lighting, or the like is vigorously studied. Color conversion refers to wavelength conversion of light emission from a light emitting body to light having a longer wavelength, for example, converting ultraviolet light or blue light into green light or red light emission. By filming the wavelength conversion material having this color conversion function and combining it with a blue light source, for example, 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. A full-color display can be manufactured by combining such a blue light source and a white light source obtained by combining a wavelength conversion film having a color conversion function as a light source unit and a liquid crystal driving part and a color filter. Moreover, if there is no liquid crystal drive part, it can be used as a white light source as it is, For example, it can apply as white light sources, such as LED lighting. In addition, 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, a full color organic EL display that does not use a metal mask can be produced. Furthermore, by using a blue microLED as a light source in combination with a wavelength conversion film that converts blue light into green light and red light, a low-cost full color microLED display can be manufactured.

The polycyclic aromatic compound of the present invention can be used as this wavelength conversion material. Using the wavelength conversion material containing the polycyclic aromatic compound of the present invention, the light from a light source or light emitting element that generates ultraviolet light or blue light of a shorter wavelength is converted into a display device (a display device or a liquid crystal display device using an organic EL device) It can be converted into blue light or green light with high color purity suitable for use in Adjustment of the color to be converted can be performed by appropriately selecting a substituent for the polycyclic aromatic compound of the present invention, a binder resin used in the composition for converting a wavelength described later, and the like. A wavelength conversion material can be prepared as a composition for wavelength conversion containing the polycyclic aromatic compound of this invention. Moreover, you may form a wavelength conversion film using this composition for wavelength conversion.

The composition for wavelength conversion may contain binder resin, other additives, and a solvent other than the polycyclic aromatic compound of this invention. As binder resin, the thing of Paragraph 0173-0176 of International Publication No. 2016/190283 can be used, for example. As other additives, the compounds described in paragraphs 0177 to 0181 of International Publication No. 2016/190283 can be used. As a solvent, the description of the solvent contained in the said composition for light emitting layer formation can be referred.

The wavelength conversion film includes a wavelength conversion layer formed by curing the composition for wavelength conversion. As a manufacturing method of the wavelength conversion layer from the composition for wavelength conversion, a well-known film formation method can be referred. The wavelength conversion film may consist only of a wavelength conversion layer formed from the composition containing the polycyclic aromatic compound of the present invention, or another wavelength conversion layer (for example, a wavelength conversion layer for converting blue light into green light or red light, blue light or green light) A wavelength conversion layer that converts into red light) may be included. Moreover, the wavelength conversion film may contain the barrier layer for preventing deterioration by oxygen, water|moisture content, or a heat|fever of a base material layer and a color conversion layer.

[Example]

Hereinafter, the present invention will be more specifically described by way of examples, but the present invention is not limited thereto. First, the synthesis example of a polycyclic aromatic compound is demonstrated below.

Synthesis Example (1): Synthesis of compound (1-2)

In a flask containing compound (Int-1-2) (2.4 g, 3.0 mmol, 1eq.) and tert-butyl benzene ( ^t Bu-benzene, 50 ml), in a nitrogen atmosphere at 0 ° C, 1.60 M tert-butyl Lithium pentane solution ( ^t BuLi, 3.75 ml) was added. After completion of the dropwise addition, the temperature was raised to 70° C. and stirred for 0.5 hours, and then the components having a lower boiling point than tert-butylbenzene were distilled off under reduced pressure. After cooling to -50°C, boron tribromide (0.62 g) was added, the temperature was raised to room temperature, and the mixture was stirred for 0.5 hours. After that, it is cooled to 0°C again, N,N-diisopropylethylamine (EtN ⁱ Pr ₂ , 0.39g) is added, and the mixture is stirred at room temperature until the exotherm subsides, then the temperature is raised to 100°C and heated for 1 hour. stirred. The reaction solution was cooled to room temperature, an aqueous sodium acetate solution cooled in an ice bath, followed by ethyl acetate was added to separate the mixture. After the organic layer was concentrated, it was purified by silica gel short pass column (eluent: chlorobenzene). The obtained crude product was recrystallized from toluene to obtain compound (1-2) (0.20 g). By MS, the target compound (1-2) was confirmed at m/z (M+H) = 773.501.

Synthesis Example (2): Synthesis of compound (1-31)

Compound (Int-1-2) (2.40 g, 3.0 mmol, 1eq.) was replaced with Compound (Int-1-31) (2.40 g, 3.0 mmol, 1eq.) in the same procedure as in Synthesis Example 1 (1-31) was obtained (0.13 g).

By MS, the target compound (1-31) was confirmed at m/z (M+H) = 773.501.

Synthesis Example (3): Synthesis of compound (1-44)

Compound (Int-1-2) (2.40 g, 3.0 mmol, 1eq.) was replaced with compound (Int-1-44) (2.40 g, 3.0 mmol, 1eq.) in the same manner as in Synthesis Example 1 (1-44) was obtained (0.16 g).

By MS, the target compound (1-44) was confirmed at m/z (M+H) = 773.501.

Synthesis Example (4): Synthesis of compound (1-71)

In a flask containing compound (Int-1-71) (2.88 g, 3.0 mmol, 1eq.) and tert-butyl benzene ( ^t Bu-benzene, 50 ml), under nitrogen atmosphere, at 0° C., 1.60 M tert-butyl Lithium pentane solution ( ^t BuLi, 7.50 ml) was added. After completion of the dropwise addition, the temperature was raised to 70° C. and stirred for 0.5 hours, and then the components having a lower boiling point than tert-butylbenzene were distilled off under reduced pressure. After cooling to -50°C, boron tribromide (1.23 g) was added, the temperature was raised to room temperature, and the mixture was stirred for 0.5 hours. After that, it is cooled to 0°C again, N,N-diisopropylethylamine (EtN ⁱ Pr ₂ , 0.78g) is added, and the mixture is stirred at room temperature until the exotherm subsides, then the temperature is raised to 100°C and heated for 1 hour. stirred. The reaction solution was cooled to room temperature, an aqueous sodium acetate solution cooled in an ice bath, followed by ethyl acetate was added to separate the mixture. After the organic layer was concentrated, it was purified by silica gel short pass column (eluent: chlorobenzene). The obtained crude product was recrystallized from toluene to obtain compound (1-71) (0.26 g).

By MS, the target compound (1-71) was identified at m/z (M+H) = 907.320.

Synthesis Example (5): Synthesis of compound (1-73)

Compound (Int-1-71) (2.88 g, 3.0 mmol, 1eq.) was replaced with compound (Int-1-73) (2.88 g, 3.0 mmol, 1eq.) in the same manner as in Synthesis Example 4 (1-73) was obtained (0.09 g).

By MS, the target compound (1-73) was identified at m/z (M+H) = 907.320.

Synthesis Example (6): Synthesis of compound (1-81)

Compound (Int-1-71) (2.88 g, 3.0 mmol, 1eq.) was replaced with compound (Int-1-81) (2.88 g, 3.0 mmol, 1eq.) in the same manner as in Synthesis Example 4 (1-81) was obtained (0.21 g).

By MS, the target compound (1-81) was identified at m/z (M+H) = 907.320.

Synthesis of comparative compound (1)

It was synthesized according to the method described in Korean Patent Application Laid-Open No. 2020/121228. By MS, the target comparative compound (1) was identified at m/z (M+H) = 775.516.

[Formula 136]

Other polycyclic aromatic compounds of the present invention can be synthesized by a method similar to the above-mentioned synthesis examples by appropriately changing the raw material compounds.

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

Evaluation items and evaluation methods

Evaluation items include driving voltage (V), emission wavelength (nm), CIE chromaticity (x, y), external quantum efficiency (%), maximum wavelength (nm) and full width at half maximum (nm) of the emission spectrum. For these evaluation items, an appropriate value at the time of light emission luminance can be used.

Quantum efficiency of a light emitting device includes internal quantum efficiency and external quantum efficiency, and the internal quantum efficiency represents a ratio in which external energy injected as electrons (or holes) into the light emitting layer of the light emitting device is purely converted into photons. On the other hand, the external quantum efficiency is calculated based on the amount of this photon emitted to the outside of the light emitting element, and the photon generated in the light emitting layer is partially absorbed or continuously reflected inside the light emitting element, Since it is not emitted as , the external quantum efficiency is lower than the internal quantum efficiency.

