Organic electroluminescent devices and benzanthracene compounds

Abstract

Provided are an organic EL device having high external quantum efficiency and a compound that can be used therefor. 【Solution】A benzanthracene compound represented by the following formula (1'a). JPEG2026143789000394.jpg60170 X a ' and X b ' is a group having substituted / unsubstituted phenyl, substituted / unsubstituted biphenylyl, substituted / unsubstituted naphthyl, substituted / unsubstituted phenanthryl, or a specific heterocyclic ring, and Ar 7 ', Ar 8 ', Ar 1 1 ', and Ar 1 2 ' is hydrogen, methyl, t-butyl, phenyl, biphenylyl, or naphthyl.

Description

Technical Field

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

Background Art

[0002] Conventionally, display devices using electroluminescent light emitting elements have been variously studied because they can achieve power saving and thickness reduction. Furthermore, organic electroluminescent elements made of organic materials (hereinafter sometimes referred to as "organic EL elements") have been actively investigated because they can be easily reduced in weight and increased in size. In particular, the development of organic materials having light emitting properties such as blue, which is one of the three primary colors of light, and the combination of a plurality of materials to achieve optimal light emitting properties have been actively researched regardless of whether they are high molecular compounds or low molecular compounds.

[0003] An organic EL element has a structure comprising a pair of electrodes consisting of an anode and a cathode, and one or more layers containing an organic compound disposed between the pair of electrodes. Layers containing organic compounds include a light emitting layer, and charge transport / injection layers that transport or inject charges such as holes and electrons. 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 for organic electroluminescent elements, and Patent Document 3 discloses the use of a benzanthracene compound as a host material in the light emitting layer of an organic electroluminescent element.

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

Prior Art Literature

Patent Documents

[0006]

Patent Document 1

[0007] As described above, various materials have been developed for use in organic EL devices, but in order to increase the range of materials for organic EL devices, there is a need for the development of materials composed of compounds different from conventional ones. The object of the present invention is to provide an organic EL device using a new combination of materials. The object of the present invention is to provide an organic EL device having high external quantum efficiency. [Means for solving the problem]

[0008] As a result of diligent research to solve the above problems, the present inventors have found that an excellent organic electroluminescent element can be obtained by using an emissive layer containing a specific benzanthracene compound as a host material and a polycyclic aromatic compound formed by the condensation of multiple aromatic rings as a dopant material, and have completed the present invention. That is, the present invention provides the following organic electroluminescent element and benzanthracene compound.

[0009] <1> An organic electroluminescent element having a pair of electrodes consisting of an anode and a cathode, and a light-emitting layer disposed between the pair of electrodes, wherein the light-emitting layer comprises 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 multiple 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, and 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, 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 in these rings may be substituted, X 1 and X 2Each of these is independently >O, >NR, >C(-R)2, >S, or >Se, where R in >NR is an optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl, or optionally substituted cycloalkyl, where R in >C(-R)2 is hydrogen, optionally substituted aryl, optionally substituted alkyl, or optionally substituted cycloalkyl, and where R in >NR and / or R in >C(-R)2 may be bonded to the A ring, B ring, and / or C ring by a linking group or single bond. In the compound represented by formula (2) or its polymer, at least one selected from the group consisting of aryl rings and heteroaryl rings may be condensed with at least one cycloalkane, at least one hydrogen in the cycloalkane may be substituted, and at least one -CH2- in the cycloalkane may be substituted with -O- At least one hydrogen atom in the compound or structure represented by formula (2) may be substituted with deuterium, cyano, or halogen.

[0013] <2> In equation (2), Rings A, B, and C are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen in these rings may be substituted with a substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, or substituted or unsubstituted aryloxy, and these rings may also contain a boron atom, X 1 and X 2 Formula (2) consists of a central condensed two-ring structure and a five-membered or six-membered ring that shares a bond with it. X 1 and X 2Each of these is independently >O, >NR, >C(-R)2, >S, or >Se, where R in >NR is an aryl, heteroaryl, alkyl, or cycloalkyl which may be substituted with an alkyl or cycloalkyl, where R in >C(-R)2 is a hydrogen, an aryl, alkyl, or cycloalkyl which may be substituted with an alkyl or cycloalkyl, and where R in >NR and / or R in >C(-R)2 may be -O-, -S-, -C(-R)2-, or bonded to the A, B, and / or C rings by a single bond, where R in -C(-R)2- is hydrogen, alkyl, or cycloalkyl. In the compound represented by formula (2) or its polymer, at least one selected from the group consisting of aryl rings and heteroaryl rings may be condensed with at least one cycloalkane, at least one hydrogen in the cycloalkane may be substituted, and at least one -CH2- in the cycloalkane may be substituted with -O- At least one hydrogen atom in the compound or structure represented by formula (2) may be substituted 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> Organic electroluminescent device as described above.

[0014] <3> The polycyclic aromatic compound or its polymer 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 polymer of a polycyclic aromatic compound having multiple structures represented by formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e), or formula (2-f). <1> Organic electroluminescent device as described above.

[0015] [ka]

[0016] (In equations (2-a), (2-b), (2-c), (2-d), (2-e), and (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 Each of these is independently a hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (the two aryls may be linked by a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyl, wherein at least one hydrogen in each may be substituted with an aryl, heteroaryl, alkyl, cycloalkyl, or substituted silyl, and R 1 ~R 11 Adjacent groups among them may bond together to form an aryl ring or heteroaryl ring with the a, b, or c ring, and at least one hydrogen in the formed ring may be substituted with an aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (the two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyl, and at least one hydrogen in these may be substituted with an aryl, heteroaryl, alkyl, cycloalkyl, or substituted silyl. X XEach of these is independently >O, >S, >NR, or >C(-R)2, where R in >NR is an optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl, or optionally substituted cycloalkyl, and each of the R in >C(-R)2 is independently hydrogen, an optionally substituted aryl, optionally substituted alkyl, or optionally substituted cycloalkyl heteroaryl, alkyl, or cycloalkyl. X 1 and X 2 Each of these is independently >O, >NR, >C(-R)2, >S, or >Se, where R in >NR is a C6-C12 aryl which may be substituted with a C1-C6 alkyl or a C3-C14 cycloalkyl, a C2-C15 heteroaryl which may be substituted with a C1-C6 alkyl or a C3-C14 cycloalkyl, a C1-C6 alkyl, or a C3-C14 cycloalkyl, and R in >C(-R)2 is hydrogen, C4 A C6-C12 aryl, C1-C6 alkyl, or C3-C14 cycloalkyl which may be substituted with 1-6 alkyl or C3-C14 cycloalkyl, and the R in >NR and / or the R in >C(-R)2 may be -O-, -S-, -C(-R)2-, or bonded to the a, b and / or c rings by a single bond, and the R in -C(-R)2- is a C1-C6 alkyl or a C3-C14 cycloalkyl. In the compounds represented by formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e), or formula (2-f), or their polymers, at least one selected from the group consisting of aryl rings and heteroaryl rings may be condensed with at least one cycloalkane, at least one hydrogen in the cycloalkane may be substituted, and at least one -CH2- in the cycloalkane may be substituted with -O-. In the compounds or structures represented by formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e), or formula (2-f), at least one hydrogen atom may be substituted 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-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e), or formula (2-f).

[0017] <4> The polycyclic aromatic compound or its polymer is a polycyclic aromatic compound represented by formula (2-a) or a polymer of a polycyclic aromatic compound having multiple structures represented by formula (2-a). <3> Organic electroluminescent device as described above.

[0018] <5> The aforementioned polycyclic aromatic compound is represented by any of the following structural formulas: <4> Organic electroluminescent element described above; [ka]

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

[0020] <6> The aforementioned polycyclic aromatic compound is represented by any of the following structural formulas: <4> Organic electroluminescent element described above; [ka] In the above formula, Me is methyl and tBu is tert-butyl.

[0021] <7> The polycyclic aromatic compound or its polymer is a polycyclic aromatic compound represented by formula (2-b) or a polymer of a polycyclic aromatic compound having multiple structures represented by formula (2-b). <3> Organic electroluminescent device as described above.

[0022] <8> The aforementioned polycyclic aromatic compound is represented by any of the following structural formulas: <7> Organic electroluminescent element described above; [ka] In the above formula, Me is methyl and tBu is tert-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 bEach of these independently consists of 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, terphenyl which may be substituted with one or more substituents selected from substituent group A, quaterphenyl 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, and any of the substituent group A Fluorenyl which may be substituted with one or more substituents, benzofluorenyl which may be substituted with one or more substituents selected from substituent group A, crisenyl 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, anthracenyl which may be substituted with one or more substituents selected from substituent group A, alkyl which has 1 to 6 carbon atoms, cycloalkyl which has 3 to 10 carbon atoms, silyl which may be substituted with alkyl which has 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 will not become hydrogen. Substituent group A consists of phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenalenyl, phenanthryl, fluorenyl, benzofluorenyl, crisenyl, triphenylenyl, pyrenyl, anthracenyl, alkyl groups having 1 to 6 carbon atoms, cycloalkyl groups having 3 to 10 carbon atoms, silyl groups that may be substituted with alkyl groups having 1 to 4 carbon atoms, the group represented by formula (A), and the group represented by formula (B). In equations (A) and (B), Y is -O-, -S-, or >NR 39 And R 21 ~R 38Each is independently hydrogen, 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, and R 21 ~R 38 Adjacent groups may be bonded to each other to form a hydrocarbon ring, aryl ring, or heteroaryl ring, and at least one hydrogen in the formed hydrocarbon ring, aryl ring, or heteroaryl ring may be substituted with an 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 an optionally substituted aryl, The group represented by formula (A) is a group obtained by removing one hydrogen atom from any position in formula (A), where * indicates the position. The group represented by formula (B) is a group obtained by removing one hydrogen atom from any position in formula (B), where * indicates the position. At least one hydrogen atom in the compound represented by formula (1) may be substituted with a halogen, cyano, or deuterium. <1> ~ <8> Organic electroluminescent element as described in any of the following.

[0024] [ka]

[0025] <10> Ar 4 Ar 5 Ar6 Ar 9 Ar 10 , and Ar 13 Both are hydrogen, and Ar 7 Ar 8 Ar 11 Ar 12 , X a and X b Each of these 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, 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, 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> Organic electroluminescent device as described above.

[0026] <11> The group represented by formula (A) is one of the groups represented by formulas (A-1) to (A-14), and the group represented by formula (B) is the group represented by formula (B-1). <9> or <10> Organic electroluminescent device as described above. [ka]

[0027] (In equations (A-1) to (A-14) and (B-1), Y is -O-, -S-, or >NR) 39 And R 39is hydrogen or aryl, and at least one hydrogen in each group represented by formulas (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 formulas (A-1) to (A-14) are groups obtained by removing one hydrogen atom from any of the positions in formulas (A-1) to (A-14), where * indicates the position. The group represented by formula (B-1) is the group obtained by removing one hydrogen atom from any position in formula (B-1), where * indicates the position.

[0028] <12> The compound represented by formula (1) is a compound represented by one of the following formulas: <1> ~ <8> Organic electroluminescent element as described in any of the following; [ka]

[0029] [ka]

[0030] [ka]

[0031] [ka]

[0032] [ka]

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

[0034] <13> The electron transport layer and / or electron injection layer are disposed between the cathode and the light-emitting layer, and at least one of the electron transport layer and the electron injection layer contains at least one selected from the group consisting of borane derivatives, pyridine derivatives, fluorantene derivatives, BO derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, arylnitrile derivatives, triazine derivatives, benzimidazole derivatives, phenanthroline derivatives, and quinolinol-based metal complexes. <1> ~ <12> Organic electroluminescent element as described in any of the following. <14> The electron transport layer and / or electron injection layer further contains at least one selected from the group consisting of alkali metals, alkaline earth metals, rare earth metals, alkali metal oxides, alkali metal halides, alkaline earth metal oxides, alkaline earth metal halides, rare earth metal oxides, rare earth metal halides, alkali metal organic complexes, alkaline earth metal organic complexes, and rare earth metal organic complexes. <13> Organic electroluminescent device as described above. <15> <1> ~ <14> A display device comprising an organic electroluminescent element as described in any of the following. <16> <1> ~ <14> A lighting device comprising an organic electroluminescent element as described in any of the following.

[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 ', Ar11 ' and Ar 12 ', Ar 13 ', X a ' and X b ' are each independently hydrogen, phenyl optionally substituted by one or more substituents selected from substituent group A, biphenylyl optionally substituted by one or more substituents selected from substituent group A, terphenylyl optionally substituted by one or more substituents selected from substituent group A, quaterphenylyl optionally substituted by one or more substituents selected from substituent group A, naphthyl optionally substituted by one or more substituents selected from substituent group A, phenalenyl optionally substituted by one or more substituents selected from substituent group A, phenanthryl optionally substituted by one or more substituents selected from substituent group A, fluorenyl optionally substituted by one or more substituents selected from substituent group A, benzofluorenyl optionally substituted by one or more substituents selected from substituent group A, chrysenyl optionally substituted by one or more substituents selected from substituent group A, triphenylenyl optionally substituted by one or more substituents selected from substituent group A, pyrenyl optionally substituted by one or more substituents selected from substituent group A, anthracenyl optionally substituted by one or more substituents selected from substituent group A, alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, silyl optionally 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); provided that neither X a ' nor X b ' is hydrogen at the same time, 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 optionally substituted by alkyl having 1 to 4 carbon atoms, the group represented by formula (A) and the group represented by formula (B), In formula (A) and formula (B), Y is -O-, -S- or >N-R 39 , and R 21 to 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, and R 21 to R 38 : adjacent groups among them 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 by 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, and R 39 is hydrogen or optionally substituted aryl, the group represented by formula (A) is a group obtained by removing one hydrogen from any position of formula (A), and * indicates said position, the group represented by formula (B) is a group obtained by removing one hydrogen from any position of formula (B), and * indicates said position, the compound represented by formula (1') contains at least one group selected from the group consisting of the group represented by formula (A) and the group represented by formula (B), at least one hydrogen in the compound represented by formula (1') may be substituted with halogen, cyano, or deuterium.

[0037]

Chemical Formula

[0038] <18> Equation (A) is one of equations (A-1) to (A-14), and equation (B) is equation (B-1), In equations (A-1) to (A-14), and in equation (B-1), Y is -O-, -S-, or >NR 39 And R 39 is hydrogen or aryl, and at least one hydrogen in each group represented by formulas (A-1) to (A-14) and formula (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 formulas (A-1) to (A-14) are groups obtained by removing one hydrogen atom from any of the positions in formulas (A-1) to (A-14), where * indicates the position. The group represented by formula (B-1) is a group obtained by removing one hydrogen atom from any position in formula (B-1), where * indicates the position. <17> The benzanthracene compounds described above.

[0039] [ka]

[0040] <19> It is expressed by the following formula (1'a) <17> or <18> The benzanthracene compounds described above; [ka]

[0041] In formula (1'a), X a 'and X b' 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), X a 'and X b At least one of the groups is a group containing a group represented by formula (A) or formula (B), Ar 7 ', Ar 8 ', Ar 11 ', and Ar 12 ' 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 a halogen, cyano, or deuterium.

[0042] <20> X a 'and X b One of the ' is hydrogen, <19> The benzanthracene compounds described above. <21> Expressed by one of the following formulas: <20> The benzanthracene compounds described above. [ka]

[0043] [ka]

[0044] <22> In equations (A) and (B), Y is -O-. <20> or <21> The benzanthracene compounds described above. <23> In equations (A) and (B), R other than the bond 21 ~R 38 Both are hydrogen. <20> or <21> The benzanthracene compounds described above. <24> X a 'and X b Both of these are groups that contain a group represented by formula (A) or formula (B). <19> The benzanthracene compounds described above.

[0045] <25> The following formula is used: <24> The benzanthracene compounds described above. [ka]

[0046] <26> Expressed by one of the following formulas: <19> The benzanthracene compounds described above. [ka]

[0047] <27> X a 'and X b 'teeth, Either one of the compounds is a phenyl compound substituted with a group represented by formula (A) or a group represented by formula (B), and the other is an unsubstituted phenyl compound. Either one naphthyl is substituted with a group represented by formula (A) or formula (B), and the other naphthyl may be substituted with a group represented by formula (A) or formula (B), or A phenanthryl in which one of the groups is substituted with a group represented by formula (A) or formula (B), and the other group may be substituted with a group represented by formula (A) or formula (B). <19> The benzanthracene compounds described above.

[0048] <28> Expressed by one of the following formulas: <27> The benzanthracene compounds described above; [ka]

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

[0050] <29> Ar 5 ', Ar 6 ', Ar 7 ', Ar 8 ', or Ar 9 One of the groups is a group that contains a group represented by formula (A) or formula (B). <17> or <18> The benzanthracene compounds described above. <30> X a 'and X b 'teeth, Either one is an unsubstituted phenyl compound, and the other is a phenyl compound that may be substituted with one or more substituents selected from substituent group A. In either case, the naphthyl may be substituted with one or more substituents selected from substituent group A, or Each of these is a phenanthryl which may be substituted with one or more substituents selected from substituent group A. X a 'and X b ' may be the same or different in terms of the presence and type of one or more substituents selected from substituent group A. <29> The benzanthracene compounds described above.

[0051] <31> Expressed by one of the following formulas: <30> The benzanthracene compounds described above. [ka]

[0052] <32> Ar 6 ', Ar 7 ', or Ar 8 One of the groups is a group that contains a group represented by formula (A) or formula (B). <30> or <31> The benzanthracene compounds described above.

[0053] <33> Expressed by one of the following formulas: <17> The benzanthracene compounds described above; [ka] In the above formula, Me represents methyl. [Effects of the Invention]

[0054] The present invention provides an organic EL element using a novel combination of materials. The organic EL element of the present invention has high external quantum efficiency and is capable of emitting light at low voltage. Furthermore, the present invention provides a benzanthracene compound that can be used in the manufacture of the above organic EL element. [Brief explanation of the drawing]

[0055] [Figure 1] This is a schematic cross-sectional view showing an example of an organic EL element of the present invention. [Modes for carrying out the invention]

[0056] The present invention will be described in detail below. The following descriptions of constituent elements may be based on representative embodiments or specific examples, but the present invention is not limited to such embodiments. In this specification, numerical ranges represented by "~" mean a range that includes the numbers written before and after "~" as the lower and upper limits. Also, in this specification, "hydrogen" in the description of structural formulas means "hydrogen atom (H)".

[0057] In this specification, chemical structures and substituents are sometimes expressed in terms of carbon number. However, when a substituent is substituted into a chemical structure, or when a substituent is further substituted into another substituent, the carbon number refers to the carbon number of the chemical structure and the substituent itself, and does not refer to the total carbon number of the chemical structure and substituent, or the total carbon number of the substituents. For example, "substituent B with carbon number Y substituted by substituent A with carbon number X" means that "substituent A with carbon number X" is substituted into "substituent B with carbon number Y," and carbon number Y is not the total carbon number of substituent A and substituent B. Also, for example, "substituent B with carbon number Y substituted by substituent A" means that "substituent A (without carbon number limitation)" is substituted into "substituent B with carbon number Y," and carbon number Y is not the total carbon number of substituent A and substituent B.

[0058] <<Organic Electroluminescent Light>> The organic electroluminescent element 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. Figure 1 is a schematic cross-sectional view showing an example of the organic EL element of the present invention.

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

[0060] The organic EL element 100 may also be configured by reversing the manufacturing order, for example, by having 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 emissive layer 105 provided on the electron transport layer 106, a hole transport layer 104 provided on the emissive 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 necessarily required; the minimum configuration unit consists of an anode 102, a light-emitting layer 105, and a cathode 108, and the hole injection layer 103, hole transport layer 104, electron transport layer 106, and electron injection layer 107 are optional layers. Furthermore, 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 / emissive layer / electron transport layer / electron injection layer / cathode" configurations, other configurations of layers constituting an organic EL element include "substrate / anode / hole transport layer / emissive layer / electron transport layer / electron injection layer / cathode", "substrate / anode / hole injection layer / emissive layer / electron transport layer / electron injection layer / cathode", "substrate / anode / hole injection layer / hole transport layer / emissive layer / electron injection layer / cathode", and "substrate / anode / hole injection layer / hole transport layer / emissive layer / electron transport The configuration may also be "transport layer / cathode", "substrate / anodode / emissive layer / electron transport layer / electron injection layer / cathode", "substrate / anodode / hole transport layer / emissive layer / electron injection layer / cathode", "substrate / anodode / hole transport layer / emissive layer / electron transport layer / cathode", "substrate / anodode / hole injection layer / emissive layer / electron injection layer / cathode", "substrate / anodode / hole injection layer / emissive layer / electron transport layer / cathode", "substrate / anodode / emissive layer / electron transport layer / cathode", or "substrate / anodode / emissive layer / electron injection layer / cathode".

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

[0064] There are mainly two light-emitting mechanisms for organic EL devices: fluorescence emission, which uses light emitted from an excited singlet state, and phosphorescence emission, which uses light emitted from an excited triplet state. Typical fluorescent materials have low exciton utilization efficiency, at approximately 25%. However, by using the phenomenon of triplet-triplet fusion (TTF), in which singlet excitons are generated from multiple triplet excitons, up to 40-62.5% of the energy can be utilized for light emission.

[0065] There are two ways in which singlet excitons can be generated from triplet excitons: on the host material molecule and on the dopant material molecule. In this case, it is preferable that the triplet energy level of the dopant material is higher than that of the host material. When this triplet energy level relationship is satisfied, triplet excitons generated on the host material do not move to the dopant material, which has a higher triplet energy. Furthermore, triplet excitons generated on the dopant material molecule rapidly transfer energy to the host material molecule. That is, singlet excitons are efficiently generated on the host material through collisions between triplet excitons without the triplet excitons moving to the dopant material. Moreover, if 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 fluorescence emission of the dopant material. This energy transfer from host to dopant is a Förster-type energy transfer. Generally, it is known that the greater the overlap integral of the host's fluorescence spectrum and the dopant's absorption spectrum, the more efficient Förster-type energy transfer occurs between the host and the dopant.

[0066] By utilizing the host material, which is a benzanthracene compound represented by formula (1) of the present invention, and the dopant material, which is a polycyclic aromatic compound containing boron represented by formula (2), it becomes possible to design materials and devices that satisfy the aforementioned conditions for an appropriate energy level relationship between the host and dopant, and a large overlap integral intensity of the spectrum. As a result, the light-emitting layer of the present invention can efficiently generate the TTF phenomenon, providing good device characteristics.

[0067] The light-emitting layer of the organic electroluminescent device of the present invention comprises 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 multiple 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 element 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 13Each is independently hydrogen, an optionally substituted aryl, an optionally substituted heteroaryl, an optionally substituted diarylamino, an optionally substituted diheteroarylamino, an optionally substituted arylheteroarylamino, an optionally substituted alkyl, an optionally substituted cycloalkyl, an optionally substituted alkenyl, an optionally substituted alkoxy, an optionally substituted aryloxy, an optionally substituted arylthio, or an optionally substituted silyl, and 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 Not all of them become hydrogen at the same time, and at least one hydrogen in the compound represented by formula (1) may be substituted with a halogen, cyano, deuterium, or an optionally substituted heteroaryl.

[0071] In formula (1), the "aryl" in "array that may be substituted" can be, for example, aryls having 6 to 30 carbon atoms, preferably aryls having 6 to 16 carbon atoms, more preferably aryls having 6 to 12 carbon atoms, and particularly preferably aryls having 6 to 10 carbon atoms.

