Aromatic amine derivative, and organic electroluminescent element using same

Patent metadata

Field	Value
Publication number	US-10014477-B2
Application number	US-201314424656-A
Country	US
Kind code	B2
Filing date	Aug 29, 2013
Priority date	Aug 31, 2012
Publication date	Jul 3, 2018
Grant date	Jul 3, 2018

Abstract

An aromatic amine derivative represented by formula (1):

wherein R 1 , R 2 , R 3 , L, AR 1 , Ar 2 , k, m, and n are the same as defined in the specification, is useful as a material for an organic EL device and realizes an organic EL device with a high efficiency and a long lifetime even when driving it at a low voltage.

First claim

What is claimed is:

1. An organic electroluminescence device comprising an anode, a cathode, and at least one organic thin film layer disposed between the anode and the cathode, wherein:
the at least one organic thin film layer comprises a light emitting layer; and
at least one organic thin film layer comprises an aromatic amine derivative represented by formula (20):

wherein:
Ar 1 represents a group represented by formula (4):

Ar 2 represents a group of formula (14):

L 3 represents a single bond;
L 8 represents a single bond;
each of R 1 , R 8 and R 17 represents a hydrogen atom;
R 2 and R 3 may be the same or different and independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 50 ring atoms, a halogen atom, a substituted or unsubstituted fluoroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted fluoroalkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms, or a cyano group;
groups R 2 may be the same or different, and groups R 3 may be the same or different;
two groups R 4 and two groups R 5 may be the same or different and independently represent a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms;
R 2 , R 3 , R 4 and R 5 may be the same or different;
k represents an integer of 1 to 5;
m represents an integer of 1 to 4;
n represents an integer of 1 to 3, and
a substituent referred to by “substituted or unsubstituted” is selected from the group consisting of an alkyl group having 1 to 50 carbon atoms, a cycloalkyl group having 3 to 50 ring carbon atoms, an aryl group having 6 to 50 ring carbon atoms, an aralkyl group having 1 to 50 carbon atoms which includes an aryl group having 6 to 50 ring carbon atoms an alkoxy group having an alkyl group having 1 to 50 carbon atoms, an aryloxy group having an aryl group having 6 to 50 ring carbon atoms, a mono-, di- or tri-substituted silyl group having a substituent selected from an alkyl group having 1 to 50 carbon atoms and an aryl group having 6 to 50 ring carbon atoms, a heteroaryl group having 5 to 50 ring atoms and having 1 to 5 hetero atoms selected from a nitrogen atom, an oxygen atom, and a sulfur atom, a halogen atom selected from a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, a cyano group, and a nitro group.

2. The organic electroluminescence device according to claim 1 , wherein the at least one organic thin film layer comprises a hole injecting layer or a hole transporting layer, and the hole injecting layer or the hole transporting layer comprises the aromatic amine derivative.

3. The organic electroluminescence device according to claim 1 , wherein Ar 1 represents a group represented by formula (30):

wherein R 4 , R 8 , and m are the same as defined in formula (4).

4. The organic electroluminescence device according to claim 3 , wherein Ar 2 is represented by

5. The organic electroluminescence device according to claim 1 , wherein a layer of the at least one organic thin film layer, which is closest to the light emitting layer, comprises the aromatic amine derivative.

6. The organic electroluminescence device according to claim 5 , wherein the aromatic amine derivative is selected from the following compounds:

7. The organic electroluminescence device according to claim 5 , wherein the aromatic amine derivative is

8. The organic electroluminescence device according to claim 1 , wherein R 2 and R 3 independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

9. The organic electroluminescence device according to claim 1 , wherein each of R 2 and R 3 is a hydrogen atom.

10. The organic electroluminescence device according to claim 1 , wherein Ar 2 is represented by

11. The organic electroluminescence device according to claim 1 , wherein each of R 4 and R 5 is a methyl group or a phenyl group.

12. The organic electroluminescence device according to claim 1 , wherein the aromatic amine derivative is selected from the following compounds:

13. The organic electroluminescence device according to claim 1 , wherein the aromatic amine derivative is

Assignees

• Idemitsu Kosan Co

Inventors

• Kato Tomoki
• Sado Takayasu
• Fujiyama Takahiro

Classifications

• C09K2211/1092

  containing sulfur as the only heteroatom · CPC title

• C09K2211/1014

  bridged by heteroatoms, e.g. N, P, Si or B · CPC title

• C09K2211/1011

  Condensed systems · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title

• C09B57/008

  Triarylamine dyes containing no other chromophores · CPC title