CN112838168A

CN112838168A - Organic electroluminescent element, display device, lighting device, and benzanthracene compound

Info

Publication number: CN112838168A
Application number: CN202011305248.0A
Authority: CN
Inventors: 畠山琢次; 藤田幸宏; 枝连一志; 田岛晶夫
Original assignee: Kansai College; JNC Corp
Current assignee: Kwansei Gakuin Educational Foundation; SK Materials JNC Co Ltd
Priority date: 2019-11-22
Filing date: 2020-11-19
Publication date: 2021-05-25
Also published as: JP7611544B2; JP2025038105A; JP2021090050A; KR20210064078A

Abstract

The present invention relates to an organic electroluminescent element, a display device, a lighting device and a benzanthracene compound. Furthermore, the present invention relates to an organic electroluminescence element having a light-emitting layer including a benzanthracene compound represented by the formula (1) and a dopant material of the formula ( 2) The represented polycyclic aromatic compound or a multimer thereof.

Description

Organic electroluminescent element, display device, lighting device, and benzanthracene compound

Technical Field

The present invention relates to an organic electroluminescent element, and a display device and a lighting device using the same. In addition, the present invention relates to a benzanthracene compound useful as a light-emitting material.

Background

Conventionally, display devices using light emitting elements that emit light in an electric field have been studied in various ways because they can achieve power saving and reduction in thickness, and organic electric field light emitting elements (hereinafter, sometimes referred to as "organic el (electroluminescence) elements") including organic materials have been studied actively because they are easy to reduce the weight and increase the 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 a combination of a plurality of materials having the most preferable light-emitting characteristics, both of high molecular compounds and low molecular compounds have been actively studied so far.

The organic EL element has a structure including: a pair of electrodes including an anode and a cathode, and one or more layers which are disposed between the pair of electrodes and include an organic compound. Among the layers containing an organic compound, there are a light-emitting layer, a charge transporting/injecting layer which transports or injects charges such as holes and electrons, and various organic materials suitable for these layers have been developed.

Patent documents 1 to 3 describe the use of a benzanthracene compound as a light-emitting material of an organic electroluminescent element, and patent document 3 discloses the use of a benzanthracene compound as a host material in a light-emitting layer of an organic electroluminescent element.

In recent years, polycyclic aromatic compounds obtained by condensing a plurality of aromatic rings with boron or the like as a central atom have been reported as materials for organic electroluminescent elements (patent document 4).

[ Prior art documents ]

[ patent document ]

[ patent document 1] Japanese patent application laid-open No. 2000-178548

[ patent document 2] Japanese patent laid-open No. 2007 and 277113

[ patent document 3] International publication No. 2009/081776

[ patent document 4] 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 EL devices, but in order to increase the options for materials for organic EL devices, it is desired to develop a material containing a compound different from the conventional materials. The problem of the present invention is to provide an organic EL element using a combination of new materials. The problem of the present invention is to provide an organic EL element having high external quantum efficiency.

[ means for solving problems ]

The present inventors have made extensive studies to solve the above problems, and as a result, have found that an excellent organic EL element can be obtained by using a light-emitting layer containing a specific benzanthracene compound as a host material and a polycyclic aromatic compound in which a plurality of aromatic rings are condensed as a dopant material, and have completed the present invention. That is, the present invention provides the following organic electroluminescent element and benzanthracene compound.

< 1 > 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, wherein the light-emitting layer contains a benzanthracene compound represented by formula (1) below as a host material and a polycyclic aromatic compound represented by formula (2) below or a polymer of polycyclic aromatic compounds having a plurality of structures represented by formula (2) below as a dopant material.

(in the formula (1),

X_a、X_b、Ar⁴、Ar⁵、Ar⁶、Ar⁷、Ar⁸、Ar⁹、Ar¹⁰、Ar¹¹、Ar¹²and Ar¹³Each independently is hydrogen, 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, X_a、X_b、Ar⁴、Ar⁵、Ar⁶、Ar⁷、Ar⁸、Ar⁹、Ar¹⁰、Ar¹¹、Ar¹²And Ar¹³Not all of them may be simultaneously hydrogen, at least one hydrogen in the compound represented by the formula (1) may be substituted by halogen, cyano or deuterium)

(in the formula (2),

ring A, ring B and ring C are each independently an aryl or heteroaryl ring, at least one hydrogen in these rings may be substituted,

X¹and X²Independently of each other > O, > N-R, > C (-R)₂R > N-R may be optionally substitutedSubstituted aryl, optionally substituted heteroaryl, optionally substituted alkyl or optionally substituted cycloalkyl, > C (-R)₂R of (a) is hydrogen, optionally substituted aryl, optionally substituted alkyl or optionally substituted cycloalkyl, and additionally, said R > N-R and/or said > C (-R)₂R of (A) may be bonded to the A ring, the B ring and/or the C ring through a linking group or a single bond,

At least one selected from the group consisting of an aryl ring and a heteroaryl ring in the compound represented by formula (2) or a multimer thereof may be condensed with at least one cycloalkane, at least one hydrogen in the cycloalkane may be substituted, at least one-CH in the cycloalkane₂-may be substituted by-O-,

at least one hydrogen in the compound or structure represented by formula (2) may be substituted with deuterium, cyano or halogen)

< 2 > the organic electroluminescent element according to < 1 > wherein,

in the formula (2), the reaction mixture is,

the A, B and C rings are each independently an aryl or heteroaryl ring, at least one hydrogen in these rings may be substituted by a substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, or substituted or unsubstituted aryloxy, and further, these rings have a substituent comprising a boron atom, X, and¹and X²The condensed bicyclic structure at the center of formula (2) has a 5-or 6-membered ring bonded thereto in common,

X¹And X²Independently of each other > O, > N-R, > C (-R)₂R > N-R is aryl which may be substituted by alkyl or cycloalkyl, heteroaryl which may be substituted by alkyl or cycloalkyl, > C (-R)₂R of (a) is hydrogen, aryl which may be substituted by alkyl or cycloalkyl, and additionally, said R > N-R and/or said > C (-R)₂R of (a) can be represented by-O-, -S-, -C (-R)₂-or a single bond to the A ring, B ring and/or C ring, the-C (-R)₂R of-is hydrogen, alkyl or cycloalkyl,

at least one hydrogen in the compound or structure represented by formula (2) may be substituted with deuterium, cyano or halogen,

in the case of multimers, dimers or trimers having 2 or 3 structures represented by formula (2).

< 3 > the organic electroluminescent element according to < 1 >, wherein the polycyclic aromatic compound or the multimer thereof is a polycyclic aromatic compound represented by formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e) or formula (2-f) or a multimer of a polycyclic aromatic compound having a plurality of structures represented by formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e) or formula (2-f).

(in the formula (2-a), the formula (2-b), the formula (2-c), the formula (2-d), the formula (2-e) and the formula (2-f),

R¹、R²、R³、R⁴、R⁵、R⁶、R⁷、R⁸、R⁹、R¹⁰and R¹¹Each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryl groups may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyl, at least one of which may be substituted with aryl, heteroaryl, alkyl, cycloalkyl, or substituted silyl, and R¹～R¹¹Can be bonded to each other and together with the a-, b-or c-ring form an aryl or heteroaryl ringA cyclic ring, at least one hydrogen in the formed cyclic ring may be substituted by an aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryl groups may be bonded via a single bond or a linking group), an alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyl group, at least one hydrogen of which may be substituted by an aryl, heteroaryl, alkyl, cycloalkyl, or substituted silyl group,

X_xeach independently > O, > S, > N-R or > C (-R)₂R of said > N-R is optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl or optionally substituted cycloalkyl, and additionally said > C (-R) ₂Each R of (A) is independently hydrogen, aryl which may be substituted with alkyl or cycloalkyl, heteroaryl which may be substituted with alkyl or cycloalkyl,

X¹and X²Independently of each other > O, > N-R, > C (-R)₂And & gt S or & gt Se, wherein R & gt N-R is C (-R), R is C6-12 aryl which may be substituted by C1-6 alkyl or C3-14 cycloalkyl, R is C2-15 heteroaryl which may be substituted by C1-6 alkyl or C3-14 cycloalkyl, C1-6 alkyl or C3-14 cycloalkyl₂R in (b) is hydrogen, an aryl group having 6 to 12 carbon atoms which may be substituted with an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 14 carbon atoms, and R > N-R and/or C (-R)₂R of (a) can be represented by-O-, -S-, -C (-R)₂-or a single bond to the a-ring, b-ring and/or C-ring, the-C (-R)₂R is C1-C6 alkyl or C3-C14 cycloalkyl,

at least one selected from the group consisting of an aryl ring and a heteroaryl ring in a compound represented by formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e) or formula (2-f) or a multimer thereof may be condensed with at least one cycloalkane, at least one of the cycloalkane may be substituted with hydrogen, and at least one-CH in the cycloalkane may be substituted ₂-may be substituted by-O-,

at least one hydrogen in the compound or structure represented by formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e), or formula (2-f) may be substituted with deuterium, cyano, or halogen,

in the case of multimers, are dimers or trimers having 2 or 3 structures represented by formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e) or formula (2-f)

< 4 > the organic electroluminescent element according to < 3 >, wherein the polycyclic aromatic compound or a multimer thereof is a polycyclic aromatic compound represented by formula (2-a) or a multimer of polycyclic aromatic compounds having a plurality of structures represented by formula (2-a).

< 5 > the organic electroluminescent element according to < 4 >, wherein the polycyclic aromatic compound is represented by any one of the following structural formulae;

in the formula, Me is methyl, tBu is tert-butyl, tAm is tert-amyl, and D is deuterium.

< 6 > the organic electroluminescent element according to < 4 >, wherein the polycyclic aromatic compound is represented by any one of the following structural formulae;

in the formula, Me is methyl, and tBu is tert-butyl.

< 7 > the organic electroluminescent element according to < 3 >, wherein the polycyclic aromatic compound or the multimer thereof is a polycyclic aromatic compound represented by formula (2-b) or a multimer of a plurality of polycyclic aromatic compounds having a structure represented by formula (2-b).

< 8 > the organic electroluminescent element according to < 7 > wherein the polycyclic aromatic compound is represented by any one of the following structural formulae;

in the formula, Me is methyl, and tBu is tert-butyl.

< 9 > the organic electroluminescent element according to any one of < 1 > to < 8 >, wherein,

in the formula (1), the reaction mixture is,

Ar⁴、Ar⁵、Ar⁶、Ar⁷、Ar⁸、Ar⁹、Ar¹⁰、Ar¹¹、Ar¹²、Ar¹³、X_aand X_bEach of which is independently hydrogen, phenyl which may be substituted with any one or more substituents selected from substituent group A, biphenyl which may be substituted with any one or more substituents selected from substituent group A, terphenyl which may be substituted with any one or more substituents selected from substituent group A, quaterphenyl which may be substituted with any one or more substituents selected from substituent group A, naphthyl which may be substituted with any one or more substituents selected from substituent group A, phenalkenyl which may be substituted with any one or more substituents selected from substituent group A, phenanthrenyl which may be substituted with any one or more substituents selected from substituent group A, fluorenyl which may be substituted with any one or more substituents selected from substituent group A, benzofluorenyl, which may be substituted with any one or more substituents selected from substituent group A, benzofluorenyl, biphenyl which may be substituted with any one or more substituents selected from substituent group A, biphenyl, substituted by any one or more substituents selected from substituent group A

A group, a triphenylene group which may be substituted with any one or more substituents selected from the substituent group A, a pyrenyl group which may be substituted with any one or more substituents selected from the substituent group A, an anthracenyl group which may be substituted with any one or more substituents selected from the substituent group A, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a silyl group which may be substituted with an alkyl group having 1 to 4 carbon atoms, a group represented by the following formula (A) or a group represented by the following formula (B),

wherein, X_aAnd X_bBoth of these will not be hydrogen,

substituent group A includes phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, phenalkenyl, phenanthryl, fluorenyl, benzofluorenyl, and,

A group, a triphenylene group, a pyrenyl group, an anthracenyl group, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a silyl group which may be substituted with an alkyl group having 1 to 4 carbon atoms, a group represented by the formula (A) and a group represented by the formula (B),

in the formulae (A) and (B), Y is-O-, -S-or > N-R³⁹，R²¹～R³⁸Each independently 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 substituted, aryloxy which may be substituted, arylthio which may be substituted, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkylbicycloalkylsilyl, amino which may be substituted, halogen, hydroxy or cyano, R ²¹～R³⁸Wherein adjacent groups in (A) may be bonded to each other to form a hydrocarbon ring, an aryl ring or a heteroaryl ring, and at least one hydrogen in the formed hydrocarbon ring, aryl ring or heteroaryl ring may be substituted with an alkyl group which may be substituted, a cycloalkyl group which may be substituted, an aryl group which may be substituted, a heteroaryl group which may be substituted, an alkoxy group which may be substituted, an aryloxy group which may be substituted, an arylthio group which may be substituted, a trialkylsilyl group, a tricycloalkylsilyl group, a dialkylcycloalkylsilyl group, an alkylbicycloalkylsilyl group, an amino group which may be substituted, a halogen, a hydroxyl group or a cyano group, R³⁹Is hydrogen or a substituted aryl group,

the group represented by formula (A) is a group obtained by removing one hydrogen at any position of formula (A), and represents the position,

the group represented by formula (B) is a group obtained by removing one hydrogen at any position of formula (B), and represents the position,

at least one hydrogen in the compound represented by formula (1) may be substituted with halogen, cyano, or deuterium.

< 10 > the organic electroluminescent element according to < 9 >, wherein Ar⁴、Ar⁵、Ar⁶、Ar⁹、Ar¹⁰And Ar¹³Are each hydrogen, Ar⁷、Ar⁸、Ar¹¹、Ar¹²、X_aAnd X_bEach of which is independently hydrogen, phenyl which may be substituted with any one or more substituents selected from substituent group A, biphenyl which may be substituted with any one or more substituents selected from substituent group A, terphenyl which may be substituted with any one or more substituents selected from substituent group A, naphthyl which may be substituted with any one or more substituents selected from substituent group A, phenalkenyl which may be substituted with any one or more substituents selected from substituent group A, phenanthryl which may be substituted with any one or more substituents selected from substituent group A, fluorenyl which may be substituted with any one or more substituents selected from substituent group A, triphenylenyl which may be substituted with any one or more substituents selected from substituent group A, pyrenyl which may be substituted with any one or more substituents selected from substituent group A, triphenylenyl, and the like, An alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a silyl group which may be substituted with an alkyl group having 1 to 4 carbon atoms, a group represented by the formula (A) or a group represented by the formula (B).

< 11 > the organic electroluminescent element according to < 9 > or < 10 >, wherein the group represented by formula (A) is a group represented by any one of formulae (A-1) to (A-14), and the group represented by formula (B) is a group represented by formula (B-1).

(formula (A-1) to formula (A-14) and formula (B-1) wherein Y is-O-, -S-or > N-R³⁹，R³⁹At least one hydrogen in each of the groups represented by the formulae (A-1) to (A-14) and (B-1) may be substituted by 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 diaryl-substituted amino group, a diheteroaryl-substituted amino group, an arylheteroaryl-substituted amino group, a halogen group, a hydroxyl group or a cyano group,

the groups represented by the formulae (A-1) to (A-14) are each a group obtained by removing one hydrogen at any position of the formulae (A-1) to (A-14),

the group represented by the formula (B-1) is a group obtained by removing one hydrogen at any position of the formula (B-1), and represents the position)

< 12 > the organic electroluminescent element according to any one of < 1 > to < 8 >, wherein the compound represented by formula (1) is a compound represented by any one of the following formulae;

In the formula, Me is methyl, and tBu is tert-butyl.

< 13 > the organic electroluminescent element according to any one of < 1 > to < 12 > having an electron transport layer and/or an electron injection layer disposed between the cathode and the light-emitting layer, wherein at least one of the electron transport layer and the electron injection layer contains at least one selected from the group consisting of borane derivatives, pyridine derivatives, fluoranthene derivatives, BO derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, arylnitrile derivatives, triazine derivatives, benzimidazole derivatives, phenanthroline derivatives, and hydroxyquinoline metal complexes.

< 14 > the organic electroluminescent element according to < 13 >, wherein the electron transport layer and/or the electron injection layer further contains at least one selected from the group consisting of alkali metals, alkaline earth metals, rare earth metals, oxides of alkali metals, halides of alkali metals, oxides of alkaline earth metals, halides of alkaline earth metals, oxides of rare earth metals, halides of rare earth metals, organic complexes of alkali metals, organic complexes of alkaline earth metals and organic complexes of rare earth metals.

< 15 > a display device comprising the organic electroluminescent element according to any one of < 1 > to < 14 >.

< 16 > a lighting device comprising the organic electroluminescent element according to any one of < 1 > to < 14 >.

< 17 > a benzanthracene compound represented by the following formula (1');

in the formula (1'), in the presence of a catalyst,

Ar⁴'、Ar⁵'、Ar⁶'、Ar⁷'、Ar⁸'、Ar⁹'、Ar¹⁰'、Ar¹¹'、Ar¹²'、Ar¹³'、X_a' and X_b' are each independently hydrogen, phenyl which may be substituted with at least one substituent selected from substituent group A, or biphenyl which may be substituted with at least one substituent selected from substituent group APhenyl, terphenyl which may be substituted with any one or more substituents selected from substituent group A, naphthyl which may be substituted with any one or more substituents selected from substituent group A, phenalkenyl which may be substituted with any one or more substituents selected from substituent group A, phenanthryl which may be substituted with any one or more substituents selected from substituent group A, fluorenyl which may be substituted with any one or more substituents selected from substituent group A, benzofluorenyl which may be substituted with any one or more substituents selected from substituent group A

wherein, X_a' and X_b' both of these will not be hydrogen,

in the formulae (A) and (B), Y is-O-, -S-or > N-R³⁹，R²¹～R³⁸Each independently is hydrogen, alkyl which may be substituted, cycloalkyl which may be substituted, aryl which may be substituted, hetero which may be substitutedAryl, alkoxy which may be substituted, aryloxy which may be substituted, arylthio which may be substituted, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkylbicycloalkylsilyl, amino which may be substituted, halogen, hydroxy or cyano, R ²¹～R³⁸Wherein adjacent groups in (A) may be bonded to each other to form a hydrocarbon ring, an aryl ring or a heteroaryl ring, and at least one hydrogen in the formed hydrocarbon ring, aryl ring or heteroaryl ring may be substituted with an alkyl group which may be substituted, a cycloalkyl group which may be substituted, an aryl group which may be substituted, a heteroaryl group which may be substituted, an alkoxy group which may be substituted, an aryloxy group which may be substituted, an arylthio group which may be substituted, a trialkylsilyl group, a tricycloalkylsilyl group, a dialkylcycloalkylsilyl group, an alkylbicycloalkylsilyl group, an amino group which may be substituted, a halogen, a hydroxyl group or a cyano group, R³⁹Is hydrogen or a substituted aryl group,

the compound represented by the formula (1') contains at least one group selected from the group consisting of the group represented by the formula (A) and the group represented by the formula (B),

at least one hydrogen in the compound represented by formula (1') may be substituted with halogen, cyano, or deuterium.

< 18 > the benzanthracene compound according to < 17 > wherein,

the formula (A) is any one of the formulae (A-1) to (A-14), the formula (B) is the formula (B-1),

In the formulae (A-1) to (A-14) and (B-1), Y is-O-, -S-or > N-R³⁹，R³⁹Is hydrogen or aryl, at least one hydrogen in each of the groups represented by the formulae (A-1) to (A-14) and (B-1) may be an alkyl group, a cycloalkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryl groupOxy, arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkylbicycloalkylsilyl, diarylsubstituted amino, diheteroarylsubstituted amino, arylheteroaryl substituted amino, halogen, hydroxy or cyano,

the group represented by formula (B-1) is a group obtained by removing one hydrogen at any position of formula (B-1), and represents the position.

< 19 > the benzanthracene compound according to < 17 > or < 18 > which is represented by the following formula (1' a);

in the formula (1' a), the metal oxide,

X_a' and X_b' are each independently hydrogen, a phenyl group which may be substituted with any one or more substituents selected from substituent group A, a biphenyl group which may be substituted with any one or more substituents selected from substituent group A, a naphthyl group which may be substituted with any one or more substituents selected from substituent group A, a phenanthryl group which may be substituted with any one or more substituents selected from substituent group A, a group represented by formula (A) or a group represented by formula (B), X _a' and X_bAt least one of' is a group containing a group represented by the formula (A) or the formula (B),

Ar⁷'、Ar⁸'、Ar¹¹' and Ar¹²' are each independently hydrogen, methyl, tert-butyl, phenyl, biphenyl, or naphthyl,

at least one hydrogen in the compound represented by formula (1' a) may be substituted with halogen, cyano, or deuterium.

< 20 > according to < 19 > saidWherein X is_a' and X_bEither of' is hydrogen.

< 21 > the benzanthracene compound according to < 20 > which is represented by any one of the following formulae.

< 22 > the benzanthracene compound according to < 20 > or < 21 >, wherein, in the formulae (A) and (B), Y is-O-.

< 23 > the benzanthracene compound according to < 20 > or < 21 >, wherein R other than a bond in the formulae (A) and (B)²¹～R³⁸Are all hydrogen.

< 24 > the benzanthracene compound according to < 19 > wherein X_a' and X_b' both are groups containing a group represented by the formula (A) or the formula (B).

< 25 > the benzanthracene compound according to < 24 > which is represented by the following formula.

< 26 > the benzanthracene compound according to < 19 > which is represented by any one of the following formulae.

< 27 > the benzanthracene compound according to < 19 > wherein, with respect to X_a' and X_b'，

Any one of which is a phenyl group substituted with a group represented by the formula (A) or a group represented by the formula (B), and the other is an unsubstituted phenyl group;

Any one of which is a naphthyl group substituted by a group represented by formula (A) or a group represented by formula (B), and the other is a naphthyl group which may be substituted by a group represented by formula (A) or a group represented by formula (B); or

Any one of them is a phenanthryl group substituted with a group represented by formula (a) or a group represented by formula (B), and the other is a phenanthryl group which may be substituted with a group represented by formula (a) or a group represented by formula (B).

< 28 > the benzanthracene compound according to < 27 > represented by any one of the following formulae;

in the formula, tBu is tert-butyl.

< 29 > the benzanthracene compound according to < 17 > or < 18 >, wherein Ar⁵'、Ar⁶'、Ar⁷'、Ar⁸' or Ar⁹' is a group containing a group represented by the formula (A) or the formula (B).

< 30 > the benzanthracene compound according to < 29 > wherein, with respect to X_a' and X_b'，

Any one of them is unsubstituted phenyl, and the other is phenyl which may be substituted with any one or more substituents selected from substituent group a;

each of which is naphthyl that may be substituted by any one or more substituents selected from substituent group a; or

Phenanthryl which may be substituted with any one or more substituents selected from substituent group a,

X_a' and X_b' may be the same or different in the presence or absence and kind of any one or more substituents selected from substituent group A.

< 31 > the benzanthracene compound according to < 30 > which is represented by any one of the following formulae.

< 32 > the benzanthracene compound according to < 30 > or < 31 > wherein Ar⁶'、Ar⁷' or Ar⁸' is a group containing a group represented by the formula (A) or the formula (B).

< 33 > the benzanthracene compound according to < 17 > which is represented by any one of the following formulae;

in the formula, Me is methyl.

[ Effect of the invention ]

The present invention can provide an organic EL device using a combination of new materials. The organic EL element of the present invention has high external quantum efficiency and can realize light emission at low voltage. Further, the present invention can provide a benzanthracene compound which can be used for producing the organic EL device.

Drawings

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

Description of the symbols

100: organic electroluminescent element

101: substrate

102: anode

103: hole injection layer

104: hole transport layer

105: luminescent layer

106: electron transport layer

107: electron injection layer

108: cathode electrode

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 the present specification, the chemical structure or the substituent may be represented by carbon number, but the carbon number when the substituent is substituted on the chemical structure or when the substituent is 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 with the substituent a" means that the substituent a "(not limited to a carbon number) 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.

Organic electroluminescent element

The organic electroluminescent element of the present invention comprises: a pair of electrodes including an anode and a cathode; and a light-emitting layer disposed between the pair of electrodes. Fig. 1 is a schematic cross-sectional view showing an example of an organic EL device of the present invention.

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 element 100 may have a configuration in which the order of production is reversed, for example, the configuration including: the organic light emitting diode comprises a substrate 101, a cathode 108 arranged on the substrate 101, an electron injection layer 107 arranged on the cathode 108, an electron transport layer 106 arranged on the electron injection layer 107, a light emitting layer 105 arranged on the electron transport layer 106, a hole transport layer 104 arranged on the light emitting layer 105, a hole injection layer 103 arranged on the hole transport layer 104, and an anode 102 arranged on the hole injection layer 103.

All of the layers are not indispensable, and the minimum constituent unit is constituted by 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 form of the "substrate/anode/hole injection layer/hole transport layer/light-emitting layer/electron transport layer/electron injection layer/cathode", substrate/anode/hole injection layer/light-emitting layer/electron transport layer/electron injection layer/cathode "," substrate/anode/hole injection layer/hole transport layer/light-emitting layer/electron 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".

1. Light-emitting layer in organic electroluminescent element

The light-emitting layer 105 emits light by recombination of holes injected from the anode 102 and electrons injected from the cathode 108 between the electrodes to which an electric field is supplied. 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.

As the light emission mechanism of the organic EL element, there are mainly two types of light emission, i.e., fluorescence light emission using light emission from an excited singlet state and phosphorescence light emission using light emission from an excited triplet state. The exciton utilization efficiency of a typical fluorescent light-emitting material is low, about 25%. However, the phenomenon of generating singlet excitons from a plurality of Triplet excitons (Triplet-Triplet Fusion) is used, and a maximum of 40% to 62.5% of energy is used for light emission.

There are two cases of generating singlet excitons from triplet excitons: the case of generation on host material molecules and the case of generation on dopant material molecules. At this time, the triplet energy level of the dopant material is preferably higher than that of the host material. If the relation of the triplet energy levels is satisfied, triplet excitons generated on the host material do not migrate to the dopant material having a higher triplet energy. In addition, triplet excitons generated on the dopant material molecules rapidly undergo energy transfer to the host material molecules. That is, triplet excitons of the host material do not migrate to the dopant material and triplet excitons efficiently collide with each other on the host material, whereby singlet excitons can be generated. Further, when the singlet level of the dopant material is lower than the singlet level of the host material, singlet excitons generated by the TTF phenomenon undergo energy transfer from the host material to the dopant material, contributing to fluorescent emission of the dopant material. In addition, the energy transfer from the host to the dopant at this time is a forster type energy transfer. In general, known are: the larger the overlap integral of the fluorescence spectrum of the host and the absorption spectrum of the dopant between the host and the dopant, the more efficiently the forster-type energy transfer occurs.

When the host material that is the benzanthracene compound represented by formula (1) and the dopant material that is the polycyclic aromatic compound having boron represented by formula (2) of the present invention are used, material/element design that satisfies the conditions of the relationship between the appropriate energy levels of the host and the dopant and a large overlap integral intensity of the spectrum can be realized. As a result, the TTF phenomenon can be efficiently generated in the light-emitting layer of the present invention, and favorable element characteristics can be provided.

The light-emitting layer of the organic electroluminescent element of the present invention contains a benzanthracene compound represented by formula (1) as a host material and a polycyclic aromatic compound represented by formula (2) or a polymer of polycyclic aromatic compounds having a plurality of structures represented by formula (2) as a dopant material.

1-1-1 benzanthracene compounds

The benzanthracene compound contained in the light-emitting layer of the organic EL element of the present invention is a compound represented by the following formula (1).

