Organic compound and electronic device comprising an organic layer comprising the organic compound

Patent metadata

Field	Value
Publication number	US-10294203-B2
Application number	US-201515537444-A
Country	US
Kind code	B2
Filing date	Nov 11, 2015
Priority date	Dec 26, 2014
Publication date	May 21, 2019
Grant date	May 21, 2019

Abstract

An organic compound suitable for organic layers of electronic devices that show improved luminescent properties.

First claim

What is claimed is:

1. An organic compound having the structure represented by Formula (1):

wherein X 1 through X 4 are each independently a chemical bond, or each independently selected from the group consisting of a substituted or unsubstituted C 6 -C 60 arylene and a substituted or unsubstituted C 1 -C 60 heteroarylene; and X 1 through X 4 may each independently form fused rings with the phenyl rings they are bonded to;
R 1 through R 4 are each independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C 1 -C 50 alkyl, a substituted or unsubstituted C 1 -C 50 alkoxy, a substituted or unsubstituted C 1 -C 50 alkoxycarbonyl, a substituted or unsubstituted C 6 -C 60 aryl, a substituted or unsubstituted C 6 -C 60 aryloxy, a substituted or unsubstituted C 6 -C 50 arylthio, a substituted or unsubstituted C 1 -C 60 heteroaryl, a halogen, a cyano, a hydroxyl, a carbonyl, and an amino group substituted with a substituted or unsubstituted C 6 -C 60 aryl or a substituted or unsubstituted C 1 -C 60 heteroaryl; and only one of R 1 through R 4 is an amino group having the structure

wherein Ar 1 and Ar 2 are each independently selected from the group consisting of a substituted or unsubstituted C 6 -C 60 aryl and a substituted or unsubstituted C 1 -C 60 heteroaryl; and
R 5 is selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C 1 -C 50 alkyl, a substituted or unsubstituted C 1 -C 50 alkoxycarbonyl, a substituted or unsubstituted C 6 -C 60 aryl, and a substituted or unsubstituted C 1 -C 60 heteroaryl.

2. The organic compound of claim 1 , wherein the organic compound has the structure represented by Formula (2):

wherein Ar 1 and Ar 2 are each independently selected from the group consisting of a substituted or unsubstituted C 6 -C 60 aryl and a substituted or unsubstituted C 1 -C 60 heteroaryl;
R 1 , R 2 and R 4 are each independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C 1 -C 50 alkyl, a substituted or unsubstituted C 1 -C 50 alkoxy, a substituted or unsubstituted C 1 -C 50 alkoxycarbonyl, a substituted or unsubstituted C 6 -C 60 aryl, a substituted or unsubstituted C 6 -C 50 aryloxy, a substituted or unsubstituted C 6 -C 60 arylthio, a substituted or unsubstituted C 1 -C 60 heteroaryl, a halogen, a cyano, a hydroxyl, and a carbonyl;
R 5 is selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C 1 -C 50 alkyl, a substituted or unsubstituted C 1 -C 50 alkoxycarbonyl, a substituted or unsubstituted C 6 -C 60 aryl, and a substituted or unsubstituted C 1 -C 60 heteroaryl; and
X 1 through X 4 are each independently a chemical bond, or each independently selected from the group consisting of a substituted or unsubstituted C 6 -C 60 arylene and a substituted or unsubstituted C 1 -C 60 heteroarylene; and X 1 through X 4 may each independently form fused rings with the phenyl rings they are bonded to.

3. The organic compound of claim 1 , wherein the organic compound has the structure represented by Formula (3):

wherein Ar 1 and Ar 2 are each independently selected from the group consisting of a substituted or unsubstituted C 6 -C 60 aryl and a substituted or unsubstituted C 1 -C 60 heteroaryl; and
R 1 , R 2 , and R 3 are each independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C 1 -C 50 alkyl, a substituted or unsubstituted C 1 -C 50 alkoxy, a substituted or unsubstituted C 1 -C 50 alkoxycarbonyl, a substituted or unsubstituted C 6 -C 60 aryl, a substituted or unsubstituted C 6 -C 60 aryloxy, a substituted or unsubstituted C 6 -C 60 arylthio, a substituted or unsubstituted C 1 -C 60 heteroaryl, a halogen, a cyano, a hydroxyl, and a carbonyl;
R 5 is selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C 1 -C 50 alkyl, a substituted or unsubstituted C 1 -C 50 alkoxycarbonyl, a substituted or unsubstituted C 6 -C 60 aryl, and a substituted or unsubstituted C 1 -C 60 heteroaryl; and
X 1 through X 4 are each independently a chemical bond, or each independently selected from the group consisting of a substituted or unsubstituted C 6 -C 60 arylene and a substituted or unsubstituted C 1 -C 60 heteroarylene; and X 1 through X 4 may each independently form fused rings with the phenyl rings they are bonded to.

4. The organic compound of claim 1 , wherein the organic compound has the structure represented by Formula (4):

wherein Ar 1 and Ar 2 are each independently selected from the group consisting of a substituted or unsubstituted C 6 -C 60 aryl and a substituted or unsubstituted C 1 -C 60 heteroaryl;
X 3 is a chemical bond, or selected from the group consisting of a substituted or unsubstituted C 6 -C 60 arylene and a substituted or unsubstituted C 1 -C 60 heteroarylene; and X 3 may form fused rings with the phenyl ring it is bonded to; and
R 5 is selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C 1 -C 50 alkyl, a substituted or unsubstituted C 1 -C 50 alkoxycarbonyl, a substituted or unsubstituted C 6 -C 60 aryl, and a substituted or unsubstituted C 1 -C 60 heteroaryl.

5. The organic compound of claim 1 , wherein the organic compound has the structure represented by Formula (4-I):

wherein Ar 1 and Ar 2 are each independently selected from the group consisting of a substituted or unsubstituted C 6 -C 60 aryl and a substituted or unsubstituted C 1 -C 60 heteroaryl;
X 4 is a chemical bond, or selected from the group consisting of a substituted or unsubstituted C 6 -C 60 arylene and a substituted or unsubstituted C 1 -C 60 heteroarylene; and X 4 may form fused rings with the phenyl ring it is bonded to; and
R 5 is selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C 1 -C 50 alkyl, a substituted or unsubstituted C 1 -C 50 alkoxycarbonyl, a substituted or unsubstituted C 6 -C 60 aryl, and a substituted or unsubstituted C 1 -C 60 heteroaryl.

6. The organic compound of claim 1 , wherein the structure

is selected from the following structures (5-1) through (5-9);

7. The organic compound of claim 1 , wherein R 5 is selected from the group consisting of : —CH 3 , —CH 2 CH 3 ,

8. The organic compound of claim 1 , wherein X 1 through X 4 are each independently selected from a chemical bond,

Assignees

• Dow Global Technologies Llc
• Rohm & Haas Elect Materials Korea Ltd

Inventors

• Tang Zhengming
• Xing Chong
• Feng Shaoguang
• Zhu Minrong
• Ren Hua
• Na Hong-Yeop
• Liu Yuchen
• Wright Robert J
• Devore David D

Classifications

• C09K2211/1011

  Condensed systems · CPC title

• C09K2211/1007

  Non-condensed systems · CPC title

• C07D207/335 Primary

  Radicals substituted by nitrogen atoms not forming part of a nitro radical · CPC title

• C09K2211/1029

  containing one nitrogen atom as the heteroatom · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title