[0072] Specific examples of "aryl" include monocyclic phenyl, bicyclic biphenylyl, condensed bicyclic naphthyl, tricyclic terpheniryl (m-terpheniryl, o-terpheniryl, p-terpheniryl), condensed tricyclic anthracenyl, acenaphthirenyl, fluorenyl, phenalenyl, phenantrenyl, condensed tetracyclic triphenylenyl, pyrenyl, naphthacenyl, and condensed pentacyclic perilenyl, pentacenyl, etc.

[0073] In formula (1), the "heteroaryl" in "may be substituted" can be, for example, a heteroaryl having 2 to 30 carbon atoms, preferably a heteroaryl having 2 to 25 carbon atoms, more preferably a heteroaryl having 2 to 20 carbon atoms, even more preferably a heteroaryl having 2 to 15 carbon atoms, and particularly preferably a heteroaryl having 2 to 10 carbon atoms. Examples of heteroaryls include heterocycles containing 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen in addition to carbon as ring constituent atoms.

[0074] Specific examples of "heteroaryls" include pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridyl, pyrimidinyl, pyridadinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, and s Examples include linnolyl, quinazolyl, quinoxalinyl, phthalazinyl, naphthilidinyl, prinyl, pteridinyl, carbazolyl, acridinyl, phenoxathiinyl, phenoxadinyl, phenothiazinyl, phenadinyl, indolidinyl, furyl, benzofuranil, isobenzofuranil, dibenzofuranil, thienyl, benzo[b]thienyl, dibenzothienyl, flazanil, oxadiazolyl, thianthrenyl, naphthobenzofuranil, and naphthobenzothienyl.

[0075] Examples of "heteroaryls that may be substituted" include the group represented by formula (A) and the group represented by formula (B), which will be described later.

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

[0077] Specifically, examples include diphenylamino, dinaphthylamino, phenylnaphthylamino, dipyridylamino, phenylpyridylamino, and naphthylpyridylamino.

[0078] In formula (1), the "alkyl" in "optionally substituted alkyl" may be either linear or branched, for example, a linear alkyl having 1 to 24 carbon atoms or a branched alkyl having 3 to 24 carbon atoms. A C1 to C18 alkyl (a branched alkyl having 3 to 18 carbon atoms) is preferred, a C1 to C12 alkyl (a branched alkyl having 3 to 12 carbon atoms) is more preferred, a C1 to C6 alkyl (a branched alkyl having 3 to 6 carbon atoms) is even more preferred, and a C1 to C4 alkyl (a 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] In formula (1), the "cycloalkyl" in "may be substituted" can be, for example, a cycloalkyl having 3 to 24 carbon atoms, preferably a cycloalkyl having 3 to 20 carbon atoms, more preferably a cycloalkyl having 3 to 16 carbon atoms, even more preferably a cycloalkyl having 3 to 14 carbon atoms, even more preferably a cycloalkyl having 5 to 10 carbon atoms, particularly preferably a cycloalkyl having 5 to 8 carbon atoms, and most preferably a cycloalkyl having 5 to 6 carbon atoms.

[0081] Specific examples of cycloalkyls include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and their alkyl (especially methyl) substituted derivatives having 1 to 4 carbon atoms, as well as norbornel, 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 decahydroazlenyl.

[0082] In formula (1), the "alkenyl" in "may be substituted" can be a straight-chain alkenyl having 2 to 24 carbon atoms or a branched-chain alkenyl having 4 to 24 carbon atoms. Alkenyls having 2 to 18 carbon atoms are preferred, alkenyls having 2 to 12 carbon atoms are more preferred, alkenyls having 2 to 6 carbon atoms are even more preferred, and alkenyls having 2 to 4 carbon atoms are particularly preferred. Specific examples of "alkenyls" include vinyl, allyl, and butadienyl.

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

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

[0085] In formula (1), the "aryloxy" in "arranged aryloxy" refers to a group in which the hydrogen of the -OH group is replaced with an aryl group, and the explanation of this aryl can be found by referring to the above explanation for "aryl".

[0086] In formula (1), the "arylthio" in "arrangethio which may be substituted" refers to a group in which the hydrogen of the -SH group is substituted with an aryl group, and the explanation of this aryl can be found by referring to the above explanation for "aryl".

[0087] Examples of "optionally substituted silyls" in formula (1) include trialkylsilyls. A "trialkylsilyl" is a silyl in which each of the three hydrogen atoms is independently substituted with an alkyl group. The description of this alkyl group can be found above by referring to "alkyl". Preferred alkyl groups for substitution are those having 1 to 4 carbon atoms, specifically including methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, t-butyl, and cyclobutyl.

[0088] Specific examples of "trialkylsilyls" include trimethylsilyl, triethylsilyl, tripropylsilyl, tri-i-propylsilyl, tributylsilyl, trisec-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 equation (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 Regarding the term "may be substituted," examples of substituents include alkyl, aryl, or heteroaryl compounds. These alkyl, aryl, or heteroaryl compounds can be those mentioned above as "alkyl," "aryl," and "heteroaryl." The number of substituents may be any number up to the maximum number of substitutions possible, 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 substituted with a halogen, cyano, or deuterium. Examples of halogens in this case include 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 of these independently may be phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, phenalenyl, phenanthryl, phenanthryl, or one or more substituents selected from substituent group A. Preferably, the group is a fluorenyl which may be substituted with a substituent, a benzofluorenyl which may be substituted with one or more substituents selected from substituent group A, a crisenyl which may be substituted with one or more substituents selected from substituent group A, a triphenylenyl which may be substituted with one or more substituents selected from substituent group A, a pyrenyl which may be substituted with one or more substituents selected from substituent group A, anthracenyl which may be substituted with one or more substituents selected from substituent group A, an alkyl which has 1 to 6 carbon atoms, a cycloalkyl which has 3 to 10 carbon atoms, a silyl which may be substituted with an alkyl which has 1 to 4 carbon atoms, or a group represented by the following formula (A) or formula (B), in which case X a and X b Either of them may be hydrogen.

[0092] Here, substituent group A consists of phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenalenyl, phenanthryl, fluorenyl, benzofluorenyl, crisenyl, triphenylenyl, pyrenyl, anthracenyl, a group represented by the following formula (A), and a group represented by the following formula (B). The substituent selected from 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 It is more preferable that each of these independently is a phenyl group which may be substituted with one or more substituents selected from substituent group A, a biphenylyl group which may be substituted with one or more substituents selected from substituent group A, a terphenylyl group which may be substituted with one or more substituents selected from substituent group A, a naphthyl group which may be substituted with one or more substituents selected from substituent group A, a phenalenyl group which may be substituted with one or more substituents selected from substituent group A, a phenanthryl group which may be substituted with one or more substituents selected from substituent group A, a fluorenyl group which may be substituted with one or more substituents selected from substituent group A, a triphenylenyl group which may be substituted with one or more substituents selected from substituent group A, a pyrenyl group 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 case X a and X b Either of them may be hydrogen.

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

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

[0096] In equation (1), X a and X b It is also preferable that each of these groups be independently represented by one of the following formulas (1-X1) to (1-X6).

[0097] [ka]

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

[0099] The naphthylene moieties in each of the formulas (1-X1) to (1-X3) may be condensed with a single benzene ring. Examples of structures formed by this condensation are shown below. Note that * indicates the bond position in each formula. [ka]

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

[0101] In equations (1-X4), (1-X5), and (1-X6), Ar 24 Ar 25 , and Ar 26Each of these is preferably independently hydrogen, phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl, fluorenyl, crisenyl, triphenylenyl, pyrenyl, a group represented by formula (A) or 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 Each of these is preferably independently hydrogen, phenyl, biphenylyl, terphenylyl, naphthyl, a C1-C4 alkyl, a C5-C10 cycloalkyl substituted silyl, a group represented by the following formula (A), or the following formula (B); more preferably hydrogen, phenyl, biphenylyl, naphthyl, a group represented by the following formula (A), or the following formula (B); and even more preferably hydrogen, phenyl, naphthyl, or a group represented by the following formula (A).

[0103] X a and X b If at least one of them is a group represented by formula (A) or formula (B), or a group represented by any of formulas (1-X1) to (1-X6) having a group represented by formula (A) or formula (B), then Ar 4 Ar 5 Ar 6 Ar 9 Ar 10 , and Ar 13 Preferably, both are hydrogen. In that case, Ar 7 Ar 8 Ar 11 , and Ar 12Each is preferably independently a silyl substituted with hydrogen, phenyl, biphenylyl, terphenylyl, naphthyl, a C1-C4 alkyl, or a C5-C10 cycloalkyl, more preferably hydrogen, phenyl, biphenylyl, or naphthyl, and even more preferably hydrogen, phenyl, or naphthyl, Ar 7 Ar 8 Ar 11 , and Ar 12 It is most preferable that all of these be hydrogen.

[0104] In another aspect, Ar 5 Ar 6 Ar 7 Ar 8 , or Ar 9 Preferably, one of the groups is a group containing a group represented by formula (A) or formula (B), and Ar 6 Ar 7 , or Ar 8 It is more preferable that one of the groups contains a group represented by formula (A) or formula (B).

[0105] The compound represented by formula (1) may also preferably be the 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 equation (1) above. a , X b Ar 4 Ar 5 Ar 6 Ar7 Ar 8 Ar 9 Ar 10 Ar 11 Ar 12 , and Ar 13 Similar to the above, however, the compound represented by formula (1') contains at least one group selected from the group consisting of the group represented by formula (A) and the group represented by formula (B).

[0107] In formula (1'), X a 'and X b Preferably, each of these 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 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 Preferably, each of these is 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 a compound represented by formula (1) is the compound represented by formula (1'a) below. [ka]

[0110] In formula (1'a), X a 'and X b ' 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), X a 'and X b At least one of the groups is a group containing a group represented by formula (A) or formula (B), Ar 7 ', Ar 8 ', Ar 11 ', and Ar 12 ' 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 a halogen, cyano, or deuterium.

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

[0112] In equation (1'a), Ar7 ', Ar 8 ', Ar 11 ', and Ar 12 Each of these is preferably independently hydrogen, phenyl, biphenylyl, or naphthyl.

[0113] A preferred embodiment of the compound represented by formula (1'a) is X a 'and X b Examples of compounds in which one of the elements is hydrogen are given. a 'and X b Compounds in which either of the elements is hydrogen and Y is -O- in formulas (A) and (B), and X a 'and X b Either of the ' is hydrogen, and in formulas (A) and (B), R other than the bond. 21 ~R 38 Compounds in which both are hydrogen are more preferable.

[0114] Another preferred embodiment of the compound represented by formula (1'a) is X a 'and X b Examples of compounds include those in which either formula (A) or formula (B) is represented by a group. In this case, it is preferable that Y is -O-. Also, Ar 7 ', Ar 8 ', Ar 11 ', and Ar 12 ' is preferably hydrogen in all cases.

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

[0116] Specifically, these are compounds having a structure represented by the following formulas (C), (D), (E), (F), (G), (H), (I), or (J) as a substructure. However, the structures represented by formulas (C), (D), (E), (F), (G), (H), (I), or (J) do not form a fused ring as the basic structure, and in compounds having the structure represented by formula (C) as a substructure, at least one of the two phenyl groups in formula (C) is unsubstituted.

[0117] [ka]

[0118] More specifically, X a 'and X b ' is a compound represented by formula (1'a) such that ' is one of the following: Either one of the compounds is a phenyl compound substituted with a group represented by formula (A) or a group represented by formula (B), and the other is an unsubstituted phenyl compound. Naphthyl (1-naphthyl or 2-naphthyl) in which one of the groups is substituted with the group represented by formula (A) or the group represented by formula (B), and the other may be substituted with the group represented by formula (A) or the group represented by formula (B), A phenanthryl (1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, or 9-phenanthryl) in which one of the molecules is substituted with a group represented by formula (A) or formula (B), and the other molecule may be substituted with a group represented by formula (A) or formula (B).

[0119] Another preferred example of a compound represented by formula (1') is one in which, in formula (1'), Ar 5 Ar 6 Ar 7 Ar 8 , or Ar 9 Examples include compounds in which one of the groups is represented by formula (A) or formula (B). In particular, Ar 6 Ar 7 , or Ar 8 Preferably, one of the groups is a group containing a group represented by formula (A) or formula (B). Compounds having such a structure may further preferably have a structure represented by the above formulas (C), (D), (E), (F), (G), (H), or (I) as a substructure. More specifically, X a 'and X b It is more preferable that ' is one of the following: Either one is an unsubstituted phenyl compound, and the other is a phenyl compound that may be substituted with one or more substituents selected from substituent group A. In either case, the naphthyl (1-naphthyl or 2-naphthyl) may be substituted with one or more substituents selected from substituent group A. Each of these is a phenanthryl (1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, or 9-phenanthryl) which may be substituted with one or more substituents selected from substituent group A. In the above, X a 'and X bThe substituents ' may be the same or different in terms of the presence and type of one or more substituents selected from substituent group A. From the viewpoint of compound synthesis, it is preferable that they be the same, and from the viewpoint of device characteristics, it is preferable that they be different.

[0120] The following describes the group represented by formula (A) and the group represented by formula (B) mentioned above. [ka]

[0121] In equation (A), Y is -O-, -S-, or >NR 39 That is. R 39 R is hydrogen or an optionally substituted aryl. Also, in formula (A), R 21 ~R 28 Each is independently hydrogen, 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, and R 21 ~R 28Adjacent groups may bond to each other to form a hydrocarbon ring, aryl ring, or heteroaryl ring. Furthermore, at least one hydrogen in the formed hydrocarbon ring, aryl ring, or heteroaryl ring may be substituted with an 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. The group represented by formula (A) is the group obtained by removing one hydrogen at any position in formula (A), where * indicates the position.

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

[0123] In equation (B), Y is -O-, -S-, or >NR 39 That is. R 39 R is hydrogen or an optionally substituted aryl. Also, in formula (B), R 29 ~R 38Each is independently hydrogen, 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, and R 29 ~R 38 Adjacent groups may bond to each other to form a hydrocarbon ring, aryl ring, or heteroaryl ring. Furthermore, at least one hydrogen in the formed hydrocarbon ring, aryl ring, or heteroaryl ring may be substituted with an 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. The group represented by formula (B) is the group obtained by removing one hydrogen at any position in formula (B), where * indicates the position.

[0124] R in equation (B) 29 ~R 38 Of these, 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 bond to each other to form a hydrocarbon ring, aryl ring, or heteroaryl ring, the substituents bonded to that ring and the remaining R 29 ~R 38 The total number of groups other than hydrogen is preferably 0 to 2, more preferably 0 to 1, and even more preferably 0.

[0125] R in equations (A) and (B) 21 ~R 38In the "alkyl which may be substituted" part, the "alkyl" can be either linear or branched, for example, a linear alkyl having 1 to 24 carbon atoms or a branched alkyl having 3 to 24 carbon atoms. A alkyl having 1 to 18 carbon atoms (a branched alkyl having 3 to 18 carbon atoms) is preferred, a alkyl having 1 to 12 carbon atoms (a branched alkyl having 3 to 12 carbon atoms) is more preferred, a alkyl having 1 to 6 carbon atoms (a branched alkyl having 3 to 6 carbon atoms) is even more preferred, and a alkyl having 1 to 4 carbon atoms (a 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 equations (A) and (B) 21 ~R 38 In the "aryl that may be substituted" in this expression, examples of "aryl" include aryls having 6 to 30 carbon atoms, preferably aryls having 6 to 16 carbon atoms, more preferably aryls having 6 to 12 carbon atoms, and particularly preferably aryls having 6 to 10 carbon atoms.

[0128] Specific examples of "aryl" include monocyclic phenyl, bicyclic biphenylyl, condensed bicyclic naphthyl, tricyclic terpheniryl (m-terpheniryl, o-terpheniryl, p-terpheniryl), condensed tricyclic acenaphthirenyl, fluorenyl, phenalenyl, phenantrenyl, tetracyclic triphenylenyl, pyrenyl, naphthacenyl, and condensed pentacyclic perilenyl, pentacenyl, etc.

[0129] R in equations (A) and (B) 21 ~R 38 In the "heteroaryl that may be substituted" in this context, examples of "heteroaryl" include heteroaryls having 2 to 30 carbon atoms, with heteroaryls having 2 to 25 carbon atoms being preferred, heteroaryls having 2 to 20 carbon atoms being more preferred, heteroaryls having 2 to 15 carbon atoms being even more preferred, and heteroaryls having 2 to 10 carbon atoms being particularly preferred. Examples of heteroaryls include heterocycles containing 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen in addition to carbon as ring constituent atoms.

[0130] Specific examples of "heteroaryls" include pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridyl, pyrimidinyl, pyridadinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoxyl Examples include noryl, cinnoryl, quinazolyl, quinoxalinyl, phthalazinyl, naphthilidinyl, prinyl, pteridinyl, carbazolyl, acridinyl, phenoxathiinyl, phenoxadinyl, phenothiazinyl, phenadinyl, indolidinyl, furyl, benzofuranil, isobenzofuranil, dibenzofuranil, thienyl, benzo[b]thienyl, dibenzothienyl, flazanil, thiantrenil, naphtobenzofuranil, and naphtobenzothienyl.

[0131] R in equations (A) and (B) 21 ~R 38 In the "alkoxy that may be substituted" in the formula, examples of "alkoxy" include linear alkoxys with 1 to 24 carbon atoms or branched alkoxys with 3 to 24 carbon atoms. Alkoxys with 1 to 18 carbon atoms (branched alkoxys with 3 to 18 carbon atoms) are preferred, alkoxys with 1 to 12 carbon atoms (branched alkoxys with 3 to 12 carbon atoms) are more preferred, alkoxys with 1 to 6 carbon atoms (branched alkoxys with 3 to 6 carbon atoms) are even more preferred, and alkoxys with 1 to 4 carbon atoms (branched alkoxys with 3 to 4 carbon atoms) are particularly preferred.

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

[0133] R in equations (A) and (B) 21 ~R 38 In the phrase "aryloxy which may be substituted," the "aryloxy" refers to a group in which the hydrogen of the -OH group is substituted with an aryl group, and this aryl is the R mentioned above. 21 ~R 38 We can cite the base described as "aryl" in this context.

[0134] R in equations (A) and (B) 21 ~R 38 In the context of "arylthio which may be substituted", the "arylthio" refers to a group in which the hydrogen of the -SH group is substituted with an aryl group, and this aryl is the same as the R mentioned above. 21 ~R 38 We can cite the base described as "aryl" in the context of this.

[0135] R in equations (A) and (B) 21 ~R 38 In this context, "trialkylsilyl" refers to a group in which the three hydrogen atoms of the silyl group are each independently substituted with alkyl groups, and this alkyl group is the R mentioned above. 21~R 38 The group described as "alkyl" in the above can be referenced. Preferred alkyl groups for substitution are alkyl groups having 1 to 4 carbon atoms, specifically including methyl, ethyl, propyl, i-propyl, n-butyl, s-butyl, t-butyl, and cyclobutyl.

[0136] Specific examples of "trialkylsilyls" 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 equations (A) and (B) 21 ~R 38 In the context of "aminos that may be substituted," examples of "substituted aminos" include aminos in which two hydrogens are substituted with aryl or heteroaryl groups. Aminos in which two hydrogens are substituted with aryl groups are diaryl-substituted aminos, aminos in which two hydrogens are substituted with heteroaryl groups are diheteroaryl-substituted aminos, and aminos in which two hydrogens are substituted with aryl and heteroaryl groups are arylheteroaryl-substituted aminos. These aryl and heteroaryl groups are the same as those mentioned above in R 21 ~R 38 The bases described as "aryl" and "heteroaryl" in the above can be cited.

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

[0139] R in equations (A) and (B) 21 ~R 38 Examples of "halogens" in this context include fluorine, chlorine, bromine, and iodine.

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

[0141] In equations (A) and (B), Y is represented as ">NR 39 R in " 39 is hydrogen or an aryl that may be substituted, and this aryl is as described above R 21 ~R 38 The group described as "aryl" in the above can be cited, and its substituent is R 21 ~R 38 The groups described as substituents on can be cited.

[0142] R in equations (A) and (B) 21 ~R 38Adjacent groups may bond to each other to form a hydrocarbon ring, an aryl ring, or a heteroaryl ring. For example, the group in formula (A) that does not form a ring is represented by formula (A-1) below, and the groups that do form a ring are, for example, represented by formulas (A-2) to (A-14) below. Note that at least one hydrogen in any of the groups represented by 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 R 21 ~R 38 The groups described in the above can be cited as each group.

[0143] Examples of rings formed by the bonding of adjacent groups include the cyclohexane ring in the case of hydrocarbon rings, and the aforementioned R in the case of aryl rings and heteroaryl rings. 21 ~R 28 Examples include the ring structures described as "aryl" and "heteroaryl" in formula (A-1), where these rings are formed to condense with one or two benzene rings.

[0144] Examples of groups represented by formula (A) include any group selected from the group consisting of formulas (A-1) to (A-14), and examples of groups represented by formula (B) include the group represented by formula (B-1). A group selected from the group consisting of formulas (A-1) to (A-4) and formula (B-1) is preferred, a group represented by any of formulas (A-1), (A-3), or (A-4) is more preferred, and the group represented by formula (A-1) is 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 from either position in formula (A) and formula (B), respectively, where * indicates the position. In other words, the group represented by formula (A) and the group represented by formula (B) may have any position as the bond position. Among these, either carbon atom on the two benzene rings in the respective structures of formula (A) and formula (B), and R in the respective structures of formula (A) and formula (B). 21 ~R 38 Among them, an atom on any ring formed by the bonding of adjacent groups to each other, or "NR" as Y in the structure of formulas (A) and (B). 39 It is preferable that the group directly bonds with N in the compound (having a bonding bond with them).

[0147] It is preferable that Y in formulas (A) and (B), and Y in formulas (A-1) to (A-14) and (B-1) respectively, be -O-.

[0148] Examples of the groups represented by formula (A) and formula (B) include the groups represented by the following formulas. In the formulas, Y and * have the same definitions as above, and Y is preferably -O-. [ka]

[0149] Specific examples of compounds represented by formula (1) include the compounds represented by the following formulas. In the formulas below, "Me" represents methyl and "tBu" represents tert-butyl. In each formula, Y represents -O-, -S-, or >NR. 39 (R 39 (is defined as above) and R 39 For example, phenyl or deuterium-substituted phenyl. The formula number is, for example, if Y is -O-, then formula (1-331-Y) becomes formula (1-331-O), and if Y is -S- or >NR 39 In these cases, the formulas are (1-331-S) or (1-331-N), respectively. If Y is -O- or >NR 39Examples where this is the case are preferred, and examples where this is the case are particularly preferred.

