WO2022230327A1 - 硬化膜及び表示装置 - Google Patents
硬化膜及び表示装置 Download PDFInfo
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- WO2022230327A1 WO2022230327A1 PCT/JP2022/007016 JP2022007016W WO2022230327A1 WO 2022230327 A1 WO2022230327 A1 WO 2022230327A1 JP 2022007016 W JP2022007016 W JP 2022007016W WO 2022230327 A1 WO2022230327 A1 WO 2022230327A1
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- meth
- mass
- acrylate
- cured film
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Classifications
-
- 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
- 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
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
-
- 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
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/02—Diffusing elements; Afocal elements
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/20—Exposure; Apparatus therefor
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- G—PHYSICS
- G09—EDUCATION; CRYPTOGRAPHY; DISPLAY; ADVERTISING; SEALS
- G09F—DISPLAYING; ADVERTISING; SIGNS; LABELS OR NAME-PLATES; SEALS
- G09F9/00—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements
- G09F9/30—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements in which the desired character or characters are formed by combining individual elements
Definitions
- the present invention relates to a cured film and a display device including the cured film.
- Patent Document 1 describes a photosensitive resin composition used for forming a pattern of red, green, blue, etc. or a white (transparent) pattern, and a cured film and a color filter formed from the composition. .
- the white (transparent) pattern described above does not contain a colorant that allows the wavelength of light incident on it to exit as a desired wavelength (e.g., red, green, etc.), while scattering the incident light.
- a light scattering agent is usually included for transmission.
- An object of the present invention is to provide a cured film of a curable composition containing a light scattering agent, which is resistant to deformation and damage, and a method capable of producing the cured film.
- Another object of the present invention is to provide a display device including the cured film.
- the present invention provides a cured film, a method for producing a cured film, and a display device described below.
- C photopolymerization initiator
- a method for producing a cured film that satisfies [6] The manufacturing method according to [5], wherein the thermosetting step is performed in a vacuum atmosphere.
- a display device comprising the cured film according to any one of [1] to [4].
- a cured film of a curable composition containing a light scattering agent which is resistant to deformation and damage, a method capable of producing the cured film, and a display device containing the cured film.
- the cured film according to the present invention is a cured film of a curable composition, and can be formed by curing the curable composition.
- the curable composition contains at least a light scattering agent (A) and a photopolymerizable compound (B).
- the cured film according to the present invention can be a white (transparent, achromatic) cured film, for example, a cured pattern. It does not contain colorants (quantum dots, pigments, dyes, etc.) that allow the light to be emitted. That is, the cured film according to the present invention normally emits light having the same or substantially the same wavelength as the incident light while scattering the light.
- the cured pattern is one aspect of a cured film, and refers to a cured film formed in a pattern.
- the cured film has a Martens hardness of 0.10 GPa or more as measured by the method described in Examples below.
- the Martens hardness of the cured film is preferably 0.12 GPa or more, more preferably 0.15 GPa or more, still more preferably 0.20 GPa or more, even more preferably 0.23 GPa or more, and particularly preferably 0.24 GPa or more.
- Martens hardness is a hardness that includes both components of plastic deformation and elastic deformation of a cured film, and is a characteristic value that includes not only hardness and resistance to deformation of a cured film, but also flexibility.
- the deformation resistance and breakage resistance of the cured film can be enhanced.
- a cured film is used as the white (transparent) pattern, deformation or breakage of the film can be prevented during manufacture or use of a device containing the film.
- Cured films can also have high abrasion resistance.
- the abrasion resistance of the cured film can be evaluated by pencil hardness. Specifically, the pencil hardness measured by the method described in the following Examples is preferably B or higher, more preferably H or higher, and still more preferably 2H or higher. Still more preferably 3H or more, particularly preferably 4H or more.
- the cured film having a pencil hardness of 2B or more the surface of the cured film is less likely to be scratched during the manufacturing process of the display device, and the deterioration of the cured film during long-term use and reduction in the intensity of emitted light due to scratches on the surface can be prevented. can be suppressed.
- the Martens hardness of the cured film is preferably 0.35 GPa or less, more preferably 0.32 GPa or less, still more preferably 0.30 GPa or less, even more preferably 0.30 GPa or less, and particularly preferably 0.28 GPa or less. , 0.26 GPa or less, or even 0.25 GPa or less. If the Martens hardness of the cured film is excessively high, the emitted light intensity may decrease when the cured film is used as a white (transparent) pattern.
- a decrease in the intensity of emitted light is caused, for example, by shrinkage of the cured film, which causes aggregation and proximity of the light scattering agent (A) in the cured film, which causes light scattering in the cured film and reduces light extraction efficiency. It is thought that this is due to the fact that
- the emitted light intensity when light is incident on the cured film can be evaluated by the optical density (OD value) measured by the method described in the examples below. Since the OD value also depends on the film thickness T of the cured film, in this specification, the value obtained by dividing the OD value by the film thickness T (unit: ⁇ m) (OD value/T) was used as an indicator of the emitted light intensity. . The smaller the OD value/T, the greater the emitted light intensity. On the other hand, by increasing the OD value/T, the viewing angle characteristics of the cured film can be improved.
- the OD value/T of the cured film is preferably 0.0400 or less, more preferably 0.0350 or less, still more preferably 0.0200 or less, even more preferably 0.0190 or less, still more preferably 0.0180 or less, It is even more preferably 0.0170 or less, particularly preferably 0.0160 or less, and even more preferably less than 0.0145.
- the OD value/T may be 0.0050 or greater, 0.0100 or greater, 0.0130 or greater, 0.0140 or greater, or 0.0146 or greater. When the OD value/T is within the above range, it becomes easy to adjust the color balance when a pixel is configured by combining a pattern made of the cured film and a chromatic pattern.
