CN114989198A

CN114989198A - Polycyclic aromatic compound, material for organic device, organic electroluminescent element, display device, and lighting device

Info

Publication number: CN114989198A
Application number: CN202210200726.4A
Authority: CN
Inventors: 畠山琢次; 小田晋; 川角亮介
Original assignee: Kwansei Gakuin Educational Foundation; SK Materials JNC Co Ltd
Current assignee: Kwansei Gakuin Educational Foundation; SK Materials JNC Co Ltd
Priority date: 2021-03-02
Filing date: 2022-03-02
Publication date: 2022-09-02
Also published as: JP2022133578A; KR20220124097A

Abstract

The invention provides a polycyclic aromatic compound, a material for an organic device, an organic electroluminescent element, a display device, and a lighting device. A polycyclic aromatic compound having one or more structures containing a structural unit represented by the formula (1A-1), wherein A is represented by the formula (1A-1)Ring 2, ring A3, and ring a4 are substituted or unsubstituted aryl rings, or substituted or unsubstituted heteroaryl rings, ring a1 and ring a5 are substituted or unsubstituted aryl rings, or substituted or unsubstituted heteroaryl rings, or substituted or unsubstituted cycloalkyl rings; n, m, q and r are each independently 0 or 1, where n + m is 1 and is not q + r is 0; y is ¹ B, P, P ═ O, P ═ S, Al, Ga, As, Si — R, or Ge — R; l is a radical of an alcohol ¹ 、L ² 、L ³ And L ⁴ Each independently a single bond or a linking group.

Description

Polycyclic aromatic compound, material for organic device, organic electroluminescent element, display device, and lighting device

Technical Field

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

Background

Conventionally, various studies have been made on display devices using light-emitting elements that perform electroluminescence, because they can achieve power saving and reduction in thickness, and further, organic electroluminescence elements including organic materials are actively studied because they are easy to reduce weight or increase size. In particular, in the development of an organic material having light-emitting characteristics such as blue, which is one of the three primary colors of light, and in the development of an organic material having charge transport capabilities (having a possibility of becoming a semiconductor or a superconductor) including holes, electrons, and the like, both high molecular compounds and low molecular compounds have been actively studied so far.

The organic electroluminescent element has a structure including: the organic light-emitting device includes a pair of electrodes including an anode and a cathode, and one or more layers including an organic compound and disposed between the pair of electrodes. The layer containing an organic compound includes a light-emitting layer, a charge transport/injection layer for transporting or injecting 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 effectively used as a material for an organic electroluminescent element or the like. It has been reported that the organic electroluminescent element containing the polycyclic aromatic compound has good external quantum efficiency.

[ Prior art documents ]

[ patent document ]

[ patent document 1] International publication No. 2015/102118

Disclosure of Invention

[ problems to be solved by the invention ]

As described above, various materials have been developed as materials used for organic Electroluminescence (EL) devices, but in order to increase the selection of materials for organic EL devices, it is desired to develop a material containing a compound different from the conventional one.

The problem of the present invention is to provide a novel compound which is effectively used as an organic device material for an organic EL element or the like.

[ means for solving the problems ]

The present inventors have made extensive studies to solve the above-mentioned problems, and have succeeded in producing a novel polycyclic aromatic compound having more excellent light-emitting characteristics among polycyclic aromatic compounds having a structure similar to that of the compound described in patent document 1.

Specifically, the present invention has the following configuration.

< 1 > a polycyclic aromatic compound having one or more structures containing a structural unit represented by the following formula (1A-1),

[ solution 1]

In the formula (1A-1),

the A2 ring, the A3 ring, and the 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, or 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, said Si-R and R of said Ge-R being 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 Independently of one another, a single bond, a substituted or unsubstituted arylene group, a substituted or unsubstituted heteroarylene group, a substituted or unsubstituted alkylene group, a substituted or unsubstituted cycloalkylene group, a substituted or unsubstituted alkenylene group, > O, > N-R, > C (-R) ₂ 、＞Si(-R) ₂ R > N-R, said > Si (-R) ₂ R of (b), and the & gtC (-R) ₂ Each R of (A) is independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, > Si (-R) ₂ And said > C (-R) ₂ Two R's are not bonded to each other to form a ring, or are bonded to each other to form a ring, R > N-R, the > C (-R) ₂ R of (b), and said > Si (-R) ₂ Is independently bonded to at least one of the A1 ring, the A2 ring, the A3 ring, the A4 ring, and the A5 ring, either not via a single bond or a linking group, or via 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 represents hydrogen or a substituent in place of L ¹ 、L ² 、L ³ Or L ⁴ And wherein n + m is 1 and is not q + r is 0,

the polycyclic aromatic compound having one or more than two structures containing the structural unit represented by the formula (1A-1) is not condensed by at least one cycloalkane, at least one hydrogen in the cycloalkane being unsubstituted,or substituted, at least one-CH in said cycloalkane ₂ -is unsubstituted-O-or-S-substituted, or is substituted, 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),

[ solution 2]

In the formula (1a-1),

Y ¹ is B, P, P ═ O, P ═ S, Al, Ga, As, Si-R, or Ge-R, R of said Si-R and said Ge-R is a 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 Independently of one another, a single bond, substituted or unsubstituted arylene, substituted or unsubstituted heteroarylene, substituted or unsubstituted alkylene, substituted or unsubstituted cycloalkylene, substituted or unsubstituted alkenylene, > O, > N-R, > C (-R) ₂ 、＞Si(-R) ₂ R > N-R, said > Si (-R) ₂ R of (b), and the & gtC (-R) ₂ Each R of (A) is independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, > Si (-R) ₂ Two R of (a) and said > C (-R) ₂ The two R's are not bonded to each other to form a ring, or are bonded to each other to form a ring, the R > N-R, the R > C (-R) ₂ R of (b), and said > Si (-R) ₂ Each of at least one R independently of the others is as C-R ^Z R in Z of (A) ^Z Does not utilize-O-, -S-, -C (-R) ₂ -or by a single bond, orwith-O-, -S-, -C (-R) ₂ -or a single bond, and is bonded to,

n, m, q, and R are each independently 0 or 1, and in the case of 0, each independently means R ¹ In place of L ¹ 、L ² 、L ³ Or L ⁴ And wherein n + m is 1 and is not q + r is 0,

z is each independently N or C-R ¹ Or each Z ═ Z is independently > O, > N-R, > C (-R) ₂ 、＞Si(-R) ₂ S or Se, the C-R ¹ R of (A) to (B) ¹ Independently of one another, hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboron, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or substituted silyl, at least one of which is unsubstituted or substituted by aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, the two aryl radicals of the diarylamino radical being unbound to one another or bound via a linking group, the two heteroaryl radicals of the diheteroarylamino radical being unbound to one another or bound via a linking group, the aryl and heteroaryl radicals of the arylheteroarylamino radical being unbound to one another or bound via a linking group, the two aryl radicals of the diarylboron radical being unbound to one another or bound via a single bond or a linking group,

two adjacent R ¹ At least one hydrogen of the formed aryl ring and the formed heteroaryl ring is unsubstituted or substituted by aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboron, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or substituted silyl, at least one hydrogen of them is unsubstituted or substituted by aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, the two aryl groups of the diarylamino group are not bonded to each other or bonded via a linking group, the two heteroaryl groups of the diheteroarylamino group are not bonded to each other or bonded via a linking group A bond, the aryl and heteroaryl of the arylheteroarylamino group being unbound to one another or bound via a linking group, the two aryl groups of the diarylboron group being unbound to one another or bound via a single bond or a linking group, the > N-R, the > C (-R) ₂ And said > Si (-R) ₂ Each R of (A) is independently hydrogen, aryl, heteroaryl, alkyl, cycloalkyl, at least one of which hydrogen is unsubstituted or substituted with aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, > C (-R) ₂ And said > Si (-R) ₂ Two R's are not bonded to each other to form a ring, or are bonded to each other to form a ring,

a polycyclic aromatic compound having one or more structures containing a structural unit represented by the formula (1a-1) is not condensed with at least one cycloalkane in which at least one hydrogen is unsubstituted or substituted, or is condensed with at least one cycloalkane in which at least one-CH is present ₂ -is unsubstituted-O-or-S-substituted, or is substituted, and,

< 3 > the polycyclic aromatic compound according to < 1 > wherein the structural units are each a structural unit represented by the following formula (1b-1) or formula (1b-2),

[ solution 3]

In the formulae (1b-1) and (1b-2),

L ³ 、L ⁴ each independently being a single bond, an arylene group, a heteroarylene group, or an alkenylene group, at least one hydrogen of which is unsubstituted or substituted by an alkyl group, a cycloalkyl group, a diarylamino group, or a substituted silyl group, two aryl groups of the diarylamino group being bonded either unsubstituted or via a linking group,

q and r are each independently 0 or 1 and are each 0In the case of each R independently of the other ¹ In place of L ³ Or L ⁴ And wherein q + r is not 0,

z is each independently N or C-R ¹ Or each Z ═ Z is independently > O, > N-R, > C (-R) ₂ 、＞Si(-R) ₂ S or Se, the C-R ¹ R of (A) ¹ Independently of one another, hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboron, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or substituted silyl, at least one of which is unsubstituted or substituted by aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, the two aryl radicals of the diarylamino radical being unbound to one another or bound via a linking group, the two heteroaryl radicals of the diheteroarylamino radical being unbound to one another or bound via a linking group, the aryl and heteroaryl radicals of the arylheteroarylamino radical being unbound to one another or bound via a linking group, the two aryl radicals of the diarylboron radical being unbound to one another or bound via a single bond or a linking group,

Two adjacent R ¹ Are not bonded to each other to form an aryl or heteroaryl ring, or are bonded to each other to form an aryl or heteroaryl ring, at least one hydrogen of the formed aryl ring and the formed heteroaryl ring, respectively, being unsubstituted or substituted by aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboron, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or substituted silyl, at least one hydrogen of which being unsubstituted or substituted by aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, both aryl groups of the diarylamino group being not bonded to each other, or being substituted by aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silylA linking group, the two heteroaryl groups of the diheteroarylamino group being not bonded to each other or bonded via the linking group, the aryl and heteroaryl groups of the arylheteroarylamino group being not bonded to each other or bonded via the linking group, the two aryl groups of the diarylboron group being not bonded to each other or bonded via a single bond or the linking group, the > N-R, the > C (-R) ₂ And said > Si (-R) ₂ Each R of (A) is independently hydrogen, aryl, heteroaryl, alkyl, cycloalkyl, at least one of which hydrogen is unsubstituted or substituted with aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, > C (-R) ₂ And said > Si (-R) ₂ Two R's are not bonded to each other to form a ring, or are bonded to each other to form a ring,

a polycyclic aromatic compound having one or more structures containing a structural unit represented by formula (1b-1) or formula (1b-2) is not condensed with at least one cycloalkane in which at least one hydrogen is unsubstituted or substituted, or is condensed with at least one cycloalkane in which at least one-CH is present ₂ -is unsubstituted-O-or-S-substituted, or is substituted, and,

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

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

[ solution 4]

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

z is each independently N or C-R ¹ Or each Z ═ Z is independently > O, > N-R, > C (-R) ₂ 、＞Si(-R) ₂ S or Se, the C-R ¹ R of (A) ¹ Each independently is hydrogen, aryl, heteroarylA group, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or substituted silyl, at least one of which is hydrogen unsubstituted or substituted by aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, the two aryl groups of the diarylamino group being unbound to one another or bound via a linking group, the two heteroaryl groups of the diheteroarylamino group being unbound to one another or bound via a linking group, the aryl and heteroaryl groups of the arylheteroarylamino group being unbound to one another or bound via a linking group, the two aryl groups of the diarylboryl group being unbound to one another or bound via a single bond or a linking group,

Two adjacent R ¹ (ii) are not bonded to each other to form an aryl or heteroaryl ring, or are bonded to each other to form an aryl or heteroaryl ring, at least one hydrogen of the formed aryl ring and the formed heteroaryl ring, respectively, is unsubstituted or substituted by aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboron, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or substituted silyl, at least one hydrogen of which is unsubstituted or substituted by aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, the two aryl groups of the diarylamino group being unbound or bound via a linking group, the two heteroaryl groups of the diheteroarylamino group being unbound or bound via a linking group, the aryl and heteroaryl groups of the arylheteroarylamino group being unbound or bound to each other, or bonded via a linking group, the two aryl groups of the diarylboron group being not bonded to each other, or bonded via a single bond or a linking group, the > N-R, the > C (-R) ₂ And said > Si (-R) ₂ Each R of (A) is independently hydrogen, aryl, heteroaryl, alkyl, cycloalkyl, at least one of which is unsubstituted or substituted with aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, > C (-R) ₂ And said > Si (-R) ₂ Two R's are not each otherBonded to form a ring, or bonded to each other to form a ring,

a polycyclic aromatic compound having a structure containing one or more than two structural units represented by formula (1c-1), formula (1c-2), formula (1c-3), or formula (1c-4) is not condensed with at least one cycloalkane in which at least one hydrogen is unsubstituted or substituted, or is condensed with at least one cycloalkane in which at least one-CH is present ₂ -is unsubstituted-O-or-S-substituted, or is substituted, and,

at least one hydrogen in the structure represented by formula (1c-1), formula (1c-2), formula (1c-3), or formula (1c-4) is unsubstituted or substituted with cyano, halogen, or deuterium.

< 5 > the polycyclic aromatic compound of < 1 > wherein the structural unit is a structural unit represented by the formula (1d-1) or the formula (1d-2),

[ solution 5]

In the formula (1d-1) and the formula (1d-2),

q and R are each independently 0 or 1, and in the case of 0, each independently means R ¹ In place of L ³ Or L ⁴ And wherein q + r is not 0,

z is each independently N or C-R ¹ Or Z is Z independentlyIndependently > O, > N-R, > C (-R) ₂ 、＞Si(-R) ₂ S or Se, the C-R ¹ R of (A) to (B) ¹ Independently of one another, hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboron, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or substituted silyl, at least one of which is unsubstituted or substituted by aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, the two aryl radicals of the diarylamino radical being unbound to one another or bound via a linking group, the two heteroaryl radicals of the diheteroarylamino radical being unbound to one another or bound via a linking group, the aryl and heteroaryl radicals of the arylheteroarylamino radical being unbound to one another or bound via a linking group, the two aryl radicals of the diarylboron radical being unbound to one another or bound via a single bond or a linking group,

Two adjacent R ¹ (ii) are not bonded to each other to form an aryl or heteroaryl ring, or are bonded to each other to form an aryl or heteroaryl ring, at least one hydrogen of the formed aryl ring and the formed heteroaryl ring, respectively, is unsubstituted or substituted by aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboron, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or substituted silyl, at least one hydrogen of which is unsubstituted or substituted by aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, the two aryl groups of the diarylamino group being unbound or bound via a linking group, the two heteroaryl groups of the diheteroarylamino group being unbound or bound via a linking group, the aryl and heteroaryl groups of the arylheteroarylamino group being unbound or bound to each other, or bonded via a linking group, the two aryl groups of the diarylboron group being not bonded to each other, or bonded via a single bond or a linking group, the > N-R, the > C (-R) ₂ And said > Si (-R) ₂ Each R of (A) is independently hydrogen, aryl, heteroaryl, alkyl, cycloalkyl, at least one of which is not aryl, heteroaryl Substituted with a radical, diarylamino, alkyl, cycloalkyl, or substituted silyl radical, the > C (-R) ₂ And said > Si (-R) ₂ Two R's are not bonded to each other to form a ring, or are bonded to each other to form a ring,

R ^d each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboron, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or substituted silyl, at least one of which is unsubstituted or substituted by aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, the two aryl groups of the diarylamino group being unbound to one another or bound via a linking group, the two heteroaryl groups of the diheteroarylamino group being unbound to one another or bound via a linking group, the aryl and heteroaryl groups of the arylheteroarylamino group being unbound to one another or bound via a linking group, the two aryl groups of the diarylboron group being unbound to one another or bound via a single bond or a linking group,

a polycyclic aromatic compound having one or more structures containing a structural unit represented by formula (1d-1) or formula (1d-2) is not condensed with at least one cycloalkane in which at least one hydrogen is unsubstituted or substituted, or is condensed with at least one cycloalkane in which at least one-CH is present ₂ -is unsubstituted or substituted by-O-or-S-, and,

at least one hydrogen in the structure represented by formula (1d-1) or formula (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),

[ solution 6]

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

z is each independently N or C-R ¹ Or each Z ═ Z is independently > O, > N-R, > C (-R) ₂ 、＞Si(-R) ₂ S or Se, the C-R ¹ R of (A) to (B) ¹ Each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboron, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or substituted silyl, at least one of which is unsubstituted or substituted by aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, the two aryl groups of the diarylamino group being unbound to one another or bound via a linking group, the two heteroaryl groups of the diheteroarylamino group being unbound to one another or bound via a linking group, the aryl and heteroaryl groups of the arylheteroarylamino group being unbound to one another or bound via a linking group, the two aryl groups of the diarylboron group being unbound to one another or bound via a single bond or a linking group,

Two adjacent R ¹ (ii) are not bonded to each other to form an aryl or heteroaryl ring, or are bonded to each other to form an aryl or heteroaryl ring, at least one hydrogen of the formed aryl ring and the formed heteroaryl ring, respectively, is unsubstituted or substituted by aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboron, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or substituted silyl, at least one hydrogen of which is unsubstituted or substituted by aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, the two aryl groups of the diarylamino group being unbound or bound via a linking group, the two heteroaryl groups of the diheteroarylamino group being unbound or bound via a linking group, the aryl and heteroaryl groups of the arylheteroarylamino group being unbound or bound to each other, or bonded via a linking group, the two aryl groups of the diarylboron group being not bonded to each other, or bonded via a single bond or a linking group, the > N-R, the > C (-R) ₂ And said > Si (-R) ₂ R of (A) is respectivelyIndependently hydrogen, aryl, heteroaryl, alkyl, cycloalkyl, at least one of which hydrogen is unsubstituted or substituted with aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or a substituted silyl group, said > C (-R) ₂ And said > Si (-R) ₂ Two R's are not bonded to each other to form a ring, or are bonded to each other to form a ring,

R ^d independently of one another, hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboron, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or substituted silyl, at least one of which is unsubstituted or substituted by aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, the two aryl radicals of the diarylamino radical being unbound to one another or bound via a linking group, the two heteroaryl radicals of the diheteroarylamino radical being unbound to one another or bound via a linking group, the aryl and heteroaryl radicals of the arylheteroarylamino radical being unbound to one another or bound via a linking group, the two aryl radicals of the diarylboron radical being unbound to one another or bound via a single bond or a linking group,

a polycyclic aromatic compound having a structure containing one or more than two structural units represented by formula (1e-1), formula (1e-2), formula (1e-3) or formula (1e-4) is not condensed with at least one cycloalkane in which at least one hydrogen is unsubstituted or substituted, or is condensed with at least one cycloalkane in which at least one-CH is present ₂ -is unsubstituted-O-or-S-substituted, or is substituted, 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 of < 1 > wherein the structural unit is a structural unit represented by the formula (1f-1) or the formula (1f-2),

[ solution 7]

In the formulae (1f-1) and (1f-2),

x is an integer of 1 to 3,

L ¹ 、L ² 、L ³ and L ⁴ Independently of one another, a single bond, substituted or unsubstituted arylene, substituted or unsubstituted heteroarylene, substituted or unsubstituted alkylene, substituted or unsubstituted cycloalkylene, substituted or unsubstituted alkenylene, > O, > N-R, > C (-R) ₂ 、＞Si(-R) ₂ R > N-R, said > Si (-R) ₂ R of (b), and the & gtC (-R) ₂ Each R of (A) is independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, > Si (-R) ₂ And said > C (-R) ₂ The two R's are not bonded to each other to form a ring, or are bonded to each other to form a ring, the R > N-R, the R > C (-R) ₂ R of (b), and said > Si (-R) ₂ Each of at least one R independently of the others is as C-R ^Z R in Z of (A) ^Z Does not utilize-O-, -S-, -C (-R) ₂ -or a single bond, or with-O-, -S-, -C (-R) ₂ -or a single bond to a substrate,

n, m, q and r are each independently 0 or 1, and in the case of 0, each independently represents hydrogen or a substituent in place of L ¹ 、L ² 、L ³ Or L ⁴ And wherein n + m is 1 and is not q + r is 0,

a is each independently > (CR) -, where R of the > (CR) -is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl,

e is independently > O, > N-R, > C (-R) ₂ 、＞Si(-R) ₂ R > N-R, said > Si (-R) ₂ R of (b), and the & gtC (-R) ₂ Each R of (A) is independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, > Si (-R) ₂ And said > C (-R) ₂ Two R's are not bonded to each other to form a ring, or are bonded to each other to form a ring,

two adjacent R ¹ Are not bonded to each other to form an aryl or heteroaryl ring, or are bonded to each other to form an aryl or heteroaryl ring, at least one hydrogen of the formed aryl ring and the formed heteroaryl ring, respectively, being unsubstituted or substituted by aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboron, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or substituted silyl, at least one hydrogen of which is unsubstituted Substituted or substituted with an aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl group, the two aryl groups of the diarylamino group being unbound to each other or bound via a linking group, the two heteroaryl groups of the diheteroarylamino group being unbound to each other or bound via a linking group, the aryl and heteroaryl groups of the arylheteroarylamino group being unbound to each other or bound via a linking group, the two aryl groups of the diarylboron group being unbound to each other or bound via a single bond or a linking group, the > N-R, the > C (-R) ₂ And said > Si (-R) ₂ Each R of (A) is independently hydrogen, aryl, heteroaryl, alkyl, cycloalkyl, at least one of which hydrogen is unsubstituted or substituted with aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, > C (-R) ₂ And said > Si (-R) ₂ Two R's are not bonded to each other to form a ring, or are bonded to each other to form a ring,

a polycyclic aromatic compound having one or more structures containing structural units represented by the formulae (1f-1) and (1f-2) is not condensed with at least one cycloalkane, at least one hydrogen in the cycloalkane being unsubstituted or substituted, at least one-CH in the cycloalkane being unsubstituted or substituted, or is condensed with at least one cycloalkane ₂ -is unsubstituted-O-or-S-substituted, or is substituted, and,

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

< 8 > the polycyclic aromatic compound of < 1 > wherein the structural units are each a structural unit represented by the following formula (1g-1) or formula (1g-2),

[ solution 8]

In the formulae (1g-1) and (1g-2),

x is an integer of 1 to 3,

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

z is each independently N or C-R ¹ Or each Z ═ Z is independently > O, > N-R, > C (-R) ₂ 、＞Si(-R) ₂ S or Se, the C-R ¹ R of (A) to (B) ¹ Each independently is hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or substituted silyl, at least one of which is not hydrogen, aryl, heteroaryl, diarylamino, or substituted silyl, Heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, or substituted, the two aryl groups of the diarylamino being not bonded to each other or bonded via a linking group, the two heteroaryl groups of the diarylamino being not bonded to each other or bonded via a linking group, the aryl and heteroaryl groups of the arylheteroarylamino being not bonded to each other or bonded via a linking group, the two aryl groups of the diarylboron group being not bonded to each other or bonded via a single bond or a linking group,

two adjacent R ¹ (ii) are not bonded to each other to form an aryl or heteroaryl ring, or are bonded to each other to form an aryl or heteroaryl ring, at least one hydrogen of the formed aryl ring and the formed heteroaryl ring, respectively, is unsubstituted or substituted by aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboron, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or substituted silyl, at least one hydrogen of which is unsubstituted or substituted by aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, the two aryl groups of the diarylamino group being unbound or bound via a linking group, the two heteroaryl groups of the diheteroarylamino group being unbound or bound via a linking group, the aryl and heteroaryl groups of the arylheteroarylamino group being unbound or bound to each other, or bonded via a linking group, the two aryl groups of the diarylboron group being not bonded to each other, or bonded via a single bond or a linking group, the > N-R, the > C (-R) ₂ And said > Si (-R) ₂ Each R of (A) is independently hydrogen, aryl, heteroaryl, alkyl, cycloalkyl, at least one of which hydrogen is unsubstituted or substituted with aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, > C (-R) ₂ And said > Si (-R) ₂ Two R's are not bonded to each other to form a ring, or are bonded to each other to form a ring,

the polycyclic aromatic compound having one or more structures containing a structural unit represented by the formula (1g-1) or the formula (1g-2) is not substituted with at least oneCondensed with, or condensed with, at least one cycloalkane, at least one hydrogen of said cycloalkane being unsubstituted or substituted, at least one-CH of said cycloalkane ₂ -is unsubstituted or substituted by-O-or-S-, and,

at least one hydrogen in the structure represented by formula (1g-1) or formula (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), formula (1h-2), formula (1h-3) or formula (1h-4),

[ solution 9]

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

x is an integer of 1 to 3,

z is each independently N or C-R ¹ Or Z is independently > O, > N-R, > C (-R) ₂ 、＞Si(-R) ₂ S or Se, the C-R ¹ R of (A) to (B) ¹ Each independently is hydrogen, aryl, heteroaryl, diarylamino, diheteroarylaminoA group, arylheteroarylamino, diarylboron, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or substituted silyl, at least one of which is hydrogen unsubstituted or substituted by aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, the two aryl groups of the diarylamino group being unbound to one another or bound via a linking group, the two heteroaryl groups of the diheteroarylamino group being unbound to one another or bound via a linking group, the aryl and heteroaryl groups of the arylheteroarylamino group being unbound to one another or bound via a linking group, the two aryl groups of the diarylboron group being unbound to one another or bound via a single bond or a linking group,

Two adjacent R ¹ (ii) are not bonded to each other to form an aryl or heteroaryl ring, or are bonded to each other to form an aryl or heteroaryl ring, at least one hydrogen of the formed aryl ring and the formed heteroaryl ring, respectively, is not substituted or substituted by aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboron, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or substituted silyl, at least one hydrogen of which is not substituted or substituted by aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, the two aryl groups of the diarylamino group being not bonded to each other or being bonded via a linking group, the two heteroaryl groups of the diheteroarylamino group being not bonded to each other or being bonded via a linking group, the aryl and heteroaryl groups of the arylheteroarylamino group being not bonded to each other, or bonded via a linking group, the two aryl groups of the diarylboron group being not bonded to each other, or bonded via a single bond or a linking group, the > N-R, the > C (-R) ₂ And said > Si (-R) ₂ Each R of (A) is independently hydrogen, aryl, heteroaryl, alkyl, cycloalkyl, at least one of which is unsubstituted or substituted with aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, > C (-R) ₂ And said > Si (-R) ₂ Two R's are not bonded to each other to form a ring, or are bonded to each otherSo as to form a ring,

a polycyclic aromatic compound having one or more structures containing a structural unit represented by formula (1h-1), formula (1h-2), formula (1h-3), or formula (1h-4) is not condensed with at least one cycloalkane in which at least one hydrogen is unsubstituted or substituted, or is condensed with at least one cycloalkane in which at least one-CH is present ₂ -is unsubstituted-O-or-S-substituted, or is substituted, and,

at least one hydrogen in the structure represented by formula (1h-1), formula (1h-2), formula (1h-3), or formula (1h-4) is unsubstituted or substituted with cyano, halogen, or deuterium.

< 10 > the polycyclic aromatic compound of < 1 > wherein the structural unit is a structural unit represented by the formula (1i-1) or the formula (1i-2),

[ solution 10]

In the formulae (1i-1) and (1i-2),

x is an integer of 1 to 3,

two adjacent R ¹ Are not bonded to each other to form an aryl ring or heteroaryl ring, or are bonded to each other to form an aryl ring or heteroaryl ring, at least one hydrogen of the formed aryl ring and the formed heteroaryl ring being free of aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboron, alkyl, cycloalkylamino, respectively A group, an alkenyl group, an alkoxy group, an aryloxy group, an arylthio group, or a substituted silyl group, or substituted, at least one of which is hydrogen unsubstituted or substituted with an aryl group, a heteroaryl group, a diarylamino group, an alkyl group, a cycloalkyl group, or a substituted silyl group, or substituted, the two aryl groups of the diarylamino group being unbound to each other or bound via a linking group, the two heteroaryl groups of the diheteroarylamino group being unbound to each other or bound via a linking group, the aryl and heteroaryl groups of the arylheteroarylamino group being unbound to each other or bound via a linking group, the two aryl groups of the diarylboron group being unbound to each other or bound via a single bond or a linking group, the > N-R, the > C (-R) ₂ And said > Si (-R) ₂ Each R of (A) is independently hydrogen, aryl, heteroaryl, alkyl, cycloalkyl, at least one of which hydrogen is unsubstituted or substituted with aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, > C (-R) ₂ And said > Si (-R) ₂ Two R's are not bonded to each other to form a ring, or are bonded to each other to form a ring,

The polycyclic aromatic compound having one or two or more structures containing the structural unit represented by the formula (1i-1) or the formula (1i-2) is condensed not with at least one cycloalkane, or with at least one cycloalkane,at least one hydrogen in the cycloalkane being unsubstituted or substituted, at least one-CH in the cycloalkane ₂ -is unsubstituted or substituted by-O-or-S-, and,

at least one hydrogen in the structure represented by formula (1i-1) or formula (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 formula (1k-1), formula (1k-2), formula (1k-3) or formula (1k-4),

[ solution 11]

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

x is an integer of 1 to 3,

z is each independently N or C-R ¹ Or each Z ═ Z is independently > O, > N-R, > C (-R) ₂ 、＞Si(-R) ₂ S or Se, the C-R ¹ R of (A) to (B) ¹ Each independently is hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboron, alkyl, cycloalkyl, or a substituted aryl or heteroaryl group,Alkenyl, alkoxy, aryloxy, arylthio or substituted silyl, at least one of which is hydrogen-unsubstituted or substituted by aryl, heteroaryl, diarylamino, alkyl, cycloalkyl or substituted silyl, the two aryl radicals of the diarylamino group being unbound to one another or bound via a linking group, the two heteroaryl radicals of the diarylamino group being unbound to one another or bound via a linking group, the aryl and heteroaryl radicals of the arylheteroarylamino group being unbound to one another or bound via a linking group, the two aryl radicals of the diarylboron group being unbound to one another or bound via a single bond or a linking group,

R ^d each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboron, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or substituted silyl, at least one of which is unsubstituted or substituted by aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, two aryl groups of the diarylamino groups being unbound to one another or bound via a linking group, two heteroaryl groups of the diheteroarylamino groups being unbound to one another or bound via a linking group, two aryl groups of the arylheteroarylamino groups being unbound to one another or bound via a linking group, two aryl groups of the diarylboron groups being unbound to one another or bound via a single bond or a linking group;

a polycyclic aromatic compound having a structure containing one or more than two structural units represented by formula (1k-1), formula (1k-2), formula (1k-3), or formula (1k-4) is not condensed with at least one cycloalkane in which at least one hydrogen is unsubstituted or substituted, or is condensed with at least one cycloalkane in which at least one-CH is present ₂ -is unsubstituted-O-or-S-substituted, or is substituted, and,

at least one hydrogen in the structure represented by formula (1k-1), formula (1k-2), formula (1k-3) or formula (1k-4) is unsubstituted or substituted with cyano, halogen, or deuterium.

< 12 > the polycyclic aromatic compound according to < 1 > represented by any one of the following structural formulae,

[ solution 12]

In the formula, tBu is tert-butyl.

< 13 > the polycyclic aromatic compound according to < 1 > represented by any one of the following structural formulae,

[ solution 13]

< 14 > a material for organic devices, comprising the polycyclic aromatic compound according to any one of < 1 > to < 13 >.

< 15 > an organic electroluminescent element having: a pair of electrodes including 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 >.

< 16 > the organic electroluminescent element according to < 15 > wherein the light-emitting layer comprises a host and the polycyclic aromatic compound as a dopant.

< 17 > a display device or a lighting device comprising the organic electroluminescent element according to any one of < 15 > or < 16 >.

[ Effect of the invention ]

The present invention provides a novel polycyclic aromatic compound which is useful as a material for an organic device such as an organic electroluminescent element. The polycyclic aromatic compound of the present invention can be used for producing an organic device such as an organic electroluminescent element.

Drawings

Fig. 1 is a schematic sectional view showing an example of an organic electroluminescent element.

Fig. 2 is an energy level diagram showing the energy relationship among the host, the assist dopant, and the emissive dopant of a TAF element using a general fluorescent dopant.

Fig. 3 is a level diagram showing an example of an energy relationship among a host, an auxiliary dopant, and an emitting dopant in an organic electroluminescent device according to an embodiment of the present invention.

[ description of symbols ]

100: organic electroluminescent element

101: substrate board

102: anode

103: hole injection layer

104: hole transport layer

105: luminescent layer

106: electron transport layer

107: electron injection layer

108: and a cathode.

Detailed Description

The present invention will be described in detail below. The following description of the constituent elements may be based on typical embodiments or specific examples, but the present invention is not limited to such embodiments. In the present specification, the numerical range expressed by the term "to" means a range including the numerical values described before and after the term "to" as the lower limit value and the upper limit value. In the present specification, "hydrogen" in the description of the structural formulae means "hydrogen atom (H)".

