Barrier coating compositions, composites prepared therefrom, and quantum dot polymer composite articles including the same

Patent metadata

Field	Value
Publication number	US-2016160060-A1
Application number	US-201514920189-A
Country	US
Kind code	A1
Filing date	Oct 22, 2015
Priority date	Dec 5, 2014
Publication date	Jun 9, 2016
Grant date	—

Abstract

A barrier coating composition including: a monomer combination including a first monomer having at least two thiol groups at its terminal end and a second monomer having at least two carbon-carbon unsaturated bond-containing groups at its terminal end; and a plurality of organo-modified clay particles dispersed in the monomer combination, wherein the organo-modified clay particles include a compound having a hydrocarbyl group linked to a heteroatom, and wherein the compound is a primary, secondary, or tertiary amine, a quaternary organoammonium salt, a primary, secondary, or tertiary phosphine, a quaternary organophosphonium salt, a thiol including an amine group, or a combination thereof.

First claim

What is claimed is:

1 . A barrier coating composition comprising:
a monomer combination comprising a first monomer comprising at least two thiol groups at its terminal end and a second monomer comprising at least two carbon-carbon unsaturated bond-containing groups at its terminal end; and a plurality of organo-modified clay particles dispersed in the monomer combination, wherein the organo-modified clay particles comprise a compound comprising a hydrocarbyl group linked to a heteroatom, and wherein the compound is a primary, secondary, or tertiary amine, a quaternary organoammonium salt, a primary, secondary, or tertiary phosphine, a quaternary organophosphonium salt, a thiol comprising an amine group, or a combination thereof.

2 . The barrier coating composition of claim 1 , wherein the amount of the clay particles is about 0.1 to about 20 parts by weight based on 100 parts by weight of the monomer combination.

3 . The barrier coating composition of claim 1 , wherein the clay particles comprise smectite clay, mica clay, vermiculite clay, montmorillonite clay, iron-containing montmorillonite clay, beidellite clay, saponite clay, hectorite clay, stibensite clay, nontronite clay, anionic clay, zirconium phosphate, kaolinite, atapulgite, illite, halloysite, diatomaceous earth, fuller's earth, calcined aluminum silicate, hydrated aluminum silicate, magnesium aluminum silicate, sodium silicate, magnesium silicate, or a combination thereof.

4 . The barrier coating composition of claim 1 , wherein the compound is a primary, secondary, or tertiary amine compound comprising at least one substituted or unsubstituted C6 to C20 hydrocarbyl group linked to a nitrogen atom, a quaternary organoammonium salt compound comprising at least one substituted or unsubstituted C6 to C20 hydrocarbyl group linked to a nitrogen atom, a primary, secondary, or tertiary phosphine compound comprising at least one substituted or unsubstituted C6 to C20 hydrocarbyl group linked to a phosphorus atom, an organophosphonium salt compound comprising at least one substituted or unsubstituted C6 to C20 hydrocarbyl group linked to a phosphorus atom, a C6 or greater thiol compound comprising an amine group(H 2 N-) or a combination thereof.

5 . The barrier coating composition of claim 1 , wherein the compound is n-hexyltrimethyl ammonium salt, a dioctadecyldimethylammonium salt, a methyltrioctylammonium salt, a hexyltriphenylphosphonium salt, a tributylmethylphosphonium salt, a triethylpentylphosphonium salt, 8-amino-1-octanethiol, a triethyloctylphosphonium salt, a tetraphenylphosphonium salt, or a combination thereof.

6 . The barrier coating composition of claim 1 , wherein the clay particle has an average of a longest diameter of about 50 nanometers to about 10 micrometers, and an average thickness of about 1 nanometer to about 10 nanometers.

7 . The barrier coating composition of claim 1 , wherein the composition has a transmittance of greater than or equal to about 85% for visible light.

