Quantum dot, method of preparing the quantum dot, composition including the quantum dot, optical member including the quantum dot, and electronic apparatus including the quantum dot

Patent metadata

Field	Value
Publication number	US-12460126-B2
Application number	US-202217807693-A
Country	US
Kind code	B2
Filing date	Jun 17, 2022
Priority date	Jun 21, 2021
Publication date	Nov 4, 2025
Grant date	Nov 4, 2025

Abstract

A quantum dot, a method of manufacturing the quantum dot, a composition including the quantum dot, an optical member including the quantum dot, and an electronic apparatus including the quantum dot are disclosed. The quantum dot includes: a nanomaterial; and a first ligand arranged on a surface of the nanomaterial, wherein the nanomaterial includes a core and a shell that covers at least a part of the core, wherein the first ligand includes a condensed polycyclic group in which two or more rings are condensed.

First claim

What is claimed is:

1 . A quantum dot comprising:
a nanomaterial; and a first ligand on a surface of the nanomaterial, wherein the nanomaterial comprises a core and a shell that covers at least a part of the core, and the first ligand is represented by Formula 1:

wherein, in Formula 1,
L 1 is N(Z 1a ), O, S, or C(Z 1a )(Z 1b ),
L 2 is N(Z 2a ), O, S, or C(Z 2a )(Z 2b ),
L 3 is N(Z 3a ), O, S, or C(Z 3a )(Z 3b ),
L 4 is N(Z 4a ), O, S, or C(Z 4a )(Z 4b ),
L 5 is N(Z 5a ), O, S, or C(Z 5a )(Z 5b ),
L 6 is N(Z 6a ), O, S, or C(Z 6a )(Z 6b ),
n1 to n6 are each independently an integer from 0 to 10,
R 1 to R 4 , Z 1a to Z 6a , and Z 1b to Z 6b are each independently selected from: hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a thiol group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone 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 1 -C 60 alkylthio 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 ), —O(Q 1 ), —S(Q 1 ), —B(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —S(═O) 2 (Q 1 ), —P(Q 1 )(Q 2 ), and —P(═O)(Q 1 )(Q 2 ); and a conjugate base thereof,
R 10a is:
deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a thio group, a cyano group, a nitro group, an amidino group, a hydrazine group, or a hydrazone 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 1 -C 60 alkylthio group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a thio group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone 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 ), —O(Q 11 ), —S(Q 11 ), —B(Q 11 )(Q 12 ), —C(═O)(Q 11 ), —S(═O) 2 (Q 11 ), —P(Q 11 )(Q 12 ), —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 thio 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 1 -C 60 alkylthio 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 ), —O(Q 21 ), —S(Q 21 ), —B(Q 21 )(Q 22 ), —C(═O)(Q 21 ), —S(═O) 2 (Q 21 ), —P(Q 21 )(Q 22 ), —P(═O)(Q 21 )(Q 22 ), or any combination thereof; or
—Si(Q 31 )(Q 32 )(Q 33 ), —N(Q 31 )(Q 32 ), —O(Q 31 ), —S(Q 31 ), —B(Q 31 )(Q 32 ), —C(═O)(Q 31 ), —S(═O) 2 (Q 31 ), —P(Q 31 )(Q 32 ), 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:
hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a thio group; an amino 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 quantum dot of claim 1 , wherein the core comprises a Group II-VI semiconductor compound, a Group III-V semiconductor compound, or any combination thereof.

3 . The quantum dot of claim 1 , wherein the core comprises ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, GaN, GaP, GaAs, ZnSeS, ZnSeTe, ZnSTe, InP, InAs, InZnP, InGaP, InGaN, or any combination thereof.

4 . The quantum dot of claim 1 , wherein the shell comprises ZnS, ZnSe, ZnTe, ZnO, ZnSeS, ZnTeS, GaAs, GaP, GaN, Ga 2 O 3 , GaSb, HgS, HgSe, HgTe, InAs, InP, InS, InGaP, InSb, InZnP, InZnS, InGaP, InGaN, AlAs, AlP, AlSb, PbS, TiO 2 , SrSe, or any combination thereof.