[0150] [ka]

[0151] [ka]

[0152] [ka]

[0153] [ka]

[0154] [ka]

[0155] [ka]

[0156] [ka]

[0157] [ka]

[0158] [ka]

[0159] [ka]

[0160]

change

[0161]

change

[0162]

change

[0163]

change

[0164]

change

[0165]

change

[0166]

change

[0167]

change

[0168]

change

[0169]

change

[0170]

change

[0171]

change

[0172]

change

[0173]

change

[0174]

change

[0175]

change

[0176]

change

[0177]

change

[0178]

change

[0179]

change

[0180]

change

[0181]

change

[0182]

change

[0183]

change

[0184]

change

[0185]

change

[0186]

change

[0187]

change

[0188]

change

[0189]

change

[0190]

change

[0191]

change

[0192]

change

[0193]

change

[0194]

change

[0195]

change

[0196]

change

[0197]

change

[0198]

change

[0199]

change

[0200]

change

[0201]

change

[0202]

change

[0203]

change

[0204]

change

[0205]

change

[0206]

change

[0207]

change

[0208]

change

[0209]

change

[0210]

change

[0211]

change

[0212]

change

[0213]

change

[0214]

change

[0215]

change

[0216]

change

[0217]

change

[0218]

change

[0219]

change

[0220]

change

[0221]

change

[0222]

change

[0223]

change

[0224]

change

[0225]

change

[0226]

change

[0227]

change

[0228]

change

[0229]

change

[0230]

change

[0231]

change

[0232]

change

[0233]

change

[0234]

change

[0235]

change

[0236]

change

[0237]

change

[0238]

change

[0239]

change

[0240]

change

[0241]

change

[0242]

change

[0243]

change

[0244]

change

[0245]

change

[0246]

change

[0247]

change

[0248]

change

[0249]

change

[0250]

change

[0251]

change

[0252]

change

[0253]

change

[0254]

change

[0255]

change

[0256]

change

[0257]

change

[0258]

change

[0259]

change

[0260]

change

[0261]

change

[0262]

change

[0263] Among the above compounds, formulas (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), (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 Compounds represented by formula (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 methods relating to those described in International Publication No. 2009 / 081776 and Japanese Patent No. 5018138. An example of a reaction pathway to obtain the benzanthracene compound represented by formula (1) by these methods is as follows. In the following formula, Ar and Ar' represent, for example, aryl and heteroaryl compounds.

[0265] [ka]

[0266] Furthermore, the benzanthracene compound represented by formula (1) can also be produced by the reaction pathway 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 polymers The organic EL element of the present invention includes, as a dopant material in the light-emitting layer, a polycyclic aromatic compound represented by the following formula (2) and a polymer of a polycyclic aromatic compound having multiple 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 polymer of a polycyclic aromatic compound having multiple structures represented by the following formulas (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, benzene ring, or five-membered ring structure, respectively, while the other symbols have the same definitions as described above.

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

[0272] Preferred substituents in this case are substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino, substituted or unsubstituted diheteroarylamino, substituted or unsubstituted arylheteroarylamino (amino having an aryl and a heteroaryl), substituted or unsubstituted diarylboryl (the two aryls may be linked by 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 substituents, examples of substituents include aryl, heteroaryl, alkyl, cycloalkyl, diarylamino, and substituted silyl.

[0273] In particular, preferred substituents are substituted or unsubstituted alkyls (especially neopentyls) and cycloalkyls such as adamantyls. Tertiary alkyls (tRs) are also preferred. This is because such bulky substituents prevent deactivation due to molecular aggregation, thereby improving the luminescence quantum yield (PLQY). Substitutive or unsubstituted diarylaminos are also preferred substituents.

[0274] The aforementioned tertial alkyl is represented by the following formula (tR). [ka]

[0275] In the formula (tR), R a , R b , and R c Each of these is an alkyl group having 1 to 24 carbon atoms, and any -CH2- in the alkyl group may be substituted with -O-, and the group represented by formula (tR) is substituted with at least one hydrogen in the compound or structure represented by formula (2) in *.

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

[0277] In equation (tR) of equation (2), R 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 alkyl groups 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 include -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 groups represented by 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, and 1,1-dimethylhexyl groups. Of these, t-butyl and t-amyl are preferred.

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

[0281] The aryl rings or heteroaryl rings in rings A, B, and C are "B", "X 1 " and "X 2 Formula (2) consists of " and preferably has a 5-membered ring or 6-membered ring that shares a bond with the central condensed two-ring structure.

[0282] Here, the "condensed two-ring structure" refers to the "B" and "X" shown in the middle of equation (2). 1 " and "X 2 This refers to a structure formed by the condensation of two saturated hydrocarbon rings, including the above. Furthermore, "a six-membered ring sharing a bond with the condensed bi-ring structure" refers to an a-ring (benzene ring (six-membered ring)) condensed with the condensed bi-ring structure, as shown in formulas (2-a), (2-b), (2-c), (2-d), (2-e), and (2-f). Furthermore, "an aryl ring or heteroaryl ring (which is the A-ring) having this six-membered ring" means that the A-ring is formed by this six-membered ring alone, or that the A-ring is formed by the condensation of other rings, etc., to this six-membered ring. In other words, "an aryl ring or heteroaryl ring (which is the A-ring) having a six-membered ring" here means that a six-membered ring constituting all or part of the A-ring is condensed with the condensed bi-ring structure. The same explanation applies to "five-membered rings". The same explanation also applies to "B-ring (b-ring)" and "C-ring (c-ring)".

[0283] In formula (2), the A ring is 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 This corresponds to the B ring in formula (2), the b ring and its substituent R in formulas (2-a), (2-b), and (2-c). 8 ~R 11 , the b ring and its substituent R in formula (2-d) 10 and R 11 , as well as the b-ring and its substituent R in formulas (2-e) and (2-f) 8 and R 9 This corresponds to the C ring in formula (2), which is the c ring and its substituent R in formula (2-a). 4 ~R 7 , the c ring and its substituent R in formulas (2-b), (2-d), and (2-f) 4 and R 5 , as well as the c ring and its substituent R in formulas (2-c) and (2-e) 6 and R 7 This corresponds to the following: Equation (2-a) corresponds to a structure in which rings having at least a 6-membered ring structure are selected as rings A to C in equation (2), and equations (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 in equation (2), respectively. In this sense, each ring in equations (2-a), etc., is represented by lowercase letters a to c.

[0284] X in equations (2-b), (2-c), (2-d), (2-e), and (2-f) XEach of these is independently >O, >S, >NR, or >C(-R)2. Here, R in >NR is an optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl, or optionally substituted cycloalkyl, and is preferably an optionally substituted aryl, and more preferably an unsubstituted aryl. Also, each of the R in >C(-R)2 is independently hydrogen, an optionally substituted aryl with alkyl or cycloalkyl, an optionally substituted heteroaryl with alkyl or cycloalkyl, an alkyl, or a cycloalkyl, and is preferably an alkyl, and more preferably a methyl. It is preferable that the two Rs in >C(-R)2 are the same. It is also preferable that the two Rs in >C(-R)2 form a ring with each other. X Each of these is preferably >O, >S, or >NR, more preferably >O or >S, and even more preferably >S.

[0285] In equations (2-a), (2-b), (2-c), (2-d), (2-e), and (2-f), R 1 ~R 11 Each of these is independently a hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (the two aryls may be linked by a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyl, wherein at least one hydrogen in each may be substituted with an aryl, heteroaryl, alkyl, cycloalkyl, or substituted silyl.

[0286] R in equations (2-a), (2-b), (2-c), (2-d), (2-e), and (2-f) respectively. 1 ~R 3 Among them, 0 to 1 are substituents other than hydrogen, and the rest are hydrogen, R 4 ~R 7 Among them, 0 to 1 are substituents other than hydrogen, and the rest are hydrogen, R8 ~R 11 Preferably, 0 to 1 substituent is a substituent other than hydrogen, and the rest are hydrogen atoms. R 1 ~R 3 In this molecule, one substituent is not hydrogen, and the others are hydrogen, R 4 ~R 7 In this molecule, one substituent is not hydrogen, and the others are hydrogen, R 8 ~R 11 It is more preferable that one substituent is a non-hydrogen substituent and the others are hydrogen. For preferred non-hydrogen substituents, refer to the description of substituents later as the first substituent (which may have a second substituent). Particularly preferred non-hydrogen substituents are alkyl groups (especially tertiary-alkyl (tR), neopentyl, etc.), cycloalkyl groups (e.g., adamantyl), or substituted or unsubstituted diarylamino groups.

[0287] In formulas (2-a), (2-b), (2-c), (2-d), (2-e), and (2-f), substituents R of the a, b, and c rings are shown. 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 them may bond together to form an aryl ring or heteroaryl ring with the a, b, or c ring, and at least one hydrogen in the formed ring may be substituted with an aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (the two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, or substituted silyl, and at least one hydrogen in these may be substituted with an aryl, heteroaryl, alkyl, cycloalkyl, or substituted silyl.

[0288] For example, the compound represented by formula (2-a) has a ring structure that changes depending on the bonding configuration of the substituents in the a, b, and c rings, as shown in formulas (2-a-1) and (2-a-2) below. The A', B', and C' rings in each formula correspond to the A, B, and C rings in formula (2), respectively. Also, 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 The definition is the same as the definition in equation (2-a).

[0289] [ka]

[0290] The A', B', and C' rings in formulas (2-a-1) and (2-a-2) are, as explained in formula (2-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 The adjacent groups among these rings bond together to form an aryl ring or heteroaryl ring with the a, b, and c rings, respectively (these can also be called fused rings formed by the fusion of other ring structures with the a, b, or c ring). Although not shown in the formulas, there are also compounds in which all of the a, b, and c rings have been changed to A', B', and C' rings. Furthermore, as can be seen from formulas (2-a-1) and (2-a-2), for example, the R of the b ring... 8 and the R of the c ring 7 , R of ring b 11 and the R of ring a1 , the R of the c ring 4 and the R of ring a 3 These groups do not qualify as "adjacent groups," and therefore cannot bond with each other. In other words, "adjacent groups" refers to groups adjacent to each other on the same ring.

[0291] The compounds represented by formulas (2-a-1) and (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 as specific compounds later. That is, for example, a compound having an A' ring (or B' or C' ring) formed by the condensation of a benzene ring (or b or c ring) with a benzene ring, indole ring, pyrrole ring, furan ring, thiophene ring, benzofuran ring, benzothiophene ring, cyclohexene ring, or indene ring, where the resulting condensed ring A' (or condensed ring B' or condensed ring C') is a naphthalene ring, carbazole ring, indole ring, benzofuran ring, benzothiophene ring, dibenzofuran ring, dibenzothiophene ring, tetraline ring, or fluorene ring, respectively.

[0292] Furthermore, in formulas (2-b), (2-c), (2-d), (2-e), and (2-f), similarly, fused rings may be formed by the condensation of other ring structures to the a-ring, b-ring, or c-ring, respectively. For example, the benzene ring, which is the a-ring or b-ring, may be fused with other ring structures to form a fused ring, similar to the benzene ring in formula (2-a) above. In formulas (2-b), (2-c), (2-d), (2-e), and (2-f), in a 5-membered ring that is a b-ring or a c-ring, R 4 ~R 11 It is particularly preferable that adjacent groups among them bond to form a ring and thus a fused ring is formed. For example, in the c ring of formulas (2-b) and (2-c), and the b and c rings of formulas (2-d), (2-e), and (2-f), R 3 ~R 11When adjacent groups bond together to form a ring, a fused ring, such as a B' ring or a C' ring, can be formed. Examples of fused rings when the formed ring is a benzene ring include indole rings, benzofuran rings, and benzothiophene rings.

[0293] As an example, in the 5-membered ring which is the c ring in formula (2-b), R 4 and R 5 Examples of fused rings formed by the bonding of two molecules to form a benzene ring are shown below. [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 These are equivalent to each of the terms in equation (2-b), and their preferred ranges are also the same. 4b , R 5b , R 6b , R 7b R is a hydrogen atom, or a substituent selected from the group consisting of aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (the two aryls may be linked by a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, and substituted silyl, wherein at least one hydrogen atom in these substituents may be substituted with an aryl, heteroaryl, alkyl, cycloalkyl, or substituted silyl. 4b , R 5b , R 6b , R 7bPreferably, 0 to 2 substituents are non-hydrogen and the rest are hydrogen, and more preferably, 1 substituent is non-hydrogen and the rest are hydrogen. For preferred non-hydrogen substituents, refer to the description of substituents later as the first substituent (which may have a second substituent). Particularly preferred non-hydrogen substituents are alkyl groups (especially tertiary alkyl (tR), neopentyl, etc.), cycloalkyl groups (e.g., adamantyl), or substituted or unsubstituted diarylamino groups.

[0295] For example, in equations (2-b), (2-c), (2-d), (2-e), and (2-f), X X When >O, the b ring and / or c ring become furan rings, and the rings corresponding to the B' ring and / or C' ring of formula (2-a-1) formed by the condensation of a benzene ring with these furan rings are benzofuran rings. Also, for example, in equations (2-b), (2-c), (2-d), (2-e), and (2-f), X X When >S, the b ring and / or c ring become thiophene rings, and the rings corresponding to the B' ring and / or C' ring of formula (2-a-1) formed by the condensation of a benzene ring with these thiophene rings are benzothiophene rings. Examples of such structures include compounds represented by any of the following formulas (2-572) to (1-588).

[0296] X in equation (2) 1 and X 2Each of these is independently >O, >NR, >C(-R)2, >S, or >Se, where R in >NR is an optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkyl, or optionally substituted cycloalkyl, where R in >C(-R)2 is hydrogen, optionally substituted aryl, optionally substituted alkyl, or optionally substituted cycloalkyl, where R in >NR and / or R in >C(-R)2 may be bonded to the B ring and / or C ring by a linking group or single bond, with -O-, -S-, or -C(-R)2- being preferred as the linking group. Note that R in "-C(-R)2-" is hydrogen, alkyl, or cycloalkyl. This explanation applies to X in formulas (2-a), (2-b), (2-c), (2-d), (2-e), and (2-f). 1 and X 2 But it's the same.

[0297] In equation (2) and equations (2-a), (2-b), (2-c), (2-d), (2-e), and (2-f), X 1 and X 2 Each is preferably independently >O or >NR, more preferably >NR which is an optionally substituted phenyl, even more preferably >NR which is a phenyl substituted with one or two t-butyl, t-amyl, methyl or phenyl molecules, and particularly preferably >NR which is a phenyl substituted with one t-butyl or t-amyl molecule. 1 and X 2 These elements may be the same or different from each other.

[0298] Here, the provision in formula (2) that "R in >NR and / or R in >C(-R)2 are bonded to the A, B, and / or C rings by a linking group or a single bond" corresponds to the provision in formulas (2-a), (2-b), (2-c), (2-d), (2-e), and (2-f) that "R in >NR and / or R in >C(-R)2 are bonded to the a, b, and / or c rings by -O-, -S-, -C(-R)2- or a single bond."

[0299] This provision is represented by the following formula (2-a-3-1), X 1 Ya X 2 This can be represented by compounds having a ring structure in which X is incorporated into fused rings B' and C'. That is, for example, for the benzene ring which is the b ring (or c ring) in formula (2-a), X 1 (or X 2 These compounds have a B' ring (or C' ring) formed by the condensation of another ring, incorporating the B' ring. The resulting condensed ring B' (or C') is, for example, a carbazole ring, a phenoxazine ring, a phenothiazine ring, or an acridine ring.

[0300] Furthermore, the above provisions are expressed by the following formulas (2-a-3-2) and (2-a-3-3), X 1 and / or X 2 It can also be represented by compounds having a ring structure in which X is incorporated into the fused ring A'. That is, for example, with respect to the benzene ring which is ring a in formula (2-a), X 1 (and / or X 2 These compounds have an A' ring formed by the condensation of another ring, incorporating the A' ring. The resulting condensed ring A' is, for example, a carbazole ring, a phenoxazine ring, a phenothiazine ring, or an acridine ring.

[0301] [ka]

[0302] The "aryl rings" that make up rings A, B, and C in formula (2) include, for example, aryl rings having 6 to 30 carbon atoms, preferably aryl rings having 6 to 16 carbon atoms, more preferably aryl rings having 6 to 12 carbon atoms, and particularly preferably aryl rings having 6 to 10 carbon atoms. Note that these "aryl rings" are defined as "R" in formula (2). 1 ~R 11 This corresponds to an aryl ring formed by the bonding of adjacent groups with an a-ring, b-ring, or c-ring. Furthermore, since the a-ring (or b-ring, c-ring) is already composed of a benzene ring with 6 carbon atoms, the lower limit of carbon atoms is 9, which is the total number of carbon atoms in the fused ring formed by the fusion of a 5-membered ring with the a-ring.

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

[0304] Examples of heteroaryl rings, which are rings A, B, and C in formula (2), include heteroaryl rings having 2 to 30 carbon atoms, with heteroaryl rings having 2 to 25 carbon atoms being preferred, heteroaryl rings having 2 to 20 carbon atoms being more preferred, heteroaryl rings having 2 to 15 carbon atoms being even more preferred, and heteroaryl rings having 2 to 10 carbon atoms being particularly preferred. Furthermore, examples of heteroaryl rings include heterocycles containing 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen in addition to carbon as ring constituent atoms. Note that these heteroaryl rings are defined in formulas (2-a), (2-b), (2-c), (2-d), (2-e), and (2-f) as "R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9, R 10 , and R 11 This corresponds to a heteroaryl ring formed by the bonding of adjacent groups with an a-ring, b-ring, or c-ring. Furthermore, since the a-ring (or b-ring, c-ring) is already composed of a benzene ring with 6 carbon atoms, the lower limit of carbon atoms is 6, which is the total carbon number of the fused ring formed by the fusion of this ring and a 5-membered ring.

[0305] Specific examples of "heteroaryl rings" include, for example, pyrrole rings, oxazole rings, isoxazole rings, thiazole rings, isothiazole rings, imidazole rings, oxadiazole rings, thiadiazole rings, triazole rings, tetrazole rings, pyrazole rings, pyridine rings, pyrimidine rings, pyridazine rings, pyrazine rings, triazine rings, indole rings, isoindole rings, 1H-indazole rings, benzimidazole rings, benzoxazole rings, benzothiazole rings, and 1H-benzotriazole rings. Examples include the ru ring, quinoline ring, isoquinoline ring, cinnoline ring, quinazoline ring, quinoxaline ring, phthalazine ring, naphthyridine ring, purine ring, pteridine ring, carbazole ring, acridine ring, phenoxatiin ring, phenoxazine ring, phenothiazine ring, phenazine ring, indoridine ring, furan ring, benzofuran ring, isobenzofuran ring, dibenzofuran ring, thiophene ring, benzothiophene ring, dibenzothiophene ring, furazan ring, oxadiazole ring, and thianthrene ring.

[0306] At least one hydrogen 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 (the two aryls may be linked by 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 this first substituent include the aryl in "aryl" and "heteroaryl", the aryl in "diarylamino", the heteroaryl in "diheteroarylamino", the aryl and heteroaryl in "arylheteroarylamino", the aryl in "diarylboryl", and the aryl in "aryloxy", which are the monovalent groups of the above-mentioned "aryl ring" or "heteroaryl ring".

[0307] Furthermore, the "alkyl" as the first substituent may be either linear or branched, for example, a linear alkyl group having 1 to 24 carbon atoms or a branched alkyl group having 3 to 24 carbon atoms. A alkyl group having 1 to 18 carbon atoms (a branched alkyl group having 3 to 18 carbon atoms) is preferred, a alkyl group having 1 to 12 carbon atoms (a branched alkyl group having 3 to 12 carbon atoms) is more preferred, a alkyl group having 1 to 6 carbon atoms (a branched alkyl group having 3 to 6 carbon atoms) is even more preferred, and a alkyl group having 1 to 5 carbon atoms (a branched alkyl group having 3 to 5 carbon atoms) is particularly preferred.

[0308] Specific alkyl groups 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 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.

[0309] As for the "cycloalkyl" as the first substituent, examples include cycloalkyls having 3 to 24 carbon atoms, with cycloalkyls having 3 to 20 carbon atoms being preferred, cycloalkyls having 3 to 16 carbon atoms being more preferred, cycloalkyls having 3 to 14 carbon atoms being even more preferred, cycloalkyls having 5 to 10 carbon atoms being even more preferred, cycloalkyls having 5 to 8 carbon atoms being particularly preferred, and cycloalkyls having 5 to 6 carbon atoms being most preferred.

[0310] Specific examples of cycloalkyls include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and their alkyl (especially methyl) substituted derivatives having 1 to 4 carbon atoms, as well as norbornel, 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 decahydroazlenyl.

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

[0312] Specific examples of alkoxys include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, s-butoxy, t-butoxy, pentyloxy, hexyloxy, heptyloxy, and octyloxy.

[0313] Furthermore, as the first substituent, a "substituted silyl" can be a silyl substituted with three substituents selected from the group consisting of alkyl, cycloalkyl, and aryl. Examples include trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, triarylsilyl, dialkylarylsilyl, and alkyldiarylsilyl.

[0314] "Trialkylsilyl" refers to a group in which each of the three hydrogen atoms in the silyl group is independently substituted with an alkyl group. This alkyl group can be the same group described as "alkyl" in the first substituent mentioned above. Preferred alkyl groups for substitution are those having 1 to 5 carbon atoms, specifically including methyl, ethyl, propyl, i-propyl, butyl, sec-butyl, t-butyl, and t-amyl.

[0315] Specific examples of trialkylsilyls 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, buty Examples include dipropylsilyl, 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] "Tricycloalkylsilyl" refers to a group in which each of the three hydrogen atoms in the silyl group is independently substituted with a cycloalkyl group. This cycloalkyl group can be the same as the "cycloalkyl" group described above in the first substituent. Preferred cycloalkyl groups for substitution are those having 5 to 10 carbon atoms, specifically including 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, and decahydroazlenyl.

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

[0318] Specific examples of dialkylcycloalkylsilyls substituted with two alkyl groups and one cycloalkyl group, and alkyldicycloalkylsilyls substituted with one alkyl group and two cycloalkyl groups, include silyls substituted with groups selected from the specific alkyl and cycloalkyl groups mentioned above.

[0319] Specific examples of dialkylarylsilyls, alkyldiarylsilyls, and triarylsilyls, which are substituted with two alkyl groups and one aryl group, respectively, include silyls substituted with groups selected from the specific alkyl and aryl groups mentioned above. A particularly specific example of a triarylsilyl is triphenylsilyl.

[0320] Furthermore, the explanation of aryl in "diarylboryl" as the first substituent can be referenced from the explanation of aryl described above. These two aryls may also be linked by a single bond or a linking group (e.g., >C(-R)2, >O, >S, or >NR). Here, R in >C(-R)2 and >NR is aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, or aryloxy (the above are the first substituents), and the first substituent may be further substituted with aryl, heteroaryl, alkyl, or cycloalkyl (the above are the second substituents). Specific examples of these groups can be referenced from the explanation of aryl, heteroaryl, diarylamino, alkyl, cycloalkyl, alkoxy, or aryloxy as the first substituent described above.

[0321] Specifically, the emission wavelength can be adjusted by the steric hindrance, electron-donating, and electron-withdrawing properties of the structure of the first substituent, and preferably the group is 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, greater steric hindrance is preferable 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" represents methyl, "tBu" represents t-butyl, "tAm" represents t-amyl, "tOct" represents t-octyl, and * indicates a bond position. [ka]

[0323] [ka]

[0324] [ka]

[0325] [ka]

[0326] [ka]

[0327] [ka]

[0328] [ka]

[0329] [ka]

[0330] [ka]

[0331] [ka]

[0332] [ka]

[0333] [ka]

[0334] [ka]

[0335] In equation (2-a), R 1 , R 2 , R 3 , R 4 , R5 , R 6 , R 7 , R 8 , R 9 , R 10 , and R 11 Of these, 1 to 4 are preferably groups represented by one of the above structural formulas, and the rest are hydrogen atoms. 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , and R 11 Of these, 1 to 3 are groups represented by one of the above structural formulas, and the remaining ones are more preferably hydrogen atoms. 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , and R 11 It is even more preferable that 1 to 3 of these atoms are methyl, t-butyl, or t-amyl, and the remainder are hydrogen atoms.

