WO2023106141A1 - 低屈折率層形成用塗液、低屈折率層、および反射防止フィルム - Google Patents

低屈折率層形成用塗液、低屈折率層、および反射防止フィルム Download PDF

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WO2023106141A1
WO2023106141A1 PCT/JP2022/043628 JP2022043628W WO2023106141A1 WO 2023106141 A1 WO2023106141 A1 WO 2023106141A1 JP 2022043628 W JP2022043628 W JP 2022043628W WO 2023106141 A1 WO2023106141 A1 WO 2023106141A1
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refractive index
low refractive
index layer
coating liquid
forming
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PCT/JP2022/043628
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English (en)
French (fr)
Japanese (ja)
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健弘 鈴木
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東洋インキＳｃホールディングス株式会社
トーヨーケム株式会社
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Application filed by 東洋インキＳｃホールディングス株式会社, トーヨーケム株式会社 filed Critical 東洋インキＳｃホールディングス株式会社
Priority to CN202280061285.2A priority Critical patent/CN117916634A/zh
Publication of WO2023106141A1 publication Critical patent/WO2023106141A1/ja

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • 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
    • C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • 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
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/60—Additives non-macromolecular
    • C09D7/61—Additives non-macromolecular inorganic
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • 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
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/65—Additives macromolecular
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K3/00—Materials not provided for elsewhere
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/10—Optical coatings produced by application to, or surface treatment of, optical elements
    • G02B1/11—Anti-reflection coatings
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/10—Optical coatings produced by application to, or surface treatment of, optical elements
    • G02B1/11—Anti-reflection coatings
    • G02B1/111—Anti-reflection coatings using layers comprising organic materials
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/10—Optical coatings produced by application to, or surface treatment of, optical elements
    • G02B1/14—Protective coatings, e.g. hard coatings
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/10—Optical coatings produced by application to, or surface treatment of, optical elements
    • G02B1/16—Optical coatings produced by application to, or surface treatment of, optical elements having an anti-static effect, e.g. electrically conducting coatings

Definitions

  • the present invention relates to a coating liquid for forming a low refractive index layer, a low refractive index layer, and an antireflection film.
  • An antireflection film, an antiglare film, or the like having a low refractive index layer is applied to the image display surface of an image display device such as a liquid crystal display, an organic electroluminescence (EL) display, a touch panel, etc., in order to suppress reflection of external light. is provided.
  • an image display device such as a liquid crystal display, an organic electroluminescence (EL) display, a touch panel, etc.
  • the antireflection film consists of light reflected on the surface of the low refractive index layer and light reflected on the interface between the low refractive index layer and a layer adjacent to the low refractive index layer (for example, a hard coat layer or a high refractive index layer). , the reflectance is reduced by the interference effect of light.
  • Antireflection films are often laminated on the outermost layer of displays, and are required to be scratch and abrasion resistant.
  • antireflection films are used in image display devices such as various displays, antifouling properties on the surface, wiping off of dirt, etc. are required.
  • wiping off dirt it is often wiped off with gauze, cloth, or the like impregnated with alcohol such as ethanol, and abrasion resistance against gauze or the like is required.
  • surface smoothness is used to form a low refractive index layer that has high scratch resistance to both rigid fibers such as steel wool and flexible fibers such as gauze.
  • the purpose is to achieve both the durability and the inorganic oxide fine particles.
  • Another object of the present invention is to achieve the transparency, low reflectance, and antifouling properties required for antireflection films.
  • the problem to be solved by the present invention is to provide a coating liquid for forming a low refractive index layer for an antireflection film which is excellent in scratch resistance against various abrasives and also excellent in antifouling properties. .
  • the first invention is a hollow particle (A) having a particle diameter (D50) of 150 nm or less and an inorganic oxide having a particle diameter (D50) of 10 to 90 nm and a particle diameter (D99) of 150 to 300 nm.
  • Fine particles (B) (excluding hollow particles (A)) and polyfunctional (meth)acrylate (C), wherein the inorganic oxide fine particles (B) are added to 100 parts by mass of the hollow particles (A) 0.5 to 15 parts by mass of a coating liquid for forming a low refractive index layer.
  • a second invention relates to the coating liquid for forming a low refractive index layer, which further contains a fluorine-containing (meth)acrylate (D).
  • the third invention is the content of the fluorine-containing (meth)acrylate (D) is 0.5 to 10% by mass in 100% by mass of the non-volatile matter of the low refractive index layer-forming coating liquid. It relates to a coating liquid for forming a low refractive index layer.
  • a fourth invention relates to the coating liquid for forming a low refractive index layer, wherein the polyfunctional (meth)acrylate (C) contains a polyfunctional (meth)acrylate having a silicone chain.
  • a fifth invention relates to a low refractive index layer formed from the coating liquid for forming a low refractive index layer.
  • the sixth invention is the above-mentioned low-temperature adhesive, wherein the water contact angle on the surface is 90 ° or more, and the change in haze is 0.1 or less when 10 reciprocations are performed with a 200 g / cm 2 load according to a steel wool test. Refractive index layer.
  • a seventh invention relates to an antireflection film including a transparent substrate and the low refractive index layer provided on the transparent substrate.
