Aromatic amine derivative, and organic electroluminescent element comprising the same

1. An organic electroluminescence device comprising one or more organic thin film layers comprising an emitting layer between an anode and a cathode,

wherein at least one layer of the one or more organic thin film layers comprises:

an aromatic amine derivative represented by the following formula (A1):

wherein

R 101 to R 108 are independently a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 8 to 30 ring carbon atoms or a cyano group, and

Ar 101 to Ar 104 are independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms,

provided that at least one of Ar 101 to Ar 104 is a heterocyclic group represented by the following formula (A2):

wherein R 111 to R 117 are independently a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 8 to 30 ring carbon atoms, a cyano group, a substituted or unsubstituted aryl group having 6 to 20 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 20 ring atoms,

adjacent substituents of R 11 to R 117 may be bonded to each other to form a saturated or unsaturated ring, and

X 101 is an oxygen atom or a sulfur atom; and

an anthracene derivative represented by the following formula (5):

wherein

Ar 11 and Ar 12 are independently a substituted or unsubstituted monocyclic group having 5 to 50 ring atoms, a substituted or unsubstituted fused ring group having 8 to 50 ring atoms, or a group formed by combination of the monocyclic group and the fused ring group,

provided that at least one of Ar 11 and Ar 12 is a substituted or unsubstituted dibenzofuranyl group, and

R 101 to R 108 are independently a hydrogen atom, a halogen atom, or a group selected from the group consisting of a substituted or unsubstituted monocyclic group having 5 to 50 ring atoms, a substituted or unsubstituted fused ring group having 8 to 50 ring atoms, a group formed by combination of the monocyclic group and the fused ring group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms, a substituted or unsubstituted silyl group and a cyano group.

2. The organic electroluminescence device according to claim 1 , wherein the aromatic amine derivative is represented by the following formula (A3):

wherein

R 101 to R 108 , Ar 102 and Ar 104 are the same as those in formula (A1),

R 121 to R 127 and R 131 to R 137 are independently a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 8 to 30 ring carbon atoms, a cyano group, a substituted or unsubstituted aryl group having 6 to 20 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 20 ring atoms,

adjacent substituents of R 121 to R 127 and R 131 to R 137 may be bonded to each other to form a saturated or unsaturated ring, and

X 102 and X 103 are independently an oxygen atom or a sulfur atom.

3. The organic electroluminescence device according to claim 2 wherein in the formula (A3),

Ar 102 and Ar 104 are a heterocyclic group represented by the following formula (A4):

wherein

one of R 141 to R 148 is used for connection to the nitrogen atom, and the others are independently a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 8 to 30 ring carbon atoms, a cyano group, a substituted or unsubstituted aryl group having 6 to 20 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 20 ring atoms,

adjacent substituents of R 141 to R 148 may be bonded to each other to form a saturated or unsaturated ring, and

X 104 is an oxygen atom or a sulfur atom.

4. The organic electroluminescence device according to claim 1 wherein in the formula (A1),

R 101 to R 108 are a hydrogen atom.

5. The organic electroluminescence device according to claim 4 wherein in the formula (A1),

R 102 is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms or a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, and

R 101 and R 103 to R 108 are a hydrogen atom.

6. The organic electroluminescence device according to claim 1 wherein in the formula (A1),

R 102 and R 106 are a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, or a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, and

R 101 , R 103 , R 104 , R 105 , R 107 and R 108 are a hydrogen atom.

7. The organic electroluminescence device according to claim 1 wherein in the formula (A2),

X 101 is an oxygen atom.

8. The organic electroluminescence device according to claim 2 wherein in the formula (A3),

X 102 and X 103 are an oxygen atom.

9. The organic electroluminescence device according to claim 3 wherein in the formula (A4),

X 104 is an oxygen atom.

