IP Library Granted Patent US 12,016,242
Granted Patent B2
US 12,016,242 · App. 17/191,837 · Granted Jun 18, 2024

Heterocyclic compound and application thereof

Inventors: Wei Gao (Shanghai, CN); Wenpeng Dai (Shanghai, CN); Lei Zhang (Shanghai, CN); Quan Ran (Shanghai, CN); Lu Zhai (Shanghai, CN); Lilian Kuang (Shanghai, CN)
Assignees: Wuhan Tianma Micro-Electronics Co., Ltd.; Wuhan Tianma Microelectronics Co., Ltd. Shanghai Branch
H10K85/636C07D491/048C07D491/147C07D495/14C09K11/06H10K85/633C09K2211/1018H10K50/15H10K50/16H10K50/858H10K85/626H10K85/657H10K85/6574
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Quick Facts
Patent No.
US 12,016,242
App. No.
17/191,837
Granted
Jun 18, 2024
Kind
B2
Abstract

A heterocyclic compound containing heteroatom substituted fluorene is provided in the present disclosure. The heterocyclic compound includes a structure: Y1 is selected from O or S; X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , and X 8 are independently selected from CR a or N; X 9 , X 10 , X 11 , X 12 , X 13 , X 14 , X 15 , X 16 , X 17 , X 18 , X 19 , X 20 , X 21 , X 22 , X 23 , and X 24 are independently selected from CR 1 or N; R a is independently selected from hydrogen, deuterium, tritium, halogen, nitrile, cyano, nitro, hydroxyl, carbonyl, ester, carboxyl, imide, amide, C1-C20 alkoxy, C1-C20 alkyl, C3-C20 cycloalkyl, C2-C20 alkenyl, C3-C20 cycloalkenyl, silyl, boron, phosphine oxide, phosphine, sulfonyl, amine, C6-C30 aryl, C3-C30 heteroaryl, or a ring structure; Y 2 , and Y 3 are independently selected from O, S or NR 2 ; Ar 1 and Ar 2 are independently selected from aryl or heteroaryl; and R 1 and R 2 are independently selected from hydrogen, deuterium, C1-C20 alkyl, C6-C30 aryl, or C3-C30 heteroaryl.

Claims (81)

1. A heterocyclic compound, having a structure shown in formula I, comprising:

wherein:

Y1 is selected from 0 or S;

X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , and X 8 are independently selected from CR a or N, and at least one of X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , and X 8 is N;

X 9 , X 10 , X 11 , X 12 , X 13 , X 14 , X 15 , X 16 , X 17 , X 18 , X 19 , X 20 , X 21 , X 22 , X 23 , and X 24 are independently selected from CR 1 or N;

when there are a plurality of CR a in X 1 -X 8 , R a are same or different; and R a is independently selected from hydrogen, deuterium, tritium, halogen, nitrile, cyano, nitro, hydroxyl, carbonyl, ester, carboxyl, imide, amide, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C3-C20 cycloalkenyl, substituted or unsubstituted silyl, substituted or unsubstituted boron, substituted or unsubstituted phosphine oxide, substituted or unsubstituted phosphine, substituted or unsubstituted sulfonyl, substituted or unsubstituted amine, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, or a ring structure formed by bonding adjacent groups;

Y2, and Y3 are independently selected from O, S or NR 2 ;

Ar 1 and Ar 2 are independently selected from substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl; and

R 1 and R 2 are independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C3-C30 heteroaryl.

2. The heterocyclic compound according to claim 1 , wherein:

Ar 1 and Ar 2 are independently selected from phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, pyrenyl, fluoranthyl, triphenyl, pyrrolyl, pyranyl, thienyl, pyridyl, pyrimidinyl, triazinyl, benzofuranyl, benzothienyl, dibenzofuranyl, or dibenzothienyl.

3. The heterocyclic compound according to claim 2 , wherein Ar 1 and Ar 2 are independently selected from any one of following structures:

wherein # denotes a connection location.

4. The heterocyclic compound according to claim 1 , wherein:

Y2 and Y3 are independently selected from O, S, or NR 2 , wherein R 2 is selected from phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, pyrenyl, fluoranthyl, triphenyl, pyrrolyl, pyranyl, thienyl, pyridyl, pyrimidinyl, triazinyl, benzofuranyl, benzothienyl, dibenzofuranyl, or dibenzothienyl.

5. The heterocyclic compound according to claim 1 , wherein:

in the structure

in the formula I, X 9 , X 10 , X 11 , X 12 , X 13 , X 14 , X 15 , and X 16 are independently selected from CR 1 or N, and at least one of X 9 , X 10 , X 11 , X 12 , X 13 , X 14 , X 15 , and X 16 is N; and

R 1 is selected from hydrogen, deuterium, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C3-C30 heteroaryl.

6. The heterocyclic compound according to claim 5 , wherein: the structure of

is selected from any one of following structures:

7. The heterocyclic compound according to claim 1 , wherein:

the structure of

is selected from:

8. The heterocyclic compound according to claim 1 , wherein:

in the structure

in the formula I, X 17 , X 18 , X 19 , X 20 , X 21 , X 22 , X 23 , and X 24 are independently selected from CR 1 or N, and at least one of X 17 , X 18 , X 19 , X 20 , X 21 , X 22 , X 23 , and X 24 is N; and

R 1 is selected from hydrogen, deuterium, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C3-C30 heteroaryl.