  • the eighth invention relates to the antireflection film having a luminous reflectance of 1.5% or less.
  • a coating liquid for forming a low refractive index layer for an antireflection film that has excellent scratch resistance against various abrasives and excellent antifouling properties.
  • FIG. 1 is a schematic cross-sectional view showing one form of the antireflection film.
  • FIG. 2 is a schematic cross-sectional view showing another form of the antireflection film.
  • the low refractive index layer preferably has a refractive index of 1.45 or less.
  • the refractive indices of the low refractive index layer, hard coat layer, and optical adjustment layer are the refractive indices at a wavelength of 594 nm.
  • the particle diameter (D50) and the particle diameter (D99) refer to particles whose cumulative values are 50% by volume and 99% by volume, respectively, in the volume-based particle size distribution obtained from the particle size distribution measurement value. represents the diameter.
  • the particle size (D50) and the particle size (D99) can each be determined by a Nanotrack particle size distribution analyzer using a dynamic light scattering method.
  • the luminous reflectance is determined according to JIS Z8722. Unless otherwise noted, the various components appearing in this specification may be used singly or in admixture of two or more.
  • the coating liquid for forming a low refractive index layer includes hollow particles (A) having a particle size (D50) of 150 nm or less, and particles having a particle size (D50) of 10 to 90 nm and a particle size (D99) of 150 to 300 nm.
  • Hollow particles (A) are hollow particles having a particle diameter (D50) of 150 nm or less.
  • the hollow particles (A) may be inorganic hollow particles or organic hollow particles.
  • the hollow particles may be hollow silica particles, hollow polymer particles, etc. having voids inside.
  • Polymers constituting the hollow polymer particles include crosslinked acrylic polymers, crosslinked styrene polymers, vinyl polymers and the like.
  • a crosslinked acrylic polymer is preferable from the viewpoint of achieving a low refractive index.
  • Commercially available hollow silica particles include "Sururia 4320" (particle diameter (D50): 60 nm, Nikki Shokubai Kasei Co., Ltd.).
  • the particle diameter (D50) is 150 nm or less, preferably 100 nm or less, more preferably 80 nm or less from the viewpoint of haze and gauze resistance.
  • the lower limit is not particularly limited, it is preferably 40 nm or more, more preferably 60 nm or more, in order to improve the refractive index.
  • the particle diameter (D50) of the hollow particles (A) may be 40-150 nm, 40-100 nm, or 60-80 nm.
  • the particle diameter (D50) of the hollow particles can be determined by a Nanotrack particle size distribution measuring device using a dynamic light scattering method.
  • Nanotrac particle size distribution analyzer examples include “Nanotrac UPA” manufactured by Nikkiso Co., Ltd., and the like. Specifically, measurement can be performed using a sample obtained by adding hollow particles (A) to a diluted solution so that the loading index value in the analysis software "Microtrac" becomes 1.0.
  • the diluent preferably uses the same dispersion solvent as the main component of the dispersion solvent for the hollow particles (A), and examples thereof include methyl isobutyl ketone, methyl ethyl ketone, and propylene glycol monomethyl ether.
  • the content of the hollow particles is preferably 10 to 80% by mass in 100% by mass of the non-volatile matter of the coating liquid for forming the low refractive index layer in order to reduce the refractive index. More preferably 15 to 70% by mass.
  • the weight of the non-volatile matter of the low refractive index layer-forming coating liquid is the weight of the components remaining after drying the low refractive index layer-forming coating liquid by heating at 120° C. for 20 minutes. The same shall apply hereinafter unless otherwise specified.
  • the inorganic oxide fine particles (B) are inorganic oxide fine particles having a particle diameter (D50) of 10 to 90 nm and a particle diameter (D99) of 150 to 300 nm.
  • the particle diameter (D99) is preferably 180-280 nm, more preferably 200-250 nm.
  • the particle diameter (D50) of the inorganic oxide fine particles (B) is preferably 50 to 90 nm, more preferably 65 to 90 nm.
  • the particle size of the inorganic oxide fine particles can be determined by a Microtrac particle size distribution measuring device using a dynamic light scattering method or the like. Examples of the Microtrac particle size distribution analyzer include "Nanotrac UPA" manufactured by Nikkiso Co., Ltd., and the like. Specifically, an inorganic oxide fine particle dispersion obtained by dispersing the inorganic oxide fine particles (B) in a solvent can be added to a diluted solution so that the loading index value becomes 1.0, and the measurement can be performed.
  • the diluent it is preferable to use the same dispersing solvent as the main component of the dispersing solvent for the inorganic oxide fine particles, and examples thereof include methyl isobutyl ketone, methyl ethyl ketone, and propylene glycol monomethyl ether.
  • the inorganic oxide fine particles (B) to be used are not particularly limited, aluminum oxide (Al 2 O 3 ) fine particles, silica (SiO 2 ) fine particles, or the like can be mentioned from the viewpoint of transparency and scratch resistance.
  • the inorganic oxide fine particles (B) may be used singly or in combination of two or more.
  • Aluminum oxide fine particles are preferred from the viewpoint of transparency and scratch resistance.