In the formula (1), the reaction mixture is,

X_a、X_b、Ar⁴、Ar⁵、Ar⁶、Ar⁷、Ar⁸、Ar⁹、Ar¹⁰、Ar¹¹、Ar¹²and Ar¹³Each independently is hydrogen, 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, X _a、X_b、Ar⁴、Ar⁵、Ar⁶、Ar⁷、Ar⁸、Ar⁹、Ar¹⁰、Ar¹¹、Ar¹²And Ar¹³Not all of which are hydrogen at the same time, at least one hydrogen in the compound represented by formula (1) may be substituted by halogen, cyano, deuterium, or a substitutable heteroaryl group.

Examples of the "aryl group" of the "aryl group which may be substituted" in the formula (1) include aryl groups having 6 to 30 carbon atoms, preferably aryl groups having 6 to 16 carbon atoms, more preferably aryl groups having 6 to 12 carbon atoms, and particularly preferably aryl groups 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.

Examples of the "heteroaryl group" of the "heteroaryl group which may be substituted" in the formula (1) 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: 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, oxadiazolyl, thianthrenyl, naphthobenzofuryl, naphthobenzothienyl, and the like.

Examples of the "heteroaryl group which may be substituted" include a group represented by the formula (A) and a group represented by the formula (B) which will be described later.

As the aryl or heteroaryl group in each of the "diarylamino group which may be substituted", "diheteroarylamino group which may be substituted", "arylheteroarylamino group which may be substituted" in the formula (1), the group described as "aryl" or "heteroaryl" may be cited.

Specifically, there may be mentioned: diphenylamino, dinaphthylamino, phenylnaphthylamino, bipyrylamino, phenylpyridylamino, naphthylpyridylamino and the like.

The "alkyl group" of the "alkyl group which may be substituted" in the formula (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-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), 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.

Examples of the "cycloalkyl group" of the "optionally substituted cycloalkyl group" in the formula (1) include cycloalkyl groups having 3 to 24 carbon atoms, preferably cycloalkyl groups having 3 to 20 carbon atoms, more preferably cycloalkyl groups having 3 to 16 carbon atoms, still more preferably cycloalkyl groups having 3 to 14 carbon atoms, still more preferably cycloalkyl groups having 5 to 10 carbon atoms, particularly preferably cycloalkyl groups having 5 to 8 carbon atoms, and most preferably cycloalkyl groups having 5 to 6 carbon atoms.

As specific cycloalkyl groups, there may be mentioned: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and alkyl (particularly methyl) substituents having 1 to 4 carbon atoms thereof, or norbornenyl, bicyclo [1.0.1] butyl, bicyclo [1.1.1] pentyl, bicyclo [2.0.1] pentyl, bicyclo [1.2.1] hexyl, bicyclo [3.0.1] hexyl, bicyclo [2.1.2] heptyl, bicyclo [2.2.2] octyl, adamantyl, diamantanyl, decahydronaphthyl, decahydroazulenyl, and the like.

Examples of the "alkenyl group" of the "alkenyl group which may be substituted" in the formula (1) 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 "alkenyl" may include: vinyl, allyl, butadienyl, and the like.

Examples of the "alkoxy group" of the "alkoxy group which may be substituted" in the formula (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 (an alkoxy group having a branched chain having 3 to 18 carbon atoms), more preferably an alkoxy group having 1 to 12 carbon atoms (an alkoxy group having a branched chain having 3 to 12 carbon atoms), yet more preferably an alkoxy group having 1 to 6 carbon atoms (an alkoxy group having a branched chain having 3 to 6 carbon atoms), and particularly preferably an alkoxy group having 1 to 4 carbon atoms (an alkoxy group having a branched chain 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.

The "aryloxy group" of the "aryloxy group which may be substituted" in the formula (1) is a group in which hydrogen of an-OH group is substituted with an aryl group, and the aryl group may refer to the group described as the "aryl group".

The "arylthio group" of the "arylthio group which may be substituted" in the formula (1) is a group in which the hydrogen of the-SH group is substituted with an aryl group, and the description of the aryl group may refer to the description recited as the "aryl group".

Examples of the "silyl group which may be substituted" in the formula (1) include trialkylsilyl groups. The "trialkylsilyl group" includes trialkylsilyl groups in which three hydrogens of the silyl group are independently replaced with an alkyl group, and the description of the alkyl group may refer to the description given as the "alkyl group". Preferred alkyl groups for substitution are alkyl groups having 1 to 4 carbon atoms, and specific examples thereof include: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-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.

With respect to X in the formula (1)_a、X_b、Ar⁴、Ar⁵、Ar⁶、Ar⁷、Ar⁸、Ar⁹、Ar¹⁰、Ar¹¹、Ar¹²And Ar¹³As the substituent in the case of "may be substituted", there may be mentioned: alkyl, aryl or heteroaryl. As the alkyl group, aryl group or heteroaryl group, a group described as "alkyl group", "aryl group" or "heteroaryl group" may be cited. The number of the substituent may be any number up to the maximum number that can be substituted, and is preferably 0 to 3, more preferably 0 to 2, and still more preferably 0 to 1.

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.

In the formula (1), X_a、X_b、Ar⁴、Ar⁵、Ar⁶、Ar⁷、Ar⁸、Ar⁹、Ar¹⁰、Ar¹¹、Ar¹²And Ar¹³Each of which is independently preferably a phenyl group which may be substituted with any one or more substituents selected from substituent group A, a biphenyl group which may be substituted with any one or more substituents selected from substituent group A, a terphenyl group which may be substituted with any one or more substituents selected from substituent group A, a quaterphenyl group which may be substituted with any one or more substituents selected from substituent group A, a naphthyl group which may be substituted with any one or more substituents selected from substituent group A, a phenalkenyl group which may be substituted with any one or more substituents selected from substituent group A, a phenanthryl group which may be substituted with any one or more substituents selected from substituent group A, a fluorenyl group which may be substituted with any one or more substituents selected from substituent group A, a benzofluorenyl group which may be substituted with any one or more substituents selected from substituent group A, Substituted by any one or more substituents selected from substituent group A

A group, a triphenylene group which may be substituted with any one or more substituents selected from the substituent group A, a pyrenyl group which may be substituted with any one or more substituents selected from the substituent group A, an anthracenyl group which may be substituted with any one or more substituents selected from the substituent group A, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a silyl group which may be substituted with an alkyl group having 1 to 4 carbon atoms, a group represented by the following formula (A) or the following formula (B), in which X is a group represented by the formula_aAnd X_bMay be hydrogen.

Here, the substituent group A includes phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, phenalkenyl, phenanthryl, fluorenyl, benzofluorenyl, fluorenyl, and the like,

A phenyl group, a triphenylene group, a pyrenyl group, an anthracenyl group, a group represented by the following formula (A), and a group represented by the following formula (B). The substituent selected from the substituent group A is preferably a phenyl group, a naphthyl group, a phenalkenyl group, a phenanthrenyl group, a fluorenyl group, a triphenylenyl group, a pyrenyl group, a group represented by the following formula (A) or a group represented by the following formula (B), more preferablyPreferably, the group is a phenyl group, a naphthyl group, a phenanthryl group, a fluorenyl group, a group represented by the following formula (A) or a group represented by the following formula (B).

X_aAnd X_bEach of which is independently more preferably a phenyl group which may be substituted with any one or more substituents selected from the substituent group a, a biphenyl group which may be substituted with any one or more substituents selected from the substituent group a, a terphenyl group which may be substituted with any one or more substituents selected from the substituent group a, a naphthyl group which may be substituted with any one or more substituents selected from the substituent group a, a phenalkenyl group which may be substituted with any one or more substituents selected from the substituent group a, a phenanthrenyl group which may be substituted with any one or more substituents selected from the substituent group a, a fluorenyl group which may be substituted with any one or more substituents selected from the substituent group a, a triphenylenyl group which may be substituted with any one or more substituents selected from the substituent group a, a pyrenyl group which may be substituted with any one or more substituents selected from the substituent group a, A group represented by the following formula (A) or a group represented by the following formula (B), in which case X _aAnd X_bMay be hydrogen.

X_aAnd X_bEach of which is independently further preferred is a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthryl group, a fluorenyl group, a triphenylene group, a pyrenyl group, a group represented by the following formula (a) or a group represented by the following formula (B), which may be substituted by any one or more substituents selected from the substituent group a, a naphthyl group, a phenanthryl group, a fluorenyl group, a triphenylene group, a pyrenyl group, a group represented by the following formula (a) or a group represented by the following formula (B), which may be substituted by any one or more substituents selected from the substituent group a.

As an example, in formula (1), X_aAnd X_bEither of the group represented by the formula (a) or the group represented by the formula (B) described later, or the group having the group represented by the formula (a) or the group having the group represented by the formula (B) as a substituent described later is preferred. The group having the group represented by the formula (a) or the formula (B) as a substituent is preferably an aryl group having the group represented by the formula (a) or the formula (B) as a substituent. In addition, in this specificationIn the above description, any group selected from the group consisting of a group represented by the formula (a) or a group represented by the formula (B), and a group having a group represented by the formula (a) as a substituent or a group having a group represented by the formula (B) as a substituent is sometimes referred to as a "group containing a group represented by the formula (a) or the formula (B)". In the formula (1), X _aAnd X_bIt is also preferable that any one of them is hydrogen and the other is a group containing a group represented by the formula (A) or the formula (B).

In the formula (1), X_aAnd X_bEach of the groups is preferably a group represented by any one of the following formulae (1-X1) to (1-X6).

In formulae (1-X1) to (1-X6), a represents a bonding position.

In the formulae (1-X1) to (1-X6), Ar²¹、Ar²²、Ar²³、Ar²⁴、Ar²⁵And Ar²⁶Each independently is hydrogen, phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, or,

A phenyl group, a triphenylene group, a pyrenyl group, an anthracenyl group, a group represented by the formula (A) or a group represented by the formula (B) described later. In the formulae (1-X1) to (1-X6), Ar²¹、Ar²²、Ar²³、Ar²⁴、Ar²⁵And Ar²⁶The case of being a group represented by the formula (A) or a group represented by the formula (B) is a preferable example of the aryl group having the group represented by the formula (A) or the formula (B) as a substituent.

The naphthylene moiety in each of the formulae (1-X1) to (1-X3) may be condensed with one benzene ring. Examples of the structure condensed in the above-described manner are as follows. In addition, each equation indicates a bonding position.

In the formula, Ar²¹、Ar²²Are as defined above.

In the formulae (1-X4), (1-X5) and (1-X6), Ar²⁴、Ar²⁵And Ar²⁶Each independently preferably hydrogen, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, fluorenyl,

A group, a triphenylene group, a pyrenyl group, a group represented by the formula (A) described later or a group represented by the formula (B).

In the formula (1), Ar⁴、Ar⁵、Ar⁶、Ar⁷、Ar⁸、Ar⁹、Ar¹⁰、Ar¹¹、Ar¹²And Ar¹³Each independently is preferably hydrogen, phenyl, biphenyl, terphenyl, naphthyl, alkyl having 1 to 4 carbon atoms, a silyl group which may be substituted with cycloalkyl having 5 to 10 carbon atoms, a group represented by the following formula (A) or a group represented by the following formula (B), more preferably hydrogen, phenyl, biphenyl, naphthyl, a group represented by the following formula (A) or a group represented by the following formula (B), and still more preferably hydrogen, phenyl, naphthyl or a group represented by the following formula (A).

At X_aAnd X_bWhen at least one of (A) and (B) is a group represented by the formula (A) or a group represented by the formula (B), or a group represented by any one of the formulae (1-X1) to (1-X6) having a group represented by the formula (A) or a group represented by the formula (B), Ar is⁴、Ar⁵、Ar⁶、Ar⁹、Ar¹⁰And Ar¹³Preferably both are hydrogen. At this time, Ar⁷、Ar⁸、Ar¹¹And Ar¹²Each independently preferably represents hydrogen, phenyl, biphenyl, terphenyl, naphthyl, alkyl group having 1 to 4 carbon atoms or silyl group which may be substituted by cycloalkyl group having 5 to 10 carbon atoms, more preferably represents hydrogen, phenyl, biphenyl or naphthyl, further preferably represents hydrogen, phenyl or naphthyl, Ar⁷、Ar⁸、Ar¹¹And Ar¹²Most preferably both are hydrogen.

As another embodiment, Ar is preferred ⁵、Ar⁶、Ar⁷、Ar⁸Or Ar⁹Is a group containing a group represented by the formula (A) or the formula (B), and is more preferably Ar⁶、Ar⁷Or Ar⁸Is a group containing a group represented by the formula (A) or the formula (B).

The compound represented by the formula (1) is also preferably a compound represented by the following formula (1').

In the formula (1'), X_a'、X_b'、Ar⁴'、Ar⁵'、Ar⁶'、Ar⁷'、Ar⁸'、Ar⁹'、Ar¹⁰'、Ar¹¹'、Ar¹²' and Ar¹³' is defined as in the formula (1) and X_a、X_b、Ar⁴、Ar⁵、Ar⁶、Ar⁷、Ar⁸、Ar⁹、Ar¹⁰、Ar¹¹、Ar¹²And Ar¹³The same applies to the case where the compound represented by the formula (1') contains at least one group selected from the group consisting of the group represented by the formula (A) and the group represented by the formula (B).

In the formula (1'), X_a' and X_b' is independently preferably hydrogen, a phenyl group which may be substituted with any one or more substituents selected from the substituent group A, a biphenyl group which may be substituted with any one or more substituents selected from the substituent group A, a naphthyl group which may be substituted with any one or more substituents selected from the substituent group A, a phenanthryl group which may be substituted with any one or more substituents selected from the substituent group A, a group represented by the formula (A), or a group represented by the following formula (B).

In the formula (1'), Ar⁴'、Ar⁵'、Ar⁶'、Ar⁷'、Ar⁸'、Ar⁹'、Ar¹⁰'、Ar¹¹'、Ar¹²' and Ar¹³' are each independently preferably hydrogen, phenyl which may be substituted with at least one substituent selected from substituent group A, or at least one substituent selected from substituent group A A substituted naphthyl group, a phenanthryl group which may be substituted with any one or more substituents selected from substituent group a, a group represented by the following formula (a), or a group represented by the following formula (B).

As a preferable example of the compound represented by the formula (1), a compound represented by the following formula (1' a) can be mentioned.

In the formula (1' a), the metal oxide,

X_a' and X_b' are each independently hydrogen, a phenyl group which may be substituted with any one or more substituents selected from substituent group A, a biphenyl group which may be substituted with any one or more substituents selected from substituent group A, a naphthyl group which may be substituted with any one or more substituents selected from substituent group A, a phenanthryl group which may be substituted with any one or more substituents selected from substituent group A, a group represented by formula (A) or a group represented by formula (B), X_a' and X_bAt least one of' is a group containing a group represented by the formula (A) or the formula (B),

In the formula (1' a), X is not hydrogen_a' and X_bIn the present invention, the substituent group selected from the substituent group a, which may be substituted for each of phenyl, biphenyl, naphthyl and phenanthryl, is preferably phenyl, biphenyl, naphthyl, phenanthryl, a group represented by the formula (a) or a group represented by the formula (B). In the formula (1' a), X which is not hydrogen _a' and X_bThe phenyl group, biphenyl group, naphthyl group and phenanthryl group in' are preferably unsubstituted or substituted with a phenyl group, a group represented by formula (a) or a group represented by formula (B).

In the formula (1' a), Ar⁷'、Ar⁸'、Ar¹¹' and Ar¹²'minute' toIndependently of one another, hydrogen, phenyl, biphenyl or naphthyl are preferred.

As a preferred embodiment of the compound represented by the formula (1' a), X is mentioned_a' and X_b' is a hydrogen compound. More preferably X_a' and X_b' is hydrogen and in formula (A) and formula (B), Y is-O-; and X_a' and X_bEither one of' is hydrogen and R other than a bond in the formula (A) and the formula (B)²¹～R³⁸All are hydrogen compounds.

As another preferred embodiment of the compound represented by the formula (1' a), X is mentioned_a' and X_b' both are compounds containing a group represented by the formula (A) or the formula (B). In this case, Y is preferably-O-. In addition, Ar⁷'、Ar⁸'、Ar¹¹' and Ar¹²' preferably both are hydrogen.

As still another preferred embodiment of the compound represented by the formula (1' a), X is mentioned_a' and X_b' are the same aryl groups selected from phenyl, naphthyl and phenanthryl, and any aryl group may be substituted with any one or more substituents selected from substituent group A, and a compound wherein at least any one aryl group has a group represented by formula (A) or a group represented by formula (B) as a substituent. The reason is that: x _a' and X_b' both have the same aryl group as the basic structure, and thus are easily synthesized. In this case, the aryl group is preferably a phenyl group, a naphthyl group (1-naphthyl group or 2-naphthyl group), or a phenanthryl group (1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group, or 9-phenanthryl group). The reason is that: with pyrene,

Compounds having a condensed ring group containing 3 or less aromatic rings such as phenyl, naphthyl, and phenanthryl are easier to synthesize than compounds having a condensed ring group containing 4 or more aromatic rings such as benzopyrene. The phenanthryl group is preferably a 9-phenanthryl group.

Specifically, the compound has a structure represented by the following formula (C), formula (D), formula (E), formula (F), formula (G), formula (H), formula (I) or formula (J) as a partial structure. However, in a compound which does not form a condensed ring with the structure represented by formula (C), formula (D), formula (E), formula (F), formula (G), formula (H), formula (I) or formula (J) as a base structure and has the structure represented by formula (C) as a partial structure, at least one of the two phenyl groups in formula (C) is unsubstituted.

More specifically X_a' and X_b'A compound represented by the formula (1' a) which is any one of the following:

Any one of which is naphthyl (1-naphthyl or 2-naphthyl) substituted by a group represented by formula (A) or a group represented by formula (B), and the other is naphthyl (1-naphthyl or 2-naphthyl) which may be substituted by a group represented by formula (A) or a group represented by formula (B); or

Any one of them is a phenanthryl group (1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, or 9-phenanthryl) substituted with a group represented by formula (A) or a group represented by formula (B), and the other is a phenanthryl group (1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, or 9-phenanthryl) which may be substituted with a group represented by formula (A) or a group represented by formula (B).

As another preferable example of the compound represented by the formula (1'), Ar in the formula (1') can be mentioned⁵、Ar⁶、Ar⁷、Ar⁸Or Ar⁹Is a compound containing a group represented by the formula (A) or the formula (B). Particularly preferably Ar⁶、Ar⁷Or Ar⁸Is a group containing a group represented by the formula (A) or the formula (B). The compound having such a structure also more preferably has, as a partial structure, a structure represented by the above formula (C), formula (D), formula (E), formula (F), formula (G), formula (H) or formula (I). More specifically, X is more preferable_a' and X_b' is any one of:

Naphthyl (1-naphthyl or 2-naphthyl) each of which may be substituted by any one or more substituents selected from substituent group a; or

Each of which is a phenanthryl group (1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, or 9-phenanthryl) that may be substituted with any one or more substituents selected from substituent group A.

In the above, X_a' and X_b' may be the same or different in the presence or absence and kind of any one or more substituents selected from substituent group A. From the viewpoint of compound synthesis, the compounds are preferably the same, and from the viewpoint of device characteristics, the compounds are preferably different.

The following describes the group represented by the above formula (a) and the group represented by the above formula (B).

In the formula (A), Y is-O-, -S-or > N-R³⁹。R³⁹Is hydrogen or a substituted aryl group. In the formula (A), R²¹～R²⁸Each independently 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 substituted, aryloxy which may be substituted, arylthio which may be substituted, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkylbicycloalkylsilyl, amino which may be substituted, halogen, hydroxy or cyano, R ²¹～R²⁸Adjacent groups in (a) may be bonded to each other to form a hydrocarbon ring, an aryl ring or a heteroaryl ring. In addition, at least one hydrogen in the hydrocarbon ring, aryl ring or heteroaryl ring formed can be replaced by an alkyl group which can be substituted, a cycloalkyl group which can be substituted, an aryl group which can be substituted, a heteroaryl group which can be substituted, an alkoxy group which can be substituted, an aryloxy group which can be substituted, an arylthio group which can be substituted, a trialkylsilyl group, a tricycloalkylsilyl group, a dialkylcycloalkylsilyl group, an alkylbicycloalkylsilyl group, an amino group which can be substituted, a halogen, a hydroxyl group or a heteroaryl groupCyano substitution. The group represented by formula (a) is a group obtained by removing one hydrogen at any position of formula (a), and represents the position.

R in the formula (A)²¹～R²⁸In (3), the number of groups other than hydrogen is preferably 0 to 2, more preferably 0 to 1. At R²¹～R²⁸When adjacent groups in (1) are bonded to each other to form a hydrocarbon ring, an aryl ring or a heteroaryl ring, the substituent bonded to the ring and the remaining R²¹～R²⁸The total number of groups other than hydrogen in (b) is preferably 0 to 2, more preferably 0 to 1.

In the formula (B), Y is-O-, -S-or > N-R³⁹。R³⁹Is hydrogen or a substituted aryl group. In the formula (B), R²⁹～R³⁸Each independently 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 substituted, aryloxy which may be substituted, arylthio which may be substituted, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkylbicycloalkylsilyl, amino which may be substituted, halogen, hydroxy or cyano, R ²⁹～R³⁸Adjacent groups in (a) may be bonded to each other to form a hydrocarbon ring, an aryl ring or a heteroaryl ring. In addition, at least one hydrogen of the formed hydrocarbon ring, aryl ring or heteroaryl ring can be substituted with an alkyl group which may be substituted, a cycloalkyl group which may be substituted, an aryl group which may be substituted, a heteroaryl group which may be substituted, an alkoxy group which may be substituted, an aryloxy group which may be substituted, an arylthio group which may be substituted, a trialkylsilyl group, a tricycloalkylsilyl group, a dialkylcycloalkylsilyl group, an alkylbicycloalkylsilyl group, an amino group which may be substituted, a halogen, a hydroxyl group or a cyano group. The group represented by formula (B) is a group obtained by removing one hydrogen at any position of formula (B), and represents the position.

R in the formula (B)²⁹～R³⁸In (b), the number of groups other than hydrogen is preferably 0 to 2, more preferably 0 to 1, and still more preferably 0. At R²⁹～R³⁸When adjacent groups in (1) are bonded to each other to form a hydrocarbon ring, an aryl ring or a heteroaryl ring, the substituent bonded to the ring and the remaining R²⁹～R³⁸The total number of groups other than hydrogen in (b) is preferably 0 to 2, more preferably 0 to 1, and still more preferably 0.

R in the formula (A) and the formula (B)²¹～R³⁸The "alkyl group" of the "alkyl group which may be substituted" in (1) may be 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).

As R in the formula (A) and the formula (B)²¹～R³⁸The "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.

As R in the formula (A) and the formula (B)²¹～R³⁸Examples of the "heteroaryl group" of the "heteroaryl group which may be substituted" in (1) 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: 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 in the formula (A) and the formula (B)²¹～R³⁸Examples 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 (an alkoxy group having a branched chain having 3 to 18 carbon atoms), more preferably an alkoxy group having 1 to 12 carbon atoms (an alkoxy group having a branched chain having 3 to 12 carbon atoms), yet more preferably an alkoxy group having 1 to 6 carbon atoms (an alkoxy group having a branched chain having 3 to 6 carbon atoms), and particularly preferably an alkoxy group having 1 to 4 carbon atoms (an alkoxy group having a branched chain having 3 to 4 carbon atoms).

R in the formula (A) and the formula (B)²¹～R³⁸The "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 R²¹～R³⁸The "aryl" in (1).

R in the formula (A) and the formula (B)²¹～R³⁸The "arylthio" of the "arylthio 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 R²¹～R³⁸The "aryl" in (1).

As R in the formula (A) and the formula (B)²¹～R³⁸As the "trialkylsilyl group" in (1), there can be mentioned groups in which three hydrogens in the silyl group are each independently substituted by an alkyl group, and the alkyl group may be referred to as R²¹～R³⁸The "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, n-butyl, sec-butyl, tert-butyl, cyclobutyl and the like.

As R in the formula (A) and the formula (B)²¹～R³⁸OfThe "substituted amino group" of the substituted amino group "may include, 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. The aryl or heteroaryl groups may be referred to as R²¹～R³⁸The "aryl" or "heteroaryl" in (1).

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

As R in the formula (A) and the formula (B)²¹～R³⁸Examples of the "halogen" in (1) include: fluorine, chlorine, bromine, iodine.

As R in the formula (A) and the formula (B)²¹～R³⁸Some of the groups described above may be substituted as described above, and examples of the substituent in the above case include: alkyl, aryl or heteroaryl. The alkyl, aryl or heteroaryl groups may be referred to as R²¹～R³⁸The "alkyl", "aryl" or "heteroaryl" in (1).

"> N-R as Y in formula (A) and formula (B)³⁹R in `³⁹Is hydrogen or a substituted aryl group, and as said aryl group, the reference may be made to R²¹～R³⁸The substituent mentioned for the "aryl" in (1) may be cited as the substituent mentioned for R²¹～R³⁸The substituent(s) of (1).

R in the formula (A) and the formula (B)²¹～R³⁸Adjacent groups in (a) may be bonded to each other to form a hydrocarbon ring, an aryl ring or a heteroaryl ring. For example, the case where a ring in the formula (A) is not formed is a group represented by the following formula (A-1), and examples of the case where a ring is formed include groups represented by the following formulae (A-2) to (A-14). Furthermore, at least one hydrogen in the group represented by any one of the formulae (A-1) to (A-14) or (B-1) may be an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, or an aryloxy groupArylthio, trialkylsilyl, diarylsubstituted amino, diheteroarylsubstituted amino, arylhetarylsubstituted amino, halogen, hydroxy or cyano substitution, which may be cited as R²¹～R³⁸The groups in (1) above.

Examples of the ring in which adjacent groups are bonded to each other include a hydrocarbon ring, a cyclohexane ring, and an aryl ring or a heteroaryl ring²¹～R²⁸The ring structure illustrated in the "aryl" or "heteroaryl" in (1), which is formed by condensation with one or two benzene rings in the formula (A-1).

Examples of the group represented by formula (A) include a group represented by any one selected from the group consisting of the following formulae (A-1) to (A-14), and examples of the group represented by formula (B) include a group represented by formula (B-1). The group is preferably a group represented by any one selected from the group consisting of the formulae (A-1) to (A-4) and (B-1), more preferably a group represented by any one of the formulae (A-1), (A-3) or (A-4), and still more preferably a group represented by the formula (A-1).

The group represented by formula (a) and the group represented by formula (B) are each a group obtained by removing one hydrogen at any one position of formula (a) and formula (B), and represents the position. That is, any of the group represented by the formula (A) and the group represented by the formula (B) may be a bonding position. Among them, preferred are those having carbon atoms on two benzene rings in the structures of the formulae (A) and (B) and R in the structures of the formulae (A) and (B)²¹～R³⁸Wherein adjacent groups are bonded to each other to form an atom on any ring or "> N-R" as Y in the structures of the formula (A) and the formula (B)³⁹The N in "is a group directly bonded (having a bond in them).

Y in the formulae (A) and (B) and Y in each of the formulae (A-1) to (A-14) and (B-1) is preferably-O-.

Examples of the group represented by the formula (a) and the group represented by the formula (B) include groups represented by the following formulae. Y and x in the formula are as defined above, and Y is preferably-O-.

Specific examples of the compound represented by the formula (1) include compounds represented by the following formulae. In the following formulae, "Me" represents a methyl group and "tBu" represents a tert-butyl group. Y in each formula may be-O-, -S-or > N-R³⁹(R³⁹Is as defined in (1), R³⁹For example phenyl or phenyl substituted by deuterium. With respect to formula number, for example, in the case where Y is-O-, formula (1-331-Y) is set to formula (1-331-O) and Y is-S-or > N-R³⁹In the case of (1), the formula (1-331-S) or the formula (1-331-N) is used. Preferably Y is-O-or > N-R³⁹The above-mentioned compound (1) is particularly preferably an example in which Y is-O-.

