# US 10,768,342 B2 · Antireflection film comprising a low refractive index layer and a hard coating layer > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 10,768,342 B2 - Document ID: US10768342B2 - Status: Granted - Kind: B2 - Application number: 16/067,857 - Filed: 2017-03-03 - Published: 2019-01-10 - Granted: 2020-09-08 - Earliest claimed: 2016-03-04 - Assignees: LG Chem, Ltd. - Applicants: LG Chem, Ltd. - Inventors: Boo Kyung Kim; Jin Seok Byun; In Young Song; Yeong Rae Chang; Seok Hoon Jang - Web page: https://patentgrep.com/patent/US10768342B2 ## CPC - C08J 7/046: Forming abrasion-resistant coatings; Forming surface-hardening coatings - C08J 3/24: Crosslinking, e.g. vulcanising, of macromolecules (mechanical aspects B29C35/00; crosslinking agents C08K) - C08J 5/18: Manufacture of films or sheets - C08J 7/042: {with two or more layers, where at least one layer of a composition contains a polymer binder} - C08J 7/0427: {with only one layer of a composition containing a polymer binder (with more layers C08J7/042)} - C08J 7/044: Forming conductive coatings; Forming coatings having anti-static properties - C08L 33/08: Homopolymers or copolymers of acrylic acid esters - C09D 5/006: {Anti-reflective coatings} - C09D 7/61: inorganic - C09D 7/67: {Particle size smaller than 100 nm} - C09D 7/70: {characterised by shape, e.g. fibres, flakes or microspheres} - C09D 133/08: Homopolymers or copolymers of acrylic acid esters - G02B 1/115: Multilayers - G02B 1/14: Protective coatings, e.g. hard coatings - C08G 77/045: {containing less than 25 silicon atoms} - C08J 2301/12: Cellulose acetate - C08J 2433/08: Homopolymers or copolymers of acrylic acid esters - C08K 3/36: Silica - C08K 7/24: inorganic - C08J: WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H (working, e.g. shaping, of plastics B29) - C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06) - 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) - G02B: OPTICAL ELEMENTS, SYSTEMS OR APPARATUS - C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS - C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09) ## Abstract An antireflection film including a low reflective index layer and a hard coating layer, the low reflective index layer including: a binder resin including a crosslinked polymer of a photopolymerizable compound and polysilsesquioxane having at least one reactive functional group substituted thereon; and inorganic fine particles dispersed in the binder resin, wherein a ratio of internal haze (Hi) to total haze (Ha) is 97% or less and a variation in color coordinate value (b*) before and after alkaline treatment is 0.7 or less. ## Claims ### Claim 1 An antireflection film comprising: a low refractive index layer and a hard coating layer, wherein the low refractive index layer includes a binder resin containing a crosslinked polymer of a photopolymerizable compound and a polysilsesquioxane substituted with one or more reactive functional groups and inorganic fine particles dispersed in the binder resin; wherein a ratio of internal haze (Hi) to total haze (Ha) of the antireflection film is 97% or less, and a variation in color coordinate value V) of the antireflection film before and after alkali treatment is 0.7 or less. ### Claim 2 (depends on 1) The antireflection film of claim 1, wherein the variation in the color coordinate value (b*) of the antireflection film before and after the alkali treatment is determined by measuring the color coordinate values of the antireflection film before and after the alkali treatment in which the antireflection film is immersed for 1 second to 100 seconds in an aqueous alkaline solution diluted to 5 to 50% with distilled water. ### Claim 3 (depends on 1) The antireflection film of claim 1, wherein the low reflective index layer has polarization ellipticity measured by an ellipsometry method using a Cauchy model of the following General Formula 1 in which A is 1.20 to 1.65, B is 0 to 0.05, and C is 0 to 0.05: n ⁡ ( λ ) = A + B λ 2 + C λ 4 [ General ⁢ ⁢ Formula ⁢ ⁢ 1 ] wherein, in the above General Formula 1, n(λ) is a refractive index at a wavelength λ, λ is in a range of 300 nm to 1800 nm, and A, B, and C are Cauchy parameters. ### Claim 4 (depends on 1) The antireflection film of claim 1, wherein the hard coating layer has polarization ellipticity measured by an ellipsometry method using a Cauchy model of the following General Formula 1, in which A is 1.30 to 1.75, B is 0 to 0.05, and C is 0 