IP Library › Granted Patent US 12,396,363
Granted Patent B2
US 12,396,363 · App. 17/533,135 · Granted Aug 19, 2025

Light-emitting device and an electronic apparatus including the same

Inventors: Seulong Kim (Yongin-si, KR); Soungwook Kim (Yongin-si, KR); Sungsoo Bae (Yongin-si, KR); Hyein Jeong (Yongin-si, KR); Hyewon Choi (Yongin-si, KR); Jaeweon Hur (Yongin-si, KR)
Assignee: Samsung Display Co., Ltd.
H10K85/6572H10K85/615H10K85/636H10K50/166H10K2101/90
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 12,396,363
App. No.
17/533,135
Granted
Aug 19, 2025
Kind
B2
Abstract

A light-emitting device includes: a first electrode; a second electrode facing the first electrode; an interlayer between the first electrode and the second electrode and including an emission layer; and a capping layer disposed on the second electrode, wherein the interlayer further includes an electron transport region between the emission layer and the second electrode, the capping layer includes at least one first material represented by Formula 1 or Formula 2, and the electron transport region satisfies at least one of Condition (1) and Condition (2), as defined herein.

Claims (186)

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; and

a capping layer disposed on the second electrode,

wherein the interlayer further comprises an electron transport region between the emission layer and the second electrode,

the capping layer comprises at least one first material represented by Formula 1 or Formula 2, and

the electron transport region satisfies at least one of Condition (1) and Condition (2):

Condition (1)

the electron transport region further comprises a first electron transport layer,

wherein the first electron transport layer comprises a mixture comprising an organic electron transport material and a metal element-containing material, and the organic electron transport material and the metal element-containing material are different from each other; and

Condition (2)

the electron transport region comprises at least one second material represented by Formula 1 or Formula 2:

wherein, in Formula 1,

X 11 is N or C(R 11 ),

X 12 is N or C(R 12 ),

A 11 and A 12 are each, independently from one another, a C 1 -C 60 heterocyclic group comprising at least one N,

L 11 and L 12 are each, independently from one another, a single bond, a C 5 -C 60 carbocyclic group unsubstituted or substituted with at least one R 10a , or a C 1 -C 60 heterocyclic group unsubstituted or substituted with at least one R 10a ,

a11 and a12 are each, independently from one another, an integer selected from 1 to 3,

E 11 , E 12 , R 11 , and R 12 are each, independently from one another, 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 ), or —P(═O)(Q 1 )(Q 2 ),

b11 and b12 are each, independently from one another, an integer selected from 1 to 8,

d11 and d12 are each, independently from one another, an integer selected from 1 to 8,

R 11 and R 12 are optionally linked to each other to form a C 5 -C 60 carbocyclic group unsubstituted or substituted with at least one R 10a or a C 2 -C 30 heterocyclic group unsubstituted or substituted with at least one R 10a ,

wherein, in Formula 2,

Y 21 is O, S, or Se,

A 21 is a C 5 -C 60 carbocyclic group unsubstituted or substituted with at least one R 10a or a C 1 -C 60 heterocyclic group unsubstituted or substituted with at least one R 10a ,

n21 is an integer selected from 1 to 3,

L 21 to L 23 are each, independently from one another, a single bond, a C 5 -C 60 carbocyclic group unsubstituted or substituted with at least one R 10a , or a C 1 -C 60 heterocyclic group unsubstituted or substituted with at least one R 10a ,

a21 to a23 are each, independently from one another, an integer selected from 1 to 3,

T 22 and T 23 are each, independently from one another, 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 ), or —P(═O)(Q 1 )(Q 2 ),

b22 and b23 are each, independently from one another, an integer selected from 1 to 8,

T 22 and T 23 are optionally linked to each other to form a C 2 -C 30 heterocyclic group unsubstituted or substituted with at least one R 10a , and

R 10a is:

deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, or a nitro group;

a C 1 -Coo 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, —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, or a C 6 -C 60 arylthio group, each independently from one another, 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 -C 60 arylthio 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 ),

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 from one another: 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; or 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, and

wherein the electron transport region further comprises a second electron transport layer between the first electron transport layer and the emission layer.

