Organic electroluminescence device and amine compound for organic electroluminescence device

Patent metadata

Field	Value
Publication number	US-11737356-B2
Application number	US-202016997595-A
Country	US
Kind code	B2
Filing date	Aug 19, 2020
Priority date	Nov 29, 2019
Publication date	Aug 22, 2023
Grant date	Aug 22, 2023

Abstract

An organic electroluminescence device includes a first electrode, a second electrode facing the first electrode, and a plurality of organic layers between the first electrode and the second electrode, wherein at least one of the plurality of organic layers includes an amine compound, the amine compound includes a central nitrogen atom, a carbazole group substituted to the central nitrogen atom, and a dibenzoselenophene group substituted to the central nitrogen atom, and a nitrogen atom of the carbazole group is substituted with a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. The organic electroluminescence device thereby has high efficiency and long-life.

First claim

What is claimed is:

1. An organic electroluminescence device comprising:
a first electrode;
a second electrode facing the first electrode; and
a plurality of organic layers between the first electrode and the second electrode,
wherein at least one of the plurality of organic layers comprises an amine compound,
the amine compound comprises a central nitrogen atom, a carbazole group substituted to the central nitrogen atom, and a dibenzoselenophene group substituted to the central nitrogen atom, and
a nitrogen atom of the carbazole group is substituted with a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group,
wherein the plurality of organic layers comprise a hole transport region, an emission layer, and an electron transport region, and
the hole transport region comprises the amine compound, and
wherein the amine compound is represented by Formula 1:

wherein in Formula 1,
Ar 1 and Ar 2 are each independently a substituted or unsubstituted aryl group having 6 to 60 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 60 ring-forming carbon atoms,
L 1 to L 4 are each independently a direct linkage, a substituted or unsubstituted arylene group having 6 to 60 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group having 3 to 60 ring-forming carbon atoms,
R 1 to R 4 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 60 ring-forming carbon atoms,
m 1 to m 4 are each independently an integer of 0 to 4, and
n 1 to n 4 are each independently an integer of 0 to 1.

2. The organic electroluminescence device of claim 1 , wherein the amine compound further comprises, a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group, substituted to the central nitrogen atom.

3. The organic electroluminescence device of claim 1 , wherein the amine compound further comprises, a substituted or unsubstituted arylene group or a substituted or unsubstituted heteroarylene group, connecting the central nitrogen atom and the carbazole group and the central nitrogen atom and the dibenzoselenophene group, respectively.

4. The organic electroluminescence device of claim 1 , wherein the hole transport region comprises a hole transport layer and a hole injection layer, and
the hole transport layer comprises the amine compound.

5. The organic electroluminescence device of claim 1 , wherein the amine compound represented by Formula 1 is represented by Formula 1-1:

wherein in Formula 1-1,
Ar 2 , L 2 to L 4 , R 1 to R 4 , m 1 to m 4 , and n 2 to n 4 are the same as defined in Formula 1,
R 5 is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 60 ring-forming carbon atoms, and
m is an integer of 0 to 5.

6. The organic electroluminescence device of claim 1 , wherein the amine compound represented by Formula 1 is represented by any one of Formulae 2-1 to 2-4:

wherein in Formulae 2-1 to 2-4,
Ar 1 , Ar 2 , L 1 to L 4 , R 1 to R 4 , m 1 to m 4 , and n 1 to n 4 are the same as defined in Formula 1,
R 11 and R 12 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 60 ring-forming carbon atoms, and
m 11 and m 12 are each independently an integer of 0 to 4.

7. The organic electroluminescence device of claim 1 , wherein the amine compound represented by Formula 1 is represented by any one of Formulae 3-1 to 3-4:

wherein in Formulae 3-1 to 3-4,
Ar 1 , Ar 2 , L 1 to L 4 , R 1 to R 4 , m 1 to m 4 , and n 1 to n 4 are the same as defined in Formula 1.

8. The organic electroluminescence device of claim 1 , wherein Ar 2 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

9. The organic electroluminescence device of claim 1 , wherein the amine compound represented by Formula 1 is any one of compounds represented by Compound Group 1:

Assignees

• Samsung Display Co Ltd

Inventors

• Kim Dongjun
• Kim Minji
• Jeong Eunjae
• Jo Sohee
• Han Sanghyun

Classifications

• H10K85/636 Primary

  comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom · CPC title

• C07D421/12 Primary

  linked by a chain containing hetero atoms as chain links · CPC title

• H10K50/17

  Carrier injection layers · CPC title

• H10K50/15

  Hole transporting layers · CPC title

• H10K85/6572

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