[0336] The first substituents, which are substituted or unsubstituted "aryl", substituted or unsubstituted "heteroaryl", substituted or unsubstituted "diarylamino", substituted or unsubstituted "diheteroarylamino", substituted or unsubstituted "arylheteroarylamino", substituted or unsubstituted "diarylboryl (the two aryls may be linked by 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 substituted by the second substituent, as described as substituted or unsubstituted. Examples of this second substituent include aryl, heteroaryl, alkyl, or cycloalkyl, and specific examples can be found in the descriptions of the monovalent group of the "aryl ring" or "heteroaryl ring" and the "alkyl" or "cycloalkyl" as first substituents described above. Furthermore, aryl and heteroaryl structures with a second substituent also include those in which at least one hydrogen atom is substituted with an aryl group such as phenyl (specific examples are the groups mentioned above), an alkyl group such as methyl (specific examples are the groups mentioned above), or a cycloalkyl group such as cyclohexyl (specific examples are the groups mentioned above). For example, in the case of a carbazolyl with a second substituent, a carbazolyl in which at least one hydrogen atom at the 9-position is substituted with an aryl group such as phenyl, an alkyl group such as methyl, or a cycloalkyl group such as cyclohexyl is also included in heteroaryl structures with a second substituent.

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

[0338] X in equation (2) 1 and X 2In formulas (2-a), (2-b), (2-c), (2-d), (2-e), and (2-f), R is an aryl, heteroaryl, alkyl, or cycloalkyl group, which may be substituted with the second substituent described above, and at least one hydrogen in the aryl or heteroaryl group may be substituted with, for example, an alkyl or cycloalkyl group. Examples of these aryl, heteroaryl, alkyl, and cycloalkyl groups include those described above. Particularly preferred are aryl groups with 6 to 10 carbon atoms (e.g., phenyl, naphthyl), heteroaryl groups with 2 to 15 carbon atoms (e.g., carbazolyl), alkyl groups with 1 to 5 carbon atoms (e.g., methyl, ethyl), or cycloalkyl groups with 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl). This explanation applies to X in formulas (2-a), (2-b), (2-c), (2-d), (2-e), and (2-f). 1 and X 2 But the same applies to X in equations (2-a), (2-b), (2-c), (2-d), (2-e), and (2-f). 1 and X 2 In >NR, R is a C6-12 aryl which may be substituted with a C1-6 alkyl or a C3-14 cycloalkyl, a C2-15 heteroaryl which may be substituted with a C1-6 alkyl or a C3-14 cycloalkyl, a C1-6 alkyl, or a C3-14 cycloalkyl, and preferably a C6-10 aryl which may be substituted with a C1-4 alkyl or a C5-10 cycloalkyl, a C1-4 alkyl, or a C5-10 cycloalkyl.

[0339] X in equation (2) 1 and X 2In formulas (2-a), (2-b), (2-c), (2-d), (2-e), and (2-f), R is an aryl, alkyl, or cycloalkyl group, which may be substituted with hydrogen or the second substituent described above, and at least one hydrogen in the aryl group may be substituted with, for example, an alkyl or cycloalkyl group. Examples of these aryl, alkyl, and cycloalkyl groups include those described above. Particularly preferred are aryl groups with 6 to 10 carbon atoms (e.g., phenyl, naphthyl), alkyl groups with 1 to 5 carbon atoms (e.g., methyl, ethyl), or cycloalkyl groups with 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl). This explanation applies to X in formulas (2-a), (2-b), (2-c), (2-d), (2-e), and (2-f). 1 and X 2 But the same applies to X in equations (2-a), (2-b), (2-c), (2-d), (2-e), and (2-f). 1 and X 2 In >C(-R)2, R is a C6-C12 aryl which may be substituted with hydrogen, a C1-C6 alkyl or a C3-C14 cycloalkyl, a C1-C6 alkyl, or a C3-C14 cycloalkyl, and preferably a C6-C10 aryl which may be substituted with hydrogen, a C1-C4 alkyl or a C5-C10 cycloalkyl.

[0340] In formula (2), the linking group "-C(-R)2-" has R as hydrogen, alkyl, or cycloalkyl, and the alkyl and cycloalkyl groups mentioned above are examples of such groups. Particularly preferred are alkyl groups with 1 to 5 carbon atoms (e.g., methyl, ethyl, etc.) or cycloalkyl groups with 5 to 10 carbon atoms (preferably cyclohexyl or adamantyl). This explanation is the same for the linking group "-C(-R)2-" in formulas (2-a), (2-b), (2-c), (2-d), (2-e), and (2-f).

[0341] The dopant material may be a polymer of a polycyclic aromatic compound having multiple unit structures represented by formula (2). The polymer is preferably a polymer of a polycyclic aromatic compound having multiple unit structures represented by formula (2-a), formula (2-b), formula (2-c), formula (2-d), formula (2-e), or formula (2-f). The polymer is preferably a 2-6 mer, more preferably a 2-3 mer, and particularly preferably a dimer. A polymer can be any form in which a single compound has multiple of the above-mentioned unit structures. For example, in addition to a form in which the above-mentioned unit structures are linked together by single bonds, alkylene groups having 1 to 3 carbon atoms, phenylene groups, naphthylene groups, and other linking groups, it can also be a form in which any ring (A ring, B ring, or C ring, a ring, b ring, or c ring) included in the above-mentioned unit structure is shared among multiple unit structures, or it can be a form in which any ring (A ring, B ring, or C ring, a ring, b ring, or c ring) included in the above-mentioned unit structure is linked together by condensation.

[0342] Examples of such polymers include the polymer compounds represented by the following formulas (2-4), (2-4-1), (2-4-2), (2-5-1) to (2-5-4), or (2-6). The polymer compound represented by formula (2-4) is a polymer compound that, in terms of formula (2-a), has multiple unit structures represented by formula (2-a) in one compound, sharing a benzene ring (a ring). The polymer compound represented by formula (2-4-1) is a polymer compound that, in terms of formula (2-a), has two unit structures represented by formula (2-a) in one compound, sharing a benzene ring (a ring). The polymer compound represented by formula (2-4-2) is a polymer compound that, in terms of formula (2-a), has three unit structures represented by formula (2-a) in one compound, sharing a benzene ring (a ring). Furthermore, the polymer compounds represented by formulas (2-5-1) to (2-5-4) below are polymer compounds that, as explained by formula (2-a), have multiple unit structures represented by formula (2-a) in a single compound, by sharing a benzene ring which is a b-ring (or c-ring). Furthermore, the polymer compounds represented by formula (2-6) below are polymer compounds that, as explained by formula (2-a), have multiple unit structures represented by formula (2-a) in a single compound, by condensing, for example, a benzene ring which is a b-ring (or a-ring, c-ring) of a certain unit structure with a benzene ring which is a b-ring (or a-ring, c-ring) of a certain unit structure.

[0343] [ka]

[0344] The polymeric compound may be a polymer formed by combining a polymerized form represented by formula (2-4), formula (2-4-1), or formula (2-4-2) with a polymerized form represented by any of formulas (2-5-1) to (2-5-4) or formula (2-6), or a polymer formed by combining a polymerized form represented by any of formulas (2-5-1) to (2-5-4) with a polymerized form represented by formula (2-6), or a polymer formed by combining a polymerized form represented by formula (2-4), formula (2-4-1), or formula (2-4-2) with a polymerized form represented by any of formulas (2-5-1) to (2-5-4) and a polymerized form represented by formula (2-6).

[0345] Furthermore, the hydrogen atoms in the chemical structure of polycyclic aromatic compounds and their polymers 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 all or part deuterium, cyano, or halogen. For example, in formula (2), the A ring, B ring, C ring (A to C rings are aryl rings or heteroaryl rings), substituents on the A to C rings, and X 3 and X 4 When R is >NR or >C(-R)2, the hydrogen in R (=alkyl, cycloalkyl, aryl) can be substituted with deuterium, cyano, or halogen, among which embodiments include those in which all or some of the hydrogen in the aryl or heteroaryl is substituted with deuterium, cyano, or halogen. The halogen is fluorine, chlorine, bromine, or iodine, preferably fluorine, chlorine, or bromine, more preferably fluorine or chlorine.

[0346] Furthermore, at least one selected from the group consisting of aryl rings and heteroaryl rings in the chemical structure of a 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 its polymer may be condensed with at least one cycloalkane.

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

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

[0349] More preferably, an aryl ring which is ring A, ring B, ring C, ring a, ring b, ring c, an aryl (aryl moiety in aryl or diarylamino) and heteroaryl (heteroaryl moiety in heteroaryl) as a first substituent in rings A to C, an aryl (same as above) and heteroaryl (same as above) as a first substituent to ring a, ring b, ring c, and X 1 , X 2At least one of the aryls (as above) as R in >NR may be condensed with at least one cycloalkane.

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

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

[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 (especially methyl), halogen (especially fluorine), and deuterium-substituted compounds of these compounds having 1 to 5 carbon atoms.

[0353] Among these, a structure in which at least one hydrogen atom at the α-position carbon of the cycloalkane (the carbon adjacent to the carbon at the condensation site in a cycloalkane condensed to an aryl or heteroaryl ring) is substituted is preferred, a structure in which two hydrogen atoms at the α-position carbon are substituted is more preferred, and a structure in which a total of four hydrogen atoms at two α-position carbons are substituted is even more preferred. Examples of substituents include alkyl (especially methyl) substituted compounds having 1 to 5 carbon atoms, halogen (especially fluorine) substituted compounds, and deuterium substituted compounds. In particular, a structure in which a substructure represented by the following formula (B10) or formula (B11) is bonded to an adjacent carbon atom in the aryl or heteroaryl ring is preferred.

[0354] [ka] In the formula, Me represents a methyl group, and * indicates the bond position.

[0355] In formula (B), Me represents a methyl group, and * indicates a bond position, where the group represented by formula (B) is bonded to two adjacent elements on the aryl or heteroaryl ring to which it is bonded. Examples of such structures include the structures of compounds represented by formulas (2-559) to (2-563) and (2-580), which will be discussed later.

[0356] The number of cycloalkanes condensed to a single aromatic 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 a single benzene ring (phenyl) is shown below. Condensed cycloalkanes may also be condensed with each other, as shown in formulas (Cy-1-4) and (Cy-2-4). The same applies when the ring (group) to be condensed is an aromatic or heteroaromatic ring other than a benzene ring (phenyl), and when the cycloalkanes to be condensed are cyclopentanes other than cyclohexane. [ka]

[0357] At least one -CH2- in a cycloalkane may be substituted with -O-. For example, the following shows a cycloalkane condensed to a single benzene ring (phenyl) in which one or more -CH2- groups are substituted with -O-. The same applies when the condensed ring (group) is an aromatic ring or heteroaromatic ring other than a benzene ring (phenyl), and 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. Examples of such substituents include aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (the two aryls may be linked by a single bond or a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, substituted silyl, deuterium, cyano, or halogen. Details of these substituents can be found in the description of the first substituent above. Among these substituents, alkyl (e.g., alkyls with 1 to 6 carbon atoms), cycloalkyl (e.g., cycloalkyls with 3 to 14 carbon atoms), halogen (e.g., fluorine), and deuterium are preferred. Furthermore, when cycloalkyl is substituted, the substitution may form a spiro structure, an example of which is shown below.

[0360] [ka]

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

[0362] Furthermore, as a more specific example, consider the R in the chemical structure of polycyclic aromatic compounds and their polymers represented by formulas (2-a), (2-b), (2-c), (2-d), (2-e), or (2-f). 2 Examples include diarylamino compounds condensed with cycloalkanes (condensation on the aryl portion) or carbazolyls condensed with cycloalkanes (condensation on the benzene ring portion).

[0363] The following are preferred substituent combinations in formulas (2-a), (2-b), (2-c), (2-d), (2-e), and (2-f): R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , and R 11Each of these is independently hydrogen, a C6-C30 aryl which may be substituted with a C1-C6 alkyl or a C3-C4 cycloalkyl, a C2-C30 heteroaryl which may be substituted with a C1-C6 alkyl or a C3-C4 cycloalkyl, a diarylamino (where the aryl is a C6-C12 aryl which may be substituted with a C1-C6 alkyl or a C3-C4 cycloalkyl), a diarylboryl (where the aryl is a C6-C12 aryl which may be substituted with a C1-C6 alkyl or a C3-C4 cycloalkyl), a C1-C24 alkyl, or a C3-C24 cycloalkyl, and 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 them may bond together to form a C9-C16 aryl ring or a C6-C15 heteroaryl ring with the a, b, or c ring, and at least one hydrogen in the formed ring may be substituted with a C6-C30 aryl which may be substituted with a C1-C6 alkyl or a C3-C14 cycloalkyl, a C2-C30 heteroaryl which may be substituted with a C1-C6 alkyl or a C3-C14 cycloalkyl, a diarylamino (where the aryl is a C6-C12 aryl which may be substituted with a C1-C6 alkyl or a C3-C14 cycloalkyl), a diarylboryl (where the aryl is a C6-C12 aryl which may be substituted with a C1-C6 alkyl or a C3-C14 cycloalkyl), a C1-C24 alkyl, or a C3-C24 cycloalkyl. X 1 and X 2Each of these is independently >O, >NR, >C(-R)2, or >S, where R in >NR is a C6-C10 aryl, C1-C4 alkyl, or C5-C10 cycloalkyl which may be substituted with a C1-C4 alkyl or a C5-C10 cycloalkyl, and R in >C(-R)2 is hydrogen, a C6-C10 aryl, C1-C4 alkyl, or C5-C10 cycloalkyl which may be substituted with a C1-C4 alkyl or a C5-C10 cycloalkyl.

[0364] The following are more preferred substituent combinations in formulas (2-a), (2-b), (2-c), (2-d), (2-e), and (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 Each of these is independently hydrogen, a C6-C16 aryl which may be substituted with a C1-C4 alkyl or a C5-C10 cycloalkyl, a C2-C20 heteroaryl which may be substituted with a C1-C4 alkyl or a C5-C10 cycloalkyl, a diarylamino (where the aryl is a C6-C10 aryl which may be substituted with a C1-C4 alkyl or a C5-C10 cycloalkyl), a diarylboryl (where the aryl is a C6-C10 aryl which may be substituted with a C1-C4 alkyl or a C5-C10 cycloalkyl), a C1-C12 alkyl, or a C3-C16 cycloalkyl, and also R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , and R11 Adjacent groups among them may bond together to form a C9-C16 aryl ring or a C6-C15 heteroaryl ring with the a, b, or c ring, and at least one hydrogen in the formed ring may be substituted with a C6-C13 aryl which may be substituted with a C1-C4 alkyl or a C3-C10 cycloalkyl, a C2-C12 heteroaryl which may be substituted with a C1-C4 alkyl or a C3-C10 cycloalkyl, a diarylamino (where the aryl is a C6-C12 aryl which may be substituted with a C1-C4 alkyl or a C3-C10 cycloalkyl), a diarylboryl (where the aryl is a C6-C12 aryl which may be substituted with a C1-C4 alkyl or a C3-C10 cycloalkyl), a C1-C12 alkyl, or a C3-C20 cycloalkyl. X 1 and X 2 Each of these is independently >O, >NR, or >C(-R)2, where R in >NR is a C6-C10 aryl, C1-C4 alkyl, or C5-C10 cycloalkyl which may be substituted with a C1-C4 alkyl or a C5-C10 cycloalkyl, and R in >C(-R)2 is hydrogen, a C6-C10 aryl, C1-C4 alkyl, or C5-C10 cycloalkyl which may be substituted with a C1-C4 alkyl or a C5-C10 cycloalkyl.

[0365] Further preferred substituent combinations in formulas (2-a), (2-b), (2-c), (2-d), (2-e), and (2-f) are as follows: R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , and R 11Each of these is independently hydrogen, a C6-C16 aryl which may be substituted with a C1-C4 alkyl or a C5-C10 cycloalkyl, a C2-C20 heteroaryl which may be substituted with a C1-C4 alkyl or a C5-C10 cycloalkyl, a diarylamino (where the aryl is a C6-C10 aryl which may be substituted with a C1-C4 alkyl or a C5-C10 cycloalkyl), a diarylboryl (where the aryl is a C6-C10 aryl which may be substituted with a C1-C4 alkyl or a C5-C10 cycloalkyl), a C1-C12 alkyl, or a C3-C16 cycloalkyl. 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 them may bond together to form a C9-C16 aryl ring or a C6-C15 heteroaryl ring with the a, b, or c ring, and at least one hydrogen in the formed ring may be substituted with a C6-C13 aryl group which may be substituted with a C1-C4 alkyl group or a C3-C10 cycloalkyl group, a C2-C12 heteroaryl group which may be substituted with a C1-C4 alkyl group or a C3-C10 cycloalkyl group, a diarylamino group (where the aryl group is a C6-C12 aryl group which may be substituted with a C1-C4 alkyl group or a C3-C10 cycloalkyl group), a C1-C6 alkyl group, or a C3-C10 cycloalkyl group. X 1 and X 2 Each of these is independently >O or >NR, where R in >NR is a C6-C10 aryl, C1-C4 alkyl, or C5-C10 cycloalkyl which may be substituted with a C1-C4 alkyl or a C5-C10 cycloalkyl.

[0366] A more specific example of a polycyclic aromatic compound represented by formula (2) is the compound represented by the following formula. In the formula below, "Me" represents methyl, "tBu" represents tert-butyl (t-butyl), "iPr" represents isopropyl, "Ph" represents phenyl, "tAm" represents tert-amyl (tert-pentyl), and "D" represents deuterium.

[0367] [ka]

[0368] [ka]

[0369] [ka]

[0370] [ka]

[0371] [ka]

[0372] [ka]

[0373] [ka]

[0374] [ka]

[0375] [ka]

[0376]

change

[0377]

change

[0378]

change

[0379]

change

[0380]

change

[0381]

change

[0382]

change

[0383]

change

[0384]

change

[0385]

change

[0386]

change

[0387]

change

[0388]

change

[0389]

change

[0390]

change

[0391]

change

[0392]

change

[0393]

change

[0394]

change

[0395]

change

[0396]

change

[0397]

change

[0398]

change

[0399]

change

[0400]

change

[0401]

change

[0402]

change

[0403]

change

[0404]

change

[0405]

change

[0406]

change

[0407]

change

[0408] [ka]

[0409] [ka]

[0410] 1-2-2. Method for producing polycyclic aromatic compounds represented by formula (2) and their polymers The polycyclic aromatic compounds represented by formula (2) and their polymers can be synthesized, for example, by the method disclosed in International Publication No. 2019 / 009052 as "Method for producing polycyclic aromatic compounds represented by formula (2) and their polymers."

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

[0412] The dopant material may be contained throughout or partially within the host material. Doping can be achieved by co-deposition with the host material, or by pre-mixing with the host material and then simultaneously depositing the dopant material.

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

[0414] The amount of dopant material used varies depending on the type of dopant material and should be determined according to the characteristics of that dopant material. A guideline for the amount of dopant used is preferably 0.001 to 50% by mass of the total material for the light-emitting layer, more preferably 0.05 to 20% by mass, and even more preferably 0.1 to 10% by mass. Within this range, for example, it is preferable in that it can prevent density quenching.

[0415] Examples of host materials that can be used in combination with the compound represented by formula (1) include condensed ring derivatives such as pyrene, which have been known as luminescent materials for some time, bis-styryl derivatives such as bis-styrylanthracene derivatives and distylylbenzene derivatives, tetraphenylbutadiene derivatives, cyclopentadiene derivatives, fluorene derivatives, and benzofluorene derivatives.

[0416] Examples of dopant materials that can be used in combination with the compound represented by formula (2) include condensed ring derivatives such as anthracene and pyrene, which have been known as luminescent materials for some time, 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 devices The electron injection layer 107 plays the 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 the 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 and mixing one or more types of electron transport / injection materials, or by a mixture of electron transport / injection materials and a polymer binder.

[0418] The electron injection and transport layer is responsible for injecting electrons from the cathode and transporting them. It is desirable for this layer to have high electron injection efficiency and to efficiently transport the injected electrons. To achieve this, it is preferable for the material to have high electron affinity, high electron mobility, excellent stability, and to be a material that does not easily generate trapping impurities during manufacturing and use. However, when considering the balance between hole and electron transport, if the main role is to efficiently prevent holes from the anode from flowing to the cathode side without recombining, then even if the electron transport capacity is not very high, the effect of improving luminescence efficiency will be equivalent to that of a material with high electron transport capacity. Therefore, the electron injection and transport layer in this embodiment may also include the function of a layer that can efficiently prevent the movement of holes.

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

[0420] The 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 fused ring derivatives, and metal complexes having electron-accepting nitrogen. Specifically, examples include fused ring aromatic ring derivatives such as naphthalene and anthracene, styryl aromatic ring derivatives represented by 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 individually or in combination with different materials.

[0421] Furthermore, specific examples of other electron transfer compounds include borane derivatives, pyridine derivatives, naphthalene derivatives, fluorantene 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-based metal complexes, quinoxaline derivatives, polymers of quinoxaline derivatives, benzazole compounds, gallium complexes, pyrazole derivatives, perfluorinated phenylene derivatives, and triazine derivatives. Examples include pyrazine derivatives, benzoquinoline derivatives (such as 2,2'-bis(benzo[h]quinoline-2-yl)-9,9'-spirobifluorene), imidazopyridine derivatives, benzimidazole derivatives (such as tris(N-phenylbenzimidazole-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-naphthyridine-2-yl)phenylphosphine oxide), aldazine derivatives, pyrimidine derivatives, arylnitrile derivatives, indole derivatives, phosphorus oxide derivatives, bisstyryl derivatives, silole derivatives, and azoline derivatives.

[0422] Furthermore, metal complexes containing electron-accepting nitrogen can also be used, such as quinolinol-based metal complexes, hydroxyazole complexes such as hydroxyphenyl oxazole complexes, azomethine complexes, tropolone metal complexes, flavonol metal complexes, and benzoquinoline metal complexes.

[0423] The materials mentioned above can be used individually, but they can also be used in combination with other materials.

[0424] Among the materials mentioned above, borane derivatives, pyridine derivatives, fluorantene derivatives, BO 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] <Bolan derivatives> Borane derivatives are compounds represented by the following formula (ETM-1), for example, and are disclosed in detail in Japanese Patent Application Publication No. 2007-27587. [ka]

[0426] In formula (ETM-1), R 11 and R 12 Each is independently at least one of hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, or cyano, and R 13 ~R 16 Each of the following is independently an optionally substituted alkyl, optionally substituted cycloalkyl, or optionally substituted aryl; X is an optionally substituted arylene; Y is an optionally substituted aryl with 16 or fewer carbon atoms, a substituted boryl, or an optionally substituted carbazolyl; and each of the following is independently an integer from 0 to 3. Examples of substituents that are "optionally substituted" or "substituted" include aryl, heteroaryl, alkyl, or cycloalkyl groups.

[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 Each is independently at least one of hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, or cyano, and R 13 ~R 16 Each of these is independently an optionally substituted alkyl, an optionally substituted cycloalkyl, or an optionally substituted aryl, and R 21 and R 22 Each is independently at least one of hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, or cyano, and X 1 is an arylene with 20 or fewer carbon atoms, which may be substituted, where n is an independent integer between 0 and 3, and m is an independent integer between 0 and 4. Substituents that may or may be substituted include aryl, heteroaryl, alkyl, or cycloalkyl groups.

