WO2013062043A1 - 4-アミノカルバゾール化合物及びその用途 - Google Patents
4-アミノカルバゾール化合物及びその用途 Download PDFInfo
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- WO2013062043A1 WO2013062043A1 PCT/JP2012/077592 JP2012077592W WO2013062043A1 WO 2013062043 A1 WO2013062043 A1 WO 2013062043A1 JP 2012077592 W JP2012077592 W JP 2012077592W WO 2013062043 A1 WO2013062043 A1 WO 2013062043A1
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- 0 *c1cccc(N(c2ccccc2)c2c(c(cccc3)c3[n]3-c(cc4)ccc4-c4ccccc4)c3ccc2)c1 Chemical compound *c1cccc(N(c2ccccc2)c2c(c(cccc3)c3[n]3-c(cc4)ccc4-c4ccccc4)c3ccc2)c1 0.000 description 14
- QHXNRWQZMLMHCY-UHFFFAOYSA-N C(C1)C=CC=C1C(C=C1)=CCC1[n](c1c2cccc1)c1c2c(N(c2ccccc2)c2ccc3[s]c(cccc4)c4c3c2)ccc1 Chemical compound C(C1)C=CC=C1C(C=C1)=CCC1[n](c1c2cccc1)c1c2c(N(c2ccccc2)c2ccc3[s]c(cccc4)c4c3c2)ccc1 QHXNRWQZMLMHCY-UHFFFAOYSA-N 0.000 description 1
- DYNJAIYOTQFHTQ-UHFFFAOYSA-N FC(C=C1)=C=C1N(c1ccccc1)c1cccc2c1c(cccc1)c1[n]2-c(cc1)ccc1-c1ccccc1 Chemical compound FC(C=C1)=C=C1N(c1ccccc1)c1cccc2c1c(cccc1)c1[n]2-c(cc1)ccc1-c1ccccc1 DYNJAIYOTQFHTQ-UHFFFAOYSA-N 0.000 description 1
- SSLRGMOKSIIGSQ-UHFFFAOYSA-N N#Cc(cc1)ccc1N(C1=C(c(cccc2)c2N2c(cc3)ccc3-c3ccccc3)C2=CCC1)C1=CC=CC2C1C2 Chemical compound N#Cc(cc1)ccc1N(C1=C(c(cccc2)c2N2c(cc3)ccc3-c3ccccc3)C2=CCC1)C1=CC=CC2C1C2 SSLRGMOKSIIGSQ-UHFFFAOYSA-N 0.000 description 1
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Definitions
- the present invention relates to a novel 4-aminocarbazole compound and an organic EL device using the same.
- An organic EL element is a surface-emitting element in which an organic thin film is held between a pair of electrodes, and has features such as a thin and light weight, a high viewing angle, and a high-speed response, and is expected to be applied to various display elements. . Recently, organic EL elements have been put into practical use in mobile phone displays and the like.
- the organic EL element is an element that utilizes light emitted when holes injected from the anode and electrons injected from the cathode are recombined in the light emitting layer, and the structure thereof is a hole transport layer, a light emitting layer, A multilayer stack type in which an electron transport layer and the like are stacked is the mainstream.
- the charge transport layer such as the hole transport layer and the electron transport layer does not emit light itself, but facilitates the injection of charge into the light emitting layer, and the charge injected into the light emitting layer and the excitation generated by the light emitting layer. It plays the role of confining the child's energy. Therefore, the charge transport layer is very important for lowering the driving voltage and improving the light emission efficiency of the organic EL element.
- an amine compound having an appropriate ionization potential and hole transport ability is used.
- NPD 4,4′-bis [N- (1-naphthyl) -N-phenyl] biphenyl
- the driving voltage and luminous efficiency of an element using NPD for the hole transport layer are not sufficiently good, and development of a new material is required.
- development of an organic EL element using a phosphorescent material for a light emitting layer has been promoted.
- a hole transport material having a high triplet level is required.
- NPD is not sufficient from the point of triplet level, and for example, it has been reported that an organic EL element in which a phosphorescent material having green light emission and NPD are combined reduces the light emission efficiency (for example, non-patent document). 1).
- the 3-aminocarbazole compound has a higher triplet level than NPD, but its ionization potential is lower than that of NPD.
- the reason for the low ionization potential of the 3-aminocarbazole compound seems to be that the amino group is activated by the nitrogen atom at the 9-position of the carbazole ring.
- the ionization potential of the material is an important physical property value that affects the characteristics of the organic EL element.
- it greatly affects the light emission efficiency of the organic EL element.
- the light emission efficiency of the organic EL element decreases due to exciplex formation with the light emitting material (see, for example, Non-Patent Document 2). Therefore, in an organic EL device using a 3-aminocarbazole compound for the hole transport layer, a sufficiently high luminous efficiency could not be obtained.
- the 2-aminocarbazole compound has an ionization potential equivalent to or higher than that of NPD and a triplet level higher than that of NPD. For this reason, in an element using a green phosphorescent material, the 2-aminocarbazole compound has a higher light emission efficiency than NPD, but it has been desired to develop a compound having a higher light emission efficiency.
- the present invention has been made in view of the background art described above, and an object thereof is to provide a compound having an appropriate ionization potential and a high triplet level and having excellent luminous efficiency.
- the novel 4-aminocarbazole compound represented by the following general formula (1) has an appropriate ionization potential and a high triplet level, and device luminous efficiency (current efficiency). As a result, the present invention was completed.
- Ar 1 to Ar 4 are each independently an aryl group having 6 to 30 carbon atoms, a thienyl group, a pyridyl group, a benzothienyl group, a dibenzothienyl group, a dibenzofuranyl group, 4-carbazolyl Group, dibenzothienylphenyl group, dibenzofuranylphenyl group, or 9-carbazolylphenyl group (these groups are each independently a methyl group, an ethyl group, a straight chain having 3 to 18 carbon atoms, branched, or A cyclic alkyl group, a methoxy group, an ethoxy group, a linear, branched, or cyclic alkoxy group having 3 to 18 carbon atoms, a halogenated alkyl group having 1 to 3 carbon atoms, a halogenated alkoxy group having 1 to 3 carbon atoms, C6-C30 aryl group,
- R 1 to R 7 are each independently an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, or a heteroarylphenyl group having 9 to 26 carbon atoms (these groups are each independently A methyl group, an ethyl group, a linear, branched or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, a linear, branched or cyclic alkoxy group having 3 to 18 carbon atoms, carbon A halogenated alkyl group having 1 to 3 carbon atoms, a halogenated alkoxy group having 1 to 3 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aryloxy group having 6 to 18 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, (It may have at least one substituent selected from the group consisting of a trialkylsilyl group having 3 to 18 carbon atoms,
- N represents an integer of 0-2.
- X is an (n + 1) -valent aromatic hydrocarbon group having 6 to 17 carbon atoms, an (n + 1) -valent heteroaromatic group having 3 to 20 carbon atoms, or an (n + 1) -valent heteroarylphenyl group having 9 to 26 carbon atoms
- a group (these groups are each independently a methyl group, an ethyl group, a linear, branched or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, a straight chain having 3 to 18 carbon atoms, Branched or cyclic alkoxy group, halogenated alkyl group having 1 to 3 carbon atoms, halogenated alkoxy group having 1 to 3 carbon atoms, aryl group having 6 to 12 carbon atoms, aryloxy group having 6 to 18 carbon atoms, carbon It has at least one substituent selected from the group consisting of a heteroaryl group having 3 to 20 carbon atoms, a trialkyls
- the present invention relates to a 4-aminocarbazole compound as shown below and its use.
- Ar 1 to Ar 4 are each independently an aryl group having 6 to 30 carbon atoms, a thienyl group, a pyridyl group, a benzothienyl group, a dibenzothienyl group, a dibenzofuranyl group, 4-carbazolyl Group, dibenzothienylphenyl group, dibenzofuranylphenyl group, or 9-carbazolylphenyl group (these groups are each independently a methyl group, an ethyl group, a straight chain having 3 to 18 carbon atoms, branched, or A cyclic alkyl group, a methoxy group, an ethoxy group, a linear, branched, or cyclic alkoxy group having 3 to 18 carbon atoms, a halogenated alkyl group having 1 to 3 carbon atoms, a halogenated alkoxy group having 1 to 3 carbon atoms, C6-C30 aryl group,
- R 1 to R 7 are each independently an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, or a heteroarylphenyl group having 9 to 26 carbon atoms (these groups are each independently A methyl group, an ethyl group, a linear, branched or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, a linear, branched or cyclic alkoxy group having 3 to 18 carbon atoms, carbon A halogenated alkyl group having 1 to 3 carbon atoms, a halogenated alkoxy group having 1 to 3 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aryloxy group having 6 to 18 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, (It may have at least one substituent selected from the group consisting of a trialkylsilyl group having 3 to 18 carbon atoms,
- N represents an integer of 0-2.
- X is an (n + 1) -valent aromatic hydrocarbon group having 6 to 17 carbon atoms, an (n + 1) -valent heteroaromatic group having 3 to 20 carbon atoms, or an (n + 1) -valent heteroarylphenyl group having 9 to 26 carbon atoms
- a group (these groups are each independently a methyl group, an ethyl group, a linear, branched or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, a straight chain having 3 to 18 carbon atoms, Branched or cyclic alkoxy group, halogenated alkyl group having 1 to 3 carbon atoms, halogenated alkoxy group having 1 to 3 carbon atoms, aryl group having 6 to 12 carbon atoms, aryloxy group having 6 to 18 carbon atoms, carbon It has at least one substituent selected from the group consisting of a heteroaryl group having 3 to 20 carbon atoms, a trialkyls
- R 1 to R 7 are each independently an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, a methyl group, an ethyl group, a linear, branched or cyclic group having 3 to 18 carbon atoms.
- R 1 to R 7 are each independently a phenyl group, a methylphenyl group, a methoxyphenyl group, a biphenylyl group, a dibenzothienyl group, a dibenzofuranyl group, a methyl group, a methoxy group, or a hydrogen atom.
- Ar 1 to Ar 4 are each independently an aryl group having 6 to 30 carbon atoms, a dibenzothienyl group, a dibenzofuranyl group, a 4-carbazolyl group, a dibenzofuranylphenyl group, a dibenzothienylphenyl group, or a 9-carba Zolylphenyl group (these groups are each independently a methyl group, an ethyl group, a linear, branched, or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, or a group having 3 to 18 carbon atoms.
- the 4-aminocarbazole compound according to any one of [1] to [6] above.
- Ar 1 to Ar 4 are each independently a phenyl group, biphenylyl group, terphenylyl group, fluorenyl group, benzofluorenyl group, dibenzothienyl group, dibenzofuranyl group, dibenzofuranylphenyl group, dibenzothienylphenyl group, Or 9-carbazolylphenyl group (these groups are each independently a methyl group, an ethyl group, a linear, branched or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, a carbon number) 3 to 18 linear, branched or cyclic alkoxy groups, which may have at least one substituent selected from the group consisting of, or a 4-carbazolyl group (methyl group, ethyl group, carbon number) 3-18 linear, branched, or cyclic alkyl group, methoxy group, ethoxy group, 3-18 carbon linear,
- Ar 1 to Ar 4 are each independently a phenyl group, a methylphenyl group, a methoxyphenyl group, a biphenylyl group, a terphenylyl group, a 9,9′-dimethylfluorenyl group, or 11,11′-dimethylbenzo [a].
- X is (n + 1) -valent benzene, (n + 1) -valent biphenyl, (n + 1) -valent naphthalene, (n + 1) -valent phenanthrene, (n + 1) -valent fluorene, (n + 1) -valent naphthylbenzene, (n + 1) -valent Pyridine, (n + 1) -valent pyrimidine, (n + 1) -valent 1,3,5-triazine, (n + 1) -valent quinoline, (n + 1) -valent dibenzothiophene, (n + 1) -valent dibenzofuran, (n + 1) -valent Pyridylbenzene, (n + 1) -valent imidazolylbenzene, (n + 1) -valent benzimidazolylbenzene, and (n + 1) -valent benzothiazolylbenzene (these aromatic rings are a methyl group, an ethyl group, Chain, branched or
- X is (n + 1) -valent benzene, (n + 1) -valent biphenyl, (n + 1) -valent quinoline, (n + 1) -valent dibenzothiophene, (n + 1) -valent 1,3,5-triazine, and (n + 1) -valent (These aromatic rings are a methyl group, an ethyl group, a linear or branched alkyl group having 3 to 18 carbon atoms, or a cyclic alkyl group, a methoxy group, an ethoxy group, a linear or branched group having 3 to 18 carbon atoms, Or at least one substituent selected from the group consisting of a cyclic alkoxy group, an aryl group having 6 to 12 carbon atoms, a cyano group, and a halogen atom).
- the 4-aminocarbazole compound as described in any one of [10].
- X is (n + 1) -valent benzene, (n + 1) -valent biphenyl, (n + 1) -valent quinoline, (n + 1) -valent dibenzothiophene, (n + 1) -valent 2,4-diphenyl-1,3,5-triazine Or the 4-aminocarbazole compound according to any one of [1] to [11] above, which is (n + 1) -valent pyridylbenzene.
- An organic EL device comprising at least one layer selected from the group consisting of a light emitting layer, a hole transport layer and a hole injection layer, comprising a 4-aminocarbazole compound represented by the formula:
- Ar 1 to Ar 4 are each independently an aryl group having 6 to 30 carbon atoms, a thienyl group, a furanyl group, a pyridyl group, a benzothienyl group, a dibenzothienyl group, a dibenzofuranyl group, 4-carbazolyl group, dibenzothienylphenyl group, dibenzofuranylphenyl group, or 9-carbazolylphenyl group (these groups are each independently a methyl group, an ethyl group, a straight chain having 3 to 18 carbon atoms, Branched or cyclic alkyl group, methoxy group, ethoxy group, linear, branched or cyclic alkoxy group having 3 to 18 carbon atoms, halogenated alkyl group having 1 to 3 carbon atoms, halogenated having 1 to 3 carbon atoms Alkoxy group, aryl group having 6 to 30 carbon atoms, aryl group having 6 to
- R 1 to R 7 are each independently an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, or a heteroarylphenyl group having 9 to 26 carbon atoms (these groups are each independently A methyl group, an ethyl group, a linear, branched or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, a linear, branched or cyclic alkoxy group having 3 to 18 carbon atoms, carbon A halogenated alkyl group having 1 to 3 carbon atoms, a halogenated alkoxy group having 1 to 3 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aryloxy group having 6 to 18 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, (It may have at least one substituent selected from the group consisting of a trialkylsilyl group having 3 to 18 carbon atoms,
- N represents an integer of 0-2.
- X is an (n + 1) -valent aromatic hydrocarbon group having 6 to 17 carbon atoms, an (n + 1) -valent heteroaromatic group having 3 to 20 carbon atoms, or an (n + 1) -valent heteroarylphenyl group having 9 to 26 carbon atoms
- a group (these groups are each independently a methyl group, an ethyl group, a linear, branched or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, a straight chain having 3 to 18 carbon atoms, Branched or cyclic alkoxy group, halogenated alkyl group having 1 to 3 carbon atoms, halogenated alkoxy group having 1 to 3 carbon atoms, aryl group having 6 to 12 carbon atoms, aryloxy group having 6 to 18 carbon atoms, carbon It has at least one substituent selected from the group consisting of a heteroaryl group having 3 to 20 carbon atoms, a trialkyls
- Ar 1 to Ar 4 are each independently an aryl group having 6 to 30 carbon atoms, a thienyl group, a pyridyl group, a benzothienyl group, a dibenzothienyl group, a dibenzofuranyl group, 4-carbazolyl Group, dibenzothienylphenyl group, dibenzofuranylphenyl group, or 9-carbazolylphenyl group (these groups are each independently a methyl group, an ethyl group, a straight chain having 3 to 18 carbon atoms, branched, or A cyclic alkyl group, a methoxy group, an ethoxy group, a linear, branched, or cyclic alkoxy group having 3 to 18 carbon atoms, a halogenated alkyl group having 1 to 3 carbon atoms, a halogenated alkoxy group having 1 to 3 carbon atoms, C6-C30 aryl group,
- R 1 to R 7 are each independently an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, or a heteroarylphenyl group having 9 to 26 carbon atoms (these groups are each independently A methyl group, an ethyl group, a linear, branched or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, a linear, branched or cyclic alkoxy group having 3 to 18 carbon atoms, carbon A halogenated alkyl group having 1 to 3 carbon atoms, a halogenated alkoxy group having 1 to 3 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aryloxy group having 6 to 18 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, (It may have at least one substituent selected from the group consisting of a trialkylsilyl group having 3 to 18 carbon atoms,
- N represents an integer of 0-2.
- X is an (n + 1) -valent aromatic hydrocarbon group having 6 to 17 carbon atoms, an (n + 1) -valent heteroaromatic group having 3 to 20 carbon atoms, or an (n + 1) -valent heteroarylphenyl group having 9 to 26 carbon atoms
- a group (these groups are each independently a methyl group, an ethyl group, a linear, branched or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, a straight chain having 3 to 18 carbon atoms, Branched or cyclic alkoxy group, halogenated alkyl group having 1 to 3 carbon atoms, halogenated alkoxy group having 1 to 3 carbon atoms, aryl group having 6 to 12 carbon atoms, aryloxy group having 6 to 18 carbon atoms, carbon It has at least one substituent selected from the group consisting of a heteroaryl group having 3 to 20 carbon atoms, a trialkyls
- the phosphorescent or fluorescent organic EL device having at least one layer containing the 4-aminocarbazole compound of the present invention has a higher luminous efficiency (compared to a conventional organic EL device containing a material into which a carbazole ring is introduced). Current efficiency), and a remarkable effect that the driving voltage is low can be expected. Therefore, according to the present invention, a phosphorescent or fluorescent organic EL element having high luminance and low power consumption can be provided.
- Ar 1 to Ar 4 are each independently an aryl group having 6 to 30 carbon atoms, thienyl group, pyridyl group, benzothienyl group, dibenzothienyl group, dibenzofuranyl group, 4-carbazolyl group, dibenzothienylphenyl group, Represents a dibenzofuranylphenyl group or a 9-carbazolylphenyl group.
- the straight-chain, branched, or cyclic alkyl group having 3 to 18 carbon atoms that Ar 1 to Ar 4 may have as a substituent is not particularly limited, and examples thereof include a propyl group, an isopropyl group, and butyl. Group, sec-butyl group, tert-butyl group, pentyl group, hexyl group, heptyl group, octyl group, stearyl group, cyclopropyl group, cyclohexyl group and the like.
- the linear, branched, or cyclic alkoxy group having 3 to 18 carbon atoms that Ar 1 to Ar 4 may have as a substituent is not particularly limited, and examples thereof include a propoxy group, an isopropoxy group, Examples thereof include an n-butoxy group, a sec-butoxy group, a tert-butoxy group, a pentyloxy group, a hexyloxy group, and a stearyloxy group.
- the halogenated alkyl group having 1 to 3 carbon atoms that Ar 1 to Ar 4 may have as a substituent is not particularly limited, and examples thereof include a trifluoromethyl group, a trichloromethyl group, and 2-fluoroethyl. Groups and the like.
- the halogenated alkoxy group having 1 to 3 carbon atoms that Ar 1 to Ar 4 may have as a substituent is not particularly limited, and examples thereof include a trifluoromethoxy group, a trichloromethoxy group, and 2-fluoroethoxy. Groups and the like.
- the aryl group having 6 to 30 carbon atoms that Ar 1 to Ar 4 may have as a substituent is not particularly limited, and examples thereof include a phenyl group, a 2-methylphenyl group, a 3-methylphenyl group, 4-methylphenyl group, 2-methoxyphenyl group, 3-methoxyphenyl group, 4-methoxyphenyl group, 2-cyanophenyl group, 3-cyanophenyl group, 4-cyanophenyl group, biphenylyl group, terphenylyl group, naphthyl group Fluorenyl group, phenanthryl group, benzofluorenyl group and the like.
- the aryloxy group having 6 to 18 carbon atoms that Ar 1 to Ar 4 may have as a substituent is not particularly limited, and examples thereof include a phenoxy group, a 2-methylphenoxy group, and a 3-methylphenoxy group.
