CN114730027A - Ultraviolet-curable composition for light-shielding, light-shielding film, and method for producing article having light-shielding film - Google Patents
Ultraviolet-curable composition for light-shielding, light-shielding film, and method for producing article having light-shielding film Download PDFInfo
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- CN114730027A CN114730027A CN201980102453.6A CN201980102453A CN114730027A CN 114730027 A CN114730027 A CN 114730027A CN 201980102453 A CN201980102453 A CN 201980102453A CN 114730027 A CN114730027 A CN 114730027A
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- light
- shielding
- ultraviolet
- curable composition
- meth
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Classifications
-
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D3/00—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials
- B05D3/06—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by exposure to radiation
- B05D3/061—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by exposure to radiation using U.V.
- B05D3/065—After-treatment
- B05D3/067—Curing or cross-linking the coating
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/34—Silicon-containing compounds
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- 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
- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
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- 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
- C09D201/00—Coating compositions based on unspecified macromolecular compounds
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- 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
- C09D7/66—Additives characterised by particle size
- C09D7/69—Particle size larger than 1000 nm
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/22—Absorbing filters
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/22—Absorbing filters
- G02B5/223—Absorbing filters containing organic substances, e.g. dyes, inks or pigments
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Abstract
Disclosed is an ultraviolet-curable composition for light shielding, which contains a photopolymerizable monomer, an organic black pigment, and a particulate light-scattering material. An article provided with a light-shielding film having high light-shielding properties can be manufactured by a method including the steps of: a step of forming a resin film containing a light-shielding ultraviolet-curable composition on a substrate; and a step of forming a light-shielding film comprising a cured product of the ultraviolet-curable light-shielding composition by curing the resin film by irradiation with ultraviolet rays.
Description
Technical Field
The present invention relates to a light-shielding ultraviolet-curable composition, a light-shielding film, and a method for producing an article having a light-shielding film.
Background
A light-shielding film provided in various display devices such as a liquid crystal display device is sometimes formed using a thermosetting or ultraviolet-curable ink containing a black pigment such as carbon black (for example, patent document 1). Ultraviolet-curable inks are advantageous over thermosetting inks in terms of suppressing damage to peripheral components of the light-shielding film and printing devices, and in terms of printing accuracy.
Prior art documents
Patent document
Patent document 1: japanese laid-open patent publication No. 2009-37234
Disclosure of Invention
Technical problem to be solved by the invention
Although a light-shielding film containing carbon black has high light-shielding properties, an ultraviolet-curable composition (or ink) containing carbon black is difficult to have sufficient ultraviolet curability because carbon black does not substantially transmit ultraviolet rays. The use of an organic black pigment which transmits ultraviolet rays to some extent is expected to improve ultraviolet curability, but in this case, the light-shielding property of the light-shielding film tends to be insufficient.
Accordingly, an aspect of the present invention provides a light-shielding ultraviolet-curable composition capable of forming a light-shielding film having sufficient ultraviolet curability and high light-shielding property.
Means for solving the technical problem
One aspect of the present invention provides an ultraviolet curable composition for light shielding, comprising a photopolymerizable monomer, an organic black pigment, and a particulate light scattering material.
Another aspect of the present invention provides a light-shielding film comprising a cured product of the above light-shielding ultraviolet curable composition.
Still another aspect of the present invention provides a method of manufacturing an article having a light-shielding film, including the steps of: a step of forming a resin film containing the ultraviolet curable composition for light shielding on a substrate; and a step of forming a light-shielding film comprising a cured product of the ultraviolet-curable light-shielding composition by irradiating the resin film with ultraviolet light.
Effects of the invention
According to one aspect of the present invention, there is provided an ultraviolet-curable composition for light-shielding capable of forming a light-shielding film having sufficient ultraviolet-curability and having high light-shielding properties.
Detailed Description
Hereinafter, some embodiments of the present invention will be described in detail. However, the present invention is not limited to the following embodiments. In the present specification, "(meth) acryloyl" means methacryloyl or acryloyl. This is also the same with respect to other similar performances.
An ultraviolet curable composition for light shielding according to an embodiment includes a photopolymerizable monomer, an organic black pigment, and a particulate light scattering material. The ultraviolet curable composition can be used for forming a light-shielding film. The ultraviolet curable composition according to the present embodiment may be an ink for forming a light-shielding film by a printing method (for example, an ink for ink jet printing).