Among the compounds, preferred are the compounds of the formula (1-7), the formula (1-45), the formula (1-242), the formula (1-90), the formula (1-78), the formula (1-93), the formula (1-158), the formula (1-161), the formula (1-170), the formula (1-8), the formula (1-48), the formula (1-185), the formula (1-203), the formula (1-129), the formula (1-244), the formula (1-753-O), the formula (1-551-O), the formula (1-381-O), the formula (1-717-O), the formula (1-755-O), the formula (1-778-O), the formula (1-752-O), the formula (1-785-O), the formula (1-790-O), Formula (1-763-O), formula (1-387-O), formula (1-1699-O), formula (1-1663-O), formula (1-383-N), formula (1-1552-O), formula (1-1683-O), formula (1-1680-O), formula (1-1599-O), formula (1-1116-O), formula (1-1025-O), formula (1-1703-O), formula (1-1751-O), formula (1-1665-O), formula (1-1584-S), formula (1-1538-N), formula (1-1001-O), formula (1-1716-O), formula (1-1184-O), formula (1-1140-O), A compound represented by formula (1-1347-O), formula (1-1783-O), formula (1-1759-O), formula (1-1767-O), formula (1-1777-O) or formula (1-1781-O).

1-1-2 process for producing benzanthracene compound

The benzanthracene compound represented by formula (1) can be produced by a method according to the production method described in international publication No. 2009/081776 and japanese patent No. 5018138. Examples of reaction routes for obtaining the benzanthracene compound represented by formula (1) based on these methods are described below. In the formula, Ar and Ar' represent, for example, an aryl group and a heteroaryl group.

Further, the benzanthracene compound represented by formula (1) can also be produced by the reaction pathway shown below. In the formula, Ar and Ar' represent, for example, an aryl group or a heteroaryl group.

1-2-1 polycyclic aromatic compound represented by formula (2) and multimer thereof

The organic EL element of the present invention contains, as a dopant material, a polycyclic aromatic compound represented by the following formula (2) and a polymer of the polycyclic aromatic compound having a plurality of structures represented by the formula (2) in a light-emitting layer. The polycyclic aromatic compound is preferably a polycyclic aromatic compound represented by formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e) or formula (2-f), or a polymer of a polycyclic aromatic compound having a plurality of structures represented by formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e) or formula (2-f).

In each structural formula, "a" to "C" and "a" to "C" are symbols representing a ring, a benzene ring, or a ring structure represented by a 5-membered ring, respectively, and the other symbols are as defined above.

The a ring, the B ring and the C ring in formula (2) are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen in these rings may be substituted by a substituent. Preferably, at least any one of rings a, B, and C is an aryl ring having at least one substituent or a heteroaryl ring having at least one substituent, more preferably, rings a, B, and C are each an aryl ring having at least one substituent or a heteroaryl ring having at least one substituent, and further preferably, rings a, B, and C are each an aryl ring having one substituent or a heteroaryl ring having one substituent.

As the substituent at this time, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted diarylamino group, a substituted or unsubstituted diheteroarylamino group, a substituted or unsubstituted arylheteroarylamino group (an amino group having an aryl group and a heteroaryl group), a substituted or unsubstituted diarylboron group (two aryl groups may be bonded via a single bond or a linking group), a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, or a substituted silane group is preferable. Examples of the substituent in the case where these groups have a substituent include: aryl, heteroaryl, alkyl, cycloalkyl, diarylamino, substituted silyl.

As the substituent, a cycloalkyl group such as a substituted or unsubstituted alkyl group (particularly, a neopentyl group) or an adamantyl group is particularly preferable. Further, a tertiary alkyl group (tR) is preferable. The reason is that: deactivation due to aggregation of molecules is prevented by such bulky substituents, and the luminescence quantum yield (PLQY) is improved. In addition, as the substituent, a substituted or unsubstituted diarylamino group is also preferable.

The tertiary alkyl group is represented by the following formula (tR).

In the formula (tR), R^a、R^bAnd R^cEach independently represents an alkyl group having 1 to 24 carbon atoms, wherein-CH is optionally contained in the alkyl group₂-may be substituted by-O-where the group represented by formula (tR) is substituted with at least one hydrogen in the compound or structure represented by formula (2).

R^a、R^bAnd R^cThe "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 (a branched alkyl group having 3 to 18 carbon atoms), an alkyl group having 1 to 12 carbon atoms (a branched alkyl group having 3 to 12 carbon atoms), an alkyl group having 1 to 6 carbon atoms (a branched alkyl group having 3 to 6 carbon atoms), and an alkyl group having 1 to 4 carbon atoms (a branched alkyl group having 3 to 4 carbon atoms).

R in formula (tR) of formula (2) ^a、R^bAnd R^cThe total number of carbon atoms of (A) is preferably 3 to 20, and particularly preferably 3 to 10.

As R^a、R^bAnd R^cSpecific examples of the alkyl group of (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, tert-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-hexyldecylHeptyl, 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 group, t-pentyl group, 1-ethyl-1-methylpropyl group, 1-diethylpropyl group, 1-dimethylbutyl group, 1-ethyl-1-methylbutyl group, 1,3, 3-tetramethylbutyl group, 1, 4-trimethylpentyl group, 1, 2-trimethylpropyl group, 1-dimethyloctyl group, 1-dimethylpentyl group, 1-dimethylheptyl group, 1, 5-trimethylhexyl group, 1-ethyl-1-methylhexyl group, 1-ethyl-1, 3-dimethylbutyl group, 1,2, 2-tetramethylpropyl group, 1-butyl-1-methylpentyl group, 1-diethylbutyl group, 1-ethyl-1-methylpentyl group, 1-diethylbutyl group, 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 other preferable substituents in the a ring, the B ring and the C ring include a diarylamino group substituted with a group of the formula (tR), a carbazolyl group substituted with a group of the formula (tR) and a benzocarbazolyl group substituted with a group of the formula (tR). 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).

The aryl or heteroaryl ring in the A, B and C rings preferably has a structure similar to that containing "B", "X¹"and" X²"the condensed bicyclic structure in the center of formula (2)" has a bonded 5-or 6-membered ring in common.

Here, the term "condensed bicyclic structure" means a structure containing "B" and "X" represented at the center of formula (2)¹"and" X²"two saturated hydrocarbon rings condensed. The "6-membered ring bonded in common to the condensed bicyclic structure" means, for example, a ring (benzene ring (6-membered ring)) condensed in the condensed bicyclic structure as shown in the formula (2-a), the formula (2-b), the formula (2-c), the formula (2-d), the formula (2-e) and the formula (2-f). In addition, the term "as Aryl ring or heteroaryl ring of ring a) having the 6-membered ring "means that ring a is formed only from the 6-membered ring, or ring a is formed by further condensing another ring or the like in the 6-membered ring so as to include the 6-membered ring. In other words, the "aryl ring or heteroaryl ring having 6-membered rings (as A ring)" as used herein means that 6-membered rings constituting all or part of A ring are condensed in a condensed bicyclic structure. The same applies with respect to the "5-membered ring". The same description applies to "ring B (ring B)" and "ring C (ring C)".

The ring A in the formula (2) corresponds to the ring a in the formula (2-a), the formula (2-b), the formula (2-c), the formula (2-d), the formula (2-e) and the formula (2-f) and a substituent R thereof¹Substituent R³. The ring B in the formula (2) corresponds to the ring B in the formulae (2-a), (2-B) and (2-c) and the substituent R thereof⁸Substituent R¹¹The b ring in the formula (2-d) and a substituent R thereof¹⁰And a substituent R¹¹And the b-ring in the formula (2-e) and the formula (2-f) and the substituent R thereof⁸And a substituent R⁹. The C ring in formula (2) corresponds to the C ring in formula (2-a) and its substituent R⁴Substituent R⁷The c-ring in the formula (2-b), the formula (2-d) and the formula (2-f) and a substituent R thereof⁴And a substituent R⁵And the c-ring in formula (2-c) and formula (2-e) and its substituent R ⁶And a substituent R⁷. That is, formula (2-a) corresponds to a structure in which a ring having at least a 6-membered ring structure is selected as the A-ring to C-ring of formula (2), and formulae (2-b), (2-C), (2-d), (2-e) and (2-f) correspond to a structure in which a ring having at least a 6-membered ring structure and a ring having at least a 5-membered ring structure are selected as the A-ring to C-ring of formula (2), respectively. Each ring in the formula (2-a) and the like is represented by a lowercase letter a to c in the above-mentioned meaning.

X in the formula (2-b), the formula (2-c), the formula (2-d), the formula (2-e) and the formula (2-f)_xEach independently > O, > S, > N-R or > C (-R)₂. Here, R of the > N-R is an optionally substituted aryl group, an optionally substituted heteroaryl group, an optionally substituted alkyl group or an optionally substituted cycloalkyl group, preferably an optionally substituted aryl group, more preferably an unsubstituted aryl group. Additionally, the > C (-R)₂R of (A) is independently hydrogen, may beAlkyl or cycloalkyl substituted aryl, heteroaryl which may be substituted by alkyl or cycloalkyl, preferably alkyl, more preferably methyl. Preferably > C (-R)₂Two of R are the same. In addition, > C (-R) is also preferable₂Two R in (1) form a ring with each other. X_xIndependently of each other, is preferably > O, > S or > N-R, more preferably > O or > S, and still more preferably > S.

In the formula (2-a), the formula (2-b), the formula (2-c), the formula (2-d), the formula (2-e) and the formula (2-f), R¹～R¹¹Each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryl groups may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyl, at least one of which may be substituted with aryl, heteroaryl, alkyl, cycloalkyl, or substituted silyl.

Preferably: r in each of the formula (2-a), the formula (2-b), the formula (2-c), the formula (2-d), the formula (2-e) and the formula (2-f)¹～R³In which 0 to 1 are substituents other than hydrogen and the others are hydrogen, R⁴～R⁷In which 0 to 1 are substituents other than hydrogen and the others are hydrogen, R⁸～R¹¹In which 0 to 1 are substituents other than hydrogen and the others are hydrogen,

more preferably: r¹～R³In which 1 is a substituent other than hydrogen and the others are hydrogen, R⁴～R⁷In which 1 is a substituent other than hydrogen and the others are hydrogen, R⁸～R¹¹In (1) are substituents other than hydrogen and the others are hydrogen. As for the substituent other than hydrogen, the preferable range can be referred to the description of the substituent described later as the first substituent (which may have the second substituent). The substituent other than hydrogen is particularly preferably an alkyl group (particularly, the above-mentioned tertiary alkyl group (tR), neopentyl group, etc.), a cycloalkyl group (e.g., adamantyl group, etc.), or a substituted or unsubstituted diarylamino group.

In the formula (2-a), the formula (2-b), the formula (2-c), the formula (2-d), the formula (2-e) and the formula (2-f), the substituent R of the ring a, the ring b and the ring c¹A substituent R²A substituent R³A substituent R⁴A substituent R⁵A substituent R⁶A substituent R⁷A substituent R⁸A substituent R⁹A substituent R¹⁰And a substituent R¹¹May be bonded to each other and together with the a-ring, b-ring or c-ring form an aryl ring or heteroaryl ring, at least one hydrogen in the formed ring may be substituted by an aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryl groups may be bonded via a single bond or a linking group), an alkyl, cycloalkyl, alkoxy, aryloxy or substituted silane group, at least one of which may be substituted by an aryl, heteroaryl, alkyl, cycloalkyl or substituted silane group.

For example, the compound represented by the formula (2-a) has a structure of a ring constituting the compound changed depending on the bonding form among substituents in the a ring, the b ring and the c ring, as shown in the following formulae (2-a-1) and (2-a-2). The A ' ring, B ' ring and C ' ring in the formulae correspond to the A ring, B ring and C ring in formula (2), respectively. In addition, R in each formula¹、R²、R³、R⁴、R⁵、R⁶、R⁷、R⁸、R⁹、R¹⁰、R¹¹、a、b、c、X¹And X²Is the same as defined in the formula (2-a).

When the formula (2-a) is used for illustration, the A ' ring, the B ' ring and the C ' ring in the formula (2-a-1) and the formula (2-a-2) represent a substituent R¹A substituent R²A substituent R³A substituent R⁴A substituent R⁵A substituent R⁶A substituent R⁷A substituent R⁸A substituent R⁹A substituent R¹⁰And a substituent R¹¹The adjacent groups in (b) are bonded to each other and form an aryl ring or a heteroaryl ring together with the a-ring, the b-ring and the c-ring, respectively (may also be referred to as a fused ring in which other ring structures are condensed in the a-ring, the b-ring or the c-ring). Although not shown in the formula, the following may be presentA compound in which the a, B and C rings are all changed to the A ', B ' and C ' rings. Further, as is apparent from the formulae (2-a-1) and (2-a-2), for example, R of ring b⁸R with ring c⁷R of ring b¹¹R with ring a¹R of ring c⁴R with ring a³Etc. do not correspond to "adjacent radicals to each other", they are not bonded. That is, the term "adjacent group" refers to a group adjacent to the same ring.

The compounds represented by the formulae (2-a-1) and (2-a-2) correspond to, for example, compounds represented by the formulae (2-67) to (2-74), the formulae (2-76) to (2-83), the formulae (2-273) to (2-276), the formulae (2-290) to (2-295), and the formulae (2-350) to (2-355), which are described below as specific compounds. That is, for example, the compound is a compound having an a 'ring (or B' ring or C 'ring) formed by condensation of a benzene ring as an a-ring (or B-ring or C-ring) with a benzene ring, an indole ring, a pyrrole ring, a furan ring, a thiophene ring, a benzofuran ring, a benzothiophene ring, a cyclohexene ring or an indene ring, and the fused ring a' (or the fused ring B 'or the fused ring C') formed is a naphthalene ring, a carbazole ring, an indole ring, a benzofuran ring, a benzothiophene ring, a dibenzofuran ring, a dibenzothiophene ring, a tetrahydronaphthalene ring or a fluorene ring, respectively.

In the formulae (2-b), (2-c), (2-d), (2-e) and (2-f), fused rings in which other ring structures are condensed in the a-ring, the b-ring or the c-ring may be formed in the same manner. For example, the benzene ring as the a-ring or b-ring may be condensed with another ring structure to form a condensed ring, similarly to the benzene ring in the formula (2-a).

In the formula (2-b), the formula (2-c), the formula (2-d), the formula (2-e) and the formula (2-f), R is particularly preferably in a 5-membered ring which is a b-ring or a c-ring⁴～R¹¹Adjacent groups in (a) are bonded to each other to form a ring to form a condensed ring. For example, in the c-rings of the formulae (2-b) and (2-c) and the b-and c-rings of the formulae (2-d), (2-e) and (2-f), R³～R¹¹The adjacent groups in (1) are bonded to each other to form a ring, whereby a B 'ring or a C' ring can be formed as a condensed ring. Examples of the condensed ring in the case where the ring to be formed is a benzene ring include: indole ring, benzofuran ring, benzothiophene ring.

As an example, R in a 5-membered ring as a c-ring of the formula (2-b) is shown below⁴And R⁵And bonded to each other to form a benzene ring to form a condensed ring.

In the formula (2-b-1), R¹、R²、R³、R⁸、R⁹、R¹⁰、R¹¹、X_x、X¹And X²The same meanings as in the formula (2-b), and the same preferable ranges. R^4b、R^5b、R^6b、R^7bIs hydrogen or a substituent selected from the group consisting of aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryl groups may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, and substituted silyl, at least one of which may be substituted with aryl, heteroaryl, alkyl, cycloalkyl, or substituted silyl. R ^4b、R^5b、R^6b、R^7bOf these, 0 to 2 substituents other than hydrogen and the others are preferred, and 1 substituent other than hydrogen and the others are more preferred. As for the substituent other than hydrogen, the preferable range can be referred to the description of the substituent described later as the first substituent (which may have the second substituent). The substituent other than hydrogen is particularly preferably an alkyl group (particularly, the above-mentioned tertiary alkyl group (tR), neopentyl group, etc.), a cycloalkyl group (e.g., adamantyl group, etc.), or a substituted or unsubstituted diarylamino group.

For example, in the formulae (2-b), (2-c), (2-d), (2-e) and (2-f), when X is_xWhen the number is > O, the B-ring and/or C-ring is a furan ring, but a ring corresponding to the B 'ring and/or C' ring of formula (2-a-1) formed by condensation of a benzene ring with respect to the furan ring is a benzofuran ring.

Further, for example, in the formula (2-b), the formula (2-c), the formula (2-d), the formula (2-e) and the formula (2-f), when X is_xWhen > S, the b-ring and/or c-ring is a thiophene ring but para to the benzene ringThe ring corresponding to the B 'ring and/or the C' ring of the formula (2-a-1) formed by condensation of the thiophene ring is a benzothiophene ring.

Examples of such a structure include compounds represented by any of the following formulae (2 to 572) to (1 to 588).

X in the formula (2)¹And X²Independently of each other > O, > N-R, > C (-R)₂R > N-R is aryl which may be substituted, heteroaryl which may be substituted, alkyl which may be substituted or cycloalkyl which may be substituted, said > C (-R)₂R of (a) is hydrogen, optionally substituted aryl, optionally substituted alkyl or optionally substituted cycloalkyl, R of said > N-R and/or said > C (-R)₂R of (2) may be bonded to the B ring and/or the C ring by a linking group or a single bond, and the linking group is preferably-O-, -S-or-C (-R)₂-. Furthermore, the "-C (-R)₂R of the-is hydrogen, alkyl or cycloalkyl. The same applies to X in the formulae (2-a), (2-b), (2-c), (2-d), (2-e) and (2-f)¹And X²。

In the formula (2) and the formulae (2-a), (2-b), (2-c), (2-d), (2-e) and (2-f), X¹And X²Each independently is preferably > O or > N-R, more preferably > N-R where R is a phenyl group which may be substituted, even more preferably > N-R where at least one R is a phenyl group substituted with one or two tert-butyl, tert-amyl, methyl or phenyl groups, and especially preferably > N-R where at least one R is a phenyl group substituted with one tert-butyl or tert-amyl group. X¹And X²The groups may be the same or different from each other.

Here, "> R of N-R and/or > C (-R) in the formula (2)₂The definition that R of (A) is bonded to the ring A, the ring B and/or the ring C through a linking group or a single bond "corresponds to R > N-R and/or > C (-R) in the formulae (2-a), (2-B), (2-C), (2-d), (2-e) and (2-f)₂R of (2) is represented by-O-, -S-, -C (-R)₂-or a single bond to the a-ring, b-ring and/or c-ring.

The definition can be expressed by a compound represented by the following formula (2-a-3-1)And has X¹Or X²A ring structure introduced into the condensed rings B 'and C'. I.e. for example with other rings to introduce X¹(or X)²) The compound of (1) is a compound of ring B '(ring C') formed by condensation of benzene rings of ring B (or ring C) in the formula (2-a). The condensed ring B '(or the condensed ring C') formed is, for example, a carbazole ring, a phenoxazine ring, a phenothiazine ring or an acridine ring.

Further, the regulation may be represented by a compound represented by the following formula (2-a-3-2) or formula (2-a-3-3) and having X¹And/or X²A ring structure introduced into the condensed ring A'. I.e. for example with other rings to introduce X¹(and/or X)²) The compound of formula (2-a) has an A' ring formed by condensation of a benzene ring as the a ring. The condensed ring A' formed is, for example, a carbazole ring, a phenoxazine ring, a phenothiazine ring or an acridine ring.

Examples of the "aryl ring" of the ring A, ring B and ring C of the formula (2) 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. Furthermore, the "aryl ring" corresponds to the "R" specified in the formula (2)¹～R¹¹The "aryl ring" in which adjacent groups in (a) are bonded to each other and form together with the a-ring, the b-ring, or the c-ring "and the a-ring (or the b-ring, or the c-ring) already contains a benzene ring having 6 carbon atoms, and therefore the total carbon number 9 of the condensed rings in which the 5-membered ring is condensed is the lower limit carbon number.

Specific "aryl ring" may include: the benzene ring as the monocyclic system, the biphenyl ring as the bicyclic system, the naphthalene ring and the tetrahydronaphthalene ring as the condensed bicyclic system, the terphenyl ring (m-terphenyl group, o-terphenyl group, p-terphenyl group) as the tricyclic system, the acenaphthene ring, the fluorene ring, the phenalene ring, and the phenanthrene ring as the condensed tricyclic system, the triphenylene ring, the pyrene ring, and the tetracene ring as the condensed tricyclic system, the perylene ring, and the pentacene ring as the condensed pentacene ring, and the like.

Examples of the "heteroaryl ring" of the a ring, B ring and C ring of formula (2) include heteroaryl rings having 2 to 30 carbon atoms, preferably heteroaryl rings having 2 to 25 carbon atoms, more preferably heteroaryl rings having 2 to 20 carbon atoms, still more preferably heteroaryl rings having 2 to 15 carbon atoms, and particularly preferably heteroaryl rings having 2 to 10 carbon atoms. Examples of the "heteroaryl ring" include heterocyclic rings containing 1 to 5 heteroatoms selected from oxygen, sulfur and nitrogen as ring-constituting atoms in addition to carbon. Further, the "heteroaryl ring" corresponds to "R" specified in the formula (2-a), the formula (2-b), the formula (2-c), the formula (2-d), the formula (2-e) and the formula (2-f) ¹、R²、R³、R⁴、R⁵、R⁶、R⁷、R⁸、R⁹、R¹⁰And R¹¹The heteroaryl ring "in which adjacent groups in (a) are bonded to each other and form a ring a, a ring b, or a ring c" and the ring a (or the ring b or the ring c) already contains a benzene ring having 6 carbon atoms, and therefore the total carbon number of the condensed rings in which the 5-membered ring is condensed is 6 carbon atoms as the lower limit.

Specific examples of the "heteroaryl ring" include: a pyrrole ring, an oxazole ring, an isoxazole ring, a thiazole ring, an isothiazole ring, an imidazole ring, an oxadiazole ring, a thiadiazole ring, a triazole ring, a tetrazole ring, a pyrazole ring, a pyridine ring, a pyrimidine ring, a pyridazine ring, a pyrazine ring, a triazine ring, an indole ring, an isoindole ring, a 1H-indazole ring, a benzimidazole ring, a benzoxazole ring, a benzothiazole ring, a 1H-benzotriazole ring, a quinoline ring, an isoquinoline ring, a cinnoline ring, a quinazoline ring, a quinoxaline ring, a oxazine ring, a naphthyridine ring, a purine ring, a pteridine ring, a carbazole ring, an acridine ring, a phenoxathiin ring, a phenoxazine ring, a phenothiazine ring, a phenazine ring, an indolizine ring, a furan ring, a benzofuran ring, an isobenzofuran ring, a dibenzofuran ring, a thiophene ring, a benzothiophene ring, and the like.

At least one of the "aryl ring" or "heteroaryl 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" (two aryl groups may be bonded via a single bond or a linking group), a substituted or unsubstituted "alkyl", a substituted or unsubstituted "cycloalkyl", a substituted or unsubstituted "alkoxy", or a substituted or unsubstituted "aryloxy" as a first substituent, but the heteroaryl group, the diarylamino group, the diheteroarylamino group, or the like as a first substituent is substituted with a heteroaryl group, an aryl group, a heteroaryl group, a diarylamino group, or a heteroaryl group as a second substituent, The aryl and heteroaryl groups of the "arylheteroarylamino group", the aryl group of the "diarylboron group" and the aryl group of the "aryloxy group" may be exemplified by the monovalent radicals of the "aryl ring" or the "heteroaryl ring".

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), 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 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-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, tert-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 "cycloalkyl group" as the first substituent include cycloalkyl groups having 3 to 24 carbon atoms, preferably cycloalkyl groups having 3 to 20 carbon atoms, more preferably cycloalkyl groups having 3 to 16 carbon atoms, still more preferably cycloalkyl groups having 3 to 14 carbon atoms, still more preferably cycloalkyl groups having 5 to 10 carbon atoms, particularly preferably cycloalkyl groups having 5 to 8 carbon atoms, and most preferably cycloalkyl groups having 5 to 6 carbon atoms.

Examples of the "alkoxy group" 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. The alkoxy group is preferably an alkoxy group having 1 to 18 carbon atoms (an alkoxy group having a branched chain having 3 to 18 carbon atoms), more preferably an alkoxy group having 1 to 12 carbon atoms (an alkoxy group having a branched chain having 3 to 12 carbon atoms), yet more preferably an alkoxy group having 1 to 6 carbon atoms (an alkoxy group having a branched chain having 3 to 6 carbon atoms), and particularly preferably an alkoxy group having 1 to 4 carbon atoms (an alkoxy group having a branched chain having 3 to 4 carbon atoms).

Specific examples of the alkoxy group include: methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy 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 groups in which three hydrogens of the silyl group are each independently substituted with an alkyl group, and the alkyl group may refer to the group described as the "alkyl group" in the first substituent. Preferred alkyl groups for substitution are alkyl groups 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, Ethyldiisopropylsilane, butyldiisopropylsilane, sec-butyldiisopropylsilane, tert-amyldiisopropylsilane, etc.

As the "tricycloalkylsilyl group", there can be cited groups in which three hydrogens in the silyl group are each independently substituted with a cycloalkyl group, and the cycloalkyl group can cite the 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 [2.0.1] 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 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.

In addition, "aryl" of "diarylboron group" as 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)₂A > O, > S, or > N-R) bond. Here, > C (-R)₂And R > N-R is aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, or aryloxy (above which is the first substituent), and in the first substituent may be further substituted aryl, heteroaryl, alkyl, or cycloalkyl (above which is the second substituent), and as specific examples of these groups, the description of aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, or aryloxy as the first substituent may be cited.

Specifically, the emission wavelength can be adjusted by steric hindrance, electron donating property, and electron withdrawing property of the structure of the first substituent, and the group represented by the following structural formula is preferable, and methyl group, tert-butyl group, tert-amyl (t-amyl), phenyl group, o-tolyl group, p-tolyl group, 2, 4-xylyl group, 2, 5-xylyl group, 2, 6-xylyl group, 2,4, 6-mesityl group, diphenylamino group, di-p-tolylamino group, bis (p-tert-butyl) phenyl group), carbazolyl group, 3, 6-dimethylcarbazolyl group, 3, 6-di-tert-butylcarbazolyl group, and phenoxy group are more preferable, and methyl group, tert-butyl group, phenyl group, o-tolyl group, 2, 6-xylyl group, 2,4, 6-mesityl group, diphenylamino group, di-tolylamino group, and phenoxy group are further preferable, Bis (p- (tert-butyl) phenyl) amino, 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, a tert-butyl group, a tert-amyl (t-amyl), an o-tolyl group, a p-tolyl group, a 2, 4-xylyl group, a 2, 5-xylyl group, a 2, 6-xylyl group, a 2,4, 6-mesityl group, a di-p-tolylamino group, a bis (p-tert-butyl) phenyl) amino group, a 3, 6-dimethylcarbazolyl group, and a 3, 6-di-tert-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.

In the formula (2-a), it is preferable that: r¹、R²、R³、R⁴、R⁵、R⁶、R⁷、R⁸、R⁹、R¹⁰And R¹¹Wherein 1 to 4 of the groups are represented by any one of the structural formulae, and the remainder is hydrogen; more preferably: r¹、R²、R³、R⁴、R⁵、R⁶、R⁷、R⁸、R⁹、R¹⁰And R¹¹Wherein 1 to 3 of the groups are represented by any one of the structural formulae, and the remainder is hydrogen; more preferably: r¹、R²、R³、R⁴、R⁵、R⁶、R⁷、R⁸、R⁹、R¹⁰And R¹¹Of these, 1 to 3 are methyl, tert-butyl or tert-pentyl, and the remainder are hydrogen.

