IP Library Granted Patent US 12,421,448
Granted Patent B2
US 12,421,448 · App. 17/365,251 · Granted Sep 23, 2025

Organic compound and electroluminescence application thereof

Inventors: Dongyang Deng (Shanghai, CN); Qing Chen (Shanghai, CN); Ying Liu (Shanghai, CN); Lei Zhang (Shanghai, CN)
Assignees: Wuhan Tianma Micro-Electronics Co., Ltd.; Wuhan Tianma MicroElectronics Co., Ltd. Shanghai Branch.
C09K11/06C07F5/027C07F7/0816H10K85/322H10K85/40H10K85/658C09K2211/1018H10K50/11H10K50/16H10K2101/10H10K2101/20
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 12,421,448
App. No.
17/365,251
Granted
Sep 23, 2025
Kind
B2
Abstract

An organic compound, having a structure shown in formula (I), is provided. The organic compound includes: where X and Y are each independently selected from substituted carbon, divalent heteroatom or substituted heteroatom with a valence greater than 2; A and R are each independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C2-C30 heterocyclic; and when one of A and R is hydrogen or deuterium, another of A and R is not hydrogen or deuterium; and substituents of the substituted carbon, the substituted heteroatom with the valence greater than 2, the substituted C1-C10 alkyl, the substituted C6-C30 aryl and the substituted C2-C30 heterocyclic are each independently selected from one or a combination of deuterium, nitro, cyano, substituted or unsubstituted C1˜C10 alkyl, substituted or unsubstituted C6˜C30 aryl, or substituted and unsubstituted C2˜C30 heterocyclic.

Claims (30)

1. An organic compound, having one of structures shown in formula (II) to formula (VII):

wherein, X 1 and Y 1 are each independently selected from oxygen or sulfur; X 2 is boron and Y 2 is selected from nitrogen or boron; and X 3 is selected from carbon or silicon;

A and R are each independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C2-C30 heterocyclic, wherein when one of A and R is hydrogen or deuterium, another of A and R is not hydrogen or deuterium;

the substituted C1-C10 alkyl, the substituted C6-C30 aryl and the substituted C2-C30 heterocyclic are each independently selected from one or a combination of deuterium, nitro, cyano, substituted or unsubstituted C1˜C10 alkyl, substituted or unsubstituted C6˜C30 aryl, or substituted and unsubstituted C2˜C30 heterocyclic; and

R 1 to R 4 are each independently selected from substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C2-C30 heterocyclic.

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

A and R are each independently selected from hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted tetraphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrenyl, substituted or substituted chrysenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted pyrrolyl, substituted or unsubstituted furyl, substituted or unsubstituted thienyl, substituted or unsubstituted indolyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted phenanthrolinyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted fluoranthryl, substituted or unsubstituted indenocarbazolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted indolocarbazolyl, substituted or unsubstituted indolobenzofuranyl, substituted or unsubstituted indolobenzothienyl, substituted or unsubstituted benzofuran pyrimidinyl, or substituted or unsubstituted benzothiophene pyrimidinyl.