In this specification, an organic electroluminescent element is sometimes referred to as an organic EL element.

In the present specification, the chemical structure or the substituent may be represented by a carbon number, but the carbon number when the substituent is substituted in the chemical structure, when the substituent is further substituted on the substituent, or the like, refers to the carbon number of each of the chemical structure or the substituent, and does not refer to the total carbon number of the chemical structure and the substituent or the total carbon number of the substituent and the substituent. For example, the "substituent B having a carbon number Y substituted with the substituent a having a carbon number X" means that the "substituent a having a carbon number X" is substituted with the "substituent B having a carbon number Y, and the carbon number Y is not the total carbon number of the substituent a and the substituent B. For example, the "substituent B having a carbon number Y substituted by the substituent a" means that the substituent a "(not limited to a carbon number) is substituted on the" substituent B having a carbon number Y ", and the carbon number Y is not the total carbon number of the substituent a and the substituent B.

Since the chemical structural formula described in the present specification (including the general formula depicted by markush (markush) structural formula) is a planar structural formula, various isomer structures such as a mirror image isomer (enantiomer), a non-mirror image isomer, and a rotamer may actually exist. In the present specification, unless otherwise specified, the compounds described may have any isomeric structure that can be considered from the plane structural formula thereof, and may be a mixture of possible isomers in any ratio.

The present specification describes structural formulae of a plurality of aromatic compounds. Although the aromatic compound is described by combining a double bond and a single bond, actually, since pi-electron resonance exists, there is an equivalent resonance structure in which a plurality of double bonds and single bonds are alternately replaced with each other for a single substance. In the present specification, only one resonance structural formula is described for one substance, but other resonance structural formulas that are equivalent in organic chemistry are also included unless otherwise specified. The above-mentioned case is referred to in the description of "Z ═ Z" and the like described later. That is, for example, "Z ═ Z" in formula (1a-1) described below shows an example as follows. However, the present invention is not limited to this, and it is needless to say that the present invention is applicable not only to one resonance structural formula described above but also to other equivalent resonance structural formulas.

[ solution 14]

In the present specification, the expression "may" is used to mean "not", "already", "having", and the like, but both expressions have the same meaning.

< polycyclic aromatic Compound >

The polycyclic aromatic compound of the present invention is a polycyclic aromatic compound having one or more structures containing the structural unit represented by the formula (1A-1). The polycyclic aromatic compound of the present invention has a high luminescence quantum yield (PLQY), a narrow luminescence half-value width, and excellent color purity.

[ solution 15]

In formula (1A-1), ring a2, ring A3, and ring a4 are each independently a substituted or unsubstituted aryl ring or a substituted or unsubstituted heteroaryl ring, and 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.

Examples of the "aryl ring" of the ring A1, the ring A2, the ring A3, the ring A4 and the ring A5 in the formula (1A-1) include aryl rings having 6 to 30 carbon atoms, preferably aryl rings having 6 to 16 carbon atoms, more preferably aryl rings having 6 to 12 carbon atoms, and particularly preferably aryl rings having 6 to 10 carbon atoms.

Specific "aryl ring" includes: benzene ring as a monocyclic system, biphenyl ring as a bicyclic system, naphthalene ring and indene ring as a condensed bicyclic system, tribiphenyl ring (m-terphenyl, o-terphenyl, p-terphenyl) as a tricyclic system, acenaphthylene ring (acenaphthylene ring), fluorene ring (fluorene ring), phenalene ring (phenalene ring), phenanthrene ring (phenanthlene ring), anthracene ring as a condensed tricyclic system, triphenylbenzene ring, pyrene ring, tetracene ring, perylene ring, anthracene ring as a condensed tricyclic system,

Examples of the ring include a perylene ring and pentacene ring which are condensed five-ring systems. The fluorene ring, the benzfluorene ring, and the indene ring also include a structure in which a fluorene ring, a benzfluorene ring, a cyclopentane ring, and the like are spiro-bonded. In addition, of the fluorene ring, the benzofluorene ring, and the indene ring, two of the two hydrogens including methylene group are each substituted with an alkyl group such as a methyl group as a first substituent described later to form a ring such as a dimethylfluorene ring, a dimethylbenzene ring, or a dimethylindene ring.

Examples of the "heteroaryl ring" of the ring A1, the ring A2, the ring A3, the ring A4 and the ring A5 in the formula (1A-1) include a heteroaryl ring having 2 to 30 carbon atoms, preferably a heteroaryl ring having 2 to 25 carbon atoms, more preferably a heteroaryl ring having 2 to 20 carbon atoms, further preferably a heteroaryl ring having 2 to 15 carbon atoms, and particularly preferably a heteroaryl ring having 2 to 10 carbon atoms. Examples of the "heteroaryl ring" include a heterocyclic ring containing 1 to 5 heteroatoms selected from oxygen, sulfur and nitrogen as ring-constituting atoms in addition to carbon.

Specific examples of the "heteroaryl ring" include: pyrrole ring, oxazole ring, isoxazole ring, thiazole ring, isothiazole ring, imidazole ring, oxadiazole ring, thiadiazole ring, triazole ring, tetrazole ring, pyrazole ring, pyridine ring, pyrimidine ring, pyridazine ring, pyrazine ring, triazine ring, indole ring, isoindole ring, 1H-indazole ring, benzimidazole ring, benzoxazole ring, benzothiazole ring, 1H-benzotriazole ring, quinoline ring, isoquinoline ring, cinnoline ring, quinazoline ring, quinoxaline ring, phthalazine ring, naphthyridine ring, purine ring, pteridine ring, carbazole ring, carboline ring (carboline), acridine ring, phenoxathiin ring, phenoxazine ring, phenothiazine (phenazaline) ring, indolizine ring, furan ring, benzofuran ring, isobenzofuran ring, dibenzofuran ring, thiophene ring, benzothiophene ring, furo ring, azazine ring, indolizine ring, indole ring, and indole ring, Dibenzoindolocarbazole ring, naphthobenzofuran ring, dioxin ring, dihydroacridine ring, xanthene ring, thioxanthene ring, dibenzodioxin ring, and the like. In addition, it is also preferable that two of the two hydrogens of the methylene group are substituted with an alkyl group such as a methyl group as a first substituent described later to form a ring such as a dimethylacridine ring, a dimethylxanthene ring, or a dimethylthioxanthene ring. In addition, a bipyridine ring, a phenylpyridine ring, a pyridylphenyl ring as a bicyclic system, a terpyridine (terpyridyl) ring, a bispyridylphenyl ring, and a pyridylbiphenyl ring as a tricyclic system may also be exemplified as the "heteroaryl ring". In addition, the "heteroaryl ring" also includes a pyran ring.

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

[ solution 16]

Examples of the "cycloalkyl ring" of the ring A1 and the ring A5 in the formula (1A-1) include cycloalkyl rings having 6 to 30 carbon atoms, preferably cycloalkyl rings having 6 to 16 carbon atoms, more preferably cycloalkyl rings having 6 to 12 carbon atoms, and particularly preferably cycloalkyl rings having 6 to 10 carbon atoms.

As specific cycloalkyl rings, there may be mentioned: cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclononane, cyclodecane, norbornane, 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, bisadamantane, decahydronaphthalene, decahydroazulene, and alkyl (particularly methyl) substituents having 1 to 4 carbon atoms thereof.

Examples of the "cycloheteroalkyl ring" of the ring A1 and the ring A5 in the formula (1A-1) include cycloheteroalkyl rings having 4 to 30 carbon atoms, preferably cycloheteroalkyl rings having 4 to 16 carbon atoms, more preferably cycloheteroalkyl rings having 4 to 12 carbon atoms, and particularly preferably cycloheteroalkyl rings having 4 to 10 carbon atoms.

Cycloheteroalkyl rings refer to rings in which one or more carbon atoms of the cycloalkyl ring is replaced with a heteroatom (oxygen, nitrogen, sulfur, etc.). Specific examples of the cycloheteroalkyl ring include: tetrahydropyrrole ring, tetrahydrofuran ring, tetrahydrothiophene ring, piperidine ring, pyrrolidine ring, tetrahydropyran ring, tetrahydrothiopyran ring, dioxane ring, oxathiane ring, dithiane ring, morpholine ring, piperazine ring, etc.

At least one of the "aryl ring", "heteroaryl ring", "cycloalkyl ring", or "cycloheteroalkyl ring" may be substituted with a substituted or unsubstituted "aryl", a substituted or unsubstituted "heteroaryl", a substituted or unsubstituted "diarylamino", a substituted or unsubstituted "diheteroarylamino", a substituted or unsubstituted "arylheteroarylamino", a substituted or unsubstituted "diarylboryl", a substituted or unsubstituted "alkyl", a substituted or unsubstituted "cycloalkyl", a substituted or unsubstituted "alkenyl", a substituted or unsubstituted "alkoxy", a substituted or unsubstituted "aryloxy", a substituted or unsubstituted "arylthio", or a substituted "silyl" as a first substituent. In addition, the two aryl groups of the diarylamino group are not bonded to each other or bonded via a linking group, the two heteroaryl groups of the diarylamino group are not bonded to each other or bonded via a linking group, the aryl and heteroaryl groups of the arylheteroarylamino group are not bonded to each other or bonded via a linking group, and the two aryl groups of the diarylboron group are not bonded to each other or bonded via a single bond or a linking group. These terms and their preferred ranges may be referred to in the specification unless otherwise specified.

Specifically, the "aryl group" includes, for example, an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 24 carbon atoms, more preferably an aryl group having 6 to 20 carbon atoms, further preferably an aryl group having 6 to 16 carbon atoms, particularly preferably an aryl group having 6 to 12 carbon atoms, and most preferably an aryl group having 6 to 10 carbon atoms.

Specific examples of the aryl group include: phenyl as monocyclic aryl group, (2-, 3-, 4-) biphenyl as bicyclic aryl group, (1-, 2-) naphthyl, (2-, 3-, 4-, 5-, 6-, 7-) indenyl as condensed bicyclic aryl group, terphenyl groups (m-terphenyl-2 '-yl, m-terphenyl-4' -yl, m-terphenyl-5 '-yl, o-terphenyl-3' -yl, o-terphenyl-4 '-yl, p-terphenyl-2' -yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-3-yl, p-terphenyl-2-yl, p-4-yl, p-terphenyl-4-yl, p-4-l-terphenyl-2-l-, O-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), acenaphthylene- (1-, 3-, 4-, 5-) yl, fluorene- (1-, 2-, 3-, 4-, 9-) yl, phenalene- (1-, 2-) yl, (1-, 2-, 3-, 4-, 9-) phenanthryl as condensed tricyclic aryl, tetraphenyl (5' -phenyl-m-terphenyl-2-yl, 5' -phenyl-m-terphenyl-3-yl, 5' -phenyl-m-terphenyl-4-yl, p-terphenyl-4-yl as tetracyclic aryl, M-quaterphenyl), a triphenylene- (1-, 2-) group, a pyrene- (1-, 2-, 4-) group, and a tetracene- (1-, 2-, 5-) group as condensed tetracyclic aryl groups, a perylene- (1-, 2-, 3-) group, and a pentacene- (1-, 2-, 5-, 6-) group as condensed pentacyclic aryl groups, and the like.

Examples of the "heteroaryl group" include a heteroaryl group having 2 to 30 carbon atoms, preferably a heteroaryl group having 2 to 25 carbon atoms, more preferably a heteroaryl group having 2 to 20 carbon atoms, still more preferably a heteroaryl group having 2 to 15 carbon atoms, and particularly preferably a heteroaryl group having 2 to 10 carbon atoms. Examples of the heteroaryl group include heterocyclic rings containing 1 to 5 heteroatoms selected from oxygen, sulfur and nitrogen as ring-constituting atoms in addition to carbon.

Specific examples of the heteroaryl group include: furyl, thienyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, furazanyl, thiadiazolyl, triazolyl, tetrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, benzo [ b ] thienyl, dibenzothienyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, carbolinyl, acridinyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenoxathiin, thianthrenyl, thiaindolizinyl, and the like.

The "alkyl group" as the first substituent may be either a straight chain or a branched chain, and examples thereof include a straight-chain alkyl group having 1 to 24 carbon atoms and a branched-chain alkyl group having 3 to 24 carbon atoms. Preferably an alkyl group having 1 to 18 carbon atoms (branched alkyl group having 3 to 18 carbon atoms), more preferably an alkyl group having 1 to 12 carbon atoms (branched alkyl group having 3 to 12 carbon atoms), further preferably an alkyl group having 1 to 8 carbon atoms (branched alkyl group having 3 to 8 carbon atoms), particularly preferably an alkyl group having 1 to 6 carbon atoms (branched alkyl group having 3 to 6 carbon atoms), and most preferably an alkyl group having 1 to 5 carbon atoms (branched alkyl group having 3 to 5 carbon atoms).

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

As the substituent containing the "alkyl group", a tertiary alkyl group represented by the following formula (tR) is one of particularly preferable substituents as a substituent for an aryl ring or a heteroaryl ring in the a ring, the B ring, and the C ring. The reason for this is that the intermolecular distance is increased by such bulky substituents, and thus the luminescence quantum yield (PLQY) is improved. In addition, a tertiary alkyl group represented by the formula (tR) is also preferable as a substituent in which a second substituent is substituted with another substituent. Specifically, a tertiary alkyl-substituted diarylamino group represented by (tR), a tertiary alkyl-substituted carbazolyl group represented by (tR) (preferably, an N-carbazolyl group), or a tertiary alkyl-substituted benzocarbazolyl group represented by (tR) (preferably, an N-benzocarbazolyl group) may be mentioned. In addition, the two aryl groups of the diarylamino group are not bonded to each other, or are bonded via a linking group. The "diarylamino group" includes groups described as the "first substituent" described below. Examples of substitution patterns of the group of formula (tR) for the diarylamino group, the carbazolyl group, and the benzocarbazolyl group include substitution of a part or all of hydrogen in an aryl ring or a benzene ring in these groups with a group of formula (tR).

[ solution 17]

In the formula (tR), R ^a 、R ^b And R ^c Are respectively and independentlyIs an alkyl group having 1 to 24 carbon atoms, any-CH in the alkyl group ₂ -unsubstituted or substituted by-O-substitution, the radical of formula (tR) being substituted at one site with at least one hydrogen of the structure comprising the structural unit of formula (1).

R ^a 、R ^b And R ^c The "alkyl group having 1 to 24 carbon atoms" may be either a straight chain or a branched chain, and examples thereof include: a linear alkyl group having 1 to 24 carbon atoms, a branched alkyl group having 3 to 24 carbon atoms, an alkyl group having 1 to 18 carbon atoms (branched alkyl group having 3 to 18 carbon atoms), an alkyl group having 1 to 12 carbon atoms (branched alkyl group having 3 to 12 carbon atoms), an alkyl group having 1 to 6 carbon atoms (branched alkyl group having 3 to 6 carbon atoms), and an alkyl group having 1 to 4 carbon atoms (branched alkyl group having 3 to 4 carbon atoms).

R in formula (tR) of formula (1) ^a 、R ^b And R ^c The total number of carbon atoms of (2) is preferably 3 to 20 carbon atoms, and more preferably 3 to 10 carbon atoms.

As R ^a 、R ^b And R ^c Specific examples of the alkyl group in (1) include: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 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 and the like.

Examples of the group represented by formula (tR) include: t-butyl, t-pentyl, 1-ethyl-1-methylpropyl, 1-diethylpropyl, 1-dimethylbutyl, 1-ethyl-1-methylbutyl, 1,3, 3-tetramethylbutyl, 1, 4-trimethylpentyl, 1, 2-trimethylpropyl, 1-dimethyloctyl, 1-dimethylpentyl, 1-dimethylheptyl, 1, 5-trimethylhexyl, 1-ethyl-1-methylhexyl, 1-ethyl-1, 3-dimethylbutyl, 1,2, 2-tetramethylpropyl, 1-butyl-1-methylpentyl, 1-diethylbutyl, 1-ethyl-1-methylpentyl, 1-dimethylpentyl, 1-ethyl-1-dimethylpentyl, 1-dimethylpropyl, 1, 2-dimethylpentyl, 1,2, 2-dimethylpentyl, 2, or a, 1,1, 3-trimethylbutyl, 1-propyl-1-methylpentyl, 1, 2-trimethylpropyl, 1-ethyl-1, 2, 2-trimethylpropyl, 1-propyl-1-methylbutyl, 1-dimethylhexyl and the like. Of these, preferred are tert-butyl and tert-amyl.

Examples of the "cycloalkyl group" as the first substituent include a cycloalkyl group having 3 to 24 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a cycloalkyl group having 3 to 16 carbon atoms, a cycloalkyl group having 3 to 14 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, a cycloalkyl group having 5 to 8 carbon atoms, a cycloalkyl group having 5 to 6 carbon atoms, and a cycloalkyl group having 5 carbon atoms. The cyclohexyl group in the present specification includes, as will be described later, a monocyclic cyclohexyl group and the like, and also includes a polycyclic cyclohexyl group such as an adamantyl group.

As specific cycloalkyl groups, there may be mentioned: 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, diamantanyl, decahydronaphthyl, decahydroazulenyl, and alkyl (particularly methyl) substituents having 1 to 5 carbon atoms thereof.

Examples of the "alkoxy" as the first substituent include a linear alkoxy group having 1 to 24 carbon atoms and a branched alkoxy group having 3 to 24 carbon atoms. Preferably an alkoxy group having 1 to 18 carbon atoms (branched alkoxy group having 3 to 18 carbon atoms), more preferably an alkoxy group having 1 to 12 carbon atoms (branched alkoxy group having 3 to 12 carbon atoms), still more preferably an alkoxy group having 1 to 6 carbon atoms (branched alkoxy group having 3 to 6 carbon atoms), and particularly preferably an alkoxy group having 1 to 5 carbon atoms (branched alkoxy group having 3 to 5 carbon atoms).

Specific examples of the alkoxy group include: methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-pentoxy, hexoxy, heptoxy, octoxy and the like.

Examples of the "substituted silyl group" as the first substituent include a silyl group substituted with three substituents selected from the group consisting of an alkyl group, a cycloalkyl group, and an aryl group. Examples thereof include: trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkylbicycloalkylsilyl, triarylsilyl, dialkylarylsilyl, and alkyldiarylsilyl groups.

As the "trialkylsilyl group", there may be mentioned a group in which three hydrogens of the silyl group are each independently substituted with an alkyl group, and the alkyl group may refer to a group described as the "alkyl group" in the first substituent. The alkyl group preferably used for substitution is an alkyl group having 1 to 5 carbon atoms, and specific examples thereof include: methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-pentyl, and the like.

Specific examples of the trialkylsilyl group include: trimethylsilyl group, triethylsilyl group, tripropylsilyl group, triisopropylsilyl group, tributylsilyl group, tri-sec-butylsilyl group, tri-tert-pentylsilyl group, ethyldimethylsilyl group, propyldimethylsilyl group, isopropyldimethylsilyl group, butyldimethylsilyl group, sec-butyldimethylsilyl group, tert-pentyldimethylsilyl group, methyldiethylsilyl group, propyldiethylsilyl group, isopropyldiethylsilyl group, butyldiethylsilyl group, sec-butyldiethylsilyl group, tert-butyldiethylsilyl group, methyldipropylsilyl group, ethyldipropylsilyl group, butyldipropylsilyl group, sec-butyldipropylsilyl group, tert-pentyldipropylsilyl group, methyldiisopropylsilyl group, methyl-propylsilyl group, ethyl-dimethylsilyl group, tert-butyldimethylsilyl group, tert-butyldipropylsilyl group, tert-butyldimethylsilyl group, tert-pentyldipropylsilyl group, methyl-butyldi-butylsilyl group, methyl-butyldimethylsilyl group, a, Ethyldiisopropylsilane, butyldiisopropylsilane, sec-butyldiisopropylsilane, tert-amyldiisopropylsilane, etc.

As the "tricycloalkylsilyl group", there can be cited a group in which three hydrogens in the silyl group are each independently substituted with a cycloalkyl group, and the cycloalkyl group can refer to a group described as the "cycloalkyl group" in the first substituent. Preferred cycloalkyl groups for substitution are those having 5 to 10 carbon atoms, and specific examples thereof include: cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, bicyclo [1.1.1] pentyl, bicyclo [2.1.0] pentyl, bicyclo [2.1.1] hexyl, bicyclo [3.1.0] hexyl, bicyclo [2.2.1] heptyl, bicyclo [2.2.2] octyl, adamantyl, decahydronaphthyl, decahydroazulenyl and the like.

Specific examples of the tricycloalkylsilyl group include tricyclopentylsilyl groups and tricyclohexylsilyl groups.

Specific examples of the dialkylcycloalkylsilyl group substituted with two alkyl groups and one cycloalkyl group and the alkylbicycloalkylsilyl group substituted with one alkyl group and two cycloalkyl groups include silyl groups substituted with a group selected from the specific alkyl groups and cycloalkyl groups.

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

The "aryloxy" as the first substituent is a group in which hydrogen of an-OH group is substituted with an aryl group, and this aryl group may be referred to as the aryl group described as the "aryl group".

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

Examples of the "alkenyl group" as the first substituent include a linear alkenyl group having 2 to 24 carbon atoms and a branched alkenyl group having 4 to 24 carbon atoms. Preferably C2-18 alkenyl, more preferably C2-12 alkenyl, further preferably C2-6 alkenyl, especially preferably C2-4 alkenyl.

Specific examples of the "alkenyl group" include vinyl, allyl, and butadienyl groups.

In addition, "aryl" in "diarylboron group" of the first substituent may refer to the description of the aryl. In addition, the two aryl groups may be linked via a single bond or a linking group (e.g., > C (-R) ₂ A > O, > S, or > N-R) bond. Here, > C (-R) ₂ And R > N-R is aryl, heteroaryl, alkyl, cycloalkyl, alkoxy or aryloxy (orAbove is a first substituent), at least one hydrogen of said first substituent is not further substituted or substituted with an aryl, heteroaryl, alkyl or cycloalkyl group (above is a second substituent), and as specific examples of these groups, mention may be made of said first substituent. In addition, the two aryl groups of the diarylboron group are not bonded to each other, or are bonded via a single bond or a linking group.

The aryl or heteroaryl group of each of "diarylamino group which may be substituted", "diheteroarylamino group which may be substituted", "arylheteroarylamino group which may be substituted" as the first substituent may be referred to as the group described as the "aryl" or "heteroaryl". In addition, at least one hydrogen of the aryl group and the heteroaryl group is unsubstituted or substituted, and as a substituent, reference is made to the description relating to "substituted or unsubstituted" described later, and a tertiary alkyl group described later is preferable. In addition, the two aryl groups of the diarylamino group are not bonded to each other or bonded via a linking group, the two heteroaryl groups of the diheteroarylamino group are not bonded to each other or bonded via a linking group, and the aryl group and the heteroaryl group of the arylheteroarylamino group are not bonded to each other or bonded via a linking group.

As for the diarylamino group, diheteroarylamino group, arylheteroarylamino group as the first substituent, "two aryl groups are bonded via a linking group or are not bonded via a linking group," "two heteroaryl groups are bonded via a linking group or are not bonded via a linking group," or "heteroaryl groups are bonded via a linking group or are not bonded via a linking group," but the description is as described below, for example, two phenyl groups showing a diphenylamino group are bonded via a linking group. In addition, the description also applies to diheteroarylamino and arylheteroarylamino groups formed from aryl or heteroaryl groups.

[ solution 18]

Specific examples of the linking group include: > O, > N-R ^X 、＞C(-R ^X ) ₂ 、＞Si(-R ^X ) ₂ 、＞S、＞CO、＞CS、＞SO、＞SO ₂ And > Se, R ^X Each independently is alkyl, cycloalkyl, aryl or heteroaryl, which is unsubstituted or substituted with alkyl, cycloalkyl, aryl or heteroaryl and > C (-R) ^X ) ₂ 、＞Si(-R ^X ) ₂ R in (1) ^X Can be via a single bond or a linking group X ^Y Bonded to form a ring. X ^Y Mention may be made of > O, > N-R ^Y 、＞C(-R ^Y ) ₂ 、＞Si(-R ^Y ) ₂ 、＞S、＞CO、＞CS、＞SO、＞SO ₂ And > Se, R ^Y Each independently is alkyl, cycloalkyl, aryl or heteroaryl, which may be substituted with alkyl, cycloalkyl, aryl or heteroaryl. Wherein, in X ^Y Is > C (-R) ^Y ) ₂ And > Si (-R) ^Y ) ₂ In the case of (2), two R ^Y No further ring formation occurs due to the bonding. Further, as the linking group, an alkenylene group may be mentioned. Any at least one hydrogen of alkenylene is independently not substituted by R ^X Substituted or substituted, R ^X Each independently is an alkyl group, a cycloalkyl group, a substituted silyl group, an aryl group, or a heteroaryl group, at least one hydrogen of which is substituted with an alkyl group (particularly, a tertiary alkyl group described later), a cycloalkyl group, a substituted silyl group, an aryl group, or is unsubstituted.

In the present specification, when only "diarylamino", "diheteroarylamino" or "arylheteroarylamino" is described, the following description is added, if not otherwise specified: "two aryl groups are bonded via a linking group or are not bonded via a linking group", "two heteroaryl groups are bonded via a linking group or are not bonded via a linking group", and "aryl and heteroaryl groups are bonded via a linking group or are not bonded via a linking group".

As a first substituent, a substituted or unsubstituted "aryl", a substituted or unsubstituted "heteroaryl", a substituted or unsubstituted "diarylamino", a substituted or unsubstituted "diheteroarylamino", a substituted or unsubstituted "arylheteroarylamino", a substituted or unsubstituted "diarylboryl", a substituted or unsubstituted "alkyl", a substituted or unsubstituted "alkenyl", a substituted or unsubstituted "cycloalkyl", a substituted or unsubstituted "alkoxy", a substituted or unsubstituted "aryloxy", a substituted or unsubstituted "arylthio", or a "substituted silyl" may be substituted with a second substituent, as illustrated by being substituted or unsubstituted. The second substituent is preferably an aryl group, a heteroaryl group, an alkyl group, a cycloalkyl group, or a substituted silyl group, and specific examples thereof can be referred to the description in the present specification. Unless otherwise specified, this statement may also be referred to in the present specification in other "substituted or unsubstituted" statements. In the aryl or heteroaryl group as the second substituent, a structure in which at least one hydrogen atom is substituted with an aryl group such as a phenyl group (specifically, the above-mentioned group), an alkyl group such as a methyl group or a tert-butyl group (specifically, the above-mentioned group), or a cycloalkyl group such as a cyclohexyl group (specifically, the above-mentioned group) is also included in the aryl or heteroaryl group as the second substituent. For example, when the second substituent is a carbazolyl group, a carbazolyl group in which at least one hydrogen at the 9-position is substituted with an aryl group such as a phenyl group, an alkyl group such as a methyl group, or a cycloalkyl group such as a cyclohexyl group is also included in the heteroaryl group as the second substituent. In addition, the two aryl groups of the diarylamino group are not bonded to each other or bonded via a linking group, the two heteroaryl groups of the diarylamino group are not bonded to each other or bonded via a linking group, the aryl and heteroaryl groups of the arylheteroarylamino group are not bonded to each other or bonded via a linking group, and the two aryl groups of the diarylboron group are not bonded to each other or bonded via a linking group.

The emission wavelength can be adjusted by steric hindrance, electron donating property, and electron withdrawing property of the structure of the first substituent. The group represented by the following structural formula is preferable, and methyl, tert-butyl, tert-amyl, tert-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- (tert-butyl) phenyl) amino, carbazolyl, 3, 6-dimethylcarbazolyl, 3, 6-di-tert-butylcarbazolyl and phenoxy are more preferable, and methyl, tert-butyl, tert-amyl, tert-octyl, neopentyl, adamantyl, phenyl, o-tolyl, 2, 6-xylyl, 2,4, 6-mesityl, diphenylamino, di-p-tolylamino, bis (p- (tert-butyl) phenyl) amino are more preferable, Carbazolyl, 3, 6-dimethylcarbazolyl and 3, 6-di-tert-butylcarbazolyl. From the viewpoint of ease of synthesis, a group having a large steric hindrance is preferable for selective synthesis, and specifically, t-butyl group, t-amyl group, t-octyl group, adamantyl group, o-tolyl group, p-tolyl group, 2, 4-xylyl group, 2, 5-xylyl group, 2, 6-xylyl group, 2,4, 6-mesityl group, di-p-tolylamino group, bis (p- (t-butyl) phenyl) amino group, 3, 6-dimethylcarbazolyl group, and 3, 6-di-t-butylcarbazolyl group are preferable.

In the following structural formulae, "Me" represents a methyl group, "tBu" represents a tert-butyl group, "tAm" represents a tert-pentyl group, "thoct" represents a tert-octyl group, and a bond site.

[ solution 19]

[ solution 20]

[ solution 21]

[ solution 22]

[ solution 23]

[ solution 24]

[ solution 25]

[ solution 26]

[ solution 27]

[ solution 28]

[ solution 29]

[ solution 30]

[ solution 31]

The polycyclic aromatic compound having one or two or more structures containing a structural unit represented by the formula (1A-1) is preferably a structure containing at least one tertiary alkyl group (such as a tertiary butyl group or a tertiary pentyl group), a neopentyl group, or an adamantyl group represented by the formula (tR), and more preferably a structure containing a tertiary alkyl group (such as a tertiary butyl group or a tertiary pentyl group) represented by the formula (tR). The reason for this is that the intermolecular distance is increased by such bulky substituents, and thus the luminescence quantum yield (PLQY) is improved. In addition, as the substituent, a diarylamino group is more preferable. Further, a diarylamino group substituted with a group of the formula (tR), a carbazolyl group substituted with a group of the formula (tR) (preferably an N-carbazolyl group), or a benzocarbazolyl group substituted with a group of the formula (tR) (preferably an N-benzocarbazolyl group) is preferable. Examples of the substitution pattern of the group of formula (tR) for the diarylamino group, the carbazolyl group, and the benzocarbazolyl group include those in which some or all of the hydrogen atoms of the aryl ring or the benzene ring are substituted with the group of formula (tR). In addition, the two aryl groups of the diarylamino group are not bonded to each other, or are bonded via a linking group.

Y ¹ Is B, P, P ═ O, P ═ S, Al, Ga, As, Si-R, or Ge-R, the Si-R and the R of the Ge-R being substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl. Y is ¹ Preferably B, P, P ═ O, P ═ S, more preferably B, P ═ O, and most preferably B.

n, m, q, and r are each independently 0 or 1, and in the case of 0, L in parentheses ¹ 、L ² 、L ³ Or L ⁴ The carbon atom to which the bond is bonded being substituted by hydrogen or a substituent (or R described later) ¹ ) But preferably both are substituted with hydrogen. And in the case of 1, means L ¹ 、L ² 、L ³ And L ⁴ Directly bonded. Specifically, if the formula (A) is1A-1) is an example illustrating the case where n, q and r are 1 and m is 0, as follows. Unless otherwise specified, this description also applies to the preferred embodiment of formula (1A-1). Further, n + m is 1 and q + r is not 0, but q + r is preferably 1.

[ solution 32]

L ¹ 、L ² 、L ³ And L ⁴ Independently of one another, a single bond, substituted or unsubstituted arylene, substituted or unsubstituted heteroarylene, substituted or unsubstituted alkylene, substituted or unsubstituted cycloalkylene, substituted or unsubstituted alkenylene, > O, > N-R, > C (-R) ₂ 、＞Si(-R) ₂ R > N-R, said > Si (-R) ₂ R of (b), and the & gtC (-R) ₂ Each R of (A) is independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, > Si (-R) ₂ And said > C (-R) ₂ The two R's are not bonded to each other to form a ring, or are bonded to each other to form a ring, the R > N-R, the R > C (-R) ₂ R of (b), and said > Si (-R) ₂ Is independently bonded to at least one of the rings a1 through a5 via a single bond or a linking group, or is not bonded via a single bond or a linking group. "arylene", "heteroarylene", "alkylene", "cycloalkylene" and "alkenylene" are divalent radicals obtained by removing one hydrogen from "aryl", "heteroaryl", "alkyl", "cycloalkyl" and "alkenyl", respectively, and preferred ranges thereof may also be referred to with reference to these ranges.

