# US 11,993,725 B2 · Barrier films and quantum dot polymer composite articles including the same

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- Number: US 11,993,725 B2
- Document ID: US11993725B2
- Status: Granted
- Kind: B2
- Application number: 16/812,447
- Filed: 2020-03-09
- Published: 2020-07-02
- Granted: 2024-05-28
- Earliest claimed: 2015-03-11
- Assignees: Samsung Electronics Co., Ltd.
- Applicants: Samsung Electronics Co., Ltd.
- Inventors: Tomoyuki Kikuchi; EunJoo Jang; Hyun A Kang; Nayoun Won; Oul Cho
- Web page: https://patentgrep.com/patent/US11993725B2

## CPC

- C09D 181/00: 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
- B32B 1/08: Tubular products
- B32B 7/04: Interconnection of layers
- B32B 15/082: comprising vinyl resins; comprising acrylic resins
- B32B 15/092: comprising epoxy resins
- B32B 15/095: comprising polyurethanes
- B32B 15/20: comprising aluminium or copper {(B32B15/016 and B32B15/017 take precedence)}
- B32B 17/00: Layered products essentially comprising sheet glass, or glass, slag, or like fibres
- B32B 27/00: Layered products comprising {a layer of} synthetic resin {(fibrous or filamentary layer made of a synthetic resin B32B5/02; particulate layer made of a synthetic resin B32B5/16; foamed layer made of a synthetic resin B32B5/18)}
- B32B 27/08: of synthetic resin
- B32B 27/18: characterised by the use of special additives
- B32B 27/20: using fillers, pigments, thixotroping agents
- B32B 27/281: {comprising polyimides}
- B32B 27/285: {comprising polyethers}
- B32B 27/286: {comprising polysulphones; polysulfides}
- B32B 27/288: {comprising polyketones}
- B32B 27/30: comprising vinyl {(co)polymers; comprising acrylic (co)polymers}
- B32B 27/302: {comprising aromatic vinyl (co)polymers, e.g. styrenic (co)polymers}
- B32B 27/304: {comprising vinyl halide (co)polymers, e.g. PVC, PVDC, PVF, PVDF}
- B32B 27/308: {comprising acrylic (co)polymers}
- B32B 27/32: comprising polyolefins {(comprising vinyl (co)polymers or acrylic (co)polymers B32B27/30)}
- B32B 27/325: {comprising polycycloolefins}
- B32B 27/34: comprising polyamides
- B32B 27/36: comprising polyesters
- B32B 27/365: {comprising polycarbonates}
- B32B 27/38: comprising epoxy resins
- C09D 183/16: in which all the silicon atoms are connected by linkages other than oxygen atoms
- C09K 11/02: Use of particular materials as binders, particle coatings or suspension media therefor
- C09K 11/623: {with zinc or cadmium}
- B32B 2250/03: 3 layers
- B32B 2255/10: on synthetic resin layer or on natural or synthetic rubber layer
- B32B 2255/20: Inorganic coating
- B32B 2255/26: Polymeric coating
- B32B 2255/28: Multiple coating on one surface
- B32B 2264/10: Inorganic particles
- B32B 2270/00: Resin or rubber layer containing a blend of at least two different polymers
- B32B 2307/412: Transparent
- B32B 2307/422: Luminescent, fluorescent, phosphorescent
- B32B 2307/7242: Non-permeable
- B32B 2307/7244: Oxygen barrier
- B32B 2307/7265: Non-permeable
- B32B 2307/728: Hydrophilic
- B32B 2307/732: Dimensional properties
- B32B 2457/12: Photovoltaic modules
- B32B 2457/202: LCD, i.e. liquid crystal displays
- C08G 77/62: Nitrogen atoms
- C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D)
- B32B: LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS

## 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 R1 and R2 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.

## Claims

### Claim 1

A quantum dot-polymer composite article comprising:
a quantum dot-polymer composite comprising a polymer host matrix and a plurality of quantum dots dispersed in the polymer host matrix; and
a barrier film disposed on at least a portion of surface of the quantum dot-polymer composite,
wherein the barrier film comprises:
a substrate;
a first layer disposed on the substrate and comprising an oxidation product of polysilazane, wherein the polysilazane consists of a repeating unit represented by Chemical Formula 1, wherein each occurrence of the repeating unit represented by Chemical Formula 1 may be the same or different,
wherein R1 and R2 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
a second layer disposed directly on the first layer and comprising a thiol-ene polymer, the thiol-ene polymer comprising a polymerization product of a first monomer having at least two thiol groups, wherein at least one thiol group is present at one terminal end and at least one thiol group is present at another terminal end, and a second monomer represented by 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,
R2 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 Cl to C10 alkoxy group; a hydroxy group; NH2; a substituted or unsubstituted C1 to C30 amine group (-NRR′, wherein R and R′ are independently hydrogen or a Cl 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 Cl 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 Cl to C20 linear or branched alkyl group); —CN; or —C(═O)ONRR′ (wherein R and R′ are independently hydrogen or a Cl to C20 linear or branched alkyl group),
L2 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,
Y2 is a single bond; a substituted or unsubstituted C1 to C30 alkylene group; a substituted or unsubstituted C2 to C30 alkenylene group; or a Cl to C30 alkylene group or a C2 to C30 alkenylene group wherein at least one methylene (-CH2-) 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 Cl to C10 linear or branched alkyl group), imine (—NR—) (wherein R is hydrogen or a Cl 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 Y2 is not a single bond, n does not exceed the valence of Y2, and
provided that the sum of k3 and k4 does not exceed the valence of L2 and
wherein a surface of the second layer contacts at least a portion of the surface of the quantum dot-polymer composite.

### Claim 2 (depends on 1)

The quantum dot-polymer composite article of claim 1, wherein the polymer host matrix comprises a thiol-ene polymer, a cross-linked or non-cross-linked poly(meth)acrylate, a melamine(meth)acrylate polymer, an epoxy polymer, an epoxy(meth)acrylate polymer, a silicone polymer, a silicon(meth)acrylate polymer, a polyurethane(meth)acrylate, a vinyl polymer, or a combination thereof.

### Claim 3 (depends on 1)

The quantum dot-polymer composite article of claim 1, wherein the quantum dot-polymer composite has a sheet shape, a bar shape, a pipe shape, or a tube shape.

### Claim 4 (depends on 1)

The quantum dot-polymer composite article of claim 1, wherein the oxidation product of the polysilazane consists of a silicon oxide, a silicon oxynitride, a polysiloxane, a polysiloxazane, or a combination thereof.

### Claim 5 (depends on 1)

The quantum dot-polymer composite article 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.

### Claim 6 (depends on 1)

An electronic device comprising the quantum dot-polymer composite article of claim 1.

### Claim 7 (depends on 6)

The electronic device of claim 6, wherein the electronic device is a display, a light emitting device, a memory device, a laser device, or a solar cell.

### Claim 8 (depends on 7)

The electronic device of claim 7, wherein the light emitting device comprises a light source and the quantum dot-polymer composite article positioned on the light source.