Organic compound, electroluminescent material, and use thereof

Patent metadata

Field	Value
Publication number	US-12428431-B2
Application number	US-202117544946-A
Country	US
Kind code	B2
Filing date	Dec 8, 2021
Priority date	Jul 26, 2021
Publication date	Sep 30, 2025
Grant date	Sep 30, 2025

Abstract

Provided are an organic compound, an electroluminescent material and use thereof. The organic compound has a structure as shown in Formula I. Through the molecular structure design, the organic compound has a deep LUMO energy level, which can reduce electron injection potential barrier and improve electron injection ability; it has a deep HOMO, which can effectively block holes and make more electron-holes recombine in the light-emitting layer; it has a high triplet energy level E T1 , which can effectively block light-emitting layer excitons. The molecule has a twisted spiro structure, which can reduce molecules stacking, avoid crystallization, show excellent thermal stability and film stability, and help improve luminous efficiency and lifetime. As electroluminescent materials, the organic compound is suitable for an electron transport layer and/or a hole blocking layer of OLED devices and can reduce voltage and power consumption, improve luminous efficiency and working lifetime to have better comprehensive performance.

First claim

What is claimed is:

1. An organic compound, having a structure as shown in Formula I:

wherein X 1 , X 2 , and X 3 are all N;
wherein Y is selected from O, S, NR N or CR C1 R C2 , and Z is NR N;
wherein L is selected from any one of a single bond, substituted or unsubstituted C6 to C40 arylene, or substituted or unsubstituted C3 to C40 heteroarylene;
wherein R 1 , R 2 , R, R N , R C1 , and R C2 are each independently selected from any one of hydrogen, substituted or unsubstituted C1 to C20 linear or branched alkyl, substituted or unsubstituted C6 to C40 aryl, or substituted or unsubstituted C2 to C40 heteroaryl;
wherein Ar 1 and Ar 2 are each independently selected from any one of deuterium, halogen, cyano, substituted or unsubstituted C1 to C20 linear or branched alkyl, C1 to C20 alkoxy, C1 to C20 alkylthio, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C6 to C40 aryl, substituted or unsubstituted C2 to C40 heteroaryl, or substituted or unsubstituted C6 to C40 arylamino; and
wherein n 1 and n 2 are each independently selected from integers from 0 to 4.

2. The organic compound according to claim 1 , wherein the substituted substituents in L, R 1 , R 2 , R, R N , R C1 , R C2 , Ar 1 , and Ar 2 are each independently selected from at least one of deuterium, cyano, halogen, unsubstituted or halogenated C1 to C10 linear or branched alkyl, unsubstituted or halogenated C1 to C10 alkoxy, C1 to C10 alkylthio, C6 to C20 aryl, C2 to C20 heteroaryl, or C6 to C18 arylamino.

3. The organic compound according to claim 1 , having a structure as shown in Formula II-1 or Formula II-2:

wherein Y, Z, L, R 1 , R 2 , Ar 1 , Ar 2 , n 1 , and n 2 have the same ranges as defined in Formula I.

4. The organic compound according to claim 1 , wherein Y is selected from O, S or NR N , and Z is NR N .

5. The organic compound according to claim 1 , wherein R N , R C1 , and R C2 are each independently selected from methyl or phenyl.

6. The organic compound according to claim 1 , wherein L is selected from any one of a single bond, phenylene, biphenylene, terphenylene, naphthylene or pyridinylene.

7. The organic compound according to claim 1 , wherein R 1 and R 2 are each independently selected from hydrogen or any one of the following groups:

wherein the dashed line represents a linkage site of a group;
wherein L 1 is selected from any one of a single bond or substituted or unsubstituted C6 to C20 arylene;
wherein X 4 is selected from O, S or NR N1 ;
wherein X 5 is selected from O, S, NR N2 or CR C3 R C4 ;
wherein R N1 , R N2 , R C3 , and R C4 are each independently selected from any one of hydrogen, substituted or unsubstituted C1 to C20 linear or branched alkyl, substituted or unsubstituted C6 to C20 aryl, or substituted or unsubstituted C2 to C20 heteroaryl;
wherein R 11 and R 12 are each independently selected from any one of deuterium, cyano, halogen, unsubstituted or halogenated C1 to C10 linear or branched alkyl, unsubstituted or halogenated C1 to C10 alkoxy, C1 to C10 alkylthio, C6 to C20 aryl, C2 to C20 heteroaryl, or C6 to C18 arylamino;
wherein m 1 is selected from integers from 0 to 5;
wherein m 2 is selected from integers from 0 to 6;
wherein m 3 is selected from integers from 0 to 9;
wherein m 4 and m 6 are each independently selected from integers from 0 to 4; and
wherein m 5 is selected from integers from 0 to 3.

8. The organic compound according to claim 1 , wherein R 1 and R 2 are each independently selected from hydrogen, or any one of the following groups, or any one of the following groups substituted with a substituent:

wherein the dashed line represents a linkage site of a group;
wherein the substituted substituents are each independently selected from at least one of deuterium, cyano, halogen, unsubstituted or halogenated C1 to C10 linear or branched alkyl, unsubstituted or halogenated C1 to C10 alkoxy, C1 to C10 alkylthio, C6 to C20 aryl, C2 to C20 heteroaryl, or C6 to C18 arylamino.

9. The organic compound according to claim 1 , wherein Ar 1 and Ar 2 are each independently selected from any one of deuterium, halogen, cyano, phenyl, or unsubstituted or halogenated C1 to C10 linear or branched alkyl.

10. The organic compound according to claim 1 , wherein the organic compound is selected from any one of the following compounds:

11. An electroluminescent material, comprising the organic compound according to claim 1 .

12. An OLED device, comprising an anode, a cathode, and an organic thin film layer located between the anode and the cathode, wherein a material of the organic thin film layer comprises the electroluminescent material according to claim 11 .

13. The OLED device according to claim 12 , wherein the organic thin film layer comprises an electron transport layer whose material comprises the electroluminescent material.

14. The OLED device according to claim 12 , wherein the organic thin film layer comprises a hole blocking layer whose material comprises the electroluminescent material.

15. The OLED device according to claim 12 , wherein the organic thin film layer comprises a light-emitting layer whose material comprises the electroluminescent material.

16. A display panel, comprising the OLED device according to claim 12 .

Assignees

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

Inventors

• Ran Quan
• Gao Wei
• Zhang Lei

Classifications

• H10K2101/40

  Interrelation of parameters between multiple constituent active layers or sublayers, e.g. HOMO values in adjacent layers · CPC title

• H10K2101/30

  Highest occupied molecular orbital [HOMO], lowest unoccupied molecular orbital [LUMO] or Fermi energy values · CPC title

• H10K2101/10

  Triplet emission · CPC title

• H10K50/18

  Carrier blocking layers · CPC title

• H10K50/16

  Electron transporting layers · CPC title