Organic electroluminescence element and benzanthracene compound

Abstract

To provide an organic EL element with high external quantum efficiency, and a compound that can be used for the same.SOLUTION: The present invention provides a benzanthracene compound represented by a formula (1'), where Ar4'-Ar13' each represent hydrogen or the like, and Xa' and Xb' each represent an optionally substituted aryl or an optionally substituted heteroaryl or the like.SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to an organic electroluminescent device, a display device and a lighting device using the same, and a benzanthracene compound that can be used as a light-emitting material. [Background technology]

[0002] Conventionally, display devices using electroluminescent light-emitting elements have been extensively studied because they can be made more energy-efficient and thinner, and organic electroluminescent elements (hereinafter sometimes referred to as "organic EL elements") made of organic materials have been actively studied because they can be easily made lighter and larger. In particular, the development of organic materials with luminescent properties such as blue, one of the three primary colors of light, and combinations of multiple materials that provide optimal luminescent properties have been actively researched, regardless of whether they are polymeric or low molecular weight compounds.

[0003] An organic EL element has a structure consisting of a pair of electrodes consisting of an anode and a cathode, and one or more layers containing organic compounds that are disposed between the pair of electrodes. The layers containing organic compounds include a light-emitting layer and a charge transport / injection layer that transports or injects charges such as holes and electrons, and various organic materials suitable for these layers have been developed.

[0004] Patent Documents 1 to 3 describe the use of benzanthracene compounds as light-emitting materials in organic electroluminescent devices, and Patent Document 3 discloses the use of benzanthracene compounds as host materials in the light-emitting layer of organic electroluminescent devices.

[0005] In recent years, polycyclic aromatic compounds in which a plurality of aromatic rings are condensed with a central atom such as boron have been reported as materials for organic electroluminescent devices (Patent Document 4). [Prior art documents] [Patent documents]

[0006] [Patent Document 1] JP 2000-178548 A [Patent Document 2] JP 2007-277113 A [Patent Document 3] International Publication No. 2009 / 081776 [Patent Document 4] International Publication No. 2015 / 102118 Summary of the Invention [Problem to be solved by the invention]

[0007] As described above, various materials have been developed for use in organic EL elements, but in order to increase the options of materials for organic EL elements, it is desirable to develop materials made of compounds different from conventional ones. An object of the present invention is to provide an organic EL element using a new combination of materials. An object of the present invention is to provide an organic EL element having high external quantum efficiency. [Means for solving the problem]

[0008] As a result of intensive research to solve the above problems, the present inventors have found that an excellent organic EL device can be obtained by using an emission layer containing a specific benzanthracene compound as a host material and a polycyclic aromatic compound in which multiple aromatic rings are condensed as a dopant material, and have completed the present invention. That is, the present invention provides an organic electroluminescence device and a benzanthracene compound as follows.

[0009] <1> The organic electroluminescence device has a pair of electrodes consisting of an anode and a cathode, and a light-emitting layer disposed between the pair of electrodes, the light-emitting layer containing a benzanthracene compound represented by the following formula (1) as a host material, and a polycyclic aromatic compound represented by the following formula (2) or a polymer of a polycyclic aromatic compound having a plurality of structures represented by the following formula (2) as a dopant material.

[0010] [ka]

[0011] (In formula (1), X a , X b , Ar 4 , Ar 5 , Ar 6 , Ar 7 , Ar 8 , Ar 9 , Ar 10 , Ar 11 , Ar 12 , and Ar 13 are each independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted diarylamino, optionally substituted diheteroarylamino, optionally substituted arylheteroarylamino, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted arylthio, or optionally substituted silyl; X a , X b , Ar 4 , Ar 5 , Ar 6 , Ar 7 , Ar 8 , Ar 9 , Ar 10 , Ar 11 , Ar 12 , and Ar 13 are not all hydrogen at the same time, and at least one hydrogen in the compound represented by formula (1) may be substituted with a halogen, cyano, or deuterium.

[0012] (In formula (2), ring A, ring B and ring C are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen atom in these rings may be substituted; X 1 and X 2 are independently >O, >NR, >C(-R) 2, >S, or >Se, and R of the >NR is optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl, or optionally substituted cycloalkyl, and the >C(-R) 2 R is hydrogen, optionally substituted aryl, optionally substituted alkyl, or optionally substituted cycloalkyl, and R in >NR and / or >C(-R) 2 R may be bonded to the ring A, ring B, and / or ring C via a linking group or a single bond; In the compound represented by formula (2) or a multimer thereof, at least one selected from the group consisting of an aryl ring and a heteroaryl ring may be condensed with at least one cycloalkane, at least one hydrogen in the cycloalkane may be substituted, and at least one -CH 2 - may be replaced by -O-; At least one hydrogen atom in the compound or structure represented by formula (2) may be replaced with deuterium, cyano, or halogen.

[0013] <2> In formula (2), Ring A, ring B, and ring C are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen atom in these rings may be replaced by a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted diarylamino, a substituted or unsubstituted diheteroarylamino, a substituted or unsubstituted arylheteroarylamino, a substituted or unsubstituted alkyl, a substituted or unsubstituted cycloalkyl, a substituted or unsubstituted alkoxy, or a substituted or unsubstituted aryloxy. In addition, these rings may each independently be replaced by a boron atom, X 1 and X 2 Formula (2) having a 5- or 6-membered ring sharing a bond with the central fused 2-ring structure, X 1 and X 2 are independently >O, >NR, >C(-R) 2, >S, or >Se, and R of the >NR is aryl optionally substituted with alkyl or cycloalkyl, heteroaryl optionally substituted with alkyl or cycloalkyl, alkyl, or cycloalkyl, and the >C(-R) 2 R is hydrogen, aryl, alkyl or cycloalkyl which may be substituted with alkyl or cycloalkyl, and R in >NR and / or >C(-R) 2 R is -O-, -S-, -C(-R) 2 - or a single bond may be bonded to the ring A, ring B, and / or ring C, and the -C(-R) 2 R in - is hydrogen, alkyl, or cycloalkyl; In the compound represented by formula (2) or a multimer thereof, at least one selected from the group consisting of an aryl ring and a heteroaryl ring may be condensed with at least one cycloalkane, at least one hydrogen in the cycloalkane may be substituted, and at least one -CH 2 - may be replaced by -O-; At least one hydrogen atom in the compound or structure represented by formula (2) may be replaced with deuterium, cyano, or halogen; In the case of a polymer, it is a dimer or trimer having two or three structures represented by formula (2). <1> The organic electroluminescent device according to claim 1.

[0014] <3> 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 plurality of structures represented by formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e), or formula (2-f); <1> The organic electroluminescent device according to claim 1.

[0015] [ka]

[0016] (In formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e), and formula (2-f), R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , and R 11 are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyl, in which at least one hydrogen may be replaced by an aryl, heteroaryl, alkyl, cycloalkyl, or substituted silyl; and R 1 ~R 11 adjacent groups among the above may be bonded to each other to form an aryl ring or a heteroaryl ring together with the a ring, the b ring, or the c ring, and at least one hydrogen atom in the formed ring may be replaced by an aryl, a heteroaryl, a diarylamino, a diheteroarylamino, an arylheteroarylamino, a diarylboryl (two aryls may be bonded via a single bond or a linking group), an alkyl, a cycloalkyl, an alkoxy, an aryloxy, or a substituted silyl, and at least one hydrogen atom in these may be replaced by an aryl, a heteroaryl, an alkyl, a cycloalkyl, or a substituted silyl; X X are each independently >O, >S, >NR, or >C(-R) 2 R of the >NR is an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl, or an optionally substituted cycloalkyl, and the >C(-R) 2R is each independently hydrogen, aryl optionally substituted with alkyl or cycloalkyl, heteroaryl optionally substituted with alkyl or cycloalkyl, alkyl, or cycloalkyl; X 1 and X 2 are independently >O, >NR, >C(-R) 2 , >S, or >Se, and R of the >NR is an aryl having 6 to 12 carbon atoms which may be substituted with an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms, a heteroaryl having 2 to 15 carbon atoms which may be substituted with an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms, an alkyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 14 carbon atoms, and the >C(-R) 2 R is hydrogen, an aryl having 6 to 12 carbon atoms which may be substituted with an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms, an alkyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 14 carbon atoms, and R in the >NR and / or the >C(-R) 2 R is -O-, -S-, -C(-R) 2 - or may be bonded to the ring a, ring b and / or ring c via a single bond, and the -C(-R) 2 R in - is alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 14 carbon atoms, In the 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, at least one selected from the group consisting of an aryl ring and a heteroaryl ring may be condensed with at least one cycloalkane, at least one hydrogen in the cycloalkane may be substituted, and at least one -CH in the cycloalkane may be substituted. 2 - may be replaced by -O-; At least one hydrogen atom 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 replaced with deuterium, cyano, or halogen; In the case of a multimer, it is a dimer or trimer having two or three structures represented by formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e), or formula (2-f).

[0017] <4> The polycyclic aromatic compound or a multimer thereof is a polycyclic aromatic compound represented by formula (2-a) or a multimer of a polycyclic aromatic compound having a plurality of structures represented by formula (2-a). <3> The organic electroluminescent device according to claim 1.

[0018] <5> The polycyclic aromatic compound is represented by any one of the following structural formulas: <4> The organic electroluminescent device according to the present invention; [ka]

[0019] [ka] In the above formula, Me is methyl, tBu is tertiary butyl, tAm is tertiary amyl, and D is deuterium.

[0020] <6> The polycyclic aromatic compound is represented by any one of the following structural formulas: <4> The organic electroluminescent device according to the present invention; [ka] In the above formula, Me is methyl and tBu is tertiary butyl.

[0021] <7> The polycyclic aromatic compound or a multimer thereof is a polycyclic aromatic compound represented by formula (2-b) or a multimer of a polycyclic aromatic compound having a plurality of structures represented by formula (2-b). <3> The organic electroluminescent device according to claim 1.

[0022] <8> The polycyclic aromatic compound is represented by any one of the following structural formulas: <7> The organic electroluminescent device according to the present invention; [ka] In the above formula, Me is methyl and tBu is tertiary butyl.

[0023] <9> In formula (1), Ar 4 , Ar 5 , Ar 6 , Ar 7 , Ar 8 , Ar 9 , Ar 10 , Ar 11 , Ar 12 , Ar 13 , X a and X b each independently represents hydrogen, phenyl which may be substituted with one or more substituents selected from substituent group A, biphenylyl which may be substituted with one or more substituents selected from substituent group A, terphenylyl which may be substituted with one or more substituents selected from substituent group A, quaterphenylyl which may be substituted with one or more substituents selected from substituent group A, naphthyl which may be substituted with one or more substituents selected from substituent group A, phenalenyl which may be substituted with one or more substituents selected from substituent group A, phenanthryl which may be substituted with one or more substituents selected from substituent group A, any one selected from substituent group A or one or more substituents selected from substituent group A; fluorenyl which may be substituted by any one or more substituents selected from substituent group A; benzofluorenyl which may be substituted by any one or more substituents selected from substituent group A; chrysenyl which may be substituted by any one or more substituents selected from substituent group A; triphenylenyl which may be substituted by any one or more substituents selected from substituent group A; pyrenyl which may be substituted by any one or more substituents selected from substituent group A; anthracenyl which may be substituted by any one or more substituents selected from substituent group A; alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, silyl which may be substituted by alkyl having 1 to 4 carbon atoms, a group represented by the following formula (A) or a group represented by the following formula (B): However, X a and X b Both cannot be hydrogen. Substituent group A consists of phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenalenyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenyl, anthracenyl, alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, silyl which may be substituted by alkyl having 1 to 4 carbon atoms, a group represented by formula (A) and a group represented by formula (B); In formula (A) and formula (B), Y is -O-, -S- or >NR 39 and R 21 ~R 38 are each independently hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, optionally substituted amino, halogen, hydroxy, or cyano; R 21 ~R 38 adjacent groups among these 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 optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, optionally substituted amino, halogen, hydroxy, or cyano; R 39 is hydrogen or optionally substituted aryl, The group represented by formula (A) is a group obtained by removing one hydrogen atom from any position of formula (A), and * indicates the position, The group represented by formula (B) is a group obtained by removing one hydrogen atom from any position of formula (B), and * indicates the position, At least one hydrogen atom in the compound represented by formula (1) may be substituted with halogen, cyano, or deuterium. <1> ~ <8> 13. The organic electroluminescent device according to claim 12,

[0024] [ka]

[0025] <10> Ar 4 , Ar 5 , Ar 6 , Ar 9 , Ar 10 , and Ar 13 are both hydrogen, and Ar 7 , Ar 8 , Ar 11 , Ar 12 , X a and X b are each independently hydrogen, phenyl which may be substituted with any one or more substituents selected from substituent group A, biphenylyl which may be substituted with any one or more substituents selected from substituent group A, terphenylyl 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, phenalenyl 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, alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, silyl which may be substituted with alkyl having 1 to 4 carbon atoms, a group represented by formula (A) or a group represented by formula (B). <9> The organic electroluminescent device according to claim 1.

[0026] <11> The group represented by formula (A) is a group represented by any one of formulas (A-1) to (A-14), and the group represented by formula (B) is a group represented by formula (B-1). <9> or <10> The organic electroluminescent device according to claim 1. [ka]

[0027] In the formulae (A-1) to (A-14) and (B-1), Y is -O-, -S- or >NR 39 and R 39 is hydrogen or aryl, and at least one hydrogen in each of the groups represented by formulae (A-1) to (A-14) and (B-1) may be substituted with alkyl, cycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, diaryl-substituted amino, diheteroaryl-substituted amino, arylheteroaryl-substituted amino, halogen, hydroxy, or cyano; The groups represented by formulae (A-1) to (A-14) are groups obtained by removing one hydrogen atom from any one of positions in formulae (A-1) to (A-14), respectively, and * indicates the position. The group represented by formula (B-1) is a group obtained by removing one hydrogen atom from any position of formula (B-1), and * indicates the position.

[0028] <12> The compound represented by formula (1) is a compound represented by any one of the following formulas: <1> ~ <8> The organic electroluminescent device according to any one of the preceding claims. [ka]

[0029] [ka]

[0030] [ka]

[0031] [ka]

[0032] [ka]

[0033] [ka] In the above formula, Me is methyl and tBu is tertiary butyl.

[0034] <13> an electron transport layer and / or an electron injection layer disposed between the cathode and the light emitting layer, at least one of the electron transport layer and the electron injection layer containing 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 quinolinol metal complexes; <1> ~ <12> 13. The organic electroluminescent device according to claim 12, <14> the electron transport layer and / or the electron injection layer further contains at least one selected from the group consisting of an alkali metal, an alkaline earth metal, a rare earth metal, an oxide of an alkali metal, a halide of an alkali metal, an oxide of an alkaline earth metal, a halide of an alkaline earth metal, an oxide of a rare earth metal, a halide of a rare earth metal, an organic complex of an alkali metal, an organic complex of an alkaline earth metal, and an organic complex of a rare earth metal; <13> The organic electroluminescent device according to claim 1. <15> <1> ~ <14> A display device comprising the organic electroluminescent device according to any one of claims 1 to 4. <16> <1> ~ <14> 2. A lighting device comprising the organic electroluminescent element according to claim 1.

[0035] <17> A benzanthracene compound represented by the following formula (1'): [ka]

[0036] In formula (1'), Ar 4 ', Ar 5 ', Ar 6 ', Ar 7 ', Ar 8 ', Ar 9 ', Ar 10 ', Ar 11 ', Ar 12 ', Ar 13 ', X a ' and X b' each independently represents hydrogen, phenyl which may be substituted with one or more substituents selected from substituent group A, biphenylyl which may be substituted with one or more substituents selected from substituent group A, terphenylyl which may be substituted with one or more substituents selected from substituent group A, quaterphenylyl which may be substituted with one or more substituents selected from substituent group A, naphthyl which may be substituted with one or more substituents selected from substituent group A, phenalenyl which may be substituted with one or more substituents selected from substituent group A, phenanthryl which may be substituted with one or more substituents selected from substituent group A, any one selected from substituent group A or one or more substituents selected from substituent group A; fluorenyl which may be substituted by any one or more substituents selected from substituent group A; benzofluorenyl which may be substituted by any one or more substituents selected from substituent group A; chrysenyl which may be substituted by any one or more substituents selected from substituent group A; triphenylenyl which may be substituted by any one or more substituents selected from substituent group A; pyrenyl which may be substituted by any one or more substituents selected from substituent group A; anthracenyl which may be substituted by any one or more substituents selected from substituent group A; alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, silyl which may be substituted by alkyl having 1 to 4 carbon atoms, a group represented by the following formula (A) or a group represented by the following formula (B): However, X a ' and X b ' cannot both be hydrogen, Substituent group A consists of phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenalenyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenyl, anthracenyl, alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, silyl which may be substituted by alkyl having 1 to 4 carbon atoms, a group represented by formula (A) and a group represented by formula (B); In formula (A) and formula (B), Y is -O-, -S- or >NR 39 and R 21 ~R 38are each independently hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, optionally substituted amino, halogen, hydroxy, or cyano; R 21 ~R 38 adjacent groups among these 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 optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, optionally substituted amino, halogen, hydroxy, or cyano; R 39 is hydrogen or optionally substituted aryl, The group represented by formula (A) is a group obtained by removing one hydrogen atom from any position of formula (A), and * indicates the position, The group represented by formula (B) is a group obtained by removing one hydrogen atom from any position of formula (B), and * indicates the position, The compound represented by formula (1') contains at least one group selected from the group consisting of a group represented by formula (A) and a group represented by formula (B), At least one hydrogen atom in the compound represented by formula (1') may be substituted with halogen, cyano, or deuterium.

[0037] [ka]

[0038] <18> Formula (A) is any one of formulas (A-1) to (A-14), and formula (B) is formula (B-1), In the formulae (A-1) to (A-14) and (B-1), Y is -O-, -S-, or >NR 39 and R 39 is hydrogen or aryl, and at least one hydrogen in each of the groups represented by formulae (A-1) to (A-14) and (B-1) may be substituted with alkyl, cycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, diaryl-substituted amino, diheteroaryl-substituted amino, arylheteroaryl-substituted amino, halogen, hydroxy, or cyano; The groups represented by formulae (A-1) to (A-14) are groups obtained by removing one hydrogen atom from any one of the positions of formulae (A-1) to (A-14), respectively, and * indicates the position. The group represented by formula (B-1) is a group obtained by removing one hydrogen atom from any position of formula (B-1), and * indicates the position. <17> The benzanthracene compound according to claim 1.

[0039] [ka]

[0040] <19> Represented by the following formula (1'a) <17> or <18> Benzanthracene compounds according to the above formula (1); [ka]

[0041] In formula (1'a), X a ' and X beach ' is independently hydrogen, phenyl which may be substituted with one or more substituents selected from substituent group A, biphenylyl which may be substituted with one or more substituents selected from substituent group A, naphthyl which may be substituted with one or more substituents selected from substituent group A, phenanthryl which may be substituted with one or more substituents selected from substituent group A, a group represented by formula (A) or a group represented by formula (B), and X a ' and X b At least one of ' is a group containing a group represented by formula (A) or formula (B), Ar 7 ', Ar 8 ', Ar 11 ', and Ar 12 ' are each independently hydrogen, methyl, t-butyl, phenyl, biphenylyl, or naphthyl; At least one hydrogen atom in the compound represented by formula (1'a) may be substituted with halogen, cyano, or deuterium.

[0042] <20> X a ' and X b ' is hydrogen, <19> The benzanthracene compound according to claim 1. <21> Represented by one of the following formulas: <20> The benzanthracene compound according to claim 1. [ka]

[0043] [ka]

[0044] <22> In formula (A) and formula (B), Y is -O-. <20> or <21> The benzanthracene compound according to claim 1. <23> In formula (A) and formula (B), R other than a bond 21 ~R 38 are both hydrogen <20> or <21> The benzanthracene compound according to claim 1. <24> X a ' and X b ' is a group containing a group represented by formula (A) or formula (B), <19> The benzanthracene compound according to claim 1.

[0045] <25> Represented by the following formula: <24> The benzanthracene compound according to claim 1. [ka]

[0046] <26> Represented by one of the following formulas: <19> The benzanthracene compound according to claim 1. [ka]

[0047] <27> X a ' and X b 'teeth, one of them is a phenyl substituted with a group represented by formula (A) or a group represented by formula (B), and the other is an unsubstituted phenyl, one of them is naphthyl substituted with a group represented by formula (A) or a group represented by formula (B), and the other is naphthyl which may be substituted with a group represented by formula (A) or a group represented by formula (B), or one of them is a phenanthryl substituted with a group represented by formula (A) or a group represented by formula (B), and the other is a phenanthryl which may be substituted with a group represented by formula (A) or a group represented by formula (B); <19> The benzanthracene compound according to claim 1.

[0048] <28> Represented by one of the following formulas: <27> Benzanthracene compounds according to the above formula (1); [ka]

[0049] [ka] In the above formula, tBu is tertiary butyl.

[0050] <29> Ar 5 ', Ar 6 ', Ar 7 ', Ar 8 ', or Ar 9 ' is a group containing a group represented by formula (A) or formula (B) <17> or <18> The benzanthracene compound according to claim 1. <30> X a ' and X b 'teeth, one of them is unsubstituted phenyl and the other is phenyl which may be substituted with one or more substituents selected from Substituent group A, or Each of them is naphthyl optionally substituted with one or more substituents selected from Substituent Group A, or Each of them is phenanthryl optionally substituted with 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 type of any one or more substituents selected from the substituent group A; <29> The benzanthracene compound according to claim 1.

[0051] <31> Represented by one of the following formulas: <30> The benzanthracene compound according to claim 1. [ka]

[0052] <32> Ar 6 ', Ar 7 ', or Ar 8 ' is a group containing a group represented by formula (A) or formula (B) <30> or <31> The benzanthracene compound according to claim 1.

[0053] <33> Represented by one of the following formulas: <17> Benzanthracene compounds according to the above formula (1); [ka] In the above formula, Me is methyl. Effect of the Invention

[0054] The present invention provides an organic EL device using a new combination of materials. The organic EL device of the present invention has high external quantum efficiency and can emit light at a low voltage. The present invention also provides a benzanthracene compound that can be used in the production of the organic EL device. [Brief description of the drawings]

[0055] [Figure 1] FIG. 1 is a schematic cross-sectional view showing an example of an organic EL element of the present invention. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0056] The present invention will be described in detail below. The following description of the constituent elements may be based on representative embodiments or specific examples, but the present invention is not limited to such embodiments. In this specification, a numerical range expressed using "~" means a range including the numerical values ​​before and after "~" as the lower and upper limits. In this specification, "hydrogen" in the explanation of the structural formula means "hydrogen atom (H)".

[0057] In this specification, the chemical structure or the substituent may be expressed by the number of carbon atoms, but the number of carbon atoms in the case where a substituent is substituted on the chemical structure or where a substituent is further substituted on the substituent means the number of carbon atoms in each of the chemical structure and the substituent, and does not mean the total number of carbon atoms in the chemical structure and the substituent, or the total number of carbon atoms in the substituent and the substituent. For example, "substituent B of carbon number Y substituted with substituent A of carbon number X" means that "substituent B of carbon number Y" is substituted with "substituent A of carbon number X", and the carbon number Y is not the total number of carbon atoms in the substituent A and the substituent B. Also, for example, "substituent B of carbon number Y substituted with substituent A" means that "substituent B of carbon number Y" is substituted with "substituent A (without carbon number limit)", and the carbon number Y is not the total number of carbon atoms in the substituent A and the substituent B.

[0058] <<Organic electroluminescent device>> The organic electroluminescent device of the present invention has a pair of electrodes consisting of 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 one example of the organic EL device of the present invention.

[0059] The organic EL element 100 shown in FIG. 1 has a substrate 101, an anode 102 provided on the substrate 101, a hole injection layer 103 provided on the anode 102, a hole transport layer 104 provided on the hole injection layer 103, an emitting layer 105 provided on the hole transport layer 104, an electron transport layer 106 provided on the emitting layer 105, an electron injection layer 107 provided on the electron transport layer 106, and a cathode 108 provided on the electron injection layer 107.

[0060] The organic EL element 100 may be fabricated in the reverse order, for example, to have a substrate 101, a cathode 108 provided on the substrate 101, an electron injection layer 107 provided on the cathode 108, an electron transport layer 106 provided on the electron injection layer 107, an emitting layer 105 provided on the electron transport layer 106, a hole transport layer 104 provided on the emitting layer 105, a hole injection layer 103 provided on the hole transport layer 104, and an anode 102 provided on the hole injection layer 103.

[0061] Not all of the above layers are essential, and the minimum structural unit is a structure consisting of an anode 102, an emitting layer 105, and a cathode 108. The hole injection layer 103, the hole transport layer 104, the electron transport layer 106, and the electron injection layer 107 are layers that may be provided optionally. Each of the above layers may consist of a single layer or multiple layers.

[0062] In addition to the above-mentioned "substrate / anode / hole injection layer / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode" configuration, the layers constituting the organic EL element may be configured as "substrate / anode / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode", "substrate / anode / hole injection ...hole transport layer / light-emitting layer / electron injection layer / cathode", "substrate / anode / hole injection layer / hole transport layer / light-emitting layer / electron injection layer / cathode", or "substrate / anode / hole injection layer / hole transport layer / light-emitting layer / electron transport The configuration may be, for example, "substrate / anode / light-emitting layer / electron transport layer / electron injection layer / cathode", "substrate / anode / hole transport layer / light-emitting layer / electron injection layer / cathode", "substrate / anode / hole transport layer / light-emitting layer / electron transport layer / cathode", "substrate / anode / hole transport layer / light-emitting layer / electron injection layer / cathode", "substrate / anode / hole injection layer / light-emitting layer / electron injection layer / cathode", "substrate / anode / hole injection layer / light-emitting layer / electron transport layer / cathode", "substrate / anode / hole injection layer / light-emitting layer / electron transport layer / cathode", "substrate / anode / light-emitting layer / electron transport layer / cathode", or "substrate / anode / light-emitting layer / electron injection layer / cathode".

[0063] 1. Light-emitting layer in organic electroluminescent device The light-emitting layer 105 emits light by recombining holes injected from the anode 102 and electrons injected from the cathode 108 between the electrodes to which an electric field is applied. The material for the light-emitting layer 105 may be a compound (light-emitting compound) that is excited to emit light by the recombination of holes and electrons, and is preferably a compound that can be formed into a stable thin film shape and exhibits strong luminescence (fluorescence) efficiency in a solid state.

[0064] There are two main emission mechanisms for organic EL elements: fluorescence, which uses light emitted from an excited singlet state, and phosphorescence, which uses light emitted from an excited triplet state. General fluorescent materials have a low exciton utilization efficiency of approximately 25%. However, by using a phenomenon in which singlet excitons are generated from multiple triplet excitons (triplet-triplet fusion (TTF)), it is possible to utilize up to 40-62.5% of the energy for emission.

[0065] The generation of singlet excitons from triplet excitons can occur in two ways: on the host material molecules and on the dopant material molecules. In this case, the triplet energy level of the dopant material is preferably higher than that of the host material. When this triplet energy level relationship is satisfied, the triplet excitons generated on the host material do not move to the dopant material having a higher triplet energy. In addition, the triplet excitons generated on the dopant material molecules quickly transfer energy to the host material molecules. That is, the triplet excitons of the host material do not move to the dopant material, but instead collide with each other efficiently on the host material to generate singlet excitons. Furthermore, when the singlet energy level of the dopant material is lower than that of the host material, the singlet excitons generated by the TTF phenomenon transfer energy from the host material to the dopant material, contributing to the fluorescent emission of the dopant material. In addition, the energy transfer from the host to the dopant at this time is a Förster type energy transfer. It is generally known that the greater the overlap integral between the fluorescence spectrum of the host and the absorption spectrum of the dopant, the more efficiently Forster type energy transfer occurs between the host and the dopant.

[0066] By using a host material, which is a benzanthracene compound represented by formula (1) of the present invention, and a dopant material, which is a polycyclic aromatic compound having boron represented by formula (2), it becomes possible to design materials and devices that satisfy the above-mentioned appropriate energy level relationship between the host and dopant, and the condition of a large overlap integral intensity of the spectrum. As a result, the TTF phenomenon can be efficiently generated in the light-emitting layer of the present invention, and good device characteristics can be obtained.

[0067] The light-emitting layer of the organic electroluminescent device 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 a polycyclic aromatic compound having a plurality of structures represented by formula (2) as a dopant material.

[0068] 1-1-1. Benzanthracene compounds The benzanthracene compound contained in the light-emitting layer of the organic EL device of the present invention is a compound represented by the following formula (1).

[0069] [ka]

[0070] In formula (1), X a , X b , Ar 4 , Ar 5 , Ar 6 , Ar 7 , Ar 8 , Ar 9 , Ar 10 , Ar 11 , Ar 12 , and Ar 13are each independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted diarylamino, optionally substituted diheteroarylamino, optionally substituted arylheteroarylamino, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted arylthio, or optionally substituted silyl; X a , X b , Ar 4 , Ar 5 , Ar 6 , Ar 7 , Ar 8 , Ar 9 , Ar 10 , Ar 11 , Ar 12 , and Ar 13 are not all hydrogen at the same time, and at least one hydrogen in the compound represented by formula (1) may be substituted with halogen, cyano, deuterium, or optionally substituted heteroaryl.

[0071] The "aryl" in the "optionally substituted aryl" in formula (1) is, for example, an aryl having 6 to 30 carbon atoms, preferably an aryl having 6 to 16 carbon atoms, more preferably an aryl having 6 to 12 carbon atoms, and particularly preferably an aryl having 6 to 10 carbon atoms.

[0072] Specific examples of "aryl" include a monocyclic ring system such as phenyl, a bicyclic ring system such as biphenylyl, a fused bicyclic ring system such as naphthyl, a tricyclic ring system such as terphenylyl (m-terphenylyl, o-terphenylyl, p-terphenylyl), a fused tricyclic ring system such as anthracenyl, acenaphthylenyl, fluorenyl, phenalenyl, and phenanthrenyl, a fused tetracyclic ring system such as triphenylenyl, pyrenyl, and naphthacenyl, and a fused pentacyclic ring system such as perylenyl and pentacenyl.

[0073] Examples of the "heteroaryl" in the "optionally substituted heteroaryl" in formula (1) include heteroaryl having 2 to 30 carbon atoms, preferably heteroaryl having 2 to 25 carbon atoms, more preferably heteroaryl having 2 to 20 carbon atoms, further preferably heteroaryl having 2 to 15 carbon atoms, and particularly preferably heteroaryl having 2 to 10 carbon atoms. Examples of the heteroaryl include heterocycles containing, as ring-constituting atoms other than carbon, 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen.

