IP Library › Granted Patent US 11,374,182
Granted Patent B2
US 11,374,182 · App. 16/524,363 · Granted Jun 28, 2022

Organic electroluminescence device and amine compound for organic electroluminescence device

Inventors: Xiulan Jin (Yokohama, JP); Ichinori Takada (Yokohama, JP)
Assignee: Samsung Display Co., Ltd.
H01L51/0094C07F7/0816C09K11/06C09K2211/1018H01L51/006H01L51/0052H01L51/0061H01L51/0071H01L51/0074H01L51/5012H01L51/5016H01L51/5056H01L51/5072H01L51/5088
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Quick Facts
Patent No.
US 11,374,182
App. No.
16/524,363
Granted
Jun 28, 2022
Kind
B2
Abstract

Provided is an organic electroluminescence device, including a first electrode, a hole transport region that is on the first electrode and includes an amine compound represented by the following Formula 1, an emission layer on the hole transport region, an electron transport region on the emission layer, and a second electrode on the electron transport region,

Claims (69)

1. An organic electroluminescence device, comprising:

a first electrode;

a hole transport region that is on the first electrode and includes an amine compound represented by the following Formula 1;

an emission layer on the hole transport region;

an electron transport region on the emission layer; and

a second electrode on the electron transport region:

in Formula 1,

R 1 is a substituted or unsubstituted aryl group having 6 to 40 ring carbon atoms,

R 2 and R 3 are each independently a substituted or unsubstituted aryl group having 6 to 40 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 40 ring carbon atoms,

R 4 to R 11 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 40 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 40 ring carbon atoms, or form a ring by combining adjacent groups with each other,

Ar 1 and Ar 2 are each independently a substituted or unsubstituted aryl group having 6 to 40 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 40 ring carbon atoms,

L is a direct linkage, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms, and

n is an integer of 1 to 4.

2. The organic electroluminescence device as claimed in claim 1 , wherein:

the hole transport region includes a hole injection layer disposed between the first electrode and the emission layer and a hole transport layer disposed between the hole injection layer and the emission layer; and

the hole transport layer includes the amine compound represented by Formula 1.

3. The organic electroluminescence device as claimed in claim 1 , wherein Formula 1 is represented by the following Formula 1-1 or 1-2:

in Formula 1-1 and Formula 1-2, R 1 to R 11 , Ar 1 , Ar 2 , L, and n are the same as defined in Formula 1.

4. The organic electroluminescence device as claimed in claim 1 , wherein Formula 1 is represented by the following Formula 2-1 or 2-2:

in Formula 2-1 and Formula 2-2,

X and Y are each independently a hydrocarbon ring having 6 to 40 ring carbon atoms, or a heterocycle having 2 to 40 ring carbon atoms,

R 12 and R 13 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 40 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 40 ring carbon atoms,

p and q are each independently an integer of 0 to 3, and

R 1 to R 11 , Ar 1 , Ar 2 , L, and n are the same as defined in Formula 1.

5. The organic electroluminescence device as claimed in claim 4 , wherein Formulae 2-1 and 2-2 are represented by the following Formulae 2-1A and 2-2A, respectively:

in Formula 2-1A and Formula 2-2A,

R 12 and p are the same as defined in Formula 2-1,

R 13 and q are the same as defined in Formula 2-2, and

R 1 to R 11 , Ar 1 , Ar 2 , L, and n are the same as defined in Formula 1.

6. The organic electroluminescence device as claimed in claim 1 , wherein R 1 is an unsubstituted phenyl group.

7. The organic electroluminescence device as claimed in claim 1 , wherein R 2 and R 3 are each independently an unsubstituted phenyl group, an unsubstituted dibenzofuranyl group, or an unsubstituted dibenzothiophenyl group.

8. The organic electroluminescence device as claimed in claim 1 , wherein Ar 1 and Ar 2 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted quinolinyl group, or a substituted or unsubstituted fluorenyl group.