3. The organic compound according to claim 1 , wherein:

A and R are each independently selected from hydrogen, deuterium, phenyl, nitro-substituted phenyl, cyano-substituted phenyl, biphenyl, nitro-substituted biphenyl, cyano-substituted biphenyl, terphenyl, nitro-substituted terphenyl, cyano-substituted terphenyl, tetraphenyl, nitro-substituted tetraphenyl, cyano-substituted tetraphenyl, naphthyl, nitro-substituted naphthyl, cyano-substituted naphthyl, phenanthrenyl, nitro-substituted phenanthrenyl, cyano-substituted phenanthrenyl, anthracenyl, nitro-substituted anthryl, cyano-substituted anthracenyl, triphenylene, nitro-substituted triphenylene, cyano-substituted triphenylene, pyrenyl, nitro-substituted pyrenyl, cyano-substituted pyrenyl, chrysenyl, nitro-substituted chrysenyl, cyano-substituted chrysenyl, fluorenyl, nitro-substituted fluorene, cyano-substituted fluorenyl, spirobifluorenyl, nitro-substituted spirobifluorenyl, cyano-substituted spirobifluorenyl, pyrrolyl, nitro-substituted pyrrolyl, cyano-substituted pyrrolyl, furyl, nitro-substituted furyl, cyano-substituted furyl, thienyl, nitro-substituted thienyl, cyano-substituted thienyl, indolyl, nitro-substituted indolyl, cyano-substituted indolyl, benzofuranyl, nitro-substituted benzofuranyl, cyano-substituted benzofuranyl, benzothienyl, nitro-substituted benzothienyl, cyano-substituted benzothienyl, phenanthrolinyl, nitro-substituted phenanthrolinyl, cyano-substituted phenanthrolinyl, carbazolyl, nitro-substituted carbazolyl, cyano-substituted carbazolyl, dibenzofuranyl, nitro-substituted dibenzofuranyl, cyano-substituted dibenzofuranyl, dibenzothienyl, nitro-substituted dibenzothienyl, cyano-substituted dibenzothienyl, fluoranthryl, nitro-substituted fluoranthryl, cyano-substituted fluoranthryl, indenocarbazolyl, nitro-substituted indenocarbazolyl, cyano-substituted indenocarbazolyl, pyridyl, nitro-substituted pyridyl, cyano-substituted pyridyl, pyrimidinyl, nitro-substituted pyrimidinyl, cyano-substituted pyrimidinyl, pyrazinyl, nitro-substituted pyrazinyl, cyano-substituted pyrazinyl, pyridazinyl, nitro-substituted pyridazinyl azinyl, cyano-substituted pyridazinyl, triazinyl, nitro-substituted triazinyl, cyano-substituted triazinyl, indolocarbazolyl, nitro-substituted indolocarbazolyl, cyano-substituted indolocarbazolyl, indolobenzofuranyl, nitro-substituted indolobenzofuranyl, cyano-substituted indolobenzofuranyl, indolobenzothienyl, nitro-substituted indolobenzothienyl, cyano-substituted indolobenzothienyl, benzofuran pyrimidinyl, nitro-substituted benzofuran pyrimidinyl, cyano-substituted benzofuran pyrimidinyl, benzothiophene pyrimidinyl, nitro-substituted benzothiophene pyrimidinyl, cyano-substituted benzothiophene pyrimidinyl, a group formed by a combination of the above-mentioned groups, or a group formed by fusing the above-mentioned groups.

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

R 1 to R 4 are each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted tetraphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted pyrenyl, substituted or substituted chrysenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted pyrrolyl, substituted or unsubstituted furyl, substituted or unsubstituted thienyl, substituted or unsubstituted indolyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted phenanthrolinyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted fluoranthryl, substituted or unsubstituted indenocarbazolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted indolocarbazolyl, substituted or unsubstituted indolobenzofuranyl, substituted or unsubstituted indolobenzothienyl, substituted or unsubstituted benzofuran pyrimidinyl, or substituted or unsubstituted benzothiophene pyrimidinyl.

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

R 1 to R 4 are each independently selected from phenyl, nitro-substituted phenyl, cyano-substituted phenyl, biphenyl, nitro-substituted biphenyl, cyano-substituted biphenyl, terphenyl, nitro-substituted terphenyl, cyano-substituted terphenyl, tetraphenyl, nitro-substituted tetraphenyl, cyano-substituted tetraphenyl, naphthyl, nitro-substituted naphthyl, cyano-substituted naphthyl, phenanthrenyl, nitro-substituted phenanthrenyl, cyano-substituted phenanthrenyl, anthracenyl, nitro-substituted anthryl, cyano-substituted anthracenyl, triphenylene, nitro-substituted triphenylene, cyano-substituted triphenylene, pyrenyl, nitro-substituted pyrenyl, cyano-substituted pyrenyl, chrysenyl, nitro-substituted chrysenyl, cyano-substituted chrysenyl, fluorenyl, nitro-substituted fluorene, cyano-substituted fluorenyl, spirobifluorenyl, nitro-substituted spirobifluorenyl, cyano-substituted spirobifluorenyl, pyrrolyl, nitro-substituted pyrrolyl, cyano-substituted pyrrolyl, furyl, nitro-substituted furyl, cyano-substituted furyl, thienyl, nitro-substituted thienyl, cyano-substituted thienyl, indolyl, nitro-substituted indolyl, cyano-substituted indolyl, benzofuranyl, nitro-substituted benzofuranyl, cyano-substituted benzofuranyl, benzothienyl, nitro-substituted benzothienyl, cyano-substituted benzothienyl, phenanthrolinyl, nitro-substituted phenanthrolinyl, cyano-substituted phenanthrolinyl, carbazolyl, nitro-substituted carbazolyl, cyano-substituted carbazolyl, dibenzofuranyl, nitro-substituted dibenzofuranyl, cyano-substituted dibenzofuranyl, dibenzothienyl, nitro-substituted dibenzothienyl, cyano-substituted dibenzothienyl, fluoranthryl, nitro-substituted fluoranthryl, cyano-substituted fluoranthryl, indenocarbazolyl, nitro-substituted indenocarbazolyl, cyano-substituted indenocarbazolyl, pyridyl, nitro-substituted pyridyl, cyano-substituted pyridyl, pyrimidinyl, nitro-substituted pyrimidinyl, cyano-substituted pyrimidinyl, pyrazinyl, nitro-substituted pyrazinyl, cyano-substituted pyrazinyl, pyridazinyl, nitro-substituted pyridazinyl azinyl, cyano-substituted pyridazinyl, triazinyl, nitro-substituted triazinyl, cyano-substituted triazinyl, indolocarbazolyl, nitro-substituted indolocarbazolyl, cyano-substituted indolocarbazolyl, indolobenzofuranyl, nitro-substituted indolobenzofuranyl, cyano-substituted indolobenzofuranyl, indolobenzothienyl, nitro-substituted indolobenzothienyl, cyano-substituted indolobenzothienyl, benzofuran pyrimidinyl, nitro-substituted benzofuran pyrimidinyl, cyano-substituted benzofuran pyrimidinyl, benzothiophene pyrimidinyl, nitro-substituted benzothiophene pyrimidinyl, cyano-substituted benzothiophene pyrimidinyl, a group formed by a combination of the above-mentioned groups, or a group formed by fusing the above-mentioned groups.

