IP Library › Granted Patent US 11,121,329
Granted Patent B2
US 11,121,329 · App. 16/040,332 · Granted Sep 14, 2021

Amine compound and organic electroluminescence device including the same

Inventor: Takuya Uno (Yokohama, JP)
Assignee: SAMSUNG DISPLAY CO., LTD.
H01L51/0094C07F7/0812C09K11/06H01L27/12H01L51/006H01L51/0061H01L51/0073H01L51/0074C09K2211/1018H01L51/0052H01L51/5012H01L51/5056
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Quick Facts
Patent No.
US 11,121,329
App. No.
16/040,332
Granted
Sep 14, 2021
Kind
B2
Abstract

An amine compound which improves emission efficiency and an organic electroluminescence device including the same are provided. The amine compound is represented by the structure below, wherein X is O or S, Y is C or Si, each of Ar 1 and Ar 2 is independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms for forming a ring, which includes O or S as a heteroatom, and each of L 1 and L 2 is independently a direct linkage, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms for forming a ring. R1 through R5 are defined in the description.

Claims (65)

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

wherein

X is O or S,

Y is C or Si,

each of Ar 1 and Ar 2 is independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms for forming a ring, which includes O or S as a heteroatom,

each of L 1 and L 2 is independently a direct linkage, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms for forming a ring,

R 1 is an unsubstituted phenyl group,

each of R 2 to R 5 is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, 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 arylthio group having 1 to 10 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 10 carbon atoms, a substituted or unsubstituted arylamino group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms for forming a ring, or combined with an adjacent group to form a ring,

“a” is 1,

“b” is an integer of 0 to 3,

“c” is 0 or 1, and

“d” and “e” are each independently an integer of 0 to 5.

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

wherein

X, Ar 1 , Ar 2 , L 1 , L 2 , R 1 to R 3 , and “a” to “c” are the same as defined in Formula 1.

3. The amine compound of claim 1 , wherein Formula 1 is represented by the following Formula 1-2:

wherein

X, Ar 1 , Ar 2 , L 1 , L 2 , R 1 to R 3 , and “a” to “c” are the same as defined in Formula 1.

4. The amine compound of claim 1 , wherein

part in Formula 1 is represented by one of the following H-1 to H-4:

in H-1 to H-4,

X, R 1 , R 2 and “b” are the same as defined in Formula 1.

5. The amine compound of claim 1 , wherein Ar 1 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted phenanthryl group.

6. The amine compound of claim 1 , wherein Ar 1 is a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophene group.

7. The amine compound of claim 1 , wherein Ar 2 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophene group.

8. The amine compound of claim 1 , wherein L 1 and L 2 are each independently a direct linkage, a substituted or unsubstituted phenylene group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted naphthalene group, or a substituted or unsubstituted fluorenylene group.

9. The amine compound of claim 1 , wherein

R 1 is a substituted or unsubstituted phenyl group, and

each of R 2 to R 5 is a hydrogen atom, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted triphenylsilyl group, or combined with an adjacent group to form a ring.

10. The amine compound of claim 1 , wherein Formula 1 is any one selected from compounds represented in the following Compound Group 1:

11. The amine compound of claim 1 , wherein Formula 1 is any one selected from compounds represented in the following Compound Group 2:

12. An organic electroluminescence device, comprising:

a first electrode;

a hole transport region disposed on the first electrode;

an emission layer disposed on the hole transport region;

an electron transport region disposed on the emission layer; and

a second electrode disposed on the electron transport region,

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

wherein

X is O or S,

Y is C or Si,

each of Ar 1 and Ar 2 is independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms for forming a ring, which includes O or S as a heteroatom,

each of L 1 and L 2 is independently a direct linkage, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms for forming a ring,

R 1 is an unsubstituted phenyl group,

each of R 2 to R 5 is independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, 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 arylthio group having 1 to 10 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 10 carbon atoms, a substituted or unsubstituted arylamino group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms for forming a ring, or combined with an adjacent group to form a ring,

“a” is 1,

“b” is an integer of 0 to 3,

“c” is 0 or 1, and

“d” and “e” are each independently an integer of 0 to 5.

13. The organic electroluminescence device of claim 12 , wherein the hole transport region comprises:

a hole injection layer; and

a hole transport layer disposed between the hole injection layer and the emission layer,

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

14. The organic electroluminescence device of claim 12 , wherein the emission layer emits blue light.

15. The organic electroluminescence device of claim 12 , wherein Formula 1 is represented by the following Formula 1-1 or Formula 1-2:

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

X, Ar 1 , Ar 2 , L 1 , L 2 , R 1 to R 3 , and “a” to “c” are the same as defined in Formula 1.

16. The organic electroluminescence device of claim 12 , wherein

part in Formula 1 is represented by one of the following H-1 to H-4:

in H-1 to H-4,

X, R 1 , R 2 and “b” are the same as defined in Formula 1.

17. The organic electroluminescence device of claim 12 , wherein Ar 1 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophene group.

18. The organic electroluminescence device of claim 12 , wherein Ar 2 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophene group.

19. The organic electroluminescence device of claim 12 , wherein L 1 and L 2 are each independently a direct linkage, a substituted or unsubstituted phenylene group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted naphthalene group, or a substituted or unsubstituted fluorenylene group.

20. The organic electroluminescence device of claim 12 , wherein the hole transport region comprises at least one of amine compounds represented in the following Compound Group 1 or Compound Group 2:

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 19, 2018
From: UNO, TAKUYA
To: SAMSUNG DISPLAY CO., LTD.
Reel/Frame 046405/0648 →
Priority Claims (1)
KR 10-2017-0158831 · Nov 24, 2017 · national
Continuity (1)
Related Publication 20190165285A1 · May 30, 2019
Cited By (3)
US 12,584,068 US 12,660,502 US 12,685,011