IP Library › Granted Patent US 12,501,825

Granted Patent B2

US 12,501,825 · App. 17/447,256 · Granted Dec 16, 2025

Organic electroluminescence device and amine compound for organic electroluminescence device

Inventor: Takao Sakuma (Yokohama, JP)

Assignee: Samsung Display Co., Ltd.

H10K85/636 H10K85/626 H10K85/6572 H10K85/6574 H10K85/6576 H10K50/15 H10K50/18

View Patent ↗

Loading inventors, assignments & file history…

Monitor This Case

Get email alerts when status or documents change.

Order Certified Copies

Most orders are placed with the USPTO same day — all within 24 business hours.

Order via The Patent Place →

Pre-filled with this patent's details

Quick Facts

Patent No.: US 12,501,825
App. No.: 17/447,256
Granted: Dec 16, 2025
Kind: B2

External Links

USPTO Patent Center↗ Full Patent PDF↗

Abstract

An organic electroluminescence device of an embodiment includes a first electrode, a hole transport region on the first electrode, an emission layer on the hole transport region, an electron transport region on the emission layer, and a second electrode on the electron transport region, wherein the hole transport region includes an amine compound represented by Formula 1, thereby showing long life:

Claims (1062)

1 . An organic electroluminescence device, comprising:

a first electrode;

a hole transport region on the first electrode;

an emission layer on the hole transport region;

an electron transport region on the emission layer; and

a second electrode on the electron transport region,

wherein the hole transport region comprises a plurality of layers, one layer from the plurality of layers consisting of an amine compound represented by Formula 1 and the amine compound represented by Formula 1 is only in the one layer:

wherein in Formula 1,

Ar 1 is represented by Formula 2-1, Ar 2 is represented by Formula 2-2, and Ar 3 is represented by Formula 2-3:

and

wherein in Formula 2-1 to Formula 2-3,

R 1 and R 2 are each independently a hydrogen atom, a deuterium atom, a chlorine atom, a bromine atom, an iodine atom, a cyano group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted silyl group, 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,

R 3 to R 5 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted oxy group, a substituted or unsubstituted thiol group, a substituted or unsubstituted silyl group, 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,

L 1 is a direct linkage, a substituted or unsubstituted arylene group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group of 2 to 30 ring-forming carbon atoms,

R 6 to R 9 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group of 2 to 20 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, and/or combined with an adjacent group to form a ring, where a fluorenyl group is excluded,

R 10 is a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group of 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group of 2 to 20 carbon atoms, a substituted phenyl group, a substituted or unsubstituted aryl group of 7 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroaryl group of 2 to 30 ring-forming carbon atoms, and/or combined with an adjacent group to form a ring, where a fluorenyl group is excluded,

R 6 to R 10 are not all hydrogen atoms,

a to d are each independently an integer of 0 to 4,

e is an integer of 0 to 7,

f is an integer of 0 to 2,

when f is 1 and L 1 is a phenylene group, then R 10 is not an unsubstituted heteroaryl group, an unsubstituted naphthalene group, an unsubstituted p-biphenyl group, a substituted or unsubstituted phenanthryl group, or a phenyl group para-substituted by an unsubstituted naphthalene group, and R 6 to R 9 are not a substituted or unsubstituted phenanthryl group,

when L 1 is a direct linkage, one selected from R 6 to R 9 is an unsubstituted phenyl group and the rest selected from R 6 to R 9 and R 10 are each a hydrogen atom, and all R 1 to R 3 groups are each a hydrogen atom, then all R 5 groups are each a hydrogen atom, and

when L 1 is a direct linkage and the carbon at position 3 of the dibenzothiophene group of Formula 2-2 is combined with N of Formula 1, then R 10 is not combined with an adjacent group to form a 3-dibenzothiophene group, or a 3-dibenzofuran group.

2 . The organic electroluminescence device of claim 1 , wherein the hole transport region comprises:

a hole injection layer on the first electrode; and

a hole transport layer on the hole injection layer, and

the hole injection layer or the hole transport layer consists of the amine compound represented by Formula 1.

