IP Library › Granted Patent US 11,832,512
Granted Patent B2
US 11,832,512 · App. 16/565,332 · Granted Nov 28, 2023

Organic electroluminescence device and monoamine compound for organic electroluminescence device

Inventor: Ichinori Takada (Tsurumi-ku, JP)
Assignee: Samsung Display Co., Ltd.
H10K85/633C07C211/54C07D307/91H10K85/636H10K50/15H10K50/17H10K71/00H10K71/164H10K85/6574H10K2102/351
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Quick Facts
Patent No.
US 11,832,512
App. No.
16/565,332
Granted
Nov 28, 2023
Kind
B2
Abstract

An organic electroluminescence device including a monoamine compound represented by the following Formula 1 in at least one of a plurality of organic layers, and a monoamine compound represented by the following Formula 1 are provided. The monoamine compound represented by Formula 1 may be represented by the following Formula 2-1 or 2-2.

Claims (55)

1. An organic electroluminescence device, comprising:

a first electrode;

a second electrode on the first electrode; and

a plurality of organic layers between the first electrode and the second electrode,

wherein at least one of the plurality of organic layers comprises a monoamine compound represented by the following Formula 1:

wherein in Formula 1,

L 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 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,

Ar 3 is 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,

R 1 to R 6 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, or a substituted or unsubstituted silyl group having 1 to 40 carbon atoms, and

one pair of R 2 and R 3 , or R 4 and R 5 combine with each other to form a substituted or unsubstituted benzene ring.

2. The organic electroluminescence device of claim 1 , wherein L is a substituted or unsubstituted phenylene group, a substituted or unsubstituted divalent biphenyl group, or a substituted or unsubstituted dibenzofuranylene group.

3. 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 fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

4. The organic electroluminescence device of claim 1 , wherein Ar 1 and Ar 2 are each independently an aryl group having 6 to 30 carbon atoms for forming a ring substituted with a phenyl group or a naphthyl group.

5. The organic electroluminescence device 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.

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

wherein in Formulae 2-1 and 2-2,

R 7 and R 8 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, or a substituted or unsubstituted silyl group having 1 to 40 carbon atoms,

m and n are each independently an integer of 0 to 4, and

L, Ar 1 to Ar 3 , and R 1 to R 6 are the same as respectively defined with respect to Formula 1.

7. The organic electroluminescence device of claim 1 , wherein the monoamine compound represented by Formula 1 is represented by the following Formula 3:

wherein in Formula 3, L, Ar 1 , Ar 2 , and R 1 to R 6 are the same as respectively defined with respect to Formula 1.

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

wherein in Formula 4,

another pair of R 2 and R 3 , or R 4 and R 5 , which do not form the substituted or unsubstituted benzene ring, are each a hydrogen atom, and

L and Ar 1 to Ar 3 are the same as respectively defined with respect to Formula 1.

9. The organic electroluminescence device of claim 1 , wherein the plurality of organic layers comprises:

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, and

the hole transport region comprises the monoamine compound represented by Formula 1.

10. The organic electroluminescence device of claim 9 , wherein the emission layer is to emit blue light with a wavelength range of about 440 nm to about 490 nm.

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

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

wherein in Formula 1,

L 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 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,

Ar 3 is 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,

R 1 to R 6 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, or a substituted or unsubstituted silyl group having 1 to 40 carbon atoms, and

one pair of R 2 and R 3 , or R 4 and R 5 combine with each other to form a substituted or unsubstituted benzene ring.

13. The monoamine compound of claim 12 , wherein L is a substituted or unsubstituted phenylene group, a substituted or unsubstituted divalent biphenyl group, or a substituted or unsubstituted dibenzofuranylene group.

14. The monoamine 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 fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

15. The monoamine compound of claim 12 , wherein Ar 1 and Ar 2 are each independently an aryl group having 6 to 30 carbon atoms for forming a ring substituted with a phenyl group or a naphthyl group.

16. The monoamine compound of claim 12 , wherein Ara is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group.

17. The monoamine compound of claim 12 , wherein the monoamine compound represented by Formula 1 is represented by the following Formula 2-1 or 2-2:

wherein in Formulae 2-1 and 2-2,

R 7 and R 8 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms for forming a ring, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms for forming a ring, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, or a substituted or unsubstituted silyl group having 1 to 40 carbon atoms,

m and n are each independently an integer of 0 to 4, and

L, Ar 1 to Ar 3 , and R 1 to R 6 are the same as respectively defined with respect to Formula 1.

18. The monoamine compound of claim 12 , wherein the monoamine compound represented by Formula 1 is represented by the following Formula 3:

wherein in Formula 3, L, Ar 1 , Ar 2 , and R 1 to R 6 are the same as respectively defined with respect to Formula 1.

19. The monoamine compound of claim 12 , wherein the monoamine compound represented by Formula 1 is represented by the following Formula 4:

wherein Formula 4, another pair of R 2 and R 3 , or R 4 and R 5 , which do not form the substituted or unsubstituted benzene ring, are each a hydrogen atom, and

L, and Ar 1 to Ar 3 are the same as respectively defined with respect to Formula 1.

20. The monoamine compound of claim 12 , wherein the monoamine compound represented by Formula 1 is represented by any one of compounds represented in the following Compound Group 1:

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 9, 2019
From: TAKADA, ICHINORI
To: SAMSUNG DISPLAY CO., LTD.
Reel/Frame 050319/0771 →
Priority Claims (1)
KR 10-2018-0146635 · Nov 23, 2018 · national
Continuity (1)
Related Publication 20200168797A1 · May 28, 2020