Barrier films and quantum dot polymer composite articles including the same

Patent metadata

Field	Value
Publication number	US-2016264820-A1
Application number	US-201615042983-A
Country	US
Kind code	A1
Filing date	Feb 12, 2016
Priority date	Mar 11, 2015
Publication date	Sep 15, 2016
Grant date	—

Abstract

A barrier film comprising: a substrate; a first layer disposed on the substrate and comprising an oxidation product of polysilazane; and a second layer disposed directly on the first layer and comprising a thiol-ene polymer, wherein the polysilazane comprises a repeating unit represented by Chemical Formula 1,

wherein R 1 and R 2 are each independently hydrogen, an aliphatic hydrocarbon group, an alicyclic hydrocarbon group, an alkylsilyl group, an alkylamino group, an alkoxy group, or an aromatic hydrocarbon group, and wherein the thiol-ene polymer is a polymerization product of 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.

First claim

What is claimed is:

1 . A barrier film comprising:
a substrate; a first layer disposed on the substrate and comprising an oxidation product of polysilazane; and a second layer disposed directly on the first layer and comprising a thiol-ene polymer, and wherein the polysilazane comprises a repeating unit represented by Chemical Formula 1,

wherein R 1 and R 2 are each independently hydrogen, an aliphatic hydrocarbon group, an alicyclic hydrocarbon group, an alkylsilyl group, an alkylamino group, an alkoxy group, or an aromatic hydrocarbon group; and
wherein the thiol-ene polymer is a polymerization product of a monomer combination comprising 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.

2 . The barrier film of claim 1 , wherein the substrate comprises a polymer, a metal oxide, a metal, or a combination thereof.

3 . The barrier film of claim 1 , wherein the oxidation product of the polysilazane comprises a silicon oxide, a silicon oxynitride, a polysiloxane, a polysiloxazane, or a combination thereof.

4 . The barrier film of claim 1 , wherein in the oxidation product of the polysilazane, a ratio of a Si—O moiety to a Si—H moiety determined from FTIR analysis data is greater than or equal to about 0.1 and less than or equal to about 15.

5 . The barrier film of claim 4 , wherein in the oxidation product of the polysilazane, a ratio of a Si—O moiety to a Si—H moiety determined from FTIR analysis data is greater than or equal to about 2 and less than or equal to about 13.

6 . The barrier film of claim 1 , wherein the oxidation product of the polysilazane is obtained by treating the polysilazane in contact with oxygen or in contact with oxygen and moisture at a temperature of about 20° C. to about 200° C.

7 . The barrier film of claim 6 , wherein the polysilazane is treated in contact with a catalyst selected from an amine compound, a platinum compound, a palladium compound, a rhodium compound, and a combination thereof.

8 . The barrier film of claim 6 , wherein the treating comprises UV irradiation, heating, or a combination thereof.

9 . The barrier film of claim 1 , wherein the first monomer is represented by Chemical Formula 2 and the second monomer is represented by Chemical Formula 3:
[R 1  k1 L 1 Y 1 —(SH) m ] k2   Chemical Formula 2
wherein, in Chemical Formula 2, R 1 is selected from 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 C3 to C30 heteroaryl 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 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 at least one methylene (—CH 2 —) group of the substituted C1 to C30 alkylene group is optionally replaced by sulfonyl (—SO 2 —), carbonyl (—CO—), ether (—O—), sulfide (—S—), sulfoxide (—SO—), 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 —) 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 linear or branched alkyl group), imine (—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 when Y 1 is not a single bond, 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 ;
[R 21  k3 L 2 Y 2 —(X) n ] k4   Chemical Formula 3

wherein, in Chemical Formula 3, X is an aliphatic organic group comprising a carbon-carbon double bond or a carbon-carbon triple bond, an aromatic organic group comprising a carbon-carbon double bond or a carbon-carbon triple bond, or an alicyclic organic group comprising a carbon-carbon double bond or a carbon-carbon triple bond, R 2 is selected from 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 C3 to C30 heteroaryl 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 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 —) 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 linear or branched alkyl group), imine (—NR—) (wherein R is hydrogen or a C1 to C10 linear or branched alkyl group), or a combination thereof, n is an integer of 1 or more, k3 is an integer of 0 or more, k4 is an integer of 1 or more, and the sum of n and k4 is an integer of 3 or more, provided that when Y 2 is not a single bond, n does not exceed the valence of Y 2 , and provided that the sum of k3 and k4 does not exceed the valence of L 2 .

10 . The barrier film of claim 1 , wherein the second layer further comprises a plurality of clay particles dispersed in the thi

Assignees

• Samsung Electronics Co Ltd

Inventors

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

Classifications

• C09D181/00 Primary

  Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur, with or without nitrogen, oxygen, or carbon only; Coating compositions based on polysulfones; Coating compositions based on derivatives of such polymers · CPC title

• C09K11/623

  with zinc or cadmium · CPC title

• C09D183/04 Primary

  Polysiloxanes · CPC title

• B32B27/288

  comprising polyketones · CPC title

• B32B2307/7265

  Non-permeable · CPC title