9. The heterocyclic compound according to claim 8 , wherein:

the structure of

is selected from any one of following structures:

10. The heterocyclic compound according to claim 1 , wherein:

the structure of

is selected from:

11. The heterocyclic compound according to claim 1 , wherein:

any 1 to 6 of X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , and X 8 are N.

12. The heterocyclic compound according to claim 1 , wherein:

the structure of

is selected from any one of following structures:

13. The heterocyclic compound according to claim 12 , wherein:

the structure of

is selected from any one of following structures:

14. The heterocyclic compound according to claim 1 , wherein:

the structure of

is selected from any one of following structures:

15. The heterocyclic compound according to claim 14 , wherein:

the structure of

is selected from any one of following structures:

16. The heterocyclic compound according to claim 1 , wherein:

the structure of

is selected from any one of following structures:

17. The heterocyclic compound according to claim 16 , wherein:

the structure of

is selected from any one of following structures:

18. The heterocyclic compound according to claim 1 , wherein:

the structure of

is selected from any one of following structures:

19. The heterocyclic compound according to claim 1 , wherein the heterocyclic compound has any one of following structures:

20. The heterocyclic compound according to claim 1 , wherein the heterocyclic compound has any one of following structures:

21. The heterocyclic compound according to claim 1 , wherein the heterocyclic compound has any one of following structures:

22. The heterocyclic compound according to claim 1 , wherein the heterocyclic compound has any one of following structures:

23. The heterocyclic compound according to claim 1 , wherein the heterocyclic compound has any one of following structures:

24. The heterocyclic compound according to claim 1 , wherein the heterocyclic compound has any one of following structures:

25. A display panel, comprising an organic light-emitting device, wherein the organic light-emitting device includes an anode, a cathode, and an organic thin film layer between the anode and the cathode; the cathode is covered with a capping layer (CPL); and the CPL layer contains at least a heterocyclic compound, having a structure shown in formula I, the heterocyclic compound comprising:

wherein:

Y1 is selected from 0 or S;

X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , and X 8 are independently selected from CR a or N, and at least one of X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , and X 8 is N;

X 9 , X 10 , X 11 , X 12 , X 13 , X 14 , X 15 , X 16 , X 17 , X 18 , X 19 , X 20 , X 21 , X 22 , X 23 , and X 24 are independently selected from CR 1 or N;

when there are a plurality of CR a in X 1 -X 8 , R a are same or different; and R a is independently selected from hydrogen, deuterium, tritium, halogen, nitrile, cyano, nitro, hydroxyl, carbonyl, ester, carboxyl, imide, amide, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C3-C20 cycloalkenyl, substituted or unsubstituted silyl, substituted or unsubstituted boron, substituted or unsubstituted phosphine oxide, substituted or unsubstituted phosphine, substituted or unsubstituted sulfonyl, substituted or unsubstituted amine, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, or a ring structure formed by bonding adjacent groups;

Y 2 , and Y 3 are independently selected from 0, S or NR 2 ;

Ar 1 and Ar 2 are independently selected from substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl; and

R 1 and R 2 are independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C3-C30 heteroaryl.

26. A display panel, comprising an organic light-emitting device, wherein the organic light-emitting device includes an anode, a cathode, and an organic thin film layer between the anode and the cathode; the organic thin film layer includes a hole transport layer and/or an electron transport layer, wherein at least one of the hole transport layer and the electron transport layer contains at least a heterocyclic compound, having a structure shown in formula I, the heterocyclic compound comprising:

wherein:

Y1 is selected from 0 or S;

X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , and X 8 are independently selected from CR a or N, and at least one of X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , and X 8 is N;

X 9 , X 10 , X 11 , X 12 , X 13 , X 14 , X 15 , X 16 , X 17 , X 18 , X 19 , X 20 , X 21 , X 22 , X 23 , and X 24 are independently selected from CR 1 or N;

when there are a plurality of CR a in X 1 -X 8 , R a are same or different; and R a is independently selected from hydrogen, deuterium, tritium, halogen, nitrile, cyano, nitro, hydroxyl, carbonyl, ester, carboxyl, imide, amide, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C3-C20 cycloalkenyl, substituted or unsubstituted silyl, substituted or unsubstituted boron, substituted or unsubstituted phosphine oxide, substituted or unsubstituted phosphine, substituted or unsubstituted sulfonyl, substituted or unsubstituted amine, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, or a ring structure formed by bonding adjacent groups;

Y 2 , and Y 3 are independently selected from O, S or NR 2 ;

Ar 1 and Ar 2 are independently selected from substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl; and

R 1 and R 2 are independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C3-C30 heteroaryl.

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 Mar 4, 2021
From: GAO, WEI; DAI, WENPENG; ZHANG, LEI; RAN, QUAN; ZHAI, LU; KUANG, LILIAN
To: SHANGHAI TIANMA AM-OLED CO.,LTD.
Reel/Frame 055490/0468 →
Priority Claims (1)
CN 202110009324.1 · Jan 5, 2021 · national
Continuity (1)
Related Publication 20220223794A1 · Jul 14, 2022