[0074] Specific examples of "heteroaryl" 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, cyclohex ... Examples of such aryl groups include aryl, aryloxy, aryloxy, aryloxy, and aryloxy groups. Examples of such aryl groups include aryloxy, aryloxy, aryloxy, and aryloxy groups include aryloxy, aryloxy, and aryloxy groups. Examples of such aryl groups include aryloxy, aryloxy, and aryloxy groups include aryloxy, aryloxy, and aryloxy groups. Examples of such aryl groups include aryloxy, aryloxy, and aryloxy groups include aryloxy, aryloxy, and aryloxy groups.

[0075] The "optionally substituted heteroaryl" also includes groups represented by formula (A) and formula (B) described below.

[0076] The aryl and heteroaryl in each of the "optionally substituted diarylamino", "optionally substituted diheteroarylamino", and "optionally substituted arylheteroarylamino" in formula (1) can be those described above as the "aryl" and "heteroaryl".

[0077] Specific examples include diphenylamino, dinaphthylamino, phenylnaphthylamino, dipyridylamino, phenylpyridylamino, naphthylpyridylamino, and the like.

[0078] The "alkyl" in the "optionally substituted alkyl" in formula (1) may be either linear or branched, and examples thereof include linear alkyl having 1 to 24 carbon atoms or branched alkyl having 3 to 24 carbon atoms. An alkyl having 1 to 18 carbon atoms (branched alkyl having 3 to 18 carbon atoms) is preferred, an alkyl having 1 to 12 carbon atoms (branched alkyl having 3 to 12 carbon atoms) is more preferred, an alkyl having 1 to 6 carbon atoms (branched alkyl having 3 to 6 carbon atoms) is even more preferred, and an alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms) is particularly preferred.

[0079] Specific examples of "alkyl" include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl, 1-methylheptyl, Examples include 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, and n-eicosyl.

[0080] Examples of the "cycloalkyl" in the "optionally substituted cycloalkyl" in formula (1) include cycloalkyl having 3 to 24 carbon atoms, preferably cycloalkyl having 3 to 20 carbon atoms, more preferably cycloalkyl having 3 to 16 carbon atoms, even more preferably cycloalkyl having 3 to 14 carbon atoms, still more preferably cycloalkyl having 5 to 10 carbon atoms, particularly preferably cycloalkyl having 5 to 8 carbon atoms, and most preferably cycloalkyl having 5 to 6 carbon atoms.

[0081] Specific examples of cycloalkyl include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and alkyl (particularly methyl) substituted derivatives of these having 1 to 4 carbon atoms, as well as norbornenyl, bicyclo[1.0.1]butyl, bicyclo[1.1.1]pentyl, bicyclo[2.0.1]pentyl, bicyclo[1.2.1]hexyl, bicyclo[3.0.1]hexyl, bicyclo[2.1.2]heptyl, bicyclo[2.2.2]octyl, adamantyl, diamantyl, decahydronaphthalenyl, and decahydroazulenyl.

[0082] The "alkenyl" in the "optionally substituted alkenyl" in formula (1) includes linear alkenyl having 2 to 24 carbon atoms and branched alkenyl having 4 to 24 carbon atoms. Alkenyl having 2 to 18 carbon atoms is preferred, alkenyl having 2 to 12 carbon atoms is more preferred, alkenyl having 2 to 6 carbon atoms is further preferred, and alkenyl having 2 to 4 carbon atoms is particularly preferred. Specific examples of "alkenyl" include vinyl, allyl, butadienyl, and the like.

[0083] Examples of the "alkoxy" in the "optionally substituted alkoxy" in formula (1) include linear alkoxy having 1 to 24 carbon atoms or branched alkoxy having 3 to 24 carbon atoms. An alkoxy having 1 to 18 carbon atoms (branched alkoxy having 3 to 18 carbon atoms) is preferred, an alkoxy having 1 to 12 carbon atoms (branched alkoxy having 3 to 12 carbon atoms) is more preferred, an alkoxy having 1 to 6 carbon atoms (branched alkoxy having 3 to 6 carbon atoms) is even more preferred, and an alkoxy having 1 to 4 carbon atoms (branched alkoxy having 3 to 4 carbon atoms) is particularly preferred.

[0084] Specific examples of "alkoxy" include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, s-butoxy, t-butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, and the like.

[0085] The "aryloxy" in the "optionally substituted aryloxy" in formula (1) is a group in which the hydrogen of the -OH group is substituted with an aryl, and the explanation of this aryl can be cited from the above-mentioned "aryl".

[0086] The "arylthio" in the "optionally substituted arylthio" in formula (1) is a group in which the hydrogen of the -SH group is replaced by an aryl, and the explanation of this aryl can be cited from the above-mentioned "aryl".

[0087] The "optionally substituted silyl" in formula (1) includes trialkylsilyl. The "trialkylsilyl" includes silyl in which three hydrogen atoms are independently substituted with alkyl, and the explanation of this alkyl can be cited from the above for "alkyl". The alkyl to be substituted is preferably an alkyl having 1 to 4 carbon atoms, and specific examples thereof include methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, t-butyl, and cyclobutyl.

[0088] Specific examples of the "trialkylsilyl" include trimethylsilyl, triethylsilyl, tripropylsilyl, tri-i-propylsilyl, tributylsilyl, tri-sec-butylsilyl, tri-t-butylsilyl, ethyldimethylsilyl, propyldimethylsilyl, i-propyldimethylsilyl, butyldimethylsilyl, s-butyldimethylsilyl, t-butyldimethylsilyl, methyldiethylsilyl, propyldiethylsilyl, i-propyldiethylsilyl, butyldiethylsilyl, s-butyldiethylsilyl, t-butyldiethylsilyl, methyldipropylsilyl, ethyldipropylsilyl, butyldipropylsilyl, s-butyldipropylsilyl, t-butyldipropylsilyl, methyldi-i-propylsilyl, ethyldi-i-propylsilyl, butyldi-i-propylsilyl, s-butyldi-i-propylsilyl, and t-butyldi-i-propylsilyl.

[0089] X in formula (1) a , X b , Ar 4 , Ar 5 , Ar 6 , Ar 7 , Ar 8 , Ar 9 , Ar 10 , Ar 11 , Ar 12 , and Ar 13 When the term "optionally substituted" is used, examples of the substituent include alkyl, aryl, and heteroaryl. As the alkyl, aryl, and heteroaryl, those mentioned above as "alkyl", "aryl", and "heteroaryl" can be cited. The number of the substituents may be any number up to the maximum number of substitutions, and is preferably 0 to 3, more preferably 0 to 2, and even more preferably 0 to 1.

[0090] At least one hydrogen atom in the compound represented by formula (1) may be replaced by a halogen atom, a cyano atom, or a deuterium atom. In this case, "halogen" includes fluorine, chlorine, bromine, and iodine.

[0091] In formula (1), X a , X b , Ar 4 , Ar 5 , Ar 6 , Ar 7 , Ar 8 , Ar 9 , Ar 10 , Ar 11 , Ar 12 , and Ar 13 each independently represents phenyl which may be substituted with one or more substituents selected from substituent group A, biphenylyl which may be substituted with one or more substituents selected from substituent group A, terphenylyl which may be substituted with one or more substituents selected from substituent group A, quaterphenylyl which may be substituted with one or more substituents selected from substituent group A, naphthyl which may be substituted with one or more substituents selected from substituent group A, phenalenyl which may be substituted with one or more substituents selected from substituent group A, phenanthryl which may be substituted with one or more substituents selected from substituent group A, any one or more selected from substituent group A

[0043] In the above, X may be optionally substituted by one or more substituents selected from the substituent group A, benzofluorenyl may be optionally substituted by one or more substituents selected from the substituent group A, chrysenyl may be optionally substituted by one or more substituents selected from the substituent group A, triphenylenyl may be optionally substituted by one or more substituents selected from the substituent group A, pyrenyl may be optionally substituted by one or more substituents selected from the substituent group A, anthracenyl may be optionally substituted by one or more substituents selected from the substituent group A, alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, silyl may be optionally substituted by alkyl having 1 to 4 carbon atoms, or a group represented by the following formula (A) or the following formula (B), in which a and X b Either one of them may be hydrogen.

[0092] Here, the substituent group A consists of phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenalenyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenyl, anthracenyl, 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 phenyl, naphthyl, phenalenyl, phenanthryl, fluorenyl, triphenylenyl, pyrenyl, a group represented by the following formula (A), or a group represented by the following formula (B), and more preferably phenyl, naphthyl, phenanthryl, fluorenyl, a group represented by the following formula (A), or a group represented by the following formula (B).

[0093] X a and X b are each independently preferably phenyl which may be substituted with one or more substituents selected from substituent group A, biphenylyl which may be substituted with one or more substituents selected from substituent group A, terphenylyl which may be substituted with one or more substituents selected from substituent group A, naphthyl which may be substituted with one or more substituents selected from substituent group A, phenalenyl which may be substituted with one or more substituents selected from substituent group A, phenanthryl which may be substituted with one or more substituents selected from substituent group A, fluorenyl which may be substituted with one or more substituents selected from substituent group A, triphenylenyl which may be substituted with one or more substituents selected from substituent group A, pyrenyl which may be substituted with 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), in which a and X b Either one of them may be hydrogen.

[0094] X a and X bare each independently preferably phenyl which may be substituted with one or more substituents selected from substituent group A, biphenylyl, terphenylyl, naphthyl which may be substituted with one or more substituents selected from substituent group A, phenanthryl which may be substituted with one or more substituents selected from substituent group A, fluorenyl, triphenylenyl, pyrenyl which may be substituted with one or more substituents selected from substituent group A, a group represented by formula (A) or a group represented by formula (B) described below.

[0095] As an example, in formula (1), X a and X b is preferably a group represented by formula (A) or (B) described below, or a group having a group represented by formula (A) or (B) as a substituent. As the group having a group represented by formula (A) or (B) as a substituent, an aryl having a group represented by formula (A) or (B) as a substituent is preferred. In this specification, any group selected from the group consisting of a group represented by formula (A) or (B) and a group having a group represented by formula (A) or (B) as a substituent, or a group having a group represented by formula (B) as a substituent, may be referred to as a "group containing a group represented by formula (A) or (B)". In formula (1), X a and X b It is also preferable that one of these is hydrogen and the other is a group containing a group represented by formula (A) or formula (B).

[0096] In formula (1), X a and X b are each preferably independently a group represented by any one of the following formulas (1-X1) to (1-X6).

[0097] [ka]

[0098] In formulas (1-X1) to (1-X6), * indicates a bonding position. In formulas (1-X1) to (1-X6), Ar 21 , Ar 22 , Ar 23 , Ar 24 , Ar 25 , and Ar 26 are each independently hydrogen, phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenyl, anthracenyl, a group represented by formula (A) or a group represented by formula (B) described below. 21 , Ar 22 , Ar 23 , Ar 24 , Ar 25 , and Ar 26 When is a group represented by formula (A) or a group represented by formula (B), it is a preferred example of an aryl having a group represented by formula (A) or formula (B) as a substituent.

[0099] The naphthylene moiety in each of formulas (1-X1) to (1-X3) may be condensed with one benzene ring. Examples of such condensed structures are as follows. In each formula, * indicates the bond position. [ka]

[0100] In the above formula, Ar 21 , Ar 22 The definition is the same as above.

[0101] In formulas (1-X4), (1-X5), and (1-X6), Ar 24 , Ar 25 , and Ar 26are preferably each independently hydrogen, phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, chrysenyl, triphenylenyl, pyrenyl, a group represented by formula (A) or a group represented by formula (B) described below.

[0102] In formula (1), Ar 4 , Ar 5 , Ar 6 , Ar 7 , Ar 8 , Ar 9 , Ar 10 , Ar 11 , Ar 12 , and Ar 13 are each preferably independently hydrogen, phenyl, biphenylyl, terphenylyl, naphthyl, alkyl having 1 to 4 carbon atoms, silyl substituted with cycloalkyl having 5 to 10 carbon atoms, a group represented by formula (A) below or formula (B) below, more preferably hydrogen, phenyl, biphenylyl, naphthyl, a group represented by formula (A) below or formula (B) below, and even more preferably hydrogen, phenyl, naphthyl, or a group represented by formula (A) below.

[0103] X a and X b is a group represented by formula (A) or a group represented by formula (B), or is a group represented by any one of formulas (1-X1) to (1-X6) having a group represented by formula (A) or a group represented by formula (B), 4 , Ar 5 , Ar 6 , Ar 9 , Ar 10 , and Ar 13 are preferably hydrogen. 7 , Ar 8 , Ar 11 , and Ar 12are each independently preferably hydrogen, phenyl, biphenylyl, terphenylyl, naphthyl, alkyl having 1 to 4 carbon atoms, or silyl substituted with cycloalkyl having 5 to 10 carbon atoms, more preferably hydrogen, phenyl, biphenylyl, or naphthyl, and further preferably hydrogen, phenyl, or naphthyl; Ar 7 , Ar 8 , Ar 11 , and Ar 12 Most preferably, each of the groups is hydrogen.

[0104] In another embodiment, Ar 5 , Ar 6 , Ar 7 , Ar 8 , or Ar 9 is preferably a group containing a group represented by formula (A) or formula (B), 6 , Ar 7 , or Ar 8 It is more preferable that any one of the above is a group containing a group represented by formula (A) or formula (B).

[0105] The compound represented by formula (1) is also preferably a compound represented by the following formula (1'). [ka]

[0106] In formula (1'), X a ', X b ', Ar 4 ', Ar 5 ', Ar 6 ', Ar 7 ', Ar 8 ', Ar 9 ', Ar 10 ', Ar 11 ', Ar 12 ', and Ar 13 The definition of ' is X in the above formula (1). a , X b , Ar 4 , Ar 5 , Ar 6 , Ar7 , Ar 8 , Ar 9 , Ar 10 , Ar 11 , Ar 12 , and Ar 13 The compound represented by formula (1') is similar to the compound represented by formula (1), except that the compound represented by formula (1') contains at least one group selected from the group consisting of a group represented by formula (A) and a group represented by formula (B).

[0107] In formula (1'), X a ' and X b Each ' is preferably independently hydrogen, phenyl which may be substituted with one or more substituents selected from substituent group A, biphenylyl which may be substituted with one or more substituents selected from substituent group A, naphthyl which may be substituted with one or more substituents selected from substituent group A, phenanthryl which may be substituted with one or more substituents selected from substituent group A, a group represented by formula (A), or a group represented by the following formula (B).

[0108] In formula (1'), Ar 4 ', Ar 5 ', Ar 6 ', Ar 7 ', Ar 8 ', Ar 9 ', Ar 10 ', Ar 11 ', Ar 12 ', and Ar 13 Each ' is preferably independently hydrogen, phenyl which may be substituted with one or more substituents selected from substituent group A, naphthyl which may be substituted with one or more substituents selected from substituent group A, phenanthryl which may be substituted with 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).

[0109] A preferred example of the compound represented by formula (1) is a compound represented by the following formula (1'a). [ka]

[0110] In formula (1'a), X a ' and X b each ' is independently hydrogen, phenyl which may be substituted with one or more substituents selected from substituent group A, biphenylyl which may be substituted with one or more substituents selected from substituent group A, naphthyl which may be substituted with one or more substituents selected from substituent group A, phenanthryl which may be substituted with one or more substituents selected from substituent group A, a group represented by formula (A) or a group represented by formula (B), and X a ' and X b At least one of ' is a group containing a group represented by formula (A) or formula (B), Ar 7 ', Ar 8 ', Ar 11 ', and Ar 12 ' are each independently hydrogen, methyl, t-butyl, phenyl, biphenylyl, or naphthyl; At least one hydrogen atom in the compound represented by formula (1'a) may be substituted with halogen, cyano, or deuterium.

[0111] In formula (1'a), X is not hydrogen. a ' and X b In the formula (1'a), one or more substituents selected from the group A of substituents which may each be substituted with phenyl, biphenylyl, naphthyl, and phenanthryl are preferably phenyl, biphenylyl, naphthyl, phenanthryl, a group represented by formula (A), or a group represented by formula (B). a ' and X b The above phenyl, biphenylyl, naphthyl, and phenanthryl in the formula (1) are preferably unsubstituted or substituted with phenyl, a group represented by formula (A) or a group represented by formula (B).

[0112] In formula (1'a), Ar7 ', Ar 8 ', Ar 11 ', and Ar 12 It is preferred that each ' is independently hydrogen, phenyl, biphenylyl, or naphthyl.

[0113] As a preferred embodiment of the compound represented by formula (1'a), X a ' and X b Compounds in which either X' is hydrogen are included. a ' and X b Compounds in which either of X′ is hydrogen and Y in the formula (A) and the formula (B) is —O—, and a ' and X b ' is hydrogen, and in formula (A) and formula (B), R other than a bond 21 ~R 38 and R are each preferably hydrogen.

[0114] As another preferred embodiment of the compound represented by formula (1'a), X a ' and X b In this case, it is preferable that Y is -O-. 7 ', Ar 8 ', Ar 11 ', and Ar 12 It is preferable that each of the ' is hydrogen.

[0115] As yet another preferred embodiment of the compound represented by formula (1'a), X a ' and X b Each of the aryls X' is the same aryl selected from phenyl, naphthyl, and phenanthryl, and each of the aryls may be substituted with one or more substituents selected from the substituent group A, and at least one of the aryls has a group represented by formula (A) or a group represented by formula (B) as a substituent. a ' and X b', but all of them have the same aryl as a basic structure, and therefore the synthesis is easy. In this case, the aryl is preferably phenyl, naphthyl (1-naphthyl or 2-naphthyl), or phenanthryl (1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, or 9-phenanthryl). Compounds having a condensed ring group consisting of three or less aromatic rings, such as phenyl, naphthyl, and phenanthryl, are easier to synthesize than compounds having a condensed ring group consisting of four or more aromatic rings, such as pyrene, chrysene, and benzopyrene. As the phenanthryl, 9-phenanthryl is preferable.

[0116] Specifically, it is a compound having a structure represented by the following formula (C), (D), (E), (F), (G), (H), (I), or (J) as a partial structure, provided that no fused ring is formed with the structure represented by formula (C), (D), (E), (F), (G), (H), (I), or (J) as a basic structure, and in the compound having the structure represented by formula (C) as a partial structure, at least one of the two phenyls in formula (C) is unsubstituted.

[0117] [ka]

[0118] More specifically, X a ' and X b is a compound of formula (1'a), wherein: one of them is a phenyl substituted with a group represented by formula (A) or a group represented by formula (B), and the other is an unsubstituted phenyl, one of them is naphthyl (1-naphthyl or 2-naphthyl) substituted with 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 with a group represented by formula (A) or a group represented by formula (B), One of them is phenanthryl (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 phenanthryl (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).

[0119] Another preferred example of the compound represented by formula (1') is a compound represented by formula (1') in which Ar 5 , Ar 6 , Ar 7 , Ar 8 , or Ar 9 In particular, the compound in which any one of the following is a group containing a group represented by formula (A) or formula (B) is included. 6 , Ar 7 , or Ar 8 It is preferable that any one of X is a group containing a group represented by formula (A) or formula (B). It is also preferable that the compound having such a structure further has a structure represented by the above formula (C), (D), (E), (F), (G), (H), or (I) as a partial structure. More specifically, X a ' and X b ' is preferably one of the following: one of them is unsubstituted phenyl and the other is phenyl which may be substituted with one or more substituents selected from Substituent group A, or Each of them is naphthyl (1-naphthyl or 2-naphthyl) which may be substituted with one or more substituents selected from Substituent group A, Any of these is phenanthryl optionally substituted with one or more substituents selected from Substituent group A (1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, or 9-phenanthryl). In the above, X a ' and X b' may be the same or different in terms of the presence or absence and type of one or more substituents selected from Substituent Group A. From the viewpoint of compound synthesis, it is preferable that they are the same, and from the viewpoint of device characteristics, it is preferable that they are different.

[0120] The group represented by the above formula (A) and the group represented by the formula (B) will be described below. [ka]

[0121] In formula (A), Y is -O-, -S- or >NR 39 R 39 is hydrogen or an optionally substituted aryl. 21 ~R 28 are each independently hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, optionally substituted amino, halogen, hydroxy or cyano; R 21 ~R 28Adjacent groups among may be bonded to each other to form a hydrocarbon ring, an aryl ring, or a heteroaryl ring. At least one hydrogen atom in the formed hydrocarbon ring, aryl ring, or heteroaryl ring may be substituted with an optionally substituted alkyl, an optionally substituted cycloalkyl, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkoxy, an optionally substituted aryloxy, an optionally substituted arylthio, a trialkylsilyl, a tricycloalkylsilyl, a dialkylcycloalkylsilyl, an alkyldicycloalkylsilyl, an optionally substituted amino, a halogen, a hydroxyl, or a cyano. The group represented by formula (A) is a group obtained by removing one hydrogen atom from any position of formula (A), and * indicates the position.

[0122] R in formula (A) 21 ~R 28 Among R, the number of groups other than hydrogen is preferably 0 to 2, and more preferably 0 to 1. 21 ~R 28 When adjacent groups among R are bonded to each other to form a hydrocarbon ring, an aryl ring, or a heteroaryl ring, the substituents bonded to the ring and the remaining R 21 ~R 28 The total number of these groups other than hydrogen is preferably 0 to 2, and more preferably 0 to 1.

[0123] In formula (B), Y is -O-, -S- or >NR 39 R 39 is hydrogen or an optionally substituted aryl. 29 ~R 38are each independently hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, optionally substituted amino, halogen, hydroxy or cyano; R 29 ~R 38 Adjacent groups among the above may be bonded to each other to form a hydrocarbon ring, an aryl ring, or a heteroaryl ring. At least one hydrogen atom in the formed hydrocarbon ring, aryl ring, or heteroaryl ring may be substituted with an optionally substituted alkyl, an optionally substituted cycloalkyl, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkoxy, an optionally substituted aryloxy, an optionally substituted arylthio, a trialkylsilyl, a tricycloalkylsilyl, a dialkylcycloalkylsilyl, an alkyldicycloalkylsilyl, an optionally substituted amino, a halogen, a hydroxyl, or a cyano. The group represented by formula (B) is a group obtained by removing one hydrogen atom from any position of formula (B), and * indicates the position.

[0124] R in formula (B) 29 ~R 38 Among R, the number of groups other than hydrogen is preferably 0 to 2, more preferably 0 to 1, and even more preferably 0. 29 ~R 38 When adjacent groups among R are bonded to each other to form a hydrocarbon ring, an aryl ring, or a heteroaryl ring, the substituents bonded to the ring and the remaining R 29 ~R 38 The total number of these groups other than hydrogen is preferably 0 to 2, more preferably 0 to 1, and even more preferably 0.

[0125] R in formula (A) and formula (B) 21 ~R 38The "alkyl" in the "optionally substituted alkyl" may be either linear or branched, and examples thereof include linear alkyl having 1 to 24 carbon atoms or branched alkyl having 3 to 24 carbon atoms. An alkyl having 1 to 18 carbon atoms (branched alkyl having 3 to 18 carbon atoms) is preferred, an alkyl having 1 to 12 carbon atoms (branched alkyl having 3 to 12 carbon atoms) is more preferred, an alkyl having 1 to 6 carbon atoms (branched alkyl having 3 to 6 carbon atoms) is even more preferred, and an alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms) is particularly preferred.

[0126] Specific examples of "alkyl" include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl, 1-methylheptyl, Examples include 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, and n-eicosyl.

[0127] R in formula (A) and formula (B) 21 ~R 38 In the above, the "aryl" in the "optionally substituted aryl" includes, for example, aryl having 6 to 30 carbon atoms, preferably aryl having 6 to 16 carbon atoms, more preferably aryl having 6 to 12 carbon atoms, and particularly preferably aryl having 6 to 10 carbon atoms.

[0128] Specific examples of "aryl" include a monocyclic ring system such as phenyl, a bicyclic ring system such as biphenylyl, a fused bicyclic ring system such as naphthyl, a tricyclic ring system such as terphenylyl (m-terphenylyl, o-terphenylyl, p-terphenylyl), a fused tricyclic ring system such as acenaphthylenyl, fluorenyl, phenalenyl, and phenanthrenyl, a fused tetracyclic ring system such as triphenylenyl, pyrenyl, and naphthacenyl, and a fused pentacyclic ring system such as perylenyl and pentacenyl.

[0129] R in formula (A) and formula (B) 21 ~R 38 Examples of the "heteroaryl" in the "optionally substituted heteroaryl" include heteroaryl having 2 to 30 carbon atoms, preferably heteroaryl having 2 to 25 carbon atoms, more preferably heteroaryl having 2 to 20 carbon atoms, further preferably heteroaryl having 2 to 15 carbon atoms, and particularly preferably heteroaryl having 2 to 10 carbon atoms. Examples of the heteroaryl include heterocycles containing, as ring-constituting atoms other than carbon, 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen.

[0130] Specific examples of "heteroaryl" 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, isoxyl, and aryl. Examples include noryl, cinnolyl, quinazolyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxathiinyl, phenoxazinyl, phenothiazinyl, phenazinyl, indolizinyl, furyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thienyl, benzo[b]thienyl, dibenzothienyl, furazanyl, thianthrenyl, naphthobenzofuranyl, and naphthobenzothienyl.

[0131] R in formula (A) and formula (B) 21 ~R 38 Examples of the "alkoxy" in the "optionally substituted alkoxy" include linear alkoxy having 1 to 24 carbon atoms or branched alkoxy having 3 to 24 carbon atoms. An alkoxy having 1 to 18 carbon atoms (branched alkoxy having 3 to 18 carbon atoms) is preferred, an alkoxy having 1 to 12 carbon atoms (branched alkoxy having 3 to 12 carbon atoms) is more preferred, an alkoxy having 1 to 6 carbon atoms (branched alkoxy having 3 to 6 carbon atoms) is even more preferred, and an alkoxy having 1 to 4 carbon atoms (branched alkoxy having 3 to 4 carbon atoms) is particularly preferred.

[0132] Specific examples of "alkoxy" include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, s-butoxy, t-butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, and the like.

[0133] R in formula (A) and formula (B) 21 ~R 38 The "aryloxy" in the "optionally substituted aryloxy" is a group in which the hydrogen of the -OH group is replaced by an aryl, and this aryl is one of the above-mentioned R 21 ~R 38 The group described as "aryl" in the above formula can be used.

[0134] R in formula (A) and formula (B) 21 ~R 38 The "arylthio" in the "optionally substituted arylthio" is a group in which the hydrogen of the -SH group is replaced by an aryl, and this aryl is the same as R 21 ~R 38 The group described as "aryl" in the above formula can be used.

[0135] R in formula (A) and formula (B) 21 ~R 38 The "trialkylsilyl" in the above formula is a silyl group in which each of the three hydrogen atoms is independently replaced by an alkyl group, and the alkyl group is the same as the above-mentioned R 21~R 38 The groups described as "alkyl" in the above can be cited. Preferred alkyl groups for substitution are alkyl groups having 1 to 4 carbon atoms, and specific examples thereof include methyl, ethyl, propyl, i-propyl, n-butyl, s-butyl, t-butyl, cyclobutyl, and the like.

[0136] Specific examples of the "trialkylsilyl" include trimethylsilyl, triethylsilyl, tripropylsilyl, tri-i-propylsilyl, tributylsilyl, tri-s-butylsilyl, tri-t-butylsilyl, ethyldimethylsilyl, propyldimethylsilyl, i-propyldimethylsilyl, butyldimethylsilyl, s-butyldimethylsilyl, t-butyldimethylsilyl, methyldiethylsilyl, propyldiethylsilyl, i-propyldiethylsilyl, butyldiethylsilyl, s-butyldiethylsilyl, t-butyldiethylsilyl, methyldipropylsilyl, ethyldipropylsilyl, butyldipropylsilyl, s-butyldipropylsilyl, t-butyldipropylsilyl, methyldi-i-propylsilyl, ethyldi-i-propylsilyl, butyldi-i-propylsilyl, s-butyldi-i-propylsilyl, and t-butyldi-i-propylsilyl.

[0137] R in formula (A) and formula (B) 21 ~R 38 The "substituted amino" in the "optionally substituted amino" in the above is, for example, an amino in which two hydrogen atoms are substituted with aryl or heteroaryl. An amino in which two hydrogen atoms are substituted with aryl is a diaryl-substituted amino, an amino in which two hydrogen atoms are substituted with heteroaryl is a diheteroaryl-substituted amino, and an amino in which two hydrogen atoms are substituted with an aryl and a heteroaryl is an arylheteroaryl-substituted amino. The aryl and heteroaryl are as defined above in R 21 ~R 38 The groups described above as "aryl" and "heteroaryl" can be cited.

[0138] Specific examples of the "substituted amino" include diphenylamino, dinaphthylamino, phenylnaphthylamino, dipyridylamino, phenylpyridylamino, naphthylpyridylamino, and the like.

[0139] R in formula (A) and formula (B) 21 ~R 38 "Halogen" in the above formula includes fluorine, chlorine, bromine, and iodine.

[0140] R in formula (A) and formula (B) 21 ~R 38 Some of the groups described as may be substituted as described above, and in this case, the substituents include alkyl, aryl, or heteroaryl. The alkyl, aryl, or heteroaryl may be any of the groups described above as R 21 ~R 38 The groups described above as "alkyl", "aryl" or "heteroaryl" can be referenced.

[0141] ">NR" as Y in formula (A) and formula (B) 39 " R in 39 is hydrogen or an optionally substituted aryl, and the aryl is as defined above in R 21 ~R 38 The group described as "aryl" in the above formula can be cited, and the substituents thereof include R 21 ~R 38 The groups described above as substituents for the above can be cited.

[0142] R in formula (A) and formula (B) 21 ~R 38Among these, adjacent groups may be bonded to each other to form a hydrocarbon ring, an aryl ring, or a heteroaryl ring. For example, the group represented by the following formula (A-1) does not form a ring in formula (A), and examples of the group represented by the following formulas (A-2) to (A-14) include groups represented by the following formulas. At least one hydrogen atom in the group represented by any one of formulas (A-1) to (A-14) or formula (B-1) may be substituted with alkyl, aryl, heteroaryl, alkoxy, aryloxy, arylthio, trialkylsilyl, diaryl-substituted amino, diheteroaryl-substituted amino, arylheteroaryl-substituted amino, halogen, hydroxy, or cyano, and these are the same as those in the above-mentioned R. 21 ~R 38 The groups described above as each group in the above formula can be cited.

