Optical medium composition with nanosized light emitting material and (meth)acrylic polymer

Patent metadata

Field	Value
Publication number	US-11965049-B2
Application number	US-201917265330-A
Country	US
Kind code	B2
Filing date	Jul 31, 2019
Priority date	Aug 3, 2018
Publication date	Apr 23, 2024
Grant date	Apr 23, 2024

Abstract

Photosensitive compositions containing nanosized light emitting materials and (meth)acrylic polymer are suitable for use in a variety of optical applications, for example the preparation of quantum material doped photoresist films, especially for optical devices. Optical films can be prepared be by: a) providing the photosensitive composition onto a substrate, and b) polymerizing the photosensitive composition by exposing the photosensitive composition to radiation.

First claim

The invention claimed is:

1. A composition comprising at least one nanosized light emitting material and a (meth)acrylic polymer, wherein the (meth)acrylic polymer comprises at least one (meth)acrylic structural unit represented by the following chemical formula (1):

in which:
R 1 denotes, identically or differently at each occurrence, hydrogen, a straight-chain alkyl group having 1 to 20 C atoms, a branched or cyclic alkyl group having 3 to 20 C atoms, an alkenyl or alkynyl group having 2 to 20 C atoms, an aryl or heteroaryl group having 5 to 24 C atoms, where one or more non-adjacent methylene structural units (—CH 2 —) in said alkyl, alkenyl, alkynyl, aryl or heteroaryl groups may in each case be replaced by a sulfonyl group, a carbonyl group, an ether group, a sulfide group, a sulfoxide group, an ester group, an amide group or an imine group,
and wherein said alkyl, alkenyl, alkynyl, aryl or heteroaryl groups one or more H atoms may be replaced by F, Cl, Br, I, CN or OH, a carboxyl group (—COOH), a straight-chain alkyl or alkoxy group having 2 to 20 C atoms, a branched alkyl or alkoxy group having 3 to 20 C atoms, or an alkenyl or alkynyl group having 2 to 20 C atoms;

R 2 , R 2 ′ denote, identically or differently at each occurrence, hydrogen, a hydroxyl group (—OH) a carboxyl group (—COOH), a straight-chain alkyl group having 1 to 20 C atoms, a branched or cyclic alkyl group having 3 to 20 C atoms, an alkenyl or alkynyl group having 2 to 20 C atoms, an aryl or heteroaryl group having 5 to 24 C atoms, where one or more non-adjacent methylene structural units (—CH 2 —) in said alkyl, alkenyl, alkynyl, aryl or heteroaryl groups may in each case be replaced by a sulfonyl group, a carbonyl group, an ether group, a sulfide group, a sulfoxide group, an ester group, an amide group or an imine group,
and wherein said alkyl, alkenyl, alkynyl, aryl or heteroaryl groups one or more H atoms may be replaced by F, Cl, Br, I, CN or OH, a carboxyl group (—COOH), a straight-chain alkyl or alkoxy group having 2 to 20 C atoms, a branched alkyl or alkoxy group having 3 to 20 C atoms, or an alkenyl or alkynyl group having 2 to 20 C atoms, with the proviso that both radicals R 2 and R 2 ′ bonded to the same C atom can denote carboxyl groups at the same time;

R 3 denotes, identically or differently at each occurrence, hydrogen, a straight-chain alkyl group having 1 to 20 C atoms, a branched or cyclic alkyl group having 3 to 20 C atoms, an alkenyl or alkynyl group having 2 to 20 C atoms, an aryl or heteroaryl group having 5 to 24 C atoms, where one or more non-adjacent methylene structural units (—CH 2 —) in said alkyl, alkenyl, alkynyl, aryl or heteroaryl groups may in each case be replaced by a sulfonyl group, a carbonyl group, an ether group, a sulfide group, a sulfoxide group, an ester group, an amide group or an imine group,
and wherein said alkyl, alkenyl, alkynyl, aryl or heteroaryl groups one or more H atoms may be replaced by F, Cl, Br, I, CN or OH, a carboxyl group (—COOH), a straight-chain alkyl or alkoxy group having 2 to 20 C atoms, a branched alkyl or alkoxy group having 3 to 20 C atoms, or an alkenyl or alkynyl group having 2 to 20 C atoms;