- the heteroaryl group having 3 to 11 carbon atoms that Ar 1 to Ar 4 may have as a substituent is an aromatic group containing at least one heteroatom among an oxygen atom, a nitrogen atom and a sulfur atom, Imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridyl group, 2-methylpyridyl group, 3-methylpyridyl group, 4-methylpyridyl group, 2-methoxypyridyl group, 3-methoxypyridyl group 4-methoxypyridyl group, 2-cyanopyridyl group, 3-cyanopyridyl group, 4-cyanopyridyl group, pyrimidyl group, pyrazyl group, 1,3,5-triazyl group, benzoimidazolyl group, indazolyl group, benzothiazolyl group, benzo Isothiazoly
- the trialkylsilyl group having 3 to 18 carbon atoms that Ar 1 to Ar 4 may have as a substituent is not particularly limited, and examples thereof include a trimethylsilyl group, a triethylsilyl group, and a tributylsilyl group. It is done.
- the triarylsilyl group having 18 to 40 carbon atoms that Ar 1 to Ar 4 may have as a substituent is not particularly limited, and examples thereof include a triphenylsilyl group and tri (4-methylphenyl) silyl. Group, tri (3-methylphenyl) silyl group, tri (4-methylphenyl) silyl group, tri (4-biphenylyl) silyl group and the like.
- halogen atom examples include fluorine, chlorine, bromine, and iodine.
- Ar 1 to Ar 4 include phenyl group, 4-methylphenyl group, 3-methylphenyl group, 2-methylphenyl group, 4-ethylphenyl group, 3-ethylphenyl group, 2-ethylphenyl group, 4-n-propylphenyl group, 4-isopropylphenyl group, 2-isopropylphenyl group, 4-n-butylphenyl group, 4-isobutylphenyl group, 4-sec-butylphenyl group, 4-tert-butylphenyl group, 4-n-pentylphenyl group, 4-isopentylphenyl group, 4-neopentylphenyl group, 4-n-hexylphenyl group, 4-n-octylphenyl group, 4-n-decylphenyl group, 4-n- Dodecylphenyl group, 4-cyclopentylphenyl group, 4-cyclohexylphenyl group, 4-tr
- Ar 1 to Ar 4 may have 6 to 30 carbon atoms.
- Aryl group, dibenzothienyl group, dibenzofuranyl group, 4-carbazolyl group, dibenzofuranylphenyl group, dibenzothienylphenyl group, or 9-carbazolylphenyl group (these groups are each independently a methyl group, Ethyl group, straight chain, branched or cyclic alkyl group having 3 to 18 carbon atoms, methoxy group, ethoxy group, straight chain, branched or cyclic alkoxy group having 3 to 18 carbon atoms, aryl having 6 to 30 carbon atoms And may have at least one substituent selected from the group consisting of a group having 3 to 11 carbon atoms and a heteroaryl group having 3 to 11 carbon atoms.
- An alkoxy group which may have at least one substituent selected from the group consisting of), or a 4-carbazolyl group (a methyl group, an ethyl group, a linear, branched, or cyclic group having 3 to 18 carbon atoms)
- Phenyl group methylphenyl group, methoxyphenyl group, biphenylyl group, terphenylyl group, 9,9′-dimethylfluorenyl group, 11,11′-dimethylbenzo [a] fluorenyl group, dibenzothienyl group, dibenzofuranyl group, Dibenzothienylphenyl group, 4- (9-carbazolyl) phenyl group, 9-phenylcarbazol-4-yl group, 9-biphenylylcarbazol-4-yl group, 9-quinolylcarbazol-4-yl group, 9-dibenzo More preferred is a thienylcarbazol-4-yl group.
- R 1 to R 7 each independently represents an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, or 9 carbon atoms.
- -26 heteroarylphenyl group, methyl group, ethyl group, linear, branched or cyclic alkyl group having 3 to 18 carbon atoms, methoxy group, ethoxy group, linear, branched or cyclic group having 3 to 18 carbon atoms Represents an alkoxy group, a cyano group, a hydrogen atom, or a halogen atom.
- the aryl group having 6 to 30 carbon atoms, the heteroaryl group having 3 to 20 carbon atoms, and the heteroarylphenyl group having 9 to 26 carbon atoms are each independently a methyl group, an ethyl group, or a carbon number.
- the aryl group having 6 to 30 carbon atoms that R 1 to R 7 may have as a substituent is not particularly limited.
- the aryl group having 6 to 30 carbon atoms shown in the aforementioned Ar 1 to Ar 4 may be used. And the same substituents as the aryl group.
- the heteroaryl group having 9 to 26 carbon atoms that R 1 to R 7 may have as a substituent is not particularly limited, and includes, for example, at least one heteroatom among an oxygen atom, a nitrogen atom, and a sulfur atom.
- the aromatic group to contain is mentioned.
- Specific examples thereof include imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridyl group, 2-methylpyridyl group, 3-methylpyridyl group, 4-methylpyridyl group, 2-methoxypyridyl group 3-methoxypyridyl group, 4-methoxypyridyl group, 2-cyanopyridyl group, 3-cyanopyridyl group, 4-cyanopyridyl group, pyrimidyl group, pyrazyl group, 1,3,5-triazyl group, benzoimidazolyl group, indazolyl Group, benzothiazolyl group, benzoisothiazolyl group, 2,1,3-benzothiadiazolyl group, benzoxazolyl group, benzoisoxazolyl group, 2,1,3-benzooxadiazolyl group, quinolyl
- the heteroarylphenyl group having 9 to 26 carbon atoms that R 1 to R 7 may have as a substituent is not particularly limited, and examples thereof include a pyridylphenyl group, an imidazolylphenyl group, a benzoimidazolylphenyl group, a benzoyl group. Examples thereof include a thiazolylphenyl group, a triazylphenyl group, a pyrrolylphenyl group, a furanylphenyl group, a dibenzofuranylphenyl group, and a dibenzothienylphenyl group.
- the linear, branched, or cyclic alkyl group having 3 to 18 carbon atoms that R 1 to R 7 may have as a substituent is not particularly limited.
- the linear, branched, or cyclic alkoxy group having 3 to 18 carbon atoms that R 1 to R 7 may have as a substituent is not particularly limited, and examples thereof include the aforementioned Ar 1 to Ar 4. And the same substituent as the linear, branched, or cyclic alkoxy group having 3 to 18 carbon atoms shown in FIG.
- the halogenated alkyl group having 1 to 3 carbon atoms that R 1 to R 7 may have as a substituent is not particularly limited, but for example, the number of carbon atoms represented by Ar 1 to Ar 4 described above is 1
- the same substituent as the halogenated alkyl group of 3 to 3 can be mentioned.
- the halogenated alkoxy group having 1 to 3 carbon atoms that R 1 to R 7 may have as a substituent is not particularly limited, but for example, the number of carbon atoms represented by Ar 1 to Ar 4 described above is 1 The same substituent as the halogenated alkoxy group of 3 to 3 can be mentioned.
- the aryloxy group having 6 to 18 carbon atoms that R 1 to R 7 may have as a substituent is not particularly limited, and examples thereof include, for example, those having 6 to 6 carbon atoms represented by Ar 1 to Ar 4 described above. Examples include the same substituents as the 18 aryloxy groups.
- the trialkylsilyl group having 3 to 18 carbon atoms that R 1 to R 7 may have as a substituent is not particularly limited, but for example, the number of carbon atoms represented by Ar 1 to Ar 4 is 3 And the same substituents as those of the trialkylsilyl group of -18.
- the triarylsilyl group having 18 to 40 carbon atoms that R 1 to R 7 may have as a substituent is not particularly limited, for example, the carbon number of 18 shown in the above Ar 1 to Ar 4 Examples include the same substituents as those of 40 to 40 triarylsilyl groups.
- Examples of the halogen atom that R 1 to R 7 may have as a substituent include the same atoms as the halogen atoms shown for the aforementioned Ar 1 to Ar 4 .
- each of R 1 to R 7 independently represents the number of carbon atoms 6-30 aryl groups, C3-C20 heteroaryl groups, methyl groups, ethyl groups, C3-C18 linear, branched, or cyclic alkyl groups, methoxy groups, ethoxy groups, C3-C3 It is preferably an 18 straight-chain, branched or cyclic alkoxy group, cyano group, hydrogen atom, or halogen atom.
- R 1 to R 7 are each independently a phenyl group, methylphenyl group, methoxyphenyl group, biphenylyl group, dibenzothienyl group, dibenzofuranyl group, methyl group It is more preferably a group, a methoxy group, or a hydrogen atom. More preferably, R 1 to R 7 are each independently a phenyl group, a methylphenyl group, a methoxyphenyl group, or a hydrogen atom.
- R 4 , R 5 , R 6 , and R 7 are more preferably hydrogen atoms, and R 1 , R 2 , R 4 , R 5 , R 6 , and R It is even more preferable that 7 is a hydrogen atom
- n represents an integer of 0 to 2.
- X is an (n + 1) -valent aromatic hydrocarbon group having 6 to 17 carbon atoms, an (n + 1) -valent heteroaromatic group having 3 to 20 carbon atoms, or an (n + 1) -valent heteroarylphenyl group having 9 to 26 carbon atoms Represents a group.
- These groups are each independently a methyl group, an ethyl group, a linear, branched or cyclic alkyl group having 3 to 18 carbon atoms, a methoxy group, an ethoxy group, a straight chain having 3 to 18 carbon atoms, Branched or cyclic alkoxy group, halogenated alkyl group having 1 to 3 carbon atoms, halogenated alkoxy group having 1 to 3 carbon atoms, aryl group having 6 to 12 carbon atoms, aryloxy group having 6 to 18 carbon atoms, carbon It has at least one substituent selected from the group consisting of heteroaryl groups having 3 to 20 carbon atoms, trialkylsilyl groups having 3 to 18 carbon atoms, triarylsilyl groups having 18 to 40 carbon atoms, cyano groups, and halogen atoms. You may do it.
- the (n + 1) -valent aromatic hydrocarbon group having 6 to 17 carbon atoms in X is not particularly limited, and examples thereof include a phenyl group, a phenylene group, a benzenetriyl group, a 2-methylphenyl group, 3- Methylphenyl group, 4-methylphenyl group, methylbenzenediyl group, methylbenzenetriyl group, 2-methoxyphenyl group, 3-methoxyphenyl group, 4-methoxyphenyl group, methoxybenzenediyl group, methoxybenzenetriyl group, 2-cyanophenyl group, 3-cyanophenyl group, cyanobenzenediyl group, cyanobenzenetriyl group, biphenylyl group, biphenylylene group, biphenyltriyl group, naphthyl group, naphthylene group, naphthalenetriyl group, fluorenyl group, full orange Yl group, fluoren
- the (n + 1) -valent heteroaromatic group having 3 to 20 carbon atoms in X is not particularly limited, and an (n + 1) -valent heteroaromatic group containing at least one heteroatom among an oxygen atom, a nitrogen atom and a sulfur atom. Refers to an aromatic group.
- imidazolyl group examples thereof include imidazolyl group, imidazole diyl group, imidazole triyl group, pyrazolyl group, pyrazole diyl group, pyrazole triyl group, thiazolyl group, thiazole diyl group, thiazole triyl group, isothiazolyl group, isothiazol diyl group, Isothiazoletriyl group, oxazolyl group, oxazolediyl group, oxazoletriyl group, isoxazolyl group, isoxazolediyl group, isoxazoletriyl group, pyridyl group, pyridinediyl group, pyridinetriyl group, 2-methylpyridyl group, 3-methylpyridyl group, 4-methylpyridyl group, methylpyridinediyl group, methylpyridinetriyl group, 2-methoxypyridyl group, 3-methoxypyrid
- the (n + 1) -valent heteroarylphenyl group having 9 to 26 carbon atoms in X is not particularly limited, and examples thereof include a pyridylphenylyl group, a pyridylphenyldiyl group, a pyridylphenyltriyl group, and an imidazolylphenylyl group.
- Imidazolylphenyldiyl group imidazolylphenyltriyl group, benzoimidazolylphenylyl group, benzoimidazolylphenyldiyl group, benzoimidazolylphenyltriyl group, benzothiazolylphenylyl group, benzothiazolylphenyldiyl group, benzothiazolylphenyltri Yl, triazylphenylyl, triazylphenyldiyl, triazylphenyltriyl, pyrrolylphenylyl, pyrrolylphenyldiyl, pyrrolylphenyltriyl, furanylphenylyl, furyl Ruphenyldiyl group, furanylphenyltriyl group, dibenzofuranylphenylyl group, dibenzofuranylphenyldiyl group, dibenzofuranylphenyltriyl group, dibenzofur
- the linear, branched, or cyclic alkyl group having 3 to 18 carbon atoms that X may have as a substituent is not particularly limited, and examples thereof include 3 to 18 carbon atoms in Ar 1 to Ar 4 . And the same substituent as the linear, branched or cyclic alkyl group.
- the linear, branched, or cyclic alkoxy group having 3 to 18 carbon atoms that X may have as a substituent is not particularly limited, but examples thereof include 3 to 18 carbon atoms in Ar 1 to Ar 4 . And the same substituent as the linear, branched or cyclic alkoxy group.
- the halogenated alkyl group having 1 to 3 carbon atoms that X may have as a substituent is not particularly limited, and examples thereof include a halogenated alkyl group having 1 to 3 carbon atoms in Ar 1 to Ar 4 and The same substituents can be mentioned.
- the halogenated alkoxy group having 1 to 3 carbon atoms that X may have as a substituent is not particularly limited.
- a halogenated alkoxy group having 1 to 3 carbon atoms in Ar 1 to Ar 4 and The same substituents can be mentioned.
- the aryl group having 6 to 12 carbon atoms that X may have as a substituent is not particularly limited, and examples thereof include a phenyl group, a 2-methylphenyl group, a 3-methylphenyl group, and a 4-methylphenyl group. Group, 2-methoxyphenyl group, 3-methoxyphenyl group, 4-methoxyphenyl group, 2-cyanophenyl group, 3-cyanophenyl group, biphenylyl group, naphthyl group and the like.
- the aryloxy group having 6 to 18 carbon atoms that X may have as a substituent is not particularly limited, but for example, the carbon that Ar 1 to Ar 4 may have as a substituent Examples thereof include the same substituents as those of the aryloxy group of Formula 6-18.
- the heteroaryl group having 3 to 20 carbon atoms that X may have as a substituent is not particularly limited, but for example, the number of carbon atoms that R 1 to R 7 may have as a substituent Examples include the same substituents as 3 to 20 heteroaryl groups.
- the trialkylsilyl group having 3 to 18 carbon atoms that X may have as a substituent is not particularly limited, but for example, the carbon that Ar 1 to Ar 4 may have as a substituent Examples thereof include the same substituents as those of the trialkylsilyl group of Formula 3-18.
- the triarylsilyl group having 18 to 40 carbon atoms that X may have as a substituent is not particularly limited, but for example, the carbon that Ar 1 to Ar 4 may have as a substituent Examples thereof include the same substituents as those of the triarylsilyl group of formulas 18 to 40.
- X include phenyl group, 4-methylphenyl group, 3-methylphenyl group, 2-methylphenyl group, 4-ethylphenyl group, 3-ethylphenyl group, 2-ethylphenyl group, 4-n- Propylphenyl group, 4-isopropylphenyl group, 2-isopropylphenyl group, 4-n-butylphenyl group, 4-isobutylphenyl group, 4-sec-butylphenyl group, 4-tert-butylphenyl group, 4-n- Pentylphenyl group, 4-isopentylphenyl group, 4-neopentylphenyl group, 4-n-hexylphenyl group, 4-n-octylphenyl group, 4-n-decylphenyl group, 4-n-dodecylphenyl group, 4-cyclopentylphenyl group, 4-cyclohexylphenyl group, 4-trityl
- X represents (n + 1) -valent benzene, (n + 1) -valent biphenyl, (n + 1) -valent naphthalene, (N + 1) -valent phenanthrene, (n + 1) -valent fluorene, (n + 1) -valent naphthylbenzene, (n + 1) -valent pyridine, (n + 1) -valent pyrimidine, (n + 1) -valent 1,3,5-triazine, ( n + 1) -valent quinoline, (n + 1) -valent dibenzothiophene, (n + 1) -valent dibenzofuran, (n + 1) -valent pyridylbenzene, (n + 1) -valent imidazolylbenzene, (n + 1) -valent benzimidazolylbenzene, and (n + 1) -valent Benzothiazolylbenzene (
- the triplet level of the hole transport material needs to be higher than the triplet level of the light emitting material.
- the triplet level of the material is 2. Since it is 42 eV (Non-Patent Document 1), the triplet level of the 4-aminocarbazole compound represented by the general formula (1) is not particularly limited, but may be 2.43 eV or more. preferable. More preferably, it is 2.50 eV or more.
- the triplet level of the material is 2.65 eV (Applied Physics Letters, 2003, Vol. 82, p. 2422), so that the general formula (1
- the triplet level of the 4-aminocarbazole compound represented by () is not particularly limited, but is preferably 2.66 eV or more, and more preferably 2.70 eV or more.
- the 4-aminocarbazole compound represented by the general formula (1) is a known method (Tetrahedron Letters, 1998, Vol. 39, 2367) using, for example, a 9H-carbazole compound halogenated at the 4-position as a raw material. Page). Specifically, it can be synthesized by the following route a and route b.
- Route a Route a includes the following reaction steps.
- a copper catalyst or palladium catalyst comprising a 9H-carbazole compound represented by the general formula (2) halogenated at the 4-position and a compound having a halogen atom represented by the general formula (3) in the presence of a base
- a 4-halogenated-9-substituted carbazole compound represented by the general formula (4) is obtained.
- the secondary amine compound is reacted with a copper catalyst or a palladium catalyst in the presence of a base.
- Ar 1 to Ar 4 , R 1 to R 7 , X, and n are as defined above, and A, B, C, and D are each independently a halogen atom [ Represents iodine, bromine, chlorine, or fluorine].
- Route b includes the following reaction steps.
- the reaction is performed to obtain a carbazole compound in which the 4- and 9-position substituents X represented by the general formula (8) are halogenated.
- the secondary amine compound is reacted with a copper catalyst or a palladium catalyst in the presence of a base.
- Ar 1 to Ar 4 , R 1 to R 7 , and X are as defined above, and A, B, C, and D are each Independently represents a halogen atom [iodine, bromine, chlorine, or fluorine].
- m represents an integer of 0-2.
- the method for synthesizing the 4-aminocarbazole compound represented by the general formula (1) is not limited to the route a and the route b, and can be synthesized by other routes.
- the 4-aminocarbazole compound represented by the general formula (1) of the present invention can be used as a constituent material of a light emitting layer, a hole transport layer or a hole injection layer of an organic EL device.
- the 4-aminocarbazole compound represented by the general formula (1) includes at least one hole injection layer, hole transport layer, or light emitting layer in an element using a fluorescent light emitting material or a phosphorescent light emitting material for the light emitting layer. It can be preferably used as a constituent material.
- the 4-aminocarbazole compound represented by the general formula (1) is used as a hole injection layer and / or a hole transport layer of an organic EL device
- a known fluorescent or conventionally used light emitting layer is used.
- Phosphorescent materials can be used.
- the light emitting layer may be formed of only one kind of light emitting material, or one or more kinds of light emitting materials may be doped in the host material.
- the hole injection layer and / or hole transport layer made of the 4-aminocarbazole compound represented by the general formula (1) two or more kinds of materials may be contained or laminated as necessary.
- oxides such as molybdenum oxide, 7,7,8,8-tetracyanoquinodimethane, 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane,
- a known electron-accepting material such as hexacyanohexaazatriphenylene may be contained or laminated.
- the 4-aminocarbazole compound represented by the general formula (1) of the present invention can also be used as a light emitting layer of an organic EL device.
- the 4-aminocarbazole compound represented by the general formula (1) is used as the light emitting layer of the organic EL device, the 4-aminocarbazole compound is used alone, used by doping a known light emitting host material, or It can be used by doping a known light-emitting dopant.
- Examples of a method for forming a hole injection layer, a hole transport layer, or a light emitting layer containing the 4-aminocarbazole compound represented by the general formula (1) include a vacuum deposition method, a spin coating method, and a casting method. A known method can be applied.
- the FDMS measurement was performed using M-80B manufactured by Hitachi.
- the triplet level was evaluated using an F2500 spectrofluorometer manufactured by Hitachi High-Technologies Corporation.
- the ionization potential was evaluated by cyclic voltammetry using HA-501 and HB-104 manufactured by Hokuto Denko.
- the glass transition temperature was measured using a DSC-3100 manufactured by Mac Science under a temperature rising condition of 10 ° C./min.
