Organic electroluminescence device and amine compound for organic electroluminescence device

Patent metadata

Field	Value
Publication number	US-12441699-B2
Application number	US-202318496738-A
Country	US
Kind code	B2
Filing date	Oct 27, 2023
Priority date	Nov 21, 2019
Publication date	Oct 14, 2025
Grant date	Oct 14, 2025

Abstract

An organic electroluminescence device of an embodiment of the present disclosure includes a first electrode, a second electrode facing the first electrode, and a plurality of organic layers disposed between the first electrode and the second electrode, wherein at least one organic layer of the plurality of organic layers includes an amine compound containing a fluorene group; an aryl group having 6 to 60 ring-forming carbon atoms, which is substituted to the fluorene group; a heteroaryl group having 2 to 60 ring-forming carbon atoms, which is substituted to the fluorene group; and at least one amine group, which is substituted to the fluorene group; wherein all the carbons of the aryl group are substituted with deuterium, and the organic electroluminescence device exhibits high efficiency and a long service 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 organic layers comprises an amine compound;
the amine compound comprises a fluorene group; an aryl group having 6 to 60 ring-forming carbon atoms, which is substituted to the fluorene group; a heteroaryl group having 2 to 60 ring-forming carbon atoms, which is substituted to the fluorene group; and at least one aryl amine or heteroaryl amine group which is substituted to the fluorene group;
all substitutable carbons of the aryl group are substituted with deuterium, and
wherein the amine group is connected to at least one of 3-position carbon or 6-position carbon of the fluorene group.

2. The organic electroluminescence device of claim 1 , wherein the heteroaryl group is a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted dibenzothiophene group, or a substituted or unsubstituted carbazole group.

3. The organic electroluminescence device of claim 1 , wherein the organic layers comprise a hole transport region, an emission layer, and an electron transport region, and the hole transport region comprises the amine compound.

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

wherein, in Formula 1,
X is O, S, or NAr 6 ;
L 1 and L 2 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 2 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 2 to 60 ring-forming carbon atoms, and/or are optionally bonded to an adjacent group to form a ring;
m 1 , m 2 , and m 4 are each independently an integer of 0 to 4;
m 3 is an integer of 0 to 3;
Ar 1 is a phenyl group substituted with deuterium, a naphthyl group substituted with deuterium, or a biphenyl group substituted with deuterium;
Ar 2 to Ar 6 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; and
n 1 and n 2 are each independently 0 or 1; and
at least one of n 1 or n 2 is 1.

5. The organic electroluminescence device of claim 4 , wherein the amine compound represented by Formula 1 is represented by at least one of Formula 1-1 to Formula 1-3:

wherein, in Formula 1-1 to Formula 1-3,
L 1 , L 2 , R 1 to R 4 , m 1 to m 4 , Ar 1 to Ar 6 , n 1 and n 2 are each independently the same as defined in Formula 1.

6. The organic electroluminescence device of claim 4 , wherein the amine compound represented by Formula 1 is represented by at least one of Formula 2-1 to Formula 2-5:

wherein, in Formula 2-1 to Formula 2-5,
R 11 to R 17 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 2 to 60 ring-forming carbon atoms, and/or are optionally bonded to an adjacent group to form a ring;
o 1 to o 4 and o 6 are each independently an integer of 0 to 5;
o 5 is an integer of 0 to 4;
o 7 is an integer of 0 to 7; and
X, R 1 to R 4 , L 1 , L 2 , n 1 , n 2 , m 1 to m 4 and Ar 1 are each independently the same as defined in Formula 1.

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

wherein, in Formula 3-1,
X, Ar 1 to Ar 5 , R 1 to R 4 , n 1 , n 2 , and m 1 to m 4 are each independently the same as defined in Formula 1.

8. The organic electroluminescence device of claim 4 , wherein the amine compound represented by Formula 1 is represented by at least one of Formula 4-1 and Formula 4-2:

wherein, in Formula 4-1 and Formula 4-2,
X, Ar 1 to Ar 5 , R 1 to R 4 , and m 1 to m 4 are each independently the same as defined in Formula 1.

9. The organic electroluminescence device of claim 4 , wherein X is NAr 6 , and Ar 6 is a substituted or unsubstituted phenyl group.

10. The organic electroluminescence device of claim 4 , wherein the amine compound represented by Formula 1 is at least one of the compounds represented by Compound Group 1:

Assignees

• Samsung Display Co Ltd

Inventors

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

Classifications

• H10K85/6576 Primary

  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

• H10K50/17

  Carrier injection layers · CPC title

• H10K50/15

  Hole transporting layers · CPC title