The method for measuring spectral radiance (emission spectrum) and external quantum efficiency is as follows. A voltage/current generator R6144 manufactured by Advantist was used, and the device was made to emit light by applying a voltage. The spectral emission luminance in the visible region was measured from a direction perpendicular to the light emitting surface using a spectral emission luminance meter SR-3AR manufactured by TOPCON. Assuming that the light emitting surface is a perfect diffusion surface, the value obtained by dividing the measured spectral radiance luminance of each wavelength component by the wavelength energy and multiplied by π is the number of photons at each wavelength. Then, the number of photons in the observed wavelength region was accumulated, and it was taken as the total number of photons emitted from the device. The value obtained by dividing the applied current value by the basic charge is the number of carriers injected into the device, and the number of total photons emitted from the device divided by the number of carriers injected into the device is the external quantum efficiency. In addition, the half width of the emission spectrum is calculated|required as the width between the upper and lower wavelengths at which the intensity|strength becomes 50% centering on the maximum emission wavelength.

<Evaluation of vapor deposition organic EL device>

Organic EL devices according to Examples 1-1 to 1-6 and Comparative Example 1-1 were fabricated, and driving voltage, external quantum efficiency (EQE), and LT50 (constant current driving) at a luminance of 500 cd/m ² and the time to maintain the luminance of 50% or more, in this case, the time to maintain the luminance of 250 cd/m ² or more when continuously driven at the current density at the initial luminance of 500 cd/m ² ) was measured.

[Table 1]

Chemical structures of "NPD", "TcTa", "mCP", "Ir(ppy) ₃ ", "2CzBN", "BPy-TP2""GH-1", and comparative compound (1) in Table 1 is shown below.

<Example 1-1>

A 26 mm x 28 mm x 0.7 mm glass substrate (manufactured by Optoscience Co., Ltd.) which polished ITO formed into a film to a thickness of 200 nm by sputtering to 50 nm was used as a transparent support substrate. This transparent support substrate was fixed to a substrate holder of a commercially available vapor deposition apparatus (manufactured by Showa Vacuum Co., Ltd.), and NPD, TcTa, mCP, GH-1, compound (1-2), 2CzBN, and BPy-TP2 were each applied thereto. A molybdenum vapor deposition boat and a tungsten vapor deposition boat into which LiF and aluminum were respectively placed were mounted.

Each of the following layers was sequentially formed on the ITO film of the transparent support substrate. The vacuum chamber was pressure-reduced to 5x10 ^-4 Pa, and first, NPD was heated and vapor-deposited so that it might become a film thickness of 40 nm, and the hole injection layer was formed. Next, TcTa was heated to vapor-deposit to a film thickness of 15 nm, and mCP was further heated to vapor-deposit to a film thickness of 15 nm to form a two-layer hole transporting layer. Next, GH-1 and compound (1-2) were simultaneously heated and vapor-deposited to a film thickness of 20 nm to form a light emitting layer. The deposition rate was controlled so that the weight ratio of GH-1 and compound (1-2) was about 99:1. Next, 2CzBN was heated to vapor-deposit to a film thickness of 10 nm, and BPy-TP2 was further heated to vapor-deposit to a film thickness of 20 nm to form an electron transporting layer comprising two layers. The deposition rate of each layer was 0.01 to 1 nm/sec. Thereafter, LiF was heated and vapor-deposited at a deposition rate of 0.01 to 0.1 nm/sec to a film thickness of 1 nm, and then, aluminum was heated and vapor-deposited to 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.

<Example 1-2 to Example 1-6, Comparative Example 1-1>

Each device was manufactured by changing the compound (1-2), which is the dopant of Example 1, to each dopant shown in Table 1.

Table 2 shows the evaluation results of each element.

[Table 2]

In Examples 1-1 to 1-6, as compared with Comparative Example 1-1, the external quantum efficiency was high and the result of the long LT50 was obtained.

<Evaluation of vapor deposition organic EL device>

Organic EL devices according to Examples G2-1 to G2-6, Comparative Example G2-1, Example G3-1 to Example G3-6 and Comparative Example G3-1 were fabricated, and the luminance was 500 cd/m ² . , emission wavelength, full width at half maximum, driving voltage, external quantum efficiency, and LT50 (constant current driving and maintaining 50% or more of luminance, in this case, continuous driving with current density at initial luminance of 500 cd/m ² ) time to maintain luminance of 250 cd/m ² or more) was measured.

[Table 3]

The chemical structures of "HATCN", "TBB", "CBP" and "GH-2" are shown below.

<Example G2-1>

A glass substrate (manufactured by Optoscience Co., Ltd.) having a size of 26 mm x 28 mm x 0.7 mm in which ITO formed by sputtering to a thickness of 200 nm was polished to 50 nm was used as a transparent support substrate. This transparent support substrate is fixed to a substrate holder of a commercially available vapor deposition apparatus (manufactured by Showa Vacuum Co., Ltd.), and HATCN, TBB, TcTa, CBP, compound (1-2) and TPBi are put in a molybdenum vapor deposition boat; A tungsten deposition boat containing LiF and aluminum, respectively, was mounted.

Each of the following layers was sequentially formed on the ITO film of the transparent support substrate. The vacuum chamber was pressure-reduced to 5x10 ^-4 Pa, and first, HATCN was heated and vapor-deposited to a film thickness of 5 nm to form a hole injection layer. Next, TBB was heated to vapor-deposit to a film thickness of 65 nm, followed by heating to vapor-deposit TcTa to a film thickness of 10 nm to form a two-layer hole transport layer. Next, CBP and compound (1-2) were simultaneously heated and vapor-deposited to a film thickness of 30 nm to form a light emitting layer. The deposition rate was controlled so that the weight ratio of CBP and compound (1-2) was about 99:1. Next, TPBi was heated and vapor-deposited to a film thickness of 50 nm to form an electron transport layer. The deposition rate of each layer was 0.01 to 1 nm/sec. Thereafter, LiF was heated and vapor-deposited at a deposition rate of 0.01 to 0.1 nm/sec to a film thickness of 1 nm, and then, aluminum was heated and vapor-deposited to 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.

<Example G2-2 to Example G2-6, Comparative Example G2-1, Example G3-1 to Example G3-6 and Comparative Example G3-1>

Each device was manufactured by changing the host CBP, dopant compound (1-2), and host:dopant mixing ratio of Example G2-1 to each host, dopant, and mixing ratio shown in Table 3.

Table 4 shows the evaluation results of each element.

[Table 4]

In Example G2-1 to Example G2-6 and Example G3-1 to Example G3-6, compared with Comparative Example G2-1 and Comparative Example G3-1, high efficiency and long device lifetime were obtained.

<Evaluation of vapor deposition organic EL device>

Organic EL devices according to Examples G4-1 to G4-4 and Comparative Example G4-1 were fabricated, and at a luminance of 500 cd/m ² , emission wavelength, full width at half maximum, driving voltage, external quantum efficiency, and LT50 (constant current driving) and the time to maintain the luminance of 50% or more, in this case, the time to maintain the luminance of 250 cd/m ² or more when continuously driven at the current density at the initial luminance of 500 cd/m ² ) was measured.

[Table 5]

Below, the chemical structures of "T2T", "4CzIPN", "BCC-TPTA" and "Liq" are shown.

<Example G4-1>

A glass substrate (manufactured by Optoscience Co., Ltd.) having a size of 26 mm x 28 mm x 0.7 mm in which ITO formed by sputtering to a thickness of 200 nm 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 vapor deposition apparatus (manufactured by Showa Vacuum Co., Ltd.), and HATCN, TBB, TcTa, BCC-TPTA, compound (1-2), T2T, Liq, and TPBi were each placed thereinto. A molybdenum vapor deposition boat and a tungsten vapor deposition boat containing LiF and aluminum, respectively, were mounted.

