Nitrogen heterocycle fused ring-indene compound and organic light-emitting display device

Patent metadata

Field	Value
Publication number	US-11183643-B2
Application number	US-201816212292-A
Country	US
Kind code	B2
Filing date	Dec 6, 2018
Priority date	Jul 26, 2018
Publication date	Nov 23, 2021
Grant date	Nov 23, 2021

Abstract

The present disclosure relates to a nitrogen heterocycle fused ring-indene compound having a structure represented by the Formula (I),in which Ar1 represents a substituted or unsubstituted aromatic fused ring group containing at least one nitrogen heteroaryl; Ar2 represents a chemical group acting as an electron donor; R1 and R2 are independently selected from the group consisting of hydrogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C3-C20 heterocyclyl, substituted or unsubstituted C6-C40 aryl, and substituted or unsubstituted C5-C40 heteroaryl. The compounds according to the present disclosure have high glass transition temperature and thermal stability, and are easy to form a high-quality amorphous film, so that a driving voltage can be lowered, the luminous efficiency and lifetime of the device are improved.

First claim

What is claimed is:

1. A nitrogen heterocycle fused ring-indene compound being any one of following compounds:

wherein
Ar 2 is an electron donor; and
R 1 and R 2 are independently selected from the group consisting of hydrogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C3-C20 heterocyclyl, substituted or unsubstituted C6-C40 aryl, and substituted or unsubstituted C5-C40 heteroaryl.

2. The nitrogen heterocycle fused ring-indene compound according to claim 1 , wherein R 1 and R 2 are each methyl.

3. The nitrogen heterocycle fused ring-indene compound according to claim 1 , wherein Ar 2 is selected from the group consisting of substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted silicylene, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C3-C20 heterocyclyl, substituted or unsubstituted C6-C40 aryl, and substituted or unsubstituted C5-C40 heteroaryl.

4. The nitrogen heterocycle fused ring-indene compound according to claim 1 , wherein Ar 2 is any one of following groups:

wherein m, n and p are integers independently selected from 0, 1, 2 and 3;
U 1 , U 2 and U 3 are independently selected from the group consisting of hydrogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted silicylene, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C10-C 30 fused aryl; and
# indicates a bonding position to which a benzene ring in the compounds I-2, I-3, I-5, or I-6 is bonded.

5. The nitrogen heterocycle fused ring-indene compound according to claim 4 , wherein Ar 2 is any one of following groups:

wherein R is selected from the group consisting of hydrogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted silicylene, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C10-C30 fused aryl.

6. The nitrogen heterocycle fused ring-indene compound according to claim 1 , wherein Ar 2 is any one of following groups:

wherein Z is selected from a group consisting of carbon atom, nitrogen atom, oxygen atom, sulfur atom, and silicon atom;
q is an integer selected from 0, 1, 2 and 3;
U 4 is selected from the group consisting of hydrogen atom, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted silicylene, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C10-C30 fused aryl;
when Z is oxygen or sulfur, q=0; and
# indicates a bonding position to which a benzene ring in the compounds I-2, I-3, I-5, or I-6 is bonded.

7. The nitrogen heterocycle fused ring-indene compound according to claim 6 , wherein Ar 2 is any one of following groups:

8. The nitrogen heterocycle fused ring-indene compound according to claim 1 , wherein Ar2 is any one of following groups:

wherein Z is selected from the group consisting of carbon, nitrogen, oxygen, sulfur, and silicon;
X is selected from the group consisting of carbon, nitrogen, oxygen, and sulfur;
m, n, p and q are integers independently selected from 0, 1, 2 and 3;
U 1 , U 2 , U 3 and U 4 are independently selected from the group consisting of hydrogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted silicylene, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C10-C30 fused aryl;
when Z or X is oxygen or sulfur, p or q is 0; and
# indicates a bonding position to which a benzene ring in the compounds I-2, I-3, I-5, or I-6 is bonded.

9. The nitrogen heterocycle fused ring-indene compound according to claim 8 , wherein Ar 2 is any one of following groups:

wherein R is selected from the group consisting of hydrogen atom, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C3-C20 heterocyclyl, substituted or unsubstituted C6-C40 aryl, and substituted or unsubstituted C5-C40 heteroaryl.

10. The nitrogen heterocycle fused ring-indene compound according to claim 1 , wherein Ar 2 is any one of following groups:

wherein X is selected from the group consisting of oxygen atom, sulfur atom, and silicon atom;
m and n are integers independently selected from 0, 1, 2 and 3;
U 1 and U 2 are independently selected from the group consisting of hydrogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted silicylene, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C10-C30 fused aryl; and
# indicates a bonding position to which a benzene ring in the compounds I-2, I-3, I-5, or I-6 is bonded.

11. The nitrogen heterocycle fused ring-indene compound according to claim 10 , wherein Ar 2 is any one of following groups:

12. The nitrogen heterocycle fused ring-indene compound according to claim 1 , wherein Ar 2 is any one of following groups:

wherein R is selected from the group consisting of hydrogen atom, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C3-C20 heterocyclyl, substituted or unsubstituted C6-C40 aryl, and substituted or unsubstituted C5-C40 heteroaryl.

13. The nitrogen heterocycle fused ring-indene compound according to claim 1 , wherein the nitrogen heterocycle fused ring-indene compound is any one of following compounds:

Assignees

• Shanghai Tianma Am Oled Co Ltd

Inventors

• Zhang Lei
• Wang Xiangcheng
• Gao Wei
• Niu Jinghua
• Liu Ying
• Huang Gaojun
• An Ping
• Luo Xueqiang

Classifications

• C07D403/04

  directly linked by a ring-member-to-ring-member bond · CPC title

• C07D403/10

  linked by a carbon chain containing aromatic rings · CPC title

• C07D241/38

  with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms · CPC title

• C07D417/04

  directly linked by a ring-member-to-ring-member bond · CPC title

• C07D495/04

  Ortho-condensed systems · CPC title