The photopolymerizable monomer is composed of one or more compounds having one or more photopolymerizable functional groups. The photopolymerizable functional group may be an ethylenically unsaturated group. The photopolymerizable monomer may be a compound having one or more (meth) acryloyl groups. The compound having a (meth) acryloyl group used as the polymerizable monomer may be an alkyl (meth) acrylate, a (meth) acrylic acid, a (meth) acrylamide, an N-alkyl (meth) acrylamide, an N, N-dialkyl (meth) acrylamide, or a combination of two or more selected from these, and the alkyl group of the alkyl (meth) acrylate, the N-alkyl (meth) acrylamide, and the N, N-dialkyl (meth) acrylamide may have a substituent. Examples of the substituent include an aryl group, a hydroxyl group, a carboxyl group, a glycidyl group, and an amino group.
The photopolymerizable monomer may be in a liquid state at room temperature (25 ℃). The ultraviolet curable composition containing a liquid photopolymerizable monomer may be solvent-free, and may have fluidity suitable for printing. The photopolymerizable monomer may be a monofunctional acrylic monomer having one (meth) acryloyl group, a polyfunctional acrylic monomer having two or more (meth) acryloyl groups, or a combination thereof.
The monofunctional acrylic monomer is not particularly limited, and specific examples thereof include methyl (meth) acrylate and (meth) acrylic acid(meth) acrylic esters having an alkyl group having 1 to 18 carbon atoms such as ethyl enoate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, t-butyl (meth) acrylate, n-pentyl (meth) acrylate, n-hexyl (meth) acrylate, n-octyl (meth) acrylate, isooctyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, dodecyl (meth) acrylate, and stearyl (meth) acrylate; (meth) acrylates having a hydroxyl group such as 2-hydroxyethyl (meth) acrylate, 1-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 3-hydroxypropyl (meth) acrylate, 1-hydroxypropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, 3-hydroxybutyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate and 1-hydroxybutyl (meth) acrylate; (meth) acrylates having an epoxypropyl group such as glycidyl (meth) acrylate, α -ethyl glycidyl (meth) acrylate, α -propyl glycidyl (meth) acrylate, α -butyl glycidyl (meth) acrylate, 2-methyl glycidyl (meth) acrylate, 2-ethyl glycidyl (meth) acrylate, 2-propyl glycidyl (meth) acrylate, 3, 4-epoxybutyl (meth) acrylate, 3, 4-epoxyheptyl (meth) acrylate, α -ethyl-6, 7-epoxyheptyl (meth) acrylate, and 3, 4-epoxycyclohexylmethyl (meth) acrylate; and cyclopentyl (meth) acrylate, cyclohexyl (meth) acrylate, methylcyclohexyl (meth) acrylate, trimethylcyclohexyl (meth) acrylate, norbornyl methyl (meth) acrylate, phenylnorbornyl (meth) acrylate, cyanonorbornyl (meth) acrylate, isoryyl (meth) acrylate, ryegranyl (meth) acrylate, adamantyl (meth) acrylate, dimethyladamantyl (meth) acrylate, tricyclo [5.2.1.02.6]Decyl-8-yl (meth) acrylate, tricyclo [5.2.1.02.6]And (meth) acrylates having an alicyclic group such as decyl-4-methyl (meth) acrylate and cyclodecyl (meth) acrylate.
The curable composition may contain a liquid photopolymerizable monomer and a polymer and/or oligomer. The polymer and oligomer may have a photopolymerizable group. In the present specification, a polymer or oligomer having a photopolymerizable group is regarded as a photopolymerizable monomer.
The content of the photopolymerizable monomer may be 10 mass% or more, 20 mass% or more, 30 mass% or more, and 95 mass% or less based on the mass of the ultraviolet curable composition. The content herein means the total content of two or more compounds when these compounds are used as the photopolymerizable monomer.
The ultraviolet curable composition for light shielding may further contain a photopolymerization initiator. The photopolymerization initiator is a compound that initiates a polymerization reaction of a photopolymerizable monomer by absorbing ultraviolet rays. The photopolymerization initiator may be, for example, a photo radical polymerization initiator or a photo cation polymerization initiator, and particularly, may be a photo radical polymerization initiator. The photopolymerization initiator may contain a compound having a maximum value in an absorption spectrum in a range of 300 to 400nm from the viewpoint of ultraviolet curability. The composition containing the photopolymerizable monomer, the organic black pigment, and the particulate light scattering material may be mixed with a photopolymerization initiator to produce a light-shielding ultraviolet curable composition.