  • the crystal structure of the aluminum oxide fine particles is preferably ⁇ -type and/or ⁇ -type.
  • the content of the inorganic oxide fine particles (B) is from 0.3 to 0.3 in the non-volatile content of 100% by mass of the coating liquid for forming the low refractive index layer, from the viewpoint of achieving both scratch resistance, low refractive index, and transparency. It is preferably 5% by mass, more preferably 0.4 to 3% by mass.
  • the content of the inorganic oxide fine particles (B) is 0.5 to 15 parts by mass, preferably 1 to 10 parts by mass, and 1 to 5 parts by mass with respect to 100 parts by mass of the hollow particles (A). It is more preferable to have Within this range, both scratch resistance and transparency can be achieved.
  • Polyfunctional (meth)acrylate (C) is not limited as long as it is a compound having two or more (meth)acrylate groups.
  • Polyfunctional (meth)acrylates (C) include trimethylolpropane tri(meth)acrylate, glycerin tri(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, pentaerythritol tri( Polyol poly (meth) acrylate compounds such as meth) acrylate and pentaerythritol tetra (meth) acrylate; tris (2-acryloxyethyl) isocyanurate, EO-modified tris (2-acryloxyethyl) isocyanurate, PO-modified tris ( 2-acryloxyethyl)isocyanurate, and ⁇ -caprolactone-modified tris(
  • the polyfunctional (meth)acrylate (C) is preferably a polyfunctional (meth)acrylate having a silicone chain.
  • the silicone chain is a skeleton having a siloxane bond.
  • polyfunctional (meth)acrylates (C) include tris(2-acryloxyethyl) isocyanurate ("FANCRYL FA-731A” manufactured by Hitachi Chemical Co., Ltd., and “NEW FRONTIER TEICA” manufactured by Daiichi Kogyo Seiyaku Co., Ltd. GX-8430)", etc.), EO-modified tris(2-acryloxyethyl) isocyanurate ("Aronix M-313, M-315" manufactured by Toagosei Co., Ltd., "NK Ester A-9300” manufactured by Shin-Nakamura Chemical Co., Ltd.
  • KAYARAD DPHA-2C dipentaerythritol hexaacrylate and pentaerythritol tetraacrylate
  • Miramer SIU2400 polyfunctional urethane acrylate having a silicone chain
  • the content of the polyfunctional (meth)acrylate (C) is 10 to 90% by mass in 100% by mass of the non-volatile content of the low refractive index layer-forming coating liquid, from the viewpoint of achieving both scratch resistance and a low refractive index. is preferred, and 20 to 80% by mass is more preferred.
  • the polyfunctional (meth)acrylate (C) may be 10 to 90 parts by mass, or 20 to 80 parts by mass with respect to 100 parts by mass of the hollow particles (A), from the viewpoint of scratch resistance and low refractive index, 30 to 70 parts by mass, or more preferably 40 to 60 parts by mass.
  • the coating liquid for forming a low refractive index layer may optionally further contain a fluorine-containing (meth)acrylate (D).
  • the fluorine-containing (meth)acrylate (D) is not limited as long as it is a (meth)acrylate having a fluorine atom, and examples thereof include (meth)acrylates having a perfluoropolyether skeleton.
  • Commercially available products include "FLUOROLINK AD1700" (manufactured by Solvay) and "Megafac RS-90" (manufactured by DIC Corporation).
  • the fluorine-containing (meth)acrylate (D) By including the fluorine-containing (meth)acrylate (D), it is possible to improve the water contact angle on the surface of the obtained low refractive index layer and improve the antifouling property.
  • the content of the fluorine-containing (meth)acrylate (D) is preferably 1 to 11% by mass, more preferably 1.4 to 8% by mass, based on 100% by mass of the non-volatile content of the coating liquid for forming the low refractive index layer. More preferred.
  • the fluorine-containing (meth)acrylate (D) is 0.1 to 20 parts by mass, or 0.5 parts by mass when the total mass of the hollow particles (A) and the polyfunctional (meth)acrylate (C) is 100 parts by mass. It may be up to 12.5 parts by mass, more preferably 1.5 to 10 parts by mass, 3 to 9 parts by mass, or 5 to 8 parts by mass from the viewpoint of scratch resistance, low refractive index, and antifouling properties. .
  • the coating liquid for forming a low refractive index layer of the present embodiment may further contain various additives.
  • Additives include photopolymerization initiators, thermosetting resins, polymerization inhibitors, leveling agents, slip agents, antifoaming agents, surfactants, antibacterial agents, antiblocking agents, plasticizers, ultraviolet absorbers, and infrared absorbers. , antioxidants, silane coupling agents, conductive agents, inorganic fillers, and the like.
  • the antireflection film of the present embodiment comprises a transparent substrate and a low refractive index layer provided on the transparent substrate, and the low refractive index layer is formed from the coating liquid for forming the low refractive index layer of the present embodiment. It is a low refractive index layer.
  • the antireflection film may further have a hard coat layer or other cured film layer such as an optical adjustment layer, and preferably comprises a hard coat layer and a low refractive index layer on the transparent substrate in this order. .
