IP Library Granted Patent US 11,785,841
Granted Patent B2
US 11,785,841 · App. 16/732,136 · Granted Oct 10, 2023

Compound, display panel and display apparatus

Inventors: Wenpeng Dai (Shanghai, CN); Wei Gao (Shanghai, CN); Jinghua Niu (Shanghai, CN); Lei Zhang (Shanghai, CN); Yang Li (Shanghai, CN); Dongyang Deng (Shanghai, CN); Ping An (Shanghai, CN)
Assignees: WUHAN TIANMA MICROELECTRONICS CO., LTD.; WUHAN TIANMA MICROELECTRONICS CO., LTD. SHANGHAI BRANCH
H10K85/615C07D401/10C07D403/08C07D403/14C09K11/06H10K85/622H10K85/654H10K85/6572C09K2211/1018H10K50/11H10K50/15H10K50/16H10K2101/10H10K2101/30
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Quick Facts
Patent No.
US 11,785,841
App. No.
16/732,136
Granted
Oct 10, 2023
Kind
B2
Abstract

A compound having a D-(π)-σ-(π)-A chemical structure and improving brightness and efficiency of light-emitting is described. In an embodiment, the compound has a chemical structure according to Formula (I), in which L 1 and L 2 are each at least one of a single bond, C1-C20 alkylene, C3-C20 cycloalkylene, C3-C20 heterocyclic alkylene, C6-C40 arylene, C4-C40 heteroarylene, C10-C60 fused arylene, or C10-C60 fused heteroarylene; the electron donor D is C1-C20 alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C3-C20 heterocyclic group, C6-C40 aryl, C4-C40 heteroaryl, C10-C60 fused arylene, C10-C60 fused heteroarylene, C12-C40 carbazolyl and its derivative groups, C12-C40 diphenylamino and its derivative groups, C18-C60 triphenylamino and its derivative groups, or C12-C40 acridinyl and its derivative groups; and the electron acceptor A is a nitrogen-containing heterocyclic group, a cyano-containing group, a triarylboron-based group, a benzophenone-based group, an aromatic heterocyclic ketone-based group, a sulfone-based group, or a phosphoroso-containing groups.

Claims (38)

1. A compound having a chemical structure according to Formula (I):

wherein D is an electron donor, A is an electron acceptor; m is a number of the electron donors D, n is a number of the electron acceptors A, and m and n are each an integer independently selected from 1, 2 and 3; p is a number of L 1 , q is a number of L 2 , and p and q are each an integer independently selected from 0, 1, or 2;

L 1 and L 2 are each independently selected from the group consisting of a single bond, a substituted or unsubstituted C1-C20 alkylene, a substituted or unsubstituted C3-C20 cycloalkylene, a substituted or unsubstituted C3-C20 heterocyclic alkylene, a substituted or unsubstituted C6-C40 arylene, a substituted or unsubstituted C4-C40 heteroarylene, a substituted or unsubstituted C10-C60 fused arylene, a substituted or unsubstituted C10-C60 fused heteroarylene, and combinations thereof;

D is selected from the group consisting of a substituted or unsubstituted C1-C20 alkyl, a substituted or unsubstituted C3-C20 cycloalkyl, a substituted or unsubstituted C1-C20 alkoxy, a substituted or unsubstituted C3-C20 heterocyclic group, a substituted or unsubstituted C6-C40 aryl, a substituted or unsubstituted C4-C40 heteroaryl, a substituted or unsubstituted C10-C60 fused arylene, a substituted or unsubstituted C10-C60 fused heteroarylene, a substituted or unsubstituted C12-C40 carbazolyl and its derivative groups, a substituted or unsubstituted C12-C40 diphenylamino and its derivative groups, a substituted or unsubstituted C18-C60 triphenylamino and its derivative groups, a substituted or unsubstituted C12-C40 acridinyl and its derivative groups, and combinations thereof; and

A is selected from the group consisting of a nitrogen-containing heterocyclic group, a cyano-containing group, a triarylboron-based group, a benzophenone-based group, an aromatic heterocyclic ketone-based group, a sulfone-based group, a phosphoroso-containing groups, and combinations thereof;

wherein L1 and L2 are identical and are phenyl, m and n are each 1;

wherein D is any one of the following groups:

and

wherein A is any one of the following groups:

wherein R is selected from the group consisting of a hydrogen atom, C1-C20 alkyl, C1-C20 alkoxy, C4-C8 cycloalkyl, C6-C40 aryl, and C4-C40 heteroaryl; and