- the cured film has a Martens hardness of 0.10 GPa or more and an OD value/T of 0.020 or less. In another preferred embodiment, the cured film has a Martens hardness of 0.15 GPa or more and an OD value/T of 0.020 or less. In another preferred embodiment, the cured film has a Martens hardness of 0.10 GPa or more, a pencil hardness of B or more, and an OD value/T of 0.020 or less. In these embodiments, the OD value/T is preferably 0.019 or less, more preferably 0.018 or less, even more preferably 0.017 or less, and even more preferably 0.016 or less.
- the value obtained by dividing the OD value / T of the cured film by the content of the light scattering agent (A) in the curable composition (relative to the total solid content of the curable composition) is preferably 0.00450. 0.00400 or less, more preferably 0.00360 or less, even more preferably 0.00350 or less, still more preferably 0.00300 or less, particularly preferably 0.00285 or less, preferably 0.00350 or less, and still more preferably 0.00300 or less. 00100 or more, more preferably 0.00200 or more, and still more preferably 0.00250 or more.
- the cured film according to the present invention is not particularly limited, it can be suitably produced by the method described in ⁇ Method for producing cured film>> below.
- the curable composition contains a light scattering agent (A) and a photopolymerizable compound (B).
- Light scattering agent (A) The cured film formed from the curable composition containing the light scattering agent (A) can scatter and emit light having the same or substantially the same wavelength as the light incident on the cured film.
- the light scattering agent (A) in the cured film the light transmittance and viewing angle characteristics of the cured film can be controlled, and the intensity of emitted light from the cured film can be improved.
- the light scattering agent (A) inorganic particles such as metal or metal oxide particles and glass particles can be mentioned. particles.
- metal oxides include TiO 2 , SiO 2 , BaTiO 3 , ZnO, etc.
- TiO 2 particles are preferable because they efficiently scatter light.
- the inorganic particles are difficult to disperse in a solvent as they are, so a dispersant, which will be described later, is usually used.
- the light scattering agent (A) may contain two or more kinds of particles.
- the particle size of the light scattering agent (A) is, for example, about 0.03 ⁇ m or more and 20 ⁇ m or less, and is preferably 0.05 ⁇ m or more and 1 ⁇ m or less from the viewpoint of enhancing the light scattering ability and dispersibility in the curable composition. and more preferably 0.05 ⁇ m or more and 0.5 ⁇ m or less.
- a dispersing agent may be used in which the light-scattering agent is previously dispersed in part or all of the solvent (G).
- a commercial item can be used as a dispersing agent. Examples of commercially available products include: BYK-Chemie Japan DISPERBYK-101, 102, 103, 106, 107, 108, 109, 110, 111, 116, 118, 130, 140, 154, 161, 162, 163, 164, 165, 166, 170, 171, 174, 180, 181, 182, 183, 184, 185, 190, 192, 2000, 2001, 2020, 2025, 2050, 2070, 2095, 2150, 2155; ANTI-TERRA-U, U100, 203, 204, 250,; BYK-P104, P104S, P105, 220S, 6919; BYK-LPN6919, 21116; LACTIMON, LACTIMON-WS
- the content of the light scattering agent (A) in the curable composition is, for example, 0.001% by mass or more and 50% by mass or less with respect to the total solid content of the curable composition, and from the viewpoint of the developability of the cured film, From the viewpoint of enhancing the light scattering ability and improving the intensity of the emitted light of the cured film, it is preferably 1% by mass or more and 30% by mass or less, more preferably 2% by mass or more and 10% by mass or less, still more preferably 3% by mass or more and 8% by mass. % or less.
- the total amount of solid content means the total amount of components excluding the solvent (G) among the components contained in the curable composition.
- the content of each component in the solid content of the curable composition can be measured by known analytical means such as liquid chromatography or gas chromatography.
- the content of each component in the solid content of the curable composition may be calculated from the formulation during preparation of the curable composition.
- Photopolymerizable compound (B) The curable composition contains one or more photopolymerizable compounds (B).
- the photopolymerizable compound (B) is a compound that can be polymerized by an active radical generated from the photopolymerization initiator (C) described below, an acid, or the like.
- Examples of the photopolymerizable compound (B) include photoradical polymerizable compounds that cure by radical polymerization reaction upon irradiation with light, and photocationically polymerizable compounds that cure through cationic polymerization reaction upon irradiation of light.
- the photopolymerizable compound (B) is preferably a photoradical polymerizable compound.
- the weight average molecular weight of the photopolymerizable compound (B) is, for example, 150 or more and 3000 or less, preferably 150 or more and 2900 or less, more preferably 250 or more and 1500 or less.
- photoradical polymerizable compounds include compounds having a polymerizable ethylenically unsaturated bond, among which (meth)acrylate compounds are preferred.
- the (meth) acrylate compound includes a monofunctional (meth) acrylate monomer having one (meth) acryloyloxy group in the molecule (hereinafter also referred to as "compound (B-1)"), and two in the molecule.
- a bifunctional (meth)acrylate monomer having a (meth)acryloyloxy group (hereinafter also referred to as “compound (B-2)”), and a multifunctional compound having three or more (meth)acryloyloxy groups in the molecule
- a functional (meth)acrylate monomer hereinafter also referred to as “compound (B-3)
- (meth)acrylate means acrylate and/or methacrylate. The same applies to "(meth)acryloyl", “(meth)acrylic acid” and the like.
- Compound (B-1) includes, for example, methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, butyl (meth)acrylate, amyl (meth)acrylate, hexyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, octyl (meth)acrylate, nonyl (meth)acrylate, dodecyl (meth)acrylate (lauryl (meth)acrylate), hexadecyl (meth)acrylate, octadecyl (meth)acrylate, cyclohexyl (meth)acrylate, methoxyethyl (meth)acrylate, butoxyethyl (meth)acrylate, phenoxyethyl (meth)acrylate, nonylphenoxyethyl (meth)acrylate, glycidyl (meth)acrylate, dimethylamin
- Examples of the compound (B-3) include glycerin tri(meth)acrylate, trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, Dipentaerythritol hexa (meth) acrylate, tripentaerythritol octa (meth) acrylate, tripentaerythritol hepta (meth) acrylate, tetrapentaerythritol deca (meth) acrylate, tetrapentaerythritol nona (meth) acrylate, tris (2-( meth)acryloyloxyethyl)isocyanurate, ethylene glycol-modified pentaerythritol tetra(meth)acrylate, ethylene
- photocationically polymerizable compounds include compounds having at least one oxetane ring (four-membered ring ether) in the molecule (hereinafter also simply referred to as “oxetane compound”), at least one oxirane ring (3 (Membered ring ether) (hereinafter also simply referred to as “epoxy compound”), vinyl ether compounds, and the like.