As L ¹ And L ² Preferably a substituted or unsubstituted arylene, a substituted or unsubstituted heteroarylene, or a substituted or unsubstituted alkenylene, more preferably a substituted or unsubstituted arylene, or a substituted or unsubstituted arylene Alkenylene group of (a). The arylene group is preferably a phenylene group or a naphthylene group, and the heteroarylene group is preferably a benzothiophenylene group (benzothiophenylene), a benzofuranylene group (benzofuranylene), an indolyl group, a dibenzothiophenylene group, a dibenzofuranylene group, or a carbazolyl group. As a substituent, the description of "substituted or unsubstituted" in the specification may be referred to, but preferably, arylene and heteroarylene are unsubstituted, or at least one hydrogen is substituted with an alkyl group (particularly, a tertiary alkyl group such as a tertiary butyl group or a tertiary pentyl group), a cycloalkyl group, a diarylamino group, or a substituted silyl group, and more preferably, is unsubstituted, or at least one hydrogen is substituted with an alkyl group (particularly, a tertiary alkyl group such as a tertiary butyl group or a tertiary pentyl group), a cycloalkyl group, or a diarylamino group. In addition, the alkenylene group is preferably unsubstituted or at least one hydrogen is substituted with an alkyl group or an aryl group. In addition, two aryl groups of the diarylamino group are bonded via a linking group, or are not bonded via a linking group, but at least one hydrogen of the two aryl groups may be substituted with a tertiary alkyl group.

As L ³ And L ⁴ More preferably, it is a single bond.

The polycyclic aromatic compound of the present invention is a polycyclic aromatic compound having one or more structures including a structural unit represented by the formula (1A-1). Examples of the polycyclic aromatic compound having a structure containing one structural unit include the polycyclic aromatic compound represented by the above-described formula as the structural unit represented by the formula (1A-1). Examples of the polycyclic aromatic compound having a structure containing two or more structural units represented by the formula (1A-1) include compounds corresponding to multimers of the polycyclic aromatic compound represented by the formula described above as the structural unit represented by the formula (1A-1). The multimer is preferably a dimer to a hexamer, more preferably a dimer to a trimer, and particularly preferably a dimer. The multimer may be in a form having a plurality of the unit structures in one compound, and may be in a form in which any of the rings (the a1 ring, the a2 ring, the A3 ring, the a4 ring, and the a5 ring as described in the formula (1A-1)) contained in the unit structures are bonded in common in the plurality of unit structures, or in a form in which any of the rings (the a1 ring, the a2 ring, the A3 ring, the a4 ring, and the a5 ring as described in the formula (1A-1)) contained in the unit structures are bonded to each other so as to be condensed. The unit structure may be in a form in which a plurality of units are bonded by a single bond, a C1-3 alkylene group, a phenylene group, a naphthylene group, or other linking groups. Among these, the form in which the bonds are bonded so as to share a ring is more preferable. The above description is also applicable to a preferred embodiment of the polycyclic aromatic compound having one or two or more structures including the structural unit represented by formula (1A-1) described later.

The polycyclic aromatic compound having one or more structures containing the structural unit represented by the formula (1A-1) and the preferable embodiments thereof described later can be condensed with at least one cycloalkane.

The cycloalkane may be a cycloalkane having 3 to 24 carbon atoms. At least one hydrogen in the cycloalkane is not substituted or substituted by an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms, an alkyl group having 1 to 24 carbon atoms or a cycloalkyl group having 3 to 24 carbon atoms, and at least one-CH in the cycloalkane ₂ -may be substituted by-O-, or-S-.

When at least one of the structures selected from the group consisting of aryl rings and heteroaryl rings in one or more structures including the structural unit represented by the formula (1A-1) is condensed with at least one cycloalkane, the at least one cycloalkane is preferably a cycloalkane having 3 to 20 carbon atoms, and the cycloalkane may be one in which at least one hydrogen in the cycloalkane is substituted with an aryl group having 6 to 16 carbon atoms, a heteroaryl group having 2 to 22 carbon atoms, an alkyl group having 1 to 12 carbon atoms, or a cycloalkyl group having 3 to 16 carbon atoms.

Examples of the "cycloalkane" include: a C3-24 cycloalkane, a C3-20 cycloalkane, a C3-16 cycloalkane, a C3-14 cycloalkane, a C5-10 cycloalkane, a C5-8 cycloalkane, a C5-6 cycloalkane, a C5 cycloalkane, 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, bisadamantane, decahydronaphthalene, decahydroazulene, and alkyl (particularly methyl) substituents having 1 to 5 carbon atoms thereof, halogen (particularly fluorine) substituents and deuterium substituents.

Among these, a structure in which at least one hydrogen on the carbon at the α -position of a cycloalkane (in a cycloalkyl group condensed on an aryl ring or a heteroaryl ring, the carbon at a position adjacent to the carbon at the condensation site) is substituted, as shown in the following structural formula, is preferable, a structure in which two hydrogens on the carbon at the α -position are substituted is more preferable, and a structure in which a total of four hydrogens on the two carbons at the α -position are substituted is even more preferable. Examples of the substituent include an alkyl (particularly methyl) substituent having 1 to 5 carbon atoms, a halogen (particularly fluorine) substituent, and a deuterium substituent. Particularly preferred is a structure in which a partial structure represented by the following formula (Z) is bonded to adjacent carbon atoms in an aryl ring or a heteroaryl ring.

[ solution 33]

In the formula (Z), Me represents a methyl group and X represents a bonding position.

The number of cycloalkanes condensed in one aryl ring or heteroaryl ring is preferably 1 to 3, more preferably 1 or 2, and still more preferably 1. For example, examples in which 1 or more cycloalkanes are condensed in one benzene ring (phenyl group) are shown below. The bond position may be any one of carbons constituting a benzene ring and not constituting a cycloalkane. Cycloalkanes condensed as shown in the formula (Cy-1-4) and the formula (Cy-2-4) may be condensed with each other. The same applies to the case where the ring (group) to be condensed is an aryl ring or heteroaryl ring other than a benzene ring (phenyl group), and the case where the cycloalkane to be condensed is cyclopentane or a cycloalkane other than cyclohexane.

[ chemical 34]

At least one-CH in cycloalkanes ₂ -may be substituted by-O-, or-S-. For example, 1 or more-CH condensed in cycloalkane of one benzene ring (phenyl group) are shown below ₂ Examples of substitution by-O-. The same applies to the case where the ring (group) to be condensed is an aromatic or heteroaromatic ring other than a benzene ring (phenyl group), and the case where the cycloalkane to be condensed is cyclopentane or a cycloalkane other than cyclohexane.

[ solution 35]

At least one hydrogen in the cycloalkane is unsubstituted or substituted, and as the substituent, for example, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboron, alkyl, alkenyl, cycloalkyl, alkoxy, aryloxy, arylthio, substituted silyl, deuterium, cyano or halogen can be cited, and details thereof can be cited with reference to the description of the first substituent. In addition, the two aryl groups of the diarylamino group are not bonded to each other or bonded via a linking group, the two heteroaryl groups of the diheteroarylamino group are not bonded to each other or bonded via a linking group, the aryl group and the heteroaryl group of the arylheteroarylamino group are not bonded to each other or bonded via a linking group, and the two aryl groups of the diarylboron group are not bonded to each other or bonded via a linking group.

Among these substituents, preferred are alkyl groups (e.g., alkyl groups having 1 to 6 carbon atoms), cycloalkyl groups (e.g., cycloalkyl groups having 3 to 14 carbon atoms), halogens (e.g., fluorine), and deuterium. When the cycloalkyl group is substituted, it may be in a substituted form to form a spiro structure, and the following examples are given.

[ solution 36]

As a form of cycloalkane condensation, there is first mentioned a form in which, in a polycyclic aromatic compound having one or more structures including a structural unit represented by formula (1A-1), an aryl ring and a heteroaryl ring of each of rings a1 to a5 are condensed with cycloalkane.

Examples of other forms of cycloalkane condensation include polycyclic aromatic compounds having one or two or more structures containing a structural unit represented by formula (1A-1) and having diarylamino groups condensed with cycloalkane (condensed to the aryl moiety thereof), carbazolyl groups condensed with cycloalkane (condensed to the benzene ring moiety), or benzocarbazolyl groups condensed with cycloalkane (condensed to the benzene ring moiety). In addition, L may be mentioned ¹ 、L ² 、L ³ And L ⁴ The arylene group, heteroarylene group or alkenylene group of (A) is condensed with a cycloalkane, and examples thereof include N-R, > C (-R) ₂ Or > Si (-R) ₂ Is an example of an aryl group condensed with cycloalkane, or a heteroaryl group condensed with cycloalkane. As the "diarylamino group", groups described as the "first substituent" can be cited. In addition, the two aryl groups of the diarylamino group are not bonded to each other, or are bonded via a linking group.

Further, 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. In the sublimation purification, which is almost indispensable as a purification method for a material for an organic device such as an organic EL element requiring high purity, the purification can be performed at a relatively low temperature, and thus thermal decomposition of the material or the like is avoided. In addition, since the process can be performed at a relatively low temperature in the same manner as in the above-described case, thermal decomposition of the material can be avoided, and as a result, a high-performance organic device can be obtained. Further, introduction of a cycloalkane structure improves solubility in an organic solvent, and thus can be applied to device fabrication using a coating process. The present invention is not particularly limited to these principles.

In the polycyclic aromatic compound containing one or two or more structural units represented by the formula (1A-1) and in a preferred embodiment thereof described later, all or part of hydrogen may be deuterium, cyano or halogen. Halogen is fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, more preferably fluorine or chlorine, and further preferably fluorine. In addition, from the viewpoint of durability, it is also preferable that all or a part of the hydrogens of the aromatic ring portion in the structure of one or two or more containing the structural unit represented by the formula (1A-1) is deuterated, more preferably all of the aromatic ring portion is deuterated, and most preferably L is a group ¹ 、L ² 、L ³ Or L ⁴ All of the hydrogen and the aromatic ring moiety substituted with the alkenylene group of (a) are deuterated.

For example, in one or more structures containing a structural unit represented by formula (1A-1), the aryl, heteroaryl, cycloalkyl, or cycloheteroalkyl ring as the A1, A2, A3, A4, and A5 rings, or the substituent for the A1, A2, A3, A4, and A5 rings, or the substituent for the L-ring ¹ 、L ² 、L ³ And L ⁴ Substituted or unsubstituted arylene, substituted or unsubstituted heteroarylene, substituted or unsubstituted alkylene, substituted or unsubstituted cycloalkylene, substituted or unsubstituted alkenylene, > N-R, > C (-R) ₂ 、＞Si(-R) ₂ Arylene, heteroarylene, alkylene, cycloalkylene, alkenylene, > R of N-R, > Si (-R) ₂ R of (b), and the & gtC (-R) ₂ The hydrogen in R of (a) is substituted by deuterium, cyano or halogen, and among these, preferred is a case where all or a part of the hydrogens in the aromatic ring part of aryl, heteroaryl, arylene, heteroarylene are substituted by deuterium, cyano or halogen.

As a preferred example of the structural unit represented by the formula (1A-1), a structural unit represented by the following formula (1A-1) can be mentioned. In addition, with respect to the structure of the substituent or the ring contained in the formula (1a-1), and the preferable range, the respective descriptions of the corresponding formula (1a-1) can be referred to.

[ solution 37]

In the formula (1a-1), Y ¹ 、L ¹ 、L ² 、L ³ 、L ⁴ N, m, q and r have the same definitions and preferred ranges as those in the formula (1A-1), respectively.

In the formula (1a-1), Z is N or C-R independently ¹ Said C-R ¹ R of (A) to (B) ¹ Each independently is hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or substituted silyl, and is preferably hydrogen, aryl, heteroaryl, alkyl, cycloalkyl, or diarylamino. At least one hydrogen of which is unsubstituted or substituted with an aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl group. In addition, R ¹ Further preferred are hydrogen, alkyl, cycloalkyl, or diarylamino groups, which are unsubstituted or substituted with alkyl or cycloalkyl groups. In addition, the two aryl groups of the diarylamino group are not bonded to each other or bonded via a linking group, the two heteroaryl groups of the diheteroarylamino group are not bonded to each other or bonded via a linking group, the aryl group and the heteroaryl group of the arylheteroarylamino group are not bonded to each other or bonded via a linking group, and the two aryl groups of the diarylboron group are not bonded to each other or bonded via a linking group. The details of the substituents and their preferred ranges listed herein can be referred to the description in the present specification.

In the formula (1a-1), two adjacent R ¹ Are not bonded to each other to form an aryl or heteroaryl ring, or are bonded to each other to form an aryl or heteroaryl ring, at least one hydrogen of the formed aryl ring and the formed heteroaryl ring, respectively, may be substituted by aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboron, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or substituted silyl, preferably hydrogen, aryl, heteroaryl, Heteroaryl, alkyl, cycloalkyl, or diarylamino, at least one of which may be substituted with aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl. In addition, the two aryl groups of the diarylamino group are not bonded to each other or bonded via a linking group, the two heteroaryl groups of the diheteroarylamino group are not bonded to each other or bonded via a linking group, the aryl group and the heteroaryl group of the arylheteroarylamino group are not bonded to each other or bonded via a linking group, and the two aryl groups of the diarylboron group are not bonded to each other or bonded via a linking group. The details of the substituents and their preferred ranges listed herein can be referred to the description in the present specification.

Z is each independently N or C-R ¹ Or each Z ═ Z is independently > O, > N-R, > C (-R) ₂ 、＞Si(-R) ₂ And > S, or > Se, preferably all independently C-R ¹ . Said > N-R, said > C (-R) ₂ And said > Si (-R) ₂ Each R of (a) is independently hydrogen, aryl, heteroaryl, alkyl, cycloalkyl, and where at least one hydrogen of them is substituted, it is preferably aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl. Said > C (-R) ₂ And said > Si (-R) ₂ Two R's are bonded to each other to form a ring, or are not bonded to each other to form a ring. The details of the substituents and their preferred ranges listed herein can be referred to the description in the present specification.

For example, in the a2 ring in the formula (1a-1), the position "Z ═ Z" is substituted with > O, > N-R, > C (-R) ₂ 、＞Si(-R) ₂ The rings obtained by "S" or "Se" include cyclopentadiene ring, pyrrole ring, furan ring, thiophene ring, etc. Examples thereof include a2 ring, and one Z ═ Z is > N-R, > O, > S, > C (-R) ₂ And the remaining Z are examples of C-H. However, the form that can be adopted by the a2 ring and the like is not limited to the following examples. As described above, since the aromatic compound has a resonance structure which is completely equivalent in organic chemistry, it can be based on any possible resonance structure.

[ solution 38]

For L in the formula (1A-1) ¹ 、L ² 、L ³ And L ⁴ In > N-R, > Si (-R) ₂ And > C (-R) ₂ The description that R in at least one of (1) is bonded to the ring A1 to the ring A5 through a linking group or a single bond, or is not bonded to the ring A1 to the ring A5 through a linking group or a single bond, and "the R > N-R, the > C (-R) in the formula (1a-1) ₂ R of (b), and said > Si (-R) ₂ At least one R in (A) is independently of each other as C-R ^Z R in Z of (A) ^Z By at least one of-O-, -S-, -C (-R) ₂ -or a single bond, or not with-O-, -S-, -C (-R) ₂ -or single-bonded "corresponds to the definition. Specifically, R is C-R which is spatially closest to the ring a1 to ring a5 and in each ring ^Z Z of (3) is bonded or not bonded.

In the formula (1a-1) and preferred embodiments thereof, the number of rings (monocyclic rings) containing Z as N is 0 to 4, preferably 0 to 3, more preferably 0 to 2, and particularly preferably 0 to 1. In the formula (1a-1) and preferred embodiments thereof, it is also preferred that all Z's are C-R ^Z 。

In the formula (1a-1) and the ring (monocyclic ring) containing Z as N in a preferred embodiment thereof, one or two of Z are preferably N, and when two are N, it is preferable that two N are not adjacent to each other. When the six-membered ring is a ring containing Z as N, a pyridine ring, a pyrimidine ring, a pyridazine ring or a1, 2, 3-triazine ring is preferable, and a pyridine ring or a pyrimidine ring is more preferable. When the five-membered ring is a ring containing Z as N, a thiazole ring or an oxazole ring is preferable.

As a preferred example of the structural unit represented by the formula (1A-1), a structural unit represented by the formula (1b-1) or the formula (1b-2) can be mentioned. In addition, with respect to the substituent or the structure of the ring contained in the formula (1b-1) and the formula (1b-2), preferable ranges can be referred to the respective descriptions of the corresponding formula (1 a-1).

[ solution 39]

In the formula (1b-1) and the formula (1b-2), q and R are each independently 0 or 1, and in the case of 0, a carbon atom bonded to a divalent group in a bracket is bonded through R ¹ Where q + r is not 0, but is preferably 1.

L ³ 、L ⁴ Each independently a single bond, arylene, heteroarylene, or alkenylene, at least one hydrogen of which is substituted or unsubstituted with an alkyl, cycloalkyl, diarylamino, or substituted silyl group, the two aryl groups of the diarylamino group being bonded or not bonded via a linking group. L is a radical of an alcohol ³ And L ⁴ Preferably a single bond. In addition, with respect to Z and Y ¹ The definitions of (1) and preferred ranges thereof can be referred to in the description of the formula (1 a-1).

As a preferred example of the structural unit represented by the formula (1A-1), there can be mentioned the structural unit represented by the formula (1c-1), the formula (1c-2), the formula (1c-3) or the formula (1 c-4). In addition, with respect to the definitions of Z in the formula (1c-1), the formula (1c-2), the formula (1c-3) and the formula (1c-4) and preferable ranges thereof, the respective descriptions of the corresponding formula (1a-1) can be referred to.

[ solution 40]

As a preferred example of the structural unit represented by the formula (1A-1), a structural unit represented by the formula (1d-1) or the formula (1d-2) can be mentioned.

[ solution 41]

In the formulae (1d-1) and (1d-2), R ^d Each independently is hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboron, alkylAn aryl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or substituted silyl group, and is preferably hydrogen, aryl, heteroaryl, alkyl, cycloalkyl, or diarylamino, or substituted silyl, more preferably hydrogen, alkyl, cycloalkyl, aryl, or heteroaryl, and most preferably all hydrogen. In addition, at least one hydrogen of them is unsubstituted or substituted with aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl. In addition, the two aryl groups of the diarylamino group are not bonded to each other or bonded via a linking group, the two heteroaryl groups of the diheteroarylamino group are not bonded to each other or bonded via a linking group, the aryl group and the heteroaryl group of the arylheteroarylamino group are not bonded to each other or bonded via a linking group, and the two aryl groups of the diarylboron group are not bonded to each other or bonded via a single bond or a linking group. The details of the substituents listed here and their preferred ranges can be referred to the description in the present specification. For the definitions of other symbols in the formulae (1d-1) and (1d-2) and the preferable ranges, the descriptions of the formulae (1b-1) and (1b-2) can be referred to.

As a formula (1A-1) expressed by the structural unit of the preferred example, can be cited (1e-1), formula (1e-2), formula (1e-3) or formula (1e-4) expressed by the structural unit. The definitions of the symbols and the preferred ranges thereof can be found in the descriptions of the formulae (1d-1) and (1 d-2).

[ solution 42]

As a preferred example of the structural unit represented by the formula (1A-1), a structural unit represented by the formula (1f-1) or the formula (1f-2) can be mentioned.

[ solution 43]

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

[ solution 44]

Further, in the case where x is 2 or 3, 2 or 3E are continuous, these are defined as "independent" as described later, and 2 or 3E are the same or different. When x is 3, 2E's may be the same and 1E may be different. This description applies to the preferred embodiment of the formula (1f-1) or the formula (1f-2) described later unless otherwise specified.

In the formula (1f-1) or the formula (1f-2), A is each independently > (CR) -, and R of the > (CR) -is hydrogen, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted cycloalkyl group, and more preferably hydrogen, or an alkyl group. L when the subscripts (N, m, q, and r) related to N and parentheses are 1 ¹ ～L ⁴ R of the bonded A > (CR) -is preferably alkyl. The details of the substituents and their preferred ranges listed herein can be referred to the description in the present specification.

Further, in the formula (1f-1) or the formula (1f-2), L adjacent to A ³ Or L ⁴ When the subscript of the parentheses is 1, L ³ Or L ⁴ A carbon atom which is > (CR) -of A when the bond is 0, and L ³ Or L ⁴ The carbon atoms of the bonded f3 or f4 ring are each independently substituted by R ¹ And (4) substitution. This case is represented by, for example, the formula (1f-1), as follows. In the following, R represents R as "CR" of A. This description applies to the preferred embodiment of the formula (1f-1) or the formula (1f-2) described later unless otherwise specified. The details of the substituents and their preferred ranges listed herein can be referred to the description in the present specification.

[ solution 45]

Formula (1f-1)Or in the formula (1f-2), E is independently > O, > N-R, > C (-R) ₂ 、＞Si(-R) ₂ R > N-R, said > Si (-R) ₂ R of (b), and the & gtC (-R) ₂ Each R of (A) is independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, > Si (-R) ₂ And said > C (-R) ₂ Preferably, E is independently > O, > N-R, > S, or > C (-R) ₂ Most preferably, all E's are each independently > C (-R) ₂ . Furthermore, the above-mentioned > C (-R) ₂ R in (A) is hydrogen. This description applies to the preferred embodiment of the formula (1f-1) or the formula (1f-2) described later unless otherwise specified.

For other symbols in the formula (1f-1) or the formula (1f-2) and their preferred ranges, the description of the formula (1a-1) can be referred to. In addition, the details of the substituents and their preferred ranges listed herein can be referred to the description in the present specification.

As a preferred example of the structural unit represented by the formula (1f-1) or the formula (1f-2), a structural unit represented by the formula (1g-1) or the formula (1g-2) can be mentioned.

[ solution 46]

With respect to the definitions of A, E and x in formula (1g-1) or formula (1g-2) and their preferred ranges, reference is made to the descriptions in formula (1f-1) and formula (1 f-2). In addition, Z, Y ¹ 、L ³ 、L ⁴ The definitions of r and q and their preferred ranges can be found in the descriptions of the formulae (1b-1) and (1 b-2).

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

[ solution 47]

With respect to the definitions of A, E and x in formula (1h-1), formula (1h-2), formula (1h-3), and formula (1h-4), and their preferred ranges, the descriptions in formula (1f-1) and formula (1f-2) can be referred to. In addition, with respect to the definition of Z and their preferred ranges, reference is made to the descriptions of the formulae (1b-1) and (1 b-2).

As a formula (1f-1) or (1f-2) expressed by the structural unit of the preferred example, can be cited (1i-1) or (1i-2) expressed by the structural unit.

[ solution 48]

With respect to R in the formula (1i-1) or the formula (1i-2) ^d The definitions of (1) and their preferred ranges can be referred to the description of formula (1d-1) or formula (1 d-2). For other symbols and their preferred ranges, the description of formula (1b-1) or formula (1b-2) can be referred to.

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

[ solution 49]

With respect to R in the formula (1k-1), the formula (1k-2), the formula (1k-3) or the formula (1k-4) ^d The definitions of (1) and their preferred ranges can be referred to the description of formula (1d-1) or formula (1 d-2). Further, with respect to the definition of Z and their preferred ranges, reference is made to the descriptions in the formulae (1b-1) and (1 b-2).

Preferred examples of the polycyclic aromatic compound having a structure containing two structural units represented by the formula (1a-1) include the formula (1a-d-1), the formula (1a-d-2), the formula (1a-d-3) and the formula (1 a-d-4). Their structures are dimeric structures sharing a8 loop.

In the formulae (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 Independently of one another, a single bond, a substituted or unsubstituted arylene group, a substituted or unsubstituted heteroarylene group, a substituted or unsubstituted alkylene group, a substituted or unsubstituted cycloalkylene group, a substituted or unsubstituted alkenylene group, > O, > N-R, > C (-R) ₂ 、＞Si(-R) ₂ R > N-R, said > Si (-R) ₂ R of (b), and the & gtC (-R) ₂ Each R of (A) is independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, > Si (-R) ₂ Two R of (a) and said > C (-R) ₂ Two R's may be bonded to each other to form a ring. Of these, preferred is a single bond, a substituted or unsubstituted arylene group (preferably a phenylene group or a naphthylene group), or a substituted or unsubstituted heteroarylene group (preferably a benzothiophenyl group, a benzofuranylene group, an indolyl group, a dibenzothiophenylene group, a dibenzofuranylene group, or a carbazolyl group), L ⁵ ～L ¹² Is a substituted or unsubstituted arylene, a substituted or unsubstituted heteroarylene, or a substituted or unsubstituted alkenylene (in each case, the subscript of the parentheses is 1). In addition, d + e + f + h + s + t + w + w is not equal to 0. Y is ¹ And Z may apply to the definitions and preferred ranges of formula (1a-1), Z preferably being all C-R ¹ ，Y ¹ Preferably B. The substituents and their preferred ranges listed herein are described in detail in the specification.

Preferred examples of the polycyclic aromatic compound having a structure containing two structural units represented by the formulae (1c-1) to (1c-4) include: formula (1c-d-1), 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 containing two structural units represented by the formulae (1e-1) to (1e-4) include: formula (1e-d-1), 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), formula (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 (1 e-d-19).

These structures are dimeric structures sharing a c11 ring or an e11 ring, respectively. The definitions and preferred ranges of the formulae (1c-1) to (1c-4) and the formulae (1e-1) to (1e-4) can be applied to Z, respectively.

[ solution 50]

[ solution 51]

[ solution 52]

[ chemical formula 53]

[ formula 54]

[ solution 55]

More specific examples of the polycyclic aromatic compound having one or more structures containing the structural unit represented by the formula (1A-1) of the present invention include the following compounds. In the following structural formula, "Me" represents a methyl group, "tBu" represents a tert-butyl group, and "D" represents deuterium. The following configuration is an example.

[ solution 56]

[ solution 57]

[ solution 58]

[ chemical 59]

[ solution 60]

The polycyclic aromatic compound of the present invention can be produced in the following manner.

Method for producing polycyclic aromatic compound

Having a structure comprising the formula (1A-1)The polycyclic aromatic compounds having one or more structures of the structural units shown are basically prepared by first using a bonding group (L) ¹ ～L ⁴ And a group containing a nitrogen atom) to bond the A1 ring to the A5 ring, thereby producing an intermediate (first reaction), and then, using the bonding group (containing Y) ¹ Group (ii) bonds the a2 ring and the a4 ring, whereby the final product can be produced (second reaction). In the first Reaction, for example, in the case of etherification, a typical Reaction such as nucleophilic substitution Reaction or Ullmann Reaction (Ullmann Reaction) can be used, and in the case of amination, a typical Reaction such as Buchwald-Hartwig Reaction (Buchwald-Hartwig Reaction) can be used. In the second Reaction, a Tandem Hetero Friedel-Crafts Reaction (consecutive aromatic electrophilic substitution Reaction, the same applies hereinafter) can be used. The compound having a condensed ring can be produced by using a raw material having a desired condensed ring at a certain position in the reaction step or by adding a step of condensing the ring. In addition, polycyclic aromatic compounds having a structure containing two or more structural units pass through the bonding group (containing Y) in the second reaction as long as the corresponding intermediate is produced in the first reaction ¹ Group (c) may be bonded. In this case, it is only necessary to use Y introduced ¹ Is adjusted to include Y ¹ A reagent (e.g., boron tribromide) necessary for introducing the group(s) may be used.

< 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 the following steps, reference is made to the description of international publication No. 2015/102118.

The following describes a reaction including the following reaction steps: a reaction step of metallizing a halogen atom (Hal) between nitrogen atoms in the following intermediate-1 with an organic base compound; using a substance selected from the group consisting of Y ¹ Halide of (2), Y ¹ Of an aminated halide of, Y ¹ Alkoxylates of (D) and Y ¹ With Y ¹ A reaction step of performing exchange; and by successive aromatic affinities using a Bronsted baseUsing the Y for electron substitution reaction ¹ And a reaction step of bonding the B ring and the C ring.

[ solution 61]

< 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 the following steps, reference is made to the description of International publication No. 2015/102118.

The following describes a reaction including the following reaction steps: a reaction step of metallizing hydrogen atoms (H) between nitrogen atoms in the intermediate-2 with an organic basic compound; using a substance selected from the group consisting of Y ¹ Halide of (2), Y ¹ Of an aminated halide of, Y ¹ Alkoxylates of (D) and Y ¹ With Y ¹ A reaction step of exchanging; and using the Y by successive aromatic electrophilic substitution reactions using a Bronsted base ¹ And a reaction step of bonding the B ring and the C ring. In addition, The method can also be used to omit The reaction step of metalating The hydrogen atom (H) with an organic alkali compound to react with Y, as described in Journal of The American Chemistry, 2018,140,1195-1198, German applied Chemistry, 2021,60,2882-2886, or Nature Photonics 2019,13,678 ¹ A direct reaction (one-step process) of the halide (boron tribromide, etc.). At this time, can be in the same direction as Y ¹ After the reaction of the halide (e.g., boron tribromide) or in combination with a base such as an amine.

[ solution 62]

Examples of the metallizing reagent used in the halogen-metal exchange reaction in the above-described flow chart include: alkyllithium such as methyllithium, n-butyllithium, sec-butyllithium and tert-butyllithium, lithium chloride complex of isopropylmagnesium chloride, isopropylmagnesium bromide, phenylmagnesium chloride, phenylmagnesium bromide and isopropylmagnesium chloride known as a Tabo Grignard Reagent (Turbo Grignard Reagent), and the like.

In addition, examples of the metallation reagent used in the ortho-position metal exchange reaction in the above-described flow chart include: organic base compounds such as lithium diisopropylamide, lithium tetramethylpiperidide, lithium hexamethyldisilazide, potassium hexamethyldisilazide, lithium tetramethylpiperidyl magnesium chloride-lithium chloride complex, and tri-n-butyllithium magnesium chloride.

Further, as additives which promote the reaction when alkyllithium is used as a metallizing agent, there can be mentioned: n, N, N ', N' -tetramethylethylenediamine, 1, 4-diazabicyclo [2.2.2] octane, N, N-dimethylpropyleneurea, and the like.

In addition, as the lewis acid used in the scheme described so far, there can be mentioned: 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 having these lewis acids supported on a solid can be similarly used.

Further, as the bronsted acid used in the flow described so far, there can be mentioned: p-toluenesulfonic acid, methanesulfonic acid, trifluoromethanesulfonic acid, fluorosulfonic acid, carborane acid, trifluoroacetic acid, (trifluoromethanesulfonyl) imide, tris (trifluoromethanesulfonyl) methane, hydrogen chloride, hydrogen bromide, hydrogen fluoride, and the like. Further, as the solid bronsted acid, there can be mentioned: amberlyst (Amberlist) (trade name: Dow Chemical), Nafion (Nafion) (trade name: dupont), zeolite (zeolite), and thiocyanurate (taycature) (trade name: thiocyanurate (Tayca) inc.), and the like.

Further, as amines that can be added in the flow described so far, there can be mentioned: diisopropylethylamine, triethylamine, tributylamine, 1, 4-diazabicyclo [2.2.2] octane, N-dimethyl-p-toluidine, N-dimethylaniline, pyridine, 2, 6-dimethylpyridine, 2, 6-di-tert-butylamine, and the like.

In addition, as the solvent used in the flow described so far, there can be mentioned: o-dichlorobenzene, chlorobenzene, toluene, benzene, dichloromethane, chloroform, dichloroethylene, trifluorotoluene, decahydronaphthalene, cyclohexane, hexane, heptane, 1,2, 4-trimethylbenzene, xylene, diphenyl ether, anisole, cyclopentyl methyl ether, tetrahydrofuran, dioxane, methyl-tert-butyl ether, and the like.

Here, Y is described ¹ B is exemplified, but Y can also be synthesized by appropriately changing the raw materials ¹ Compounds of formula P, P ═ O, P ═ S, Al, Ga, As, Si-R or Ge-R.

As Y used ¹ Halide of (2), with respect to Y ¹ As the halide of B, there may be mentioned: boron trichloride, boron tribromide and boron triiodide.

In the scheme, a bronsted base or a lewis acid may be used to promote the tandem hybrid-schmidt reaction. However, in the use of Y ¹ Of (b) trifluoride, Y ¹ Trichloride of (a) and Y ¹ Tribromide of (5), Y ¹ Y being triiodide or the like ¹ In the case of the halide of (3), since an acid such as hydrogen fluoride, hydrogen chloride, hydrogen bromide, or hydrogen iodide is generated as the aromatic electrophilic substitution reaction proceeds, it is effective to use a bronsted base which traps an acid. On the other hand, in the use of Y ¹ Of an aminated halide of, Y ¹ In the case of the alkoxylate (b), an amine or alcohol is formed as the aromatic electrophilic substitution reaction proceeds, and therefore, in many cases, the alkoxylate (b) is not a compound having a hydroxyl groupThe bronsted base is not required, but since the ability to remove an amino group or an alkoxy group is low, it is effective to use a lewis acid for accelerating the removal.

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

< organic device >

The polycyclic aromatic compound of the present invention is useful as a material for organic devices. Examples of the organic device include: an organic electroluminescent device, an organic field effect transistor, an organic thin film solar cell, or the like, but a material for an organic electroluminescent device is preferable.