10. The organic electroluminescence device according to claim 1 , wherein in the formula (A1),

in R 101 to R 108 ,

the halogen atom is selected from the group consisting of fluorine, chlorine, bromine and iodine,

the alkyl group for the substituted or unsubstituted alkyl group is selected from the group consisting of methyl, ethyl, propyl, isopropyl, n-butyl, s-butyl, isobutyl, t-butyl, n-pentyl, n-hexyl, n-heptyl and n-octyl,

the cycloalkyl group for the substituted or unsubstituted cycloalkyl group is selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl and norbornyl, and

the substituted or unsubstituted alkylsilyl group is selected from the group consisting of trimethylsilyl, triethylsilyl, t-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl and triisopropylsilyl,

in Ar 101 to Ar 104 ,

the aryl group for the substituted or unsubstituted aryl group is selected from the group consisting of phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, naphthacenyl, pyrenyl, chrysenyl, benzo[c]phenanthryl, benzo[g]chrysenyl, triphenylenyl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9-fluorenyl, benzofluorenyl, dibenzofluorenyl, 2-biphenylyl, 3-biphenylyl, 4-biphenylyl, terphenyl and fluoranthenyl, and

the heterocyclic group for the substituted or unsubstituted heterocyclic group is selected from the group consisting of pyrrolyl, pyrazinyl, pyridinyl, indolyl, isoindolyl, imidazolyl, furyl, benzofuranyl, isobenzofuranyl, 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 1-dibenzothiophenyl, 2-dibenzothiophenyl, 3-dibenzothiophenyl, 4-dibenzothiophenyl, quinolyl, isoquinolyl, quinoxalinyl, 1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl, 9-carbazolyl, phenantridinyl, acridinyl, phenanthrolinyl, phenazinyl, phenothiazinyl, phenoxazinyl, oxazolyl, oxadiazolyl, furazanyl, thienyl and benzothiophenyl, and

in R 111 to R 117 ,

the halogen atom is selected from the group consisting of fluorine, chlorine, bromine and iodine,

the alkyl group for the substituted or unsubstituted alkyl group is selected from the group consisting of methyl, ethyl, propyl, isopropyl, n-butyl, s-butyl, isobutyl, t-butyl, n-pentyl, n-hexyl, n-heptyl and n-octyl,

the substituted or unsubstituted alkylsilyl group is selected from the group consisting of trimethylsilyl, triethylsilyl, t-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl and triisopropylsilyl,

the aryl group for the substituted or unsubstituted aryl group is selected from the group consisting of phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, naphthacenyl, pyrenyl, chrysenyl, benzo[c]phenanthryl, benzo[g] chrysenyl, triphenylenyl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9-fluorenyl, benzofluorenyl, dibenzofluorenyl, 2-biphenylyl, 3-biphenylyl, 4-biphenylyl, terphenyl and fluoranthenyl, and

the heterocyclic group for the substituted or unsubstituted heterocyclic group is selected from the group consisting of pyrrolyl, pyrazinyl, pyridinyl, indolyl, isoindolyl, imidazolyl, furyl, benzofuranyl, isobenzofuranyl, 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 1-dibenzothiophenyl, 2-dibenzothiophenyl, 3-dibenzothiophenyl, 4-dibenzothiophenyl, quinolyl, isoquinolyl, quinoxalinyl, 1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl, 9-carbazolyl, phenantridinyl, acridinyl, phenanthrolinyl, phenazinyl, phenothiazinyl, phenoxazinyl, oxazolyl, oxadiazolyl, furazanyl, thienyl and benzothiophenyl.

11. The organic electroluminescence device according to claim 10 , wherein in the formula (A1),

in R 101 to R 108 ,

the halogen atom is fluorine,

the alkyl group for the substituted or unsubstituted alkyl group is selected from the group consisting of methyl, ethyl, propyl, isopropyl, n-butyl, s-butyl, isobutyl, t-butyl, n-pentyl and n-hexyl,

the cycloalkyl group for the substituted or unsubstituted cycloalkyl group is selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and 4-methylcyclohexyl, and

the arylsilyl group for the substituted or unsubstituted arylsilyl group is triphenylsilyl,

in Ar 101 to Ar 104 ,

the heterocyclic group for the substituted or unsubstituted heterocyclic group is selected from the group consisting of 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 1-dibenzothiophenyl, 2-dibenzothiophenyl, 3-dibenzothiophenyl, 4-dibenzothiophenyl, 1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl and 9-carbazolyl, and

