IP Library Granted Patent US 11,401,285
Granted Patent B2
US 11,401,285 · App. 16/653,383 · Granted Aug 2, 2022

Compound, display panel and display apparatus

Inventors: Wei Gao (Shanghai, CN); Lei Zhang (Shanghai, CN); Wenpeng Dai (Shanghai, CN); Jinghua Niu (Shanghai, CN); Hongyan Zhu (Shanghai, CN)
Assignees: WUHAN TIANMA MICRO-ELECTRONICS CO., LTD.; WUHAN TIANMA MICROELECTRONICS CO., LTD. SHANGHAI BRANCH
C07F5/027H01L51/008H01L51/0069H01L51/0072H01L51/5206H01L51/5004H01L51/5016H01L51/5221
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Quick Facts
Patent No.
US 11,401,285
App. No.
16/653,383
Granted
Aug 2, 2022
Kind
B2
Abstract

A compound according to Formula (1), in which D is an electron donor containing a nitrogen atom and is bonded to a benzene ring through the nitrogen atom; A is an electron acceptor containing a boron atom and is bonded to a benzene ring through the boron atom; m and n are each an integer selected from 1, 2 or 3; and R 11 , R 12 , R 13 , R 14 are each independently selected from the group consisting of a hydrogen atom, alkyl, alkoxy, cyano, trifluoromethyl, an electron acceptor A′, and a nitrogen-containing electron donor D. In the compound, biphenyl acts as a linking unit between the electron donor D and the electron acceptor A, such that units D and A are located at different positions of the molecule, realizing effective separation between HOMO and LUMO. In addition, the light absorption and vibration strength of the molecule are enhanced.

Claims (68)

1. A compound, according to Formula (1):

wherein

D is an electron donor containing a nitrogen atom and is bonded to a benzene ring through the nitrogen atom, and m is an integer selected from 1, 2 or 3;

A is an electron acceptor containing a boron atom and is bonded to a benzene ring through the boron atom, and n is an integer selected from 1, 2 or 3;

the electron acceptor A has a structure represented by any one of the following Formulas (2-1) and (2-2):

wherein R 15 -R 23 are each independently selected from the group consisting of a hydrogen atom, C1-C20 alkyl, C1-C20 alkoxy, a substituted or unsubstituted C6-C40 aryl, and a substituted or unsubstituted C3-C40 heteroaryl;

X is selected from the group consisting of a boron atom, an oxygen atom, a sulfur atom, and a nitrogen atom, and R 23 is absent when X is an oxygen atom, and a sulfur atom;

R 11 , R 12 , R 13 , R 14 are each independently selected from the group consisting of a hydrogen atom, alkyl, alkoxy, cyano, trifluoromethyl, an electron acceptor A′, and a nitrogen-containing electron donor D′;

the electron acceptor A′ is any one of a carbonyl-containing group, a sulfuryl-containing group, a phosphinyl-containing six-membered phosphorus heterocyclic group, a boron-containing heterocyclic group, and an imido-containing group; and

the nitrogen-containing electron donor D′ is any one of a substituted or unsubstituted C12-C40 diphenylamino, a substituted or unsubstituted C12-C40 carbazolyl and derivative groups thereof, and a substituted or unsubstituted C13-C40 acridinyl and derivative groups thereof,

wherein an energy difference ΔE st between a lowest singlet energy level S1 of the compound and a lowest triplet energy level T1 of the compound satisfies an equation ΔE st =E S1 −E T1 ≤0.30 eV.

2. The compound of claim 1 , according to Formula (1-1):

wherein

R 11 , R 12 , R 13 and R 14 are each independently selected from the group consisting of cyano, trifluoromethyl, alkyl, alkoxy, the electron acceptor A′, and the nitrogen-containing electron donor D′.

3. The compound of claim 1 , according to Formula (1-2):

wherein

R 11 and R 12 are each independently selected from the group consisting of alkyl, alkoxy, and the nitrogen-containing electron donor D′; and

R 13 and R 14 are each independently selected from the group consisting of alkyl, alkoxy, and electron acceptor A′.

4. The compound of claim 1 , according to Formula (1-3):

wherein

R 11 and R 12 are each independently selected from the group consisting of alkyl, alkoxy, and the electron acceptor A′; and

R 13 and R 14 are each independently selected from the group consisting of alkyl, alkoxy, and the nitrogen-containing electron donor D′.

5. The compound according to claim 1 , wherein R 15 -R 23 are each independently selected from the group consisting of C1-C6 alkyl, C1-C6 alkoxy, a substituted or unsubstituted C6-C20 aryl, and a substituted or unsubstituted C3-C20 heteroaryl.

