Aromatic amine derivative, and organic electroluminescent element comprising the same

Patent metadata

Field	Value
Publication number	US-9466800-B2
Application number	US-201514850357-A
Country	US
Kind code	B2
Filing date	Sep 10, 2015
Priority date	Apr 24, 2009
Publication date	Oct 11, 2016
Grant date	Oct 11, 2016

Abstract

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.

First claim

The invention claimed is:

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, and
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,
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, 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; 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 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.

2. The organic electroluminescence device according to claim 1 wherein in formula (5), Ar 11 and Ar 12 are independently a substituted or unsubstituted fused ring group having 10 to 50 ring carbon atoms.

3. The organic electroluminescence device according to claim 1 wherein in formula (5), one of Ar 11 and Ar 12 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 10 to 50 ring atoms.

4. The organic electroluminescence device according to claim 3 wherein in formula (5), Ar 12 is a naphthyl group, a phenanthryl group, a benzanthryl group or a dibenzofuranyl group, and Ar 11 is a phenyl group which is unsubstituted or substituted by a monocyclic group or fused ring group.

5. The organic electroluminescence device according to claim 3 wherein in formula (5), Ar 12 is a substituted or unsubstituted fused ring group having 8 to 50 ring atoms, and Ar 11 is an unsubstituted phenyl group.

6. The organic electroluminescence device according to claim 1 wherein in formula (5), Ar 11 and Ar 12 are independently a substituted or unsubstituted monocyclic group having 5 to 50 ring atoms.

7. The organic electroluminescence device according to claim 6 wherein in formula (5), Ar 11 and Ar 12 are independently a substituted or unsubstituted phenyl group.

8. The organic electroluminescence device according to claim 7 wherein in formula (5), Ar 11 is an unsubstituted phenyl group and Ar 12 is a phenyl group having a monocyclic group or a fused ring group as a substituent.

9. The organic electroluminescence device according to claim 7 wherein in formula (5), Ar 11 and Ar 12 are independently a phenyl group having a monocyclic group or a fused ring group as a substituent.

10. 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.

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

12. The organic electroluminescence device according to claim 1 , wherein Ar 11 and Ar 12 are independently a phenyl group or naphthyl group which is unsubstituted or substituted by a phenyl group or naphthyl group.

13. The organic electroluminescence device according to claim 12 , wherein Ar 11 is a phenyl group which is unsubstituted or substituted by a phenyl group or a naphthyl group, and Ar 12 is a naphthyl group which is unsubstituted or substituted by a phenyl group or naphthyl group.

14. The organic electroluminescence device according to claim 13 , wherein Ar 12 is a naphthyl group substituted by a phenyl group.

15. The organic electroluminescence device according to claim 1 , wherein Ar 11 and Ar 12 are independently a naphthyl group which is unsubstituted or substituted by a phenyl group or naphthyl group.

16. 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.

Assignees

• Idemitsu Kosan Co

Inventors

• Mizuki Yumiko
• Funahashi Masakazu
• Kawamura Masahiro

Classifications

• H10K85/633

  comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom · CPC title

• C07D307/91 Primary

  Dibenzofurans; Hydrogenated dibenzofurans · CPC title

• H01L51/0052

  Electricity · mapped topic

• C09K2211/1088

  containing oxygen as the only heteroatom · CPC title

• H01L51/0068

  Electricity · mapped topic