[0143] Examples of rings formed by bonding adjacent groups to each other include a hydrocarbon ring such as a cyclohexane ring, and an aryl or heteroaryl ring such as the above-mentioned R 21 ~R 28 Examples of the ring structures include those described in the "aryl" and "heteroaryl" in the formula (A-1), and these rings are formed so as to be condensed with one or two benzene rings in the formula (A-1).

[0144] Examples of the group represented by formula (A) include groups represented by any one selected from the group consisting of the following formulas (A-1) to (A-14), and examples of the group represented by formula (B) include groups represented by formula (B-1). Groups represented by any one selected from the group consisting of formulas (A-1) to (A-4) and (B-1) are preferred, groups represented by any one of formulas (A-1), (A-3) and (A-4) are more preferred, and groups represented by formula (A-1) are even more preferred.

[0145] [ka]

[0146] The group represented by formula (A) and the group represented by formula (B) are groups obtained by removing one hydrogen atom at any position of formula (A) and formula (B), respectively, and * indicates the position. In other words, the group represented by formula (A) and the group represented by formula (B) may have any position as a bonding position. Among them, any carbon atom on the two benzene rings in the structures of formula (A) and formula (B), R in the structures of formula (A) and formula (B), 21 ~R 38 or ">NR 39 " is preferably a group that is directly bonded to the N in (has a bond thereto).

[0147] It is preferable that Y in formula (A) and formula (B) and Y in each of formulas (A-1) to (A-14) and formula (B-1) is -O-.

[0148] Examples of the group represented by formula (A) and the group represented by formula (B) include groups represented by the following formulae: In the formulae, Y and * are defined as above, and Y is preferably -O-. [ka]

[0149] Specific examples of the compound represented by formula (1) include compounds represented by the following formulas. In the following formulas, "Me" represents methyl and "tBu" represents tertiary butyl. In each formula, Y represents -O-, -S- or >NR 39 (R 39 is the same as above), and R 39 is, for example, phenyl or deuterium-substituted phenyl. For formula numbers, for example, when Y is -O-, formula (1-331-Y) becomes formula (1-331-O), and Y is -S- or >NR 39 In the case of (1-331-S) or (1-331-N), respectively, Y is -O- or >NR 39Examples of the formula are preferably -O-, and particularly preferably -O-.

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[0263] Among the above compounds, the compounds represented by the formula (1-7), (1-45), (1-242), (1-90), (1-78), (1-93), (1-158), (1-161), (1-170), (1-8), (1-48), (1-185), (1-203), (1-129), (1-244), and (1 -753-O), formula (1-551-O), formula (1-381-O), formula (1-717-O), formula (1-755-O), formula (1-778-O), formula (1-752) -O), formula (1-785-O), 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 (1-153 8-N), (1-1001-O), (1-1716-O), (1-1184-O), (1-1140-O), (1-1347-O), (1-1783-O), (1-1759-O), (1-1767-O), (1-1777-O) or (1-1781-O) are preferred.

[0264] 1-1-2. Method for producing benzanthracene compounds The benzanthracene compound represented by formula (1) can be produced by a method similar 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) by these methods are as follows. In the following formula, Ar and Ar' represent, for example, aryl and heteroaryl.

[0265] [ka]

[0266] Furthermore, the benzanthracene compound represented by formula (1) can also be produced by the reaction route shown below: In the following formula, Ar and Ar' represent, for example, aryl or heteroaryl.

[0267] [ka]

[0268] 1-2-1. Polycyclic aromatic compounds represented by formula (2) and their multimers The organic EL device of the present invention contains, as a dopant material in the light-emitting layer, a polycyclic aromatic compound represented by the following formula (2) and a multimer of a polycyclic aromatic compound having a plurality of structures represented by formula (2). 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 multimer of a polycyclic aromatic compound having a plurality of structures represented by the following formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e), or formula (2-f).

[0269] [ka]

[0270] In each structural formula, "A" to "C" and "a" to "c" are symbols indicating a ring, a benzene ring, or a ring structure represented by a five-membered ring, and the other symbols are the same as defined above.

[0271] In formula (2), ring A, ring B and ring C are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen atom in these rings may be substituted with a substituent. At least one of ring A, ring B and ring C is preferably an aryl ring having at least one substituent or a heteroaryl ring having at least one substituent, more preferably ring A, ring B and ring C are each an aryl ring having at least one substituent or a heteroaryl ring having at least one substituent, and even more preferably ring A, ring B and ring C are each an aryl ring having one substituent or a heteroaryl ring having one substituent.

[0272] In this case, the substituent is preferably substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino (amino having aryl and heteroaryl), substituted or unsubstituted diarylboryl (two aryls may be bonded via a single bond or a linking group), substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy or substituted silyl. When these groups have a substituent, the substituent is preferably aryl, heteroaryl, alkyl, cycloalkyl, diarylamino, or substituted silyl.

[0273] In particular, the substituent is preferably a substituted or unsubstituted alkyl (particularly, neopentyl) or a cycloalkyl such as adamantyl. Also, a tertiary alkyl (tR) is preferred. This is because such a bulky substituent prevents inactivation due to aggregation of molecules, and improves the luminescence quantum yield (PLQY). Also, a substituted or unsubstituted diarylamino is preferred.

[0274] The tertiary alkyl is represented by the following formula (tR): [ka]

[0275] In the formula (tR), R a , R b , and R c are each independently an alkyl group having 1 to 24 carbon atoms, and any -CH 2 - may be replaced by -O-, and the group represented by formula (tR) replaces at least one hydrogen in the compound or structure represented by formula (2) at *.

[0276] R a , R b , and R c The "alkyl having 1 to 24 carbon atoms" may be either linear or branched, and examples thereof include linear alkyl having 1 to 24 carbon atoms or branched alkyl having 3 to 24 carbon atoms, alkyl having 1 to 18 carbon atoms (branched alkyl having 3 to 18 carbon atoms), alkyl having 1 to 12 carbon atoms (branched alkyl having 3 to 12 carbon atoms), alkyl having 1 to 6 carbon atoms (branched alkyl having 3 to 6 carbon atoms), and alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms).

[0277] R in formula (tR) of formula (2) a , R b , and R c The total number of carbon atoms is preferably 3 to 20, and particularly preferably 3 to 10.

[0278] R a , R b , and R cSpecific examples of alkyl include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl, 1-methylheptyl, 2 Examples of the aryl group include n-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, and n-eicosyl.

[0279] Examples of the group represented by the formula (tR) include t-butyl, t-amyl, 1-ethyl-1-methylpropyl, 1,1-diethylpropyl, 1,1-dimethylbutyl, 1-ethyl-1-methylbutyl, 1,1,3,3-tetramethylbutyl, 1,1,4-trimethylpentyl, 1,1,2-trimethylpropyl, 1,1-dimethyloctyl, 1,1-dimethylpentyl, 1,1-dimethylheptyl, 1,1,5-trimethylhexyl, 1-ethyl- Examples include 1-methylhexyl, 1-ethyl-1,3-dimethylbutyl, 1,1,2,2-tetramethylpropyl, 1-butyl-1-methylpentyl, 1,1-diethylbutyl, 1-ethyl-1-methylpentyl, 1,1,3-trimethylbutyl, 1-propyl-1-methylpentyl, 1,1,2-trimethylpropyl, 1-ethyl-1,2,2-trimethylpropyl, 1-propyl-1-methylbutyl, 1,1-dimethylhexyl, etc. Among these, t-butyl and t-amyl are preferred.

[0280] Other preferred examples of the substituents in ring A, ring B, and ring C include, for example, diarylamino substituted with a group of formula (tR), carbazolyl substituted with a group of formula (tR), or benzocarbazolyl substituted with a group of formula (tR). For "diarylamino", the group described below as the "first substituent" is included. Examples of the substitution form of the group of formula (tR) on diarylamino, carbazolyl, and benzocarbazolyl include examples in which some or all of the hydrogen atoms on the aryl ring or benzene ring in these groups are substituted with the group of formula (tR).

[0281] The aryl or heteroaryl rings in the A, B and C rings are each defined as "B", "X", 1 " and "X 2 It is preferable that the formula (2) has a 5- or 6-membered ring sharing a bond with the central fused two-ring structure.

[0282] Here, the "fused two-ring structure" refers to the "B" and "X" shown in the center of formula (2). 1 " and "X 2 " means a structure in which two saturated hydrocarbon rings are fused together. In addition, "a six-membered ring sharing a bond with the fused two-ring structure" means, for example, an a-ring (a benzene ring (six-membered ring)) fused to the fused two-ring structure as shown in formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e), and formula (2-f). In addition, "an aryl ring or heteroaryl ring (A-ring) has this six-membered ring" means that the A-ring is formed only from this six-membered ring, or that the A-ring is formed by further condensing other rings to this six-membered ring so as to include this six-membered ring. In other words, "an aryl ring or heteroaryl ring (A-ring) having a six-membered ring" means that the six-membered ring constituting all or a part of the A-ring is fused to the fused two-ring structure. The same explanation applies to "a five-membered ring". In addition, the same explanation applies to "a B-ring (b-ring)" and "a C-ring (c-ring)".

[0283] The A ring in formula (2) is the same as the a ring and its substituent R in formulas (2-a), (2-b), (2-c), (2-d), (2-e), and (2-f). 1 ~R 3 The ring B in formula (2) corresponds to the ring b and its substituent R in formulas (2-a), (2-b), and (2-c). 8 ~R 11 , the ring b in formula (2-d) and its substituent R 10 and R 11 and the ring b and its substituent R in the formula (2-e) and the formula (2-f). 8 and R 9 The ring C in formula (2) corresponds to the ring c and its substituent R in formula (2-a). 4 ~R 7 , the ring c and its substituent R in formula (2-b), formula (2-d), and formula (2-f) 4 and R 5 and the ring c and its substituent R in formula (2-c) and formula (2-e) 6 and R 7 That is, formula (2-a) corresponds to a structure in which rings having at least a 6-membered ring structure are selected as rings A to C of formula (2), and formulas (2-b), (2-c), (2-d), (2-e), and (2-f) correspond to structures in which rings having at least a 6-membered ring structure and rings having at least a 5-membered ring structure are selected as rings A to C of formula (2), respectively. In this sense, each ring in formula (2-a) etc. is represented by lowercase letters a to c.

[0284] X in formula (2-b), formula (2-c), formula (2-d), formula (2-e), and formula (2-f) X are each independently >O, >S, >NR, or >C(-R) 2 Here, R in the >NR is an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl, or an optionally substituted cycloalkyl, preferably an optionally substituted aryl, and more preferably an unsubstituted aryl. 2R is each independently hydrogen, aryl which may be substituted with alkyl or cycloalkyl, heteroaryl which may be substituted with alkyl or cycloalkyl, alkyl, or cycloalkyl, preferably alkyl, and more preferably methyl. >C(-R) 2 In the above formula, it is preferable that the two R's are the same. 2 It is also preferable that the two R's in X form a ring together. X are each independently preferably >O, >S, or >NR, more preferably >O or >S, and even more preferably >S.

[0285] In formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e), and formula (2-f), R 1 ~R 11 are each independently a hydrogen atom, an aryl, a heteroaryl, a diarylamino, a diheteroarylamino, an arylheteroarylamino, a diarylboryl (two aryls may be bonded via a single bond or a linking group), an alkyl, a cycloalkyl, an alkoxy, an aryloxy, or a substituted silyl, in which at least one hydrogen atom may be substituted with an aryl, a heteroaryl, an alkyl, a cycloalkyl, or a substituted silyl.

[0286] R in each of formulas (2-a), (2-b), (2-c), (2-d), (2-e), and (2-f) 1 ~R 3 In R, 0 to 1 are substituents other than hydrogen and the rest are hydrogen. 4 ~R 7 In R, 0 to 1 are substituents other than hydrogen and the rest are hydrogen. 8 ~R 11 Among them, it is preferred that 0 to 1 of them are a substituent other than hydrogen and the rest are hydrogen. R 1 ~R 3 Among them, one is a substituent other than hydrogen and the others are hydrogen; R 4 ~R7 Among them, one is a substituent other than hydrogen and the others are hydrogen; R 8 ~R 11 Among them, it is more preferable that one of them is a substituent other than hydrogen and the others are hydrogen. For the preferable range of the substituent other than hydrogen, the description of the substituent described below as the first substituent (which may have a second substituent) can be referred to. As the substituent other than hydrogen, it is particularly preferable that it is alkyl (particularly the above tertiary alkyl (tR), neopentyl, etc.), cycloalkyl (for example, adamantyl, etc.), or substituted or unsubstituted diarylamino.

[0287] In the formulae (2-a), (2-b), (2-c), (2-d), (2-e), and (2-f), the substituents R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 Adjacent groups among these may be bonded to each other to form an aryl ring or a heteroaryl ring together with the a ring, the b ring or the c ring, and at least one hydrogen atom in the formed ring may be substituted with an aryl, a heteroaryl, a diarylamino, a diheteroarylamino, an arylheteroarylamino, a diarylboryl (two aryls may be bonded via a single bond or a linking group), an alkyl, a cycloalkyl, an alkoxy, an aryloxy or a substituted silyl, and at least one hydrogen atom in these may be substituted with an aryl, a heteroaryl, an alkyl, a cycloalkyl or a substituted silyl.

[0288] For example, in the compound represented by formula (2-a), the ring structure constituting the compound changes depending on the mutual bonding form of the substituents in ring a, ring b, and ring c, as shown in the following formulas (2-a-1) and (2-a-2). Ring A', ring B', and ring C' in each formula correspond to ring A, ring B, and ring C in formula (2), respectively. In addition, R in each formula 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , a, b, c, X 1 and X 2 is the same as in formula (2-a).

[0289] [ka]

[0290] The A' ring, B' ring, and C' ring in the formula (2-a-1) and the formula (2-a-2) are each independently a substituent R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , and R 11 Adjacent groups among these are bonded to each other to form an aryl or heteroaryl ring together with the ring a, ring b, and ring c, respectively (they may also be considered as fused rings formed by fusing other ring structures to the ring a, ring b, or ring c). Although not shown in the formula, there are also compounds in which the ring a, ring b, and ring c are all changed to ring A', ring B', and ring C'. As can be seen from formula (2-a-1) and formula (2-a-2), for example, R in ring b 8 and R in c-ring 7 , R in ring b 11 and a-ring R 1 , R in ring c 4and a-ring R 3 etc. are not considered to be "adjacent groups" and are not bonded to each other. In other words, "adjacent groups" refers to groups adjacent to each other on the same ring.

[0291] The compounds represented by formula (2-a-1) and formula (2-a-2) correspond to, for example, the compounds represented by formulas (2-67) to (2-74), (2-76) to (2-83), (2-273) to (2-276), (2-290) to (2-295), and (2-350) to (2-355), which are listed below as specific compounds. That is, for example, it is a compound having ring A' (or ring B' or ring C') formed by condensing 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 to a benzene ring which is ring a (or ring b or ring c), and the condensed ring A' (or condensed ring B' or condensed ring C') thus formed is a naphthalene ring, a carbazole ring, an indole ring, a benzofuran ring, a benzothiophene ring, a dibenzofuran ring, a dibenzothiophene ring, a tetralin ring, or a fluorene ring, respectively.

[0292] Similarly, in formula (2-b), formula (2-c), formula (2-d), formula (2-e), and formula (2-f), a fused ring may be formed by condensing another ring structure to ring a, ring b, or ring c. For example, the benzene ring of ring a or ring b may be condensed to another ring structure to form a fused ring, similar to the benzene ring in formula (2-a). In the formulae (2-b), (2-c), (2-d), (2-e), and (2-f), R 4 ~R 11 It is particularly preferred that adjacent groups among the above are bonded to each other to form a ring to form a condensed ring. For example, in the ring c of formula (2-b) and formula (2-c), and the rings b and c of formula (2-d), formula (2-e), and formula (2-f), R 3 ~R 11Adjacent groups among these can be bonded to each other to form a ring, thereby forming a fused ring, ring B' or ring C'. Examples of the fused ring when the ring formed is a benzene ring include an indole ring, a benzofuran ring, and a benzothiophene ring.

[0293] As an example, in the five-membered ring which is the ring c in formula (2-b), R 4 and R 5 The following is an example of a fused ring formed by bonding together to form a benzene ring. [ka]

[0294] In formula (2-b-1), R 1 , R 2 , R 3 , R 8 , R 9 , R 10 , R 11 , X X , X 1 and X 2 R has the same meaning as in formula (2-b), and the preferred ranges are also the same. 4b , R 5b , R 6b , R 7b is hydrogen or a substituent selected from the group consisting of aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, and substituted silyl, and at least one hydrogen in these substituents may be replaced with aryl, heteroaryl, alkyl, cycloalkyl, or substituted silyl. R 4b , R 5b , R 6b , R 7bAmong them, it is preferable that 0 to 2 are substituents other than hydrogen and the rest are hydrogen, and it is more preferable that one is a substituent other than hydrogen and the rest are hydrogen. For the preferable range of the substituent other than hydrogen, the description of the substituent described below as the first substituent (which may have a second substituent) can be referred to. As the substituent other than hydrogen, it is particularly preferable that it is alkyl (particularly the above tertiary alkyl (tR), neopentyl, etc.), cycloalkyl (for example, adamantyl, etc.), or substituted or unsubstituted diarylamino.

[0295] For example, in formulas (2-b), (2-c), (2-d), (2-e), and (2-f), X X When is >O, ring b and / or ring c are furan rings, and the rings corresponding to ring B' and / or ring C' in formula (2-a-1) formed by condensing a benzene ring to this furan ring are benzofuran rings. In addition, for example, in formula (2-b), formula (2-c), formula (2-d), formula (2-e), and formula (2-f), X X When is >S, ring b and / or ring c are thiophene rings, and the rings corresponding to ring B' and / or ring C' in formula (2-a-1) formed by condensing a benzene ring to this thiophene ring are benzothiophene rings. Examples of such a structure include compounds represented by any of formulas (2-572) to (1-588) described below.

[0296] X in formula (2) 1 and X 2 are independently >O, >NR, >C(-R) 2 , >S, or >Se, and R of the >NR is an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted alkyl, or an optionally substituted cycloalkyl, and the >C(-R) 2 R is hydrogen, optionally substituted aryl, optionally substituted alkyl, or optionally substituted cycloalkyl, and R in >NR and / or >C(-R)2 R may be bonded to the ring B and / or ring C via a linking group or a single bond, and the linking group is -O-, -S-, or -C(-R) 2 In addition, the above-mentioned "-C(-R) 2 R in "-" is hydrogen, alkyl, or cycloalkyl. This explanation applies to X in formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e), and formula (2-f). 1 and X 2 But it's the same.

[0297] In the formula (2) and the formulas (2-a), (2-b), (2-c), (2-d), (2-e), and (2-f), X 1 and X 2 are preferably each independently >O or >NR, more preferably >NR where R is an optionally substituted phenyl, even more preferably >NR where at least one R is a phenyl substituted with one or two t-butyl, t-amyl, methyl or phenyl, and particularly preferably >NR where at least one R is a phenyl substituted with one t-butyl or t-amyl. 1 and X 2 may be the same group or different groups.

[0298] Here, in formula (2), “R of >NR and / or >C(-R) 2 is bonded to ring A, ring B, and / or ring C by a linking group or a single bond" is defined as "R of >NR and / or >C(-R) in formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e), and formula (2-f) 2 R is -O-, -S-, -C(-R) 2 - or bonded to ring a, ring b, and / or ring c by a single bond."

[0299] This provision is expressed by the following formula (2-a-3-1), X 1 Or X 2can be expressed as a compound having a ring structure in which X is incorporated into the fused ring B' and the fused ring C'. That is, for example, the compound having X in the benzene ring which is the b ring (or the c ring) in the formula (2-a) 1 (or X 2 The compound has a ring B' (or ring C') formed by condensing another ring so as to incorporate the ring A. The condensed ring B' (or condensed ring C') formed is, for example, a carbazole ring, a phenoxazine ring, a phenothiazine ring, or an acridine ring.

[0300] In addition, the above provision is based on the following formula (2-a-3-2) or formula (2-a-3-3), X 1 and / or X 2 In other words, for example, the a-ring in formula (2-a) is a benzene ring, and X 1 (and / or X 2 The compound has a ring A' formed by condensing another ring so as to incorporate the ring A'. The condensed ring A' formed is, for example, a carbazole ring, a phenoxazine ring, a phenothiazine ring, or an acridine ring.

[0301] [ka]

[0302] The "aryl ring" which is the ring A, ring B, and ring C in formula (2) is, for example, an aryl ring having 6 to 30 carbon atoms, preferably an aryl ring having 6 to 16 carbon atoms, more preferably an aryl ring having 6 to 12 carbon atoms, and particularly preferably an aryl ring having 6 to 10 carbon atoms. The "aryl ring" is defined as "R 1 ~R 11 In addition, since ring a (or ring b or ring c) is already composed of a benzene ring having six carbon atoms, the lower limit of the carbon number is the total carbon number of the fused rings formed by condensing a 5-membered ring to this, which is nine.

[0303] Specific examples of the "aryl ring" include a monocyclic benzene ring, a bicyclic bicyclic bicyclic naphthalene ring and a tetralin ring, a tricyclic terphenyl ring (m-terphenyl, o-terphenyl, p-terphenyl), a fused tricyclic acenaphthylene ring, a fluorene ring, a phenalene ring, and a phenanthrene ring, a fused tetracyclic tricyclic triphenylene ring, a pyrene ring, and a naphthacene ring, and a fused pentacyclic perylene ring and a pentacene ring.

[0304] Examples of the "heteroaryl ring" which is the ring A, ring B and ring C in 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, further 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 heterocycles containing, in addition to carbon, 1 to 5 heteroatoms selected from oxygen, sulfur and nitrogen as ring-constituting atoms. The "heteroaryl ring" is defined as "R" as defined in formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e) and formula (2-f). 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , and R 11 In addition, since ring a (or ring b or ring c) is already composed of a benzene ring having 6 carbon atoms, the lower limit of the carbon number is the total carbon number of the fused rings fused to this 5-membered ring, which is 6.

[0305] 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, Examples of the ring include an aryl ring, a quinoline ring, an isoquinoline ring, a cinnoline ring, a quinazoline ring, a quinoxaline ring, a phthalazine ring, a naphthyridine ring, a purine ring, a pteridine ring, a carbazole ring, an acridine ring, a phenoxathiin ring, a phenoxazine ring, a phenothiazine ring, a phenazine ring, an indolizine ring, a furan ring, a benzofuran ring, an isobenzofuran ring, a dibenzofuran ring, a thiophene ring, a benzothiophene ring, a dibenzothiophene ring, a furazan ring, an oxadiazole ring, and a thianthrene ring.

[0306] At least one hydrogen atom in the above-mentioned "aryl ring" or "heteroaryl ring" may be substituted with a first substituent, which is a substituted or unsubstituted "aryl", a substituted or unsubstituted "heteroaryl", a substituted or unsubstituted "diarylamino", a substituted or unsubstituted "diheteroarylamino", a substituted or unsubstituted "arylheteroarylamino", a substituted or unsubstituted "diarylboryl (two aryls may be bonded via a single bond or a linking group)", a substituted or unsubstituted "alkyl", a substituted or unsubstituted "cycloalkyl", a substituted or unsubstituted "alkoxy", or a substituted or unsubstituted "aryloxy". Examples of the first substituent, the "aryl" or "heteroaryl" in the "diarylamino", the heteroaryl in the "diheteroarylamino", the aryl and heteroaryl in the "arylheteroarylamino", the aryl in the "diarylboryl", and the aryl in the "aryloxy" include the monovalent groups of the above-mentioned "aryl ring" or "heteroaryl ring".

[0307] The "alkyl" as the first substituent may be either linear or branched, and examples thereof include linear alkyl having 1 to 24 carbon atoms or branched alkyl having 3 to 24 carbon atoms. An alkyl having 1 to 18 carbon atoms (branched alkyl having 3 to 18 carbon atoms) is preferred, an alkyl having 1 to 12 carbon atoms (branched alkyl having 3 to 12 carbon atoms) is more preferred, an alkyl having 1 to 6 carbon atoms (branched alkyl having 3 to 6 carbon atoms) is even more preferred, and an alkyl having 1 to 5 carbon atoms (branched alkyl having 3 to 5 carbon atoms) is particularly preferred.

[0308] Specific examples of alkyl include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl (t-amyl), n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl, and 1-methylheptyl. Examples of the aryl group include aryl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, and n-eicosyl.

[0309] Furthermore, examples of the "cycloalkyl" as the first substituent include cycloalkyl having 3 to 24 carbon atoms, preferably cycloalkyl having 3 to 20 carbon atoms, more preferably cycloalkyl having 3 to 16 carbon atoms, even more preferably cycloalkyl having 3 to 14 carbon atoms, still more preferably cycloalkyl having 5 to 10 carbon atoms, particularly preferably cycloalkyl having 5 to 8 carbon atoms, and most preferably cycloalkyl having 5 to 6 carbon atoms.

[0310] Specific examples of cycloalkyl include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and alkyl (particularly methyl) substituted derivatives of these having 1 to 4 carbon atoms, as well as norbornenyl, bicyclo[1.0.1]butyl, bicyclo[1.1.1]pentyl, bicyclo[2.0.1]pentyl, bicyclo[1.2.1]hexyl, bicyclo[3.0.1]hexyl, bicyclo[2.1.2]heptyl, bicyclo[2.2.2]octyl, adamantyl, diamantyl, decahydronaphthalenyl, and decahydroazulenyl.

[0311] Furthermore, examples of the "alkoxy" as the first substituent include linear alkoxy having 1 to 24 carbon atoms or branched alkoxy having 3 to 24 carbon atoms. An alkoxy having 1 to 18 carbon atoms (branched alkoxy having 3 to 18 carbon atoms) is preferred, an alkoxy having 1 to 12 carbon atoms (branched alkoxy having 3 to 12 carbon atoms) is more preferred, an alkoxy having 1 to 6 carbon atoms (branched alkoxy having 3 to 6 carbon atoms) is even more preferred, and an alkoxy having 1 to 4 carbon atoms (branched alkoxy having 3 to 4 carbon atoms) is particularly preferred.

[0312] Specific alkoxy includes methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, s-butoxy, t-butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, and the like.

[0313] The "substituted silyl" as the first substituent includes, for example, silyl substituted with three substituents selected from the group consisting of alkyl, cycloalkyl, and aryl, such as trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, triarylsilyl, dialkylarylsilyl, and alkyldiarylsilyl.

[0314] An example of the "trialkylsilyl" is a group in which three hydrogen atoms in a silyl are each independently substituted with an alkyl, and the alkyl can be cited from the groups described as the "alkyl" in the first substituent above. Preferred alkyl groups for substitution are alkyl groups having 1 to 5 carbon atoms, and specific examples thereof include methyl, ethyl, propyl, i-propyl, butyl, sec-butyl, t-butyl, and t-amyl.

[0315] Specific examples of trialkylsilyl include trimethylsilyl, triethylsilyl, tripropylsilyl, tri-i-propylsilyl, tributylsilyl, trisec-butylsilyl, tri-t-butylsilyl, tri-t-amylsilyl, ethyldimethylsilyl, propyldimethylsilyl, i-propyldimethylsilyl, butyldimethylsilyl, sec-butyldimethylsilyl, t-butyldimethylsilyl, t-amyldimethylsilyl, methyldiethylsilyl, propyldiethylsilyl, i-propyldiethylsilyl, and butyldiethylsilyl. Examples of the silyl group include butyldiethylsilyl, sec-butyldiethylsilyl, t-butyldiethylsilyl, t-amyldiethylsilyl, methyldipropylsilyl, ethyldipropylsilyl, butyldipropylsilyl, sec-butyldipropylsilyl, t-butyldipropylsilyl, t-amyldipropylsilyl, methyldi-i-propylsilyl, ethyldi-i-propylsilyl, butyldi-i-propylsilyl, sec-butyldi-i-propylsilyl, t-butyldi-i-propylsilyl, and t-amyldi-i-propylsilyl.

[0316] Examples of "tricycloalkylsilyl" include a group in which three hydrogen atoms in silyl are independently replaced by cycloalkyl, and the cycloalkyl can be cited as the group described as "cycloalkyl" in the first substituent above. Preferred cycloalkyl for substitution is a cycloalkyl having 5 to 10 carbon atoms, specifically cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, bicyclo[1.1.1]pentyl, bicyclo[2.0.1]pentyl, bicyclo[1.2.1]hexyl, bicyclo[3.0.1]hexyl, bicyclo[2.1.2]heptyl, bicyclo[2.2.2]octyl, adamantyl, decahydronaphthalenyl, decahydroazulenyl, and the like.

[0317] Specific examples of tricycloalkylsilyl include tricyclopentylsilyl and tricyclohexylsilyl.

[0318] Specific examples of dialkylcycloalkylsilyl substituted with two alkyls and one cycloalkyl and alkyldicycloalkylsilyl substituted with one alkyl and two cycloalkyls include silyl substituted with a group selected from the specific alkyls and cycloalkyls mentioned above.

[0319] Specific examples of dialkylarylsilyl substituted with two alkyls and one aryl, alkyldiarylsilyl substituted with one alkyl and two aryls, and triarylsilyl substituted with three aryls include silyl substituted with a group selected from the above-mentioned specific alkyls and aryls. Specific examples of triarylsilyl include triphenylsilyl.

[0320] The "aryl" in the "diarylboryl" as the first substituent can be quoted from the above description of the aryl. In addition, the two aryls are not bound by a single bond or a linking group (e.g., >C(-R) 2 , >O, >S or >NR), where >C(-R)2 And R in >NR is aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, or aryloxy (the above, first substituent), and the first substituent may be further substituted with aryl, heteroaryl, alkyl, or cycloalkyl (the above, second substituent). As specific examples of these groups, the above-mentioned explanations of aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, or aryloxy as the first substituent can be cited.

[0321] Specifically, the emission wavelength can be adjusted by the steric hindrance, electron donating property and electron withdrawing property of the structure of the first substituent, and is preferably a group represented by the following structural formula, more preferably methyl, t-butyl, t-pentyl (t-amyl), phenyl, o-tolyl, p-tolyl, 2,4-xylyl, 2,5-xylyl, 2,6-xylyl, 2,4,6-mesityl, diphenylamino, di-p-tolylamino, bis(p-(t-butyl)phenyl)amino, carbazolyl, 3,6-dimethylcarbazolyl, 3,6-di-t-butylcarbazolyl and phenoxy, and even more preferably methyl, t-butyl, phenyl, o-tolyl, 2,6-xylyl, 2,4,6-mesityl, diphenylamino, di-p-tolylamino, bis(p-(t-butyl)phenyl)amino, carbazolyl, 3,6-dimethylcarbazolyl and 3,6-di-t-butylcarbazolyl. From the viewpoint of ease of synthesis, larger steric hindrance is preferred for selective synthesis, and specifically, t-butyl, t-pentyl (t-amyl), o-tolyl, p-tolyl, 2,4-xylyl, 2,5-xylyl, 2,6-xylyl, 2,4,6-mesityl, di-p-tolylamino, bis(p-(t-butyl)phenyl)amino, 3,6-dimethylcarbazolyl and 3,6-di-t-butylcarbazolyl are preferred.

