Quantum dot-containing material, and composition and electronic device including the same

Patent metadata

Field	Value
Publication number	US-12448566-B2
Application number	US-202117560951-A
Country	US
Kind code	B2
Filing date	Dec 23, 2021
Priority date	Jan 8, 2021
Publication date	Oct 21, 2025
Grant date	Oct 21, 2025

Abstract

A quantum dot-containing material includes: a quantum dot; and at least one ligand chemically bonded to the surface of the quantum dot and represented by a certain formula. A composition and an electronic apparatus, each include the quantum dot-containing material.

First claim

What is claimed is:

1. A quantum dot-containing material comprising:
a quantum dot; and
at least one ligand chemically bonded to a surface of the quantum dot and represented by Formula 1:

wherein, in Formulae 1, 2-1, and 2-2,
R a is an anchoring group comprising a moiety represented by —COOH, —PO 3 H, a dithiolane group, or —SH,
L 1 is *—(CH 2 ) n1 —*′ or *—(O—CH 2 —CH 2 ) n1 —O—*′,
b1 is an integer from 1 to 5,
P 1 is a group represented by Formula 2-1 or 2-2,
Z 1 to Z 3 are each independently selected from *—O—*′, *—C(═O)—*′, *—C(═O)O—*′, *—OC(═O)—*′, *—O—C(═O)—O—*′, *—OCH 2 —*′, *—SCH 2 —*′, *—CH 2 S—*′, *—CF 2 O—*′, *—OCF 2 —*′, *—CF 2 S—*′, *—SCF 2 —*, *—(CH 2 ) n1 —*, *—CF 2 CH 2 —*′, *—CH 2 CF 2 —*′, *—(CF 2 ) n1 —*, *—C(CH 3 )CN—*, *—CH═CH—*′, *—CF═CF—*′, *—C═C—*′, *—CH═CH—C(═O)O—*′, *—OC(═O)—CH═CH—*′, *—C(Q 1 )(Q 2 )—*′, and *—O—(CH 2 )—O(C═O)—(CH 2 ) n2 —*′,
n1 is an integer from 1 to 6, n2 is an integer from 0 to 2,
a1 to a3 are each independently an integer from 0 to 6,
R 1 is *—(CH 2 ) n3 —CH 3 , or *—(O—CH 2 —CH 2 ) n1 —OH, and
n3 is an integer from 0 to 5,
wherein Q 1 and Q 2 are each independently selected from hydrogen, deuterium, -F,-CI,-Br,-I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, 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, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group, and
* and *′ each indicate a binding site to a neighboring atom, and
wherein at least one Z 3 from among a number of a3 is *—O—*, *—C(═O)—*′, *—C(═O)O—*′, *—OC(═O)—*′, *—O—C(═O)—O—*′, *—OCH 2 —*′, *—SCH 2 —*′, *—CH 2 S—*′, *—CF 2 O—*′, *—OCF 2 —*, *—CF 2 S—*′, *—SCF 2 —*′, *—CF 2 CH 2 —*, *—CH 2 CF 2 —*′, *—(CF 2 ) n1 —*, *—CH═CH—*′, *—CF═CF—*′, *—C═C—*′, *—CH═CH—C(═O)O—*, *—OC(═O)—CH═CH—*, *—O—(CH 2 )—O (C═O)—(CH 2 ) n2 —*, or *—C(Q 1 )(Q 2 )—*′, wherein Q 1 and Q 2 are not a cyano group.

2. The quantum dot-containing material of claim 1 , wherein Ra is selected from —COOH, —PO 3 H, —SH, and a group represented by one of Formulae 3-1 to

and
wherein, in Formulae 3-1 to 3-4,
* indicates a binding site to a neighboring atom.

3. The quantum dot-containing material of claim 1 , wherein Z 1 is *—(CH 2 ) n1 —*′.

4. The quantum dot-containing material of claim 1 , wherein Z 2 and Z 3 are each independently *—O—*′, *—C(═O)O—*′, *—OC(═O)—*′, *—(CH 2 ) n1 —*′, or *—C(CH 3 )CN—*′.