Each of the following layers was sequentially formed on the ITO film of the transparent support substrate. The vacuum chamber was pressure-reduced to 5x10 ^-4 Pa, and first, HATCN was heated and vapor-deposited so that it might become a film thickness of 5 nm, and the hole injection layer was formed. Next, TBB was heated to vapor-deposit to a film thickness of 65 nm, followed by heating to vapor-deposit TcTa to a film thickness of 10 nm to form a two-layer hole transport layer. Next, TcTa, BCC-TPTA, and compound (1-2) were simultaneously heated and vapor-deposited to a thickness of 30 nm to form a light emitting layer. The deposition rate was controlled so that the weight ratio of CBP, BCC-TPTA, and compound (1-2) was about 85 to 14 to 1. Next, T2T was heated to vapor-deposit to a film thickness of 10 nm, and then TPBi and Liq were heated and vapor-deposited to a film thickness of 40 nm to form an electron transporting layer composed of two layers. The deposition rate was adjusted so that the weight ratio of TPBi and Liq was about 70:30. The deposition rate of each layer was 0.01 to 1 nm/sec. Thereafter, LiF was heated and vapor-deposited at a deposition rate of 0.01 to 0.1 nm/sec to a film thickness of 1 nm, and then, aluminum was heated and vapor-deposited to 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>

BCC-TPTA as an assisting dopant in Example G4-1, compound (1-2) as a dopant, and a mixing ratio were changed to each assisting dopant and each dopant and each mixing ratio described in Table 5 to fabricate each device.

Table 6 shows the evaluation results of each element.

[Table 6]

In Examples G4-1 to G4-4, high efficiency and long device lifetime were obtained as compared with Comparative Example G4-1. As in Examples G4-1 and G4-2, a device using an exciplex and an assisting dopant is feasible.

<Evaluation of coating type organic EL element>

Next, the organic electroluminescent element obtained by coating-forming an organic layer is demonstrated.

<Polymer host compound: Synthesis of SPH-101>

According to the method described in International Publication No. 2015/008851, SPH-101 was synthesized. A copolymer to which M2 or M3 is bonded is obtained next to M1, and it is estimated that each unit is 50:26:24 (molar ratio) from the input ratio. In the following structural formula, Me is a methyl group, Bpin is a pinacolatoboryl group, and * is a connection position of each unit.

<Polymer hole transport compound: Synthesis of XLP-101>

According to the method described in Patent Publication No. 2018-61028, XLP-101 was synthesized. A copolymer bonded with M5 or M6 is obtained next to M4, and it is estimated that each unit is 40:10:50 (molar ratio) from the input ratio. In the following structural formula, Me is a methyl group, Bpin is a pinacolatoboryl group, and * is a connection position of each unit.

<Example 2-1 to Example 2-9>

A coating-type organic EL device is prepared by preparing a solution for application of the material forming each layer.

<Production of organic EL devices of Examples 2-1 to 2-3>

Table 7 shows the material configuration of each layer in the organic EL device.

[Table 7]

The structure of "ET1" in Table 7 is shown below.

<Preparation of the composition (1) for forming a light emitting layer>

The composition (1) for light emitting layer formation is prepared by stirring the following components until it becomes a uniform solution. By spin-coating the prepared composition for light emitting layer formation on a glass substrate and heating and drying under reduced pressure, there is no film|membrane defect and the coating film excellent in smoothness is obtained.

Compound (A) 0.04% by weight

SPH-101 1.96 wt%

xylene 69.00% by weight

Decalin 29.00 wt%

Further, the compound (A) is a polycyclic aromatic compound represented by the general formula (1A-1) (eg, compound (1-2)), and the polycyclic aromatic compound is a monomer (that is, the monomer has a reactive substituent) It is a high molecular compound polymerized by using , or a polymer crosslinked product in which the high molecular compound is further crosslinked. A polymer compound for obtaining a crosslinked polymer has a crosslinkable substituent.

<PEDOT:PSS solution>

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

<Preparation of OTPD solution>

OTPD (LT-N159, manufactured by Luminescence Technology Corp.) and IK-2 (photocationic polymerization initiator, manufactured by San Apro) 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 at 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>

On a glass substrate on which ITO was deposited to a thickness of 150 nm, a PEDOT:PSS solution was spin-coated and baked on a hot plate at 200° C. for 1 hour to form a PEDOT:PSS film with a film thickness of 40 nm (hole injection layer). Then, the OTPD solution is spin-coated, dried on a hot plate at 80° C. for 10 minutes, exposed with an exposure machine at an exposure intensity of 100 mJ/cm ² , and baked on a hot plate at 100° C. for 1 hour, whereby a film insoluble in solution An OTPD film with a thickness of 30 nm is formed (hole transport layer). Then, the composition (1) for forming a light-emitting layer is spin-coated and baked on a hot plate at 120°C for 1 hour to form a light-emitting layer with a thickness of 20 nm.

The produced multilayer film is fixed to a substrate holder of a commercially available vapor deposition apparatus (manufactured by Showa Vacuum Co., Ltd.), and molybdenum vapor deposition boat containing ET1, molybdenum vapor deposition boat containing LiF, tungsten vapor deposition boat containing aluminum to install After depressurizing the vacuum chamber to 5x10 ^-4 Pa, ET1 is heated and vapor-deposited to a film thickness of 30 nm to form an electron transport layer. The deposition rate at the time of forming the electron transport layer is set to 1 nm/sec. Then, LiF is heated and vapor-deposited at the deposition rate of 0.01-0.1 nm/sec so that it may become a film thickness of 1 nm. Then, aluminum is heated and vapor-deposited to a film thickness of 100 nm to form a cathode. In this way, an organic EL element is obtained.

<Example 2-2>

An organic EL device was obtained in the same manner as in Example 2-1. In the hole transport layer, a film having a thickness of 30 nm is formed by spin-coating the XLP-101 solution and baking it on a hot plate at 200°C for 1 hour.

<Example 2-3>

An organic EL device was obtained in the same manner as in Example 2-1. Further, 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 having a thickness of 30 nm.

<Evaluation of the organic EL device of Examples 2-1 to 2-3>

It can be expected that the coating-type organic EL device obtained as described above also has excellent driving voltage and external quantum efficiency like the deposition-type organic EL device.

<Production of organic EL devices of Examples 2-4 to 2-6>

Table 8 shows the material configuration of each layer in the organic EL device.

[Table 8]

<Preparation of compositions (2) to (4) for forming a light emitting layer>

The composition (2) for light emitting layer formation is prepared by stirring the following components until it becomes a uniform solution.

Compound (A) 0.02% by weight

mCBP 1.98 wt%

98.00% by weight of toluene

The composition (3) for light emitting layer formation is prepared by stirring the following components until it becomes a uniform solution.

Compound (A) 0.02% by weight

SPH-101 1.98 wt%

98.00% by weight of xylene

The composition (4) for light emitting layer formation is prepared by stirring the following components until it becomes a uniform solution.

Compound (A) 0.02% by weight

DOBNA 1.98 wt%

98.00% by weight of toluene

In Table 8, "mCBP" is 3,3'-bis(N-carbazolyl)-1,1'-biphenyl, and "DOBNA" is 3,11-di-o-tolyl-5,9- It is dioxa-13b-boranaphtho[3,2,1-de]anthracene, and "TSPO1" is diphenyl[4-(triphenylsilyl)phenyl]phosphine oxide. The chemical structure is shown below.

<Example 2-4>

After spin-coating an ND-3202 (manufactured by Nissan Chemical Industry Co., Ltd.) solution on a glass substrate on which ITO was formed to a thickness of 45 nm, heating at 50 ° C. for 3 minutes, and further heating at 230 ° C. for 15 minutes, An ND-3202 film with a film thickness of 50 nm is formed (hole injection layer). Then, the XLP-101 solution is spin-coated and heated on a hot plate at 200° C. for 30 minutes in a nitrogen gas atmosphere to form an XLP-101 film with a thickness of 20 nm (hole transport layer). Then, the composition 2 for forming a light emitting layer is spin-coated and heated at 130° C. for 10 minutes in a nitrogen gas atmosphere to form a light emitting layer with a thickness of 20 nm.