in R 111 to R 117 ,

the halogen atom is fluorine,

the alkyl group for the substituted or unsubstituted alkyl group is selected from the group consisting of methyl, ethyl, propyl, isopropyl, n-butyl, s-butyl, isobutyl, t-butyl, n-pentyl and n-hexyl,

the alkenyl group for the substituted or unsubstituted alkenyl group is vinyl,

the alkynyl group for the substituted or unsubstituted alkynyl group is ethynyl, and

the heterocyclic group for the substituted or unsubstituted heterocyclic group is selected from the group consisting of 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 1-dibenzothiophenyl, 2-dibenzothiophenyl, 3-dibenzothiophenyl, 4-dibenzothiophenyl, 1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl and 9-carbazolyl.

12. The organic electroluminescence device according to claim 1 , wherein in the formula (A1),

R 101 to R 108 are independently a hydrogen atom, or a group selected from the group consisting of methyl, ethyl, propyl, isopropyl, n-butyl, n-hexyl, cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl,

Ar 101 to Ar 104 are independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenylyl group, a substituted or unsubstituted terphenyl group, 2-fluorenyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 2-dibenzothiophenyl, pyridinyl or quinolyl, and

R 111 to R 117 are independently a hydrogen atom, or a group selected from the group consisting of methyl, t-butyl, trimethylsilyl and phenyl.

13. The organic electroluminescence device according to claim 1 , wherein

the substituents for any substituted groups in the formula (A1) are independently selected from the group consisting of an alkyl group, a substituted or unsubstituted silyl group, an alkoxy group, an aryl group, an aryloxy group, an aralkyl group, a cycloalkyl group, a heterocyclic group, a halogen atom, an alkyl halide group, a hydroxyl group, a nitro group, a cyano group and a carboxy group.

14. The organic electroluminescence device according to claim 13 , wherein

the substituents for any substituted groups in the formula (A1) are independently selected from the group consisting of methyl, ethyl, propyl, isopropyl, n-butyl, s-butyl, isobutyl, t-butyl, n-pentyl, n-hexyl, trimethylsilyl, triethylsilyl, t-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triisopropylsilyl, triphenylsilyl, methoxy, ethoxy, phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, naphthacenyl, pyrenyl, chrysenyl, benzo[c]phenanthryl, benzo[g]chrysenyl, triphenylenyl, 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, 9-fluorenyl, benzofluorenyl, dibenzofluorenyl, 2-biphenylyl, 3-biphenylyl, 4-biphenylyl, terphenyl, fluoranthenyl, phenoxy, benzyl, phenylethyl, 2-phenylpropane-2-yl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, adamantyl, norbornyl, pyrrolyl, pyrazinyl, pyridinyl, indolyl, isoindolyl, imidazolyl, furyl, benzofuranyl, isobenzofuranyl, 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 1-dibenzothiophenyl, 2-dibenzothiophenyl, 3-dibenzothiophenyl, 4-dibenzothiophenyl, quinolyl, isoquinolyl, quinoxalinyl, 1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl, 9-carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, phenothiazinyl, phenoxazinyl, oxazolyl, oxadiazolyl, furazanyl, thienyl, benzothiophenyl, fluorine, chlorine, bromine, iodine, fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl, trifluoromethyl, hydroxyl, nitro, cyano and carboxy.

15. The organic electroluminescence device according to claim 1 , wherein

the substituents for any substituted groups in the formula (A1) are independently selected from the group consisting of methyl, ethyl, isopropyl, 2,2-dimethylpropyl, t-butyl, trimethylsilyl, methoxy, phenyl, 2-phenylpropane-2-yl, cyclopentyl, cyclohexyl, fluorine, trifluoromethyl and cyano.

16. The organic electroluminescence device according to claim 1 , wherein in the formula (5),

Ar 11 is a substituted or unsubstituted dibenzofuranyl group, and

Ar 12 is a substituted or unsubstituted monocyclic group having 5 to 50 ring atoms, a substituted or unsubstituted fused ring group having 8 to 50 ring atoms, or a group formed by combination of the monocyclic group and the fused ring group, other than a substituted or unsubstituted dibenzofuranyl group.

