IP Library › Granted Patent US 12,532,660
Granted Patent B2
US 12,532,660 · App. 17/337,911 · Granted Jan 20, 2026

Light emitting device and amine compound for the same

Inventor: Naoya Sakamoto (Yokohama, JP)
Assignee: Samsung Display Co., Ltd.
H10K85/636H10K85/40H10K85/622H10K85/654H10K85/6572H10K85/6574H10K85/6576
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Quick Facts
Patent No.
US 12,532,660
App. No.
17/337,911
Granted
Jan 20, 2026
Kind
B2
Abstract

Provided is a light emitting device including 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 may include an amine compound represented by Formula 1 below, thereby exhibiting excellent luminous efficiency and improved service life characteristics.

Claims (81)

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 and comprising an amine compound represented by one of Formula 1-1, Formula 1-2, Formula 1-3, or Formula 1-6:

wherein in Formula 1-1, Formula 1-2, Formula 1-3, and Formula 1-6,

Q 1 is a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms,

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

R 1 , R 2 , R 3 , and R 4 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms,

Ar 3 is a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms,

a1 is an integer from 0 to 4, and

R 5 is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms.

2 . The light emitting device of claim 1 , wherein

Q 1 is a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted dibenzothiophene group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted dibenzosilole group, a substituted or unsubstituted dibenzothiophene sulfone group, a substituted or unsubstituted pyridine group, a substituted or unsubstituted pyrimidine group, or a substituted or unsubstituted triazine group.

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

wherein in Formula 3,

a11, a13, and a14 are each independently an integer from 0 to 5,

a12 is an integer from 0 to 4, and

at least one of R 11 to R 14 is a deuterium atom, and

the remainder of R 11 to R 14 are hydrogen atoms.

4 . The light emitting device of claim 1 , wherein Ar 1 and Ar 2 are each independently represented by one of A-1 to A-3:

wherein in A-1,

Ar 11 is a hydrogen atom, a methyl group, or a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, and

wherein A-1 to A-3,

indicates a binding site to a neighboring atom.

5 . The light emitting device of claim 1 , wherein Ar 1 and Ar 2 are the same as each other.

6 . The light emitting device of claim 1 , wherein

Ar 3 is a substituted or unsubstituted phenyl group, an unsubstituted naphthyl group, an unsubstituted phenanthryl group, an unsubstituted triphenyl group, an unsubstituted naphthobenzofuran group, or an unsubstituted benzonaphthothiophene group.

7 . The light emitting device of claim 1 , wherein the difference value between a lowest singlet exciton energy level and a lowest triplet exciton energy level of the amine compound is equal to or less than about 0.2 eV.

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

at least one of the hole transport layer and the emission layer comprises the amine compound.

9 . 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,

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 125 to Compound 127,

D is a deuterium atom.

11 . An amine compound represented by Formula lone of Formula 1-1, Formula 1-2, Formula 1-3, or Formula 1-6:

wherein in Formula 1-1, Formula 1-2, Formula 1-3, and Formula 1-6,

Q 1 is a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms,

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

R 1 , R 2 , R 3 , and R 4 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms,

Ar 3 is a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms,

a1 is an integer from 0 to 4, and

R 5 is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms.

12 . The amine compound of claim 11 , wherein in Formula 1-2, Formula 1-3, and Formula 1-6,

Q 1 is a substituted or unsubstituted dibenzofuran group, or a substituted or unsubstituted dibenzothiophene group.

13 . The amine compound of claim 11 , wherein Q 1 is represented by one of Q-1 to Q-8:

wherein in Q-6, a51 is an integer from 0 to 2,

in Q-7, a52 is an integer from 0 to 3,

in Q-8, a53 is an integer from 0 to 4,

in Q-3 and Q-5 to Q-8,

R 51 to R 56 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring-forming carbon atoms, and

in Q-1 to Q-8,

indicates a binding site to a neighboring atom.

14 . The amine compound of claim 11 , wherein Ar 1 and Ar 2 are each independently represented by one of A-1 to A-3:

wherein in A-1,

Ar 11 is a hydrogen atom, a methyl group, or a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, and

wherein in A-1 to A-3,

indicates a binding site to a neighboring atom.

15 . The amine compound of claim 11 , wherein Ar 1 and Ar 2 are the same as each other.

16 . The amine compound of claim 11 , wherein Ar 3 is a substituted or unsubstituted phenyl group, an unsubstituted naphthyl group, an unsubstituted phenanthryl group, an unsubstituted triphenyl group, an unsubstituted naphthobenzofuran group, or an unsubstituted benzonaphthothiophene group.

17 . The amine compound of claim 11 , wherein the amine compound is represented by Formula 3:

wherein in Formula 3,

a11, a13, and a14 are each independently an integer from 0 to 5,

a12 is an integer from 0 to 4,

at least one of R 11 to R 14 is a deuterium atom, and

the remainder of R 11 to R 14 are hydrogen atoms.

18 . The amine compound of claim 11 , wherein the amine compound is one selected from Compound Group 1:

wherein in Compound 125 to Compound 127,

D is a deuterium atom.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 3, 2021
From: SAKAMOTO, NAOYA
To: SAMSUNG DISPLAY CO., LTD.
Reel/Frame 056475/0804 →
Priority Claims (1)
KR 10-2020-0136196 · Oct 20, 2020 · national
Continuity (1)
Related Publication 20220123221A1 · Apr 21, 2022
References Cited (23)
US 8039121B2 · Iwakuma et al. · 2011 [cited by applicant]
US 9278926B2 · Kato · 2016 [cited by applicant]
US 9650565B2 · Matsumoto et al. · 2017 [cited by applicant]
US 11437585B2 · Jeong et al. · 2022 [cited by applicant]
US 12289989B2 · Zhang et al. · 2025 [cited by applicant]
US 20170117488A1 · Ahn et al. · 2017 [cited by applicant]
US 20200144508A1 · Jang et al. · 2020 [cited by applicant]
CN 102596907A · 2012 [cited by applicant]
CN 110669040A · 2020 [cited by applicant]
CN 111253302 · 2020 [cited by applicant]
CN 111253302A · 2020 [cited by examiner]
CN 111564562A · 2020 [cited by applicant]
JP 2011088835A · 2011 [cited by applicant]
KR 20120066076A · 2012 [cited by examiner]
KR 101356953 · 2014 [cited by applicant]
KR 1020180027468 · 2018 [cited by applicant]
KR 101872580 · 2018 [cited by applicant]
KR 101935710 · 2019 [cited by applicant]
KR 1020200050748 · 2020 [cited by applicant]
KR 20200076003A · 2020 [cited by examiner]
WO 2011049123 · 2011 [cited by applicant]
WO WO2011049123A2 · 2011 [cited by examiner]
Search Report for Chinese Application No. 202110931238.6 dated Jun. 4, 2025. 13 pages . (see p. 11-12, categorizing the cited references). [cited by applicant]