< organic electroluminescent element >

< Structure of organic electroluminescent element >

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

The organic EL element 100 shown in fig. 1 includes: the light-emitting device comprises a substrate 101, an anode 102 disposed on the substrate 101, a hole injection layer 103 disposed on the anode 102, a hole transport layer 104 disposed on the hole injection layer 103, a light-emitting layer 105 disposed on the hole transport layer 104, an electron transport layer 106 disposed on the light-emitting layer 105, an electron injection layer 107 disposed on the electron transport layer 106, and a cathode 108 disposed on the electron injection layer 107.

In addition, the organic EL device 100 may be formed by reversing the manufacturing order, for example, by a structure including: a substrate 101, a cathode 108 disposed on the substrate 101, an electron injection layer 107 disposed on the cathode 108, an electron transport layer 106 disposed on the electron injection layer 107, an emission layer 105 disposed on the electron transport layer 106, a hole transport layer 104 disposed on the emission layer 105, a hole injection layer 103 disposed on the hole transport layer 104, and an anode 102 disposed on the hole injection layer 103.

All of the layers are not indispensable, and the minimum structural unit is configured to include the anode 102, the light-emitting layer 105, and the cathode 108, and the hole injection layer 103, the hole transport layer 104, the electron transport layer 106, and the electron injection layer 107 are layers that can be arbitrarily provided. In addition, each of the layers may include a single layer, or may include a plurality of layers.

The form of the layer constituting the organic EL element may be, in addition to the structural form of "substrate/anode/hole injection layer/hole transport layer/light-emitting layer/electron transport layer/electron injection layer/cathode", "substrate/anode/hole injection layer/hole transport layer/light-emitting layer/electron transport layer/cathode"), The structural forms of "substrate/anode/light-emitting layer/electron transport 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/light-emitting layer/electron transport layer/cathode", "substrate/anode/light-emitting layer/electron injection layer/cathode".

< light-emitting layer in organic electroluminescent element >

The polycyclic aromatic compound of the present invention is preferably used as a material for forming 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 emits light by recombination of holes injected from the anode 102 and electrons injected from the cathode 108 between electrodes to which an electric field is applied. The material for forming the light-emitting layer 105 may be a compound (light-emitting compound) which emits light by being excited by recombination of holes and electrons, and is preferably a compound which can be formed into a stable thin film shape and which exhibits strong light emission (fluorescence) efficiency in a solid state. The polycyclic aromatic compound of the present invention is useful as a material for a light-emitting layer, a dopant material, or a host material, but is preferably used as a material for a light-emitting layer, and more preferably used as a dopant material.

In addition, as the dopant, there is an example in which an auxiliary dopant and an emitting dopant are used in combination as described below, but in the present specification, when simply described as "dopant", the dopant refers to an emitting dopant, that is, a dopant which emits light by itself.

The light-emitting layer may be a single layer or may include a plurality of layers, and each of the layers is formed of a material (host material or dopant material) for the light-emitting layer. The host material and the dopant material may be one kind or a combination of two or more kinds, respectively. The dopant material may be contained within the bulk of the host material, or may be contained within a portion of the host material, either. The doping method may be a co-evaporation method with the host material, or may be a method in which the dopant is mixed with the host material and evaporated at the same time.

The amount of the host material to be used differs depending on the type of the host material, and may be determined in accordance with the characteristics of the host material. The amount of the host material used is preferably 50 to 99.999 mass%, more preferably 80 to 99.95 mass%, and still more preferably 90 to 99.9 mass%, based on the total mass of the light-emitting layer material.

The amount of the dopant material used varies depending on the kind of the dopant material, and may be determined by matching the characteristics of the dopant material. The amount of the dopant used is preferably 0.001 to 50% by mass, more preferably 0.05 to 20% by mass, and still more preferably 0.1 to 10% by mass of the entire material for the light-emitting layer. The above range is preferable, for example, in terms of preventing the concentration quenching phenomenon.

< host Material >

As the host material, anthracene, pyrene, dibenzo known as a light-emitting body from the past can be mentioned

Or a fused ring derivative such as fluorene, a bisstyryl derivative such as a bisstyrylanthracene derivative or a distyrylbenzene derivative, a tetraphenylbutadiene derivative, a cyclopentadiene derivative, a fluorene derivative, a benzofluorene derivative, or a dibenzo

And the like.

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

[ solution 63]

In the formulae (H1), (H2) and (H3), L ¹ The arylene group is an arylene group having 6 to 24 carbon atoms, a heteroarylene group having 2 to 24 carbon atoms, a heteroarylene group having 6 to 24 carbon atoms or an aryleneheteroarylene group having 6 to 24 carbon atoms, preferably an arylene group having 6 to 16 carbon atoms, more preferably an arylene group having 6 to 12 carbon atoms, particularly preferably an arylene group having 6 to 10 carbon atoms, and specifically, a divalent group such as a benzene ring, a biphenyl ring, a terphenyl ring or a fluorene ring may be mentioned. The heteroarylene group is preferably a heteroarylene group having 2 to 24 carbon atoms, more preferably a heteroarylene group having 2 to 20 carbon atoms, further preferably a heteroarylene group having 2 to 15 carbon atoms, particularly preferably a heteroarylene group having 2 to 10 carbon atoms, and specifically, the heteroarylene group includes: pyrrole ring, oxazole ring, isoxazole ring, thiazole ring, isothiazole ring, imidazole ring, oxadiazole ring, thiadiazole ring, triazole ring, tetrazole ring, pyrazole ring, pyridine ring, pyrimidine ring, pyridazine ring, pyrazine ring, triazine ring, indole ring, isoindole ring, 1H-indazole ring, benzimidazole ring, benzoxazole ring, benzothiazole ring, 1H-benzotriazole ring, quinoline ring, isoquinoline ring, cinnoline ring, quinazoline ring, quinoxaline ring, phthalazine ring, naphthyridine ring, purine ring, pteridine ring, carbazole ring, acridine ring, phenoxathiin ring, phenoxazine ring, phenothiazine ring, indolizine ring, furan ring A benzofuran ring, an isobenzofuran ring, a dibenzofuran ring, a thiophene ring, a benzothiophene ring, a dibenzothiophene ring, a furazan ring, an oxadiazole ring, a thianthracene ring, and the like.

At least one hydrogen in the compound represented by each formula may be substituted by an alkyl group having 1 to 6 carbon atoms, a cyano group, a halogen, or deuterium.

Specific preferred examples include compounds represented by any of the following structural formulae. In the following structural formulae, at least one hydrogen may be substituted by a halogen, a cyano group, an alkyl group having 1 to 4 carbon atoms (for example, a methyl group or a tert-butyl group), a phenyl group, a naphthyl group, or the like.

[ solution 64]

[ solution 65]

[ solution 66]

[ solution 67]

< Anthracene-based Compound >

As the anthracene compound as a host material, for example, a compound represented by the formula (3-H) and a compound represented by the formula (3-H2) can be mentioned.

[ solution 68]

In the formula (3-H),

x and Ar ⁴ Each independently being hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted diarylamino, optionally substituted diheteroarylamino, optionally substituted arylheteroarylamino, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted arylthio or optionally substituted silyl, X and Ar ⁴ Not all of them will be simultaneously converted to hydrogen,

at least one hydrogen in the compound represented by formula (3-H) may be substituted with halogen, cyano, deuterium, or a substituted heteroaryl. In addition, the two aryl groups of the diarylamino group are not bonded to each other or are bonded via a linking group, the two heteroaryl groups of the diheteroarylamino group are not bonded to each other or are bonded via a linking group, and the aryl group and the heteroaryl group of the arylheteroarylamino group are not bonded to each other or are bonded via a linking group.

In addition, the structure represented by formula (3-H) as a unit structure to form polymer (preferably two dimers). In this case, for example, the unit structures represented by the formula (3-H) are bonded to each other via X, and X includes a single bond, an arylene group (e.g., a phenylene group, a biphenylene group, and a naphthylene group), and a heteroarylene group (e.g., a group having a divalent bonding valence such as a pyridine ring, a dibenzofuran ring, a dibenzothiophene ring, a carbazole ring, a benzocarbazole ring, and a phenyl-substituted carbazole ring).

The details of each group in the compound represented by the formula (3-H) can be described with reference to the formula (1), and further described in the following preferred embodiment column.

Preferred embodiments of the anthracene compound will be described below. The symbols in the following structures are defined as described above.

[ solution 69]

In the formula (3-H), X is a group represented by a formula (3-X1), a formula (3-X2) or a formula (3-X3), and the group represented by the formula (3-X1), the formula (3-X2) or the formula (3-X3) is bonded to the anthracene ring of the formula (3-H) at the position. Preferably, two xs do not simultaneously form a group represented by the formula (3-X3). More preferably, both X's do not simultaneously form a group represented by the formula (3-X2).

In addition, the structure represented by formula (3-H) as a unit structure to form polymer (preferably two dimers). In this case, for example, the unit structures represented by the formula (3-H) are bonded to each other via X, and X may be a single bond, an arylene group (e.g., phenylene, biphenylene, and naphthylene), a heteroarylene group (e.g., a group having a divalent bonding valence such as a pyridine ring, a dibenzofuran ring, a dibenzothiophene ring, a carbazole ring, a benzocarbazole ring, and a phenyl-substituted carbazole ring), or the like.

The naphthylene moiety in the formulae (3-X1) and (3-X2) may be condensed with a benzene ring. The structure obtained by condensation in the above-described manner is as follows.

[ solution 70]

Ar ¹ And Ar ² Each independently is hydrogen, phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, or,

A triphenylene group, a pyrenyl group, or a group represented by the formula (A) (including a carbazolyl group, a benzocarbazolyl group, and a phenyl-substituted carbazolyl group). In addition, in Ar ¹ Or Ar ² In the case of the 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 the formula (3-X2) at the position.

Ar ³ Is phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, or the like,

A group represented by the formula (A), a triphenylene group, a pyrenyl group or a group represented by the formula (A) (including a carbazolyl groupBenzocarbazolyl groups and phenyl-substituted carbazolyl groups). In addition, in Ar ³ In the case of the group represented by formula (a), the group represented by formula (a) is bonded to a single bond represented by a straight line in formula (3-X3) at the position indicated by X. That is, the anthracene ring of the formula (3-H) is directly bonded to the group represented by the formula (A).

In addition, Ar ³ May have a substituent, Ar ³ At least one hydrogen in the above (a) may further be an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthryl group, a fluorenyl group,

A triphenylene group, a pyrenyl group, or a group represented by the formula (A) (including a carbazolyl group and a phenyl-substituted carbazolyl group). In addition, in Ar ³ When the substituent is a group represented by formula (a), the group represented by formula (a) is bonded to Ar in formula (3-X3) at the position indicated by ³ Bonding.

Ar ⁴ Each independently hydrogen, phenyl, biphenyl, terphenyl, naphthyl, or a silyl group substituted with an alkyl group having 1 to 4 carbon atoms (methyl, ethyl, tert-butyl, etc.) and/or a cycloalkyl group having 5 to 10 carbon atoms.

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

Specific examples of the "silyl group substituted with an alkyl group having 1 to 4 carbon atoms" include: trimethylsilyl group, triethylsilyl group, tripropylsilyl group, triisopropylsilyl group, tributylsilyl group, tri-sec-butylsilyl group, tri-tert-butylsilyl group, ethyldimethylsilyl group, propyldimethylsilyl group, isopropyldimethylsilyl group, butyldimethylsilyl group, sec-butyldimethylsilyl group, tert-butyldimethylsilyl group, methyldiethylsilyl group, propyldiethylsilyl group, isopropyldiethylsilyl, butyldiethylsilyl, sec-butyldiethylsilyl, tert-butyldiethylsilyl, methyldipropylsilyl, ethyldipropylsilyl, butyldipropylsilyl, sec-butyldipropylsilyl, tert-butyldipropylsilyl, methyldiisopropylsilyl, ethyldiisopropylsilyl, butyldiisopropylsilyl, sec-butyldiisopropylsilyl, tert-butyldiisopropylsilyl, and the like.

Examples of the cycloalkyl group having 5 to 10 carbon atoms substituted in the silyl group include: cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, bicyclo [1.1.1] pentyl, bicyclo [2.1.0] pentyl, bicyclo [2.1.1] hexyl, bicyclo [3.1.0] hexyl, bicyclo [2.2.1] heptyl, bicyclo [2.2.2] octyl, adamantyl, decahydronaphthyl, decahydroazulenyl, and the like, and three hydrogens in the silane group are each independently substituted by their cycloalkyl groups.

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

Examples of the substituted silyl group include a dialkylcycloalkylsilyl group substituted with two alkyl groups and one cycloalkyl group, and an alkylbicycloalkylsilyl group substituted with one alkyl group and two cycloalkyl groups.

In addition, the hydrogen in the chemical structure of the anthracene compound represented by the formula (3-H) may be substituted with a group represented by the formula (A). In the case of substitution by the group represented by formula (a), the group represented by formula (a) is substituted at said site with at least one hydrogen in the compound represented by formula (3-H).

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

[ solution 71]

In the formula (A), Y is-O-, -S-or > N-R ²⁹ ，R ²¹ ～R ²⁸ Each independently is hydrogen, alkyl which may be substituted, cycloalkyl which may be substituted, aryl which may be substituted, heteroaryl which may be substituted, alkoxy which may be substitutedSubstituted aryloxy, optionally substituted arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkylbicycloalkylsilyl, optionally substituted amino, halogen, hydroxy or cyano, R ²¹ ～R ²⁸ Wherein adjacent groups are not bonded to each other to form a hydrocarbon ring, an aryl ring or a heteroaryl ring, or are bonded to each other to form a hydrocarbon ring, an aryl ring or a heteroaryl ring, R ²⁹ Is hydrogen or a substituted aryl group.

Y in the formula (A) is preferably-O-.

As R ²¹ ～R ²⁸ The "alkyl group" of the "alkyl group which may be substituted" in (1) may be either a straight chain or a branched chain, and examples thereof include a straight chain alkyl group having 1 to 24 carbon atoms and a branched alkyl group having 3 to 24 carbon atoms. Preferably an alkyl group having 1 to 18 carbon atoms (branched alkyl group having 3 to 18 carbon atoms), more preferably an alkyl group having 1 to 12 carbon atoms (branched alkyl group having 3 to 12 carbon atoms), still more preferably an alkyl group having 1 to 6 carbon atoms (branched alkyl group having 3 to 6 carbon atoms), and particularly preferably an alkyl group having 1 to 4 carbon atoms (branched alkyl group having 3 to 4 carbon atoms).

Specific examples of the "alkyl group" include: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 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 and the like.

As R ²¹ ～R ²⁸ The "cycloalkyl group" of the "cycloalkyl group which may be substituted" in (1) may be exemplified by: a cycloalkyl group having 3 to 24 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, a cycloalkyl group having 3 to 16 carbon atoms, a cycloalkyl group having 3 to 14 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, a cycloalkyl group having 5 to 8 carbon atoms, a cycloalkyl group having 5 to 6 carbon atoms, a cycloalkyl group having 5 carbon atoms, and the like.

Specific "cycloalkyl" groups include: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and alkyl (particularly methyl) substituents having 1 to 4 carbon atoms thereof, 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, diamantanyl, decahydronaphthyl, decahydroazulenyl, and the like.

As R ²¹ ～R ²⁸ The "aryl group" of the "aryl group which may be substituted" in (1) includes, for example, an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 16 carbon atoms, more preferably an aryl group having 6 to 12 carbon atoms, and particularly preferably an aryl group having 6 to 10 carbon atoms.

Specific "aryl" groups include: phenyl as a monocyclic system, biphenyl as a bicyclic system, naphthyl as a condensed bicyclic system, terphenyl (m-terphenyl, o-terphenyl, p-terphenyl) as a tricyclic system, acenaphthyl, fluorenyl, phenaenyl, phenanthryl as a condensed tricyclic system, triphenylene, pyrenyl, tetracenyl as a condensed tetracyclic system, perylenyl, pentacenyl as a condensed pentacyclic system, and the like.

As R ²¹ ～R ²⁸ The "heteroaryl group" of the "heteroaryl group which may be substituted" in (1) includes, for example, a heteroaryl group having 2 to 30 carbon atoms, preferably a heteroaryl group having 2 to 25 carbon atoms, more preferably a heteroaryl group having 2 to 20 carbon atoms, further preferably a heteroaryl group having 2 to 15 carbon atoms, and particularly preferably a heteroaryl group having 2 to 10 carbon atoms. Examples of the heteroaryl group include a heterocyclic ring containing 1 to 5 heteroatoms selected from oxygen, sulfur and nitrogen as ring-constituting atoms in addition to carbon.

Specific "heteroaryl" groups include, for example: pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxathiyl, phenoxazinyl, phenothiazinyl, phenazinyl, indolizinyl, furyl, benzofuryl, isobenzofuryl, dibenzofuryl, thienyl, benzo [ b ] thienyl, dibenzothienyl, furazanyl, thianthrenyl, naphthobenzofuryl, naphthobenzothienyl, and the like.

As R ²¹ ～R ²⁸ Examples of the "alkoxy group" of the "alkoxy group which may be substituted" in (1) include a linear alkoxy group having 1 to 24 carbon atoms and a branched alkoxy group having 3 to 24 carbon atoms. The alkoxy group is preferably an alkoxy group having 1 to 18 carbon atoms (a branched alkoxy group having 3 to 18 carbon atoms), more preferably an alkoxy group having 1 to 12 carbon atoms (a branched alkoxy group having 3 to 12 carbon atoms), still more preferably an alkoxy group having 1 to 6 carbon atoms (a branched alkoxy group having 3 to 6 carbon atoms), and particularly preferably an alkoxy group having 1 to 4 carbon atoms (a branched alkoxy group having 3 to 4 carbon atoms).

Specific "alkoxy" may include: methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy and the like.

R ²¹ ～R ²⁸ The "aryloxy group" of the "aryloxy group which may be substituted" in (1) is a group in which hydrogen of the-OH group is substituted by an aryl group which may be cited as said R ²¹ ～R ²⁸ The "aryl" in (1).

R ²¹ ～R ²⁸ The "arylthio group" of the "arylthio group which may be substituted" in (1) is a group in which hydrogen of the-SH group is substituted with an aryl group, which may be cited as the R ²¹ ～R ²⁸ The "aryl" in (1).

As R ²¹ ～R ²⁸ As the "trialkylsilyl group" in (1), there can be mentioned groups in which three hydrogens in the silyl group are each independently substituted with an alkyl group, and the alkyl group can be cited as the R ²¹ ～R ²⁸ The "alkyl" in (1) or (b). Preferred alkyl groups for substitution are alkyl groups having 1 to 4 carbon atoms, and specific examples thereof include: methyl, ethyl, propyl, isopropyl, butyl, sec-butylTert-butyl, cyclobutyl and the like.

Specific examples of the "trialkylsilyl group" include: trimethylsilyl group, triethylsilyl group, tripropylsilyl group, triisopropylsilyl group, tributylsilyl group, tri-sec-butylsilyl group, tri-tert-butylsilyl group, ethyldimethylsilyl group, propyldimethylsilyl group, isopropyldimethylsilyl group, butyldimethylsilyl group, sec-butyldimethylsilyl group, tert-butyldimethylsilyl group, methyldiethylsilyl group, propyldiethylsilyl group, isopropyldiethylsilyl, butyldiethylsilyl, sec-butyldiethylsilyl, tert-butyldiethylsilyl, methyldipropylsilyl, ethyldipropylsilyl, butyldipropylsilyl, sec-butyldipropylsilyl, tert-butyldipropylsilyl, methyldiisopropylsilyl, ethyldiisopropylsilyl, butyldiisopropylsilyl, sec-butyldiisopropylsilyl, tert-butyldiisopropylsilyl, and the like.

As R ²¹ ～R ²⁸ As the "tricycloalkylsilyl group" in (1), there can be mentioned groups in which three hydrogens in the silyl group are each independently substituted with a cycloalkyl group, which may be cited as said R ²¹ ～R ²⁸ The "cycloalkyl group" in (1). The cycloalkyl group preferred for substitution is a cycloalkyl group having 5 to 10 carbon atoms, and specific examples thereof include: cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, bicyclo [1.1.1]Pentyl, bicyclo [2.0.1]Pentyl, bicyclo [1.2.1]Hexyl, bicyclo [3.0.1]Hexyl, bicyclo [2.1.2]Heptyl, bicyclo [2.2.2]Octyl, adamantyl, decahydronaphthyl, decahydroazulenyl, and the like.

Specific examples of the "tricycloalkylsilyl group" include tricyclopentylsilyl group and tricyclohexylsilyl group.

As R ²¹ ～R ²⁸ The "substituted amino group" of the "amino group which may be substituted" in (1) includes, for example, an amino group in which two hydrogens are substituted with an aryl group or a heteroaryl group. The amino group with two hydrogens substituted by aryl is diaryl substituted amino, the amino group with two hydrogens substituted by heteroaryl is diheteroaryl substituted amino, and the amino group with two hydrogens substituted by aryl and heteroaryl is aryl heteroaryl substituted amino. Said aryl or heteroaryl may be cited as said R ²¹ ～R ²⁸ The "aryl" or "heteroaryl" in (1). In addition, the two aryl groups of the diaryl substituted amino group are not bonded to each other or bonded via a linking group, the two heteroaryl groups of the diheteroaryl substituted amino group are not bonded to each other or bonded via a linking group, and the aryl group and the heteroaryl group of the arylheteroaryl substituted amino group are not bonded to each other or bonded via a linking group.

Specific "substituted amino group" includes: diphenylamino, dinaphthylamino, phenylnaphthylamino, bipyrylamino, phenylpyridylamino, naphthylpyridylamino and the like.

As R ²¹ ～R ²⁸ Examples of the "halogen" in (1) include: fluorine, chlorine, bromine, iodine.

As R ²¹ ～R ²⁸ Among the groups specified, some of them may be substituted in the above-mentioned manner, and as the substituents in the above-mentioned case, there may be mentioned: alkyl, cycloalkyl, aryl or heteroaryl. The alkyl, cycloalkyl, aryl or heteroaryl group may be cited as the R ²¹ ～R ²⁸ The "alkyl", "cycloalkyl", "aryl" or "heteroaryl" in (1).

"> N-R as Y ²⁹ R in ` ²⁹ Is hydrogen or a substituted aryl group, as said aryl group, the R group can be cited ²¹ ～R ²⁸ The substituent mentioned for the "aryl" in (1) may be cited as the substituent mentioned for R ²¹ ～R ²⁸ The substituent(s) of (1).

R ²¹ ～R ²⁸ Adjacent groups in (a) may be bonded to each other to form a hydrocarbon ring, an aryl ring or a heteroaryl ring. The case where no ring is formed is as followsExamples of the group represented by the formula (A-1) include groups represented by the following formulae (A-2) to (A-14) as the group forming a ring. Further, at least one hydrogen in the group represented by any one of the formulae (A-1) to (A-14) may be substituted with an alkyl group, a cycloalkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, an arylthio group, a trialkylsilyl group, a tricycloalkylsilyl group, a dialkylcycloalkylsilyl group, an alkylbicycloalkylsilyl group, a diarylsubstituted amino group, a diheteroarylsubstituted amino group, an arylheteroaryl substituted amino group, a halogen group, a hydroxyl group, or a cyano group. In addition, the two aryl groups of the diaryl substituted amino group are not bonded to each other or bonded via a linking group, the two heteroaryl groups of the diheteroaryl substituted amino group are not bonded to each other or bonded via a linking group, and the aryl group and the heteroaryl group of the arylheteroaryl substituted amino group are not bonded to each other or bonded via a linking group.

[ chemical formula 72]

As the ring formed by bonding adjacent groups to each other, a hydrocarbon ring may be mentioned, for example, a cyclohexane ring, and as the aryl ring or heteroaryl ring, the above-mentioned R ²¹ ～R ²⁸ The ring structure illustrated in the "aryl" or "heteroaryl" in (a), the ring being formed by condensation with one or two benzene rings in the formula (a-1).

The group represented by formula (a) is a group obtained by removing 1 hydrogen from any position of formula (a), and represents the position. That is, the group represented by the formula (A) may have an arbitrary position as a bonding position. For example, the structure of formula (A) may be represented by the following formula (A) and any carbon atom on two benzene rings in the structure of formula (A), or R in the structure of formula (A) ²¹ ～R ²⁸ Wherein adjacent groups are bonded to each other to form an atom on any ring, or "> N-R" as Y in the structure of the formula (A) ²⁹ "R of ²⁹ In any position or "> N-R ²⁹ N (R) of ²⁹ A bond) directly bonded. The same applies to the groups represented by any of formulae (A-1) to (A-14).

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

Examples of the group represented by the formula (a) include the following groups. Y and x in the formula are as defined above.

[ solution 73]

[ chemical formula 74]

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

Further, all or a part of the hydrogen in the chemical structure of the anthracene compound represented by the formula (3-H) may be deuterium.

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

[ solution 75]

In the 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 、A ¹⁶ 、Ar ¹⁷ And Ar ¹⁸ Each independently is hydrogen, optionally substituted aryl, optionally substituted heteroarylA substituted diarylamino group, a substitutable diheteroarylamino group, a substitutable arylheteroarylamino group, a substitutable alkyl group, a substitutable cycloalkyl group, a substitutable alkenyl group, a substitutable alkoxy group, a substitutable aryloxy group, a substitutable arylthio group, or a substitutable silyl group, at least one hydrogen in the compound represented by formula (1) may be substituted by halogen, cyano group, or deuterium. Furthermore, the two aryl groups of the optionally substituted diarylamino group are not bonded to one another or are bonded via a linking group, the two heteroaryl groups of the optionally substituted diheteroarylamino group are not bonded to one another or are bonded via a linking group, and the aryl and heteroaryl groups of the optionally substituted arylheteroarylamino group are not bonded to one another or are bonded via a linking group.

The definition of "aryl which may be substituted", "heteroaryl which may be substituted", "diarylamino which may be substituted", "diheteroarylamino which may be 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", "arylthio which may be substituted" or "silyl which may be substituted" in the formula (3-H2) is the same as that shown in the formula (3-H), and the description in the formula (1) can be cited. Furthermore, the two aryl groups of the "optionally substituted diarylamino group" are not bonded to one another or are bonded via a linking group, the two heteroaryl groups of the "optionally substituted diheteroarylamino group" are not bonded to one another or are bonded via a linking group, and the aryl and heteroaryl groups of the "optionally substituted arylheteroarylamino group" are not bonded to one another or are bonded via a linking group.

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

[ 76]

In the formulae (3-H2-X1) to (3-H2-X7) represents a bonding site. In the formulae (3-H2-X1) to (3-H2-X3), Ar ²¹ 、Ar ²² And Ar ²³ Each independently hydrogen, phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl,

A phenyl group, a triphenylene group, a pyrenyl group, an anthracenyl group or a group represented by the formula (A). In the description of the formula (3-H2), the group represented by the formula (A) is the same as the group described in the anthracene compound represented by the formula (3-H).

In the formulae (3-H2-X4) to (3-H2-X7), Ar ²⁴ 、Ar ²⁵ 、Ar ²⁶ 、Ar ²⁷ And Ar ²⁸ Each independently is hydrogen, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, fluorenyl,

A triphenylene group, a pyrenyl group, or a group represented by the formula (A). In addition, any one or two or more hydrogens of the groups represented by the formulae (3-H2-X1) to (3-H2-X7) may be substituted with an alkyl group having 1 to 6 carbon atoms (preferably a methyl group or a tert-butyl group).

Further, preferable examples of the "aryl group which may be substituted" include those selected from the group consisting of phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, fluorenyl, and the like,

Terphenyl group (particularly m-terphenyl-5' -yl group) substituted with at least one substituent group selected from the group consisting of a triphenylene group, a pyrenyl group and a group represented by the formula (A).

The "heteroaryl group which may be substituted" may include a group represented by the formula (A). In addition, specific examples of the "aryl group which may be substituted" and the "heteroaryl group which may be substituted" include dibenzofuranyl group, naphthobenzofuranyl group, phenyl-substituted dibenzofuranyl group, and the like.

At least one hydrogen in the compound represented by formula (1) may be substituted with halogen, cyano, or deuterium. Examples of the "halogen" in the above case include: fluorine, chlorine, bromine and iodine. Particularly preferred is a compound represented by the formula (3-H2) wherein all hydrogens are replaced with deuterium.

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

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

Among the anthracene-based compounds represented by the formula (3-H2), Ar is more preferred ¹¹ ～Ar ¹⁸ Two of (a) are aryl which may be substituted or heteroaryl which may be substituted, and the other six are hydrogen, alkyl which may be substituted, cycloalkyl which may be substituted, alkenyl which may be substituted or alkoxy which may be substituted. That is, the anthracene compound represented by the formula (3-H2) more preferably has a structure in which three substituents selected from the group consisting of an optionally substituted aryl group and an optionally substituted heteroaryl group are bonded to an anthracene ring.

Among the anthracene compounds represented by the formula (3-H2), Ar is more preferable ¹¹ ～Ar ¹⁸ Any two of which are optionally substituted aryl or optionally substituted heteroaryl, and the other six of which are hydrogen, methyl or tert-butyl.

Furthermore, in the formula (3-H2), R is preferable ^c Is hydrogen, and Ar ¹¹ ～Ar ¹⁸ Any six of which are hydrogen.

The anthracene compound represented by the formula (3-H2) is preferably an anthracene compound represented by the following formula (3-H2-A), formula (3-H2-B), formula (3-H2-C), formula (3-H2-D) or formula (3-H2-E).

[ solution 77]

Formula (3-H2-A), formula (3-H2-B), formula (3-H2-C), formula (3-H2)-D) or formula (3-H2-E), Ar ^c' 、Ar ^11' 、Ar ^12' 、Ar ^13' 、Ar ^14' 、Ar ^15' 、Ar ^17' And Ar ^18' Each independently is phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, or the like,

A phenyl group, a triphenylene group, a pyrenyl group, or a group represented by the formula (A), wherein at least one hydrogen in the groups is selected from the group consisting of a phenyl group, a biphenyl group, a terphenyl group, a quaterphenyl group, a naphthyl group, a phenanthryl group, a fluorenyl group, a benzofluorenyl group, a naphthoyl group, and a,

A group represented by the formula (A). Here, when the hydrogens of the methylene groups in the fluorenyl and benzofluorenyl groups are both substituted by phenyl groups, these phenyl groups may be bonded to each other by a single bond. Not bonding Ar ^c' 、Ar ^11' 、Ar ^12' 、Ar ^13' 、Ar ^14' 、Ar ^15' 、Ar ^17' And Ar ^18' Instead of hydrogen, a methyl group or a tert-butyl group may be bonded to a carbon atom of the anthracene ring of (A).

When Ar is ^c' 、Ar ^11' 、Ar ^12' 、Ar ^13' 、Ar ^14' 、Ar ^15' 、Ar ^17' And Ar ^18' In the case of a substituted or unsubstituted phenyl group or a substituted or unsubstituted naphthyl group, respectively, the group represented by any one of the above-mentioned formulae (3-H2-X1) to (3-H2-X7) is preferable.

Ar ^c' 、Ar ^11' 、Ar ^12' 、Ar ^13' 、Ar ^14' 、Ar ^15' 、Ar ^17' And Ar ^18' More preferably, each independently represents a phenyl group, a biphenyl group (particularly, biphenyl-2-yl group or biphenyl-4-yl group), a terphenyl group (particularly, m-terphenyl-5' -yl group), a naphthyl group, a phenanthryl group, a fluorenyl group, or a group represented by any one of the formulae (A-1) to (A-4), and in this case, at least one hydrogen of these groups may be substituted by a phenyl group, a biphenyl group, a naphthyl group, a phenanthryl group, a fluorenyl group, or a group represented by any one of the formulae (A-1) to (A-4)。

In addition, at least one hydrogen in the compound represented by formula (3-H2-A), formula (3-H2-B), formula (3-H2-C), formula (3-H2-D), or formula (3-H2-E) may be substituted with halogen, cyano, or deuterium. The deuteration is preferably a method in which all the anthracyclines are deuterated or a method in which all the hydrogen atoms are deuterated.

As a particularly preferred anthracene compound represented by the formula (3-H2), an anthracene compound represented by the following formula (3-H2-Aa) can be mentioned.

[ solution 78]

In the formula (3-H2-Aa), Ar ^c' 、Ar ^14' And Ar ^15' Each independently is phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, or the like,

A phenyl group, a triphenylene group, a pyrenyl group, or a group represented by any one of the formulae (A-1) to (A-11), wherein at least one hydrogen of these groups may be a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthryl group, a fluorenyl group, a benzofluorenyl group, a naphthofluorenyl group, a phenanthryl group, a naphthofluorenyl group, or a naphthoyl group,

A triphenylene group, a pyrenyl group, or a group represented by any one of the formulae (A-1) to (A-11). Here, when the hydrogen of the methylene group in the fluorenyl group and the benzofluorenyl group is substituted by a phenyl group, the phenyl groups may be bonded to each other by a single bond. In addition, no Ar bond is formed ^c' 、Ar ^14' And Ar ^15' The carbon atom of the anthracene ring of (a) may be substituted with a methyl group or a tert-butyl group instead of hydrogen. At least one hydrogen in the compound represented by formula (3-H2-Aa) is unsubstituted or substituted with a halogen or cyano group, and at least one hydrogen in the compound represented by formula (3-H2-Aa) is substituted with deuterium.