The photo radical polymerization initiator is not particularly limited, and may be, for example, an α -cleavage type (cleavage type) compound or a hydrogen abstraction type (hydrogen abstraction type) compound, or may be a bimolecular radical polymerization initiator. Examples of the photopolymerization initiator include benzophenone, 4-methylbenzophenone, N, N, N ', N' -tetramethyl-4, 4 '-diaminobenzophenone (Michler's ketone), N, N-tetraethyl-4, 4 '-diaminobenzophenone, 4-methoxy-4' -dimethylaminobenzone, α -hydroxyisobutylbenzophenone, 2-ethylanthraquinone, tert-butylanthraquinone, 1, 4-dimethylanthraquinone, 1-chloroanthraquinone, 2, 3-dichloroanthraquinone, 3-chloro-2-methylanthraquinone, 1, 2-benzoanthraquinone, 2-phenylanthraquinone, 1, 4-naphthoquinone, 9, 10-phenanthrenequinone, thioxanthone, 2-chlorothioxanthone, 1-hydroxycyclohexylphenylketone, and, Aromatic ketone compounds such as 2, 2-dimethoxy-1, 2-diphenylethane-1-one, 1- [4- (2-hydroxyethoxy) phenyl ] -2-hydroxy-2-methyl-1-propan-1-one, and 2-hydroxy-2-methyl-1-phenylpropan-1-one; benzoin compounds such as benzoin, methyl benzoin, and ethyl benzoin; benzoin ether compounds such as benzoin methyl ether, benzoin ethyl ether, benzoin isobutyl ether, and benzoin phenyl ether; diphenylethanedione; 2, 2-diethoxyacetophenone; benzyl dimethyl ketal; an ester compound of β - (acridin-9-yl) (meth) acrylic acid; acridine compounds such as 9-phenylacridine, 9-pyridylacridine and 1, 7-bisacridinoheptane; 2- (o-chlorophenyl) -4, 5-diphenylimidazole dimer, 2- (o-chlorophenyl) -4, 5-bis (m-methoxyphenyl) imidazole dimer, 2- (o-fluorophenyl) -4, 5-diphenylimidazole dimer, 2- (o-methoxyphenyl) -4, 5-diphenylimidazole dimer, 2,4, 5-triarylimidazole dimers such as 2- (p-methoxyphenyl) -4, 5-diphenylimidazole dimer, 2, 4-bis (p-methoxyphenyl) 5-phenylimidazole dimer, 2- (2, 4-dimethoxyphenyl) -4, 5-diphenylimidazole dimer, and 2- (p-methylmercaptophenyl) -4, 5-diphenylimidazole dimer; 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -1-butanone; 2-methyl-1- [4- (methylthio) phenyl ] -2-morpholino-1-propanolane; bis (2,4, 6-trimethylbenzoyl) -phenylphosphine oxide; and polymerizing (2-hydroxy-2-methyl-1- (4- (1-methylvinyl) phenyl) propanone). These photopolymerization initiators may be used singly or in combination of two or more.
The content of the photopolymerization initiator may be, for example, 0.1 to 10% by mass based on the mass of the ultraviolet-curable composition. The content herein means the total content of two or more compounds when these compounds are used as photopolymerization initiators.
The organic black pigment is black particles containing an organic pigment, which can be selected from pigments generally used as black pigments. The organic black pigment may be at least one selected from the group consisting of perylene (perylene) based pigments (perylene black), lactam based pigments (lactam black), aniline black, cyanine black, lignin black, and RGB black, for example.
The average particle diameter (dispersed particle diameter) of the organic black pigment dispersed in the ultraviolet-curable composition is not particularly limited, and may be, for example, 0.01 to 1.0 μm.
From the viewpoint of appropriate light-shielding properties of the light-shielding film, the content of the organic black pigment may be 0.5 mass% or more or 1.0 mass% or more, and may be 50 mass% or less, based on the mass of the ultraviolet curable composition. The content herein refers to the total content of two or more organic black pigments when used.