3 . The organic electroluminescence device of claim 1 , wherein the hole transport region comprises:

a hole transport layer on the first electrode; and

an electron blocking layer on the hole transport layer, and

the electron blocking layer consists of the amine compound represented by Formula 1.

4 . The organic electroluminescence device of claim 1 , wherein Formula 1 is represented by any one among Formula 3-1 to Formula 3-4:

and

wherein in Formula 3-1 to Formula 3-4,

R 1 to R 10 , a to f, and L 1 are each independently the same as defined in Formula 1 and Formula 2.

5 . The organic electroluminescence device of claim 1 , wherein L 1 is a direct linkage, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, or a substituted or unsubstituted biphenylene group.

6 . The organic electroluminescence device of claim 1 , wherein L 1 is a direct linkage or represented by any one among L-1 to L-4:

and

wherein in L-1 to L-4,

R 11 to R 15 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group of 1 to 20 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,

g to j are each independently an integer of 0 to 4, and

k is an integer of 0 to 6.

7 . The organic electroluminescence device of claim 1 , wherein Ar 3 is represented by any one among Formula 4-1 to Formula 4-4:

and

wherein in Formula 4-1 to Formula 4-4,

R 6-1 to R 9-1 are each independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted aryl group of 6 to 20 ring-forming carbon atoms,

R 10-1 is a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group of 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group of 7 to 20 ring-forming carbon atoms,

where R 6-1 to R 10-1 are not all hydrogen atoms,

R b1 to R b3 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group of 1 to 20 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,

X is O or S,

m1 and m3 are each independently an integer of 0 to 7,

m2 is an integer of 0 to 9,

when L 1 is a direct linkage and the carbon at position 3 of the dibenzothiophene group of Formula 2-2 is combined with N of Formula 1, then Formula 4-4 is not a 3-dibenzofuran group or a 3-dibenzothiophene group, and

when f is 1 and L 1 is a phenylene group, then Ar 3 is any one among Formula 4-1 to Formula 4-3, and is not Formula 4-4, and in Formula 4-1, R 10-1 is not an unsubstituted naphthalene group, an unsubstituted p-biphenyl group, or a substituted or unsubstituted phenanthryl group, and R 6-1 to R 9-1 are not a substituted or unsubstituted phenanthryl group.

8 . The organic electroluminescence device of claim 7 , wherein A r3 represented by Formula 4-1 is represented by any one among Formula 5-1 to Formula 5-3:

and

wherein in Formula 5-1 to Formula 5-3,

P 10-2 is a substituted or unsubstituted alkyl group of 1 to 10 carbon atoms,

R c1 and R c2 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted alkyl group of 1 to 20 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,

n is 1 or 2,

m11 is an integer of 0 to 5, and

m12 is an integer of 0 to 7,

wherein when f is 1, L 1 is a phenylene group, Ar 3 is represented by Formula 5-2, and n of Formula 5-2 is 1, then m11 is 1 to 5 and at least one R c1 is not hydrogen, and

when f is 1, L 1 is a phenylene group, and Ar 3 is represented by Formula 5-3, then m12 is 1 to 7 and at least one R c2 of Formula 5-3 is not hydrogen.

9 . The organic electroluminescence device of claim 1 , wherein R 3 and R 4 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, or a substituted or unsubstituted alkyl group of 1 to 10 carbon atoms.

10 . The organic electroluminescence device of claim 1 , wherein the emission layer comprises an anthracene derivative represented by Formula 6:

and

wherein in Formula 6,

R 31 to R 40 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group of 1 to 10 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, and/or combined with an adjacent group to form a ring, and

q and r are each independently an integer of 0 to 5.