The produced multilayer film is fixed to the substrate holder of a commercial vapor deposition apparatus (manufactured by Showa Vacuum Co., Ltd.), and molybdenum vapor deposition boat containing TSPO1, molybdenum vapor deposition boat containing LiF, tungsten vapor deposition boat containing aluminum to install After depressurizing the vacuum chamber to 5x10 ^-4 Pa, TSPO1 is heated and vapor-deposited so as to have a film thickness of 30 nm to form an electron transport layer. The deposition rate at the time of forming the electron transport layer is set to 1 nm/sec. Then, LiF is heated and vapor-deposited at the deposition rate of 0.01-0.1 nm/sec so that it may become a film thickness of 1 nm. Then, aluminum is heated and vapor-deposited to a film thickness of 100 nm to form a cathode. In this way, an organic EL element is obtained.

<Examples 2-5 and Examples 2-6>

An organic EL device is obtained in the same manner as in Example 2-4 using the composition (3) or (4) for forming a light emitting layer.

<Evaluation of the organic EL device of Examples 2-4 to 2-6>

It can be expected that the coating-type organic EL device obtained as described above also has excellent driving voltage and external quantum efficiency like the deposition-type organic EL device.

<Production of organic EL devices of Examples 2-7 to 2-9>

Table 9 shows the material configuration of each layer in the organic EL device.

[Table 9]

<Preparation of compositions (5) to (7) for forming a light emitting layer>

The composition (5) for light emitting layer formation is prepared by stirring the following components until it becomes a uniform solution.

Compound (A) 0.02% by weight

2PXZ-TAZ 0.18 wt%

mCBP 1.80 wt%

98.00% by weight of toluene

The composition (6) for light emitting layer formation is prepared by stirring the following components until it becomes a uniform solution.

Compound (A) 0.02% by weight

2PXZ-TAZ 0.18 wt%

SPH-101 1.80 wt%

98.00% by weight of xylene

The composition (7) for light emitting layer formation is prepared by stirring the following components until it becomes a uniform solution.

Compound (A) 0.02% by weight

2PXZ-TAZ 0.18 wt%

DOBNA 1.80 wt%

98.00% by weight of toluene

In Table 9, "2PXZ-TAZ" is 10,10'-((4-phenyl-4H-1,2,4-triazole-3,5-diyl)bis(4,1-phenylene)) bis(10H-phenoxazine). The chemical structure is shown below.

<Example 2-7>

After spin-coating ND-3202 (manufactured by Nissan Chemical Industry Co., Ltd.) solution on a glass substrate on which ITO was deposited to a thickness of 45 nm, heated at 50 ° C. for 3 minutes in an atmospheric atmosphere, and then heated again at 230 ° C. for 15 minutes, An ND-3202 film with a film thickness of 50 nm is formed (hole injection layer). Then, the XLP-101 solution is spin-coated and heated on a hot plate at 200° C. for 30 minutes in a nitrogen gas atmosphere to form an XLP-101 film with a thickness of 20 nm (hole transport layer). Then, the composition 5 for forming a light emitting layer is spin-coated and heated at 130° C. for 10 minutes in a nitrogen gas atmosphere to form a light emitting layer with a thickness of 20 nm.

The produced multilayer film is fixed to the substrate holder of a commercial vapor deposition apparatus (manufactured by Showa Vacuum Co., Ltd.), and molybdenum vapor deposition boat containing TSPO1, molybdenum vapor deposition boat containing LiF, tungsten vapor deposition boat containing aluminum to install After depressurizing the vacuum chamber to 5x10 ^-4 Pa, TSPO1 is heated and vapor-deposited so as to have a film thickness of 30 nm to form an electron transport layer. The deposition rate at the time of forming the electron transport layer is set to 1 nm/sec. Then, LiF is heated and vapor-deposited at the deposition rate of 0.01-0.1 nm/sec so that it may become a film thickness of 1 nm. Then, aluminum is heated and vapor-deposited to a film thickness of 100 nm to form a cathode. In this way, an organic EL element is obtained.

<Examples 2-8 and Examples 2-9>

An organic EL device was obtained in the same manner as in Example 2-7 using the composition (6) or (7) for forming a light emitting layer.

<Evaluation of the organic EL device of Examples 2-7 to 2-9>

It can be expected that the coating-type organic EL device obtained as described above also has excellent driving voltage and external quantum efficiency like the deposition-type organic EL device.

As described above, some of the compounds according to the present invention were evaluated as materials for organic EL devices and were shown to be excellent materials. Since it is a compound having a compound, it can be understood by those skilled in the art that it is an excellent material for an organic EL device as well.

100 organic electroluminescent device
101 board
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 (17)

A polycyclic aromatic compound represented by the following formula (1A-1) and having a structure comprising one or two or more structural units.

In formula (1A-1),
A2 ring, A3 ring, and A4 ring are each independently a substituted or unsubstituted aryl ring, or a substituted or unsubstituted heteroaryl ring,
ring A1 and ring A5 are each independently a substituted or unsubstituted aryl ring, a substituted or unsubstituted heteroaryl ring, a substituted or unsubstituted cycloalkyl ring, or a cycloheteroalkyl ring;
Y ¹ is B, P, P=O, P=S, Al, Ga, As, Si-R, or Ge-R, wherein R of Si-R and Ge-R is substituted or unsubstituted aryl , substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl;
L ¹ , L ² , L ³ , and L ⁴ are each independently a single bond, substituted or unsubstituted arylene, substituted or unsubstituted heteroarylene, substituted or unsubstituted alkylene, substituted or unsubstituted cycloalkylene, substituted or unsubstituted alkenylene, >O, >NR, >C(-R) ₂ , >Si(-R) ₂ , >S, or >Se, wherein R of >NR, said R of >Si(-R) ₂ and R of >C(-R) ₂ are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, wherein two R of >Si(-R) ₂ and two R of >C(-R) ₂ are not bonded to each other to form a ring, or , R of >NR, R of >C(-R) ₂ , and at least one R of >Si(-R) ₂ Each independently represents an A1 ring, A2 ring, A3 ring, A4 ring, and At least one of the A5 rings is not bonded to, or is bonded to, through a single bond or a linking group;
n, m, q, and r are each independently 0 or 1, and in the case of 0, each independently means that hydrogen or a substituent is present instead of L ¹ , L ² , L ³ or L ⁴ , provided that , n+m=1 and not q+r=0;
The polycyclic aromatic compound having a structure consisting of one or two or more of the structural units represented by the formula (1A-1) is not condensed with at least one cycloalkane or is condensed with at least one cycloalkane one hydrogen is unsubstituted or substituted, and at least one -CH ₂ - in the corresponding cycloalkane is unsubstituted or substituted with -O- or -S-, and;
At least one hydrogen in the structure represented by formula (1A-1) is unsubstituted or substituted with cyano, halogen, or deuterium. According to claim 1,
The polycyclic aromatic compound wherein the structural unit is a structural unit represented by the following formula (1a-1).