  • Another cured film layer or the like may be provided between the transparent substrate layer and the hard coat layer or between the hard coat layer and the low refractive index layer. It is also preferable to provide a hard coat layer, an optical adjustment layer and a low refractive index layer in this order on a transparent substrate.
  • the luminous reflectance of the antireflection film of the present embodiment is preferably 1.5% or less, more preferably 1.2% or less, more preferably 1.0% or less from the viewpoint of antireflection properties. Yes, more preferably 0.5% or less.
  • Fig. 1 shows one form of the antireflection film.
  • the antireflection film 10 shown in FIG. 1 includes a transparent substrate 3 and a low refractive index layer 1 provided on the transparent substrate 3. A hard coat layer 2 is provided. Another form of the antireflection film is shown in FIG.
  • the antireflection film 10 shown in FIG. 2 includes a transparent substrate 3 and a low refractive index layer 1 provided on the transparent substrate 3, and a hard coat layer 2 is provided, and an optical adjustment layer 4 is further provided between the hard coat layer 2 and the low refractive index layer 1 .
  • it may be an antireflection film that does not have one or both of the hard coat layer and the optical adjustment layer. It should be noted that the present invention is not limited to the specific examples in the drawings.
  • the low refractive index layer of this embodiment is formed from the low refractive index layer-forming coating liquid of this embodiment.
  • it can be obtained by coating a coating liquid for forming a low refractive index layer on a transparent substrate, a hard coat layer, or the like, drying it, and then curing it.
  • the low refractive index layer preferably has a refractive index of 1.45 or less, and more preferably has a refractive index of 1.41 or less in order to reduce the reflectance.
  • the thickness of the low refractive index layer is preferably 80 to 150 nm, more preferably 100 to 140 nm, in order to reduce the reflectance.
  • the thickness of the low refractive index layer can be measured using an optical non-contact film thickness gauge.
  • the water contact angle on the surface of the low refractive index layer is preferably 90° or more. As a result, an antireflection film having excellent antifouling properties can be obtained. Further, the higher the water contact angle, the higher the antifouling property. Therefore, it is preferably 100° or more, more preferably 110° or more.
  • the amount of change in haze when reciprocating 10 times with a load of 200 g/cm 2 in a steel wool test is preferably 0.2 or less, more preferably 0.1 or less, and 0.1. 05 or less is more preferable. More preferably, the surface of the low refractive index layer has a water contact angle of 90° or more, and a haze change of 0.2 or less, 0.2 or less, when 10 reciprocations are carried out with a load of 200 g/cm 2 according to a steel wool test. 1 or less, or 0.05 or less.
  • the surface of the low refractive index layer has a water contact angle of 90° or more, or 100° or more, and a change in haze of 0.1 or less after 10 reciprocations with a 200 g/cm 2 load according to a steel wool test. is preferably
  • the transparent substrate is not particularly limited as long as it is a substrate having optical transparency, and examples thereof include glass, synthetic resin moldings, and films.
  • the thickness of the base material is not particularly limited, it is usually about 50 to 200 ⁇ m.
  • Synthetic resin moldings include polymethyl (meth) acrylate resin, copolymer resin containing methyl (meth) acrylate as a main component, polystyrene resin, styrene-methyl (meth) acrylate copolymer resin, styrene-(meth) acrylonitrile.
  • Examples include moldings of synthetic resins such as copolymer resins, polycarbonate resins, cellulose acetate butyrate resins, polyallyl diglycol carbonate resins, polyvinyl chloride resins, and polyester resins.
  • films include polyester film, polyethylene film, polypropylene film, cellophane film, diacetylcellulose film, triacetylcellulose (TAC) film, acetylcellulose butyrate film, polyvinyl chloride film, polyvinylidene chloride film, and polyvinyl alcohol.
  • Film ethylene vinyl alcohol film, polyolefin film, polystyrene film, polycarbonate film, polymethylpentel film, polysulfone film, polyetheretherketone film, polyethersulfone film, polyetherimide film, polyimide film, fluororesin film, nylon film , acrylic film, and the like.
  • the hard coat layer can be formed using a conventionally known coating liquid for forming a hard coat layer, and is not particularly limited. It is obtained by laminating a coating liquid for forming a coat layer on a substrate.
  • the thickness of the hard coat layer is usually about 0.5 ⁇ m to 5 ⁇ m, preferably about 3 to 5 ⁇ m for scratch resistance.
  • the refractive index is preferably about 1.5 to 1.8. From the viewpoint of antireflection, the refractive index is preferably 1.50 or more, more preferably 1.60 or more.
  • the optical adjustment layer can be formed using a conventionally known coating liquid for forming an optical adjustment layer, and is not particularly limited. is obtained by laminating a known coating liquid for forming an optical adjustment layer containing the above on the substrate or the hard coat layer.
  • the thickness of the optical adjustment layer is usually about 30 to 500 nm, preferably about 50 to 300 nm from the viewpoint of antireflection.
  • the refractive index is preferably about 1.60 to 1.9. From the viewpoint of antireflection, it is preferably 1.65 or more.
  • the method for producing the antireflection film is not particularly limited.
  • the antireflection film can be obtained by forming a low refractive index layer on a base material using a low refractive index layer-forming coating liquid.