- the light emission characteristics of the organic EL element were evaluated by applying a direct current to the produced element and using a luminance meter of LUMINANCEMETER (BM-9) manufactured by TOPCON.
- Synthesis Example 2 (Synthesis of 4-chlorocarbazole [Formula (10)]) Under a nitrogen stream, 60.0 g (257.4 mmol) of 2-nitro-6-chlorobiphenyl obtained in Synthesis Example 1 was placed in a 500 mL eggplant-shaped flask, heated to 140 ° C., and then 106 g of triethyl phosphite was added for 2 hours. It was dripped at. After dropping, the mixture was further stirred at 140 ° C. for 2 hours, and triethyl phosphite was distilled off under reduced pressure. Toluene was added to the residue and purified by silica gel column chromatography (toluene) to isolate 18.9 g (93.72 mmol) of 4-chlorocarbazole white powder (yield 36%).
- Synthesis Example 4 (Synthesis of 4-chloro-9- (3-quinolyl) carbazole) In a 100 mL three-necked flask under a nitrogen stream, 5.0 g (24.7 mmol) of 4-chlorocarbazole obtained in Synthesis Example 2, 5.1 g (24.7 mmol) of 3-bromoquinoline, 4.7 g of potassium carbonate (34. 7 mmol), 25 mL of o-xylene, 276 mg (1.23 mmol) of palladium acetate and 869 mg (4.3 mmol) of tri (tert-butyl) phosphine were added and stirred at 140 ° C. for 24 hours.
- Synthesis Example 5 (Synthesis of 4-chloro-9- (2-dibenzothienyl) carbazole) In a 50 mL three-neck flask under a nitrogen stream, 2.6 g (12.9 mmol) of 4-chlorocarbazole obtained in Synthesis Example 2, 3.4 g (12.9 mmol) of 2-bromodibenzothiophene, 3.5 g of potassium carbonate (25 0.9 mmol), 13 mL of o-xylene, 29 mg (0.12 mmol) of palladium acetate, and 91 mg (0.45 mmol) of tri (tert-butyl) phosphine were added and stirred at 140 ° C. for 18 hours.
- Synthesis Example 8 (Synthesis of 4-chloro-9-phenylcarbazole) In a 200 mL three-necked flask under a nitrogen stream, 17.0 g (84.3 mmol) of 4-chlorocarbazole obtained in Synthesis Example 2, 15.8 g (101.1 mmol) of bromobenzene, 19.5 g (141.6 mmol) of potassium carbonate. ), 85 mL of o-xylene, 227 mg (1.0 mmol) of palladium acetate, and 714 mg (3.5 mmol) of tri (tert-butyl) phosphine were added and stirred at 130 ° C. for 24 hours.
- Synthesis Example 10 (Synthesis of 4-chloro-6-phenyl-9-biphenylylcarbazole)
- 1.8 g (5.2 mmol) of 4-chloro-9- (4-biphenylyl) carbazole obtained in Synthesis Example 3 was charged, and 10 mL of dimethylformamide, 0.93 g of N-bromosuccinimide (5.2 mmol) was added.
- the mixture was stirred at room temperature for 2 hours, 10 mL of pure water was added, and the precipitated white powder was collected by filtration. The powder was washed with pure water and methanol and dried under reduced pressure.
- the product in the form of white powder is 4-chloro-9- (4-biphenylyl) carbazole, 4-chloro-6-bromo-9- (4-biphenylyl) carbazole and 4-chloro-3,6-dibromo as raw materials. It was a mixture of -9- (4-biphenylyl) carbazole (the purity of 4-chloro-6-bromo-9- (4-biphenylyl) carbazole was 72%).
- Synthesis Example 12 (Synthesis of N-biphenylyl-N- (m-terphenyl) amine) In a 300 mL three-necked flask under a nitrogen stream, 12.0 g (37.1 mmol) of N- (4-bromophenyl) -N-biphenylylamine obtained in Synthesis Example 11 and 7.7 g of 3-biphenylylboronic acid (38 0.9 mmol), 2.1 g (1.8 mmol) of tetrakis (triphenylphosphine) palladium, 60 mL of toluene, 10 mL of ethanol, and 49 g (92.8 mmol) of 40 wt% tripotassium phosphate aqueous solution were added and heated to reflux for 5 hours.
- Example 1 (Synthesis of Compound (A5)) In a 100 mL three-necked flask under a nitrogen stream, 3.5 g (9.9 mmol) of 4-chloro-9- (4-biphenylyl) carbazole obtained in Synthesis Example 3 and 2.4 g of N-phenyl-N-biphenylylamine were obtained. (9.9 mmol), 1.3 g (13.8 mmol) of sodium-tert-butoxide, 35 mL of o-xylene, 22 mg (0.09 mmol) of palladium acetate, and 69 mg (0.34 mmol) of tri (tert-butyl) phosphine were added. And stirred at 140 ° C.
- Example 2 (Synthesis of Compound (A8)) In a 100 mL three-necked flask under a nitrogen stream, 3.5 g (9.9 mmol) of 4-chloro-9- (4-biphenylyl) carbazole obtained in Synthesis Example 3 and N, N-bis (4-biphenylyl) amine 3 0.1 g (9.9 mmol), sodium tert-butoxide 1.3 g (13.8 mmol), o-xylene 35 mL, palladium acetate 22 mg (0.09 mmol), tri (tert-butyl) phosphine 69 mg (0.34 mmol) The mixture was added and stirred at 140 ° C. for 12 hours.
- Example 3 (Synthesis of Compound (A15)) In a 50 mL three-necked flask under a nitrogen stream, 4.6 g (13.0 mmol) of 4-chloro-9- (4-biphenylyl) carbazole obtained in Synthesis Example 3 and N- (p-tolyl) -N- (9 , 9′-dimethylfluoren-2-yl) amine 4.2 g (14.3 mmol), sodium tert-butoxide 1.7 g (18.2 mmol), o-xylene 25 mL, palladium acetate 58 mg (0.26 mmol), tri 184 mg (0.91 mmol) of (tert-butyl) phosphine was added and stirred at 140 ° C.
- Example 4 (Synthesis of Compound (A278)) In a 50 mL three-necked flask under a nitrogen stream, 4.0 g (11.3 mmol) of 4-chloro-9- (4-biphenylyl) carbazole obtained in Synthesis Example 3 and N- (2-dibenzofuranyl) -N— Phenylamine 3.2 g (12.4 mmol), sodium-tert-butoxide 1.5 g (15.8 mmol), o-xylene 20 mL, palladium acetate 50 mg (0.22 mmol), tri (tert-butyl) phosphine 155 mg (0. 77 mmol) was added and stirred at 140 ° C. for 12 hours.
- Example 5 (Synthesis of Compound (A286)) In a 50 mL three-necked flask under nitrogen flow, 0.48 g (1.7 mmol) of 4-chloro-9-phenylcarbazole obtained in Synthesis Example 8 and N-biphenylyl-N- (m- Terphenyl) amine 0.70 g (1.7 mmol), sodium tert-butoxide 0.23 g (2.4 mmol), o-xylene 10 mL, palladium acetate 8 mg (0.03 mmol), tri (tert-butyl) phosphine 24 mg ( 0.12 mmol) was added and the mixture was stirred at 140 ° C. for 14 hours.
- Example 6 (Synthesis of Compound (A289)) In a 100 mL three-necked flask under a nitrogen stream, 4.0 g (14.4 mmol) of 4-chloro-9-phenylcarbazole obtained in Synthesis Example 8 and N-phenyl-N- (11,11′-dimethylbenzo [a Fluoren-9-yl) amine 4.8 g (14.4 mmol), sodium-tert-butoxide 1.9 g (20.1 mmol), o-xylene 30 mL, palladium acetate 64 mg (0.28 mmol), tri (tert-butyl) ) 197 mg (0.98 mmol) of phosphine was added and stirred at 140 ° C.
- Example 7 (Synthesis of Compound (A292)) In a 50 mL three-necked flask under a nitrogen stream, 0.72 g (2.6 mmol) of 4-chloro-9-phenylcarbazole obtained in Synthesis Example 8 and N-biphenylyl-N- (4- (4-Dibenzothienyl) phenyl) amine 1.2 g (2.8 mmol), sodium tert-butoxide 0.35 g (3.6 mmol), o-xylene 10 mL, palladium acetate 17 mg (0.07 mmol), tri (tert- Butyl) phosphine 55 mg (0.27 mmol) was added and stirred at 140 ° C. for 14 hours.
- Example 8 (Synthesis of Compound (A124)) In a 50 mL three-necked flask under a nitrogen stream, 3.0 g (6.9 mmol) of 4-chloro-9- (4,6-diphenyl-1,3,5-triazin-2-yl) carbazole obtained in Synthesis Example 9 was obtained.
- N, N-bis (4-biphenylyl) amine 2.2 g (6.9 mmol), sodium tert-butoxide 0.93 g (9.7 mmol), o-xylene 20 mL, palladium acetate 31 mg (0.13 mmol), 97 mg (0.48 mmol) of tri (tert-butyl) phosphine was added and stirred at 140 ° C. for 8 hours. After cooling to room temperature, 10 mL of pure water was added and stirred. The precipitated brown powder was collected by filtration and washed with pure water and ethanol. The brown powder was dried under reduced pressure and recrystallized from o-xylene to isolate 2.9 g (4.0 mmol) of a gray powder of compound (A124) (yield 59%).
- Example 10 (Synthesis of Compound (A148)) In a 50 mL three-necked flask under nitrogen flow, 4.0 g (10.4 mmol) of 4-chloro-9- (2-dibenzothienyl) carbazole obtained in Synthesis Example 5 and N-phenyl-N- (2-dibenzothienyl) were obtained. ) Amine 3.1 g (11.4 mmol), sodium tert-butoxide 1.4 g (14.6 mmol), o-xylene 20 mL, palladium acetate 70 mg (0.31 mmol), tri (tert-butyl) phosphine 221 mg (1. 0 mmol) was added and stirred at 140 ° C. for 10 hours.
- Example 11 (Synthesis of Compound (A153)) In a 50 mL three-necked flask under a nitrogen stream, 4.0 g (10.4 mmol) of 4-chloro-9- (2-dibenzothienyl) carbazole obtained in Synthesis Example 5 and N-phenyl-N- (4- (9 -Carbazolyl) phenyl) amine 3.8 g (11.4 mmol), sodium-tert-butoxide 1.4 g (14.6 mmol), o-xylene 20 mL, palladium acetate 70 mg (0.31 mmol), tri (tert-butyl) phosphine 221 mg (1.0 mmol) was added and stirred at 140 ° C. for 12 hours.
- Example 12 (Synthesis of Compound (A318)) In a 50 mL three-necked flask under a nitrogen stream, 500 mg (1.1 mmol) of 4-chloro-6-phenyl-9-biphenylylcarbazole obtained in Synthesis Example 10 and N-phenyl-N- (2-dibenzothienyl) amine were obtained. 302 mg (1.1 mmol), sodium-tert-butoxide 147 mg (1.5 mmol), o-xylene 10 mL, palladium acetate 7 mg (0.03 mmol), tri (tert-butyl) phosphine 21 mg (0.10 mmol) were added. The mixture was stirred at 140 ° C. for 10 hours.
- Example 13 (Synthesis of Compound (B1)) In a 200 mL three-necked flask under a nitrogen stream, 7.0 g (19.8 mmol) of 4-chloro-9- (4-biphenylyl) carbazole obtained in Synthesis Example 3, 0.87 g (9.4 mmol) of aniline, sodium- 5.3 g (55.4 mmol) of tert-butoxide, 70 mL of o-xylene, 44 mg (0.19 mmol) of palladium acetate, and 139 mg (0.69 mmol) of tri (tert-butyl) phosphine were added and stirred at 140 ° C. for 12 hours. .
- Example 14 (Synthesis of Compound (B2)) In a 200 mL three-neck flask under a nitrogen stream, 7.0 g (19.8 mmol) of 4-chloro-9- (4-biphenylyl) carbazole obtained in Synthesis Example 3 and 1.0 g (9.4 mmol) of 4-methylaniline were obtained. , Sodium-tert-butoxide 5.3 g (55.4 mmol), o-xylene 70 mL, palladium acetate 88 mg (0.39 mmol), tri (tert-butyl) phosphine 279 mg (1.38 mmol) and 140 ° C. Stir for hours. After cooling to room temperature, 40 mL of pure water was added and stirred.
- Example 15 (Synthesis of Compound (B27)) In a 50 mL three-necked flask under a nitrogen stream, 4.0 g (12.1 mmol) of 4-chloro-9- (3-quinolyl) carbazole obtained in Synthesis Example 4 and 652 mg (6.0 mmol) of 4-methylaniline, sodium -1.6 g (17.0 mmol) of tert-butoxide, 20 mL of o-xylene, 27 mg (0.12 mmol) of palladium acetate, and 85 mg (0.42 mmol) of tri (tert-butyl) phosphine were added and stirred at 140 ° C. for 17 hours. did.
- Example 16 (Synthesis of Compound (B30)) In a 50 mL three-necked flask under a nitrogen stream, 2.7 g (7.0 mmol) of 4-chloro-9- (2-dibenzothienyl) carbazole obtained in Synthesis Example 5, 297 mg (3.2 mmol) of aniline, sodium-tert -947 mg (9.8 mmol) of butoxide, 13 mL of o-xylene, 15 mg (0.07 mmol) of palladium acetate, and 49 mg (0.24 mmol) of tri (tert-butyl) phosphine were added and stirred at 140 ° C. for 20 hours.
- Example 17 (Synthesis of Compound (B36)) In a 50 mL three-necked flask under a nitrogen stream, 4.0 g (11.2 mmol) of 4-chloro-9- [4- (2-pyridyl) phenyl] carbazole obtained in Synthesis Example 6 and 477 mg (5.1 mmol) of aniline were obtained. Sodium-tert-butoxide 1.5 g (15.8 mmol), o-xylene 25 mL, palladium acetate 25 mg (0.11 mmol), tri (tert-butyl) phosphine 79 mg (0.39 mmol), Stir for hours. After cooling to room temperature, 15 mL of pure water was added and stirred.
- Example 18 (Synthesis of Compound (C5)) In a 100 mL three-necked flask under a nitrogen stream, 3.0 g (9.6 mmol) of 4-chloro-9- (4-chlorophenyl) carbazole obtained in Synthesis Example 7 and N- (4-methylphenyl) -N-biphenyl were obtained. Lylamine 5.2 g (20.2 mmol), sodium-tert-butoxide 2.5 g (26.9 mmol), o-xylene 50 mL, palladium acetate 43 mg (0.19 mmol), tri (tert-butyl) phosphine 135 mg (0. 67 mmol) was added and stirred at 140 ° C. for 12 hours.
- Example 19 (Synthesis of Compound (C11)) In a 200 mL three-necked flask under a nitrogen stream, 6.0 g (19.2 mmol) of 4-chloro-9- (4-chlorophenyl) carbazole obtained in Synthesis Example 7 and N, N-bis (4-biphenylyl) amine 13 0.0 g (40.5 mmol), sodium-tert-butoxide 5.1 g (54.0 mmol), o-xylene 60 mL, palladium acetate 86 mg (0.38 mmol), tri (tert-butyl) phosphine 272 mg (1.3 mmol) The mixture was added and stirred at 140 ° C. for 14 hours.
- Example 20 (Evaluation of Triplet Level of Compound (A8)) A solution in which the compound (A8) was dissolved in 2-methyltetrahydrofuran at a concentration of 0.0001 mol / L was prepared, and the phosphorescence spectrum was measured under liquid nitrogen cooling. The maximum wavelength of the phosphorescence spectrum was 480 nm. Table 1 shows triplet levels estimated from the maximum wavelength of the phosphorescence spectrum.
- Example 21 Evaluation of Triplet Level of Compound (A15)
- a phosphorescence spectrum was measured by the same method as in Example 20.
- the maximum wavelength of the phosphorescence spectrum was 482 nm.
- Table 1 shows triplet levels estimated from the maximum wavelength of the phosphorescence spectrum.
- Example 22 Evaluation of Triplet Level of Compound (A278)
- a phosphorescence spectrum was measured by the same method as in Example 20.
- the maximum wavelength of the phosphorescence spectrum was 448 nm.
- Table 1 shows triplet levels estimated from the maximum wavelength of the phosphorescence spectrum.
- Example 23 Evaluation of Triplet Level of Compound (A286)
- a phosphorescence spectrum was measured by the same method as in Example 20.
- the maximum wavelength of the phosphorescence spectrum was 486 nm.
- Table 1 shows triplet levels estimated from the maximum wavelength of the phosphorescence spectrum.
- Example 24 Evaluation of Triplet Level of Compound (A292)
- a phosphorescence spectrum was measured by the same method as in Example 20.
- the maximum wavelength of the phosphorescence spectrum was 483 nm.
- Table 1 shows triplet levels estimated from the maximum wavelength of the phosphorescence spectrum.
- Example 25 Evaluation of Triplet Level of Compound (A124)
- a phosphorescence spectrum was measured by the same method as in Example 20.
- the maximum wavelength of the phosphorescence spectrum was 479 nm.
- Table 1 shows triplet levels estimated from the maximum wavelength of the phosphorescence spectrum.
- Example 26 Evaluation of Triplet Level of Compound (A139)
- a phosphorescence spectrum was measured in the same manner as in Example 20.
- the maximum wavelength of the phosphorescence spectrum was 480 nm.
- Table 1 shows triplet levels estimated from the maximum wavelength of the phosphorescence spectrum.
- Example 27 Evaluation of Triplet Level of Compound (A148)
- a phosphorescence spectrum was measured by the same method as in Example 20.
- the maximum wavelength of the phosphorescence spectrum was 449 nm.
- Table 1 shows triplet levels estimated from the maximum wavelength of the phosphorescence spectrum.
- Example 28 Evaluation of Triplet Level of Compound (A153)
- a phosphorescence spectrum was measured by the same method as in Example 20.
- the maximum wavelength of the phosphorescence spectrum was 445 nm.
- Table 1 shows triplet levels estimated from the maximum wavelength of the phosphorescence spectrum.
- Example 29 Evaluation of Triplet Level of Compound (A318)
- a phosphorescence spectrum was measured in the same manner as in Example 20.
- the maximum wavelength of the phosphorescence spectrum was 457 nm.
- Table 1 shows triplet levels estimated from the maximum wavelength of the phosphorescence spectrum.
- Example 30 Evaluation of Triplet Level of Compound (B1)
- compound (B1) a phosphorescence spectrum was measured in the same manner as in Example 20.
- the maximum wavelength of the phosphorescence spectrum was 450 nm.
- Table 1 shows triplet levels estimated from the maximum wavelength of the phosphorescence spectrum.
- Example 31 Evaluation of Triplet Level of Compound (B2)
- compound (B2) a phosphorescence spectrum was measured by the same method as in Example 20.
- the maximum wavelength of the phosphorescence spectrum was 450 nm.
- Table 1 shows triplet levels estimated from the maximum wavelength of the phosphorescence spectrum.
- Example 32 Evaluation of Triplet Level of Compound (B30)
- a phosphorescence spectrum was measured by the same method as in Example 20.
- the maximum wavelength of the phosphorescence spectrum was 442 nm.
- Table 1 shows triplet levels estimated from the maximum wavelength of the phosphorescence spectrum.
- Example 33 Evaluation of Triplet Level of Compound (B36)
- a phosphorescence spectrum was measured by the same method as in Example 20.
- the maximum wavelength of the phosphorescence spectrum was 452 nm.
- Table 1 shows triplet levels estimated from the maximum wavelength of the phosphorescence spectrum.
- Comparative Example 1 NPD triplet level evaluation
- the phosphorescence spectrum was measured in the same manner as in Example 20.
- the maximum wavelength of the phosphorescence spectrum was 525 nm.
- Table 1 shows triplet levels estimated from the maximum wavelength of the phosphorescence spectrum.
- the compound of the present invention had a higher triplet level than NPD and compound (c).
- Example 34 Evaluation of ionization potential of compound (A5)
- Compound (A5) was dissolved at a concentration of 0.001 mol / L in an anhydrous dichloromethane solution having a tetrabutylammonium perchlorate concentration of 0.1 mol / L, and the ionization potential was measured by cyclic voltammetry.
- Glassy carbon was used for the working electrode
- platinum wire was used for the counter electrode
- silver wire immersed in an acetonitrile solution of AgNO 3 was used for the reference electrode.