In formula (1a-1),
Y ¹ is B, P, P=O, P=S, Al, Ga, As, Si-R, or Ge-R, wherein R of Si-R and Ge-R is substituted or unsubstituted aryl , substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl;
L ¹ , L ² , L ³ , and L ⁴ are each independently a single bond, substituted or unsubstituted arylene, substituted or unsubstituted heteroarylene, substituted or unsubstituted alkylene, substituted or unsubstituted cycloalkylene, substituted or unsubstituted alkenylene, >O, >NR, >C(-R) ₂ , >Si(-R) ₂ , >S, or >Se, wherein R of >NR, said R of >Si(-R) ₂ and R of >C(-R) ₂ are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, wherein two R of >Si(-R) ₂ and two R of >C(-R) ₂ are not bonded to each other to form a ring, or , R of >NR, R of >C(-R) ₂ , and at least one R of >Si(-R) ₂ are each independently at least one of R ^Z in Z that is CR ^Z and -O-, -S-, -C(-R) ₂ - or not bonded by a single bond or bonded;
n, m, q, and r are each independently 0 or 1, the case of 0 means that each independently R ¹ is present instead of L ¹ , L ² , L ³ or L ⁴ , provided that n+m=1 and not q+r=0;
each Z is, independently, N or CR ¹ , or Z=Z is each independently >O, >NR, >C(-R) ₂ , >Si(-R) ₂ , >S, or >Se , wherein R ¹ of CR ¹ is each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio or substituted silyl, wherein at least one hydrogen is unsubstituted or substituted with aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, The two aryls are not bonded to each other or are bonded through a linking group, and the two heteroaryls of the diheteroarylamino are not bonded to each other or are bonded through a linking group, and the aryl and heteroaryl of the arylheteroarylamino are hetero Aryl is not bonded to each other or is bonded through a linking group, and the two aryls of the diarylboryl are not bonded to each other, or are bonded to each other through a single bond or a linking group;
Two adjacent R ¹ are bonded to each other, do not form or form an aryl ring or a heteroaryl ring, and at least one hydrogen of the formed aryl ring and the formed aryl heteroaryl ring is, respectively, aryl, hetero unsubstituted or substituted with aryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or substituted silyl; At least one hydrogen in is unsubstituted or substituted with aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, and the two aryls of the diarylamino are not bonded to each other, Or they are bonded through a linking group, and the two heteroaryls of the diheteroarylamino are not bonded to each other, or are bonded through a linking group, and the aryl and heteroaryl of the arylheteroarylamino are not bonded to each other, or a linking group are bonded through, and the two aryls of the diarylboryl are not bonded to each other, or are bonded through a single bond or a linking group, and the >NR, the >C(-R) ₂ and the >Si(-R) ) ₂ R is each independently hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, wherein at least one hydrogen is aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl unsubstituted or substituted, and two R of >C(-R) ₂ and >Si(-R) ₂ are not bonded to each other to form a ring;
The polycyclic aromatic compound having a structure comprising one or two or more of the structural units represented by the formula (1a-1) is not condensed with at least one cycloalkane or is condensed with at least one cycloalkane one hydrogen is unsubstituted or substituted, and at least one -CH ₂ in the cycloalkane is unsubstituted or substituted with -O- or -S-, and;
At least one hydrogen in the structure represented by formula (1a-1) is unsubstituted or substituted with cyano, halogen, or deuterium. According to claim 1,
The polycyclic aromatic compound, wherein the structural unit is a structural unit represented by the following formula (1b-1) or (1b-2), respectively.

In formulas (1b-1) and (1b-2),
L ³ , L ⁴ are each independently a single bond, arylene, heteroarylene or alkenylene, at least one of which hydrogen is not substituted with alkyl, cycloalkyl, diarylamino, or substituted silyl, or is substituted, and the two aryls of the diarylamino are not bonded or bonded through a linking group;
q, and r are each independently 0 or 1, the case of 0 means that each independently R ¹ is present instead of L ³ or L ⁴ , provided that q+r=0;
Y ¹ is B, P, P=O, P=S, Al, Ga, As, Si-R, or Ge-R, wherein R of Si-R and Ge-R is substituted or unsubstituted aryl , substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl;
each Z is, independently, N or CR ¹ , or Z=Z is each independently >O, >NR, >C(-R) ₂ , >Si(-R) ₂ , >S, or >Se , wherein R ¹ of CR ¹ is each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio or substituted silyl, wherein at least one hydrogen is unsubstituted or substituted with aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, The two aryls are not bonded to each other or are bonded through a linking group, and the two heteroaryls of the diheteroarylamino are not bonded to each other or are bonded through a linking group, and the aryl and heteroaryl of the arylheteroarylamino are hetero Aryl is not bonded to each other or is bonded through a linking group, and the two aryls of the diarylboryl are not bonded to each other, or are bonded to each other through a single bond or a linking group;
Two adjacent R ¹ are bonded to each other, do not form or form an aryl ring or a heteroaryl ring, and at least one hydrogen of the formed aryl ring and the formed aryl heteroaryl ring is, respectively, aryl, hetero unsubstituted or substituted with aryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or substituted silyl; At least one hydrogen in is unsubstituted or substituted with aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, and the two aryls of the diarylamino are not bonded to each other, Or they are bonded through a linking group, and the two heteroaryls of the diheteroarylamino are not bonded to each other, or are bonded through a linking group, and the aryl and heteroaryl of the arylheteroarylamino are not bonded to each other, or a linking group are bonded through, and the two aryls of the diarylboryl are not bonded to each other, or are bonded through a single bond or a linking group, and the >NR, the >C(-R) ₂ and the >Si(-R) ) ₂ R is each independently hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, wherein at least one hydrogen is aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl is unsubstituted or substituted, and the >C(-R) ₂ and the >Si(-R) ₂ , two R of which are not bonded to each other to form a ring;
The polycyclic aromatic compound having a structure comprising one or two or more of the structural units represented by formula (1b-1) or formula (1b-2) is not condensed with at least one cycloalkane or is condensed; At least one hydrogen in the cycloalkane is unsubstituted or substituted, and at least one -CH ₂ - in the cycloalkane is unsubstituted or substituted with -O- or -S-, , and;
At least one hydrogen in the structure represented by the formula (1b-1) or (1b-2) is unsubstituted or substituted with cyano, halogen, or deuterium. According to claim 1,
A polycyclic aromatic compound, wherein the structural unit is a structural unit represented by the following formula (1c-1), (1c-2), (1c-3), or (1c-4).

In formula (1c-1), formula (1c-2), formula (1c-3) and formula (1c-4),
each Z is, independently, N or CR ¹ , or Z=Z is each independently >O, >NR, >C(-R) ₂ , >Si(-R) ₂ , >S, or >Se , wherein R ¹ of CR ¹ is each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio or substituted silyl, wherein at least one hydrogen is unsubstituted or substituted with aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, The two aryls are not bonded to each other or are bonded through a linking group, and the two heteroaryls of the diheteroarylamino are not bonded to each other or are bonded through a linking group, and the aryl and heteroaryl of the arylheteroarylamino are hetero Aryl is not bonded to each other or is bonded through a linking group, and the two aryls of the diarylboryl are not bonded to each other, or are bonded to each other through a single bond or a linking group;
Two adjacent R ¹ are bonded to each other, do not form or form an aryl ring or a heteroaryl ring, and at least one hydrogen of the formed aryl ring and the formed aryl heteroaryl ring is, respectively, aryl, hetero unsubstituted or substituted with aryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or substituted silyl; At least one hydrogen in is unsubstituted or substituted with aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, and the two aryls of the diarylamino are not bonded to each other, Or they are bonded through a linking group, and the two heteroaryls of the diheteroarylamino are not bonded to each other, or are bonded through a linking group, and the aryl and heteroaryl of the arylheteroarylamino are not bonded to each other, or a linking group are bonded through, and the two aryls of the diarylboryl are not bonded to each other, or are bonded through a single bond or a linking group, and the >NR, the >C(-R) ₂ and the >Si(-R) ) ₂ R is each independently hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, wherein at least one hydrogen is aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl unsubstituted or substituted, and two R of >C(-R) ₂ and >Si(-R) ₂ are not bonded to each other to form a ring;
A polycyclic aromatic compound having a structure comprising one or two or more of the structural units represented by formula (1c-1), formula (1c-2), formula (1c-3), or formula (1c-4) is uncondensed or condensed with at least one cycloalkane, at least one hydrogen in the cycloalkane is unsubstituted or substituted, and at least one -CH ₂ - in the cycloalkane is - unsubstituted or substituted with O- or -S-, and;
At least one hydrogen in the structure represented by formula (1c-1), formula (1c-2), formula (1c-3), or formula (1c-4) is not substituted with cyano, halogen, or deuterium or is substituted. According to claim 1,
The polycyclic aromatic compound, wherein the structural unit is a structural unit represented by formula (1d-1) or (1d-2).

