IP Library › Granted Patent US 12,649,724
Granted Patent B2
US 12,649,724 · App. 17/740,509 · Granted Jun 9, 2026

Light emitting device and amine compound for the same

Inventor: Naoya Sakamoto (Yokohama, JP)
Assignee: SAMSUNG DISPLAY CO., LTD.
C07D307/91C07C211/54C07C211/57C07C211/61C07D209/86C07D213/38C07D333/76C07D409/12H10K85/615H10K85/622H10K85/631H10K85/633H10K85/636H10K85/657H10K85/6572H10K85/6574H10K85/6576C07B2200/05H10K50/15H10K50/16
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Quick Facts
Patent No.
US 12,649,724
App. No.
17/740,509
Granted
Jun 9, 2026
Kind
B2
Abstract

A light emitting device includes a first electrode, a second electrode disposed on the first electrode, and at least one functional layer disposed between the first electrode and the second electrode. The at least one functional layer includes an amine compound represented by Formula 1. A light emitting device including the amine compound may show improved efficiency and life characteristics.

Claims (86)

1 . A light emitting device, comprising:

a first electrode;

a second electrode disposed on the first electrode; and

at least one functional layer disposed between the first electrode and the second electrode, the at least one functional layer comprising an amine compound represented by the Formula 1:

wherein in Formula 1,

L 1 is direct linkage, a substituted or unsubstituted arylene group of 6 to 15 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group of 2 to 15 ring-forming carbon atoms,

Ar 1 is a phenyl group substituted with a substituted or unsubstituted alkyl group, a phenyl group substituted with a substituted or unsubstituted phenyl group, a phenyl group substituted with a substituted or unsubstituted naphthyl group, an unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted phenanthrene group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted dibenzothiophene group, a substituted or unsubstituted naphthobenzofuran group, or a substituted or unsubstituted benzonaphthothiophene group, wherein Ar 1 does not include an adamantyl group,

Ar 2 is a group represented by Formula 2,

n1 is an integer from 0 to 4,

R 1 is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group of 1 to 15 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms, or is combined with an adjacent group to form a ring,

at least one of R 2 to R 8 is a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms, and

the remainder of R 2 to R 8 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group of 1 to 15 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms:

wherein in Formula 2,

n11 is an integer from 0 to 6,

n12 is an integer from 0 to 7, and

R 11 and R 12 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group of 1 to 15 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms.

2 . The light emitting device of claim 1 , wherein the amine compound represented by Formula 1 is represented by Formula 1-A1 or Formula 1-A2:

wherein in Formula 1-A1 and Formula 1-A2,

Ar 1 , L 1 , n1, n11, n12, R 1 to R 8 , R 11 , and R 12 are the same as defined in Formula 1 and Formula 2.

3 . The light emitting device of claim 1 , wherein the amine compound represented by Formula 1 is represented by Formula 1-B1 or Formula 1-B2:

wherein in Formula 1-B1 and Formula 1-B2,

Ar 1 , L 1 , n1, n11, n12, R 1 to R 8 , R 11 , and R 12 are the same as defined in Formula 1 and Formula 2.

4 . The light emitting device of claim 1 , wherein the amine compound represented by Formula 1 is represented by Formula 1-C1 or Formula 1-C2:

wherein in Formula 1-C1 and Formula 1-C2,

Ar 1 , Ar 2 , n1, and R 1 to R 8 are the same as defined in Formula 1.

5 . The light emitting device of claim 1 , wherein Ar 1 is a group represented by one of Ar1-1 to Ar1-6:

wherein in Ar1-1,

n15 is an integer from 0 to 5, and

R 15 is a hydrogen atom, a substituted or unsubstituted alkyl group of 1 to 10 carbon atoms, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted naphthyl group,

wherein in Ar1-2,

n16 is an integer from 0 to 7, and

R 16 is a hydrogen atom, a halogen atom, or a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms,

wherein in Ar1-5,

X 1 is N(R 18 ), O, or S,

n17 is an integer from 0 to 7, and

R 17 and R 18 are each independently a hydrogen atom, or a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms,

wherein in Ar1-6,

X 2 is O or S.