- Ferrocene is used as the standard substance, and the ionization potential of the compound (A5) based on the oxidation-reduction potential of ferrocene is 0.43 V vs.
- Fc / Fc + This value was slightly higher than the ionization potential (0.31 V vs. Fc / Fc + ) of NPD that has been conventionally known as a hole transport material, and was a preferable ionization potential as a hole transport material.
- Example 35 Evaluation of ionization potential of compound (A8)
- the ionization potential of the compound (A8) was evaluated in the same manner as in Example 34.
- the ionization potential of the compound (A8) based on the oxidation-reduction potential of ferrocene is 0.44 V vs. Fc / Fc +, which is slightly higher than the ionization potential (0.31 V vs. Fc / Fc + ) of NPD, which has been conventionally known as a hole transport material, and is a preferable ionization potential as a hole transport material. It was.
- Example 36 Evaluation of ionization potential of compound (A15)
- the ionization potential of the compound (A15) was evaluated in the same manner as in Example 34.
- the ionization potential of the compound (A15) based on the redox potential of ferrocene is 0.40 V vs. Fc / Fc +, which is slightly higher than the ionization potential (0.31 V vs. Fc / Fc + ) of NPD, which has been conventionally known as a hole transport material, and is a preferable ionization potential as a hole transport material. It was.
- Example 37 Evaluation of ionization potential of compound (A278)
- the ionization potential of the compound (A278) was evaluated in the same manner as in Example 34.
- the ionization potential of the compound (A278) based on the oxidation-reduction potential of ferrocene is 0.45 V vs. Fc / Fc +, which is slightly higher than the ionization potential (0.31 V vs. Fc / Fc + ) of NPD, which has been conventionally known as a hole transport material, and is a preferable ionization potential as a hole transport material. It was.
- Example 38 Evaluation of ionization potential of compound (A286)
- the ionization potential of the compound (A286) was evaluated in the same manner as in Example 34.
- the ionization potential of the compound (A286) based on the oxidation-reduction potential of ferrocene is 0.44 V vs. Fc / Fc +, which is slightly higher than the ionization potential (0.31 V vs. Fc / Fc + ) of NPD, which has been conventionally known as a hole transport material, and is a preferable ionization potential as a hole transport material. It was.
- Example 39 Evaluation of ionization potential of compound (A289)
- the ionization potential of the compound (A289) was evaluated in the same manner as in Example 34.
- the ionization potential of the compound (A289) based on the oxidation-reduction potential of ferrocene is 0.39 V vs. Fc / Fc +, which is slightly higher than the ionization potential (0.31 V vs. Fc / Fc + ) of NPD, which has been conventionally known as a hole transport material, and is a preferable ionization potential as a hole transport material. It was.
- Example 40 Evaluation of ionization potential of compound (A292)
- the ionization potential of the compound (A292) was evaluated in the same manner as in Example 34.
- the ionization potential of the compound (A292) based on the oxidation-reduction potential of ferrocene is 0.43 V vs. Fc / Fc +, which is slightly higher than the ionization potential (0.31 V vs. Fc / Fc + ) of NPD, which has been conventionally known as a hole transport material, and is a preferable ionization potential as a hole transport material. It was.
- Example 41 Evaluation of ionization potential of compound (A124)
- the ionization potential of the compound (A124) was evaluated in the same manner as in Example 34.
- the ionization potential of the compound (A124) based on the oxidation-reduction potential of ferrocene is 0.44 V vs. Fc / Fc +, which is slightly higher than the ionization potential (0.31 V vs. Fc / Fc + ) of NPD, which has been conventionally known as a hole transport material, and is a preferable ionization potential as a hole transport material. It was.
- Example 42 Evaluation of ionization potential of compound (A139)
- the ionization potential of the compound (A139) was evaluated in the same manner as in Example 34.
- the ionization potential of the compound (A139) based on the oxidation-reduction potential of ferrocene is 0.45 V vs. Fc / Fc +, which is slightly higher than the ionization potential (0.31 V vs. Fc / Fc + ) of NPD, which has been conventionally known as a hole transport material, and is a preferable ionization potential as a hole transport material. It was.
- Example 43 Evaluation of ionization potential of compound (A148)
- the ionization potential of the compound (A148) was evaluated in the same manner as in Example 34.
- the ionization potential of the compound (A148) based on the oxidation-reduction potential of ferrocene is 0.45 V vs. Fc / Fc +, which is slightly higher than the ionization potential (0.31 V vs. Fc / Fc + ) of NPD, which has been conventionally known as a hole transport material, and is a preferable ionization potential as a hole transport material. It was.
- Example 44 Evaluation of ionization potential of compound (A153)
- the ionization potential of the compound (A153) was evaluated in the same manner as in Example 34.
- the ionization potential of the compound (A153) based on the oxidation-reduction potential of ferrocene is 0.47 V vs. Fc / Fc +, which is slightly higher than the ionization potential (0.31 V vs. Fc / Fc + ) of NPD, which has been conventionally known as a hole transport material, and is a preferable ionization potential as a hole transport material. It was.
- Example 45 Evaluation of ionization potential of compound (A318)
- the ionization potential of the compound (A318) was evaluated in the same manner as in Example 34.
- the ionization potential of the compound (A318) based on the oxidation-reduction potential of ferrocene is 0.44 V vs. Fc / Fc +, which is slightly higher than the ionization potential (0.31 V vs. Fc / Fc + ) of NPD, which has been conventionally known as a hole transport material, and is a preferable ionization potential as a hole transport material. It was.
- Example 46 Evaluation of ionization potential of compound (B1)
- the ionization potential of the compound (B1) was evaluated in the same manner as in Example 34.
- the ionization potential of the compound (B1) based on the redox potential of ferrocene is 0.48 V vs. Fc / Fc +, which is slightly higher than the ionization potential (0.31 V vs. Fc / Fc + ) of NPD, which has been conventionally known as a hole transport material, and is a preferable ionization potential as a hole transport material. It was.
- Example 47 Evaluation of ionization potential of compound (B2)
- the ionization potential of the compound (B2) was evaluated in the same manner as in Example 34.
- the ionization potential of the compound (B2) based on the oxidation-reduction potential of ferrocene is 0.46 V vs. Fc / Fc +, which is slightly higher than the ionization potential (0.31 V vs. Fc / Fc + ) of NPD, which has been conventionally known as a hole transport material, and is a preferable ionization potential as a hole transport material. It was.
- Example 48 Evaluation of ionization potential of compound (B27)
- the ionization potential of the compound (B27) was evaluated in the same manner as in Example 34.
- the ionization potential of the compound (B27) based on the redox potential of ferrocene is 0.48 V vs. Fc / Fc +, which is slightly higher than the ionization potential (0.31 V vs. Fc / Fc + ) of NPD, which has been conventionally known as a hole transport material, and is a preferable ionization potential as a hole transport material. It was.
- Example 49 Evaluation of ionization potential of compound (B30)
- the ionization potential of the compound (B30) was evaluated in the same manner as in Example 34.
- the ionization potential of the compound (B30) based on the oxidation-reduction potential of ferrocene is 0.48 V vs. Fc / Fc +, which is slightly higher than the ionization potential (0.31 V vs. Fc / Fc + ) of NPD, which has been conventionally known as a hole transport material, and is a preferable ionization potential as a hole transport material. It was.
- Example 50 Evaluation of ionization potential of compound (B36)
- the ionization potential of the compound (B36) was evaluated in the same manner as in Example 34.
- the ionization potential of the compound (B36) based on the oxidation-reduction potential of ferrocene is 0.48 V vs. Fc / Fc +, which is slightly higher than the ionization potential (0.31 V vs. Fc / Fc + ) of NPD, which has been conventionally known as a hole transport material, and is a preferable ionization potential as a hole transport material. It was.
- Example 51 Evaluation of ionization potential of compound (C5)
- the ionization potential of the compound (C5) was evaluated in the same manner as in Example 34.
- the ionization potential of the compound (C5) based on the oxidation-reduction potential of ferrocene is 0.40 V vs. Fc / Fc +, which is slightly higher than the ionization potential (0.31 V vs. Fc / Fc + ) of NPD, which has been conventionally known as a hole transport material, and is a preferable ionization potential as a hole transport material. It was.
- Example 52 Evaluation of ionization potential of compound (C11)
- the ionization potential of the compound (C11) was evaluated in the same manner as in Example 34.
- the ionization potential of the compound (C11) based on the oxidation-reduction potential of ferrocene is 0.45 V vs. Fc / Fc +, which is slightly higher than the ionization potential (0.31 V vs. Fc / Fc + ) of NPD, which has been conventionally known as a hole transport material, and is a preferable ionization potential as a hole transport material. It was.
- Comparative Example 2 Evaluation of ionization potential of compound (a)
- the ionization potential of the compound (a) in which an amino group was bonded to the 3-position of the carbazole ring was evaluated.
- the ionization potential of the compound (a) is 0.13 V vs.
- NPD (0.31 V vs. Fc / Fc + )
- Fc / Fc + which is conventionally known as a hole transport material
- it is an Fc / Fc + and is an unfavorable ionization potential as a hole transport material. It was.
- Example 53 Measurement of Glass Transition Temperature of Compound (A139) 5 mg of the compound (A139) was placed in an Al pan, and the glass transition temperature was measured under a temperature increase condition of 10 ° C./min in a nitrogen atmosphere. Al 2 O 3 was used as a standard sample. The glass transition temperature of the compound (A139) was 143 ° C., and it was found that the stability of the thin film state was higher than that of NPD (96 ° C.) and the compound (b) (100 ° C.).
- Example 54 Measurement of glass transition temperature of compound (A148)
- the glass transition temperature of compound (A148) was measured in the same manner as in Example 53.
- the glass transition temperature of the compound (A148) was 142 ° C., and it was found that the stability of the thin film state was higher than that of NPD (96 ° C.) and the compound (b) (100 ° C.).
- Example 55 Measurement of glass transition temperature of compound (A153)
- the glass transition temperature of compound (A153) was measured in the same manner as in Example 53.
- the glass transition temperature of the compound (A153) was 150 ° C., and it was found that the stability of the thin film state was higher than that of NPD (96 ° C.) and the compound (b) (100 ° C.).
- Example 56 Measurement of glass transition temperature of compound (B1)
- the glass transition temperature of compound (B1) was measured in the same manner as in Example 53.
- the glass transition temperature of the compound (B1) was 169 ° C., and it was found that the stability of the thin film state was higher than that of NPD (96 ° C.) and the compound (b) (100 ° C.).
- Example 57 Measurement of glass transition temperature of compound (B30)
- the glass transition temperature of compound (B30) was measured in the same manner as in Example 53.
- the glass transition temperature of the compound (B30) was 191 ° C., and it was found that the stability of the thin film state was higher than that of NPD (96 ° C.) and the compound (b) (100 ° C.).
- Example 58 (Element Evaluation of Compound (A5))
- the glass substrate on which the ITO transparent electrode (anode) having a thickness of 200 nm was laminated was subjected to ultrasonic cleaning with acetone and pure water and boiling cleaning with isopropyl alcohol. Further, ultraviolet ozone cleaning was performed, and after evacuation with a vacuum pump until the pressure became 5 ⁇ 10 ⁇ 4 Pa or less after installation in a vacuum deposition apparatus. First, copper phthalocyanine was deposited on the ITO transparent electrode at a deposition rate of 0.1 nm / second to form a 10 nm hole injection layer.
- NPD was deposited at a deposition rate of 0.3 nm / second to 25 nm
- compound (A5) was deposited at a deposition rate of 0.1 nm / second to 5 nm to form two hole transport layers.
- tris (2-phenylpyridine) iridium (Ir (ppy) 3 ) as a phosphorescent dopant material and 4,4′-bis (N-carbazolyl) biphenyl (CBP) as a host material have a weight ratio of 1:11.
- BAlq bis (2-methyl-8-quinolinolato) (p-phenylphenolato) aluminum
- Alq 3 Tris (8-quinolinolato) aluminum
- lithium fluoride was deposited as an electron injection layer to a thickness of 0.5 nm at a deposition rate of 0.01 nm / second
- aluminum was further deposited to a thickness of 100 nm at a deposition rate of 0.25 nm / second to form a cathode.
- a sealing glass plate was bonded with a UV curable resin to obtain an organic EL element for evaluation.
- Example 59 (Element Evaluation of Compound (A8)) An organic EL device was produced in the same manner as in Example 58 except that the compound (A5) was changed to the compound (A8).
- Table 2 shows the drive voltage and current efficiency when a current of 20 mA / cm 2 was applied.
- Example 60 (Element Evaluation of Compound (A15)) An organic EL device was produced in the same manner as in Example 58 except that the compound (A5) was changed to the compound (A15). Table 2 shows the drive voltage and current efficiency when a current of 20 mA / cm 2 was applied.
- Example 61 (Element Evaluation of Compound (A278)) An organic EL device was produced in the same manner as in Example 58 except that the compound (A5) was changed to the compound (A278).
- Table 2 shows the drive voltage and current efficiency when a current of 20 mA / cm 2 was applied.
- Example 62 (Element Evaluation of Compound (A139)) An organic EL device was produced in the same manner as in Example 58 except that the compound (A5) was changed to the compound (A139). Table 2 shows the drive voltage and current efficiency when a current of 20 mA / cm 2 was applied.
- Example 63 (Device Evaluation of Compound (A148)) An organic EL device was produced in the same manner as in Example 58 except that the compound (A5) was changed to the compound (A148). Table 2 shows the drive voltage and current efficiency when a current of 20 mA / cm 2 was applied.
- Example 64 (Device Evaluation of Compound (A153)) An organic EL device was produced in the same manner as in Example 58 except that the compound (A5) was changed to the compound (A153). Table 2 shows the drive voltage and current efficiency when a current of 20 mA / cm 2 was applied.
- Example 65 (Device Evaluation of Compound (B2)) An organic EL device was produced in the same manner as in Example 58 except that the compound (A5) was changed to the compound (B2). Table 2 shows the drive voltage and current efficiency when a current of 20 mA / cm 2 was applied.
- Example 66 (Element Evaluation of Compound (B27)) An organic EL device was produced in the same manner as in Example 58 except that the compound (A5) was changed to the compound (B27). Table 2 shows the drive voltage and current efficiency when a current of 20 mA / cm 2 was applied.
- Example 67 (Device Evaluation of Compound (B30)) An organic EL device was produced in the same manner as in Example 58 except that the compound (A5) was changed to the compound (B30). Table 2 shows the drive voltage and current efficiency when a current of 20 mA / cm 2 was applied.
- Example 68 (Device Evaluation of Compound (B36)) An organic EL device was produced in the same manner as in Example 58 except that the compound (A5) was changed to the compound (B36). Table 2 shows the drive voltage and current efficiency when a current of 20 mA / cm 2 was applied.
- Example 69 (Device Evaluation of Compound (C5)) An organic EL device was produced in the same manner as in Example 58 except that the compound (A5) was changed to the compound (C5).
- Table 2 shows the drive voltage and current efficiency when a current of 20 mA / cm 2 was applied.
- Comparative Example 3 An organic EL device was produced in the same manner as in Example 58 except that the compound (A5) was changed to NPD.
- Table 2 shows the driving voltage and current efficiency when a current of 20 mA / cm 2 was applied.
- Comparative Example 4 An organic EL device was produced in the same manner as in Example 58 except that the compound (A5) was changed to the compound (a). Table 2 shows the drive voltage and current efficiency when a current of 20 mA / cm 2 was applied.
- Reference example 2 An organic EL device was produced in the same manner as in Example 58 except that the compound (A5) was changed to the compound (b). Table 2 shows the drive voltage and current efficiency when a current of 20 mA / cm 2 was applied.
- the 4-aminocarbazole compound of the present invention showed higher current efficiency (luminescence efficiency) than NPD, compound (a) and compound (b). In the device using the 4-aminocarbazole compound, the driving voltage could be kept low.
- the phosphorescent or fluorescent organic EL device having at least one layer containing the 4-aminocarbazole compound of the present invention has a higher luminous efficiency than the organic EL device including a conventionally known carbazole ring-introduced material. (Current efficiency) and a remarkable effect that the driving voltage is low. Therefore, the 4-aminocarbazole compound of the present invention can provide a phosphorescent or fluorescent organic EL device having high luminance and low power consumption.