In the formula (3-H2-Aa), Ar ^c' 、Ar ^14' And Ar ^15' Preferably phenyl, biphenyl, terphenyl, naphthylA phenanthryl group, a fluorenyl group, or a group represented by any one of the formulae (A-1) to (A-4), wherein at least one hydrogen of these groups may be substituted by a phenyl group, a naphthyl group, a phenanthryl group, a fluorenyl group, or a group represented by any one of the formulae (A-1) to (A-4).

In the compound represented by the formula (3-H2-Aa), at least the carbon bonded to the 10-position of the anthracene ring (Ar is bonded to ^c' The bonded carbon is set to be in the 9-position) is replaced 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, Ar ^c' 、Ar ^14' And Ar ^15' The same as defined in formula (1 Aa). D in the formula (1Ab) represents that at least the position is deuterium, any one or more of other hydrogens in the formula (3-H2-Aa) may be deuterium at the same time, and it is also preferable that all hydrogens in the formula (3-H2-Aa) are deuterium.

[ solution 79]

Specific examples of the anthracene compound include compounds represented by the following formulae. In the following structural formulae, "Me" represents a methyl group, "D" represents deuterium, and "tBu" represents a tert-butyl group.

[ solution 80]

[ solution 81]

[ solution 82]

[ solution 83]

[ solution 84]

[ solution 85]

[ solution 86]

[ solution 87]

Further, other specific examples of the anthracene-based compound include compounds represented by the following formulae (3-131-Y) to (3-179-Y), compounds represented by the following formulae (3-180-Y) to (3-182-Y), compounds represented by the following formulae (3-183-N), compounds represented by the following formulae (3-184-Y) to (3-254-Y), compounds represented by the following formulae (3-255-Y) to (3-269-Y), compounds represented by the following formulae (3-500) to (3-557), and compounds represented by the following formulae (3-600) to (3-620). The hydrogen atoms in the compounds represented by the following formulae (3-131-Y) to (3-179-Y), the compounds represented by the following formulae (3-180-Y) to (3-182-Y), the compounds represented by the following formulae (3-183-N), the following formulae (3-184-Y) to (3-254-Y), the formulae (3-255-Y) to (3-269-Y), the formulae (3-500) to (3-557), and the formulae (3-600) to (3-620) may be partially or completely substituted by deuterium. Wherein Y may be-O-, -S-, > N-R ²⁹ (R ²⁹ Is as defined above) or > C (-R) ³⁰ ) ₂ (R ³⁰ Is an attachable aryl, or alkyl), R ²⁹ For example, phenyl, R ³⁰ For example methyl. The formula number is, for example, when Y is O, the formula(3-131-Y) is represented by the formula (3-131-O) wherein Y is-S-or > N-R ²⁹ In the case of (2), the following formulae are given as (3-131-S) and (3-131-N), respectively.

[ solution 88]

[ solution 89]

[ solution 90]

[ solution 91]

[ chemical No. 92]

[ chemical No. 93]

[ solution 94]

[ solution 95]

[ solution 96]

[ solution 97]

[ solution 98]

[ solution 99]

[ solution 100]

[ solution 101]

[ solution 102]

[ solution 103]

[ solution 104]

[ solution 105]

[ solution 106]

Among the compounds, preferred are those of the formulae (3-131-Y) to (3-134-Y), the formulae (3-138-Y), the formulae (3-140-Y) to (3-143-Y), the formulae (3-150-Y), the formulae (3-153-Y) to (3-156-Y), the formulae (3-166-Y), the formulae (3-168-Y), the formulae (3-173-Y), the formulae (3-177-Y), the formulae (3-180-Y) to (3-183-N), the formulae (3-185-Y), the formulae (3-190-Y), the formulae (3-223-Y), the formulae (3-241-Y), the formulae (3-250-Y), A compound represented by the formula (3-252-Y) to the formula (3-254-Y), the formula (3-501), the formula (3-507), the formula (3-508), the formula (3-509), the formula (3-513), the formula (3-514), the formula (3-519), the formula (3-521), the formula (3-538) to the formula (3-547) or the formula (3-600) to the formula (3-620). In addition, Y is preferably-O-.

The anthracene compound may be a compound having a reactive group at a desired position of an anthracene skeleton as a starting material, and if the anthracene compound is an anthracene compound represented by a formula (3-H), the anthracene compound may be X, Ar ⁴ And a compound having a reactive group in a partial structure such as the structure of the formula (A) as a starting material, and produced by suzuki coupling, radicel coupling or other known coupling reaction. Examples of the reactive group of the reactive compound include halogen and boric acid. As specific production methods, for example, reference is made to: international publication No. 2014/141725 paragraph [0089]～[0175]The synthesis method of (1).

< fluorene-based Compound >

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

[ chemical No. 107]

In the formula (4-H), the compound (A),

R ¹ to R ¹⁰ Each independently of the others is hydrogen, aryl, heteroaryl (which may be bonded via a linking group to the fluorene skeleton in formula (4-H)), diarylamino (two aryl groups are not bonded to each other or may be bonded via a linking group), diheteroarylamino (two heteroaryl groups are not bonded to each other or may be bonded via a single bond or a linking group), arylheteroarylamino (aryl and heteroaryl groups are not bonded to each other or may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkenyl, alkoxy or aryloxy, at least one of which is hydrogen which is unsubstituted or substituted by aryl, heteroaryl, alkyl or cycloalkyl, or R is substituted, in addition 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 Not independently bonded to form a fused ring or spiro ring, or independently bonded to form a fused ring or spiro ring, at least one hydrogen in the formed ring being unsubstituted or bonded to an aryl group, a heteroaryl group (the heteroaryl group may be bonded to the formed ring via a linking group), a diarylamino group (the two aryl groups are not bonded to each other or bonded via a linking group), a diheteroarylamino group (the two heteroaryl groups are not bonded to each other or bonded via a single bond or a linking group), an arylheteroarylamino group (the aryl group and the heteroaryl group are not bonded to each other or may be bonded via a single bond or a linking group), an alkyl group, a cycloalkyl group, an alkenyl group, an alkoxy group, or an aryloxy group, or substituted, at least one hydrogen thereof being unsubstituted or substituted, at least one hydrogen of the compounds represented by formula (4-H) being unsubstituted or substituted with hydrogen, Cyano or deuterium substitution.

The details of each group in the definition of the formula (4-H) may be referred to the description of the polycyclic aromatic compound of the formula (1) described above.

As R ¹ To R ¹⁰ The alkenyl group in (1) includes, for example, an alkenyl group having 2 to 30 carbon atoms, preferably an alkenyl group having 2 to 20 carbon atoms, more preferably an alkenyl group having 2 to 10 carbon atoms, and further preferably an alkenyl group having 2 carbon atoms The alkenyl group having 6 carbon atoms is particularly preferably an alkenyl group having 2 to 4 carbon atoms. Preferred alkenyl groups are vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl or 5-hexenyl.

Specific examples of the heteroaryl group include a monovalent group represented by a compound of the following formula (4-Ar1), formula (4-Ar2), formula (4-Ar3), formula (4-Ar4) or formula (4-Ar5) in which any hydrogen atom is removed.

[ solution 108]

In the formulae (4-Ar1) to (4-Ar5), Y ¹ Each independently O, S or N-R, R is phenyl, biphenyl, naphthyl, anthracenyl or hydrogen, at least one hydrogen in the structures of formulae (4-Ar1) to (4-Ar5) may be substituted with phenyl, biphenyl, naphthyl, anthracenyl, phenanthryl, methyl, ethyl, propyl or butyl.

These heteroaryl groups may be bonded to the fluorene skeleton in the formula (4-H) through a linking group. That is, the fluorene skeleton in the formula (4-H) and the heteroaryl group may be bonded not only directly but also via a linking group therebetween. 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-, etc.

In addition, R in the formula (4-H) 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 Each of which may independently be bonded to form a fused ring, R ⁹ And R ¹⁰ Can bond and form a spiro ring. From R ¹ To R ⁸ The condensed ring to be formed is a ring condensed on the benzene ring in the formula (4-H), and is an aliphatic ring or an aromatic ring. An aromatic ring is preferable, and a structure containing a benzene ring in the formula (4-H) includesNaphthalene rings or phenanthrene rings, and the like. From R ⁹ And R ¹⁰ The spiro ring formed is a ring spiro-bonded to the five-membered ring in the formula (4-H), and is an aliphatic ring or an aromatic ring. Preferred is an aromatic ring, and fluorene rings and the like can be mentioned.

The compound represented by the formula (4-H) is preferably a compound represented by the following formula (4-H-1), formula (4-H-2) or formula (4-H-3), and is R in the formula (4-H) ¹ And R ² A compound formed by condensation of bonded benzene rings, R in the formula (4-H) ³ And R ⁴ A compound formed by condensation of bonded benzene rings, R in the formula (4-H) ¹ To R ⁸ Is not bonded to any of them.

[ chemical 109]

R in the formula (4-H-1), the formula (4-H-2) and the formula (4-H-3) ¹ To R ¹⁰ Is defined as R corresponding to formula (4-H) ¹ To R ¹⁰ R in the same formulae (4-H-1) and (4-H-2) ¹¹ To R ¹⁴ Is also defined as R in the formula (4) ¹ To R ¹⁰ The same is true.

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

[ solution 110]

R in the formulae (4-H-1A), (4-H-2A) and (4-H-3A) ² To R ⁷ Are defined as R corresponding to the formulae (4-H-1), (4-H-2) and (4-H-3) ² To R ⁷ Same, and R in the formula (4-H-1A) and the formula (4-H-2A) ¹¹ To R ¹⁴ Is also defined as R in the formula (4-H-1) and the formula (4-H-2) ¹¹ To R ¹⁴ The same is true.

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

More specific examples of the fluorene-based compound as a main component of the present invention include compounds represented by the following structural formulae. Further, "Me" represents a methyl group.

[ solution 111]

< dibenzo >

Series compound >

Dibenzo as host

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

[ solution 112]

In the formula (5-H), R ¹ To R ¹⁶ Independently of one another, hydrogen, aryl, heteroaryl (which may be bonded to the dibenzo of formula (5-H) via a linking group

Backbone-bonded), diarylamino (two aryl groups are not bonded to each other or can be bonded via a linking group), diheteroarylamino (two heteroaryl groups are not bonded to each other or can be bonded via a single bond or a linking group), arylheteroarylamino (aryl and heteroaryl groups are not bonded to each other or can be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkenyl, alkoxy, or aryloxy, at least one of which is hydrogen unsubstituted or substituted with aryl, heteroaryl, alkyl, or cycloalkyl, and R is additionally ¹ To R ¹⁶ Adjacent groups in (1) are not bonded to each otherThe bond forms a fused ring or is bonded to form a fused ring, at least one hydrogen in the formed ring is not substituted with an aryl group, a heteroaryl group (the heteroaryl group may be bonded to the formed ring via a linking group), a diarylamino group (two aryl groups are not bonded to each other or may be bonded via a linking group), a diheteroarylamino group (two heteroaryl groups are not bonded to each other or may be bonded via a single bond or a linking group), an arylheteroarylamino group (aryl group, heteroaryl group are not bonded to each other or may be bonded via a single bond or a linking group), an alkyl group, a cycloalkyl group, an alkenyl group, an alkoxy group, or an aryloxy group, or is substituted, at least one hydrogen thereof is not substituted with an aryl group, a heteroaryl group, an alkyl group, or a cycloalkyl group, or is substituted, and at least one hydrogen in the compound represented by formula (5-H) may be substituted with halogen, cyano, or deuterium.

The details of each group in the definition of the formula (5-H) may be referred to the description of the polycyclic aromatic compound of the formula (1) described above.

Examples of the alkenyl group in the definition of the formula (5-H) include alkenyl groups having 2 to 30 carbon atoms, preferably alkenyl groups having 2 to 20 carbon atoms, more preferably alkenyl groups having 2 to 10 carbon atoms, further preferably alkenyl groups having 2 to 6 carbon atoms, and particularly preferably alkenyl groups having 2 to 4 carbon atoms. Preferred alkenyl groups are vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl or 5-hexenyl.

Specific examples of the heteroaryl group include a monovalent group represented by a compound of the following formula (5-Ar1), formula (5-Ar2), formula (5-Ar3), formula (5-Ar4) or formula (5-Ar5) in which any one hydrogen atom is removed.

[ solution 113]

In the formulae (5-Ar1) to (5-Ar5), Y ¹ Each independently is O, S or N-R, R is phenyl, biphenyl, naphthyl, anthracenyl or hydrogen, at least one hydrogen in the structures of formulae (5-Ar1) to (5-Ar5) can be substituted by phenyl, biphenylPhenyl, naphthyl, anthryl, phenanthryl, methyl, ethyl, propyl or butyl.

These heteroaryl groups may be bonded to the dibenzo of formula (5-H) via a linking group

The skeleton is bonded. Namely, dibenzo in the formula (5-H)

The backbone and the heteroaryl group may be bonded not only directly but also via a linking group therebetween. 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-, etc.

The compound represented by the formula (5-H) is preferably R ¹ 、R ⁴ 、R ⁵ 、R ⁸ 、R ⁹ 、R ¹² 、R ¹³ And R ¹⁶ Is hydrogen. In the case, R in the formula (5-H) ² 、R ³ 、R ⁶ 、R ⁷ 、R ¹⁰ 、R ¹¹ 、R ¹⁴ And R ¹⁵ Preferably, the monovalent group is a monovalent group having a structure represented by formula (5-Ar1), formula (5-Ar2), formula (5-Ar3), formula (5-Ar4) or formula (5-Ar5) (the monovalent group having the structure may be represented by phenylene, biphenylene, naphthylene, anthrylene, methylene, ethylene, -OCH, or the like ₂ CH ₂ -、-CH ₂ CH ₂ O-, or-OCH ₂ CH ₂ O-and dibenzo in formula (5-H)

Backbone bond), methyl, ethyl, propyl, or butyl.

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 the case, R in the formula (5-H) ³ 、R ⁶ 、R ¹¹ 、R ¹⁴ At least one (preferably one or two, more preferably one) of (A) and (B) is a group having a single intervening bond, phenylene group, biphenylene group, naphthylene group, anthracenylene group, methylene group, ethylene group, -OCH group ₂ CH ₂ -、-CH ₂ CH ₂ O-or-OCH ₂ CH ₂ O-is a monovalent group having a structure represented by formula (5-Ar1), formula (5-Ar2), formula (5-Ar3), formula (5-Ar4) or formula (5-Ar5), at least one other than the monovalent group (i.e., other than the position substituted by the monovalent group having the structure) is hydrogen, phenyl, biphenyl, naphthyl, anthryl, methyl, ethyl, propyl or butyl, and at least one hydrogen of these may be substituted by phenyl, biphenyl, naphthyl, anthryl, methyl, ethyl, propyl or butyl.

In addition, R in the formula (5-H) ² 、R ³ 、R ⁶ 、R ⁷ 、R ¹⁰ 、R ¹¹ 、R ¹⁴ And R ¹⁵ In the case of selecting a monovalent group having a structure represented by formula (5-Ar1) to formula (5-Ar5), at least one hydrogen in the structure may react with R in formula (5-H) ¹ To R ¹⁶ Any of which is bonded to form a single bond.

Dibenzo as subject of the invention

More specific examples of the series of compounds include compounds represented by the following structural formulae. Further, "tBu" represents a tert-butyl group.

[ chemical formula 114]

[ solution 115]

The material for the light-emitting layer (host material and dopant material) may be used as a polymer compound obtained by polymerizing a reactive compound, which is obtained by substituting a reactive substituent in the material for the light-emitting layer (host material and dopant material), as a monomer, or as a crosslinked polymer compound thereof obtained by reacting a main chain polymer with the reactive compound, or as a suspended polymer compound obtained by substituting a reactive substituent in the material for the light-emitting layer (host material and dopant material) or as a crosslinked polymer compound thereof. As the reactive substituent in the above case, the description of the polycyclic aromatic compound represented by the formula (1) can be cited.

Luminescent layer comprising an auxiliary dopant and an emissive dopant

A light-emitting layer in an organic electroluminescent element may include a host compound as a first component, an auxiliary dopant (compound) as a second component, and an emitting dopant (compound) as a third component. The polycyclic aromatic compounds of the invention are also preferably used as emissive dopants. As the auxiliary dopant (compound), a thermally active type retardation phosphor can be used.

In the following description, an organic electroluminescent element using a Thermally active Delayed phosphor as an auxiliary dopant is sometimes referred to as a "TAF element" (Thermally active Delayed Fluorescence (TADF) assisted Fluorescence (assisted Fluorescence) element). The "host compound" in the TAF element is a compound having a lower excited singlet level determined from a shoulder on the short wavelength side of the peak of the fluorescence spectrum, which is higher than the lower excited singlet level of the thermally active retardation phosphor as the second component and the emission dopant as the third component.

The "thermally active delayed phosphor" refers to a compound that absorbs thermal energy, generates reverse intersystem crossing from a lowest excited triplet state to a lowest excited singlet state, and is radioactive-inactivated from the lowest excited singlet state, thereby being capable of emitting delayed fluorescence. The term "thermally active delayed fluorescence" includes the case where a higher-order triplet state passes through during excitation from the lowest excited triplet state to the lowest excited singlet state. Examples of this include a paper published by Monkman (Monkman) et al of the university of Durham (Durham) (Nature-COMMUNICATIONS), 7: 13680, digital object unique identifier (DOI) 10.1038/ncomms13680), a paper published by Beebel et al of the institute of Industrial and technology (Hosokai et al), Scientific Advances (Science Advances, Sci. Adv.)2017, 3: e1603282), a paper published by Zodiac et al of the university of Kyoto (Scientific Reports, 7: 4820, DOI 10.1038/s41598-017 07-7), and a paper published by Zodiac et al of the university of Kyoto (Nutgaric report, BNia publication in the New Yokogaku Kogyo (Kogyo et al, No. 2: 2I 41598-017-7), a paper published by Zodiac et al of the university of the Japan society of the Japan (Durham 98, No. 2: 2I4-15, Biocal boron used as a luminescence mechanism in Anthracene luminescence, Anthracene molecular luminescence, Takara, Bioluminescence mechanism, kyoto university college engineering research department), and the like. In the present invention, regarding a sample containing a target compound, the target compound is judged to be a "thermally active type delayed phosphor" from the fact that a slow fluorescence component is observed when the fluorescence lifetime is measured at 300K. The slow fluorescence component herein refers to a component having a fluorescence lifetime of 0.1 μ sec or more. The fluorescence lifetime can be measured, for example, using a fluorescence lifetime measuring apparatus (manufactured by Hamamatsu Photonics, Inc., C11367-01).

The polycyclic aromatic compound of the present invention can function as an emitting dopant, and the "thermally active retardation phosphor" can function as an auxiliary dopant for assisting the 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 element using a general fluorescent dopant for an Emitting Dopant (ED). In the figure, the energy level of the ground state of the host is E (1, G), the lowest excited singlet state energy level of the host obtained from the shoulder on the short-wavelength side of the fluorescence spectrum is E (1, S, Sh), the lowest excited triplet state energy level of the host obtained from the shoulder on the short-wavelength side of the phosphorescence spectrum is E (1, T, Sh), the energy level of the ground state of the auxiliary dopant as the second component is E (2, G), the lowest excited singlet state energy level of the auxiliary dopant as the second component obtained from the shoulder on the short-wavelength side of the fluorescence spectrum is E (2, S, Sh), the lowest excited triplet state energy level of the auxiliary dopant as the second component obtained from the shoulder on the short-wavelength side of the phosphorescence spectrum is E (2, T, Sh), the energy level of the ground state of the emissive dopant as the third component is E (3, G), and the lowest excited singlet state energy level of the emissive dopant as the third component obtained from the shoulder on the short-wavelength side of the fluorescence spectrum is E (2, T, Sh) E (3, S, Sh), the lowest excited triplet level determined from the shoulder at the short wavelength side of the phosphorescence spectrum of the emission dopant as the third component, E (3, T, Sh), h + for holes, E-for electrons, and FRET (fluorescence Resonance Energy transfer). In the TAF device, when a general fluorescent dopant is used as the Emitting Dopant (ED), the energy of Up-Conversion (Up Conversion) from the auxiliary dopant is transferred to the lowest excited singlet level E (3, S, Sh) of the emitting dopant, and light is emitted. However, a part of the lowest excited triplet level E (2, T, Sh) on the auxiliary dopant moves to the lowest excited triplet level E (3, T, Sh) of the emitting dopant, or intersystem crossing from the lowest excited singlet level E (3, S, Sh) to the lowest excited triplet level E (3, T, Sh) occurs on the emitting dopant, followed by thermal deactivation to the ground state E (3, G). Due to the path, a part of the energy is not used for light emission, and waste of energy occurs.

In contrast, in the organic electroluminescent element according to this embodiment, energy efficiency in moving from the auxiliary dopant to the emitting dopant can be used for light emission, and thus high light emission efficiency can be achieved. The reason for this is presumed to be the following light emission mechanism.

Fig. 3 shows a preferable energy relationship in the organic electroluminescent element according to the present embodiment. In the organic electroluminescent element according to the present embodiment, the compound having a boron atom as an emission dopant has a high lowest excited triplet level E (3, T, Sh). Therefore, in the case where the lowest excited singlet energy up-converted by the auxiliary dopant is intersystem crossing to the lowest excited triplet level E (3, T, Sh), for example, by the emitting dopant, the lowest excited triplet level E (2, T, Sh) on the emitting dopant is up-converted or recovered to the auxiliary dopant (thermally active type delayed phosphor). Therefore, the generated excitation energy can be used for light emission without waste. Further, it is expected that by assigning the functions of up-conversion and light emission to two kinds of molecules whose respective functions are highlighted, the retention time of high energy is reduced, and the load on the compound is reduced.

In the present embodiment, as the main compound, a known compound can be used, and examples thereof include a compound having at least one of a carbazole ring and a furan ring, and among them, a compound in which at least one of a furyl group and a carbazole group is bonded to at least one of an arylene group and a heteroarylene group is preferably used. Specific examples thereof include mCP and mCBP.

From the viewpoint of promoting but not inhibiting the generation of Thermally Active Delayed Fluorescence (TADF) in the light-emitting layer, the lowest excited triplet level E (1, T, Sh) of the host compound determined from the shoulder on the short wavelength side of the peak of the phosphorescence spectrum is preferably higher than the lowest excited triplet levels E (2, T, Sh) and E (3, T, Sh) of the emitting dopant or the assist dopant having the highest lowest excited triplet level in the light-emitting layer, and specifically, the lowest excited triplet level E (1, T, Sh) of the host compound is preferably 0.01eV or more, more preferably 0.03eV or more, and still more preferably 0.1eV or more, as compared with E (2, T, Sh) and E (3, T, Sh). In addition, a compound having TADF activity may also be used as the host compound.

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

< thermally active type delayed phosphor (auxiliary dopant) >)

The thermally active retardation phosphor (TADF compound) used in the TAF element is preferably a donor-acceptor type thermally active retardation phosphor (D-a type TADF compound) as follows: it is designed to localize the Highest Occupied Molecular Orbital (HOMO) and the Lowest Unoccupied Molecular Orbital (LUMO) within a molecule using an electron donating substituent called donor and an electron accepting substituent called acceptor to produce efficient reverse interbody crossing. Here, in the present specification, the "electron donating substituent" (donor) refers to a substituent and a partial structure locally existing in the HOMO orbital of the molecule of the thermally active retardation phosphor, and the "electron accepting substituent" (acceptor) refers to a substituent and a partial structure locally existing in the LUMO orbital of the molecule of the thermally active retardation phosphor.

In general, a thermally active retardation phosphor using a donor or acceptor has a large Spin Orbit Coupling (SOC) and a small exchange interaction between HOMO and LUMO, and a small Δ E (ST) due to its structure, and thus can obtain a very fast reverse intersystem crossing rate. On the other hand, a thermally active type delayed phosphor using a donor or an acceptor has a large structural relaxation in an excited state (in a molecule, since a stable structure is different between a ground state and an excited state, when a transition from the ground state to the excited state occurs by an external stimulus, the structure is changed to the stable structure in the excited state thereafter), and provides a broad emission spectrum, and thus when used as a light emitting material, there is a possibility that the color purity is lowered.

As the thermally active type retardation phosphor in the TAF device, for example, a compound in which a donor and an acceptor are bonded directly or via a spacer can be used. As the electron donating group (structure of donor) and the electron accepting group (structure of acceptor) used in the thermally active retardation phosphor of the present invention, for example, the structures described in Chemistry of Materials, 2017, 29, 1946-1963 can be used. Examples of the structure of the applicator include: carbazole, dimethylcarbazole, di-tert-butylcarbazole, dimethoxycarbazole, tetramethylcarbazole, benzofluorocarbazole, benzothienocarbazole, phenylindolinocarbazole, phenylbicarbazole, bicarbazole, tercarbazole (tercarbazole), diphenylcarbazolyamine, tetraphenylcarbazolylamine, phenoxazine, dihydrophenazine, phenothiazine, dimethyldihydroacridine, diphenylamine, bis (tert-butylphenyl) amine, N1- (4- (diphenylamino) phenyl) -N4, N4-diphenylbenzene-1, 4-diamine, dimethyltetraphenyldihydroacridine diamine, tetramethyl-dihydro-indenocridine, and diphenyl-dihydrodibenzoazasilaline, and the like. Examples of acceptor structures include: sulfonylbenzophenones, benzophenones, phenylenebis (phenylmethanone), benzonitrile, isonicotinonitrile, phthalonitrile, isophthalonitrile, terephthalonitrile, benzenetricarboxylonitrile, triazole, oxazole, thiadiazole, benzothiazole, benzobis (thiazole), benzoxazole, benzobis (oxazole), quinoline, benzimidazole, dibenzoquinoline, heptaazaphenalene, thioxanthone dioxide, dimethylanthrone, anthracenedione, 5H-cyclohepta [1,2-b:5,4-b' ] bipyridine, fluorenedicarbonitrile, triphenyltriazine, pyrazinedicarboxonitrile, pyrimidine, phenylpyrimidine, methylpyrimidine, pyridinedicarbonitrile, dibenzoquinoxalinedicarbonitrile, bis (phenylsulfonyl) benzene, dimethylthioxanthene dioxide, thianthrene tetraoxide and tris (dimethylphenyl) borane. In particular, the compound having a thermally active delayed fluorescence in the TAF element is preferably a compound having at least one selected from carbazole, phenoxazine, acridine, triazine, pyrimidine, pyrazine, thioxanthene, benzonitrile, phthalonitrile, isophthalonitrile, diphenylsulfone, triazole, oxadiazole, thiadiazole, and benzophenone as a partial structure.

The compound used as the second component of the light-emitting layer in the TAF device is a thermally active retardation phosphor, and is preferably a compound having an emission spectrum at least partially overlapping with an absorption peak of the emitting dopant. Hereinafter, a compound which can be used as a second component (a thermally active retardation phosphor) of a light-emitting layer in a TAF device is exemplified. However, the compounds that can be used as the thermally active retardation phosphors in the TAF device are not to be construed as being limited to the following exemplified compounds. In the following formula, Me represents a methyl group, t-Bu represents a tert-butyl group, and the wavy line represents a bonding position.

[ solution 116]

[ solution 117]

[ chemical formula 118]

[ solution 119]

[ chemical formula 120]

Further, as the thermally active retardation phosphor, a compound represented by any one of the following formulae (AD1), (AD2) and (AD3) may be used.

[ solution 121]

In the formulas (AD1), (AD2) and (AD3), M is independently a single bond, -O-, > N-Ar or > CAr ₂ From the viewpoint of the depth of HOMO of the partial structure to be formed and the heights of the lowest excited singlet level and the lowest excited triplet level, a single bond, -O-, or > N-Ar is preferable. J is a spacer structure for separating a donor partial structure from a receptor partial structure, and is each independently an arylene group having 6 to 18 carbon atoms, and preferably an arylene group having 6 to 12 carbon atoms from the viewpoint of the size of a conjugate exuded between the donor partial structure and the receptor partial structure. More specifically, phenylene, methylphenylene and dimethylphenylene are mentioned. Each Q is independently ═ C (-H) -or ═ N-, and in terms of the shallowness of LUMO of the partial structure formed and the heights of the lowest excited singlet level and the lowest excited triplet level, it is preferably ═ N-. Ar is independently hydrogen, aryl with 6-24 carbon atoms, heteroaryl with 2-24 carbon atoms, alkyl with 1-12 carbon atoms or cycloalkyl with 3-18 carbon atoms, and the depth and the lowest excitation unit of HOMO of the formed partial structure From the viewpoint of the height of the singlet level and the lowest excited triplet level, hydrogen, aryl having 6 to 12 carbon atoms, heteroaryl having 2 to 14 carbon atoms, alkyl having 1 to 4 carbon atoms, or cycloalkyl having 6 to 10 carbon atoms is preferred, and hydrogen, phenyl, tolyl, xylyl, mesityl, biphenyl, pyridyl, bipyridyl, triazinyl, carbazolyl, dimethylcarbazolyl, di-tert-butylcarbazolyl, benzimidazolyl, or phenylbenzimidazolyl is more preferred, and hydrogen, phenyl, or carbazolyl is still more preferred. m is 1 or 2. n is an integer of from (6-m) to (6-m), and preferably an integer of from 4 to (6-m) from the viewpoint of steric hindrance. Further, at least one hydrogen in the compounds represented by each of the formulae may be substituted by halogen or deuterium.

More specifically, the compound used as the second component of the present embodiment is preferably 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, spiro AC-TRZ, Ac-HPM, Ac-PPM, Ac-MPM, TCzTrz, TmCzTrz, and DCzmCZTrz.

The compound used as the second component of the present embodiment may be a donor-acceptor type TADF compound represented by D-a in which one donor D is directly bonded to one acceptor a or bonded via a linking group, and a compound having a structure represented by the following formula (DAD1) in which a plurality of donors D are directly bonded or bonded to one acceptor a via a linking group is preferable because it is a compound having more excellent characteristics of an organic electroluminescent element.

(D ¹ -L ¹ )n-A ¹ (DAD1)

The formula (DAD1) includes a compound represented by the following formula (DAD 2).

D ² -L ² -A ² -L ³ -D ³ (DAD2)

In the formulae (DAD1) and (DAD2), D ¹ 、D ² And D ³ Each independently represents a donor group. As the donor group, a structure of the donor can be used. A. the ¹ And A ² Each independently represents a receptor group. The acceptor group may be a structure of the acceptor. L is ¹ 、L ² And L ³ Are respectively provided withIndependently represents a single bond or a conjugated linking group. The conjugated linking group has a spacer structure for separating the donor group and the acceptor group, and is preferably an arylene group having 6 to 18 carbon atoms, and more preferably an arylene group having 6 to 12 carbon atoms. L is ¹ 、L ² And L ³ Further, it is preferably phenylene, methylphenylene or dimethylphenylene each independently. N in the formula (DAD1) is 2 or more and represents an integer of not more than the maximum number of substitutions of a 1. n is selected from the range of 2 to 10, or from the range of 2 to 6. When n is 2, the compound is represented by formula (DAD 2). n number of D ¹ Identical or different, n L ¹ May be the same or different. Preferred examples of the compounds represented by the formulae (DAD1) and (DAD2) include 2PXZ-TAZ and the following compounds, and the second component employable in the present invention is not limited to these compounds.

[ chemical formula 122]

In this embodiment mode, the light-emitting layer may be a single layer or may include a plurality of layers. The host compound, the thermally active retardation phosphor, and the polycyclic aromatic compound of the present invention may be contained in the same layer, or may contain at least one component in each of a plurality of layers. The host compound, the thermally active retardation phosphor, and the polycyclic aromatic compound of the present invention contained in the light-emitting layer may be one kind or a combination of plural kinds. The auxiliary dopant and the emission dopant may be included in the entirety of the host compound as the host, or may be included in a portion of the host compound as the host. The light-emitting layer doped with the assist dopant and the emission dopant can be formed by a method in which a host compound, an assist dopant, and an emission dopant are formed into a film by a ternary co-evaporation method; a method of simultaneously vapor-depositing a host compound, an auxiliary dopant and an emitting dopant after they are mixed in advance; and a wet film-forming method for applying a light-emitting layer-forming composition (coating material) prepared by dissolving a host compound, an auxiliary dopant, and an emission dopant in an organic solvent.

The amount of the host compound to be used varies depending on the kind of the host compound, and may be determined according to the characteristics of the host compound. The amount of the host compound used is preferably 40 to 99.999 mass%, more preferably 50 to 99.99 mass%, and still more preferably 60 to 99.9 mass%, based on the total mass of the light-emitting layer material. Within the above range, the dopant is preferably used, for example, in terms of efficient charge transport and efficient energy transfer to the dopant.

