IP Library Granted Patent US 11,667,618
Granted Patent B2
US 11,667,618 · App. 16/875,606 · Granted Jun 6, 2023

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

Inventors: Tiezhen Gao (Shanghai, CN); Wei Gao (Shanghai, CN); Jinghua Niu (Shanghai, CN)
Assignee: Wuhan Tianma Micro-Electronics Co., Ltd.
C07D307/93C07C211/19C07D209/82C07D221/06C07D221/18C07D265/38C07D279/18C07D333/78C07D403/14C07D409/04C07D471/04C07D487/04C07D491/048C07D495/04H10K85/40H10K85/622H10K85/633H10K85/636H10K85/6572H10K85/6574H10K85/6576C07C2603/40H10K50/11
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Quick Facts
Patent No.
US 11,667,618
App. No.
16/875,606
Granted
Jun 6, 2023
Kind
B2
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.

Claims (34)

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 according to claim 16 , wherein the organic thin film layer includes at least one light-emitting layer; and

the light-emitting layer includes a host material and a guest material, and the host material or the guest material of the light-emitting layer includes the azulene ring-containing compound according to claim 1 .

18. The organic optoelectronic device according to claim 17 , wherein the organic thin film layer further comprises one or a combination of at least two of a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer.

19. The organic optoelectronic device according to claim 17 , wherein the organic optoelectronic device comprises an anode, a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer and a cathode which are sequentially laminated; and

the guest material of the light-emitting layer is selected from one or a combination of at least two of the azulene ring-containing compound according to claim 1 .

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 May 15, 2020
From: GAO, TIEZHEN; GAO, WEI; NIU, JINGHUA
To: SHANGHAI TIANMA AM-OLED CO., LTD.
Reel/Frame 052679/0516 →
Priority Claims (1)
CN 201910472989.9 · May 31, 2019 · national
Continuity (1)
Related Publication 20200377467A1 · Dec 3, 2020