2. The light-emitting device of claim 1 , wherein the first electrode comprises an anode,

the second electrode comprises a cathode,

the interlayer further comprises a hole transport region between the emission layer and the first electrode,

the hole transport region comprises a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron blocking layer, or any combination thereof, and

the electron transport region comprises a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

3. The light-emitting device of claim 1 , wherein the second electrode comprises silver.

4. The light-emitting device of claim 3 , wherein silver in the second electrode comprises about 95 parts or more by mass based on the total 100 parts by mass of the second electrode.

5. The light-emitting device of claim 1 , wherein the electron transport region satisfies the Condition (2),

the electron transport region further comprises the first electron transport layer, and

the first electron transport layer comprises the second material represented by Formula 1 or Formula 2.

6. The light-emitting device of claim 1 , wherein the second electrode and the capping layer directly contact each other.

7. The light-emitting device of claim 1 , wherein the electron transport region satisfies the Condition (1), and

the organic electron transport material comprises the second material represented by Formula 1 or Formula 2.

8. The light-emitting device of claim 1 , wherein the metal element-containing material comprises an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof.

9. The light-emitting device of claim 1 , wherein the metal element-containing material in the first electron transport layer comprises about 5 parts or less by mass based on the total 100 parts by mass of the first electron transport layer.

10. The light-emitting device of claim 1 , wherein the interlayer further comprises a hole transport region between the emission layer and the first electrode, and

the hole transport region comprises a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof:

wherein, in Formulae 201 and 202,

L 201 to L 204 are each, independently from one another, a C 3 -C 60 carbocyclic group unsubstituted or substituted with at least one R 10a or a C 1 -C 60 heterocyclic group unsubstituted or substituted with at least one R 10a ,

L 205 is *—O—*, *—S—*′, *—N(Q 201 )-*′, a C 1 -C 20 alkylene group unsubstituted or substituted with at least one R 10a , a C 2 -C 20 alkenylene 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 , or a C 1 -C 60 heterocyclic group unsubstituted or substituted with at least one R 10a ,

xa1 to xa4 are each, independently from one another, an integer selected from 0 to 5,

xa5 is an integer selected from 1 to 10,

R 201 to R 204 and Q 201 are each, independently from one another, a C 3 -C 60 carbocyclic group unsubstituted or substituted with at least one R 10a or a C 1 -C 60 heterocyclic group unsubstituted or substituted with at least one R 10a ,

R 201 and R 202 are optionally linked to each other via a single bond, a C 1 -C 5 alkylene group unsubstituted or substituted with at least one R 10a , or a C 2 -C 5 alkenylene group unsubstituted or substituted with at least one R 10a , to form a C 8 -C 60 polycyclic group unsubstituted or substituted with at least one R 10a ,

R 203 and R 204 are optionally linked to each other via a single bond, a C 1 -C 5 alkylene group unsubstituted or substituted with at least one R 10a , or a C 2 -C 5 alkenylene group unsubstituted or substituted with at least one R 10a , to form a C 8 -C 60 polycyclic group unsubstituted or substituted with at least one R 10a ,

na1 is an integer selected from 1 to 4, and

R 10a has the same meaning as in claim 1 .

11. The light-emitting device of claim 1 , wherein the emission layer comprises a first host, a second host, and a dopant, and

the first host and the second host are different from each other.

12. The light-emitting device of claim 11 , wherein the first host is a hole transport compound comprising at least one electron withdrawing group, and

the second host is an electron transport compound comprising at least one electron donating group.