[0322] In the structural formula below, "Me" is methyl, "tBu" is t-butyl, "tAm" is t-amyl, "tOct" is t-octyl, and * indicates the bond position. [ka]

[0323]

change

[0324]

change

[0325]

change

[0326]

change

[0327]

change

[0328]

change

[0329]

change

[0330]

change

[0331]

change

[0332]

change

[0333] [ka]

[0334] [ka]

[0335] In formula (2-a), R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , and R 11 Among these, it is preferred that 1 to 4 are groups represented by any one of the structural formulas above, and the remainder are hydrogen. 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , and R 11 It is more preferable that one to three of R are groups represented by any one of the structural formulas above, and the rest are hydrogen. 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , and R 11 It is more preferable that one to three of these are methyl, t-butyl or t-amyl, and the remainder are hydrogen.

[0336] The first substituent, substituted or unsubstituted "aryl", substituted or unsubstituted "heteroaryl", substituted or unsubstituted "diarylamino", substituted or unsubstituted "diheteroarylamino", substituted or unsubstituted "arylheteroarylamino", substituted or unsubstituted "diarylboryl (two aryls may be bonded via a single bond or a linking group)", substituted or unsubstituted "alkyl", substituted or unsubstituted "cycloalkyl", substituted or unsubstituted "alkoxy", or substituted or unsubstituted "aryloxy", may have at least one hydrogen atom substituted with a second substituent, as described above as substituted or unsubstituted. Examples of the second substituent include aryl, heteroaryl, alkyl, or cycloalkyl, and specific examples thereof can be found in the description of the monovalent group of the "aryl ring" or "heteroaryl ring" and the "alkyl" or "cycloalkyl" as the first substituent. The aryl and heteroaryl as the second substituent also include structures in which at least one hydrogen atom in the aryl and heteroaryl as the second substituent is substituted with an aryl such as phenyl (specific examples are the groups mentioned above), an alkyl such as methyl (specific examples are the groups mentioned above), or a cycloalkyl such as cyclohexyl (specific examples are the groups mentioned above). As an example, when the second substituent is carbazolyl, the heteroaryl as the second substituent also includes a carbazolyl in which at least one hydrogen atom at the 9-position is substituted with an aryl such as phenyl, an alkyl such as methyl, or a cycloalkyl such as cyclohexyl.

[0337] R in formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e), and formula (2-f) 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , and R 11The aryl, heteroaryl, aryl of diarylamino, heteroaryl of diheteroarylamino, aryl and heteroaryl of arylheteroarylamino, aryl of diarylboryl, and aryl of aryloxy in the formula (1) include the monovalent groups of "aryl ring" or "heteroaryl ring" described in formula (2). 1 ~R 11 For the alkyl, cycloalkyl, or alkoxy in R, the explanation of "alkyl," "cycloalkyl," or "alkoxy" as the first substituent in the explanation of formula (2) above can be referred to. Furthermore, the same applies to aryl, heteroaryl, alkyl, or cycloalkyl as substituents to these groups. 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , and R 11 When adjacent groups among these are bonded to form an aryl ring or a heteroaryl ring together with the a ring, the b ring, or the c ring, the same applies to the heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl, alkyl, cycloalkyl, alkoxy, or aryloxy as substituents on these rings, and the aryl, heteroaryl, alkyl, or cycloalkyl as further substituents.

[0338] X in Equation (2) 1 and X 2In the formula (2-a), R in >NR is an aryl, heteroaryl, alkyl, or cycloalkyl, which may be substituted with the second substituent described above, and at least one hydrogen in the aryl or heteroaryl may be substituted with, for example, an alkyl or cycloalkyl. Examples of the aryl, heteroaryl, alkyl, and cycloalkyl include the groups described above. In particular, an aryl having 6 to 10 carbon atoms (e.g., phenyl, naphthyl, etc.), a heteroaryl having 2 to 15 carbon atoms (e.g., carbazolyl, etc.), an alkyl having 1 to 5 carbon atoms (e.g., methyl, ethyl, etc.), or a cycloalkyl having 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl) is preferred. This explanation applies to X in formulas (2-a), (2-b), (2-c), (2-d), (2-e), and (2-f). 1 and X 2 The same is true for X in formulas (2-a), (2-b), (2-c), (2-d), (2-e), and (2-f). 1 and X 2 R in >NR is an aryl having 6 to 12 carbon atoms which may be substituted with an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms, a heteroaryl having 2 to 15 carbon atoms which may be substituted with an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms, an alkyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 14 carbon atoms, and is preferably an aryl having 6 to 10 carbon atoms which may be substituted with an alkyl having 1 to 4 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms, an alkyl having 1 to 4 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms.

[0339] X in Equation (2) 1 and X 2 >C(-R) in 2R is hydrogen, an aryl, an alkyl, or a cycloalkyl which may be substituted with the second substituent described above, and at least one hydrogen in the aryl may be substituted with, for example, an alkyl or a cycloalkyl. Examples of the aryl, alkyl, and cycloalkyl include the groups described above. In particular, an aryl having 6 to 10 carbon atoms (e.g., phenyl, naphthyl, etc.), an alkyl having 1 to 5 carbon atoms (e.g., methyl, ethyl, etc.), or a cycloalkyl having 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl) is preferred. This explanation applies to X in formulas (2-a), (2-b), (2-c), (2-d), (2-e), and (2-f). 1 and X 2 The same is true for X in formulas (2-a), (2-b), (2-c), (2-d), (2-e), and (2-f). 1 and X 2 >C(-R) in 2 R is hydrogen, an aryl having 6 to 12 carbon atoms which may be substituted with an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms, an alkyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 14 carbon atoms, and is preferably hydrogen, an aryl having 6 to 10 carbon atoms which may be substituted with an alkyl having 1 to 4 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms, an alkyl having 1 to 4 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms.

[0340] The linking group in formula (2) is "-C(-R) 2 R in "-" is hydrogen, alkyl, or cycloalkyl, and examples of the alkyl and cycloalkyl include the groups described above. In particular, alkyl having 1 to 5 carbon atoms (e.g., methyl, ethyl, etc.) or cycloalkyl having 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl) is preferred. This explanation applies to the linking group "-C(-R)" in formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e), and formula (2-f). 2 -" is also the same.

[0341] The dopant material may be a multimer of a polycyclic aromatic compound having a plurality of unit structures represented by formula (2). The multimer is preferably a multimer of a polycyclic aromatic compound having a plurality of unit structures represented by formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e), or formula (2-f). The multimer is preferably a dimer to hexamer, more preferably a dimer to trimer, and particularly preferably a dimer. The multimer may be in a form having a plurality of the above unit structures in one compound. For example, in addition to a form in which a plurality of the above unit structures are bonded together via a linking group such as a single bond, an alkylene group having 1 to 3 carbon atoms, a phenylene group, or a naphthylene group, the multimer may be in a form in which any ring (ring A, ring B or ring C, ring a, ring b or ring c) contained in the above unit structure is bonded so as to be shared by a plurality of unit structures, or the multimer may be in a form in which any ring (ring A, ring B or ring C, ring a, ring b or ring c) contained in the above unit structure is bonded together so as to be condensed.

[0342] 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). The multimer compound represented by the following formula (2-4) is a multimer compound having a plurality of unit structures represented by formula (2-a) in one compound, with the benzene ring being the a-ring shared, as explained by formula (2-a). The multimer compound represented by the following formula (2-4-1) is a multimer compound having two unit structures represented by formula (2-a) in one compound, with the benzene ring being the a-ring shared, as explained by formula (2-a). The multimer compound represented by the following formula (2-4-2) is a multimer compound having three unit structures represented by formula (2-a) in one compound, with the benzene ring being the a-ring shared, as explained by formula (2-a). Moreover, the multimeric compounds represented by the following formulae (2-5-1) to (2-5-4) are multimeric compounds having a plurality of unit structures represented by formula (2-a) in one compound, with the benzene ring being the b ring (or c ring) shared when explained by formula (2-a). Moreover, the multimeric compound represented by the following formula (2-6) is a multimeric compound having a plurality of unit structures represented by formula (2-a) in one compound, with the benzene ring being the b ring (or a ring, c ring) of a certain unit structure condensed with the benzene ring being the b ring (or a ring, c ring) of a certain unit structure when explained by formula (2-a).

[0343] [ka]

[0344] The multimeric compound may be a multimer in which a multimerization form represented by formula (2-4), formula (2-4-1) or formula (2-4-2) is combined with a multimerization form represented by any one of formulas (2-5-1) to (2-5-4) or formula (2-6), a multimer in which a multimerization form represented by any one of formulas (2-5-1) to (2-5-4) is combined with a multimerization form represented by formula (2-6), or a multimer in which a multimerization form represented by formula (2-4), formula (2-4-1) or formula (2-4-2), a multimerization form represented by any one of formulas (2-5-1) to (2-5-4), and a multimerization form represented by formula (2-6).

[0345] In addition, all or a part of hydrogen in the chemical structure of the polycyclic aromatic compound and its multimer represented by formula (2) or formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e), or formula (2-f) may be deuterium, cyano, or halogen. For example, in formula (2), the A ring, the B ring, the C ring (A to C rings are aryl rings or heteroaryl rings), the substituents on the A to C rings, and X 3 and X 4 >NR or >C(-R) 2 In the above formula, hydrogen atoms in R (=alkyl, cycloalkyl, aryl) may be replaced by deuterium, cyano, or halogen atoms, and among these, examples include embodiments in which all or a part of hydrogen atoms in aryl or heteroaryl are replaced by deuterium, cyano, or halogen atoms. Halogen atoms are fluorine, chlorine, bromine, or iodine, preferably fluorine, chlorine, or bromine, and more preferably fluorine or chlorine.

[0346] In addition, at least one selected from the group consisting of aryl rings and heteroaryl rings in 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 the multimer thereof may be condensed with at least one cycloalkane.

[0347] For example, aryl and heteroaryl rings in the aryl and heteroaryl rings which are ring A, ring B, ring C, ring a, ring b, and ring c, aryl (aryl moiety in aryl, diarylamino, arylheteroarylamino, diarylboryl, or aryloxy) and heteroaryl (heteroaryl moiety in heteroaryl, diheteroarylamino, or arylheteroarylamino) as the first and second substituents in ring A to ring C, aryl (similar to above) and heteroaryl (similar to above) as the first and second substituents on ring a, ring b, and ring c, and X 1 , X 2 At least one of the aryl (as above) and heteroaryl (as above) as R in >NR may be fused with at least one cycloalkane.

[0348] Preferably, the aryl and heteroaryl rings are ring A, ring B, ring C, ring a, ring b, and ring c; the aryl (aryl moiety in aryl, diarylamino, diarylboryl, or aryloxy) and the heteroaryl (heteroaryl moiety in heteroaryl or diheteroarylamino) as the first substituents in ring A to ring C; the aryl (similar to above) and the heteroaryl (similar to above) as the first substituents on ring a to ring c; and X 1 , X 2 At least one of the aryl (as above) and heteroaryl (as above) as R in >NR may be fused with at least one cycloalkane.

[0349] More preferably, the aryl rings are ring A, ring B, ring C, ring a, ring b, and ring c; the aryl (aryl moiety in aryl or diarylamino) and heteroaryl (heteroaryl moiety in heteroaryl) as the first substituents in ring A to ring C; the aryl (similar to above) and heteroaryl (similar to above) as the first substituents on ring a, ring b, and ring c; and X 1 , X 2At least one of the aryls (as above) as R in >NR may be fused with at least one cycloalkane.

[0350] More preferably, the aryl rings are ring A, ring B, ring C, ring a, ring b, and ring c, the aryl as the first substituent in ring A to ring C (aryl or aryl moiety in diarylamino), the aryl as the first substituent on ring a, ring b, and ring c (similar to the above), and X 1 , X 2 At least one of the aryls (as above) as R in >NR may be fused with at least one cycloalkane.

[0351] Examples of "cycloalkane" include cycloalkanes having 3 to 24 carbon atoms, cycloalkanes having 3 to 20 carbon atoms, cycloalkanes having 3 to 16 carbon atoms, cycloalkanes having 3 to 14 carbon atoms, cycloalkanes having 5 to 10 carbon atoms, cycloalkanes having 5 to 8 carbon atoms, cycloalkanes having 5 to 6 carbon atoms, and cycloalkanes having 5 carbon atoms.

[0352] Specific examples of cycloalkanes 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, and decahydroazulene, as well as alkyl (particularly methyl) substituted, halogen (particularly fluorine) substituted, and deuterium substituted derivatives of these having 1 to 5 carbon atoms.

[0353] Among these, for example, as shown in the following structural formula, a structure in which at least one hydrogen atom is substituted on the carbon atom at the α-position of a cycloalkane (a carbon atom at a position adjacent to the carbon atom at the condensation site in a cycloalkane fused to an aryl ring or heteroaryl ring) is preferred, a structure in which two hydrogen atoms are substituted on the carbon atom at the α-position is more preferred, and a structure in which a total of four hydrogen atoms are substituted on the two carbon atoms at the α-position is even more preferred. Examples of this substituent include an alkyl (particularly methyl) substituent having 1 to 5 carbon atoms, a halogen (particularly fluorine) substituent, and a deuterium substituent. In particular, 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 is preferred.

[0354] [ka] In the formula, Me represents methyl, and * represents the bonding position.

[0355] In formula (B), Me represents methyl, and * represents a bonding position, which is bonded to two adjacent elements on the aryl ring or heteroaryl ring to which the group represented by formula (B) is bonded. Examples of such structures include the structures of compounds represented by any of formulas (2-559) to (2-563) and (2-580) described below.

[0356] The number of cycloalkanes condensed to one aromatic ring or heteroaromatic ring is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1. For example, an example in which one or more cycloalkanes are condensed to one benzene ring (phenyl) is shown below. Cycloalkanes condensed to each other as in formula (Cy-1-4) and formula (Cy-2-4) may be condensed. The same applies when the condensed ring (group) is an aromatic ring or heteroaromatic ring other than a benzene ring (phenyl), or when the condensed cycloalkane is a cycloalkane other than cyclopentane or cyclohexane. [ka]

[0357] At least one -CH in the cycloalkane 2 - may be replaced by -O-. For example, one or more -CH 2 Examples in which - is replaced by -O- are shown below. The same applies even when the condensed ring (group) is an aromatic ring or heteroaromatic ring other than a benzene ring (phenyl), and even when the condensed cycloalkane is a cycloalkane other than cyclopentane or cyclohexane.

[0358] [ka]

[0359] At least one hydrogen atom in the cycloalkane may be substituted, and examples of the substituent include aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, substituted silyl, deuterium, cyano, and halogen. For details, the description of the first substituent mentioned above can be cited. Among these substituents, alkyl (e.g., alkyl having 1 to 6 carbon atoms), cycloalkyl (e.g., cycloalkyl having 3 to 14 carbon atoms), halogen (e.g., fluorine), and deuterium are preferred. In addition, when cycloalkyl is substituted, it may be substituted to form a spiro structure, and examples of this are shown below.

[0360] [ka]

[0361] Other forms of cycloalkane condensation include polycyclic aromatic compounds represented by formula (2), formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e), or formula (2-f) and their multimers, whose chemical structures include, for example, >NR, where R is an aryl condensed with a cycloalkane, diarylamino condensed with a cycloalkane (condensed to this aryl portion), carbazolyl condensed with a cycloalkane (condensed to this benzene ring portion), or benzocarbazolyl condensed with a cycloalkane (condensed to this benzene ring portion). For "diarylamino", the groups described above as "first substituent" are included.

[0362] Further, as a more specific example, R in the chemical structure of a polycyclic aromatic compound and a multimer thereof represented by formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e), or formula (2-f) is 2 is a diarylamino fused to a cycloalkane (fused to the aryl moiety) or a carbazolyl fused to a cycloalkane (fused to the benzene ring moiety).

[0363] Preferred combinations of substituents in formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e), and formula (2-f) include the following. R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , and R 11are each independently hydrogen, an aryl having 6 to 30 carbon atoms which may be substituted with an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms, a heteroaryl having 2 to 30 carbon atoms which may be substituted with an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms, a diarylamino (wherein the aryl is an aryl having 6 to 12 carbon atoms which may be substituted with an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms), a diarylboryl (wherein the aryl is an aryl having 6 to 12 carbon atoms which may be substituted with an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms), an alkyl having 1 to 24 carbon atoms, or a cycloalkyl having 3 to 24 carbon atoms; 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , and R 11 adjacent groups among the above may be bonded to each other to form an aryl ring having 9 to 16 carbon atoms or a heteroaryl ring having 6 to 15 carbon atoms together with ring a, ring b or ring c, and at least one hydrogen atom in the formed ring may be substituted by an aryl having 6 to 30 carbon atoms which may be substituted with an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms, a heteroaryl having 2 to 30 carbon atoms which may be substituted with an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms, a diarylamino (wherein the aryl is an aryl having 6 to 12 carbon atoms which may be substituted with an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms), a diarylboryl (wherein the aryl is an aryl having 6 to 12 carbon atoms which may be substituted with an alkyl having 1 to 6 carbon atoms or a cycloalkyl having 3 to 14 carbon atoms), an alkyl having 1 to 24 carbon atoms, or a cycloalkyl having 3 to 24 carbon atoms; X 1 and X 2 are independently >O, >NR, >C(-R) 2or >S, and R of the >NR is an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 4 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms, which may be substituted with an alkyl having 1 to 4 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms, and the >C(-R) 2 R is hydrogen, aryl having 6 to 10 carbon atoms which may be substituted with alkyl having 1 to 4 carbon atoms or cycloalkyl having 5 to 10 carbon atoms, alkyl having 1 to 4 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms.

[0364] More preferred combinations of substituents in formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e), and formula (2-f) include the following. R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , and R 11 are each independently hydrogen, an aryl having 6 to 16 carbon atoms which may be substituted with an alkyl having 1 to 4 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms, a heteroaryl having 2 to 20 carbon atoms which may be substituted with an alkyl having 1 to 4 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms, a diarylamino (wherein the aryl is an aryl having 6 to 10 carbon atoms which may be substituted with an alkyl having 1 to 4 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms), a diarylboryl (wherein the aryl is an aryl having 6 to 10 carbon atoms which may be substituted with an alkyl having 1 to 4 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms), an alkyl having 1 to 12 carbon atoms, or a cycloalkyl having 3 to 16 carbon atoms; 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , and R 11adjacent groups among these may be bonded to each other to form an aryl ring having 9 to 16 carbon atoms or a heteroaryl ring having 6 to 15 carbon atoms together with ring a, ring b or ring c, and at least one hydrogen in the formed ring may be substituted by an aryl having 6 to 13 carbon atoms which may be substituted with an alkyl having 1 to 4 carbon atoms or a cycloalkyl having 3 to 10 carbon atoms, a heteroaryl having 2 to 12 carbon atoms which may be substituted with an alkyl having 1 to 4 carbon atoms or a cycloalkyl having 3 to 10 carbon atoms, a diarylamino (wherein the aryl is an aryl having 6 to 12 carbon atoms which may be substituted with an alkyl having 1 to 4 carbon atoms or a cycloalkyl having 3 to 10 carbon atoms), a diarylboryl (wherein the aryl is an aryl having 6 to 12 carbon atoms which may be substituted with an alkyl having 1 to 4 carbon atoms or a cycloalkyl having 3 to 10 carbon atoms), an alkyl having 1 to 12 carbon atoms, or a cycloalkyl having 3 to 20 carbon atoms; X 1 and X 2 are each independently >O, >NR, or >C(-R) 2 R in the >NR is an aryl having 6 to 10 carbon atoms, an alkyl having 1 to 4 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms, which may be substituted with an alkyl having 1 to 4 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms; and the >C(-R) 2 R is hydrogen, aryl having 6 to 10 carbon atoms which may be substituted with alkyl having 1 to 4 carbon atoms or cycloalkyl having 5 to 10 carbon atoms, alkyl having 1 to 4 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms.

[0365] More preferred combinations of substituents in formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e), and formula (2-f) include the following. R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , and R 11each independently represents a hydrogen atom, an aryl having 6 to 16 carbon atoms which may be substituted with an alkyl having 1 to 4 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms, a heteroaryl having 2 to 20 carbon atoms which may be substituted with an alkyl having 1 to 4 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms, a diarylamino (wherein the aryl is an aryl having 6 to 10 carbon atoms which may be substituted with an alkyl having 1 to 4 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms), a diarylboryl (wherein the aryl is an aryl having 6 to 10 carbon atoms which may be substituted with an alkyl having 1 to 4 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms), an alkyl having 1 to 12 carbon atoms, or a cycloalkyl having 3 to 16 carbon atoms; Also, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , and R 11 adjacent groups among these may be bonded to each other to form an aryl ring having 9 to 16 carbon atoms or a heteroaryl ring having 6 to 15 carbon atoms together with ring a, ring b or ring c, and at least one hydrogen atom in the formed ring may be substituted by an aryl having 6 to 13 carbon atoms which may be substituted with an alkyl having 1 to 4 carbon atoms or a cycloalkyl having 3 to 10 carbon atoms, a heteroaryl having 2 to 12 carbon atoms which may be substituted with an alkyl having 1 to 4 carbon atoms or a cycloalkyl having 3 to 10 carbon atoms, a diarylamino (wherein the aryl is an aryl having 6 to 12 carbon atoms which may be substituted with an alkyl having 1 to 4 carbon atoms or a cycloalkyl having 3 to 10 carbon atoms), an alkyl having 1 to 6 carbon atoms, or a cycloalkyl having 3 to 10 carbon atoms; X 1 and X 2 are each independently >O or >NR, and R in the >NR is an aryl having 6 to 10 carbon atoms which may be substituted with an alkyl having 1 to 4 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms, an alkyl having 1 to 4 carbon atoms, or a cycloalkyl having 5 to 10 carbon atoms.

[0366] More specific examples of the polycyclic aromatic compound represented by formula (2) include compounds represented by the following formula: In the following formula, "Me" represents methyl, "tBu" represents tertiary butyl (t-butyl), "iPr" represents isopropyl, "Ph" represents phenyl, "tAm" represents tertiary amyl (tertiary pentyl), and "D" represents deuterium.

[0367] [ka]

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[0410] 1-2-2. Method for producing polycyclic aromatic compounds represented by formula (2) and their multimers The polycyclic aromatic compound represented by formula (2) and its multimer can be synthesized, for example, by the method disclosed in International Publication No. 2019 / 009052 as “Method for Producing Polycyclic Aromatic Compound Represented by Formula (2) and Its Multimer.”

[0411] 1-3.Emitting layer The light-emitting layer may be a single layer or multiple layers, each of which is formed from a material for the light-emitting layer (host material, dopant material). The host material may be one compound represented by formula (1), a combination of two or more compounds represented by formula (1), or 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 compound represented by formula (2), a combination of two or more compounds represented by formula (2), or 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).

[0412] The dopant material may be entirely or partially contained in the host material. As a doping method, the dopant material may be formed by co-evaporation with the host material, or the dopant material may be mixed with the host material in advance and then vapor-deposited at the same time.

[0413] The amount of the host material used varies depending on the type of the host material and may be determined according to the properties of the host material. The amount of the host material used is preferably 50 to 99.999% by mass, more preferably 80 to 99.95% by mass, and even more preferably 90 to 99.9% by mass, of the total material for the light-emitting layer.

[0414] The amount of the dopant material used varies depending on the type of the dopant material, and may be determined according to 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 even more preferably 0.1 to 10% by mass, based on the total material for the light-emitting layer. The above range is preferable in that, for example, concentration quenching can be prevented.

[0415] Examples of host materials that can be used in combination with the compound represented by formula (1) include fused ring derivatives such as pyrene, which have long been known as light-emitting bodies, bisstyryl derivatives such as bisstyryl anthracene derivatives and distyrylbenzene derivatives, tetraphenylbutadiene derivatives, cyclopentadiene derivatives, fluorene derivatives, and benzofluorene derivatives.

[0416] Dopant materials that can be used in combination with the compound represented by formula (2) include fused ring derivatives such as anthracene and pyrene, which have long been known as light-emitting bodies, bisstyryl derivatives such as bisstyrylanthracene derivatives and distyrylbenzene derivatives, tetraphenylbutadiene derivatives, cyclopentadiene derivatives, fluorene derivatives, and benzofluorene derivatives.

[0417] 2. Electron injection layer and electron transport layer in organic electroluminescent device The electron injection layer 107 plays a role of efficiently injecting electrons moving from the cathode 108 into the light-emitting layer 105 or the electron transport layer 106. The electron transport layer 106 plays a role of efficiently transporting electrons injected from the cathode 108 or electrons injected from the cathode 108 via the electron injection layer 107 to the light-emitting layer 105. The electron transport layer 106 and the electron injection layer 107 are each formed by laminating or mixing one or more types of electron transport / injection materials, or by a mixture of an electron transport / injection material and a polymer binder.

[0418] The electron injection / transport layer is a layer that is responsible for injecting electrons from the cathode and transporting the electrons. It is desirable that the electron injection efficiency is high and that the injected electrons are efficiently transported. For this purpose, it is preferable that the material has a large electron affinity, a large electron mobility, and excellent stability, and impurities that become traps are unlikely to occur during manufacture and use. However, when considering the balance of transport of holes and electrons, if the material mainly plays a role of efficiently preventing holes from flowing from the anode to the cathode without recombining, even if the electron transport ability is not so high, it has the effect of improving the luminous efficiency equivalent to a material with a high electron transport ability. Therefore, the electron injection / transport layer in this embodiment may also include the function of a layer that can efficiently block the movement of holes.

[0419] The material (electron transport material) for forming the electron transport layer 106 or the electron injection layer 107 can be arbitrarily selected from compounds conventionally used as electron transport compounds in photoconductive materials and known compounds used in the electron injection layer and electron transport layer of organic EL elements.

[0420] Materials used in the electron transport layer or electron injection layer preferably contain at least one selected from compounds consisting of aromatic rings or heteroaromatic rings composed of one or more atoms selected from carbon, hydrogen, oxygen, sulfur, silicon, and phosphorus, pyrrole derivatives and their condensed ring derivatives, and metal complexes having electron-accepting nitrogen. Specific examples include condensed ring aromatic ring derivatives such as naphthalene and anthracene, styryl aromatic ring derivatives such as 4,4'-bis(diphenylethenyl)biphenyl, perinone derivatives, coumarin derivatives, naphthalimide derivatives, quinone derivatives such as anthraquinone and diphenoquinone, phosphine oxide derivatives, arylnitrile derivatives, and indole derivatives. Examples of metal complexes having electron-accepting nitrogen include hydroxyazole complexes such as hydroxyphenyloxazole complexes, azomethine complexes, tropolone metal complexes, flavonol metal complexes, and benzoquinoline metal complexes. These materials can be used alone or in combination with different materials.

[0421] Specific examples of other electron transfer compounds 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 (such as 1,3-bis[(4-t-butylphenyl)1,3,4-oxadiazolyl]phenylene), thiophene derivatives, triazole derivatives (such as N-naphthyl-2,5-diphenyl-1,3,4-triazole), thiadiazole derivatives, metal complexes of oxine derivatives, quinolinol metal complexes, quinoxaline derivatives, polymers of quinoxaline derivatives, benzazole compounds, gallium complexes, pyrazole derivatives, perfluorinated phenylene derivatives, and triazine derivatives. , pyrazine derivatives, benzoquinoline derivatives (such as 2,2'-bis(benzo[h]quinolin-2-yl)-9,9'-spirobifluorene), imidazopyridine derivatives, benzimidazole derivatives (such as tris(N-phenylbenzimidazol-2-yl)benzene), benzoxazole derivatives, thiazole derivatives, benzothiazole derivatives, quinoline derivatives, oligopyridine derivatives such as terpyridine, bipyridine derivatives, terpyridine derivatives (such as 1,3-bis(4'-(2,2':6',2"-terpyridinyl))benzene), naphthyridine derivatives (such as bis(1-naphthyl)-4-(1,8-naphthyridin-2-yl)phenylphosphine oxide), aldazine derivatives, pyrimidine derivatives, arylnitrile derivatives, indole derivatives, phosphorus oxide derivatives, bisstyryl derivatives, silole derivatives and azoline derivatives.

[0422] Further, a metal complex having an electron-accepting nitrogen can also be used, and examples thereof include hydroxyazole complexes such as quinolinol metal complexes and hydroxyphenyloxazole complexes, azomethine complexes, tropolone metal complexes, flavonol metal complexes, and benzoquinoline metal complexes.

[0423] The above-mentioned materials may be used alone or in combination with different materials.

[0424] Among the above-mentioned materials, 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, quinolinol-based metal complexes, thiazole derivatives, benzothiazole derivatives, silole derivatives and azoline derivatives are preferred.

[0425] <Borane derivatives> The borane derivative is, for example, a compound represented by the following formula (ETM-1), and is disclosed in detail in JP-A-2007-27587. [ka]

[0426] In formula (ETM-1), R 11 and R 12 are each independently at least one of hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, or cyano; R 13 ~R 16 are each independently an optionally substituted alkyl, an optionally substituted cycloalkyl, or an optionally substituted aryl, X is an optionally substituted arylene, Y is an optionally substituted aryl having 16 or less carbon atoms, a substituted boryl, or an optionally substituted carbazolyl, and each n is independently an integer of 0 to 3. In addition, examples of the substituent in the case of "optionally substituted" or "substituted" include aryl, heteroaryl, alkyl, and cycloalkyl.

[0427] Among the compounds represented by formula (ETM-1), compounds represented by the following formula (ETM-1-1) and compounds represented by the following formula (ETM-1-2) are preferred. [ka]

[0428] In formula (ETM-1-1), R 11 and R 12 are each independently at least one of hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, or cyano; R 13 ~R 16 are each independently optionally substituted alkyl, optionally substituted cycloalkyl, or optionally substituted aryl; R 21 and R 22 are each independently at least one of hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, or cyano; X 1 is an optionally substituted arylene having 20 or less carbon atoms, each n is independently an integer of 0 to 3, and each m is independently an integer of 0 to 4. In addition, examples of the substituent in the case where "optionally substituted" or "substituted" include aryl, heteroaryl, alkyl, and cycloalkyl.

