IP Library Granted Patent US 11,950,499
Granted Patent B2
US 11,950,499 · App. 17/240,590 · Granted Apr 2, 2024

Light-emitting device comprising first and second capping layers and electronic apparatus including the same

Inventors: Bora Lee (Yongin-si, KR); Hyomin Ko (Yongin-si, KR); Ilsoo Oh (Yongin-si, KR)
Assignee: SAMSUNG DISPLAY CO., LTD.
H10K85/636G02B5/20G02B5/30H01L33/50H10K85/624H10K85/6572H10K50/15H10K50/171H10K50/18
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Quick Facts
Patent No.
US 11,950,499
App. No.
17/240,590
Granted
Apr 2, 2024
Kind
B2
Abstract

A light-emitting device includes a first electrode, a second electrode facing the first electrode, an interlayer disposed between the first electrode and the second electrode and including an emission layer, a first capping layer, and a second capping layer. A refractive index of the first capping layer is greater than a refractive index of the second capping layer, and the first capping layer and the second capping layer are each an organic layer. An electronic apparatus including the light-emitting device is also provided.

Claims (70)

1. A light-emitting device comprising:

a first electrode;

a second electrode facing the first electrode;

an interlayer disposed between the first electrode and the second electrode, the interlayer including an emission layer;

a first capping layer; and

a second capping layer, wherein

a refractive index of the first capping layer is greater than a refractive index of the second capping layer,

the first capping layer and the second capping layer are each an organic layer, and

the first capping layer comprises a compound represented by Formula 1:

wherein in Formula 1,

R 1 to R 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 , —B(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —Si(Q 1 )(Q 2 )(Q 3 ), and —P(═O)(Q 1 )(Q 2 ),

Ar 1 and Ar 2 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 a t least one R 10a , a C 10 -C 60 alkoxy 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 , —B(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —Si(Q 1 )(Q 2 )(Q 3 ), and —P(═O)(Q 1 )(Q 2 ),

X is selected from a C 3 -C 60 carbocyclic group unsubstituted or substituted with at least one R 10a and a C 1 -C 60 heterocyclic group unsubstituted or substituted with at least one R 10a ,

m is an integer from 1 to 3,

a3 and a4 are each independently an integer from 1 to 3,

a5 and a6 are each independently an integer from 1 to 4,

when a3 is 2 or more, a plurality of R 3 (s) are identical to or different from each other,

when a4 is 2 or more, a plurality of R 4 (s) are identical to or different from each other,

when a5 is 2 or more, a plurality of R 5 (s) are identical to or different from each other,

when a6 is 2 or more, a plurality of R 6 (s) are identical to or different from each other, 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, —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 a 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 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 a 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 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 a combination thereof.

2. The light-emitting device of claim 1 , wherein the first capping layer contacts the second capping layer.

3. The light-emitting device of claim 1 , wherein the first capping layer contacts the second electrode.

4. The light-emitting device of claim 1 , wherein the first capping layer is disposed outside the second electrode.

5. The light-emitting device of claim 1 , wherein

the first electrode is an anode,

the second electrode is a cathode,

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

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

6. The light-emitting device of claim 1 , wherein

the first electrode is an anode,

the second electrode is a cathode,

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

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

7. The light-emitting device of claim 1 , wherein a refractive index of the first capping layer is in a range of about 1.7 to about 2.2, at a wavelength of about 550 nm.

8. The light-emitting device of claim 1 , wherein a refractive index of the second capping layer is in a range of about 1.2 to about 1.7, at a wavelength of about 550 nm.

9. The light-emitting device of claim 1 , wherein a thickness of the second capping layer is greater than a thickness of the first capping layer.

10. The light-emitting device of claim 1 , wherein a thickness of the first capping layer is in a range of about 60 nm to about 100 nm.

11. The light-emitting device of claim 1 , wherein a thickness of the second capping layer is in a range of about 40 nm to about 120 nm.

12. The light-emitting device of claim 1 , wherein R 3 to R 6 are each independently hydrogen or deuterium.

13. The light-emitting device of claim 1 , wherein the second capping layer comprises a compound represented by Formula 2:

wherein in Formula 2,

R 11 to R 25 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 , —B(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —Si(Q 1 )(Q 2 )(Q 3 ), and —P(═O)(Q 1 )(Q 2 ),

two neighboring substituents of R 11 to R 15 are connected to form a ring group, two neighboring substituents of R 16 to R 20 are connected to form a ring group, or two neighboring substituents of R 21 to R 25 are connected to form a ring group, and

R 10a is the same as defined in Formula 1.

14. The light-emitting device of claim 13 , wherein the ring group is represented by Formula 2-1:

wherein in Formula 2-1,

Y is —N(R 31 ) or —C(R 32 )(R 33 ),

R 31 to R 33 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a nitro group, a C 1 -C 60 alkyl 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 , and a C 1 -C 60 heterocyclic group unsubstituted or substituted with at least one R 10a ,

R 32 and R 33 are optionally connected to form a ring,

a21 is an integer from 1 to 4,

* indicates a binding site to a neighboring atom, 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, —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 a 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 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 a 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 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 a combination thereof.

15. The light-emitting device of claim 1 , wherein the first capping layer further comprises one of the following compounds:

16. The light-emitting device of claim 1 , wherein the second capping layer comprises one of the following compounds:

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

18. The electronic apparatus of claim 17 , 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 at least one of the source electrode and the drain electrode of the thin-film transistor.

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

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 26, 2021
From: LEE, BORA; KO, HYOMIN; OH, ILSOO
To: SAMSUNG DISPLAY CO., LTD.
Reel/Frame 056043/0267 →
Priority Claims (1)
KR 10-2020-0114860 · Sep 8, 2020 · national
Continuity (1)
Related Publication 20220077395A1 · Mar 10, 2022
Cited By (1)
US 12,490,647