Aromatic amine derivative and organic electroluminescence element using same

Patent metadata

Field	Value
Publication number	US-9634255-B2
Application number	US-201214345066-A
Country	US
Kind code	B2
Filing date	Sep 11, 2012
Priority date	Sep 15, 2011
Publication date	Apr 25, 2017
Grant date	Apr 25, 2017

Abstract

An aromatic amine derivative represented by formula (1):

wherein L 1 , L 2 , Ar 1 , Ar 2 , R 1 , R 2 , a, b, and Q are as defined in the specification. An organic electroluminescence device having at least one organic thin film layer which includes the aromatic amine derivative has high emission efficiency and long lifetime.

First claim

What is claimed is:

1. An aromatic amine derivative of formula (1):

wherein:
L 1 is a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 30 ring carbon atoms;
L 2 is a single bond, a substituted or unsubstituted heteroarylene group having 5 to 30 ring carbon atoms, or a substituted or unsubstituted arylene group, wherein the arylene group is selected from a phenylene group, a biphenylene group, a terphenylene group, a naphthylene group, a phenanthrylene group, a chrysenylene group, a perylenylene group, and a fluorenylene group;
each of Ar 1 and Ar 2 are independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 30 ring carbon atoms;
each of R 1 and R 2 are independently a fluorine atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted haloalkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 10 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring carbon atoms, wherein adjacent R 1 groups and adjacent R 2 groups may be respectively bonded to each other to form a ring structure together with ring carbon atoms of the benzene ring;
the optional substituent of each substituted or unsubstituted group is selected from the group consisting of a fluorine atom, a cyano group, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a haloalkyl group having 1 to 20 carbon atoms, a haloalkoxy group having 1 to 20 carbon atoms, an alkylsilyl group having 1 to 10 carbon atoms, an aryl group having 6 to 30 ring carbon atoms, an aryloxy group having 6 to 30 ring carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, an aralkyl group having 7 to 30 carbon atoms, and a heteroaryl group having 5 to 30 ring atoms;
a is an integer of 0 to 3;
b is an integer of 0 to 4; and
Q is a group of formula (a):

wherein:
X is an oxygen atom or a sulfur atom;
each of R 3 and R 4 are independently a fluorine atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted haloalkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 10 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring carbon atoms, wherein adjacent R 3 groups and adjacent R 4 groups may be respectively bonded to each other to form a ring structure together with ring carbon atoms of the benzene ring;
c is an integer of 0 to 3; and
d is an integer of 0 to 4.

2. The aromatic amine derivative according to claim 1 , wherein the aromatic amine derivative is of formula (1-1):

wherein L 1 , L 2 , Ar 1 , Ar 2 , R 1 , R 2 , a, b, and Q are as defined in formula (1).

3. The aromatic amine derivative according to claim 1 , wherein Q is of formula (a-1):

wherein R 3 , R 4 , c, d, and X are as defined in formula (a).

4. The aromatic amine derivative according to claim 1 , wherein Q is of formula (a-2):

wherein R 3 , R 4 , c, d, and X are as defined in formula (a).

5. The aromatic amine derivative according to claim 1 , wherein at least one of L 1 and L 2 is a single bond or a linking group of any one of formulae (b-1) to (b-3):

wherein:
each of R 11 to R 13 are independently a fluorine atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted haloalkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 10 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring carbon atoms, wherein adjacent R 11 groups, adjacent R 12 groups, and adjacent R 13 groups may be respectively bonded to each other to form a ring structure together with ring carbon atoms of the benzene ring:
each of R 14 and R 15 are independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring carbon atoms; and
each of k 1 to k 3 are independently an integer of 0 to 4.

6. The aromatic amine derivative according to claim 5 , wherein L 1 is a linking group of any one of formulae (b-1) to (b-3).

7. The aromatic amine derivative according to claim 5 , wherein L 2 is a single bond or a linking group of any one of formulae (b-1) to (b-3).

8. The aromatic amine derivative according to claim 7 , wherein L 2 is a single bond or a linking group of formula (b-1).

9. The aromatic amine derivative according to claim 1 , wherein X is an oxygen atom.

10. The aromatic amine derivative according to claim 1 , wherein X is a sulfur atom.

11. A material, comprising the aromatic amine derivative according to claim 1 .

12. The material according to claim 11 , wherein the material is a hole transporting material.

13. An organic electroluminescence device comprising an anode, a cathode, and an organic thin film layer between the anode and the cathode, wh

Assignees

• Kato Tomoki
• Fujiyama Takahiro
• Idemitsu Kosan Co

Inventors

• Kato Tomoki
• Fujiyama Takahiro

Classifications

• H10K85/626

  containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene · CPC title

• C09K11/06 Primary

  containing organic luminescent materials · CPC title

• H01L51/0061

  Electricity · mapped topic

• C07D409/04

  directly linked by a ring-member-to-ring-member bond · CPC title

• H01L51/006

  Electricity · mapped topic