Organic electroluminescent element, material for organic electroluminescent element and light emitting device, display device, and illumination device, each employing organic electroluminescent element

Patent metadata

Field	Value
Publication number	US-9728726-B2
Application number	US-201214350745-A
Country	US
Kind code	B2
Filing date	Nov 1, 2012
Priority date	Nov 2, 2011
Publication date	Aug 8, 2017
Grant date	Aug 8, 2017

Abstract

This application relates in part to an organic electroluminescent element including a substrate, a pair of electrodes including an anode and a cathode, disposed on the substrate, and an organic layer(s) including a light emitting layer, in which the organic layer(s) contains a compound represented by the following formula (1), in which R 1 to R 8 are each hydrogen or a substituent, at least one of R 1 to R 4 and at least one of R 5 to R 8 are each a substituent represented by the formula (2); R 9 to R 12 , Z 1 to Z 4 , Ar 1 , Ar 2 , and L 1 are as defined herein.

First claim

The invention claimed is:

1. An organic electroluminescent element comprising:
a substrate;
a pair of electrodes including an anode and a cathode, disposed on the substrate; and
at least one organic layer including a light emitting layer, disposed between the electrodes,
wherein the organic layer(s) contains a compound represented by the following general formula (1):

wherein R 1 to R 8 each independently represent a hydrogen atom or a substituent, these may be bonded to each other to form a ring, and at least one of R 1 to R 8 is a substituent represented by the following general formula (2);
R 9 to R 12 each independently represent an aryl group or an alkyl group having 1 to 5 carbon atoms, wherein when R 9 and R 10 are each an alkyl group or an aryl group having an alkyl chain, the total number of carbon atoms in the alkyl groups represented by R 9 and R 10 is from 2 to 8, and wherein when R 11 and R 12 are each an alkyl group or an aryl group having an alkyl chain, the total number of carbon atoms in the alkyl groups represented by R 11 and R 12 is from 2 to 8;
Z 1 and Z 2 and Z 3 and Z 4 may be respectively bonded to each other to form a ring, but they do not form an aromatic ring in any case;
when Z 1 and Z 2 and Z 3 and Z 4 are respectively bonded to each other to form a ring, Z 1 to Z 4 each independently represent an alkyl group, an aryl group, a heteroaryl group, a silyl group, —O—, or —NY—, provided that Y is an alkyl group or an aryl group and provided that Z 1 and Z 2 are not both alkyl groups in any case and Z 3 and Z 4 are not both alkyl groups in any case;
when Z 1 and Z 2 and Z 3 and Z 4 are not respectively bonded to each other to form a ring, Z 1 to Z 4 each independently represent a hydrogen atom, a deuterium atom, an alkyl group, an aryl group, a heteroaryl group, a fluorine atom, a silyl group, or a cyano group:

wherein Ar 1 and Ar 2 each independently represent an alkyl group, an aryl group, or a heteroaryl group and may be bonded to each other to form a ring; L 1 represents an arylene group or a heteroarylene group; Ar 1 and Ar 2 , and L 1 and Ar 1 and/or L 1 and Ar 2 may be bonded to each other to form a ring; n represents 0 or 1, and when n is 0, L 1 represents a single bond.

2. The organic electroluminescent element according to claim 1 , wherein at least one of R 1 to R 4 and at least one of R 5 to R 8 in the general formula (1) are each a substituent represented by the general formula (2).

3. The organic electroluminescent element according to claim 1 , wherein the compound represented by the general formula (1) is a compound represented by the following general formula (3):

