IP Library › Granted Patent US 11,770,973
Granted Patent B2
US 11,770,973 · App. 16/858,392 · Granted Sep 26, 2023

Organic electroluminescence device and amine compound for organic electroluminescence device

Inventors: Sanghyun Han (Hwaseong-si, KR); Dongjun Kim (Suwon-si, KR); Minji Kim (Hwaseong-si, KR); Jongwoo Kim (Hwaseong-si, KR); Eunjae Jeong (Hwaseong-si, KR); Sohee Jo (Seoul, KR)
Assignee: Samsung Display Co., Ltd.
H10K85/6574H10K85/633H10K85/656H10K85/6572H10K85/6576H10K50/15H10K50/16
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Quick Facts
Patent No.
US 11,770,973
App. No.
16/858,392
Granted
Sep 26, 2023
Kind
B2
Abstract

An organic electroluminescence device of an embodiment includes a first electrode and a second electrode which are faced to each other, and a plurality of organic layers between the first electrode and the second electrode, and at least one organic layer selected from among the organic layers includes an amine compound represented by Formula 1 below, and thus, the organic electroluminescence device can exhibit improved emitting efficiency and long device lifespan.

Claims (75)

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 selected from among the organic layers includes an amine compound,

wherein the amine compound is represented by Formula 1 below:

in Formula 1 above,

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

Ar 1 and Ar 2 are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring, and

M is represented by Formula 2 below:

in Formula 2 above,

R 11 to R 21 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 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms for forming a ring, and

one selected from among R 11 to R 21 is a part linked to L of Formula 1.

2. The organic electroluminescence device of claim 1 , wherein the 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,

wherein the hole transport region includes the amine compound.

3. The organic electroluminescence device of claim 2 , wherein the hole transport region comprises:

a hole injection layer on the first electrode; and

a hole transport layer on the hole injection layer,

wherein the hole transport layer includes the amine compound.

4. The organic electroluminescence device of claim 2 , wherein:

the hole transport region comprises a plurality of organic layers, and

the organic layer selected from among the plurality of organic layers which is adjacent to the emission layer includes the amine compound.

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

in Formula 3-1 and Formula 3-2 above,

R 1 and R 2 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 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms for forming a ring,

n 1 is an integer of 0 to 2,

n 2 is an integer of 0 to 3, and

R 11 to R 21 , Ar 1 , Ar 2 , and L are the same as defined with respect to Formula 1 and Formula 2.

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

in Formula 4-1 to Formula 4-6 above,

R 11 to R 21 , Ar 1 , Ar 2 , and L are the same as defined with respect to Formula 1 and Formula 2.

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

in Formula 5-1 above,

Ar 1 , Ar 2 , and M are the same as defined with respect to Formula 1.

8. The organic electroluminescence device of claim 1 , wherein Ar 1 and Ar 2 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 fluorenyl group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted dibenzofuran group, or a substituted or unsubstituted dibenzothiophene group.

9. The organic electroluminescence device of claim 1 , wherein Ar 1 and Ar 2 are different from each other.

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

11. 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 organic layer selected from among the organic layers comprises an amine compound represented by Formula 1 below:

in Formula 1 above,

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

Ar 1 and Ar 2 are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring, and

M is represented by Formula 2 below:

in Formula 2,

R 11 to R 21 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 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms for forming a ring, and

one selected from among R 11 to R 21 is a part linked to L of Formula 1.

12. An amine compound represented by Formula 1 below:

in Formula 1,

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

Ar 1 and Ar 2 are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring, and

M is represented by Formula 2 below:

in Formula 2 above,

R 11 to R 21 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 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms for forming a ring, and

one selected from among R 11 to R 21 is a part linked to L to Formula 1.

13. The amine compound of claim 12 , wherein the amine compound represented by Formula 1 is represented by Formula 3-1 or Formula 3-2 below:

in Formula 3-1 and Formula 3-2 above,

R 1 and R 2 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 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms for forming a ring,

n 1 is an integer of 0 to 2,

n 2 is an integer of 0 to 3, and

R 11 to R 21 , Ar 1 , Ar 2 , and L are the same as defined with respect to Formula 1 and Formula 2.

14. The amine compound of claim 12 , wherein the amine compound represented by Formula 1 is represented by any one selected from among Formula 4-1 to Formula 4-6 below:

in Formula 4-1 to Formula 4-6,

R 11 to R 21 , Ar 1 , Ar 2 , and L are the same as defined with respect to Formula 1 and Formula 2.

15. The amine compound of claim 12 , wherein the amine compound represented by Formula 1 is represented by Formula 5 below:

in Formula 5 above,

Ar 1 , Ar 2 , and M are the same as defined with respect to Formula 1.

16. The amine compound of claim 12 , wherein Ar 1 and Ar 2 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 fluorenyl group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted dibenzofuran group, or a substituted or unsubstituted dibenzothiophene group.

17. The amine compound of claim 12 , wherein Ar 1 and Ar 2 are different from each other.

18. The amine compound of claim 12 , wherein the amine compound is at least one selected from among compounds represented in Compound Group 1 below:

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 24, 2020
From: HAN, SANGHYUN; KIM, DONGJUN; KIM, MINJI; KIM, JONGWOO; JEONG, EUNJAE; JO, SOHEE
To: SAMSUNG DISPLAY CO., LTD.
Reel/Frame 052495/0387 →
Priority Claims (1)
KR 10-2019-0072824 · Jun 19, 2019 · national
Continuity (1)
Related Publication 20200403164A1 · Dec 24, 2020
Cited By (1)
US 12,588,409