- Oxetane compounds include 3-ethyl-3-hydroxymethyloxetane, 1,4-bis[(3-ethyl-3-oxetanyl)methoxymethyl]benzene, 3-ethyl-3-(phenoxymethyl)oxetane, di[( 3-ethyl-3-oxetanyl)methyl]ether, 3-ethyl-3-(2-ethylhexyloxymethyl)oxetane, phenol novolak oxetane and the like. These oxetane compounds can be easily obtained as commercial products, and as commercial products, all of them are sold by Toagosei Co., Ltd.
- epoxy compounds include aromatic epoxy compounds, glycidyl ethers of polyols having alicyclic rings, aliphatic epoxy compounds, and alicyclic epoxy compounds.
- aromatic epoxy compounds include bisphenol-type epoxy resins such as diglycidyl ether of bisphenol A, diglycidyl ether of bisphenol F and diglycidyl ether of bisphenol S; Novolac type epoxy resins such as resins; polyfunctional epoxy resins such as glycidyl ether of tetrahydroxyphenylmethane, glycidyl ether of tetrahydroxybenzophenone, and epoxidized polyvinylphenol;
- bisphenol-type epoxy resins such as diglycidyl ether of bisphenol A, diglycidyl ether of bisphenol F and diglycidyl ether of bisphenol S
- Novolac type epoxy resins such as resins
- polyfunctional epoxy resins such as glycidyl ether of tetrahydroxyphenylmethane, glycidyl ether of tetrahydroxybenzophenone, and epoxidized polyvinylphenol
- glycidyl ether of a polyol having an alicyclic ring a nucleus-hydrogenated polyhydroxy compound obtained by selectively hydrogenating the aromatic ring of an aromatic polyol under pressure in the presence of a catalyst is used as glycidyl ether.
- aromatic polyols include bisphenol type compounds such as bisphenol A, bisphenol F and bisphenol S; novolac type resins such as phenol novolak resin, cresol novolak resin and hydroxybenzaldehyde phenol novolak resin; tetrahydroxydiphenylmethane, tetrahydroxybenzophenone and polyvinylphenol. and polyfunctional compounds such as.
- a glycidyl ether can be obtained by reacting epichlorohydrin with an alicyclic polyol obtained by hydrogenating the aromatic ring of these aromatic polyols.
- an alicyclic polyol obtained by hydrogenating the aromatic ring of these aromatic polyols.
- hydrogenated diglycidyl ethers of bisphenol A are preferred.
- Aliphatic epoxy compounds include polyglycidyl ethers of aliphatic polyhydric alcohols or their alkylene oxide adducts. Specifically, diglycidyl ether of 1,4-butanediol; diglycidyl ether of 1,6-hexanediol; triglycidyl ether of glycerin; triglycidyl ether of trimethylolpropane; diglycidyl ether of polyethylene glycol; diglycidyl ether of neopentyl glycol; obtained by adding one or more alkylene oxides (ethylene oxide or propylene oxide) to an aliphatic polyhydric alcohol such as ethylene glycol, propylene glycol or glycerin and polyglycidyl ether of polyether polyol.
- an aliphatic polyhydric alcohol such as ethylene glycol, propylene glycol or glycerin and polyglycidyl ether of polyether polyol.
- Alicyclic epoxy compounds are compounds that have at least one structure in the molecule that forms an oxirane ring with the carbon atoms of the alicyclic ring. (manufactured by Dow Chemical), "Cyracure UVR” series (manufactured by Dow Chemical), etc. can be used.
- vinyl ether compounds include 2-hydroxyethyl vinyl ether, triethylene glycol vinyl monoether, tetraethylene glycol divinyl ether, trimethylolpropane trivinyl ether, and the like.
- the photopolymerizable compound (B) preferably contains a polyfunctional (meth)acrylate monomer (compound (B-3)) having 3 or more (meth)acryloyloxy groups in the molecule.
- compound (B-3) a polyfunctional (meth)acrylate monomer having 3 or more (meth)acryloyloxy groups in the molecule.
- the curable composition contains the compound (B-3)
- the heat resistance and mechanical strength of the curable composition and the cured film can be increased, and it is also advantageous for improving the emitted light intensity of the cured film. can be.
- the curable composition contains the compound (B-3)
- the curability of the curable composition can be improved.
- a compound (B-3a) having 3 or more (meth)acryloyloxy groups in the molecule and having an acidic functional group, and 3 or more (meth) in the molecule A compound (B-3b) having an acryloyloxy group and no acidic functional group can be mentioned.
- the photopolymerizable compound (B) preferably contains at least one of compound (B-3a) and compound (B-3b), two or more kinds of compound (B-3a), and compound (B-3b). It may contain two or more kinds, or at least one kind of compound (B-3a) and at least one kind of compound (B-3b).
- the curable composition preferably contains compound (B-3a) as a photopolymerizable compound.
- compound (B-3a) as a photopolymerizable compound.
- the curable composition contains the compound (B-3a)
- the curability of the curable composition can be improved.
- the heat resistance of the curable composition and the cured film can be improved.
- the photopolymerizable compound (B) is the total amount of the photopolymerizable compound (B) contained in the curable composition, the compound Contains 50% by mass or more of (B-3b).
- the photopolymerizable compound (B) includes compound (B-3a) and compound (B-3b) from the viewpoint of improving the solvent resistance (remaining film rate) of the cured film.