The amount of the auxiliary dopant (thermally active retardation phosphor) used varies depending on the kind of the auxiliary dopant, and may be determined depending on the characteristics of the auxiliary dopant. The amount of the auxiliary dopant used is preferably 1 to 60 mass%, more preferably 2 to 50 mass%, and still more preferably 5 to 30 mass% of the entire material for the light-emitting layer. In the above range, it is preferable, for example, in terms of efficiently transferring energy to the emitting dopant.

The amount of the emitting dopant (compound having a boron atom) used varies depending on the kind of the emitting dopant, and may be determined according to the characteristics of the emitting dopant. The amount of the emitting dopant used is preferably 0.001 to 30% by mass, more preferably 0.01 to 20% by mass, and still more preferably 0.1 to 10% by mass of the entire material for the light-emitting layer. The above range is preferable, for example, in terms of preventing the concentration quenching phenomenon.

In terms of preventing the concentration quenching phenomenon, it is preferable that the amount of the emitting dopant used is low. In terms of the efficiency of the thermally active delayed fluorescence mechanism, it is preferable that the amount of the auxiliary dopant used be high. Further, in terms of the efficiency of the thermally active delayed fluorescence mechanism of the auxiliary dopant, it is preferable that the amount of the emitting dopant used is lower than the amount of the auxiliary dopant used.

2-1-3. substrate in organic electroluminescent element

The substrate 101 is a support for the organic EL element 100, and quartz, glass, or gold is usually usedMetal, plastic, etc. The substrate 101 is formed in a plate shape, a film shape, or a sheet shape according to the purpose, and for example, a glass plate, a metal foil, a plastic film, a plastic sheet, or the like can be used. Among them, a glass plate and a plate made of a transparent synthetic resin such as polyester, polymethacrylate, polycarbonate, polysulfone are preferable. In the case of a glass substrate, soda-lime glass, alkali-free glass, or the like can be used, and the thickness is sufficient to maintain mechanical strength, and therefore, for example, it is sufficient if the thickness is 0.2mm or more. The upper limit of the thickness is, for example, 2mm or less, preferably 1mm or less. The material of the glass is preferably alkali-free glass because it is preferable that the amount of eluted ions from the glass is small, and SiO is added ₂ Etc. of barrier coating (barrier coat) are also commercially available, and therefore the soda-lime glass can be used. In addition, in order to improve the gas barrier property, a gas barrier film such as a fine silicon oxide film may be provided on at least one surface of the substrate 101, and when a synthetic resin plate, film or sheet having low gas barrier property is used as the substrate 101, it is particularly preferable to provide a gas barrier film.

2-1-4 anode in organic electroluminescent element

The anode 102 functions to inject holes into the light-emitting layer 105. Further, when the hole injection layer 103 and/or the hole transport layer 104 are provided between the anode 102 and the light-emitting layer 105, holes are injected into the light-emitting layer 105 via these layers.

As a material for forming the anode 102, an inorganic compound and an organic compound can be cited. 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.), metal halides (copper iodide, etc.), copper sulfide, carbon black, ITO glass, or NESA glass, etc. Examples of the organic compound include: polythiophene such as poly (3-methylthiophene), and conductive polymer such as polypyrrole and polyaniline. Further, the organic EL element can be used by being appropriately selected from substances used as an anode of the organic EL 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 in terms of power consumption of the light-emitting element. For example, an ITO substrate of 300. omega./□ or less functions as an element electrode, but a substrate of about 10. omega./□ can be provided at present, and therefore, a low-resistance product of, for example, 100. omega./□ to 5. omega./□, preferably 50. omega./□ to 5. omega./□, is particularly preferably used. The thickness of ITO can be arbitrarily selected depending on the resistance value, but usually 50nm to 300nm is used in many cases.

2-1-5 hole injection layer and hole transport layer in organic electroluminescent element

The hole injection layer 103 functions to efficiently inject holes transferred from the anode 102 into the light-emitting layer 105 or the hole transport layer 104. The hole transport layer 104 functions 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. The hole injection layer 103 and the hole transport layer 104 are formed by laminating and mixing one or more kinds of hole injection/transport materials, or are formed by mixing a hole injection/transport material and a polymer binder. Further, an inorganic salt such as iron (III) chloride may be added to the hole injecting/transporting material to form a layer.

The hole injecting/transporting substance needs to efficiently inject/transport holes from the positive electrode between electrodes to which an electric field is applied, and it is desirable that the hole injecting efficiency is high and the injected holes are efficiently transported. Therefore, a substance which has a small ionization potential, a large hole mobility, and excellent stability and in which impurities which become traps are not easily generated at the time of production or use is preferable.

As the material for forming the hole injection layer 103 and the hole transport layer 104, any compound can be selected from compounds conventionally used as charge transport materials for holes in photoconductive materials, p-type semiconductors, and known compounds used in hole injection layers and hole transport layers of organic EL devices. Specific examples of these compounds include carbazole derivatives (e.g., N-phenylcarbazole, polyvinylcarbazole, etc.), biscarbazole derivatives (e.g., bis (N-arylcarbazole) or bis (N-alkylcarbazole), bis (carbazole) derivatives,Triarylamine derivatives (4,4 '-tris (N-carbazolyl) triphenylamine, polymers having an aromatic tertiary amino group in the main chain or side chain, 1-bis (4-di-p-tolylaminophenyl) cyclohexane, N' -diphenyl-N, N '-bis (3-methylphenyl) -4,4' -diaminobiphenyl, N '-diphenyl-N, N' -dinaphthyl-4, 4 '-diaminobiphenyl, N' -diphenyl-N, N '-bis (3-methylphenyl) -4,4' -diphenyl-1, 1 '-diamine, N' -dinaphthyl-N, N '-diphenyl-4, 4' -diphenyl-1, 1' -diamine, N ⁴ ,N ^4' -diphenyl-N ⁴ ,N ^4' -bis (9-phenyl-9H-carbazol-3-yl) - [1,1' -biphenyl]4,4' -diamine, N ⁴ ,N ⁴ ,N ^4' ,N ^4' -tetrakis [1,1' -biphenyl]-4-yl- [1,1' -biphenyl]Triphenylamine derivatives such as-4, 4 '-diamine, 4',4 ″ -tris (3-methylphenyl (phenyl) amino) triphenylamine, starburst amine derivatives, and the like), stilbene derivatives, phthalocyanine derivatives (metal-free, copper phthalocyanine, and the like), pyrazoline derivatives, hydrazone-based compounds, benzofuran derivatives or thiophene derivatives, oxadiazole derivatives, quinoxaline derivatives (for example, 1,4,5,8,9, 12-hexaazatriphenylene-2, 3,6,7,10, 11-hexacarbonitrile, and the like), heterocyclic compounds such as porphyrin derivatives, polysilanes, and the like. In the polymer system, polycarbonate or styrene derivative, polyvinylcarbazole, polysilane, or the like having the monomer in the side chain is preferable, but there is no particular limitation as long as it is a compound which forms a thin film necessary for manufacturing a light-emitting element, can inject holes from an anode, and can transport holes.

Further, it is also known that the conductivity of an organic semiconductor is strongly affected by doping. Such an organic semiconductor matrix material contains a compound having a good electron donating property or a compound having a good electron accepting property. For the doping of electron-donating substances, strong electron acceptors such as Tetracyanoquinodimethane (TCNQ) or 2,3,5, 6-tetrafluorotetracyanoquinodimethane (2,3,5, 6-tetrafluorolotetracynano-1, 4-benzoquinodimethane (2,3,5, 6-tetrafluoro-1, 4-benzoquinodimethane, F4TCNQ) are known (see, for example, documents "m. faffy, a. bayer, t. frietz, k. rio (m.pfeiffer, a.beyer, t.fritz, k.leo)," applied physics article (app. phys.lett.), 73- (22), 3202-4 (1998) "and documents" j. bulovertz, m. faffy, t. friez, k. litt. pff.731, p. teff, k.73-k., "applied physics article" (app. k.3, p.p.), "applied physics article"). They generate so-called holes by an electron transfer process in an electron-donating base substance (hole-transporting substance). The conductivity of the base material varies considerably depending on the number and mobility of holes. As a matrix material having a hole transporting property, for example, a benzidine derivative (N, N ' -bis (3-methylphenyl) -N, N ' -bis (phenyl) benzidine, TPD) or a starburst amine derivative (4,4',4 ″ -tris (N, N-diphenylamino) triphenylamine, TDATA) or a specific metal phthalocyanine (particularly zinc phthalocyanine (ZnPc)) is known (japanese patent laid-open No. 2005-167175). The polycyclic aromatic compound of the present invention can also 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 element

An electron blocking layer for preventing diffusion of electrons from the light-emitting layer may be provided between the hole injection/transport layer and the light-emitting layer. The electron blocking layer may be formed using a compound represented by any one of the formulae (H1), (H2), and (H3). The polycyclic aromatic compound of the present invention is useful as a material for forming an electron blocking layer.

< Electron injection layer, Electron transport layer in organic electroluminescent element >

The electron injection layer 107 functions to efficiently inject electrons transferred from the cathode 108 into the light-emitting layer 105 or the electron transport layer 106. The electron transport layer 106 functions 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 transporting layer 106 and the electron injecting layer 107 are formed by laminating and mixing one or more kinds of electron transporting/injecting materials, or are formed by mixing an electron transporting/injecting material and a polymer binder.

The electron injection/transport layer is a layer that is responsible for injecting electrons from the cathode and transporting the electrons, and is preferably a layer that has high electron injection efficiency and transports the injected electrons with good efficiency. Therefore, a substance having a high electron affinity, a high electron mobility, and excellent stability is preferable, and impurities that become traps are less likely to be generated during production and use. However, when the balance between the transport of holes and electrons is considered, if the effect of efficiently preventing holes from the anode from flowing to the cathode side without being recombined is mainly exerted, the effect of improving the light emission efficiency is obtained as in the case of a material having a high electron transport ability even if the electron transport ability is not so high. Therefore, the electron injection/transport layer in this embodiment mode may also include a function of a layer capable of efficiently preventing hole transfer.

The material (electron transport material) for forming the electron transport layer 106 or the electron injection layer 107 can be selected and used as desired from compounds conventionally used as electron transport compounds in photoconductive materials, and known compounds used for electron injection layers and electron transport layers of organic EL devices.

The material used for the electron transport layer or the electron injection layer preferably contains at least one compound selected from the following compounds: a compound containing an aromatic ring or a heteroaromatic ring containing at least one atom selected from carbon, hydrogen, oxygen, sulfur, silicon, and phosphorus; pyrrole derivatives and fused ring derivatives thereof; and a metal complex having electron-accepting nitrogen. Specifically, there may be mentioned: fused ring aromatic ring derivatives such as naphthalene and anthracene, styrene aromatic ring derivatives represented by 4,4' -bis (diphenylvinyl) biphenyl, perinone derivatives, coumarin derivatives, naphthalimide derivatives, 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: and hydroxyoxazole complexes such as hydroxyphenyl oxazole complexes, azomethine complexes, tropolone metal complexes, flavonol metal complexes, and benzoquinoline metal complexes. These materials may be used alone or in combination with different materials.

Specific examples of the other electron transport compound include: 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-tert-butylphenyl) 1,3, 4-oxadiazolyl ] phenylene, etc.), thiophene derivatives, triazole derivatives (N-naphthyl-2, 5-diphenyl-1, 3, 4-triazole, etc.), thiadiazole derivatives, metal complexes of 8-hydroxyquinoline (oxine) derivatives, hydroxyquinoline metal complexes, quinoxaline derivatives, polymers of quinoxaline derivatives, indole (benzazole) compounds, gallium complexes, pyrazole derivatives, perfluorinated phenylene derivatives, etc, Triazine derivatives, pyrazine derivatives, benzoquinoline derivatives (e.g., 2 '-bis (benzo [ h ] quinolin-2-yl) -9,9' -spirobifluorene), imidazopyridine derivatives, borane derivatives, benzimidazole derivatives (e.g., tris (N-phenylbenzimidazol-2-yl) benzene), benzoxazole derivatives, thiazole derivatives, benzothiazole derivatives, quinoline derivatives, terpyridine and other oligopyridine derivatives, bipyridine derivatives, terpyridine derivatives (e.g., 1, 3-bis (2,2 ': 6',2 '-terpyridin-4' -yl) benzene), naphthyridine derivatives (e.g., bis (1-naphthyl) -4- (1, 8-naphthyridin-2-yl) phenylphosphine oxide), aldazine derivatives, and the like, Pyrimidine derivatives, arylnitrile derivatives, indole derivatives, phosphine oxide derivatives, bisstyryl derivatives, silole derivatives, oxazoline derivatives, and the like.

In addition, a metal complex having electron-accepting nitrogen may also be used, and examples thereof include: hydroxyoxazole complexes such as hydroxyquinoline metal complexes and hydroxyphenyl oxazole complexes, azomethine complexes, tropolone metal complexes, flavonol metal complexes, and benzoquinoline metal complexes.

The materials can be used alone or in admixture with different materials.

Among the above materials, preferred are borane derivatives, pyridine derivatives, fluoranthene derivatives, BO derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, arylnitrile derivatives, triazine derivatives, benzimidazole derivatives, phenanthroline derivatives, hydroxyquinoline metal complexes, thiazole derivatives, benzothiazole derivatives, thiaole derivatives, and oxazoline derivatives.

The polycyclic aromatic compound of the present invention can also 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 a material forming the electron transport layer or the electron injection layer. As the reducing substance, various substances can be used as long as they have a certain reducing property, and for example, at least one selected from the group consisting of alkali metals, alkaline earth metals, rare earth metals, oxides of alkali metals, halides of alkali metals, oxides of alkaline earth metals, halides of alkaline earth metals, oxides of rare earth metals, halides of rare earth metals, organic complexes of alkali metals, organic complexes of alkaline earth metals, and organic complexes of rare earth metals can be preferably used.

Preferable reducing substances include alkali metals such as Na (work function 2.36eV), K (work function 2.28eV), Rb (work function 2.16eV), and Cs (work function 1.95eV), and alkaline earth metals such as Ca (work function 2.9eV), Sr (work function 2.0 to 2.5eV), and Ba (work function 2.52eV), and particularly preferable substances have a work function of 2.9eV or less. Among these, K, Rb or Cs as an alkali metal is more preferable as the reducing substance, Rb or Cs is more preferable, and Cs is most preferable. These alkali metals have particularly high reducing power, and by adding a relatively small amount of the alkali metals to a material forming the electron transporting layer or the electron injecting layer, improvement in light emission luminance or prolongation in life in the organic EL element can be achieved. In addition, as the reducing substance having a work function of 2.9eV or less, a combination of two or more of these alkali metals is also preferable, and a combination including Cs, for example, a combination of Cs and Na, Cs and K, Cs and Rb, or Cs and Na and K is particularly preferable. By including Cs, the reducing ability can be efficiently exerted, and by adding Cs to a material for forming an electron transporting layer or an electron injecting layer, improvement in light emission luminance or prolongation in life of the organic EL element can be achieved.

In addition, one or more organic layers such as a cap layer having various functions according to the characteristics of the organic electroluminescent element may be included.

< cathode in organic electroluminescent element >

The cathode 108 functions to inject electrons into the light-emitting layer 105 through the electron injection layer 107 and the electron transport layer 106.

The material forming the cathode 108 is not particularly limited as long as it can efficiently inject electrons into the organic layer, and the same material as the material 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, and alloys thereof (e.g., magnesium-silver alloys, magnesium-indium alloys, and aluminum-lithium alloys such as lithium fluoride and aluminum) are preferable. In order to improve the electron injection efficiency to improve the element characteristics, lithium, sodium, potassium, cesium, calcium, magnesium, or an alloy containing these low work function metals is effective. However, in general, these low work function metals are most often unstable in the atmosphere. In order to improve this, for example, a method of doping a minute amount of lithium, cesium, or magnesium into an organic layer and using an electrode having high stability is known. As other dopants, inorganic salts such as lithium fluoride, cesium fluoride, lithium oxide, and cesium oxide can also be used. However, the present invention is not limited to these examples.

Further, the following are preferable examples: metals such as platinum, gold, silver, copper, iron, tin, aluminum, and indium, alloys using these metals, inorganic substances such as silicon dioxide, titanium dioxide, and silicon nitride, polyvinyl alcohol, vinyl chloride, hydrocarbon-based polymer compounds, and the like are laminated to protect the electrodes. The method of manufacturing these electrodes is not particularly limited as long as conduction can be achieved by resistance heating, electron beam evaporation, sputtering, ion plating, coating, or the like.

< Binders usable in the layers >

The materials used for the hole injection layer, the hole transport layer, the light emitting layer, the electron transport layer, and the electron injection layer may be formed individually, or may be dispersed in a solvent-soluble resin such as polyvinyl chloride, polycarbonate, polystyrene, poly (N-vinylcarbazole), polymethyl methacrylate, polybutyl methacrylate, polyester, polysulfone, polyphenylene oxide, polybutadiene, a hydrocarbon resin, a ketone resin, a phenoxy resin, polyamide, ethyl cellulose, a vinyl acetate resin, an Acrylonitrile-Butadiene-Styrene (ABS) resin, or a polyurethane resin as a polymer binder, or a curable resin such as phenol resin, xylene resin, petroleum resin, urea resin, melamine resin, unsaturated polyester resin, alkyd resin, epoxy resin, or silicone resin.

< 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 element 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 contains a polycyclic aromatic compound (or a polymer compound thereof) as a first component, at least one host material as a second component, and at least one organic solvent as a third component. The first component functions as a dopant component of the light-emitting layer obtained from the composition, and the second component functions as a host component of the light-emitting layer. The third component acts as a solvent for dissolving the first component and the second component in the composition, and gives a smooth and uniform surface shape by controlling the evaporation rate of the third component itself at the time of application.

< organic solvent >

The composition for forming an organic layer contains at least one organic solvent. The film forming property, the presence or absence of defects in the film, the surface roughness, and the smoothness can be controlled and improved by controlling the evaporation rate of the organic solvent during film formation. In addition, in the film formation by the ink jet method, the stability of the meniscus at the pinhole of the ink jet head can be controlled to control and improve the ejection property. In addition, by controlling the drying rate of the film and the orientation of the derivative molecules, the electrical characteristics, light emission characteristics, efficiency, and lifetime of an organic EL device having an organic layer obtained from the organic layer forming composition can be improved.

(1) Physical Properties of organic solvent

The boiling point of the at least one organic solvent is 130 to 300 ℃, more preferably 140 to 270 ℃, and still more preferably 150 to 250 ℃. From the viewpoint of the ejection property of the inkjet, the boiling point is preferably higher than 130 ℃. In addition, from the viewpoint of defects, surface roughness, residual solvent and smoothness of the coating film, the boiling point is preferably less than 300 ℃. The organic solvent is more preferably a composition containing two or more kinds of organic solvents from the viewpoint of good ejection properties, film-forming properties, smoothness and low residual solvent of the inkjet. On the other hand, the composition may be a solid state obtained by removing the solvent from the composition for forming an organic layer, in consideration of the transportability and the like, depending on the case.

The organic solvent further contains at least one of a Good Solvent (GS) and a Poor Solvent (PS) with respect to the solute, and the Boiling Point (BP) of the Good Solvent (GS) is particularly preferred _GS ) Boiling Point (BP) of Poor Solvent (PS) _PS ) Low in composition.

By adding the poor solvent with high boiling point, the good solvent with low boiling point volatilizes first during film forming, the concentration of the content in the composition and the concentration of the poor solvent are increased, and the rapid film forming is promoted. As a result, a coating film having few defects, small surface roughness, and high smoothness is obtained.

Difference in solubility (S) _GS -S _PS ) Preferably 1% or more, more preferably 3% or more, and still more preferably 5% or more. Difference in Boiling Point (BP) _PS -BP _GS ) Preferably 10 ℃ or higher, more preferably 30 ℃ or higher, and still more preferably 50 ℃ or higher.

The organic solvent is removed from the coating film by a drying step such as vacuum, reduced pressure, or heating after film formation. In the case of heating, it is preferable to perform the heating under the condition that the glass transition temperature (Tg) of at least one of the solutes is +30 ℃ or lower, from the viewpoint of improving the coating film formability. From the viewpoint of reducing the residual solvent, it is preferable to heat at least one solute at a glass transition temperature (Tg) of-30 ℃ or higher. Even if the heating temperature is lower than the boiling point of the organic solvent, the organic solvent is sufficiently removed because the film is thin. Further, the drying may be performed a plurality of times at different temperatures, or a plurality of drying methods may be used in combination.

(2) Specific examples of organic solvents

Examples of the organic solvent used in the composition for forming an organic layer include: an alkylbenzene solvent, a phenyl ether solvent, an alkyl ether solvent, a cyclic ketone solvent, an aliphatic ketone solvent, a monocyclic ketone solvent, a solvent having a diester skeleton, a fluorine-containing solvent, and the like. Specific examples thereof include: pentanol, hexanol, heptanol, octanol, nonanol, decanol, undecanol, dodecanol, tetradecanol, hexan-2-ol, heptan-2-ol, octan-2-ol, decan-2-ol, dodecane-2-ol, cyclohexanol, alpha-terpineol, beta-terpineol, gamma-terpineol, delta-terpineol, terpineol (mixture), ethylene glycol monomethyl ether acetate, propylene glycol monomethyl ether acetate, diethylene glycol dimethyl ether, dipropylene glycol dimethyl ether, diethylene glycol ethyl methyl ether, diethylene glycol isopropyl methyl ether, dipropylene glycol monomethyl ether, diethylene glycol diethyl ether, diethylene glycol monomethyl ether, diethylene glycol butyl methyl ether, tripropylene glycol dimethyl ether, triethylene glycol dimethyl ether, diethylene glycol monobutyl ether, ethylene glycol monophenyl ether, triethylene glycol monomethyl ether, Diethylene glycol dibutyl ether, triethylene glycol butyl methyl ether, polyethylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, p-xylene, m-xylene, o-xylene, 2, 6-lutidine, 2-fluoro-m-xylene, 3-fluoro-o-xylene, 2-chlorobenzotrifluoride, cumene, toluene, 2-chloro-6-fluorotoluene, 2-fluorophenylmethyl ether, anisole, 2, 3-dimethylpyrazine, bromobenzene, 4-fluorophenylmethyl ether, 3-trifluoromethylanisole, mesitylene, 1,2, 4-trimethylbenzene, tert-butylbenzene, 2-methylanisole, phenetole, benzodioxole (benzodioxole), 4-methylanisole, sec-butylbenzene, 3-methylanisole, 4-fluoro-3-methylanisole, Isopropyltoluene (cymene), 1,2, 3-trimethylbenzene, 1, 2-dichlorobenzene, 2-fluorobenzonitrile, 4-fluoro-o-dimethoxybenzene (4-fluoroveratrole), 2, 6-dimethylanisole, n-butylbenzene, 3-fluorobenzonitrile, decahydronaphthalene (decahydroaphtalene), neopentylbenzene, 2, 5-dimethylanisole, 2, 4-dimethylanisole, benzonitrile, 3, 5-dimethylanisole, diphenylether, 1-fluoro-3, 5-dimethoxybenzene, methyl benzoate, isoamylbenzene, 3, 4-dimethylanisole, o-tolunitrile (o-tolunitrile), n-pentylbenzene, o-dimethoxybenzene (veratrole), 1,2,3, 4-tetrahydronaphthalene, ethyl benzoate, n-hexylbenzene, propyl benzoate, cyclohexylbenzene, 1-methylnaphthalene, Butyl benzoate, 2-methylbiphenyl, 3-phenoxytoluene, 2 '-dimethylbiphenyl (2,2' -bitolyl), dodecylbenzene, dipentylbenzene, tetramethylbenzene, trimethoxybenzene, trimethoxytoluene, 2, 3-dihydrobenzofuran, 1-methyl-4- (propoxymethyl) benzene, 1-methyl-4- (butoxymethyl) benzene, 1-methyl-4- (pentyloxymethyl) benzene, 1-methyl-4- (hexyloxymethyl) benzene, 1-methyl-4- (heptyloxymethyl) benzene, benzylbutyl ether, benzylpentyl ether, benzylhexyl ether, benzylheptyl ether, benzyloctyl ether and the like, but not limited thereto. The solvents may be used alone or in combination.

< optional component >

The composition for forming an organic layer may contain any component within a range not impairing the properties thereof. Examples of the optional component include a binder and a surfactant.

(1) Adhesive agent

The organic layer forming composition may contain a binder. The binder forms a film at the time of film formation, while joining the obtained film to a substrate. In addition, the organic layer forming composition plays a role in dissolving, dispersing, and binding other components.

Examples of the binder used in the organic layer-forming composition include: acrylic resins, polyethylene terephthalate, ethylene-vinyl acetate copolymers, ethylene-vinyl alcohol copolymers, Acrylonitrile-ethylene-Styrene copolymers (AES) resins, ionomer resins, chlorinated polyethers, diallyl phthalate resins, unsaturated polyester resins, polyethylene, polypropylene, polyvinyl chloride, polyvinylidene chloride (polyvinylidene chloride), polystyrene, polyvinyl acetate, Teflon (Teflon), Acrylonitrile-Butadiene-Styrene copolymers (Acrylonitrile-Butadiene-Styrene copolymers, ABS) resins, Acrylonitrile-Styrene copolymers (AS) resins, phenol resins, epoxy resins, melamine resins, urea resins, alkyd resins, polyurethanes, and copolymers of the resins and polymers, but is not limited thereto.

The binder used in the organic layer-forming composition may be one type alone, or a mixture of a plurality of types may be used.

(2) Surface active agent

The organic layer-forming composition may contain a surfactant, for example, in order to control the film surface uniformity, the solvent affinity and the liquid repellency of the film surface. Surfactants are classified into ionic and nonionic surfactants according to the structure of a hydrophilic group, and further classified into alkyl surfactants, silicone surfactants, and fluorine surfactants according to the structure of a hydrophobic group. Further, depending on the molecular structure, the polymer molecules are classified into monomolecular systems having a small molecular weight and a simple structure, and macromolecular systems having a large molecular weight and side chains or branches. Further, the compositions are classified into a single system and a mixed system in which two or more surfactants and a base are mixed. As the surfactant that can be used in the composition for forming an organic layer, all kinds of surfactants can be used.

Examples of the surfactant include: perlipalo (Polyflow) No.45, Perlipalo (Polyflow) KL-245, Perlipalo (Polyflow) No.75, Perlipalo (Polyflow) No.90, Perlipalo (Polyflow) No.95 (trade name, manufactured by Co., Ltd.) chemical industry (Ltd.), Diperbyk (Disperbyk)161, Diperbyk (Disperbyk)162, Diperbyk (Disperbyk)163, Diperbyk (Disperbyk)164, Diperbyk (Disperbyk)166, Diperbyk (Disperbyk)170, Diperbyk (Disperbyk)180, Diperbyk (Disperyk) 181, Diperbyk) 182, ByK 300, ByK 306, DiperbyK-368, Japan KF (KF) 310, KbByK-368, KyK-342, KbByK) 320, DiperbyK-320, Diperbyk (Disperbyk)170, Diperbyk (Byk) 150, Dipybk) 150, Dipyk (Byk) 150, Dipyk-K-150, Dipyk (EMByk) 342, Japan KF-K-310, Ky (KF-K-310, Ky) 180, Ky-K-180, Ky (Ky) 180, Ky-K-III, Ky-K-III, Ky-K-III, Ky (Ky-III, Ky (Ky-K-III, Ky-K, Ky-III, Ky-K-III, Ky-III, Ky-K, Ky-K, Ky-III, Ky-K, Ky-K, Ky-K, Ky-K, Ky, KF-50-100CS (trade name, manufactured by shin-Etsu chemical industries, Ltd.), Shafu Long (Surflon) SC-101, Shafu Long (Surflon) KH-40 (trade name, manufactured by Qingmei chemical industries, Ltd.), Fojite (Ftergent)222F, Fojite (Ftergent)251, FTX-218 (trade name, manufactured by Neios (Neos) (stock)), EFTOPEF-351, EFTOPEF-352, EFTOPEF-601, EFTOPEF-801, EFTOP EF-802 (trade name, manufactured by Mitsubishi materials (stock)), Meijia Fa (Megafac) F-470, Meijia Fa (Megafac) F-471, Meijia Fa (Megafac) F-475, Meijiafac (Megafac) R-08, Meijiafac (Megafac) F-477, Meijia Fac (Megafac) 553, Meijia Fac (Megafac) 479, Meigafac (Megac) F-554, DIC (Strand corporation), fluoroalkyl benzenesulfonate, fluoroalkyl carboxylate, fluoroalkyl polyoxyethylene ether, fluoroalkyl ammonium iodide, fluoroalkyl betaine, fluoroalkyl sulfonate, diglycerol tetra (fluoroalkyl polyoxyethylene ether), fluoroalkyl trimethylammonium salt, fluoroalkyl sulfamate, polyoxyethylene nonylphenyl ether, polyoxyethylene octylphenyl ether, polyoxyethylene alkyl ether, and polyoxyethylene laurate, polyoxyethylene oleate, polyoxyethylene stearate, polyoxyethylene laurylamine, sorbitan laurate, sorbitan palmitate, sorbitan stearate, sorbitan oleate, sorbitan fatty acid esters, polyoxyethylene sorbitan laurate, polyoxyethylene sorbitan palmitate, polyoxyethylene sorbitan stearate, polyoxyethylene sorbitan oleate, polyoxyethylene naphthyl ether, alkylbenzenesulfonate, and alkyldiphenyloxide disulfonate.

One kind of surfactant may be used, or two or more kinds may be used in combination.

< composition and Property of composition for Forming organic layer >

The content of each component in the composition for forming an organic layer is determined in consideration of the following points: the composition for forming an organic layer has good solubility, storage stability and film-forming properties of each component, and also has good film quality of a coating film obtained from the composition for forming an organic layer, good ejection properties when an ink jet method is used, and good electrical characteristics, light-emitting characteristics, efficiency and lifetime of an organic EL element having an organic layer produced using the composition. For example, in the case of the composition for forming a light-emitting layer, it is preferable that the first component is 0.0001 to 2.0 mass% based on the total mass of the composition for forming a light-emitting layer, the second component is 0.0999 to 8.0 mass% based on the total mass of the composition for forming a light-emitting layer, and the third component is 90.0 to 99.9 mass% based on the total mass of the composition for forming a light-emitting layer.

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

The composition for forming an organic layer can be produced by appropriately selecting the above components by a known method, and stirring, mixing, heating, cooling, dissolving, dispersing, or the like. After the preparation, filtration, degassing (also referred to as degassing), ion exchange treatment, inert gas substitution, and enclosing treatment may be appropriately selected and performed.

The organic layer-forming composition has a high viscosity, and can provide a good film-forming property and a good ejection property when an ink jet method is used. On the other hand, a film having a low viscosity can be easily produced. Accordingly, the viscosity of the organic layer forming composition is preferably 0.3 to 3mPa · s, more preferably 1 to 3mPa · s, at 25 ℃. In the present invention, the viscosity is a value measured using a cone-plate type rotational viscometer (cone-plate type).

The surface tension of the composition for forming an organic layer is low, and a coating film having good film-forming properties and no defects can be obtained. On the other hand, the higher the ink-jet recording rate, the better the ink-jet ejection property can be obtained. Therefore, the surface tension of the organic layer forming composition at 25 ℃ is preferably 20 to 40mN/m, and more preferably 20 to 30 mN/m. In the present invention, the surface tension is a value measured by the pendant drop method.

< crosslinkable Polymer Compound: a compound represented by the formula (XLP-1) >

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

[ solution 123]

In the formula (XLP-1),

mux, ECx and k are as defined for MU, EC and k in the formula (SPH-1), wherein the compound represented by the formula (XLP-1) has at least one crosslinkable substituent (XLS), and preferably the content of the monovalent or divalent aromatic group having the crosslinkable substituent is 0.1 to 80% by mass in the molecule.

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

The crosslinkable substituent (XLS) is not particularly limited as long as it is a group capable of further crosslinking the polymer compound, and is preferably a substituent having the following structure. Each structural formula represents a bonding site.

[ chemical 124]

L is independently a single bond, -O-, -S-, > C ═ O, -O-C (═ O) -, C1-12 alkylene, C1-12 oxyalkylene, or C1-12 polyoxyalkylene. Among the substituents, preferred are those represented by the formula (XLS-1), the formula (XLS-2), the formula (XLS-3), the formula (XLS-9), the formula (XLS-10) or the formula (XLS-17), and more preferred are those represented by the formula (XLS-1), the formula (XLS-3) or the formula (XLS-17).

Examples of the divalent aromatic compound having a crosslinkable substituent include compounds having the following partial structures.