13. The light-emitting device of claim 1 , wherein the moiety represented by

in Formula 1 is represented by one of Formulae 1-1 to 1-32:

wherein, in Formulae 1-1 to 1-32,

X 11 and X 12 are each independently from one another, have the same meaning as in claim 1 ,

X 13 is N or C(R 13 ),

X 14 is N or C(R 14 ),

X 15 is N or C(R 15 ),

X 16 is N or C(R 16 ),

X 17 is N or C(R 17 ),

X 18 is N or C(R 18 ),

X 19 is N or C(R 19 ),

X 20 is N or C(R 20 ),

A 1 to A 3 are each, independently from one another, a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a cyclopentadiene group, a thiophene group, a furan group, an indole group, an indene group, a benzosilole group, a benzogermole group, a benzothiophene group, a benzoselenophene group, a benzofuran group, a carbazole group, an azaindole group, an azabenzoborole group, an azabenzophosphole group, an azaindene group, an azabenzosilole group, an azabenzogermole group, an azabenzothiophene group, an azabenzoselenophene group, an azabenzofuran group, an azacarbazole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isooxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, or a 5,6,7,8-tetrahydroquinoline group,

Y 1 is O, S, N(R 1a ), or C(R 1a ) (R 1b ),

R 11 to R 20 , R 1a , and R 1b each have, independently from one another, the same meaning as *-(L 11 ) a11 -(E 11 ) b11 in Formula 1,

R 11 to R 20 , R 1a , and R 1b are optionally linked to each other to form a C 5 -C 60 carbocyclic group unsubstituted or substituted with at least one R 10a or a C 2 -C 30 heterocyclic group unsubstituted or substituted with at least one R 10a , and

L 11 , a 11 , E 11 , b 11 and R 10a each have the same meaning as in claim 1 .

14. The light-emitting device of claim 1 , wherein Formula 2 is represented by one of Formulae 2-1 to 2-4:

wherein, in Formulae 2-1 to 2-4,

Z 21 is a non-bond, a single bond, O, S, N(R 21a ), or C(R 21a )(R 21b ),

R 21a and R 21b each have, independently from one another, the same meaning as T 22 in claim 1 ,

Y 21 , A 21 , L 21 to L 23 , a21 to a23, T 22 , T 23 , b22 and b23 are each have, independently from one another, the same meaning as described in claim 1 ,

Y 22 has the same meaning as Y 21 in claim 1 ,

L 24 to L 26 are each have, independently from one another, the same meaning as L 21 in claim 1 ,

a24 to a26 are each, independently from one another, an integer selected from 1 to 3,

T 24 to T 26 are each have, independently from one another, the same meaning as T 22 in claim 1 ,

A 22 to A 24 are each, independently from one another, a C 5 -C 60 carbocyclic group or C 2 -C 30 heterocyclic group, and

b24 to b26 are each have, independently from one another, an integer selected from 1 to 8.

15. The light-emitting device of claim 1 , wherein A 21 in Formula 2 is represented by one of Formulae 3-1 to 3-7:

wherein, in Formulae 3-1 to 3-7,

S 21 to S 25 are each, independently from one another, a benzene group, a naphthalene group, a phenanthrene group, an anthracene group, a triphenylene group, a pyrrole group, an imidazole group, a benzoxazole group, a benzothiazole group, a benzimidazole group, a pyridine group, a pyrazine group, a pyrimidine group, an indole group, a quinoline group, an isoquinoline group, a benzoquinoline group, a phenanthridine group, an acridine group, a phenanthroline group, a triazole group, a tetrazole group, or a triazine group, each independently from one another, unsubstituted or substituted with at least one R 10a , and

R 10a has the same meaning as described in claim 1 .

16. An electronic apparatus comprising:

the light-emitting device of claim 1 and

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.

17. The electronic apparatus of claim 16 , further comprising a color filter, a color conversion layer, a touch screen layer, a polarizing layer, or any combination thereof.