6 . The light emitting device of claim 1 , wherein

at least one of R 1 to R 8 comprises a deuterium atom as a substituent, or

at least one of R 11 and R 12 is a deuterium atom.

7 . The light emitting device of claim 1 , wherein at least one of R 4 and R 8 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted pyridine group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted dibenzofuran group, or a substituted or unsubstituted dibenzothiophene group.

8 . The light emitting device of claim 1 , wherein

the at least one functional layer comprises:

an emission layer;

a hole transport region disposed between the first electrode and the emission layer; and

an electron transport region disposed between the emission layer and the second electrode, and

the hole transport region comprises the amine compound.

9 . The light emitting device of claim 8 , wherein

the hole transport region comprises:

a hole injection layer disposed on the first electrode;

a hole transport layer disposed on the hole injection layer; and

an electron blocking layer disposed on the hole transport layer, and

at least one of the hole injection layer, the hole transport layer, and the electron blocking layer comprises the amine compound.

10 . The light emitting device of claim 1 , wherein the amine compound is one selected from Compound Group 1:

wherein in Compound Group 1,

D is a deuterium atom.

11 . An amine compound represented by Formula 1:

wherein in Formula 1,

L 1 is direct linkage, a substituted or unsubstituted arylene group of 6 to 15 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group of 2 to 15 ring-forming carbon atoms,

Ar 1 is a phenyl group substituted with a substituted or unsubstituted alkyl group, a phenyl group substituted with a substituted or unsubstituted phenyl group, a phenyl group substituted with a substituted or unsubstituted naphthyl group, an unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted phenanthrene group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted dibenzothiophene group, a substituted or unsubstituted naphthobenzofuran group, or a substituted or unsubstituted benzonaphthothiophene group, wherein Ar 1 does not include an adamantyl group,

Ar 2 is a group represented by Formula 2,

n1 is an integer from 0 to 4,

R 1 is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted oxy group, a substituted or unsubstituted alkyl group of 1 to 15 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms, or is combined with an adjacent group to form a ring,

at least one of R 2 to R 8 is a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms, and

the remainder of R 2 to R 8 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group of 1 to 15 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms:

wherein in Formula 2,

n11 is an integer from 0 to 6,

n12 is an integer from 0 to 7, and

R 11 and R 12 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group of 1 to 15 carbon atoms, a substituted or unsubstituted aryl group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms.

12 . The amine compound of claim 11 , wherein the amine compound represented by Formula 1 is represented by Formula 1-A1 or Formula 1-A2:

wherein in Formula 1-A1 and Formula 1-A2,

Ar 1 , L 1 , n1, n11, n12, R 1 to R 8 , R 11 , and R 12 are the same as defined in Formula 1 and Formula 2.

13 . The amine compound of claim 11 , wherein the amine compound represented by Formula 1 is represented by Formula 1-B1 or Formula 1-B2:

wherein in Formula 1-B1 and Formula 1-B2,

Ar 1 , L 1 , n1, n11, n12, R 1 to R 8 , R 11 , and R 12 are the same as defined in Formula 1 and Formula 2.

14 . The amine compound of claim 11 , wherein the amine compound represented by Formula 1 is represented by Formula 1-C1 or Formula 1-C2:

wherein in Formula 1-C1 and Formula 1-C2,

Ar 1 , Ar 2 , n1, and R 1 to R 8 are the same as defined in Formula 1.

15 . The amine compound of claim 11 , wherein at least one of R 4 and R 8 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted pyridine group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted dibenzofuran group, or a substituted or unsubstituted dibenzothiophene group.

16 . The amine compound of claim 11 , wherein

at least one of R 1 to R 8 comprises a deuterium atom as a substituent, or

at least one of R 11 and R 12 is a deuterium atom.

17 . The amine compound of claim 11 , wherein the amine compound represented by Formula 1 is one selected from Compound Group 1:

wherein in Compound Group 1,

D is a deuterium atom.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 10, 2022
From: SAKAMOTO, NAOYA
To: SAMSUNG DISPLAY CO., LTD.
Reel/Frame 059883/0653 →
Priority Claims (1)
KR 10-2021-0076002 · Jun 11, 2021 · national
Continuity (1)
Related Publication 20230012692A1 · Jan 19, 2023
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