IP Library Granted Patent US 11,691,991
Granted Patent B2
US 11,691,991 · App. 16/922,566 · Granted Jul 4, 2023

Compound, a display panel and a display device

Inventors: Wei Gao (Shanghai, CN); Wenpeng Dai (Shanghai, CN); Lei Zhang (Shanghai, CN); Quan Ran (Shanghai, CN); Jinghua Niu (Shanghai, CN); Xia Li (Shanghai, CN)
Assignee: Shanghai Tianma AM-OLED Co., Ltd.
C07F5/02C07F7/0816H01L51/006H01L51/0072H01L51/0094H01L51/5012
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Quick Facts
Patent No.
US 11,691,991
App. No.
16/922,566
Granted
Jul 4, 2023
Kind
B2
Abstract

The present invention relates to a compound, a display panel and a display device. The compound has a structure represented by Formula I. The compound takes a spiro structure as a non-conjugated connecting unit, and a boron-containing group as an electron-accepting group. A light-emitting compound obtained by taking the group as a building block has a narrower half-peak width and higher color purity. The boron-containing spiro structure is connected with an electron-donating group to obtain a bipolar compound, and as a thermal activation delay fluorescence material, the bipolar compound can be used a light-emitting layer material, particularly a doped material, and can also be used as a fluorescent host material or a phosphorescent host material. The compound provided herein can achieve low drive voltages and high luminescence efficiencies when applied to organic electroluminescent devices.

Claims (47)

1. A compound, having a structure represented by Formula I:

wherein m and n are each independently an integer selected from 1 to 4;

in Formula I, D 1 and D 2 are each independently selected from any one of a substituted or unsubstituted C12-C40 carbazole group, a substituted or unsubstituted C12-C40 acridine group, a substituted or unsubstituted C12-C40 arylamine group, a substituted or unsubstituted fluorenyl, or a substituted or unsubstituted spirofluorenyl;

in Formula I, Ar 1 and Ar 2 are each independently selected from a C1-C20 alkyl, a C1-C20 alkoxy, or a substituted or unsubstituted C6-C40 aryl;

in Formula I, X1 and X2 are each independently selected from any one of an oxygen atom, a sulfur atom,

 wherein #represents a linking bond;

R is selected from a C1-C20 alkyl, a C1-C20 alkoxy, or a substituted or unsubstituted C6-C40 aryl;

in D 1 , D 2 , Ar 1 , Ar 2 and R, substituent is selected from any one or a combination of at least two of a cyano, a halogen, a phenoxy, a C1-C20 alkyl, a C1-C20 alkoxy, a C6-C40 aryl, a C4-C40 heteroaryl, or a C6-C40 arylamine group.

2. The compound according to claim 1 , wherein the compound has a structure represented by Formula II:

wherein D 1 , D 2 , Ar 1 , Ar 2 , X 1 and X 2 each has the same range as defined in claim 1 .

3. The compound according to claim 1 , wherein the compound has a structure represented by Formula III:

wherein D 1 , D 2 , Ar 1 , Ar 2 , X 1 and X 2 each has the same range as defined in claim 1 .

4. The compound according to claim 1 , wherein the substituted or unsubstituted C12-C40 carbazole group comprises any one of the following groups:

wherein X is selected from a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom or a silicon atom; r and s are each independently selected from 0, 1, 2 or 3; when X is an oxygen atom or a sulfur atom, R 3 does not exist;

R 1 , R 2 , R 3 and R 4 are each independently selected from any one of a hydrogen atom, a C1-C20 alkyl, a C1-C20 alkoxy or any one of groups represented be the following chemical formula:

R 5 , R 6 , R 7 and R 8 are each independently selected from any one of a hydrogen atom, a C1-C20 alkyl, a C1-C20 alkoxy or a phenyl;

u and v are each independently selected from 0, 1, 2 or 3;

#represents a linking bond.

5. The compound according to claim 1 , wherein the substituted or unsubstituted C12-C40 carbazole group comprises any one of the following substituted or unsubstituted groups:

R′ is selected from any one of a hydrogen atom, a substituted or unsubstituted C1-C20 alkyl, a substituted or unsubstituted C1-C20 alkoxy, a substituted or unsubstituted C6-C30 aryl, or a substituted or unsubstituted C3-C30 heteroaryl;

#represents a linking bond.