[0429] [ka]

[0430] In formula (ETM-1-2), R 11 and R 12 are each independently at least one of hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, or cyano; R 13 ~R 16are each independently an optionally substituted alkyl, an optionally substituted cycloalkyl, or an optionally substituted aryl; X 1 is an optionally substituted arylene having 20 or less carbon atoms, and each n is independently an integer of 0 to 3. Examples of the substituent in the case where it is "optionally substituted" or "substituted" include aryl, heteroaryl, alkyl, and cycloalkyl.

[0431] X 1 Specific examples of the group include divalent groups represented by any of the following formulae (X-1) to (X-9). [ka] (In each formula, R a are each independently an alkyl, cycloalkyl or an optionally substituted phenyl group, and * represents the bonding position.)

[0432] Specific examples of the borane derivative include the following compounds: [ka]

[0433] The borane derivative can be produced using known raw materials and known synthesis methods.

[0434] <Pyridine derivatives> The pyridine derivative is, for example, a compound represented by the following formula (ETM-2), preferably a compound represented by formula (ETM-2-1) or formula (ETM-2-2). [ka]

[0435] φ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring or triphenylene ring), and n is an integer of 1 to 4.

[0436] In formula (ETM-2-1), R 11 ~R 18 are each independently hydrogen, alkyl (preferably alkyl having 1 to 24 carbon atoms), cycloalkyl (preferably cycloalkyl having 3 to 12 carbon atoms) or aryl (preferably aryl having 6 to 30 carbon atoms).

[0437] In formula (ETM-2-2), R 11 and R 12 are each independently hydrogen, alkyl (preferably alkyl having 1 to 24 carbon atoms), cycloalkyl (preferably cycloalkyl having 3 to 12 carbon atoms) or aryl (preferably aryl having 6 to 30 carbon atoms); R 11 and R 12 may be bonded to form a ring.

[0438] In each formula, the "pyridine-based substituent" is any one of the following formulae (Py-1) to (Py-15) (in the formula, * indicates a bonding position), and each pyridine-based substituent may be independently substituted with an alkyl having 1 to 4 carbon atoms or a cycloalkyl having 5 to 10 carbon atoms. Specific examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, and t-butyl, and methyl is preferred. In addition, the pyridine-based substituent may be bonded to the φ, anthracene ring, or fluorene ring in each formula via a phenylene group or naphthylene group.

[0439] [ka]

[0440] The pyridine-based substituent is any one of the formulae (Py-1) to (Py-15), and among these, any one of the following formulae (Py-21) to (Py-44) (in the formulae, * indicates a bonding position) is preferable. [ka]

[0441] At least one hydrogen atom in each pyridine derivative may be replaced by deuterium, and one of the two "pyridine-based substituents" in formulae (ETM-2-1) and (ETM-2-2) may be replaced by aryl.

[0442] R 11 ~R 18 The "alkyl" in the above may be either linear or branched, and examples thereof include linear alkyl having 1 to 24 carbon atoms or branched alkyl having 3 to 24 carbon atoms. A preferred "alkyl" is an alkyl having 1 to 18 carbon atoms (branched alkyl having 3 to 18 carbon atoms). A more preferred "alkyl" is an alkyl having 1 to 12 carbon atoms (branched alkyl having 3 to 12 carbon atoms). An even more preferred "alkyl" is an alkyl having 1 to 6 carbon atoms (branched alkyl having 3 to 6 carbon atoms). An especially preferred "alkyl" is an alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms).

[0443] Specific examples of "alkyl" include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl, 1-methylheptyl, Examples include 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n-undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, and n-eicosyl.

[0444] As for the alkyl having 1 to 4 carbon atoms with which the pyridine-based substituent is substituted, the above description of the alkyl can be cited.

[0445] R 11 ~R 18 In the above, the "cycloalkyl" is, for example, a cycloalkyl having 3 to 12 carbon atoms. A preferred "cycloalkyl" is a cycloalkyl having 3 to 10 carbon atoms. A more preferred "cycloalkyl" is a cycloalkyl having 3 to 8 carbon atoms. An even more preferred "cycloalkyl" is a cycloalkyl having 3 to 6 carbon atoms. Specific examples of "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, and dimethylcyclohexyl.

[0446] R 11 ~R 18 As for the "aryl" in the above, a preferable aryl is an aryl having 6 to 30 carbon atoms, a more preferable aryl is an aryl having 6 to 18 carbon atoms, an even more preferable aryl is an aryl having 6 to 14 carbon atoms, and an especially preferable aryl is an aryl having 6 to 12 carbon atoms.

[0447] Specific examples of the "aryl having 6 to 30 carbon atoms" include monocyclic aryl phenyl, fused bicyclic aryl (1-, 2-)naphthyl, fused tricyclic aryl acenaphthylene-(1-, 3-, 4-, 5-)yl, fluoren-(1-, 2-, 3-, 4-, 9-)yl, phenalene-(1-, 2-)yl, (1-, 2-, 3-, 4-, 9-)phenanthryl, fused tetracyclic aryl triphenylene-(1-, 2-)yl, pyrene-(1-, 2-, 4-)yl, naphthacene-(1-, 2-, 5-)yl, fused pentacyclic aryl perylene-(1-, 2-, 3-)yl, pentacene-(1-, 2-, 5-, 6-)yl, and the like.

[0448] Preferred examples of the "aryl having 6 to 30 carbon atoms" include phenyl, naphthyl, phenanthryl, chrysenyl, and triphenylenyl, more preferably phenyl, 1-naphthyl, 2-naphthyl, and phenanthryl, and particularly preferably phenyl, 1-naphthyl, and 2-naphthyl.

[0449] R in formula (ETM-2-2) 11 and R 12 may be bonded to form a ring, and as a result, cyclobutane, cyclopentane, cyclopentene, cyclopentadiene, cyclohexane, fluorene, indene, or the like may be spiro-bonded to the five-membered ring of the fluorene skeleton.

[0450] Specific examples of the pyridine derivative include the following compounds: [ka]

[0451] This pyridine derivative can be produced using known raw materials and known synthesis methods.

[0452] <Fluoranthene derivatives> The fluoranthene derivative is, for example, a compound represented by the following formula (ETM-3), and is specifically disclosed in International Publication No. 2010 / 134352. [Chemical formula]

[0453] In formula (ETM-3), X 12 ~X 21 represents hydrogen, halogen, linear, branched or cyclic alkyl, linear, branched or cyclic alkoxy, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl. Here, examples of the substituent in the case of being substituted include aryl, heteroaryl, alkyl or cycloalkyl.

[0454] Specific examples of this fluoranthene derivative include, for example, the following compounds. [Chemical formula]

[0455] [BO-based derivative] The BO-based derivative is, for example, a polycyclic aromatic compound represented by the following formula (ETM-4), or a multimer of a polycyclic aromatic compound having a plurality of structures represented by the following formula (ETM-4). [Chemical formula]

[0456] R 61 ~R 71 are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkoxy or aryloxy, and at least one hydrogen in these may be substituted with aryl, heteroaryl, alkyl or cycloalkyl.

[0457] Also, R 61 ~R 71Adjacent groups among these may be bonded to each other to form an aryl ring or a heteroaryl ring together with the a ring, the b ring, or the c ring, and at least one hydrogen atom in the formed ring may be substituted with an aryl, a heteroaryl, a diarylamino, a diheteroarylamino, an arylheteroarylamino, an alkyl, a cycloalkyl, an alkoxy, or an aryloxy, and at least one hydrogen atom in these rings may be substituted with an aryl, a heteroaryl, an alkyl, or a cycloalkyl.

[0458] In addition, at least one hydrogen in the compound or structure represented by formula (ETM-4) may be substituted with a halogen or deuterium.

[0459] For an explanation of the substituents and the form of ring formation in formula (ETM-4), the explanation of the polycyclic aromatic compound represented by formula (1) or formula (2) can be cited.

[0460] Specific examples of the BO derivative include the following compounds: [ka]

[0461] The BO derivative can be produced using known raw materials and known synthesis methods.

[0462] <Anthracene derivatives> The anthracene derivative is, for example, a compound represented by the following formula (ETM-5). [ka]

[0463] Ar 1 are each independently a single bond, or a divalent benzene, naphthalene, anthracene, fluorene, or phenalene.

[0464] Ar 2are each independently an aryl having 6 to 20 carbon atoms, preferably an aryl having 6 to 16 carbon atoms, more preferably an aryl having 6 to 12 carbon atoms, and particularly preferably an aryl having 6 to 10 carbon atoms. Specific examples of "aryl having 6 to 20 carbon atoms" include monocyclic aryls such as phenyl, (o-, m-, p-)tolyl, (2,3-, 2,4-, 2,5-, 2,6-, 3,4-, 3,5-)xylyl, mesityl (2,4,6-trimethylphenyl), and (o-, m-, p-)cumenyl, bicyclic aryls such as (2-, 3-, 4-)biphenylyl, condensed bicyclic aryls such as (1-, 2-)naphthyl, and tricyclic aryls such as terphenylyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4'-yl, p-terphenyl-2 ...4'-yl, p-terphenyl-2-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4'-yl, p-terphenyl-2-yl, m-terphenyl-4'-yl, p-terphenyl-2-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m aryl, o-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl; condensed tricyclic aryls, anthracene-(1-,2-,9-)yl, acenaphthylene-(1-,3-,4-,5-)yl, fluorene-(1-,2-,3-,4-,9-)yl, phenalene-(1-,2-)yl, (1-,2-,3-,4-,9-)phenanthryl; condensed tetracyclic aryls, triphenylene-(1-,2-)yl, pyrene-(1-,2-,4-)yl, tetracene-(1-,2-,5-)yl; condensed pentacyclic aryls, perylene-(1-,2-,3-)yl, and the like. Specific examples of the "aryl having 6 to 10 carbon atoms" include phenyl, biphenylyl, naphthyl, terphenylyl, anthracenyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, tetracenyl, and perylenyl.

[0465] R 1 ~R 4 are each independently hydrogen, alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, or aryl having 6 to 20 carbon atoms.

[0466] R 1 ~R 4 The alkyl having 1 to 6 carbon atoms in the formula (I) may be either linear or branched. That is, it is a linear alkyl having 1 to 6 carbon atoms or a branched alkyl having 3 to 6 carbon atoms. More preferably, it is an alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms). Specific examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, and 2-ethylbutyl. Methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, and t-butyl are preferred, and methyl, ethyl, and t-butyl are more preferred.

[0467] R 1 ~R 4 Specific examples of the cycloalkyl having 3 to 6 carbon atoms include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, and dimethylcyclohexyl.

[0468] R 1 ~R 4 In the above, the aryl having 6 to 20 carbon atoms is preferably an aryl having 6 to 16 carbon atoms, more preferably an aryl having 6 to 12 carbon atoms, and particularly preferably an aryl having 6 to 10 carbon atoms. Specific examples of "aryl having 6 to 20 carbon atoms" include Ar 2 Specific examples of "aryl having 6 to 20 carbon atoms" in the above can be cited. Preferred "aryl having 6 to 20 carbon atoms" are phenyl, biphenylyl, terphenylyl, or naphthyl, more preferably phenyl, biphenylyl, 1-naphthyl, 2-naphthyl, or m-terphenyl-5'-yl, further preferably phenyl, biphenylyl, 1-naphthyl, or 2-naphthyl, and most preferably phenyl.

[0469] Specific examples of these anthracene derivatives include the following compounds. [ka]

[0470] These anthracene derivatives can be produced using known raw materials and known synthesis methods.

[0471] <Benzofluorene derivatives> The benzofluorene derivative is, for example, a compound represented by the following formula (ETM-6). [ka]

[0472] Ar 1 are each independently an aryl having 6 to 20 carbon atoms, and Ar 2 The same explanation as for "aryl having 6 to 20 carbon atoms" in the above can be cited. An aryl having 6 to 16 carbon atoms is preferable, an aryl having 6 to 12 carbon atoms is more preferable, and an aryl having 6 to 10 carbon atoms is particularly preferable. Specific examples include phenyl, biphenylyl, naphthyl, terphenylyl, anthracenyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, etc.

[0473] Ar 2 are each independently hydrogen, alkyl (preferably alkyl having 1 to 24 carbon atoms), cycloalkyl (preferably cycloalkyl having 3 to 12 carbon atoms) or aryl (preferably aryl having 6 to 30 carbon atoms), and two Ar 2 may be bonded to form a ring.

[0474] Ar 2The "alkyl" in the above may be either linear or branched, and examples thereof include linear alkyl having 1 to 24 carbon atoms or branched alkyl having 3 to 24 carbon atoms. A preferred "alkyl" is an alkyl having 1 to 18 carbon atoms (branched alkyl having 3 to 18 carbon atoms). A more preferred "alkyl" is an alkyl having 1 to 12 carbon atoms (branched alkyl having 3 to 12 carbon atoms). An even more preferred "alkyl" is an alkyl having 1 to 6 carbon atoms (branched alkyl having 3 to 6 carbon atoms). An especially preferred "alkyl" is an alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms). Specific examples of "alkyl" include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl, n-hexyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, and the like.

[0475] Ar 2 In the above, the "cycloalkyl" is, for example, a cycloalkyl having 3 to 12 carbon atoms. A preferred "cycloalkyl" is a cycloalkyl having 3 to 10 carbon atoms. A more preferred "cycloalkyl" is a cycloalkyl having 3 to 8 carbon atoms. An even more preferred "cycloalkyl" is a cycloalkyl having 3 to 6 carbon atoms. Specific examples of the "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, and dimethylcyclohexyl.

[0476] Ar 2 As for the "aryl" in the above, a preferable aryl is an aryl having 6 to 30 carbon atoms, a more preferable aryl is an aryl having 6 to 18 carbon atoms, an even more preferable aryl is an aryl having 6 to 14 carbon atoms, and an especially preferable aryl is an aryl having 6 to 12 carbon atoms.

[0477] Specific examples of the "aryl having 6 to 30 carbon atoms" include phenyl, naphthyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, naphthacenyl, perylenyl, and pentacenyl.

[0478] Two Ar 2 may be bonded to form a ring, and as a result, cyclobutane, cyclopentane, cyclopentene, cyclopentadiene, cyclohexane, fluorene, indene, or the like may be spiro-bonded to the five-membered ring of the fluorene skeleton.

[0479] Specific examples of the benzofluorene derivative include the following compounds: [ka]

[0480] The benzofluorene derivative can be produced using known raw materials and known synthesis methods.

[0481] <Phosphine oxide derivatives> The phosphine oxide derivative is, for example, a compound represented by the following formula (ETM-7-1): The details are also described in WO 2013 / 079217 and WO 2013 / 079678. [ka]

[0482] R 5 is a substituted or unsubstituted alkyl having 1 to 20 carbon atoms, cycloalkyl having 3 to 16 carbon atoms, aryl having 6 to 20 carbon atoms, or heteroaryl having 5 to 20 carbon atoms, R 6 is CN, a substituted or unsubstituted alkyl having 1 to 20 carbon atoms, a cycloalkyl having 3 to 16 carbon atoms, a heteroalkyl having 1 to 20 carbon atoms, an aryl having 6 to 20 carbon atoms, a heteroaryl having 5 to 20 carbon atoms, an alkoxy having 1 to 20 carbon atoms, or an aryloxy having 6 to 20 carbon atoms, R 7 and R 8 each independently represents a substituted or unsubstituted aryl having 6 to 20 carbon atoms or a heteroaryl having 5 to 20 carbon atoms, R 9 is oxygen or sulfur, j is 0 or 1, k is 0 or 1, r is an integer of 0 to 4, and q is an integer of 1 to 3. When substituted, the substituent may be an aryl, heteroaryl, alkyl or cycloalkyl.

[0483] The phosphine oxide derivative may be, for example, a compound represented by the following formula (ETM-7-2). [ka]

[0484] R 1 ~R 3 may be the same or different and are selected from hydrogen, alkyl, cycloalkyl, aralkyl, alkenyl, cycloalkenyl, alkynyl, alkoxy, alkylthio, cycloalkylthio, an aryl ether group, an aryl thioether group, aryl, a heterocyclic group, halogen, cyano, formyl, carbonyl, carboxyl, amino, nitro, silyl, and a fused ring formed between adjacent substituents.

[0485] Ar 1 may be the same or different and are arylene or heteroarylene. Ar 2 may be the same or different and are aryl or heteroaryl, provided that Ar 1 and Ar 2 At least one of R has a substituent or forms a condensed ring with the adjacent substituent. n is an integer of 0 to 3. When n is 0, there is no unsaturated structural portion. When n is 3, R 1 does not exist.

[0486] Among these substituents, alkyl refers to saturated aliphatic hydrocarbon groups such as methyl, ethyl, propyl, and butyl, which may be unsubstituted or substituted. If substituted, the substituent is not particularly limited, and may be, for example, alkyl, aryl, or heterocyclic groups, which is also the case in the following description. The number of carbon atoms in the alkyl is not particularly limited, but is usually in the range of 1 to 20 in terms of availability and cost.

[0487] The term "cycloalkyl" refers to a saturated alicyclic hydrocarbon group, such as cyclopropyl, cyclohexyl, norbornyl, adamantyl, etc., which may be unsubstituted or substituted. The number of carbon atoms in the alkyl portion is not particularly limited, but is usually in the range of 3 to 20.

[0488] The term "aralkyl" refers to an aromatic hydrocarbon group mediated by an aliphatic hydrocarbon such as benzyl or phenylethyl, and both the aliphatic hydrocarbon and the aromatic hydrocarbon may be unsubstituted or substituted. The number of carbon atoms in the aliphatic portion is not particularly limited, but is usually in the range of 1 to 20.

[0489] The alkenyl refers to an unsaturated aliphatic hydrocarbon group containing a double bond, such as vinyl, allyl, butadienyl, which may be unsubstituted or substituted. The number of carbon atoms in the alkenyl is not particularly limited, but is usually in the range of 2 to 20.

[0490] Moreover, cycloalkenyl refers to an unsaturated alicyclic hydrocarbon group containing a double bond, such as cyclopentenyl, cyclopentadienyl, cyclohexene, etc., which may be unsubstituted or substituted.

[0491] The term "alkynyl" refers to an unsaturated aliphatic hydrocarbon group containing a triple bond, such as acetylenyl, which may be unsubstituted or substituted. The number of carbon atoms in the alkynyl is not particularly limited, but is usually within the range of 2 to 20.

[0492] The term "alkoxy" refers to an aliphatic hydrocarbon group, such as methoxy, which is bonded via an ether bond, and the aliphatic hydrocarbon group may be unsubstituted or substituted. The number of carbon atoms in the alkoxy is not particularly limited, but is usually in the range of 1 to 20.

[0493] Moreover, alkylthio is a group in which the oxygen atom of the ether bond of alkoxy is replaced with a sulfur atom.

[0494] Moreover, cycloalkylthio is a group in which the oxygen atom of the ether bond of a cycloalkoxy group is replaced with a sulfur atom.

[0495] The aryl ether group refers to an aromatic hydrocarbon group such as phenoxy, which is bonded via an ether bond, and the aromatic hydrocarbon group may be unsubstituted or substituted. The number of carbon atoms in the aryl ether group is not particularly limited, but is usually in the range of 6 to 40.

[0496] An aryl thioether group is a group in which the oxygen atom of the ether bond of an aryl ether group is substituted with a sulfur atom.

[0497] The aryl group refers to an aromatic hydrocarbon group such as phenyl, naphthyl, biphenylyl, phenanthryl, terphenyl, and pyrenyl. The aryl group may be unsubstituted or substituted. The number of carbon atoms in the aryl group is not particularly limited, but is usually in the range of 6 to 40.

[0498] The heterocyclic group refers to a cyclic structure group having atoms other than carbon, such as furanyl, thienyl, oxazolyl, pyridyl, quinolinyl, carbazolyl, etc., which may be unsubstituted or substituted. The number of carbon atoms in the heterocyclic group is not particularly limited, but is usually in the range of 2 to 30.

[0499] Halogen refers to fluorine, chlorine, bromine and iodine.

[0500] Formyl, carbonyl and amino may also include groups substituted with aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons, heterocycles and the like.

[0501] Furthermore, the aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons and heterocycles may be either unsubstituted or substituted.

[0502] Silyl refers to a silicon compound group such as trimethylsilyl, which may be unsubstituted or substituted. The number of carbon atoms in silyl is not particularly limited, but is usually in the range of 3 to 20. The number of silicon atoms is usually 1 to 6.

[0503] The condensed ring formed between adjacent substituents is, for example, Ar 1 and R 2 , Ar 1 and R 3 , Ar 2 and R 2 , Ar 2 and R 3 , R 2 and R 3 , Ar 1 and Ar 2 etc., where n is 1, two R 1 They may form conjugated or non-conjugated fused rings together. These fused rings may contain nitrogen, oxygen, or sulfur atoms in the ring structure, and may be fused to further rings.

[0504] Specific examples of the phosphine oxide derivative include the following compounds: [ka]

[0505] The phosphine oxide derivative can be produced using known raw materials and known synthesis methods.

[0506] <Pyrimidine derivatives> The pyrimidine derivative is, for example, a compound represented by the following formula (ETM-8), preferably a compound represented by the following formula (ETM-8-1). Details are also described in WO 2011 / 021689. [ka]

[0507] Each Ar is independently an optionally substituted aryl or an optionally substituted heteroaryl, and n is an integer of 1 to 4, preferably an integer of 1 to 3, and more preferably 2 or 3.

[0508] The "aryl" in the "optionally substituted aryl" includes, for example, an aryl having 6 to 30 carbon atoms, preferably an aryl having 6 to 24 carbon atoms, more preferably an aryl having 6 to 20 carbon atoms, and further preferably an aryl having 6 to 12 carbon atoms.

[0509] Specific examples of "aryl" include monocyclic aryl phenyl, bicyclic aryl (2-, 3-, 4-) biphenylyl, condensed bicyclic aryl (1-, 2-) naphthyl, tricyclic aryl terphenylyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), condensed tricyclic aryl Examples of the aryl include acenaphthylene-(1-,3-,4-,5-)yl, fluorene-(1-,2-,3-,4-,9-)yl, phenalene-(1-,2-)yl, (1-,2-,3-,4-,9-)phenanthryl, the tetracyclic aryl group is quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl), the condensed tetracyclic aryl group is triphenylene-(1-,2-)yl, pyrene-(1-,2-,4-)yl, naphthacene-(1-,2-,5-)yl, the condensed pentacyclic aryl group is perylene-(1-,2-,3-)yl, pentacene-(1-,2-,5-,6-)yl, and the like.

[0510] Examples of the "heteroaryl" in "optionally substituted heteroaryl" include heteroaryl having 2 to 30 carbon atoms, preferably heteroaryl having 2 to 25 carbon atoms, more preferably heteroaryl having 2 to 20 carbon atoms, further preferably heteroaryl having 2 to 15 carbon atoms, and particularly preferably heteroaryl having 2 to 10 carbon atoms. Examples of the heteroaryl include heterocycles containing, as ring-constituting atoms other than carbon, 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen.

[0511] Specific examples of heteroaryl 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, cinnolyl, quinazolyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenoxathiinyl, thianthrenyl, and indolizinyl.

[0512] The above aryl and heteroaryl may be substituted, for example, by the above aryl or heteroaryl, respectively.

[0513] Specific examples of the pyrimidine derivative include the following compounds: [ka]

[0514] The pyrimidine derivative can be produced using known raw materials and known synthesis methods.

[0515] <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 such compounds are bonded together via single bonds, etc. Details are described in the specification of US Patent Publication No. 2014 / 0197386. [ka]

[0516] Ar niFrom the viewpoint of fast electron transport property, it is preferable that the number of carbon atoms is large, and from the viewpoint of high T1, it is preferable that the number of carbon atoms is small. ni Specifically, it is preferable that the aryl group has a high T1 when used in a layer adjacent to the light-emitting layer, and is an aryl group having 6 to 20 carbon atoms, preferably an aryl group having 6 to 14 carbon atoms, and more preferably an aryl group having 6 to 10 carbon atoms. In addition, the number of nitrile group substitutions, n, is preferably large from the viewpoint of high T1, and is preferably small from the viewpoint of high S1. Specifically, the number of nitrile group substitutions, n, is an integer of 1 to 4, preferably an integer of 1 to 3, more preferably an integer of 1 to 2, and even more preferably 1.

[0517] Each Ar is independently an aryl which may be substituted or a heteroaryl which may be substituted. From the viewpoint of high S1 and high T1, it is preferable that the heteroaryl has donor properties, and it is preferable that the heteroaryl has few donor properties because it is used as an electron transport layer. From the viewpoint of charge transportability, it is preferable that the aryl or heteroaryl has many carbon atoms, and it is preferable that the aryl or heteroaryl has many substituents. The number of substitutions m of Ar is specifically an integer of 1 to 4, preferably an integer of 1 to 3, and more preferably 1 to 2.

[0518] The "aryl" in the "optionally substituted aryl" includes, for example, an aryl having 6 to 30 carbon atoms, preferably an aryl having 6 to 24 carbon atoms, more preferably an aryl having 6 to 20 carbon atoms, and further preferably an aryl having 6 to 12 carbon atoms.

[0519] Specific examples of "aryl" include monocyclic aryl phenyl, bicyclic aryl (2-, 3-, 4-) biphenylyl, condensed bicyclic aryl (1-, 2-) naphthyl, tricyclic aryl terphenylyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), condensed tricyclic aryl Examples of the aryl include acenaphthylene-(1-,3-,4-,5-)yl, fluorene-(1-,2-,3-,4-,9-)yl, phenalene-(1-,2-)yl, (1-,2-,3-,4-,9-)phenanthryl, the tetracyclic aryl group is quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl), the condensed tetracyclic aryl group is triphenylene-(1-,2-)yl, pyrene-(1-,2-,4-)yl, naphthacene-(1-,2-,5-)yl, the condensed pentacyclic aryl group is perylene-(1-,2-,3-)yl, pentacene-(1-,2-,5-,6-)yl, and the like.

[0520] Examples of the "heteroaryl" in "optionally substituted heteroaryl" include heteroaryl having 2 to 30 carbon atoms, preferably heteroaryl having 2 to 25 carbon atoms, more preferably heteroaryl having 2 to 20 carbon atoms, further preferably heteroaryl having 2 to 15 carbon atoms, and particularly preferably heteroaryl having 2 to 10 carbon atoms. Examples of the heteroaryl include heterocycles containing, as ring-constituting atoms other than carbon, 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen.

[0521] Specific examples of heteroaryl 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, cinnolyl, quinazolyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenoxathiinyl, thianthrenyl, and indolizinyl.

[0522] The above aryl and heteroaryl may be substituted, for example, by the above aryl or heteroaryl, respectively.

[0523] The arylnitrile derivative may be a polymer in which a plurality of compounds represented by formula (ETM-9) are bonded together via single bonds, etc. In this case, they may be bonded together via 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.

[0524] Specific examples of the arylnitrile derivative include the following compounds: [ka]

[0525] The arylnitrile derivatives can be produced using known raw materials and known synthesis methods.

[0526] <Triazine derivatives> The triazine derivative is, for example, a compound represented by the following formula (ETM-10), preferably a compound represented by the following formula (ETM-10-1), the details of which are described in the specification of US Patent Publication No. 2011 / 0156013. [ka]

[0527] Each Ar is independently an optionally substituted aryl or an optionally substituted heteroaryl, and n is an integer of 1 to 3, preferably 2 or 3.

[0528] The "aryl" in the "optionally substituted aryl" includes, for example, an aryl having 6 to 30 carbon atoms, preferably an aryl having 6 to 24 carbon atoms, more preferably an aryl having 6 to 20 carbon atoms, and further preferably an aryl having 6 to 12 carbon atoms.

[0529] Specific examples of "aryl" include monocyclic aryl phenyl, bicyclic aryl (2-, 3-, 4-) biphenylyl, condensed bicyclic aryl (1-, 2-) naphthyl, tricyclic aryl terphenylyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), condensed tricyclic aryl Examples of the aryl include acenaphthylene-(1-,3-,4-,5-)yl, fluorene-(1-,2-,3-,4-,9-)yl, phenalene-(1-,2-)yl, (1-,2-,3-,4-,9-)phenanthryl, the tetracyclic aryl group is quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl), the condensed tetracyclic aryl group is triphenylene-(1-,2-)yl, pyrene-(1-,2-,4-)yl, naphthacene-(1-,2-,5-)yl, the condensed pentacyclic aryl group is perylene-(1-,2-,3-)yl, pentacene-(1-,2-,5-,6-)yl, and the like.

[0530] Examples of the "heteroaryl" in "optionally substituted heteroaryl" include heteroaryl having 2 to 30 carbon atoms, preferably heteroaryl having 2 to 25 carbon atoms, more preferably heteroaryl having 2 to 20 carbon atoms, further preferably heteroaryl having 2 to 15 carbon atoms, and particularly preferably heteroaryl having 2 to 10 carbon atoms. Examples of the heteroaryl include heterocycles containing, as ring-constituting atoms other than carbon, 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen.

[0531] Specific examples of heteroaryl 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, cinnolyl, quinazolyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxazinyl, phenothiazinyl, phenazinyl, phenoxathiinyl, thianthrenyl, and indolizinyl.

[0532] The above aryl and heteroaryl may be substituted, for example, by the above aryl or heteroaryl, respectively.

[0533] Specific examples of the triazine derivative include the following compounds: [ka]

[0534] The triazine derivative can be produced using known raw materials and known synthesis methods.

[0535] <Benzimidazole derivatives> The benzimidazole derivative is, for example, a compound represented by the following formula (ETM-11). [ka]

[0536] φ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring, or triphenylene ring), n is an integer from 1 to 4, and the "benzoimidazole-based substituent" is a substituent in which the pyridyl in the "pyridine-based substituent" in the formulae (ETM-2), (ETM-2-1), and (ETM-2-2) is replaced with benzimidazolyl, and at least one hydrogen in the benzimidazole derivative may be replaced with deuterium. [ka]

[0537] R in the above benzimidazolyl 11 is hydrogen, alkyl having 1 to 24 carbon atoms, cycloalkyl having 3 to 12 carbon atoms, or aryl having 6 to 30 carbon atoms, and R in formula (ETM-2-1) and formula (ETM-2-2) 11 The explanation can be cited.