The light scattering material is composed of a plurality of particles. These plural particles are generally dispersed in the ultraviolet-curable composition. The average particle diameter of the light scattering material may be 0.05 μm or more, and may be 5.0 μm or less, 4.0 μm or less, 3.0 μm or less, 2.0 μm or less, or 1.0 μm or less. From the viewpoint of appropriate light-shielding properties of the light-shielding film, the average particle diameter of the light-scattering material may be 0.1 to 1.0 μm. The average particle diameter of the light scattering material may be a value obtained from a volume-based particle size distribution obtained by a laser diffraction/scattering method.
The light scattering material may for example comprise silicone (silicone) particles, silica particles or a combination of these. The light scattering material may also contain silicone particles and other particles selected from silica particles, alumina particles, and titania particles. Some or all of the light scattering material may be hollow particles. The silicone particles are particles containing silicone having a polysiloxane chain, and the silicone may have a structure in which polysiloxane chains are crosslinked, or may be polyorganosilsesquioxane. The silicone particles may be composite particles having core particles (core particles) containing a silicone having a polysiloxane chain and a film formed on the surface of the core particles and containing polyorganosilsesquioxane.
The content of the light scattering material may be 0.5% by mass or more or 1.0% by mass or more based on the mass of the ultraviolet curable composition, and may be 10% by mass or less, 9.0% by mass or less, 8.0% by mass or less, 7.0% by mass or less, 6.0% by mass or less, 5.0% by mass or less, or 4.0% by mass or less. The content herein refers to the total content of these when two or more light scattering materials are used.
The ultraviolet-curable composition may be a solvent-free composition substantially containing no solvent. More specifically, the content of the solvent may be 1.0% by mass or less, or may be 0% by mass, based on the mass of the ultraviolet-curable composition. The composition (ink) containing substantially no solvent is advantageous in preventing damage to a member around the light-shielding film, preventing damage to a printing device, and forming a highly accurate light-shielding film, for example.
A cured film formed by film curing of the ultraviolet curable composition has high light-shielding properties. For example, the OD value (optical density) of the formed cured film may be 1.5 or more, 2.0 or more, or 2.5 or more. The OD value is calculated from the average transmittance of the cured film having a thickness of 130 [ mu ] m + -5 [ mu ] m to light having a wavelength of 400 to 700 nm.
Various articles having a light-shielding film can be produced by using the ultraviolet-curable composition according to the above-described exemplary embodiment. One embodiment of a method of manufacturing an article having a light-shielding film includes the steps of: a step of forming a resin film containing an ultraviolet-curable composition on a substrate; and a step of forming a light-shielding film of a cured product of the ultraviolet-curable composition by irradiating the resin film with ultraviolet light. The resin film may also be formed by printing (for example, inkjet printing) using the ultraviolet curable composition as an ink. The wavelength of ultraviolet rays for curing the ultraviolet curable composition for forming a resin film may be 300 to 400 nm. The thickness of the resin film (light-shielding film) may be, for example, 20 to 1000 μm.
Examples of articles having a light-shielding film include an image display device, an optical sensor, and a lens.
Examples
The present invention will be further specifically described below with reference to examples. However, the present invention is not limited to these examples.
1. Raw materials
1-1. Black pigment
Organic black pigments
Lactam pigment (dispersed particle size: 0.17 μm)
Perylene pigment (dispersed particle diameter: 0.17 μm)
The transmission spectra of these lactam pigments and perylene pigments include a portion having a transmittance of more than 10% in the wavelength range of 300 to 400 nm.
Other pigments
Carbon Black (dispersed particle size: 0.15 μm)
1-2. light scattering materials
Silicone particles (Shin-Etsu Chemical Co., Ltd., product name: X-52-854, average particle diameter: 0.7 μm)
Silicone particles (Shin-Etsu Chemical Co., Ltd., product name: KMP-706, average particle diameter: 2.0 μm)
Silicone composite particles (Shin-Etsu Chemical Co., Ltd., product name: X-52-7030, average particle diameter: 0.8 μm)
Silica particles (manufactured by Admatechs Co., Ltd., product name: S0-C1, average particle diameter: 0.3 μm)
Silica particles (Admatechs Co., Ltd., product name: S0-C2, average particle diameter: 0.5 μm)
1-3. photopolymerizable monomer
4-hydroxybutyl acrylate (4-HBA)
1-4 photo radical polymerization initiator
1-Hydroxycyclohexyl phenyl ketone (product name: Irgacure-184, manufactured by BASF Co.)
