Organic compound and application thereof

Patent metadata

Field	Value
Publication number	US-12378262-B2
Application number	US-202217583266-A
Country	US
Kind code	B2
Filing date	Jan 25, 2022
Priority date	Sep 24, 2021
Publication date	Aug 5, 2025
Grant date	Aug 5, 2025

Abstract

Provided are an organic compound and use thereof. The organic compound has a structure shown in Formula I. Through molecular structure design, the organic compound is endowed with suitable HOMO and LUMO energy levels, which is conducive to matching energy levels of compounds in adjacent layers and achieving efficient exciton recombination. The organic compound has small overlap of HOMO/LUMO energy level, high singlet energy level E S , high triplet energy level E T and small energy level difference ΔE ST , which is conducive to reverse intersystem crossing and achieving higher luminescence efficiency. The organic compound molecule has high stability and low stacking degree, which is conducive to reducing concentration quenching and has excellent thermal and film stability. The organic compound is suitable as TADF materials, which is use for OLED devices, conducive to preparing OLED devices, can improve luminescence efficiency and stability of devices, reduce turn-on voltage and extend lifetime of devices.

First claim

What is claimed is:

1. An organic compound having a structure represented by Formula I:

wherein X is selected from O, S, NR 3 , CR 4 R 5 or SiR 6 R 7 ;
wherein Y is C or Si;
wherein L is selected from any one of a single bond, substituted or unsubstituted C6-C30 arylene or substituted or unsubstituted C3-C30 heteroarylene;
wherein Z is selected from any one of substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C6-C30 arylamine, or substituted or unsubstituted C6-C30 heteroarylamine;
wherein R 1 , R 2 , R 1 ′ and R 2 ′ are each independently selected from any one of deuterium, halogen, cyano, substituted or unsubstituted C1-C30 linear or branched alkyl, substituted or unsubstituted C3-C30 cycloalkyl, C1-C30 alkoxy, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C6-C30 arylamine, or substituted or unsubstituted C6-C30 heteroarylamine;
wherein R 3 , R 4 , R 5 , R 6 and R 7 are each independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C30 linear or branched alkyl, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C3-C30 heteroaryl;
wherein n 1 , n 2 and n 3 are each independently selected from an integer from 0 to 4; and
wherein n 4 is selected from an integer from 0 to 3.

2. The organic compound according to claim 1 , wherein the substituted substituents in L, Z, R 1 , R 2 , R 1 ′, R 2 ′, R 3 , R 4 , R 5 , R 6 and R 7 are each independently selected from at least one of deuterium, halogen, cyano, unsubstituted or halogenated C1-C10 linear or branched alkyl, C3-C10 cycloalkyl, unsubstituted or halogenated C1-C10 alkoxy, C6-C20 aryl, C2-C20 heteroaryl, or C6-C20 arylamine.

3. The organic compound according to claim 1 , wherein L is selected from a single bond, 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 the group; and
wherein the substituents are each independently selected from at least one of deuterium, C1-C10 linear or branched alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C6-C20 aryl, C2-C20 heteroaryl, or C6-C20 arylamine.

4. The organic compound according to claim 1 , wherein Z is selected from 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 the group; and
wherein the substituents are selected from at least one of deuterium, halogen, cyano, unsubstituted or halogenated C1-C10 linear or branched alkyl, C3-C10 cycloalkyl, unsubstituted or halogenated C1-C10 alkoxy, C6-C20 aryl, C2-C20 heteroaryl, or C6-C20 arylamine.

5. The organic compound according to claim 1 , wherein Z is selected from any one of the following groups:

wherein the dashed line represents a linkage site of the group;
wherein U 1 and U 2 are each independently selected from O, S, NR 14 , CR 15 R 16 or SiR 17 R 18 ;
wherein R 11 and R 12 are each independently selected from any one of deuterium, halogen, cyano, unsubstituted or halogenated C1-C1 linear or branched alkyl, C3-C10 cycloalkyl, unsubstituted or halogenated C1-C10 alkoxy, C6-C20 aryl, C2-C20 heteroaryl, or C6-C20 arylamine;
wherein R 13 , R 14 , R 15 , R 16 , R 17 and R 18 are each independently selected from any one of hydrogen, deuterium, halogen, cyano, unsubstituted or halogenated C1-C10 linear or branched alkyl, C3-C10 cycloalkyl, unsubstituted or halogenated C1-C10 alkoxy, C6-C20 aryl, C2-C20 heteroaryl, or C6-C20 arylamine;
wherein R 15 and R 16 are not linked or linked by a chemical bond to form a ring, and R 17 and R 18 are not linked or linked by a chemical bond to form a ring;
wherein m 1 and m 3 are each independently selected from an integer from 0 to 4;
wherein m 2 is selected from an integer from 0 to 3; and
wherein m 4 is selected from an integer from 0 to 2.

6. The organic compound according to claim 5 , wherein Z is selected from 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 the group; and
wherein the substituents are selected from at least one of deuterium, C1-C10 linear or branched alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C6-C20 aryl, C2-C20 heteroaryl, or C6-C20 arylamine.

7. The organic compound according to claim 1 , wherein R 1 , R 2 , R 1 ′ and R 2 ′ are each independently selected from any one of deuterium, halogen, cyano, C1-C10 linear or branched alkyl, C1-C10 alkoxy, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C3-C20 heteroaryl, substituted or unsubstituted C6-C20 arylamine or substituted or unsubstituted C6-C20 heteroarylamine; and
wherein the substituted substituents in R 1 , R 2 , R 1 ′ and R 2 ′ are each independently selected from at least one of deuterium, C1-C10 linear or branched alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C6-C20 aryl, C2-C20 heteroaryl, or C6-C20 arylamine.

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

wherein the dashed line represents a linkage site of the group.

9. The organic compound according to claim 1 , wherein R 3 , R 4 , R 5 , R 6 and R 7 are each independently selected from any one of C1-C10 linear or branched alkyl, substituted or unsubstituted C6-C20 aryl, or substituted or unsubstituted C3-C20 heteroaryl; and
wherein the substituted substituents are each independently selected from at least one of deuterium, C1-C10 linear or branched alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C6-C20 aryl, C2-C20 heteroaryl or C6-C20 arylamine.

10. The organic compound according to claim 9 , wherein R 3 , R 4 , R 5 , R 6 and R 7 are each independently selected from any one of methyl, phenyl, biphenyl, terphenyl, naphthyl or pyridyl.

11. The organic compound according to claim 1 , wherein n 1 , n 2 , n 3 and n 4 are each independently 0, 1 or 2.

12. The organic compound according to claim 1 , wherein the organic compound is selected from any one of the following Compound M1 to Compound M140:

Assignees

• Wuhan Tianma Micro Electronics Co Ltd

Inventors

• Deng Dongyang
• Liu Ying
• Zhang Lei
• Gao Wei

Classifications

• H10K85/322

  comprising boron · CPC title

• H10K85/658

  Organoboranes · CPC title

• H10K2101/20

  Delayed fluorescence emission · CPC title

• H10K50/11

  characterised by the electroluminescent [EL] layers · CPC title

• H10K85/6576

  comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene · CPC title