8 . The barrier coating composition of claim 1 , wherein the first monomer is represented by Chemical Formula 1 and the second monomer is represented by Chemical Formula 2:

wherein, in Chemical Formula 1,
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 C7 to C30 arylalkyl group; a substituted or unsubstituted C3 to C30 heteroaryl group; a substituted or unsubstituted C4 to C30 heteroarylalkyl 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; hydroxy group; —NH 2 ; a substituted or unsubstituted C1 to C30 amine group (—NRR′, wherein R and R′ are independently hydrogen or a C1 to C30 linear or branched alkyl group); an isocyanate group; a halogen; —ROR′ (wherein R is a substituted or unsubstituted C1 to C20 alkylene group and R′ is hydrogen or a C1 to C20 linear or branched alkyl group); an acyl halide (—RC(═O)X, wherein R is a substituted or unsubstituted alkylene group and X is a halogen); —C(═O)OR′ (wherein R′ is hydrogen or a C1 to C20 linear or branched alkyl group); —CN; or —C(═O)ONRR′ (wherein R and R′ are independently hydrogen or a C1 to C20 linear or branched alkyl group),
L 1 is a carbon atom, a substituted or unsubstituted C1 to C30 alkylene group, a substituted or unsubstituted C6 to C30 cycloalkylene group, a substituted or unsubstituted C6 to C30 arylene group, or a substituted or unsubstituted C6 to C30 heteroarylene group, wherein a non-adjacent methylene (—CH 2 —) of the substituted C1 to C30 alkylene group is replaced by sulfonyl (—S(═O) 2 —), carbonyl (—C(═O)—), ether (—O—), sulfide (—S—), sulfoxide (—S(═O)—), ester (—C(═O)O—), amide (—C(═O)NR—) (wherein R is hydrogen or a C1 to C10 alkyl group), or a combination thereof,
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 (—CH 2 —) is replaced by sulfonyl (—S(═O) 2 —), carbonyl (—C(═O)—), ether (—O—), sulfide (—S—), sulfoxide (—S(═O)—), ester (—C(═O)O—), amide (—C(═O)NR—) (wherein R is hydrogen or a C1 to C10 linear or branched alkyl group), imine (—C(═NR)—) (wherein R is hydrogen or a C1 to C10 linear or branched alkyl group), or a combination thereof,
m is an integer of 1 or more,
k1 is an integer of 1 or more and k2 is an integer of 1 or more, and
the sum of m and k2 is an integer of 3 or more,
provided that m does not exceed the valence of Y 1 , and provided that the sum of k1 and k2 does not exceed the valence of L 1 ;

wherein, in Chemical Formula 2,
X is an aliphatic organic group having a carbon-carbon double bond or a carbon-carbon triple bond, an aromatic organic group having a carbon-carbon double bond or a carbon-carbon triple bond, or an alicyclic organic group having a carbon-carbon double bond or a carbon-carbon triple bond,
R 2 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 C7 to C30 arylalkyl group; a substituted or unsubstituted C3 to C30 heteroaryl group; a substituted or unsubstituted C3 to C30 heteroarylalkyl 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 C1 to C30 amine group (—NRR′, wherein R and R′ are independently hydrogen or a C1 to C30 linear or branched alkyl group); an isocyanate group; a halogen; —ROR′ (wherein R is a substituted or unsubstituted C1 to C20 alkylene group and R′ is hydrogen or a C1 to C20 linear or branched alkyl group); an acyl halide (—RC(═O)X, wherein R is a substituted or unsubstituted alkylene group and X is a halogen); —C(═O)OR′ (wherein R′ is hydrogen or a C1 to C20 linear or branched alkyl group); —CN; or —C(═O)ONRR′ (wherein R and R′ are independently hydrogen or a C1 to C20 linear or branched alkyl group),
L 2 is a carbon atom, a substituted or unsubstituted C1 to C30 alkylene group, a substituted or unsubstituted C6 to C30 cycloalkylene group, a substituted or unsubstituted C6 to C30 arylene group, or a substituted or unsubstituted C3 to C30 heteroarylene group,
Y 2 is a single

Assignees

• Samsung Electronics Co Ltd

Inventors

• Kikuchi Tomoyuki
• Jang Eunjoo
• Kang Hyun A
• Won Nayoun
• Cho Oul
• Koh Haeng Deog

Classifications

• C08J7/0427

  with only one layer of a composition containing a polymer binder (with more layers C08J7/042) · CPC title

• B32B2250/40

  Symmetrical or sandwich layers, e.g. ABA, ABCBA, ABCCBA · CPC title

• C08K9/04 Primary

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

• B32B2255/10

  on synthetic resin layer or on natural or synthetic rubber layer · CPC title

• B32B27/281

  comprising polyimides · CPC title