5 . The quantum dot of claim 1 , wherein
L 1 is C(Z 1a )(Z 1b ), L 2 is C(Z 2a )(Z 2b ), L 3 is C(Z 3a )(Z 3b ), L 4 is C(Z 4a )(Z 4b ), L 5 is C(Z 5a )(Z 5b ), L 6 is C(Z 6a )(Z 6b ), and Z 1a to Z 6a and Z 1b to Z 6b are each as defined in Formula 1.

6 . The quantum dot of claim 1 , wherein R 1 to R 4 , Z 1a to Z 6a , and Z 1b to Z 6b are each independently selected from:
hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a thio group, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, and a C 1 -C 20 alkylthio group; a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, and a C 1 -C 20 alkylthio group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, —CD 3 , —CD 2 H, —CDH 2 , —CF 3 , —CF 2 H, —CFH 2 , a C 1 -C 10 alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, —N(Q 31 )(Q 32 ), —O(Q 31 ), —S(Q 31 ), —P(Q 31 )(Q 32 ), —C(═O)(Q 31 ), —S(═O) 2 (Q 31 ), and —P(═O)(Q 31 )(Q 32 ); a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a phenyl group, a biphenyl group, a C 1 -C 10 alkylphenyl group, and a naphthyl group, each unsubstituted or substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, —CD 3 , —CD 2 H, —CDH 2 , —CF 3 , —CF 2 H, —CFH 2 , a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a C 1 -C 20 alkylthio group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, —N(Q 31 )(Q 32 ), —O(Q 31 ), —S(Q 31 ), —P(Q 31 )(Q 32 ), —C(═O)(Q 31 ), —S(═O) 2 (Q 31 ), and —P(═O)(Q 31 )(Q 32 ); —N(Q 1 )(Q 2 ), —O(Q 1 ), —S(Q 1 ), —C(═O)(Q 1 ), —S(═O) 2 (Q 1 ), —P(Q 1 )(Q 2 ), and —P(═O)(Q 1 )(Q 2 ); and a conjugate base thereof, and wherein Q 1 , Q 2 , Q 31 , and Q 32 are each independently selected from: hydrogen, deuterium, —CH 3 , —CD 3 , —CD 2 H, —CDH 2 , —CH 2 CH 3 , —CH 2 CD 3 , —CH 2 CD 2 H, —CH 2 CDH 2 , —CHDCH 3 , —CHDCD 2 H, —CHDCDH 2 , —CHDCD 3 , —CD 2 CD 3 , —CD 2 CD 2 H, and —CD 2 CDH 2 ; and —F, —Cl, —Br, —I, a hydroxyl group, a thio group, an amino group, and a C 1 -C 10 alkyl group.

7 . The quantum dot of claim 1 , wherein R 1 to R 4 are each independently selected from:
hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a thio group, and a C 1 -C 20 alkylthio group; a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, and a C 1 -C 20 alkylthio group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, —CD 3 , —CD 2 H, —CDH 2 , —CF 3 , —CF 2 H, —CFH 2 , a C 1 -C 10 alkyl group, —N(Q 31 )(Q 32 ), —O(Q 31 ), —S(Q 31 ), —P(Q 31 )(Q 32 ), and —C(═O)(Q 31 ); —N(Q 1 )(Q 2 ), —C(═O)(Q 1 ), and —P(Q 1 )(Q 2 ); and a conjugate base thereof, and wherein R 10a , Q 1 , Q 2 , Q 31 , and Q 32 are as defined in Formula 1.

8 . The quantum dot of claim 1 , wherein the first ligand is selected from among

Assignees

• Samsung Display Co Ltd
• Univ Hannam Inst Ind Acad Coop
• Hannam Univ Institute For Industry—Academia Cooperation

Inventors

• Ko Yunhyuk
• Lee Changhee
• Prabhakaran prem
• Whang Dongryeol
• Kim Gyeongju
• Lee Kwangsup

Classifications

• H10H20/8512

  Wavelength conversion materials · CPC title

• H10K50/115

  comprising active inorganic nanostructures, e.g. luminescent quantum dots · CPC title

• B82Y20/00

  Nanooptics, e.g. quantum optics or photonic crystals · CPC title

• B82Y40/00

  Manufacture or treatment of nanostructures · CPC title

• C09K11/883

  with zinc or cadmium · CPC title