IP Library › Granted Patent US 10,361,374
Granted Patent B2
US 10,361,374 · App. 15/199,764 · Granted Jul 23, 2019

Amine compound and organic light emitting device including the same

Inventor: Hiroaki Itoi (Yokohama, JP)
Assignee: Samsung Display Co., Ltd.
H01L51/0061C07C211/54C07C211/58C07C211/61C07D307/91C07D307/93C07D333/76C07D409/12C09K11/00C09K11/06H01L51/006H01L51/0059H01L51/0073C07C2603/18C07C2603/40C09K2211/1014C09K2211/1022H01L51/0054H01L51/0058H01L51/0081H01L51/5056
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Quick Facts
Patent No.
US 10,361,374
App. No.
15/199,764
Granted
Jul 23, 2019
Kind
B2
Abstract

An amine compound represented by Formula 1, and an organic light emitting device including the same: wherein X may be selected from the compounds represented by Formula 2: When the amine compound represented by Formula 1 is included in the hole transport region of an organic light emitting device, the organic light emitting device may achieve long lifespan and high efficiency.

Claims (54)

1. A monoamine compound represented by Formula 1, 4, 7, or 8:

wherein, in Formula 1,

X is selected from the compounds in Formula 2:

Y is C, Si, or Ge,

Z 1 to Z 6 are each independently CR or N,

Ar 1 to Ar 3 are each independently hydrogen, deuterium, a halogen atom, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, a substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms for forming a ring, an alkyl group having 1 to 20 carbon atoms, or a silyl group having 3 to 20 carbon atoms,

L 1 is a divalent phenyl group,

L 2 and L 3 are each 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 5 to 30 carbon atoms for forming a ring, and

R and R′ are each independently hydrogen, deuterium, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, a substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms for forming a ring, or an alkyl group having 1 to 20 carbon atoms;

wherein, in Formula 4,

A is O, S or CR 2 R 3 ,

R 2 and R 3 are each independently hydrogen, deuterium, an alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms for forming a ring, and

L 1 , L 3 , and Ar 3 are each independently the same as described herein in connection with Formula 1; and

wherein, in Formulae 7 and 8,

L 1 is 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 5 to 30 carbon atoms for forming a ring,

L 2 , L 3 , and Ar 1 to Ar 3 are each independently the same as described herein in connection with Formula 1,

A is O, S or CR 2 R 3 , and

R 2 and R 3 are each independently the same as described herein in connection with Formula 4.

2. The monoamine compound of claim 1 , wherein the monoamine compound is represented by Formula 4:

3. The monoamine compound of claim 1 , wherein Formula 1 is represented by Formula 5:

wherein L 1 to L 3 and Ar 1 to Ar 3 are each independently the same as described herein in connection with Formula 1.

4. The monoamine compound of claim 1 , wherein Formula 1 is represented by Formula 6:

wherein A is O, S, or CR 2 R 3 ,

R 2 and R 3 are each independently hydrogen, deuterium, an alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms for forming a ring, and

L 1 , L 3 , and Ar 3 are each independently the same as described herein in connection with Formula 1.

5. The monoamine compound of claim 1 , wherein the monoamine compound is represented by Formula 7:

6. The monoamine compound of claim 1 , wherein the monoamine compound is represented by Formula 8:

7. The monoamine compound of claim 1 , wherein L 1 in Formulae 7 and 8 is a direct linkage, a substituted or unsubstituted divalent phenyl group, or a substituted or unsubstituted divalent biphenyl group.

8. The monoamine compound of claim 1 , wherein Ar 2 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophene group, or a substituted or unsubstituted fluorene group.

9. The monoamine compound of claim 1 , wherein Ar 3 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group.

10. A monoamine compound selected from the compounds represented by Compound Group 1:

11. An organic light emitting device, comprising:

an anode;

a hole transport region on the anode;

an emission layer on the hole transport region;

an electron transport region on the emission layer; and

a cathode on the electron transport region,

the hole transport region comprising the monoamine compound of claim 1 .

12. The organic light emitting device of claim 11 , wherein the monoamine compound is represented by Formula 4:

13. The organic light emitting device of claim 11 , wherein Formula 1 is represented by Formula 5:

14. The organic light emitting device of claim 11 , wherein Formula 1 is represented by Formula 6:

wherein A is O, S, or CR 2 R 3 ,

R 2 and R 3 are each independently hydrogen, deuterium, an alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, or a substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms for forming a ring, and

L 1 , L 3 , and Ar a are independently the same as described herein in connection with Formula 1.

15. The organic light emitting device of claim 11 , wherein the monoamine compound is represented by Formula 7:

16. The organic light emitting device of claim 11 , wherein the monoamine compound is represented by Formula 8:

17. An organic light emitting device, comprising:

an anode;

a hole transport region on the anode;

an emission layer on the hole transport region;

an electron transport region on the emission layer; and

a cathode on the electron transport region,

the hole transport region comprising at least one selected from the compounds represented by Compound Group 1:

18. The monoamine compound of claim 1 , wherein in Formulae 7 and 8, L 1 is a divalent phenyl group.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 1, 2016
From: ITOI, HIROAKI
To: SAMSUNG DISPLAY CO., LTD.
Reel/Frame 039064/0825 →
Priority Claims (1)
KR 10-2015-0179445 · Dec 15, 2015 · national
Continuity (1)
Related Publication 20170170402A1 · Jun 15, 2017