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" (two aryl groups may be bonded via a single bond or a linking group), a substituted or unsubstituted "alkyl", a substituted or unsubstituted "cycloalkyl", a substituted or unsubstituted "alkoxy", or a substituted or unsubstituted "aryloxy" as indicated as substituted or unsubstituted, at least one of which may be substituted with a second substituent. Examples of the second substituent include aryl, heteroaryl, alkyl, and cycloalkyl, and specific examples thereof are described with reference to the monovalent group of the "aryl ring" or the "heteroaryl ring" and the "alkyl" or the "cycloalkyl" as the first substituent. In addition, among the aryl or heteroaryl groups as the second substituent, a structure in which at least one hydrogen of them is substituted with an aryl group such as a phenyl group (specifically, the group described above), an alkyl group such as a methyl group (specifically, the group described above), or a cycloalkyl group such as a cyclohexyl group (specifically, the group described above) is also included in the aryl or heteroaryl groups 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.

R as formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e) and formula (2-f)¹、R²、R³、R⁴、R⁵、R⁶、R⁷、R⁸、R⁹、R¹⁰And R¹¹The aryl, heteroaryl, diarylamino aryl, diheteroarylamino heteroaryl, arylheteroarylamino aryl and heteroaryl, diarylboron aryl or aryloxy aryl group in (1) may be exemplified by a monovalent group of the "aryl ring" or "heteroaryl ring" illustrated in formula (2). In addition, as R¹～R¹¹The alkyl group, cycloalkyl group or alkoxy group in (1) can be referred to the description of "alkyl", "cycloalkyl" or "alkoxy" as the first substituent in the description of the formula (2). Further, aryl, heteroaryl, alkyl or cycloalkyl groups as substituents for these groups are also the same. In addition, as R¹、R²、R³、R⁴、R⁵、R⁶、R⁷、R⁸、R⁹、R¹⁰And R¹¹The heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkoxy, or aryloxy groups as substituents for the a-ring, b-ring, or c-ring when these adjacent groups are bonded to each other and form an aryl ring or heteroaryl ring together with these rings, and aryl, heteroaryl, alkyl, or cycloalkyl groups as further substituents are also the same.

X of formula (2)¹And X²R > N-R in (A) is aryl, heteroaryl, alkyl or cycloalkyl which may be substituted by said second substituent, at least one hydrogen in aryl or heteroaryl may for example be substituted by alkyl or cycloalkyl. As said aryl, heteroaryl, alkyl and cycloalkyl radicals, mention may be made of The radicals mentioned above are mentioned. Particularly preferred is an aryl group having 6 to 10 carbon atoms (e.g., phenyl group, naphthyl group, etc.), a heteroaryl group having 2 to 15 carbon atoms (e.g., carbazolyl group, etc.), an alkyl group having 1 to 5 carbon atoms (e.g., methyl group, ethyl group, etc.), or a cycloalkyl group having 5 to 10 carbon atoms (preferably cyclohexyl group or adamantyl group). The same applies to X in the formulae (2-a), (2-b), (2-c), (2-d), (2-e) and (2-f)¹And X². X of the formula (2-a), the formula (2-b), the formula (2-c), the formula (2-d), the formula (2-e) and the formula (2-f)¹And X²R > N-R in (1) is an aryl group having 6 to 12 carbon atoms which may be substituted with an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 14 carbon atoms, a heteroaryl group having 2 to 15 carbon atoms which may be substituted with an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 14 carbon atoms, and preferably an aryl group having 6 to 10 carbon atoms, an alkyl group having 1 to 4 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms which may be substituted with an alkyl group having 1 to 4 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms.

X of formula (2)¹And X²Middle > C (-R)₂R of (a) is hydrogen, aryl which may be substituted by said second substituent, alkyl or cycloalkyl, at least one hydrogen in the aryl group being for example substituted by alkyl or cycloalkyl. Examples of the aryl group, the alkyl group and the cycloalkyl group include the groups described above. Particularly preferred is an aryl group having 6 to 10 carbon atoms (e.g., phenyl group, naphthyl group, etc.), an alkyl group having 1 to 5 carbon atoms (e.g., methyl group, ethyl group, etc.), or a cycloalkyl group having 5 to 10 carbon atoms (preferably cyclohexyl group or adamantyl group). The same applies to X in the formulae (2-a), (2-b), (2-c), (2-d), (2-e) and (2-f) ¹And X². X of the formula (2-a), the formula (2-b), the formula (2-c), the formula (2-d), the formula (2-e) and the formula (2-f)¹And X²Middle > C (-R)₂R in (A) is hydrogen, an aryl group having 6 to 12 carbon atoms which may be substituted with an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 14 carbon atoms, and preferably hydrogen, an aryl group having 6 to 10 carbon atoms which may be substituted with an alkyl group having 1 to 4 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms, an alkyl group having 1 to 4 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms.

-C (-R) as a linking group in the formula (2)₂R of- "is hydrogen, alkyl or cycloalkyl as said alkylAnd cycloalkyl groups, the radicals mentioned above being able to be cited. Particularly preferably an alkyl group having 1 to 5 carbon atoms (for example, methyl group, ethyl group, etc.) or a cycloalkyl group having 5 to 10 carbon atoms (preferably cyclohexyl group or adamantyl group). The same applies to the linkage group of the formula (2-a), the formula (2-b), the formula (2-C), the formula (2-d), the formula (2-e) and the formula (2-f) — C (-R)₂-”。

The dopant material may be a polymer of a polycyclic aromatic compound having a plurality of unit structures represented by formula (2). The polymer is preferably a polymer of a polycyclic aromatic compound having a plurality of unit structures represented by the formula (2-a), the formula (2-b), the formula (2-c), the formula (2-d), the formula (2-e) or the formula (2-f). The multimer is preferably a dimer to a hexamer, more preferably a dimer to a trimer, and particularly preferably a dimer. The polymer may be in a form having a plurality of the unit structures in one compound, and for example, in addition to a form in which a plurality of the unit structures are bonded by a single bond, a linking group having 1 to 3 carbon atoms, a phenylene group, a naphthylene group, or the like, a form in which the unit structures are bonded so as to share any ring (a ring, B ring, or C ring, a ring, B ring, or C ring) included in the unit structures in a plurality of the unit structures, or a form in which the unit structures are bonded so as to condense any ring (a ring, B ring, or C ring, a ring, B ring, or C ring) included in the unit structures.

Examples of such multimers include multimer compounds represented by the following formula (2-4), formula (2-4-1), formula (2-4-2), formula (2-5-1) to formula (2-5-4), or formula (2-6). When the formula (2-a) is used for explanation, the multimeric compound represented by the following formula (2-4) is a multimeric compound having a plurality of unit structures represented by the formula (2-a) in one compound so as to share a benzene ring as an a-ring. In addition, the expression (2-a) is described, the following formula (2-4-1) expressed polymer compounds are a compound with a common as a ring benzene ring in a compound with two formula (2-a) unit structure. In addition, the expression (2-a) is described, the following formula (2-4-2) expressed polymer compound is a compound with a common as a ring benzene ring in three formula (2-a) unit structure polymer. In addition, the polymer compound represented by the following formula (2-a) is a polymer compound having a plurality of unit structures represented by the formula (2-a) in one compound so as to share a benzene ring as a b-ring (or c-ring) in the formula (2-a) described below to the formula (2-5-1) to the formula (2-5-4). In addition, when the formula (2-a) is described, the multimeric compound represented by the following formula (2-6) is a multimeric compound having a plurality of unit structures represented by the formula (2-a) in one compound, for example, in such a manner that a benzene ring of a b-ring (or a-ring, c-ring) as a certain unit structure is condensed with a benzene ring of a b-ring (or a-ring, c-ring) as a certain unit structure.

The polymer compound may be a polymer in which the polymerization form expressed by the formula (2-4), the formula (2-4-1), or the formula (2-4-2) and the polymerization form expressed by any one of the formulae (2-5-1) to (2-5-4), or the formula (2-6) are combined, a polymer in which the polymerization form expressed by any one of the formulae (2-5-1) to (2-5-4) and the polymerization form expressed by the formula (2-6) are combined, or a polymer in which the polymerization form expressed by the formula (2-4), the formula (2-4-1), or the formula (2-4-2) and the polymerization form expressed by any one of the formulae (2-5-1) to (2-5-4) and the polymerization form expressed by the formula (2-6) are combined And (3) a body.

Further, all or a part of hydrogen in the chemical structure of the polycyclic aromatic compound represented by the formula (2) or the formula (2-a), the formula (2-b), the formula (2-c), the formula (2-d), the formula (2-e) or the formula (2-f) and the multimer thereof may be deuterium, cyano or halogen. For example, in formula (2), ring A, ring B, ring C (ring A to ring C are aryl or heteroaryl rings), substituents for ring A to ring C, and X³And X⁴Is > N-R or > C (-R)₂When R (═ alkyl, cycloalkyl, aryl) the hydrogen may be substituted by deuterium, cyano or halogen, this being the caseIn these, all or a part of hydrogen in the aryl group or the heteroaryl group may be replaced with deuterium, cyano group or halogen. Halogen is fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, more preferably fluorine or chlorine.

In addition, at least one selected from the group consisting of an aryl ring and a heteroaryl ring in the chemical structures of the polycyclic aromatic compound represented by formula (2), formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e) or formula (2-f) and the multimer thereof may be condensed with at least one cycloalkane.

For example, aryl and heteroaryl rings as in A, B, C, a, B, C, and heteroaryl rings; aryl (aryl moiety in aryl, diarylamino, arylheteroarylamino, diarylboron, or aryloxy) and heteroaryl (heteroaryl moiety in heteroaryl, diheteroarylamino, or arylheteroarylamino) as the first and second substituents in the a-C ring; aryl (same as described above) and heteroaryl (same as described above) as the first substituent and the second substituent for the a-ring, the b-ring and the c-ring; and as (as X)¹、X²N-R at least one of aryl (same as above) and heteroaryl (same as above) of R may be condensed with at least one cycloalkane.

Preferably: aryl and heteroaryl rings as ring a, ring B, ring C, ring a, ring B, ring C; aryl (aryl moiety in aryl, diarylamino, diarylboron, or aryloxy) and heteroaryl (heteroaryl moiety in heteroaryl or diheteroarylamino) as first substituents in the A-C rings; aryl (same as above) and heteroaryl (same as above) as a first substituent for the a-ring to the c-ring; and as (as X) ¹、X²N-R at least one of aryl (same as above) and heteroaryl (same as above) of R may be condensed with at least one cycloalkane.

More preferably: aryl rings as ring a, ring B, ring C, ring a, ring B, ring C; aryl (aryl moiety in aryl or diarylamino) and heteroaryl (heteroaryl moiety in heteroaryl) as first substituents in the A-ring to the C-ring; as the second to the a-ring, b-ring, c-ringAryl (same as above) and heteroaryl (same as above) as a substituent; and as (as X)¹、X²At least one of the aryl groups (same as above) of R of N-R may be condensed with at least one cycloalkane.

More preferably: aryl rings as ring a, ring B, ring C, ring a, ring B, ring C; aryl as a first substituent in the A-ring to the C-ring (aryl moiety in aryl or diarylamino); aryl as a first substituent for the a-ring, b-ring and c-ring (the same as described above); and as (as X)¹、X²At least one of the aryl groups (same as above) of R of N-R may be condensed with at least one cycloalkane.

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, norbornene, bicyclo [1.0.1] butane, bicyclo [1.1.1] pentane, bicyclo [2.0.1] pentane, bicyclo [1.2.1] hexane, bicyclo [3.0.1] hexane, bicyclo [2.1.2] heptane, bicyclo [2.2.2] octane, adamantane, diamantane, decahydronaphthalene, decahydroazulene, and alkyl (particularly methyl) substituents, halogen (particularly fluorine) substituents and deuterium substituents each having 1 to 5 carbon atoms.

Among these, for example, a structure in which at least one hydrogen on the carbon at the α -position of a cycloalkane (in a cycloalkane condensed in 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 carbon at the two α -positions 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 (B10) or formula (B11) is bonded to adjacent carbon atoms in an aryl ring or heteroaryl ring.

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

In the formula (B), Me represents a methyl group and x represents a bonding position, and the group represented by the formula (B) is bonded to two adjacent elements on the bonded aryl ring or heteroaryl ring.

Examples of such a structure include structures of compounds represented by any of formulae (2-559) to (2-563) and (2-580) described later.

The number of cycloalkanes condensed in one aromatic ring or heteroaromatic ring is preferably 1 to 3, more preferably 1 or 2, and still more preferably 1. For example, examples in which one or more cycloalkanes are condensed in one benzene ring (phenyl group) are shown below. Cycloalkanes condensed as shown in the formula (Cy-1-4) and the formula (Cy-2-4) may also be condensed with each other. The same applies to the case where the condensed ring (group) is an aromatic ring or a 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.

At least one-CH in cycloalkanes₂-may be substituted by-O-. For example, the following shows one or more-CH condensed in cycloalkane of one benzene ring (phenyl group)₂Examples of substitution by-O-. The same applies to the case where the condensed ring (group) is an aromatic ring or a 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.

At least one hydrogen in the cycloalkane may be substituted, and as the substituent, for example, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryl groups may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, substituted silyl, deuterium, cyano, or halogen may be cited as a detailed description of the first substituent. 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.

Other forms of the cycloalkane condensation include: the chemical structure of the polycyclic aromatic compound represented by formula (2), formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e) or formula (2-f) and multimers thereof has, for example, an example where R is > N-R of an aryl group condensed by cycloalkane, a diarylamino group condensed by cycloalkane (condensed to an aryl moiety thereof), a carbazolyl group condensed by cycloalkane (condensed to a benzene ring moiety thereof) or a benzocarbazolyl group condensed by cycloalkane (condensed to a benzene ring moiety thereof). As the "diarylamino group", groups described as the "first substituent" can be cited.

Further, as more specific examples, there are: r in the chemical structure of a polycyclic aromatic compound represented by the formula (2-a), the formula (2-b), the formula (2-c), the formula (2-d), the formula (2-e) or the formula (2-f) and a multimer thereof²Are examples of diarylamino groups (condensed to the aryl portion thereof) condensed from cycloalkane or carbazolyl groups (condensed to the benzene ring portion thereof) condensed from cycloalkane.

Preferred combinations of substituents in the formula (2-a), the formula (2-b), the formula (2-c), the formula (2-d), the formula (2-e) and the formula (2-f) are as follows.

R¹、R²、R³、R⁴、R⁵、R⁶、R⁷、R⁸、R⁹、R¹⁰And R¹¹Independently hydrogen, aryl group having 6 to 30 carbon atoms which may be substituted with alkyl group having 1 to 6 carbon atoms or cycloalkyl group having 3 to 14 carbon atoms, heteroaryl group having 2 to 30 carbon atoms which may be substituted with alkyl group having 1 to 6 carbon atoms or cycloalkyl group having 3 to 14 carbon atoms, diarylamino group (wherein aryl group is aryl group having 6 to 12 carbon atoms which may be substituted with alkyl group having 1 to 6 carbon atoms or cycloalkyl group having 3 to 14 carbon atoms), diarylboron group (wherein aryl group is aryl group having 6 to 12 carbon atoms which may be substituted with alkyl group having 1 to 6 carbon atoms or cycloalkyl group having 3 to 14 carbon atoms), alkyl group having 1 to 24 carbon atoms or cycloalkyl group having 3 to 24 carbon atoms, and R is R¹、R²、R³、R⁴、R⁵、R⁶、R⁷、R⁸、R⁹、R¹⁰And R¹¹Wherein adjacent groups in the (a) ring, the (b) ring or the (c) ring may be bonded to each other to form an aryl ring having 9 to 16 carbon atoms or a heteroaryl ring having 6 to 15 carbon atoms, and at least one hydrogen in the ring may be substituted by an aryl group having 6 to 30 carbon atoms which may be substituted by an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 14 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms which may be substituted by an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 14 carbon atoms, a diarylamino group (wherein the aryl group is an aryl group having 6 to 12 carbon atoms which may be substituted by an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 14 carbon atoms), a diarylboron group (wherein the aryl group is an aryl group having 6 to 12 carbon atoms which may be substituted by an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 14 carbon atoms), an alkyl group having 1 to 24 carbon,

X¹And X²Independently of each other > O, > N-R, > C (-R)₂Or > S, wherein R > N-R is aryl group having 6 to 10 carbon atoms, alkyl group having 1 to 4 carbon atoms or cycloalkyl group having 5 to 10 carbon atoms, which may be substituted with alkyl group having 1 to 4 carbon atoms or cycloalkyl group having 5 to 10 carbon atoms, and > C (-R)₂R in (A) is hydrogen, an aryl group having 6 to 10 carbon atoms which may be substituted with an alkyl group having 1 to 4 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms, an alkyl group having 1 to 4 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms.

More preferable combinations of the substituents in the formula (2-a), (2-b), (2-c), (2-d), (2-e) and (2-f) are as follows.

R¹、R²、R³、R⁴、R⁵、R⁶、R⁷、R⁸、R⁹、R¹⁰And R¹¹Independently hydrogen, aryl group having 6 to 16 carbon atoms which may be substituted with alkyl group having 1 to 4 carbon atoms or cycloalkyl group having 5 to 10 carbon atoms, heteroaryl group having 2 to 20 carbon atoms which may be substituted with alkyl group having 1 to 4 carbon atoms or cycloalkyl group having 5 to 10 carbon atoms, diarylamino group (wherein aryl group is aryl group having 6 to 10 carbon atoms which may be substituted with alkyl group having 1 to 4 carbon atoms or cycloalkyl group having 5 to 10 carbon atoms), diarylboron group (wherein aryl group is aryl group having 6 to 10 carbon atoms which may be substituted with alkyl group having 1 to 4 carbon atoms or cycloalkyl group having 5 to 10 carbon atoms), alkyl group having 1 to 12 carbon atoms or cycloalkyl group having 3 to 16 carbon atoms, and R is¹、R²、R³、R⁴、R⁵、R⁶、R⁷、R⁸、R⁹、R¹⁰And R¹¹Wherein adjacent groups are bonded to each other and form an aryl ring having 9 to 16 carbon atoms or a heteroaryl ring having 6 to 15 carbon atoms together with the a, b or c ring, and at least one hydrogen in the ring can be substituted by an aryl group having 6 to 13 carbon atoms which may be substituted by an alkyl group having 1 to 4 carbon atoms or a cycloalkyl group having 3 to 10 carbon atoms, a heteroaryl group having 2 to 12 carbon atoms which may be substituted by an alkyl group having 1 to 4 carbon atoms or a cycloalkyl group having 3 to 10 carbon atoms, a diarylamino group (wherein the aryl group is an aryl group having 6 to 12 carbon atoms which may be substituted by an alkyl group having 1 to 4 carbon atoms or a cycloalkyl group having 3 to 10 carbon atoms), a diarylboron group (wherein the aryl group is an aryl group having 6 to 12 carbon atoms which may be substituted by an alkyl group having 1 to 4 carbon atoms or a cycloalkyl group having 3 to 10 carbon atoms), an alkyl group having 1 to 12 carbon atoms or a cycloalkyl group having 3 to 20 carbon,

X¹And X²Each independently > O, > N-R or > C (-R)₂R > N-R is aryl group with 6-10 carbon atoms, alkyl group with 1-4 carbon atoms or cycloalkyl group with 5-10 carbon atoms, which can be substituted by alkyl group with 1-4 carbon atoms or cycloalkyl group with 5-10 carbon atoms, and the R > C (-R)₂R in (A) is hydrogen, an aryl group having 6 to 10 carbon atoms which may be substituted with an alkyl group having 1 to 4 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms, an alkyl group having 1 to 4 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms.

Further preferable combinations of the substituents in the formulae (2-a), (2-b), (2-c), (2-d), (2-e) and (2-f) are as follows.

R¹、R²、R³、R⁴、R⁵、R⁶、R⁷、R⁸、R⁹、R¹⁰And R¹¹Independently hydrogen, an aryl group having 6 to 16 carbon atoms which may be substituted with an alkyl group having 1 to 4 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms, a heteroaryl group having 2 to 20 carbon atoms which may be substituted with an alkyl group having 1 to 4 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms, a diarylamino group (wherein the aryl group is an aryl group having 6 to 10 carbon atoms which may be substituted with an alkyl group having 1 to 4 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms), a diarylboron group (wherein the aryl group is an aryl group having 6 to 10 carbon atoms which may be substituted with an alkyl group having 1 to 4 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms), an alkyl group having 1 to 12 carbon atoms or a cycloalkyl group having 3 to 16 carbon atoms,

in addition, R¹、R²、R³、R⁴、R⁵、R⁶、R⁷、R⁸、R⁹、R¹⁰And R¹¹Wherein adjacent groups are bonded to each other and form an aryl ring having 9 to 16 carbon atoms or a heteroaryl ring having 6 to 15 carbon atoms together with the a, b or c ring, and at least one hydrogen in the ring can be substituted by an aryl group having 6 to 13 carbon atoms which may be substituted by an alkyl group having 1 to 4 carbon atoms or a cycloalkyl group having 3 to 10 carbon atoms, a heteroaryl group having 2 to 12 carbon atoms which may be substituted by an alkyl group having 1 to 4 carbon atoms or a cycloalkyl group having 3 to 10 carbon atoms, a diarylamino group (wherein the aryl group is an aryl group having 6 to 12 carbon atoms which may be substituted by an alkyl group having 1 to 4 carbon atoms or a cycloalkyl group having 3 to 10 carbon atoms), an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 10 carbon atoms),

X¹And X²Each independently represents > O or > N-R, wherein R > N-R is C6-10 aryl, C1-4 alkyl or C5-10 cycloalkyl which may be substituted by C1-4 alkyl or C5-10 cycloalkyl.

More specific examples of the polycyclic aromatic compound represented by the formula (2) include compounds represented by the following formulae. In the following formulae, "Me" represents a methyl group, "tBu" represents a tert-butyl group (t-butyl), "iPr" represents an isopropyl group, "Ph" represents a phenyl group, "tAm" represents a tert-amyl group (t-amyl), and "D" represents deuterium.

1-2-2 polycyclic aromatic Compound represented by formula (2) and method for producing multimer thereof

The polycyclic aromatic compound represented by the formula (2) and the multimer thereof can be synthesized, for example, by the method disclosed in international publication No. 2019/009052 as "method for producing the polycyclic aromatic compound represented by the formula (2) and the multimer thereof".

1-3. luminescent layer

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 may be one kind of compound represented by formula (1), may be a combination of two or more kinds of compounds represented by formula (1), and may be a combination of a compound represented by formula (1) and a compound other than the compound represented by formula (1). The host material is preferably one compound represented by formula (1) or a combination of two or more compounds represented by formula (1). The dopant material may be one kind of compound represented by formula (2), may be a combination of two or more kinds of compounds represented by formula (2), or may be a combination of a compound represented by formula (2) and a compound other than the compound represented by formula (2). The dopant material is preferably one compound represented by formula (2) or a combination of two or more compounds represented by formula (2).

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 host material is mixed in advance and then 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% of the total of the light-emitting layer material.

The amount of the dopant material used differs depending on the type 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. In the above range, for example, concentration quenching is preferably prevented.

Examples of the host material that can be used in combination with the compound represented by formula (1) include fused ring derivatives of pyrene and the like, bisstyryl derivatives such as bisstyrylanthracene derivatives and distyrylbenzene derivatives, tetraphenylbutadiene derivatives, cyclopentadiene derivatives, fluorene derivatives, benzofluorene derivatives, and the like, which are known as light-emitting substances.

Examples of the dopant material that can be used in combination with the compound represented by formula (2) include condensed ring derivatives such as anthracene and pyrene, bisstyryl derivatives such as bisstyrylanthracene derivatives and distyrylbenzene derivatives, tetraphenylbutadiene derivatives, cyclopentadiene derivatives, fluorene derivatives, and benzofluorene derivatives, which are known as light-emitting substances.

2. Electron injection layer and 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 high in electron injection efficiency and capable of transporting the injected electrons efficiently. 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 in organic EL devices.

The material used for the electron transport layer or the electron injection layer preferably contains at least one selected from the following materials: 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, phosphorus 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: borane derivatives, pyridine derivatives, naphthalene derivatives, fluoranthene derivatives, BO derivatives, anthracene derivatives, benzofluorene 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, benzoxazole (benzoxazole) compounds, gallium complexes, quinoline derivatives, phenanthrene derivatives, phenanthroline derivatives, perinone or more kinds of derivatives, and the like, Pyrazole derivatives, perfluorinated phenylene derivatives, triazine derivatives, pyrazine derivatives, benzoquinoline derivatives (e.g., 2 '-bis (benzo [ h ] quinolin-2-yl) -9,9' -spirobifluorene), imidazopyridine 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 (4'- (2, 2': 6 '2' -terpyridyl)) benzene), naphthyridine derivatives (e.g., bis (1-naphthyl) -4- (1, 8-naphthyridin-2-yl) phenylphosphine oxide, etc.), and the like, Aldazine derivatives, pyrimidine derivatives, arylnitrile derivatives, indole derivatives, phosphorus 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-based derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, arylnitrile derivatives, triazine derivatives, benzimidazole derivatives, phenanthroline derivatives, hydroxyquinoline-based metal complexes, thiazole derivatives, benzothiazole derivatives, silole derivatives, and oxazoline derivatives.

Borane derivatives

The borane derivative is, for example, a compound represented by the following formula (ETM-1), and is disclosed in detail in Japanese patent laid-open No. 2007-27587.

In the formula (ETM-1), R¹¹And R¹²Each independently is at least one of hydrogen, alkyl, cycloalkyl, aryl which may be substituted, silyl which may be substituted, a nitrogen-containing heterocycle which may be substituted, or cyano, R ¹³～R¹⁶Each independently is an alkyl group which may be substituted, a cycloalkyl group which may be substituted or an aryl group which may be substituted, X is an arylene group which may be substituted, Y is an aryl group having 16 or less carbon atoms which may be substituted, a substitutedAnd n is an integer of 0 to 3, independently. In addition, as the substituent in the case of "may be substituted" or "substituted", there may be mentioned: aryl, heteroaryl, alkyl or cycloalkyl, and the like.

Among the compounds represented by the formula (ETM-1), a compound represented by the following formula (ETM-1-1) or a compound represented by the following formula (ETM-1-2) is preferable.

In the formula (ETM-1-1), R¹¹And R¹²Each independently is at least one of hydrogen, alkyl, cycloalkyl, aryl which may be substituted, silyl which may be substituted, a nitrogen-containing heterocycle which may be substituted, or cyano, R¹³～R¹⁶Each independently is an alkyl group which may be substituted, a cycloalkyl group which may be substituted, or an aryl group which may be substituted, R²¹And R²²Each independently is at least one of hydrogen, alkyl, cycloalkyl, aryl which may be substituted, silyl which may be substituted, a nitrogen-containing heterocycle which may be substituted, or cyano, X¹Is an arylene group having 20 or less carbon atoms which may be substituted, n is independently an integer of 0 to 3, and m is independently an integer of 0 to 4. In addition, as the substituent in the case of "may be substituted" or "substituted", there may be mentioned: aryl, heteroaryl, alkyl or cycloalkyl, and the like.

In the formula (ETM-1-2), R¹¹And R¹²Each independently is at least one of hydrogen, alkyl, cycloalkyl, aryl which may be substituted, silyl which may be substituted, a nitrogen-containing heterocycle which may be substituted, or cyano, R¹³～R¹⁶Each independently is an alkyl group which may be substituted, a cycloalkyl group which may be substituted or an aryl group which may be substituted, X¹Is an arylene group having 20 or less carbon atoms which may be substituted, and n is an integer of 0 to 3 independently. In addition, as "may be substitutedThe substituents in the case of "or" substituted "include: aryl, heteroaryl, alkyl or cycloalkyl, and the like.

As X¹Specific examples of (2) include divalent groups represented by any one of the following formulae (X-1) to (X-9).

(in the formulae, R^aEach independently being an alkyl, cycloalkyl or optionally substituted phenyl group, representing a bonding position)

Specific examples of the borane derivative include the following compounds.

The borane derivative can be produced using a known raw material and a known synthesis method.