# indicates a bonding position.

2. The compound according to claim 1 , wherein L 1 and L 2 are different.

3. The compound according to claim 1 , wherein p is 0, and q is 1.

4. The compound according to claim 1 , wherein D is any one of the following formulas:

wherein m, n and p are each an integer independently selected from 0, 1, 2 or 3;

U 1 , U 2 , and U 3 are each independently selected from the group consisting of a hydrogen atom, a substituted or unsubstituted C1-C30 alkyl, a substituted or unsubstituted silylene, a substituted or unsubstituted C3-C20 cycloalkyl, a substituted or unsubstituted C1-C30 alkoxy, a substituted or unsubstituted C6-C30 aryl, a substituted or unsubstituted C10-C30 fused aryl, and combinations thereof; and

# indicates a bonding position.

5. The compound according to claim 4 , wherein the electron donor D is any one of the following groups:

wherein R is selected from the group consisting of a hydrogen atom, a substituted or unsubstituted C1-C20 alkyl, a substituted or unsubstituted silylene, a substituted or unsubstituted C3-C20 cycloalkyl, a substituted or unsubstituted C1-C20 alkoxy, a substituted or unsubstituted C3-C20 heterocyclic group, a substituted or unsubstituted C6-C40 aryl, a substituted or unsubstituted C10-C30 fused aryl, and a substituted or unsubstituted C4-C40 heteroaryl.

6. The compound according to claim 1 , D is any one of the following groups:

wherein Z is selected from the group consisting of a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom and a silicon atom;

X is selected from the group consisting of a carbon atom, a nitrogen atom, an oxygen atom and a sulfur atom;

m, n, p and q are each an integer independently selected from 0, 1, 2 or 3;

U 1 , U 2 , U 3 and U 4 are each independently selected from the group consisting of a hydrogen atom, a substituted or unsubstituted C1-C30 alkyl, a substituted or unsubstituted silylene, a substituted or unsubstituted C3-C20 cycloalkyl, a substituted or unsubstituted C1-C30 alkoxy, a substituted or unsubstituted C6-C30 aryl, and a substituted or unsubstituted C10-C30 fused aryl;

when Z or X is an oxygen atom or a sulfur atom, p or q is 0; and

# indicates a bonding position.

7. The compound according to claim 6 , wherein D is any one of the following groups:

wherein R 1 , R 2 , R 3 and R 4 are each independently selected from the group consisting of a hydrogen atom, a substituted or unsubstituted C1-C20 alkyl, a substituted or unsubstituted C3-C20 cycloalkyl, a substituted or unsubstituted C1-C20 alkoxy, a substituted or unsubstituted C3-C20 heterocyclic group, a substituted or unsubstituted C6-C40 aryl, and a substituted or unsubstituted C4-C40 heteroaryl.

8. The compound according to claim 1 , wherein A is any one of the following groups:

wherein # indicates a bonding position.

9. The compound according to claim 1 , wherein A is any one of the following groups:

wherein # indicates a bonding position.

10. The compound according to claim 1 , wherein A is any one of the following groups:

wherein # indicates a bonding position.

11. The compound according to claim 1 , wherein the compound is any one of the following compounds:

12. A display panel, comprising an organic light-emitting device,

wherein the organic light-emitting device comprises an anode, a cathode arranged opposite to the anode, a capping layer disposed at a side of the cathode facing away from the anode, and an organic layer disposed between the anode and the cathode, the organic layer comprising an electron transmission layer, a hole transmission layer, and a light-emitting layer, wherein at least one of the capping layer, the electron transmission layer, the hole transmission layer, and the light-emitting layer is made of the compound according to claim 1 .

13. A display apparatus, comprising the display panel according to claim 12 .

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 4, 2022
From: SHANGHAI TIANMA AM-OLED CO.,LTD.
To: WUHAN TIANMA MICRO-ELECTRONICS CO., LTD.; WUHAN TIANMA MICROELECTRONICS CO., LTD. SHANGHAI BRANCH
Reel/Frame 059498/0307 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 21, 2020
From: DAI, WENPENG; GAO, WEI; NIU, JINGHUA; ZHANG, LEI; LI, YANG; DENG, DONGYANG; AN, PING
To: SHANGHAI TIANMA AM-OLED CO., LTD.
Reel/Frame 051893/0141 →
Priority Claims (1)
CN 201910441335.X · May 24, 2019 · national
Continuity (1)
Related Publication 20200373493A1 · Nov 26, 2020