- the acidic functional group examples include a carboxy group, a sulfonic acid group, a phosphoric acid group, and the like. Among them, the acidic functional group is preferably a carboxy group.
- the number of (meth)acryloyloxy groups possessed by one molecule of the compound (B-3) is, for example, 3 or more and 6 or less, preferably 3 or more and 5 or less, more preferably 3.
- the number of acidic functional groups per molecule of compound (B-3a) is one or more, preferably one. When it has two or more acidic functional groups, each acidic functional group may be different or the same, but preferably has at least one carboxy group.
- a compound having three or more (meth)acryloyloxy groups and hydroxy groups such as pentaerythritol tri(meth)acrylate or dipentaerythritol penta(meth)acrylate, is esterified with a dicarboxylic acid. and a compound obtained by the conversion.
- Examples of the compound include a compound obtained by monoesterifying pentaerythritol tri(meth)acrylate and succinic acid, a compound obtained by monoesterifying dipentaerythritol penta(meth)acrylate and succinic acid, and pentaerythritol tri(meth)
- a compound obtained by monoesterifying acrylate and maleic acid, a compound obtained by monoesterifying dipentaerythritol penta(meth)acrylate and maleic acid, and the like can be mentioned.
- a compound obtained by monoesterifying pentaerythritol tri(meth)acrylate and succinic acid is preferable.
- the content of the compound (B-3) is the curability of the curable composition and the cured film.
- the amount is preferably 5% by mass or more, more preferably 10% by mass or more, and still more preferably 20% by mass or more, relative to the total amount of the photopolymerizable compound (B). and is preferably 70% by mass or less, more preferably 60% by mass or less, still more preferably 50% by mass or less, even more preferably 40% by mass or less, and particularly preferably 30% by mass or less.
- the content of the compound (B-3) is the curability of the curable composition and the cured film.
- the total amount of the curable composition or the total amount of solid content of the curable composition is preferably 0.1% by mass or more and 50% by mass or less, more preferably 1% by mass. % or more and 40 mass % or less, more preferably 2 mass % or more and 30 mass % or less, still more preferably 5 mass % or more and 20 mass % or less, and particularly preferably 5 mass % or more and 15 mass % or less.
- the photopolymerizable compound (B) is a (meth)acrylate monomer having a vinyl ether group and a (meth)acryloyl group (preferably a (meth)acryloyloxy group) in the same molecule (hereinafter, “compound (B-4)” Also called.) is preferably included.
- compound (B-4) By including the compound (B-4) in the curable composition, it is possible to improve the dispersibility of the light scattering agent (A) in the curable composition, thereby improving the emitted light intensity of the cured film.
- the viscosity of the curable composition can be reduced and the coatability can be improved.
- Compound (B-4) can be a compound belonging to any one of compounds (B-1) to (B-3).
- the number of vinyl ether groups possessed by the compound (B-4) is preferably 1 or more and 4 or less, more preferably 1 or more and 2 or less, and particularly preferably 1.
- the number of (meth)acryloyl groups possessed by the compound (B-4) is preferably 1 or more and 4 or less, more preferably 1 or more and 2 or less, and particularly preferably 1.
- Examples of the compound (B-4) include 2-vinyloxyethyl (meth)acrylate, 3-vinyloxypropyl (meth)acrylate, 2-vinyloxypropyl (meth)acrylate, 1-vinyloxypropyl (meth)acrylate, 1-methyl -2-vinyloxyethyl (meth)acrylate, 4-vinyloxybutyl (meth)acrylate, 3-vinyloxybutyl (meth)acrylate, 2-vinyloxybutyl (meth)acrylate, 1-methyl-3-vinyloxypropyl (meth)acrylate, 2-methyl -3-vinyloxypropyl (meth)acrylate, 1-methyl-2-vinyloxypropyl (meth)acrylate, 1,1-dimethyl-2-vinyloxyethyl (meth)acrylate, 6-vinyloxyhexyl (meth)acrylate, 4 - vinyloxycyclohexyl (meth)acrylate, (4-vinyloxymethyl
- the compound (B-4) is preferably vinyloxy C 1-6 alkyl (meth)acrylate or (vinyloxy C 1-4 alkoxy) C 1-4 alkyl (meth) acrylate, and (vinyloxy C 1-4 alkoxy) C 1 -4 Alkyl (meth)acrylates are more preferred, and 2-(2-vinyloxyethoxy)ethyl (meth)acrylate is particularly preferred.
- the content of the compound (B-4) is from the viewpoint of reducing the viscosity of the curable composition and the viewpoint of increasing the emitted light intensity of the cured film. Therefore, the total amount of the photopolymerizable compound (B) is preferably 5% by mass or more, more preferably 10% by mass or more, still more preferably 20% by mass or more, and even more preferably 25% by mass or more. Also, it is preferably 85% by mass or less, more preferably 75% by mass or less, still more preferably 65% by mass or less, even more preferably 60% by mass or less, and particularly preferably 55% by mass or less.
- the content of the compound (B-4) is from the viewpoint of reducing the viscosity of the curable composition and the viewpoint of increasing the emitted light intensity of the cured film. From, relative to the total amount of the curable composition or the total amount of solid content of the curable composition, preferably 3% by mass or more and 50% by mass or less, more preferably 5% by mass or more and 45% by mass or less, more preferably 10% by mass % or more and 40 mass % or less, and still more preferably 10 mass % or more and 35 mass % or less.
- the photopolymerizable compound (B) preferably contains a monofunctional (meth)acrylate monomer (compound (B-1)) having one (meth)acryloyloxy group in the molecule.
- compound (B-1) a monofunctional (meth)acrylate monomer having one (meth)acryloyloxy group in the molecule.
- the curable composition has a temperature of 1 at 80°C. It preferably contains a polymerizable compound having a volatilization amount of 10% by mass or less when heated for a period of time. From the same point of view, the photopolymerizable compound (B) more preferably contains compound (B-1) having a volatilization amount of 10% by mass or less when heated at 80° C. for 1 hour.
