Light emitting element and amine compound for the same

Patent metadata

Field	Value
Publication number	US-12497348-B2
Application number	US-202217588041-A
Country	US
Kind code	B2
Filing date	Jan 28, 2022
Priority date	Feb 3, 2021
Publication date	Dec 16, 2025
Grant date	Dec 16, 2025

Abstract

A light-emitting element includes a first electrode, a second electrode, and at least one functional layer disposed between the first electrode and the second electrode and including an amine compound represented by Formula 1. The light-emitting element may exhibit high emission efficiency and improved service life characteristics:

First claim

What is claimed is:

1 . A light-emitting element comprising:
a first electrode; a second electrode on the first electrode; and at least one functional layer between the first electrode and the second electrode and comprising an amine compound represented by Formula 1:

wherein, in Formula 1,
R 1 is an adamantyl group, a cyclohexyl group, or a bicycloheptyl group,
Ar 1 and Ar 2 are each independently a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms,
L is a direct linkage, a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring-forming carbon atoms, and
FR is represented by Formula 2:

wherein, in Formula 2,
X is CR a R b , N, NR c , O, or S,
R a to R c are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, and/or bonded to an adjacent group to form a ring,
d and e are each independently an integer of 0 to 4, and
R a and R e are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, and/or bonded to an adjacent group to form a ring, and
wherein when R 1 is a bicycloheptyl group,
then at least one of Ar 1 or Ar 2 is a substituted or unsubstituted phenylene group.

2 . The light-emitting element of claim 1 , wherein:
the at least one functional layer comprises an emission layer, a hole transport region between the first electrode and the emission layer, and an electron transport region between the emission layer and the second electrode, and the hole transport region comprises the amine compound.

3 . The light-emitting element of claim 2 , wherein:
the hole transport region comprises a hole injection layer on the first electrode, and a hole transport layer on the hole injection layer, and the hole transport layer comprises the amine compound.

4 . The light-emitting element of claim 1 , wherein the amine compound represented by Formula 1 is represented by Formula 1-1 or Formula 1-2:

and
wherein, in Formula 1-1 and Formula 1-2, R 1 , L, Ar 1 , and Ar 2 are each independently the same as defined in Formula 1, and X, R d , R e , d, and e are each independently the same as defined in Formula 2.

5 . The light-emitting element of claim 4 , wherein the amine compound represented by Formula 1-2 is represented by Formula 1-2A:

and
wherein, in Formula 1-2A, R 1 , L, Ar 1 , and Ar 2 are each independently the same as defined in Formula 1, and R a , R d , R e , d, and e are each independently the same as defined in Formula 2.

6 . The light-emitting element of claim 1 , wherein in Formula 1, Ar 1 and Ar 2 are a substituted or unsubstituted phenylene group.

7 . The light-emitting element of claim 1 , wherein the amine compound represented by Formula 1 is represented by Formula 1A:

and
wherein, in Formula 1A, R 1 , L, and FR are each independently the same as defined in Formula 1.

8 . The light-emitting element of claim 1 , wherein the amine compound represented by Formula 1 is represented by any one of compounds in Compound Group 1:

9 . The light-emitting element of claim 1 , wherein:
the at least one functional layer comprises: an emission layer; a first hole transport layer between the first electrode and the emission layer; a second hole transport layer between the first hole transport layer and the emission layer; and an electron transport region between the emission layer and the second electrode, and the first hole transport layer comprises the amine compound.

10 . The light-emitting element of claim 9 , wherein the second hole transport layer comprises an amine derivative compound represented by Formula 3:

and
wherein, in Formula 3,
L 11 is a direct linkage, a substituted or unsubstituted arylene group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring-forming carbon atoms, and
R 11 to R 14 are each independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted ar

Assignees

• Samsung Display Co Ltd

Inventors

• Han Sanghyun
• Kim Dongjun
• Kim Minji
• Pak Hankyu
• Jeong Eunjae
• Jo Sohee
• Oh Ilsoo
• Cho Illhun

Classifications

• H10K59/12

  Active-matrix OLED [AMOLED] displays · CPC title

• H10K50/156

  comprising a multilayered structure · CPC title

• H10K85/6576

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

• H10K85/6574

  comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes · CPC title

• H10K85/6572

  comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole · CPC title