IP Library › Granted Patent US 12,559,477
Granted Patent B2
US 12,559,477 · App. 17/660,006 · Granted Feb 24, 2026

Light-emitting device including heterocyclic compound and electronic apparatus including the light-emitting device

Inventors: Hyunwoo Lee (Yongin-si, KR); Jungsub Lee (Yongin-si, KR); Hyojeong Kim (Yongin-si, KR)
Assignee: Samsung Display Co., Ltd.
C07D403/10C07D405/14C07D409/14C07D487/04C07F7/0812H10K85/40H10K85/654H10K85/6572H10K85/6574H10K85/6576C07B2200/05H10K50/11H10K50/12H10K2101/10
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Quick Facts
Patent No.
US 12,559,477
App. No.
17/660,006
Granted
Feb 24, 2026
Kind
B2
Abstract

A light-emitting device and an electronic apparatus (including the light-emitting device) are provided. The light-emitting device includes a first compound represented by Formula 1 and a second compound represented by Formula 2: wherein detailed descriptions of Formula 1 and Formula 2 are the same as described in the present specification.

Claims (81)

1 . A light-emitting device comprising:

a first electrode;

a second electrode facing the first electrode;

an interlayer between the first electrode and the second electrode and comprising an emission layer;

a first compound represented by Formula 1; and

a second compound represented by Formula 2:

wherein, in Formulae 1 and 2,

X 1 is N, B, P(═O), or P(═S),

X 2 is N, B, P(═O), or P(═S),

X 3 is N, B, P(═O), or P(═S),

X 4 is N, B, P(═O), or P(═S), L 1 is a single bond, a C 5 -C 30 carbocyclic group unsubstituted or substituted with at least one R 10a , or a C 1 -C 30 heterocyclic group unsubstituted or substituted with at least one R 10a ,

a1 is an integer from 0 to 3,

ring CY2 to ring CY5 are each independently a C 3 -C 60 carbocyclic group or a C 1 -C 60 heterocyclic group,

Ar 1 to Ar 6 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 1 -C 60 alkyl group unsubstituted or substituted with at least one R 10a , a C 2 -C 60 alkenyl group unsubstituted or substituted with at least one R 10a , a C 2 -C 60 alkynyl group unsubstituted or substituted with at least one R 10a , a C 1 -C 60 alkoxy group unsubstituted or substituted with at least one R 10a , a C 3 -C 60 carbocyclic group unsubstituted or substituted with at least one R 10a , a C 1 -C 60 heterocyclic group unsubstituted or substituted with at least one R 10a , a C 6 -C 60 aryloxy group unsubstituted or substituted with at least one R 10a , a C 6 -C 60 arylthio group unsubstituted or substituted with at least one R 10a , —Si(Q 1 )(Q 2 )(Q 3 ), —N(Q 1 )(Q 2 ), —B(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —S(═O) 2 (Q 1 ), and —P(═O)(Q 1 )(Q 2 ),

b1 to b5 are each an integer from 0 to 10, and

R 10a is:

deuterium (-D), —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, or a nitro group;

a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, or a C 1 -C 60 alkoxy group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 3 -C 60 carbocyclic group, a C 1 -C 60 heterocyclic group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 7 -C 60 aryl alkyl group, a C 2 -C 60 heteroaryl alkyl group, —Si(Q 11 )(Q 12 )(Q 13 ), —N(Q 11 )(Q 12 ), —B(Q 11 )(Q 12 ), —C(═O)(Q 11 ), —S(═O) 2 (Q 11 ), —P(═O)(Q 11 )(Q 12 ), or any combination thereof;

a C 3 -C 60 carbocyclic group, a C 1 -C 60 heterocyclic group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 7 -C 60 aryl alkyl group, or a C 2 -C 60 heteroaryl alkyl group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 3 -C 60 carbocyclic group, a C 1 -C 60 heterocyclic group, a C 6 -C 60 aryloxy group, a C 6 -Coo arylthio group, a C 7 -Coo aryl alkyl group, a C 2 -C 60 heteroaryl alkyl group, —Si(Q 21 )(Q 22 )(Q 23 ), —N(Q 21 )(Q 22 ), —B(Q 21 )(Q 22 ), —C(═O)(Q 21 ), —S(═O) 2 (Q 21 ), —P(═O)(Q 21 )(Q 22 ), or any combination thereof; or

—Si(Q 31 )(Q 32 )(Q 33 ), —N(Q 31 )(Q 32 ), —B(Q 31 )(Q 32 ), —C(═O)(Q 31 ), —S(═O) 2 (Q 31 ), or —P(═O)(Q 31 )(Q 32 ), and

wherein Q 1 to Q 3 , Q 11 to Q 13 , Q 21 to Q 23 , and Q 31 to Q 33 are each independently hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; a C 1 -C 60 alkyl group; a C 2 -C 60 alkenyl group; a C 2 -C 60 alkynyl group; a C 1 -C 60 alkoxy group; a C 3 -C 60 carbocyclic group or a C 1 -C 60 heterocyclic group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C 1 -C 60 alkyl group, a C 1 -C 60 alkoxy group, a phenyl group, a biphenyl group, or any combination thereof; a C 7 -C 60 aryl alkyl group; or a C 2 -C 60 heteroaryl alkyl group.