- the volatilization amount is preferably 8% by mass or less, more preferably 7% by mass or less, still more preferably 5% by mass or less, even more preferably 3% by mass or less, still more preferably 2% by mass or less, particularly preferably 1% by mass or less. % by mass or less, and may be 0.01% by mass or more, or 0.1% by mass or more.
- the curable composition preferably contains a polymerizable compound whose homopolymer has a glass transition temperature of -50°C or higher.
- the photopolymerizable compound more preferably contains a compound (B-1) whose homopolymer has a glass transition temperature of ⁇ 50° C. or higher.
- the glass transition temperature is preferably ⁇ 30° C. or higher, more preferably ⁇ 20° C. or higher, and may be 0° C. or higher or 200° C. or lower.
- the glass transition temperature may be a catalog value or a numerical value described in a general physical property table, or may be measured by a commercially available differential scanning calorimeter or the like.
- the curable composition is a compound (B-1) in which the group bonded to the (meth)acryloyloxy group is an oxygen atom, a heteroatom such as a nitrogen atom. It is preferred to include a compound that is a hydrocarbon group that does not contain The hydrocarbon group is more preferably a chain hydrocarbon group or an alicyclic hydrocarbon group.
- the content of the compound (B-1) is, from the viewpoint of reducing the viscosity of the curable composition, the photopolymerizable compound (B). It is preferably 5% by mass or more, more preferably 10% by mass or more, still more preferably 15% by mass or more, still more preferably 20% by mass or more, and particularly preferably 25% by mass or more, based on the total amount. Also, it is preferably 75% by mass or less, more preferably 65% by mass or less, still more preferably 60% by mass or less, even more preferably 55% by mass or less, and particularly preferably 50% by mass or less.
- the content of the compound (B-1) is, from the viewpoint of reducing the viscosity of the curable composition, the total amount of the curable composition or curing preferably 5% by mass or more and 50% by mass or less, more preferably 8% by mass or more and 45% by mass or less, still more preferably 10% by mass or more and 40% by mass or less, still more preferably is 15% by mass or more and 35% by mass or less.
- the content of the photopolymerizable compound (B) in the curable composition is, for example, 5% by mass or more and 80% by mass or less, preferably 7% by mass or more and 75% by mass or less, relative to the total solid content of the curable composition. , more preferably 10% by mass or more and 70% by mass or less, and still more preferably 13% by mass or more and 68% by mass or less.
- the content of the photopolymerizable compound (B) is within the above range, the solvent resistance (residual film ratio) of the cured film tends to be improved.
- the content of the photopolymerizable compound (B) is preferably 13% by mass or more, more preferably 15% by mass, based on the total solid content of the curable composition. It is at least 20% by mass, more preferably at least 20% by mass.
- the curable composition can further contain one or more photoinitiators (C).
- the photopolymerization initiator (C) is a compound capable of initiating polymerization by generating active radicals, acids, etc. by the action of light or heat.
- the photopolymerization initiator (C) preferably contains an oxime compound having a first molecular structure represented by the following formula (1).
- the oxime compound is also referred to as "oxime compound (1)”.
- Inclusion of the oxime compound (1) as the photopolymerization initiator (C) can be advantageous from the viewpoint of increasing the emitted light intensity of the cured film.
- One of the reasons why such an effect can be exhibited is that the oxime compound (1) is necessary when the oxime compound (1) initiates photopolymerization due to the unique molecular structure of the oxime compound (1). Since the absorption wavelength of the oxime compound (1) changes greatly before and after the cleavage (decomposition) of the oxime compound (1), it is presumed that the oxime compound (1) has a high ability to initiate radical photopolymerization.
- R 1 represents R 11 , OR 11 , COR 11 , SR 11 , CONR 12 R 13 or CN.
- R 11 , R 12 and R 13 each independently represent a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aralkyl group having 7 to 30 carbon atoms or an aralkyl group having 2 to 20 carbon atoms. represents a heterocyclic group.
- R 21 , R 22 and R 23 each independently represent a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aralkyl group having 7 to 30 carbon atoms or an aralkyl group having 2 to 20 carbon atoms. represents a heterocyclic group.
- a hydrogen atom in the group represented by R 21 , R 22 or R 23 may be substituted with CN, a halogen atom, a hydroxy group or a carboxy group.
- the alkylene moiety is -O-, -S-, -COO-, -OCO-, It may be interrupted 1 to 5 times by -NR 24 -, -NR 24 CO-, -NR 24 COO-, -OCONR 24 -, -SCO-, -COS-, -OCS- or -CSO-.
- R 24 represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aralkyl group having 7 to 30 carbon atoms or a heterocyclic group having 2 to 20 carbon atoms.
- the alkyl moiety may be branched or cyclic.
- R 12 and R 13 and R 22 and R 23 may together form a ring.
- * represents a bond with the second molecular structure, which is a molecular structure other than the first molecular structure of the oxime compound (1).
- alkyl groups having 1 to 20 carbon atoms represented by R 11 , R 12 , R 13 , R 21 , R 22 , R 23 and R 24 in formula (1) include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group, pentyl group, isopentyl group, tert-pentyl group, hexyl group, heptyl group, octyl group, isooctyl group, 2-ethylhexyl group, tert -octyl group, nonyl group, isononyl group, decyl group, isodecyl group, undecyl group, dodecyl group, tetradecyl group, hexadecyl group, octadecyl group, icosyl group, cyclopentyl group
- Examples of aryl groups having 6 to 30 carbon atoms represented by R 11 , R 12 , R 13 , R 21 , R 22 , R 23 and R 24 in formula (1) include phenyl, tolyl and xylyl. group, ethylphenyl group, naphthyl group, anthryl group, phenanthryl group, phenyl group substituted with one or more of the above alkyl groups, biphenylyl group, naphthyl group, anthryl group, and the like.