18. A light-emitting device comprising:

a plurality of first electrodes patterned according to each of a first subpixel, a second subpixel, and a third subpixel;

a second electrode facing the plurality of the first electrodes;

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

a capping layer on the second electrode,

wherein the emission layer comprises a first emission layer disposed in the first subpixel to emit a first-color light, a second emission layer disposed in the second subpixel to emit a second-color light, and a third emission layer disposed in the third subpixel to emit a third-color light,

the interlayer further comprises an electron transport region between the emission layer and the second electrode,

the capping layer comprises at least one first material represented by Formula 1 or Formula 2, and

the electron transport region satisfies at least one of Condition (11) and Condition (12):

Condition (11)

the electron transport region further comprises a first electron transport layer which is formed as a common layer in all of the first subpixel, the second subpixel, and the third subpixel, the first electron transport layer comprises a mixture comprising an organic electron transport material and a metal element-containing material, and the organic electron transport material and the metal element-containing material are different from each other; and

Condition (12)

the electron transport region comprises at least one second material represented by Formula 1 or Formula 2:

wherein, in Formula 1,

X 11 is N or C(R 11 ),

X 12 is N or C(R 12 ),

A 11 and A 12 are each, independently from one another, a C 1 -C 60 heterocyclic group including at least one N,

L 11 and L 12 are each, independently from one another, a single bond, a C 5 -C 60 carbocyclic group unsubstituted or substituted with at least one R 10a , or a C 1 -C 60 heterocyclic group unsubstituted or substituted with at least one R 10a ,

a11 and a12 are each, independently from one another, an integer selected from 1 to 3,

E 11 , E 12 , R 11 , and R 12 are each, independently from one another, 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 ), or —P(═O)(Q 1 )(Q 2 ),

b11 and b12 are each, independently from one another, an integer selected from 1 to 8,

d11 and d12 are each, independently from one another, an integer selected from 1 to 8,

R 11 and R 12 are optionally linked to each other to form a C 5 -C 60 carbocyclic group unsubstituted or substituted with at least one R 10a or a C 2 -C 30 heterocyclic group unsubstituted or substituted with at least one R 10a ,

wherein, in Formula 2,

Y 21 is O, S, or Se,

A 21 is a C 5 -C 60 carbocyclic group unsubstituted or substituted with at least one R 10a or a C 1 -C 60 heterocyclic group unsubstituted or substituted with at least one R 10a ,

n21 is an integer selected from 1 to 3,

L 21 to L 23 are each, independently from one another, a single bond, a C 5 -C 60 carbocyclic group unsubstituted or substituted with at least one R 10a , or a C 1 -C 60 heterocyclic group unsubstituted or substituted with at least one R 10a ,

a21 to a23 are each, independently from one another, an integer selected from 1 to 3,

T 22 and T 23 are each, independently from one another, 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 ), or —P(═O)(Q 1 )(Q 2 ),

b22 and b23 are each, independently from one another, an integer selected from 1 to 8,

T 22 and T 23 are optionally linked to each other to form a C 2 -C 30 heterocyclic group unsubstituted or substituted with at least one R 10a , and

R 10a is:

deuterium, —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 independently from one another, 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, —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, or a C 6 -C 60 arylthio group, each independently from one another, 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 -C 60 arylthio 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 ),

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; or a C 3 -C 60 carbocyclic group or a C 1 -C 60 heterocyclic group, each independently from one another, 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, and

wherein the electron transport region further comprises a second electron transport layer between the first electron transport layer and the emission layer.

19. 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; and

a capping layer disposed on the second electrode,

wherein the interlayer further comprises an electron transport region between the emission layer and the second electrode,

the capping layer comprises at least one first material represented by Formula 1 or Formula 2, and

the electron transport region satisfies at least one of Condition (1) and Condition (2):

Condition (1)

the electron transport region further comprises a first electron transport layer,

wherein the first electron transport layer comprises a mixture comprising an organic electron transport material and a metal element-containing material, and the organic electron transport material and the metal element-containing material are different from each other; and

Condition (2)

the electron transport region comprises at least one second material represented by Formula 1 or Formula 2:

wherein, in Formula 1,

X 11 is N or C(R 11 ),

X 12 is N or C(R 12 ),

A 11 and A 12 are each, independently from one another, a C 1 -C 60 heterocyclic group comprising at least one N,

L 11 and L 12 are each, independently from one another, a single bond, a C 5 -C 60 carbocyclic group unsubstituted or substituted with at least one R 10a , or a C 1 -C 60 heterocyclic group unsubstituted or substituted with at least one R 10a ,

a11 and a12 are each, independently from one another, an integer selected from 1 to 3,

