IP Library › Granted Patent US 12,035,552
Granted Patent B2
US 12,035,552 · App. 17/210,322 · Granted Jul 9, 2024

Organic electroluminescence device and amine compound for organic electroluminescence device

Inventors: Eunjae Jeong (Hwaseong-si, KR); Dongjun Kim (Suwon-si, KR); Minji Kim (Hwaseong-si, KR); Sohee Jo (Cheonan-si, KR); Sanghyun Han (Hwaseong-si, KR)
Assignee: Samsung Display Co., Ltd.
H10K50/15C09K11/07H05B33/14H10K85/615H10K85/633H10K85/636H10K85/6572H10K85/6574H10K85/6576H10K50/16H10K50/171
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Quick Facts
Patent No.
US 12,035,552
App. No.
17/210,322
Granted
Jul 9, 2024
Kind
B2
Abstract

An organic electroluminescence device (OLED) of an embodiment includes a first electrode, 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. The hole transport region may include an amine compound represented by Formula 1, and the OLED may thereby exhibit high luminous efficiency:

Claims (71)

1. An organic electroluminescence device comprising:

a first electrode;

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,

wherein the hole transport region comprises an amine compound represented by Formula 1:

and

wherein, in Formula 1,

L 1 and L 2 are each independently 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,

m and n are each independently an integer of 0 to 2,

Ar 1 and Ar 2 are each independently 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,

R 1 to R 4 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 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,

a and b are each independently an integer of 0 to 4, and

c and d are each independently an integer of 0 to 5.

2. The organic electroluminescence device of claim 1 , 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

wherein the hole injection layer or the hole transport layer comprises the amine compound.

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

and

wherein, in Formula 2,

Ar 1 , Ar 2 , L 1 , R 1 to R 4 , n, and a to d are each independently the same as defined in Formula 1.

4. The organic electroluminescence device of claim 3 , wherein the amine compound represented by Formula 2 is represented by Formula 3:

and

wherein, in Formula 3,

Ar 1 , Ar 2 , L 1 , R 1 to R 4 , n, and a to d are each independently the same as defined in Formula 2.

5. The organic electroluminescence device of claim 4 , wherein the amine compound represented by Formula 3 is represented by Formula 4-1 or Formula 4-2:

and

wherein, in Formula 4-1 and Formula 4-2,

Ar 1 , Ar 2 , L 1 , R 1 to R 4 , n, and a to d are each independently the same as defined in Formula 3.

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

and

wherein, in Formula 4-3 and Formula 4-4,

Ar 1 , Ar 2 , L 1 , R 1 to R 4 , n, and a to d are each independently the same as defined in Formula 3.

7. The organic electroluminescence device of claim 1 , wherein L 1 is a direct linkage, a substituted or unsubstituted phenylene, or a substituted or unsubstituted naphthylene.

8. The organic electroluminescence device of claim 1 , wherein L 1 is represented by Formula 5:

9. The organic electroluminescence device of claim 1 , wherein Ar 2 is a substituted or unsubstituted aryl group having 6 to 16 ring-forming carbon atoms.

10. The organic electroluminescence device of claim 9 , wherein Ar 2 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted phenanthrenyl group.

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

12. The organic electroluminescence device of claim 1 , wherein Ar 1 is represented by Formula 6:

and

wherein, in Formula 6,

R 5 is a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 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

e is an integer of 0 to 5.

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

14. An amine compound represented by Formula 1:

wherein, in Formula 1,

L 1 and L 2 are each independently 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,

m and n are each independently an integer of 0 to 2,

Ar 1 and Ar 2 are each independently 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,

R 1 to R 4 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 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,

a and b are each independently an integer of 0 to 4, and

c and d are each independently an integer of 0 to 5.

15. The amine compound of claim 14 , wherein the amine compound represented by Formula 1 is represented by Formula 2:

and

wherein, in Formula 2,

Ar 1 , Ar 2 , L 1 , R 1 to R 4 , n, and a to d are each independently the same as defined in Formula 1.

16. The amine compound of claim 15 , wherein the amine compound represented by Formula 2 is represented by Formula 3:

and

wherein, in Formula 3,

Ar 1 , Ar 2 , L 1 , R 1 to R 4 , n, and a to d are each independently the same as defined in Formula 2.

17. The amine compound of claim 16 , wherein the amine compound represented by Formula 3 is represented by Formula 4-1 or Formula 4-2:

and

wherein, in Formula 4-1 and Formula 4-2,

Ar 1 , Ar 2 , L 1 , R 1 to R 4 , n, and a to d are each independently the same as defined in Formula 3.

18. The amine compound of claim 16 , wherein the amine compound represented by Formula 3 is represented by Formula 4-3 or Formula 4-4:

and

wherein, in Formula 4-3 and Formula 4-4,

Ar 1 , Ar 2 , L 1 , R 1 to R 4 , n, and a to d are each independently the same as defined in Formula 3.

19. The amine compound of claim 14 , wherein Ar 2 is a substituted or unsubstituted aryl group having 6 to 16 ring-forming carbon atoms.

20. The amine compound of claim 14 , wherein the amine compound represented by Formula 1 is any one selected from the compounds represented by Compound Group 1:

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 23, 2021
From: JEONG, EUNJAE; KIM, DONGJUN; KIM, MINJI; JO, SOHEE; HAN, SANGHYUN
To: SAMSUNG DISPLAY CO., LTD.
Reel/Frame 055691/0905 →
Priority Claims (1)
KR 10-2020-0070839 · Jun 11, 2020 · national
Continuity (1)
Related Publication 20210399250A1 · Dec 23, 2021