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

Patent metadata

Field	Value
Publication number	US-12545835-B2
Application number	US-202217695740-A
Country	US
Kind code	B2
Filing date	Mar 15, 2022
Priority date	Mar 17, 2021
Publication date	Feb 10, 2026
Grant date	Feb 10, 2026

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 heterocyclic compound of Formula 1:

wherein, in Formula 1, the variables are defined herein.

First claim

What is claimed is:

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 heterocyclic compound of Formula 1:

wherein, in Formulae 1 and 2,
X 1 is O, S, B(Z 1a ), N(Z 1a ), C(Z 1a )(Z 1b ), or Si(Z 1a )(Z 1b ),
Y is B or N,
X 4 is O, S, B(T 4 ), N(T 4 ), B(Ar 4 ), or N(Ar 4 ),
X 5 is O, S, B(T 5 ), N(T 5 ), B(Ar 5 ), or N(Ar 5 ),
each of Ar 1 to Ar 5 is, independently from one another, a group of Formula 2,
a1 to a3 are each, independently from one another, an integer from 0 to 4, wherein a sum of a1 to a3 is an integer of 1 or more,
b1 is 0 or 1, wherein, when b1 is 0, X 1 is not present,
rings CY 2 and CY 3 and rings CY 6 to CY 7 are each, independently from one another, a C 3 -C 60 carbocyclic group or a C 1 -C 60 heterocyclic group,
CY 1 is a carbazole group, a fluorene group, a dibenzofuran group, a dibenzothiophene group, or a dibenzosilole group,
T 1 is *′-(L 1 ) d1 -(R 1 ) e1 ,
T 2 is *′-(L 2 ) d2 -(R 2 ) e2 ,
T 3 is *′-(L 3 ) d3 -(R 3 ) e3 ,
T 4 is *′-(L 4 ) d4 -(R 4 ) e4 ,
T 5 is *′-(L 5 ) d5 -(R 5 ) e5 ,
T 6 is *′-(L 6 ) d6 -(R 6 ) e6 ,
T 7 is *′-(L 7 ) d7 -(R 7 ) e7 ,
*′ in T 1 to T 7 is a binding site to a neighboring atom,
c1 to c3, c6, and c7 are each independently from one another, an integer from 0 to 10,
L 1 to L 8 are each independently from one another, 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 ,
d1 to d8 are each, independently from one another, an integer from 0 to 3,
Z 1a , Z 1b , and R 1 to R 7 are each independently a group of Formula 2, 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 , a C 7 -C 60 aryl alkyl group unsubstituted or substituted with at least one R 10a , a C 2 -C 60 heteroaryl alkyl 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 6 and R 7 are each not a group of Formula 2,
e1 to e7 are each, independently from one another, an integer from 0 to 10,
* in Formula 2 is a binding site to a neighboring atom, 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, 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, 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 -Coo 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 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 from one another: hydrogen; deuterium; —F; —CI; —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 7 -C 60 aryl alkyl group, or a C 2 -C 60 heteroaryl alkyl 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.

2 . The light-emitting device of claim 1 , wherein the emission layer comprises the heterocyclic compound of Formula 1.

3 . The light-emitting device of claim 2 , wherein the emission layer further comprises a host and a dopant, and the dopant includes the heterocyclic compound of Formula 1.

4 . The light-emitting device of claim 3 , wherein the emission layer further comprises a phosphorescent dopant.

5 . The light-emitting device of claim 1 , further comprising a capping layer outside the first electrode or the second electrode, wherein the capping layer comprises the heterocyclic compound of Formula 1.

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

7 . The electronic apparatus of claim 6 , 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.

8 . The electronic apparatus of claim 6 , further comprising a color filter, a color conversion layer, a touch screen layer, a polarizing layer, or any combination thereof.

9 . The light-emitting device of claim 1 , wherein, in Formula 1, at least one of rings CY 2 and CY 3 is a naphthalene group, an anthracene group, a carbazole group, a fluorene group, a dibenzofuran group, a dibenzothiophene group, or a dibenzosilole group.

10 . The light-emitting device of claim 1 , wherein, in Formula 1, Y 1 is B, X 4 is N(T 4 ), and X 5 is N(T 5 ) wherein T 4 and T 5 have, independently from one another, the same meaning as in claim 1 .

11 . The light-emitting device of claim 1 , wherein, in Formula 1, a1 is 0, Ar 1 is not present, and a2 and a3 are each, independently from one another, 0 or 1, wherein a sum of a2 and a3 is an integer of 1 or more.

12 . The light-emitting device of claim 1 , wherein, in Formula 1, rings CY 2 and CY 3 are each, independently from

Assignees

• Samsung Display Co Ltd

Inventors

• Park Junha
• Kim Taeil
• Pak Sunyoung
• Baek Jangyeol
• Sunwoo Kyoung
• Sim Munki
• Oh Chanseok
• Jung Minjung

Classifications

• H10K59/40

  OLEDs integrated with touch screens · CPC title

• H10K59/38

  comprising colour filters or colour changing media [CCM] · CPC title

• H10K59/123

  Connection of the pixel electrodes to the thin film transistors [TFT] · CPC title

• C09K11/06 Primary

  containing organic luminescent materials · CPC title

• H10K85/658 Primary

  Organoboranes · CPC title