IP Library Granted Patent US 12,201,017
Granted Patent B2
US 12,201,017 · App. 17/369,366 · Granted Jan 14, 2025

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

Inventors: Yoonkyoo Lee (Yongin-si, KR); Jinwon Sun (Yongin-si, KR); Jungsub Lee (Yongin-si, KR)
Assignee: SAMSUNG DISPLAY CO., LTD.
H10K85/40C07D209/86C07F7/0812C09K11/06H10K85/6572C07B2200/05C09K2211/1018H10K50/11H10K50/844H10K59/123H10K85/654H10K2101/10H10K2101/90
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Quick Facts
Patent No.
US 12,201,017
App. No.
17/369,366
Granted
Jan 14, 2025
Kind
B2
Abstract

The disclosure relates to a light-emitting device including a first electrode, a second electrode facing the first electrode, and an interlayer disposed between the first electrode and the second electrode and including an emission layer. The interlayer includes a first compound represented by Formula 1 of the specification, a second compound represented by Formula 2 of the specification, and a third compound, which is a blue phosphorescent compound. The disclosure also relates to an electronic apparatus including the light-emitting device.

Claims (71)

1. A light-emitting device comprising:

a first electrode;

a second electrode facing the first electrode; and

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

the interlayer includes:

a first compound represented by Formula 1;

a second compound selected from one of Compounds 2-1 to 2-24; and

a third compound, and

the third compound is a blue phosphorescent compound:

wherein in Formula 1,

X 1 is C(R 1 )(R 2 ), Si(R 1 )(R 2 ), N—[(L 1 ) a1 -(R 1 ) b1 ], O, or S,

L 1 is a C 4 -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 ,

a1 is an integer from 0 to 5,

R 1 to R 4 are each independently hydrogen, deuterium, —F, —C 1 , —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 ), —P (Q 1 )(Q 2 ), —C(═O) (Q 1 ), or —Si(Q 1 )(Q 2 )(Q 3 ),

b1 is an integer from 0 to 10,

b3 is an integer from 0 to 7,

b4 is an integer from 0 to 8, and

the first compound includes at least one deuterium (D), and

R 10a is:

deuterium (-D), —F, —C 1 , —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, —C 1 , —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, —C(Q 11 )(Q 12 )(Q 13 ), —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, —C 1 , —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, —C(Q 21 )(Q 22 )(Q 23 ), —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

—C(Q 31 )(Q 32 )(Q 33 ), —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

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; —C 1 ; —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 L 1 in Formula 1 is a π electron-rich C 3 -C 60 cyclic group unsubstituted or substituted with at least one R 10a .

3. The light-emitting device of claim 1 , wherein R 1 to R 4 in Formula 1 are each independently:

hydrogen, deuterium, —F, —C 1 , —Br, —I, a hydroxyl group, a cyano group, or a nitro group;

a C 1 -C 20 alkyl group, a C 2 -C 20 alkenyl group, a C 2 -C 20 alkynyl group, or a C 1 -C 20 alkoxy group, each unsubstituted or substituted with deuterium, —F, —C 1 , —Br, —I, —CD 3 , —CD 2 H, —CDH 2 , —CF 3 , —CF 2 H, —CFH 2 , a hydroxyl group, a cyano group, a nitro group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, —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 ), —P(═O) (Q 31 )(Q 32 ), or a combination thereof; or

a π electron-rich C 3 -C 60 cyclic group unsubstituted or substituted with at least one R 10a .

4. The light-emitting device of claim 1 , wherein the first compound is represented by one of Formulae 1(1) to 1(4):

wherein in Formulae 1(1) to 1(4),

X 1 , R 3 , R 4 , b3, and b4 are the same as described in connection with Formula 1.

5. The light-emitting device of claim 1 , wherein the first compound is selected from one of Compounds 1-1 to 1-9:

wherein Ph represents a phenyl group.

6. The light-emitting device of claim 1 , wherein the third compound is a platinum (Pt) complex including a tetradentate ligand.

7. The light-emitting device of claim 1 , wherein the third compound includes a carbene moiety in which carbon and Pt are bonded.

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

wherein in Formula 3,

Y 20 , Y 30 , and Y 40 are each independently C or N,

T 10 to T 30 are each independently selected from a single bond, *—O—*′, *—S—*′*—C(Z 10a )(Z 10b )—*′, *—C(Z 10a )═*′, *—C(Z 10a )═C(Z 10b )—*′, *—C(═O)—*′, *—C(═S)—*′, *—C═C—*′, *—B(Z 10a )—*′, *—N(Z 10a )—*′, *—P(Z 10a )—*′, and *—Si(Z 10a ) (Z 10b )—*′,

A 10 , A 20 , and A 30 are each independently a C 4 -C 60 carbocyclic group or a C 1 -C 60 heterocyclic group,

R 10 , R 20 , R 30 , and R 40 are each independently the same as described in connection with R 1 in Formula 1,

Z 10a and Z 10b are each independently the same as defined in connection with R 1 in Formula 1,

b10, b20, and b30 are each independently an integer from 0 to 10,

b40 is an integer from 0 to 5, and

and *′ each indicate a binding site to a neighboring atom.

9. The light-emitting device of claim 8 , wherein Y 40 is C, and a bond between Y 40 and Pt is a coordinate bond.

10. The light-emitting device of claim 8 , wherein T 10 and T 30 are single bonds, and T 20 is not a single bond.

11. The light-emitting device of claim 8 , wherein Formula 3 satisfies at least one of three conditions:

(i) A 10 is a pyridine group,

(ii) A 20 is a carbazole group, and/or

(iii) A 30 is a benzene group.

12. The light-emitting device of claim 8 , wherein the third compound is represented by one of Formulae 3(1) and 3(2):

wherein in Formulae 3(1) and 3(2),

Y 20 , Y 30 , T 10 , T 20 , T 30 , A 10 , A 20 , A 30 , R 10 , R 20 , R 30 , R 40 , bio, b20, and b30 are the same as described in connection with Formula 3,

Y 41 is C,

R 41 is the same as described in connection with R 40 in Formula 3,

b41 is 1, and

b44 is an integer from 0 to 4.

13. The light-emitting device of claim 1 , wherein the third compound is selected from one of Compounds 3-1 to 3-4:

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

the light-emitting device emits blue light having a maximum luminescence wavelength in a range of about 400 nm to about 500 nm, and

the emission layer has a difference of equal to or less than about 0.5 eV between a singlet energy level and a triplet energy level.

15. The light-emitting device of claim 1 , further comprising a capping layer disposed outside the second electrode,

wherein the capping layer includes a carbocyclic compound, a heterocyclic compound, an amine group-containing compound, a porphyrine derivative, a phthalocyanine derivative, a naphthalocyanine derivative, an alkali metal complex, an alkaline earth-metal complex, or a combination thereof.

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

17. The electronic apparatus of claim 16 , further comprising an encapsulation portion,

wherein the encapsulation portion comprises an organic layer, an inorganic layer, or a combination thereof.

18. The electronic apparatus of claim 16 , 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 Jul 7, 2021
From: LEE, YOONKYOO; SUN, JINWON; LEE, JUNGSUB
To: SAMSUNG DISPLAY CO., LTD.
Reel/Frame 056785/0716 →
Priority Claims (1)
KR 10-2020-0089156 · Jul 17, 2020 · national
Continuity (1)
Related Publication 20220020939A1 · Jan 20, 2022
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