Organic electroluminescent element

Patent metadata

Field	Value
Publication number	US-9082986-B2
Application number	US-201214122131-A
Country	US
Kind code	B2
Filing date	May 23, 2012
Priority date	May 27, 2011
Publication date	Jul 14, 2015
Grant date	Jul 14, 2015

Abstract

An organic electroluminescence device includes a first organic thin-film layer and a second organic thin-film layer between an anode and a cathode opposing the anode in this order from the anode side. The first organic thin-film layer includes a specific aromatic heterocyclic derivative A, and the second organic thin-film layer includes a specific aromatic heterocyclic derivative B. The aromatic heterocyclic derivative A and the aromatic heterocyclic derivative B are different from each other. The organic electroluminescence device is capable of driving at a low voltage and has a long lifetime.

First claim

What is claimed is:

1. An organic electroluminescence device, comprising a first organic thin-film layer and a second organic thin-film layer between an anode and a cathode opposing the anode in this order from the anode side,
wherein the first organic thin-film layer comprises an aromatic heterocyclic derivative A represented by formula (1-1), the second organic thin-film layer comprises an aromatic heterocyclic derivative B represented by formula (2-1), and the aromatic heterocyclic derivative A and the aromatic heterocyclic derivative B are different from each other:

wherein:
each of W 1 and W 2 independently represents a single bond, CR 1 R 2 or SiR 1 R 2 ;
each of R 1 and R 2 independently represents 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 2 to 30 ring carbon atoms;
each of A 1 and A 2 independently represents a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms;
each of L 1 and L 2 independently represents a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms;
one of X 5 to X 8 and one of X 9 to X 12 represent carbon atoms which are bonded to each other and the others of X 1 to X 16 independently represent CR 3 or a nitrogen atom; and
R 3 independently represents a hydrogen atom, 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 2 to 30 ring carbon atoms or adjacent R 3 groups are bonded to each other to form a ring structure;

wherein:
each of W 3 and W 4 independently represents a single bond, CR 4 R 5 or SiR 4 R 5 ;
each of R 4 and R 5 independently represents 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 2 to 30 ring carbon atoms;
each of L 3 and L 4 independently represents a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms;
one of Y 5 to Y 8 and one of Y 9 to Y 12 represent carbon atoms which are bonded to each other and the others of Y 1 to Y 16 independently represent CR 6 or a nitrogen atom;
R 6 independently represents a hydrogen atom, 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 2 to 30 ring carbon atoms, or adjacent R 6 groups are bonded to each other to form a ring structure; and
each of A 3 and A 4 independently represents a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms,
with the proviso that at least one of A 3 and A 4 is represented by formula (2-a):

wherein:
each of Z 1 to Z 5 independently represents CR 7 or a nitrogen atom; and
R 7 independently represents a hydrogen atom, 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 2 to 30 ring carbon atoms, or adjacent R 7 groups are bonded to each other to form a ring structure.

2. The organic electroluminescence device according to claim 1 , wherein the aromatic heterocyclic derivative A is represented by formula (1-2) and the aromatic heterocyclic derivative B is represented by formula (2-2):

wherein A 1 , A 2 , L 1 , L 2 , and X 1 to X 16 are as defined in formula (1-1); and

wherein A 3 , A 4 , L 3 , L 4 , and Y 1 to Y 16 are as defined in formula (2-1).

3. The organic electroluminescence device according to claim 1 , wherein the aromatic heterocyclic derivative A is represented by formula (1-3):

wherein A 1 , A 2 , L 1 , L 2 , and X 1 to X 16 are as defined in formula (1-1).

4. The organic electroluminescence device according to claim 1 , wherein the aromatic heterocyclic derivative A is represented by formula (1-4) or (1-5):

wherein A 1 , A 2 , L 1 , L 2 , and X 1 to X 16 are as defined in formula (1-1).

5. The organic electroluminescence device according to claim 1 , wherein the aromatic heterocyclic derivative B is re

Assignees

• Kato Tomoki
• Yabunouchi Nobuhiro
• Sado Takayasu
• Idemitsu Kosan Co

Inventors

• Kato Tomoki
• Yabunouchi Nobuhiro
• Sado Takayasu

Classifications

• H01L51/5016

  Electricity · mapped topic

• H01L51/0072

  Electricity · mapped topic

• H01L51/5012

  Electricity · mapped topic

• H01L51/0056 Primary

  Electricity · mapped topic

• H01L51/5056

  Electricity · mapped topic