[0538] φ is preferably an anthracene ring or a fluorene ring. In this case, the structure can be as described in the formula (ETM-2-1) or the formula (ETM-2-2). R 11 ~R 18 The explanation for formula (ETM-2-1) or formula (ETM-2-2) can be cited. In addition, in formula (ETM-2-1) or formula (ETM-2-2), the two pyridine-based substituents are explained as being bonded, but when these are replaced with benzimidazole-based substituents, both pyridine-based substituents may be replaced with benzimidazole-based substituents (i.e., n=2), or one of the pyridine-based substituents may be replaced with a benzimidazole-based substituent and the other pyridine-based substituent may be replaced with R 11 ~R 18 (i.e., n=1). Furthermore, for example, R in formula (ETM-2-1) 11 ~R 18 At least one of the above is replaced with a benzimidazole-based substituent to form a "pyridine-based substituent" R 11~R 18 may be substituted.

[0539] Specific examples of the benzimidazole derivative include 1-phenyl-2-(4-(10-phenylanthracen-9-yl)phenyl)-1H-benzo[d]imidazole, 2-(4-(10-(naphthalen-2-yl)anthracen-9-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole, 2-(3-(10-(naphthalen-2-yl)anthracen-9-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole, and 5-(10-(naphthalen-2-yl)anthracen-9-yl)-1,2-diphenyl-1H-benzo[d]imidazole. , 1-(4-(10-(naphthalene-2-yl)anthracen-9-yl)phenyl)-2-phenyl-1H-benzo[d]imidazole, 2-(4-(9,10-di(naphthalene-2-yl)anthracen-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole, 1-(4-(9,10-di(naphthalene-2-yl)anthracen-2-yl)phenyl)-2-phenyl-1H-benzo[d]imidazole, 5-(9,10-di(naphthalene-2-yl)anthracen-2-yl)-1,2-diphenyl-1H-benzo[d]imidazole, and the like.

[0540] [ka]

[0541] The benzimidazole derivative can be produced using known raw materials and known synthesis methods.

[0542] <Phenanthroline derivatives> The phenanthroline derivative is, for example, a compound represented by the following formula (ETM-12) or formula (ETM-12-1), the details of which are described in WO 2006 / 021982. [ka]

[0543] φ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring or triphenylene ring), and n is an integer of 1 to 4.

[0544] R of each formula 11 ~R 18 are each independently hydrogen, alkyl (preferably alkyl having 1 to 24 carbon atoms), cycloalkyl (preferably cycloalkyl having 3 to 12 carbon atoms), or aryl (preferably aryl having 6 to 30 carbon atoms). 11 ~R 18 Either one of these bonds becomes a bond to the aryl ring φ.

[0545] At least one hydrogen atom in each of the phenanthroline derivatives may be replaced with deuterium.

[0546] R 11 ~R 18 As the alkyl, cycloalkyl and aryl in the formula (ETM-2), R 11 ~R 18 can be cited. In addition to the above examples, φ can have the following structural formula. In the structural formula, R is independently hydrogen, methyl, ethyl, isopropyl, cyclohexyl, phenyl, 1-naphthyl, 2-naphthyl, biphenylyl, or terphenylyl, and * indicates a bonding position.

[0547] [ka]

[0548] Specific examples of the phenanthroline derivative include 4,7-diphenyl-1,10-phenanthroline, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline, 9,10-di(1,10-phenanthroline-2-yl)anthracene, 2,6-di(1,10-phenanthroline-5-yl)pyridine, 1,3,5-tri(1,10-phenanthroline-5-yl)benzene, 9,9'-difluoro-bi(1,10-phenanthroline-5-yl), bathocuproine, 1,3-bis(2-phenyl-1,10-phenanthroline-9-yl)benzene, and compounds represented by the following structural formula. [ka]

[0549] The phenanthroline derivative can be produced using known raw materials and known synthesis methods.

[0550] <Quinolinol metal complexes> The quinolinol metal complex is, for example, a compound represented by the following formula (ETM-13). [ka] In the formula, R 1 ~R 6 are each independently hydrogen, fluorine, alkyl, cycloalkyl, aralkyl, alkenyl, cyano, alkoxy or aryl; M is Li, Al, Ga, Be or Zn; and n is an integer of 1 to 3.

[0551] Specific examples of quinolinol-based metal complexes include 8-quinolinol lithium, tris(8-quinolinolato)aluminum, tris(4-methyl-8-quinolinolato)aluminum, tris(5-methyl-8-quinolinolato)aluminum, tris(3,4-dimethyl-8-quinolinolato)aluminum, tris(4,5-dimethyl-8-quinolinolato)aluminum, tris(4,6-dimethyl-8-quinolinolato)aluminum, bis(2-methyl-8-quinolinolato)(phenolate)aluminum, bis(2-methyl-8-quinolinolato)(phenolate), and bis(2-methyl-8-quinolinolato). Bis(2-methylphenolate)aluminum, bis(2-methyl-8-quinolinate)(3-methylphenolate)aluminum, bis(2-methyl-8-quinolinate)(4-methylphenolate)aluminum, bis(2-methyl-8-quinolinate)(2-phenylphenolate)aluminum, bis(2-methyl-8-quinolinate)(3-phenylphenolate)aluminum, bis(2-methyl-8-quinolinate)(4-phenylphenolate)aluminum, bis(2-methyl-8-quinolinate)(2,3 -dimethylphenolate)aluminum, bis(2-methyl-8-quinolinate)(2,6-dimethylphenolate)aluminum, bis(2-methyl-8-quinolinate)(3,4-dimethylphenolate)aluminum, bis(2-methyl-8-quinolinate)(3,5-dimethylphenolate)aluminum, bis(2-methyl-8-quinolinate)(3,5-di-t-butylphenolate)aluminum, bis(2-methyl-8-quinolinate)(2,6-diphenylphenolate)aluminum, bis(2-methyl-8-quinolinate)(3,5-di-t-butylphenolate)aluminum linolate)(2,4,6-triphenylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(2,4,6-trimethylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(2,4,5,6-tetramethylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(1-naphtholate)aluminum, bis(2-methyl-8-quinolinolate)(2-naphtholate)aluminum, bis(2,4-dimethyl-8-quinolinolate)(2-phenylphenolate)aluminum, bis(2,4-Dimethyl-8-quinolinolate)(3-phenylphenolate)aluminum, bis(2,4-dimethyl-8-quinolinolate)(4-phenylphenolate)aluminum, bis(2,4-dimethyl-8-quinolinolate)(3,5-dimethylphenolate)aluminum, bis(2,4-dimethyl-8-quinolinolate)(3,5-di-t-butylphenolate)aluminum, bis(2-methyl-8-quinolinolate)aluminum-μ-oxo-bis(2-methyl-8-quinolinolate)aluminum, bis(2,4-dimethyl-8-quinolinolate)aluminum-μ-oxo-bis(2,4-dimethyl-8-quinolinolate)aluminum, bis(2-methyl-4-ethyl-8- quinolinolate)aluminum-μ-oxo-bis(2-methyl-4-ethyl-8-quinolinolate)aluminum, bis(2-methyl-4-methoxy-8-quinolinolate)aluminum-μ-oxo-bis(2-methyl-4-methoxy-8-quinolinolate)aluminum, bis(2-methyl-5-cyano-8-quinolinolate)aluminum-μ-oxo-bis(2-methyl-5-cyano-8-quinolinolate)aluminum, bis(2-methyl-5-trifluoromethyl-8-quinolinolate)aluminum-μ-oxo-bis(2-methyl-5-trifluoromethyl-8-quinolinolate)aluminum, bis(10-hydroxybenzo[h]quinoline)beryllium, etc.

[0552] The quinolinol metal complex can be produced using known raw materials and known synthesis methods.

[0553] <Thiazole derivatives and benzothiazole derivatives> The thiazole derivative is, for example, a compound represented by the following formula (ETM-14-1). [ka] The benzothiazole derivative is, for example, a compound represented by the following formula (ETM-14-2). [ka]

[0554] In each formula, φ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring, or triphenylene ring), and n is an integer from 1 to 4. A "thiazole-based substituent" or a "benzothiazole-based substituent" is a substituent in which the pyridyl in the "pyridine-based substituent" in the formulae (ETM-2), (ETM-2-1), and (ETM-2-2) is replaced with the below-mentioned thiazolyl or benzothiazolyl, and at least one hydrogen in the thiazole derivative and the benzothiazole derivative may be replaced with a deuterium.

[0555] [ka]

[0556] φ is preferably an anthracene ring or a fluorene ring. In this case, the structure can be as described in the formula (ETM-2-1) or the formula (ETM-2-2). R 11 ~R 18 The explanation for formula (ETM-2-1) or formula (ETM-2-2) can be cited. In addition, in formula (ETM-2-1) or formula (ETM-2-2), two pyridine-based substituents are described as being bonded together, but when these are replaced with a thiazole-based substituent (or a benzothiazole-based substituent), both pyridine-based substituents may be replaced with a thiazole-based substituent (or a benzothiazole-based substituent) (i.e., n=2), or one of the pyridine-based substituents may be replaced with a thiazole-based substituent (or a benzothiazole-based substituent) and the other pyridine-based substituent may be replaced with R 11 ~R 18 (i.e., n=1). Furthermore, for example, R in formula (ETM-2-1) 11 ~R 18 At least one of the substituents is replaced with a thiazole-based substituent (or a benzothiazole-based substituent) to form a "pyridine-based substituent" R 11 ~R 18 may be substituted.

[0557] These thiazole or benzothiazole derivatives can be produced using known raw materials and known synthesis methods.

[0558] <Silole derivatives> The silole derivative is, for example, a compound represented by the following formula (ETM-15), the details of which are described in JP-A-9-194487. [ka]

[0559] X and Y are each independently alkyl, cycloalkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, aryl, or heteroaryl, which may be substituted. For details of these groups, the explanations in formula (1) and formula (2) and further the explanation in formula (ETM-7-2) can be cited. In addition, alkenyloxy and alkynyloxy are groups in which the alkyl portion of alkoxy is replaced with alkenyl or alkynyl, respectively, and for details of these alkenyls and alkynyls, the explanation in formula (ETM-7-2) can be cited. In addition, X and Y may be bonded to form a cycloalkyl ring (or a ring in which a part is unsaturated), and details of this cycloalkyl ring can be found in the description of cycloalkyl in formula (1) and formula (2).

[0560] R 1 ~R 4are each independently hydrogen, halogen, alkyl, cycloalkyl, alkoxy, aryloxy, amino, alkylcarbonyl, arylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, azo group, alkylcarbonyloxy, arylcarbonyloxy, alkoxycarbonyloxy, aryloxycarbonyloxy, sulfinyl, sulfonyl, sulfanyl, silyl, carbamoyl, aryl, heteroaryl, alkenyl, alkynyl, nitro, formyl, nitroso, formyloxy, isocyano, cyanate group, isocyanate group, thiocyanate group, isothiocyanate group, or cyano, which may be substituted with alkyl, cycloalkyl, aryl or halogen, and may form a condensed ring with an adjacent substituent.

[0561] R 1 ~R 4 For details of halogen, alkyl, cycloalkyl, alkoxy, aryloxy, amino, aryl, heteroaryl, alkenyl and alkynyl in, the descriptions in formula (1) and formula (2) can be cited.

[0562] R 1 ~R 4 For details of the alkyl, aryl and alkoxy in the alkylcarbonyl, arylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, alkylcarbonyloxy, arylcarbonyloxy, alkoxycarbonyloxy and aryloxycarbonyloxy in the above, the explanations in the formula (1) and the formula (2) can be cited.

[0563] Examples of silyl include silyl and groups in which at least one of the three hydrogen atoms of silyl is independently substituted with an aryl, alkyl, or cycloalkyl, and tri-substituted silyl is preferable, such as triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, and alkyldicycloalkylsilyl. For details of the aryl, alkyl, and cycloalkyl, see the explanations in formula (1) and formula (2).

[0564] The condensed ring formed between adjacent substituents is, for example, R 1 and R 2 , R 2 and R 3 , R 3 and R 4 etc. These fused rings may contain nitrogen, oxygen, or sulfur atoms in the ring structure, and may be fused with another ring.

[0565] However, preferably, R 1 and R 4 is a phenyl group, X and Y are not alkyl or phenyl. 1 and R 4 When R is thienyl, X and Y are alkyl, R is thienyl, 2 and R 3 is alkyl, aryl, alkenyl or R 2 and R 3 In addition, it is preferable that R 1 and R 4 If is Cyril, then R 2 , R 3 , X and Y are each independently not hydrogen or alkyl having 1 to 6 carbon atoms. 1 and R 2 In the case of a structure in which a benzene ring is condensed, X and Y are not alkyl and phenyl.

[0566] These silole derivatives can be produced using known raw materials and known synthesis methods.

[0567] <Azoline derivatives> The azoline derivative is, for example, a compound represented by the following formula (ETM-16), details of which are described in International Publication No. 2017 / 014226. [ka]

[0568] In formula (ETM-16), φ 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, and at least one hydrogen of φ is optionally substituted by alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, aryl having 6 to 18 carbon atoms, or heteroaryl having 2 to 18 carbon atoms; Y's are each independently -O-, -S- or >N-Ar, Ar is an aryl having 6 to 12 carbon atoms or a heteroaryl having 2 to 12 carbon atoms, at least one hydrogen of Ar may be substituted by an alkyl having 1 to 4 carbon atoms, a cycloalkyl having 5 to 10 carbon atoms, an aryl having 6 to 12 carbon atoms or a heteroaryl having 2 to 12 carbon atoms, R 1 ~R 5 are each independently hydrogen, alkyl having 1 to 4 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms, provided that Ar in the >N-Ar and R 1 ~R 5 one of which is a site for binding to L; Each 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):

[0569] [ka]

[0570] In formula (L-1), X 1 ~X 6are each independently =CR 6 - or =N- and X 1 ~X 6 At least two of the =CR 6 - and X 1 ~X 6 Two of =CR 6 -R in 6 is the site of binding to φ or the azoline ring, and the other =CR 6 -R in 6 is hydrogen, In formula (L-2), X 7 ~X 14 are each independently =CR 6 - or =N- and X 7 ~X 14 At least two of the =CR 6 - and X 7 ~X 14 Two of =CR 6 -R in 6 is the site of binding to φ or the azoline ring, and the other =CR 6 -R in 6 is hydrogen, at least one hydrogen atom of L may be substituted with alkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, aryl having 6 to 10 carbon atoms, or heteroaryl having 2 to 10 carbon atoms; m is an integer of 1 to 4, and when m is an integer of 2 to 4, the groups formed by the azoline ring and L may be the same or different, and At least one hydrogen atom in the compound represented by formula (ETM-16) may be substituted with deuterium.

[0571] Specific azoline derivatives are compounds represented by the following formula (ETM-16-1) or formula (ETM-16-2). [ka]

[0572] In formula (ETM-16-1) and formula (ETM-16-2), φ 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, and at least one hydrogen of φ is optionally substituted by alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, aryl having 6 to 18 carbon atoms, or heteroaryl having 2 to 18 carbon atoms; In formula (ETM-16-1), each Y is independently -O-, -S- or >N-Ar, Ar is an aryl having 6 to 12 carbon atoms or a heteroaryl having 2 to 12 carbon atoms, and at least one hydrogen of Ar is optionally substituted by an alkyl having 1 to 4 carbon atoms, a cycloalkyl having 5 to 10 carbon atoms, an aryl having 6 to 12 carbon atoms, or a heteroaryl having 2 to 12 carbon atoms; In formula (ETM-16-1), R 1 ~R 4 are each independently hydrogen, alkyl having 1 to 4 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms, with the proviso that R 1 and R 2 are identical, and R 3 and R 4 are identical, In formula (ETM-16-2), R 1 ~R 5 are each independently hydrogen, alkyl having 1 to 4 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms, with the proviso that R 1 and R 2 are identical, and R 3 and R 4 are identical, In formula (ETM-16-1) and formula (ETM-16-2), Each 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):

[0573] [ka] In formula (L-1), X 1 ~X 6 are each independently =CR 6 - or =N- and X 1 ~X 6 At least two of the =CR6 - and X 1 ~X 6 Two of =CR 6 -R in 6 is the site of binding to φ or the azoline ring, and the other =CR 6 -R in 6 is hydrogen, In formula (L-2), X 7 ~X 14 are each independently =CR 6 - or =N- and X 7 ~X 14 At least two of the =CR 6 - and X 7 ~X 14 Two of =CR 6 -R in 6 is the site of binding to φ or the azoline ring, and the other =CR 6 -R in 6 is hydrogen, at least one hydrogen atom of L may be substituted with alkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, aryl having 6 to 10 carbon atoms, or heteroaryl having 2 to 10 carbon atoms; m is an integer of 1 to 4, and when m is an integer of 2 to 4, the groups formed by the azoline ring and L may be the same or different, and At least one hydrogen atom in the compound represented by formula (ETM-16-1) or formula (ETM-16-2) may be replaced with deuterium.

[0574] Preferably, φ is selected from the group consisting of monovalent groups represented by the following formulas (φ1-1) to (φ1-18), divalent groups represented by the following formulas (φ2-1) to (φ2-34), trivalent groups represented by the following formulas (φ3-1) to (φ3-3), and tetravalent groups represented by the following formulas (φ4-1) to (φ4-2), and at least one hydrogen of φ may be substituted by alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, aryl having 6 to 18 carbon atoms, or heteroaryl having 2 to 18 carbon atoms.

[0575] [ka]

[0576] [ka] [ka]

[0577] In the formula, Z is >CR 2 , >N-Ar, >NL, -O- or -S-, >CR 2 R in the formula (1) 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, and 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, and L in >NL is L in formula (ETM-16), formula (ETM-16-1), or formula (ETM-16-2). * in the formula indicates a bonding position.

[0578] Preferably, L is a divalent ring group 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 may be substituted with 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.

[0579] Preferably, Ar in >N-Ar as Y or Z is selected from the group consisting of phenyl, naphthyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, naphthyridinyl, phthalazinyl, quinoxalinyl, quinazolinyl, cinnolinyl, and pteridinyl, and at least one hydrogen of Ar in >N-Ar as Y may be substituted with alkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, or aryl having 6 to 10 carbon atoms.

[0580] Preferably, R 1 ~R 4 are each independently hydrogen, alkyl having 1 to 4 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms, with the proviso that R 1 and R 2 are identical, and R 3 and R 4 are identical, and R 1 ~R 4 are not all hydrogen at the same time, and m is 1 or 2. When m is 2, the groups formed by the azoline ring and L are the same.

[0581] Specific examples of azoline derivatives include the following compounds: In the structural formula, "Me" represents methyl. [ka] [ka]

[0582] More preferably, φ is selected from the group consisting of divalent groups represented by the following formulas (φ2-1), (φ2-31), (φ2-32), (φ2-33) and (φ2-34), and at least one hydrogen of φ may be substituted by an aryl having 6 to 18 carbon atoms: [ka]

[0583] L is a divalent ring group selected from the group consisting of benzene, pyridine, pyrazine, pyrimidine, pyridazine, and triazine, and at least one hydrogen of L is optionally substituted by alkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, aryl having 6 to 10 carbon atoms, or heteroaryl having 2 to 14 carbon atoms; Ar in >N-Ar as Y is selected from the group consisting of phenyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl, and at least one hydrogen of the Ar may be substituted by alkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, or aryl having 6 to 10 carbon atoms; R 1 ~R 4 are each independently hydrogen, alkyl having 1 to 4 carbon atoms, or cycloalkyl having 5 to 10 carbon atoms, with the proviso that R 1 and R 2 are identical, and R 3 and R 4 are identical, and R 1 ~R 4 cannot all become hydrogen at the same time, and m is 2, and the groups formed by the azoline ring and L are the same.

[0584] Other specific examples of azoline derivatives include the following compounds: In the structural formula, "Me" represents methyl. [ka]

[0585] For details of the alkyl, cycloalkyl, aryl or heteroaryl in the above formulas defining this azoline derivative, the explanations in formula (1) and formula (2) can be cited.

[0586] The azoline derivative can be produced using known raw materials and known synthesis methods.

[0587] <Reducing substances> The electron transport layer or the electron injection layer may further contain a substance capable of reducing the material forming the electron transport layer or the electron injection layer. As the reducing substance, various substances may be used as long as they have a certain degree of reducing ability, 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 may be preferably used.

[0588] Preferred reducing substances include alkali metals such as Na (work function 2.36 eV), K (2.28 eV), Rb (2.16 eV) or Cs (1.95 eV), and alkaline earth metals such as Ca (2.9 eV), Sr (2.0 to 2.5 eV) or Ba (2.52 eV), and those with a work function of 2.9 eV or less are particularly preferred. Among these, more preferred reducing substances are alkali metals such as K, Rb or Cs, more preferably Rb or Cs, and most preferably Cs. These alkali metals have particularly high reducing ability, and by adding a relatively small amount to the material forming the electron transport layer or electron injection layer, the luminance of the organic EL element can be improved and the life can be extended. Furthermore, as a reducing substance having a work function of 2.9 eV or less, a combination of two or more of these alkali metals is also preferred, and in particular, a combination containing Cs is preferred, for example, a combination of Cs and Na, Cs and K, Cs and Rb, or a combination of Cs, Na and K. By containing Cs, the reducing ability can be efficiently exhibited, and by adding it to a material forming an electron transport layer or an electron injection layer, the luminance of the organic EL element can be improved and the life span can be extended.

[0589] 3. Substrate for organic electroluminescent device The substrate 101 is a support for the organic EL element 100, and is usually made of quartz, glass, metal, plastic, or the like. The substrate 101 is formed into a plate, film, or sheet shape depending on the purpose, and for example, a glass plate, a metal plate, a metal foil, a plastic film, or a plastic sheet is used. Among them, a glass plate and a plate made of a transparent synthetic resin such as polyester, polymethacrylate, polycarbonate, or polysulfone are preferable. For a glass substrate, soda lime glass or non-alkali glass is used, and the thickness is sufficient to maintain mechanical strength, and may be, for example, 0.2 mm or more. The upper limit of the thickness is, for example, 2 mm or less, and preferably 1 mm or less. As for the material of the glass, it is preferable to use non-alkali glass because less ions are eluted from the glass, but SiO 2 Soda lime glass coated with a barrier coat such as a silicon oxide film is commercially available and can be used. In order to improve the gas barrier properties, a gas barrier film such as a dense silicon oxide film may be provided on at least one side of the substrate 101. In particular, when a synthetic resin plate, film, or sheet with low gas barrier properties is used as the substrate 101, it is preferable to provide a gas barrier film.

[0590] 4. Anode in organic electroluminescent device The anode 102 serves to inject holes into the light-emitting layer 105. When the hole injection layer 103 and / or the hole transport layer 104 are provided between the anode 102 and the light-emitting layer 105, holes are injected into the light-emitting layer 105 via these layers.

[0591] Materials for forming the anode 102 include inorganic compounds and organic compounds. Examples of inorganic compounds include metals (aluminum, gold, silver, nickel, palladium, chromium, etc.), metal oxides (indium oxide, tin oxide, indium-tin oxide (ITO), indium-zinc oxide (IZO), etc.), metal halides (copper iodide, etc.), copper sulfide, carbon black, ITO glass, and Nesa glass. Examples of organic compounds include polythiophenes such as poly(3-methylthiophene), polypyrrole, polyaniline, and other conductive polymers. In addition, materials that are used as anodes in organic EL elements can be appropriately selected and used.

[0592] The resistance of the transparent electrode is not limited as long as it can supply a sufficient current for the light emission of the light emitting element, but it is desirable that the resistance is low from the viewpoint of the power consumption of the light emitting element. For example, an ITO substrate of 300Ω / □ or less functions as an element electrode, but since it is now possible to supply substrates of about 10Ω / □, it is particularly desirable to use a low resistance product of, for example, 100 to 5Ω / □, preferably 50 to 5Ω / □. The thickness of the ITO can be selected arbitrarily according to the resistance value, but it is usually used in the range of 50 to 300 nm.

[0593] 5. Hole injection layer and hole transport layer in organic electroluminescent device The hole injection layer 103 plays a role of efficiently injecting holes moving from the anode 102 into the light emitting layer 105 or the hole transport layer 104. The hole transport layer 104 plays a role of efficiently transporting holes injected from the anode 102 or holes injected from the anode 102 via the hole injection layer 103 to the light emitting layer 105. The hole injection layer 103 and the hole transport layer 104 are each formed by laminating and mixing one or more types of hole injection / transport materials, or by a mixture of a hole injection / transport material and a polymer binder. Alternatively, a layer may be formed by adding an inorganic salt such as iron (III) chloride to the hole injection / transport material.

[0594] A hole injection / transport material is required to efficiently inject / transport holes from the positive electrode between electrodes to which an electric field is applied, and it is desirable for the material to have high hole injection efficiency and efficiently transport the injected holes. For this purpose, it is preferable for the material to have a small ionization potential, a large hole mobility, excellent stability, and a low probability of generating impurities that act as traps during manufacture and use.

[0595] Materials for forming the hole injection layer 103 and the hole transport layer 104 can be arbitrarily selected from compounds conventionally used as charge transport materials for holes in photoconductive materials, p-type semiconductors, and known materials used in hole injection layers and hole transport layers of organic EL elements. Specific examples of such compounds include carbazole derivatives (N-phenylcarbazole, polyvinylcarbazole, etc.), biscarbazole derivatives such as bis(N-arylcarbazole) or bis(N-alkylcarbazole), triarylamine derivatives (polymers having an aromatic tertiary amino in the main chain or side chain, 1,1-bis(4-di-p-tolylaminophenyl)cyclohexane, N,N'-diphenyl-N,N'-di(3-methylphenyl)-4,4'-diaminobiphenyl, N,N'-diphenyl-N,N'-dinaphthyl-4,4'-diaminobiphenyl, N,N'-diphenyl-N,N'-di(3-methylphenyl)-4,4'-diphenyl-1,1'-diamine, N,N'-dinaphthyl-N,N'-diphenyl-4,4'-diphenyl-1,1'-diamine, N 4 ,N 4’ -Diphenyl-N 4 ,N 4’ -Bis(9-phenyl-9H-carbazol-3-yl)-[1,1'-biphenyl]-4,4'-diamine, N 4 ,N 4 ,N 4’ ,N 4’-Tetra[1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine, 4,4',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,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, thiophene derivatives, oxadiazole derivatives, quinoxaline derivatives (for example, 1,4,5,8,9,12-hexaazatriphenylene-2,3,6,7,10,11-hexacarbonitrile, etc.), heterocyclic compounds such as porphyrin derivatives, polysilanes, etc. As for polymers, polycarbonates and styrene derivatives having the above-mentioned monomers in the side chains, polyvinylcarbazole, polysilanes, etc. are preferred, but there is no particular limitation as long as the compound can form a thin film necessary for the production of a light-emitting element, can inject holes from the anode, and can transport holes.

[0596] It is also known that the electrical conductivity of organic semiconductors is strongly influenced by their doping. Such organic semiconductor matrix substances consist of compounds with good electron donating or accepting properties. For doping with electron donating substances, strong electron acceptors such as tetracyanoquinone dimethane (TCNQ) or 2,3,5,6-tetrafluorotetracyano-1,4-benzoquinone dimethane (F4TCNQ) are known (see, for example, the references "M. Pfeiffer, A. Beyer, T. Fritz, K. Leo, Appl. Phys. Lett., 73(22), 3202-3204 (1998)" and "J. Blochwitz, M. Pfeiffer, T. Fritz, K. Leo, Appl. Phys. Lett., 73(6), 729-731 (1998)"). These generate so-called holes by an electron transfer process in the electron donating base substance (hole transport substance). The conductivity of the base material varies considerably depending on the number and mobility of holes. Matrix materials having hole transport properties are known, for example, benzidine derivatives (TPD, etc.) or starburst amine derivatives (TDATA, etc.), or certain metal phthalocyanines (especially zinc phthalocyanine (ZnPc) and the like) (JP 2005-167175 A).

[0597] 6. Cathode in organic electroluminescent devices The cathode 108 serves to inject electrons into the light-emitting layer 105 via the electron injection layer 107 and the electron transport layer 106 .

[0598] The material for forming the cathode 108 is not particularly limited as long as it is a material that can efficiently inject electrons into the organic layer, but the same material as that for forming the anode 102 can be used. Among them, metals such as tin, indium, calcium, aluminum, silver, copper, nickel, chromium, gold, platinum, iron, zinc, lithium, sodium, potassium, cesium, and magnesium, or alloys thereof (magnesium-silver alloy, magnesium-indium alloy, aluminum-lithium alloy such as lithium fluoride / aluminum, etc.), etc. are preferable. In order to increase the electron injection efficiency and improve the device characteristics, lithium, sodium, potassium, cesium, calcium, magnesium, or alloys containing these low work function metals are effective. However, these low work function metals are generally unstable in the air. To improve this point, for example, a method is known in which a trace amount of lithium, cesium, or magnesium is doped into the organic layer to use a highly stable electrode. As other dopants, inorganic salts such as lithium fluoride, cesium fluoride, lithium oxide, and cesium oxide can also be used. However, the dopants are not limited to these.

[0599] Further, for electrode protection, preferred examples include lamination of metals such as platinum, gold, silver, copper, iron, tin, aluminum, and indium, or alloys using these metals, inorganic substances such as silica, titania, and silicon nitride, polyvinyl alcohol, vinyl chloride, hydrocarbon polymer compounds, etc. The method of producing these electrodes is also not particularly limited as long as it can provide electrical continuity, and may be resistance heating, electron beam deposition, sputtering, ion plating, coating, or the like.

[0600] 7. Binders that may be used in each layer of the organic electroluminescent device The materials used for the hole injection layer, hole transport layer, light emitting layer, electron transport layer and electron injection layer can form each layer alone, but they can also be used as a polymer binder by being dispersed in a solvent-soluble resin such as polyvinyl chloride, polycarbonate, polystyrene, poly(N-vinylcarbazole), polymethyl methacrylate, polybutyl methacrylate, polyester, polysulfone, polyphenylene oxide, polybutadiene, hydrocarbon resin, ketone resin, phenoxy resin, polyamide, ethyl cellulose, vinyl acetate resin, ABS resin, polyurethane resin, or a curable resin such as phenol resin, xylene resin, petroleum resin, urea resin, melamine resin, unsaturated polyester resin, alkyd resin, epoxy resin, silicone resin, or the like.