11 . The organic electroluminescence device of claim 10 , wherein Formula 6 is represented by any one among Compound 7-1 to Compound 7-19:

12 . The organic electroluminescence device of claim 1 , wherein the amine compound represented by Formula 1 is any one among combinations represented in Compound Group 1:

Compound Group 1

For-

mula

Ar 1

Ar 2

Ar 3

A10

A11

A12

A13

A14

A15

A16

A17

A18

A19

A20

A21

A22

A23

B10

B11

B12

B13

B14

B15

B16

B17

B18

B19

B20

B21

B22

B23

C10

C11

C12

C13

C14

C15

C16

C17

C18

C19

C20

C21

C22

C23

D10

D11

D12

D13

D14

D15

D16

D17

D18

D19

D20

D21

D22

D23

E10

E11

E12

E13

E14

E15

E16

E17

E18

E19

E20

E21

E22

E23

F10

F11

F12

F13

F14

F15

F16

F17

F18

F19

F20

F21

F22

G10

G11

G12

G13

G14

G15

G16

G17

G18

G19

G20

G21

G22

H10

H11

H13

H14

H15

H16

H17

H18

H19

H20

H21

H22

H23

I10

I11

I12

I13

I14

I15

I16

I17

I18

I19

I20

I21

I22

I23

J10

J11

J12

J13

J14

J15

J16

J17

J18

J19

J20

J21

J22

J23

K10

K11

K12

K13

K14

K15

K16

K17

K18

K19

K20

K21

M10

M11

M13

M14

M15

M16

M17

M18

M19

M20

M21

M22

M23

N10

N11

N13

N14

N15

N16

N17

N18

N19

N20

N21

N22

N23

O10

O11

O12

O13

O14

O15

O16

O17

O18

O19

O20

O21

O22

O23

P10

P11

P12

P13

P14

P15

P16

P17

P18

P19

P20

P21

P22

P23

Q10

Q11

Q12

Q13

Q14

Q15

Q16

Q17

Q18

Q19

Q20

Q21

Q22

Q23

Q24

Q25

Q26

Q27

S10

S11

S13

S14

S15

S16

S17

S18

S19

S20

S21

S22

S23

T10

T11

T13

T14

T15

T16

T17

T18

T19

T20

T21

T22

T23

U10

U11

U12

U13

U14

U15

U16

U17

U18

U19

U20

U21

U22

U23

V10

V11

V12

V13

V14

V15

V16

V17

V18

V19

V20

V21

V22

V23

13 . An amine compound represented by Formula 1:

wherein in Formula 1,

Ar 1 is represented by Formula 2-1, Ar 2 is represented by Formula 2-2, and Ar 3 is represented by Formula 2-3:

and

wherein in Formula 2-1 to Formula 2-3,

L 1 is a direct linkage, a substituted or unsubstituted arylene group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group of 2 to 30 ring-forming carbon atoms,

R 6 to R 10 are not all hydrogen atoms,

a to d are each independently an integer of 0 to 4,

e is an integer of 0 to 7,

f is an integer of 0 to 2,

when L 1 is a direct linkage, and R 1 to R 5 are each a hydrogen atom, then Ar 3 is not a naphthyl group, and

14 . The amine compound of claim 13 , wherein Formula 1 is represented by any one among Formula 3-1 to Formula 3-4:

and

wherein in Formula 3-1 to Formula 3-4,

R 1 to R 10 , a to f, and L 1 are each independently the same as defined in Formula 1 and Formula 2.

15 . The amine compound of claim 13 , wherein L 1 is a direct linkage, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, or a substituted or unsubstituted biphenylene group.

16 . The amine compound of claim 13 , wherein L 1 is a direct linkage or represented by any one among L-1 to L-4:

and

wherein in L-1 to L-4,

g to j are each independently an integer of 0 to 4, and

k is an integer of 0 to 6.

17 . The amine compound of claim 13 , wherein Ar 3 is represented by any one among Formula 4-1 to Formula 4-4:

and

wherein in Formula 4-1 to Formula 4-4,

R 6-1 to R 9-1 are each independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted aryl group of 6 to 20 ring-forming carbon atoms,

R 10-1 is a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group of 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group of 7 to 20 ring-forming carbon atoms,

where R 6-1 to R 10-1 are not all hydrogen atoms,

X is O or S,

m1 and m3 are each independently an integer of 0 to 7,

m2 is an integer of 0 to 9,

when f is 1 and L 1 is a phenylene group, then Ar 3 is any one among Formula 4-1 to Formula 4-3 and is not Formula 4-4, and in Formula 4-1, R 10-1 is not an unsubstituted naphthalene group, an unsubstituted p-biphenyl group, or a substituted or unsubstituted phenanthryl group, and R 6-1 to R 9-1 are not a substituted or unsubstituted phenanthryl group.