< pyridine derivatives >

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

Phi- (pyridine substituent)_n (ETM-2)

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

In the formula (ETM-2-1), R¹¹～R¹⁸Each independently represents hydrogen, an alkyl group (preferably an alkyl group having 1 to 24 carbon atoms), a cycloalkyl group (preferably a cycloalkyl group having 3 to 12 carbon atoms) or an aryl group (preferably an aryl group having 6 to 30 carbon atoms).

In the formula (ETM-2-2), R¹¹And R¹²Independently represents hydrogen or alkyl (preferably having carbon number of 1 to c)24 alkyl group), cycloalkyl group (preferably C3-C12 cycloalkyl group), or aryl group (preferably C6-C30 aryl group), R¹¹And R¹²May be bonded to form a ring.

In each formula, the "pyridine substituent" is any one of the following formulas (Py-1) to (Py-15) (wherein:. represents a bonding site), and the pyridine substituent may be independently substituted with an alkyl group having 1 to 4 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms. Specific examples thereof include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl and the like, and methyl is preferable. In addition, the pyridine substituent may be bonded to the phi, anthracene ring or fluorene ring in each formula via phenylene or naphthylene.

The pyridine substituent is any one of the formulae (Py-1) to (Py-15), and among these, any one of the formulae (Py-21) to (Py-44) (wherein:. represents a bonding site) is preferable.

At least one hydrogen of each pyridine derivative may be substituted by deuterium, and one of the two "pyridine substituents" in the formula (ETM-2-1) and the formula (ETM-2-2) may be substituted by an aryl group.

R¹¹～R¹⁸The "alkyl group" in (1) may be 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. The preferred "alkyl group" is an alkyl group having 1 to 18 carbon atoms (branched alkyl group having 3 to 18 carbon atoms). More preferably, the "alkyl group" is an alkyl group having 1 to 12 carbon atoms (branched alkyl group having 3 to 12 carbon atoms). Further preferred "alkyl group" is an alkyl group having 1 to 6 carbon atoms (branched alkyl group having 3 to 6 carbon atoms). Particularly preferred "alkyl group" is an alkyl group having 1 to 4 carbon atoms (branched alkyl group having 3 to 4 carbon atoms).

As the alkyl group having 1 to 4 carbon atoms substituted in the pyridine substituent, the description of the alkyl group can be cited.

As R¹¹～R¹⁸Examples of the "cycloalkyl group" in (1) include cycloalkyl groups having 3 to 12 carbon atoms. The preferable "cycloalkyl group" is a cycloalkyl group having 3 to 10 carbon atoms. More preferably, the "cycloalkyl group" is a cycloalkyl group having 3 to 8 carbon atoms. Further preferred "cycloalkyl group" is a cycloalkyl group having 3 to 6 carbon atoms.

Specific "cycloalkyl" groups include: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, dimethylcyclohexyl, or the like.

As R¹¹～R¹⁸The "aryl group" in (1) is preferably an aryl group having 6 to 30 carbon atoms, more preferably an aryl group having 6 to 18 carbon atoms, still more preferably an aryl group having 6 to 14 carbon atoms, and particularly preferably an aryl group having 6 to 12 carbon atoms.

Specific examples of the "aryl group having 6 to 30 carbon atoms" include: phenyl as monocyclic aryl, (1-, 2-) naphthyl as condensed bicyclic aryl, acenaphthene- (1-, 3-, 4-, 5-) as condensed tricyclic aryl, fluorene- (1-, 2-, 3-, 4-, 9-) as non- (1-, 2-) as condensed tricyclic aryl, (1-, 2-, 3-, 4-, 9-) phenanthrene, triphenylene- (1-, 2-) as condensed tetracyclic aryl, pyrene- (1-, 2-, 4-) as condensed tetracyclic aryl, tetracene- (1-, 2-, 5-) as condensed pentacyclic aryl, perylene- (1-, 2-, 3-) as condensed tetracyclic aryl, perylene- (2-, 3-) as condensed tetracyclic aryl, perylene, and the like, Pentacene- (1-, 2-, 5-, 6-) radicals and the like.

It is preferable thatExamples of the "aryl group having 6 to 30 carbon atoms" include phenyl, naphthyl, phenanthryl,

Examples of the group include a phenyl group, a 1-naphthyl group, a 2-naphthyl group and a phenanthryl group, and examples of the group include a phenyl group, a 1-naphthyl group and a 2-naphthyl group.

R in the formula (ETM-2-2)¹¹And R¹²A ring may be bonded to form a ring, and as a result, cyclobutane, cyclopentane, cyclopentene, cyclopentadiene, cyclohexane, fluorene, indene, or the like may be spiro-bonded to the 5-membered ring of the fluorene skeleton.

Specific examples of the pyridine derivative include the following compounds.

The pyridine derivative can be produced using a known raw material and a known synthesis method.

< fluoranthene derivative >

The fluoranthene derivative is, for example, a compound represented by the following formula (ETM-3), and is disclosed in detail in international publication No. 2010/134352.

In the formula (ETM-3), X¹²～X²¹Represents hydrogen, halogen, linear, branched or cyclic alkyl, linear, branched or cyclic alkoxy, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl. Here, as the substituent at the time of substitution, there may be mentioned: aryl, heteroaryl, alkyl or cycloalkyl, and the like.

Specific examples of the fluoranthene derivative include the following compounds.

< BO series derivative >

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

R⁶¹～R⁷¹Each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkoxy, or aryloxy, at least one of which may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl.

In addition, R⁶¹～R⁷¹May be bonded to each other and together with the a-ring, b-ring or c-ring form an aryl or heteroaryl ring, at least one hydrogen in the formed ring may be substituted by aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkoxy or aryloxy, at least one of which may be substituted by aryl, heteroaryl, alkyl or cycloalkyl.

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

As for the explanation of the form of the substituent or ring in the formula (ETM-4), the explanation of the polycyclic aromatic compound represented by the formula (1) or the formula (2) can be cited.

Specific examples of the BO-based derivative include the following compounds.

The BO-based derivative can be produced using a known raw material and a known synthesis method.

< Anthracene derivatives >

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

Ar¹Each independently a single bond, a divalent benzene, naphthalene, anthracene, fluorene or phenalene.

Ar²Each independently an aryl group having 6 to 20 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 examples of the "aryl group having 6 to 20 carbon atoms" include: phenyl group, (o, m, p) tolyl group, (2,3-, 2,4-, 2,5-, 2,6-, 3,4-, 3,5-) xylyl group, mesityl (2,4, 6-trimethylphenyl group), (o, m, p) cumenyl group as monocyclic aryl group, (2-, 3-, 4-) biphenyl group as bicyclic aryl group, (1-, 2-) naphthyl group as condensed bicyclic aryl group, (m-terphenyl-2 ' -yl group, m-terphenyl-4 ' -yl group, m-terphenyl-5 ' -yl group, o-terphenyl-3 ' -yl group, o-terphenyl-4 ' -yl group, p-terphenyl-2 ' -yl group, m-terphenyl-2-yl group, p-terphenyl-4 ' -yl group, p-terphenyl-2-yl group, p-terphenyl, M-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), anthracene- (1-, 2-, 9-) yl, acenaphthene- (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, triphenylene- (1-, 9-) -as condensed tricyclic aryl, 2-) group, pyrene- (1-, 2-, 4-) group, tetracene- (1-, 2-, 5-) group, perylene- (1-, 2-, 3-) group as condensed pentacyclic aryl group, and the like. Specific examples of the "aryl group having 6 to 10 carbon atoms" include: phenyl, biphenyl, naphthyl, terphenyl, anthracenyl, acenaphthenyl, fluorenyl, phenalkenyl, phenanthrenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, and the like.

R¹～R⁴Each independently represents hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms or an aryl group having 6 to 20 carbon atoms.

R¹～R⁴Carbon of (5)The alkyl group having a number of 1 to 6 may be either a straight chain or a branched chain. Namely, a C1-6 linear alkyl group or a C3-6 branched alkyl group. More preferably an alkyl group having 1 to 4 carbon atoms (branched alkyl group having 3 to 4 carbon atoms). Specific examples thereof 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, and 2-ethylbutyl, and preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, and tert-butyl, and more preferably methyl, ethyl, or tert-butyl.

As R¹～R⁴Specific examples of the cycloalkyl group having 3 to 6 carbon atoms in (b) include: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, dimethylcyclohexyl, or the like.

With respect to R¹～R⁴The aryl group having 6 to 20 carbon atoms in (A) is 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. As a specific example of "aryl group having 6 to 20 carbon atoms", Ar ²Specific examples of the "aryl group having 6 to 20 carbon atoms" in (1). The "aryl group having 6 to 20 carbon atoms" is preferably a phenyl group, a biphenyl group, a terphenyl group or a naphthyl group, more preferably a phenyl group, a biphenyl group, a 1-naphthyl group, a 2-naphthyl group or an m-terphenyl-5' -yl group, further preferably a phenyl group, a biphenyl group, a 1-naphthyl group or a 2-naphthyl group, and most preferably a phenyl group.

Specific examples of the anthracene derivative include the following compounds.

These anthracene derivatives can be produced using a known raw material and a known synthesis method.

< benzofluorene derivative >

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

Ar¹Each independently an aryl group having 6 to 20 carbon atoms, and Ar of the formula (ETM-5)²The "aryl group having 6 to 20 carbon atoms" in (A) is the same as defined above. 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 examples thereof include: phenyl, biphenyl, naphthyl, terphenyl, anthracenyl, acenaphthenyl, fluorenyl, phenalkenyl, phenanthrenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, and the like.

Ar²Independently represents hydrogen, alkyl (preferably C1-C24 alkyl), cycloalkyl (preferably C3-C12 cycloalkyl) or aryl (preferably C6-C30 aryl), or two Ar ²May be bonded to form a ring.

Ar²The "alkyl group" in (1) may be 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. The preferred "alkyl group" is an alkyl group having 1 to 18 carbon atoms (branched alkyl group having 3 to 18 carbon atoms). More preferably, the "alkyl group" is an alkyl group having 1 to 12 carbon atoms (branched alkyl group having 3 to 12 carbon atoms). Further preferred "alkyl group" is an alkyl group having 1 to 6 carbon atoms (branched alkyl group having 3 to 6 carbon atoms). Particularly preferred "alkyl group" is 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 and the like.

As Ar²Examples of the "cycloalkyl group" in (1) include cycloalkyl groups having 3 to 12 carbon atoms. The preferable "cycloalkyl group" is a cycloalkyl group having 3 to 10 carbon atoms. More preferably, the "cycloalkyl group" is a cycloalkyl group having 3 to 8 carbon atoms. Further preferred "cycloalkyl group" is a cycloalkyl group having 3 to 6 carbon atoms. Specific "cycloalkyl" groups include: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl Methylcyclohexyl, cyclooctyl, dimethylcyclohexyl, or the like.

As Ar²The "aryl group" in (1) is preferably an aryl group having 6 to 30 carbon atoms, more preferably an aryl group having 6 to 18 carbon atoms, still more preferably an aryl group having 6 to 14 carbon atoms, and particularly preferably an aryl group having 6 to 12 carbon atoms.

Specific examples of the "aryl group having 6 to 30 carbon atoms" include: phenyl, naphthyl, acenaphthenyl, fluorenyl, phenalkenyl, phenanthrenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, pentacenyl, and the like.

Two Ar²A ring may be bonded to form a ring, and as a result, cyclobutane, cyclopentane, cyclopentene, cyclopentadiene, cyclohexane, fluorene, indene, or the like may be spiro-bonded to the 5-membered ring of the fluorene skeleton.

Specific examples of the benzofluorene derivative include the following compounds.

The benzofluorene derivative can be produced using a known raw material and a known synthesis method.

< phosphine oxide derivative >

The phosphine oxide derivative is, for example, a compound represented by the following formula (ETM-7-1). Details are also described in international publication No. 2013/079217 and international publication No. 2013/079678.

R⁵Is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 16 carbon atoms, an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 5 to 20 carbon atoms,

R⁶CN, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, cycloalkyl group having 3 to 16 carbon atoms, heteroalkyl group having 1 to 20 carbon atoms, aryl group having 6 to 20 carbon atoms, heteroaryl group having 5 to 20 carbon atoms, alkoxy group having 1 to 20 carbon atoms or aryl group having 6 to 20 carbon atomsThe oxygen radical is selected from the group consisting of oxygen radicals,

R⁷and R⁸Independently represents a substituted or unsubstituted aryl group having 6 to 20 carbon atoms or a heteroaryl group having 5 to 20 carbon atoms,

R⁹is oxygen or sulfur, and is selected from the group consisting of,

j is 0 or 1, k is 0 or 1, r is an integer of 0 to 4, and q is an integer of 1 to 3.

Here, as the substituent at the time of substitution, there may be mentioned: aryl, heteroaryl, alkyl or cycloalkyl, and the like.

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

R¹～R³Which may be the same or different, are selected from the group consisting of hydrogen, alkyl, cycloalkyl, aralkyl, alkenyl, cycloalkenyl, alkynyl, alkoxy, alkylthio, cycloalkylthio, aryl ether, arylthioether, aryl, heterocyclic, halogen, cyano, formyl, carbonyl, carboxyl, amino, nitro, silane, and fused rings formed between adjacent substituents.

Ar¹May be the same or different and is an arylene or heteroarylene group. Ar (Ar)²May be the same or different and is aryl or heteroaryl. Wherein Ar is¹And Ar ²Has a substituent, or forms a condensed ring with an adjacent substituent. n is an integer of 0 to 3, and when n is 0, no unsaturated moiety is present, and when n is 3, R is not present¹。

Among these substituents, the alkyl group means, for example, a saturated aliphatic hydrocarbon group such as a methyl group, an ethyl group, a propyl group, or a butyl group, and the alkyl group may be unsubstituted or substituted. The substituent to be substituted is not particularly limited, and examples thereof include an alkyl group, an aryl group, and a heterocyclic group, and these are also common in the following description. The number of carbons of the alkyl group is not particularly limited, and is usually in the range of 1 to 20 in terms of easiness of obtaining and cost.

The cycloalkyl group means a saturated alicyclic hydrocarbon group such as a cyclopropyl group, a cyclohexyl group, a norbornyl group, an adamantyl group and the like, and the cycloalkyl group may be unsubstituted or substituted. The number of carbon atoms in the alkyl moiety is not particularly limited, and is usually within a range of 3 to 20.

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

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

The cycloalkenyl group means an unsaturated alicyclic hydrocarbon group having a double bond, such as a cyclopentenyl group, a cyclopentadienyl group, or a cyclohexenyl group, and the cycloalkenyl group may be unsubstituted or substituted.

The alkynyl group means an unsaturated aliphatic hydrocarbon group containing a triple bond such as an ethynyl group, and the alkynyl group may be unsubstituted or substituted. The carbon number of the alkynyl group is not particularly limited, and is usually in the range of 2 to 20.

The alkoxy group means, for example, an aliphatic hydrocarbon group having an ether bond such as a methoxy group, and the aliphatic hydrocarbon group may be unsubstituted or substituted. The number of carbon atoms of the alkoxy group is not particularly limited, and is usually in the range of 1 to 20.

The alkylthio group is a group in which an oxygen atom of an ether bond of an alkoxy group is substituted with a sulfur atom.

The cycloalkylthio group is a group in which an oxygen atom of an ether bond of a cycloalkoxy group is substituted with a sulfur atom.

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

The arylthioether group is a group in which an oxygen atom of an ether bond of an arylether group is substituted with a sulfur atom.

The aryl group represents, for example, an aromatic hydrocarbon group such as a phenyl group, a naphthyl group, a biphenyl group, a phenanthryl group, a terphenyl group, or a pyrenyl group. The aryl group may be unsubstituted or substituted. The number of carbons of the aryl group is not particularly limited, and is usually in the range of 6 to 40.

The heterocyclic group means a cyclic structural group having an atom other than carbon, such as a furyl group, a thienyl group, an oxazolyl group, a pyridyl group, a quinolyl group, and a carbazolyl group, and the heterocyclic group may be unsubstituted or substituted. The number of carbon atoms of the heterocyclic group is not particularly limited, and is usually in the range of 2 to 30.

Halogen means fluorine, chlorine, bromine and iodine.

The formyl group, the carbonyl group, and the amino group may contain a group substituted with an aliphatic hydrocarbon, an alicyclic hydrocarbon, an aromatic hydrocarbon, a heterocycle, or the like.

Further, the aliphatic hydrocarbon, alicyclic hydrocarbon, aromatic hydrocarbon, and heterocyclic ring may be unsubstituted or substituted.

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

The condensed ring formed between the adjacent substituent is, for example, Ar¹And R²、Ar¹And R³、Ar²And R²、Ar²And R³、R²And R³、Ar¹And Ar²Etc. are formed between them. Here, when n is 1, two R are¹May form conjugated or non-conjugated fused rings with each other. These condensed rings may contain a nitrogen atom, an oxygen atom, a sulfur atom in the ring inner structure, or may be further condensed with other rings.

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

The phosphine oxide derivatives can be produced using known starting materials and known synthesis methods.

[ pyrimidine derivative ]

The pyrimidine derivative is, for example, a compound represented by the following formula (ETM-8), and preferably a compound represented by the following formula (ETM-8-1). Details are also described in international publication No. 2011/021689.

Ar is independently aryl which may be substituted or heteroaryl which may be substituted. n is an integer of 1 to 4, preferably an integer of 1 to 3, more preferably 2 or 3.

Examples of the "aryl group" of the "aryl group which may be substituted" include aryl groups having 6 to 30 carbon atoms, preferably aryl groups having 6 to 24 carbon atoms, more preferably aryl groups having 6 to 20 carbon atoms, and still more preferably aryl groups having 6 to 12 carbon atoms.

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

Examples of the "heteroaryl group" of the "optionally substituted 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, benzo [ b ] thienyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenoxathinyl, thianthrenyl, indolizinyl and the like.

Additionally, the aryl and heteroaryl groups may be substituted, such as by the aryl or heteroaryl groups, respectively.

Specific examples of the pyrimidine derivative include the following compounds.

The pyrimidine derivative can be produced using a known raw material and a known synthesis method.

< aryl nitrile derivatives >

The arylnitrile derivative is, for example, a compound represented by the following formula (ETM-9), or a multimer in which a plurality of the compounds are bonded by a single bond or the like. Details are described in U.S. patent application publication No. 2014/0197386.

From the viewpoint of fast electron-transporting property, Ar_niPreferably a large number of carbon atoms, and Ar is Ar from the viewpoint of a high T1_niPreferably, the number of carbon atoms is small. Specifically, when used for a layer adjacent to the light-emitting layer, T1 is preferably high so that Ar is high_niThe aryl group has 6 to 20 carbon atoms, preferably 6 to 14 carbon atoms, and more preferably 6 to 10 carbon atoms. The number n of nitrile groups substituted is preferably large in view of high T1, and preferably small in view of high S1. Specifically, the number n of substitution of nitrile groups is an integer of 1 to 4, preferably an integer of 1 to 3, more preferably an integer of 1 to 2, and still more preferably 1.

Ar is independently aryl which may be substituted or heteroaryl which may be substituted. From the viewpoint of high S1 and high T1, donor heteroaryl groups are preferable, and since they are used as an electron transport layer, donor heteroaryl groups are preferably small in number. From the viewpoint of charge transport properties, aryl or heteroaryl groups having a large number of carbon atoms are preferable, and a large number of substituents are preferable. Specifically, the number m of substitution of Ar is an integer of 1 to 4, preferably an integer of 1 to 3, and more preferably 1 to 2.

The arylnitrile derivative may be a polymer in which a plurality of compounds represented by the formula (ETM-9) are bonded by a single bond or the like. In this case, the bond may be formed by an aryl ring (preferably, a polyvalent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring, or triphenylene ring) in addition to a single bond.

Specific examples of the arylnitrile derivative include the following compounds.

The aryl nitrile derivative can be produced using a known raw material and a known synthesis method.

< triazine derivative >

The triazine derivative is, for example, a compound represented by the following formula (ETM-10), and preferably a compound represented by the following formula (ETM-10-1). Details are described in U.S. patent application publication No. 2011/0156013.

Ar is independently aryl which may be substituted or heteroaryl which may be substituted. n is an integer of 1 to 3, preferably 2 or 3.

Specific examples of the triazine derivative include the following compounds.

The triazine derivative can be produced using a known raw material and a known synthesis method.

< benzimidazole derivative >

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

Phi- (benzimidazole substituent)_n (ETM-11)

Phi is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring or triphenylene ring), n is an integer of 1 to 4, the "benzimidazole substituent" is a substituent in which the pyridyl group in the "pyridine substituent" of the formulae (ETM-2), (ETM-2-1) and (ETM-2-2) is substituted with a benzimidazole group, and at least one hydrogen in the benzimidazole derivative may be substituted with deuterium.

Denotes a bonding site.

R in said benzimidazolyl group¹¹Hydrogen, alkyl group having 1 to 24 carbon atoms, cycloalkyl group having 3 to 12 carbon atoms or aryl group having 6 to 30 carbon atoms, R in the formulae (ETM-2-1) and (ETM-2-2)¹¹And (4) description.

φ is further preferably an anthracene ring or a fluorene ring, and the structure in that case can be referred to the description in the formula (ETM-2-1) or the formula (ETM-2-2), R in each formula ¹¹～R¹⁸Reference may be made to the description in formula (ETM-2-1) or formula (ETM-2-2). In addition, although the formula (ETM-2-1) or the formula (ETM-2-2) has been described as the form in which two pyridine substituents are bonded, when these are substituted with benzimidazole substituents, two pyridine substituents may be substituted with benzimidazole substituents (that is, n ═ 2), and either one of the pyridine substituents may be substituted with benzimidazole substituents and R may be substituted with benzimidazole substituents¹¹～R¹⁸Substituted with another pyridine substituent (i.e., n ═ 1). Further, R in the formula (ETM-2-1) may be substituted with a benzimidazole substituent¹¹～R¹⁸And R is¹¹～R¹⁸Substituted "pyridine-based substituents".

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

The benzimidazole derivative can be produced using a known raw material and a known synthesis method.

[ phenanthroline derivative ]

The phenanthroline derivative is, for example, a compound represented by the following formula (ETM-12) or formula (ETM-12-1). Details are described in international publication No. 2006/021982.

Of the formulae R¹¹～R¹⁸Each independently hydrogen, alkyl (preferably C1-C24 alkyl), cycloalkyl (preferably C3-C12 cycloalkyl) or aryl (preferably C6-C30 aryl). Further, in the formula (ETM-12-1), R¹¹～R¹⁸Any of these bonds to φ as an aryl ring.

At least one hydrogen in each phenanthroline derivative may be substituted by deuterium.

As R¹¹～R¹⁸Alkyl, cycloalkyl and aryl in (1), may be citedBy R in formula (ETM-2)¹¹～R¹⁸And (4) description. Further, phi may be represented by the following structural formula in addition to the above examples. In the following structural formulae, R is independently hydrogen, methyl, ethyl, isopropyl, cyclohexyl, phenyl, 1-naphthyl, 2-naphthyl, biphenyl, or terphenyl, and represents a bonding position.

Specific examples of the phenanthroline derivative include: 4, 7-diphenyl-1, 10-phenanthroline, 2, 9-dimethyl-4, 7-diphenyl-1, 10-phenanthroline, 9, 10-bis (1, 10-phenanthroline-2-yl) anthracene, 2, 6-bis (1, 10-phenanthroline-5-yl) pyridine, 1,3, 5-tris (1, 10-phenanthrolin-5-yl) benzene, 9' -difluoro-bis (1, 10-phenanthrolin-5-yl), 2, 9-dimethyl-4, 7-biphenyl-1, 10-phenanthroline (bathocuproine), 1, 3-bis (2-phenyl-1, 10-phenanthrolin-9-yl) benzene, a compound represented by the following structural formula, or the like.

The phenanthroline derivative can be produced using a known raw material and a known synthesis method.

< hydroxyquinoline-based metal complex >

The hydroxyquinoline metal complex is, for example, a compound represented by the following formula (ETM-13).

In the formula, R¹～R⁶Each independently is hydrogen, fluorine, alkyl, cycloalkyl, aralkyl, alkenyl, cyano, alkoxy or aryl, M is Li, Al, Ga, Be or Zn, and n is an integer of 1 to 3.

Specific examples of the hydroxyquinoline metal complex include: lithium 8-quinolinolate, aluminum tris (8-quinolinolate), aluminum tris (4-methyl-8-quinolinolate), aluminum tris (5-methyl-8-quinolinolate), aluminum tris (3, 4-dimethyl-8-quinolinolate), aluminum tris (4, 5-dimethyl-8-quinolinolate), aluminum tris (4, 6-dimethyl-8-quinolinolate), aluminum bis (2-methyl-8-quinolinolate) (phenoxide), aluminum bis (2-methyl-8-quinolinolate) (2-methylphenol), aluminum bis (2-methyl-8-quinolinolate) (3-methylphenol), aluminum bis (2-methyl-8-quinolinolate) (4-methylphenol), aluminum tris (4-methyl-8-quinolinolate), Bis (2-methyl-8-quinolinolato) (2-phenylphenol) aluminum, bis (2-methyl-8-quinolinolato) (3-phenylphenol) aluminum, bis (2-methyl-8-quinolinolato) (4-phenylphenol) aluminum, bis (2-methyl-8-quinolinolato) (2, 3-dimethylphenol) aluminum, bis (2-methyl-8-quinolinolato) (2, 6-dimethylphenol) aluminum, bis (2-methyl-8-quinolinolato) (3, 4-dimethylphenol) aluminum, bis (2-methyl-8-quinolinolato) (3, 5-dimethylphenol) aluminum, bis (2-methyl-8-quinolinolato) (3, 5-di-tert-butylphenol) aluminum, bis (2-methyl-8-quinolinolato) (2, 6-diphenylphenol) aluminum, bis (2-methyl-8-quinolinolato) (2,4, 6-triphenylpheno) aluminum, bis (2-methyl-8-quinolinolato) (2,4, 6-trimethylphenol) aluminum, bis (2-methyl-8-quinolinolato) (2,4,5, 6-tetramethylphenol) aluminum, bis (2-methyl-8-quinolinolato) (1-naphthol) aluminum, bis (2-methyl-8-quinolinolato) (2-naphthol) aluminum, bis (2, 4-dimethyl-8-quinolinolato) (2-phenylphenolate) aluminum, bis (2-methyl-8-quinolinolato) (2-naphthol) aluminum, bis (2, 4-dimethyl-8-quinolinolato) (3-phenylphenol) aluminum, bis (2, 4-dimethyl-8-quinolinolato) (4-phenylphenol) aluminum, bis (2, 4-dimethyl-8-quinolinolato) (3, 5-dimethylphenol) aluminum, bis (2, 4-dimethyl-8-quinolinolato) (3, 5-di-tert-butylphenol) aluminum, bis (2-methyl-8-quinolinolato) aluminum- μ -oxo-bis (2-methyl-8-quinolinolato) aluminum, bis (2, 4-dimethyl-8-quinolinolato) aluminum- μ -oxo-bis (2, 4-dimethyl-8-quinolinolato) aluminum, aluminum, Bis (2-methyl-4-ethyl-8-quinolinolato) aluminum- μ -oxo-bis (2-methyl-4-ethyl-8-quinolinolato) aluminum, bis (2-methyl-4-methoxy-8-quinolinolato) aluminum- μ -oxo-bis (2-methyl-4-methoxy-8-quinolinolato) aluminum, bis (2-methyl-5-cyano-8-quinolinolato) aluminum- μ -oxo-bis (2-methyl-5-cyano-8-quinolinolato) aluminum, bis (2-methyl-5-trifluoromethyl-8-quinolinolato) aluminum- μ -oxo-bis (2-methyl-5-trifluoromethyl-8-quinolinolato) aluminum -hydroxyquinoline) aluminum, bis (10-hydroxybenzo [ h ] quinoline) beryllium, and the like.

The hydroxyquinoline metal complex can be produced using a known raw material and a known synthesis method.

