Quantum dot composition, quantum dot polymer composite, and layered structure and electronic devices including the same

Patent metadata

Field	Value
Publication number	US-10759993-B2
Application number	US-201816180376-A
Country	US
Kind code	B2
Filing date	Nov 5, 2018
Priority date	Nov 3, 2017
Publication date	Sep 1, 2020
Grant date	Sep 1, 2020

Abstract

A quantum dot composition comprising a quantum dot, a metal thiolate complex compound, and a solvent, wherein the metal thiolate complex compound includes a hydrophobic moiety, a thioether moiety (—S—), and a polyvalent metal, and wherein the hydrophobic moiety includes a fluorinated organic group, a multi-aromatic ring-containing group having a backbone structure that includes 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.

First claim

What is claimed is:

1. A quantum dot composition comprising:
a quantum dot,
a metal thiolate complex compound, and
a solvent,
wherein the metal thiolate complex compound comprises a hydrophobic moiety, a thioether moiety, and a polyvalent metal, and
wherein the hydrophobic moiety comprises a fluorinated organic group, a multi-aromatic ring-containing group having a backbone structure comprising 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 metal thiolate complex compound is represented by Chemical Formula 1:

wherein,
R 1 is hydrogen; a substituted or unsubstituted C1 to C30 linear or branched alkyl group; a substituted or unsubstituted C6 to C30 aryl group; a substituted or unsubstituted C3 to C30 heteroaryl group; a substituted or unsubstituted C3 to C30 cycloalkyl group; a substituted or unsubstituted C3 to C30 heterocycloalkyl group; a C1 to C10 alkoxy group; a hydroxy group; —NH 2 ; a substituted or unsubstituted —NR a R a ′, wherein R a and R a ′ are the same or different, and are independently hydrogen or a C1 to C30 linear or branched alkyl group and provided that R a and R a ′ are not both hydrogen; an isocyanate group; a halogen; —R b OR b ′ wherein R b is a substituted or unsubstituted C1 to C20 alkylene group and R b ′ is hydrogen or a C1 to C20 linear or branched alkyl group; an acyl halide group; —C(═O)OR c ′ wherein R c ′ is hydrogen or a C1 to C20 linear or branched alkyl group; —CN; —C(═O)ONR d R d ′ wherein R d and R d ′ are the same or different, and are independently hydrogen or a C1 to C20 linear or branched alkyl group; or a combination thereof,
L 1 is a carbon atom; a substituted or unsubstituted C2 to C30 alkylene group; a substituted or unsubstituted C2 to C30 alkylene group having at least one methylene replaced with a sulfonyl group, a carbonyl group, an ether group, a sulfide group, a sulfoxide group, an ester group, an amide group, or a combination thereof; a substituted or unsubstituted C3 to C30 cycloalkylene group; a substituted or unsubstituted C3 to C30 heterocycloalkylene group; a substituted or unsubstituted C6 to C30 arylene group; or a substituted or unsubstituted C3 to C30 heteroarylene group,
Y 1 is a single bond, a substituted or unsubstituted C1 to C30 alkylene group, a substituted or unsubstituted C2 to C30 alkenylene group, or a C1 to C30 alkylene group or a C2 to C30 alkenylene group wherein at least one methylene is replaced by a sulfonyl group, a carbonyl group, an ether group, a sulfide group, a sulfoxide group, an ester group, an amide group, an imine group, or a combination thereof,
A is -M(R 2 ) a-1 , —CR═CR 3 —Y 2 —R 4 , or —CHRCHR 3 —Y 2 —R 4 , wherein R is hydrogen or a methyl group, M is Al, Mg, Ca, Sc, Ti, V, Cr, Mn, Fe, Co, Ni, Cu, Zn, Ga, Sr, Y, Zr, Nb, Mo, Cd, In, Ba, Au, Hg, Tl, or a combination thereof, a is a valance of the M, R 2 is a group selected from a thiolate containing organic group, a halide, a (meth)acrylate group, a dialkyldithiocarbamate group, an acetate group, a propionate group, a butyrate group, a valerate group, and a carboxy ethyl acrylate group, R 3 is hydrogen, —COOH, or a C1 to C10 alkyl group, Y 2 is a single bond, a substituted or unsubstituted divalent C1 to C10 alkylene group, a sulfonyl group, a carbonyl group, an ether group, a sulfide group, a sulfoxide group, an ester group, an amide group, an imine group, or a combination thereof, and R 4 is the fluorinated organic group or the multi-aromatic ring-containing group, provided that at least one of the A is -M(R 2 ) a-1 and at least one of the A is —CR═CR 3 —Y 2 —R 4 or —CHRCHR 3 —Y 2 —R 4 ,
m is an integer of at least 1,
k1 is 0 or an integer of 1 or more and k2 is an integer of 1 or more,
the sum of m and k2 is an integer of greater than or equal to 3,
m does not exceed the valence of Y 1 ; and
the sum of k1 and k2 does not exceed the valence of L 1 .