[0429] [ka]

[0430] In formula (ETM-1-2), R 11 and R 12 Each is independently at least one of hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, or cyano, and R 13 ~R 16Each of these is independently an optionally substituted alkyl, an optionally substituted cycloalkyl, or an optionally substituted aryl, and X 1 is an arylene with 20 or fewer carbon atoms, which may be substituted, and n is an independent integer between 0 and 3. Substituents that may or may be substituted include aryl, heteroaryl, alkyl, or cycloalkyl groups.

[0431] X 1 A specific example of this is a divalent group represented by any of the following equations (X-1) to (X-9). [ka] (In each formula, R a Each of these is independently an alkyl, cycloalkyl, or optionally substituted phenyl group, and * indicates the bond position.

[0432] Specific examples of these borane derivatives include the following compounds. [ka]

[0433] This 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), and 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 from 1 to 4.

[0436] In equation (ETM-2-1), R 11 ~R 18 Each of these is 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 equation (ETM-2-2), R 11 and R 12 Each of these is independently hydrogen, alkyl (preferably alkyl with 1 to 24 carbon atoms), cycloalkyl (preferably cycloalkyl with 3 to 12 carbon atoms), or aryl (preferably aryl with 6 to 30 carbon atoms), and R 11 and R 12 They may be joined together to form a ring.

[0438] In each formula, the "pyridine substituent" is one of the following formulas (Py-1) to (Py-15) (where * indicates the bond position), and each pyridine substituent may be independently substituted with an alkyl group having 1 to 4 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms. Specific examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, or t-butyl, with methyl being preferred. Furthermore, the pyridine 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 substituent is one of formulas (Py-1) to (Py-15), but among these, it is preferably one of formulas (Py-21) to (Py-44) below (where * indicates the bond position). [ka]

[0441] At least one hydrogen atom in each pyridine derivative may be substituted with deuterium, and one of the two "pyridine substituents" in formulas (ETM-2-1) and (ETM-2-2) may be substituted with an aryl atom.

[0442] R 11 ~R 18 The "alkyl" in this context can be either linear or branched, for example, a linear alkyl group with 1 to 24 carbon atoms or a branched alkyl group with 3 to 24 carbon atoms. A preferred "alkyl" is an alkyl group with 1 to 18 carbon atoms (a branched alkyl group with 3 to 18 carbon atoms). A more preferred "alkyl" is an alkyl group with 1 to 12 carbon atoms (a branched alkyl group with 3 to 12 carbon atoms). A still preferred "alkyl" is an alkyl group with 1 to 6 carbon atoms (a branched alkyl group with 3 to 6 carbon atoms). A particularly preferred "alkyl" is an alkyl group with 1 to 4 carbon atoms (a branched alkyl group with 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] For alkyl groups with 1 to 4 carbon atoms to be substituted for pyridine substituents, the above description of alkyl groups can be referenced.

[0445] R 11 ~R 18 Examples of "cycloalkyl" in this context include cycloalkyls having 3 to 12 carbon atoms. Preferred "cycloalkyls" are those having 3 to 10 carbon atoms. More preferred "cycloalkyls" are those having 3 to 8 carbon atoms. Even more preferred "cycloalkyls" are those having 3 to 6 carbon atoms. Specific examples of "cycloalkyl" compounds include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, or dimethylcyclohexyl.

[0446] R 11 ~R 18 In this context, the preferred aryl is an aryl having 6 to 30 carbon atoms, a more preferred aryl is an aryl having 6 to 18 carbon atoms, an even more preferred aryl is an aryl having 6 to 14 carbon atoms, and a particularly preferred aryl is an aryl having 6 to 12 carbon atoms.

[0447] Specific examples of "aryl compounds with 6 to 30 carbon atoms" include the monocyclic aryl phenyl, the condensed bicyclic aryl (1-,2-)naphthyl, the condensed tricyclic aryls acenaphthylene-(1-,3-,4-,5-)yl, fluoren-(1-,2-,3-,4-,9-)yl, phenalen-(1-,2-)yl, (1-,2-,3-,4-,9-)phenanthryl, the condensed tetracyclic aryls triphenylene-(1-,2-)yl, pyren-(1-,2-,4-)yl, naphthacene-(1-,2-,5-)yl, and the condensed pentacyclic aryls perylene-(1-,2-,3-)yl, pentacene-(1-,2-,5-,6-)yl.

[0448] Preferred "aryl compounds having 6 to 30 carbon atoms" include phenyl, naphthyl, phenanthryl, crisenyl, or triphenylenyl, more preferably phenyl, 1-naphthyl, 2-naphthyl, or phenanthryl, and particularly preferably phenyl, 1-naphthyl, or 2-naphthyl.

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

[0450] Specific examples of pyridine derivatives include the following compounds. [ka]

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

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

Chemical Formula

[0453] In formula (ETM-3), X 12 to X 21 each represent hydrogen, halogen, linear, branched or cyclic alkyl, linear, branched or cyclic alkoxy, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl. Here, when substituted, examples of the substituent include aryl, heteroaryl, alkyl or cycloalkyl.

[0454] Specific examples of this fluoranthene derivative include 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 to R 71 are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkoxy or aryloxy, and at least one hydrogen in these groups may be substituted with aryl, heteroaryl, alkyl or cycloalkyl.

[0457] Further, R 61 to R 71Adjacent groups among them may bond together to form an aryl ring or heteroaryl ring with the a, b, or c ring, and at least one hydrogen in the formed ring may be substituted with 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.

[0458] Furthermore, at least one hydrogen atom 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 ring formation in formula (ETM-4), refer to the explanation of polycyclic aromatic compounds represented by formula (1) or formula (2).

[0460] Specific examples of these BO derivatives include the following compounds. [ka]

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

[0462] <Anthracene derivatives> Anthracene derivatives are compounds represented by the following formula (ETM-5), for example. [ka]

[0463] Ar 1 These are, independently, single-bonded, divalent benzene, naphthalene, anthracene, fluorene, or phenalene.

[0464] Ar 2Each of these is independently an aryl group having 6 to 20 carbon atoms, preferably an aryl group having 6 to 16 carbon atoms, more preferably an aryl group having 6 to 12 carbon atoms, and particularly preferably an aryl group having 6 to 10 carbon atoms. Specific examples of "aryls with 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), (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 Examples include nyl-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), the condensed tricyclic aryls anthracene-(1-,2-,9-)yl, acenaphthylene-(1-,3-,4-,5-)yl, fluoren-(1-,2-,3-,4-,9-)yl, phenalen-(1-,2-)yl, (1-,2-,3-,4-,9-)phenanthryl, the condensed tetracyclic aryls triphenylene-(1-,2-)yl, pyren-(1-,2-,4-)yl, tetracene-(1-,2-,5-)yl, and the condensed pentacyclic aryl perylene-(1-,2-,3-)yl. Specific examples of "aryl compounds with 6 to 10 carbon atoms" include phenyl, biphenylyl, naphthyl, terphenylyl, anthracenyl, acenaphthirenyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, tetracerenyl, and perilenyl.

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

[0466] R 1 ~R 4 The C1-C6 alkyl group in the formula may be either linear or branched. That is, it may be a linear alkyl group with C1-C6 or a branched alkyl group with C3-C6. More preferably, it may be an alkyl group with C1-C4 (a branched alkyl group with C3-C4). 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, or 2-ethylbutyl, with methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, or t-butyl being preferred, and methyl, ethyl, or t-butyl being more preferred.

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

[0468] R 1 ~R 4 Regarding the aryl compounds having 6 to 20 carbon atoms, aryl compounds having 6 to 16 carbon atoms are preferred, aryl compounds having 6 to 12 carbon atoms are more preferred, and aryl compounds having 6 to 10 carbon atoms are particularly preferred. Specific examples of "aryl compounds having 6 to 20 carbon atoms" include Ar 2 Specific examples of "aryls having 6 to 20 carbon atoms" can be cited. Preferred "aryls 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, even more 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> Benzofluorene derivatives are compounds represented by the following formula (ETM-6), for example. [ka]

[0472] Ar 1 Each of these is an aryl group with 6 to 20 carbon atoms, and is represented by the formula (ETM-5) Ar 2 The same explanation as for "aryls with 6 to 20 carbon atoms" can be cited. Aryls with 6 to 16 carbon atoms are preferred, aryls with 6 to 12 carbon atoms are more preferred, and aryls with 6 to 10 carbon atoms are particularly preferred. Specific examples include phenyl, biphenylyl, naphthyl, terphenylyl, anthracenyl, acenaphthirenyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, tetracenyl, and perilenyl.

[0473] Ar 2 Each of these is independently hydrogen, alkyl (preferably alkyl with 1 to 24 carbon atoms), cycloalkyl (preferably cycloalkyl with 3 to 12 carbon atoms), or aryl (preferably aryl with 6 to 30 carbon atoms), and two Ar 2 They may be joined together to form a ring.

[0474] Ar 2The "alkyl" in this context can be either linear or branched, for example, a linear alkyl group with 1 to 24 carbon atoms or a branched alkyl group with 3 to 24 carbon atoms. A preferred "alkyl" is an alkyl group with 1 to 18 carbon atoms (a branched alkyl group with 3 to 18 carbon atoms). A more preferred "alkyl" is an alkyl group with 1 to 12 carbon atoms (a branched alkyl group with 3 to 12 carbon atoms). A still preferred "alkyl" is an alkyl group with 1 to 6 carbon atoms (a branched alkyl group with 3 to 6 carbon atoms). A particularly preferred "alkyl" is an alkyl group with 1 to 4 carbon atoms (a branched alkyl group with 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, and 1-methylhexyl.

[0475] Ar 2 Examples of "cycloalkyl" in this context include cycloalkyls having 3 to 12 carbon atoms. Preferred "cycloalkyls" are those having 3 to 10 carbon atoms. More preferred "cycloalkyls" are those having 3 to 8 carbon atoms. Even more preferred "cycloalkyls" are those having 3 to 6 carbon atoms. Specific examples of "cycloalkyls" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, or dimethylcyclohexyl.

[0476] Ar 2 In this context, the preferred aryl is an aryl having 6 to 30 carbon atoms, a more preferred aryl is an aryl having 6 to 18 carbon atoms, an even more preferred aryl is an aryl having 6 to 14 carbon atoms, and a particularly preferred aryl is an aryl having 6 to 12 carbon atoms.

[0477] Specific examples of "aryl compounds with 6 to 30 carbon atoms" include phenyl, naphthyl, acenaphthirenyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, naphthacenyl, perilenyl, and pentacenyl.

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

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

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

[0481] <Phosphine oxide derivatives> Phosphine oxide derivatives are compounds represented by formula (ETM-7-1) below, for example. Further details are also described in International Publication Nos. 2013 / 079217 and 2013 / 079678. [ka]

[0482] R 5 These are substituted or unsubstituted alkyl groups with 1 to 20 carbon atoms, cycloalkyl groups with 3 to 16 carbon atoms, aryl groups with 6 to 20 carbon atoms, or heteroaryl groups with 5 to 20 carbon atoms. R 6 These are CN, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, cycloalkyl groups having 3 to 16 carbon atoms, heteroalkyl groups having 1 to 20 carbon atoms, aryl groups having 6 to 20 carbon atoms, heteroaryl groups having 5 to 20 carbon atoms, alkoxy groups having 1 to 20 carbon atoms, or aryloxy groups having 6 to 20 carbon atoms. R 7 and R 8 These are, independently, substituted or unsubstituted aryls with 6 to 20 carbon atoms or heteroaryls with 5 to 20 carbon atoms. R 9 It is oxygen or sulfur, j is 0 or 1, k is 0 or 1, r is an integer between 0 and 4, and q is an integer between 1 and 3. Examples of substituents that may be substituted include aryl, heteroaryl, alkyl, or cycloalkyl compounds.

[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 These may be the same or different, and are selected from hydrogen, alkyl, cycloalkyl, aralkyl, alkenyl, cycloalkenyl, alkynyl, alkoxy, alkylthio, cycloalkylthio, aryl ether group, arylthioether group, aryl, heterocyclic group, halogen, cyano, formyl, carbonyl, carboxyl, amino, nitro, silyl, and condensed rings formed between adjacent substituents.

[0485] Ar 1 These can be the same or different, and are either arylenes or heteroarylenes. 2 They may be the same or different, and are aryl or heteroaryl. However, Ar 1 and Ar 2 At least one of them has a substituent or forms a fused ring with an adjacent substituent. n is an integer from 0 to 3, when n is 0 there is no unsaturated structural part, and when n is 3 there is R 1 It does not exist.

[0486] Of these substituents, alkyl refers to saturated aliphatic hydrocarbon groups such as methyl, ethyl, propyl, and butyl, which may be unsubstituted or substituted. There are no particular restrictions on the substituents when substituted; for example, alkyl, aryl, and heterocyclic groups can be used, and this point is also common to the following description. Furthermore, the number of carbon atoms in alkyl is not particularly limited, but for reasons of availability and cost, it is usually in the range of 1 to 20.

[0487] Furthermore, cycloalkyl refers to saturated alicyclic hydrocarbon groups such as cyclopropyl, cyclohexyl, norbornyl, and adamantyl, 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] Furthermore, aralkyl refers to an aromatic hydrocarbon group mediated by an aliphatic hydrocarbon such as benzyl or phenylethyl, and both the aliphatic and aromatic hydrocarbons 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] Furthermore, an alkenyl refers to an unsaturated aliphatic hydrocarbon group containing a double bond, such as vinyl, allyl, or butadienyl, which may be unsubstituted or substituted. The number of carbon atoms in an alkenyl is not particularly limited, but is usually in the range of 2 to 20.

[0490] Furthermore, cycloalkenyl refers to unsaturated alicyclic hydrocarbon groups containing double bonds, such as cyclopentenyl, cyclopentadienyl, and cyclohexene, which may be unsubstituted or substituted.

[0491] Furthermore, "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 an alkynyl group is not particularly limited, but is usually in the range of 2 to 20.

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

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

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

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

[0496] Furthermore, an arylthioether group is a group in which the oxygen atom in the ether bond of an aryl ether group is replaced by a sulfur atom.

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

[0498] Furthermore, heterocyclic groups refer to cyclic structural groups that have atoms other than carbon, such as furanyl, thienyl, oxazolyl, pyridyl, quinolinyl, and carbazolyl, and these can be unsubstituted or substituted. The number of carbon atoms in a heterocyclic group is not particularly limited, but it is usually in the range of 2 to 30.

[0499] Halogens refer to fluorine, chlorine, bromine, and iodine.

[0500] Formyl, carbonyl, and amino groups can also include groups substituted with aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons, heterocyclic groups, etc.

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

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

[0503] The fused 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 It is a conjugated or unconjugated fused ring formed between the following elements. Here, when n is 1, two R 1 These rings may form conjugated or non-conjugated fused rings. These fused rings may contain nitrogen, oxygen, and sulfur atoms in their intraring structure, and may also be fused with other rings.

[0504] Specific examples of these phosphine oxide derivatives include the following compounds. [ka]

[0505] This 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), and preferably a compound represented by the following formula (ETM-8-1). Further details are also described in International Publication No. 2011 / 021689. [ka]

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

[0508] Examples of "aryls that may be substituted" include aryls having 6 to 30 carbon atoms, preferably aryls having 6 to 24 carbon atoms, more preferably aryls having 6 to 20 carbon atoms, and even more preferably aryls having 6 to 12 carbon atoms.

[0509] Specific examples of "aryl" include monocyclic aryls such as phenyl, bicyclic aryls such as (2-,3-,4-)biphenylyl, condensed bicyclic aryls such as (1-,2-)naphthyl, 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, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), and condensed tricyclic aryls. Examples of aryl compounds include acenaphthylene-(1-,3-,4-,5-)yl, fluoren-(1-,2-,3-,4-,9-)yl, phenalen-(1-,2-)yl, (1-,2-,3-,4-,9-)phenanthryl; tetracyclic aryl compounds include quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl); condensed tetracyclic aryl compounds include triphenylene-(1-,2-)yl, pyren-(1-,2-,4-)yl, naphthacene-(1-,2-,5-)yl; and condensed pentacyclic aryl compounds include perylene-(1-,2-,3-)yl, pentacene-(1-,2-,5-,6-)yl.

[0510] Examples of "heteroaryls that may be substituted" include heteroaryls having 2 to 30 carbon atoms, with heteroaryls having 2 to 25 carbon atoms being preferred, heteroaryls having 2 to 20 carbon atoms being more preferred, heteroaryls having 2 to 15 carbon atoms being even more preferred, and heteroaryls having 2 to 10 carbon atoms being particularly preferred. Examples of heteroaryls include heterocycles containing 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen in addition to carbon as ring constituent atoms.

[0511] Specific heteroaryl compounds include, for example, furyl, thienyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, flazanil, thiadiazolyl, triazolyl, tetrazolyl, pyridyl, pyrimidinil, pyridadinil, pyrazinil, triazinil, benzofuranil, isobenzofuranil, benzo[b]thienyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, cinnolyl, quinazolyl, quinoxalinil, phthalazinil, naphthilidinil, prinyl, pteridinil, carbazolyl, acridinil, phenoxazinil, phenothiazinil, phenazinil, phenoxathiinil, thianthrenil, and indolidinil.

[0512] Furthermore, the above-mentioned aryl and heteroaryl may be substituted, for example, they may be substituted with the above-mentioned aryl or heteroaryl.

[0513] Specific examples of these pyrimidine derivatives include the following compounds. [ka]

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

[0515] <Arylnitrile derivatives> Arylnitrile derivatives are compounds represented by formula (ETM-9) below, for example, or polymers formed by the linkage of multiple such compounds via single bonds or other means. Further details are described in U.S. Patent Application Publication No. 2014 / 0197386. [ka]

[0516] Ar niFrom the viewpoint of fast electron transport, a high number of carbon atoms is preferable, and from the viewpoint of high T1, a low number of carbon atoms is preferable. ni Specifically, for use in a layer adjacent to the light-emitting layer, it is preferable to have a high T1, 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. Furthermore, the number of substituted nitrile groups n is preferably large from the viewpoint of high T1, and preferably small from the viewpoint of high S1. Specifically, the number of substituted nitrile groups n is an integer from 1 to 4, preferably an integer from 1 to 3, more preferably an integer from 1 to 2, and even more preferably 1.

[0517] Each Ar is independently a substituted or substituted heteroaryl. From the viewpoint of high S1 and high T1, a donor heteroaryl is preferred, and since it is used as an electron transport layer, it is preferable to have few donor heteroaryls. From the viewpoint of charge transport, an aryl or heteroaryl with a large number of carbon atoms is preferred, and it is preferable to have many substituents. Specifically, the number of substitutions m of Ar is an integer from 1 to 4, preferably an integer from 1 to 3, and more preferably 1 to 2.

[0518] Examples of "aryls that may be substituted" include aryls having 6 to 30 carbon atoms, preferably aryls having 6 to 24 carbon atoms, more preferably aryls having 6 to 20 carbon atoms, and even more preferably aryls having 6 to 12 carbon atoms.

[0519] Specific examples of "aryl" include monocyclic aryls such as phenyl, bicyclic aryls such as (2-,3-,4-)biphenylyl, condensed bicyclic aryls such as (1-,2-)naphthyl, 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, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), and condensed tricyclic aryls. Examples of aryl compounds include acenaphthylene-(1-,3-,4-,5-)yl, fluoren-(1-,2-,3-,4-,9-)yl, phenalen-(1-,2-)yl, (1-,2-,3-,4-,9-)phenanthryl; tetracyclic aryl compounds include quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl); condensed tetracyclic aryl compounds include triphenylene-(1-,2-)yl, pyren-(1-,2-,4-)yl, naphthacene-(1-,2-,5-)yl; and condensed pentacyclic aryl compounds include perylene-(1-,2-,3-)yl, pentacene-(1-,2-,5-,6-)yl.

[0520] Examples of "heteroaryls that may be substituted" include heteroaryls having 2 to 30 carbon atoms, with heteroaryls having 2 to 25 carbon atoms being preferred, heteroaryls having 2 to 20 carbon atoms being more preferred, heteroaryls having 2 to 15 carbon atoms being even more preferred, and heteroaryls having 2 to 10 carbon atoms being particularly preferred. Examples of heteroaryls include heterocycles containing 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen in addition to carbon as ring constituent atoms.

[0521] Specific heteroaryl compounds include, for example, furyl, thienyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, flazanil, thiadiazolyl, triazolyl, tetrazolyl, pyridyl, pyrimidinil, pyridadinil, pyrazinil, triazinil, benzofuranil, isobenzofuranil, benzo[b]thienyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, cinnolyl, quinazolyl, quinoxalinil, phthalazinil, naphthilidinil, prinyl, pteridinil, carbazolyl, acridinil, phenoxazinil, phenothiazinil, phenazinil, phenoxathiinil, thianthrenil, and indolidinil.

[0522] Furthermore, the above-mentioned aryl and heteroaryl may be substituted, for example, they may be substituted with the above-mentioned aryl or heteroaryl.

[0523] The arylnitrile derivative may be a polymer in which multiple compounds represented by formula (ETM-9) are linked by single bonds or other means. In this case, in addition to single bonds, the linkage may also be by aryl rings (preferably polyvalent benzene rings, naphthalene rings, anthracene rings, fluorene rings, benzofluorene rings, phenalene rings, phenanthrene rings, or triphenylene rings).

[0524] Specific examples of these arylnitrile derivatives include the following compounds. [ka]

[0525] This arylnitrile derivative can be produced using known raw materials and known synthesis methods.

[0526] <Triadine derivatives> The triazine derivative is, for example, a compound represented by the following formula (ETM-10), and preferably a compound represented by the following formula (ETM-10-1). Further details are described in U.S. Patent Publication No. 2011 / 0156013. [ka]

[0527] Each Ar is independently a substituted or substituted heteroaryl. n is an integer between 1 and 3, preferably 2 or 3.

[0528] Examples of "aryls that may be substituted" include aryls having 6 to 30 carbon atoms, preferably aryls having 6 to 24 carbon atoms, more preferably aryls having 6 to 20 carbon atoms, and even more preferably aryls having 6 to 12 carbon atoms.

[0529] Specific examples of "aryl" include monocyclic aryls such as phenyl, bicyclic aryls such as (2-,3-,4-)biphenylyl, condensed bicyclic aryls such as (1-,2-)naphthyl, 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, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), and condensed tricyclic aryls. Examples of aryl compounds include acenaphthylene-(1-,3-,4-,5-)yl, fluoren-(1-,2-,3-,4-,9-)yl, phenalen-(1-,2-)yl, (1-,2-,3-,4-,9-)phenanthryl; tetracyclic aryl compounds include quaterphenylyl (5'-phenyl-m-terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl); condensed tetracyclic aryl compounds include triphenylene-(1-,2-)yl, pyren-(1-,2-,4-)yl, naphthacene-(1-,2-,5-)yl; and condensed pentacyclic aryl compounds include perylene-(1-,2-,3-)yl, pentacene-(1-,2-,5-,6-)yl.

[0530] Examples of "heteroaryls that may be substituted" include heteroaryls having 2 to 30 carbon atoms, with heteroaryls having 2 to 25 carbon atoms being preferred, heteroaryls having 2 to 20 carbon atoms being more preferred, heteroaryls having 2 to 15 carbon atoms being even more preferred, and heteroaryls having 2 to 10 carbon atoms being particularly preferred. Examples of heteroaryls include heterocycles containing 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen in addition to carbon as ring constituent atoms.