2 . The light-emitting device of claim 1 , wherein the emission layer comprises the first compound and the second compound.

3 . The light-emitting device of claim 2 , wherein each of the first compound and the second compound is a host.

4 . The light-emitting device of claim 2 , wherein the first compound and the second compound are different from each other.

5 . The light-emitting device of claim 2 , wherein the emission layer further comprises a dopant.

6 . The light-emitting device of claim 5 , wherein the dopant comprises a phosphorescent dopant, a delayed fluorescence material, or any combination thereof.

7 . The light-emitting device of claim 1 , wherein the emission layer is to emit blue light.

8 . The light-emitting device of claim 1 , wherein a ratio of an amount of the first compound to an amount of the second compound is in a range of 1:0.1 to 1:10.

9 . The light-emitting device of claim 1 , wherein, in Formulae 1 and 2,

X 1 is N, P(═O), or P(═S),

X 2 is N, P(═O), or P(═S),

X 3 is N, P(═O), or P(═S), and

X 4 is N, P(═O), or P(═S).

10 . The light-emitting device of claim 1 , wherein, in Formula 1, L 1 is:

a single bond; or

a benzene group or a carbazole group, each unsubstituted or substituted with at least one R 10a .

11 . The light-emitting device of claim 1 , wherein, in Formulae 1 and 2, ring CY2 to ring CY5 are each independently a benzene group, a naphthalene group, a carbazole group, a dibenzofuran group, a fluorene group, a dibenzothiophene group, or a dibenzosilole group, each unsubstituted or substituted with at least one R 10a .

12 . The light-emitting device of claim 1 , wherein, in Formula 1, ring CY2 is a group represented by one of Formulae CY2-1 to CY2-5:

wherein, in Formulae CY2-1 to CY2-5,

Ar 2 is the same as described in connection with Formula 1,

* indicates a binding site to X 1 in Formula 1, and

*′ indicates a binding site to an element included in ring CY3 in Formula 1.

13 . The light-emitting device of claim 1 , wherein, in Formula 1, ring CY3 is a group represented by one of Formulae CY3-1 to CY3-5:

wherein, in Formulae CY3-1 to CY3-5,

Ar 3 is the same as described in connection with Formula 1,

* indicates a binding site to X 1 in Formula 1, and

**′ indicates a binding site to an element included in ring CY2 in Formula 1.

14 . The light-emitting device of claim 1 , wherein, in Formula 2, ring CY4 is a group represented by one of Formulae CY4-1 to CY4-5:

wherein, in Formulae CY4-1 to CY4-5,

Ar 4 is the same as described in connection with Formula 1,

* indicates a binding site to X 2 in Formula 2, and

**′ indicates a binding site to X 3 in Formula 2.

15 . The light-emitting device of claim 1 , wherein, in Formula 2, ring CY5 is a group represented by one of Formulae CY5-1 to CY5-5:

wherein, in Formulae CY5-1 to CY5-5, Ar 3 is the same as described in connection with Formula 1,

* indicates a binding site to X 4 in Formula 2, and

**′ indicates a binding site to X 3 in Formula 2.

16 . The light-emitting device of claim 1 , wherein, in Formula 1, Ar 1 to Ar 3 are each independently:

hydrogen, deuterium, a group represented by —Si(Q 1 )(Q 2 )(Q 3 ); or a group represented by one of Formulae 4-1 to 4-10:

wherein, in Formulae 4-1 to 4-10,

X 41 is C(R 41a )(R 41b ), Si(R 41a )(R 41b ), N(R 41a ), O, S, or Se,

Q 1 to Q 3 are each independently the same as described in connection with Formula 1,

R 41a , R 41b , Z 41 , and Z 42 are each independently hydrogen or the same as described in connection with R 10a ,

e2 is an integer from 0 to 2,

e3 is an integer from 0 to 3,

e4 is an integer from 0 to 4,

e5 is an integer from 0 to 5,

e7 is an integer from 0 to 7, and

* indicates a binding site to a neighboring group.

17 . The light-emitting device of claim 1 , wherein, in Formula 2, Ar 4 to Ar 6 are each independently:

hydrogen, deuterium, a cyano group; or a group represented by one of Formulae 5-1 to 5-3:

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

Z 51 and Z 52 are each independently hydrogen or the same as described in connection with R 10a ,

f2 is an integer from 0 to 2,

f4 is an integer from 0 to 4,

f5 is an integer from 0 to 4, and

* indicates a binding site to a neighboring group.

18 . An electronic apparatus comprising the light-emitting device of claim 1 .

19 . The electronic apparatus of claim 18 , further comprising a thin-film transistor, wherein

the thin-film transistor comprises a source electrode and a drain electrode, and

the first electrode of the light-emitting device is electrically connected to the source electrode or the drain electrode of the thin-film transistor.

20 . The electronic apparatus of claim 18 , further comprising a color filter, a color conversion layer, a touch screen layer, a polarizing layer, or any combination thereof.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 5, 2022
From: LEE, HYUNWOO; LEE, JUNGSUB; KIM, HYOJEONG
To: SAMSUNG DISPLAY CO., LTD.
Reel/Frame 059829/0119 →
Priority Claims (1)
KR 10-2021-0062759 · May 14, 2021 · national
Continuity (1)
Related Publication 20220388989A1 · Dec 8, 2022
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