Heterocyclic compound, light-emitting device including the heterocyclic compound, and electronic apparatus including the light-emitting device

Patent metadata

Field	Value
Publication number	US-12433151-B2
Application number	US-202117453484-A
Country	US
Kind code	B2
Filing date	Nov 3, 2021
Priority date	Nov 5, 2020
Publication date	Sep 30, 2025
Grant date	Sep 30, 2025

Abstract

Provided are a heterocyclic compound represented by Formula 1, an organic light-emitting device including the heterocyclic compound, and an electronic apparatus including the light-emitting device. The 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.

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
at least one heterocyclic compound represented by Formulae 1-11, 1-12 and 1-14:

wherein, in Formulae 1-11, 1-12 and 1-14,
X 1 is O, S, or Si(R 11 )(R 12 ),
Ar is a C 5 -C 60 carbocyclic group or a C 1 -C 60 heterocyclic group,
A 1 is a C 3 -C 60 carbocyclic group unsubstituted or substituted with at least one R 10 , a C 1 -C 60 heterocyclic group unsubstituted or substituted with at least one R 10 , or a group represented by Formula 2,

L 1 is 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 ,
n1 is an integer selected from 1 to 3,
wherein, in Formula 2,
Y 1 is N or C(R 1a ),
Y 2 is N or C(R 2a ),
Y 3 is N or C(R 3a ),
L 21 and L 22 are each independently 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 ,
n21 and n22 are each independently an integer selected from 1 to 3,
* indicates a binding site to a neighboring atom,
in Formulae 1-11, 1-12, 1-14 and 2,
R 1 to R 3 , R 10 , R 11 , R 12 , R 1a to R 3a , R 21 and R 22 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 ),
d1 is an integer selected from 1 to 8,
d2 is an integer selected from 1 to 10,
d3 is an integer selected from 1 to 7, and
R 10a is:
deuterium (-D), —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, an amidino group, a hydrazino group, a hydrazono 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 ), —P(═O)(Q 31 )(Q 32 ), or —P(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,
when L 1 is a single bond, A 1 is a group represented by Formula 2 and Y 1 to Y 3 are N, then at least one of R 21 and R 22 is a carbazole group.

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 a hole transport region between the first electrode and the emission layer and 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 buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer, or any combination thereof.

3. The light-emitting device of claim 1 , wherein the emission layer comprises the at least one heterocyclic compound.

4. The light-emitting device of claim 1 , wherein the emission layer comprises a host and a dopant,
the host and the dopant are different from each other,
an amount of the host is greater than an amount of the dopant, and
the host comprises the at least one heterocyclic compound.

5. The light-emitting device of claim 4 , wherein the dopant comprises a transition metal.

6. The light-emitting device of claim 3 , wherein the emission layer emits blue light or blue-green light.

7. 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 coupled to the source electrode or the drain electrode.

8. The electronic apparatus of claim 7 , further comprising a color filter, a color conversion layer, a touch screen layer, a polarizing layer, or any combination thereof.

9. A heterocyclic compound represented by Formulae 1-11, 1-12 and 1-14:

wherein, in Formulae 1-11, 1-12 and 1-14,
X 1 is O, S, or Si(R 11 )(R 12 ),
Ar is a C 5 -C 60 carbocyclic group or a C 1 -C 60 heterocyclic group,
A 1 is a C 3 -C 60 carbocyclic group unsubstituted or substituted with at least one R 10 , a C 1 -C 60 heterocyclic group unsubstituted or substituted with at least one R 10 , or a group represented by Formula 2,

L 1 is 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 ,
n1 is an integer selected from 1 to 3,
wherein, in Formula 2,
Y 1 is N or

Assignees

• Samsung Display Co Ltd

Inventors

• Kim Hyeongmin
• Ahn Heechoon
• Um Hyunah
• Lee Yeseul
• Lee Hyoyoung
• Im Yirang
• Cho Seowon

Classifications

• H10K2101/10

  Triplet emission · CPC title

• H10K50/11

  characterised by the electroluminescent [EL] layers · CPC title

• H10K85/6572

  comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole · CPC title

• H10K85/654

  comprising only nitrogen as heteroatom (H10K85/652 takes precedence) · CPC title

• C07F7/0812

  comprising a heterocyclic ring · CPC title