- Examples of aralkyl groups having 7 to 30 carbon atoms represented by R 11 , R 12 , R 13 , R 21 , R 22 , R 23 and R 24 in formula (1) include benzyl group, ⁇ -methylbenzyl group, ⁇ , ⁇ -dimethylbenzyl group, phenylethyl group and the like.
- Examples of the heterocyclic group having 2 to 20 carbon atoms represented by R 11 , R 12 , R 13 , R 21 , R 22 , R 23 and R 24 in formula (1) include pyridyl group, pyrimidyl group, furyl group, thienyl group, tetrahydrofuryl group, dioxolanyl group, benzoxazol-2-yl group, tetrahydropyranyl group, pyrrolidyl group, imidazolidyl group, pyrazolidyl group, thiazolidyl group, isothiazolidyl group, oxazolidyl group, isoxazolidyl group, A piperidyl group, a piperazyl group, a morpholinyl group, etc., and preferably a 5- to 7-membered heterocyclic ring.
- R 12 and R 13 and R 22 and R 23 in formula (1) may together form a ring means that R 12 and R 13 and R 22 and R 23 may together It means that a ring may be formed together with the nitrogen atom, carbon atom or oxygen atom to which it is connected.
- rings that can be formed by Ra 12 and Ra 13 and Ra 22 and Ra 23 together in formula (1) include a cyclopentane ring, a cyclohexane ring, a cyclopentene ring, a benzene ring, a piperidine ring, a morpholine ring, A lactone ring, a lactam ring and the like can be mentioned, and a 5- to 7-membered ring is preferred.
- the halogen atoms which R 11 , R 12 , R 13 , R 21 , R 22 and R 23 in formula (1) may have as substituents include fluorine, chlorine, bromine and iodine atoms. be done.
- R 1 in formula (1) is preferably R 11 , more preferably an alkyl group having 1 to 20 carbon atoms, still more preferably an alkyl group having 1 to 10 carbon atoms, even more preferably 1 ⁇ 6 alkyl groups.
- the second molecular structure linked to the first molecular structure represented by Formula (1) is the structure represented by Formula (2) below.
- the second molecular structure means a portion of the molecular structure other than the first molecular structure of the oxime compound (1).
- the bond represented by "*" in formula (2) is directly bonded to the bond represented by "*" in formula (1). That is, when the second molecular structure is a structure represented by formula (2), the benzene ring having "-*" in formula (2) and the carbonyl group having "-*" in formula (1) are directly connected.
- R 2 and R 3 are each independently R 11 , OR 11 , SR 11 , COR 11 , CONR 12 R 13 , NR 12 COR 11 , OCOR 11 , COOR 11 , SCOR 11 , OCSR 11 , COSR 11 , CSOR 11 , CN or a halogen atom.
- R 2 When multiple R 2 are present, they may be the same or different.
- R3 When two or more R3 are present, they may be the same or different.
- R 11 , R 12 and R 13 have the same meanings as above.
- s and t each independently represent an integer of 0 to 4;
- L represents a sulfur atom, CR 31 R 32 , CO or NR 33 ;
- R 31 , R 32 and R 33 each independently represent a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms or an aralkyl group having 7 to 30 carbon atoms.
- R 31 , R 32 or R 33 has an alkyl moiety, the alkyl moiety may be branched or cyclic, and R 31 , R 32 and R 33 may each independently form a ring together with either adjacent benzene ring.
- R 4 is a hydroxy group, a carboxy group or the following formula (2-1)
- L 1 represents -O-, -S-, -NR 22 -, -NR 22 CO-, -SO 2 -, -CS-, -OCO- or -COO- .
- R22 has the same meaning as above.
- L 2 is a group obtained by removing v hydrogen atoms from an alkyl group having 1 to 20 carbon atoms, a group obtained by removing v hydrogen atoms from an aryl group having 6 to 30 carbon atoms, and an aralkyl group having 7 to 30 carbon atoms. represents a group obtained by removing v hydrogen atoms from or a group obtained by removing v hydrogen atoms from a heterocyclic group having 2 to 20 carbon atoms.
- the alkylene moiety is -O-, -S-, -COO-, -OCO-, -NR 22 -, -NR 22 COO-, -OCONR 22 - , -SCO-, -COS-, -OCS- or -CSO- may be interrupted 1 to 5 times, and the alkylene moiety may be branched or cyclic.
- R4a represents OR41 , SR41 , CONR42R43 , NR42COR43 , OCOR41 , COOR41 , SCOR41 , OCSR41 , COSR41 , CSOR41 , CN or a halogen atom.
- R 41 , R 42 and R 43 each independently represent a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms or an aralkyl group having 7 to 30 carbon atoms ;
- the group represented by 42 and R 43 has an alkyl moiety, the alkyl moiety may be branched or cyclic, and R 42 and R 43 together form a ring. may be formed.
- v represents an integer of 1 to 3;
- Represents a group represented by * represents a bond with the first molecular structure of the oxime compound (1).
- Examples of alkyl groups having 1 to 20 carbon atoms, aryl groups having 6 to 30 carbon atoms, and aralkyl groups having 7 to 30 carbon atoms represented by 41 , R 42 and R 43 are R 11 , Similar to the examples for R 12 , R 13 , R 21 , R 22 , R 23 and R 24 .
- R 31 , R 32 and R 33 in formula (2) may each independently form a ring together with any adjacent benzene ring means that R 31 , R 32 and R 33 means that each independently may form a ring together with either adjacent benzene ring together with the connecting nitrogen atom.
- Examples of rings that can be formed together with any of the adjacent benzene rings of R 31 , R 32 and R 33 in formula (2) are Ra 12 , Ra 13 and Ra 22 in formula (1). It is the same as the example for the ring that Ra 23 can form together.
- L 2 in the above formula (2-1) is an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aralkyl group having 7 to 30 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms. represents a group excluding v hydrogen atoms.