18 . The amine compound of claim 17 , wherein Ar 3 represented by Formula 4-1 is represented by any one among Formula 5-1 to Formula 5-3:

and

wherein in Formula 5-1 to Formula 5-3,

P 10-2 is a substituted or unsubstituted alkyl group of 1 to 10 carbon atoms,

n is 1 or 2,

m11 is an integer of 0 to 5, and

m12 is an integer of 0 to 7, and

wherein

when f is 1, L 1 is a phenylene group, Ar 3 is represented by Formula 5-2, and n of Formula 5-2 is 1, then m11 is 1 to 5 and at least one R c1 is not hydrogen, and

when f is 1, L 1 is a phenylene group, and Ar 3 is represented by Formula 5-3, then m12 is 1 to 7 and at least one R c2 of Formula 5-3 is not hydrogen.

19 . The amine compound of claim 13 , wherein R 3 and R 4 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, or a substituted or unsubstituted alkyl group of 1 to 10 carbon atoms.

20 . An amine compound, wherein the amine compound is any one among combinations represented in Compound Group 1:

Compound Group 1

For-

mu-

la 1

Ar 1

Ar 2

Ar 3

A10

A11

A12

A13

A14

A15

A16

A17

A18

A19

A20

A21

A22

A23

B10

B11

B12

B13

B14

B15

B16

B17

B18

B19

B20

B21

B22

B23

C10

C11

C12

C13

C14

C15

C16

C17

C18

C19

C20

C21

C22

C23

D10

D11

D12

D13

D14

D15

D16

D17

D18

D19

D20

D21

D22

D23

E10

E11

E12

E13

E14

E15

E16

E17

E18

E19

E20

E21

E22

E23

F10

F11

F12

F13

F14

F15

F16

F17

F18

F19

F20

F21

F22

G10

G11

G12

G13

G14

G15

G16

G17

G18

G19

G20

G21

G22

H10

H11

H12

H13

H14

H15

H16

H17

H18

H19

H20

H21

H22

H23

I10

I11

I12

I13

I14

I15

I16

I17

I18

I19

I20

I21

I22

I23

J10

J11

J12

J13

J14

J15

J16

J17

J18

J19

J20

J21

J22

J23

K10

K11

K12

K13

K14

K15

K16

K17

K18

K19

K20

K21

M10

M11

M12

M13

M14

M15

M16

M17

M18

M19

M20

M21

M22

M23

N10

N11

N12

N13

N14

N15

N16

N17

N18

N19

N20

N21

N22

N23

O10

O11

O12

O13

O14

O15

O16

O17

O18

O19

O20

O21

O22

O23

P10

P11

P12

P13

P14

P15

P16

P17

P18

P19

P20

P21

P22

P23

Q10

Q11

Q12

Q13

Q14

Q15

Q16

Q17

Q18

Q19

Q20

Q21

Q22

Q23

Q24

Q25

Q26

Q27

S10

S11

S12

S13

S14

S15

S16

S17

S18

S19

S20

S21

S22

S23

T10

T11

T12

T13

T14

T15

T16

T17

T18

T19

T20

T21

T22

T23

U10

U11

U12

U13

U14

U15

U16

U17

U18

U19

U20

U21

U22

U23

V10

V11

V12

V13

V14

V15

V16

V17

V18

V19

V20

V21

V22

V23

21 . A display device including an organic electroluminescence device,

wherein the organic electroluminescence device comprising:

a first electrode;

a hole transport region on the first electrode;

an emission layer on the hole transport region;

an electron transport region on the emission layer; and

a second electrode on the electron transport region,

wherein in Formula 1,

Ar 1 is represented by Formula 2-1, Ar 2 is represented by Formula 2-2, and Ar 3 is represented by Formula 2-3:

and

wherein in Formula 2-1 to Formula 2-3,

L 1 is a direct linkage, a substituted or unsubstituted arylene group of 6 to 30 ring-forming carbon atoms, or a substituted or unsubstituted heteroarylene group of 2 to 30 ring-forming carbon atoms,