2. The quantum dot composition of claim 1 , wherein the metal thiolate complex compound is bound to a surface of the quantum dot and is present as a part of a quantum dot complex.

3. The quantum dot composition of claim 2 , wherein in the quantum dot complex, the polyvalent metal binds the metal thiolate complex compound to the quantum dot.

4. The quantum dot composition of claim 1 , wherein the polyvalent metal comprises Al, Mg, Ca, Sc, Ti, V, Cr, Mn, Fe, Co, Ni, Cu, Zn, Ga, Sr, Y, Zr, Nb, Mo, Cd, In, Ba, Au, Hg, Tl, or a combination thereof.

5. The quantum dot composition of claim 1 , wherein the metal thiolate complex compound comprises a dithiolene moiety represented by *—S-M-S—*, wherein * is a portion linked to an atom constituting the metal thiolate complex compound.

6. The quantum dot composition of claim 1 , wherein in the metal thiolate complex compound, the polyvalent metal is directly linked to the thioether moiety.

7. The quantum dot composition of claim 1 , wherein the fluorinated organic group comprises a fluorinated hydrocarbon group, and
wherein the backbone structure of the multi-aromatic ring-containing group comprises a moiety represented by Chemical Formula A:

wherein
* indicates a portion that is linked to an adjacent atom,
each of R 1 and R 2 is independently hydrogen, a halogen, or a substituted or unsubstituted C1 to C20 alkyl group,
m1 and m2 are the same or different, and are independently an integer ranging from 0 to 4,
Z 1 is a linking moiety represented by any one of Chemical Formulae A-1 to A-6, and, in Chemical Formulae A-1 to A-6, * indicates a portion that is linked to an adjacent atom in the aromatic ring:

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,

8. The quantum dot composition of claim 7 , wherein the fluorinated hydrocarbon group comprises a C1 to C50 fluorinated linear or branched alkyl group or a C1 to C50 fluorinated linear or branched alkenyl group.

9. The quantum dot composition of claim 1 , wherein the metal thiolate complex compound is represented by Chemical Formula 1-1:

wherein
L 1 ′ is carbon; a substituted or unsubstituted C2 to C30 alkylene group; a substituted or unsubstituted C2 to C30 alkylene group having at least one methylene replaced with a sulfonyl group, a carbonyl group, an ether group, a sulfide group, a sulfoxide, an ester group, an amide group, or a combination thereof; a substituted or unsubstituted C6 to C30 arylene group; a substituted or unsubstituted C3 to C30 heteroarylene group; a substituted or unsubstituted C3 to C30 cycloalkylene group; or a substituted or unsubstituted C3 to C30 heterocycloalkylene group,
Y a to Y d are the same or different, and are independently a single bond, a substituted or unsubstituted C1 to C30 alkylene group, a substituted or unsubstituted C2 to C30 alkenylene group, or a substituted or unsubstituted C1 to C30 alkylene group or a substituted or unsubstituted C2 to C30 alkenylene group wherein at least one methylene is replaced by a sulfonyl group, a carbonyl group, an ether group, a sulfide group

Assignees

• Samsung Electronics Co Ltd

Inventors

• Yang Hyeyeon
• Lee Jongmin
• Jun Shin Ae

Classifications

• H10H20/8513

  having two or more wavelength conversion materials · CPC title

• G03F7/033

  the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers · CPC title

• G03F7/027

  Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds (G03F7/075 takes precedence) · CPC title

• G03F7/028

  with photosensitivity-increasing substances, e.g. photoinitiators · CPC title

• C09K11/02 Primary

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