E 11 , E 12 , R 11 , and R 12 are each, independently from one another, 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 ), or —P(═O)(Q 1 )(Q 2 ),

b11 and b12 are each, independently from one another, an integer selected from 1 to 8,

d11 and d12 are each, independently from one another, an integer selected from 1 to 8,

R 11 and R 12 are optionally linked to each other to form a C 5 -C 60 carbocyclic group unsubstituted or substituted with at least one R 10a or a C 2 -C 30 heterocyclic group unsubstituted or substituted with at least one R 10a ,

wherein, in Formula 2,

Y 21 is O, S, or Se,

A 21 is a C 5 -C 60 carbocyclic group unsubstituted or substituted with at least one R 10a or a C 1 -C 60 heterocyclic group unsubstituted or substituted with at least one R 10a ,

n21 is an integer selected from 1 to 3,

L 21 to L 23 are each, independently from one another, a single bond, a C 5 -C 60 carbocyclic group unsubstituted or substituted with at least one R 10a , or a C 1 -C 60 heterocyclic group unsubstituted or substituted with at least one R 10a ,

a21 to a23 are each, independently from one another, an integer selected from 1 to 3,

T 22 and T 23 are each, independently from one another, 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 ), or —P(═O)(Q 1 )(Q 2 ),

b22 and b23 are each, independently from one another, an integer selected from 1 to 8,

T 22 and T 23 are optionally linked to each other to form a C 2 -C 30 heterocyclic group unsubstituted or substituted with at least one R 10a , and

R 10a is:

deuterium, —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 -Coo arylthio 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, or a C 6 -C 60 arylthio group, each independently from one another, 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 -C 60 arylthio 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 ),

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 from one another: 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; or 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, and

wherein the first electron transport layer and the second electrode directly contact each other.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 23, 2021
From: KIM, SEULONG; KIM, SOUNGWOOK; BAE, SUNGSOO; JEONG, HYEIN; CHOI, HYEWON; HUR, JAEWEON
To: SAMSUNG DISPLAY CO., LTD.
Reel/Frame 058188/0386 →
Priority Claims (1)
KR 10-2020-0159093 · Nov 24, 2020 · national
Continuity (1)
Related Publication 20220173331A1 · Jun 2, 2022
References Cited (23)
US 10193078B2 · Ito et al. · 2019 [cited by applicant]
US 20030230972A1 · Cok · 2003 [cited by examiner]
US 20080074038A1 · Kim et al. · 2008 [cited by applicant]
US 20160149157A1 · Cho · 2016 [cited by examiner]
US 20160204356A1 · Yang et al. · 2016 [cited by applicant]
US 20160308162A1 · Yoo · 2016 [cited by examiner]
US 20170263876A1 · Kim · 2017 [cited by examiner]
US 20170346023A1 · Jankus · 2017 [cited by examiner]
US 20180069187A1 · Ito · 2018 [cited by examiner]
US 20180118742A1 · Joo · 2018 [cited by examiner]
US 20180190922A1 · Gölfert et al. · 2018 [cited by examiner]
US 20190019959A1 · Sakamoto · 2019 [cited by examiner]
US 20190051841A1 · Sim · 2019 [cited by examiner]
US 20200095224A1 · Zhang · 2020 [cited by examiner]
US 20200395550A1 · Sim · 2020 [cited by examiner]
CN 110903159 · 2020 [cited by applicant]
KR 1020080028212 · 2008 [cited by applicant]
KR 1020160005196 · 2016 [cited by applicant]
KR 1020160086449A · 2016 [cited by applicant]
KR 1020160124285A · 2016 [cited by applicant]
KR 1020190016638A · 2019 [cited by applicant]
Lee, Jun Yeob. “Mixed-host-emitting layer for high-efficiency organic light-emitting diodes.” Journal of Information Display 15.3 (2014): 139-144. (Year: 2014). [cited by examiner]
Qiang Huang et al., Performance improvement of top-emitting organic light-emitting diodes by an organic capping layer: An experimental study, Journal of Applied Physics 100, 064507, 2006. [cited by applicant]