9. The organic electroluminescence device as claimed in claim 1 , wherein the emission layer includes an anthracene derivative represented by the following Formula 3:

in Formula 3,

R 21 to R 30 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms, or form a ring by combining adjacent groups with each other, and

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

10. The organic electroluminescence device as claimed in claim 1 , wherein the hole transport region includes at least one selected from the group of compounds represented in the following Compound Groups A and B:

11. An amine compound represented by the following Formula 1:

in Formula 1,

R 1 is a substituted or unsubstituted aryl group having 6 to 40 ring carbon atoms,

R 2 and R 3 are each independently a substituted or unsubstituted aryl group having 6 to 40 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 40 ring carbon atoms,

R 4 to R 11 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 40 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 40 ring carbon atoms, or form a ring by combining adjacent groups with each other,

Ar 1 and Ar 2 are each independently a substituted or unsubstituted aryl group having 6 to 40 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 40 ring carbon atoms,

L is a direct linkage, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms, and

n is an integer of 1 to 4.

12. The amine compound as claimed in claim 11 , wherein Formula 1 is represented by the following Formula 1-1 or 1-2:

in Formula 1-1 and Formula 1-2, R 1 to R 11 , Ar 1 , Ar 2 , L, and n are the same as defined in Formula 1.

13. The amine compound as claimed in claim 11 , wherein R 1 is an unsubstituted phenyl group.

14. The amine compound as claimed in claim 11 , wherein R 2 and R 3 are each independently an unsubstituted phenyl group, an unsubstituted dibenzofuranyl group, or an unsubstituted dibenzothiophenyl group.

15. The amine compound as claimed in claim 11 , wherein R 2 and R 3 are the same as each other.

16. The amine compound as claimed in claim 11 , wherein Ar 1 and Ar 2 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted quinolinyl group, or a substituted or unsubstituted fluorenyl group.

17. The amine compound as claimed in claim 11 , wherein L is a direct linkage, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted divalent dibenzofuran group.

18. The amine compound as claimed in claim 11 , wherein the amine compound represented by Formula 1 is any one selected from the group of compounds represented in the following Compound Groups A and B:

19. An amine compound represented by the following Formula 2-1 or 2-2:

in Formula 2-1 and Formula 2-2,

R 1 is a substituted or unsubstituted aryl group having 6 to 40 ring carbon atoms,

R 2 and R 3 are each independently a substituted or unsubstituted aryl group having 6 to 40 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 40 ring carbon atoms,

R 4 to R 11 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 40 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 40 ring carbon atoms, or form a ring by combining adjacent groups with each other,

Ar 1 and Ar 2 are each independently a substituted or unsubstituted aryl group having 6 to 40 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 40 ring carbon atoms,

L is a direct linkage, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms,

n is an integer of 1 to 4,

X and Y are each independently a hydrocarbon ring having 6 to 40 ring carbon atoms, or a heterocycle having 2 to 40 ring carbon atoms,

R 12 and R 13 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 40 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 40 ring carbon atoms, and

p and q are each independently an integer of 0 to 3.

20. The amine compound as claimed in claim 19 , wherein Formulae 2-1 and 2-2 are represented by the following Formulae 2-1A and 2-2A, respectively:

in Formula 2-1A and Formula 2-2A,

R 12 and p are the same as defined in Formula 2-1,

R 13 and q are the same as defined in Formula 2-2, and

R 1 to R 11 , Ar 1 , Ar 2 , L, and n are the same as defined in Formula 1.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 29, 2019
From: JIN, XIULAN; TAKADA, ICHINORI
To: SAMSUNG DISPLAY CO., LTD.
Reel/Frame 049885/0396 →
Priority Claims (1)
KR 10-2018-0108393 · Sep 11, 2018 · national
Continuity (1)
Related Publication 20200083466A1 · Mar 12, 2020
Cited By (1)
US 12,588,409