IP Library Granted Patent US 11,780,831
Granted Patent B2
US 11,780,831 · App. 17/035,952 · Granted Oct 10, 2023

Compound, display panel and display apparatus

Inventors: Wei Gao (Shanghai, CN); Lei Zhang (Shanghai, CN); Wenpeng Dai (Shanghai, CN); Quan Ran (Shanghai, CN); Lu Zhai (Shanghai, CN); Wenjing Xiao (Shanghai, CN); Jinghua Niu (Shanghai, CN)
Assignees: SHANGHAI TIANMA AM-OLED CO., LTD.; WUHAN TIANMA MICRO-ELECTRONICS CO., LTD
C07D409/14C07D519/00H10K85/40H10K85/631H10K85/653H10K85/654H10K85/6572H10K85/6574H10K85/6576H10K50/15H10K50/16H10K50/171H10K50/18
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Quick Facts
Patent No.
US 11,780,831
App. No.
17/035,952
Granted
Oct 10, 2023
Kind
B2
Abstract

Provided is a compound represented by formula 1, and a display panel and a display apparatus including the compound. In formula 1, L 1 and L 2 are each independently selected from the group consisting of a single bond, C6-C30 aryl, and C4-C30 heteroaryl; a and b are each independently selected from 0, 1, 2, 3, or 4; D 1 and D 2 are each independently a nitrogen-containing electron donor unit selected from the group consisting of carbazolyl and derivative groups thereof, acridinyl and derivative groups thereof, diarylamino and derivative groups thereof, and triarylamino and derivative groups thereof; and c and d are each independently selected from 0, 1, 2, 3, or 4, and c+d≥1.

Claims (53)

1. A compound, having a structure represented by formula 1:

wherein L 1 and L 2 are each independently selected from the group consisting of a single bond, a substituted or unsubstituted C6-C30 aryl, and a C4-C30 heteroaryl; a and b are each independently selected from 0, 1, 2, 3, or 4;

D 1 and D 2 are each independently a nitrogen-containing electron donor unit selected from the group consisting of carbazolyl and derivative groups thereof, acridinyl and derivative groups thereof, diarylamino and derivative groups thereof, and triarylamino and derivative groups thereof; and

c and d are each independently selected from 0, 1, 2, 3, or 4, and c+d≥1.

2. The compound according to claim 1 , wherein the compound has a structure represented by formula 1-1 or formula 1-2:

3. The compound according to claim 1 , wherein L 1 and L 2 are each independently selected from the group consisting of phenyl, biphenyl, naphthyl, anthracyl, phenanthryl, acenaphthylenyl, pyrenyl, perylenyl, fluorenyl, spirodifluorenyl, chrysenyl, benzophenanthryl, and benzanthracyl.

4. The compound according to claim 1 , wherein D 1 and D 2 are each independently selected from the group consisting of:

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

q is 0, 1 or 2;

U 1 , U 2 , and U 3 are each independently selected from the group consisting of a hydrogen atom, C1-C6 alkyl, C1-C6 alkoxy, and C6-C12 aryl;

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

# indicates a bonding position.

5. The compound according to claim 4 , wherein D 1 and D 2 are each independently selected from the group consisting of:

6. The compound according to claim 1 , wherein D 1 and D 2 are each independently selected from the group consisting of:

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, a sulfur atom, and a silicon atom;

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

U 1 , U 2 , U 3 and U 4 are each independently selected from the group consisting of a hydrogen atom, C1-C6 alkyl, C3-C6 cycloalkyl, C1-C6 alkoxy, C6-C12 aryl, and C12-C20 substituted or unsubstituted diphenylamino;

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

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

# indicates a bonding position.

7. The compound according to claim 6 , wherein D 1 and D 2 are each independently selected from the group consisting of:

wherein R and R′ are each independently selected from the group consisting of a hydrogen atom, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 cycloalkyl, C6-C12 aryl, and C4-C12 heteroaryl.

8. The compound according to claim 1 , wherein D 1 and D 2 are each independently selected from the group consisting of:

wherein U 1 , U 2 and U 3 are each independently selected from the group consisting of a hydrogen atom, C1-C6 alkyl, and C1-C6 alkoxy;

m, n, and p are each independently selected from 0, 1 or 2; and

# indicates a bonding position.

9. The compound according to claim 8 , wherein D 1 and D 2 are each independently selected from the group consisting of:

wherein # indicates a bonding position.

10. The compound according to claim 1 , wherein D 1 and D 2 are each independently selected from the group consisting of:

wherein X is an oxygen atom or a sulfur atom;

m and n are each independently selected from 0, 1 or 2;

U 1 and U 2 are each independently selected from the group consisting of a hydrogen atom, C1-C6 alkyl, C3-C6 cycloalkyl, and C1-C6 alkoxy; and

# indicates a bonding position.

11. The compound according to claim 1 , wherein the compound is selected from the following compounds:

12. The compound according to claim 1 , wherein the compound satisfies ΔE ST ≤0.30 eV.

13. A display panel, comprising an organic light-emitting device, wherein the organic light-emitting device comprises:

an anode;

a cathode; and

a light-emitting layer disposed between the anode and the cathode, wherein the light-emitting layer comprises one or more compounds having a structure represented by formula 1 and configured to emit light:

wherein L 1 and L 2 are each independently selected from the group consisting of a single bond, a substituted or unsubstituted C6-C30 aryl, and a C4-C30 heteroaryl; a and b are each independently selected from 0, 1, 2, 3, or 4;

D 1 and D 2 are each independently a nitrogen-containing electron donor unit selected from the group consisting of carbazolyl and derivative groups thereof, acridinyl and derivative groups thereof, diarylamino and derivative groups thereof, and triarylamino and derivative groups thereof; and

c and d are each independently selected from 0, 1, 2, 3, or 4, and c+d≥1.

14. The display panel according to claim 13 , wherein a host material or a guest material of the light-emitting layer is at least one of the one or more compounds.

15. The display panel according to claim 13 , wherein the light-emitting layer comprises a host material and a guest material, the host material is at least one of the one or more compounds, and the guest material is a red phosphorescent material and/or a green phosphorescent material.

16. The display panel according to claim 13 , further comprising one or more of a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, or an electron injection layer.

17. A display apparatus, comprising a display panel, wherein the display panel comprises an organic light-emitting device comprising:

an anode;

a cathode; and

a light-emitting layer disposed between the anode and the cathode, wherein a light-emitting material of the light-emitting layer comprises one or more compounds having a structure represented by formula 1:

wherein L 1 and L 2 are each independently selected from the group consisting of a single bond, a substituted or unsubstituted C6-C30 aryl, and a C4-C30 heteroaryl; a and b are each independently selected from 0, 1, 2, 3, or 4;

D 1 and D 2 are each independently a nitrogen-containing electron donor unit selected from the group consisting of carbazolyl and derivative groups thereof, acridinyl and derivative groups thereof, diarylamino and derivative groups thereof, and triarylamino and derivative groups thereof; and

c and d are each independently selected from 0, 1, 2, 3, or 4, and c+d≥1.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 10, 2022
From: GAO, WEI; ZHANG, LEI; DAI, WENPENG; RAN, QUAN; ZHAI, LU; XIAO, WENJING; NIU, JINGHUA
To: SHANGHAI TIANMA AM-OLED CO., LTD.
Reel/Frame 059885/0604 →
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 →
Continuity (1)
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