< thiazole derivatives and benzothiazole derivatives >

Examples of the thiazole derivative include compounds represented by the following formula (ETM-14-1).

Phi- (thiazole series substituents)_n (ETM-14-1)

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

Phi- (benzothiazole substituent)_n (ETM-14-2)

Phi is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring or triphenylene ring), n is an integer of 1 to 4, and a "thiazole substituent" or a "benzothiazole substituent" is a substituent in which a pyridyl group in the "pyridine substituent" of the formulae (ETM-2), (ETM-2-1) and (ETM-2-2) is substituted with a thiazolyl or benzothiazolyl group as described below, and at least one of the thiazole derivative and the benzothiazole derivative may be substituted with deuterium.

Denotes a bonding site.

φ is further preferably an anthracene ring or a fluorene ring, and the structure in that case can be referred to the description in the formula (ETM-2-1) or the formula (ETM-2-2), R in each formula¹¹～R¹⁸Reference may be made to the description in formula (ETM-2-1) or formula (ETM-2-2). In addition, although the formula (ETM-2-1) or the formula (ETM-2-2) has been described as the form in which two pyridine substituents are bonded, when these are substituted with a thiazole substituent (or a benzothiazole substituent), two pyridine substituents (that is, n ═ 2) may be substituted with a thiazole substituent (or a benzothiazole substituent), and either one of the pyridine substituents may be substituted with a thiazole substituent (or a benzothiazole substituent) and R may be substituted with an R ¹¹～R¹⁸Substituted with another pyridine substituent (i.e., n ═ 1). Further, R in the formula (ETM-2-1) may be substituted with, for example, a thiazole-based substituent (or a benzothiazole-based substituent)¹¹～R¹⁸At least one ofAnd from R¹¹～R¹⁸Substituted "pyridine-based substituents".

These thiazole derivatives and benzothiazole derivatives can be produced using known starting materials and known synthetic methods.

Silole derivatives

Examples of the silole derivative include compounds represented by the following formula (ETM-15). The details are described in Japanese patent laid-open No. 9-194487.

X and Y are each independently alkyl, cycloalkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, aryl, heteroaryl, which may be substituted. As for the details of these groups, the descriptions in the formulae (1) and (2) and the description in the formula (ETM-7-2) can be cited. Further, alkenyloxy and alkynyloxy are each a group in which an alkyl moiety in an alkoxy group is substituted with an alkenyl group or an alkynyl group, and the details of these alkenyl group and alkynyl group can be referred to the description in the formula (ETM-7-2).

In addition, X and Y may be bonded to form a cycloalkyl ring (a ring in which a part thereof becomes unsaturated), and details of the cycloalkyl ring can be referred to the description of the cycloalkyl group in the formulae (1) and (2).

R¹～R⁴Each independently hydrogen, halogen, alkyl, cycloalkyl, alkoxy, aryloxy, amino, alkylcarbonyl, arylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, azo, alkylcarbonyloxy, arylcarbonyloxy, alkoxycarbonyloxy, aryloxycarbonyloxy, sulfinyl, sulfonyl, mercapto, silyl, carbamoyl, aryl, heteroaryl, alkenyl, alkynyl, nitro, formyl, nitroso, formyloxy, isocyano, cyanate, isocyanate, thiocyanate, isocyanate or cyano, which may be substituted with alkyl, cycloalkyl, aryl or halogen, or may form a fused ring with an adjacent substituent.

With respect to R¹～R⁴The halogen, alkyl, cycloalkyl, alkoxy, aryloxy, amino, aryl, heteroaryl, alkenyl and alkynyl in (1) and (2) can be cited as detailed in the description.

With respect to R¹～R⁴In the above (1), the alkyl, aryl and alkoxy groups in the alkylcarbonyl, arylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, alkylcarbonyloxy, arylcarbonyloxy, alkoxycarbonyloxy and aryloxycarbonyloxy groups can be mentioned in detail as well as the descriptions in the formulae (1) and (2).

Examples of the silyl group include a silyl group and a group in which at least one of the three hydrogens of the silyl group is independently substituted with an aryl group, an alkyl group or a cycloalkyl group, preferably a trisubstituted silyl group, and examples thereof include: triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkylbicycloalkylsilyl, and the like. As for details of the aryl group, the alkyl group and the cycloalkyl group, the descriptions in the formula (1) and the formula (2) can be cited.

The condensed ring formed between the adjacent substituent is, for example, R¹And R²、R²And R³、R³And R⁴Etc. are formed between them. These condensed rings may contain a nitrogen atom, an oxygen atom, a sulfur atom in the ring inner structure, or may be further condensed with other rings.

Among them, it is preferable that when R is¹And R⁴When phenyl, X and Y are not alkyl or phenyl. In addition, it is preferable that R is not satisfied simultaneously¹And R⁴When it is thienyl, X and Y are alkyl and R²And R³Is alkyl, aryl, alkenyl or R²And R³A cycloalkyl group bonded to form a ring. In addition, it is preferable that when R is¹And R⁴When it is a silane group, R²、R³X and Y are each independently not hydrogen or alkyl of 1 to 6 carbon atoms. In addition, it is preferable that when R is in ¹And R²Wherein X and Y are not alkyl or phenyl when a benzene ring is condensed.

These silole derivatives can be produced using known starting materials and known synthetic methods.

< oxazoline derivative >

The oxazoline derivative is, for example, a compound represented by the following formula (ETM-16). Details are described in international publication No. 2017/014226.

In the formula (ETM-16),

phi is an m-valent group derived from an aromatic hydrocarbon having 6 to 40 carbon atoms or an m-valent group derived from an aromatic heterocycle having 2 to 40 carbon atoms, at least one hydrogen of phi is substituted by an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 14 carbon atoms, an aryl group having 6 to 18 carbon atoms or a heteroaryl group having 2 to 18 carbon atoms,

y is-O-, -S-or > N-Ar, Ar is aryl with 6-12 carbon atoms or heteroaryl with 2-12 carbon atoms, at least one hydrogen of Ar is substituted by alkyl with 1-4 carbon atoms, cycloalkyl with 5-10 carbon atoms, aryl with 6-12 carbon atoms or heteroaryl with 2-12 carbon atoms, R is¹～R⁵Each independently represents hydrogen, an alkyl group having 1 to 4 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms, wherein Ar in the above-mentioned formula > N-Ar and R are¹～R⁵Any one of which is a site bonded to L,

l is independently selected from the group consisting of a divalent group represented by the following formula (L-1) and a divalent group represented by the following formula (L-2),

In the formula (L-1), X¹～X⁶Each independently is ═ CR⁶-or ═ N-, X¹～X⁶At least two of which are ═ CR⁶-，X¹～X⁶Two of (CR)⁶R in (A-C)⁶Is a site bonded to the phi or oxazoline ring, other than CR⁶R in (A-C)⁶Is a hydrogen atom, and is,

in the formula (L-2), X⁷～X¹⁴Each independently is ═ CR⁶-or ═ N-, X⁷～X¹⁴At least two of which are ═ CR⁶-，X⁷～X¹⁴Two of (CR)⁶R in (A-C)⁶Is a site bonded to the phi or oxazoline ring, other than CR⁶R in (A-C)⁶Is a hydrogen atom, and is,

at least one hydrogen of L is substituted by an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms or a heteroaryl group having 2 to 10 carbon atoms,

m is an integer of 1 to 4, and when m is 2 to 4, the groups formed by the oxazoline ring and L may be the same or different, and,

at least one hydrogen in the compound represented by formula (ETM-16) may be substituted with deuterium.

The specific oxazoline derivative is a compound represented by the following formula (ETM-16-1) or formula (ETM-16-2).

In the formulae (ETM-16-1) and (ETM-16-2),

In the formula (ETM-16-1), Y is-O-, -S-or > N-Ar, Ar is aryl with 6-12 carbon atoms or heteroaryl with 2-12 carbon atoms, at least one hydrogen of Ar is substituted by alkyl with 1-4 carbon atoms, cycloalkyl with 5-10 carbon atoms, aryl with 6-12 carbon atoms or heteroaryl with 2-12 carbon atoms,

in the formula (ETM-16-1), R¹～R⁴Each independently hydrogen, C1-C4 alkyl or C5-C10 cycloalkyl, wherein R is¹And R²Are the same, and R³And R⁴In the same way, the first and second,

in the formula (ETM-16-2), R¹～R⁵Each independently hydrogen, C1-C4 alkyl or C5-C10 cycloalkyl, wherein R is¹And R²Are the same, and R³And R⁴In the same way, the first and second,

in the formulae (ETM-16-1) and (ETM-16-2),

in the formula (L-2), X⁷～X¹⁴Each independently is ═ CR⁶-or ═ N-, X⁷～X¹⁴At least two of which are ═ CR⁶-，X⁷～X¹⁴Two of (CR)⁶R in (A-C)⁶Is a site bonded to the phi or oxazoline ring, other than CR ⁶R in (A-C)⁶Is a hydrogen atom, and is,

at least one hydrogen in the compound represented by formula (ETM-16-1) or formula (ETM-16-2) may be substituted with deuterium.

Preferably: and phi is selected from the group consisting of a monovalent group represented by the following formulas (phi 1-1) to (phi 1-18), a divalent group represented by the following formulas (phi 2-1) to (phi 2-34), a trivalent group represented by the following formulas (phi 3-1) to (phi 3-3), and a tetravalent group represented by the following formulas (phi 4-1) to (phi 4-2), wherein at least one hydrogen of phi is substituted by an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 14 carbon atoms, an aryl group having 6 to 18 carbon atoms, or a heteroaryl group having 2 to 18 carbon atoms.

Wherein Z is > CR₂N-Ar, > N-L, -O-or-S-, > CR₂Wherein R is independently an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an aryl group having 6 to 12 carbon atoms or a heteroaryl group having 2 to 12 carbon atoms, R may be bonded to each other to form a ring, > Ar in N-Ar is an aryl group having 6 to 12 carbon atoms or a heteroaryl group having 2 to 12 carbon atoms, > L in N-L is L in the formula (ETM-16), the formula (ETM-16-1) or the formula (ETM-16-2). Wherein denotes a bonding site.

Preferably: l is a divalent group of a ring selected from the group consisting of benzene, naphthalene, pyridine, pyrazine, pyrimidine, pyridazine, triazine, quinoline, isoquinoline, naphthyridine, phthalazine, quinoxaline, quinazoline, cinnoline and pteridine, and at least one hydrogen of L is substituted by an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms or a heteroaryl group having 2 to 10 carbon atoms.

Preferably: ar in > N-Ar as Y or Z is selected from the group consisting of phenyl, naphthyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolyl, isoquinolyl, naphthyridinyl, phthalazinyl, quinoxalinyl, quinazolinyl, cinnolinyl and pteridinyl, and at least one hydrogen of Ar in > N-Ar as Y is substituted by an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms or an aryl group having 6 to 10 carbon atoms.

Preferably: r¹～R⁴Each independently hydrogen, C1-C4 alkyl or C5-C10 cycloalkyl, wherein R is¹And R²Same as R³And R⁴Are the same, and R¹～R⁴All of which are not simultaneously hydrogen, and m is 1 or 2, and when m is 2, the groups formed by the oxazoline rings and L are the same.

Specific examples of the oxazoline derivative include the following compounds. Further, "Me" in the structural formula represents a methyl group.

More preferably: φ is selected from the group consisting of divalent radicals represented by the following formulae (φ 2-1), (φ 2-31), formulae (φ 2-32), formulae (φ 2-33), and formulae (φ 2-34), wherein at least one hydrogen of φ is substituted by an aryl group having 6 to 18 carbon atoms,

(indicates bonding position)

L is a divalent group of a ring selected from the group consisting of benzene, pyridine, pyrazine, pyrimidine, pyridazine and triazine, at least one hydrogen of L is substituted by an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms or a heteroaryl group having 2 to 14 carbon atoms,

ar in > N-Ar as Y is selected from the group consisting of phenyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl and triazinyl, wherein at least one hydrogen of Ar is substituted by an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms or an aryl group having 6 to 10 carbon atoms,

R¹～R⁴each independently hydrogen, C1-C4 alkyl or C5-C10 cycloalkyl, wherein R is¹And R²Same as R³And R⁴Are the same, and R¹～R⁴All of which are not simultaneously hydrogen, and,

m is 2 and the group formed by the oxazoline ring and L is the same.

Other specific examples of the oxazoline derivative include the following compounds. Further, "Me" in the structural formula represents a methyl group.

With respect to details of the alkyl group, cycloalkyl group, aryl group or heteroaryl group in the formulae for specifying the oxazoline derivative, the descriptions in the formulae (1) and (2) may be cited.

The oxazoline derivative can be produced using a known raw material and a known synthesis method.

< reducing substance >

The electron transport layer or the electron injection layer may also 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 examples of the reducing substance 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 examples thereof are reducing substances having a work function of 2.9eV or less. Among these, K, Rb or Cs is more preferable as the alkali metal, 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 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.

3. Substrate in organic electroluminescent element

The substrate 101 is a support of the organic EL element 100, and quartz, glass, metal, plastic, or the like is generally used. 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 added₂Etc. soda lime glass for barrier coating (barrier coat) is 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 particularly, in the case where a synthetic resin plate, film or sheet having low gas barrier property is used as the substrate 101, it is preferable to provide a gas barrier film.

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 the layers.

Examples of the material for forming the anode 102 include inorganic compounds and organic compounds. Examples of the inorganic compound include: metals (aluminum, gold, silver, nickel, palladium, chromium, etc.), metal oxides (Indium Oxide, Tin Oxide, Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), etc.), 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 polymers such as polypyrrole and polyaniline. Further, it can be suitably selected from substances used as an anode of an 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 Ω/□ or less functions as an element electrode, but a substrate of about 10 Ω/□ is now available, so that a low-resistance product of, for example, 100 Ω/γ to 5 Ω/γ, preferably 50 Ω/γ to 5 Ω/γ is particularly preferably used. The thickness of ITO can be arbitrarily selected depending on the resistance value, but is usually used in a range of 50nm to 300nm in many cases.

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 injection/transport material to form a layer.

As the hole injecting/transporting substance, it is necessary to efficiently inject/transport holes from the positive electrode between the 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 having a small ionization potential, a large hole mobility, and excellent stability, and in which impurities serving as traps are not easily generated during production and 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. These can be changed into Specific examples of the compound include carbazole derivatives (e.g., N-phenylcarbazole and polyvinylcarbazole), biscarbazole derivatives such as bis (N-arylcarbazole) and bis (N-alkylcarbazole), triarylamine derivatives (e.g., 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' -di (3-methylphenyl) -4,4 '-diaminobiphenyl, N' -diphenyl-N, N '-dinaphthyl-4, 4' -diaminobiphenyl, N '-diphenyl-N, N' -di (3-methylphenyl) -4,4 '-diphenyl-1, 1' -diamine, and mixtures thereof, N, N '-dinaphthyl-N, N' -diphenyl-4, 4 '-diphenyl-1, 1' -diamine, N⁴,N^4'-diphenyl-N⁴,N^4'-bis (9-phenyl-9H-carbazol-3-yl) - [1,1' -biphenyl]4,4' -diamine, N⁴,N⁴,N^4',N^4'-tetrakis [1,1' -biphenyl]-4-yl- [1,1' -biphenyl]-4,4' -diamine, 4' -tris (3-methylphenyl (phenyl) amino) triphenylamine, N- ([1,1' -biphenyl]-4-yl) -9, 9-dimethyl-N- (4- (9-phenyl-9H-carbazol-3-yl) phenyl) -9H-fluoren-2-amine, N-bis (4- (dibenzo [ b, d)]Furan-4-yl) phenyl) - [1, 1': 4', 1' -terphenyl]Triphenylamine derivatives such as-4-amine, starburst amine derivatives, etc.), stilbene derivatives, phthalocyanine derivatives (metal-free, copper phthalocyanine, etc.), pyrazoline derivatives, hydrazone compounds, benzofuran derivatives or thiophene derivatives, oxadiazole derivatives, quinoxaline derivatives (e.g., 1,4,5,8,9, 12-hexaazatriphenylene-2, 3,6,7,10, 11-hexacarbonitrile, etc.), heterocyclic compounds such as porphyrin derivatives, polysilanes, etc. 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, and which can inject holes from an anode and can further 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, etc.) or a starburst amine derivative (4,4',4 ″ -Tris (N, N-diphenylamino) triphenylamine, TDATA, etc.), or a specific metal phthalocyanine (particularly zinc phthalocyanine (ZnPc), etc.) is known (japanese patent laid-open No. 2005-167175).

6. 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. In general, however, these low work function metals are most often unstable in the atmosphere. In order to improve the above-mentioned aspect, 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 preferable examples are listed: 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.

7. Binder usable in each layer in organic electroluminescent element

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.

Method for making 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 according to the properties of the material, but is usually in the range of 2nm to 5000 nm. The film thickness can be measured by a quartz oscillation type film thickness measuring apparatus or the like. When the film is made thin by vapor deposition The 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^-6Pa～10^-3Pa, a deposition rate of 0.01nm/sec to 50nm/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 vapor deposition 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 + polarity and the cathode may be applied with a-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. In addition, the waveform of the applied alternating current may be arbitrary.

Application example of organic electroluminescent element

In addition, the present invention is also applicable to a display device including an organic EL element, an illumination device including an organic EL element, or the like.

A display device or an illumination device including an organic EL element can be manufactured by a known method such as connecting the organic EL element of this embodiment to a known driving device, and can be driven by a known driving method such as dc driving, pulse driving, or ac 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 (see, for example, 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).

The matrix is a matrix in which 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 lighting device include: a lighting device such as an indoor lighting, a backlight of a liquid crystal display device, and the like (for example, refer to 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, as a backlight for personal computer applications in which thinning of a liquid crystal display device is becoming a problem, when it is considered that thinning of a conventional backlight is difficult because the backlight includes a fluorescent lamp or a light guide plate, the backlight using the light emitting element of the present embodiment has features of being thin and lightweight.

[ examples ]

The present invention will be described more specifically with reference to the following examples, but the present invention is not limited to these examples. First, a synthesis example of the compounds used in the examples will be described below.

Synthesis example (1-1)

Synthesis of Compound (1-45)

A solution of 9-bromophenanthrene (12.4g) in cyclopentyl Methyl ether (CPME (cyclopentyl Methyl ether), 150mL) was cooled to-49 deg.C, and a solution of n-butyllithium in hexane (1.6M, 30mL) was added dropwise to the resultant. The reaction mixture was warmed to-8 ℃ and then a solution of 1, 2-benzoanthraquinone (5g) in CPME (100mL) was added dropwise and stirred at room temperature for 2 hours. Water (100mL) was added to stop the reaction, and the aqueous layer was separated and removed. The organic layer was concentrated under reduced pressure, and the precipitated solid was washed with Somex (Solmix) A-11 (trade name, manufactured by Nippon alcohol Co., Ltd.) (200mL) to obtain a pale yellow solid.

To the solid were added potassium iodide (8.7g), sodium phosphinate monohydrate (2.5g) and acetic acid (100mL), and the mixture was stirred at reflux temperature for 2 hours. The reaction mixture was cooled to 60 ℃, the precipitated solid was filtered under reduced pressure, and the solid was washed and purified with water (100mL), somite (Solmix) a-11(100mL), and toluene (100mL) in this order to obtain 3.5g of compound (1-45) as a yellow solid.

The structure of the obtained compound was confirmed by Nuclear Magnetic Resonance (NMR) measurement.

¹H-NMR(400MHz,CDCl₃)：δ＝9.00～8.85(m,4H),8.00～7.55(m,14H),7.54～7.15(m,9H),6.85～6.75(m,1H).

Synthesis example (1-2)

Synthesis of Compound (1-7)

The compound (1-7) was synthesized according to the method described in the synthesis example (1-1). The obtained compound was confirmed to be compound (1-7) by mass spectrometry. Electron Ionization Mass Spectrometry (Electron Ionization Mass Spectrometry, EI-MS): and m/z is 481.

Synthesis example (1-3)

Synthesis of Compound (1-242)

Compound (1-242) was synthesized according to the method described in synthetic example (1-1). The obtained compound was confirmed to be compound (1-242) by mass spectrometry. EI-MS: m/z is 633.

Synthesis examples (1-4)

Synthesis of Compound (1-90)

The compounds (1 to 90) were synthesized according to the method described in International publication No. 2009/081776. The obtained compound was confirmed to be compound (1-90) by mass spectrometry. EI-MS: and m/z is 557.

Synthesis examples (1-5)

Synthesis of Compound (1-78)

The compounds (1 to 78) were synthesized according to the method described in International publication No. 2009/081776. The obtained compound was confirmed to be compound (1-78) by mass spectrometry. EI-MS: and m/z is 557.

Synthesis examples (1-6)

Synthesis of Compound (1-93)

The compounds (1 to 93) were synthesized according to the method described in International publication No. 2009/081776. The obtained compound was confirmed to be compound (1-93) by mass spectrometry. EI-MS: and m/z is 557.

Synthesis examples (1-7)

Synthesis of Compound (1-158)

The compound (1-158) was synthesized according to the method described in the synthesis example (1-1). The obtained compound was confirmed to be compound (1-158) by mass spectrometry. EI-MS: m/z is 633.

Synthesis examples (1-8)

Synthesis of Compound (1-161)

The compounds (1 to 161) were synthesized according to the method described in International publication No. 2009/081776. The obtained compound was confirmed to be compound (1-161) by mass spectrometry. EI-MS: m/z is 633.

Synthesis examples (1-9)

Synthesis of Compound (1-170)

The compounds (1 to 170) were synthesized according to the method described in International publication No. 2009/081776. The obtained compound was confirmed to be compound (1-170) by mass spectrometry. EI-MS: and m/z 683.

Synthesis examples (1-10)

Synthesis of Compound (1-8)

The compounds (1 to 8) were synthesized according to the method described in International publication No. 2009/081776. The obtained compound was confirmed to be compound (1-8) by mass spectrometry. EI-MS: and m/z is 481.

Synthesis examples (1-11)

Synthesis of Compound (1-48)

The compounds (1 to 48) were synthesized according to the method described in International publication No. 2009/081776. The obtained compound was confirmed to be compound (1-48) by mass spectrometry. EI-MS: and m/z is 531.

Synthesis examples (1-12)

Synthesis of Compound (1-185)

The compounds (1-185) were synthesized according to the method described in International publication No. 2009/081776. The obtained compound was confirmed to be compound (1-185) by mass spectrometry. EI-MS: m/z 547.

Synthesis example (1-13)

Synthesis of Compound (1-203)

The compounds (1 to 203) were synthesized according to the method described in International publication No. 2009/081776. The obtained compound was confirmed to be compound (1-203) by mass spectrometry. EI-MS: m/z is 583.

Synthesis examples (1-14)

Synthesis of Compound (1-129)

The compounds (1 to 129) were synthesized according to the method described in International publication No. 2009/081776. The obtained compound was confirmed to be compound (1-129) by mass spectrometry. EI-MS: and m/z is 557.

Synthesis examples (1-15)

Synthesis of Compound (1-244)

The compound (1-244) was synthesized according to the method described in the synthesis example (1-1). The obtained compound was confirmed to be compound (1-244) by mass spectrometry. EI-MS: and m/z is 613.

Synthesis example (1-16)

Synthesis of Compound (1-753-O)

To 7-bromobenzo [ a ] anthracene (1.0g), 4,5, 5-tetramethyl-2- (naphtho [2,3-b ] benzofuran-2-yl) -1,3, 2-dioxaborane (1.18g), potassium phosphate (1.4g), xylene (10mL), tert-butanol (3mL), water (2mL) was added Pd-132 (Johnson Matthey) (23mg) under a nitrogen atmosphere, and the mixture was heated and stirred at 110 ℃ for 1 hour. After cooling to room temperature, water and ethyl acetate were added, and after stirring for a while, the organic layer was concentrated, heptane was added and a precipitate was recovered. To the precipitate was added 1/1 (volume ratio) toluene/heptane and the soluble component was recovered, followed by purification by silica gel short path column (developing solution: 1/1 (volume ratio) toluene/heptane), and heptane reprecipitation to obtain compound (1-753-O) (1.0 g).

The structure of the obtained compound was confirmed by NMR measurement.

¹H-NMR(CDCl₃)：σ＝7.42～7.64(m,8H),7.71～7.74(m,2H),7.78(dd,1H),7.82(dd,1H),7.98～8.01(m,3h),8.14(d,1H),8.21(d,1H),8.37(s,1h),8.93(d,1H),9.31(s,1H).

Synthesis example (1-17)

Synthesis of Compound (1-714-O)

2-bromo-benzofuran (24.71g) was added dropwise to a flask containing magnesium (2.92g) and tetrahydrofuran (40mL) under a nitrogen atmosphere, and then stirred with heating at 40 ℃ for 1 hour. After cooling to 0 ℃ tetrahydrofuran (100mL) was added dropwise and benzo [ a ] anthracen-12 (7H) -one (24.43g) was added and the reaction medium was refluxed for 2 hours. After cooling to 0 deg.C, 1N-HCl aqueous solution (100mL) was added dropwise and stirred for 1 hour. The organic layer was extracted with ethyl acetate, washed with an aqueous potassium carbonate solution and pure water in this order, and dried with sodium sulfate. The organic phase was concentrated under reduced pressure, followed by purification by silica gel column chromatography to obtain a compound represented by the formula (1-714-O) (28.40 g). The obtained compound was confirmed to be compound (1-714-O) by mass spectrometry. EI-MS: 395 in m/z.

Synthesis examples (1-18)

Synthesis of Compound (1-703-O)

The compound (1-703-O) was synthesized according to the method described in the above synthesis examples (1-17). The obtained compound was confirmed to be compound (1-703-O) by mass spectrometry. EI-MS: m/z 445.

Synthesis examples (1-19)

Synthesis of Compound (1-702-O)

The compound (1-702-O) was synthesized according to the method described in the above synthesis examples (1-17). The obtained compound was confirmed to be compound (1-702-O) by mass spectrometry. EI-MS: m/z 445.

Synthesis examples (1-20)

Synthesis of Compound (1-705-O)

The compound (1-705-O) was synthesized according to the method described in the above synthesis examples (1-17). The obtained compound was confirmed to be compound (1-705-O) by mass spectrometry. EI-MS: m/z 445.

Synthesis examples (1-21)

Synthesis of Compound (1-713-O)

The compound (1-713-O) was synthesized according to the method described in the synthesis examples (1-17). The obtained compound was confirmed to be compound (1-713-O) by mass spectrometry. EI-MS: m/z 445.

Synthesis example (1-22)

Synthesis of Compound (1-718-O)

Compound (1-718-O) was synthesized according to the method described in the above synthesis examples (1-16). The obtained compound was confirmed to be compound (1-718-O) by mass spectrometry. EI-MS: 395 in m/z.

Synthesis example (1-23)

Synthesis of Compound (1-715-O)

Compound (1-715-O) was synthesized according to the method described in the synthesis examples (1-17). The obtained compound was confirmed to be compound (1-715-O) by mass spectrometry. EI-MS: 395 in m/z.

Synthesis example (1-24)

Synthesis of Compound (1-717-S)

The compound (1-717-S) was synthesized according to the method described in the synthesis examples (1-16). The obtained compound was confirmed to be compound (1-717-S) by mass spectrometry. EI-MS: m/z 411.

Synthesis example (1-25)

Synthesis of Compound (1-714-S)

The compound (1-714-S) was synthesized according to the method described in the above synthesis examples (1-17). The obtained compound was confirmed to be compound (1-714-S) by mass spectrometry. EI-MS: m/z 411.

Synthesis examples (1-26)

Synthesis of Compound (1-718-N)

Compound (1-718-N) was synthesized according to the method described in the above synthesis examples (1-16). The obtained compound was confirmed to be compound (1-718-N) by mass spectrometry. EI-MS: 470 m/z.