17. The organic electroluminescence device according to claim 16 , wherein in the formula (5),

Ar 11 is a substituted or unsubstituted 2-dibenzofuranyl group or a substituted or unsubstituted 4-dibenzofuranyl group.

18. The organic electroluminescence device according to claim 17 , wherein in the formula (5),

Ar 11 is a substituted or unsubstituted 2-dibenzofuranyl group.

19. The organic electroluminescence device according to claim 16 , wherein in the formula (5),

in Ar 12 ,

the monocyclic group for the substituted or unsubstituted monocyclic group is an aromatic group or a heterocyclic group,

the aromatic group is selected from the group consisting of a phenyl group, biphenyl group, terphenyl group and quaterphenyl group, and

the heterocyclic group is selected from the group consisting of a pyridyl group, pyradyl group, pyrimidyl group, triadinyl group, furyl group and thienyl group; and

the fused ring group for the substituted or unsubstituted fused ring group is selected from the group consisting of a fused aromatic ring group and a fused heterocyclic group,

the fused aromatic ring group is selected from the group consisting of a naphthyl group, phenanthryl group, anthryl group, chrysenyl group, benzanthryl group, benzophenanthryl group, triphenylenyl group, benzochrysenyl group, indenyl group, fluorenyl group, 9,9-dimethylfluorenyl group, benzofluorenyl group, dibenzofluorenyl group, fluoranthenyl group and benzofluoranthenyl group, and

the fused heterocyclic group is selected from the group consisting of a benzofuranyl group, benzothiophenyl group, indolyl group, dibenzofuranyl group, dibenzothiophenyl group, carbazolyl group, quinolyl group and phenanthrolinyl group.

20. The organic electroluminescence device according to claim 19 , wherein

in Ar 12 ,

the monocyclic group for the substituted or unsubstituted monocyclic group is selected from the group consisting of a phenyl group, biphenyl group or terphenyl group, and

the fused ring group for the substituted or unsubstituted fused ring group is selected from the group consisting of a naphthyl group, phenanthryl group, anthryl group, 9,9-dimethylfluorenyl group, fluoranthenyl group, benzanthryl group, dibenzothiophenyl group, dibenzofuranyl group and carbazolyl group.

21. The organic electroluminescence device according to claim 19 , wherein

Ar 12 is a substituted or unsubstituted aromatic group having 6 to 50 ring atoms.

22. The organic electroluminescence device according to claim 21 , wherein

Ar 12 is a substituted or unsubstituted phenyl group.

23. The organic electroluminescence device according to claim 1 , wherein

the substituents for any substituted groups in the formula (5) are independently selected from the group consisting of a monocyclic group having 5 to 50 ring atoms, a fused ring group having 8 to 50 ring atoms, an alkyl group having 1 to 50 carbon atoms, a cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted silyl group, an alkoxy group having 1 to 50 carbon atoms, a cyano group and a halogen atom.

24. The organic electroluminescence device according to claim 23 , wherein

the substituents for any substituted groups in the formula (5) are independently selected from the group consisting of a monocyclic group having 5 to 50 ring atoms and a fused ring group having 8 to 50 ring atoms.

25. The organic electroluminescence device according to claim 24 , wherein

the substituents for any substituted groups in the formula (5) are independently selected from the group consisting of a phenyl group, a biphenyl group, a terphenyl group, a quaterphenyl group, a pyridyl group, a pyradyl group, a pyrimidyl group, a triadinyl group, a furyl group and a thienyl group.

26. The organic electroluminescence device according to claim 19 , wherein,

Ar 12 is a naphthyl group, a phenanthryl group or a benzanthryl group.

27. The organic electroluminescence device according to claim 1 , wherein in formula (5),

R 101 to R 108 are independently a hydrogen atom.

28. The organic electroluminescence device according to claim 4 , wherein in formula (5),

R 101 to R 108 are independently a hydrogen atom.

29. The organic electroluminescence device according to claim 1 , which comprises the aromatic amine derivative represented by the formula (A1) as a dopant material, and the anthracene derivative represented by the formula (5) as a host material.

30. An electronic equipment comprising the organic electroluminescence device according to claim 1 .