5. The quantum dot-containing material of claim 1 , wherein *—(Z 2 ) a2 —*′ and *—(Z 3 ) a3 —*′ are each independently a group represented by one of Formulae 4-1 to 4-4:

and
wherein, in Formulae 4-1 to 4-4,
* and *′ each indicate a binding site to a neighboring atom.

6. A quantum dot-containing material comprising:
a quantum dot; and
at least one ligand chemically bonded to a surface of the quantum dot,
wherein the ligand is represented by Formula 1A or 1B:

and
wherein, in Formulae 1A and 1B,
R a , L 1 , b1, and R 1 are the same as described in connection with Formula 1.

7. The quantum dot-containing material of claim 1 , wherein the ligand comprises two or more ligands, and the two or more ligands are identical to or different from each other.

8. The quantum dot-containing material of claim 1 , wherein the ligand is chemically bonded to the surface of the quantum dot through the anchoring group.

9. The quantum dot-containing material of claim 1 , wherein the quantum dot is: a semiconductor nanoparticle; a particle having a core-shell structure comprising a core comprising a first semiconductor and a shell comprising a second semiconductor; or a perovskite compound.

10. The quantum dot-containing material of claim 9 , wherein the semiconductor nanoparticle, the first semiconductor, and the second semiconductor each independently comprise a Group 10 compound, a Group 11 compound, a Group 12-16 compound, a Group 13-15 compound, a Group 14-16 compound, a Group 14 compound, a Group Nov. 13, 2016 compound, a Group Nov. 12, 2013-16 compound, or a combination thereof.

11. The quantum dot-containing material of claim 9 , wherein the semiconductor nanoparticle, the first semiconductor, and the second semiconductor each independently comprise:
Au, Pd, or Ag;
CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgS, MgSe;
CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnS, MgZnSe; CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, or HgZnSTe;
GaN, GaP, GaAs, GaSb, AlN, AIP, AIAs, AISb, InN, InP, InAs, InSb; GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AIPAs, AIPSb, InGaP, InAIP, InNP, InNAs, InNSb, InPAs, InPSb, GaAINP; GaAINAs, GaAINSb, GaAIPAs, GaAIPSb, GalnNP, GalnNAs, GalnNSb, GalnPAs, GalnPSb, InAINP, InAINAs, InAINSb, InAIPAs, InAIPSb, or InZnP;
SnS, SnSe, SnTe, PbS, PbSe, PbTe; SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbTe; SnPbSSe, SnPbSeTe, or SnPbSTe;
Si, Ge, SiC, or SiGe;
AglnS, AglnS 2 , CulnS, CulnS 2 , CuGaO 2 , AgGaO 2 , or AgAIO 2 ; or
any combination thereof.

12. The quantum dot-containing material of claim 1 , wherein an average particle diameter (D50) of the quantum dot is from about 2 nm to about 10 nm.

13. A composition comprising:
the quantum dot-containing material of claim 1 ; and
at least one solvent.

14. The composition of claim 13 , further comprising a monomer comprising at least one double bond.

15. The composition of claim 13 , wherein the composition does not include an initiator.

16. An electronic apparatus comprising the quantum dot-containing material of claim 1 .

17. The electronic apparatus of claim 16 , further comprising a light-emitting device comprising:
a first electrode,
a second electrode facing the first electrode, and
an emission layer between the first electrode and the second electrode,
wherein the quantum dot-containing material is comprised in the emission layer.

18. The electronic apparatus of claim 16 , further comprising a light source, wherein the quantum dot-containing material is located on a path of light emitted from the light source.

19. The electronic apparatus of claim 18 , further comprising a color conversion layer,
wherein the color conversion layer comprises the quantum dot-containing material.

20. The electronic apparatus of claim 18 , wherein the light source is an organic light-emitting device (OLED) or a light-emitting diode (LED).

Assignees

• Samsung Display Co Ltd

Inventors

• Park Chulsoon
• Lee Donghee

Classifications

• H10K59/12

  Active-matrix OLED [AMOLED] displays · CPC title

• H10K2102/00

  Constructional details relating to the organic devices covered by this subclass · CPC title

• H10K2101/10

  Triplet emission · CPC title

• H10K50/115

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

• H10K50/11

  characterised by the electroluminescent [EL] layers · CPC title