[0531] Specific heteroaryl compounds include, for example, furyl, thienyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, oxadiazolyl, flazanil, thiadiazolyl, triazolyl, tetrazolyl, pyridyl, pyrimidinil, pyridadinil, pyrazinil, triazinil, benzofuranil, isobenzofuranil, benzo[b]thienyl, indolyl, isoindolyl, 1H-indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolyl, isoquinolyl, cinnolyl, quinazolyl, quinoxalinil, phthalazinil, naphthilidinil, prinyl, pteridinil, carbazolyl, acridinil, phenoxazinil, phenothiazinil, phenazinil, phenoxathiinil, thianthrenil, and indolidinil.

[0532] Furthermore, the above-mentioned aryl and heteroaryl may be substituted, for example, they may be substituted with the above-mentioned aryl or heteroaryl.

[0533] Specific examples of these triazine derivatives include the following compounds. [ka]

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

[0535] <Benzimidazole derivatives> Benzimidazole derivatives are compounds represented by the following formula (ETM-11), for example. [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 "benzimidazole substituent" is a substituent in which pyridyl in the "pyridine substituent" in formulas (ETM-2), (ETM-2-1), and (ETM-2-2) is replaced with benzimidazol, and at least one hydrogen in the benzimidazole derivative may be substituted with deuterium. [ka]

[0537] R in the above benzimidazolyl 11 R is hydrogen, an alkyl group having 1 to 24 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, or an aryl group having 6 to 30 carbon atoms, and R in formulas (ETM-2-1) and (ETM-2-2) 11 You can quote the explanation.

[0538] φ is further preferably an anthracene ring or a fluorene ring, and the structure in this case can be described by referring to formula (ETM-2-1) or formula (ETM-2-2), where R in each formula 11 ~R 18 The explanation in formula (ETM-2-1) or formula (ETM-2-2) can be cited. Also, although formula (ETM-2-1) or formula (ETM-2-2) is explained in a form in which two pyridine substituents are bonded, when replacing these with benzimidazole substituents, both pyridine substituents may be replaced with benzimidazole substituents (i.e., n=2), or one of the pyridine substituents may be replaced with a benzimidazole substituent and the other pyridine substituent may be R 11 ~R 18 It can also be replaced with (i.e., n=1). Furthermore, for example, in equation (ETM-2-1) R 11 ~R 18 Replace at least one of the "pyridine substituents" with a benzimidazole substituent and R 11~R 18 You can replace it with this.

[0539] Specific examples of these benzimidazole derivatives include, for example, 1-phenyl-2-(4-(10-phenylanthracene-9-yl)phenyl)-1H-benzo[d]imidazole, 2-(4-(10-(naphthalene-2-yl)anthracene-9-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole, 2-(3-(10-(naphthalene-2-yl)anthracene-9-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole, and 5-(10-(naphthalene-2-yl)anthracene-9-yl)-1,2-diphenyl-1H-benzo[d]imidazole Examples include 1-(4-(10-(naphthalene-2-yl)anthracene-9-yl)phenyl)-2-phenyl-1H-benzo[d]imidazole, 2-(4-(9,10-di(naphthalene-2-yl)anthracene-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole, 1-(4-(9,10-di(naphthalene-2-yl)anthracene-2-yl)phenyl)-2-phenyl-1H-benzo[d]imidazole, and 5-(9,10-di(naphthalene-2-yl)anthracene-2-yl)-1,2-diphenyl-1H-benzo[d]imidazole.

[0540] [ka]

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

[0542] <Phenanthroline derivatives> Phenanthroline derivatives are compounds represented, for example, by the following formulas (ETM-12) or (ETM-12-1). Further details are described in International Publication No. 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 from 1 to 4.

[0544] R in each formula 11 ~R 18 Each of these is independently hydrogen, alkyl (preferably alkyl with 1 to 24 carbon atoms), cycloalkyl (preferably cycloalkyl with 3 to 12 carbon atoms), or aryl (preferably aryl with 6 to 30 carbon atoms). Also, in formula (ETM-12-1), R 11 ~R 18 One of these forms a bond with the aryl ring φ.

[0545] At least one hydrogen atom in each phenanthroline derivative may be substituted with deuterium.

[0546] R 11 ~R 18 The alkyl, cycloalkyl, and aryl elements in formula (ETM-2) are R 11 ~R 18 The explanation can be quoted. In addition to the examples above, φ can also be represented by the following structural formula. Note that in the following structural formulas, R is independently hydrogen, methyl, ethyl, isopropyl, cyclohexyl, phenyl, 1-naphthyl, 2-naphthyl, biphenylyl, or terphenylyl, and * indicates the bond position.

[0547] [ka]

[0548] Specific examples of phenanthroline derivatives include, for example, 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), basocproine, 1,3-bis(2-phenyl-1,10-phenanthroline-9-yl)benzene, and compounds represented by the following structural formula. [ka]

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

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

[0551] Specific examples of quinolinol-based metal complexes include 8-quinolinollithium, tris(8-quinolinolate)aluminum, tris(4-methyl-8-quinolinolate)aluminum, tris(5-methyl-8-quinolinolate)aluminum, tris(3,4-dimethyl-8-quinolinolate)aluminum, tris(4,5-dimethyl-8-quinolinolate)aluminum, tris(4,6-dimethyl-8-quinolinolate)aluminum, bis(2-methyl-8-quinolinolate)(phenolate)aluminum, and bis(2-methyl-8-quinolinolate) (2-methylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(3-methylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(4-methylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(2-phenylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(3-phenylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(4-phenylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(2,3 -Dimethylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(2,6-dimethylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(3,4-dimethylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(3,5-dimethylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(3,5-di-t-butylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(2,6-diphenylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(2,6-diphenylphenolate)aluminum, bis(2-methyl-8-quinolinolate) (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- Examples include 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, and bis(10-hydroxybenzo[h]quinoline)beryllium.

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

[0553] <Thiazole derivatives and benzothiazole derivatives> Thiazole derivatives are compounds represented by the following formula (ETM-14-1), for example. [ka] Benzothiazole derivatives are compounds represented by, for example, 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. The "thiazole substituent" and "benzothiazole substituent" are substituents in which the pyridyl in the "pyridine substituent" in formulas (ETM-2), (ETM-2-1), and (ETM-2-2) is replaced with thiazolyl or benzothiazol as described below, and at least one hydrogen in the thiazole derivative and benzothiazole derivative may be substituted with deuterium.

[0555] [ka]

[0556] φ is further preferably an anthracene ring or a fluorene ring, and the structure in this case can be described by referring to formula (ETM-2-1) or formula (ETM-2-2), where R in each formula 11 ~R 18 The explanation in formula (ETM-2-1) or formula (ETM-2-2) can be cited. Also, although formula (ETM-2-1) or formula (ETM-2-2) is explained in a form in which two pyridine substituents are bonded, when replacing these with thiazole substituents (or benzothiazole substituents), both pyridine substituents may be replaced with thiazole substituents (or benzothiazole substituents) (i.e., n=2), or one of the pyridine substituents may be replaced with a thiazole substituent (or benzothiazole substituent) and the other pyridine substituent may be R 11 ~R 18 It can also be replaced with (i.e., n=1). Furthermore, for example, in equation (ETM-2-1) R 11 ~R 18 Replace at least one of the "pyridine substituents" with a thiazole substituent (or benzothiazole substituent) 11 ~R 18 You can replace it with this.

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

[0558] <Silole derivatives> Silole derivatives are compounds represented by the following formula (ETM-15), for example. Further details are described in Japanese Patent Publication No. 9-194487. [ka]

[0559] X and Y are independently alkyl, cycloalkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, aryl, and heteroaryl groups, which may be substituted. For details of these groups, refer to the explanations in formulas (1) and (2), and further to the explanation in formula (ETM-7-2). Alkenyloxy and alkynyloxy are groups in which the alkyl portion of an alkoxy is replaced by an alkenyl or alkynyl, respectively, and for details of these alkenyl and alkynyl groups, refer to the explanation in formula (ETM-7-2). Furthermore, X and Y may be bonded to form a cycloalkyl ring (or a ring in which a portion is unsaturated), and details of this cycloalkyl ring can be found in the explanation of cycloalkyl in formulas (1) and (2).

[0560] R 1 ~R 4Each of these is 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 on halogens, alkyls, cycloalkyls, alkoxys, aryloxys, aminos, aryls, heteroaryls, alkenyls, and alkynyls in formulas (1) and (2), refer to the explanations provided.

[0562] R 1 ~R 4 Details regarding the alkyl, aryl, and alkoxy elements in alkylcarbonyl, arylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, alkylcarbonyloxy, arylcarbonyloxy, alkoxycarbonyloxy, and aryloxycarbonyloxy can also be found by referring to the explanations in formulas (1) and (2).

[0563] Examples of silyls include silyl and groups in which at least one of the three hydrogen atoms of the silyl is independently substituted with an aryl, alkyl, or cycloalkyl group. Tri-substituted silyls are preferred, and examples include triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, and alkyldicycloalkylsilyl. Details of the aryl, alkyl, and cycloalkyl groups in these can be found in the explanations for formulas (1) and (2).

[0564] The fused ring formed between adjacent substituents is, for example, R 1 and R 2 , R 2 and R 3 , R 3 and R 4 These are conjugated or unconjugated fused rings formed between such rings. These fused rings may contain nitrogen, oxygen, and sulfur atoms in their intraring structure, or they may be further fused with other rings.

[0565] However, preferably, R 1 and R 4 If is a phenyl group, then X and Y are not alkyl or phenyl. Also, preferably R 1 and R 4 If is thienyl, then X and Y are alkyl, R 2 and R 3 is alkyl, aryl, alkenyl or R 2 and R 3 It is a structure that does not simultaneously satisfy the requirement of a cycloalkyl group that is bonded to form a ring. Furthermore, preferably, R 1 and R 4 If R is cyllic, 2 , R 3 X and Y are, independently, not hydrogen or an alkyl group having 1 to 6 carbon atoms. Also, preferably, R 1 and R 2 In the case of a structure in which a benzene ring is fused, 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> Azoline derivatives are compounds represented by formula (ETM-16) below, for example. Further details 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 atom of φ may be substituted with an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 14 carbon atoms, an aryl group having 6 to 18 carbon atoms, or a heteroaryl group having 2 to 18 carbon atoms. Y is independently -O-, -S-, or >N-Ar, where Ar is a C6-C12 aryl or C2-C12 heteroaryl, and at least one hydrogen of Ar may be substituted with a C1-C4 alkyl, a C5-C10 cycloalkyl, a C6-C12 aryl, or a C2-C12 heteroaryl, R 1 ~R 5 Each of these is independently hydrogen, an alkyl group having 1 to 4 carbon atoms, or a cycloalkyl group having 5 to 10 carbon atoms, provided that Ar and R in >N-Ar are different. 1 ~R 5 One of these is a site that binds to L, L is independently selected from the group consisting of a divalent group represented by the following formula (L-1) and a divalent group represented by the following formula (L-2).

[0569] [ka]

[0570] In formula (L-1), X 1 ~X 6Each of them is independent of =CR 6 - or = N- and X 1 ~X 6 At least two of them are =CR 6 - and X 1 ~X 6 Two of the =CR 6 -R in 6 The φ or azoline ring is the site that binds to the ring, while the others are =CR. 6 -R in 6 It is hydrogen, In formula (L-2), X 7 ~X 14 Each of them is independent of =CR 6 - or = N- and X 7 ~X 14 At least two of them are =CR 6 - and X 7 ~X 14 Two of the =CR 6 -R in 6 The φ or azoline ring is the site that binds to the ring, while the others are =CR. 6 -R in 6 It is hydrogen, At least one hydrogen atom 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. m is an integer from 1 to 4, and when m is from 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 formulas (ETM-16-1) or (ETM-16-2). [ka]

[0572] In equations (ETM-16-1) and (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 atom of φ may be substituted with an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 14 carbon atoms, an aryl group having 6 to 18 carbon atoms, or a heteroaryl group having 2 to 18 carbon atoms. In formula (ETM-16-1), Y is independently -O-, -S-, or >N-Ar, where Ar is a C6-C12 aryl or C2-C12 heteroaryl, and at least one hydrogen atom of Ar may be substituted with a C1-C4 alkyl, a C5-C10 cycloalkyl, a C6-C12 aryl, or a C2-C12 heteroaryl. In formula (ETM-16-1), R 1 ~R 4 Each of these is independently hydrogen, an alkyl group having 1 to 4 carbon atoms, or a cycloalkyl group having 5 to 10 carbon atoms, where R 1 and R 2 They are identical, and R 3 and R 4 They are identical, In formula (ETM-16-2), R 1 ~R 5 Each of these is independently hydrogen, an alkyl group having 1 to 4 carbon atoms, or a cycloalkyl group having 5 to 10 carbon atoms, where R 1 and R 2 They are identical, and R 3 and R 4 They are identical, In equations (ETM-16-1) and (ETM-16-2), 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 Each of them is independent of =CR 6 - or = N- and X 1 ~X 6 At least two of them are =CR6 - and X 1 ~X 6 Two of the =CR 6 -R in 6 The φ or azoline ring is the site that binds to the ring, while the others are =CR. 6 -R in 6 It is hydrogen, In formula (L-2), X 7 ~X 14 Each of them is independent of =CR 6 - or = N- and X 7 ~X 14 At least two of them are =CR 6 - and X 7 ~X 14 Two of the =CR 6 -R in 6 The φ or azoline ring is the site that binds to the ring, while the others are =CR. 6 -R in 6 It is hydrogen, At least one hydrogen atom 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. m is an integer from 1 to 4, and when m is from 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 substituted with deuterium.

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

[0575] [ka]

[0576] [ka] [ka]

[0577] In the formulas, Z is >CR2, >N-Ar, >NL, -O-, or -S-, where R in >CR2 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, where 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 where L in >NL is L in formula (ETM-16), formula (ETM-16-1), or formula (ETM-16-2). The asterisk (*) in the formulas indicates a bond 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, sinnoline, and pteridine, and at least one hydrogen of L may be substituted with a C1-C4 alkyl, a C5-C10 cycloalkyl, a C6-C10 aryl, or a C2-C10 heteroaryl.

[0579] Preferably, in >N-Ar as Y or Z, Ar is selected from the group consisting of phenyl, naphthyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridadinyl, triazinyl, quinolinyl, isoquinolinyl, naphthyridinyl, phthalazinyl, quinoxalinyl, quinazolinyl, synnolinyl, and pteridinyl, and at least one hydrogen of Ar in >N-Ar as Y may be substituted with a C1-C4 alkyl, a C5-C10 cycloalkyl, or a C6-C10 aryl.

[0580] Preferably, R 1 to R 4 are each independently hydrogen, alkyl having 1 to 4 carbon atoms or cycloalkyl having 5 to 10 carbon atoms, provided that R 1 and R 2 are identical, R 3 and R 4 are identical, not all of R 1 to R 4 are hydrogen at the same time, and m is 1 or 2, and 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 addition, "Me" in the structural formula represents methyl.

Chemical Formula

Chemical Formula

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

Chemical Formula

[0583] L is a divalent group of a ring selected from the group consisting of benzene, pyridine, pyrazine, pyrimidine, pyridazine, and triazine, and at least one hydrogen 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 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 said Ar 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, R 1 ~R 4 are each independently hydrogen, alkyl having 1 to 4 carbon atoms or cycloalkyl having 5 to 10 carbon atoms, provided that R 1 and R 2 are the same, R 3 and R 4 are the same, and not all of R 1 ~R 4 are 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 addition, "Me" in the structural formula represents methyl.

Chemical Formula

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

[0586] This azoline derivative can be produced using known raw materials and known synthetic methods.

[0587] <Reducing Substance> The electron transport layer or electron injection layer may further contain a substance capable of reducing the material forming the electron transport layer or electron injection layer. Various reducing substances can be used, as long as they possess a certain reducing property. For example, at least one selected from the group consisting of alkali metals, alkaline earth metals, rare earth metals, alkali metal oxides, alkali metal halides, alkaline earth metal oxides, alkaline earth metal halides, rare earth metal oxides, rare earth metal halides, alkali metal organic complexes, alkaline earth metal organic complexes, and rare earth metal organic complexes can be suitably 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 (2.0-2.5 eV), or Ba (2.52 eV), with those having a work function of 2.9 eV or less being particularly preferred. Of these, alkali metals K, Rb, or Cs are more preferred reducing substances, Rb or Cs are even more preferred, and Cs is the most preferred. These alkali metals have particularly high reducing ability, and their addition in relatively small amounts to materials forming electron transport layers or electron injection layers can improve the luminescence brightness and extend the lifespan of organic EL devices. Furthermore, combinations of two or more alkali metals are also preferred as reducing substances with a work function of 2.9 eV or less, and combinations including Cs, such as Cs and Na, Cs and K, Cs and Rb, or Cs, Na, and K, are particularly preferred. By including Cs, the reducing ability can be efficiently exhibited, and by adding it to the material forming the electron transport layer or electron injection layer, improvements in luminescence brightness and extended lifespan can be achieved in organic EL devices.

[0589] 3. Substrates in organic electroluminescent devices The substrate 101 serves as a support for the organic EL element 100, and is typically made of quartz, glass, metal, or plastic. Depending on the purpose, the substrate 101 can be formed into a plate, film, or sheet, and examples include glass plates, metal plates, metal foils, plastic films, and plastic sheets. Among these, glass plates and transparent synthetic resin plates such as polyester, polymethacrylate, polycarbonate, and polysulfone are preferred. If a glass substrate is used, soda-lime glass or alkali-free glass can be used, and the thickness only needs to be sufficient to maintain mechanical strength, for example, 0.2 mm or more is sufficient. The upper limit of the thickness is, for example, 2 mm or less, preferably 1 mm or less. Regarding the glass material, alkali-free glass is preferred because it is better to have fewer ions eluted from the glass, but soda-lime glass with a barrier coating such as SiO2 is also commercially available and can be used. Furthermore, to enhance the gas barrier properties, the substrate 101 may be provided with a gas barrier film, such as a dense silicon oxide film, on at least one side. It is particularly preferable to provide a gas barrier film when using a synthetic resin plate, film, or sheet with low gas barrier properties as the substrate 101.

[0590] 4. Anode in an organic electroluminescent device The anode 102 plays the role of injecting holes into the light-emitting layer 105. If a hole injection layer 103 and / or a hole transport layer 104 are provided between the anode 102 and the light-emitting layer 105, holes will be 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), conductive polymers such as polypyrrole and polyaniline. In addition, other materials 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 sufficient current for the light-emitting element to emit light, but from the viewpoint of the power consumption of the light-emitting element, low resistance is desirable. For example, an ITO substrate with a resistance of 300 Ω / □ or less will function as an element electrode, but since substrates of about 10 Ω / □ are now available, it is particularly desirable to use a low-resistance product of, for example, 100 to 5 Ω / □, preferably 50 to 5 Ω / □. The thickness of the ITO can be arbitrarily selected according to the resistance value, but it is usually used between 50 and 300 nm.

[0593] 5. Hole injection layer and hole transport layer in organic electroluminescent element The hole injection layer 103 plays the 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 the 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 hole injection / transport materials and a polymer binder. Alternatively, an inorganic salt such as iron(III) chloride may be added to the hole injection / transport material to form a layer.

[0594] For hole-injecting and transporting materials, it is necessary to efficiently inject and transport holes from the positive electrode between electrodes under an applied electric field. Therefore, it is desirable to have high hole injection efficiency and efficient transport of the injected holes. To achieve this, it is preferable to have a low ionization potential, high hole mobility, excellent stability, and a material that does not easily generate trapping impurities during manufacturing and use.

[0595] As the material for forming the hole injection layer 103 and the hole transport layer 104, any material can be selected from among compounds conventionally used as charge transport materials for holes in photoconductive materials, p-type semiconductors, and known materials used in the hole injection layer and hole transport layer of organic EL devices. Specific examples include carbazole derivatives (N-phenylcarbazole, polyvinylcarbazole, etc.), biscarbazole derivatives such as bis(N-arylcarbazole) or bis(N-alkylcarbazole), and triarylamine derivatives (polymers having aromatic tertiary amino acids 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-carbazole-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-carbazole-3-yl)phenyl)-9H-fluoren-2-amine, N,N-bis(4-(dibenzo[b,d]furan-4-yl)phenyl)-[1,1':4',1”-terphenyl]- Examples include triphenylamine derivatives such as 4-amines, starburstamine derivatives, stilbene derivatives, phthalocyanine derivatives (metal-free, copper phthalocyanine, etc.), pyrazoline derivatives, hydrazone compounds, benzofuran derivatives and thiophene derivatives, oxadiazole derivatives, quinoxaline derivatives (e.g., 1,4,5,8,9,12-hexaazatriphenylene-2,3,6,7,10,11-hexacarbonitrine, etc.), heterocyclic compounds such as porphyrin derivatives, and polysilanes. Among polymer systems, polycarbonates and styrene derivatives having the above monomers in their side chains, polyvinylcarbazoles, and polysilanes are preferred, but the compound is not particularly limited as long as it can form a thin film necessary for the fabrication of a light-emitting device, allow holes to be injected from the anode, and transport holes.

[0596] Furthermore, the conductivity of organic semiconductors is known to be strongly influenced by doping. Such organic semiconductor matrix materials are composed of compounds with good electron-donating properties or compounds with good electron-accepting properties. Strong electron acceptors such as tetracyanoquinone dimethane (TCNQ) or 2,3,5,6-tetrafluorotetracyano-1,4-benzoquinone dimethane (F4TCNQ) are known for doping with electron-donating substances (see, for example, "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 through an electron transfer process in the electron-donating base material (hole transporter). The conductivity of the base material changes considerably depending on the number and mobility of holes. Examples of matrix materials having hole transport properties include benzidine derivatives (such as TPD) or starburst amine derivatives (such as TDATA), or certain metal phthalocyanines (especially zinc phthalocyanine (ZnPc)) (Japanese Patent Publication No. 2005-167175).

[0597] 6. Cathode in an Organic Electroluminescent Device The cathode 108 plays the role of injecting electrons into the light-emitting layer 105 via the electron injection layer 107 and the electron transport layer 106.

[0598] The material forming the cathode 108 is not particularly limited as long as it can efficiently inject electrons into the organic layer, but the same material as that forming the anode 102 can be used. Among these, metals such as tin, indium, calcium, aluminum, silver, copper, nickel, chromium, gold, platinum, iron, zinc, lithium, sodium, potassium, cesium, and magnesium, or their alloys (such as magnesium-silver alloys, magnesium-indium alloys, and aluminum-lithium alloys such as lithium fluoride / aluminum), are preferred. To increase electron injection efficiency and improve device characteristics, alloys containing lithium, sodium, potassium, cesium, calcium, magnesium, or these low work function metals are effective. However, these low work function metals are generally unstable in the atmosphere. To improve this, for example, a method is known in which the organic layer is doped with trace amounts of lithium, cesium, or magnesium to use electrodes with high stability. Other dopants that can be used include inorganic salts such as lithium fluoride, cesium fluoride, lithium oxide, and cesium oxide. However, the material is not limited to these.