6. The compound according to claim 1 , wherein D is according to the following formulas:

wherein

Y, Y 1 and Y 2 are each independently selected from the group consisting of a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom, and a silicon atom;

x and y are integers each independently selected from 0, 1, 2 or 3;

# indicates a bonding position to Formula (1), Formula (1-1), Formula (1-2), or Formula (1-3);

R 1 , R 2 , R 3 , and R 4 are each independently selected from the group consisting of a hydrogen atom, C1-C20 alkyl, C1-C20 alkoxy, a substituted or unsubstituted C6-C40 aryl, a substituted or unsubstituted C4-C40 heteroaryl, a substituted or unsubstituted C12-C40 carbazolyl and derivative groups thereof, a substituted or unsubstituted C12-C40 diphenylamino and derivative groups thereof, a substituted or unsubstituted C13-C40 acridinyl and derivative groups thereof;

when Y is an oxygen atom or a sulfur atom, R 3 is absent;

when Y 1 is an oxygen atom or a sulfur atom, R 3 is absent; and

when Y 2 is an oxygen atom or a sulfur atom, R 4 is absent.

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

wherein

R is C1-C20 alkyl, C1-C20 alkoxy, C2-C20 alkenyl, C2-C20 alkynyl, C6-C40 aryl, C4-C40 heteroaryl; and

# is a bonding position to Formula (1).

8. The compound according to claim 1 , wherein D is according to the following formulas:

wherein

Y, Y 1 and Y 2 are each independently selected from the group consisting of a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom, and a silicon atom;

# indicates a bonding position to Formula (1);

r and s are integers each independently selected from 0, 1, 2 or 3, p and q are integers each independently selected from 0, 1 or 2;

R 1 , R 2 , R 3 , and R 4 are each independently selected from the group consisting of a hydrogen atom, C1-C20 alkyl, C1-C20 alkoxy, a substituted or unsubstituted C6-C40 aryl, a substituted or unsubstituted C4-C40 heteroaryl, a substituted or unsubstituted C12-C40 carbazolyl and derivative groups thereof, a substituted or unsubstituted C12-C40 diphenylamino and derivative groups thereof, a substituted or unsubstituted C13-C40 acridinyl and derivative groups thereof;

when Y, Y 1 or Y 2 is an oxygen atom or a sulfur atom, p=0 or q=0;

when Y, Y 1 or Y 2 is a nitrogen atom, p and q are each independently 0 or 1; and

when Y, Y 1 or Y 2 is a carbon atom or a silicon atom, p and q are integers each independently selected from 0, 1, or 2.

9. The compound according to claim 8 , wherein D is according to the following groups:

wherein # indicates a bonding position to Formula (1).

10. The compound according to claim 1 , wherein D is according to the following formula:

wherein

R 1 , R 2 are each independently selected from the group consisting of a hydrogen atom, C1-C20 alkyl, C1-C20 alkoxy, a substituted or unsubstituted C6-C40 aryl, a substituted or unsubstituted C4-C40 heteroaryl, a substituted or unsubstituted C12-C40 carbazolyl and derivative groups thereof, a substituted or unsubstituted C12-C40 diphenylamino and derivative groups thereof, a substituted or unsubstituted C13-C40 acridinyl and derivative groups thereof;

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

# indicates a bonding position to Formula (1), Formula (1-1), Formula (1-2), or Formula (1-3).

11. The compound according to claim 10 , wherein D is according to the following groups:

wherein # indicates a bonding position to Formula (1).

12. The compound according to claim 1 , wherein D is according to the following groups:

wherein # indicates a bonding position to Formula (1), Formula (1-1), Formula (1-2), or Formula (1-3).

13. The compound of claim 1 , according to the following compounds:

14. A display panel, 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 a host material and a guest material, the host material or the guest material being the compound according to claim 1 .

15. The display panel according to claim 14 , wherein the guest material is the compound according to claim 1 ;

wherein an energy difference between a HOMO level of the guest material and a HOMO level of the host material is less than 0.6 eV, or an energy difference between a LUMO level of the guest material and a LUMO level of the host material is less than 0.6 eV.

16. The display panel according to claim 14 , wherein the host material is the compound of claim 1 , and the guest material is a fluorescent material, a thermally activated delayed fluorescent material, or a phosphorescent light-emitting material;

wherein an energy difference between a HOMO energy level of the host material and a HOMO energy level of the guest material is less than 0.6 eV, or an energy difference between a LUMO energy level of the guest material and a LUMO energy level of the host material is less than 0.6 eV.

17. The display panel according to claim 14 , wherein a singlet energy level of the host material is higher than a singlet energy level of the guest material, and an energy difference between the singlet energy level of the host material and the singlet energy level of the guest material is less than 1.0 eV.

18. A display apparatus, comprising the display panel according to claim 14 .

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 Oct 15, 2019
From: GAO, WEI; ZHANG, LEI; DAI, WENPENG; NIU, JINGHUA; ZHU, HONGYAN
To: SHANGHAI TIANMA AM-OLED CO.,LTD.
Reel/Frame 050721/0559 →
Priority Claims (1)
CN 201910361227.1 · Apr 30, 2019 · national
Continuity (1)
Related Publication 20200347081A1 · Nov 5, 2020