  • a hard coat layer for example, an antireflection film can be obtained by forming a hard coat layer on a base material and further laminating a low refractive index layer on the hard coat layer.
  • another cured film layer such as an optical adjustment layer may be provided between the base material layer and the hard coat layer or between the hard coat layer and the low refractive index layer.
  • the film thickness of the antireflection film is usually about 50 to 200 ⁇ m.
  • the present invention will be described in more detail below with reference to examples and comparative examples, but the following examples in no way limit the technical scope of the present invention.
  • the compounding amounts in the table are expressed in % by mass, and values other than the solvent are converted to non-volatile matter.
  • a blank column in the table indicates that it was not blended.
  • the particle diameters of the hollow particles and the inorganic oxide fine particles and the film thickness of the low refractive index layer were measured by the following methods.
  • ⁇ Particle diameters of hollow particles and inorganic oxide fine particles The particle size distribution of the sample was measured using "Nanotrack UPA" manufactured by Nikkiso Co., Ltd. as a Nanotrack particle size distribution measuring device using a dynamic light scattering method. From the obtained particle size distribution, the particle diameter corresponding to 50% by volume was determined as D50, and the particle diameter corresponding to 99% by volume was determined as D99 in the integrated value in terms of volume. Samples were prepared by the following procedure. A sample was prepared by adding each of the hollow particles and the inorganic oxide fine particles to the diluted solution so that the loading index value was 1.0, and the particle size distribution was measured using this sample. As the diluent, the same dispersion solvent as the main component was used according to the dispersion solvent for the hollow particles and the inorganic oxide fine particles.
  • ⁇ Film thickness of low refractive index layer> The film thickness of the low refractive index layer was measured using an optical non-contact film thickness meter (FILMETRICS, Inc, F20 film thickness measurement device).
  • This resin composition was obtained as a polyfunctional polyester acrylate PE1 solution.
  • Polyfunctional polyester acrylate PE1 had 8 functional groups and a weight average molecular weight of 3,500.
  • Aluminum oxide fine particles (B) ⁇ Production of Aluminum Oxide Fine Particle Dispersion>
  • Aluminum oxide fine particle dispersion (1) 35 parts of aluminum oxide (1) ( ⁇ type crystal, primary particle diameter 10 nm), 14 parts of polyfunctional polyester acrylate PE1 in solid content, 25.5 parts of methyl ethyl ketone as an organic solvent, and 25.5 parts of methoxybutanol are mixed. Then, after stirring with a disper, dispersion treatment was performed in a sand mill to obtain a uniform aluminum oxide fine particle dispersion (1) containing ⁇ -type crystal aluminum oxide fine particles (B-1).
  • the aluminum oxide fine particles (B-1) had a particle size (D50) of 80 nm and a particle size (D99) of 200 nm.
  • Al oxide fine particle dispersion (2) The same procedure as in Production Example 1 except that 14.3 parts of aluminum oxide (1), 5.7 parts of polyfunctional polyester acrylate PE1 in solid content, 40 parts of methyl ethyl ketone as an organic solvent, and 40 parts of methoxybutanol were mixed. to obtain a uniform aluminum oxide fine particle dispersion (2) containing ⁇ -type crystal aluminum oxide fine particles (B-2).
  • the aluminum oxide fine particles (B-2) had a particle size (D50) of 60 nm and a particle size (D99) of 160 nm.
  • Al oxide fine particle dispersion (3) Dispersion treatment was carried out in the same manner as in Production Example 1 except that aluminum oxide (2) ( ⁇ -type crystal, primary particle size: 30 nm) was used, and uniform oxidation containing aluminum oxide fine particles (B-3) of ⁇ -type crystal An aluminum fine particle dispersion (3) was obtained.
  • the aluminum oxide fine particles (B-3) had a particle size (D50) of 90 nm and a particle size (D99) of 280 nm.
  • Al oxide fine particle dispersion (4) Dispersion treatment was carried out in the same manner as in Production Example 2 except that aluminum oxide (3) ( ⁇ -type crystals, primary particle size, 30 nm) was used, resulting in a uniform dispersion containing aluminum oxide fine particles (B-4) of ⁇ -type crystals. An aluminum oxide fine particle dispersion (4) was obtained.
  • the aluminum oxide fine particles (B-4) had a particle size (D50) of 80 nm and a particle size (D99) of 200 nm.
  • Al oxide fine particle dispersion (5) Dispersion treatment was carried out in the same manner as in Production Example 1 except that aluminum oxide (4) ( ⁇ -type crystals, primary particle size: 10 nm) was used, and uniform alumina containing fine aluminum oxide particles (B-5) of ⁇ -type crystals was obtained. Dispersion (5) was obtained.
  • the aluminum oxide fine particles (B-5) had a particle size (D50) of 80 nm and a particle size (D99) of 200 nm.
  • Al oxide fine particle dispersion (6) Dispersion treatment was carried out in the same manner as in Production Example 2, except that aluminum oxide (5) ( ⁇ -type crystal, primary particle size: 50 nm) was used. An aluminum oxide fine particle dispersion (6) was obtained.