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Abstract
Description
R1~R7が、各々独立して、炭素数6~30のアリール基、炭素数3~20のヘテロアリール基、メチル基、エチル基、炭素数3~18の直鎖、分岐、若しくは環状のアルキル基、メトキシ基、エトキシ基、炭素数3~18の直鎖、分岐、若しくは環状のアルコキシ基、シアノ基、水素原子、又はハロゲン原子である上記[1]に記載の4-アミノカルバゾール化合物。
R1~R7が、各々独立して、フェニル基、メチルフェニル基、メトキシフェニル基、ビフェニリル基、ジベンゾチエニル基、ジベンゾフラニル基、メチル基、メトキシ基、又は水素原子である上記[1]または[2]に記載の4-アミノカルバゾール化合物。
R1~R7が、各々独立して、フェニル基、メチルフェニル基、メトキシフェニル基、又は水素原子である上記[1]乃至[3]のいずれか一項に記載の4-アミノカルバゾール化合物。
R4、R5、R6、及びR7が水素原子である上記[1]乃至[4]のいずれか一項に記載の4-アミノカルバゾール化合物。
R1、R2、R4、R5、R6、及びR7が水素原子である上記[1]乃至[5]のいずれか一項に記載の4-アミノカルバゾール化合物。
Ar1~Ar4が、各々独立して、炭素数6~30のアリール基、ジベンゾチエニル基、ジベンゾフラニル基、4-カルバゾリル基、ジベンゾフラニルフェニル基、ジベンゾチエニルフェニル基、又は9-カルバゾリルフェニル基(これらの基は、各々独立して、メチル基、エチル基、炭素数3~18の直鎖、分岐、若しくは環状のアルキル基、メトキシ基、エトキシ基、炭素数3~18の直鎖、分岐、若しくは環状のアルコキシ基、炭素数6~30のアリール基、及び炭素数3~11のヘテロアリール基からなる群より選ばれる少なくとも一つの置換基を有していてもよい)である上記[1]乃至[6]のいずれか一項に記載の4-アミノカルバゾール化合物。
Ar1~Ar4が、各々独立して、フェニル基、ビフェニリル基、ターフェニリル基、フルオレニル基、ベンゾフルオレニル基、ジベンゾチエニル基、ジベンゾフラニル基、ジベンゾフラニルフェニル基、ジベンゾチエニルフェニル基、又は9-カルバゾリルフェニル基(これらの基は、各々独立して、メチル基、エチル基、炭素数3~18の直鎖、分岐、若しくは環状のアルキル基、メトキシ基、エトキシ基、炭素数3~18の直鎖、分岐、若しくは環状のアルコキシ基、からなる群より選ばれる少なくとも一つの置換基を有していてもよい)、又は、4-カルバゾリル基(メチル基、エチル基、炭素数3~18の直鎖、分岐、若しくは環状のアルキル基、メトキシ基、エトキシ基、炭素数3~18の直鎖、分岐、若しくは環状のアルコキシ基、炭素数6~30のアリール基、及び炭素数3~11のヘテロアリール基からなる群より選ばれる少なくとも一つの置換基を有していてもよい)である上記[1]乃至[7]のいずれか一項に記載の4-アミノカルバゾール化合物。
Ar1~Ar4が、各々独立して、フェニル基、メチルフェニル基、メトキシフェニル基、ビフェニリル基、ターフェニリル基、9,9’-ジメチルフルオレニル基、11,11’-ジメチルベンゾ[a]フルオレニル基、ジベンゾチエニル基、ジベンゾフラニル基、ジベンゾチエニルフェニル基、4-(9-カルバゾリル)フェニル基、9-フェニルカルバゾール-4-イル基、9-ビフェニリルカルバゾール-4-イル基、9-キノリルカルバゾール-4-イル基、または9-ジベンゾチエニルカルバゾール-4-イル基である上記[1]乃至[8]のいずれか一項に記載の4-アミノカルバゾール化合物。
Xが、(n+1)価のベンゼン、(n+1)価のビフェニル、(n+1)価のナフタレン、(n+1)価のフェナントレン、(n+1)価のフルオレン、(n+1)価のナフチルベンゼン、(n+1)価のピリジン、(n+1)価のピリミジン、(n+1)価の1,3,5-トリアジン、(n+1)価のキノリン、(n+1)価のジベンゾチオフェン、(n+1)価のジベンゾフラン、(n+1)価のピリジルベンゼン、(n+1)価のイミダゾリルベンゼン、(n+1)価のベンゾイミダゾリルベンゼン、及び(n+1)価のベンゾチアゾリルベンゼン(これらの芳香環は、メチル基、エチル基、炭素数3~18の直鎖、分岐、若しくは環状のアルキル基、メトキシ基、エトキシ基、炭素数3~18の直鎖、分岐、若しくは環状のアルコキシ基、炭素数6~12のアリール基、炭素数3~20のヘテロアリール基、シアノ基、及びハロゲン原子からなる群より選ばれる少なくとも一つの置換基を有していてもよい)から選ばれる1種である上記[1]乃至[9]のいずれか一項に記載の4-アミノカルバゾール化合物。
Xが、(n+1)価のベンゼン、(n+1)価のビフェニル、(n+1)価のキノリン、(n+1)価のジベンゾチオフェン、(n+1)価の1,3,5-トリアジン、及び(n+1)価のピリジルフェニル(これらの芳香環は、メチル基、エチル基、炭素数3~18の直鎖、分岐、若しくは環状のアルキル基、メトキシ基、エトキシ基、炭素数3~18の直鎖、分岐、若しくは環状のアルコキシ基、炭素数6~12のアリール基、シアノ基、及びハロゲン原子からなる群より選ばれる少なくとも一つの置換基を有していてもよい)から選ばれる1種である上記[1]乃至[10]のいずれか一項に記載の4-アミノカルバゾール化合物。
Xが、(n+1)価のベンゼン、(n+1)価のビフェニル、(n+1)価のキノリン、(n+1)価のジベンゾチオフェン、(n+1)価の2,4-ジフェニル-1,3,5-トリアジン、又は(n+1)価のピリジルベンゼンである上記[1]乃至[11]のいずれか一項に記載の4-アミノカルバゾール化合物。
n=0又は1である上記[1]乃至[12]のいずれか一項に記載の4-アミノカルバゾール化合物。
したがって、本発明によれば、輝度が高く、消費電力の少ない燐光発光性または蛍光発光性有機EL素子を提供できる。
なお、工業的製造方法を鑑みた場合、R4、R5、R6、及びR7が水素原子であることがいっそう好ましく、R1、R2、R4、R5、R6、及びR7が水素原子であることが、よりいっそう好ましい
Xは炭素数6~17の(n+1)価の芳香族炭化水素基、炭素数3~20の(n+1)価のヘテロ芳香族基、又は炭素数9~26の(n+1)価のヘテロアリールフェニル基を表す。
ピコリレート(以下、FIrpicと略す)と組み合わせて使用する場合、当該材料の三重項準位が2.65eVであることから(Applied Physics Letters,2003,第82巻,2422頁)、前記一般式(1)で表される4-アミノカルバゾール化合物の三重項準位は、特に限定するものではないが、2.66eV以上であることが好ましく、2.70eV以上であることが更に好ましい。
ルートaは、下記の反応工程を含む。一般式(2)で表される、4位がハロゲン化された9H-カルバゾール化合物と、一般式(3)で表されるハロゲン原子を有する化合物とを、塩基の存在下、銅触媒又はパラジウム触媒を用いて反応させ、一般式(4)で表される4-ハロゲン化-9-置換カルバゾール化合物を得る。更に、得られた一般式(4)で表される4-ハロゲン化-9-置換カルバゾール化合物と、一般式(5)で表される2級アミン化合物又は一般式(6)で表される1級アミン化合物とを、塩基の存在下、銅触媒又はパラジウム触媒を用いて反応させる。
ルートbは、下記の反応工程を含む。一般式(2)で表される4位がハロゲン化された9H-カルバゾール化合物と、一般式(7)で表されるハロゲン化化合物とを、塩基の存在下、銅触媒又はパラジウム触媒を用いて反応させ、一般式(8)で表される4位及び9位の置換基Xがハロゲン化されたカルバゾール化合物を得る。更に、塩基の存在下、銅触媒又はパラジウム触媒を用いて2級アミン化合物を反応させる。
三重項準位は、日立ハイテクノロジーズ社製のF2500形分光蛍光光度計を使用して評価した。
窒素気流下、1Lの三口フラスコに、2,3-ジクロロニトロベンゼン 75.0g(390.6mmol)、フェニルボロン酸 47.6g(390.6mmol)、テトラキス(トリフェニルホスフィン)パラジウム 9.0g(7.8mmol)、テトラヒドロフラン 250mL、40wt%のりん酸三カリウム水溶液 518g(976.5mmol)を加え、8時間加熱還流した。室温まで冷却した後、水層と有機層を分液し、有機層を飽和塩化アンモニウム水溶液と飽和塩化ナトリウム水溶液で洗浄した後、無水硫酸マグネシウムで乾燥後、減圧下に溶媒留去した。得られた固体をエタノールで再結晶し、2-ニトロ-6-クロロビフェニルの薄黄色針状結晶を62.8g単離した(収率68%)。
1H-NMR(CDCl3);7.66-7.74(m,2H),7.41-7.45(m,4H),7.22-7.27(m,2H)
窒素気流下、500mLのナス型フラスコに合成例1で得られた2-ニトロ-6-クロロビフェニル 60.0g(257.4mmol)を仕込み、140℃に加熱後、亜リン酸トリエチル 106gを2時間で滴下した。滴下後、140℃で更に2時間攪拌し、減圧下に亜リン酸トリエチルを留去した。残渣にトルエンを加え、シリカゲルカラムクロマトグラフィー(トルエン)で精製することにより、4-クロロカルバゾールの白色粉末を18.9g(93.72mmol)単離した(収率36%)。
1H-NMR(Acetone-d6);10.71(br-s,1H),8.52(d,1H),7.15-7.59(m,6H)
窒素気流下、200mLの三口フラスコに合成例2で得られた4-クロロカルバゾール 10.0g(49.5mmol)、4-ブロモビフェニル 11.6g(52.0mmol)、炭酸カリウム 9.5g(69.4mmol)、o-キシレン 100mL、酢酸パラジウム 111mg(0.49mmol)、トリ(tert-ブチル)ホスフィン 349mg(1.73mmol)を添加して130℃で14時間攪拌した。室温まで冷却後、純水 50mLを加え、有機層を分離した。有機層を純水、飽和食塩水で洗浄した後、無水硫酸マグネシウムで乾燥し、減圧下に溶媒留去した。得られた粉末をエタノールで洗浄し、4-クロロ-9-(4-ビフェニリル)カルバゾールの薄茶色粉末を12.5g(35.4mmol)単離した(収率71%)。
1H-NMR(CDCl3);8.68(d,1H),7.80(d,2H),7.67(d,2H),7.22-7.59(m,11H)
窒素気流下、100mLの三口フラスコに合成例2で得られた4-クロロカルバゾール 5.0g(24.7mmol)、3-ブロモキノリン 5.1g(24.7mmol)、炭酸カリウム 4.7g(34.7mmol)、o-キシレン 25mL、酢酸パラジウム 276mg(1.23mmol)、トリ(tert-ブチル)ホスフィン 869mg(4.3mmol)を添加して140℃で24時間攪拌した。室温まで冷却後、純水 20mLを加え、有機層を分離した。有機層を水、飽和食塩水で洗浄した後、無水硫酸マグネシウムで乾燥し、減圧下に溶媒留去した。残渣をシリカゲルカラムクロマトグラフィー(トルエンとヘキサンの混合溶媒(体積比=3:1))で精製し、4-クロロ-9-(3-キノリル)カルバゾールの茶色ガラス状固体を4.6g(14.0mmol)単離した(収率56%)。
1H-NMR(CDCl3);9.09(s,1H),8.70(d,1H),8.31(s,1H),8.26(d,1H),7.90(d,1H),7.82(d,1H),7.66(t,1H),7.22-7.51(m,6H)
窒素気流下、50mLの三口フラスコに合成例2で得られた4-クロロカルバゾール 2.6g(12.9mmol)、2-ブロモジベンゾチオフェン 3.4g(12.9mmol)、炭酸カリウム 3.5g(25.9mmol)、o-キシレン 13mL、酢酸パラジウム 29mg(0.12mmol)、トリ(tert-ブチル)ホスフィン 91mg(0.45mmol)を添加して140℃で18時間攪拌した。室温まで冷却後、純水 10mLを加え、有機層を分離した。有機層を水、飽和食塩水で洗浄した後、無水硫酸マグネシウムで乾燥し、減圧下に溶媒留去した。残渣をシリカゲルカラムクロマトグラフィー(トルエンとヘキサンの混合溶媒(体積比=1:2))で精製し、4-クロロ-9-(2-ジベンゾチエニル)カルバゾールの茶色ガラス状固体を3.5g(9.1mmol)単離した(収率70%)。
1H-NMR(CDCl3);8.71(d,1H),8.27(d,1H),8.04-8.16(m,3H),7.83-7.94(m,2H),7.25-7.61(m,7H)
窒素気流下、100mLの三口フラスコに合成例2で得られた4-クロロカルバゾール 5.0g(24.7mmol)、4-(2-ピリジル)ブロモベンゼン 6.0g(26.0mmol)、炭酸カリウム 4.7g(34.7mmol)、o-キシレン 25mL、酢酸パラジウム 55mg(0.24mmol)、トリ(tert-ブチル)ホスフィン 174mg(0.86mmol)を添加して140℃で14時間攪拌した。室温まで冷却後、純水 20mLを加え、有機層を分離した。有機層を水、飽和食塩水で洗浄した後、無水硫酸マグネシウムで乾燥し、減圧下に溶媒留去した。残渣をシリカゲルカラムクロマトグラフィー(トルエンとヘキサンの混合溶媒(体積比=2:1))で精製し、4-クロロ-9-[4-(2-ピリジル)フェニル]カルバゾールの茶色ガラス状固体を4.5g(12.7mmol)単離した(収率51%)。
1H-NMR(CDCl3);8.66-8.75(m,2H)8.20(d,2H),7.77(d,2H),7.61(d,2H),7.22-7.46(m,7H)
窒素気流下、100mLの三口フラスコに、合成例2で得られた4-クロロカルバゾール 5.0g(24.7mmol)、p-ブロモクロロベンゼン 5.1g(27.2mmol)、炭酸カリウム 4.7g(34.7mmol)、o-キシレン 50mL、酢酸パラジウム 55mg(0.24mmol)、トリ(tert-ブチル)ホスフィン 174mg(0.86mmol)を添加して130℃で24時間攪拌した。室温まで冷却後、純水 30mLを加え、有機層を分離した。有機層を水、飽和食塩水で洗浄した後、無水硫酸マグネシウムで乾燥し、減圧下に溶媒留去した。残渣をシリカゲルカラムクロマトグラフィー(ヘキサン)で精製し、4-クロロ-9-(4-クロロフェニル)カルバゾールの白色固体を4.4g(14.1mmol)単離した(収率56%)。
1H-NMR(CDCl3);8.64(d,1H),7.53(d,2H),7.15-7.45(m,8H)
窒素気流下、200mLの三口フラスコに、合成例2で得られた4-クロロカルバゾール 17.0g(84.3mmol)、ブロモベンゼン 15.8g(101.1mmol)、炭酸カリウム 19.5g(141.6mmol)、o-キシレン 85mL、酢酸パラジウム 227mg(1.0mmol)、トリ(tert-ブチル)ホスフィン 714mg(3.5mmol)を添加して130℃で24時間攪拌した。室温まで冷却後、純水 60mLを加え、有機層を分離した。有機層を水、飽和食塩水で洗浄した後、無水硫酸マグネシウムで乾燥し、減圧下に溶媒留去した。残渣をシリカゲルカラムクロマトグラフィー(ヘキサン)で精製し、無色オイル状の4-クロロ-9-フェニルカルバゾールを14.3g(51.6mmol)単離した(収率61%)。
1H-NMR(CDCl3);8.67(d,1H),7.23-7.65(m,11H)
窒素気流下、100mLの三口フラスコに、水素化ナトリウム(油性、60%) 0.53g(13.4mmol)を仕込み、脱水ジメチルホルムアミド 15mLを加えて攪拌した。スラリー状の溶液に、脱水ジメチルホルムアミド 15mLに溶解させた4-クロロカルバゾール 2.2g(11.2mmol)を滴下し、30分攪拌した。更に、反応液に脱水ジメチルホルムアミド 40mLに溶解させた2-クロロ-4,6-ジフェニル-1,3,5-トリアジン 3.0g(11.2mmol)を滴下した。室温で2時間攪拌後、メタノール 10mL、純水 100mLを加え、反応を停止した。純水添加時に析出した白色粉末を回収し、純水とエタノールで洗浄した。得られた粉末をo-キシレンで再結晶し、4-クロロ-9-(4,6-ジフェニル-1,3,5-トリアジン-2-イル)カルバゾールの白色結晶を3.1g(7.2mmol)単離した(収率64%)。
1H-NMR(CDCl3);8.72(d,1H),8.71(d,4H),7.91-8.01(m,2H),7.37-7.65(m,10H)
窒素気流下、50mlの三口フラスコに、合成例3で得た4-クロロ-9-(4-ビフェニリル)カルバゾール 1.8g(5.2mmol)を仕込み、ジメチルホルムアミド 10mL、N-ブロモスクシンイミド 0.93g(5.2mmol)を添加した。室温で2時間攪拌し、純水 10mLを加え析出した白色粉末をろ取した。粉末を純水及びメタノールで洗浄し、減圧下で乾燥した。白色粉末状の生成物は、原料である4-クロロ-9-(4-ビフェニリル)カルバゾールと4-クロロ-6-ブロモ-9-(4-ビフェニリル)カルバゾール及び4-クロロ-3,6-ジブロモ-9-(4-ビフェニリル)カルバゾールの混合物であった(4-クロロ-6-ブロモ-9-(4-ビフェニリル)カルバゾールの純度は72%であった)。窒素気流下、上記の混合物 0.90gを10mLの三口フラスコに仕込み、フェニルボロン酸 0.26g(2.1mmol)、テトラキス(トリフェニルホスフィン)パラジウム 0.11g(0.09mmol)、テトラヒドロフラン 5mL、20wt%の炭酸カリウム水溶液 2.5g(4.8mmol)を加え、14時間加熱還流した。室温まで冷却した後、水層と有機層を分液し、有機層を純水と飽和塩化ナトリウム水溶液で洗浄した。無水硫酸マグネシウムで有機層を乾燥後、減圧下に溶媒留去し、残渣をシリカゲルカラムクロマトグラフィー(ヘキサン)で精製し、4-クロロ-6-フェニル-9-(4-ビフェニリル)カルバゾールの白色粉末を0.51g(1.0mmol)単離した(収率19%)。
1H-NMR(CDCl3);8.39(s,1H),7.23-7.82(m,19H)
窒素気流下、100mLの三口フラスコに、N-フェニル-N-ビフェニリルアミン 15.0g(61.1mmol)を仕込み、ジメチルホルムアミド 100mL、N-ブロモスクシンイミド 10.8g(61.1mmol)を添加し、室温で2時間攪拌した。トルエン 10mL、純水 10mLを加え、水層と有機層に分液した。有機層を純水と飽和塩化ナトリウム水溶液で洗浄し、無水硫酸マグネシウムで乾燥後、減圧下に溶媒留去した。得られた固体をトルエンで再結晶し、N-(4-ブロモフェニル)-N-ビフェニリルアミンの灰色粉末を13.4g(41.4mmol)単離した(収率67%)。
1H-NMR(Acetone-d6);7.55-7.64(m,5H),7.27-7.45(m,5H),7.21(d,2H),7.11(d,2H)
窒素気流下、300mLの三口フラスコに合成例11で得られたN-(4-ブロモフェニル)-N-ビフェニリルアミン 12.0g(37.1mmol)、3-ビフェニリルボロン酸 7.7g(38.9mmol)、テトラキス(トリフェニルホスフィン)パラジウム 2.1g(1.8mmol)、トルエン 60mL、エタノール 10mL、40wt%のりん酸三カリウム水溶液 49g(92.8mmol)を加え、5時間加熱還流した。室温まで冷却した後、水層と有機層を分液し、有機層を純水と飽和塩化ナトリウム水溶液で洗浄した。無水硫酸マグネシウムで有機層を乾燥後、減圧下に溶媒留去し、残渣をシリカゲルカラムクロマトグラフィー(トルエンとヘキサンの混合溶媒(体積比=1:1))で精製し、N-ビフェニリル-N-(m-ターフェニル)アミンの薄黄色粉末を10.2g(25.6mmol)単離した(収率69%)。
1H-NMR(Acetone-d6);7.89(s,1H),7.37-7.73(m,17H),7.26-7.32(m,5H)
窒素気流下、300mlの三口フラスコに合成例11で得られたN-(4-ブロモフェニル)-N-ビフェニリルアミン 7.0g(21.6mmol)、ジベンゾチオフェン-4-ボロン酸 5.9g(25.9mmol)、テトラキス(トリフェニルホスフィン)パラジウム 1.2g(1.0mmol)、トルエン 35mL、エタノール 5mL、40wt%のりん酸三カリウム水溶液 28g(54.1mmol)を加え、3時間加熱還流した。室温まで冷却した後、水層と有機層を分液し、有機層を純水と飽和塩化ナトリウム水溶液で洗浄した。無水硫酸マグネシウムで有機層を乾燥後、減圧下に溶媒留去し、残渣をシリカゲルカラムクロマトグラフィー(トルエンとヘキサンの混合溶媒(体積比=1:1))で精製し、N-ビフェニリル-N-(4-(4-ジベンゾチエニル)フェニル)アミンの薄黄色粉末を5.2g(12.1mmol)単離した(収率56%)。
1H-NMR(Acetone-d6);8.22-8.32(m,2H),7.90-7.95(m,1H),7.77(s,1H),7.27-7.70(m,17H)
窒素気流下、100mLの三口フラスコに、合成例3で得られた4-クロロ-9-(4-ビフェニリル)カルバゾール 3.5g(9.9mmol)、N-フェニル-N-ビフェニリルアミン 2.4g(9.9mmol)、ナトリウム-tert-ブトキシド 1.3g(13.8mmol)、o-キシレン 35mL、酢酸パラジウム 22mg(0.09mmol)、トリ(tert-ブチル)ホスフィン 69mg(0.34mmol)を添加して140℃で12時間攪拌した。室温まで冷却後、純水を25mL添加し攪拌した。水層と有機層を分液し、さらに有機層を純水と飽和塩化ナトリウム水溶液で洗浄した。有機層を無水硫酸マグネシウムで乾燥後、減圧下に溶媒留去した。残渣をシリカゲルカラムクロマトグラフィー(トルエンとヘキサンの混合溶媒(体積比=1:2))で精製し、化合物(A5)の白色ガラス状固体を3.4g(6.0mmol)単離した(収率60%)。
