IP Library › Granted Patent US 11,557,735
Granted Patent B2
US 11,557,735 · App. 16/735,545 · Granted Jan 17, 2023

Organic electroluminescence device and monoamine compound for organic electroluminescence device

Inventor: Takao Sakuma (Yokohama, JP)
Assignee: Samsung Display Co., Ltd.
H01L51/0074H01L51/006H01L51/0052H01L51/0073H01L51/0094H01L51/5012H01L51/5056H01L51/5072
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Quick Facts
Patent No.
US 11,557,735
App. No.
16/735,545
Granted
Jan 17, 2023
Kind
B2
Abstract

An organic electroluminescence device of one or more embodiments includes a first electrode, a hole transport region on the first electrode, 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, wherein the hole transport region includes a monoamine compound represented by Formula 1, thereby showing high emission efficiency:

Claims (73)

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;

an electron transport region on the emission layer; and

a second electrode on the electron transport region,

wherein the hole transport region comprises a monoamine compound represented by the following Formula 1:

in Formula 1,

Ar 1 and Ar 2 are each independently a substituted or unsubstituted alkyl group of 1 to 10 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group of 2 to 30 carbon atoms for forming a ring,

L is a substituted or unsubstituted arylene group of 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroarylene group of 2 to 30 carbon atoms for forming a ring, where L is not a polyacenylene having three or more rings,

R 1 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 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group of 2 to 30 carbon atoms for forming a ring,

“m” is an integer of 1 to 5, and

“n” is an integer of 0 to 7.

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

in Formula 2 and Formula 3,

Ar 1 , Ar 2 , L, R 1 , and “m” are the same as defined in Formula 1,

in Formula 2, “n” is an integer of 0 to 5, and

in Formula 3, “n” is an integer of 0 to 6.

3. The organic electroluminescence device of claim 1 , wherein L is a substituted or unsubstituted arylene group of 6 to 12 carbon atoms for forming a ring.

4. The organic electroluminescence device of claim 3 , wherein L is a substituted or unsubstituted phenylene group.

5. The organic electroluminescence device of claim 1 , wherein at least one selected from Ar 1 and Ar 2 is a substituted or unsubstituted aryl group of 10 to 20 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group of 10 to 20 carbon atoms for forming a ring.

6. The organic electroluminescence device of claim 5 , wherein at least one selected from Ar 1 and Ar 2 is a condensed structure with three or more rings.

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

in Formula 4,

L′ is a substituted or unsubstituted arylene group of 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroarylene group of 2 to 30 carbon atoms for forming a ring, where L′ is not a polyacenylene having three or more rings,

R 2 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 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group of 2 to 30 carbon atoms for forming a ring,

“p” is an integer of 0 to 5,

“a” is an integer of 0 to 7, and

Ar 1 , L, R 1 , “m” and “n” are the same as defined in Formula 1.

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

in Formula 5,

L′ and L″ are each independently a substituted or unsubstituted arylene group of 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroarylene group of 2 to 30 carbon atoms for forming a ring, where L′ and L″ are each independently not a polyacenylene having three or more rings,

R 2 and R 3 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 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group of 2 to 30 carbon atoms for forming a ring,

“p” and “q” are each independently an integer of 0 to 5,

“a” and “b” are each independently an integer of 0 to 7, and

L, R 1 , “m” and “n” are the same as defined in Formula 1.

9. The organic electroluminescence device of claim 1 , wherein Formula 1 is represented by the following Formula 6:

in Formula 6,

Ar 1 , Ar 2 , L, R 1 and “m” and “n” are the same as defined in Formula 1, and “n” is an integer of 0 to 3.

10. 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,

wherein the hole transport layer comprises the monoamine compound represented by Formula 1.

11. The organic electroluminescence device of claim 10 , wherein the hole transport region further comprises an electron blocking layer on the hole transport layer.

12. The organic electroluminescence device of claim 1 , wherein the monoamine compound represented by Formula 1 is at least one selected from compounds in the following Compound Group 1:

13. A monoamine compound represented by the following Formula 1:

in Formula 1,

Ar 1 and Ar 2 are each independently a substituted or unsubstituted alkyl group of 1 to 10 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group of 2 to 30 carbon atoms for forming a ring,

L is a substituted or unsubstituted arylene group of 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroarylene group of 2 to 30 carbon atoms for forming a ring, where L is not a polyacenylene having three or more rings,

R 1 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 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group of 2 to 30 carbon atoms for forming a ring,

“m” is an integer of 1 to 5, and

“n” is an integer of 0 to 7.

14. The monoamine compound of claim 13 , wherein Formula 1 is represented by the following Formula 2 or Formula 3:

in Formula 2 and Formula 3,

Ar 1 , Ar 2 , L, R 1 , and “m” the same as defined in Formula 1,

In Formula 2, “n” is an integer of 0 to 5, and

In Formula 3, “n” is an integer of 0 to 6.

15. The monoamine compound of claim 13 , wherein L is a substituted or unsubstituted arylene group of 6 to 12 carbon atoms for forming a ring.

16. The monoamine compound of claim 13 , wherein at least one selected from Ar 1 and Ar 2 is a condensed structure with three or more rings.

17. A monoamine compound-represented by the following Formula 4:

in Formula 4,

Ar 1 is a substituted or unsubstituted alkyl group of 1 to 10 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group of 2 to 30 carbon atoms for forming a ring,

L and L′ are each independently a substituted or unsubstituted arylene group of 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroarylene group of 2 to 30 carbon atoms for forming a ring, where L and L′ are each not a polyacenylene having three or more rings,

R 1 and R 2 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 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group of 2 to 30 carbon atoms for forming a ring,

“m” is an integer of 0 to 5,

“p” is an integer of 0 to 5,

“n” is an integer of 0 to 7, and

“a” is an integer of 0 to 7.

18. The monoamine compound of claim 13 , wherein Formula 1 is represented by the following Formula 6:

in Formula 6,

Ar 1 , Ar 2 , L, R 1 , and “m” are the same as defined in Formula 1, and “n” is an integer of 0 to 3.

19. The monoamine compound of claim 13 , wherein the monoamine compound represented by Formula 1 is a material for a hole transport region.

20. The monoamine compound of claim 13 , wherein the monoamine compound represented by Formula 1 is at least one selected from compounds in the following Compound Group 1:

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 6, 2020
From: SAKUMA, TAKAO
To: SAMSUNG DISPLAY CO., LTD.
Reel/Frame 051429/0330 →
Priority Claims (1)
KR 10-2019-0015550 · Feb 11, 2019 · national
Continuity (1)
Related Publication 20200259104A1 · Aug 13, 2020