Heterocyclic compound, hole transport composition including the same, light-emitting device including the hole transport composition, method of manufacturing the light-emitting device, and electronic apparatus including the light-emitting device

Patent metadata

Field	Value
Publication number	US-12391699-B2
Application number	US-202117447685-A
Country	US
Kind code	B2
Filing date	Sep 14, 2021
Priority date	Sep 18, 2020
Publication date	Aug 19, 2025
Grant date	Aug 19, 2025

Abstract

Provided are a heterocyclic compound represented by Formula 1, a hole transport composition containing the same, a light-emitting device including the hole transport composition, a method of manufacturing the light-emitting device, and an electronic apparatus including the light-emitting device, wherein each substituent in Formula 1 is the same as described in the present specification.

First claim

What is claimed is:

1. A heterocyclic compound represented by Formula 1:

wherein, in Formula 1,
L 11 to L 13 and L 21 to L 23 are each independently a C 2 -C 20 alkenylene group unsubstituted or substituted with at least one R 10a , or a C 2 -C 20 alkynylene group unsubstituted or substituted with at least one R 10a ,
a11 to a13 and a21 to a23 are each independently 0, 1, 2, 3, 4, or 5, wherein at least one selected from a11 to a13 and a21 to a23 is 1, 2, 3, 4, or 5,
Z 11 to Z 13 , Z 21 to Z 23 , and R 1 to R 9 are each independently hydrogen, deuterium, an azide group (—N 3 ), —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono 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 10 cycloalkyl group unsubstituted or substituted with at least one R 10a , a C 1 -C 10 heterocycloalkyl group unsubstituted or substituted with at least one R 10a , a C 3 -C 10 cycloalkenyl group unsubstituted or substituted with at least one R 10a , a C 1 -C 10 heterocycloalkenyl group unsubstituted or substituted with at least one R 10a , a C 6 -C 60 aryl 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 1 -C 60 heteroaryl group unsubstituted or substituted with at least one R 10a , a C 1 -C 60 heteroaryloxy group unsubstituted or substituted with at least one R 10a , a C 1 -C 60 heteroarylthio group unsubstituted or substituted with at least one R 10a , a monovalent non-aromatic condensed polycyclic group unsubstituted or substituted with at least one R 10a , a monovalent non-aromatic condensed heteropolycyclic group unsubstituted or substituted with at least one R 10a , —Si(Q 1 )(Q 2 )(Q 3 ), —B(Q 1 )(Q 2 ), —N(Q 1 )(Q 2 ), —P(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —S(═O)(Q 1 ), —S(═O) 2 (Q 1 ), —P(═O)(Q 1 )(Q 2 ), or —P(═S)(Q 1 )(Q 2 ),
at least one selected from Z 11 to Z 13 , Z 21 to Z 23 , and R 1 to R 9 is —N 3 ,
when each of Z 11 to Z 13 is —N 3 , at least one selected from -(L 21 ) a21 -Z 21 , -(L 22 ) a22 -Z 22 , and -(L 23 ) a23 -Z 23 is hydrogen,
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, 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.

2. The heterocyclic compound of claim 1 , wherein Z 11 to Z 13 are each —N 3 .

3. The heterocyclic compound of claim 1 , wherein Z 21 to Z 23 are each —N 3 .

4. The heterocyclic compound of claim 1 , wherein the heterocyclic compound is represented by one selected from Formulae 2A and 2B:

wherein, in Formulae 2A and 2B,
L 11 to L 13 , L 21 to L 23 , Z 11 to Z 13 , Z 21 to Z 23 , and R 1 to R 9 are the same as described in claim 1 ,
R 11 to R 13 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono 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 10 cycloalkyl group unsubstituted or substituted with at least one R 10a , a C 1 -C 10 heterocycloalkyl group unsubstituted or substituted with at least one R 10a , a C 3 -C 10 cycloalkenyl group unsubstituted or substituted with at least one R 10a , a C 1 -C 10 heterocycloalkenyl group unsubstituted or substituted with at least one R 10a , a C 6 -C 60 aryl 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 1 -C 60 heteroaryl group unsubstituted or substituted with at least one R 10a , a C 1 -C 60 heteroaryloxy group unsubstituted or substituted with at least one R 10a , a C 1 -C 60 heteroarylthio group unsubstituted or substituted with at least one R 10a , a monovalent non-aromatic condensed polycyclic group unsubstituted or substituted with at least one R 10a , a monovalent non-aromatic condensed heteropolycyclic group unsubstituted or substituted with at least one R 10a , —Si(Q 1 )(Q 2 )(Q 3 ), —B(Q 1 )(Q 2 ), —N(Q 1 )(Q 2 ), —P(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —S(═O)(Q 1 ), —S(═O) 2 (Q 1 ), —P(═O)(Q 1 )(Q 2 ), or —P(═S)(Q 1 )(Q 2 ), and
R 10a is the same as described in claim 1 .

5. The heterocyclic compound of claim 1 , wherein R 1 to R 9 are each independently:
hydrogen, deuterium, —F, —Cl, —Br, —I, a cyano group, a C 1 -C 20 alkyl group, or a C 1 -C 20 alkoxy group,
a C 1 -C 20 alkyl group or a C 1 -C 20 alkoxy group, each substituted with deuterium, —F, —Cl, —Br, —I, a cyano group, a phenyl group, a biphenyl group, or any combination thereof; or
a group represented by one selected from Formulae 5-1 to 5-26 and Formulae 6-1 to 6-55:

Assignees

• Samsung Display Co Ltd

Inventors

• Park Junwoo

Classifications

• H10K50/15

  Hole transporting layers · CPC title

• H10K85/6572

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

• C07D487/14 Primary

  Ortho-condensed systems · CPC title

• C07D487/16 Primary

  Peri-condensed systems · CPC title