4-methylbenzophenone (manufactured by Sort Co., Ltd., product name: SB-PI712)
2. Ultraviolet-curable composition (ink)
Example 1
A dispersion of a lactam pigment having a dispersion particle size of 0.17 μm was obtained by dispersing 3.0 parts by mass of the lactam pigment in 91.7 parts by mass of 4-hydroxybutyl acrylate. To the dispersion, 2.0 parts by mass of silicone particles (X-52-854), 3.0 parts by mass of 1-hydroxycyclohexyl phenyl ketone (Irgacure-184), and 0.3 parts by mass of 4-methylbenzophenone (SB-PI712) were added, and the mixture was stirred at 2,000rpm for 5 minutes using a revolution and rotation mixer (THINKY CORPORATION, product name: ARE-250), thereby obtaining an ultraviolet curable composition.
Examples 2 to 8 and comparative examples 1 to 3
An ultraviolet-curable composition was prepared in the same manner as in example 1, except that the materials and the blending amounts were changed as shown in table 1.
3. Production of laminated film
Each of the ultraviolet-curable compositions of examples and comparative examples was coated on a support film (polyethylene terephthalate film, manufactured by FUJIMORI KOGYO CO., LTD, product name: 75E-0010HTA) having a thickness of 75 μm of a surface subjected to mold release treatment using an applicator (applicator). A protective film (polyethylene terephthalate film, manufactured by FUJIMORI KOGYO CO., LTD, product name: 50E-0010BD) having a thickness of 50 μm subjected to mold release treatment was overlaid on the formed resin film. Ultraviolet rays (3,000 mJ/cm) were irradiated from the protective film side by using an ultraviolet irradiation apparatus (EYE GRAPHICS Co., Ltd., manufactured by Metal halide Lamp)2) The resin film was cured to obtain a laminated film having a light-shielding film (thickness of about 130 μm) of a cured product of the ultraviolet-curable resin composition.
4. Evaluation of
4-1 reaction Rate (ultraviolet curing)
About 1g of each of the ultraviolet curable compositions of examples and comparative examples was dropped on a glass plate to form a resin film as a measurement sample before UV irradiation. Using a Fourier transform infrared absorption spectrometer (manufactured by SHIMADZU CORPORATION, product name: IR Spirit (QATR-S unit), the optical resolution was 2cm at room temperature (25 ℃ C.) in an environment-1And accumulating: the infrared absorption spectrum of the formed resin film was measured by the ATR method under the condition of 64 times.
A measurement sample having a size of 10mm × 10mm was cut out from the laminated film having the light-shielding film, and the protective film was peeled off from the measurement sample. The exposed light-shielding film was bonded to a glass plate, and then the support film was peeled off from the light-shielding film. The infrared absorption spectrum of the exposed light-shielding film (measurement sample after UV irradiation) was measured by the same method as described above.
In each of the obtained infrared absorption spectra, the spectrum was determined to be 810cm-1The intensity (A) of the absorption peak of acryloyl group showing a maximum in the vicinity thereof and the value assigned to 1720cm-1The intensity (B) of an absorption peak showing a maximum in the vicinity of the carbonyl groupThe acryloyl group absorption peak ratio was calculated by the following formula.
Acryl absorption peak ratio ═ (a)/(B)
The reaction rate of acryloyl groups was calculated from the acryloyl absorption peak ratio α obtained from the infrared absorption spectrum of the measurement sample before UV irradiation and the acryloyl absorption peak ratio β obtained from the infrared absorption spectrum of the measurement sample after UV irradiation using the following formula. The large value of the reaction rate means that curing is efficiently performed by ultraviolet irradiation.
Reaction rate (%) - (β/α) × 100
OD value (light-shielding property)
The transmittance of a light-shielding film having a size of 40mm × 50mm was measured at each wavelength of 5nm from 400nm to 700nm using a haze meter (NIPPON DENSHOKU industriees co., ltd., product name: SH7000) equipped with D65 as a light source. The OD value was calculated from the average value C of the transmittance at each wavelength by the following equation. A large OD value means that the light-shielding film has high shielding properties (light-shielding properties) against visible light.