  • the aluminum oxide fine particles (B'-1) had a particle size (D50) of 110 nm and a particle size (D99) of 280 nm.
  • Al oxide fine particle dispersion (7) Dispersion treatment was carried out in the same manner as in Production Example 1 except that aluminum oxide (3) ( ⁇ -type crystal, primary particle size 30 nm) was used, and a uniform dispersion containing aluminum oxide fine particles (B′-2) of ⁇ -type crystal was obtained. An aluminum oxide fine particle dispersion (5) was obtained.
  • the aluminum oxide fine particles (B'-2) had a particle diameter (D50) of 90 nm and a particle diameter (D99) of 320 nm.
  • Al oxide fine particle dispersion (8) Dispersion treatment was carried out in the same manner as in Production Example 2 except that aluminum oxide (4) ( ⁇ -type crystals, primary particle size: 10 nm) was used, resulting in a uniform dispersion containing aluminum oxide fine particles (B′-3) of ⁇ -type crystals. An alumina dispersion (8) was obtained.
  • the aluminum oxide fine particles (B'-3) had a particle diameter (D50) of 60 nm and a particle diameter (D99) of 140 nm.
  • the type, crystal system, and average particle size of the inorganic oxide fine particles are summarized below.
  • Coating solution 1 for forming hard coat layer or optical adjustment layer 100 parts of zirconium oxide particles, 155.4 parts of polyfunctional polyester acrylate PE1, 4.6 parts of ESACURE ONE (manufactured by IGM RESINS Co., Ltd.) as a photopolymerization initiator, and propylene glycol monomethyl ether as an organic solvent.
  • the coating liquid 1 for forming a hard coat layer or an optical adjustment layer was obtained by adjusting the content to 40%.
  • Coating solution 2 for forming hard coat layer or optical adjustment layer (coating solution 2)] 155.4 parts of polyfunctional polyester acrylate PE1, 4.6 parts of ESACURE ONE (manufactured by IGM RESINS Co., Ltd.) as a photopolymerization initiator, and propylene glycol monomethyl ether as an organic solvent were adjusted so that the concentration of nonvolatile matter was 40%. Thus, a coating liquid 2 for forming a hard coat layer or an optical adjustment layer (coating liquid 2) was obtained.
  • Coating solution 3 for forming hard coat layer or optical adjustment layer 100 parts of titanium oxide particles, 60 parts of polyfunctional polyester acrylate PE1, 3 parts of ESACURE ONE (manufactured by IGM RESINS Co., Ltd.) as a photopolymerization initiator, and propylene glycol monomethyl ether as an organic solvent to a non-volatile content of 40%.
  • a coating liquid 3 for forming a hard coat layer or an optical adjustment layer (coating liquid 3) was obtained by adjusting as follows.
  • Hollow particles A-1
  • hollow polymer particles crosslinked acrylic resin, particle diameter (D50) 80 nm, hollowness 43%, solid content 10% Hollow particles (A-2); hollow polymer particles, vinyl resin, particle diameter (D50) 150 nm, solid content 10% Hollow particles (A-3): Sururia 4320 (hollow silica particles, particle diameter (D50) 60 nm, particle refractive index 1.30, solid content 20.5%, manufactured by JGC Catalysts & Chemicals Co., Ltd.) ⁇ Hollow particles (A'-1); hollow silica particles, particle diameter (D50) 200 nm, solid content 20.5%
  • Example 1 ⁇ Preparation of coating solution for forming low refractive index layer> Hollow particles (A-1) (hollow polymer particles, crosslinked acrylic resin, average particle size 80 nm) as hollow particles (A) 100 parts (converted to 100% solid content), Miramer as polyfunctional (meth) acrylate (C) SIU2400 (manufactured by Miwon) 100 parts, fluorine-containing (meth)acrylate (D-1) as fluorine-containing (meth)acrylate (D) (FLUOROLINK AD1700 (manufactured by Solvay)) 15 parts (solid content 100% conversion value), alumina 4 parts of the dispersion (1) and 5 parts of OMNIRAD907 (manufactured by IGM RESINS Co., Ltd.) as a photopolymerization initiator are mixed well, and propylene glycol monomethyl ether as an organic solvent is adjusted to a nonvolatile content of 4% to obtain a low refractive index.
  • A-1 hinderethacryl
  • a thin layer forming coating liquid X1 was obtained. Since the aluminum fine particles (B-1) are contained in the alumina dispersion (1) in an amount of 25% by mass, the ratio of the hollow particles (A-1) to the alumina fine particles (B-1) is 100:1. In addition, the fluorine-containing (meth)acrylate (D) is contained in the non-volatile matter in an amount of 6.78% by mass. Polyfunctional polyester acrylate PE1 is contained in alumina dispersion (1) in an amount of 10% by mass.
  • a hard coat layer forming coating liquid 1 (coating liquid 1) is applied using a bar coater to obtain a film thickness after drying. After coating so as to have a thickness of 3.0 ⁇ m, a hard coat layer was formed by irradiating ultraviolet rays of 400 mJ/cm 2 with a high-pressure mercury lamp. On the hard coat layer, the obtained coating liquid X1 for forming a low refractive index layer was coated using a bar coater so that the film thickness after drying was 100 nm, and then the oxygen concentration was 500 ppm or less. A low refractive index layer was formed by irradiating ultraviolet rays of 400 mJ/cm 2 with a high-pressure mercury lamp in a nitrogen atmosphere to obtain an antireflection film.