Synthesis example (1-27)

Synthesis of Compound (1-715-N)

The compound (1-715-N) was synthesized according to the method described in the synthesis examples (1-17). The obtained compound was confirmed to be compound (1-715-N) by mass spectrometry. EI-MS: 470 m/z.

Synthesis example (1-28)

Synthesis of Compound (1-551-O)

Compound (1-551-O) was synthesized according to the method described in International publication No. 2009/081776. The obtained compound was confirmed to be compound (1-551-O) by mass spectrometry. EI-MS: and m/z 471.

Synthesis example (1-29)

Synthesis of Compound (1-381-O)

Compound (1-381-O) was synthesized according to the method described in International publication No. 2009/081776. The obtained compound was confirmed to be compound (1-381-O) by mass spectrometry. EI-MS: and m/z 471.

Synthesis example (1-30)

Synthesis of Compound (1-755-O)

The compound (1-755-O) was synthesized according to the method described in the above synthesis examples (1-16). The obtained compound was confirmed to be compound (1-755-O) by mass spectrometry. EI-MS: m/z 445.

Synthesis example (1-31)

Synthesis of Compound (1-778-O)

Compound (1-778-O) was synthesized according to the method described in Synthesis example (1-1). The obtained compound was confirmed to be compound (1-778-O) by mass spectrometry. EI-MS: and m/z is 661.

Synthesis example (1-32)

Synthesis of Compound (1-752-O)

Compound (1-752-O) was synthesized according to the method described in the above-mentioned synthesis examples (1-16). The obtained compound was confirmed to be compound (1-752-O) by mass spectrometry. EI-MS: m/z 445.

Synthesis example (1-33)

Synthesis of Compound (1-717-O)

Compound (1-717-O) was synthesized according to the method described in the above synthesis examples (1-16). The obtained compound was confirmed to be compound (1-717-O) by mass spectrometry. EI-MS: 395 in m/z.

Synthesis example (1-34)

Synthesis of Compound (1-785-O)

Compound (1-785-O) was synthesized according to the method described in International publication No. 2009/081776. The obtained compound was confirmed to be compound (1-785-O) by mass spectrometry. EI-MS: 571 m/z.

Synthesis example (1-35)

Synthesis of Compound (1-790-O)

Compound (1-790-O) was synthesized according to the method described in International publication No. 2009/081776. The obtained compound was confirmed to be compound (1-790-O) by mass spectrometry. EI-MS: 571 m/z.

Synthesis examples (1-36)

Synthesis of Compound (1-763-O)

Compound (1-763-O) was synthesized according to the method described in the above synthesis examples (1-16). The obtained compound was confirmed to be compound (1-763-O) by mass spectrometry. EI-MS: m/z 445.

Synthesis example (1-37)

Synthesis of Compound (1-387-O)

Compound (1-387-O) was synthesized according to the method described in International publication No. 2009/081776. The obtained compound was confirmed to be compound (1-387-O) by mass spectrometry. EI-MS: m/z 547.

Synthesis example (1-38)

Synthesis of Compound (1-1699-O)

Compound (1-1699-O) was synthesized according to the method described in International publication No. 2009/081776. The obtained compound was confirmed to be compound (1-1699-O) by mass spectrometry. EI-MS: 697.

Synthesis example (1-39)

Synthesis of Compound (1-1663-O)

Compound (1-1663-O) was synthesized according to the method described in International publication No. 2009/081776. The obtained compound was confirmed to be compound (1-1663-O) by mass spectrometry. EI-MS: 723 m/z.

Synthesis examples (1-40)

Synthesis of Compound (1-383-N)

The compound (1-383-N) was synthesized according to the method described in International publication No. 2009/081776. The obtained compound was confirmed to be compound (1-383-N) by mass spectrometry. EI-MS: and m/z is 546.

Synthesis example (1-41)

Synthesis of Compound (1-1552-O)

Compound (1-1552-O) was synthesized according to the method described in International publication No. 2009/081776. The obtained compound was confirmed to be compound (1-1552-O) by mass spectrometry. EI-MS: and m/z is 673.

Synthesis example (1-42)

Synthesis of Compound (1-1683-O)

Compound (1-1683-O) was synthesized according to the method described in International publication No. 2009/081776. The obtained compound was confirmed to be compound (1-1683-O) by mass spectrometry. EI-MS: 723 m/z.

Synthesis example (1-43)

Synthesis of Compound (1-1680-O)

Compound (1-1680-O) was synthesized according to the method described in International publication No. 2009/081776. The obtained compound was confirmed to be compound (1-1680-O) by mass spectrometry. EI-MS: and m/z is 647.

Synthesis example (1-44)

Synthesis of Compound (1-1599-O)

Compound (1-1599-O) was synthesized according to the method described in International publication No. 2009/081776. The obtained compound was confirmed to be compound (1-1599-O) by mass spectrometry. EI-MS: 623 m/z.

Synthesis examples (1-45)

Synthesis of Compound (1-1116-O)

Compound (1-1116-O) was synthesized according to the method described in Synthesis example (1-1). The obtained compound was confirmed to be compound (1-1116-O) by mass spectrometry. EI-MS: 597 m/z.

Synthesis example (1-46)

Synthesis of Compound (1-1025-O)

Compound (1-1025-O) was synthesized according to the method described in International publication No. 2009/081776. The obtained compound was confirmed to be compound (1-1025-O) by mass spectrometry. EI-MS: and m/z is 713.

Synthesis example (1-47)

Synthesis of Compound (1-1703-O)

Compound (1-1703-O) was synthesized according to the method described in International publication No. 2009/081776. The obtained compound was confirmed to be compound (1-1703-O) by mass spectrometry. EI-MS: and m/z is 747.

Synthesis examples (1-48)

Synthesis of Compound (1-1751-O)

Compound (1-1751-O) was synthesized according to the method described in International publication No. 2009/081776. The obtained compound was confirmed to be compound (1-1751-O) by mass spectrometry. EI-MS: and m/z is 603.

Synthesis example (1-49)

Synthesis of Compound (1-1665-O)

Compound (1-1665-O) was synthesized according to the method described in International publication No. 2009/081776. The obtained compound was confirmed to be compound (1-1665-O) by mass spectrometry. EI-MS: and m/z is 863.

Synthesis examples (1-50)

Synthesis of Compound (1-1584-S)

Compound (1-1584-S) was synthesized by the method described in International publication No. 2009/081776. The obtained compound was confirmed to be compound (1-1584-S) by mass spectrometry. EI-MS: m/z 563.

Synthesis example (1-51)

Synthesis of Compound (1-1538-N)

Compound (1-1538-N) was synthesized according to the method described in International publication No. 2009/081776. The obtained compound was confirmed to be compound (1-1538-N) by mass spectrometry. EI-MS: and m/z 622.

Synthesis example (1-52)

Synthesis of Compound (1-1001-O)

The compound (1-1001-O) was synthesized according to the method described in the above synthesis example (1-1). The obtained compound was confirmed to be compound (1-1001-O) by mass spectrometry. EI-MS: m/z 547.

Synthesis example (1-53)

Synthesis of Compound (1-1716-O)

Compound (1-1716-O) was synthesized according to the method described in International publication No. 2009/081776. The obtained compound was confirmed to be compound (1-1716-O) by mass spectrometry. EI-MS: 623 m/z.

Synthesis example (1-54)

Synthesis of Compound (1-1184-O)

Compound (1-1184-O) was synthesized according to the method described in Synthesis example (1-1). The obtained compound was confirmed to be compound (1-1184-O) by mass spectrometry. EI-MS: and m/z is 647.

Synthesis example (1-55)

Synthesis of Compound (1-1140-O)

Compound (1-1140-O) was synthesized according to the method described in International publication No. 2009/081776. The obtained compound was confirmed to be compound (1-1140-O) by mass spectrometry. EI-MS: 773.

Synthesis example (1-56)

Synthesis of Compound (1-1347-O)

Compound (1-1347-O) was synthesized according to the method described in synthetic example (1-1). The obtained compound was confirmed to be compound (1-1347-O) by mass spectrometry. EI-MS: and m/z is 823.

Synthesis example (1-57)

Synthesis of Compound (1-1783-O)

Compound (1-1783-O) was synthesized according to the method described in the above synthetic example (1-1). The obtained compound was confirmed to be compound (1-1783-O) by mass spectrometry. EI-MS: m/z 547.

Synthesis example (1-58)

Synthesis of Compound (1-1759-O)

Compound (1-1759-O) was synthesized according to the method described in the above synthetic example (1-1). The obtained compound was confirmed to be compound (1-1759-O) by mass spectrometry. EI-MS: m/z 547.

Synthesis example (1-59)

Synthesis of Compound (1-1767-O)

Compound (1-1767-O) was synthesized according to the method described in Synthesis example (1-1). The obtained compound was confirmed to be compound (1-1767-O) by mass spectrometry. EI-MS: and m/z is 647.

Synthesis examples (1-60)

Synthesis of Compound (1-1777-O)

Compound (1-1777-O) was synthesized according to the method described in International publication No. 2009/081776. The obtained compound was confirmed to be compound (1-1777-O) by mass spectrometry. EI-MS: 623 m/z.

Synthesis example (1-61)

Synthesis of Compound (1-1781-O)

Compound (1-1781-O) was synthesized according to the method described in International publication No. 2009/081776. The obtained compound was confirmed to be compound (1-1781-O) by mass spectrometry. EI-MS: m/z is 561.

Synthesis example (1-62)

Synthesis of Compound (1-1592-O)

Compound (1-1592-O) was synthesized according to the method described in International publication No. 2009/081776. The obtained compound was confirmed to be compound (1-1592-O) by mass spectrometry. EI-MS: 623 m/z.

Synthesis example (1-63)

Synthesis of Compound (1-1798-O)

Compound (1-1798-O) was synthesized according to the method described in the above-mentioned synthesis examples (1-17). The obtained compound was confirmed to be compound (1-1798-O) by mass spectrometry. EI-MS: and m/z 471.

Synthesis example (1-64)

Synthesis of Compound (1-1795-O)

Compound (1-1795-O) was synthesized according to the method described in the above-mentioned synthesis examples (1-17). The obtained compound was confirmed to be compound (1-1795-O) by mass spectrometry. EI-MS: and m/z is 431.

Synthesis example (1-65)

Synthesis of Compound (1-1797-O)

Compound (1-1797-O) was synthesized according to the method described in the above-mentioned synthesis examples (1-17). The obtained compound was confirmed to be compound (1-1797-O) by mass spectrometry. EI-MS: and m/z is 431.

Synthesis example (1-66)

Synthesis of Compound (1-1805-O)

Compound (1-1805-O) was synthesized according to the method described in the above synthesis examples (1-17). The obtained compound was confirmed to be compound (1-1805-O) by mass spectrometry. EI-MS: and m/z 471.

Synthesis example (2-1): synthesis of Compound (2-41)

The compounds (2 to 41) were synthesized according to the method described in "synthetic example (32)" of International publication No. 2015/102118.

The structure of the obtained compound was confirmed by NMR measurement.

¹H-NMR(500MHz,CDCl₃)：δ＝1.47(s,36H),2.17(s,3H),5.97(s,2H),6.68(d,2H),7.28(d,4H),7.49(dd,2H),7.67(d,4H),8.97(d,2H).

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

The compounds (2 to 31) were synthesized according to the method described in "synthetic example (32)" of International publication No. 2015/102118.

The structure of the obtained compound was confirmed by NMR measurement.

¹H-NMR(500MHz,CDCl₃)：δ＝1.46(s,18H),1.47(s,18H),6.14(d,2H),6.75(d,2H),7.24(t,1H),7.29(d,4H),7.52(dd,2H),7.67(d,4H),8.99(d,2H).

Synthesis example (2-3): synthesis of Compound (2-46)

The compounds (2 to 46) were synthesized according to the method described in "synthetic example (32)" of International publication No. 2015/102118.

The structure of the obtained compound was confirmed by NMR measurement.

¹H-NMR(CDCl₃)：δ＝1.20(s,9H),1.37(s,18H),1.46(s,9H),1.47(s,9H),2.18(s,3H),5.97(s,1H),6.08(d,1H),6.63(d,1H),6.66(d,1H),7.20(d,2H),7.27(d,2H),7.32(dd,1H),7.48(dd,1H),7.61(t,1H),7.67(d,2H),8.84(d,1H),8.94(d,1H).

Synthesis examples (2 to 4): synthesis of Compound (2-37)

The compounds (2 to 37) were synthesized according to the method described in "synthetic example (32)" of International publication No. 2015/102118.

The structure of the obtained compound was confirmed by NMR measurement.

¹H-NMR(CDCl₃)：δ＝1.20(s,9H),1.36(s,18H),1.46(s,9H),1.47(s,9H),6.14(d,1H),6.25(d,1H),6.68(d,1H),6.73(d,1H),7.21(d,2H),7.29(d,3H),7.34(dd,1H),7.51(dd,1H),7.61(t,1H),7.67(d,2H),8.86(d,1H),8.96(d,1H).

Synthesis examples (2 to 5): synthesis of Compound (2-42)

The compounds represented by the formulae (2 to 42) were synthesized using the same method as in the synthesis example.

The structure of the obtained compound was confirmed by NMR measurement.

¹H-NMR(CDCl₃)：δ＝1.37(s,18H),1.46(s,9H),1.47(s,9H),2.17(s,3H),5.56(s,1H),5.99(s,1H),6.68(d,1H),6.74(d,1H),7.19(d,2H),7.24～7.29(m,3H),7.42(t,1H),7.49(dd,1H),7.61(t,1H),7.68(d,2H),8.91(dd,1H),8.92(d,1H).

Synthesis examples (2 to 6): synthesis of Compound (2-49)

The compound (2-49) was synthesized according to the method described in "comparative synthesis example (1)" of Japanese patent laid-open No. 2016-88927.

The structure of the obtained compound was confirmed by NMR measurement.

¹H-NMR(CDCl₃)：δ＝1.33(s,18H),1.46(s,18H),5.55(s,2H),6.75(d,2H),6.89(t,2H),6.94(d,4H),7.06(t,4H),7.13(d,4H),7.43～7.46(m,6H),8.95(d,2H).

Synthesis examples (2 to 7): synthesis of Compound (2-50)

The compounds (2 to 50) were synthesized according to the method described in "synthetic example (32)" of International publication No. 2015/102118.

The structure of the obtained compound was confirmed by NMR measurement.

¹H-NMR(CDCl₃)：δ＝1.3(s,18H),1.3(s,18H),1.5(s,18H),5.8(s,2H),6.6(d,2H),6.8(dd,4H),7.1(dd,4H),7.1(dd,4H),7.4～7.5(m,6H),8.9(d,2H).

Synthesis examples (2 to 8): synthesis of Compound (2-53)

The compounds (2 to 53) were synthesized according to the method described in "synthetic example (32)" of International publication No. 2015/102118.

The structure of the obtained compound was confirmed by NMR measurement.

¹H-NMR(CDCl₃)：δ＝1.35(s,18H),1.50(s,18H),6.34(s,2H),6.85(d,2H),7.16(t,2H),7.23(t,2H),7.32～7.35(m,6H),7.56(dd,2H),7.63(d,4H),7.99(d,2H),9.05(d,2H).

Synthesis examples (2 to 9): synthesis of Compound (2-33)

The compounds (2 to 33) were synthesized according to the method described in "synthetic example (32)" of International publication No. 2015/102118.

The structure of the obtained compound was confirmed by NMR measurement.

¹H-NMR(CDCl₃)：δ＝1.22(s,9H),1.37(s,9H),1.46(s,9H),1.47(s,9H),6.14(d,1H),6.18(d,1H),6.72(d,1H),6.74(d,1H),7.19(ddd,1H),7.23～7.30(m,3H),7.34(dd,1H),7.41(t,1H),7.51(dd,1H),7.58～7.64(m,2H),7.67(d,2H),8.86(d,1H),8.96(d,1H).

Synthesis examples (2 to 10): synthesis of Compound (2-508)

4- (tert-amyl) aniline (15.0g) was dissolved in acetonitrile (150ml) under a nitrogen atmosphere, and to the resultant was added dropwise bromine (22.5g) with stirring for 0.5 hour under cooling in an ice bath. After the reaction, water and ethyl acetate were added to the reaction solution and stirred, and then the organic layer was separated and washed with water. Then, the organic layer was concentrated to obtain a crude product. The crude product was purified by means of a silica gel short path column (eluent: toluene), whereby intermediate (I-A) (20.0g) was obtained.

Copper chloride (10.1g) and intermediate (I-A) (20.0g) were dissolved in acetonitrile (100ml) under a nitrogen atmosphere, and tert-butyl nitrite (9.6g) dissolved in acetonitrile (50ml) was added dropwise to the resultant at 60 ℃ and stirred at the temperature for 0.5 hour. After the reaction, dilute hydrochloric acid and ethyl acetate were added to the reaction solution and stirred, and then the organic layer was separated and washed with water. Then, the organic layer was concentrated to obtain a crude product. The crude product was purified by means of a silica gel short path column (eluent: toluene/heptane 1/4 (vol.)), whereby intermediate (I-B) (19.0g) was obtained.

Intermediate (I-B) (10.0g), bis (4-tert-butylphenyl) amine (18.2g), dichlorobis (di-tert-butyl (4-dimethylaminophenyl) phosphino) palladium (Pd-132, 0.21g) as a palladium catalyst, sodium tert-butoxide (NaOtBu, 7.1g) and xylene (100ml) were placed in a flask and heated at 100 ℃ for 1 hour under a nitrogen atmosphere. After the reaction, water and toluene were added to the reaction solution and stirred, and then the organic layer was separated and washed with water. Then, the organic layer was concentrated to obtain a crude product. The crude product was purified by means of a silica gel short path column (eluent: toluene), whereby intermediate (I-C) (18.0g) was obtained.

To a flask containing intermediate (I-C) (18.0g) and tert-butylbenzene (500ml) was added 1.56M t-butyllithium pentane solution (28.9ml) under nitrogen at 0 ℃. 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 (11.3g) was added, warmed to room temperature and stirred for 0.5 h. Then, it was cooled again to 0 ℃ and N, N-diisopropylethylamine (5.8g) was added, and stirred at room temperature until the heat generation ended, then warmed to 100 ℃ and heated and stirred for 1 hour. The reaction solution was cooled to room temperature, and an aqueous sodium acetate solution cooled by an ice bath and ethyl acetate were sequentially added thereto to separate the reaction solution. The organic layer was concentrated and then purified using a silica gel short path column (eluent: toluene). The obtained crude product was recrystallized using chlorobenzene, whereby compound (2-508) (7.1g) was obtained.

The structure of the obtained compound was confirmed by NMR measurement.

¹H-NMR(CDCl₃)：δ＝0.49(t,3H),0.92(s,6H),1.28(q,2H),1.46(s,18H),1.47(s,18H),6.05(s,2H),6.77(d,2H),7.28(m,4H),7.50(m,2H),7.67(m,4H),8.97(d,2H).

Synthesis examples (2 to 11): synthesis of Compound (2-538)

Under nitrogen atmosphere, 3,4, 5-trichloroaniline (12.0g), d⁵Bromobenzene (30.0g), dichlorobis (di-tert-butyl (4-dimethylaminophenyl) phosphino) palladium (Pd-132, 0.43g) as a palladium catalyst, sodium tert-butoxide (NaOtBu, 14.7g) and xylene (200mL) were placed in a flask and heated at 120 ℃ for 3 hours. After the reaction, water and ethyl acetate were added to the reaction solution and stirred, and then the organic layer was separated and added Washed with water. Then, the organic layer was concentrated to obtain a crude product. The crude product was purified by means of a silica gel short path column (eluent: toluene/heptane 1/1 (vol.)), whereby 15.0g of intermediate (I-D) was obtained.

Intermediate (I-D) (15.0g), bis (4-tert-butylphenyl) amine (25.9g), bis (dibenzylideneacetone) palladium (0.48g), 2-dicyclohexylphosphino-2 ',6' -dimethoxybiphenyl (SPhos, 0.86g), sodium tert-butoxide (10.0g) and xylene (130mL) were placed in a flask under a nitrogen atmosphere, and heated at 100 ℃ for 1 hour. After the reaction, water and toluene were added to the reaction solution and stirred, and then the organic layer was separated and washed with water. Then, the organic layer was concentrated to obtain a crude product. The crude product was purified by means of a silica gel short path column (eluent: toluene), whereby 23.0g of intermediate (I-E) was obtained.

To a flask containing intermediate (I-E) (23.0g) and tert-butyl benzene (250ml) was added 1.62M t-butyllithium pentane solution (33.5ml) under nitrogen at 0 ℃. After the completion of the dropwise addition, the temperature was raised to 60 ℃ and the mixture was stirred for 1 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 (13.6g) was added, warmed to room temperature and stirred for 0.5 h. Then, it was cooled again to 0 ℃ and N, N-diisopropylethylamine (7.0g) was added, and stirred at room temperature until the heat generation ended, then warmed to 100 ℃ and heated and stirred for 1 hour. The reaction solution was cooled to room temperature, and an aqueous sodium acetate solution cooled by an ice bath and ethyl acetate were sequentially added thereto to separate the reaction solution. The organic layer was concentrated and then purified using a short path column of silica gel (eluent: heated chlorobenzene). The obtained crude product was washed with refluxed heptane and refluxed ethyl acetate, and then reprecipitated from chlorobenzene, thereby obtaining compound (2-538) (12.9 g).

The structure of the obtained compound was confirmed by NMR measurement.

¹H-NMR(CDCl₃)：δ＝1.3(s,18H),1.5(s,18H),5.6(s,2H),6.8(d,2H),7.1(m,4H),7.4～7.5(m,6H),9.0(d,2H).

Synthesis examples (2 to 12): synthesis of Compound (2-541)

Under nitrogen atmosphere, mixing⁵Aniline (5.0g), d⁵Bromobenzene (8.25g), Pd-132(0.36g) as a palladium catalyst, NaOtBu (7.1g) and xylene (100mL) were placed in a flask and heated at 120 ℃ for 1.5 hours. After the reaction, water and ethyl acetate were added to the reaction solution and stirred, and then the organic layer was separated and washed with water. Then, the organic layer was concentrated to obtain a crude product. The crude product was purified by means of a silica gel short path column (eluent: toluene/heptane 1/1 (vol.)), whereby 8.1g of intermediate (I-F) was obtained.

Intermediate (I-F) (8.0G), intermediate (I-G) (20.6G), Pd-132(0.31G) as a palladium catalyst, NaOtBu (6.4G) and xylene (100mL) were placed in a flask and heated at 120 ℃ for 1 hour under a nitrogen atmosphere. After the reaction, water and ethyl acetate were added to the reaction solution and stirred, and then the organic layer was separated and washed with water. Then, the organic layer was concentrated to obtain a crude product. The crude product was purified by means of a silica gel short path column (eluent: toluene/heptane 1/1 (vol.)), whereby 20.2g of intermediate (I-H) was obtained.

To a flask containing intermediate (I-H) (10.0g) and tert-butyl benzene (150ml) was added 1.62M t-butyllithium pentane solution (21.2ml) under nitrogen at 0 ℃. After the completion of the dropwise addition, the temperature was raised to 60 ℃ 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 (8.6g) was added, warmed to room temperature and stirred for 0.5 h. Then, it was cooled again to 0 ℃ and N, N-diisopropylethylamine (4.4g) was added, and stirred at room temperature until the heat generation ended, then warmed to 100 ℃ and heated and stirred for 1 hour. The reaction solution was cooled to room temperature, and an aqueous sodium acetate solution cooled by an ice bath and ethyl acetate were sequentially added thereto to separate the reaction solution. The organic layer was concentrated and then purified using a silica gel short path column (eluent: toluene). The obtained crude product was dissolved in toluene, followed by addition of heptane, filtration of the precipitated crystal, and washing of the crystal separated by filtration with cooled heptane, whereby compound (2-541) (3.1g) was obtained.

The structure of the obtained compound was confirmed by NMR measurement.

¹H-NMR(CDCl₃)：δ＝1.46(s,9H),1.47(s,9H),2.16(s,3H),5.92(s,1H),6.00(s,1H),6.69(d,1H),7.25-7.28(m,2H),7.49-7.51(m,1H),7.66-7.69(m,2H),8.92(d,1H).

Synthesis examples (2 to 13): synthesis of Compound (2-544)

Intermediate (I-I) (8.4g), intermediate (I-J) (4.6g), bis (dibenzylideneacetone) palladium (0.23g), 2-dicyclohexylphosphino-2 ',6' -dimethoxybiphenyl (SPhos, 0.32g), sodium tert-butoxide (3.2g) and xylene (40ml) were placed in a flask under a nitrogen atmosphere and heated at 100 ℃ for 1.5 hours. After the reaction, water and toluene were added to the reaction solution and stirred, and then the organic layer was separated and washed with water. Then, the organic layer was concentrated to obtain a crude product. The crude product was purified by means of a silica gel short path column (eluent: toluene), whereby intermediate (I-K) (8.6g) was obtained.

To a flask containing intermediate (I-K) (8.6g) and tert-butyl benzene (90ml) was added 1.62M t-butyllithium pentane solution (12.9ml) under nitrogen at 0 ℃. 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 (5.0g) was added, warmed to room temperature and stirred for 0.5 h. Then, it was cooled again to 0 ℃ and N, N-diisopropylethylamine (2.6g) was added, and stirred at room temperature until the heat generation ended, then warmed to 100 ℃ and heated and stirred for 1 hour. The reaction solution was cooled to room temperature, and an aqueous sodium acetate solution cooled by an ice bath and ethyl acetate were sequentially added thereto and stirred for 1 hour. The yellow suspension was filtered, and the precipitate was washed twice with methanol and pure water, and then washed again with methanol. The yellow crystals were dissolved in chlorobenzene under heating and then purified using a short-path column of silica gel (eluent: heated chlorobenzene). With respect to the obtained crude product, heptane was added and filtration was performed, and then the crystals were washed with heptane, whereby compound (2-544) (6.5g) was obtained.

The structure of the obtained compound was confirmed by NMR measurement.

¹H-NMR(CDCl₃)：δ＝1.33(s,18H),1.46(s,18H),5.55(s,2H),6.88(t,2H),6.94(d,4H),7.06(dd,4H).

Synthesis examples (2 to 14): synthesis of Compound (2-542)

Intermediate (I-I) (10.7g), intermediate (I-D) (6.0g), bis (dibenzylideneacetone) palladium (0.58g), 2-dicyclohexylphosphino-2 ',6' -dimethoxybiphenyl (SPhos, 0.82g), sodium tert-butoxide (4.0g) and xylene (60ml) were placed in a flask under a nitrogen atmosphere and heated at 100 ℃ for 1.5 hours. After the reaction, water and toluene were added to the reaction solution and stirred, and then the organic layer was separated and washed with water. Then, the organic layer was concentrated to obtain a crude product. The crude product was purified by means of a silica gel short path column (eluent: toluene), and the obtained solid was washed with cooled heptane, whereby intermediate (I-L) (9.4g) was obtained.

To a flask containing intermediate (I-L) (8.6g) and tert-butylbenzene (100ml) was added 1.62M t-butyllithium pentane solution (13.8ml) under nitrogen at 0 ℃. After the completion of the dropwise addition, the temperature was raised to 60 ℃ 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 (5.4g) was added, warmed to room temperature and stirred for 0.5 h. Then, it was cooled again to 0 ℃ and N, N-diisopropylethylamine (2.8g) was added, and stirred at room temperature until the heat generation ended, then warmed to 100 ℃ and heated and stirred for 1 hour. The reaction solution was cooled to room temperature, and an aqueous sodium acetate solution cooled by an ice bath and ethyl acetate were sequentially added thereto and stirred for 1 hour. The yellow suspension was filtered, and the precipitate was washed twice with methanol and pure water, and then washed again with methanol. The yellow crystals were dissolved in chlorobenzene under heating and then purified using a short-path column of silica gel (eluent: heated chlorobenzene). With respect to the obtained crude product, heptane was added and filtration was performed, and then the crystals were washed with heptane, whereby compound (2-542) (5.9g) was obtained.