In formulas (1d-1) and (1d-2),
L ³ , L ⁴ are each independently a single bond, arylene, heteroarylene or alkenylene, at least one of which hydrogen is not substituted with alkyl, cycloalkyl, diarylamino, or substituted silyl, or is substituted, and the two aryls of the diarylamino are not bonded or bonded through a linking group;
q, and r are each independently 0 or 1, the case of 0 means that each independently R ¹ is present instead of L ³ or L ⁴ with the proviso that q+r=0;
Y ¹ is B, P, P=O, P=S, Al, Ga, As, Si-R, or Ge-R, wherein R of Si-R and Ge-R is substituted or unsubstituted aryl , substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl;
each Z is, independently, N or CR ¹ , or Z=Z is each independently >O, >NR, >C(-R) ₂ , >Si(-R) ₂ , >S, or >Se , wherein R ¹ of CR ¹ is each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio or substituted silyl, wherein at least one hydrogen is unsubstituted or substituted with aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, The two aryls are not bonded to each other or are bonded through a linking group, and the two heteroaryls of the diheteroarylamino are not bonded to each other or are bonded through a linking group, and the aryl and heteroaryl of the arylheteroarylamino are hetero Aryl is not bonded to each other or is bonded through a linking group, and the two aryls of the diarylboryl are not bonded to each other, or are bonded to each other through a single bond or a linking group;
Two adjacent R ¹ are bonded to each other, do not form or form an aryl ring or a heteroaryl ring, and at least one hydrogen of the formed aryl ring and the formed aryl heteroaryl ring is, respectively, aryl, hetero unsubstituted or substituted with aryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or substituted silyl; At least one hydrogen in is unsubstituted or substituted with aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, and the two aryls of the diarylamino are not bonded to each other, Or they are bonded through a linking group, and the two heteroaryls of the diheteroarylamino are not bonded to each other, or are bonded through a linking group, and the aryl and heteroaryl of the arylheteroarylamino are not bonded to each other, or a linking group are bonded through, and the two aryls of the diarylboryl are not bonded to each other, or are bonded through a single bond or a linking group, and the >NR, the >C(-R) ₂ and the >Si(-R) ) ₂ R is each independently hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, wherein at least one hydrogen is aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl unsubstituted or substituted, and two R of >C(-R) ₂ and >Si(-R) ₂ are not bonded to each other to form a ring;
each R ^d is independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or substituted silyl, wherein at least one hydrogen is unsubstituted or substituted with aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, wherein the two aryls of the diarylamino are not bonded to each other or is bonded through a linking group, the two heteroaryls of the diheteroarylamino are not bonded to each other, or are bonded through a linking group, and the aryl and heteroaryl of the arylheteroarylamino are not bonded to each other, Or they are bonded through a linking group, and the two aryls of the diarylboryl are not bonded to each other, or are bonded through a single bond or a linking group;
The polycyclic aromatic compound having a structure consisting of one or two or more of the structural units represented by formula (1d-1) or formula (1d-2) is not condensed with at least one cycloalkane or is condensed; At least one hydrogen in the cycloalkane is unsubstituted or substituted, and at least one -CH ₂ - in the cycloalkane is unsubstituted or substituted with -O- or -S-, , and;
At least one hydrogen in the structure represented by the formula (1d-1) or (1d-2) is unsubstituted or substituted with cyano, halogen, or deuterium. According to claim 1,
The polycyclic aromatic compound, wherein the structural unit is a structural unit represented by formula (1e-1), formula (1e-2), formula (1e-3) or formula (1e-4).

In formula (1e-1), formula (1e-2), formula (1e-3) and formula (1e-4),
each Z is, independently, N or CR ¹ , or Z=Z is each independently >O, >NR, >C(-R) ₂ , >Si(-R) ₂ , >S, or >Se , wherein R ¹ of CR ¹ is each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio or substituted silyl, wherein at least one hydrogen is unsubstituted or substituted with aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, The two aryls are not bonded to each other or are bonded through a linking group, and the two heteroaryls of the diheteroarylamino are not bonded to each other or are bonded through a linking group, and the aryl and heteroaryl of the arylheteroarylamino are hetero Aryl is not bonded to each other or is bonded through a linking group, and the two aryls of the diarylboryl are not bonded to each other, or are bonded to each other through a single bond or a linking group;
Two adjacent R ¹ are bonded to each other, do not form or form an aryl ring or a heteroaryl ring, and at least one hydrogen of the formed aryl ring and the formed aryl heteroaryl ring is, respectively, aryl, hetero unsubstituted or substituted with aryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or substituted silyl; At least one hydrogen in is unsubstituted or substituted with aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, and the two aryls of the diarylamino are not bonded to each other, Or they are bonded through a linking group, and the two heteroaryls of the diheteroarylamino are not bonded to each other, or are bonded through a linking group, and the aryl and heteroaryl of the arylheteroarylamino are not bonded to each other, or a linking group are bonded through, and the two aryls of the diarylboryl are not bonded to each other, or are bonded through a single bond or a linking group, and the >NR, the >C(-R) ₂ and the >Si(-R) ) ₂ R is each independently hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, wherein at least one hydrogen is aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl unsubstituted or substituted, and two R of >C(-R) ₂ and >Si(-R) ₂ are not bonded to each other to form a ring;
each R ^d is independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or substituted silyl, wherein at least one hydrogen is unsubstituted or substituted with aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, wherein the two aryls of the diarylamino are not bonded to each other or is bonded through a linking group, the two heteroaryls of the diheteroarylamino are not bonded to each other, or are bonded through a linking group, and the aryl and heteroaryl of the arylheteroarylamino are not bonded to each other, Or they are bonded through a linking group, and the two aryls of the diarylboryl are not bonded to each other, or are bonded through a single bond or a linking group;
A polycyclic aromatic compound having a structure comprising one or two or more of the structural units represented by formula (1e-1), formula (1e-2), formula (1e-3) or formula (1e-4) is at least uncondensed or condensed with one cycloalkane, at least one hydrogen in the cycloalkane is unsubstituted or substituted, and at least one -CH ₂ - in the cycloalkane is -O unsubstituted or substituted with - or -S-, and;
At least one hydrogen in the structure represented by formula (1e-1), formula (1e-2), formula (1e-3) or formula (1e-4) is not substituted with cyano, halogen, or deuterium or is substituted. According to claim 1,
The polycyclic aromatic compound, wherein the structural unit is a structural unit represented by the formula (1f-1) or (1f-2).

In formulas (1f-1) and (1f-2),
x is an integer from 1 to 3;
Y ¹ is B, P, P=O, P=S, Al, Ga, As, Si-R, or Ge-R, wherein R of Si-R and Ge-R is substituted or unsubstituted aryl , substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl;
L ¹ , L ² , L ³ , and L ⁴ are each independently a single bond, substituted or unsubstituted arylene, substituted or unsubstituted heteroarylene, substituted or unsubstituted alkylene, substituted or unsubstituted cycloalkylene, substituted or unsubstituted alkenylene, >O, >NR, >C(-R) ₂ , >Si(-R) ₂ , >S, or >Se, wherein R of >NR, said R of >Si(-R) ₂ and R of >C(-R) ₂ are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, wherein two R of >Si(-R) ₂ and two R of >C(-R) ₂ are not bonded to each other to form a ring, or wherein R of >NR, R of >C(-R) ₂ , and at least one R of >Si(-R) ₂ are each independently at least one of R ^Z in Z that is CR ^Z One and -O-, -S-, -C(-R) ₂ - or not bonded by a single bond, or bonded;
n, m, q, and r are each independently 0 or 1, the case of 0 means that each independently hydrogen or a substituent is present instead of L ¹ , L ² , L ³ or L ⁴ , provided that , n+m=1 and not q+r=0;
A is each independently >(CR)-, wherein R of >(CR)- is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl;
each E is, independently, >O, >NR, >C(-R) ₂ , >Si(-R) ₂ , >S, or >Se, wherein R of >NR, the >Si(-R) R of ₂ and R of >C(-R) ₂ are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, wherein two R of >Si(-R) ₂ and two R of >C(-R) ₂ are not bonded to each other to form a ring;
each Z is, independently, N or CR ¹ , or Z=Z is each independently >O, >NR, >C(-R) ₂ , >Si(-R) ₂ , >S, or >Se , wherein R ¹ of CR ¹ is each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio or substituted silyl, wherein at least one hydrogen is unsubstituted or substituted with aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, The two aryls are not bonded to each other or are bonded through a linking group, and the two heteroaryls of the diheteroarylamino are not bonded to each other or are bonded through a linking group, and the aryl and heteroaryl of the arylheteroarylamino are hetero Aryl is not bonded to each other or is bonded through a linking group, and the two aryls of the diarylboryl are not bonded to each other, or are bonded to each other through a single bond or a linking group;
Two adjacent R ¹ are bonded to each other, do not form or form an aryl ring or a heteroaryl ring, and at least one hydrogen of the formed aryl ring and the formed aryl heteroaryl ring is, respectively, aryl, hetero unsubstituted or substituted with aryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or substituted silyl; At least one hydrogen in is unsubstituted or substituted with aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, and the two aryls of the diarylamino are not bonded to each other, Or they are bonded through a linking group, and the two heteroaryls of the diheteroarylamino are not bonded to each other, or are bonded through a linking group, and the aryl and heteroaryl of the arylheteroarylamino are not bonded to each other, or a linking group are bonded through, and the two aryls of the diarylboryl are not bonded to each other, or are bonded through a single bond or a linking group, and the >NR, the >C(-R) ₂ and the >Si(-R) ) ₂ R is each independently hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, wherein at least one hydrogen is aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl unsubstituted or substituted, and two R of >C(-R) ₂ and >Si(-R) ₂ are not bonded to each other to form a ring;
The polycyclic aromatic compound having a structure consisting of one or two or more of the structural units represented by the formulas (1f-1) and (1f-2) is not condensed with at least one cycloalkane or is condensed; At least one hydrogen in the cycloalkane is unsubstituted or substituted, and at least one -CH ₂ - in the cycloalkane is unsubstituted or substituted with -O- or -S-, , and;
At least one hydrogen in the structures represented by formulas (1f-1) and (1f-2) is unsubstituted or substituted with cyano, halogen, or deuterium. According to claim 1,
A polycyclic aromatic compound, wherein the structural unit is a structural unit represented by the following formula (1g-1) or (1g-2), respectively.