- the group obtained by removing v hydrogen atoms from an alkyl group having 1 to 20 carbon atoms for example, when v is 1, methylene group, ethylene group, propylene group, methylethylene group, butylene group, 1-methylpropylene group , 2-methylpropylene group, 1,2-dimethylpropylene group, 1,3-dimethylpropylene group, 1-methylbutylene group, 2-methylbutylene group, 3-methylbutylene group, 4-methylbutylene group, 2,4 -dimethylbutylene group, 1,3-dimethylbutylene group, pentylene group, hexylene group, heptylene group, octylene group, nonylene group, decylene group, dodecylene group, tridecylene group, tetradecylene group, pentadecylene group, ethane-1,1- Alkylene groups such as a diyl group and a propane-2,2-diyl group can be mentioned.
- Examples of groups obtained by removing v hydrogen atoms from an aryl group having 6 to 30 carbon atoms include, for example, when v is 1, a 1,2-phenylene group, a 1,3-phenylene group, a 1,4-phenylene group, 2,6-naphthylene group, 1,4-naphthylene group, 2,5-dimethyl-1,4-phenylene group, diphenylmethane-4,4'-diyl group, 2,2-diphenylpropane-4,4'-diyl and arylene groups such as diphenylsulfide-4,4'-diyl group and diphenylsulfone-4,4'-diyl group.
- the group obtained by removing v hydrogen atoms from an aralkyl group having 7 to 30 carbon atoms for example, when v is 1, a group represented by the following formula (a) and a group represented by the following formula (b) etc.
- L 3 and L 5 represent an alkylene group having 1 to 10 carbon atoms
- L 4 and L 6 represent a single bond or an alkylene group having 1 to 10 carbon atoms.
- alkylene group having 1 to 10 carbon atoms examples include methylene group, ethylene group, propylene group, methylethylene group, butylene group, 1-methylpropylene group, 2-methylpropylene group, 1,2-dimethylpropylene group, 1 , 3-dimethylpropylene group, 1-methylbutylene group, 2-methylbutylene group, 3-methylbutylene group, 4-methylbutylene group, 2,4-dimethylbutylene group, 1,3-dimethylbutylene group, pentylene group, A hexylene group, a heptylene group, an octylene group, a nonylene group, a decylene group and the like can be mentioned.
- Examples of groups obtained by removing v hydrogen atoms from a heterocyclic group having 2 to 20 carbon atoms include, for example, when v is 1, a 2,5-pyridinediyl group, a 2,6-pyridinediyl group, a 2,5- pyrimidinediyl group, 2,5-thiophenediyl group, 3,4-tetrahydrofurandiyl group, 2,5-tetrahydrofurandiyl group, 2,5-furandiyl group, 3,4-thiazoldiyl group, 2,5-benzofurandiyl group 2,5-benzothiophenediyl group, N-methylindole-2,5-diyl group, 2,5-benzothiazoldiyl group, and 2,5-benzoxazoldiyl group. be done.
- halogen atoms represented by R 2 and R 3 in formula (2) and R 4a in formula (2-1) above include fluorine, chlorine, bromine and iodine atoms.
- a preferred example of the structure represented by formula (2) is the structure represented by formula (2a) below. .
- L′ represents a sulfur atom or NR 50
- R 50 represents a linear, branched or cyclic alkyl group having 1 to 20 carbon atoms
- R 2 , R 3 , R 4 , s and t have the same meanings as above.
- R 44 is a hydroxy group, a carboxy group, or the following formula (2-2)
- L 11 represents —O— or *—OCO—
- * represents a bond with L 12
- L 12 represents an alkylene group having 1 to 20 carbon atoms
- the alkylene group may be interrupted by 1 to 3 —O—
- R 44a represents OR 55 or COOR 55
- R 55 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms .
- R 44 is preferably a group represented by formula (2-2). In this case, it is advantageous in terms of the solubility of the oxime compound (1) in the solvent (G) and the development speed of the curable composition.
- the alkylene group represented by L 12 preferably has 1 to 10 carbon atoms, more preferably 1 to 4 carbon atoms.
- R 44a is preferably a hydroxy group or a carboxy group, more preferably a hydroxy group.
- the method for producing the oxime compound (1) having the second molecular structure represented by formula (2) is not particularly limited, it can be produced, for example, by the method described in JP-A-2011-132215.
- Another example of the second molecular structure linked to the first molecular structure represented by Formula (1) is the structure represented by Formula (3) below.
- the bond represented by "*" in formula (3) is directly bonded to the bond represented by "*” in formula (1). That is, when the second molecular structure is a structure represented by formula (3), the benzene ring having "-*" in formula (3) and the carbonyl group having "-*" in formula (1) are directly connected.
- R 5 is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms. represents When the group represented by R 5 has an alkyl moiety, the alkyl moiety may be branched or cyclic.
- R 21 , R 22 and R 23 have the same meanings as above.
- a hydrogen atom in the group represented by R 21 , R 22 or R 23 may be substituted with CN, a halogen atom, a hydroxy group or a carboxy group.
- the groups represented by R 21 , R 22 and R 23 have an alkylene moiety, the alkylene moiety is -O-, -S-, -COO-, -OCO-, -NR 24 -, -NR 24 CO It may be interrupted 1 to 5 times by -, -NR 24 COO-, -OCONR 24 -, -SCO-, -COS-, -OCS- or -CSO-.
- R 24 has the same meaning as above.
- R 21 , R 22 and R 23 When the groups represented by R 21 , R 22 and R 23 have an alkyl moiety, the alkyl moiety may be branched or cyclic, and R 22 and R 23 are Together they may form a ring.
- R6 , R7 , R8 and R9 are each independently R61 , OR61 , SR61 , COR62 , CONR63R64 , NR65COR61 , OCOR61 , COOR62 , SCOR61 , OCSR61 , COSR 62 , CSOR 61 , a hydroxyl group, a nitro group, CN or a halogen atom.
- R 61 , R 62 , R 63 , R 64 and R 65 are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms or represents a heterocyclic group having 2 to 20 carbon atoms.