6. The organic compound according to claim 1 , wherein X 1 and Y 1 are both oxygen or both sulfur.

7. The organic compound according to claim 1 , wherein one of X 1 and Y 1 is oxygen, and another one of X 1 and Y 1 is sulfur.

8. The organic compound according to claim 1 , having a structure corresponding to formula (III).

9. A display panel, comprising an organic light-emitting element, wherein:

the organic light-emitting element includes an anode, a cathode, and at least one organic compound layer between the anode and the cathode; and

the organic compound layer includes at least one organic compound according to claim 1 .

10. The display panel according to claim 9 , wherein the organic compound layer includes an electron transport layer, and the electron transport layer includes at least one organic compound according to claim 1 .

11. The display panel according to claim 9 , wherein the organic compound layer includes a light-emitting layer, and the light-emitting layer includes at least one organic compound according to claim 1 .

12. The organic compound according to claim 6 , wherein the organic compound has any one of structures shown in formula (001) to formula (038):

13. The organic compound according to claim 7 , wherein the organic compound has any one of structures shown in formula (039) to formula (074):

14. The organic compound according to claim 8 , wherein the organic compound has any one of structures shown in formula (111) to formula (144):

15. An organic compound, having a structure shown in formula (I), comprising:

wherein X and Y are each independently selected from substituted carbon, divalent heteroatom, or substituted heteroatom with a valence greater than 2;

A and R are each independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C2-C30 heterocyclic; and when one of A and R is hydrogen or deuterium, another of A and R is not hydrogen or deuterium; and

substituents of the substituted carbon, the substituted heteroatom with the valence greater than 2, the substituted C1-C10 alkyl, the substituted C6-C30 aryl and the substituted C2-C30 heterocyclic are each independently selected from one or a combination of deuterium, nitro, cyano, substituted or unsubstituted C1˜C10 alkyl, substituted or unsubstituted C6˜C30 aryl, or substituted and unsubstituted C2˜C30 heterocyclic,

wherein X is a divalent heteroatom, and Y is a trivalent heteroatom; or X and Y are both trivalent heteroatoms; or X is substituted carbon or a tetravalent heteroatom, and Y is a divalent heteroatom; or X is substituted carbon or a tetravalent heteroatom, and Y is a trivalent heteroatom.

16. The organic compound according to claim 15 , wherein the organic compound has any one of structures shown in formula (145) to formula (400):

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 Aug 23, 2021
From: DENG, DONGYANG; CHEN, QING; LIU, YING; ZHANG, LEI
To: SHANGHAI TIANMA AM-OLED CO.,LTD.
Reel/Frame 057264/0407 →
Priority Claims (1)
CN 202110367101.2 · Apr 6, 2021 · national
Continuity (1)
Related Publication 20220328765A1 · Oct 13, 2022
References Cited (10)
CN 106831817A · 2017 [cited by applicant]
CN 110790782A · 2020 [cited by applicant]
CN 111018898A · 2020 [cited by applicant]
CN 112592363A · 2021 [cited by applicant]
CN 112778343A · 2021 [cited by applicant]
WO 2021008374A1 · 2021 [cited by applicant]
WO WO2022042737A1 · 2022 [cited by examiner]
Machine English translation of Li et al. (WO 2022/042737 A1). Apr. 19, 2024. [cited by examiner]
CAS No. 2098942-23-3. [cited by applicant]
CAS No. 2468706-54-7. [cited by applicant]