[0599] Furthermore, for electrode protection, it is preferable to laminate metals such as platinum, gold, silver, copper, iron, tin, aluminum, and indium, or alloys using these metals, as well as inorganic materials such as silica, titania, and silicon nitride, polyvinyl alcohol, vinyl chloride, and hydrocarbon polymer compounds. The method for fabricating these electrodes is not particularly limited as long as conductivity can be achieved, such as resistance heating, electron beam deposition, sputtering, ion plating, and coating.

[0600] 7. Binding agents that may be used in each layer of an organic electroluminescent device The materials used in the hole injection layer, hole transport layer, light emission layer, electron transport layer, and electron injection layer described above can form each layer individually, but they can also be dispersed in solvent-soluble resins such as polyvinyl chloride, polycarbonate, polystyrene, poly(N-vinylcarbazole), polymethyl methacrylate, polybutyl methacrylate, polyester, polysulfone, polyphenylene oxide, polybutadiene, hydrocarbon resins, ketone resins, phenoxy resins, polyamides, ethylcellulose, vinyl acetate resins, ABS resins, and polyurethane resins, or in curable resins such as phenolic resins, xylene resins, petroleum resins, urea resins, melamine resins, unsaturated polyester resins, alkyd resins, epoxy resins, and silicone resins as polymer binders.

[0601] <<Method for fabricating organic electroluminescent devices>> Each layer constituting an organic EL element can be formed by thinning the material to be composed of each layer using methods such as vapor deposition, resistance heating deposition, electron beam deposition, sputtering, molecular stacking, printing, inkjet, spin coating or casting, or coating. There are no particular limitations on the thickness of each layer formed in this way, and it can be set appropriately according to the properties of the material, but it is usually in the range of 2 nm to 5000 nm. The thickness can usually be measured with a quartz crystal oscillating film thickness analyzer. When thinning using vapor deposition, the deposition conditions vary depending on the type of material, the desired crystal structure and association structure of the film, etc. Generally, the deposition conditions are a boat heating temperature of +50 to +400°C and a vacuum of 10°C. -6 ~10 -3 It is preferable to appropriately set the Pa, deposition rate to 0.01 to 50 nm / second, substrate temperature to -150 to +300°C, and film thickness to 2 nm to 5 μm.

[0602] Next, as an example of a method for fabricating an organic EL element, we will describe a method for fabricating an organic EL element consisting of an anode, a hole injection layer, a hole transport layer, an emissive layer made of host material and dopant material, an electron transport layer, an electron injection layer, and a cathode. An anode is fabricated by forming a thin film of anode material on a suitable substrate by vapor deposition or the like, and then thin films of a hole injection layer and a hole transport layer are formed on this anode. A thin film of host material and dopant material is co-deposited on this to form an emissive layer, and then an electron transport layer and an electron injection layer are formed on this emissive layer. Furthermore, a thin film made of cathode material is formed by vapor deposition or the like to form the cathode, thereby obtaining the desired organic EL element. In addition, in the fabrication of the organic EL element described above, it is also possible to reverse the fabrication order and fabricate the cathode, electron injection layer, electron transport layer, emissive layer, hole transport layer, hole injection layer, and anode in that order.

[0603] When applying a DC voltage to the organic EL element obtained in this way, the voltage should be applied with the anode as + and the cathode as -. When a voltage of approximately 2 to 40V is applied, light emission can be observed from the transparent or semi-transparent electrode side (anode or cathode, or both). Furthermore, this organic EL element will also emit light when a pulsed current or alternating current is applied. The waveform of the applied AC current can be arbitrary.

[0604] <<Application Examples of Organic Electroluminescent Devices>> Furthermore, the present invention can also be applied to display devices equipped with organic EL elements or lighting devices equipped with organic EL elements. A display device or lighting device equipped with an organic EL element can be manufactured by known methods, such as connecting the organic EL element according to this embodiment with a known driving device, and can be driven using known driving methods such as DC driving, pulse driving, or AC driving as appropriate.

[0605] Examples of display devices include panel displays such as color flat panel displays, and flexible displays such as flexible color organic electroluminescent (EL) displays (see, for example, Japanese Patent Publication No. 10-335066, Japanese Patent Publication No. 2003-321546, and Japanese Patent Publication No. 2004-281086). Examples of display methods include matrix and / or segment displays. Matrix and segment displays may coexist on the same panel.

[0606] A matrix is ​​a two-dimensional arrangement of pixels for display purposes, such as a grid or mosaic pattern, used to display characters and images. The shape and size of the pixels are determined by their application. For example, for displaying images and text on personal computers, monitors, and televisions, square pixels with sides of 300 μm or less are typically used, while large displays such as display panels use pixels with sides on the order of millimeters. For monochrome displays, pixels of the same color can be arranged, but for color displays, red, green, and blue pixels are arranged side by side. In this case, there are typically delta type and stripe type matrices. The matrix can be driven by either a line-sequential drive method or an active matrix. Line-sequential drive has the advantage of a simpler structure, but considering the operating characteristics, the active matrix may be superior in some cases, so it is necessary to choose the appropriate method depending on the application.

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

[0608] Examples of lighting devices include lighting devices such as indoor lighting and backlights for liquid crystal display devices (see, for example, Japanese Patent Publication No. 2003-257621, Japanese Patent Publication No. 2003-277741, and Japanese Patent Publication No. 2004-119211). Backlights are mainly used to improve the visibility of non-self-illuminating display devices and are used in liquid crystal display devices, clocks, audio equipment, automobile panels, display boards, and signs. In particular, for liquid crystal display devices, especially backlights for personal computers where miniaturization is a challenge, conventional methods consist of fluorescent lamps and light guide plates, making miniaturization difficult. Therefore, the backlight using the light-emitting element according to this embodiment is characterized by being thin and lightweight. [Examples]

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

[0610] Synthesis example (1-1) Synthesis of compounds (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. After raising the reaction mixture to -8°C, a solution of 1,2-benzanthraquinone (5 g) in CPME (100 mL) was added dropwise, and the mixture was stirred at room temperature for 2 hours. Water (100 mL) was added to stop the reaction, and the aqueous layer was removed by liquid-liquid extraction. The organic layer was concentrated under reduced pressure, and the precipitated solid was washed with Solmix A-11 (trade name, manufactured by Nippon Alcohol Sales Co., Ltd.) (200 mL) to obtain a pale yellow solid. Potassium iodide (8.7 g), sodium phosphinate monohydrate (2.5 g), and acetic acid (100 mL) were added to this solid, and the mixture was stirred under reflux temperature for 2 hours. The reaction mixture was cooled to 60°C, and the precipitated solid was filtered under reduced pressure. This solid was then washed and purified 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 compound obtained by NMR measurement was confirmed. 1 H-NMR (400MHz, CDCl3): δ=9.00~8.85(m,4H), 8.00~7.55(m,14H), 7.54~7.15(m,9H), 6.85~6.75(m,1H).

[0614] Synthesis examples (1-2) Synthesis of compounds (1-7) [ka]

[0615] Compound (1-7) was synthesized according to the method described in the aforementioned synthesis example (1-1). Mass spectrometry confirmed that the obtained compound was compound (1-7). EI-MS: m / z = 481.

[0616] Synthesis examples (1-3) Synthesis of compounds (1-242) [ka]

[0617] Compound (1-242) was synthesized according to the method described in the aforementioned synthesis example (1-1). Mass spectrometry confirmed that the obtained compound was compound (1-242). EI-MS: m / z = 633.

[0618] Synthesis examples (1-4) Synthesis of compounds (1-90) [ka]

[0619] Compound (1-90) was synthesized according to the method described in International Publication No. 2009 / 081776. Mass spectrometry confirmed the obtained compound to be compound (1-90). EI-MS: m / z = 557.

[0620] Synthesis examples (1-5) Synthesis of compounds (1-78) [ka]

[0621] Compound (1-78) was synthesized according to the method described in International Publication No. 2009 / 081776. Mass spectrometry confirmed the obtained compound to be compound (1-78). EI-MS: m / z = 557.

[0622] Synthesis examples (1-6) Synthesis of compounds (1-93) [ka]

[0623] Compound (1-93) was synthesized according to the method described in International Publication No. 2009 / 081776. Mass spectrometry confirmed the obtained compound to be compound (1-93). EI-MS: m / z = 557.

[0624] Synthesis examples (1-7) Synthesis of compounds (1-158) [ka]

[0625] Compound (1-158) was synthesized according to the method described in the aforementioned synthesis example (1-1). Mass spectrometry confirmed that the obtained compound was compound (1-158). EI-MS: m / z = 633.

[0626] Synthesis examples (1-8) Synthesis of compounds (1-161) [ka]

[0627] Compound (1-161) was synthesized according to the method described in International Publication No. 2009 / 081776. Mass spectrometry confirmed the obtained compound to be compound (1-161). EI-MS: m / z = 633.

[0628] Synthesis examples (1-9) Synthesis of compounds (1-170) [ka]

[0629] Compound (1-170) was synthesized according to the method described in International Publication No. 2009 / 081776. Mass spectrometry confirmed the obtained compound to be compound (1-170). EI-MS: m / z = 683.

[0630] Synthesis examples (1-10) Synthesis of compounds (1-8) [ka]

[0631] Compounds (1-8) were synthesized according to the method described in International Publication No. 2009 / 081776. Mass spectrometry confirmed that the obtained compounds were compounds (1-8). EI-MS: m / z = 481.

[0632] Synthesis examples (1-11) Synthesis of compounds (1-48) [ka]

[0633] Compound (1-48) was synthesized according to the method described in International Publication No. 2009 / 081776. Mass spectrometry confirmed the obtained compound to be compound (1-48). EI-MS: m / z = 531.

[0634] Synthesis examples (1-12) Synthesis of compounds (1-185) [ka]

[0635] Compound (1-185) was synthesized according to the method described in International Publication No. 2009 / 081776. Mass spectrometry confirmed the obtained compound to be compound (1-185). EI-MS: m / z = 547.

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

[0637] Compound (1-203) was synthesized according to the method described in International Publication No. 2009 / 081776. Mass spectrometry confirmed the obtained compound to be compound (1-203). EI-MS: m / z = 583.

[0638] Synthesis examples (1-14) Synthesis of compounds (1-129) [ka]

[0639] Compound (1-129) was synthesized according to the method described in International Publication No. 2009 / 081776. Mass spectrometry confirmed the obtained compound to be compound (1-129). EI-MS: m / z = 557.

[0640] Synthesis examples (1-15) Synthesis of compounds (1-244) [ka]

[0641] Compound (1-244) was synthesized according to the method described in the aforementioned synthesis example (1-1). Mass spectrometry confirmed that the obtained compound was compound (1-244). EI-MS: m / z = 613.

[0642] Synthesis examples (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 at 110°C for 1 hour with stirring. After cooling to room temperature, water and ethyl acetate were added and stirred for a while. The organic layer was then concentrated, and heptane was added to collect the precipitate. Toluene / heptane = 1 / 1 (volume ratio) was added to this precipitate to collect the soluble components, and after purification using a silica gel short-pass column (eluent: toluene / heptane = 1 / 1 (volume ratio)), the compound (1-753-O) (1.0 g) was obtained by heptane reprecipitation.

[0644] [ka]

[0645] The structure of the compound obtained by NMR measurement was confirmed. 1 H-NMR (CDCl3): σ=7.42~7.64(m, 8H), 7.71~7.74(m, 2H), 7.78(dd, 1H), 7.82(dd, 1H), 7.98~8.01(m, 3h), 8.14(d, 1H), 8.21(d, 1H), 8.37(s, 1h), 8.93(d, 1H), 9.31(s, 1H).

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

[0647] Under a 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, followed by the dropwise addition of benz[a]anthracene-12(7H)-one (24.43 g), 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 then with pure water, and dried over sodium sulfate. The organic phase was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain the compound represented by formula (1-714-O) (28.40 g). Mass spectrometry confirmed that the obtained compound was (1-714-O). EI-MS: m / z = 395.

[0648] [ka]

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

[0650] Compound (1-703-O) was synthesized according to the method described in the aforementioned synthesis example (1-17). Mass spectrometry confirmed that the obtained compound was compound (1-703-O). EI-MS: m / z = 445.

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

[0652] Compound (1-702-O) was synthesized according to the method described in the aforementioned synthesis example (1-17). Mass spectrometry confirmed that the obtained compound was compound (1-702-O). EI-MS: m / z = 445.

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

[0654] Compound (1-705-O) was synthesized according to the method described in the aforementioned synthesis example (1-17). Mass spectrometry confirmed that the obtained compound was compound (1-705-O). EI-MS: m / z = 445.

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

[0656] Compound (1-713-O) was synthesized according to the method described in the aforementioned synthesis example (1-17). Mass spectrometry confirmed that the obtained compound was compound (1-713-O). EI-MS: m / z = 445.

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

[0658] Compound (1-718-O) was synthesized according to the method described in the aforementioned synthesis example (1-16). Mass spectrometry confirmed that the obtained compound was compound (1-718-O). EI-MS: m / z = 395.

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

[0660] Compound (1-715-O) was synthesized according to the method described in the aforementioned synthesis example (1-17). Mass spectrometry confirmed that the obtained compound was compound (1-715-O). EI-MS: m / z = 395.

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

[0662] Compound (1-717-S) was synthesized according to the method described in the aforementioned synthesis example (1-16). Mass spectrometry confirmed that the obtained compound was compound (1-717-S). EI-MS: m / z = 411.

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

[0664] Compound (1-714-S) was synthesized according to the method described in the aforementioned synthesis example (1-17). Mass spectrometry confirmed that the obtained compound was compound (1-714-S). EI-MS: m / z = 411.

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

[0666] Compound (1-718-N) was synthesized according to the method described in the aforementioned synthesis example (1-16). Mass spectrometry confirmed that the obtained compound was compound (1-718-N). EI-MS: m / z = 470.

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

[0668] Compound (1-715-N) was synthesized according to the method described in the aforementioned synthesis example (1-17). Mass spectrometry confirmed that the obtained compound was compound (1-715-N). EI-MS: m / z = 470.

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

[0670] Compound (1-551-O) was synthesized according to the method described in International Publication No. 2009 / 081776. Mass spectrometry confirmed the obtained compound to be compound (1-551-O). EI-MS: m / z = 471.

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

[0672] Compound (1-381-O) was synthesized according to the method described in International Publication No. 2009 / 081776. Mass spectrometry confirmed the obtained compound to be compound (1-381-O). EI-MS: m / z = 471.

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

[0674] Compound (1-755-O) was synthesized according to the method described in the aforementioned synthesis example (1-16). Mass spectrometry confirmed that the obtained compound was compound (1-755-O). EI-MS: m / z = 445.

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

[0676] Compound (1-778-O) was synthesized according to the method described in the aforementioned synthesis example (1-1). Mass spectrometry confirmed that the obtained compound was compound (1-778-O). EI-MS: m / z = 661.

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

[0678] Compound (1-752-O) was synthesized according to the method described in the aforementioned synthesis example (1-16). Mass spectrometry confirmed that the obtained compound was compound (1-752-O). EI-MS: m / z = 445.

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

[0680] Compound (1-717-O) was synthesized according to the method described in the aforementioned synthesis example (1-16). Mass spectrometry confirmed that the obtained compound was compound (1-717-O). EI-MS: m / z = 395.

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

[0682] Compound (1-785-O) was synthesized according to the method described in International Publication No. 2009 / 081776. Mass spectrometry confirmed the obtained compound to be compound (1-785-O). EI-MS: m / z = 571.

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

[0684] Compound (1-790-O) was synthesized according to the method described in International Publication No. 2009 / 081776. Mass spectrometry confirmed the obtained compound to be (1-790-O). EI-MS: m / z = 571.

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

[0686] Compound (1-763-O) was synthesized according to the method described in the aforementioned synthesis example (1-16). Mass spectrometry confirmed that the obtained compound was compound (1-763-O). EI-MS: m / z = 445.

[0687] Synthesis examples (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 spectrometry confirmed the obtained compound to be compound (1-387-O). EI-MS: m / z = 547.

[0689] Synthesis examples (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 spectrometry confirmed the obtained compound to be compound (1-1699-O). EI-MS: m / z = 697.

[0691] Synthesis examples (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 spectrometry confirmed the obtained compound to be compound (1-1663-O). EI-MS: m / z = 723.

[0693] Synthesis examples (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 spectrometry confirmed the obtained compound to be compound (1-383-N). EI-MS: m / z = 546.

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

[0696] Compound (1-1552-O) was synthesized according to the method described in International Publication No. 2009 / 081776. Mass spectrometry confirmed the obtained compound to be compound (1-1552-O). EI-MS: m / z = 673.

[0697] Synthesis examples (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 spectrometry confirmed the obtained compound to be compound (1-1683-O). EI-MS: m / z = 723.

[0699] Synthesis examples (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 spectrometry confirmed the obtained compound to be compound (1-1680-O). EI-MS: m / z = 647.

[0701] Synthesis examples (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 spectrometry confirmed the obtained compound to be compound (1-1599-O). EI-MS: m / z = 623.

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

[0704] Compound (1-1116-O) was synthesized according to the method described in the aforementioned synthesis example (1-1). Mass spectrometry confirmed that the obtained compound was compound (1-1116-O). EI-MS: m / z = 597.

[0705] Synthesis examples (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 spectrometry confirmed the obtained compound to be (1-1025-O). EI-MS: m / z = 713.

[0707] Synthesis examples (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 spectrometry confirmed the obtained compound to be compound (1-1703-O). EI-MS: m / z = 747.

[0709] Synthesis examples (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 spectrometry confirmed the obtained compound to be compound (1-1751-O). EI-MS: m / z = 603.

[0711] Synthesis examples (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 spectrometry confirmed the obtained compound to be compound (1-1665-O). EI-MS: m / z = 863.

[0713] Synthesis examples (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 spectrometry confirmed the obtained compound to be compound (1-1584-S). EI-MS: m / z = 563.

[0715] Synthesis examples (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 spectrometry confirmed the obtained compound to be compound (1-1538-N). EI-MS: m / z = 622.

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

[0718] Compound (1-1001-O) was synthesized according to the method described in the aforementioned synthesis example (1-1). Mass spectrometry confirmed that the obtained compound was compound (1-1001-O). EI-MS: m / z = 547.

[0719] Synthesis examples (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 spectrometry confirmed the obtained compound to be compound (1-1716-O). EI-MS: m / z = 623.

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

[0722] Compound (1-1184-O) was synthesized according to the method described in the aforementioned synthesis example (1-1). Mass spectrometry confirmed that the obtained compound was compound (1-1184-O). EI-MS: m / z = 647.

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

[0724] Compound (1-1140-O) was synthesized according to the method described in International Publication No. 2009 / 081776. Mass spectrometry confirmed the obtained compound to be compound (1-1140-O). EI-MS: m / z = 773.

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

[0726] Compound (1-1347-O) was synthesized according to the method described in the aforementioned synthesis example (1-1). Mass spectrometry confirmed that the obtained compound was compound (1-1347-O). EI-MS: m / z = 823.

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

[0728] Compound (1-1783-O) was synthesized according to the method described in the aforementioned synthesis example (1-1). Mass spectrometry confirmed that the obtained compound was compound (1-1783-O). EI-MS: m / z = 547.

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

[0730] Compound (1-1759-O) was synthesized according to the method described in the aforementioned synthesis example (1-1). Mass spectrometry confirmed that the obtained compound was compound (1-1759-O). EI-MS: m / z = 547.

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

[0732] Compound (1-1767-O) was synthesized according to the method described in the aforementioned synthesis example (1-1). Mass spectrometry confirmed that the obtained compound was compound (1-1767-O). EI-MS: m / z = 647.

[0733] Synthesis examples (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 spectrometry confirmed the obtained compound to be compound (1-1777-O). EI-MS: m / z = 623.

[0735] Synthesis examples (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 spectrometry confirmed the obtained compound to be compound (1-1781-O). EI-MS: m / z = 561.

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

[0738] Compound (1-1592-O) was synthesized according to the method described in International Publication No. 2009 / 081776. Mass spectrometry confirmed the obtained compound to be compound (1-1592-O). EI-MS: m / z = 623.

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

[0740] Compound (1-1798-O) was synthesized according to the method described in the aforementioned synthesis example (1-17). Mass spectrometry confirmed that the obtained compound was compound (1-1798-O). EI-MS: m / z = 471.

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

[0742] Compound (1-1795-O) was synthesized according to the method described in the aforementioned synthesis example (1-17). Mass spectrometry confirmed that the obtained compound was compound (1-1795-O). EI-MS: m / z = 431.

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

[0744] Compound (1-1797-O) was synthesized according to the method described in the aforementioned synthesis example (1-17). Mass spectrometry confirmed that the obtained compound was compound (1-1797-O). EI-MS: m / z = 431.

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

[0746] Compound (1-1805-O) was synthesized according to the method described in the aforementioned synthesis example (1-17). Mass spectrometry 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 International Publication No. 2015 / 102118. The structure of the compound obtained by NMR measurement was confirmed. 1 H-NMR (500MHz, CDCl3): δ=1.47(s,36H), 2.17(s,3H), 5.97(s,2H), 6.68(d,2H), 7.28(d,4H), 7.49(dd,2H), 7.67(d,4H), 8.97(d,2H).

[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 International Publication No. 2015 / 102118.

[0751] The structure of the compound obtained by NMR measurement was confirmed. 1H-NMR (500MHz, CDCl3): δ=1.46(s,18H), 1.47(s,18H), 6.14(d,2H), 6.75(d,2H), 7.24(t,1H), 7.29(d,4H), 7.52(dd,2H), 7.67(d,4H), 8.99(d,2H).

[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 International Publication No. 2015 / 102118.

[0754] The structure of the compound obtained by NMR measurement was confirmed. 1 H-NMR (CDCl3): δ=1.20(s,9H), 1.37(s,18H), 1.46(s,9H), 1.47(s,9H), 2.18(s,3H), 5.97(s,1H), 6.08(d,1H), 6.63(d,1H) ), 6.66(d,1H), 7.20(d,2H), 7.27(d,2H), 7.32(dd,1H), 7.48(dd,1H), 7.61(t,1H), 7.67(d,2H), 8.84(d,1H), 8.94(d,1H).

[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 International Publication No. 2015 / 102118.

[0757] The structure of the compound obtained by NMR measurement was confirmed. 1H-NMR (CDCl3): δ=1.20(s,9H), 1.36(s,18H), 1.46(s,9H), 1.47(s,9H), 6.14(d,1H), 6.25(d,1H), 6.68(d,1H), 6.73 (d,1H), 7.21(d,2H), 7.29(d,3H), 7.34(dd,1H), 7.51(dd,1H), 7.61(t,1H), 7.67(d,2H), 8.86(d,1H), 8.96(d,1H).

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

[0759] Using the same method as described in the synthesis example above, the compound represented by formula (2-42) was synthesized.

[0760] The structure of the compound obtained by NMR measurement was confirmed. 1 H-NMR (CDCl3): δ=1.37(s,18H), 1.46(s,9H), 1.47(s,9H), 2.17(s,3H), 5.56(s,1H), 5.99(s,1H), 6.68(d,1H), 6.74(d ,1H), 7.19(d,2H), 7.24~7.29(m,3H), 7.42(t,1H), 7.49(dd,1H), 7.61(t,1H), 7.68(d,2H), 8.91(dd,1H), 8.92(d,1H).

[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 Japanese Patent Publication No. 2016-88927.