[ 125]

[ solution 126]

[ solution 127]

[ solution 128]

< Process for producing Polymer and crosslinkable Polymer

The production methods of the polymer compound and 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: examples of the aromatic solvent, saturated/unsaturated hydrocarbon solvent, alcohol solvent, and ether solvent include: dimethoxyethane, 2- (2-methoxyethoxy) ethane, 2- (2-ethoxyethoxy) ethane, and the like.

Alternatively, the reaction may be carried out in a two-phase system. In the case of reaction in a two-phase system, a quaternary ammonium salt phase transfer catalyst may also be added as required.

When the compound of formula (SPH-1) or the compound of formula (XLP-1) is produced, it can be produced in one stage or through a plurality of stages. The polymerization can be carried out by an all-round polymerization method in which the reaction is started after all the raw materials are placed in a reaction vessel, by a dropping polymerization method in which the raw materials are dropped into the reaction vessel, by a precipitation polymerization method in which a product precipitates as the reaction proceeds, or by an appropriate combination of these methods. For example, when a compound represented by the formula (SPH-1) is synthesized in one stage, a monomer having a polymerizable group bonded to a Monomer Unit (MU) and a monomer having a polymerizable group bonded to an end cap unit (EC) are reacted in a state where they are charged into a reaction vessel, whereby a target compound is obtained. In the case of synthesizing the compound represented by the formula (SPH-1) in multiple stages, a monomer having a polymerizable group bonded to a Monomer Unit (MU) is polymerized to a target molecular weight, and then a monomer having a polymerizable group bonded to an end-capping unit (EC) is added and reacted to obtain a target product. When a monomer having a polymerizable group bonded to different types of Monomer Units (MU) is added in multiple stages to carry out the reaction, a polymer having a concentration gradient in the structure of the monomer units can be produced. Alternatively, after the precursor polymer is prepared, the target polymer can be obtained by post-reaction.

In addition, if the polymerizable group of the monomer is selected, the primary structure of the polymer can be controlled. For example, as shown in 1 to 3 of the synthesis scheme, a polymer having a random primary structure (1 of the synthesis scheme), a polymer having a regular primary structure (2 and 3 of the synthesis scheme), and the like can be synthesized, and can be used in appropriate combinations according to the target. Furthermore, if a monomer unit having three or more polymerizable groups is used, a hyperbranched polymer or a dendrimer can be synthesized.

[ solution 129]

a, b is MU or MUx

A polymerizable group x, y (each x and y bond)

1) Polymers synthesized using two monomers (x-a-b) and (x-b-y)

2) Polymers synthesized using two monomers (x-a-x) and (y-b-y)

3) Polymers synthesized using two monomers (x-a-y) and (y-b-y)

The monomers usable in the present invention can be synthesized by the methods described in Japanese patent 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, International publication No. 2016/031639, Japanese patent laid-open No. 2011-174062, and International publication No. 2002/045184.

Further, the specific polymer synthesis procedure can be synthesized by the methods described in Japanese patent laid-open Nos. 2012-036388, 2015/008851, 2012-36381, 2012-144722, 2015/194448, 2013/146806, 2015/145871, 2016/031639, 2016/125560, 2015/145871 and 2011/049241.

< method for producing organic electroluminescent element >

Each layer constituting the organic EL element can be formed by forming a material constituting each layer into a thin film by a method such as vapor deposition, resistance heating vapor deposition, electron beam vapor deposition, sputtering, molecular lamination, printing, ink jet, spin coating, casting, or coating. The film thickness of each layer formed in the above-described manner is not particularly limited, and may be appropriately set depending on the properties of the material, but is generally in the range of 2nm to 5000 nm. The film thickness can be measured by a crystal oscillation film thickness measuring apparatus or the like. In the case of forming a thin film by vapor depositionThe deposition conditions vary depending on the type of material, the target crystal structure and the associated structure of the film, and the like. The deposition conditions are preferably set to +50 ℃ to +400 ℃ in the boat heating temperature and 10 degrees of vacuum ^-6 Pa～10 ^-3 Pa, a deposition rate of 0.01 nm/sec to 50 nm/sec, a substrate temperature of-150 ℃ to +300 ℃, and a film thickness of 2nm to 5 μm.

Next, as an example of a method for manufacturing an organic EL element, a method for manufacturing an organic EL element including an anode, a hole injection layer, a hole transport layer, a light-emitting layer including a host material and a dopant material, an electron transport layer, an electron injection layer, and a cathode will be described. An anode is formed by forming a thin film of an anode material on an appropriate substrate by an evaporation method or the like, and then a thin film of a hole injection layer and a hole transport layer is formed on the anode. A target organic EL element is obtained by co-evaporating a host material and a dopant material on the thin film to form a thin film as a light-emitting layer, forming an electron transport layer and an electron injection layer on the light-emitting layer, and further forming a thin film containing a substance for a cathode as a cathode by an evaporation method or the like. In the production of the organic EL element, the order of production may be reversed, and 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 may be produced in this order.

When a dc voltage is applied to the organic EL element obtained as described above, the anode may be applied with a positive polarity and the cathode with a negative polarity, and when a voltage of about 2V to 40V is applied, light emission can be observed from the transparent or translucent electrode side (anode or cathode, or both). In addition, the organic EL element emits light even when a pulse current or an alternating current is applied thereto. Further, the waveform of the applied alternating current may be arbitrary.

< example of application of organic electroluminescent element >

The organic EL element is also applicable to a display device, an illumination device, or the like.

A display device or a lighting device including an organic EL element can be manufactured by a known method such as connecting the organic EL element to a known driving device, and can be driven by a known driving method such as direct current driving, pulse driving, or alternating current driving.

Examples of the display device include: a panel display such as a color flat panel display, a flexible display such as a flexible color organic Electroluminescence (EL) display, and the like (for example, refer to japanese patent laid-open No. 10-335066, japanese patent laid-open No. 2003-321546, and japanese patent laid-open No. 2004-281086). Examples of the display mode of the display include a matrix mode and a segment mode. Further, the matrix display and the segment display may coexist in the same panel (panel).

In the matrix, pixels for display are two-dimensionally arranged in a lattice shape, a mosaic shape, or the like, and characters or images are displayed by a set of pixels. The shape or size of the pixel is determined according to the application. For example, in image and character display of a personal computer, a monitor, and a television, a rectangular pixel having a side of 300 μm or less is generally used, and in the case of a large-sized display such as a display panel, a pixel having a side of mm level is used. In the case of monochrome display, pixels of the same color may be arranged, and in the case of color display, pixels of red, green, and blue are arranged in parallel to perform display. In this case, a triangular shape and a striped shape are typical. Also, as a driving method of the matrix, any one of a line-sequential (line-sequential) driving method or an active matrix may be used. The line sequential driving has an advantage of a simple structure, but when the operation characteristics are taken into consideration, the active matrix is sometimes more excellent, and therefore the driving method needs to be used separately depending on the application.

In the segment method (type), a pattern is formed so as to display information determined in advance, and the determined region is caused to emit light. Examples thereof include: time and temperature display in a digital clock or a thermometer, operation state display of an audio device or an induction cooker, panel display of an automobile, and the like.

Examples of the illumination device include an illumination device such as an indoor illumination, and a backlight of a liquid crystal display device (see, for example, japanese patent laid-open nos. 2003-257621, 2003-277741, and 2004-119211). Backlights are used mainly for improving visibility of display devices that do not emit light, and are used for liquid crystal display devices, clocks, audio devices, automobile panels, display panels, signs, and the like. In particular, when considering that conventional systems including fluorescent lamps and light guide plates are difficult to be thinned as backlights for personal computers, which are problematic in thinning of liquid crystal display devices, backlights using organic EL elements have thin and lightweight features.

< other organic devices >

The polycyclic aromatic compound of the present invention can be used for the production of an organic field effect transistor, an organic thin film solar cell, or the like, in addition to the organic electroluminescent element.

The organic field effect transistor is a transistor in which current is controlled by an electric field generated by voltage input, and includes a gate electrode in addition to an active electrode and a drain electrode. The organic field effect transistor is a transistor as follows: when a voltage is applied to the gate electrode, an electric field is generated, and the flow of electrons (or holes) flowing between the source electrode and the drain electrode is arbitrarily blocked to control the current. A field effect transistor is easy to be miniaturized compared with a single transistor (bipolar transistor), and is often used as an element constituting an integrated circuit or the like.

In general, the organic field effect transistor may be configured such that a source electrode and a drain electrode are provided in contact with an organic semiconductor active layer formed using the polycyclic aromatic compound of the present invention, and a gate electrode is provided through an insulating layer (dielectric layer) in contact with the organic semiconductor active layer. Examples of the element structure include the following structures.

(1) Substrate/gate electrode/insulator layer/source and drain electrodes/organic semiconductor active layer

(2) Substrate, gate electrode, insulator layer, organic semiconductor active layer, source electrode and drain electrode

(3) Substrate/organic semiconductor active layer/source electrode and drain electrode/insulator layer/gate electrode

(4) Substrate/source and drain electrodes/organic semiconductor active layer/insulator layer/gate electrode

The organic field effect transistor configured as described above can be used as a pixel driving switching element of an active matrix driving type liquid crystal display, an organic electroluminescence display, or the like.

An organic thin-film solar cell has a structure in which an anode such as ITO, a hole transport layer, a photoelectric conversion layer, an electron transport layer, and a cathode are stacked 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 of 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. In the organic thin film solar cell, the polycyclic aromatic compound of the present invention can function as a hole transport material or an electron transport material. The organic thin film solar cell may suitably include a hole blocking layer, an electron injection layer, a hole injection layer, a smoothing layer, and the like, in addition to the layers. In the organic thin film solar cell, known materials used in the organic thin film solar cell may be appropriately selected and used in combination.

< wavelength converting Material >

The polycyclic aromatic compound of the present invention is useful as a wavelength converting material.

Now, studies are actively being made to apply a multicolor technology based on a color conversion scheme to a liquid crystal display or an organic EL display, illumination, and the like. Color conversion is to convert light emitted from the phosphor into light having a longer wavelength, and means, for example, converting ultraviolet light or blue light into green light or red light. The wavelength conversion material having the color conversion function is formed into a film, and for example, is combined with a blue light source, whereby three primary colors of blue, green, and red, that is, white light can be extracted from the blue light source. A full color display (full color display) can be manufactured by using a white light source in which a blue light source and a wavelength conversion film having a color conversion function are combined as a light source unit, and combining the white light source with a liquid crystal driving portion and a color filter. In addition, without a liquid crystal driving portion, the liquid crystal display device can be directly used as a white light source, and can be applied to a white light source such as a light-emitting diode (LED) lighting. Further, a full-color organic EL display can be manufactured without using a metal mask by using a blue organic EL element as a light source and using it in combination with a wavelength conversion film that converts blue light into green light and red light. Further, a low-cost full-color micro LED display can be manufactured by using a blue micro LED as a light source in combination with a wavelength conversion film that converts blue light into green light and red light.

The polycyclic aromatic compound of the present invention is useful as the wavelength converting material. Ultraviolet light or light from a light source or a light-emitting element that generates blue light having a shorter wavelength can be converted into blue light or green light having high color purity and suitable for use in a display device (a display device or a liquid crystal display device using an organic EL element) using a wavelength conversion material containing the polycyclic aromatic compound of the present invention. The color to be converted can be adjusted by appropriately selecting the substituent of the polycyclic aromatic compound of the present invention, a binder resin used in a wavelength converting composition described later, and the like. The wavelength converting material is prepared as a wavelength converting composition containing the polycyclic aromatic compound of the present invention. In addition, a wavelength conversion film can also be formed using the wavelength conversion composition.

The wavelength conversion composition may contain a binder resin, other additives, and a solvent in addition to the polycyclic aromatic compound of the present invention. Examples of the binder resin include resins described in paragraphs 0173 to 0176 of International publication No. 2016/190283. As the other additives, the compounds described in paragraphs 0177 to 0181 of International publication No. 2016/190283 can be used. As the solvent, the description of the solvent contained in the composition for forming a light-emitting layer can be referred to.

The wavelength conversion film includes a wavelength conversion layer formed by curing the wavelength conversion composition. As a method for producing a wavelength conversion layer from the wavelength conversion composition, a known film forming method can be referred to. The wavelength conversion film may contain only a wavelength conversion layer formed of the composition containing the polycyclic aromatic compound of the present invention, or may contain other wavelength conversion layers (for example, a wavelength conversion layer that converts blue light into green light or red light, or a wavelength conversion layer that converts blue light or green light into red light). Further, the wavelength conversion film may include a base material layer or a barrier layer for preventing the color conversion layer from being deteriorated by oxygen, moisture, or heat.

[ examples ]

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

Synthesis example (1): synthesis of Compound (1-2)

Under nitrogen atmosphere, at 0 deg.C, compound (Int-1-2) (2.4g, 3.0mmol, 1eq.) and tert-butyl benzene (t-butyl benzene) (T-butyl benzene) ^t Bu-benzene, 50ml) flask was charged with 1.60M t-butyllithium pentane solution ( ^t BuLi, 3.75 ml). After the completion of the dropwise addition, the temperature was raised to 70 ℃ and the mixture was stirred for 0.5 hour, and then a component having a boiling point lower than that of tert-butylbenzene was distilled off under reduced pressure. Cooled to-50 ℃ and boron tribromide (0.62g) was added, and the mixture was stirred for 0.5 hour after warming to room temperature. Thereafter, it was cooled again to 0 ℃ and N, N-diisopropylethylamine (EtN) was added ⁱ Pr ₂ 0.39g) was added thereto, and the mixture was stirred at room temperature until heat generation was completed, and then heated to 100 ℃ and stirred for 1 hour. The reaction solution was cooled to room temperature, and an aqueous sodium acetate solution cooled with an ice bath and ethyl acetate were added in this order to separate the reaction solution. The organic layer was concentrated and purified by silica gel short path column chromatography (eluent: chlorobenzene). The obtained crude product was recrystallized using toluene, whereby compound (1-2) (0.20g) was obtained. The compound (1-2) as a target was confirmed at M/z (M + H) 773.501 by Mass Spectrometry (MS).

[ chemical formula 130]

Synthesis example (2): synthesis of Compound (1-31)

Compound (1-31) (0.13g) was obtained in the same procedure as in Synthesis example 1, except that compound (Int-1-2) (2.40g, 3.0mmol, 1eq.) was changed to compound (Int-1-31) (2.40g, 3.0mmol, 1 eq.).

The compound (1-31) as the target compound was confirmed at M/z (M + H) ═ 773.501 by MS.

[ solution 131]

Synthesis example (3): synthesis of Compound (1-44)

Compound (1-44) (0.16g) was obtained in the same procedure as in Synthesis example 1, except that compound (Int-1-2) (2.40g, 3.0mmol, 1eq.) was changed to compound (Int-1-44) (2.40g, 3.0mmol, 1 eq.).

The compound (1-44) as the target compound was confirmed at M/z (M + H) ═ 773.501 by MS.

[ solution 132]

Synthesis example (4): synthesis of Compound (1-71)

Under nitrogen atmosphere, at 0 deg.C, compound (Int-1-71) (2.88g, 3.0mmol, 1eq.) and tert-butyl benzene (t-butyl benzene) (n-butyl benzene, n-1-71, n-1-71, n-1 ^t Bu-benzene, 50ml) flask was charged with 1.60M t-butyllithium pentane solution (Bu-benzene, N.E.) ^t BuLi, 7.50 ml). After the completion of the dropwise addition, the temperature was raised to 70 ℃ and the mixture was stirred for 0.5 hour, and then a component having a boiling point lower than that of tert-butylbenzene was distilled off under reduced pressure. Cooled to-50 ℃ and boron tribromide (1.23g) was added, and the mixture was stirred for 0.5 hour after warming to room temperature. Thereafter, it was cooled again to 0 ℃ and N, N-diisopropylethylamine (EtN) was added ⁱ Pr ₂ 0.78g) was added thereto, and the mixture was stirred at room temperature until heat generation was completed, and then heated to 100 ℃ and stirred for 1 hour. The reaction solution was cooled to room temperature, and an aqueous sodium acetate solution cooled with an ice bath and ethyl acetate were added in this order to separate the reaction solution. The organic layer was concentrated and purified by silica gel short path column chromatography (eluent: chlorobenzene). Will obtainThe obtained crude product was recrystallized from toluene, whereby compound (1-71) (0.26g) was obtained.

The compound (1-71) as the target compound was confirmed at M/z (M + H) ═ 907.320 by MS.

[ solution 133]

Synthesis example (5): synthesis of Compound (1-73)

Compound (1-73) (0.09g) was obtained in the same manner as in Synthesis example 4, except that compound (Int-1-71) (2.88g, 3.0mmol, 1eq.) was changed to compound (Int-1-73) (2.88g, 3.0mmol, 1 eq.).

The compound (1-73) as the target compound was confirmed at M/z (M + H) ═ 907.320 by MS.

[ solution 134]

Synthesis example (6): synthesis of Compound (1-81)

Compound (1-81) (0.21g) was obtained in the same manner as in Synthesis example 4, except that compound (Int-1-71) (2.88g, 3.0mmol, 1eq.) was changed to compound (Int-1-81) (2.88g, 3.0mmol, 1 eq.).

The compound (1-81) as the target compound was confirmed at M/z (M + H) ═ 907.320 by MS.

[ solution 135]

Synthesis of comparative Compound (1)

The synthesis was carried out according to the method described in Korean laid-open patent No. 2020/121228. The target compound (1) was confirmed by MS at M/z (M + H) 775.516.

[ solution 136]

Other polycyclic aromatic compounds of the present invention can be synthesized by the method based on the above synthesis example by appropriately changing the compounds as raw materials.

Next, the production 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 described below, and the film thickness and the constituent material of each layer may be appropriately changed according to the basic properties of the compound of the present invention.

Evaluation item and evaluation method

The evaluation items include a driving voltage (V), an emission wavelength (nm), a CIE chromaticity (x, y), an external quantum efficiency (%), a maximum wavelength (nm) and a half-peak width (nm) of an emission spectrum, and the like. The evaluation item may use a value at the time of appropriate light emission luminance.

The quantum efficiency of a light-emitting element includes internal quantum efficiency and external quantum efficiency, and the internal quantum efficiency indicates a proportion of external energy injected as electrons (or holes) into a light-emitting layer of the light-emitting element, which is converted into photons. On the other hand, the external quantum efficiency is calculated based on the amount of photons emitted to the outside of the light-emitting element, and since a part of the photons generated in the light-emitting layer is absorbed or continuously reflected by the inside of the light-emitting element and is not emitted to the outside of the light-emitting element, the external quantum efficiency is lower than the internal quantum efficiency.

The measurement method of the spectral emission luminance (emission spectrum) and the external quantum efficiency is as follows. A voltage was applied using a voltage/current generator R6144 manufactured by edwaten test (Advantest), inc., whereby the element was caused to emit light. The spectral radiance in the visible light region was measured from the direction perpendicular to the light-emitting surface using a spectral radiance meter SR-3AR manufactured by TOPCON (TOPCON). Assuming that the light-emitting surface is a perfect diffusion surface, the number obtained by dividing the measured value of the spectral emission luminance of each wavelength component by the wavelength energy and multiplying by pi is the number of photons at each wavelength. Then, the number of photons is integrated over the entire wavelength range to be observed, and the total number of photons emitted from the element is set. A value obtained by dividing an applied current value by an elementary charge (elementary charge) is set as a carrier number injected into the element, and a value obtained by dividing a total photon number released from the element by a carrier number injected into the element is an external quantum efficiency. The half-value width of the emission spectrum is determined as a width between upper and lower wavelengths at which the intensity becomes 50% with the maximum emission wavelength as the center.

< evaluation of vapor deposition type organic EL element >

Organic EL elements of examples 1-1 to 1-6 and comparative example 1-1 were fabricated, and luminance was measured at 500cd/m ² Driving voltage, External Quantum Efficiency (EQE), and LT50 (constant current driving, time for maintaining 50% or more of luminance, in this case, initial luminance 500 cd/m) ² The current density is maintained at 250cd/m ² The above time of brightness).

[ Table 1]

The following are "NPD", "TcTa", "mCP", "Ir (ppy) in Table 1 ₃ "," 2CzBN "," BPy-TP2 "," GH-1 ", and comparative compound (1).

[ solution 137]

< example 1-1 >

A glass substrate (manufactured by Optic Science) having a thickness of 26mm by 28mm by 0.7mm prepared by polishing ITO formed to a thickness of 200nm by sputtering to a thickness of 50nm was used as a transparent support substrate. The transparent support substrate was fixed to a substrate holder of a commercially available vapor deposition apparatus (manufactured by showa vacuum (jet)), and a molybdenum vapor deposition boat and a tungsten vapor deposition boat were respectively placed therein, the molybdenum vapor deposition boat containing NPD, TcTa, mCP, GH-1, the compound (1-2), 2CzBN, and BPy-TP2, and the tungsten vapor deposition boat containing LiF and aluminum.

The following layers are sequentially formed on the ITO film of the transparent support substrate. The vacuum vessel was depressurized to 5X 10 ^-4 Pa, NPD was heated and vapor-deposited so that the film thickness became 40nm, thereby forming a hole injection layer. Next, TcTa was heated and vapor-deposited so that the film thickness became 15nm, and mCP was heated and vapor-deposited so that the film thickness became 15nm, thereby forming a hole transport layer including two layers. Then, GH-1 and the compound (1-2) were simultaneously heated and vapor-deposited so that the film thickness became 20nm, thereby forming a light-emitting layer. The deposition rate was adjusted so that the weight ratio of GH-1 to the compound (1-2) became approximately 99 to 1. Next, 2CzBN was heated and vapor-deposited so that the film thickness became 10nm, and BPy-TP2 was heated and vapor-deposited so that the film thickness became 20nm, thereby forming an electron transport layer including two layers. The deposition rate of each layer is 0.01 nm/sec to 1 nm/sec. Then, LiF was heated and vapor-deposited at a vapor deposition rate of 0.01 nm/second to 0.1 nm/second so that the film thickness became 1nm, and then aluminum was heated and vapor-deposited so that the film thickness became 100nm to form a cathode, thereby obtaining an organic EL element. In this case, the deposition rate of aluminum is adjusted to 1 nm/sec to 10 nm/sec.

< example 1-2 to example 1-6 and comparative example 1-1 >)

Each element was produced by changing the compound (1-2) as a dopant in example 1 to each dopant shown in table 1.

The evaluation results of the respective elements are shown in table 2.

[ Table 2]

In examples 1-1 to 1-6, results of high external quantum efficiency and long LT50 were obtained as compared with comparative example 1-1.

< evaluation of vapor deposition type organic EL element >

Organic EL elements of example G2-1 to example G2-6, comparative example G2-1, example G3-1 to example G3-6 and comparative example G3-1 were prepared, and luminance was measured at 500cd/m ² Emission wavelength, half-value width, driving voltage, external quantum efficiency, and LT50 (time for constant current driving to maintain 50% or more of luminance, in this case, initial luminance of 500cd/m ² The current density is maintained at 250cd/m during continuous driving ² The above time of brightness).

[ Table 3]

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

[ 138]

< example G2-1 >)

A glass substrate (manufactured by Optic Science) having a thickness of 26mm by 28mm by 0.7mm prepared by polishing ITO formed to a thickness of 200nm by sputtering to a thickness of 50nm was used as a transparent support substrate. The transparent support substrate was fixed to a substrate holder of a commercially available vapor deposition apparatus (manufactured by showa vacuum (jet)), and a molybdenum vapor deposition boat and a tungsten vapor deposition boat were respectively placed therein, the molybdenum vapor deposition boat containing HATCN, TBB, TcTa, CBP, the compound (1-2), and TPBi, and the tungsten vapor deposition boat containing LiF and aluminum.

The following layers are sequentially formed on the ITO film of the transparent support substrate. The vacuum vessel was depressurized to 5X 10 ^-4 Pa, HATCN was first heated and vapor-deposited to a film thickness of 5nm to form a hole injection layer. Next, TBB was heated and vapor-deposited so that the film thickness became 65nm, and TcTa was heated and vapor-deposited so that the film thickness became 10nm, thereby forming a hole transport layer including two layers. Next, the CBP was treated simultaneously with the compound (1-2)The light-emitting layer was formed by heating and vapor deposition so that the film thickness became 30 nm. The deposition rate was adjusted so that the weight ratio of CBP to the compound (1-2) became approximately 99 to 1. Next, TPBi was heated and vapor-deposited so that the thickness thereof became 50nm, thereby forming an electron transport layer. The deposition rate of each layer is 0.01 nm/sec to 1 nm/sec. Then, LiF was heated and vapor-deposited at a vapor deposition rate of 0.01 nm/second to 0.1 nm/second so that the film thickness became 1nm, and then aluminum was heated and vapor-deposited so that the film thickness became 100nm to form a cathode, thereby obtaining an organic EL element. In this case, the deposition rate of aluminum is adjusted to 1 nm/sec 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 >)

The CBP as a host, the compound (1-2) as a dopant and the host of example G2-1 were: the dopant mixing ratio was changed to each host, each dopant and each mixing ratio described in table 3 to fabricate each element.

The evaluation results of the respective elements are shown in table 4.

[ Table 4]

In example G2-1 to example G2-6 and example G3-1 to example G3-6, higher efficiency and longer device life were obtained as compared with comparative example G2-1 and comparative example G3-1.

< evaluation of vapor deposition type organic EL element >

Organic EL devices of examples G4-1 to G4-4 and comparative example G4-1 were fabricated, and luminance was measured at 500cd/m ² Luminescence wavelength, half-value width, drive voltage, external quantum efficiency, and LT50 (time for constant current drive to maintain 50% or more of luminance, in this case, initial luminance of 500cd/m ² The current density is maintained at 250cd/m ² The above time of brightness).

[ Table 5]

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

[ solution 139]

< embodiment G4-1 >

ITO formed to a thickness of 200nm by sputtering was polished to a thickness of 50nm on a 26mm X28 mm X0.7 mm glass substrate (manufactured by Opto Science, Inc.) as a transparent support substrate. The transparent support substrate was fixed to a substrate holder of a commercially available vapor deposition apparatus (manufactured by Showa vacuum deposition (Strand)), and a molybdenum vapor deposition boat and a tungsten vapor deposition boat were respectively placed therein, the molybdenum vapor deposition boats containing HATCN, TBB, TcTa, BCC-TPTA, compounds (1-2), T2T, Liq, and TPBi, and the tungsten vapor deposition boats containing LiF and aluminum.

The following layers are sequentially formed on the ITO film of the transparent support substrate. The vacuum vessel was depressurized to 5X 10 ^-4 Pa, HATCN was heated and vapor-deposited so that the film thickness became 5nm, thereby forming a hole injection layer. Next, TBB was heated and vapor-deposited so that the film thickness became 65nm, and TcTa was heated and vapor-deposited so that the film thickness became 10nm, thereby forming a hole transport layer including two layers. Then, TcTa, BCC-TPTA and the compound (1-2) were simultaneously heated and vapor-deposited to a film thickness of 30nm to form a light-emitting layer. The deposition rate was adjusted so that the weight ratio of CBP, BCC-TPTA and compound (1-2) was approximately 85 to 14 to 1. Next, T2T was heated and vapor-deposited so that the film thickness became 10nm, and then TPBi and Liq were heated and vapor-deposited so that the film thickness became 40nm, thereby forming an electron transport layer including two layers. The deposition rate was adjusted so that the weight ratio of TPBi to Liq became approximately 70 to 30. The deposition rate of each layer is 0.01 nm/sec to 1 nm/sec. It is composed ofThen, LiF was heated and vapor-deposited at a vapor deposition rate of 0.01 nm/second to 0.1 nm/second so that the film thickness became 1nm, and then aluminum was heated and vapor-deposited so that the film thickness became 100nm to form a cathode, thereby obtaining an organic EL element. In this case, the deposition rate of aluminum is adjusted to 1 nm/sec to 10 nm/sec.

< example G4-2 to example G4-4 and comparative example G4-1 >)

Each element was produced by changing BCC-TPTA as an auxiliary dopant and the compound (1-2) as a dopant in example G4-1 and the mixing ratio to the respective auxiliary dopants and the respective mixing ratios described in Table 5.

The evaluation results of the respective elements are shown in table 6.

[ Table 6]

Examples G4-1 to G4-4 gave higher efficiencies and longer element lifetimes than comparative example G4-1. As in the case of the examples G4-1 and G4-2, devices using exciplex (exiplex) and auxiliary dopant were realized.

< evaluation of coated organic EL element >

Next, an organic EL device obtained by forming an organic layer by coating will be described.

< macromolecular host compound: synthesis of SPH-101

SPH-101 was synthesized according to the method described in International publication No. 2015/008851. Copolymers were obtained with M2 or M3 bonded in the ortho position to M1, each unit being assumed to be 50: 26: 24 (molar ratio). In the following structural formula, Me is a methyl group, Bpin is a pinacolato boron group, and x is a linking site of each unit.

[ solution 140]

< high molecular hole transporting Compound: synthesis of XLP-101

XLP-101 was synthesized according to the method described in Japanese patent laid-open publication No. 2018-61028. Copolymers were obtained with M5 or M6 bonded in the ortho position to M4, each unit being assumed to be 40: 10: 50 (molar ratio). In the following structural formula, Me is methyl, Bpin is pinacolato boron group, and is the connection part of each unit.

[ solution 141]

< example 2-1 to example 2-9 >

A coating solution of the material forming each layer was prepared to prepare a coating type organic EL element.

< production of organic EL elements in examples 2-1 to 2-3 >

The material composition of each layer in the organic EL device is shown in table 7.

[ Table 7]

The structure of "ET 1" in table 7 is shown below.

[ solution 142]

< preparation of composition (1) for Forming light-emitting layer >

The composition (1) for forming a light-emitting layer was prepared by stirring the following components until a uniform solution was formed. The prepared composition for forming a light-emitting layer was spin-coated on a glass substrate, and dried by heating under reduced pressure, thereby obtaining a coating film free from film defects and excellent in smoothness.

The compound (a) is a polycyclic aromatic compound represented by the general formula (1A-1) (for example, the compound (1-2)), a polymer compound obtained by polymerizing the polycyclic aromatic compound as a monomer (that is, the monomer has a reactive substituent), or a crosslinked polymer obtained by further crosslinking the polymer compound. The polymer compound used for obtaining the polymer crosslinked body has a crosslinkable substituent.

< PEDOT: PSS solution >

Commercially available PEDOT was used: PSS solution (Clevelos (TM) P VP AI4083, PEDOT: aqueous dispersion of PSS, manufactured by Heraeus Holdings).

[ solution 143]

< preparation of OTPD solution >

OTPD (LT-N159, manufactured by luminology Technology Corp) and IK-2 (photo cation polymerization initiator, manufactured by Sanapro) were dissolved in toluene to prepare an OTPD solution having an OTPD concentration of 0.7 wt% and an IK-2 concentration of 0.007 wt%.

[ solution 144]

< preparation of XLP-101 solution >

XLP-101 was dissolved in xylene at a concentration of 0.6 wt% to prepare a 0.6 wt% XLP-101 solution.

< preparation of PCz solution

PCz (polyvinylcarbazole) was dissolved in dichlorobenzene to prepare a 0.7 wt% PCz solution.

[ solution 145]

< example 2-1 >)

On a glass substrate on which ITO with a thickness of 150nm was evaporated, PEDOT: PSS solution, calcined on a hot plate at 200 ℃ for 1 hour, thus producing PEDOT: PSS film (hole injection layer). Next, the OTPD solution was spin-coated, dried on a hot plate at 80 ℃ for 10 minutes, and then exposed to light at 100mJ/cm ² The film was exposed to light and calcined on a hot plate at 100 ℃ for 1 hour to prepare an OTPD film (hole transport layer) having a film thickness of 30nm which was insoluble in the solution. Next, the composition (1) for forming a light-emitting layer was spin-coated and calcined on a hot plate at 120 ℃ for 1 hour to prepare a light-emitting layer having a thickness of 20 nm.

The multilayer film thus produced was fixed to a substrate holder of a commercially available vapor deposition apparatus (manufactured by showa vacuum (jet)), and a molybdenum vapor deposition boat containing ET1, a molybdenum vapor deposition boat containing LiF, and a tungsten vapor deposition boat containing aluminum were installed therein. The vacuum vessel was depressurized to 5X 10 ^-4 Pa, ET1 was then heated and vapor-deposited to a film thickness of 30nm, thereby forming an electron transport layer. The deposition rate in forming the electron transport layer was set to 1 nm/sec. Then, LiF is heated and vapor deposition is performed at a vapor deposition rate of 0.01 nm/sec to 0.1 nm/sec so that the film thickness becomes 1 nm. Next, aluminum was heated and vapor deposition was performed so that the film thickness became 100nm, thereby forming a cathode. An organic EL element was obtained in the manner described.

< example 2-2 >

An organic EL element was obtained in the same manner as in example 2-1. Further, the hole transport layer was formed into a film having a thickness of 30nm by spin-coating an XLP-101 solution and calcining the solution on a heating plate at 200 ℃ for 1 hour.

