Quantum dots, a composition or composite including the same, and an electronic device including the same

Patent metadata

Field	Value
Publication number	US-10988685-B2
Application number	US-201715820781-A
Country	US
Kind code	B2
Filing date	Nov 22, 2017
Priority date	Nov 25, 2016
Publication date	Apr 27, 2021
Grant date	Apr 27, 2021

Abstract

A quantum dot including a first ligand and a second ligand on a surface of the quantum dot, a composition or composite including the same, and a device including the same. The first ligand includes a compound represented by Chemical Formula 1 and the second ligand includes a compound represented by Chemical Formula 2:

MA n   Chemical Formula 1
wherein M, n, and A are the same as defined in the specification; and

wherein,
R 1 , L 1 , Y 1 , R, k1, and k2 are the same as defined in the specification.

First claim

What is claimed is:

1. A quantum dot comprising:
a semiconductor nanocrystal particle;
a first ligand bound to a surface of the semiconductor nanocrystal particle; and
a second ligand bound to the surface of the semiconductor nanocrystal particle,
wherein the second ligand comprises a compound represented by Chemical Formula 2-1, Chemical Formula 2-2, or Chemical Formula 2-3:
R a -L-(CRR) n SM  Chemical Formula 2-1

RRNCSSM  Chemical Formula 2-3

wherein
R a includes a substituted or unsubstituted C1 to C24 alkyl group, a substituted or unsubstituted C2 to C24 alkenyl group, and a substituted or unsubstituted C6 to C20 aryl group, R is the same or different, and is each independently hydrogen or a substituted or unsubstituted C1 to C24 alkyl group, n is an integer of 0 to 15, L is a direct bond, a sulfonyl (—S(═O) 2 —), carbonyl (—C(═O)—), ether group (—O—), sulfide group (—S—), sulfoxide group (—S(═O)—), ester group (—C(═O)O—), amide group (—C(═O)NR 1 —) (wherein R 1 is hydrogen or a C1 to C10 alkyl group), a substituted or a unsubstituted C1 to C10 alkylene, a C2 to C10 alkenylene, or a combination thereof, and M is hydrogen, or sodium,
wherein the first ligand comprises a compound represented by Chemical Formula 1:
MA n   Chemical Formula 1

wherein M is Mg, Ca, or Zn, n is determined depending on a valency of the M and is an integer of greater than or equal to 2, each A is the same or different, and is independently a C1 to C10 organic group, fluorine, bromine, chlorine, or a combination thereof, and
wherein the compound represented by Chemical Formula 1 comprises an organic metal salt, a halogenated metal, a hydrocarbyl metal, a hydrocarbyl metal halide, or a combination thereof, and
wherein when a plurality of the quantum dots are included in a composition comprising a binder polymer having a carboxylic acid group and the composition is left at 4° C. for 144 hours, an increase of a viscosity of the composition is less than about 10% with respect to an initial viscosity of the composition.

2. The quantum dot of claim 1 , wherein the semiconductor nanocrystal particle 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-IV compound, or a combination thereof.

3. The quantum dot of claim 1 , wherein the semiconductor nanocrystal particle comprises a core comprising a first semiconductor nanocrystal and a shell disposed on the core, and comprising a second semiconductor nanocrystal.

4. The quantum dot of claim 1 , wherein the A of Chemical Formula 1 comprises a C2 to C5 organic functional group.

5. The quantum dot of claim 1 , wherein the A of Chemical Formula 1 comprises a C2 to C5 hydrocarbyl group, RCOO— or ROCO—wherein R is a C1 to C4 hydrocarbyl group), fluorine, chlorine, bromine, or a combination thereof.

6. The quantum dot of claim 1 , wherein the first ligand comprises a metal that is the same as a metal present on the surface of the quantum dot.

7. The quantum dot of claim 1 , wherein the first ligand comprises diethyl zinc, dipropyl zinc, a zinc carboxylate, a zinc (meth)acrylate, zinc chloride, or a combination thereof.

8. The quantum dot of claim 1 , wherein the first ligand comprises a zinc acetate, a zinc propionate, a zinc butyrate, a zinc (meth)acrylate, a zinc chloride, or a combination thereof.

9. The quantum dot of claim 1 , wherein the second ligand comprises butanethiol, pentanethiol, hexanethiol, heptanethiol, octanethiol, nonanethiol, decanethiol, undecanethiol, dodecanethiol, octadecanethiol, 2-(2-methoxyethoxy)ethanethiol, 3-methoxybutyl 3-mercaptopropionate, 3-methoxybutyl mercaptoacetate, thioglycolic acid, 3-mercaptopropionic acid, thiopronine, 2-mercaptopropionic acid, 2-mercaptopropionate, 2-mercaptoethanol, cysteamine, 1-thioglycerol, mercaptosuccinic acid, L-cysteine, dihydrolipoic acid, 2-(dimethylamino)ethanethiol, 5-mercaptomethyl tetrazole, 2,3-dimercapto-1-propanol glutathione, m(PEG)-SH, di(C1 to C30 alkyl)dithiocarbamic acid, di(C1 to C30 alkyl)dithiocarbamate, or a combination thereof.

10. The quantum dot of claim 1 , wherein the quantum dot has a 5% weight loss temperature of less than or equal to about 400° C. as determined by a thermogravimetric analysis.

11. A composition comprising:
the quantum dot of claim 1 ;
a binder polymer;
a polymerizable monomer comprising a carbon-carbon double bond; and
a photoinitiator.

12. The composition of claim 11 , wherein the binder polymer comprises a copolymer of a monomer combination comprising a first monomer comprising a carboxylic acid group and a carbon-carbon double bond, a second monomer comprising a carbon-carbon double bond and a hydrophobic moiety and 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 and comprising a backbone structure in a 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.

13. The composition of claim 12 , wherein the copolymer comprises a first repeating unit derived from the first monomer, a second repeating unit derived from the second monomer, and optionally, a third repeating unit derived from the third monomer,
wherein the first repeating unit comprises a unit represented by Chemical Formula 3-1, a unit represented by Chemical Formula 3-2, 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 ) n —COOH (wherein n 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;
the second repeating unit comprises a repeating unit represented by Chemical Formula 4-1, a repeating unit represented by Chemical Formula 4-2, a repeating unit represented by Chemical Formula 4-3, a repeating unit represented by Chemical Formula 4-4, 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 substi

Assignees

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

Inventors

• Ahn Jooyeon
• Kwon Ha Il
• Park Shang Hyeun
• Won Nayoun
• Jang Eun Joo
• Jun Shin Ae

Classifications

• H10H20/812

  within the light-emitting regions, e.g. having quantum confinement structures · CPC title

• C09K11/70

  containing phosphorus · CPC title

• C09K2211/10

  Non-macromolecular compounds · CPC title

• C08L101/00

  Compositions of unspecified macromolecular compounds · CPC title

• C08L35/06

  Copolymers with vinyl aromatic monomers · CPC title