In formulas (1g-1) and (1g-2),
x is an integer from 1 to 3;
L ³ , L ⁴ are each independently a single bond, arylene, heteroarylene or alkenylene, and at least one hydrogen of these is not substituted with alkyl, cycloalkyl, diarylamino, or substituted silyl, or is substituted, and the two aryls of the diarylamino are not bonded through a linking group or are bonded;
q, and r are each independently 0 or 1, the case of 0 means that each independently R ¹ is present instead of L ³ or L ⁴ , provided that q+r=0;
Y ¹ is B, P, P=O, P=S, Al, Ga, As, Si-R, or Ge-R, wherein R of Si-R and Ge-R is substituted or unsubstituted aryl , substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl;
A is each independently >(CR)-, wherein R of >(CR)- is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl;
each E is, independently, >O, >NR, >C(-R) ₂ , >Si(-R) ₂ , >S, or >Se, wherein R of >NR, the >Si(-R) R of ₂ and R of >C(-R) ₂ are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, wherein two R of >Si(-R) ₂ and two R of >C(-R) ₂ are not bonded to each other to form a ring;
each Z is, independently, N or CR ¹ , or Z=Z is each independently >O, >NR, >C(-R) ₂ , >Si(-R) ₂ , >S, or >Se , wherein R ¹ of CR ¹ is each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio or substituted silyl, wherein at least one hydrogen is unsubstituted or substituted with aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, The two aryls are not bonded to each other or are bonded through a linking group, and the two heteroaryls of the diheteroarylamino are not bonded to each other or are bonded through a linking group, and the aryl and heteroaryl of the arylheteroarylamino are hetero Aryl is not bonded to each other or is bonded through a linking group, and the two aryls of the diarylboryl are not bonded to each other, or are bonded to each other through a single bond or a linking group;
Two adjacent R ¹ are bonded to each other, do not form or form an aryl ring or a heteroaryl ring, and at least one hydrogen of the formed aryl ring and the formed aryl heteroaryl ring is, respectively, aryl, hetero unsubstituted or substituted with aryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or substituted silyl; At least one hydrogen in is unsubstituted or substituted with aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, and the two aryls of the diarylamino are not bonded to each other, Or they are bonded through a linking group, and the two heteroaryls of the diheteroarylamino are not bonded to each other, or are bonded through a linking group, and the aryl and heteroaryl of the arylheteroarylamino are not bonded to each other, or a linking group are bonded through, and the two aryls of the diarylboryl are not bonded to each other, or are bonded through a single bond or a linking group, and the >NR, the >C(-R) ₂ and the >Si(-R) ) ₂ R is each independently hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, wherein at least one hydrogen is aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl unsubstituted or substituted, and two R of >C(-R) ₂ and >Si(-R) ₂ are not bonded to each other to form a ring;
The polycyclic aromatic compound having a structure consisting of one or two or more of the structural units represented by the formula (1g-1) or (1g-2) is not condensed with at least one cycloalkane or is condensed, At least one hydrogen in the cycloalkane is unsubstituted or substituted, and at least one -CH ₂ - in the cycloalkane is unsubstituted or substituted with -O- or -S-, , and;
At least one hydrogen in the structure represented by the formula (1g-1) or (1g-2) is unsubstituted or substituted with cyano, halogen, or deuterium. According to claim 1,
A polycyclic aromatic compound, wherein the structural unit is a structural unit represented by the following formula (1h-1), (1h-2), (1h-3), or (1h-4).

In formula (1h-1), formula (1h-2), formula (1h-3) and formula (1h-4),
x is an integer from 1 to 3;
A is, each independently, >(CR)-, wherein R of >(CR)- is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl;
E is, each independently, >O, >NR, >C(-R) ₂ , >Si(-R) ₂ , >S, or >Se, wherein R of >NR, >Si(-R) R of ₂ and R of >C(-R) ₂ are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, wherein the two Rs of >Si(-R) ₂ and the two Rs of >C(-R) ₂ are not bonded to each other to form a ring;
each Z is, independently, N or CR ¹ , or each Z=Z is independently >O, >NR, >C(-R) ₂ , >Si(-R) ₂ , >S, or >Se , wherein R ¹ of CR ¹ is each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio or substituted silyl, wherein at least one hydrogen is unsubstituted or substituted with aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, The two aryls are not bonded to each other or are bonded through a linking group, and the two heteroaryls of the diheteroarylamino are not bonded to each other or are bonded through a linking group, and the aryl and heteroaryl of the arylheteroarylamino are hetero Aryl is not bonded to each other or is bonded through a linking group, and the two aryls of the diarylboryl are not bonded to each other, or are bonded to each other through a single bond or a linking group;
Two adjacent R ¹ are bonded to each other, do not form or form an aryl ring or a heteroaryl ring, and at least one hydrogen of the formed aryl ring and the formed aryl heteroaryl ring is, respectively, aryl, hetero unsubstituted or substituted with aryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or substituted silyl; At least one hydrogen in is unsubstituted or substituted with aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, and the two aryls of the diarylamino are not bonded to each other, Or they are bonded through a linking group, and the two heteroaryls of the diheteroarylamino are not bonded to each other, or are bonded through a linking group, and the aryl and heteroaryl of the arylheteroarylamino are not bonded to each other, or a linking group are bonded through, and the two aryls of the diarylboryl are not bonded to each other, or are bonded through a single bond or a linking group, and the >NR, the >C(-R) ₂ and the >Si(-R) ) ₂ R is each independently hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, wherein at least one hydrogen is aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl unsubstituted or substituted, and two R of >C(-R) ₂ and >Si(-R) ₂ are not bonded to each other to form a ring;
A polycyclic aromatic compound having a structure comprising one or two or more of the structural units represented by formula (1h-1), formula (1h-2), formula (1h-3), or formula (1h-4) is uncondensed or condensed with at least one cycloalkane, at least one hydrogen in the cycloalkane is unsubstituted or substituted, and at least one -CH ₂ - in the cycloalkane is - unsubstituted or substituted with O- or -S-, and;
At least one hydrogen in the structure represented by formula (1h-1), formula (1h-2), formula (1h-3), or formula (1h-4) is not substituted with cyano, halogen, or deuterium or is substituted. According to claim 1,
A polycyclic aromatic compound wherein the structural unit is a structural unit represented by formula (1i-1) or (1i-2).