6. The compound according to claim 1 , wherein the substituted or unsubstituted C12-C40 acridine group comprises any one of the following groups:

wherein X and Y are each independently selected from a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom or a silicon atom; r, p and q are each independently selected from 0, 1, 2 or 3; when X is an oxygen atom or a sulfur atom, p is 0; and when Y is an oxygen atom or a sulfur atom, q is 0;

R 1 , R 2 and R 3 are each independently selected from any one of a hydrogen atom, a C1-C20 alkyl, a C1-C20 alkoxy or any one of groups represented by the following chemical formula:

R 5 , R 6 , R 7 and R 8 are each independently selected from any one of a hydrogen atom, a C1-C20 alkyl, a C1-C20 alkoxy or phenyl;

u and v are each independently selected from 0, 1, 2 or 3;

#represents a linking bond.

7. The compound according to claim 1 , wherein the substituted or unsubstituted C12-C40 acridine group comprises any one of the following substituted or unsubstituted groups:

R 9 is independently selected from any one of a hydrogen atom, a C1-C20 alkyl, a C1-C20 alkoxy or a phenyl;

#represents a linking bond.

8. The compound according to claim 1 , wherein the substituted or unsubstituted C12-C40 arylamine group comprises the following group:

wherein r and s are each independently selected from 0, 1, 2 or 3;

R 1 and R 2 are each independently selected from any one of a hydrogen atom, a C1-C20 alkyl, a C1-C20 alkoxy or any one of groups represented by the following chemical formula:

R 5 , R 6 , R 7 and R 8 are each independently selected from any one of a hydrogen atom, a C1-C20 alkyl, a C1-C20 alkoxy or a phenyl;

u and v are each independently selected from 0, 1, 2 or 3;

#represents a linking bond.

9. The compound according to claim 1 , wherein the substituted or unsubstituted C6-C40 arylamine group comprises any one of the following substituted or unsubstituted groups:

wherein #represents a linking bond.

10. The compound according to claim 1 , wherein Ar 1 and Ar 2 are each independently selected from any one of a C1-C12 alkyl, a C1-C12 alkoxy, a phenyl, a biphenyl, a naphthyl, an anthracenyl, phenanthryl or a pyrenyl.

11. The compound according to claim 1 , wherein R is selected from any one of a C1-C12 alkyl, a C1-C12 alkoxy, a phenyl, a biphenyl, a naphthyl, an anthracenyl, phenanthryl or a pyrenyl.

12. The compound according to claim 1 , wherein the compound has any one of the following structures represented by P001 to P096:

13. A display panel, comprising an organic light emitting diode (OLED) device, wherein the OLED device comprises an anode, a cathode and an organic thin film layer disposed between the anode and the cathode, wherein the organic thin film layer comprises a light-emitting layer;

wherein the light-emitting layer comprises the compound of claim 1 .

14. A display panel comprising an organic light emitting diode (OLED) device, wherein the OLED device comprises an anode, a cathode and an organic thin film layer disposed between the anode and the cathode, wherein the organic thin file layer comprises a light-emitting layer; and wherein the light emitting layer comprises the compound of claim 2 .

15. A display panel comprising an organic light emitting diode (OLED) device, wherein the OLED device comprises an anode, a cathode and an organic thin film layer disposed between the anode and the cathode, wherein the organic thin file layer comprises a light-emitting layer; and wherein the light-emitting layer comprises the compound of claim 3 .

16. The display panel according to claim 13 , wherein the compound of claim 1 is used as any one of a host material, a doped material or a co-doped material of the light-emitting layer.

17. A display device, comprising the display panel of claim 13 .

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 Jul 7, 2020
From: GAO, WEI; DAI, WENPENG; ZHANG, LEI; RAN, QUAN; NIU, JINGHUA; LI, XIA
To: SHANGHAI TIANMA AM-OLED CO., LTD.
Reel/Frame 053140/0745 →
Priority Claims (1)
CN 202010246087.6 · Mar 31, 2020 · national
Continuity (1)
Related Publication 20210309675A1 · Oct 7, 2021