Compositions, quantum dot polymer composites prepared therefrom, and devices including the same

Patent metadata

Field	Value
Publication number	US-11021650-B2
Application number	US-201715672608-A
Country	US
Kind code	B2
Filing date	Aug 9, 2017
Priority date	Aug 9, 2016
Publication date	Jun 1, 2021
Grant date	Jun 1, 2021

Abstract

A composition including a plurality of quantum dots; a binder polymer; a thiol compound having at least two thiol groups; a polyvalent metal compound; a polymerizable monomer having a carbon-carbon double bond; a photoinitiator; and a solvent.

First claim

What is claimed is:

1. A composition comprising:
a plurality of quantum dots;
a polymer;
a thiol compound comprising at least two thiol groups at its end terminals;
a polyvalent metal compound;
a polymerizable monomer comprising a carbon-carbon double bond;
a photoinitiator; and
a solvent,
wherein the polymer comprises
a copolymer of a monomer combination comprising a first monomer comprising a carboxylic acid group, a second monomer not comprising a carboxylic acid group, and optionally, a third monomer comprising a carbon-carbon double bond and a hydrophilic moiety and not comprising a carboxylic acid group;
a multiple aromatic ring-containing polymer comprising a carboxylic acid group (—COOH) and a main chain comprising a backbone structure incorporated in the main chain, wherein the backbone structure comprises a quaternary carbon atom, which is a part of a cyclic group, and two aromatic rings bound to the quaternary carbon atom; or
a combination thereof,

wherein the polyvalent metal compound comprises a metal chloride, an alkylated metal, a metal acetate, a metal (meth)acrylate, a metal dialkyldithiocarbamate, or a combination thereof, and
wherein the copolymer comprises a first repeating unit derived from the first monomer and a second repeating unit derived from the second monomer,
wherein the first repeating unit comprises a repeating unit represented by Chemical Formula 1-1, a repeating unit represented by Chemical Formula 1-2, or a combination thereof:

wherein
R 1 is hydrogen, a C1 to C3 alkyl group, or —(CH 2 ) n —COOH (wherein n is 0 to 2),
R 2 is hydrogen, a C1 to C3 alkyl group, or —COOH,
L is a single bond, a C1 to C15 aliphatic hydrocarbon group, a C6 to C30 aromatic hydrocarbon group, a C3 to C30 alicyclic hydrocarbon group, or a C1 to C15 aliphatic hydrocarbon group substituted with a C6 to C30 aromatic hydrocarbon group or a C3 to C30 alicyclic hydrocarbon group, and
* indicates a portion linked to an adjacent atom;

wherein
R 1 is hydrogen, a C1 to C3 alkyl group, or —(CH 2 ) n1 —COOH (wherein n1 is 0 to 2),
R 2 is hydrogen or a C1 to C3 alkyl group,
L is a C1 to C15 alkylene group, a C1 to C15 alkylene group wherein at least one methylene group is substituted with —C(═O)—, —O—, or —C(═O)O—, a C6 to C30 aromatic hydrocarbon group, a C3 to C30 alicyclic hydrocarbon group, or a C1 to C15 aliphatic hydrocarbon group substituted with a C6 to C30 aromatic hydrocarbon group or a C3 to C30 alicyclic hydrocarbon group,
n is an integer of 1 to 3, and
* indicates a portion linked to an adjacent atom;
wherein the second repeating unit comprises a repeating unit represented by Chemical Formula 2-1, a repeating unit represented by Chemical Formula 2-2, a repeating unit represented by Chemical Formula 2-3, a repeating unit represented by Chemical Formula 2-4, or a combination thereof:

wherein
R 1 is hydrogen or a C1 to C3 alkyl group,
R 2 is a C1 to C15 aliphatic hydrocarbon group, a C6 to C30 aromatic hydrocarbon group, a C3 to C30 alicyclic hydrocarbon group, or a C1 to C15 aliphatic hydrocarbon group substituted with a C6 to C30 aromatic hydrocarbon group or a C3 to C30 alicyclic hydrocarbon group,
R 3 is hydrogen or a C1 to C3 alkyl group,
* indicates a portion linked to an adjacent atom;