FDMS:562
1H-NMR(CDCl3);7.89(d,1H),7.80(d,2H),7.61-7.70(m,3H),7.21-7.55(m,22H),6.99-7.10(m,2H)
窒素気流下、100mLの三口フラスコに、合成例3で得られた4-クロロ-9-(4-ビフェニリル)カルバゾール 3.5g(9.9mmol)、N,N-ビス(4-ビフェニリル)アミン 3.1g(9.9mmol)、ナトリウム-tert-ブトキシド 1.3g(13.8mmol)、o-キシレン 35mL、酢酸パラジウム 22mg(0.09mmol)、トリ(tert-ブチル)ホスフィン 69mg(0.34mmol)を添加して140℃で12時間攪拌した。室温まで冷却後、純水を20mL添加し攪拌した。水層と有機層を分液し、さらに有機層を純水と飽和塩化ナトリウム水溶液で洗浄した。有機層を無水硫酸マグネシウムで乾燥後、減圧下に溶媒留去した。残渣をシリカゲルカラムクロマトグラフィー(トルエンとヘキサンの混合溶媒(体積比=1:2))で精製し、化合物(A8)の薄黄色ガラス状固体を3.4g(5.3mmol)単離した(収率53%)。
FDMS:638
1H-NMR(CDCl3);7.88(d,1H),7.81(d,2H),7.66(t,4H),7.20-7.56(m,25H),6.99-7.10(m,2H)
窒素気流下、50mLの三口フラスコに、合成例3で得られた4-クロロ-9-(4-ビフェニリル)カルバゾール 4.6g(13.0mmol)、N-(p-トリル)-N-(9,9’-ジメチルフルオレン-2-イル)アミン 4.2g(14.3mmol)、ナトリウム-tert-ブトキシド 1.7g(18.2mmol)、o-キシレン 25mL、酢酸パラジウム 58mg(0.26mmol)、トリ(tert-ブチル)ホスフィン 184mg(0.91mmol)を添加して140℃で10時間攪拌した。室温まで冷却後、純水を20mL添加し攪拌した。水層と有機層を分液し、さらに有機層を純水と飽和塩化ナトリウム水溶液で洗浄した。有機層を無水硫酸マグネシウムで乾燥後、減圧下に溶媒留去した。残渣をシリカゲルカラムクロマトグラフィー(トルエンとヘキサンの混合溶媒(体積比=1:2))で精製し、化合物(A15)の薄黄色ガラス状固体を6.0g(9.9mmol)単離した(収率75%)。
8 FDMS:616
1H-NMR(CDCl3);7.84(d,1H),6.99-7.68(m,26H),2.26(s,3H),1.39(s,6H)
窒素気流下、50mLの三口フラスコに、合成例3で得られた4-クロロ-9-(4-ビフェニリル)カルバゾール 4.0g(11.3mmol)、N-(2-ジベンゾフラニル)-N-フェニルアミン 3.2g(12.4mmol)、ナトリウム-tert-ブトキシド 1.5g(15.8mmol)、o-キシレン 20mL、酢酸パラジウム 50mg(0.22mmol)、トリ(tert-ブチル)ホスフィン 155mg(0.77mmol)を添加して140℃で12時間攪拌した。室温まで冷却後、純水を15mL添加し攪拌した。水層と有機層を分液し、さらに有機層を純水と飽和塩化ナトリウム水溶液で洗浄した。有機層を無水硫酸マグネシウムで乾燥後、減圧下に溶媒留去した。残渣をシリカゲルカラムクロマトグラフィー(トルエンとヘキサンの混合溶媒(体積比=1:2))で精製し、化合物(A278)の白色ガラス状固体を4.6g(8.0mmol)単離した(収率71%)。
FDMS:576
窒素気流下、50mLの三口フラスコに、合成例8で得られた4-クロロ-9-フェニルカルバゾール 0.48g(1.7mmol)、合成例12で得られたN-ビフェニリル-N-(m-ターフェニル)アミン 0.70g(1.7mmol)、ナトリウム-tert-ブトキシド 0.23g(2.4mmol)、o-キシレン 10mL、酢酸パラジウム 8mg(0.03mmol)、トリ(tert-ブチル)ホスフィン 24mg(0.12mmol)を添加して140℃で14時間攪拌した。室温まで冷却後、純水を10mL添加し攪拌した。水層と有機層を分液し、さらに有機層を純水と飽和塩化ナトリウム水溶液で洗浄した。有機層を無水硫酸マグネシウムで乾燥後、減圧下に溶媒留去した。残渣をシリカゲルカラムクロマトグラフィー(トルエンとヘキサンの混合溶媒(体積比=1:2))で精製し、化合物(A286)の薄黄色ガラス状固体を0.77g(1.2mmol)単離した(収率71%)。
FDMS:638
窒素気流下、100mLの三口フラスコに、合成例8で得られた4-クロロ-9-フェニルカルバゾール 4.0g(14.4mmol)、N-フェニル-N-(11,11’-ジメチルベンゾ[a]フルオレン-9-イル)アミン 4.8g(14.4mmol)、ナトリウム-tert-ブトキシド 1.9g(20.1mmol)、o-キシレン 30mL、酢酸パラジウム 64mg(0.28mmol)、トリ(tert-ブチル)ホスフィン 197mg(0.98mmol)を添加して140℃で12時間攪拌した。室温まで冷却後、純水を10mL添加し攪拌した。水層と有機層を分液し、さらに有機層を純水と飽和塩化ナトリウム水溶液で洗浄した。有機層を無水硫酸マグネシウムで乾燥後、減圧下に溶媒留去した。残渣をシリカゲルカラムクロマトグラフィー(トルエンとヘキサンの混合溶媒(体積比=1:2))で精製し、化合物(A289)の薄黄色ガラス状固体を5.4g(9.5mmol)単離した(収率66%)。
FDMS:576
1H-NMR(CDCl3);8.15(d,1H),7.89(d,1H),7.78-7.83(m,3H),7.20-7.60(m,17H),7.06(d,2H),6.91-7.99(m,2H)1.65(s,6H)
窒素気流下、50mLの三口フラスコに、合成例8で得られた4-クロロ-9-フェニルカルバゾール 0.72g(2.6mmol)、合成例13で得られたN-ビフェニリル-N-(4-(4-ジベンゾチエニル)フェニル)アミン 1.2g(2.8mmol)、ナトリウム-tert-ブトキシド 0.35g(3.6mmol)、o-キシレン 10mL、酢酸パラジウム 17mg(0.07mmol)、トリ(tert-ブチル)ホスフィン 55mg(0.27mmol)を添加して140℃で14時間攪拌した。室温まで冷却後、純水を10mL添加し攪拌した。水層と有機層を分液し、さらに有機層を純水と飽和塩化ナトリウム水溶液で洗浄した。有機層を無水硫酸マグネシウムで乾燥後、減圧下に溶媒留去した。残渣をシリカゲルカラムクロマトグラフィー(トルエンとヘキサンの混合溶媒(体積比=1:2))で精製し、化合物(A292)の薄黄色ガラス状固体を1.2g(1.9mmol)単離した(収率74%)。
FDMS:668
窒素気流下、50mLの三口フラスコに、合成例9で得られた4-クロロ-9-(4,6-ジフェニル-1,3,5-トリアジン-2-イル)カルバゾール 3.0g(6.9mmol)、N,N-ビス(4-ビフェニリル)アミン 2.2g(6.9mmol)、ナトリウム-tert-ブトキシド 0.93g(9.7mmol)、o-キシレン 20mL、酢酸パラジウム 31mg(0.13mmol)、トリ(tert-ブチル)ホスフィン 97mg(0.48mmol)を添加して140℃で8時間攪拌した。室温まで冷却後、純水を10mL添加し攪拌した。析出した茶色粉末をろ取し、純水とエタノールで洗浄した。茶色粉末を減圧下で乾燥後、o-キシレンで再結晶し、化合物(A124)の灰色粉末を2.9g(4.0mmol)単離した(収率59%)。
FDMS:717
窒素気流下、50mLの三口フラスコに、合成例5で得られた4-クロロ-9-(2-ジベンゾチエニル)カルバゾール 4.0g(10.4mmol)、N,N-ビス(4-ビフェニリル)アミン 3.3g(10.4mmol)、ナトリウム-tert-ブトキシド 1.4g(14.6mmol)、o-キシレン 20mL、酢酸パラジウム 70mg(0.31mmol)、トリ(tert-ブチル)ホスフィン 221mg(1.0mmol)を添加して140℃で6時間攪拌した。水層と有機層を分液し、さらに有機層を純水と飽和塩化ナトリウム水溶液で洗浄した。有機層を無水硫酸マグネシウムで乾燥後、減圧下に溶媒留去した。残渣をシリカゲルカラムクロマトグラフィー(トルエンとヘキサンの混合溶媒(体積比=1:2))で精製し、化合物(A139)の薄黄色ガラス状固体を4.2g(6.3mmol)単離した(収率60%)。
FDMS:668
1H-NMR(CDCl3);8.34(s,1H),8.07(t,2H),7.90(d,2H),7.64(d,1H),7.24-7.56(m,24H),7.00-7.12(m,2H)
窒素気流下、50mLの三口フラスコに、合成例5で得られた4-クロロ-9-(2-ジベンゾチエニル)カルバゾール 4.0g(10.4mmol)、N-フェニル-N-(2-ジベンゾチエニル)アミン 3.1g(11.4mmol)、ナトリウム-tert-ブトキシド 1.4g(14.6mmol)、o-キシレン 20mL、酢酸パラジウム 70mg(0.31mmol)、トリ(tert-ブチル)ホスフィン 221mg(1.0mmol)を添加して140℃で10時間攪拌した。水層と有機層を分液し、さらに有機層を純水と飽和塩化ナトリウム水溶液で洗浄した。有機層を無水硫酸マグネシウムで乾燥後、減圧下に溶媒留去した。残渣をシリカゲルカラムクロマトグラフィー(トルエンとヘキサンの混合溶媒(体積比=1:2))で精製し、化合物(A148)の白色ガラス状固体を4.4g(7.2mmol)単離した(収率70%)。
FDMS:622
1H-NMR(CDCl3);8.34(s,1H),8.07(t,2H),7.98(s,1H),7.86-7.92(m,3H),7.78(d,1H),7.63-7.69(m,2H),6.91-7.53(m,16H)
窒素気流下、50mLの三口フラスコに、合成例5で得られた4-クロロ-9-(2-ジベンゾチエニル)カルバゾール 4.0g(10.4mmol)、N-フェニル-N-(4-(9-カルバゾリル)フェニル)アミン 3.8g(11.4mmol)、ナトリウム-tert-ブトキシド 1.4g(14.6mmol)、o-キシレン 20mL、酢酸パラジウム 70mg(0.31mmol)、トリ(tert-ブチル)ホスフィン 221mg(1.0mmol)を添加して140℃で12時間攪拌した。水層と有機層を分液し、さらに有機層を純水と飽和塩化ナトリウム水溶液で洗浄した。有機層を無水硫酸マグネシウムで乾燥後、減圧下に溶媒留去した。残渣をシリカゲルカラムクロマトグラフィー(トルエンとヘキサンの混合溶媒(体積比=1:2))で精製し、化合物(A153)の白色ガラス状固体を5.2g(7.6mmol)単離した(収率74%)。
FDMS:681
1H-NMR(CDCl3);8.34(d,1H),8.03-8.12(m,4H),7.90(d,2H),7.65(d,1H),6.99-7.50(m,23H)
窒素気流下、50mLの三口フラスコに、合成例10で得られた4-クロロ-6-フェニル-9-ビフェニリルカルバゾール 500mg(1.1mmol)、N-フェニル-N-(2-ジベンゾチエニル)アミン 302mg(1.1mmol)、ナトリウム-tert-ブトキシド 147mg(1.5mmol)、o-キシレン 10mL、酢酸パラジウム 7mg(0.03mmol)、トリ(tert-ブチル)ホスフィン 21mg(0.10mmol)を添加して140℃で10時間攪拌した。水層と有機層を分液し、さらに有機層を純水と飽和塩化ナトリウム水溶液で洗浄した。有機層を無水硫酸マグネシウムで乾燥後、減圧下に溶媒留去した。残渣をシリカゲルカラムクロマトグラフィー(トルエンとヘキサンの混合溶媒(体積比=1:2))で精製し、化合物(A318)の白色ガラス状固体を411mg(0.61mmol)単離した(収率56%)。
FDMS:668
窒素気流下、200mLの三口フラスコに、合成例3で得られた4-クロロ-9-(4-ビフェニリル)カルバゾール 7.0g(19.8mmol)、アニリン 0.87g(9.4mmol)、ナトリウム-tert-ブトキシド 5.3g(55.4mmol)、o-キシレン 70mL、酢酸パラジウム 44mg(0.19mmol)、トリ(tert-ブチル)ホスフィン 139mg(0.69mmol)を添加して140℃で12時間攪拌した。室温まで冷却後、純水を40mL添加し攪拌した。水層と有機層を分液し、さらに有機層を純水と飽和塩化ナトリウム水溶液で洗浄した。有機層を無水硫酸マグネシウムで乾燥後、減圧下に溶媒留去した。残渣をシリカゲルカラムクロマトグラフィー(トルエンとヘキサンの混合溶媒(体積比=1:2))で精製し、化合物(B1)の白色ガラス状固体を5.0g(6.8mmol)単離した(収率72%)。
FDMS:727
1H-NMR(CDCl3);7.78-7.83(m,6H),7.62-7.69(m,8H),7.08-7.51(m,18H),6.77-6.98(m,5H)
窒素気流下、200mLの三口フラスコに、合成例3で得られた4-クロロ-9-(4-ビフェニリル)カルバゾール 7.0g(19.8mmol)、4-メチルアニリン 1.0g(9.4mmol)、ナトリウム-tert-ブトキシド 5.3g(55.4mmol)、o-キシレン 70mL、酢酸パラジウム 88mg(0.39mmol)、トリ(tert-ブチル)ホスフィン 279mg(1.38mmol)を添加して140℃で14時間攪拌した。室温まで冷却後、純水を40mL添加し攪拌した。水層と有機層を分液し、さらに有機層を純水と飽和塩化ナトリウム水溶液で洗浄した。有機層を無水硫酸マグネシウムで乾燥後、減圧下に溶媒留去した。残渣をシリカゲルカラムクロマトグラフィー(トルエンとヘキサンの混合溶媒)で精製し、化合物(B2)の薄黄色ガラス状固体を2.9g(3.9mmol)単離した(収率42%)。
FDMS:741
1H-NMR(CDCl3);7.77-7.85(m,6H),7.61-7.69(m,8H),7.24-7.51(m,14H),7.05(t,2H),6.81-6.95(m,6H),2.20(s,3H)
窒素気流下、50mLの三口フラスコに、合成例4で得られた4-クロロ-9-(3-キノリル)カルバゾール 4.0g(12.1mmol)、4-メチルアニリン 652mg(6.0mmol)、ナトリウム-tert-ブトキシド 1.6g(17.0mmol)、o-キシレン 20mL、酢酸パラジウム 27mg(0.12mmol)、トリ(tert-ブチル)ホスフィン 85mg(0.42mmol)を添加して140℃で17時間攪拌した。室温まで冷却後、純水を15mL添加し攪拌した。水層と有機層を分液し、さらに有機層を純水と飽和塩化ナトリウム水溶液で洗浄した。有機層を無水硫酸マグネシウムで乾燥後、減圧下に溶媒留去した。残渣をシリカゲルカラムクロマトグラフィー(トルエンと酢酸エチルの混合溶媒)で精製し、化合物(B27)の茶色ガラス状固体を2.6g(3.7mmol)単離した(収率61%)。
FDMS:691
1H-NMR(CDCl3);9.18(s,2H),8.35(s,2H),8.25(d,2H),7.86(d,4H),7.78(d,2H),7.61(t,2H),7.18-7.36(m,8H),7.06(d,2H),6.85-6.98(m,6H),2.22(s,3H)
窒素気流下、50mLの三口フラスコに、合成例5で得られた4-クロロ-9-(2-ジベンゾチエニル)カルバゾール 2.7g(7.0mmol)、アニリン 297mg(3.2mmol)、ナトリウム-tert-ブトキシド 947mg(9.8mmol)、o-キシレン 13mL、酢酸パラジウム 15mg(0.07mmol)、トリ(tert-ブチル)ホスフィン 49mg(0.24mmol)を添加して140℃で20時間攪拌した。室温まで冷却後、純水を10mL添加し攪拌した。水層と有機層を分液し、さらに有機層を純水と飽和塩化ナトリウム水溶液で洗浄した。有機層を無水硫酸マグネシウムで乾燥後、減圧下に溶媒留去した。残渣をシリカゲルカラムクロマトグラフィー(トルエンとヘキサンの混合溶媒)で精製し、化合物(B30)の白色粉末を0.9g(1.1mmol)単離した(収率35%)。
FDMS:787
1H-NMR(CDCl3);8.33(s,2H),7.99-8.08(m,4H),7.84-7.88(m,4H),7.64(d,2H),7.10-7.50(m,16H),6.79-6.99(m,5H)
窒素気流下、50mLの三口フラスコに、合成例6で得られた4-クロロ-9-[4-(2-ピリジル)フェニル]カルバゾール 4.0g(11.2mmol)、アニリン 477mg(5.1mmol)、ナトリウム-tert-ブトキシド 1.5g(15.8mmol)、o-キシレン 25mL、酢酸パラジウム 25mg(0.11mmol)、トリ(tert-ブチル)ホスフィン 79mg(0.39mmol)を添加して140℃で10時間攪拌した。室温まで冷却後、純水を15mL添加し攪拌した。水層と有機層を分液し、さらに有機層を純水と飽和塩化ナトリウム水溶液で洗浄した。有機層を無水硫酸マグネシウムで乾燥後、減圧下に溶媒留去した。残渣をシリカゲルカラムクロマトグラフィー(トルエンと酢酸エチルの混合溶媒)で精製し、化合物(B36)の茶色ガラス状固体を2.5g(3.4mmol)単離した(収率66%)。
FDMS:729
1H-NMR(CDCl3);8.71(d,2H),8.20(d,4H),7.83(d,2H),7.66-7.75(m,8H),7.40(d,2H),7.07-7.32(m,12H),6.77-6.98(m,5H)
窒素気流下、100mLの三口フラスコに、合成例7で得られた4-クロロ-9-(4-クロロフェニル)カルバゾール 3.0g(9.6mmol)、N-(4-メチルフェニル)-N-ビフェニリルアミン 5.2g(20.2mmol)、ナトリウム-tert-ブトキシド 2.5g(26.9mmol)、o-キシレン 50mL、酢酸パラジウム 43mg(0.19mmol)、トリ(tert-ブチル)ホスフィン 135mg(0.67mmol)を添加して140℃で12時間攪拌した。室温まで冷却後、純水を30mL添加し攪拌した。水層と有機層を分液し、さらに有機層を純水と飽和塩化ナトリウム水溶液で洗浄した。有機層を無水硫酸マグネシウムで乾燥後、減圧下に溶媒留去した。残渣をシリカゲルカラムクロマトグラフィー(トルエンとヘキサンの混合溶媒)で精製し、化合物(C5)の無色ガラス状固体を4.7g(6.2mmol)単離した(収率64%)。
FDMS:757
1H-NMR(CDCl3);7.84(d,1H),7.48-7.58(m,6H),7.20-7.37(m,18H),6.96-7.15(m,12H),2.34(s,3H),2.26(s,3H)
窒素気流下、200mLの三口フラスコに、合成例7で得られた4-クロロ-9-(4-クロロフェニル)カルバゾール 6.0g(19.2mmol)、N,N-ビス(4-ビフェニリル)アミン 13.0g(40.5mmol)、ナトリウム-tert-ブトキシド 5.1g(54.0mmol)、o-キシレン 60mL、酢酸パラジウム 86mg(0.38mmol)、トリ(tert-ブチル)ホスフィン 272mg(1.3mmol)を添加して140℃で14時間攪拌した。室温まで冷却後、純水を40mL添加し攪拌した。析出した茶色粉末をろ取し、純水とエタノールで洗浄した。茶色粉末を減圧下で乾燥後、o-キシレンで再結晶し、化合物(C11)の薄黄色粉末を10.5g(11.9mmol)単離した(収率62%)。
FDMS:882
化合物(A8)を2-メチルテトラヒドロフランに0.0001mol/Lの濃度で溶解させた溶液を調整し、液体窒素冷却下にて燐光スペクトルを測定した。燐光スペクトルの極大波長は480nmであった。燐光スペクトルの極大波長から見積もった三重項準位を表1に示す。
化合物(A15)について、実施例20と同様の方法で燐光スペクトルを測定した。燐光スペクトルの極大波長は482nmであった。燐光スペクトルの極大波長から見積もった三重項準位を表1に示す。
化合物(A278)について、実施例20と同様の方法で燐光スペクトルを測定した。燐光スペクトルの極大波長は448nmであった。燐光スペクトルの極大波長から見積もった三重項準位を表1に示す。
化合物(A286)について、実施例20と同様の方法で燐光スペクトルを測定した。燐光スペクトルの極大波長は486nmであった。燐光スペクトルの極大波長から見積もった三重項準位を表1に示す。
化合物(A292)について、実施例20と同様の方法で燐光スペクトルを測定した。燐光スペクトルの極大波長は483nmであった。燐光スペクトルの極大波長から見積もった三重項準位を表1に示す。
化合物(A124)について、実施例20と同様の方法で燐光スペクトルを測定した。燐光スペクトルの極大波長は479nmであった。燐光スペクトルの極大波長から見積もった三重項準位を表1に示す。
化合物(A139)について、実施例20と同様の方法で燐光スペクトルを測定した。燐光スペクトルの極大波長は480nmであった。燐光スペクトルの極大波長から見積もった三重項準位を表1に示す。
化合物(A148)について、実施例20と同様の方法で燐光スペクトルを測定した。燐光スペクトルの極大波長は449nmであった。燐光スペクトルの極大波長から見積もった三重項準位を表1に示す。
化合物(A153)について、実施例20と同様の方法で燐光スペクトルを測定した。燐光スペクトルの極大波長は445nmであった。燐光スペクトルの極大波長から見積もった三重項準位を表1に示す。
化合物(A318)について、実施例20と同様の方法で燐光スペクトルを測定した。燐光スペクトルの極大波長は457nmであった。燐光スペクトルの極大波長から見積もった三重項準位を表1に示す。
化合物(B1)について、実施例20と同様の方法で燐光スペクトルを測定した。燐光スペクトルの極大波長は450nmであった。燐光スペクトルの極大波長から見積もった三重項準位を表1に示す。