[0601] <<Method for producing organic electroluminescent device>> Each layer constituting an organic EL element can be formed by forming the material to be formed into a thin film by a method such as vapor deposition, resistance heating vapor deposition, electron beam vapor deposition, sputtering, molecular lamination, printing, inkjet, spin coating or casting, coating, etc. The thickness of each layer thus formed is not particularly limited and can be set appropriately according to the properties of the material, but is usually in the range of 2 nm to 5000 nm. The thickness of the film can usually be measured with a quartz crystal oscillation type film thickness measuring device, etc. When forming a thin film by vapor deposition, the vapor deposition conditions vary depending on the type of material, the desired crystal structure and association structure of the film, etc. The vapor deposition conditions are generally a boat heating temperature of +50 to +400°C, a vacuum degree of 10, and a vacuum of 10. -6 ~10 -3 It is preferable to appropriately set the pressure, pressure Pa, deposition rate 0.01 to 50 nm / sec, substrate temperature -150 to +300°C, and film thickness 2 nm to 5 µm.

[0602] Next, as an example of a method for producing an organic EL element, a method for producing an organic EL element consisting of an anode / hole injection layer / hole transport layer / light-emitting layer consisting of a host material and a dopant material / electron transport layer / electron injection layer / cathode will be described. After forming a thin film of an anode material on a suitable substrate by a deposition method or the like to produce an anode, thin films of a hole injection layer and a hole transport layer are formed on the anode. A host material and a dopant material are co-deposited on the anode to form a thin film to produce a light-emitting layer, an electron transport layer and an electron injection layer are formed on the light-emitting layer, and a thin film consisting of a cathode material is further formed by a deposition method or the like to produce a cathode, thereby obtaining a desired organic EL element. In the production of the above-mentioned organic EL element, the production order can also be reversed, and the elements can be produced in the order of a cathode, an electron injection layer, an electron transport layer, a light-emitting layer, a hole transport layer, a hole injection layer, and an anode.

[0603] When applying a DC voltage to the organic EL element obtained in this way, the anode should be set to + and the cathode to -. When a voltage of about 2 to 40 V is applied, light emission can be observed from the transparent or semi-transparent electrode side (anode or cathode, or both). This organic EL element also emits light when a pulse current or an AC current is applied. The waveform of the AC current applied may be any waveform.

[0604] <<Applications of organic electroluminescent devices>> The present invention can also be applied to a display device having an organic EL element or a lighting device having an organic EL element. A display device or lighting device including an organic EL element can be manufactured by a known method, for example by connecting the organic EL element according to this embodiment to a known driving device, and can be driven appropriately using a known driving method such as DC driving, pulse driving, or AC driving.

[0605] Examples of the display device include panel displays such as color flat panel displays, and flexible displays such as flexible color organic electroluminescent (EL) displays (see, for example, JP-A-10-335066, JP-A-2003-321546, JP-A-2004-281086, etc.). Examples of the display system include a matrix and / or segment system. Note that matrix display and segment display may coexist in the same panel.

[0606] A matrix is ​​a display in which pixels are arranged two-dimensionally, such as in a grid or mosaic pattern, and a collection of pixels is used to display characters and images. The shape and size of the pixels are determined by the application. For example, square pixels with sides of 300 μm or less are usually used to display images and characters on computers, monitors, and televisions, and pixels with sides of mm order are used for large displays such as display panels. For monochrome display, pixels of the same color are arranged, but for color display, red, green, and blue pixels are displayed side by side. In this case, there are typically delta types and stripe types. The driving method for this matrix can be either line sequential driving method or active matrix. Line sequential driving has the advantage of being simpler in structure, but when considering operating characteristics, active matrix may be superior, so it is necessary to use it according to the application.

[0607] In the segment type, a pattern is formed to display predetermined information, and a predetermined area is illuminated. Examples include time and temperature displays in digital clocks and thermometers, operating status displays in audio equipment and induction cookers, and panel displays in automobiles.

[0608] Examples of the lighting device include lighting devices for indoor lighting, backlights for liquid crystal display devices, etc. (see, for example, JP 2003-257621 A, JP 2003-277741 A, JP 2004-119211 A, etc.). Backlights are mainly used for the purpose of improving the visibility of non-self-luminous display devices, and are used in liquid crystal display devices, clocks, audio devices, automobile panels, display boards, signs, etc. In particular, for liquid crystal display devices, particularly backlights for personal computers, where thinning is an issue, it is difficult to make them thin because conventional types are made of fluorescent lamps and light guide plates, so the backlight using the light-emitting element according to this embodiment is characterized by its thinness and light weight. EXAMPLES

[0609] The present invention will be described in more detail below with reference to examples, but the present invention is not limited thereto. First, synthesis examples of the compounds used in the examples will be described below.

[0610] Synthesis Example (1-1) Synthesis of compound (1-45) [ka]

[0611] A solution of 9-bromophenanthrene (12.4 g) in cyclopentyl methyl ether (CPME, 150 mL) was cooled to -49°C, and a solution of n-butyllithium in hexane (1.6 M, 30 mL) was added dropwise thereto. The reaction mixture was heated to -8°C, and then a solution of 1,2-benzanthraquinone (5 g) in CPME (100 mL) was added dropwise thereto, followed by stirring at room temperature for 2 hours. Water (100 mL) 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 Solmix A-11 (trade name, manufactured by Japan Alcohol Sales Co., Ltd.) (200 mL) to obtain a pale yellow solid. To this solid, potassium iodide (8.7 g), sodium phosphinate monohydrate (2.5 g), and acetic acid (100 mL) were added, and the mixture was stirred at reflux temperature for 2 hours. The reaction mixture was cooled to 60°C, and the precipitated solid was filtered under reduced pressure. The solid was purified by washing with water (100 mL), Solmix A-11 (100 mL), and toluene (100 mL) in that order, to obtain 3.5 g of compound (1-45) as a yellow solid.

[0612] [ka]

[0613] The structure of the obtained compound was confirmed by NMR measurement. 1 H-NMR (400MHz, CDCl 3 ):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).

[0614] Synthesis Example (1-2) Synthesis of compound (1-7) [ka]

[0615] Compound (1-7) was synthesized according to the method described in the above Synthesis Example (1-1). Mass spectrum analysis confirmed that the obtained compound was compound (1-7). EI-MS: m / z=481.

[0616] Synthesis Example (1-3) Synthesis of compound (1-242) [ka]

[0617] Compound (1-242) was synthesized according to the method described in the above Synthesis Example (1-1). Mass spectrum analysis confirmed that the obtained compound was compound (1-242). EI-MS: m / z=633.

[0618] Synthesis Example (1-4) Synthesis of compound (1-90) [ka]

[0619] Compound (1-90) was synthesized according to the method described in WO 2009 / 081776. Mass spectrometry confirmed that the compound obtained was compound (1-90). EI-MS: m / z=557.

[0620] Synthesis Example (1-5) Synthesis of compound (1-78) [ka]

[0621] Compound (1-78) was synthesized according to the method described in WO 2009 / 081776. Mass spectrum analysis confirmed that the obtained compound was compound (1-78). EI-MS: m / z=557.

[0622] Synthesis Example (1-6) Synthesis of compound (1-93) [ka]

[0623] Compound (1-93) was synthesized according to the method described in WO 2009 / 081776. Mass spectrum analysis confirmed that the obtained compound was compound (1-93). EI-MS: m / z=557.

[0624] Synthesis Example (1-7) Synthesis of compound (1-158) [ka]

[0625] Compound (1-158) was synthesized according to the method described in the above Synthesis Example (1-1). Mass spectrum analysis confirmed that the obtained compound was compound (1-158). EI-MS: m / z=633.

[0626] Synthesis Example (1-8) Synthesis of compound (1-161) [ka]

[0627] Compound (1-161) was synthesized according to the method described in WO 2009 / 081776. Mass spectrometry confirmed that the compound obtained was compound (1-161). EI-MS: m / z=633.

[0628] Synthesis Example (1-9) Synthesis of compound (1-170) [ka]

[0629] Compound (1-170) was synthesized according to the method described in WO 2009 / 081776. Mass spectrometry confirmed that the compound obtained was compound (1-170). EI-MS: m / z=683.

[0630] Synthesis Example (1-10) Synthesis of compound (1-8) [ka]

[0631] Compound (1-8) was synthesized according to the method described in WO 2009 / 081776. Mass spectrometry confirmed that the compound obtained was compound (1-8). EI-MS: m / z=481.

[0632] Synthesis Example (1-11) Synthesis of compound (1-48) [ka]

[0633] Compound (1-48) was synthesized according to the method described in WO 2009 / 081776. Mass spectrometry confirmed that the compound obtained was compound (1-48). EI-MS: m / z=531.

[0634] Synthesis Example (1-12) Synthesis of compound (1-185) [ka]

[0635] Compound (1-185) was synthesized according to the method described in WO 2009 / 081776. Mass spectrometry confirmed that the compound obtained was compound (1-185). EI-MS: m / z=547.

[0636] Synthesis Example (1-13) Synthesis of compound (1-203) [ka]

[0637] Compound (1-203) was synthesized according to the method described in WO 2009 / 081776. Mass spectrometry confirmed that the compound obtained was compound (1-203). EI-MS: m / z=583.

[0638] Synthesis Example (1-14) Synthesis of compound (1-129) [ka]

[0639] Compound (1-129) was synthesized according to the method described in WO 2009 / 081776. Mass spectrometry confirmed that the compound obtained was compound (1-129). EI-MS: m / z=557.

[0640] Synthesis Example (1-15) Synthesis of compound (1-244) [ka]

[0641] Compound (1-244) was synthesized according to the method described in the above Synthesis Example (1-1). Mass spectrum analysis confirmed that the obtained compound was compound (1-244). EI-MS: m / z=613.

[0642] Synthesis Example (1-16) Synthesis of compound (1-753-O) [ka]

[0643] Under a nitrogen atmosphere, 7-bromobenzo[a]anthracene (1.0 g), 4,4,5,5-tetramethyl-2-(naphtho[2,3-b]benzofuran-2-yl)-1,3,2-dioxaborolane (1.18 g), potassium phosphate (1.4 g), xylene (10 mL), t-butanol (3 mL), and water (2 mL) were mixed with Pd-132 (Johnson Matthey) (23 mg) and heated and stirred at 110 °C for 1 hour. After cooling to room temperature, water and ethyl acetate were added and stirred for a while, the organic layer was concentrated, and heptane was added to recover the precipitate. Toluene / heptane = 1 / 1 (volume ratio) was added to this precipitate to recover the soluble components, which were purified with a silica gel short-pass column (developing solution: toluene / heptane = 1 / 1 (volume ratio)), and then re-precipitated with heptane to obtain compound (1-753-O) (1.0 g).

[0644] [ka]

[0645] The structure of the obtained compound was confirmed by NMR measurement. 1 H-NMR (CDCl 3 ):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).

[0646] Synthesis Example (1-17) Synthesis of compound (1-714-O) [ka]

[0647] Under nitrogen atmosphere, 2-bromo-benzofuran (24.71 g) was added dropwise to a flask containing magnesium (2.92 g) and tetrahydrofuran (40 mL), and the mixture was heated and stirred at 40 ° C for 1 hour. After cooling to 0 ° C, tetrahydrofuran (100 mL) was added, benz [a] anthracen-12 (7H)-one (24.43 g) was added dropwise, and the reaction medium was refluxed for 2 hours. After cooling to 0 ° C, 1N-HCl aqueous solution (100 mL) was added dropwise, and the mixture was stirred for 1 hour. The organic layer was extracted with ethyl acetate, washed with potassium carbonate aqueous solution and pure water, and then dried with sodium sulfate. The organic phase was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain the compound (28.40 g) represented by formula (1-714-O). Mass spectrum analysis confirmed that the obtained compound was compound (1-714-O). EI-MS: m / z = 395.

[0648] [ka]

[0649] Synthesis Example (1-18) Synthesis of compound (1-703-O) [ka]

[0650] Compound (1-703-O) was synthesized according to the method described in the above Synthesis Example (1-17). Mass spectrum analysis confirmed that the obtained compound was compound (1-703-O). EI-MS: m / z=445.

[0651] Synthesis Example (1-19) Synthesis of compound (1-702-O) [ka]

[0652] Compound (1-702-O) was synthesized according to the method described in the above Synthesis Example (1-17). Mass spectrum analysis confirmed that the obtained compound was compound (1-702-O). EI-MS: m / z=445.

[0653] Synthesis Example (1-20) Synthesis of compound (1-705-O) [ka]

[0654] Compound (1-705-O) was synthesized according to the method described in the above Synthesis Example (1-17). Mass spectrum analysis confirmed that the obtained compound was compound (1-705-O). EI-MS: m / z=445.

[0655] Synthesis Example (1-21) Synthesis of compound (1-713-O) [ka]

[0656] Compound (1-713-O) was synthesized according to the method described in the above Synthesis Example (1-17). Mass spectrum analysis confirmed that the obtained compound was compound (1-713-O). EI-MS: m / z=445.

[0657] Synthesis Example (1-22) Synthesis of compound (1-718-O) [ka]

[0658] Compound (1-718-O) was synthesized according to the method described in the above Synthesis Example (1-16). Mass spectrum analysis confirmed that the obtained compound was compound (1-718-O). EI-MS: m / z=395.

[0659] Synthesis Example (1-23) Synthesis of compound (1-715-O) [ka]

[0660] Compound (1-715-O) was synthesized according to the method described in the above Synthesis Example (1-17). Mass spectrum analysis confirmed that the obtained compound was compound (1-715-O). EI-MS: m / z=395.

[0661] Synthesis Example (1-24) Synthesis of compound (1-717-S) [ka]

[0662] Compound (1-717-S) was synthesized according to the method described in the above Synthesis Example (1-16). Mass spectrum analysis confirmed that the obtained compound was compound (1-717-S). EI-MS: m / z=411.

[0663] Synthesis Example (1-25) Synthesis of compound (1-714-S) [ka]

[0664] Compound (1-714-S) was synthesized according to the method described in the above Synthesis Example (1-17). Mass spectrum analysis confirmed that the obtained compound was compound (1-714-S). EI-MS: m / z=411.

[0665] Synthesis Example (1-26) Synthesis of compound (1-718-N) [ka]

[0666] Compound (1-718-N) was synthesized according to the method described in the above Synthesis Example (1-16). Mass spectrum analysis confirmed that the obtained compound was compound (1-718-N). EI-MS: m / z=470.

[0667] Synthesis Example (1-27) Synthesis of compound (1-715-N) [ka]

[0668] Compound (1-715-N) was synthesized according to the method described in the above Synthesis Example (1-17). Mass spectrum analysis confirmed that the obtained compound was compound (1-715-N). EI-MS: m / z=470.

[0669] Synthesis Example (1-28) Synthesis of compound (1-551-O) [ka]

[0670] Compound (1-551-O) was synthesized according to the method described in WO 2009 / 081776. Mass spectrum analysis confirmed that the compound obtained was compound (1-551-O). EI-MS: m / z=471.

[0671] Synthesis Example (1-29) Synthesis of compound (1-381-O) [ka]

[0672] Compound (1-381-O) was synthesized according to the method described in WO 2009 / 081776. Mass spectrum analysis confirmed that the compound obtained was compound (1-381-O). EI-MS: m / z=471.

[0673] Synthesis Example (1-30) Synthesis of compound (1-755-O) [ka]

[0674] Compound (1-755-O) was synthesized according to the method described in the above Synthesis Example (1-16). Mass spectrum analysis confirmed that the obtained compound was compound (1-755-O). EI-MS: m / z=445.

[0675] Synthesis Example (1-31) Synthesis of compound (1-778-O) [ka]

[0676] Compound (1-778-O) was synthesized according to the method described in the above Synthesis Example (1-1). Mass spectrum analysis confirmed that the obtained compound was compound (1-778-O). EI-MS: m / z=661.

[0677] Synthesis Example (1-32) Synthesis of compound (1-752-O) [ka]

[0678] Compound (1-752-O) was synthesized according to the method described in the above Synthesis Example (1-16). Mass spectrum analysis confirmed that the obtained compound was compound (1-752-O). EI-MS: m / z=445.

[0679] Synthesis Example (1-33) Synthesis of compound (1-717-O) [ka]

[0680] Compound (1-717-O) was synthesized according to the method described in the above Synthesis Example (1-16). Mass spectrum analysis confirmed that the obtained compound was compound (1-717-O). EI-MS: m / z=395.

[0681] Synthesis Example (1-34) Synthesis of compound (1-785-O) [ka]

[0682] Compound (1-785-O) was synthesized according to the method described in WO 2009 / 081776. Mass spectrum analysis confirmed that the compound obtained was compound (1-785-O). EI-MS: m / z=571.

[0683] Synthesis Example (1-35) Synthesis of compound (1-790-O) [ka]

[0684] Compound (1-790-O) was synthesized according to the method described in WO 2009 / 081776. Mass spectrum analysis confirmed that the compound obtained was compound (1-790-O). EI-MS: m / z=571.

[0685] Synthesis Example (1-36) Synthesis of compound (1-763-O) [ka]

[0686] Compound (1-763-O) was synthesized according to the method described in the above Synthesis Example (1-16). Mass spectrum analysis confirmed that the obtained compound was compound (1-763-O). EI-MS: m / z=445.

[0687] Synthesis Example (1-37) Synthesis of compound (1-387-O) [ka]

[0688] Compound (1-387-O) was synthesized according to the method described in International Publication No. 2009 / 081776. Mass spectrum analysis confirmed that the compound obtained was compound (1-387-O). EI-MS: m / z=547.

[0689] Synthesis Example (1-38) Synthesis of compound (1-1699-O) [ka]

[0690] Compound (1-1699-O) was synthesized according to the method described in International Publication No. 2009 / 081776. Mass spectrum analysis confirmed that the compound obtained was compound (1-1699-O). EI-MS: m / z=697.

[0691] Synthesis Example (1-39) Synthesis of compound (1-1663-O) [ka]

[0692] Compound (1-1663-O) was synthesized according to the method described in International Publication No. 2009 / 081776. Mass spectrum analysis confirmed that the compound obtained was compound (1-1663-O). EI-MS: m / z=723.

[0693] Synthesis Example (1-40) Synthesis of compound (1-383-N) [ka]

[0694] Compound (1-383-N) was synthesized according to the method described in International Publication No. 2009 / 081776. Mass spectrum analysis confirmed that the compound obtained was compound (1-383-N). EI-MS: m / z=546.

[0695] Synthesis Example (1-41) Synthesis of compound (1-1552-O) [ka]

[0696] Compound (1-1552-O) was synthesized according to the method described in WO 2009 / 081776. Mass spectrum analysis confirmed that the compound obtained was compound (1-1552-O). EI-MS: m / z=673.

[0697] Synthesis Example (1-42) Synthesis of compound (1-1683-O) [ka]

[0698] Compound (1-1683-O) was synthesized according to the method described in International Publication No. 2009 / 081776. Mass spectrum analysis confirmed that the compound obtained was compound (1-1683-O). EI-MS: m / z=723.

[0699] Synthesis Example (1-43) Synthesis of compound (1-1680-O) [ka]

[0700] Compound (1-1680-O) was synthesized according to the method described in International Publication No. 2009 / 081776. Mass spectrum analysis confirmed that the compound obtained was compound (1-1680-O). EI-MS: m / z=647.

[0701] Synthesis Example (1-44) Synthesis of compound (1-1599-O) [ka]

[0702] Compound (1-1599-O) was synthesized according to the method described in International Publication No. 2009 / 081776. Mass spectrum analysis confirmed that the compound obtained was compound (1-1599-O). EI-MS: m / z=623.

[0703] Synthesis Example (1-45) Synthesis of compound (1-1116-O) [ka]

[0704] Compound (1-1116-O) was synthesized according to the method described in the above Synthesis Example (1-1). Mass spectrum analysis confirmed that the obtained compound was compound (1-1116-O). EI-MS: m / z=597.

[0705] Synthesis Example (1-46) Synthesis of compound (1-1025-O) [ka]

[0706] Compound (1-1025-O) was synthesized according to the method described in International Publication No. 2009 / 081776. Mass spectrum analysis confirmed that the compound obtained was compound (1-1025-O). EI-MS: m / z=713.

[0707] Synthesis Example (1-47) Synthesis of compound (1-1703-O) [ka]

[0708] Compound (1-1703-O) was synthesized according to the method described in International Publication No. 2009 / 081776. Mass spectrum analysis confirmed that the compound obtained was compound (1-1703-O). EI-MS: m / z=747.

[0709] Synthesis Example (1-48) Synthesis of compound (1-1751-O) [ka]

[0710] Compound (1-1751-O) was synthesized according to the method described in International Publication No. 2009 / 081776. Mass spectrum analysis confirmed that the compound obtained was compound (1-1751-O). EI-MS: m / z=603.

[0711] Synthesis Example (1-49) Synthesis of compound (1-1665-O) [ka]

[0712] Compound (1-1665-O) was synthesized according to the method described in International Publication No. 2009 / 081776. Mass spectrum analysis confirmed that the compound obtained was compound (1-1665-O). EI-MS: m / z=863.

[0713] Synthesis Example (1-50) Synthesis of compound (1-1584-S) [ka]

[0714] Compound (1-1584-S) was synthesized according to the method described in International Publication No. 2009 / 081776. Mass spectrum analysis confirmed that the compound obtained was compound (1-1584-S). EI-MS: m / z=563.

[0715] Synthesis Example (1-51) Synthesis of compound (1-1538-N) [ka]

[0716] Compound (1-1538-N) was synthesized according to the method described in International Publication No. 2009 / 081776. Mass spectrum analysis confirmed that the compound obtained was compound (1-1538-N). EI-MS: m / z=622.

[0717] Synthesis Example (1-52) Synthesis of compound (1-1001-O) [ka]

[0718] Compound (1-1001-O) was synthesized according to the method described in the above Synthesis Example (1-1). Mass spectrum analysis confirmed that the obtained compound was compound (1-1001-O). EI-MS: m / z=547.

[0719] Synthesis Example (1-53) Synthesis of compound (1-1716-O) [ka]

[0720] Compound (1-1716-O) was synthesized according to the method described in International Publication No. 2009 / 081776. Mass spectrum analysis confirmed that the compound obtained was compound (1-1716-O). EI-MS: m / z=623.

[0721] Synthesis Example (1-54) Synthesis of compound (1-1184-O) [ka]

[0722] Compound (1-1184-O) was synthesized according to the method described in the above Synthesis Example (1-1). Mass spectrum analysis confirmed that the obtained compound was compound (1-1184-O). EI-MS: m / z=647.

[0723] Synthesis Example (1-55) Synthesis of compound (1-1140-O) [ka]

[0724] Compound (1-1140-O) was synthesized according to the method described in WO 2009 / 081776. Mass spectrum analysis confirmed that the compound obtained was compound (1-1140-O). EI-MS: m / z=773.

[0725] Synthesis Example (1-56) Synthesis of compound (1-1347-O) [ka]

[0726] Compound (1-1347-O) was synthesized according to the method described in the above Synthesis Example (1-1). Mass spectrum analysis confirmed that the obtained compound was compound (1-1347-O). EI-MS: m / z=823.

[0727] Synthesis Example (1-57) Synthesis of compound (1-1783-O) [ka]

[0728] Compound (1-1783-O) was synthesized according to the method described in the above Synthesis Example (1-1). Mass spectrum analysis confirmed that the obtained compound was compound (1-1783-O). EI-MS: m / z=547.

[0729] Synthesis Example (1-58) Synthesis of compound (1-1759-O) [ka]

[0730] Compound (1-1759-O) was synthesized according to the method described in the above Synthesis Example (1-1). Mass spectrum analysis confirmed that the obtained compound was compound (1-1759-O). EI-MS: m / z=547.

[0731] Synthesis Example (1-59) Synthesis of compound (1-1767-O) [ka]

[0732] Compound (1-1767-O) was synthesized according to the method described in the above Synthesis Example (1-1). Mass spectrum analysis confirmed that the obtained compound was compound (1-1767-O). EI-MS: m / z=647.

[0733] Synthesis Example (1-60) Synthesis of compound (1-1777-O) [ka]

[0734] Compound (1-1777-O) was synthesized according to the method described in International Publication No. 2009 / 081776. Mass spectrum analysis confirmed that the compound obtained was compound (1-1777-O). EI-MS: m / z=623.

[0735] Synthesis Example (1-61) Synthesis of compound (1-1781-O) [ka]

[0736] Compound (1-1781-O) was synthesized according to the method described in International Publication No. 2009 / 081776. Mass spectrum analysis confirmed that the compound obtained was compound (1-1781-O). EI-MS: m / z=561.

[0737] Synthesis Example (1-62) Synthesis of compound (1-1592-O) [ka]

[0738] Compound (1-1592-O) was synthesized according to the method described in WO 2009 / 081776. Mass spectrum analysis confirmed that the compound obtained was compound (1-1592-O). EI-MS: m / z=623.

[0739] Synthesis Example (1-63) Synthesis of compound (1-1798-O) [ka]

[0740] Compound (1-1798-O) was synthesized according to the method described in the above Synthesis Example (1-17). Mass spectrum analysis confirmed that the obtained compound was compound (1-1798-O). EI-MS: m / z=471.

[0741] Synthesis Example (1-64) Synthesis of compound (1-1795-O) [ka]

[0742] Compound (1-1795-O) was synthesized according to the method described in the above Synthesis Example (1-17). Mass spectrum analysis confirmed that the obtained compound was compound (1-1795-O). EI-MS: m / z=431.

[0743] Synthesis Example (1-65) Synthesis of compound (1-1797-O) [ka]

[0744] Compound (1-1797-O) was synthesized according to the method described in the above Synthesis Example (1-17). Mass spectrum analysis confirmed that the obtained compound was compound (1-1797-O). EI-MS: m / z=431.

[0745] Synthesis Example (1-66) Synthesis of compound (1-1805-O) [ka]

[0746] Compound (1-1805-O) was synthesized according to the method described in the above Synthesis Example (1-17). Mass spectrum analysis confirmed that the obtained compound was compound (1-1805-O). EI-MS: m / z=471.

[0747] Synthesis Example (2-1): Synthesis of Compound (2-41) [ka]

[0748] Compound (2-41) was synthesized according to the method described in “Synthesis Example (32)” of WO 2015 / 102118. The structure of the obtained compound was confirmed by NMR measurement. 1 H-NMR (500MHz, CDCl 3 ):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).

[0749] Synthesis Example (2-2): Synthesis of Compound (2-31) [ka]

[0750] Compound (2-31) was synthesized according to the method described in “Synthesis Example (32)” of WO 2015 / 102118.

[0751] The structure of the obtained compound was confirmed by NMR measurement. 1 H-NMR (500MHz, CDCl 3 ):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).

[0752] Synthesis Example (2-3): Synthesis of Compound (2-46) [ka]

[0753] Compound (2-46) was synthesized according to the method described in “Synthesis Example (32)” of WO 2015 / 102118.

[0754] The structure of the obtained compound was confirmed by NMR measurement. 1 H-NMR (CDCl 3 ):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).

[0755] Synthesis Example (2-4): Synthesis of Compound (2-37) [ka]

[0756] Compound (2-37) was synthesized according to the method described in “Synthesis Example (32)” of WO 2015 / 102118.

[0757] The structure of the obtained compound was confirmed by NMR measurement. 1 H-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).

[0758] Synthesis Example (2-5): Synthesis of Compound (2-42) [ka]

[0759] The compound represented by formula (2-42) was synthesized using the same method as in the above-mentioned synthesis example.

[0760] The structure of the obtained compound was confirmed by NMR measurement. 1 H-NMR (CDCl 3 ):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).

[0761] Synthesis Example (2-6): Synthesis of Compound (2-49) [ka]

[0762] Compound (2-49) was synthesized according to the method described in “Comparative Synthesis Example (1)” of JP2016-88927A.

[0763] The structure of the obtained compound was confirmed by NMR measurement. 1 H-NMR (CDCl 3 ):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).

[0764] Synthesis Example (2-7): Synthesis of Compound (2-50) [ka]

[0765] Compound (2-50) was synthesized according to the method described in “Synthesis Example (32)” of WO 2015 / 102118.

[0766] The structure of the obtained compound was confirmed by NMR measurement. 1 H-NMR (CDCl 3 ):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).

[0767] Synthesis Example (2-8): Synthesis of Compound (2-53) [ka]

[0768] Compound (2-53) was synthesized according to the method described in “Synthesis Example (32)” of WO 2015 / 102118.

[0769] The structure of the obtained compound was confirmed by NMR measurement. 1 H-NMR (CDCl 3):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).

[0770] Synthesis Example (2-9): Synthesis of Compound (2-33) [ka]

[0771] Compound (2-33) was synthesized according to the method described in “Synthesis Example (32)” of WO 2015 / 102118.

[0772] The structure of the obtained compound was confirmed by NMR measurement. 1 H-NMR (CDCl 3 ):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,1 H), 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).

[0773] Synthesis Example (2-10): Synthesis of Compound (2-508) [ka]

[0774] Under a nitrogen atmosphere, 4-(t-amyl)aniline (15.0 g) was dissolved in acetonitrile (150 ml), and bromine (22.5 g) was added dropwise thereto under ice cooling and stirred for 0.5 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. The organic layer was then concentrated to obtain a crude product. The crude product was purified using a silica gel short column (eluent: toluene) to obtain intermediate (IA) (20.0 g).

[0775] [ka]

[0776] Under a nitrogen atmosphere, copper chloride (10.1 g) and intermediate (IA) (20.0 g) were dissolved in acetonitrile (100 ml), to which t-butyl nitrite (9.6 g) dissolved in acetonitrile (50 ml) was added dropwise at 60°C, and the mixture was stirred at the same temperature for 0.5 hours. After the reaction, dilute hydrochloric acid and ethyl acetate were added to the reaction solution and stirred, after which the organic layer was separated and washed with water. The organic layer was then concentrated to obtain a crude product. The crude product was purified using a silica gel short column (eluent: toluene / heptane = 1 / 4 (volume ratio)) to obtain intermediate (IB) (19.0 g).

[0777] [ka]

[0778] Under a nitrogen atmosphere, intermediate (IB) (10.0 g), bis(4-t-butylphenyl)amine (18.2 g), dichlorobis(di-t-butyl(4-dimethylaminophenyl)phosphino)palladium (Pd-132, 0.21 g) as a palladium catalyst, sodium-t-butoxide (NaOtBu, 7.1 g) and xylene (100 ml) were placed in a flask and heated at 100°C 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. The organic layer was then concentrated to obtain a crude product. The crude product was purified using a silica gel short column (eluent: toluene) to obtain intermediate (IC) (18.0 g).