to 0.005: n ⁡ ( λ ) = A + B λ 2 + C λ 4 [ General ⁢ ⁢ Formula ⁢ ⁢ 1 ] wherein, in the above General Formula 1, n(λ) is a refractive index at a wavelength λ, λ is in a range of 300 nm to 1800 nm, and A, B, and C are Cauchy parameters. ### Claim 5 (depends on 1) The antireflection film of claim 1, wherein the reflective index layer has a thickness of 1 nm to 200 nm, and the hard coating layer has a thickness of 0.1 μm to 100 μm. ### Claim 6 (depends on 1) The antireflection film of claim 1, wherein a weight ratio of a portion derived from the polysilsesquioxane substituted with one or more reactive functional groups to a portion derived from the photopolymerizable compound in the binder resin contained in the low reflective index layer is 0.005 to 0.50. ### Claim 7 (depends on 1) The antireflection film of claim 1, wherein the functional group substituted on the polysilsesquioxane includes at least one functional group selected from the group consisting of an alcohol, an amine, a carboxylic acid, an epoxide, an imide, a (meth)acrylate, a nitrile, a norbornene, an olefin, polyethylene glycol, a thiol, and a vinyl group. ### Claim 8 (depends on 1) The antireflection film of claim 1, wherein at least one silicon atom of the polysilsesquioxane is substituted with a reactive functional group, and remaining silicon atoms not substituted with the reactive functional groups are substituted with unreactive functional groups. ### Claim 9 (depends on 8) The antireflection film of claim 8, wherein the polysilsesquioxane substituted with one or more reactive functional groups includes a polyhedral oligomeric silsesquioxane having a cage structure, in which one or more functional groups are substituted. ### Claim 10 (depends on 1) The antireflection film of claim 1, wherein the photopolymerizable compound includes a monomer or an oligomer containing a (meth)acrylate or vinyl group. ### Claim 11 (depends on 1) The antireflection film of claim 1, wherein the binder resin further includes a crosslinked polymer of a photopolymerizable compound, a fluorine-based compound containing a photoreactive functional group, and polysilsesquioxane substituted with one or more reactive functional groups. ### Claim 12 (depends on 11) The antireflection film of claim 11, wherein the photoreactive functional group contained in the fluorine-based compound is at least one selected from the group consisting of a (meth)acrylate group, an epoxide group, a vinyl group, and a thiol group. ### Claim 13 (depends on 11) The antireflection film of claim 11, wherein the fluorine-based compound containing photoreactive functional group has a fluorine content of 1% by weight to 60% by weight. ### Claim 14 (depends on 11) The antireflection film of claim 11, wherein the fluorine-based compound containing the photoreactive functional group includes at least one selected from the group consisting of: i) an aliphatic compound or an aliphatic cyclic compound in which at least one photoreactive functional group is substituted and at least one fluorine is substituted on at least one carbon; ii) a heteroaliphatic compound or a heteroaliphatic cyclic compound in which at least one photoreactive functional group is substituted, at least one hydrogen is substituted with fluorine, and at least one carbon is substituted with silicon; iii) a polydialkylsiloxane-based polymer in which at least one photoreactive functional group is substituted and at least one fluorine is substituted on at least one silicon; and iv) a polyether compound in which at least one photoreactive functional group is substituted and at least one hydrogen is substituted with fluorine. ### Claim 15 (depends on 11) The antireflection film of claim 11, wherein the fluorine-based compound containing the photoreactive functional group has a weight-average molecular weight of 2000 to 200,000. ### Claim 16 (depends on 1) The antireflection film of claim 1, wherein the inorganic fine particles include at least one selected from the group consisting of solid inorganic nanoparticles having a diameter of 0.5 to 100 nm, and hollow inorganic nanoparticles having a diameter of 1 to 200 nm. ### Claim 17 (depends on 1) The antireflection film of claim 1, wherein the hard coating film includes a binder resin containing a photopolymerizable resin and a high molecular weight (co)polymer having a weight average molecular weight of 10,000 or more, and an organic or inorganic fine particle dispersed in the binder resin.