IP Library Granted Patent US 12,606,737
Granted Patent B2
US 12,606,737 · App. 17/784,713 · Granted Apr 21, 2026

(meth)acrylate monomers and semiconducting light emitting nanoparticles comprising composition

Inventors: Yuki Hirayama (Tokyo, JP); Tadashi Kishimoto (Tokyo, JP); Atsushi Sawada (Tokyo, JP); Tomohisa Goto (Tokyo, JP); Teruaki Suzuki (Tokyo, JP)
Assignee: SAMSUNG ELECTRONICS CO., LTD.
C09K11/025B82Y30/00
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Quick Facts
Patent No.
US 12,606,737
App. No.
17/784,713
Granted
Apr 21, 2026
Kind
B2
Abstract

The present invention relates to a composition comprising a (meth)acrylate monomer.

Claims (41)

1 . A composition comprising:

at least one (meth)acrylate monomer represented by chemical formula (I),

at least one (meth)acrylate monomer represented by chemical formula (II),

at least one semiconducting light emitting nanoparticle comprising a 1 st semiconducting nanoparticle, optionally with one or more shell layers covering at least a part of the 1 st semiconducting nanoparticle,

scattering particles, and

at least one polymer configured to enable the scattering particles to disperse in the composition,

wherein a mixing ratio of the (meth)acrylate monomer of chemical formula (I): the (meth)acrylate monomer of chemical formula (II): the polymer is 10:89:1 to 50:40:10;

wherein

X 1 is a non-substituted or substituted alkyl group, aryl group or an alkoxy group or an ester group;

X 2 is a non-substituted or substituted alkyl group, aryl group or an alkoxy group or an ester group;

R 1 is a hydrogen atom, Cl, Br, or F, methyl group, alkyl group, aryl group, alkoxy group, ester group, or a carboxylic acid group; and

R 2 is a hydrogen atom, Cl, Br, or F, methyl group, alkyl group, aryl group, alkoxy group, ester group, or a carboxylic acid group;

wherein

X 3 is a non-substituted or substituted alkyl group, aryl group or an alkoxy group; and

R 5 is a hydrogen atom, Cl, Br, or F, methyl group, alkyl group, aryl group, alkoxy group, ester group, or a carboxylic acid group.

2 . The composition of claim 1 , wherein:

X 3 is

wherein

1 is 0 or 1;

R 6 is a straight alkylene chain or alkoxylene chain having 1 to 25 carbon atoms, which may be substituted by one or more radicals R a , where one or more non-adjacent CH 2 groups may be replaced by R a C═CR a , C═C, Si(R a ) 2 , Ge(R a ) 2 , Sn(R a ) 2 , C═O, C═S, C═Se, C═NR a , P(═O)(R a ), SO, SO 2 , NR a , OS, or CONR a and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO 2 ;

R 7 is a straight alkylene chain or alkoxylene chain having 1 to 25 carbon atoms, which may be substituted by one or more radicals R a , where one or more non-adjacent CH 2 groups may be replaced by R a C═CR a , C═C, Si(R a ) 2 , Ge(R a ) 2 , Sn(R a ) 2 , C═O, C═S, C═Se, C═NR a , P(═O)(R a ), SO, SO 2 , NR a , OS, or CONR a and where one or more H atoms may be replaced by D, F, Cl, Br, I, CN or NO 2 ; and

R a is at each occurrence, identically or differently, H, D or an alkyl group having 1 to 20 carbon atoms, cyclic alkyl or alkoxy group having 3 to 40 carbon atoms, an aromatic ring system having 5 to 60 carbon ring atoms, or a hetero aromatic ring system having 5 to 60 carbon atoms, wherein H atoms may be replaced by D, F, Cl, Br, I; two or more adjacent substituents R a here may also form a mono- or polycyclic, aliphatic, aromatic or heteroaromatic ring system with one another.

3 . The composition of claim 1 , wherein at least a purified (meth)acrylate monomer represented by chemical formula (I) or (II) is used in the composition.

4 . The composition of claim 1 , wherein the boiling point (B.P.) of said (meth)acrylate monomer of chemical formula (I) and/or chemical formula (II) is 250° C. or more.

5 . The composition of claim 1 , wherein the viscosity of the composition is 35 cP or less at room temperature.

6 . The composition of claim 1 , which further comprises one or more members selected from:

another (meth)acylate monomer, optically transparent polymers, anti-oxidants, radical quenchers, photoinitiators, and surfactants.

7 . The composition of claim 1 ,

wherein the polymer comprises at least a phosphine group, phosphine oxide group, phosphate group, phosphonate group, thiol group, tertiary amine, carboxyl group, hetero cyclic group, silane group, sulfonic acid, hydroxyl group, phosphonic acid, or a combination of thereof.

8 . The composition of claim 1 , wherein the composition has an EQE value of 23% or more and less than 95%.

9 . The composition according to claim 1 , wherein the composition comprises a solvent in an amount of 10 wt % or less based on the total amount of the composition.

10 . The composition according to claim 1 , wherein the mixing ratio of the (meth)acrylate monomer of chemical formula (I): the (meth)acrylate monomer of chemical formula (II): the polymer is 15:82:3 to 30:60:10.

11 . The composition according to claim 1 , wherein the total amount of the semiconducting light emitting nanoparticles is in the range from 0.1 wt % to 90 wt % based on the total amount of the composition.

12 . The composition of claim 1 , wherein the (meth)acrylate monomer represented by chemical formula (I) is selected from the group consisting of 1,9-nonanediol diacrylate, 1,6-hexanediol dimethacrylate, 1,6-hexanediol diacrylate, neopentyl glycol diacrylate, and dipropylene glycol diacrylate.

13 . The composition of claim 12 , wherein the (meth)acrylate monomer represented by chemical formula (II) is selected from the group consisting of lauryl acrylate and lauryl methacrylate.

14 . The composition of claim 13 , wherein the (meth)acrylate monomer represented by chemical formula (I) is 1,6-hexanediol dimethacrylate and the (meth)acrylate monomer represented by chemical formula (II) is lauryl acrylate.

15 . An electronic device, optical device, sensing device or a biomedical device, comprising the composition according to claim 1 .

16 . An optical element made from the composition according to claim 1 .

17 . An optical medium comprising the composition of claim 1 or an optical element made form said composition.

18 . An optical device comprising at least the composition of claim 1 or an optical element made from said composition.

19 . A method for fabricating an electronic device, optical device or biomedical device, comprising by ink jetting the composition of claim 1 onto a substrate.

Assignments (4)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 7, 2025
From: MERCK PATENT GMBH
To: SAMSUNG ELECTRONICS CO., LTD.
Reel/Frame 071620/0871 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 13, 2024
From: HIRAYAMA, YUKI; KISHIMOTO, TADASHI; SAWADA, ATSUSHI; GOTO, TOMOHISA; SUZUKI, TERUAKI
To: MERCK PERFORMANCE MATERIALS LTD.
Reel/Frame 066449/0581 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 13, 2024
From: MERCK PERFORMANCE MATERIALS LTD.
To: MERCK PERFORMANCE MATERIALS GERMANY GMBH
Reel/Frame 066449/0754 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 13, 2024
From: MERCK PERFORMANCE MATERIALS GERMANY GMBH
To: MERCK PATENT GMBH
Reel/Frame 066449/0863 →
Priority Claims (3)
EP 19215591 · Dec 12, 2019 · regional
EP 20164027 · Mar 18, 2020 · regional
EP 20179155 · Jun 10, 2020 · regional
Continuity (1)
Related Publication 20230052397A1 · Feb 16, 2023
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