IP Library › Granted Patent US 12,225,816
Granted Patent B2
US 12,225,816 · App. 17/446,647 · Granted Feb 11, 2025

Light-emitting device and electronic apparatus including the same

Inventors: Hyunyoung Kim (Yongin-si, KR); Minje Kim (Yongin-si, KR); Hyojeong Kim (Yongin-si, KR); Jungsub Lee (Yongin-si, KR); Jiyoung Lee (Yongin-si, KR)
Assignee: Samsung Display Co., Ltd.
H10K85/6572H10K85/342H10K85/346H10K85/40H10K85/636H10K85/654H10K85/6574H10K85/6576H10K50/11H10K50/15H10K50/16H10K2101/10H10K2101/27H10K2101/40
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Quick Facts
Patent No.
US 12,225,816
App. No.
17/446,647
Granted
Feb 11, 2025
Kind
B2
Abstract

A light-emitting device and an electronic apparatus including the same are provided.

Claims (146)

1. A light-emitting device comprising:

a first electrode;

a second electrode; and

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

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

the hole transport region comprises a first auxiliary layer and a second auxiliary layer between the first electrode and the first auxiliary layer,

the first auxiliary layer comprises a first compound,

the second auxiliary layer comprises a second compound,

the first compound and the second compound are different from each other, and

a lowest excitation triplet energy level (T1) of the first compound is equal to or greater than about 1.60 eV and less than or equal to about 1.80 eV.

2. 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 between the emission layer and the second 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 further 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 hole transport region further comprises a hole transport layer between the first electrode and the second auxiliary layer.

4. The light-emitting device of claim 1 , wherein the first compound is an anthracene-based compound.

5. The light-emitting device of claim 1 , wherein the second compound is a hole-transporting compound.

6. The light-emitting device of claim 1 , wherein a highest occupied molecular orbital (HOMO) energy level of the second compound is equal to or greater than about −5.7 eV and less than or equal to about −5.2 eV, and a lowest unoccupied molecular orbital (LUMO) energy level of the second compound is equal to or greater than about −2.0 eV and less than or equal to about −1.8 eV.

7. The light-emitting device of claim 1 , wherein the first auxiliary layer and the second auxiliary layer are in direct contact with each other.

8. The light-emitting device of claim 3 , wherein the hole transport layer and the second auxiliary layer are in direct contact with each other.

9. The light-emitting device of claim 1 , wherein the first compound is represented by Formula 1:

wherein, in Formula 1,

L 1 is a single bond, 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 , —C(Q 1 )(Q 2 )-, —Si(Q 1 )(Q 2 )-, —B(Q 1 )-, or —N(Q 1 )-,

a1 is an integer from 1 to 5,

R 1 and A 1 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 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 ),

b1 is an integer from 1 to 10,

d1 is an integer from 1 to 10,

n1 is 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, —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 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, —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 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.

10. The light-emitting device of claim 1 , wherein the second compound is represented by Formula 2:

wherein, in Formula 2,

X 2 is O, S, N(R 2a ), or C(R 2a )(R 2b ),

R 2a , R 2b and R 2 to R 9 are each independently *-(L 2 ) a2 -(A 2 ) b2 , 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 ),

L 2 is a single bond, a π electron-rich C 3 -C 60 cyclic group unsubstituted or substituted with at least one R 10a , —C(Q 1 )(Q 2 )-, —Si(Q 1 )(Q 2 )-, —B(Q 1 )-, or —N(Q 1 )-,

a2 is an integer from 1 to 5,

A 2 is a C 1 -C 60 alkyl group unsubstituted or substituted with at least one R 10a , a π electron-rich C 3 -C 60 cyclic group unsubstituted or substituted with at least one R 10a , —C(Q 1 )(Q 2 )(Q 3 ), —Si(Q 1 )(Q 2 )(Q 3 ), —N(Q 1 )(Q 2 ), or —B(Q 1 )(Q 2 ),

b2 is an integer from 1 to 5, 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 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 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 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.

11. The light-emitting device of claim 1 , wherein the emission layer comprises Compound A and Compound B, the Compound A is a hole-transporting compound and the Compound B is an electron-transporting compound.

12. The light-emitting device of claim 11 , wherein the emission layer further comprises Compound C and Compound D,

the Compound C is a phosphorescent compound, and

the Compound D is a fluorescent compound or a thermally activated delayed fluorescence (TADF) compound that satisfies Equation 1 below:

Δ E ST =S 1(TADF)− T 1(TADF)≤0.3 eV  Equation 1

wherein, in Equation 1, S1 (TADF) is a lowest excitation singlet energy level (eV) of the TADF compound, and T1 (TADF) is a lowest excitation triplet energy level (eV) of the TADF compound.