< example 2-3 >

An organic EL element was obtained in the same manner as in example 2-1. Further, the hole-transporting layer was calcined on a heating plate at 120 ℃ for 1 hour by spin-coating PCz solution to prepare a film having a thickness of 30 nm.

< evaluation of organic EL elements of examples 2-1 to 2-3 >

It is envisioned that: the coating-type organic EL element obtained as described above also has excellent driving voltage and external quantum efficiency as in the vapor deposition-type organic EL element.

< production of organic EL elements in examples 2-4 to 2-6 >

The material composition of each layer in the organic EL device is shown in table 8.

[ Table 8]

< preparation of composition (2) for Forming light-emitting layer to preparation of composition (4) for Forming light-emitting layer

The composition (2) for forming a light-emitting layer was prepared by stirring the following components until a uniform solution was formed.

Compound (A) 0.02% by weight

mCBP 1.98 wt.%

98.00% by weight of toluene

The composition (3) for forming a light-emitting layer was prepared by stirring the following components until a uniform solution was formed.

0.02% by weight of Compound (A)

SPH-1011.98 wt.%

98.00% by weight of xylene

The composition (4) for forming a light-emitting layer was prepared by stirring the following components until a uniform solution was formed.

0.02% by weight of Compound (A)

DOBNA 1.98% by weight

98.00% by weight of toluene

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

[ solution 146]

< example 2-4 >

An ND-3202 (manufactured by Nissan chemical industry) solution was spin-coated on a glass substrate on which ITO having a thickness of 45nm was formed, and then the substrate was heated at 50 ℃ for 3 minutes and 230 ℃ for 15 minutes in an atmospheric environment, thereby forming an ND-3202 film (hole injection layer) having a thickness of 50 nm. Next, the XLP-101 solution was spin-coated and heated on a heating plate at 200 ℃ for 30 minutes under a nitrogen atmosphere, thereby producing an XLP-101 film (hole transport layer) with a film thickness of 20 nm. Subsequently, the composition (2) for forming a light-emitting layer was spin-coated and heated at 130 ℃ for 10 minutes in a nitrogen atmosphere to form a 20nm light-emitting layer.

The multilayer film thus produced was fixed to a substrate holder of a commercially available vapor deposition apparatus (manufactured by showa vacuum (jet)), and a molybdenum vapor deposition boat containing TSPO1, a molybdenum vapor deposition boat containing LiF, and a tungsten vapor deposition boat containing aluminum were installed therein. The vacuum vessel was depressurized to 5X 10 ^-4 Pa, TSPO1 was then heated and vapor-deposited to a film thickness of 30nm, thereby forming an electron transport layer. The deposition rate in forming the electron transport layer was set to 1 nm/sec. Then, LiF is heated to form a film with a thickness of 1nm, and evaporation is performed at an evaporation rate of 0.01 nm/sec to 0.1 nm/sec. Next, aluminum was heated to form a cathode by vapor deposition so that the film thickness became 100 nm. In this way, an organic EL element was obtained.

< examples 2 to 5 and 2 to 6 >

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

< evaluation of organic EL elements of examples 2-4 to 2-6 >

< production of organic EL elements in examples 2-7 to 2-9 >

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

[ Table 9]

< preparation of compositions (5) to (7) for Forming light-emitting layer >

The composition (5) for forming a light-emitting layer was prepared by stirring the following components until a uniform solution was formed.

The composition (6) for forming a light-emitting layer was prepared by stirring the following components until a uniform solution was formed.

The composition (7) for forming a light-emitting layer was prepared by stirring the following components until a uniform solution was formed.

In Table 9, "2 PXZ-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.

[ solution 147]

< example 2-7 >

On a glass substrate on which 45nm thick ITO was formed, an ND-3202 (manufactured by Nissan chemical industries) solution was spin-coated, and then heated at 50 ℃ for 3 minutes and 230 ℃ for 15 minutes in an atmospheric environment, thereby forming an ND-3202 film (hole injection layer) having a thickness of 50 nm. Next, the XLP-101 solution was spin-coated and heated on a heating plate at 200 ℃ for 30 minutes under a nitrogen atmosphere, thereby forming an XLP-101 film (hole transport layer) with a film thickness of 20 nm. Next, the composition (5) for forming a light-emitting layer was spin-coated and heated at 130 ℃ for 10 minutes in a nitrogen atmosphere, thereby forming a 20nm light-emitting layer.

The multilayer film thus produced was fixed to a substrate holder of a commercially available vapor deposition apparatus (manufactured by showa vacuum (jet)), and a molybdenum vapor deposition boat containing TSPO1, a molybdenum vapor deposition boat containing LiF, and a tungsten vapor deposition boat containing aluminum were installed therein. The vacuum vessel was depressurized to 5X 10 ^-4 Pa, TSPO1 was then heated to form an electron transport layer by vapor deposition so that the film thickness became 30 nm. The deposition rate in forming the electron transport layer was set to 1 nm/sec. Then, LiF was heated to deposit at a deposition rate of 0.01 nm/sec to 0.1 nm/sec so that the film thickness became 1 nm. Next, aluminum was heated to form a cathode by vapor deposition so that the film thickness became 100 nm. In this way, an organic EL element was obtained.

< examples 2 to 8 and 2 to 9 >

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

< evaluation of organic EL elements of examples 2-7 to 2-9 >

As described above, although some of the compounds of the present invention were evaluated as materials for organic EL devices, they were shown to be excellent materials, other compounds not evaluated also had the same basic skeleton and were also compounds having similar structures as a whole, and those skilled in the art would understand that the same excellent materials for organic EL devices were also excellent.

Claims

1. A polycyclic aromatic compound having one or more structures containing a structural unit represented by the following formula (1A-1),

in the formula (1A-1),

L ¹ 、L ² 、L ³ and L ⁴ Independently of one another, a single bond, a substituted or unsubstituted arylene group, a substituted or unsubstituted heteroarylene group, a substituted or unsubstituted alkylene group, a substituted or unsubstituted cycloalkylene group, a substituted or unsubstituted alkenylene group, > O, > N-R, > C (-R) ₂ 、＞Si(-R) ₂ R > N-R, said > Si (-R) ₂ R of (b) and said > C (-R) ₂ Each R of (A) is independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, > Si (-R) ₂ Two R of (a) and said > C (-R) ₂ The two R's are not bonded to each other to form a ring, or are bonded to each other to form a ring, the R > N-R, the R > C (-R) ₂ R of (b) and said > Si (-R) ₂ At least one R ofIndependently bonded to at least one of the A1 ring, the A2 ring, the A3 ring, the A4 ring, and the A5 ring without a single bond or a linking group, or with a single bond or a linking group,

a polycyclic aromatic compound having one or more structures containing a structural unit represented by the formula (1A-1) is not condensed with at least one cycloalkane, at least one hydrogen in the cycloalkane being unsubstituted or substituted, at least one-CH in the cycloalkane ₂ -is unsubstituted-O-or-S-substituted, or is substituted, 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 claim 1, wherein the structural unit is a structural unit represented by the following formula (1a-1),

in the formula (1a-1),

L ¹ 、L ² 、L ³ and L ⁴ Independently of one another, a single bond, substituted or unsubstituted arylene, substituted or unsubstituted heteroarylene, substituted or unsubstituted alkylene, substituted or unsubstituted cycloalkylene, substituted or unsubstituted alkenylene, > O, > N-R, > C (-R) ₂ 、＞Si(-R) ₂ Is greater than S orR > N-R, said > Si (-R) ₂ R of (b) and said > C (-R) ₂ Each R of (A) is independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, > Si (-R) ₂ Two R of (a) and said > C (-R) ₂ The two R's are not bonded to each other to form a ring, or are bonded to each other to form a ring, the R > N-R, the R > C (-R) ₂ R of (a) and said > Si (-R) ₂ Each of at least one R is independently of C-R ^Z R in Z of (A) ^Z Does not utilize-O-, -S-, -C (-R) ₂ -or a single bond, or with-O-, -S-, -C (-R) ₂ -or a single bond to a substrate,

n, m, q and R are each independently 0 or 1, and in the case of 0, each independently means R ¹ In place of L ¹ 、L ² 、L ³ Or L ⁴ And wherein n + m is 1 and is not q + r is 0,

z is each independently N or C-R ¹ Or each Z ═ Z is independently > O, > N-R, > C (-R) ₂ 、＞Si(-R) ₂ S or Se, the C-R ¹ R of (A) to (B) ¹ Independently of one another, hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboron, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio or substituted silyl, at least one of which is unsubstituted or substituted by aryl, heteroaryl, diarylamino, alkyl, cycloalkyl or substituted silyl, the two aryl radicals of the diarylamino radical being unbound to one another or bound via a linking group, the two heteroaryl radicals of the diheteroarylamino radical being unbound to one another or bound via a linking group, the aryl and heteroaryl radicals of the arylheteroarylamino radical being unbound to one another or bound via a linking group, the two aryl radicals of the diarylboron radical being unbound to one another or bound via a single bond or a linking group,

Two adjacent R ¹ Are not bonded to each other to form an aryl or heteroaryl ring, or are bonded to each other to form an aryl ring or(ii) a heteroaryl ring, at least one hydrogen of the aryl ring formed and the heteroaryl ring formed being unsubstituted or substituted, respectively, with at least one hydrogen of them being unsubstituted or substituted or with a linking group, and the two heteroaryl groups of the diarylamino group being unbound or bound to one another or bound via a linking group, and the aryl and heteroaryl groups of the arylheteroarylamino group being unbound or bound to one another or bound via a linking group, and the two aryl groups of the diarylboron group being unbound or bound to one another, or bonded via a single bond or a linking group, the > N-R, the > C (-R) ₂ And said > Si (-R) ₂ Each R of (A) is independently hydrogen, aryl, heteroaryl, alkyl, cycloalkyl, at least one of which is hydrogen unsubstituted or substituted with aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, said > C (-R) ₂ And said > Si (-R) ₂ Two R's are not bonded to each other to form a ring, or are bonded to each other to form a ring,

a polycyclic aromatic compound having one or more than two structures containing a structural unit represented by the formula (1a-1) is not condensed with at least one cycloalkane, or is condensed with at least one cycloalkane, at least one hydrogen in the cycloalkane being unsubstituted or substituted, at least one-CH in the cycloalkane being unsubstituted or substituted ₂ -is unsubstituted or substituted by-O-or-S-, and,

3. The polycyclic aromatic compound according to claim 1, wherein the structural units are each a structural unit represented by the following formula (1b-1) or formula (1b-2),

in the formulae (1b-1) and (1b-2),

L ³ 、L ⁴ independently of one another, is a single bond, an arylene group, a heteroarylene group or an alkenylene group, at least one of the hydrogens of which is unsubstituted or substituted by an alkyl group, a cycloalkyl group, a diarylamino group, or a substituted silyl group, the two aryl groups of the diarylamino group being bonded without or via a linking group,

z is each independently N or C-R ¹ Or each Z ═ Z is independently > O, > N-R, > C (-R) ₂ 、＞Si(-R) ₂ S or Se, the C-R ¹ R of (A) ¹ Independently of one another, hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboron, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio or substituted silyl, at least one of which is unsubstituted or substituted by aryl, heteroaryl, diarylamino, alkyl, cycloalkyl or substituted silyl, the two aryl radicals of the diarylamino radical being unbound to one another or bound via a linking group, the two heteroaryl radicals of the diheteroarylamino radical being unbound to one another or bound via a linking group, the aryl and heteroaryl radicals of the arylheteroarylamino radical being unbound to one another or bound via a linking group, the two aryl radicals of the diarylboron radical being unbound to one another or bound via a single bond or a linking group,

Two adjacent R ¹ At least one hydrogen of the aryl ring formed and the heteroaryl ring formed is unsubstituted or substituted by aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboron, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio or substituted silyl, at least one hydrogen of which is unsubstituted or substituted by aryl, heteroaryl, diarylamino, alkyl, cycloalkyl or substituted silyl, the two aryl groups of the diarylamino groups being unbound to one another or bound via a linking group, the two heteroaryl groups of the diheteroarylamino groups being unbound or bound via a linking group, the aryl and heteroaryl groups of the arylheteroarylamino groups being unbound to one another, or bonded via a linking group, the two aryl groups of the diarylboron group being not bonded to each other, or bonded via a single bond or a linking group, the > N-R, the > C (-R) ₂ And said > Si (-R) ₂ Each R of (A) is independently hydrogen, aryl, heteroaryl, alkyl, cycloalkyl, at least one of which hydrogen is unsubstituted or substituted by aryl, heteroaryl, diarylamino, alkyl, cycloalkyl or substituted silyl, > C (-R) ₂ And said > Si (-R) ₂ Two R's are not bonded to each other to form a ring, or are bonded to each other to form a ring,

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

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

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

z is each independently N or C-R ¹ Or each Z ═ Z is independently > O, > N-R, > C (-R) ₂ 、＞Si(-R) ₂ S or Se, the C-R ¹ R of (A) to (B) ¹ Each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboron, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio or substituted silyl, at least one of which is unsubstituted or substituted by aryl, heteroaryl, diarylamino, alkyl, cycloalkyl or substituted silyl, the two aryl radicals of the diarylamino radical being unbound to one another or bound via a linking group, the two heteroaryl radicals of the diheteroarylamino radical being unbound to one another or bound via a linking group, the aryl and heteroaryl radicals of the arylheteroarylamino radical being unbound to one another or bound via a linking group, the two aryl radicals of the diarylboron radical being unbound to one another or bound via a single bond or a linking group,

Two adjacent R ¹ Are not bonded to each other to form an aryl or heteroaryl ring, or are bonded to each other to form an aryl or heteroaryl ring, at least one hydrogen of the aryl ring formed and the heteroaryl ring formed, respectively, being unsubstituted or substituted by aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboron, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio or substituted silyl, at least one hydrogen of them being unsubstituted or substituted by aryl, heteroaryl, diarylamino, alkyl, cycloalkyl or substituted silyl, the two aryl groups of the diarylamino group being unbound or bound via a linking group, the two heteroaryl groups of the diarylamino group being bound to each other to form an aryl or heteroaryl ring, the two hydrogen of the heteroaryl ring being unsubstituted or substituted by silyl groupsThe aryl and heteroaryl groups of the arylheteroarylamino group are not bonded to each other or bonded via a linking group, the two aryl groups of the diarylboron group are not bonded to each other or bonded via a single bond or a linking group, the > N-R, the > C (-R) ₂ And said > Si (-R) ₂ Each R of (A) is independently hydrogen, aryl, heteroaryl, alkyl, cycloalkyl, at least one of which is hydrogen unsubstituted or substituted with aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, said > C (-R) ₂ And said > Si (-R) ₂ Two R's are not bonded to each other to form a ring, or are bonded to each other to form a ring;

a polycyclic aromatic compound having one or more structures containing a structural unit represented by formula (1c-1), formula (1c-2), formula (1c-3), or formula (1c-4) is not condensed with at least one cycloalkane, at least one hydrogen in the cycloalkane being unsubstituted or substituted, at least one-CH in the cycloalkane being unsubstituted or substituted ₂ -is unsubstituted-O-or-S-substituted, or is substituted, 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 claim 1, wherein the structural unit is a structural unit represented by the formula (1d-1) or the formula (1d-2),

in the formulae (1d-1) and (1d-2),

L ³ 、L ⁴ each independently a single bond, arylene, heteroarylene, or alkenylene, at least one of which is hydrogen unsubstituted or substituted with alkyl, cycloalkyl, diarylamino, or substituted silyl, two aryl groups of the diarylamino group being not bound by a linking group, orWhich is bonded through the linking group,

z is each independently N or C-R ¹ Or Z is independently > O, > N-R, > C (-R) ₂ 、＞Si(-R) ₂ S or Se, the C-R ¹ R of (A) to (B) ¹ Independently of one another, hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboron, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio or substituted silyl, at least one of which is unsubstituted or substituted by aryl, heteroaryl, diarylamino, alkyl, cycloalkyl or substituted silyl, the two aryl radicals of the diarylamino radical being unbound to one another or bound via a linking group, the two heteroaryl radicals of the diheteroarylamino radical being unbound to one another or bound via a linking group, the aryl and heteroaryl radicals of the arylheteroarylamino radical being unbound to one another or bound via a linking group, the two aryl radicals of the diarylboron radical being unbound to one another or bound via a single bond or a linking group,

Two adjacent R ¹ Are not bonded to each other to form an aryl or heteroaryl ring, or are bonded to each other to form an aryl or heteroaryl ring, at least one hydrogen of the aryl ring formed and the heteroaryl ring formed, respectively, being unsubstituted or substituted by aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboron, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio or substituted silyl, or at least one hydrogen of them being unsubstituted or substituted by aryl, heteroaryl, diarylamino, alkyl, cycloalkyl or substituted silyl, orSubstituted, the two aryl groups of the diarylamino group being not bonded to each other or bonded via a linking group, the two heteroaryl groups of the diheteroarylamino group being not bonded to each other or bonded via a linking group, the aryl and heteroaryl groups of the arylheteroarylamino group being not bonded to each other or bonded via a linking group, the two aryl groups of the diarylboron group being not bonded to each other or bonded via a single bond or a linking group, > N-R, > C (-R) ₂ And said > Si (-R) ₂ Each R of (A) is independently hydrogen, aryl, heteroaryl, alkyl, cycloalkyl, at least one of which hydrogen is unsubstituted or substituted by aryl, heteroaryl, diarylamino, alkyl, cycloalkyl or substituted silyl, > C (-R) ₂ And said > Si (-R) ₂ Two R's are not bonded to each other to form a ring, or are bonded to each other to form a ring,

R ^d independently of one another, hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboron, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio or substituted silyl, at least one of which hydrogen is unsubstituted or substituted by aryl, heteroaryl, diarylamino, alkyl, cycloalkyl or substituted silyl, the two aryl radicals of the diarylamino radical being unbound to one another or bound via a linking group, the two heteroaryl radicals of the diheteroarylamino radical being unbound to one another or bound via a linking group, the aryl and heteroaryl radicals of the arylheteroarylamino radical being unbound to one another or bound via a linking group, the two aryl radicals of the diarylboron radical being unbound to one another or bound via a single bond or a linking group,

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

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

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

z is each independently N or C-R ¹ Or Z is independently > O, > N-R, > C (-R) ₂ 、＞Si(-R) ₂ S or Se, the C-R ¹ R of (A) ¹ Each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboron, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio or substituted silyl, at least one of which is unsubstituted or substituted by aryl, heteroaryl, diarylamino, alkyl, cycloalkyl or substituted silyl, the two aryl radicals of the diarylamino radical being unbound to one another or bound via a linking group, the two heteroaryl radicals of the diheteroarylamino radical being unbound to one another or bound via a linking group, the aryl and heteroaryl radicals of the arylheteroarylamino radical being unbound to one another or bound via a linking group, the two aryl radicals of the diarylboron radical being unbound to one another or bound via a single bond or a linking group,

Two adjacent R ¹ Are not bonded to each other to form an aryl ring or heteroaryl ring, or are bonded to each other to form an aryl ring or heteroaryl ring, at least one hydrogen of the aryl ring formed and the heteroaryl ring formed, respectively, being unsubstituted or substituted by aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboron, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or substituted silyl, at least one hydrogen of which beingUnsubstituted or substituted aryl, heteroaryl, diarylamino, alkyl, cycloalkyl or substituted silyl, the two aryl radicals of the diarylamino being not bonded to one another or bonded via a linking group, the two heteroaryl radicals of the diheteroarylamino being not bonded to one another or bonded via a linking group, the aryl and heteroaryl radicals of the arylheteroarylamino being not bonded to one another or bonded via a linking group, the two aryl radicals of the diarylboron being not bonded to one another or bonded via a single bond or a linking group, the > N-R, the > C (-R) ₂ And said > Si (-R) ₂ Each R of (A) is independently hydrogen, aryl, heteroaryl, alkyl, cycloalkyl, at least one of which hydrogen is unsubstituted or substituted by aryl, heteroaryl, diarylamino, alkyl, cycloalkyl or substituted silyl, > C (-R) ₂ And said > Si (-R) ₂ Two R's are not bonded to each other to form a ring, or are bonded to each other to form a ring,

R ^d each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboron, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio or substituted silyl, at least one of which is unsubstituted or substituted by aryl, heteroaryl, diarylamino, alkyl, cycloalkyl or substituted silyl, the two aryl radicals of the diarylamino radical being unbound to one another or bound via a linking group, the two heteroaryl radicals of the diheteroarylamino radical being unbound to one another or bound via a linking group, the aryl and heteroaryl radicals of the arylheteroarylamino radical being unbound to one another or bound via a linking group, the two aryl radicals of the diarylboron radical being unbound to one another or bound via a single bond or a linking group,

a polycyclic aromatic compound having one or more structures containing a structural unit represented by formula (1e-1), formula (1e-2), formula (1e-3), or formula (1e-4) is not condensed with at least one cycloalkane, at least one hydrogen in the cycloalkane being unsubstituted or substituted, at least one-CH in the cycloalkane being unsubstituted or substituted ₂ -without-O-or-S-substituted, or substituted, and,

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

in the formulae (1f-1) and (1f-2),

x is an integer of 1 to 3,

L ¹ 、L ² 、L ³ and L ⁴ Independently of one another, a single bond, substituted or unsubstituted arylene, substituted or unsubstituted heteroarylene, substituted or unsubstituted alkylene, substituted or unsubstituted cycloalkylene, substituted or unsubstituted alkenylene, > O, > N-R, > C (-R) ₂ 、＞Si(-R) ₂ R > N-R, said > Si (-R) ₂ R of (b) and said > C (-R) ₂ Each R of (A) is independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, > Si (-R) ₂ Two R of (a) and said > C (-R) ₂ Two R's are not bonded to each other to form a ring, or are bonded to each other to form a ring, R > N-R, the > C (-R) ₂ R of (b) and said > Si (-R) ₂ Each of at least one R independently of the others is as C-R ^Z R in Z of (A) ^Z At least one of-O-, -S-, -C (-R) ₂ -or a single bond, or by-O-, -S-, -C (-R) ₂ -or a single bond to a substrate,

e is independently > O, > N-R, > C (-R) ₂ 、＞Si(-R) ₂ R > N-R, said > Si (-R) ₂ R of (b) and said > C (-R) ₂ Each R of (A) is independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, > Si (-R) ₂ Two R of (a) and said > C (-R) ₂ Two R's are not bonded to each other to form a ring, or are bonded to each other to form a ring,

z is each independently N or C-R ¹ Or Z is independently > O, > N-R, > C (-R) ₂ 、＞Si(-R) ₂ S or Se, the C-R ¹ R of (A) ¹ Independently of one another, hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboron, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio or substituted silyl, at least one of which hydrogen is unsubstituted or substituted by aryl, heteroaryl, diarylamino, alkyl, cycloalkyl or substituted silyl, the two aryl radicals of the diarylamino radical being unbound to one another or bound via a linking group, the two heteroaryl radicals of the diheteroarylamino radical being unbound to one another or bound via a linking group, the aryl and heteroaryl radicals of the arylheteroarylamino radical being unbound to one another or bound via a linking group, the two aryl radicals of the diarylboron radical being unbound to one another or bound via a single bond or a substituted silyl radicalA linking group is bonded to the base,

a polycyclic aromatic compound having one or more structures containing structural units represented by the formulae (1f-1) and (1f-2) is not condensed with at least one cycloalkane, or is condensed with at least one cycloalkane, at least one hydrogen in the cycloalkane being unsubstituted or substituted, at least one-CH in the cycloalkane being unsubstituted or substituted ₂ -is unsubstituted-O-or-S-substituted, or is substituted, and,

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

8. The polycyclic aromatic compound according to claim 1, wherein the structural units are each a structural unit represented by the following formula (1g-1) or formula (1g-2),

in the formulae (1g-1) and (1g-2),

x is an integer of 1 to 3,

L ³ 、L ⁴ each independently a single bond, arylene, heteroarylene, or alkenylene, at least one of which is hydrogen unsubstituted or substituted with alkyl, cycloalkyl, diarylamino, or substituted silyl, two aryl groups of the diarylamino group being bonded without or via a linking group,

e is independently > O, > N-R, > C (-R) ₂ 、＞Si(-R) ₂ R > N-R, said > Si (-R) ₂ R of (b) and said > C (-R) ₂ Each R of (A) is independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, > Si (-R) ₂ Two R of (a) and said > C (-R) ₂ Two R's are not bonded to each other to form a ring, or are bonded to each otherSo as to form a ring,

two adjacent R ¹ At least one hydrogen of the aryl ring formed and the heteroaryl ring formed is unsubstituted or substituted by aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboron, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio or substituted silyl, at least one hydrogen of which is unsubstituted or substituted by aryl, heteroaryl, diarylamino, alkyl, cycloalkyl or substituted silyl, the two aryl groups of the diarylamino groups being unbound to one another or bound via a linking group, the two heteroaryl groups of the diheteroarylamino groups being unbound or bound via a linking group, the aryl and heteroaryl groups of the arylheteroarylamino groups being unbound to one another, or bonded via a linking group, the two aryl groups of the diarylboron group being not bonded to each other, or bonded via a single bond or a linking group, the > N-R, the > C (-R) ₂ And said > Si (-R) ₂ R of (A) are each independently hydrogen,Aryl, heteroaryl, alkyl, cycloalkyl, wherein at least one hydrogen is unsubstituted or substituted by aryl, heteroaryl, diarylamino, alkyl, cycloalkyl or substituted silyl, > C (-R) ₂ And said > Si (-R) ₂ Two R's are not bonded to each other to form a ring, or are bonded to each other to form a ring,

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

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

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

x is an integer of 1 to 3,

e is independently > O, > N-R, > C (-R) ₂ 、＞Si(-R) ₂ R > N-R, said > Si (-R) ₂ R of (b) and said > C (-R) ₂ Each R of (A) is independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, orSubstituted or unsubstituted cycloalkyl, said > Si (-R) ₂ Two R of (a) and said > C (-R) ₂ Two R's are not bonded to each other to form a ring, or are bonded to each other to form a ring,

Two adjacent R ¹ At least one hydrogen of the aryl ring formed and the heteroaryl ring formed is unsubstituted or substituted by aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboron, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio or substituted silyl, at least one hydrogen of which is unsubstituted or substituted by aryl, heteroaryl, diarylamino, alkyl, cycloalkyl or substituted silyl, the two aryl groups of the diarylamino groups being unbound to one another or bound via a linking group, the two heteroaryl groups of the diheteroarylamino groups being unbound or bound via a linking group, the aryl and heteroaryl groups of the arylheteroarylamino groups being unbound to one another, or two aryl radicals bonded via a linking group, said diarylboron radicalThe radicals are not bonded to one another or are bonded via single bonds or linking groups, the > N-R, the > C (-R) ₂ And said > Si (-R) ₂ Each R of (A) is independently hydrogen, aryl, heteroaryl, alkyl, cycloalkyl, at least one of which is hydrogen unsubstituted or substituted with aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, said > C (-R) ₂ And said > Si (-R) ₂ Two R's are not bonded to each other to form a ring, or are bonded to each other to form a ring,

a polycyclic aromatic compound having a structure containing one or more than two structural units represented by the formula (1h-1), the formula (1h-2), the formula (1h-3) or the formula (1h-4) is not condensed with at least one cycloalkane in which at least one hydrogen is unsubstituted or substituted, or is condensed with at least one cycloalkane in which at least one-CH is present ₂ -is unsubstituted-O-or-S-substituted, or is substituted, and,

at least one hydrogen in the structure represented by formula (1h-1), formula (1h-2), formula (1h-3) or formula (1h-4) is unsubstituted or substituted with cyano, halogen or deuterium.

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

in the formulae (1i-1) and (1i-2),

x is an integer of 1 to 3,

q and r are each independently 0 or 1, and in the case of 0, each is independentlyUpright finger R ¹ In place of L ³ Or L ⁴ And wherein q + r is not 0,

z is each independently N or C-R ¹ Or each Z ═ Z is independently > O, > N-R, > C (-R) ₂ 、＞Si(-R) ₂ S or Se, the C-R ¹ R of (A) to (B) ¹ Independently of one another, hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboron, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio or substituted silyl, at least one hydrogen of which is unsubstituted or substituted by aryl, heteroaryl, diarylamino, alkyl, cycloalkyl or substituted silyl, the two aryl radicals of the diarylamino radical being unbound to one another or bound via a linking group, the two heteroaryl radicals of the diheteroarylamino radical being unbound to one another or bound via a linking group, the aryl and heteroaryl radicals of the arylheteroarylamino radical being unbound to one another or bound via a linking group, the two aryl radicals of the diarylboron radical being bound to one another or bound via a linking groupThe radicals are not bonded to one another or are bonded via single bonds or linking groups,

two adjacent R ¹ (ii) are not bonded to each other to form an aryl or heteroaryl ring, or are bonded to each other to form an aryl or heteroaryl ring, at least one hydrogen of the aryl ring formed and the heteroaryl ring formed, respectively, is not substituted by aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboron, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio, or substituted silyl, or is substituted, at least one hydrogen of them is not substituted by aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, or substituted silyl, the two aryl groups of the diarylamino groups are not bonded to each other or are bonded via a linking group, the two heteroaryl groups of the diheteroarylamino groups are not bonded to each other or are bonded via a linking group, the aryl and heteroaryl groups of the arylheteroarylamino groups are not bonded to each other, or bonded via a linking group, the two aryl groups of the diarylboron group being not bonded to each other, or bonded via a single bond or a linking group, the > N-R, the > C (-R) ₂ And said > Si (-R) ₂ Each R of (A) is independently hydrogen, aryl, heteroaryl, alkyl, cycloalkyl, at least one of which hydrogen is unsubstituted or substituted by aryl, heteroaryl, diarylamino, alkyl, cycloalkyl or substituted silyl, > C (-R) ₂ And said > Si (-R) ₂ Two R's are not bonded to each other to form a ring, or are bonded to each other to form a ring,

R ^d each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboron, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio or substituted silyl, at least one of which is unsubstituted or substituted by aryl, heteroaryl, diarylamino, alkyl, cycloalkyl or substituted silyl, the two aryl radicals of the diarylamino radical being unbound to one another or bound via a linking group, the two heteroaryl radicals of the diheteroarylamino radical being unbound to one another or bound via a linking group, the aryl radicals being bound to one another or to one another via a linking groupThe aryl and heteroaryl groups of the heteroarylamino group are not bonded to each other or are bonded via a linking group, the two aryl groups of the diarylboron group are not bonded to each other or are bonded via a single bond or a linking group,

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

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

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

x is an integer of 1 to 3,

e is independently > O, > N-R, > C (-R) ₂ 、＞Si(-R) ₂ R > N-R, said > Si (-R) ₂ R of (b) and said > C (-R) ₂ Each R of (A) is independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, > Si (-R) ₂ Two R of (a) and said > C (-R) ₂ Two R's are not bonded to each otherForm a ring, or bond each other to form a ring,

z is each independently N or C-R ¹ Or Z is independently > O, > N-R, > C (-R) ₂ 、＞Si(-R) ₂ S or Se, the C-R ¹ R of (A) to (B) ¹ Each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboron, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio or substituted silyl, at least one of which is unsubstituted or substituted by aryl, heteroaryl, diarylamino, alkyl, cycloalkyl or substituted silyl, the two aryl radicals of the diarylamino radical being unbound to one another or bound via a linking group, the two heteroaryl radicals of the diheteroarylamino radical being unbound to one another or bound via a linking group, the aryl and heteroaryl radicals of the arylheteroarylamino radical being unbound to one another or bound via a linking group, the two aryl radicals of the diarylboron radical being unbound to one another or bound via a single bond or a linking group,

a polycyclic aromatic compound having a structure containing one or more than two structural units represented by formula (1k-1), formula (1k-2), formula (1k-3) or formula (1k-4) is not condensed with at least one cycloalkane in which at least one hydrogen is unsubstituted or substituted, or is condensed with at least one cycloalkane in which at least one-CH is present ₂ -is unsubstituted-O-or-S-substituted, or is substituted, and,

at least one hydrogen in the structure represented by formula (1k-1), formula (1k-2), formula (1k-3) or formula (1k-4) is unsubstituted or substituted with cyano, halogen or deuterium.

12. The polycyclic aromatic compound according to claim 1, represented by any one of the following structural formulae,

in the formula, tBu is tert-butyl.

13. The polycyclic aromatic compound according to claim 1, represented by any one of the following structural formulae,

14. a material for organic devices, comprising the polycyclic aromatic compound according to any one of claims 1 to 13.

15. An organic electroluminescent element comprising: a pair of electrodes including an anode and a cathode; and a light-emitting layer which is disposed between the pair of electrodes and contains the polycyclic aromatic compound according to any one of claims 1 to 13.

16. The organic electroluminescent element according to claim 15, wherein the light-emitting layer comprises a host and the polycyclic aromatic compound as a dopant.

17. A display device comprising the organic electroluminescent element according to any one of claims 15 or 16.

18. A lighting device comprising the organic electroluminescent element as claimed in any one of claims 15 or 16.