The structure of the obtained compound was confirmed by NMR measurement.

¹H-NMR(CDCl₃)：δ＝1.32(s,18H),1.46(s,18H),5.55(s,2H).

Synthesis examples (2 to 15): synthesis of Compound (2-290)

The compounds (2 to 290) were synthesized according to the method described in "synthetic example (1)" of International publication No. 2017/126443.

The structure of the obtained compound (2-290) was confirmed by NMR measurement.

¹H-NMR(CDCl₃)：δ＝8.64(s,2H),7.75(m,3H),7.69(d,2H),7.30(t,8H),7.25(s,2H),7.20(m,10H),7.08(m,6H),1.58(s,12H).

Synthesis examples (2 to 16): synthesis of Compound (2-351)

The compounds (2 to 351) were synthesized according to the method described in "Synthesis example (5)" of International publication No. 2017/126443.

The structure of the compound of formula (2-351) was confirmed by NMR measurement.

¹H-NMR(CDCl₃)：δ＝9.22(s,1H),8.78(s,1H),7.96(d,2H),7.80～7.77(m,6H),7.71(d,1H),7.59～7.44(m,8H),7.39(t,1H),7.32～7.29(m,4H),7.71(d,1H),7.19(dd,4H),7.12～7.06(m,4H),7.00(d,1H),6.45(d,1H),1.57(s,6H).

Further, the glass transition temperature (Tg) of the compound of the formula (2-351) was 165.6 ℃.

[ measurement machine: a delmond (Diamond) Differential Scanning Calorimeter (DSC) (manufactured by PERKIN ELMER); the measurement conditions were as follows: cooling rate of 200 deg.C/Min, heating rate of 10 deg.C/Min

Synthesis examples (2 to 17): synthesis of Compound (2-60)

Compound (2-60) was synthesized by the same method as in Synthesis example (2-1).

The structure of the obtained compound was confirmed by NMR measurement.

¹H-NMR：δ＝1.1(s,9H),1.4(s,9H),1.5(s,9H),1.5(s,9H),1.5(s,9H),2.2(s,3H),5.9(s,1H),6.1(s,1H),6.7(m,2H),7.0(d,2H),7.1(d,2H),7.2(d,1H),7.3(m,2H),7.4(m,1H),7.5(m,1H),7.6(dd,1H),7.7(m,3H),8.9(d,1H),8.9(d,1H).

Synthesis examples (2 to 18): synthesis of Compound (2-561)

Compound (2-561) was synthesized in the same manner as in Synthesis example (2-1).

The structure of the obtained compound was confirmed by NMR measurement.

¹H-NMR(CDCl₃)：δ＝1.08(s,6H),1.27(s,6H),1.42(s,6H),1.46(s,9H),1.47(s,9H),1.48(s,6H),1.69-1.81(m,8H),2.18(s,3H),5.97(s,1H),6.06(s,1H),6.52(s,1H),6.67(d,1H),7.08(dd,1H),7.25-7.29(m,3H),7.48(dd,1H),7.59(d,1H),7.67(d,2H),8.89(s,1H),8.97(d,1H).

Synthesis examples (2 to 19): synthesis of Compound (2-574)

Compound (2-574) was synthesized by the same method as in Synthesis example (2-1). The obtained compound was confirmed to be compound (2-574) by mass spectrometry.

EI-MS：m/z＝756.

Synthesis examples (2 to 20): synthesis of Compound (2-578)

Compound (2-578) was synthesized in the same manner as in Synthesis example (2-1). The obtained compound was confirmed to be compound (2-578) by mass spectrometry.

EI-MS：m/z＝889.

Synthesis examples (2 to 21): synthesis of Compound (2-580)

Compound (2-580) was synthesized by the same method as in Synthesis example (2-1). The obtained compound was confirmed to be compound (2-580) by mass spectrometry.

EI-MS：m/z＝811.

Synthesis examples (2 to 22): synthesis of Compound (2-548)

Compound (2-548) was synthesized in the same manner as in Synthesis example (2-1). The obtained compound was confirmed to be compound (2-548) by mass spectrometry.

EI-MS：m/z＝944.

Synthesis examples (2 to 23): synthesis of Compound (2-591)

Tri-p-tolylamine (0.287g, 1.00mmol), boron triiodide (0.783g, 2.00mmol) and o-dichlorobenzene (10.0ml) were heated with stirring under nitrogen at 150 ℃ for 2 hours. The reaction mixture was cooled to room temperature, and 2-isopropenylphenylmagnesium bromide (5.25ml, 1.2M, 6.30mmol) was added thereto. Then, the mixture was filtered through a magnesium silicate short path column (eluent: toluene), and the solvent was distilled off under reduced pressure. The obtained crude product was washed with hexane to thereby conduct isolation and purification, thereby obtaining 0.309g of 2, 8-dimethyl-10- (2- (prop-1-en-2-yl) phenyl) -5- (p-tolyl) -5, 10-dihydrodibenzo [ b, e ] [1,4] azaborine in a yield of 75%.

The structure of the obtained compound was confirmed by NMR measurement.

¹H-NMR(CDCl₃)：δ＝2.05(s,3H),2.31(s,6H),2.54(s,3H),4.78(s,2H),6.74(d,2H),7.20-7.28(m,4H),7.37-7.48(m,5H),7.56(d,1H),7.68(s,2H).

¹³C-NMR(CDCl₃)：δ＝20.6(s,2C),21.3(s,1C),23.8(s,1C),116.7(s,2C),116.9(s,1C),126.0(d,2C),126.8(s,1C),128.2(s,2C),130.0(d,4C),131.4(d,4C),133.0(s,1C),133.7(s,2C),136.4(s,2C),138.6(s,1C),139.3(s,1C),145.1(s,1C),147.0(d,2C).

2, 8-dimethyl-10- (2- (prop-1-en-2-yl) phenyl) -5- (p-tolyl) -5, 10-dihydrodibenzo [ b, e ] [1,4] azaborine (82.2mg, 0.20mmol), scandium trifluoromethanesulfonate (0.100g, 0.20mmol) and 1, 2-dichloroethane (55.0ml) were heated and stirred under a nitrogen atmosphere at 95 ℃ for 24 hours. The reaction mixture was cooled to room temperature, and then filtered using a magnesium silicate short path column (eluent: toluene), and the solvent was distilled off under reduced pressure. The obtained crude product was subjected to separation and purification using a silica gel column (eluent: hexane/toluene 6/1 (volume ratio)), to obtain 32.0mg of compound (2-591) in a yield of 39%.

The structure of the obtained compound was confirmed by NMR measurement.

¹H-NMR(CDCl₃)：δ＝1.98(s,6H),2.48(s,3H),2.53(s,3H),2.76(s,3H),6.61(d,1H),6.75(d,1H),7.14-7.31(m,4H),7.40-7.47(m,3H),7.57(dt,1H),7.81(d,1H),8.44(d,1H),8.50(s,1H).

¹³C-NMR(CDCl₃)：δ＝20.9(s,1C),21.4(s,1C),24.3(s,1C),32.6(s,2C),43.5(s,1C),114.0(s,1C),116.6(s,1C),124.7(s,1C),125.8(s,1C),127.0(s,1C),128.4(s,2C),130.1(s,2C),130.5(s,1C),131.4(s,2C),133.0(s,1C),135.2(s,1C),135.5(s,1C),137.7(s,1C),138.4(s,1C),139.5(s,1C),144.3(s,1C),145.4(s,1C),151.4(s,1C),159.5(s,1C).

Synthesis examples (2 to 24): synthesis of Compound (2-548)

EI-MS：m/z＝944.

Synthesis examples (2 to 25): synthesis of Compound (2-550)

Compound (2-550) was synthesized by the same method as in Synthesis example (2-1). The obtained compound was confirmed to be compound (2-550) by mass spectrometry.

EI-MS：m/z＝833.

Synthesis examples (2 to 26): synthesis of Compound (2-32)

Compound (2-32) was synthesized by the same method as in Synthesis example (2-1). The obtained compound was confirmed to be compound (2-32) by mass spectrometry.

EI-MS：m/z＝645.

Comparative Synthesis example (1)

Synthesis of Compound (H-1)

Compound (H-1) is synthesized by appropriately changing the method described in International publication No. 2015/064560.

Comparative Synthesis example (2)

Synthesis of Compound (D-1)

Compound (D-1) was synthesized according to the synthesis of Compound 1 of International publication No. 2012/118164.

The other compounds of the present invention can be synthesized by appropriately changing the compounds of the starting materials and using the method according to the synthesis example.

Hereinafter, examples of the organic EL device using the compound of the present invention will be described in more detail to explain the present invention, but the present invention is not limited to these examples.

Organic EL devices of examples 1 to 44 and comparative examples 1 to 5 were produced, and the emission wavelength (nm), voltage (V), and external quantum efficiency (%) at the time of emission at a specific luminance were measured. In addition, the time for which a specific luminance was maintained (element life) was also measured.

The quantum efficiency of a light-emitting element includes an internal quantum efficiency and an external quantum efficiency, and the internal quantum efficiency indicates a ratio of external energy injected as electrons (or holes) into a light-emitting layer of the light-emitting element to be 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 photons generated in the light-emitting layer is continuously absorbed or reflected inside the light-emitting element without being emitted to the outside of the light-emitting element, the external quantum efficiency is lower than the internal quantum efficiency.

The method for measuring the external quantum efficiency is as follows. Using a voltage/current generator R6144 manufactured by Edwarden test (Advantest), the luminance of the applied element became 1000cd/m²The element emits light by the voltage of (3). 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 spectral emission luminance value 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 the applied current value by the elementary charge (elementary charge) is set as the number of carriers (carrier) injected into the element, and a value obtained by dividing the total number of photons emitted from the element by the number of carriers injected into the element is the external quantum efficiency.

Table 1 below shows the material composition and EL characteristic data of each layer in the organic EL devices of examples 1 to 12 and comparative examples 1 to 3.

In each of the tables, "HI" is N ⁴,N^4'-diphenyl-N⁴,N^4'-bis (9-phenyl-9H-carbazol-3-yl) - [1,1' -biphenyl]-4,4 '-diamine, "HAT-CN" is 1,4,5,8,9, 12-hexaazatriphenylhexacarbonitrile, "HT-1" is N- ([1,1' -biphenyl)]-4-yl) -9, 9-dimethyl-N- (4- (9-phenyl-9H-carbazol-3-yl) phenyl) -9H-fluoren-2-amine, "HT-2" is N, N-bis (4- (dibenzo [ b, d ] s)]Furan-4-yl) phenyl) - [1, 1': 4', 1' -terphenyl]-4-amine, "HT-3" is N- ([1,1' -biphenyl)]-2-yl) -N- (9, 9-dimethyl-9H-fluoren-2-yl) -9,9' -spirobi [ fluorene]-4-amine, "ET-1" is 4,6,8,10-tetraphenyl [1,4 ]]Benzoxaborole heterocyclohexeno [2,3,4-k1]Phenoxyboranyl heterocycle hexene, "ET-2," is 3,3' - ((2-phenylanthracene-9, 10-diyl) bis (4, 1-phenylene)) bis (4-methylpyridine). The chemical structure is shown below together with "Liq".

< example 1 >

< host material: compounds (1-8), dopant materials: element of Compound (2-41)

A glass substrate (manufactured by Opto Science) having a thickness of 180nm and a thickness of 26mm × 28mm × 0.7mm obtained by polishing ITO to 150nm 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 the Changzhou industry Co., Ltd.), and vapor deposition boats of tantalum were set in which HI, HAT-CN, HT-1, HT-2, compound (1-8), compound (2-41), ET-1, and ET-2 were placed, respectively; aluminum nitride evaporation boats containing Liq, magnesium, and silver were placed in the respective containers.

As shown in table 1, the following layers were sequentially formed on the ITO film of the transparent support substrate. The vacuum vessel was depressurized to 5X 10^-4Pa, HI, HAT-CN, HT-1 and HT-2 were sequentially deposited by vapor deposition to form a hole injection layer 1 (film thickness: 40nm), a hole injection layer 2 (film thickness: 5nm), a hole transport layer 1 (film thickness: 15nm) and a hole transport layer 2 (film thickness: 10 nm). Then, the compounds (1 to 8) and the compounds (2 to 41) were simultaneously heated and vapor-deposited so that the film thickness became 25nm, thereby forming a light-emitting layer. The deposition rate was adjusted so that the mass ratio of the compounds (1-8) to the compounds (2-41) became about 98 to 2. Subsequently, ET-1 was heated and vapor-deposited to a film thickness of 5nm to form the electron transporting layer 1. Subsequently, ET-2 and Liq were simultaneously heated and vapor-deposited so that the film thickness became 25nm, thereby forming the electron transporting layer 2. The deposition rate was adjusted so that the mass ratio of ET-2 to Liq became about 50 to 50. The deposition rate of each layer is 0.01nm/sec to 1 nm/sec. Then, Liq is heated and vapor deposition is performed at 0.01nm/sec to 0.1nm/sec so that the film thickness becomes 1nmThe organic EL element was obtained by performing vapor deposition at a speed, and then heating magnesium and silver at the same time, and performing vapor deposition so that the film thickness became 100nm to form a cathode. In this case, the deposition rate is adjusted between 0.1nm/sec and 10nm/sec so that the atomic ratio of magnesium to silver is 10 to 1.

A DC voltage was applied to the ITO electrode as an anode and the magnesium/silver electrode as a cathode, and the concentration of the resultant was measured at 1000cd/m²As a result of the characteristics in light emission, as shown in Table 1, the driving voltage was 3.92V, the external quantum efficiency was 6.88%, and blue light emission having a wavelength of 461nm was obtained.

< example 2 to example 12 >

In example 1, each organic EL device was manufactured using the layer configuration described in table 1, and EL characteristic data was measured (table 1).

< comparative example 1 to comparative example 3 >

< example 13 >

< host material: compound (1-129), dopant material: element of Compound (2-41)

A glass substrate (manufactured by Opto Science) having a thickness of 180nm and a thickness of 26mm × 28mm × 0.7mm obtained by polishing ITO to 150nm 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 the Changzhou industry Co., Ltd.), and vapor deposition boats of tantalum were set in which HI, HAT-CN, HT-1, HT-3, compound (1-129), compound (2-41), ET-1, and ET-2 were placed, respectively; aluminum nitride evaporation boats containing Liq, magnesium, and silver were placed in the respective containers.

As shown in table 1, the following layers were sequentially formed on the ITO film of the transparent support substrate. The vacuum vessel was depressurized to 5X 10^-4Pa, HI, HAT-CN, HT-1 and HT-3 were sequentially deposited by vapor deposition to form a hole injection layer 1 (film thickness: 40nm), a hole injection layer 2 (film thickness: 5nm), a hole transport layer 1 (film thickness: 15nm) and a hole transport layer 2 (film thickness: 10 nm). Then, the compound (1-129) and the compound (2-41) are heated simultaneously so that the film thickness becomes equal toThe light-emitting layer was formed by evaporation at 25 nm. The deposition rate was adjusted so that the mass ratio of the compounds (1 to 129) to the compounds (2 to 41) became about 98 to 2. Subsequently, ET-1 was heated and vapor-deposited to a film thickness of 5nm to form the electron transporting layer 1. Subsequently, ET-2 and Liq were simultaneously heated and vapor-deposited so that the film thickness became 25nm, thereby forming the electron transporting layer 2. The deposition rate was adjusted so that the mass ratio of ET-2 to Liq became about 50 to 50. The deposition rate of each layer is 0.01nm/sec to 1 nm/sec. Subsequently, Liq was heated and vapor deposition was performed at a vapor deposition rate of 0.01nm/sec to 0.1nm/sec so that the film thickness became 1nm, and then magnesium and silver were simultaneously heated and vapor deposition was performed so that the film thickness became 100nm to form a cathode, thereby obtaining an organic EL element. In this case, the deposition rate is adjusted between 0.1nm/sec and 10nm/sec so that the atomic ratio of magnesium to silver is 10 to 1.

A DC voltage was applied to the ITO electrode as an anode and the magnesium/silver electrode as a cathode, and the concentration of the resultant was measured at 1000cd/m²As a result of the characteristics in light emission, the driving voltage was 4.07V and the external quantum efficiency was 6.78%, as shown in table 2. Then, the fabricated device was subjected to a constant current driving test (current density: 10 mA/cm)²) As a result, the time for which the luminance of 90% or more of the initial luminance was maintained was 153 hours.

< example 14 to example 44 >

In example 13, each organic EL device was manufactured using the layer configuration described in table 2, and EL characteristic data was measured (table 2).

< comparative example 4 to comparative example 5 >

[ industrial applicability ]

The present invention can provide an organic EL element which has high external quantum efficiency and can emit light at low voltage.

Claims

1. 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 which contains a benzanthracene compound represented by formula (1) below as a host material and a polycyclic aromatic compound represented by formula (2) below or a polymer of polycyclic aromatic compounds having a plurality of structures represented by formula (2) below as a dopant material;

In the formula (1), the reaction mixture is,

X_a、X_b、Ar⁴、Ar⁵、Ar⁶、Ar⁷、Ar⁸、Ar⁹、Ar¹⁰、Ar¹¹、Ar¹²and Ar¹³Each independently is hydrogen, 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, X_a、X_b、Ar⁴、Ar⁵、Ar⁶、Ar⁷、Ar⁸、Ar⁹、Ar¹⁰、Ar¹¹、Ar¹²And Ar¹³Not all of which are simultaneously hydrogen, at least one hydrogen in the compound represented by formula (1) may be substituted by halogen, cyano or deuterium,

in the formula (2), the reaction mixture is,

X¹and X²Independently of each other > O, > N-R, > C (-R)₂R > N-R is aryl which may be substituted, heteroaryl which may be substituted, alkyl which may be substituted or cycloalkyl which may be substituted, said > C (-R)₂R of (A) is hydrogen, optionally substituted arylAlkyl which may be substituted or cycloalkyl which may be substituted, in addition to said R > N-R and/or said > C (-R)₂R of (A) may be bonded to the A ring, the B ring and/or the C ring through a linking group or a single bond,

at least one hydrogen in the compound or structure represented by formula (2) may be substituted with deuterium, cyano, or halogen.

2. The organic electroluminescent element according to claim 1,

in the formula (2), the reaction mixture is,

X¹And X²Independently of each other > O, > N-R, > C (-R)₂R > N-R is aryl which may be substituted by alkyl or cycloalkyl, heteroaryl which may be substituted by alkyl or cycloalkyl, > C (-R)₂R of (a) is hydrogen, aryl which may be substituted by alkyl or cycloalkyl, and additionally, said R > N-R and/or said > C (-R)₂R of (a) can be represented by-O-, -S-, -C (-R)₂-or a single bond to the A ring, B ring and/or C ring, the-C (-R)₂R of-is hydrogen, alkyl or cyclicAn alkyl group, a carboxyl group,

3. The organic electroluminescent element according to claim 1, wherein the polycyclic aromatic compound or a multimer thereof is a polycyclic aromatic compound represented by formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e), or formula (2-f) or a multimer of a polycyclic aromatic compound having a structure represented by a plurality of formulae (2-a), (2-b), (2-c), (2-d), (2-e), or formula (2-f);

In the formula (2-a), the formula (2-b), the formula (2-c), the formula (2-d), the formula (2-e) and the formula (2-f),

R¹、R²、R³、R⁴、R⁵、R⁶、R⁷、R⁸、R⁹、R¹⁰and R¹¹Each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboron and wherein two aryl groups may be bonded via a single bond or a linking group, alkyl, cycloalkyl, alkoxy, aryloxy or substituted silyl, at least one of which may be substituted by aryl, heteroaryl, alkyl, cycloalkyl or substituted silyl, and further wherein R is¹～R¹¹May be bonded to each other and form, together with the a-ring, b-ring or c-ring, an aryl or heteroaryl ring, at least one hydrogen in the ring formed being substitutable fromAryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboron and wherein two aryl groups may be substituted via a single bond or a linking group bond, alkyl, cycloalkyl, alkoxy, aryloxy or substituted silane groups, at least one of which may be substituted by aryl, heteroaryl, alkyl, cycloalkyl or substituted silane groups,

in the case of multimers, are dimers or trimers having 2 or 3 structures represented by formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e) or formula (2-f).

4. The organic electroluminescent element according to claim 3, wherein the polycyclic aromatic compound or a multimer thereof is a polycyclic aromatic compound represented by formula (2-a) or a multimer of polycyclic aromatic compounds having a plurality of structures represented by formula (2-a).

5. The organic electroluminescent element according to claim 4, wherein the polycyclic aromatic compound is represented by any one of the following structural formulae;

6. The organic electroluminescent element according to claim 4, wherein the polycyclic aromatic compound is represented by any one of the following structural formulae;

in the formula, Me is methyl, and tBu is tert-butyl.

7. The organic electroluminescent element according to claim 3, wherein the polycyclic aromatic compound or a multimer thereof is a polycyclic aromatic compound represented by formula (2-b) or a multimer of polycyclic aromatic compounds having a plurality of structures represented by formula (2-b).

8. The organic electroluminescent element according to claim 7, wherein the polycyclic aromatic compound is represented by any one of the following structural formulae;

in the formula, Me is methyl, and tBu is tert-butyl.

9. The organic electroluminescent element according to any one of claims 1 to 8, wherein,

in the formula (1), the reaction mixture is,

A triphenylene group which may be substituted with any one or more substituents selected from substituent group A, a pyrenyl group which may be substituted with any one or more substituents selected from substituent group AAn anthracene group substituted with the above substituent, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a silane group which may be substituted with an alkyl group having 1 to 4 carbon atoms, a group represented by the following formula (A) or a group represented by the following formula (B),

wherein, X_aAnd X_bBoth of these will not be hydrogen,

at least one hydrogen in the compound represented by formula (1) may be substituted by halogen, cyano, or deuterium;

10. the organic electroluminescent element according to claim 9, wherein Ar⁴、Ar⁵、Ar⁶、Ar⁹、Ar¹⁰And Ar¹³Are each hydrogen, Ar⁷、Ar⁸、Ar¹¹、Ar¹²、X_aAnd X_bEach of which is independently hydrogen, phenyl which may be substituted with any one or more substituents selected from substituent group A, biphenyl which may be substituted with any one or more substituents selected from substituent group A, terphenyl which may be substituted with any one or more substituents selected from substituent group A, naphthyl which may be substituted with any one or more substituents selected from substituent group A, phenalkenyl which may be substituted with any one or more substituents selected from substituent group A, phenanthryl which may be substituted with any one or more substituents selected from substituent group A, fluorenyl which may be substituted with any one or more substituents selected from substituent group A, triphenylenyl which may be substituted with any one or more substituents selected from substituent group A, pyrenyl which may be substituted with any one or more substituents selected from substituent group A, triphenylenyl, and the like, An alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a silyl group which may be substituted with an alkyl group having 1 to 4 carbon atoms, a group represented by the formula (A) or a group represented by the formula (B).

11. The organic electroluminescent element according to claim 9 or 10, wherein the group represented by formula (a) is a group represented by any one of formulae (a-1) to (a-14), and the group represented by formula (B) is a group represented by formula (B-1);

in the formulae (A-1) to (A-14) and (B-1), Y is-O-, -S-or > N-R³⁹，R³⁹At least one hydrogen in each of the groups represented by the formulae (A-1) to (A-14) and (B-1) may be substituted by 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 diaryl-substituted amino group, a diheteroaryl-substituted amino group, an arylheteroaryl-substituted amino group, a halogen group, a hydroxyl group or a cyano group,

12. The organic electroluminescent element according to any one of claims 1 to 8, wherein the compound represented by formula (1) is a compound represented by any one of the following formulae;

In the formula, Me is methyl, and tBu is tert-butyl.

13. The organic electroluminescent element according to any one of claims 1 to 12, which comprises an electron transport layer and/or an electron injection layer disposed between the cathode and the light-emitting layer, wherein at least one of the electron transport layer and the electron injection layer contains at least one selected from the group consisting of borane derivatives, pyridine derivatives, fluoranthene derivatives, BO derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, arylnitrile derivatives, triazine derivatives, benzimidazole derivatives, phenanthroline derivatives, and hydroxyquinoline metal complexes.

14. The organic electroluminescent element according to claim 13, wherein the electron transport layer and/or the electron injection layer further contains at least one selected from the group consisting of alkali metals, alkaline earth metals, rare earth metals, oxides of alkali metals, halides of alkali metals, oxides of alkaline earth metals, halides of alkaline earth metals, oxides of rare earth metals, halides of rare earth metals, organic complexes of alkali metals, organic complexes of alkaline earth metals, and organic complexes of rare earth metals.

15. A display device comprising the organic electroluminescent element as claimed in any one of claims 1 to 14.

16. A lighting device comprising the organic electroluminescent element as claimed in any one of claims 1 to 14.

17. A benzanthracene compound represented by the following formula (1');

in the formula (1'), in the presence of a catalyst,

Ar⁴'、Ar⁵'、Ar⁶'、Ar⁷'、Ar⁸'、Ar⁹'、Ar¹⁰'、Ar¹¹'、Ar¹²'、Ar¹³'、X_a' and X_b' are each independently hydrogen, a phenyl group which may be substituted with any one or more substituents selected from substituent group A, a biphenyl group which may be substituted with any one or more substituents selected from substituent group A, a terphenyl group which may be substituted with any one or more substituents selected from substituent group A, a quaterphenyl group which may be substituted with any one or more substituents selected from substituent group A, a naphthyl group which may be substituted with any one or more substituents selected from substituent group A, a phenalkenyl group which may be substituted with any one or more substituents selected from substituent group A, a phenanthrenyl group which may be substituted with any one or more substituents selected from substituent group A, a fluorenyl group which may be substituted with any one or more substituents selected from substituent group A, a benzofluorenyl group which may be substituted with any one or more substituents selected from substituent group A, a phenyl group which may be substituted with any one or, Substituted by any one or more substituents selected from substituent group A

wherein, X_a' and X_b' both of these will not be hydrogen,

at least one hydrogen in the compound represented by formula (1') may be substituted with halogen, cyano, or deuterium;

18. the benzanthracene compound according to claim 17, wherein,

the group represented by formula (B-1) is a group obtained by removing one hydrogen at any position of formula (B-1), and represents the position;

19. the benzanthracene compound according to claim 17 or 18, which is represented by the following formula (1' a);

in the formula (1' a), the metal oxide,

20. The benzanthracene compound of claim 19, wherein X_a' and X_bEither of' is hydrogen.

21. The benzanthracene compound according to claim 20, which is represented by any one of the following formulae;

22. the benzanthracene compound according to claim 20 or 21, wherein in formula (a) and formula (B), Y is-O-.

23. The benzanthracene compound according to claim 20 or 21, wherein R other than the bond in formula (a) and formula (B)²¹～R³⁸Are all hydrogen.

24. The benzanthracene compound of claim 19, wherein X_a' andX_b' both are groups containing a group represented by the formula (A) or the formula (B).

25. The benzanthracene compound according to claim 24, which is represented by the following formula;

26. the benzanthracene compound according to claim 19, which is represented by any one of the following formulae;

27. the benzanthracene compound of claim 19, wherein with respect to X_a' and X_b'，

28. The benzanthracene compound according to claim 27, represented by any one of the following formulae;

in the formula, tBu is tert-butyl.

29. The benzanthracene compound according to claim 17 or 18, wherein Ar is⁵'、Ar⁶'、Ar⁷'、Ar⁸' or Ar⁹' is a group containing a group represented by the formula (A) or the formula (B).

30. The benzanthracene compound of claim 29, wherein with respect to X_a' and X_b'，

31. The benzanthracene compound according to claim 30, which is represented by any one of the following formulae;

32. the benzanthracene compound of claim 30 or 31, wherein Ar⁶'、Ar⁷' or Ar⁸' is a group containing a group represented by the formula (A) or the formula (B).

33. The benzanthracene compound according to claim 17, which is represented by any one of the following formulae;

in the formula, Me is methyl.