R 6 to R 10 are not all hydrogen atoms,

a to d are each independently an integer of 0 to 4,

e is an integer of 0 to 7,

f is an integer of 0 to 2,

when L 1 is a direct linkage and the carbon at position 3 of the dibenzothiophene group of Formula 2-2 is combined with N of Formula 1 , then R 10 is not combined with an adjacent group to form a 3-dibenzothiophene group, or a 3-dibenzofuran group.

Assignments (1)

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 9, 2021

From: SAKUMA, TAKAO

To: SAMSUNG DISPLAY CO., LTD.

Reel/Frame 057431/0586 →

Priority Claims (1)

KR 10-2020-0176475 · Dec 16, 2020 · national

Continuity (1)

Related Publication 20230103918A1 · Apr 6, 2023

References Cited (41)

US 8614010B2 · Yabunouchi et al. · 2013 [cited by applicant]

US 9054322B2 · Yabunouchi et al. · 2015 [cited by applicant]

US 9966536B2 · Itoi · 2018 [cited by applicant]

US 9972786B2 · Yabunouchi et al. · 2018 [cited by applicant]

US 10246441B2 · Kato · 2019 [cited by applicant]

US 10516112B2 · Kato et al. · 2019 [cited by applicant]

US 11685751B2 · Geum et al. · 2023 [cited by applicant]

US 20160372666A1 · Ryu et al. · 2016 [cited by applicant]

US 20200091435A1 · Masuda et al. · 2020 [cited by applicant]

US 20200144506A1 · Song et al. · 2020 [cited by applicant]

US 20200317653A1 · Ito · 2020 [cited by examiner]

US 20200335705A1 · Song · 2020 [cited by examiner]

US 20210167298A1 · Pang · 2021 [cited by examiner]

US 20230303537A1 · Li · 2023 [cited by examiner]

CN 102224150B · 2015 [cited by applicant]

CN 108658953A · 2018 [cited by applicant]

CN 105061371B · 2019 [cited by applicant]

CN 110431682A · 2019 [cited by applicant]

CN 111732578A · 2020 [cited by examiner]

CN 111834535A · 2020 [cited by applicant]

CN 113527271A · 2021 [cited by applicant]

CN 113994497A · 2022 [cited by applicant]

CN 114402453A · 2022 [cited by applicant]

EP 2364980B1 · 2017 [cited by applicant]

EP 3156403B1 · 2019 [cited by applicant]

JP 5608095B2 · 2014 [cited by applicant]

KR 101181261B1 · 2012 [cited by applicant]

KR 101446401B1 · 2014 [cited by applicant]

KR 101571986B1 · 2015 [cited by applicant]

KR 1020160030429A · 2016 [cited by applicant]

KR 101600127B1 · 2016 [cited by applicant]

KR 101905721B1 · 2018 [cited by applicant]

KR 102128702B1 · 2020 [cited by applicant]

KR 20200088704A · 2020 [cited by examiner]

TW I498313B · 2015 [cited by applicant]

WO WO2010061824A1 · 2010 [cited by applicant]

WO WO2014030921A1 · 2014 [cited by applicant]

WO WO2016006711A1 · 2016 [cited by applicant]

Machine translation of CN-111732578, translation generated May 2024, 13 pages. (Year: 2024). [cited by examiner]

Machine translation of KR-20200088704-A, translation generated Sep. 2024, 14 pages. (Year: 2024). [cited by examiner]

Chinese Office Action, for CN Patent Application No. 202111533153.9, dated Sep. 25, 2025, 12 pages. [cited by applicant]