Quantum dot-containing material comprising an azide group and a charge transport group, method of preparing thereof, cross-linked material thereof, method of preparing cross-linked material, and light-emitting device including cross-linked material

Patent metadata

Field	Value
Publication number	US-12497559-B2
Application number	US-202117546289-A
Country	US
Kind code	B2
Filing date	Dec 9, 2021
Priority date	Dec 23, 2020
Publication date	Dec 16, 2025
Grant date	Dec 16, 2025

Abstract

Disclosed are a quantum dot-containing material, a method of preparing the quantum dot-containing material, a cross-linked material of the quantum dot-containing material, and a method of preparing the same, and a light-emitting device comprising the quantum dot-containing material. The quantum dot-containing material may include a quantum dot and an organic group chemically bound to a surface of the quantum dot, the organic group may include an azide group and a charge transport group, and the charge transport group may not be an unsubstituted benzene group.

First claim

What is claimed is:

1 . A quantum dot-containing material comprising:
a quantum dot; and an organic group chemically bound to a surface of the quantum dot via an oxygen bond or a sulfur bond, wherein the organic group comprises: an azide group, and a charge transport group, and the charge transport group is not an unsubstituted benzene group.

2 . The quantum dot-containing material of claim 1 , wherein the quantum dot comprises:
a group II-VI semiconductor compound; a group III-V semiconductor compound; a group III-VI semiconductor compound; a group I-III-VI semiconductor compound; a group IV-VI semiconductor compound; a group IV element or compound; or any combination thereof.

3 . The quantum dot-containing material of claim 1 , wherein the charge transport group in the organic group is an electron donating group or an electron withdrawing group.

4 . The quantum dot-containing material of claim 3 , wherein the electron donating group is a π electron-rich C 3 -C 60 cyclic group unsubstituted or substituted with at least one of R 20a or N(Ar 2 )(Ar 3 ), wherein
Ar 2 and Ar 3 are each independently a π electron-rich C 3 -C 60 cyclic group unsubstituted or substituted with at least one R 20a ,
the electron withdrawing group is:
—F, —CFH 2 , —CF 2 H, —CF 3 , —CN, or —NO 2 ;
a C 1 -C 60 alkyl group substituted with at least one of —F, —CFH 2 , —CF 2 H, —CF 3 , —CN or —NO 2 ; or
a π electron-depleted nitrogen-containing C 1 -C 60 cyclic group unsubstituted or substituted with at least one R 10a ,
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, a C 1 -C 60 alkylthio group, or a C 1 -C 60 alkoxy group, each independently 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 1 -C 60 heteroaryloxy group, a C 1 -C 60 heteroarylthio 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 1 -C 60 heteroaryloxy group, or a C 1 -C 60 heteroarylthio group, each independently 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 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 1 -C 60 arylthio group, a C 1 -C 60 heteroaryloxy group, a C 1 -C 60 heteroarylthio 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 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; a C 1 -C 60 alkylthio group; a C 3 -C 60 carbocyclic group; or a C 1 -C 60 heterocyclic group, each independently unsubstituted or substituted with deuterium, —F, a cyano group, a C 1 -C 60 alkyl group, a C 1 -C 60 alkoxy group, a C 1 -C 60 alkylthio group, a phenyl group, a biphenyl group, or any combination thereof, and
R 20a is:
deuterium, a hydroxyl 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, a C 1 -C 60 alkylthio group, or a C 1 -C 60 alkoxy group, each independently unsubstituted or substituted with deuterium, a hydroxyl group, a nitro group, a π electron-rich C 3 -C 60 cyclic group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryloxy group, a C 1 -C 60 heteroarylthio group, —Si(Q 41 )(Q 42 )(Q 43 ), —N(Q 41 )(Q 42 ), —B(Q 41 )(Q 42 ), or any combination thereof;
a π electron-rich C 3 -C 60 cyclic group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryloxy group, or a C 1 -C 60 heteroarylthio group, each independently unsubstituted or substituted with deuterium, a hydroxyl 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 π electron-rich C 3 -C 60 cyclic group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryloxy group, a C 1 -C 60 heteroarylthio group, —Si(Q 51 )(Q 52 )(Q 53 ), —N(Q 51 )(Q 52 ), —B(Q 51 )(Q 52 ), or any combination thereof; or
—Si(Q 61 )(Q 62 )(Q 63 ), —N(Q 61 )(Q 62 ), or —B(Q 61 )(Q 62 ),
wherein Q 41 to Q 43 , Q 51 to Q 53 , and Q 61 to Q 63 are each independently: hydrogen; deuterium; a hydroxyl 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; or a π electron-rich C 3 -C 60 cyclic group unsubstituted or substituted with deuterium, —F, a cyano group, a C 1 -C 60 alkyl group, a C 1 -C 60 alkoxy group, a C 1 -C 60 alkylthio group, a phenyl group, a biphenyl group, or any combination thereof.

5 . The quantum dot-containing material of claim 3 , wherein the electron donating group is substituted a benzene group, a heptalene group, an indene group, a naphthalene group, an azulene group, an indacene group, an acenaphthylene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentacene group, a hexacene group, a pentaphene group, a rubicene group, a coronene group, an ovalene group, a pyrrole group, a furan group, a thiophene group, an isoindole group, an indole group, an indene group, a benzofuran group, a benzothiophene group, a benzosilole group, a naphthopyrrole group, a naphthofuran group, a naphthothiophene group, a naphthosilole group, a benzocarbazole group, a dibenzocarbazole group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, a dibenzosilole group, an indenocarbazole group, an indolocarbazole group, a benzofurocarbazole group, a benzothienocarbazole group, a benzosilolocarbazole group, a triindolobenzene group, a pyrrolophenanthrene group, a furanophenanthrene group, a thienophenanthrene group, a benzonaphthofuran group, a benzonapthothiophene group, an (indolo) phenanthrene group, a (benzofurano) phenanthrene group, a (benzothieno) phenanthrene group, or —N(Ar 2 )(Ar 3 ), each independently unsubstituted or substituted with at least one R 20a , and
descriptions of Ar 2 , Ar 3 , and R 20a are the same as set forth in claim 4 .

6 . The quantum dot-containing material of claim 1 , wherein the organic group is a group represented by Formula 1:
Formula 1 *—X 1 —Z 1 -(A 1 ) m -Z 2 -(A 2 ) n -Z 3 -T 1   1
wherein A 1 and A 2 are each independently a group represented by Formula 2-1 or Formula 2-2,

wherein, in Formula 1,
X 1 is O or S,
Z 1 to Z 3 are each independently:
a single bond;
*—N(R 1a )—*′, *—O—*′, *—S—*′, or *—C(═O)—*′; or
a C 1 -C 60 alkyl

Assignees

• Samsung Display Co Ltd

Inventors

• Park Junwoo

Classifications

• H10K50/115

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

• C09D11/037

  characterised by the pigment · CPC title

• B82Y20/00

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

• C09D11/106

  containing macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds · CPC title

• C09D11/101

  Inks specially adapted for printing processes involving curing by wave energy or particle radiation, e.g. with UV-curing following the printing · CPC title