[0779] [ka]

[0780] A 1.56M t-butyllithium pentane solution (28.9ml) was added to a flask containing intermediate (IC) (18.0g) and t-butylbenzene (500ml) under a nitrogen atmosphere at 0°C. After the dropwise addition, the temperature was raised to 70°C and stirred for 0.5 hours, and then components with a boiling point lower than that of t-butylbenzene were distilled off under reduced pressure. The mixture was cooled to -50°C and boron tribromide (11.3g) was added, and the mixture was heated to room temperature and stirred for 0.5 hours. The mixture was then cooled again to 0°C and N,N-diisopropylethylamine (5.8g) was added, and the mixture was stirred at room temperature until the heat generation subsided, and then heated to 100°C and stirred for 1 hour. The reaction solution was cooled to room temperature, and an aqueous sodium acetate solution cooled in an ice bath was added, followed by ethyl acetate, and the mixture was separated. The organic layer was concentrated and purified with a silica gel short column (eluent: toluene). The obtained crude product was recrystallized from chlorobenzene to obtain compound (2-508) (7.1 g).

[0781] [ka]

[0782] The structure of the obtained compound was confirmed by NMR measurement. 1 H-NMR (CDCl 3 ):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).

[0783] Synthesis Example (2-11): Synthesis of Compound (2-538) [ka]

[0784] Under nitrogen atmosphere, 3,4,5-trichloroaniline (12.0 g), d 5 -Bromobenzene (30.0 g), dichlorobis(di-t-butyl(4-dimethylaminophenyl)phosphino)palladium (Pd-132, 0.43 g) as a palladium catalyst, sodium-t-butoxide (NaOtBu, 14.7 g) and xylene (200 mL) were placed in a flask and heated at 120°C 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 washed with water. The organic layer was then concentrated to obtain a crude product. The crude product was purified using a silica gel short column (eluent: toluene / heptane = 1 / 1 (volume ratio)) to obtain 15.0 g of intermediate (ID).

[0785] [ka]

[0786] Under a nitrogen atmosphere, intermediate (ID) (15.0 g), bis(4-t-butylphenyl)amine (25.9 g), bis(dibenzylideneacetone)palladium (0.48 g), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (SPhos, 0.86 g), sodium-t-butoxide (10.0 g) and xylene (130 mL) were placed in a flask and heated at 100°C 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. The organic layer was then concentrated to obtain a crude product. The crude product was purified using a silica gel short column (eluent: toluene) to obtain 23.0 g of intermediate (IE).

[0787] [ka]

[0788] A 1.62M tert-butyllithium pentane solution (33.5ml) was added to a flask containing intermediate (IE) (23.0g) and tert-butylbenzene (250ml) under a nitrogen atmosphere at 0°C. After the dropwise addition, the temperature was raised to 60°C and stirred for 1 hour, and then components with a boiling point lower than that of tert-butylbenzene were distilled off under reduced pressure. The mixture was cooled to -50°C and boron tribromide (13.6g) was added, and the mixture was heated to room temperature and stirred for 0.5 hours. Then, the mixture was cooled again to 0°C and N,N-diisopropylethylamine (7.0g) was added, and the mixture was stirred at room temperature until the heat generation subsided, and then the mixture was heated to 100°C and stirred for 1 hour. The reaction solution was cooled to room temperature, and an aqueous sodium acetate solution cooled in an ice bath was added, followed by ethyl acetate, and the mixture was separated. The organic layer was concentrated and purified with a silica gel short column (eluent: heated chlorobenzene). The resulting crude product was washed with refluxing heptane and refluxing ethyl acetate, and then reprecipitated from chlorobenzene to obtain compound (2-538) (12.9 g).

[0789] [ka]

[0790] The structure of the obtained compound was confirmed by NMR measurement. 1 H-NMR (CDCl 3 ):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).

[0791] Synthesis Example (2-12): Synthesis of Compound (2-541) [ka]

[0792] Under nitrogen atmosphere, d 5 -Aniline (5.0g), d 5-Bromobenzene (8.25 g), Pd-132 (0.36 g) as a palladium catalyst, NaOtBu (7.1 g) and xylene (100 mL) were placed in a flask and heated at 120°C 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. The organic layer was then concentrated to obtain a crude product. The crude product was purified using a silica gel short column (eluent: toluene / heptane = 1 / 1 (volume ratio)) to obtain 8.1 g of intermediate (IF).

[0793] [ka]

[0794] Under a nitrogen atmosphere, intermediate (IF) (8.0 g), intermediate (IG) (20.6 g), Pd-132 (0.31 g) as a palladium catalyst, NaOtBu (6.4 g), and xylene (100 mL) were placed in a flask and heated at 120°C for 1 hour. 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. The organic layer was then concentrated to obtain a crude product. The crude product was purified using a silica gel short column (eluent: toluene / heptane = 1 / 1 (volume ratio)), and 20.2 g of intermediate (IH) was obtained.

[0795] [ka]

[0796] A 1.62M tert-butyllithium pentane solution (21.2ml) was added to a flask containing intermediate (IH) (10.0g) and tert-butylbenzene (150ml) under a nitrogen atmosphere at 0°C. After the dropwise addition, the temperature was raised to 60°C and stirred for 0.5 hours, and then components with a boiling point lower than that of tert-butylbenzene were distilled off under reduced pressure. The mixture was cooled to -50°C and boron tribromide (8.6g) was added, and the mixture was heated to room temperature and stirred for 0.5 hours. Then, the mixture was cooled again to 0°C and N,N-diisopropylethylamine (4.4g) was added, and the mixture was stirred at room temperature until the heat generation subsided, and then the mixture was heated to 100°C and stirred for 1 hour. The reaction solution was cooled to room temperature, and an aqueous sodium acetate solution cooled in an ice bath was added, followed by ethyl acetate, and the mixture was separated. The organic layer was concentrated and purified with a silica gel short column (eluent: toluene). The obtained crude product was dissolved in toluene, and then heptane was added to precipitate crystals, which were then filtered. The filtered crystals were washed with chilled heptane to obtain compound (2-541) (3.1 g).

[0797] [ka]

[0798] The structure of the obtained compound was confirmed by NMR measurement. 1 H-NMR (CDCl 3 ):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).

[0799] Synthesis Example (2-13): Synthesis of Compound (2-544) [ka]

[0800] Under a nitrogen atmosphere, intermediate (II) (8.4 g), intermediate (IJ) (4.6 g), bis(dibenzylideneacetone)palladium (0.23 g), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (SPhos, 0.32 g), sodium-t-butoxide (3.2 g) and xylene (40 ml) were placed in a flask and heated at 100°C 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. The organic layer was then concentrated to obtain a crude product. The crude product was purified using a silica gel short-path column (eluent: toluene) to obtain intermediate (IK) (8.6 g).

[0801] [ka]

[0802] A flask containing intermediate (IK) (8.6 g) and tert-butylbenzene (90 ml) was charged with 1.62 M tert-butyllithium pentane solution (12.9 ml) under nitrogen atmosphere at 0°C. After the dropwise addition, the temperature was raised to 70°C and stirred for 0.5 hours, and then components with a boiling point lower than that of tert-butylbenzene were distilled off under reduced pressure. The mixture was cooled to -50°C, boron tribromide (5.0 g) was added, the temperature was raised to room temperature and stirred for 0.5 hours. Then, the mixture was cooled again to 0°C, N,N-diisopropylethylamine (2.6 g) was added, and the mixture was stirred at room temperature until the heat generation subsided, and then the mixture was heated to 100°C and stirred for 1 hour. The reaction solution was cooled to room temperature, and an aqueous sodium acetate solution cooled in an ice bath was added, followed by ethyl acetate, and the mixture was 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 by heating, and then purified with a silica gel short-path column (eluent: heated chlorobenzene). The obtained crude product was filtered after adding heptane, and the crystals were washed with heptane to obtain compound (2-544) (6.5 g).

[0803] [ka]

[0804] The structure of the obtained compound was confirmed by NMR measurement. 1 H-NMR (CDCl 3 ):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).

[0805] Synthesis Example (2-14): Synthesis of Compound (2-542) [ka]

[0806] Under a nitrogen atmosphere, intermediate (II) (10.7 g), intermediate (ID) (6.0 g), bis(dibenzylideneacetone)palladium (0.58 g), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (SPhos, 0.82 g), sodium-t-butoxide (4.0 g) and xylene (60 ml) were placed in a flask and heated at 100°C 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. The organic layer was then concentrated to obtain a crude product. The crude product was purified using a silica gel short-path column (eluent: toluene), and the obtained solid was washed with cooled heptane to obtain intermediate (IL) (9.4 g).

[0807] [ka]

[0808] A 1.62M tert-butyllithium pentane solution (13.8ml) was added to a flask containing intermediate (IL) (8.6g) and tert-butylbenzene (100ml) under a nitrogen atmosphere at 0°C. After the dropwise addition, the temperature was raised to 60°C and stirred for 0.5 hours, and then components with a boiling point lower than that of tert-butylbenzene were distilled off under reduced pressure. The mixture was cooled to -50°C, boron tribromide (5.4g) was added, the temperature was raised to room temperature and stirred for 0.5 hours. Then, the mixture was cooled again to 0°C, N,N-diisopropylethylamine (2.8g) was added, and the mixture was stirred at room temperature until the heat generation subsided, and then the mixture was heated to 100°C and stirred for 1 hour. The reaction solution was cooled to room temperature, and an aqueous sodium acetate solution cooled in an ice bath was added, followed by ethyl acetate, and the mixture was 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 by heating, and then purified with a silica gel short-path column (eluent: heated chlorobenzene). The obtained crude product was filtered after adding heptane, and the crystals were washed with heptane to obtain compound (2-542) (5.9 g).

[0809] [ka]

[0810] The structure of the obtained compound was confirmed by NMR measurement. 1 H-NMR (CDCl 3 ):δ=1.32(s,18H), 1.46(s,18H), 5.55(s,2H).

[0811] Synthesis Example (2-15): Synthesis of Compound (2-290) [ka]

[0812] Compound (2-290) was synthesized according to the method described in “Synthesis Example (1)” of WO 2017 / 126443.

[0813] The structure of the obtained compound (2-290) was confirmed by NMR measurement. 1 H-NMR (CDCl 3 ):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).

[0814] Synthesis Example (2-16): Synthesis of Compound (2-351) [ka]

[0815] Compound (2-351) was synthesized according to the method described in “Synthesis Example (5)” of WO 2017 / 126443.

[0816] The structure of the compound of formula (2-351) was confirmed by NMR measurement.

[0817] 1 H-NMR (CDCl 3 ):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).

[0818] The glass transition temperature (Tg) of the compound of formula (2-351) was 165.6°C. [Measurement equipment: Diamond DSC (manufactured by PERKIN-ELMER); Measurement conditions: cooling rate 200℃ / min., heating rate 10℃ / min.]

[0819] Synthesis Example (2-17): Synthesis of Compound (2-60) [ka]

[0820] Compound (2-60) was synthesized in the same manner as in Synthesis Example (2-1). The structure of the obtained compound was confirmed by NMR measurement. 1 H-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).

[0821] Synthesis Example (2-18): Synthesis of Compound (2-561) [ka]

[0822] 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. 1 H-NMR (CDCl 3 ):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).

[0823] Synthesis Example (2-19): Synthesis of Compound (2-574) [ka]

[0824] Compound (2-574) was synthesized using 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.

[0825] Synthesis Example (2-20): Synthesis of Compound (2-578) [ka]

[0826] Compound (2-578) was synthesized using the same method as in Synthesis Example (2-1). The obtained compound was confirmed to be compound (2-578) by mass spectrometry. EI-MS: m / z=889.

[0827] Synthesis Example (2-21): Synthesis of Compound (2-580) [ka]

[0828] Compound (2-580) was synthesized using 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.

[0829] Synthesis Example (2-22): Synthesis of Compound (2-548) [ka]

[0830] Compound (2-548) was synthesized using the same method as in Synthesis Example (2-1). The obtained compound was confirmed to be compound (2-548) by mass spectrometry. EI-MS: m / z=944.

[0831] Synthesis Example (2-23): Synthesis of Compound (2-591) [ka]

[0832] Tri-p-tolylamine (0.287 g, 1.00 mmol), boron triiodide (0.783 g, 2.00 mmol) and o-dichlorobenzene (10.0 ml) were heated and stirred at 150°C for 2 hours under a nitrogen atmosphere. The reaction solution was cooled to room temperature, and 2-isopropenylphenylmagnesium bromide (5.25 ml, 1.2 M, 6.30 mmol) was added. The mixture was then filtered using a Florisil short-path column (eluent: toluene), and the solvent was distilled off under reduced pressure. The crude product obtained was isolated and purified by washing with hexane to obtain 0.309 g of 2,8-dimethyl-10-(2-(prop-1-pen-2-yl)phenyl)-5-(p-tolyl)-5,10-dihydrodibenzo[b,e][1,4]azaborine in a yield of 75%.

[0833] [ka]

[0834] The structure of the obtained compound was confirmed by NMR measurement. 1 H-NMR (CDCl 3 ):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). 13 C-NMR (CDCl 3):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).

[0835] 2,8-Dimethyl-10-(2-(prop-1-pen-2-yl)phenyl)-5-(p-tolyl)-5,10-dihydrodibenzo[b,e][1,4]azaborine (82.2 mg, 0.20 mmol), scandium trifluoromethanesulfonate (0.100 g, 0.20 mmol) and 1,2-dichloroethane (55.0 ml) were heated and stirred at 95°C for 24 hours under a nitrogen atmosphere. After cooling the reaction solution to room temperature, it was filtered using a Florisil short-path column (eluent: toluene) and the solvent was distilled off under reduced pressure. The obtained crude product was isolated and purified using a silica gel column (eluent: hexane / toluene = 6 / 1 (volume ratio)) to obtain 32.0 mg of compound (2-591) in a yield of 39%.

[0836] [ka]

[0837] The structure of the obtained compound was confirmed by NMR measurement. 1 H-NMR (CDCl 3 ):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), 7.1 4-7.31(m,4H), 7.40-7.47(m,3H), 7.57(dt,1H), 7.81(d,1H), 8.44(d,1H), 8.50(s,1H). 13 C-NMR (CDCl 3):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).

[0838] Synthesis Example (2-24): Synthesis of Compound (2-548) [ka]

[0839] Compound (2-548) was synthesized using the same method as in Synthesis Example (2-1). The obtained compound was confirmed to be compound (2-548) by mass spectrometry. EI-MS: m / z=944.

[0840] Synthesis Example (2-25): Synthesis of Compound (2-550) [ka]

[0841] Compound (2-550) was synthesized using the same method as in Synthesis Example (2-1). Mass spectrum analysis confirmed that the obtained compound was compound (2-550). EI-MS: m / z=833.

[0842] Synthesis Example (2-26): Synthesis of Compound (2-32) [ka]

[0843] Compound (2-32) was synthesized using the same method as in Synthesis Example (2-1). Mass spectrum analysis confirmed that the obtained compound was compound (2-32). EI-MS: m / z=645.

[0844] Comparative synthesis example (1) Synthesis of compound (H-1) [ka]

[0845] Compound (H-1) was synthesized by appropriately modifying the raw materials of the method described in WO 2015 / 064560.

[0846] Comparative synthesis example (2) Synthesis of compound (D-1) [ka]

[0847] Compound (D-1) was synthesized according to the synthetic method for compound 1 in WO 2012 / 118164.

[0848] By appropriately changing the raw material compounds, other compounds of the present invention can be synthesized according to the methods of the above-mentioned synthesis examples.

[0849] In order to explain the present invention in more detail, examples of organic EL devices using the compounds of the present invention will be shown below, but the present invention is not limited to these.

[0850] Organic EL devices according to Examples 1 to 44 and Comparative Examples 1 to 5 were prepared, and the emission wavelength (nm), voltage (V), and external quantum efficiency (%) at the time of emitting light with a specific luminance were measured. The time during which the specific luminance was maintained (device life) was also measured.

[0851] The quantum efficiency of a light-emitting element includes internal quantum efficiency and external quantum efficiency, and the internal quantum efficiency indicates the ratio at which the external energy injected as electrons (or holes) into the light-emitting layer of the light-emitting element is converted purely into photons. On the other hand, the external quantum efficiency is calculated based on the amount of these photons that are emitted to the outside of the light-emitting element, and since some of the photons generated in the light-emitting layer are absorbed or continue to be reflected inside the light-emitting element and are not emitted to the outside of the light-emitting element, the external quantum efficiency is lower than the internal quantum efficiency.

[0852] The external quantum efficiency was measured as follows: The luminance of the element was 1000 cd / m using an Advantest voltage / current generator R6144. 2 The element was made to emit light by applying a voltage that would result in a value of 10 ...

[0853] The material configuration of each layer in the fabricated organic EL devices according to Examples 1 to 12 and Comparative Examples 1 to 3, and the EL characteristic data are shown in Table 1 below.

[0854] [Table 1]

[0855] The material configuration of each layer in the organic EL devices fabricated according to Examples 13 to 44 and Comparative Examples 4 and 5, and the EL characteristic data are shown in Table 2 below.

[0856] [Table 2] TIFF2025038105000380.tif221170

[0857] In the above tables, "HI" stands for N 4 ,N 4’ -Diphenyl-N 4 ,N 4’ -bis(9-phenyl-9H-carbazol-3-yl)-[1,1'-biphenyl]-4,4'-diamine, "HAT-CN" is 1,4,5,8,9,12-hexaazatriphenylene hexacarbonitrile, "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, and "HT-2" is N,N-bis(4-(dibenzo[b,d]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]benzoxaborinino[2,3,4-kl]phenoxaborinine, and "ET-2" is 3,3'-((2-phenylanthracene-9,10-diyl)bis(4,1-phenylene))bis(4-methylpyridine). The chemical structures are shown below along with "Liq."

[0858] [ka]

[0859] <Example 1> <Device comprising host material: compound (1-8) and dopant material: compound (2-41)> A 26 mm × 28 mm × 0.7 mm glass substrate (manufactured by Optoscience Co., Ltd.) on which an ITO film having a thickness of 180 nm was formed by sputtering and polished to 150 nm was used as a transparent support substrate. This transparent support substrate was fixed to a substrate holder of a commercially available deposition device (manufactured by Choshu Sangyo Co., Ltd.), and a tantalum deposition boat containing HI, HAT-CN, HT-1, HT-2, compound (1-8), compound (2-41), ET-1, and ET-2, and an aluminum nitride deposition boat containing Liq, magnesium, and silver, respectively, were attached.

[0860] The following layers were formed in order on the ITO film of the transparent support substrate as shown in Table 1. The vacuum chamber was opened to 5×10 -4 The pressure was reduced to 100 Pa, and HI, HAT-CN, HT-1 and HT-2 were deposited in this order to form a hole injection layer 1 (film thickness 40 nm), a hole injection layer 2 (film thickness 5 nm), a hole transport layer 1 (film thickness 15 nm) and a hole transport layer 2 (film thickness 10 nm). Next, compound (1-8) and compound (2-41) were heated simultaneously and deposited to a thickness of 25 nm to form a light-emitting layer. The deposition rate was adjusted so that the mass ratio of compound (1-8) to compound (2-41) was approximately 98:2. Next, ET-1 was heated and deposited to a thickness of 5 nm to form an electron transport layer 1. Next, ET-2 and Liq were heated simultaneously and deposited to a thickness of 25 nm to form an electron transport layer 2. The deposition rate was adjusted so that the mass ratio of ET-2 to Liq was approximately 50:50. The deposition rate of each layer was 0.01 to 1 nm / sec. Then, Liq was heated and evaporated at a deposition rate of 0.01-0.1 nm / sec to a thickness of 1 nm, and then magnesium and silver were simultaneously heated and evaporated to a thickness of 100 nm to form a cathode, thereby obtaining an organic EL device. At this time, the deposition rate was adjusted between 0.1-10 nm / sec so that the atomic ratio of magnesium to silver was 10:1.

[0861] A DC voltage of 1000 cd / m was applied to the ITO electrode as the anode and the magnesium / silver electrode as the cathode. 2 When the characteristics during light emission were measured, as shown in Table 1, the driving voltage was 3.92 V, the external quantum efficiency was 6.88%, and blue light emission with a wavelength of 461 nm was obtained.

[0862] <Examples 2 to 12> According to Example 1, each organic EL element was produced with the layer structure shown in Table 1, and the EL characteristic data was measured (Table 1).

[0863] <Comparative Examples 1 to 3> According to Example 1, each organic EL element was produced with the layer structure shown in Table 1, and the EL characteristic data was measured (Table 1).

[0864] <Example 13> <Device comprising host material: compound (1-129) and dopant material: compound (2-41)> A 26 mm × 28 mm × 0.7 mm glass substrate (manufactured by Optoscience Co., Ltd.) on which an ITO film having a thickness of 180 nm was formed by sputtering and polished to 150 nm was used as a transparent support substrate. This transparent support substrate was fixed to a substrate holder of a commercially available deposition device (manufactured by Choshu Sangyo Co., Ltd.), and a tantalum deposition boat containing HI, HAT-CN, HT-1, HT-3, compound (1-129), compound (2-41), ET-1, and ET-2, and an aluminum nitride deposition boat containing Liq, magnesium, and silver, respectively, were attached.

[0865] The following layers were formed in order on the ITO film of the transparent support substrate as shown in Table 1. The vacuum chamber was opened to 5×10 -4The pressure was reduced to 100 Pa, and HI, HAT-CN, HT-1, and HT-3 were deposited in this order to form a hole injection layer 1 (film thickness 40 nm), a hole injection layer 2 (film thickness 5 nm), a hole transport layer 1 (film thickness 15 nm), and a hole transport layer 2 (film thickness 10 nm). Next, compound (1-129) and compound (2-41) were heated simultaneously and deposited to a thickness of 25 nm to form a light-emitting layer. The deposition rate was adjusted so that the mass ratio of compound (1-129) and compound (2-41) was approximately 98:2. Next, ET-1 was heated and deposited to a thickness of 5 nm to form an electron transport layer 1. Next, ET-2 and Liq were heated simultaneously and deposited to a thickness of 25 nm to form an electron transport layer 2. The deposition rate was adjusted so that the mass ratio of ET-2 and Liq was approximately 50:50. The deposition rate of each layer was 0.01 to 1 nm / sec. Then, Liq was heated and evaporated at a deposition rate of 0.01-0.1 nm / sec to a thickness of 1 nm, and then magnesium and silver were simultaneously heated and evaporated to a thickness of 100 nm to form a cathode, thereby obtaining an organic EL device. At this time, the deposition rate was adjusted between 0.1-10 nm / sec so that the atomic ratio of magnesium to silver was 10:1.

[0866] A DC voltage of 1000 cd / m was applied to the ITO electrode as the anode and the magnesium / silver electrode as the cathode. 2 When the characteristics during light emission were measured, the driving voltage was 4.07 V and the external quantum efficiency was 6.78%, as shown in Table 2. Next, the fabricated device was subjected to a constant current driving test (current density = 10 mA / cm 2 ) and found that the time for which the luminance was maintained at 90% or more of its initial luminance was 153 hours.

[0867] <Examples 14 to 44> According to Example 13, each organic EL device was produced with the layer structure shown in Table 2, and the EL characteristic data was measured (Table 2).

[0868] <Comparative Examples 4 to 5> According to Example 13, each organic EL device was produced with the layer structure shown in Table 2, and the EL characteristic data was measured (Table 2). [Industrial Applicability]

[0869] The present invention provides an organic EL device which has high external quantum efficiency and is capable of emitting light at a low voltage. [Explanation of symbols]

[0870] 100 Organic electroluminescent device 101 Substrate 102 Anode 103 Hole injection layer 104 Hole transport layer 105 Light-emitting layer 106 Electron transport layer 107 Electron injection layer 108 Cathode

Claims

1. A benzanthracene compound represented by the following formula (1'): 【Chemistry 1】 In formula (1'), Ar ４ ', Ar ５ ', Ar ６ ', Ar ７ ', Ar ８ ', Ar ９ ', Ar １０ ', Ar １１ ', Ar １２ ', Ar １３ ', X ａ ' and X ｂ ' each independently represents hydrogen, phenyl which may be substituted with one or more substituents selected from substituent group A, biphenylyl which may be substituted with one or more substituents selected from substituent group A, terphenylyl which may be substituted with one or more substituents selected from substituent group A, quaterphenylyl which may be substituted with one or more substituents selected from substituent group A, naphthyl which may be substituted with one or more substituents selected from substituent group A, phenalenyl which may be substituted with one or more substituents selected from substituent group A, phenanthryl which may be substituted with one or more substituents selected from substituent group A, any one selected from substituent group A or one or more substituents selected from substituent group A; fluorenyl which may be substituted by any one or more substituents selected from substituent group A; benzofluorenyl which may be substituted by any one or more substituents selected from substituent group A; chrysenyl which may be substituted by any one or more substituents selected from substituent group A; triphenylenyl which may be substituted by any one or more substituents selected from substituent group A; pyrenyl which may be substituted by any one or more substituents selected from substituent group A; anthracenyl which may be substituted by any one or more substituents selected from substituent group A; alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, silyl which may be substituted by alkyl having 1 to 4 carbon atoms, a group represented by the following formula (A) or a group represented by the following formula (B), However, X ａ ' and X ｂ ' cannot both be hydrogen, Substituent group A consists of phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenalenyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenyl, anthracenyl, alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, silyl which may be substituted by alkyl having 1 to 4 carbon atoms, a group represented by formula (A) and a group represented by formula (B); In formula (A) and formula (B), Y is -O-, -S- or >N-R ３９ and R ２１ ~R ３８ are each independently hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, optionally substituted amino, halogen, hydroxy, or cyano; R ２１ ~R ３８ adjacent groups among these may be bonded to each other to form a hydrocarbon ring, an aryl ring or a heteroaryl ring, and at least one hydrogen atom in the formed hydrocarbon ring, aryl ring or heteroaryl ring may be substituted with optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, optionally substituted amino, halogen, hydroxy, or cyano; R ３９ is hydrogen or optionally substituted aryl, The group represented by formula (A) is a group obtained by removing one hydrogen atom from any position of formula (A), and * indicates the position, The group represented by formula (B) is a group obtained by removing one hydrogen atom from any position of formula (B), and * indicates the position, The compound represented by formula (1') contains at least one group selected from the group consisting of a group represented by formula (A) and a group represented by formula (B), At least one hydrogen atom in the compound represented by formula (1') may be substituted with halogen, cyano, or deuterium. 【Chemistry 2】

2. Formula (A) is any one of formulas (A-1) to (A-14), and formula (B) is formula (B-1), In formula (A-1) to formula (A-14) and formula (B-1), Y is -O-, -S-, or >N-R ３９ and R ３９ is hydrogen or aryl, and at least one hydrogen in each of the groups represented by formulae (A-1) to (A-14) and (B-1) may be substituted with alkyl, cycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, arylthio, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, diaryl-substituted amino, diheteroaryl-substituted amino, arylheteroaryl-substituted amino, halogen, hydroxy, or cyano; The groups represented by formulae (A-1) to (A-14) are groups obtained by removing one hydrogen atom from any one of the positions of formulae (A-1) to (A-14), respectively, and * indicates the position. The group represented by formula (B-1) is a group obtained by removing one hydrogen atom from any position of formula (B-1), and * indicates the position. The benzanthracene compound according to claim 1. 【Chemistry 3】

3. The benzanthracene compound according to claim 1 or 2, represented by the following formula (1'a): 【Chemistry 4】 In formula (1'a), X ａ ' and X ｂ each ' is independently hydrogen, phenyl which may be substituted with one or more substituents selected from substituent group A, biphenylyl which may be substituted with one or more substituents selected from substituent group A, naphthyl which may be substituted with one or more substituents selected from substituent group A, phenanthryl which may be substituted with one or more substituents selected from substituent group A, a group represented by formula (A) or a group represented by formula (B), and X ａ ' and X ｂ At least one of ' is a group containing a group represented by formula (A) or formula (B), Ar ７ ', Ar ８ ', Ar １１ ', and Ar １２ each ' is independently hydrogen, methyl, t-butyl, phenyl, biphenylyl, or naphthyl; At least one hydrogen atom in the compound represented by formula (1'a) may be substituted with halogen, cyano, or deuterium.

4. X ａ ' and X ｂ 4. The benzanthracene compound according to claim 3, wherein any one of is hydrogen.

5. The benzanthracene compound according to claim 4, which is represented by any one of the following formulas: 【Chemistry 5】 【Chemistry 6】

6. The benzanthracene compound according to claim 4 or 5, wherein in formula (A) and formula (B), Y is -O-.

7. In formula (A) and formula (B), R other than a bond ２１ ~R ３８ The benzanthracene compound according to claim 4 or 5, wherein each of

8. X ａ ' and X ｂ The benzanthracene compound according to claim 3, wherein each of the groups represented by formula (A) or formula (B) is a group containing a group represented by formula (A).

9. The benzanthracene compound according to claim 8, which is represented by the following formula: 【Chemistry 7】

10. The benzanthracene compound according to claim 3, which is represented by any one of the following formulas: 【Chemistry 8】

11. X ａ ' and X ｂ 'teeth, one of them is a phenyl substituted with a group represented by formula (A) or a group represented by formula (B), and the other is an unsubstituted phenyl, one of them is naphthyl substituted with a group represented by formula (A) or a group represented by formula (B), and the other is naphthyl which may be substituted with a group represented by formula (A) or a group represented by formula (B), or The benzanthracene compound according to claim 3, wherein one of the benzanthracene compounds is a phenanthryl substituted with a group represented by formula (A) or a group represented by formula (B), and the other is a phenanthryl which may be substituted with a group represented by formula (A) or a group represented by formula (B).

12. The benzanthracene compound according to claim 11, which is represented by any one of the following formulas: 【Chemistry 9】 【Chemistry 10】 In the above formula, tBu is tertiary butyl.

13. Ar ５ ', Ar ６ ', Ar ７ ', Ar ８ ', or Ar ９ 3. The benzanthracene compound according to claim 1, wherein either one of the groups represented by formula (A) or (B) is a group containing a group represented by formula (A).

14. X ａ ' and X ｂ 'teeth, one of them is unsubstituted phenyl and the other is phenyl which may be substituted with one or more substituents selected from Substituent group A, or Each of them is naphthyl which may be substituted with one or more substituents selected from Substituent Group A, or Each of them is phenanthryl optionally substituted with one or more substituents selected from Substituent Group A, X ａ ' and X ｂ The benzanthracene compound according to claim 13, wherein each of the substituents may be the same or different in the presence or absence and type of one or more substituents selected from the substituent group A.

15. The benzanthracene compound according to claim 14, represented by any one of the following formulas: 【Chemistry 11】

16. Ar ６ ', Ar ７ ', or Ar ８ 16. The benzanthracene compound according to claim 14 or 15, wherein any one of the groups represented by formula (A) or formula (B) is a group containing a group represented by formula (A).

17. The benzanthracene compound according to claim 1, which is represented by any one of the following formulas: 【Chemistry 12】 In the above formula, Me is methyl.

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