13. The light-emitting device of claim 12 , wherein the Compound D is to emit light.

14. The light-emitting device of claim 12 , wherein the Compound A is represented by Formula a, the Compound B is represented by Formula b, and the Compound C is represented by Formula c:

wherein, in Formula a,

X 11 is O, S, N(R 19 ), or C(R 19 )(R 20 ),

R 11 to R 20 are each independently *-(L 11 ) a11 -(A 11 ) b11 , 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 ),

L 11 is a single bond, a π electron-rich C 3 -C 60 cyclic group unsubstituted or substituted with at least one R 10a , —C(Q 1 )(Q 2 )-, —Si(Q 1 )(Q 2 )-, —B(Q 1 )-, or —N(Q 1 )-,

a11 is an integer from 1 to 5,

A 11 is a C 1 -C 60 alkyl group unsubstituted or substituted with at least one R 10a , a π electron-rich C 3 -C 60 cyclic group unsubstituted or substituted with at least one R 10a , —C(Q 1 )(Q 2 )(Q 3 ), —Si(Q 1 )(Q 2 )(Q 3 ), —N(Q 1 )(Q 2 ), or —B(Q 1 )(Q 2 ), and

b11 is an integer from 1 to 10,

wherein, in Formula b,

X 21 to X 23 are each independently N or C(R 21 ), and at least one of X 21 to X 23 is N,

L 21 to L 23 are each independently a single bond, 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 ,

a21 to a23 are each independently an integer from 1 to 5,

A 21 to A 23 and R 21 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 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 ), —C(Q 1 )(Q 2 )(Q 3 ), —N(Q 1 )(Q 2 ), or —B(Q 1 )(Q 2 ),

b21 to b23 are each independently an integer from 1 to 10, and

in Formulae c and c-1 to c-4,

M 31 is a transition metal selected from a first-row, a second-row and a third-row of transition metals of the Periodic Table of Elements,

L 31 is a ligand represented by one of Formulae c-1 to c-4,

L 32 is a monodentate ligand, a bidentate ligand, or a tridentate ligand,

n31 is 1 or 2,

n32 is an integer from 0 to 4,

A 31 to A 34 are each independently a C 5 -C 30 carbocyclic group or a C 1 -C 30 heterocyclic group,

T 31 to T 34 are each independently a single bond, a double bond, *—O—*′, *—S—*′, *—C(═O)—*′, *—S(═O)—*′, *—C(R 35 )(R 36 )—*′, *—C(R 35 )═C(R 36 )—*′, *—C(R 35 )═*′, *—Si(R 35 )(R 36 )—*′, *—B(R 35 )—*′, *—N(R 35 )—*′, or *—P(R 35 )—*′,

k31 to k34 are each independently an integer from 1 to 3,

Y 31 to Y 34 are each independently a single bond, *—O—*′, *—S—*′, *—C(R 37 )(R 38 )—*′, *—Si(R 37 )(R 38 )—*′, *—B(R 37 )—*′, *—N(R 37 )—*′, or *—P(R 37 )—*′,

* 1 , * 2 , * 3 , and * 4 each indicate a binding site to M 31 ,

R 31 to R 38 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 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 ),

R 31 to R 38 are optionally bonded to each other to form 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 ,

b31 to b34 are each independently 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, —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 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 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.

15. The light-emitting device of claim 12 , wherein the Compound D is represented by one of Formulae d-1 and d-21 to d-23:

(D 41 ) n41 -(L 41 ) a41 -(A 41 ) m41   Formula d-21

(D 41 ) n41 -(L 41 ) a41 -(A 41 ) m41 -(L 42 ) a42 -(D 42 ) n42   Formula d-22

(A 41 ) m41 -(L 41 ) a41 -(D 41 ) n41 -(L 42 ) a42 -(A 42 ) m42   Formula d-23

wherein, in Formula d-1,

Ar 41 to Ar 43 are each independently a C 3 -C 60 carbocyclic group or a C 1 -C 60 heterocyclic group,

X 41 is N, B, P, P(═O), or P(═S),

Y 42 and Y 43 are each independently N, O, S, C(R 44 ), or Si(R 44 ),

R 41 to R 44 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 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 ),

b41 to b43 are each independently an integer from 1 to 10, and

two or more groups of R 41 to R 44 are optionally linked to each other to form a C 5 -C 30 carbocyclic group that is 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

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 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 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, in Formulae d-21 to d-23,

A 41 and A 42 are each independently a π electron-rich C 3 -C 60 cyclic group, —Si(Q 1 )(Q 2 )(Q 3 ), —B(Q 1 )(Q 2 ), or —N(Q 1 )(Q 2 );

a π electron-rich C 3 -C 60 cyclic group substituted with at least one selected from deuterium, a C 1 -C 60 alkyl group, a π electron-rich C 3 -C 60 cyclic group, —C(Q 31 )(Q 32 )(Q 33 ), —Si(Q 31 )(Q 32 )(Q 33 ), —B(Q 31 )(Q 32 ), and —N(Q 31 )(Q 32 ); or