  • PTT polyethylene terephthalate
  • Examples 2 to 19, Comparative Examples 1 to 7 Low refractive index layer-forming coating solutions X2 to X26 having a nonvolatile content concentration of 4% were obtained in the same manner as in Example 1, except that the compositions and blending amounts (in terms of nonvolatile content) shown in Tables 1 to 3 were used. Subsequently, antireflection films were obtained in the same manner as in Example 1, except that the low refractive index layer-forming coating liquids X2 to X26 were used.
  • Examples 20, 21, 28 In the same manner as in Example 1, a coating liquid X1 for forming a low refractive index layer was obtained. As shown in Table 5, a 50 ⁇ m thick polyethylene terephthalate (PET) film (“Lumirror UH-13” manufactured by Toray Industries, Inc.) or an 80 ⁇ m thick triacetyl cellulose (TAC) film (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.
  • PET polyethylene terephthalate
  • TAC triacetyl cellulose
  • “Fujitac ”) hard coat layer forming coating solutions 1 to 3 (coating solutions 1 to 3) were applied using a bar coater so that the film thickness after drying was 3.0 ⁇ m, and then high pressure mercury A hard coat layer was formed by irradiating ultraviolet rays of 400 mJ/cm 2 with a lamp.
  • the obtained coating liquid X1 for forming a low refractive index layer was coated using a bar coater so that the film thickness after drying was 100 nm, and then the oxygen concentration was 500 ppm or less.
  • a low refractive index layer was formed by irradiating ultraviolet rays of 400 mJ/cm 2 with a high-pressure mercury lamp in a nitrogen atmosphere to obtain an antireflection film.
  • Example 22 In the same manner as in Example 1, a coating liquid X1 for forming a low refractive index layer was obtained.
  • the obtained coating liquid X1 for forming a low refractive index layer was dried on a 50 ⁇ m thick polyethylene terephthalate (PET) film (“Lumirror UH-13” manufactured by Toray Industries, Inc.) using a bar coater to a film thickness of 100 nm.
  • PET polyethylene terephthalate
  • a low refractive index layer is formed by irradiating 400 mJ / cm 2 ultraviolet rays with a high pressure mercury lamp in a nitrogen atmosphere to obtain an antireflection film. rice field.
  • Examples 23 and 24 In the same manner as in Example 1, a coating liquid X1 for forming a low refractive index layer was obtained. As shown in Table 5, the coating solution 1 or 3 is applied to a 50 ⁇ m thick polyethylene terephthalate (PET) film (“Lumirror UH-13” manufactured by Toray Industries, Inc.) using a bar coater, and the film thickness after drying is After coating so as to have a thickness of 100 nm, it was irradiated with ultraviolet rays of 400 mJ/cm 2 from a high-pressure mercury lamp to form an optical adjustment layer.
  • PET polyethylene terephthalate
  • a low refractive index layer was formed by irradiating ultraviolet rays of 400 mJ/cm 2 with a high-pressure mercury lamp in a nitrogen atmosphere to obtain an antireflection film.
  • Examples 25-27 In the same manner as in Example 1, a coating liquid X1 for forming a low refractive index layer was obtained. As shown in Table 5, the coating solution 1 or 2 is applied to a 50 ⁇ m thick polyethylene terephthalate (PET) film (“Lumirror UH-13” manufactured by Toray Industries, Inc.) using a bar coater, and the film thickness after drying is After coating to a thickness of 3.0 ⁇ m, a hard coat layer was formed by irradiating ultraviolet rays of 400 mJ/cm 2 with a high-pressure mercury lamp.
  • PET polyethylene terephthalate
  • Coating solution 1 or 3 was applied on the hard coat layer using a bar coater so that the film thickness after drying was 100 nm, and then under a nitrogen atmosphere such that the oxygen concentration was 800 ppm or less, high pressure was applied.
  • a mercury lamp was used to irradiate ultraviolet rays of 400 mJ/cm 2 to form an optical adjustment layer.
  • the oxygen concentration becomes 500 ppm or less.
  • a low refractive index layer was formed by irradiating ultraviolet rays of 400 mJ/cm 2 with a high-pressure mercury lamp in a nitrogen atmosphere to obtain an antireflection film.
  • Example 29 In the same manner as in Example 1, a coating liquid X1 for forming a low refractive index layer was obtained. As shown in Table 5, a 50 ⁇ m thick polyethylene terephthalate (PET) film (“Lumirror UH-13” manufactured by Toray Industries, Inc.) was coated with a hard coat layer forming coating solution 1 (coating solution 1) using a bar coater. Then, the hard coat layer was formed by applying ultraviolet rays of 400 mJ/cm 2 from a high-pressure mercury lamp to form a hard coat layer.
  • PET polyethylene terephthalate
  • the obtained low refractive index layer forming coating solution X1 was applied using a bar coater so that the film thickness after drying was 140 nm, and then the oxygen concentration was 500 ppm or less.