R 4 denotes, identically or differently at each occurrence, a straight-chain alkylene group having 1 to 20 C atoms, a branched alkylene group having 2 to 20 C atoms, an alkenylene or alkynylene group having 2 to 20 C atoms, or an arylene or heteroarylene group having 6 to 24 C atoms, where one or more methylene structural units (—CH 2 —) in said alkylene, alkenylene, alkynylene, arylene or heteroarylene groups may in each case be 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, a group CHR′ or a group CR′R″;
R′, R″ denote, identically or differently at each occurrence, a hydroxyl group, a straight-chain alkyl group having 1 to 20 C atoms, a branched or cyclic alkyl group having 3 to 20 C atoms, an alkenyl or alkynyl group having 2 to 20 C atoms, an aryl or heteroaryl group having 5 to 24 C atoms, where one or more non-adjacent methylene structural units (—CH 2 —) in said alkyl, alkenyl, alkynyl, aryl or heteroaryl groups may in each case be replaced by a sulfonyl group, a carbonyl group, an ether group, a sulfide group, a sulfoxide group, an ester group, an amide group or an imine group, and wherein said alkyl, alkenyl, alkynyl, aryl or heteroaryl groups one or more H atoms may be replaced by F, Cl, Br, I, CN or OH, a straight-chain alkyl or alkoxy group having 2 to 20 C atoms, a branched alkyl or alkoxy group having 3 to 20 C atoms, or an alkenyl or alkynyl group having 2 to 20 C atoms.

2. The composition according to claim 1 , wherein
R 1 denotes hydrogen, a straight-chain alkyl group having 1 to 10 C atoms, or a branched alkyl group having 3 to 10 C atoms; and/or
R 2 ′ denotes hydrogen or a methyl group and R 2 denotes hydrogen, a carboxyl group, a straight-chain alkyl group having 1 to 8 C atoms, wherein one or more H atoms may be replaced by F, Cl, OH, or a carboxyl group (—COOH); and/or
R 3 denotes hydrogen, a straight-chain alkyl group having 1 to 10 C atoms, or a branched alkyl group having 3 to 10 C atoms; and/or
R 4 denotes a straight-chain alkylene group having 1 to 10 C atoms, a branched alkylene group having 2 to 10 C atoms, an alkenylene group having 2 to 10 C atoms, or an arylene group having 6 to 10 C atoms, where one or more non-adjacent methylene structural units (—CH 2 —) in said alkylene alkenylene or arylene groups may be 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, a group CHR′ or a group CR′R″.

3. The composition according to claim 1 , wherein the (meth)acrylic polymer further comprises one or more (meth)acrylic structural units selected from the following chemical formulae (2), (3) and (4):

in which
radicals R 1 , R 2 and R 2 ′ are at each occurrence, identically or differently, as defined in claim 1 ;
R 5 denotes, identically or differently at each occurrence, a straight-chain alkylene group having 1 to 20 C atoms, a branched alkylene group having 2 to 20 C atoms, an alkenylene or alkynylene group having 2 to 20 C atoms, or an arylene or heteroarylene group having 6 to 24 C atoms, where one or more methylene structural units (—CH 2 —) in said alkylene, alkenylene, alkynylene, arylene or heteroarylene groups may in each case be 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, a group CHR′ or a group CR′R″, wherein radicals R′ and R″ are as defined above; and
R 6 denotes, identically or differently at each occurrence, a straight-chain alkyl group having 1 to 20 C atoms, a branched alkyl group having 3 to 20 C atoms, or a cyclic alkyl group having 3 to 20 C atoms.

4. The composition according to claim 3 , wherein R 5 denotes a straight-chain alkylene group having 1 to 10 C atoms, a branched alkylene group having 2 to 10 C atoms, or an alkenylene group having 2 to 10 C atoms, where one or more non-adjacent methylene structural units (—CH 2 —) in said alkylene or alkenylene groups may be 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, a group CHR′ or a group CR′R″, wherein radicals R′ and R″ are as defined above, and/or R 6 denotes a straight-chain alkyl group having 1 to 10 C atoms, a branched alkyl group having 3 to 10 C atoms, or a cyclic alkyl group havin

Assignees

• Merck Patent Gmbh

Inventors

• Kishimoto Tadashi
• Arai Yuko
• Suzuki Masayoshi
• Yokoyama Daishi
• Taniguchi Katsuto

Classifications

• C08F290/126 Primary

  Polymers of unsaturated carboxylic acids or derivatives thereof · CPC title

• C09D4/06

  {Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond} in combination with a macromolecular compound other than an unsaturated polymer of groups C09D159/00 - C09D187/00 · CPC title

• C09D5/22

  Luminous paints {(luminescent compositions C09K11/00)} · CPC title

• C09D7/45

  Anti-settling agents · CPC title

• C09D7/61

  inorganic · CPC title