IP Library Granted Patent US 12,082,499
Granted Patent B2
US 12,082,499 · App. 16/831,646 · Granted Sep 3, 2024

Compound and its application

Inventors: Wenjing Xiao (Shanghai, CN); Wei Gao (Shanghai, CN); Wenpeng Dai (Shanghai, CN); Lei Zhang (Shanghai, CN); Jinghua Niu (Shanghai, CN); Yi Liu (Shanghai, CN)
Assignees: WUHAN TIANMA MICRO-ELECTRONICS CO., LTD.; WUHAN TIANMA MICROELECTRONICS CO., LTD. SHANGHAI BRANCH
H10K85/657C07F9/65685C09K11/06H10K85/636H10K85/6572C09K2211/1018H10K50/11H10K50/15H10K50/16H10K50/17H10K50/171H10K50/18H10K2101/10
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Quick Facts
Patent No.
US 12,082,499
App. No.
16/831,646
Granted
Sep 3, 2024
Kind
B2
Abstract

An organic compound has a structure as shown in Formula (I). The compound has a phosphorus-oxygen five-membered ring combined with a five-membered ring as an electron acceptor unit. The compound has a high luminous efficiency and a lower material cost than phosphorescent metal complexes. The compound can be built into a stack structure of organic optoelectronic device, such as OLED. The resultant organic optoelectronic device includes an anode, a cathode, and at least one organic thin film located between the anode and the cathode, the organic thin film contains the compound as shown in Formula (I).

Claims (40)

1. A compound, having a structure of Formula (II-1), Formula (II-2) or Formula (II-5):

wherein:

L 1 and L 2 are each independently selected from any one of a single bond, a substituted or unsubstituted C6-C40 arylene group, and a substituted or unsubstituted C3-C40 heteroarylene group; and

D 1 and D 2 are each independently selected from any one of a substituted or unsubstituted C4-C40 carbazole group, a substituted or unsubstituted C4-C40 acridine group, a substituted or unsubstituted C6-C40 arylamine group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted spirofluorenyl group, a substituted or unsubstituted diphenyl ether group, and a substituted or unsubstituted diindolocyclopentadiene group, and the D 1 and D 2 are all electron-donating groups;

wherein when a substituent is present in any one of said groups, the substituent includes any one or a combination of at least two of cyano, halogen, phenoxy, C1-C20 alkyl group, C1-C20 alkoxyl group, C6-C40 aryl group, C4-C40 heteroaryl group, and C6-C40 arylamine group.

2. The compound according to claim 1 , wherein the substituted or unsubstituted C4-C40 carbazole group includes the following groups:

wherein Y is independently selected from any one of a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom, and a silicon atom;

wherein a is selected from an integer of 0-2;

wherein R 1 is selected from any one of a hydrogen atom, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C1-C20 alkoxyl group, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted C3-C30 heteroaryl group;

wherein when a substituent is present in the substituted C4-C40 carbazole group, the substituent includes any one or a combination of at least two of cyano, halogen, phenoxy, C1-C20 alkyl group, C1-C20 alkoxyl group, C6-C40 aryl group, C4-C40 heteroaryl group, and C6-C40 arylamine group; and

wherein # represents the linking site of the group.

3. The compound according to claim 1 , wherein the substituted or unsubstituted C4-C40 acridine group includes the following groups:

wherein Y and Z are each independently selected from any one of a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom, and a silicon atom;

wherein a and b are each independently selected from an integer of 0-2;

wherein R 1 and R 2 are each independently selected from any one of a hydrogen atom, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C1-C20 alkoxyl group, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted C3-C30 heteroaryl group;

wherein when a substituent is present in the substituted C4-C40 acridine group, the substituent includes any one or a combination of at least two of cyano, halogen, phenoxy, C1-C20 alkyl group, C1-C20 alkoxyl group, C6-C40 aryl group, C4-C40 heteroaryl group, and C6-C40 arylamine group; and

wherein # represents the linking site of the group.

4. The compound according to claim 1 , wherein the substituted or unsubstituted C6-C40 arylamine group includes the following group:

wherein when a substituent is present in the substituted C6-C40 arylamine group, the substituent includes any one or a combination of at least two of cyano, halogen, phenoxy, C1-C20 alkyl group, C1-C20 alkoxyl group, C6-C40 aryl group, C4-C40 heteroaryl group, and C6-C40 arylamine group; and

wherein # represents the linking site of the group.

5. The compound according to claim 1 , wherein D 1 and D 2 are each further independently selected from any one of the following groups which are substituted or unsubstituted:

wherein Y and Z are each independently selected from any one of a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom, and a silicon atom;

wherein a and b are each independently selected from an integer of 0-2;

wherein R 1 and R 2 are each independently selected from any one of a hydrogen atom, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C1-C20 alkoxyl group, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted C3-C30 heteroaryl group;

wherein when a substituent is present in the substituted group of D 1 or D 2 , the substituent includes any one or a combination of at least two of cyano, halogen, phenoxy, C1-C20 alkyl group, C1-C20 alkoxyl group, C6-C40 aryl group, C4-C40 heteroaryl group, and C6-C40 arylamine group; and

wherein # represents the linking site of the group.

6. The compound according to claim 1 , wherein the D 1 and D 2 are each independently selected from any one of the following groups:

wherein R 1 is selected from any one of a hydrogen atom, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C1-C20 alkoxyl group, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted C3-C30 heteroaryl group;

when a substituent is present in the substituted group of D 1 or D 2 , the substituent includes any one or a combination of at least two of cyano, halogen, phenoxy, C1-C20 alkyl group, C1-C20 alkoxyl group, C6-C40 aryl group, C4-C40 heteroaryl group, and C6-C40 arylamine group; and

wherein # represents the linking site of the group.

7. The compound according to claim 1 , wherein L 1 and L 2 are each independently selected from any one of a single bond, a phenylene group, a thienylene group, a naphthylene group, an anthrylene group, a phenanthrylene group, or a pyrenylene group.

8. The compound according to claim 1 , wherein L 1 and L 2 are each independently selected from a single bond, or a phenylene group.

9. The compound according to claim 1 , wherein the compound has any one of the following structures:

10. The compound according to claim 1 , an energy level difference between the lowest singlet energy level S1 and the lowest triplet energy level T1 of the compound is ≤0.30 eV, i.e. ΔE st =E S1 −E T1 ≤0.30 eV.

11. A method of manufacturing an organic optoelectronic device, comprising:

forming an organic thin film located between an anode and a cathode of the organic optoelectronic device using the compound according to claim 1 .

12. An organic optoelectronic device, wherein the organic optoelectronic device comprises an anode, a cathode, and at least one organic thin film located between the anode and the cathode, and the organic thin film contains the compound according to claim 1 .

13. The organic optoelectronic device according to claim 12 , wherein the organic thin film further comprises a light emitting layer, and the light emitting layer contains the compound.

14. The organic optoelectronic device according to claim 13 , wherein the compound is used as a host material, a doping material, or a co-doping material of the light emitting layer.

15. The organic optoelectronic device according to claim 12 , wherein the organic thin film further comprises any one or a combination of at least two of a hole transport layer, a hole injection layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer and an electron injection layer.

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 Apr 2, 2020
From: XIAO, WENJING; GAO, WEI; DAI, WENPENG; ZHANG, LEI; NIU, JINGHUA; LIU, YI
To: SHANGHAI TIANMA AM-OLED CO., LTD.
Reel/Frame 052298/0127 →
Priority Claims (1)
CN 201910936377.0 · Sep 29, 2019 · national
Continuity (1)
Related Publication 20200227648A1 · Jul 16, 2020