In formulas (1i-1) and (1i-2),
x is an integer from 1 to 3;
L ³ , L ⁴ are each independently a single bond, arylene, heteroarylene or alkenylene, and at least one hydrogen of these is not substituted with alkyl, cycloalkyl, diarylamino, or substituted silyl, or is substituted, and the two aryls of the diarylamino are not bonded through a linking group or are bonded;
q, and r are each independently 0 or 1, the case of 0 means that each independently R ¹ is present instead of L ³ or L ⁴ , provided that q+r=0;
Y ¹ is B, P, P=O, P=S, Al, Ga, As, Si-R, or Ge-R, wherein R of Si-R and Ge-R is substituted or unsubstituted aryl , substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl;
A is each independently >(CR)-, wherein R of >(CR)- is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl;
each E is, independently, >O, >NR, >C(-R) ₂ , >Si(-R) ₂ , >S, or >Se, wherein R of >NR, the >Si(-R) R of ₂ and R of >C(-R) ₂ are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, wherein two R of >Si(-R) ₂ and two R of >C(-R) ₂ are not bonded to each other to form a ring;
each Z is, independently, N or CR ¹ , or Z=Z is each independently >O, >NR, >C(-R) ₂ , >Si(-R) ₂ , >S, or > Se , wherein R ¹ of CR ¹ is each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio or substituted silyl, wherein at least one hydrogen is unsubstituted or substituted with aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, The two aryls are not bonded to each other or are bonded through a linking group, and the two heteroaryls of the diheteroarylamino are not bonded to each other or are bonded through a linking group, and the aryl and heteroaryl of the arylheteroarylamino are hetero Aryl is not bonded to each other or is bonded through a linking group, and the two aryls of the diarylboryl are not bonded to each other, or are bonded to each other through a single bond or a linking group;
Adjacent two R ¹ are bonded to each other and do not form or form an aryl ring or a heteroaryl ring, and at least one hydrogen of the formed aryl ring and the formed aryl heteroaryl ring is, respectively, aryl, hetero unsubstituted or substituted with aryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or substituted silyl; At least one hydrogen in is unsubstituted or substituted with aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, and the two aryls of the diarylamino are not bonded to each other, Or it is bonded through a linking group, the two heteroaryls of the diheteroarylamino are not bonded to each other, or are bonded through a linking group, and the aryl and heteroaryl of the arylheteroarylamino are not bonded to each other, or a linking group are bonded through, and the two aryls of the diarylboryl are not bonded to each other, or are bonded through a single bond or a linking group, and the >NR, the >C(-R) ₂ and the >Si(-R) ) ₂ R is each independently hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, wherein at least one hydrogen is aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl unsubstituted or substituted, and two R of >C(-R) ₂ and >Si(-R) ₂ are not bonded to each other to form a ring;
each R ^d is independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or substituted silyl, wherein at least one hydrogen is unsubstituted or substituted with aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, wherein the two aryls of the diarylamino are not bonded to each other or is bonded through a linking group, the two heteroaryls of the diheteroarylamino are not bonded to each other, or are bonded through a linking group, and the aryl and heteroaryl of the arylheteroarylamino are not bonded to each other, Or they are bonded through a linking group, and the two aryls of the diarylboryl are not bonded to each other, or are bonded through a single bond or a linking group;
The polycyclic aromatic compound having a structure consisting of one or two or more of the structural units represented by formula (1i-1) or formula (1i-2) is not condensed with at least one cycloalkane or is condensed; At least one hydrogen in the cycloalkane is unsubstituted or substituted, and at least one -CH ₂ - in the cycloalkane is unsubstituted or substituted with -O- or -S-, , and;
At least one hydrogen in the structure represented by the formula (1i-1) or (1i-2) is unsubstituted or substituted with cyano, halogen, or deuterium. According to claim 1,
A polycyclic aromatic compound, wherein the structural unit is a structural unit represented by the formula (1k-1), the formula (1k-2), the formula (1k-3), or the formula (1k-4).

In formula (1k-1), formula (1k-2), formula (1k-3), and formula (1k-4),
x is an integer from 1 to 3;
A is, each independently, >(CR)-, wherein R of >(CR)- is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl;
E is, each independently, >O, >NR, >C(-R) ₂ , >Si(-R) ₂ , >S, or >Se, wherein R of >NR, >Si(-R) R of ₂ and R of >C(-R) ₂ are each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted and cycloalkyl, wherein two R of >Si(-R) ₂ and two R of >C(-R) ₂ are not bonded to each other to form a ring,
each Z is, independently, N or CR ¹ , or each Z=Z is independently >O, >NR, >C(-R) ₂ , >Si(-R) ₂ , >S, or >Se , wherein R ¹ of CR ¹ is each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio or substituted silyl, wherein at least one hydrogen is unsubstituted or substituted with aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, The two aryls are not bonded to each other or are bonded through a linking group, and the two heteroaryls of the diheteroarylamino are not bonded to each other or are bonded through a linking group, and the aryl and heteroaryl of the arylheteroarylamino are hetero Aryl is not bonded to each other or is bonded through a linking group, and the two aryls of the diarylboryl are not bonded to each other, or are bonded to each other through a single bond or a linking group;
Two adjacent R ¹ are bonded to each other, do not form or form an aryl ring or a heteroaryl ring, and at least one hydrogen of the formed aryl ring and the formed aryl heteroaryl ring is, respectively, aryl, hetero unsubstituted or substituted with aryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or substituted silyl; At least one hydrogen in is unsubstituted or substituted with aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, and the two aryls of the diarylamino are not bonded to each other, Or they are bonded through a linking group, the two heteroaryls of the diheteroarylamino are not bonded to each other, or are bonded through a linking group, and the aryl and heteroaryl of arylheteroarylamino are not bonded to each other, or a linking group and the two aryls of the diarylboryl are not bonded to each other, or are bonded through a single bond or a linking group, and the >NR, the >C(-R) ₂ and the >Si(-R) R of ₂ is each independently hydrogen, aryl, heteroaryl, alkyl, or cycloalkyl, wherein at least one hydrogen is substituted with aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl unsubstituted or substituted, and two R of >C(-R) ₂ and >Si(-R) ₂ are not bonded to each other to form a ring;
each R ^d is independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or substituted silyl, wherein at least one hydrogen is unsubstituted or substituted with aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, wherein the two aryls of the diarylamino are not bonded to each other or is bonded through a linking group, the two heteroaryls of the diheteroarylamino are not bonded to each other, or are bonded through a linking group, and the aryl and heteroaryl of the arylheteroarylamino are not bonded to each other, Or they are bonded through a linking group, and the two aryls of the diarylboryl are not bonded to each other, or are bonded through a single bond or a linking group;
A polycyclic aromatic compound having a structure comprising one or two or more of the structural units represented by formula (1k-1), formula (1k-2), formula (1k-3) or formula (1k-4) is at least uncondensed or condensed with one cycloalkane, at least one hydrogen in the cycloalkane is unsubstituted or substituted, and at least one -CH ₂ - in the cycloalkane is -O unsubstituted or substituted with - or -S-, and;
At least one hydrogen in the structure represented by formula (1k-1), formula (1k-2), formula (1k-3) or formula (1k-4) is not substituted with cyano, halogen, or deuterium or is substituted. According to claim 1,
A polycyclic aromatic compound represented by any one of the following structural formulas.

In the above formula, tBu is t-butyl. According to claim 1,
A polycyclic aromatic compound represented by any one of the following structural formulas.

The material for organic devices containing the polycyclic aromatic compound in any one of Claims 1-13. An organic electroluminescence comprising a pair of electrodes comprising an anode and a cathode, and a light emitting layer disposed between the pair of electrodes, wherein the light emitting layer contains the polycyclic aromatic compound according to any one of claims 1 to 13. device. 16. The method of claim 15,
The light emitting layer includes a host and the polycyclic aromatic compound as a dopant, an organic electroluminescent device. The display device or lighting device provided with the organic electroluminescent element in any one of Claim 15 or 16.

Images