Azulene ring-containing compound, its use, and an organic photoelectric device including the same

Patent metadata

Field	Value
Publication number	US-11667618-B2
Application number	US-202016875606-A
Country	US
Kind code	B2
Filing date	May 15, 2020
Priority date	May 31, 2019
Publication date	Jun 6, 2023
Grant date	Jun 6, 2023

Abstract

The present disclosure provides an azulene ring-containing compound, its use, and an organic photoelectric device including the same. The azulene ring-containing compound is a compound comprising a structure of Formula I. The organic photoelectric device includes an anode, a cathode, and one or more organic thin film layers located between the anode and the cathode; and at least one of the organic thin film layers contains the above-mentioned azulene ring-containing compound comprising the structure of Formula I. The azulene ring-containing compound provided by the present disclosure has an energy level difference ΔEst≤0.3 eV between the lowest singlet state S 1 and the lowest triplet state T 1 , and has a light-emitting mechanism of a thermally activated delayed fluorescent material, and can be used as a thermally activated delayed fluorescent material for organic photoelectric device, so that the light-emitting efficiency of the device is improved.

First claim

What is claimed is:

1. An azulene ring-containing compound, wherein the azulene ring-containing compound is a compound represented by the structure of Formula I:

in Formula I, Z ring

is an unsaturated five-membered ring or an unsaturated six-membered ring, and D is an electron-donating group.

2. The azulene ring-containing compound according to claim 1 , wherein the Z ring in Formula I is a benzene ring, a thiophene ring, a furan ring, or a pyridine ring.

3. The azulene ring-containing compound according to claim 1 , wherein the azulene ring-containing compound is a compound represented by the structure of Formula II:

4. The azulene ring-containing compound according to claim 1 , wherein the azulene ring-containing compound is a compound represented by the structure of Formula III:

5. The azulene ring-containing compound according to claim 1 , wherein the azulene ring-containing compound is a compound represented by the structure of Formula IV:

6. The azulene ring-containing compound according to claim 1 , wherein the azulene ring-containing compound is a compound represented by the structure of Formula V:

7. The azulene ring-containing compound according to claim 1 , wherein D is an electron-donating group containing nitrogen.

8. The azulene ring-containing compound according to claim 7 , wherein D is selected from any one of the following groups:

wherein, X and Y each is independently selected from one of a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom, and a silicon atom;
R 1 and R 2 each is independently selected from any one of a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted carbazolyl, a substituted or unsubstituted diphenylamino, r and s each is independently 0, 1, 2 or 3;
R 3 and R 4 each is independently selected from any one of a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted carbazolyl, a substituted or unsubstituted diphenylamino, p and q each is independently 0, 1, or 2;
# represents a linking site of a group.

9. The azulene ring-containing compound according to claim 8 , wherein the substituted or unsubstituted phenyl group has a structural formula of

the substituted or unsubstituted carbazolyl group has a structural formula of

and the substituted or unsubstituted diphenylamino group has a structural formula of

wherein, R 5 , R 6 , R 7 and R 8 each is independently selected from any one of an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, and a phenyl group;
u and v each is independently 0, 1, 2 or 3;
## represents a linking site of a group.

10. The azulene ring-containing compound according to claim 1 , wherein D is selected from any one of the following groups:

wherein, # represents a linking site of a group.

11. The azulene ring-containing compound according to claim 3 , wherein the azulene ring-containing compound is a compound represented by any one of the following structures;

12. The azulene ring-containing compound according to claim 4 , wherein the azulene ring-containing compound is a compound represented by any one of the following structures:

13. The azulene ring-containing compound according to claim 5 , wherein the azulene ring-containing compound is a compound represented by any one of the following structures:

14. The azulene ring-containing compound according to claim 6 , wherein the azulene ring-containing compound is a compound represented by any one of the following structures:

15. The azulene ring-containing compound according to claim 1 , wherein the azulene ring-containing compound has an energy level difference ΔE st =E S1 −E T1 ≤0.3 eV between the lowest singlet state energy level S 1 and the lowest triplet state energy level T 1 .

16. An organic photoelectric device, wherein the organic photoelectric device includes an anode, a cathode, and one or more organic thin film layers located between the anode and the cathode;
and at least one of the organic thin film layers contains the azulene ring-containing compound according to claim 1 .

17. The organic optoelectronic device

Assignees

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

Inventors

• Gao Tiezhen
• Gao Wei
• Niu Jinghua

Classifications

• H10K85/6572

  comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole · CPC title

• C07D491/048

  the oxygen-containing ring being five-membered · CPC title

• C07D209/82

  Carbazoles; Hydrogenated carbazoles · CPC title

• C07D221/06

  Ring systems of three rings · CPC title

• C07D403/14 Primary

  containing three or more hetero rings · CPC title