化合物(B2)について、実施例20と同様の方法で燐光スペクトルを測定した。燐光スペクトルの極大波長は450nmであった。燐光スペクトルの極大波長から見積もった三重項準位を表1に示す。
化合物(B30)について、実施例20と同様の方法で燐光スペクトルを測定した。燐光スペクトルの極大波長は442nmであった。燐光スペクトルの極大波長から見積もった三重項準位を表1に示す。
化合物(B36)について、実施例20と同様の方法で燐光スペクトルを測定した。燐光スペクトルの極大波長は452nmであった。燐光スペクトルの極大波長から見積もった三重項準位を表1に示す。
NPDについて、実施例20と同様の方法で燐光スペクトルを測定した。燐光スペクトルの極大波長は525nmであった。燐光スペクトルの極大波長から見積もった三重項準位を表1に示す。
化合物(c)について、実施例20と同様の方法で燐光スペクトルを測定した。燐光スペクトルの極大波長は490nmであった。燐光スペクトルの極大波長から見積もった三重項準位を表1に示す。
過塩素酸テトラブチルアンモニウムの濃度が0.1mol/Lである無水ジクロロメタン溶液に化合物(A5)を0.001mol/Lの濃度で溶解させ、サイクリックボルタンメトリーでイオン化ポテンシャルを測定した。作用電極にはグラッシーカーボン、対極に白金線、参照電極にAgNO3のアセトニトリル溶液に浸した銀線を用いた。標準物質としてフェロセンを用い、フェロセンの酸化還元電位を基準とした際の化合物(A5)のイオン化ポテンシャルは0.43V vs.Fc/Fc+であった。この値は、従来から正孔輸送材料として知られているNPDのイオン化ポテンシャル(0.31V vs.Fc/Fc+)と比較して若干高く、正孔輸送材料として好ましいイオン化ポテンシャルであった。
実施例34と同様の方法で化合物(A8)のイオン化ポテンシャルを評価した。フェロセンの酸化還元電位を基準とした際の化合物(A8)のイオン化ポテンシャルは0.44V vs.Fc/Fc+であり、従来から正孔輸送材料として知られているNPDのイオン化ポテンシャル(0.31V vs.Fc/Fc+)と比較して若干高く、正孔輸送材料として好ましいイオン化ポテンシャルであった。
実施例34と同様の方法で化合物(A15)のイオン化ポテンシャルを評価した。フェロセンの酸化還元電位を基準とした際の化合物(A15)のイオン化ポテンシャルは0.40V vs.Fc/Fc+であり、従来から正孔輸送材料として知られているNPDのイオン化ポテンシャル(0.31V vs.Fc/Fc+)と比較して若干高く、正孔輸送材料として好ましいイオン化ポテンシャルであった。
実施例34と同様の方法で化合物(A278)のイオン化ポテンシャルを評価した。フェロセンの酸化還元電位を基準とした際の化合物(A278)のイオン化ポテンシャルは0.45V vs.Fc/Fc+であり、従来から正孔輸送材料として知られているNPDのイオン化ポテンシャル(0.31V vs.Fc/Fc+)と比較して若干高く、正孔輸送材料として好ましいイオン化ポテンシャルであった。
実施例34と同様の方法で化合物(A286)のイオン化ポテンシャルを評価した。フェロセンの酸化還元電位を基準とした際の化合物(A286)のイオン化ポテンシャルは0.44V vs.Fc/Fc+であり、従来から正孔輸送材料として知られているNPDのイオン化ポテンシャル(0.31V vs.Fc/Fc+)と比較して若干高く、正孔輸送材料として好ましいイオン化ポテンシャルであった。
実施例34と同様の方法で化合物(A289)のイオン化ポテンシャルを評価した。フェロセンの酸化還元電位を基準とした際の化合物(A289)のイオン化ポテンシャルは0.39V vs.Fc/Fc+であり、従来から正孔輸送材料として知られているNPDのイオン化ポテンシャル(0.31V vs.Fc/Fc+)と比較して若干高く、正孔輸送材料として好ましいイオン化ポテンシャルであった。
実施例34と同様の方法で化合物(A292)のイオン化ポテンシャルを評価した。フェロセンの酸化還元電位を基準とした際の化合物(A292)のイオン化ポテンシャルは0.43V vs.Fc/Fc+であり、従来から正孔輸送材料として知られているNPDのイオン化ポテンシャル(0.31V vs.Fc/Fc+)と比較して若干高く、正孔輸送材料として好ましいイオン化ポテンシャルであった。
実施例34と同様の方法で化合物(A124)のイオン化ポテンシャルを評価した。フェロセンの酸化還元電位を基準とした際の化合物(A124)のイオン化ポテンシャルは0.44V vs.Fc/Fc+であり、従来から正孔輸送材料として知られているNPDのイオン化ポテンシャル(0.31V vs.Fc/Fc+)と比較して若干高く、正孔輸送材料として好ましいイオン化ポテンシャルであった。
実施例34と同様の方法で化合物(A139)のイオン化ポテンシャルを評価した。フェロセンの酸化還元電位を基準とした際の化合物(A139)のイオン化ポテンシャルは0.45V vs.Fc/Fc+であり、従来から正孔輸送材料として知られているNPDのイオン化ポテンシャル(0.31V vs.Fc/Fc+)と比較して若干高く、正孔輸送材料として好ましいイオン化ポテンシャルであった。
実施例34と同様の方法で化合物(A148)のイオン化ポテンシャルを評価した。フェロセンの酸化還元電位を基準とした際の化合物(A148)のイオン化ポテンシャルは0.45V vs.Fc/Fc+であり、従来から正孔輸送材料として知られているNPDのイオン化ポテンシャル(0.31V vs.Fc/Fc+)と比較して若干高く、正孔輸送材料として好ましいイオン化ポテンシャルであった。
実施例34と同様の方法で化合物(A153)のイオン化ポテンシャルを評価した。フェロセンの酸化還元電位を基準とした際の化合物(A153)のイオン化ポテンシャルは0.47V vs.Fc/Fc+であり、従来から正孔輸送材料として知られているNPDのイオン化ポテンシャル(0.31V vs.Fc/Fc+)と比較して若干高く、正孔輸送材料として好ましいイオン化ポテンシャルであった。
実施例34と同様の方法で化合物(A318)のイオン化ポテンシャルを評価した。フェロセンの酸化還元電位を基準とした際の化合物(A318)のイオン化ポテンシャルは0.44V vs.Fc/Fc+であり、従来から正孔輸送材料として知られているNPDのイオン化ポテンシャル(0.31V vs.Fc/Fc+)と比較して若干高く、正孔輸送材料として好ましいイオン化ポテンシャルであった。
実施例34と同様の方法で化合物(B1)のイオン化ポテンシャルを評価した。フェロセンの酸化還元電位を基準とした際の化合物(B1)のイオン化ポテンシャルは0.48V vs.Fc/Fc+であり、従来から正孔輸送材料として知られているNPDのイオン化ポテンシャル(0.31V vs.Fc/Fc+)と比較して若干高く、正孔輸送材料として好ましいイオン化ポテンシャルであった。
実施例34と同様の方法で化合物(B2)のイオン化ポテンシャルを評価した。フェロセンの酸化還元電位を基準とした際の化合物(B2)のイオン化ポテンシャルは0.46V vs.Fc/Fc+であり、従来から正孔輸送材料として知られているNPDのイオン化ポテンシャル(0.31V vs.Fc/Fc+)と比較して若干高く、正孔輸送材料として好ましいイオン化ポテンシャルであった。
実施例34と同様の方法で化合物(B27)のイオン化ポテンシャルを評価した。フェロセンの酸化還元電位を基準とした際の化合物(B27)のイオン化ポテンシャルは0.48V vs.Fc/Fc+であり、従来から正孔輸送材料として知られているNPDのイオン化ポテンシャル(0.31V vs.Fc/Fc+)と比較して若干高く、正孔輸送材料として好ましいイオン化ポテンシャルであった。
実施例34と同様の方法で化合物(B30)のイオン化ポテンシャルを評価した。フェロセンの酸化還元電位を基準とした際の化合物(B30)のイオン化ポテンシャルは0.48V vs.Fc/Fc+であり、従来から正孔輸送材料として知られているNPDのイオン化ポテンシャル(0.31V vs.Fc/Fc+)と比較して若干高く、正孔輸送材料として好ましいイオン化ポテンシャルであった。
実施例34と同様の方法で化合物(B36)のイオン化ポテンシャルを評価した。フェロセンの酸化還元電位を基準とした際の化合物(B36)のイオン化ポテンシャルは0.48V vs.Fc/Fc+であり、従来から正孔輸送材料として知られているNPDのイオン化ポテンシャル(0.31V vs.Fc/Fc+)と比較して若干高く、正孔輸送材料として好ましいイオン化ポテンシャルであった。
実施例34と同様の方法で化合物(C5)のイオン化ポテンシャルを評価した。フェロセンの酸化還元電位を基準とした際の化合物(C5)のイオン化ポテンシャルは0.40V vs.Fc/Fc+であり、従来から正孔輸送材料として知られているNPDのイオン化ポテンシャル(0.31V vs.Fc/Fc+)と比較して若干高く、正孔輸送材料として好ましいイオン化ポテンシャルであった。
実施例34と同様の方法で化合物(C11)のイオン化ポテンシャルを評価した。フェロセンの酸化還元電位を基準とした際の化合物(C11)のイオン化ポテンシャルは0.45V vs.Fc/Fc+であり、従来から正孔輸送材料として知られているNPDのイオン化ポテンシャル(0.31V vs.Fc/Fc+)と比較して若干高く、正孔輸送材料として好ましいイオン化ポテンシャルであった。
実施例34と同様の方法でカルバゾール環の3位にアミノ基が結合した化合物(a)のイオン化ポテンシャルを評価した。化合物(a)のイオン化ポテンシャルは0.13V vs.Fc/Fc+であり、従来から正孔輸送材料として知られているNPDのイオン化ポテンシャル(0.31V vs.Fc/Fc+)と比較すると低く、正孔輸送材料としては好ましくないイオン化ポテンシャルであった。
化合物(A139)5mgをAlパンに入れ、窒素雰囲気下、10℃/分の昇温条件でガラス転移温度を測定した。標準試料には、Al2O3を使用した。化合物(A139)のガラス転移温度は143℃であり、NPD(96℃)及び化合物(b)(100℃)と比較して薄膜状態の安定性が高いことがわかった。
実施例53と同様の方法で化合物(A148)のガラス転移温度を測定した。化合物(A148)のガラス転移温度は142℃であり、NPD(96℃)及び化合物(b)(100℃)と比較して薄膜状態の安定性が高いことがわかった。
実施例53と同様の方法で化合物(A153)のガラス転移温度を測定した。化合物(A153)のガラス転移温度は150℃であり、NPD(96℃)及び化合物(b)(100℃)と比較して薄膜状態の安定性が高いことがわかった。
実施例53と同様の方法で化合物(B1)のガラス転移温度を測定した。化合物(B1)のガラス転移温度は169℃であり、NPD(96℃)及び化合物(b)(100℃)と比較して薄膜状態の安定性が高いことがわかった。
実施例53と同様の方法で化合物(B30)のガラス転移温度を測定した。化合物(B30)のガラス転移温度は191℃であり、NPD(96℃)及び化合物(b)(100℃)と比較して薄膜状態の安定性が高いことがわかった。
厚さ200nmのITO透明電極(陽極)を積層したガラス基板をアセトンおよび純水による超音波洗浄、イソプロピルアルコールによる沸騰洗浄を行った。さらに紫外線オゾン洗浄を行い、真空蒸着装置へ設置後、5×10-4Pa以下になるまで真空ポンプにて排気した。まず、ITO透明電極上に銅フタロシアニンを蒸着速度0.1nm/秒で蒸着し、10nmの正孔注入層とした。引続き、NPDを蒸着速度0.3nm/秒で25nm蒸着し、その後、化合物(A5)を蒸着速度0.1nm/秒で5nm蒸着し2層の正孔輸送層とした。続いて、燐光ドーパント材料であるトリス(2-フェニルピリジン)イリジウム(Ir(ppy)3)とホスト材料である4,4’-ビス(N-カルバゾリル)ビフェニル(CBP)を重量比が1:11.5になるように蒸着速度0.25nm/秒で共蒸着し、30nmの発光層とした。
化合物(A5)を化合物(A8)に変更した以外は実施例58と同様の操作を行い有機EL素子を作製した。20mA/cm2の電流を印加した際の駆動電圧および電流効率を表2に示す。
化合物(A5)を化合物(A15)に変更した以外は実施例58と同様の操作を行い有機EL素子を作製した。20mA/cm2の電流を印加した際の駆動電圧および電流効率を表2に示す。
化合物(A5)を化合物(A278)に変更した以外は実施例58と同様の操作を行い有機EL素子を作製した。20mA/cm2の電流を印加した際の駆動電圧および電流効率を表2に示す。
化合物(A5)を化合物(A139)に変更した以外は実施例58と同様の操作を行い有機EL素子を作製した。20mA/cm2の電流を印加した際の駆動電圧および電流効率を表2に示す。
化合物(A5)を化合物(A148)に変更した以外は実施例58と同様の操作を行い有機EL素子を作製した。20mA/cm2の電流を印加した際の駆動電圧および電流効率を表2に示す。
化合物(A5)を化合物(A153)に変更した以外は実施例58と同様の操作を行い有機EL素子を作製した。20mA/cm2の電流を印加した際の駆動電圧および電流効率を表2に示す。
化合物(A5)を化合物(B2)に変更した以外は実施例58と同様の操作を行い有機EL素子を作製した。20mA/cm2の電流を印加した際の駆動電圧および電流効率を表2に示す。
化合物(A5)を化合物(B27)に変更した以外は実施例58と同様の操作を行い有機EL素子を作製した。20mA/cm2の電流を印加した際の駆動電圧および電流効率を表2に示す。
化合物(A5)を化合物(B30)に変更した以外は実施例58と同様の操作を行い有機EL素子を作製した。20mA/cm2の電流を印加した際の駆動電圧および電流効率を表2に示す。
化合物(A5)を化合物(B36)に変更した以外は実施例58と同様の操作を行い有機EL素子を作製した。20mA/cm2の電流を印加した際の駆動電圧および電流効率を表2に示す。
化合物(A5)を化合物(C5)に変更した以外は実施例58と同様の操作を行い有機EL素子を作製した。20mA/cm2の電流を印加した際の駆動電圧および電流効率を表2に示す。
化合物(A5)をNPDに変更した以外は実施例58と同様の操作を行い有機EL素子を作製した。結果を20mA/cm2の電流を印加した際の駆動電圧および電流効率を表2に示す。
化合物(A5)を化合物(a)に変更した以外は実施例58と同様の操作を行い有機EL素子を作製した。20mA/cm2の電流を印加した際の駆動電圧および電流効率を表2に示す。
化合物(A5)を化合物(b)に変更した以外は実施例58と同様の操作を行い有機EL素子を作製した。20mA/cm2の電流を印加した際の駆動電圧および電流効率を表2に示す。
したがって、本発明の4-アミノカルバゾール化合物は、輝度が高く、消費電力の少ない燐光発光性または蛍光発光性の有機EL素子を提供できる。
Claims (15)
- 一般式(1)
で表される4-アミノカルバゾール化合物。
一般式(1)中、Ar1~Ar4は、各々独立して、炭素数6~30のアリール基、チエニル基、ピリジル基、ベンゾチエニル基、ジベンゾチエニル基、ジベンゾフラニル基、4-カルバゾリル基、ジベンゾチエニルフェニル基、ジベンゾフラニルフェニル基、又は9-カルバゾリルフェニル基(これらの基は、各々独立して、メチル基、エチル基、炭素数3~18の直鎖、分岐、若しくは環状のアルキル基、メトキシ基、エトキシ基、炭素数3~18の直鎖、分岐、若しくは環状のアルコキシ基、炭素数1~3のハロゲン化アルキル基、炭素数1~3のハロゲン化アルコキシ基、炭素数6~30のアリール基、炭素数6~18のアリールオキシ基、炭素数3~11のヘテロアリール基、炭素数3~18のトリアルキルシリル基、炭素数18~40のトリアリールシリル基、シアノ基、及びハロゲン原子からなる群より選ばれる少なくとも一つの置換基を有していてもよい)を表す。
R1~R7は、各々独立して、炭素数6~30のアリール基、炭素数3~20のヘテロアリール基、又は炭素数9~26のヘテロアリールフェニル基(これらの基は、各々独立して、メチル基、エチル基、炭素数3~18の直鎖、分岐、若しくは環状のアルキル基、メトキシ基、エトキシ基、炭素数3~18の直鎖、分岐、若しくは環状のアルコキシ基、炭素数1~3のハロゲン化アルキル基、炭素数1~3のハロゲン化アルコキシ基、炭素数6~30のアリール基、炭素数6~18のアリールオキシ基、炭素数3~20のヘテロアリール基、炭素数3~18のトリアルキルシリル基、炭素数18~40のトリアリールシリル基、シアノ基、及びハロゲン原子からなる群より選ばれる少なくとも一つの置換基を有していてもよい)、又は、メチル基、エチル基、炭素数3~18の直鎖、分岐、若しくは環状のアルキル基、メトキシ基、エトキシ基、炭素数3~18の直鎖、分岐、若しくは環状のアルコキシ基、シアノ基、水素原子、又はハロゲン原子を表す。
nは0~2の整数を表す。
Xは炭素数6~17の(n+1)価の芳香族炭化水素基、炭素数3~20の(n+1)価のヘテロ芳香族基、又は炭素数9~26の(n+1)価のヘテロアリールフェニル基(これらの基は、各々独立して、メチル基、エチル基、炭素数3~18の直鎖、分岐、若しくは環状のアルキル基、メトキシ基、エトキシ基、炭素数3~18の直鎖、分岐、若しくは環状のアルコキシ基、炭素数1~3のハロゲン化アルキル基、炭素数1~3のハロゲン化アルコキシ基、炭素数6~12のアリール基、炭素数6~18のアリールオキシ基、炭素数3~20のヘテロアリール基、炭素数3~18のトリアルキルシリル基、炭素数18~40のトリアリールシリル基、シアノ基、及びハロゲン原子からなる群より選ばれる少なくとも一つの置換基を有していてもよい)を表す。 - R1~R7が、各々独立して、炭素数6~30のアリール基、炭素数3~20のヘテロアリール基、メチル基、エチル基、炭素数3~18の直鎖、分岐、若しくは環状のアルキル基、メトキシ基、エトキシ基、炭素数3~18の直鎖、分岐、若しくは環状のアルコキシ基、シアノ基、水素原子、又はハロゲン原子である請求項1に記載の4-アミノカルバゾール化合物。
- R1~R7が、各々独立して、フェニル基、メチルフェニル基、メトキシフェニル基、ビフェニリル基、ジベンゾチエニル基、ジベンゾフラニル基、メチル基、メトキシ基、又は水素原子である請求項1または請求項2に記載の4-アミノカルバゾール化合物。
- R1~R7が、各々独立して、フェニル基、メチルフェニル基、メトキシフェニル基、又は水素原子である請求項1乃至請求項3のいずれか一項に記載の4-アミノカルバゾール化合物。
- R4、R5、R6、及びR7が水素原子である請求項1乃至請求項4のいずれか一項に記載の4-アミノカルバゾール化合物。
- R1、R2、R4、R5、R6、及びR7が水素原子である請求項1乃至請求項5のいずれか一項に記載の4-アミノカルバゾール化合物。
- Ar1~Ar4が、各々独立して、炭素数6~30のアリール基、ジベンゾチエニル基、ジベンゾフラニル基、4-カルバゾリル基、ジベンゾフラニルフェニル基、ジベンゾチエニルフェニル基、又は9-カルバゾリルフェニル基(これらの基は、各々独立して、メチル基、エチル基、炭素数3~18の直鎖、分岐、若しくは環状のアルキル基、メトキシ基、エトキシ基、炭素数3~18の直鎖、分岐、若しくは環状のアルコキシ基、炭素数6~30のアリール基、及び炭素数3~11のヘテロアリール基からなる群より選ばれる少なくとも一つの置換基を有していてもよい)である請求項1乃至請求項6のいずれか一項に記載の4-アミノカルバゾール化合物。
- Ar1~Ar4が、各々独立して、フェニル基、ビフェニリル基、ターフェニリル基、フルオレニル基、ベンゾフルオレニル基、ジベンゾチエニル基、ジベンゾフラニル基、ジベンゾフラニルフェニル基、ジベンゾチエニルフェニル基、又は9-カルバゾリルフェニル基(これらの基は、各々独立して、メチル基、エチル基、炭素数3~18の直鎖、分岐、若しくは環状のアルキル基、メトキシ基、エトキシ基、炭素数3~18の直鎖、分岐、若しくは環状のアルコキシ基、からなる群より選ばれる少なくとも一つの置換基を有していてもよい)、又は、4-カルバゾリル基(メチル基、エチル基、炭素数3~18の直鎖、分岐、若しくは環状のアルキル基、メトキシ基、エトキシ基、炭素数3~18の直鎖、分岐、若しくは環状のアルコキシ基、炭素数6~30のアリール基、及び炭素数3~11のヘテロアリール基からなる群より選ばれる少なくとも一つの置換基を有していてもよい)である請求項1乃至請求項7のいずれか一項に記載の4-アミノカルバゾール化合物。
- Ar1~Ar4が、各々独立して、フェニル基、メチルフェニル基、メトキシフェニル基、ビフェニリル基、ターフェニリル基、9,9’-ジメチルフルオレニル基、11,11’-ジメチルベンゾ[a]フルオレニル基、ジベンゾチエニル基、ジベンゾフラニル基、ジベンゾチエニルフェニル基、4-(9-カルバゾリル)フェニル基、9-フェニルカルバゾール-4-イル基、9-ビフェニリルカルバゾール-4-イル基、9-キノリルカルバゾール-4-イル基、または9-ジベンゾチエニルカルバゾール-4-イル基である請求項1乃至請求項8のいずれか一項に記載の4-アミノカルバゾール化合物。
- Xが、(n+1)価のベンゼン、(n+1)価のビフェニル、(n+1)価のナフタレン、(n+1)価のフェナントレン、(n+1)価のフルオレン、(n+1)価のナフチルベンゼン、(n+1)価のピリジン、(n+1)価のピリミジン、(n+1)価の1,3,5-トリアジン、(n+1)価のキノリン、(n+1)価のジベンゾチオフェン、(n+1)価のジベンゾフラン、(n+1)価のピリジルベンゼン、(n+1)価のイミダゾリルベンゼン、(n+1)価のベンゾイミダゾリルベンゼン、及び(n+1)価のベンゾチアゾリルベンゼン(これらの芳香環は、メチル基、エチル基、炭素数3~18の直鎖、分岐、若しくは環状のアルキル基、メトキシ基、エトキシ基、炭素数3~18の直鎖、分岐、若しくは環状のアルコキシ基、炭素数6~12のアリール基、炭素数3~20のヘテロアリール基、シアノ基、及びハロゲン原子からなる群より選ばれる少なくとも一つの置換基を有していてもよい)から選ばれる1種である請求項1乃至請求項9のいずれか一項に記載の4-アミノカルバゾール化合物。