a π electron-rich C 3 -C 60 cyclic group, substituted with at least one π electron-rich C 3 -C 60 cyclic group that is substituted with at least one selected from deuterium, a C 1 -C 60 alkyl group, π electron-rich C 3 -C 60 cyclic group, —C(Q 21 )(Q 22 )(Q 23 ), —Si(Q 21 )(Q 22 )(Q 23 ), —B(Q 21 )(Q 22 ), and N(Q 21 )(Q 22 );

m41 and m42 are each independently an integer from 1 to 3,

D 41 and D 42 are each independently: —F, a cyano group, a π electron-deficient nitrogen-containing C 1 -C 60 cyclic group, a group containing C(═O), a group containing P(═O), or a group containing P(═S);

a π electron deficient nitrogen-containing C 1 -C 60 cyclic group, a C(═O)-containing group, a P(═O)-containing group, or a P(═S)-containing group, each substituted with at least one selected from deuterium, —F, a cyano group, a C 1 -C 60 alkyl group, a π electron deficient nitrogen-containing C 1 -C 60 cyclic group, and a π electron-rich C 3 -C 60 cyclic group;

a C 1 -C 60 alkyl group or a π electron-rich C 3 -C 60 cyclic group, each substituted with at least one selected from —F, a cyano group, and a π electron deficient nitrogen-containing C 1 -C 60 cyclic group;

a π electron deficient nitrogen-containing C 1 -C 60 cyclic group, a C(═O)-containing group, a P(═O)-containing group, or a P(═S)-containing group, each substituted with at least one selected from a C 1 -C 60 alkyl group, a π electron deficient nitrogen-containing C 1 -C 60 cyclic group, and a π electron-rich C 3 -C 60 cyclic group, each substituted with at least one selected from deuterium, —F, a cyano group, a C 1 -C 60 alkyl group, a π electron deficient nitrogen-containing C 1 -C 60 cyclic group, and a π electron-rich C 3 -C 60 cyclic group;

a C 1 -C 60 alkyl group or a π electron-rich C 3 -C 60 cyclic group, each substituted with at least one π electron deficient nitrogen-containing C 1 -C 60 cyclic group that is substituted with at least one selected from deuterium, —F, a cyano group, a C 1 -C 60 alkyl group, a π electron deficient nitrogen-containing C 1 -C 60 cyclic group, and a π electron-rich C 3 -C 60 cyclic group; and

a C 1 -C 60 alkyl group or a π electron-rich C 3 -C 60 cyclic group, each substituted with at least one selected from a C 1 -C 60 alkyl group and a π electron-rich C 3 -C 60 cyclic group, each substituted with at least one selected from —F, a cyano group, and a π electron deficient nitrogen-containing cyclic group,

n41 and n42 are each independently an integer from 1 to 3,

L 41 and L 42 are each independently a π electron-rich C 3 -C 60 cyclic group, —C(Q 1 )(Q 2 )-, —Si(Q 1 )(Q 2 )-, —B(Q 1 )-, or —N(Q 1 )-; or

a π electron-rich C 3 -C 60 cyclic group, substituted with at least one selected from deuterium, a C 1 -C 60 alkyl group, a π electron-rich C 3 -C 60 cyclic group, —C(Q 31 )(Q 32 )(Q 33 ), —Si(Q 31 )(Q 32 )(Q 33 ), —B(Q 31 )(Q 32 ), and —N(Q 31 )(Q 32 ); and

a41 and a42 are each independently an integer from 0 to 3,

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 any combination thereof.

16. The light-emitting device of claim 15 , wherein the Compound D is represented by one of Formulae d-11 and d-12:

wherein, in Formulae d-11 and d-12,

X 41 and X 42 are each independently the same as described in connection with X 41 of Formula d-1,

Y 42 to Y 45 are each independently the same as described in connection with Y 42 of Formula d-1, and

R 41 a to R 41d , R 42a to R 42c , R 43a to R 43d , R 44a to R 44c , R 45a , and R 45b are each independently the same as described in connection with R 41 of Formula d-1.

17. The light-emitting device of claim 12 , wherein

the Compound A is selected from compounds of Group I,

the Compound B is selected from compounds of Group II,

the Compound C is selected from compounds of Group III-I and Group III-II, and

the Compound D is selected from compounds of Group IV-I and Group IV-II:

Group I

Group II

Group III-I

Group III-II

Group IV-I

Group IV-II

18. The light-emitting device of claim 1 , wherein a maximum luminescence wavelength of the interlayer is from about 400 nm to about 510 nm.

19. 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.

20. The electronic apparatus of claim 19 , 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 Sep 1, 2021
From: KIM, HYUNYOUNG; KIM, MINJE; KIM, HYOJEONG; LEE, JUNGSUB; LEE, JIYOUNG
To: SAMSUNG DISPLAY CO., LTD.
Reel/Frame 057355/0059 →
Priority Claims (2)
KR 10-2020-0111681 · Sep 2, 2020 · national
KR 10-2021-0008316 · Jan 20, 2021 · national
Continuity (1)
Related Publication 20220069235A1 · Mar 3, 2022
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