  • a low refractive index layer was formed by irradiating ultraviolet rays of 400 mJ/cm 2 with a high-pressure mercury lamp in a nitrogen atmosphere to obtain an antireflection film.
  • Evaluation methods for the obtained low refractive index layer and antireflection film are as follows. The results are shown in Tables 2-5.
  • ⁇ HZ; measurement of haze value> The haze value (HZ) of the surface of the low refractive index layer of the produced antireflection film was measured using a "haze meter SH7000" manufactured by Nippon Denshoku Industries Co., Ltd. Incidentally, ⁇ and ⁇ are practically acceptable levels.
  • the scratch resistance of the produced antireflection film was evaluated using a "Gakushin type fastness to rubbing tester" manufactured by Tester Sangyo Co., Ltd. Steel wool #0000 was attached to a friction element (surface area: 1 cm 2 ) to which a load of 200 g was attached, and the surface (1 cm ⁇ 15 cm) of the low refractive index layer was reciprocated 10 times. After that, the haze value of the antireflection film was measured and evaluated according to the following criteria.
  • ⁇ ⁇ : ⁇ Hz 0.05% or less (very good) ⁇ : ⁇ Hz is more than 0.05% and 0.1% or less (good) ⁇ : ⁇ Hz is over 0.1% and 0.2% or less (acceptable) ⁇ ⁇ : ⁇ Hz exceeds 0.2% (defective)
  • ⁇ Hz haze value after scratch test - haze value before scratch test.
  • the scratch resistance of the produced antireflection film was evaluated using a "Gakushin type fastness to rubbing tester" manufactured by Tester Sangyo Co., Ltd.
  • a gauze Iwatsuki gauze, 100% cotton
  • a friction element surface area: 1 cm 2
  • the surface (1 cm ⁇ 15 cm) of the low refractive index layer was reciprocated 100 times.
  • the haze value of the antireflection film was measured and evaluated according to the following criteria.
  • ⁇ Contact angle is 100° or more (very good)
  • ⁇ Contact angle is 90° or more and less than 100° (good)
  • x The contact angle is less than 90° (poor).
  • the low refractive index layer formed using the coating liquid for forming a low refractive index layer of the present invention can be either rigid fibers such as steel wool or flexible fibers such as gauze. It has become clear that an antireflection film having high scratch resistance and excellent antifouling properties can be obtained.
  • Example 30 and 31 A coating liquid for forming a low refractive index layer having a non-volatile content concentration of 4% was carried out in the same manner as in Example 18, except that the hollow particles (A-3) were used instead of the hollow particles (A-1). X30 was obtained. Subsequently, an antireflection film of Example 30 was obtained in the same manner as in Example 18, except that the low refractive index layer-forming coating liquid X30 was used. A coating liquid for forming a low refractive index layer having a non-volatile content concentration of 4% was prepared in the same manner as in Example 19, except that the hollow particles (A-3) were used instead of the hollow particles (A-1). X31 was obtained.
  • Example 31 An antireflection film of Example 31 was obtained in the same manner as in Example 19, except that the coating liquid X31 for forming a low refractive index layer was used. It was evaluated in the same manner as in Example 1 above. Table 6 shows the results.
  • 1 low refractive index layer
  • 2 hard coat layer
  • 3 transparent substrate
  • 4 entire optical adjustment layer 10: antireflection film

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JP2020030363A (ja) * 2018-08-23 2020-02-27 日東電工株式会社 反射防止フィルム、反射防止フィルムの製造方法、光学部材および画像表示装置
WO2021020504A1 (ja) * 2019-07-30 2021-02-04 東山フィルム株式会社 反射防止フィルム
JP2021173831A (ja) * 2020-04-23 2021-11-01 日東電工株式会社 反射防止層付円偏光板および該反射防止層付円偏光板を用いた画像表示装置
WO2021220681A1 (ja) * 2020-04-30 2021-11-04 日東電工株式会社 反射防止層付円偏光板および該反射防止層付円偏光板を用いた画像表示装置

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US7816487B2 (en) * 2004-09-30 2010-10-19 Intel Corporation Die-attach films for chip-scale packaging, packages made therewith, and methods of assembling same
JP2008088309A (ja) * 2006-10-02 2008-04-17 Nitto Denko Corp 硬化皮膜、それを用いた反射防止ハードコートフィルム、偏光板および画像表示装置
JP2011102977A (ja) * 2009-10-16 2011-05-26 Dainippon Printing Co Ltd 光学フィルム及びディスプレイパネル
JP2020030363A (ja) * 2018-08-23 2020-02-27 日東電工株式会社 反射防止フィルム、反射防止フィルムの製造方法、光学部材および画像表示装置
WO2021020504A1 (ja) * 2019-07-30 2021-02-04 東山フィルム株式会社 反射防止フィルム
JP2021173831A (ja) * 2020-04-23 2021-11-01 日東電工株式会社 反射防止層付円偏光板および該反射防止層付円偏光板を用いた画像表示装置
WO2021220681A1 (ja) * 2020-04-30 2021-11-04 日東電工株式会社 反射防止層付円偏光板および該反射防止層付円偏光板を用いた画像表示装置

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