[0763] The structure of the compound obtained by NMR measurement was confirmed. 1H-NMR (CDCl3): δ=1.33(s,18H), 1.46(s,18H), 5.55(s,2H), 6.75(d,2H), 6.89( t,2H), 6.94(d,4H), 7.06(t,4H), 7.13(d,4H), 7.43~7.46(m,6H), 8.95(d,2H).

[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 International Publication No. 2015 / 102118.

[0766] The structure of the compound obtained by NMR measurement was confirmed. 1 H-NMR (CDCl3): δ=1.3(s,18H), 1.3(s,18H), 1.5(s,18H), 5.8(s,2H), 6.6( d,2H), 6.8(dd,4H), 7.1(dd,4H), 7.1(dd,4H), 7.4~7.5(m,6H), 8.9(d,2H).

[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 International Publication No. 2015 / 102118.

[0769] The structure of the compound obtained by NMR measurement was confirmed. 1H-NMR (CDCl3): δ=1.35(s,18H), 1.50(s,18H), 6.34(s,2H), 6.85(d,2H), 7.16(t,2H), 7.23(t,2H), 7.32~7.35(m,6H), 7.56(dd,2H), 7.63(d,4H), 7.99(d,2H), 9.05(d,2H).

[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 International Publication No. 2015 / 102118.

[0772] The structure of the compound obtained by NMR measurement was confirmed. 1 H-NMR (CDCl3): δ=1.22(s,9H), 1.37(s,9H), 1.46(s,9H), 1.47(s,9H), 6.14(d,1H), 6.18(d,1H), 6.72(d,1H), 6.74(d,1H), 7.19( ddd,1H), 7.23~7.30(m,3H), 7.34(dd,1H), 7.41(t,1H), 7.51(dd,1H), 7.58~7.64(m,2H), 7.67(d,2H), 8.86(d,1H), 8.96(d,1H).

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

[0774] Under a nitrogen atmosphere, 15.0 g of 4-(t-amyl)aniline was dissolved in 150 ml of acetonitrile, and 22.5 g of bromine was added dropwise under ice cooling. The mixture was stirred for 0.5 hours. After the reaction, water and ethyl acetate were added to the reaction mixture and stirred. The organic layer was then separated and washed with water. The organic layer was then concentrated to obtain the 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). Then, 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 mixture and stirred. The organic layer was then separated and washed with water. The organic layer was then concentrated to obtain the 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)phosphin)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 mixture and stirred, and the organic layer was separated and washed with water. The organic layer was then concentrated to obtain the 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] To a flask containing the intermediate (IC) (18.0 g) and t-butylbenzene (500 ml), 28.9 ml of 1.56 M t-butyllithium pentane solution was added under a nitrogen atmosphere at 0°C. After the addition was complete, the temperature was raised to 70°C and stirred for 0.5 hours, after which components with a lower boiling point than t-butylbenzene were removed by reduced pressure distillation. The mixture was cooled to -50°C, boron tribromide (11.3 g) was added, and the temperature was raised to room temperature and stirred for 0.5 hours. Then, it was cooled again to 0°C, N,N-diisopropylethylamine (5.8 g) was added, and the mixture was stirred at room temperature until the exothermic reaction subsided, then the temperature was raised to 100°C and heated and stirred for 1 hour. The reaction mixture was cooled to room temperature, and liquid-liquid separation was performed by adding aqueous sodium acetate, which had been cooled in an ice bath, followed by ethyl acetate. The organic layer was concentrated and purified by silica gel short column (eluent: toluene). The crude product obtained was recrystallized with chlorobenzene to obtain compound (2-508) (7.1 g).

[0781] [ka]

[0782] The structure of the compound obtained by NMR measurement was confirmed. 1 H-NMR (CDCl3): δ=0.49(t,3H), 0.92(s,6H), 1.28(q,2H), 1.46(s,18H), 1.47(s,18 H), 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 a 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 mixture and stirred, and the organic layer was separated and washed with water. The organic layer was then concentrated to obtain the 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 mixture and stirred, and the organic layer was separated and washed with water. The organic layer was then concentrated to obtain the 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] To a flask containing intermediate (IE) (23.0 g) and tert-butylbenzene (250 ml), 33.5 ml of 1.62 M tert-butyllithium pentane solution was added at 0°C under a nitrogen atmosphere. After the addition was complete, the temperature was raised to 60°C and stirred for 1 hour, then components with a lower boiling point than tert-butylbenzene were removed by distillation under reduced pressure. The mixture was cooled to -50°C, boron tribromide (13.6 g) was added, and 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 (7.0 g) was added, and the mixture was stirred at room temperature until the exothermic reaction subsided, then the temperature was raised to 100°C and heated and stirred for 1 hour. The reaction mixture was cooled to room temperature, and liquid-liquid separation was performed by adding aqueous sodium acetate cooled in an ice bath, followed by ethyl acetate. The organic layer was concentrated and purified using a silica gel short column (eluent: heated chlorobenzene). The crude product obtained was washed with refluxed heptane and refluxed ethyl acetate, and then reprecipitated from chlorobenzene to obtain compound (2-538) (12.9 g).

[0789] [ka]

[0790] The structure of the compound obtained by NMR measurement was confirmed. 1 H-NMR (CDCl3): δ=1.3(s,18H), 1.5(s,18H), 5.6(s,2H), 6.8(d,2H), 7.1(m,4H), 7.4~7.5(m,6H), 9.0(d,2H).

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

[0792] Under a nitrogen atmosphere, d 5 -Aniline (5.0g), d 5Bromobenzene (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 mixture and stirred, and the organic layer was separated and washed with water. The organic layer was then concentrated to obtain the 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), palladium catalyst Pd-132 (0.31 g), 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 mixture and stirred. The organic layer was separated and washed with water. The organic layer was then concentrated to obtain the crude product. The crude product was purified using a silica gel short column (eluent: toluene / heptane = 1 / 1 (volume ratio)) to obtain 20.2 g of intermediate (IH).

[0795] [ka]

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

[0797] [ka]

[0798] The structure of the compound obtained by NMR measurement was confirmed. 1 H-NMR (CDCl3): δ=1.46(s,9H), 1.47(s,9H), 2.16(s,3H), 5.92(s,1H), 6.00(s,1H), 6.69(d,1H), 7.25-7.28(m,2H), 7.49-7.51(m,1H), 7.66-7.69(m,2H), 8.92(d,1H).

[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 mixture and stirred, and the organic layer was separated and washed with water. The organic layer was then concentrated to obtain the crude product. The crude product was purified using a silica gel short-pass column (eluent: toluene) to obtain intermediate (IK) (8.6 g).

[0801] [ka]

[0802] To a flask containing the intermediate (IK) (8.6 g) and tert-butylbenzene (90 ml), 12.9 ml of 1.62 M tert-butyllithium pentane solution was added at 0°C under a nitrogen atmosphere. After the addition was complete, the temperature was raised to 70°C and stirred for 0.5 hours, then components with a lower boiling point than tert-butylbenzene were removed by distillation under reduced pressure. The mixture was cooled to -50°C, boron tribromide (5.0 g) was added, and 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 exothermic reaction subsided, then the temperature was raised to 100°C and heated and stirred for 1 hour. The reaction mixture was cooled to room temperature, and an aqueous sodium acetate solution cooled in an ice bath, followed by ethyl acetate, was added and stirred for 1 hour. The yellow suspension was filtered, and the precipitate was washed twice with methanol and pure water, and then washed again with methanol. The yellow crystals were heated and dissolved in chlorobenzene, then purified using a silica gel short-pass column (eluent: heated chlorobenzene). The resulting 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 compound obtained by NMR measurement was confirmed. 1 H-NMR (CDCl3): δ=1.33(s,18H), 1.46(s,18H), 5.55(s,2H), 6.88(t,2H), 6.94(d,4H), 7.06(dd,4H).

[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 mixture and stirred, and the organic layer was separated and washed with water. The organic layer was then concentrated to obtain the crude product. The crude product was purified using a silica gel short-pass column (eluent: toluene), and the resulting solid was washed with cooled heptane to obtain intermediate (IL) (9.4 g).

[0807] [ka]

[0808] To a flask containing the intermediate (IL) (8.6 g) and tert-butylbenzene (100 ml), 13.8 ml of 1.62 M tert-butyllithium pentane solution was added at 0°C under a nitrogen atmosphere. After the addition was complete, the temperature was raised to 60°C and stirred for 0.5 hours, then components with a lower boiling point than tert-butylbenzene were removed by distillation under reduced pressure. The mixture was cooled to -50°C, boron tribromide (5.4 g) was added, and 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 (2.8 g) was added, and the mixture was stirred at room temperature until the exothermic reaction subsided, then the temperature was raised to 100°C and heated and stirred for 1 hour. The reaction mixture was cooled to room temperature, and an aqueous sodium acetate solution cooled in an ice bath, followed by ethyl acetate, was added and stirred for 1 hour. The yellow suspension was filtered, and the precipitate was washed twice with methanol and pure water, and then washed again with methanol. The yellow crystals were heated and dissolved in chlorobenzene, then purified using a silica gel short-pass column (eluent: heated chlorobenzene). The resulting 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 compound obtained by NMR measurement was confirmed. 1 H-NMR (CDCl3): 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 International Publication No. 2017 / 126443.

[0813] The structure of compound (2-290) obtained by NMR measurement was confirmed. 1 H-NMR (CDCl3): δ=8.64(s,2H), 7.75(m,3H), 7.69(d,2H), 7.30(t,8H), 7.25(s,2H), 7.20(m,10H), 7.08(m,6H), 1.58(s,12H).

[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 International Publication No. 2017 / 126443.

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

[0817] 1 H-NMR (CDCl3): δ=9.22(s,1H), 8.78(s,1H), 7.96(d,2H), 7.80~7.77(m,6H), 7.71(d,1H), 7.59~7.44(m,8H), 7.39 (t,1H), 7.32~7.29(m,4H), 7.71(d,1H), 7.19(dd,4H), 7.12~7.06(m,4H), 7.00(d,1H), 6.45(d,1H), 1.57(s,6H).

[0818] Furthermore, 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°C / min, heating rate 10°C / min]

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

[0820] Compound (2-60) was synthesized using the same method as in synthesis example (2-1). The structure of the compound obtained by NMR measurement was confirmed. 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 using the same method as in synthesis example (2-1). The structure of the compound obtained by NMR measurement was confirmed. 1 H-NMR (CDCl3): δ=1.08(s,6H), 1.27(s,6H), 1.42(s,6H), 1.46(s,9H), 1.47(s,9H), 1.48(s,6H), 1.69-1.81(m,8H), 2.18(s,3H), 5.97(s,1H) , 6.06(s,1H), 6.52(s,1H), 6.67(d,1H), 7.08(dd,1H), 7.25-7.29(m,3 H), 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). Mass spectrometry confirmed that the obtained compound was compound (2-574). 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). Mass spectrometry confirmed that the obtained compound was compound (2-578). 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). Mass spectrometry confirmed that the obtained compound was compound (2-580). 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). Mass spectrometry confirmed that the obtained compound was compound (2-548). 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 mixture 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-pass column (eluent: toluene), and the solvent was removed by distillation under reduced pressure. The resulting crude product was isolated and purified by washing with hexane to obtain 0.309 g of 2,8-dimethyl-10-(2-(pro-1-pen-2-yl)phenyl)-5-(p-tolyl)-5,10-dihydrodibenzo[b,e][1,4]azavorin in 75% yield.

[0833] [ka]

[0834] The structure of the compound obtained by NMR measurement was confirmed. 1 H-NMR (CDCl3): δ=2.05(s,3H), 2.31(s,6H), 2.54(s,3H), 4.78(s,2H), 6. 74(d,2H)7.20-7.28(m,4H), 7.37-7.48(m,5H), 7.56(d,1H), 7.68(s,2H). 13 C-NMR (CDCl3): δ=20.6(s,2C), 21.3(s,1C), 23.8(s,1C), 116.7(s,2C), 116.9(s,1C), 126.0(d,2C), 126.8(s,1C), 128.2(s,2C), 130.0(d,4C), 131.4(d,4C), 133.0(s,1C), 133.7(s,2C), 136.4(s,2C), 138.6(s,1C), 139.3(s,1C), 145.1(s,1C), 147.0(d,2C).

[0835] 2,8-dimethyl-10-(2-(pro-1-pen-2-yl)phenyl)-5-(p-tolyl)-5,10-dihydrodibenzo[b,e][1,4]azavorin (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 the reaction mixture was cooled to room temperature, it was filtered using a Florisil short-pass column (eluent: toluene), and the solvent was removed by distillation under reduced pressure. The resulting crude product was isolated and purified using a silica gel column (eluent: hexane / toluene = 6 / 1 (volume ratio)) to obtain compound (2-591) in 32.0 mg in yield of 39%.

[0836] [ka]

[0837] The structure of the compound obtained by NMR measurement was confirmed. 1 H-NMR(CDCl3): δ=1.98(s,6H), 2.48(s,3H), 2.53(s,3H), 2.76(s,3H), 6.61(d,1H), 6.75(d,1H ), 7.14-7.31(m,4H), 7.40-7.47(m,3H), 7.57(dt,1H), 7.81(d,1H), 8.44(d,1H), 8.50(s,1H). 13 C-NMR (CDCl3): δ=20.9(s,1C), 21.4(s,1C), 24.3(s,1C), 32.6(s,2C), 43.5(s,1C), 114. 0(s,1C), 116.6(s,1C), 124.7(s,1C), 125.8(s,1C), 127.0(s,1C), 128.4(s,2C), 130.1(s ,2C), 130.5(s,1C), 131.4(s,2C), 133.0(s,1C), 135.2(s,1C), 135.5(s,1C), 137.7(s,1 C), 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). Mass spectrometry confirmed that the obtained compound was compound (2-548). 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 spectrometry 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 spectrometry 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 starting materials of the method described in International Publication No. 2015 / 064560.

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

[0847] Compound (D-1) was synthesized according to the synthesis method for compound 1 described in International Publication No. 2012 / 118164.

[0848] By appropriately changing the raw material compounds, other compounds of the present invention can be synthesized by a method similar to the synthesis example described above.

[0849] The following are examples of organic EL elements using the compounds of the present invention, but the present invention is not limited to these examples.

[0850] Organic EL devices according to Examples 1-44 and Comparative Examples 1-5 were fabricated, and the emission wavelength (nm), voltage (V), and external quantum efficiency (%) at specific brightness levels were measured for each. The time it took to maintain a specific brightness level (device lifetime) was also measured.

[0851] The quantum efficiency of a light-emitting device has two components: internal quantum efficiency and external quantum efficiency. Internal quantum efficiency indicates the proportion of external energy injected into the light-emitting layer of the device as electrons (or holes) that is purely converted into photons. External quantum efficiency, on the other hand, is calculated based on the amount of these photons emitted to the outside of the device. Since some of the photons generated in the light-emitting layer are absorbed or reflected within the device and not emitted to the outside, external quantum efficiency is lower than internal quantum efficiency.

[0852] The external quantum efficiency measurement method is as follows: Using an Advantest R6144 voltage / current generator, the device's brightness is 1000 cd / m². 2A voltage was applied to the element to cause it to emit light. Using a TOPCON SR-3AR spectroradiometer, the spectral radiance in the visible light region was measured perpendicular to the light-emitting surface. Assuming the light-emitting surface is a perfectly diffusive surface, the number of photons at each wavelength is obtained by dividing the measured spectral radiance value for each wavelength component by the wavelength energy and multiplying by π. Next, the number of photons was integrated across the entire observed wavelength range to obtain the total number of photons emitted from the element. The number of carriers injected into the element is obtained by dividing the applied current value by the elementary charge, and the external quantum efficiency is obtained by dividing the total number of photons emitted from the element by the number of carriers injected into the element.

[0853] Table 1 below shows the material composition of each layer and the EL characteristic data of the organic EL elements fabricated in Examples 1 to 12 and Comparative Examples 1 to 3.

[0854] [Table 1]

[0855] Table 2 below shows the material composition of each layer and the EL characteristic data of the organic EL elements fabricated in Examples 13 to 44 and Comparative Examples 4 and 5.

[0856] [Table 2] TIFF2026143789000380.tif221170

[0857] In the tables above, "HI" is N 4 ,N 4’ -diphenyl-N 4 ,N 4’-Bis(9-phenyl-9H-carbazole-3-yl)-[1,1'-biphenyl]-4,4'-diamine, "HAT-CN" is 1,4,5,8,9,12-hexaazatriphenylenehexacarbonnitrile, "HT-1" is N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)-9H-fluoren-2-amine, "HT-2" is N,N-bis(4-(dibenzo[b,d]furan-4-yl)phenyl)-[1, The chemical structures are shown below along with "Liq".

[0858] [ka]

[0859] <Example 1> <Devices with host material: compounds (1-8), dopant material: compounds (2-41)> A 26mm x 28mm x 0.7mm glass substrate (manufactured by OptoScience Co., Ltd.), which had been polished to 150nm by sputtering an ITO film to a thickness of 180nm, was used as a transparent support substrate. This transparent support substrate was fixed to the substrate holder of a commercially available deposition apparatus (manufactured by Choshu Sangyo Co., Ltd.), and tantalum deposition boats containing HI, HAT-CN, HT-1, HT-2, compound (1-8), compound (2-41), ET-1, and ET-2, respectively, and aluminum nitride deposition boats containing Liq, magnesium, and silver, respectively, were attached.

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

[0861] A DC voltage was applied to the ITO electrode as the anode and the magnesium / silver electrode as the cathode, resulting in a reading of 1000 cd / m². 2 When the characteristics during emission were measured, as shown in Table 1, the driving voltage was 3.92V, the external quantum efficiency was 6.88%, and blue light emission at a wavelength of 461nm was obtained.

[0862] <Examples 2-12> Each organic EL element was manufactured with the layer configuration shown in Table 1, in accordance with Example 1, and EL characteristic data was measured (Table 1).

[0863] <Comparative Examples 1-3> Each organic EL element was manufactured with the layer configuration shown in Table 1, in accordance with Example 1, and EL characteristic data was measured (Table 1).

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

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

[0866] A DC voltage was applied to the ITO electrode as the anode and the magnesium / silver electrode as the cathode, resulting in a reading of 1000 cd / m². 2When the characteristics during light emission were measured, the driving voltage was 4.07V and the external quantum efficiency was 6.78%, as shown in Table 2. Next, the fabricated device was subjected to a constant current drive test (current density = 10mA / cm²). 2 The time it took to maintain a brightness of 90% or more of the initial brightness was 153 hours.

[0867] <Examples 14-44> Each organic EL element was manufactured with the layer configuration described in Table 2, in accordance with Example 13, and EL characteristic data was measured (Table 2).

[0868] <Comparative Examples 4-5> Each organic EL element was manufactured with the layer configuration described in Table 2, in accordance with Example 13, and EL characteristic data was measured (Table 2). [Industrial applicability]

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

[0870] 100 Organic Electroluminescent Devices 101 circuit board 102 Anode 103 Hole injection layer 104 Hole transport layer 105 Light-emitting layer 106 Electron transport layer 107 Electron injection layer 108 Cathode

Claims

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 ' are each 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, 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, fluorenyl which may be substituted with one or more substituents selected from substituent group A, benzofluorenyl which may be substituted with one or more substituents selected from substituent group A, chrysenyl 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, anthracenyl which may be substituted with 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 the following formula (A) or a group represented by the following formula (B), However, X ａ 'and X ｂ Both of them cannot become hydrogen. The substituent group A consists of phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenalenyl, phenanthryl, fluorenyl, benzofluorenyl, crisenyl, triphenylenyl, pyrenyl, anthracenyl, alkyl groups having 1 to 6 carbon atoms, cycloalkyl groups having 3 to 10 carbon atoms, silyl groups that may be substituted with alkyl groups having 1 to 4 carbon atoms, the group represented by formula (A), and the group represented by formula (B). In equations (A) and (B), Y is -O-, -S-, or >N-R. ３９ And R ２１ ~R ３８ Each is independently hydrogen, 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, and R ２１ ~R ３８ Adjacent groups may be bonded to each other to form a hydrocarbon ring, an aryl ring, or a heteroaryl ring, and at least one hydrogen in the formed hydrocarbon ring, aryl ring, or heteroaryl ring may be substituted with an 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 an optionally substituted aryl, The group represented by formula (A) is a group obtained by removing one hydrogen atom from any position in formula (A), where * indicates the position. The group represented by formula (B) is a group obtained by removing one hydrogen atom from any position in formula (B), where * indicates the position. The compound represented by formula (1') comprises at least one group selected from the group consisting of the group represented by formula (A) and the group represented by formula (B), At least one hydrogen atom in the compound represented by formula (1') may be substituted with a halogen, cyano, or deuterium. 【Chemistry 2】

2. Equation (A) is one of equations (A-1) to (A-14), and equation (B) is equation (B-1), In equations (A-1) to (A-14), and in equation (B-1), Y is -O-, -S-, or >N-R. ３９ And R ３９ is hydrogen or aryl, and at least one hydrogen in each group represented by formulas (A-1) to (A-14) and formula (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 formulas (A-1) to (A-14) are groups obtained by removing one hydrogen atom from any of the positions in formulas (A-1) to (A-14), where * indicates the position. The group represented by formula (B-1) is a group obtained by removing one hydrogen atom from any position in formula (B-1), where * indicates the position. The benzanthracene compound according to claim 1. 【Transformation 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 ' 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), X ａ 'and X ｂ At least one of the groups is a group containing a group represented by formula (A) or formula (B), Ar ７ ', Ar ８ ', Ar １１ ', and Ar １２ ' 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 a halogen, cyano, or deuterium.

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

5. The benzanthracene compound according to claim 4, represented by one of the following formulas. 【Transformation 5】 【Transformation 6】

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

7. In equations (A) and (B), R other than the bonding ２１ ~R ３８ The benzanthracene compound according to claim 4 or 5, wherein all of the atoms are hydrogen.

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

9. The benzanthracene compound according to claim 8, represented by the following formula. 【Transformation 7】

10. The benzanthracene compound according to claim 3, represented by one of the following formulas. 【Transformation 8】

11. X ａ 'and X ｂ 'teeth, Either one is a phenyl compound substituted with a group represented by formula (A) or a group represented by formula (B), and the other is an unsubstituted phenyl compound. Either one naphthyl is substituted with a group represented by formula (A) or a group represented by formula (B), and the other naphthyl 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 compounds is a phenanthryl substituted with a group represented by formula (A) or a group represented by formula (B), and the other compound is a phenanthryl which may be substituted with a group represented by formula (A) or a group represented by formula (B).

12. A benzanthracene compound according to claim 11, represented by any of the following formulas; 【Chemistry 9】 【Chemistry 10】 In the above formula, tBu is tert-butyl.

13. Ar ５ ', Ar ６ ', Ar ７ ', Ar ８ ', or Ar ９ The benzanthracene compound according to claim 1 or 2, wherein one of the groups is a group comprising a group represented by formula (A) or formula (B).

14. X ａ 'and X ｂ 'teeth, Either one is an unsubstituted phenyl compound, and the other is a phenyl compound that may be substituted with one or more substituents selected from substituent group A. In each case, the naphthyl may be substituted with one or more substituents selected from substituent group A, or Each of these is a phenanthryl which may be substituted with one or more substituents selected from substituent group A. X ａ 'and X ｂ The benzanthracene compound according to claim 13, wherein ' may be the same or different in terms of the presence and type of one or more substituents selected from substituent group A.

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

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

17. A benzanthracene compound according to claim 1, represented by any of the following formulas; 【Chemistry 12】 In the above formula, Me represents methyl.

Images