OD value ═ Log10(C/100)
[ Table 1]
The ultraviolet-curable composition of each example was cured with good curability by ultraviolet irradiation, and a light-shielding film having sufficiently high light-shielding properties was formed. The light-shielding film formed from the ultraviolet curable composition of comparative example 1 containing the organic black pigment and not the light-scattering material had low light-shielding properties. The ultraviolet curable composition of comparative example 2 containing carbon black formed a light-shielding film having high light-shielding properties, but was insufficient in curability.
Claims (8)
1. An ultraviolet-curable composition for light shielding, comprising:
a photopolymerizable monomer;
an organic black pigment; and
a particulate light scattering material.
2. The ultraviolet-curable light-shielding composition according to claim 1,
the average particle size of the light scattering material is 0.1-3.0 μm.
3. The ultraviolet-curable composition for light-shielding according to claim 1 or 2, wherein,
the light scattering material comprises silicone particles, silica particles, or both.
4. The ultraviolet-curable light-shielding composition according to any one of claims 1 to 3,
the content of the light scattering material is 0.5-10% by mass based on the mass of the ultraviolet curable composition for shielding light.
5. The ultraviolet-curable light-shielding composition according to any one of claims 1 to 4,
an OD value of a cured film formed by curing the film of the ultraviolet-curable composition for light-shielding is 1.5 or more,
the OD value is calculated from the average transmittance of the cured film with the thickness of 130 [ mu ] m +/-5 [ mu ] m to light with the wavelength of 400-700 nm.
6. The ultraviolet-curable composition for light-shielding according to any one of claims 1 to 5, further comprising a photopolymerization initiator.
7. A light-shielding film comprising a cured product of the ultraviolet-curable composition for light-shielding described in any one of claims 1 to 6.
8. A method of manufacturing an article having a light-shielding film, comprising the steps of:
a step of forming a resin film containing the ultraviolet-curable light-shielding composition according to any one of claims 1 to 6 on a substrate; and
and a step of forming a light-shielding film comprising a cured product of the ultraviolet-curable light-shielding composition by irradiating the resin film with ultraviolet light.
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| Application Number | Priority Date | Filing Date | Title |
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| PCT/JP2019/046902 WO2021106221A1 (en) | 2019-11-29 | 2019-11-29 | Ultraviolet-curable composition for light shielding, light-shielding film, and method for manufacturing an article comprising light-shielding film |
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| CN114730027A true CN114730027A (en) | 2022-07-08 |
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| JP5346509B2 (en) | 2007-07-10 | 2013-11-20 | 新日鉄住金化学株式会社 | Photosensitive resin composition for forming color filter partition walls, light-shielding color filter partition walls and color filters formed using the same |
| KR20130021128A (en) * | 2011-08-22 | 2013-03-05 | 성균관대학교산학협력단 | Black photosensitive resin composition and display device having the same |
| KR20160145589A (en) * | 2014-04-15 | 2016-12-20 | 미쓰비시 가가꾸 가부시키가이샤 | Substrate with light-blocking material, color filter, liquid crystal display device and coloring resin composition for forming said light-blocking material |
| JP2019032351A (en) | 2015-12-25 | 2019-02-28 | Ａｇｃ株式会社 | Optical filter and optical device |
| JP7396786B2 (en) | 2017-02-24 | 2023-12-12 | 日鉄ケミカル＆マテリアル株式会社 | Photosensitive resin composition for light-shielding film, light-shielding film, liquid crystal display device, method for producing light-shielding film having spacer function, and method for producing liquid crystal display device |
| JP2018155878A (en) | 2017-03-16 | 2018-10-04 | 三菱ケミカル株式会社 | Coloring photosensitive resin composition, cured product, organic electroluminescenct element, image display device, and illumination |
-
2019
- 2019-11-29 KR KR1020227020515A patent/KR20220106151A/en not_active Application Discontinuation
- 2019-11-29 WO PCT/JP2019/046902 patent/WO2021106221A1/en active Application Filing
- 2019-11-29 JP JP2021561132A patent/JP7414076B2/en active Active
- 2019-11-29 CN CN201980102453.6A patent/CN114730027A/en active Pending
-
2020
- 2020-11-26 TW TW109141489A patent/TW202124460A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| KR20220106151A (en) | 2022-07-28 |
| JPWO2021106221A1 (en) | 2021-06-03 |
| JP7414076B2 (en) | 2024-01-16 |
| TW202124460A (en) | 2021-07-01 |
| WO2021106221A1 (en) | 2021-06-03 |
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