Aromatic amine derivative, and organic electroluminescent element comprising the same
An aromatic amine derivative represented by the following formula (1) wherein at least one of Ar 1 to Ar 4 is a heterocyclic group represented by the following formula (2) wherein X 1 is an oxygen atom or a sulfur atom.
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 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 111 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-A):
wherein
Ar 11a and Ar 12a are independently a substituted or unsubstituted fused ring group having 8 to 50 ring atoms and
R 101 to R 108 are independently a group selected from a hydrogen atom, 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, a halogen atom and a cyano group, and
an anthracene derivative represented by the following formula (5-B):
wherein
one of Ar 11b and Ar 12b is a substituted or unsubstituted monocyclic group having 5 to 50 ring atoms, and the other is a substituted or unsubstituted fused ring group having 8 to 50 ring atoms and
R 101 to R 108 are the same as defined in the formula (5-A).
2. The organic electroluminescence device according to claim 1 , wherein
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, 4-methylcyclohexyl, adamantyl and norbornyl,
the substituted silyl group is selected from the group consisting of trimethylsilyl, triethylsilyl, t-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triisopropylsilyl and triphenylsilyl, and
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, phenanthridinyl, 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 silyl group for the substituted or unsubstituted silyl group is selected from the group consisting of trimethylsilyl, triethylsilyl, t-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triisopropylsilyl and triphenylsilyl,
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, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, phenothiazinyl, phenoxazinyl, oxazolyl, oxadiazolyl, furazanyl, thienyl and benzothiophenyl.
3. The organic electroluminescence device according to claim 2 , wherein
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 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.
4. The organic electroluminescence device according to claim 1 , wherein
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, cyclohexyl, phenyl substituted by methyl and 1-naphthyl,
Ar 101 to Ar 104 are independently a group selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenylyl, substituted or unsubstituted terphenyl, 2-fluorenyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 2-dibenzothiophenyl, pyridinyl and 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.
5. The organic electroluminescence device according to claim 1 , wherein
R 101 to R 108 are independently a hydrogen atom,
Ar 101 to Ar 104 are independently a group selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenylyl, substituted or unsubstituted terphenyl, 2-fluorenyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 2-dibenzothiophenyl, pyridinyl and quinolyl,
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,
adjacent substituents of R 111 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.
6. The organic electroluminescence device according to claim 1 , wherein R 111 to R 117 are independently a hydrogen atom.
7. 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 alkyl, substituted or unsubstituted silyl, alkoxy, aryl, aryloxy, aralkyl, cycloalkyl, heterocyclic, halogen, alkyl halide, hydroxy, nitro, cyano and carboxy.
8. The organic electroluminescence device according to claim 7 , 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, hydroxy, nitro, cyano and carboxy.
9. The organic electroluminescence device according to claim 8 , 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.
10. The organic electroluminescence device according to claim 1 , wherein
Ar 101 to Ar 104 are independently a group selected from the group consisting of a phenyl group, a biphenyl group, a terphenyl group, a 2-dibenzofuranyl group, a 3-dibenzofuranyl group, and a 4-dibenzofuranyl group.
11. The organic electroluminescence device according to claim 1 , wherein
the substituted or unsubstituted fused ring groups having 8 to 50 ring atoms for Ar 11a , Ar 12a , Ar 11b and Ar 12b are independently 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, benzofluoranthenyl group, a benzofuranyl group, benzothiophenyl group, indolyl group, dibenzofuranyl group, dibenzothiophenyl group, carbazolyl group, quinolyl group and phenanthrolinyl group.
12. The organic electroluminescence device according to claim 11 , wherein
the substituted or unsubstituted fused ring groups having 8 to 50 ring atoms for Ar 11a , Ar 12a , Ar 11b and Ar 12b are independently 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.
13. The organic electroluminescence device according to claim 1 , wherein
the substituted or unsubstituted monocyclic group having 5 to 50 ring atoms for one of Ar 11b and Ar 12b is selected from the group consisting of a phenyl group, biphenyl group, terphenyl group and quaterphenyl group, pyridyl group, pyradyl group, pyrimidyl group, triadinyl group, furyl group and thienyl group.
14. The organic electroluminescence device according to claim 13 , wherein
the substituted or unsubstituted monocyclic group having 5 to 50 ring atoms for one of Ar 11b and Ar 12b is selected from the group consisting of a phenyl group, biphenyl group and terphenyl group.
15. The organic electroluminescence device according to claim 1 , wherein
one of Ar 11b and Ar 12b is a phenyl group, biphenyl group or terphenyl group which is unsubstituted or substituted by a monocyclic group or fused ring group, and
the other is a naphthyl group, phenanthryl group or anthryl group which is unsubstituted or substituted by a monocyclic group or fused ring group.
16. The organic electroluminescence device according to claim 1 , wherein
one of Ar 11b and Ar 12b is a phenyl group substituted by a phenyl group or naphthyl group, and the other is an unsubstituted naphthyl group.
17. The organic electroluminescence device according to claim 1 , wherein
Ar 11a and Ar 12a are independently a naphthyl group, phenanthryl group or anthryl group which is unsubstituted or substituted by a monocyclic group or fused ring group.
18. The organic electroluminescence device according to claim 1 , wherein
at least one of Ar 11a and Ar 12a are independently a naphthyl group, phenanthryl group or anthryl group which is unsubstituted or substituted by a monocyclic group or fused ring group.
19. The organic electroluminescence device according to claim 1 , wherein Ar 11a and Ar 12a are independently an unsubstituted naphthyl group.
20. The organic electroluminescence device according to claim 1 , wherein
the substituents for any substituted groups in the formula (5-A) and (5-B) are independently selected from the group consisting of a monocyclic group having 5 to 50 ring atoms, fused ring group having 8 to 50 ring atoms, alkyl group having 1 to 50 carbon atoms, cycloalkyl group having 3 to 50 ring carbon atoms, substituted or unsubstituted silyl group, alkoxy group having 1 to 50 carbon atoms, cyano group and halogen atom.
21. The organic electroluminescence device according to claim 18 , wherein
the substituents for any substituted groups in the formula (5-A) and (5-B) are independently selected from the group consisting of a monocyclic group having 5 to 50 ring atoms and fused ring group having 8 to 50 ring atoms.
22. The organic electroluminescence device according to claim 19 , wherein the substituents for any substituted groups in the formula (5-A) and (5-B) are independently selected from the group consisting of a phenyl group, biphenyl group, terphenyl group and quaterphenyl group, pyridyl group, pyradyl group, pyrimidyl group, triadinyl group, furyl group and thienyl group.
23. The organic electroluminescence device according to claim 1 , wherein R 101 to R 108 in the formula (5-A) and (5-B) are independently a hydrogen atom.
24. The organic electroluminescence device according to claim 6 , wherein R 101 to R 108 in the formula (5-A) and (5-B) are independently a hydrogen atom.
25. 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-A) and the anthracene derivative represented by the formula (5-B) as host materials.
26. An electronic equipment comprising the organic electroluminescence device according to claim 1 .