Semiconductor-nanoparticle-ligand complex, preparation method therefor, photosensitive resin composition, optical film, electroluminescent diode and electronic device

Patent metadata

Field	Value
Publication number	US-12504558-B2
Application number	US-202118035072-A
Country	US
Kind code	B2
Filing date	Nov 18, 2021
Priority date	Nov 18, 2020
Publication date	Dec 23, 2025
Grant date	Dec 23, 2025

Abstract

Embodiments of the present invention relate to a semiconductor-nanoparticle-ligand complex, a preparation method therefor, a photosensitive resin composition, an optical film, an electroluminescent diode and an electronic device, and, more specifically, can provide: a semiconductor-nanoparticle-ligand complex comprising a ligand represented by chemical formula 1, and thus has excellent compatibility; an optical film with excellent efficiency; an electroluminescent diode; and an electronic device.

First claim

The invention claimed is:

1 . A semiconductor nanoparticle-ligand complex including a ligand represented by chemical formula 1 below:

in chemical formula 1, wherein X is a functional group bonded to a surface of a semiconductor nanoparticle and is —S(H), —P═O(OH) 2 or —COOH,
wherein L 1 is selected from the group consisting of: an arylene group of C 6 -C 30 ; a heterocyclic group of C 2 -C 30 including at least one heteroatom selected from the group consisting of O, N, S, Si, and P; an alkylene group of C 1 -C 20 ; an alkoxyl group of C 1 -C 20 ; an alkylthio group of C 1 -C 20 ; and a combination thereof,
wherein L 2 and L 3 are, independently of each other, selected from the group consisting of a single bond; an arylene group of C 6 -C 20 ; a heterocyclic group of C 2 -C 20 including at least one heteroatom selected from the group consisting of O, N, S, Si, and P; an aliphatic ring group of C 3 -C 20 ; an alkylene group of C 1 -C 10 ; an alkoxyl group of C 1 -C 10 ; an alkylthio group of C 1 -C 10 ; and a combination thereof,
wherein R′ and R″ are, independently of each other, represented by one of chemical formulas 2 to 4 below,

in chemical formula 2,
wherein R 1 is, independently of each other, a hydrogen or methyl group,
wherein L 4 is, independently of each other, selected from the group consisting of an alkylene group of C 1 -C 20 ; an alkoxyl group of C 1 -C 20 ; an alkylthio group of C 1 -C 20 ; and chemical formula 5 below,

in chemical formula 3,
wherein R 2 to R 4 are, independently of each other, a hydrogen or methyl group,
wherein L 5 and L 6 are, independently of each other, selected from the group consisting of an alkylene group of C 1 -C 20 ; an alkoxyl group of C 1 -C 20 ; an alkylthio group of C 1 -C 20 ; and chemical formula 5,

wherein in chemical formula 4 above, R 5 is, independently of each other, an alkyl group of C 1 -C 10 ,
wherein L 7 is, independently of each other, selected from the group consisting of a single bond; an alkylene group of C 1 -C 20 ; an alkoxyl group of C 1 -C 20 ; an alkylthio group of C 1 -C 20 ; and chemical formula 5,
wherein in L 1 to L 7 in chemical formulas 1 to 4, each of the arylene group, the heterocyclic group, the alkylene group, the alkoxyl group, and the alkylthio group may further be substituted with one or more substituents selected from the group consisting of deuterium; an aryl group of C 6 -C 10 ; a heterocyclic group of C 2 -C 10 ; an aliphatic ring group of C 3 -C 10 ; and an alkyl group of C 1 -C 10 ,

in chemical formula 5,
wherein n1 is an integer from 1 to 12, and
wherein R 6 and R 7 are, independently of each other, a hydrogen or methyl group.

2 . The semiconductor nanoparticle-ligand complex of claim 1 ,
wherein the ligand represented by chemical formula 1 is represented by any one of chemical formulas below:

in chemical formula 1-1 to chemical formula 1-6 above,
X, L 1 , L 2 and L 3 are the same as those defined in chemical formula 1 above, and R 1 to R 5 and L 4 to L 7 are the same as those defined in chemical formulas 2 to 4 above.

3 . The semiconductor nanoparticle-ligand complex of claim 1 ,
wherein the ligand represented by chemical formula 1 is any one of compounds below:

4 . The semiconductor nanoparticle-ligand complex of claim 1 ,
wherein the semiconductor nanoparticle has a particle size of 1 nm to 30 nm.

5 . A method for preparing a semiconductor nanoparticle-ligand complex, comprising:
a first surface modification step surface-modifying a surface of a semiconductor nanoparticle with a compound represented by chemical formula 6 below; and a second surface modification step performing surface modification by reacting an alcohol group (—OH) of chemical formula 6 of the semiconductor nanoparticle surface-modified by the compound represented by chemical formula 6 with an acrylic compound:

in chemical formula 6,
wherein X is a functional group bonded to a surface of a semiconductor nanoparticle and is —S(H), —P═O(OH) 2 or —COOH,
wherein L 1 is selected from the group consisting of: an arylene group of C 6 -C 30 ; a heterocyclic group of C 2 -C 30 including at least one heteroatom selected from the group consisting of O, N, S, Si, and P; an alkylene group of C 1 -C 20 ; an alkoxyl group of C 1 -C 20 ; an alkylthio group of C 1 -C 20 ; and a combination thereof,
wherein L 2 and L 3 are, independently of each other, selected from the group consisting of a single bond; an arylene group of C 6 -C 20 ; a heterocyclic group of C 2 -C 20 including at least one heteroatom selected from the group consisting of O, N, S, Si, and P; an aliphatic ring group of C 3 -C 20 , an alkylene group of C 1 -C 10 ; an alkoxyl group of C 1 -C 10 ; an alkylthio group of C 1 -C 10 ; and a combination thereof,
wherein in L 1 to L 3 , each of the arylene group, the heterocyclic group, the alkylene group, the alkoxyl group, and the alkylthio group may further be substituted with one or more substituents selected from the group consisting of deuterium; an aryl group of C 6 -C 10 ; a heterocyclic group of C 2 -C 10 ; an aliphatic ring group of C 3 -C 10 ; and an alkyl group of C 1 -C 10 .

6 . The method of claim 5 ,
wherein the acrylic compound is represented by chemical formula 7 to chemical formula 9 below:

in chemical formula 7,
R 1 is a hydrogen or methyl group,
wherein L 4 is selected from the group consisting of an alkylene group of C 1 -C 20 ; an alkoxyl group of C 1 -C 20 ; an alkylthio group of C 1 -C 20 ; and chemical formula 10 below,

in chemical formula 8,
wherein R 2 to R 4 are,

Assignees

• Duk San Neolux Co Ltd

Inventors

• Lee See Maek
• Park Yum Hee
• Bang Eun Byul
• Kim Do Eon
• Kim Tae Yun
• Shin Jong Moon
• Lee Chang Min
• Lee Hyung Dong
• Oh Hyun Ji

Classifications

• H10K50/81

  Anodes · CPC title

• G02B1/10

  Optical coatings produced by application to, or surface treatment of, optical elements (G02B1/08 takes precedence) · CPC title

• C08K2201/005

  Additives being defined by their particle size in general · CPC title

• C08K9/04

  Ingredients treated with organic substances {(treated with macromolecular compounds C08K9/08)} · CPC title

• H10K59/875

  Arrangements for extracting light from the devices · CPC title