- Xが、(n+1)価のベンゼン、(n+1)価のビフェニル、(n+1)価のキノリン、(n+1)価のジベンゾチオフェン、(n+1)価の1,3,5-トリアジン、及び(n+1)価のピリジルベンゼン(これらの芳香環は、メチル基、エチル基、炭素数3~18の直鎖、分岐、若しくは環状のアルキル基、メトキシ基、エトキシ基、炭素数3~18の直鎖、分岐、若しくは環状のアルコキシ基、炭素数6~12のアリール基、シアノ基、及びハロゲン原子からなる群より選ばれる少なくとも一つの置換基を有していてもよい)から選ばれる1種である請求項1乃至請求項10のいずれか一項に記載の4-アミノカルバゾール化合物。
- Xが、(n+1)価のベンゼン、(n+1)価のビフェニル、(n+1)価のキノリン、(n+1)価のジベンゾチオフェン、(n+1)価の2,4-ジフェニル-1,3,5-トリアジン、又は(n+1)価のピリジルベンゼンである請求項1乃至請求項11のいずれか一項に記載の4-アミノカルバゾール化合物。
- n=0又は1である請求項1乃至請求項12のいずれか一項に記載の4-アミノカルバゾール化合物。
- 一般式(1)
で表される4-アミノカルバゾール化合物を含む、発光層、正孔輸送層および正孔注入層の中から選ばれる少なくとも一つの層を有することを特徴とする有機EL素子。
一般式(1)において、Ar1~Ar4は、各々独立して、炭素数6~30のアリール基、チエニル基、ピリジル基、ベンゾチエニル基、ジベンゾチエニル基、ジベンゾフラニル基、4-カルバゾリル基、ジベンゾチエニルフェニル基、ジベンゾフラニルフェニル基、又は9-カルバゾリルフェニル基(これらの基は、各々独立して、メチル基、エチル基、炭素数3~18の直鎖、分岐、若しくは環状のアルキル基、メトキシ基、エトキシ基、炭素数3~18の直鎖、分岐、若しくは環状のアルコキシ基、炭素数1~3のハロゲン化アルキル基、炭素数1~3のハロゲン化アルコキシ基、炭素数6~30のアリール基、炭素数6~18のアリールオキシ基、炭素数3~11のヘテロアリール基、炭素数3~18のトリアルキルシリル基、炭素数18~40のトリアリールシリル基、シアノ基、及びハロゲン原子からなる群より選ばれる少なくとも一つの置換基を有していてもよい)を表す。
R1~R7は、各々独立して、炭素数6~30のアリール基、炭素数3~20のヘテロアリール基、又は炭素数9~26のヘテロアリールフェニル基(これらの基は、各々独立して、メチル基、エチル基、炭素数3~18の直鎖、分岐、若しくは環状のアルキル基、メトキシ基、エトキシ基、炭素数3~18の直鎖、分岐、若しくは環状のアルコキシ基、炭素数1~3のハロゲン化アルキル基、炭素数1~3のハロゲン化アルコキシ基、炭素数6~30のアリール基、炭素数6~18のアリールオキシ基、炭素数3~20のヘテロアリール基、炭素数3~18のトリアルキルシリル基、炭素数18~40のトリアリールシリル基、シアノ基、及びハロゲン原子からなる群より選ばれる少なくとも一つの置換基を有していてもよい)、又は、メチル基、エチル基、炭素数3~18の直鎖、分岐、若しくは環状のアルキル基、メトキシ基、エトキシ基、炭素数3~18の直鎖、分岐、若しくは環状のアルコキシ基、シアノ基、水素原子、又はハロゲン原子を表す。
nは0~2の整数を表す。
Xは炭素数6~17の(n+1)価の芳香族炭化水素基、炭素数3~20の(n+1)価のヘテロ芳香族基、又は炭素数9~26の(n+1)価のヘテロアリールフェニル基(これらの基は、各々独立して、メチル基、エチル基、炭素数3~18の直鎖、分岐、若しくは環状のアルキル基、メトキシ基、エトキシ基、炭素数3~18の直鎖、分岐、若しくは環状のアルコキシ基、炭素数1~3のハロゲン化アルキル基、炭素数1~3のハロゲン化アルコキシ基、炭素数6~12のアリール基、炭素数6~18のアリールオキシ基、炭素数3~20のヘテロアリール基、炭素数3~18のトリアルキルシリル基、炭素数18~40のトリアリールシリル基、シアノ基、及びハロゲン原子からなる群より選ばれる少なくとも一つの置換基を有していてもよい)を表す。 - 一般式(1)
で表される4-アミノカルバゾール化合物を含む正孔輸送材料、又は正孔注入材料。
一般式(1)中、Ar1~Ar4は、各々独立して、炭素数6~30のアリール基、チエニル基、ピリジル基、ベンゾチエニル基、ジベンゾチエニル基、ジベンゾフラニル基、4-カルバゾリル基、ジベンゾチエニルフェニル基、ジベンゾフラニルフェニル基、又は9-カルバゾリルフェニル基(これらの基は、各々独立して、メチル基、エチル基、炭素数3~18の直鎖、分岐、若しくは環状のアルキル基、メトキシ基、エトキシ基、炭素数3~18の直鎖、分岐、若しくは環状のアルコキシ基、炭素数1~3のハロゲン化アルキル基、炭素数1~3のハロゲン化アルコキシ基、炭素数6~30のアリール基、炭素数6~18のアリールオキシ基、炭素数3~11のヘテロアリール基、炭素数3~18のトリアルキルシリル基、炭素数18~40のトリアリールシリル基、シアノ基、及びハロゲン原子からなる群より選ばれる少なくとも一つの置換基を有していてもよい)を表す。
R1~R7は、各々独立して、炭素数6~30のアリール基、炭素数3~20のヘテロアリール基、又は炭素数9~26のヘテロアリールフェニル基(これらの基は、各々独立して、メチル基、エチル基、炭素数3~18の直鎖、分岐、若しくは環状のアルキル基、メトキシ基、エトキシ基、炭素数3~18の直鎖、分岐、若しくは環状のアルコキシ基、炭素数1~3のハロゲン化アルキル基、炭素数1~3のハロゲン化アルコキシ基、炭素数6~30のアリール基、炭素数6~18のアリールオキシ基、炭素数3~20のヘテロアリール基、炭素数3~18のトリアルキルシリル基、炭素数18~40のトリアリールシリル基、シアノ基、及びハロゲン原子からなる群より選ばれる少なくとも一つの置換基を有していてもよい)、又は、メチル基、エチル基、炭素数3~18の直鎖、分岐、若しくは環状のアルキル基、メトキシ基、エトキシ基、炭素数3~18の直鎖、分岐、若しくは環状のアルコキシ基、シアノ基、水素原子、又はハロゲン原子を表す。
nは0~2の整数を表す。
Xは炭素数6~17の(n+1)価の芳香族炭化水素基、炭素数3~20の(n+1)価のヘテロ芳香族基、又は炭素数9~26の(n+1)価のヘテロアリールフェニル基(これらの基は、各々独立して、メチル基、エチル基、炭素数3~18の直鎖、分岐、若しくは環状のアルキル基、メトキシ基、エトキシ基、炭素数3~18の直鎖、分岐、若しくは環状のアルコキシ基、炭素数1~3のハロゲン化アルキル基、炭素数1~3のハロゲン化アルコキシ基、炭素数6~12のアリール基、炭素数6~18のアリールオキシ基、炭素数3~20のヘテロアリール基、炭素数3~18のトリアルキルシリル基、炭素数18~40のトリアリールシリル基、シアノ基、及びハロゲン原子からなる群より選ばれる少なくとも一つの置換基を有していてもよい)を表す。
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Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH02178670A (ja) * | 1988-12-29 | 1990-07-11 | Canon Inc | 電子写真感光体 |
JP2006028176A (ja) | 2004-07-14 | 2006-02-02 | Samsung Sdi Co Ltd | フェニルカルバゾール化合物,及びそれを利用した有機電界発光素子 |
JP2006298898A (ja) | 2004-12-28 | 2006-11-02 | Semiconductor Energy Lab Co Ltd | カルバゾール誘導体およびカルバゾール誘導体を用いた発光素子、並びに発光装置 |
JP2008019238A (ja) * | 2005-12-20 | 2008-01-31 | Canon Inc | 4−アミノフルオレン化合物及び有機発光素子 |
JP2008195841A (ja) * | 2007-02-14 | 2008-08-28 | Toray Ind Inc | 発光素子材料および発光素子 |
KR20090129799A (ko) | 2008-06-13 | 2009-12-17 | 덕산하이메탈(주) | 신규한 카바졸 유도체 및 이를 포함하는 유기 전계발광소자 |
JP2011001349A (ja) | 2009-05-20 | 2011-01-06 | Tosoh Corp | 2−アミノカルバゾール化合物及びその用途 |
JP2012049518A (ja) * | 2010-07-27 | 2012-03-08 | Konica Minolta Holdings Inc | 有機エレクトロルミネッセンス素子材料、化合物、有機エレクトロルミネッセンス素子、表示装置、並びに照明装置 |
WO2012077520A1 (ja) * | 2010-12-09 | 2012-06-14 | 新日鐵化学株式会社 | 有機電界発光素子 |
Family Cites Families (25)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP3814556B2 (ja) | 2002-04-19 | 2006-08-30 | キヤノン株式会社 | 電子写真感光体、プロセスカートリッジ及び電子写真装置 |
WO2005040117A1 (en) | 2003-10-27 | 2005-05-06 | Semiconductor Energy Laboratory Co., Ltd. | Carbazole derivative, light emitting element, and light emitting device |
JP2005154421A (ja) | 2003-10-27 | 2005-06-16 | Semiconductor Energy Lab Co Ltd | カルバゾール誘導体、発光素子、および発光装置 |
WO2005090512A1 (en) | 2004-03-19 | 2005-09-29 | Lg Chem, Ltd. | New materials for injecting or transporting holes and organic electroluminescence devices using the same |
KR100573137B1 (ko) | 2004-04-02 | 2006-04-24 | 삼성에스디아이 주식회사 | 플루오렌계 화합물 및 이를 이용한 유기 전계 발광 소자 |
KR100787425B1 (ko) | 2004-11-29 | 2007-12-26 | 삼성에스디아이 주식회사 | 페닐카바졸계 화합물 및 이를 이용한 유기 전계 발광 소자 |
US8188315B2 (en) | 2004-04-02 | 2012-05-29 | Samsung Mobile Display Co., Ltd. | Organic light emitting device and flat panel display device comprising the same |
JP5085842B2 (ja) | 2004-08-23 | 2012-11-28 | 三井化学株式会社 | アミン化合物、および該アミン化合物を含有する有機電界発光素子 |
EP1805140B1 (en) | 2004-10-19 | 2016-08-31 | Semiconductor Energy Laboratory Co., Ltd. | Carbazole derivative, and light emitting element and light emitting device using the carbazole derivative |
JP5032016B2 (ja) | 2004-10-19 | 2012-09-26 | 株式会社半導体エネルギー研究所 | カルバゾール誘導体およびカルバゾール誘導体を用いた発光素子、並びに発光装置 |
US8021765B2 (en) | 2004-11-29 | 2011-09-20 | Samsung Mobile Display Co., Ltd. | Phenylcarbazole-based compound and organic electroluminescent device employing the same |
WO2006070912A1 (en) | 2004-12-28 | 2006-07-06 | Semiconductor Energy Laboratory Co., Ltd. | Carbazole derivative, and light-emitting element and light-emitting device using the carbazole derivative |
EP1869141B1 (de) | 2005-04-14 | 2020-03-11 | Merck Patent GmbH | Verbindungen für organische elektronische vorrichtungen |
JP5082356B2 (ja) | 2005-10-07 | 2012-11-28 | 東洋インキScホールディングス株式会社 | カルバゾ−ル含有アミン化合物およびその用途 |
JP4830750B2 (ja) | 2006-09-21 | 2011-12-07 | 東レ株式会社 | 発光素子材料および発光素子 |
KR20100005903A (ko) | 2008-07-08 | 2010-01-18 | 덕산하이메탈(주) | 페닐-나프틸 유도체 및 이를 사용하는 유기전계발광소자 |
KR20100071723A (ko) | 2008-12-19 | 2010-06-29 | 엘지디스플레이 주식회사 | 아민 유도체 및 이를 포함하는 유기전계발광소자 |
KR101075215B1 (ko) | 2008-12-23 | 2011-10-19 | 덕산하이메탈(주) | 퀴놀린 유도체를 함유하는 방향족 아민계 화합물 및 이를 포함하는 유기전계발광소자 |
KR101031597B1 (ko) | 2009-06-30 | 2011-04-27 | 한국 한의학 연구원 | 이중맹검용 침자입장치 |
CN102666487B (zh) * | 2009-10-20 | 2014-11-05 | 东曹株式会社 | 咔唑化合物及其用途 |
KR101181261B1 (ko) | 2010-04-21 | 2012-09-10 | 덕산하이메탈(주) | 다이벤조사이오펜과 아릴아민 유도체를 가지는 화합물 및 이를 이용한 유기전기소자, 그 단말 |
KR20120009761A (ko) | 2010-07-21 | 2012-02-02 | 롬엔드하스전자재료코리아유한회사 | 신규한 유기 발광 화합물 및 이를 포함하는 유기 전계 발광 소자 |
US9450192B2 (en) | 2010-12-06 | 2016-09-20 | E-Ray Optoelectronics Technology | Carbazole derivative and organic electroluminescent devices utilizing the same and fabrication method thereof |
KR101298483B1 (ko) | 2011-04-01 | 2013-08-21 | 덕산하이메탈(주) | 화합물 및 이를 이용한 유기전기소자, 그 전자장치 |
KR101918953B1 (ko) * | 2012-03-06 | 2018-11-16 | 삼성디스플레이 주식회사 | 아민계 화합물, 이를 포함한 유기 발광 소자 및 이를 포함한 유기 발광 장치 |
-
2012
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- 2012-10-25 EP EP12844075.7A patent/EP2772483B1/en active Active
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- 2012-10-25 CN CN201280064781.XA patent/CN104011022B/zh active Active
- 2012-10-26 TW TW101139770A patent/TWI543968B/zh active
Patent Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH02178670A (ja) * | 1988-12-29 | 1990-07-11 | Canon Inc | 電子写真感光体 |
JP2006028176A (ja) | 2004-07-14 | 2006-02-02 | Samsung Sdi Co Ltd | フェニルカルバゾール化合物,及びそれを利用した有機電界発光素子 |
JP2006298898A (ja) | 2004-12-28 | 2006-11-02 | Semiconductor Energy Lab Co Ltd | カルバゾール誘導体およびカルバゾール誘導体を用いた発光素子、並びに発光装置 |
JP2008019238A (ja) * | 2005-12-20 | 2008-01-31 | Canon Inc | 4−アミノフルオレン化合物及び有機発光素子 |
JP2008195841A (ja) * | 2007-02-14 | 2008-08-28 | Toray Ind Inc | 発光素子材料および発光素子 |
KR20090129799A (ko) | 2008-06-13 | 2009-12-17 | 덕산하이메탈(주) | 신규한 카바졸 유도체 및 이를 포함하는 유기 전계발광소자 |
JP2011001349A (ja) | 2009-05-20 | 2011-01-06 | Tosoh Corp | 2−アミノカルバゾール化合物及びその用途 |
JP2012049518A (ja) * | 2010-07-27 | 2012-03-08 | Konica Minolta Holdings Inc | 有機エレクトロルミネッセンス素子材料、化合物、有機エレクトロルミネッセンス素子、表示装置、並びに照明装置 |
WO2012077520A1 (ja) * | 2010-12-09 | 2012-06-14 | 新日鐵化学株式会社 | 有機電界発光素子 |
Non-Patent Citations (5)
Title |
---|
APPLIED PHYSICS LETTERS, vol. 82, 2003, pages 2422 |
JOURNAL OF APPLIED PHYSICS, vol. 95, 2004, pages 7798 |
JOURNAL OF PHYSICAL CHEMISTRY C, vol. 112, 2008, pages 7735 |
See also references of EP2772483A4 |
TETRAHEDRON LETTERS, vol. 39, 1998, pages 2367 |
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US10651389B2 (en) | 2013-07-02 | 2020-05-12 | Merck Patent Gmbh | Materials for electronic devices |
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JP2019011286A (ja) * | 2017-06-30 | 2019-01-24 | 公益財団法人相模中央化学研究所 | ホスフィン化合物及びこれを配位子とするカップリング用触媒 |
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Also Published As
Publication number | Publication date |
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CN104011022B (zh) | 2016-08-24 |
EP2772483B1 (en) | 2017-03-29 |
TW201329046A (zh) | 2013-07-16 |
US9172045B2 (en) | 2015-10-27 |
US20140296519A1 (en) | 2014-10-02 |
EP2772483A4 (en) | 2015-03-11 |
KR102079834B1 (ko) | 2020-02-20 |
KR20140082847A (ko) | 2014-07-02 |
TWI543968B (zh) | 2016-08-01 |
CN104011022A (zh) | 2014-08-27 |
EP2772483A1 (en) | 2014-09-03 |
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