IP Library Granted Patent US 11,459,344
Granted Patent B2
US 11,459,344 · App. 16/691,494 · Granted Oct 4, 2022

Compound, light-emitting material, and organic light-emitting display panel

Inventors: Wei Gao (Shanghai, CN); Lei Zhang (Shanghai, CN); Wenpeng Dai (Shanghai, CN); Jinghua Niu (Shanghai, CN); Dongyang Deng (Shanghai, CN)
Assignees: WUHAN TIANMA MICROELECTRONICS CO., LTD.; WUHAN TIANMA MICROELECTRONICS CO., LTD. SHANGHAI BRANCH
C07F5/027C07D409/14C07F7/0816H01L51/008H01L51/0061H01L51/0067H01L51/0072H01L51/0074H01L51/0094H01L51/5056H01L51/5072H01L51/5092H01L51/5206H01L51/5221
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Quick Facts
Patent No.
US 11,459,344
App. No.
16/691,494
Granted
Oct 4, 2022
Kind
B2
Abstract

The present disclosure describes a compound, a light-emitting material, an organic light-emitting display panel and an organic light-emitting display device. The compound has the structure of Formula I. The light-emitting material comprises any one or a combination of at least two of the compounds. The organic light-emitting display panel comprises an anode and a cathode disposed opposite to each other, and an organic layer disposed between the anode and the cathode. The material of the organic layer comprises any one or a combination of at least two of the compounds. The organic light-emitting display device comprises the organic light-emitting display panel. The compound has an energy level difference between a singlet and a triplet states as ΔE st ≥0.30 eV, and, when used in an organic light-emitting display panel, can further increase the luminous efficiency of the device.

Claims (55)

1. A compound of Formula I:

wherein Formula I is:

wherein in Formula I, D i is any one selected from the group consisting of a substituted or unsubstituted arylamino group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted carbazole derivative group, a substituted or unsubstituted acridine group, and a substituted or unsubstituted acridine derivative group;

wherein in Formula I, A j is any one selected from an aryl group including an electron-withdrawing group;

wherein the electron-withdrawing group includes any one or a combination of at least two selected from the group consisting of carbonyl, a sulfone group, a six-membered phosphorus heterocyclic group containing phosphoryl, a boron atom and an imide;

wherein in Formula I, m is an integer from 1 to 4, and

n is an integer from 1 to 4;

wherein A j is any one selected from the group consisting of

wherein # indicates a bonding position;

wherein R 16 is any one selected from the group consisting of substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl;

X is any one selected from the group consisting of

an oxygen atom, and a sulfur atom; and

wherein R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 and R 15 are each independently any one selected from the group consisting of substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl.

2. The compound according to claim 1 , wherein m≥n.

3. The compound according to claim 1 , wherein the compound is a structure of Formula II or a structure of Formula III;

wherein Formula II is:

wherein Formula III is:

wherein D i is any one selected from the group consisting of a substituted or unsubstituted acylamino group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted carbazole derivative group, a substituted or unsubstituted acridine group, and a substituted or unsubstituted acridine derivative group; and

wherein A j is any one selected from an aryl group containing an electron-withdrawing group;

wherein the electron-withdrawing group includes any one or a combination of at least two selected from the group consisting of carbonyl, a sulfone group, phosphoryl, a boron atom and an imide.

4. The compound according to claim 1 , wherein D is selected from the group

wherein # indicates a bonding position;

wherein a and b each is independently selected from an integer from 0 to 5, and

wherein R c and R f each is independently selected from the group consisting of substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl.

5. The compound according to claim 1 , wherein D i is any one selected from the group consisting of

wherein # indicates a bonding position.

6. The compound according to claim 1 , wherein D i is any one selected from the group consisting of

wherein # indicates a bonding position;

wherein r and s each is independently selected from an integer from 0 to 4,

t is an integer from 0 to 3,

p is an integer from 0 to 2,

Y is any one selected from the group consisting of a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom, and a silicon atom; and

wherein R g , R h , R w and R v are each independently any one selected from the group consisting of substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl.

7. The compound according to claim 1 , wherein D i is any one selected from the group consisting of

wherein # indicates a bonding position; and

wherein R 5 is any one selected from the group consisting of substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl.

8. The compound according to claim 1 , wherein D i is any one selected from the group consisting of

wherein # indicates a bonding position;

wherein r and s are each independently selected from an integer from 0 to 4,

p and q are each independently selected from an integer from 0 to 2,

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

wherein R′, R g , R v , R h and R k are each independently any one selected from the group consisting of substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl.

9. The compound according to claim 1 , wherein D i is any one selected from the group consisting of

wherein # indicates a bonding position.

10. The compound according to claim 1 , wherein m is 1 and n is 1.

11. The compound according to claim 1 , wherein the compound includes an energy level difference between a singlet level and a triplet level and ΔE st =E S1 −E T1 ≤0.3 eV.

12. The compound according to claim 1 , wherein the compound is any one selected from the group consisting of compounds P1 to P15 and P17 to P28 as follows:

13. A light-emitting material comprising any one or a combination of at least two of the compounds according to claim 1 , wherein the compound having the structure of Formula I.

14. An organic light-emitting display device comprising an anode and a cathode disposed opposite to each other, and an organic layer disposed between the anode and the cathode;

wherein a material of the organic layer comprises any one or a combination of at least two of the compounds according to claim 1 , wherein the compound having the structure of Formula I.

15. The organic light-emitting display device according to claim 14 , wherein the organic light-emitting display device further comprises a cap layer deposed on the side of the cathode facing away from the anode, wherein the material of the cap layer comprises any one or a combination of at least two of the compounds according to Formula I.

16. The organic light-emitting display device according to claim 14 , wherein the organic layer comprises any one or a combination of at least two of the group consisting 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.

17. The organic light-emitting display device according to claim 14 , wherein the compound as a guest material or host material in the organic layer.

18. The organic light-emitting display device according to claim 14 , wherein the organic layer comprises a light-emitting layer, wherein the compound is a host material or guest material in the light-emitting layer.

19. The organic light-emitting display device according to claim 14 , wherein the organic light-emitting display device is an organic light-emitting display panel.

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 Dec 4, 2019
From: GAO, WEI; ZHANG, LEI; DAI, WENPENG; NIU, JINGHUA; DENG, DONGYANG
To: SHANGHAI TIANMA AM-OLED CO., LTD.
Reel/Frame 051182/0663 →
Priority Claims (1)
CN 201910340979.X · Apr 25, 2019 · national
Continuity (1)
Related Publication 20200339608A1 · Oct 29, 2020