Organic electroluminescence device and amine compound for organic electroluminescence device

Patent metadata

Field	Value
Publication number	US-12268091-B2
Application number	US-202117351049-A
Country	US
Kind code	B2
Filing date	Jun 17, 2021
Priority date	Oct 23, 2020
Publication date	Apr 1, 2025
Grant date	Apr 1, 2025

Abstract

An organic electroluminescence device includes a first electrode and a second electrode, and a plurality of organic layers disposed between the first electrode and the second electrode, wherein at least one organic layer among the plurality of organic layers includes an amine compound represented by Formula 1, and thereby exhibits improved emission efficiency.

First claim

What is claimed is:

1. An organic electroluminescence device, comprising:
a first electrode;
a second electrode opposite the first electrode; and
a plurality of organic layers between the first electrode and the second electrode,
wherein at least one organic layer among the plurality of organic layers comprises an amine compound,
the amine compound is a monoamine compound comprising a single amine group, the amine group being an aryl amine group and three aromatic ring substituents substituted at the amine group, and
the three aromatic ring substituents comprise a carbazole group, and a benzo[b]fluorenyl group.

2. The organic electroluminescence device of claim 1 , wherein the carbazole group and the benzo[b]fluorenyl group are each bonded to the amine group via a linker, or directly to the amine group.

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

4. The organic electroluminescence device of claim 3 , 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.

5. The organic electroluminescence device of claim 3 , wherein the hole transport region comprises multiple organic layers, and
an organic layer adjacent to the emission layer among the multiple organic layers comprises the amine compound.

6. An organic electroluminescence device, comprising:
a first electrode;
a second electrode opposite the first electrode; and
a plurality of organic layers between the first electrode and the second electrode,
wherein at least one organic layer among the plurality of organic layers comprises an amine compound represented by Formula 1:

and
wherein in Formula 1,
Ar 1 to Ar 4 are each independently a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms,
L 1 and L 2 are each independently a direct linkage, a substituted or unsubstituted arylene group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group of 2 to 30 ring-forming carbon atoms,
R 1 , R 3 and R 4 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted aryl group of 6 to 60 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 60 ring-forming carbon atoms,
R 2 is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 60 ring-forming carbon atoms,
“n 1 ” is an integer of 0 to 4,
“n 2 ” and “n 3 ” are each independently an integer of 0 to 3, and
“n 4 ” is an integer of 0 to 6.

7. The organic electroluminescence device of claim 6 , wherein the amine compound represented by Formula 1 is a monoamine compound comprising a single amine group and the amine group being an aryl amine group.

8. The organic electroluminescence device of claim 6 , wherein the amine compound represented by Formula 1 is represented by any one among Formula 2-1 to Formula 2-3:

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

9. The organic electroluminescence device of claim 6 , wherein the amine compound represented by Formula 1 is represented by Formula 3-1 or Formula 3-2:

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

10. The organic electroluminescence device of claim 6 , wherein the amine compound represented by Formula 1 is represented by Formula 4-1 or Formula 4-2:

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

11. The organic electroluminescence device of claim 6 , wherein the amine compound represented by Formula 1 is represented by Formula 5-1 or Formula 5-2:

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

12. The organic electroluminescence device of claim 6 , wherein Ar 1 to Ar 4 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted dibenzofuran group, or a substituted or unsubstituted dibenzothiophene group.

13. The organic electroluminescence device of claim 6 , wherein R 1 to R 4 are hydrogen atoms.

14. The organic electroluminescence device of claim 6 , wherein the amine compound is at least one selected from compounds represented in Compound Group 1:

Assignees

• Samsung Display Co Ltd

Inventors

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

Classifications

• H10K59/12

  Active-matrix OLED [AMOLED] displays · CPC title

• H10K59/8792

  comprising light absorbing layers, e.g. black layers · CPC title

• H10K85/631

  Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine · CPC title

• H10K50/15

  Hole transporting layers · CPC title

• H10K85/6574

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