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

Patent metadata

Field	Value
Publication number	US-10005729-B2
Application number	US-201515537449-A
Country	US
Kind code	B2
Filing date	Dec 25, 2015
Priority date	Dec 26, 2014
Publication date	Jun 26, 2018
Grant date	Jun 26, 2018

Abstract

Organic compounds 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 R c , R d , R c ′ and R d ′ are each independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C 1 -C 20 alkyl, a substituted or unsubstituted C 1 -C 20 alkoxy, a substituted or unsubstituted C 6 -C 20 aryl, a substituted or unsubstituted C 1 -C 20 heteroaryl, a substituted or unsubstituted C 6 -C 20 aryloxy, a halogen, and a cyano;
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 3 -C 50 cycloalkyl, a substituted or unsubstituted C 6 -C 60 aryl, and a substituted or unsubstituted C 1 -C 60 heteroaryl;
R 6 and R 7 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, 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; with the proviso that at least one of R 6 and R 7 is a substituted amino group having the structure of

wherein Ar 1 and Ar 2 are each independently a substituted or unsubstituted C 6 -C 60 aryl;
R a , R b , R a ′, and R b ′ are each independently selected from hydrogen, a substituted or unsubstituted C 6 -C 60 aryl or a substituted or unsubstituted C 1 -C 60 heteroaryl; and
X 1 and X 2 are each a chemical bond, or each independently selected from the group consisting of a substituted or unsubstituted C 1 -C 50 alkylene, a substituted or unsubstituted C 3 -C 50 cycloalkylene, a substituted or unsubstituted C 6 -C 60 arylene, and a substituted or unsubstituted C 1 -C 60 heteroarylene; and optionally X 1 and X 2 may each independently form one or more rings with the rings they are bonded to.

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

wherein R c , R d , R c ′ and R d ′ are each independently selected from the group consisting of hydrogen, deuterium, a substituted or unsubstituted C 1 -C 20 alkyl, a substituted or unsubstituted C 1 -C 20 alkoxy, a substituted or unsubstituted C 6 -C 20 aryl, a substituted or unsubstituted C 1 -C 20 heteroaryl, a substituted or unsubstituted C 6 -C 20 aryloxy, a halogen, and a cyano;
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 3 -C 50 cycloalkyl, a substituted or unsubstituted C 6 -C 60 aryl, and a substituted or unsubstituted C 1 -C 60 heteroaryl;
R 6 and R 7 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, 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; with the proviso that at least one of R 6 and R 7 is a substituted amino group having the structure of

wherein Ar 1 and Ar 2 are each independently a substituted or unsubstituted C 6 -C 60 aryl;
R a , R b , R a ′, and R b ′ are each independently selected from hydrogen, a substituted or unsubstituted C 6 -C 60 aryl or a substituted or unsubstituted C 1 -C 60 heteroaryl; and
X 1 and X 2 are each a chemical bond, or each independently selected from the group consisting of a substituted or unsubstituted C 1 -C 50 alkylene, a substituted or unsubstituted C 3 -C 50 cycloalkylene, a substituted or unsubstituted C 6 -C 60 arylene, and a substituted or unsubstituted C 1 -C 60 heteroarylene; and optionally X 1 and X 2 may each independently form one or more rings with the rings they are bonded to.

3. The organic compound of claim 1 , wherein the organic compound is represented by Formula (2b):

wherein R 5 is selected from the group consisting of hydrogen, deuterium, a substitute d or unsubstituted C 1 -C 50 alkyl, a substituted or unsubstituted C 3 -C 50 cycloalkyl, a substituted or unsubstituted C 6 -C 60 aryl, and a substituted or unsubstituted C 1 -C 60 heteroaryl;
R 7 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 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 a , R b , R a ′, and R b ′ are each independently selected from hydrogen, a substituted or unsubstituted C 6 -C 60 aryl or a substituted or unsubstituted C 1 -C 60 heteroaryl;
Ar 1 and Ar 2 are each independently a substituted or unsubstituted C 6 -C 60 aryl; and
X 1 and X 2 are each a chemical bond, or each independently selected from the group consisting of a substituted or unsubstituted C 1 -C 50 alkylene, a substituted or unsubstituted C 3 -C 50 cycloalkylene, a substituted or unsubstituted C 6 -C 60 arylene, and a substituted or unsubstituted C 1 -C 60 heteroarylene; and optionally X 1 and X 2 may each independently form one or more rings with the rings they are bonded to.

4. The organic compound of claim 1 , wherein the organic compound is represented by Formula (2c):

wherein 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 3 -C 50 cycloalkyl, a substituted or unsubstituted C 6 -C 60 aryl, and a substituted or unsubstituted C 1 -C 60 heteroaryl;
R 6 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 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 a , R b , R a ′, and R b ′ are each independently selected from hydrogen, a substituted or unsubstituted C 6 -C 60 aryl or a substituted or unsubstituted C 1 -C 60 heteroaryl;
Ar 1 and Ar 2 are each independently a substituted or unsubstituted C 6 -C 60 aryl;

Assignees

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

Inventors

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

Classifications

• C09K2211/1011

  Condensed systems · CPC title

• C07D209/14

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

• H01L51/5056

  Electricity · mapped topic

• C09K11/06

  containing organic luminescent materials · CPC title

• C07D209/58 Primary

  [b]- or [c]-condensed · CPC title