wherein R 1 , R 2 , R 4 to R 6 , and R 8 each independently represent a hydrogen atom or a substituent, and these may be bonded to each other to form a ring;
R 9 to R 12 each independently represent an aryl group or an alkyl group having 1 to 5 carbon atoms, wherein when R 9 and R 10 are each an alkyl group or an aryl group having an alkyl chain, the total number of carbon atoms in the alkyl groups represented by R 9 and R 10 is from 2 to 8, and wherein when R 11 and R 12 are each an alkyl group or an aryl group having an alkyl chain, the total number of carbon atoms in the alkyl groups represented by R 11 and R 12 is from 2 to 8;
Ar 3 to Ar 6 each independently represent an alkyl group, an aryl group, or a heteroaryl group, and Ar 3 and Ar 4 and Ar 5 and Ar 6 may be respectively bonded to each other to form a ring;
L 2 and L 3 each independently represent an arylene group or a heteroarylene group, Ar 3 and Ar 4 , L 2 and Ar 3 and/or L 2 and Ar 4 , Ar 5 and Ar 6 , and L 3 and Ar 5 and/or L 3 and Ar 6 may be bonded to each other to form a ring;
m and t each independently represent 0 or 1, and when m and t are 0, each of L 2 and L 3 represents a single bond;
Z 1 and Z 2 and Z 3 and Z 4 may be respectively bonded to each other to form a ring, but they do not form an aromatic ring in any case; when Z 1 and Z 2 and Z 3 and Z 4 are bonded to each other to form a ring, Z 1 to Z 4 each independently represent an alkyl group, an aryl group, a heteroaryl group, a silyl group, —O—, or —NY—, provided that Y is an alkyl group or an aryl group and provided that Z 1 and Z 2 are not both alkyl groups in any case and Z 3 and Z 4 are not both alkyl groups in any case; when Z 1 and Z 2 and Z 3 and Z 4 are not bonded to each other to form a ring, Z 1 to Z 4 each independently represent a hydrogen atom, a deuterium atom, an alkyl group, an aryl group, a heteroaryl group, a fluorine atom, a silyl group, or a cyano group.

4. The organic electroluminescent element according to claim 1 , wherein the compound represented by the general formula (3) is a compound represented by the following general formula (4):

wherein R 1 , R 2 , R 4 to R 6 , and R 8 each independently represent a hydrogen atom or a substituent, and these may be bonded to each other to form a ring;
R 9 to R 12 each independently represent an aryl group or an alkyl group having 1 to 5 carbon atoms, wherein when R 9 and R 10 are each an alkyl group or an aryl group having an alkyl chain, the total number of carbon atoms in the alkyl groups represented by R 9 and R 10 is from 2 to 8, and wherein when R 11 and R 12 are each an alkyl group or an aryl group having an alkyl chain, the total number of carbon atoms in the alkyl groups represented by R 11 and R 12 is from 2 to 8;
Ar 3 to Ar 6 each independently represent an alkyl group, an aryl group, or a heteroaryl group, and Ar 3 and Ar 4 and Ar 5 and Ar 6 may be respectively bonded to each other to form a ring;
Z 1 and Z 2 and Z 3 and Z 4 may be respectively bonded to each other to form a ring, but they do not form an aromatic ring in any case; when Z 1 and Z 2 and Z 3 and Z 4 are bonded to each other to form a ring, Z 1 to Z 4 each independently represent an alkyl group, an aryl group, a heteroaryl group, a silyl group, —O—, or —NY—, provided that Y is an alkyl group or an aryl group and provided that Z 1 and Z 2 are not both alkyl groups in any case and Z 3 and Z 4 are not both alkyl groups in any case; when Z 1 and Z 2 and Z 3 and Z 4 are not bonded to each other to form a ring, Z 1 to Z 4 each independently represent a hydrogen atom (including a deuterium atom), an alkyl group, an aryl group, a heteroaryl group, a fluorine atom, a silyl group, or a cyano group.

5. The organic electroluminescent element according to claim 4 , wherein Z 1 and Z 2 and Z 3 and Z 4 in the general formula (4) are not respectively bonded to each other to form a ring and Z 1 to Z 4 are each independently a hydrogen atom, a deuterium atom, an alkyl group, a fluorine atom, a silyl group, or a cyano group.

6. The organic electroluminescent element according to claim 1 , wherein the compound represented by the general formula (1) is a compound represented by the following general formula (5):

wherein R 1 , R 2 , R 4 to R 6 , and R 8 each independently represent a hydrogen atom or a substituent, and these may be bonded to each other to form a ring;

Assignees

• Udc Ireland Ltd

Inventors

• Takaku Koji
• Yonekuta Yasunori
• Kinoshita Masaru
• Sotoyama Wataru
• Ise Toshihiro
• Kaminaga Kuniyuki
• Hirayama Heijiro

Classifications

• H05B33/14

  characterised by the chemical or physical composition or the arrangement of the electroluminescent material {, or by the simultaneous addition of the electroluminescent material in or onto the light source} · CPC title

• C09K11/06 Primary

  containing organic luminescent materials · CPC title

• C09B57/008

  Triarylamine dyes containing no other chromophores · CPC title

• C09B57/00

  Other synthetic dyes of known constitution · CPC title

• C09B1/00

  Dyes with anthracene nucleus not condensed with any other ring · CPC title