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

Patent metadata

Field	Value
Publication number	US-11459344-B2
Application number	US-201916691494-A
Country	US
Kind code	B2
Filing date	Nov 21, 2019
Priority date	Apr 25, 2019
Publication date	Oct 4, 2022
Grant date	Oct 4, 2022

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 ΔEst≥0.30 eV, and, when used in an organic light-emitting display panel, can further increase the luminous efficiency of the device.

First claim

What is claimed is:

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:

Assignees

• Wuhan Tianma Micro Electronics Co Ltd
• Wuhan Tianma Microelectronics Co Ltd Shanghai Branch

Inventors

• Gao Wei
• Zhang Lei
• Dai Wenpeng
• Niu Jinghua
• Deng Dongyang

Classifications

• C09K2211/1029

  containing one nitrogen atom as the heteroatom · CPC title

• C09K2211/1037

  with sulfur · CPC title

• C09K2211/1044

  containing two nitrogen atoms as heteroatoms · CPC title

• C07F9/655345

  the sulfur atom being part of a five-membered ring · CPC title

• C07F5/02

  Boron compounds · CPC title