wherein
R 1 is hydrogen or a C1 to C3 alkyl group,
L is a C1 to C15 alkylene group, a C1 to C15 alkylene group wherein at least one methylene group is substituted with —C(═O)—, —O—, or —C(═O)O—, a C6 to C30 aromatic hydrocarbon group, a C3 to C30 alicyclic hydrocarbon group, or a C1 to C15 aliphatic hydrocarbon group substituted with a C6 to C30 aromatic hydrocarbon group or a C3 to C30 alicyclic hydrocarbon group,
R 2 is a C1 to C15 aliphatic hydrocarbon group, a C6 to C30 aromatic hydrocarbon group, a C3 to C30 alicyclic hydrocarbon group, or a C1 to C15 aliphatic hydrocarbon group substituted with a C6 to C30 aromatic hydrocarbon group or a C3 to C30 alicyclic hydrocarbon group,
R 3 is hydrogen or a C1 to C3 alkyl group,
n is an integer of 1 to 3, and
* indicates a portion linked to an adjacent atom;

wherein
each of R 1 and R 2 is independently hydrogen or a C1 to C3 alkyl group,
Ar is a substituted or unsubstituted C6 to C30 aromatic hydrocarbon group or a substituted or unsubstituted C3 to C30 alicyclic hydrocarbon group, and
* indicates a portion linked to an adjacent atom;

wherein
R 1 is hydrogen or a C1 to C3 alkyl group,
R 2 is a C1 to C15 aliphatic hydrocarbon group, a C6 to C30 aromatic hydrocarbon group, a C3 to C30 alicyclic hydrocarbon group, or a C1 to C15 aliphatic hydrocarbon group substituted with a C6 to C30 aromatic hydrocarbon group or a C3 to C30 alicyclic hydrocarbon group,
R 3 is hydrogen or a C1 to C3 alkyl group, and
* indicates a portion linked to an adjacent atom.

2. The composition of claim 1 , wherein the plurality of the quantum dots are dispersed by the polymer.

3. The composition of claim 1 , wherein the quantum dot has an organic ligand on a surface thereof, and wherein the organic ligand comprises RCOOH, RNH 2 , R 2 NH, R 3 N, RSH, R 3 PO, R 3 P, ROH, RCOOR′, RPO(OH) 2 , R 2 POOH (wherein R and R′ are independently a C5 to C24 substituted or unsubstituted aliphatic hydrocarbon group or a C6 to C20 substituted or unsubstituted aromatic hydrocarbon group), a polymeric organic ligand, or a combination thereof.

4. The composition of claim 1 , wherein the quantum dot comprises a Group II-VI compound, a Group III-V compound, a Group IV-VI compound, a Group IV element or compound, a Group compound, a Group I-II-IV-VI compound, or a combination thereof.

5. The composition of claim 1 , wherein the carboxylic acid group-containing polymer has an acid value of greater than about 60 milligrams of KOH per gram of the polymer and less than or equal to about 250 milligrams of KOH per gram of the polymer.

6. The composition of claim 1 ,
wherein
the backbone structure of the multiple aromatic ring-containing polymer comprises a unit represented by Chemical Formula B:

wherein
* indicates a portion that is linked to an adjacent atom of the main chain of the multiple aromatic ring-containing polymer,
Z 1 is a linking moiety represented by any one of Chemical Formulae B-1 to B-6, and in Chemical Formulae B-1 to B-6, * indicates a portion that is linked to an adjacent atom:

wherein R a is hydrogen, an ethyl group, C 2 H 4 Cl, C 2 H 4 OH, CH 2 CH═CH 2 , or a phenyl group,

7. The composition of claim 1 , wherein the copolymer further comprises a third repeating unit derived f

Assignees

• Samsung Electronics Co Ltd
• Samsung Display Co Ltd
• Samsung Sdi Co Ltd

Inventors

• Kwon Ha Il
• Kim Tae Gon
• Park Shang Hyeun
• Jang Eun Joo
• Jun Shin Ae
• Park Garam

Classifications

• C09K11/02 Primary

  Use of particular materials as binders, particle coatings or suspension media therefor · CPC title

• C08L2203/20

  use in electrical or conductive gadgets · CPC title

• C08L33/04

  Homopolymers or copolymers of esters {(C08L43/04 takes precedence)} · CPC title

• C08L23/00 Primary

  Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers · CPC title

• C08J3/02

  Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques · CPC title