- R 6 and R 7 , R 7 and R 8 , and R 8 and R 9 may together form a ring. * represents a bond with the first molecular structure of the oxime compound (1).
- Examples of the aryl group having 6 to 30 carbon atoms, the aralkyl group having 7 to 30 carbon atoms, and the heterocyclic group having 2 to 20 carbon atoms are R 11 , R 12 , R 13 , R 21 , R 22 , Similar to the examples for R 23 and R 24 .
- R 22 and R 23 in formula (3) may together form a ring means that R 22 and R 23 together form a ring together with the connecting nitrogen atom, carbon atom or oxygen atom. It means that it may be formed.
- Examples of rings that can be formed together by R 22 and R 23 in formula (3) are rings that can be formed together by Ra 12 and Ra 13 and Ra 22 and Ra 23 in formula (1) Similar to the example for
- Examples of halogen atoms which may substitute the hydrogen atoms of include fluorine, chlorine, bromine and iodine atoms.
- R 5 is a group represented by the following formula (3-1).
- Z is a group obtained by removing one hydrogen atom from an alkyl group having 1 to 20 carbon atoms, a group obtained by removing one hydrogen atom from an aryl group having 6 to 30 carbon atoms, represents a group obtained by removing one hydrogen atom from an aralkyl group having 7 to 30 carbon atoms or a group obtained by removing one hydrogen atom from a heterocyclic group having 2 to 20 carbon atoms,
- the alkylene portion is -O-, -S-, -COO-, -OCO-, -NR 24 -, -NR 24 COO-, -OCONR 24 -, optionally interrupted 1 to 5 times by -SCO-, -COS-, -OCS- or -CSO-, the alkylene moiety may be branched or cyclic; R 21 , R 22 and R 24 have the same meanings as above. ]
- Z in formula (3-1) is preferably a methylene group, ethylene or phenylene group from the same viewpoint as above.
- R 21 and R 22 in formula (3-1) are preferably an alkyl group having 1 to 20 carbon atoms or an aryl group having 6 to 30 carbon atoms, more preferably methyl group, ethyl group or phenyl group.
- R7 is a nitro group.
- the method for producing the oxime compound (1) having the second molecular structure represented by formula (3) is not particularly limited, but for example, the methods described in JP-A-2000-80068 and JP-A-2011-178776. can be manufactured in
- R 71 is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aralkyl group having 7 to 30 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms. show.
- the alkyl moiety may be branched or cyclic.
- R 21 , R 22 and R 23 have the same meanings as above.
- a hydrogen atom in the group represented by R 21 , R 22 or R 23 may be substituted with CN, a halogen atom, a hydroxy group or a carboxy group.
- the groups represented by R 21 , R 22 and R 23 have an alkylene moiety, the alkylene moiety is -O-, -S-, -COO-, -OCO-, -NR 24 -, -NR 24 CO It may be interrupted 1 to 5 times by -, -NR 24 COO-, -OCONR 24 -, -SCO-, -COS-, -OCS- or -CSO-.
- R 24 has the same meaning as above.
- R 72 , R 73 and three R 74 are each independently R 61 , OR 61 , SR 61 , COR 62 , CONR 63 R 64 , NR 65 COR 61 , OCOR 61 , COOR 62 , SCOR 61 , OCSR 61 , COSR 62 , CSOR 61 , a hydroxyl group, a nitro group, CN or a halogen atom.
- R 61 , R 62 , R 63 , R 64 and R 65 are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms or represents a heterocyclic group having 2 to 20 carbon atoms.
- R 72 and R 73 and two R 74 may together form a ring. * represents a bond with the first molecular structure of the oxime compound (1).
- an alkyl group having 1 to 20 carbon atoms represented by R 71 , R 21 , R 22 , R 23 , R 24 , R 61 , R 62 , R 63 , R 64 and R 65 in formula (4);
- Examples of the aryl group having 6 to 30 carbon atoms, the aralkyl group having 7 to 30 carbon atoms, and the heterocyclic group having 2 to 20 carbon atoms are R 11 , R 12 , R 13 , R 21 , R 22 , Similar to the examples for R 23 and R 24 .
- R 22 and R 23 in formula (4) may together form a ring means that R 22 and R 23 together form a ring together with the connecting nitrogen atom, carbon atom or oxygen atom. It means that it may be formed.
- Examples of rings that can be formed together by R 22 and R 23 in formula (4) are rings that can be formed together by Ra 12 and Ra 13 and Ra 22 and Ra 23 in formula (1) Similar to the example for
- halogen atoms represented by R 72 , R 73 and R 74 in formula ( 4) ;
- halogen atoms which may be substituted for include fluorine, chlorine, bromine and iodine atoms.
- the method for producing the oxime compound (1) having the second molecular structure represented by formula (4) is not particularly limited, for example, the methods described in WO2017/051680 and WO2020/004601. can be manufactured in
- R 81 is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an aralkyl group having 7 to 30 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms. show.
- the alkyl moiety may be branched or cyclic.
- R 21 , R 22 and R 23 have the same meanings as above.
- a hydrogen atom in the group represented by R 21 , R 22 or R 23 may be substituted with CN, a halogen atom, a hydroxy group or a carboxy group.
- the groups represented by R 21 , R 22 and R 23 have an alkylene moiety, the alkylene moiety is -O-, -S-, -COO-, -OCO-, -NR 24 -, -NR 24 CO It may be interrupted 1 to 5 times by -, -NR 24 COO-, -OCONR 24 -, -SCO-, -COS-, -OCS- or -CSO-.
- R 24 has the same meaning as above.
- R 21 , R 22 and R 23 When the groups represented by R 21 , R 22 and R 23 have an alkyl moiety, the alkyl moiety may be branched or cyclic, and R 22 and R 23 are Together they may form a ring.
- R 82 , R 83 , R 84 , R 85 and R 86 are each independently R 61 , OR 61 , SR 61 , COR 62 , CONR 63 R 64 , NR 65 COR 61 , OCOR 61 , COOR 62 , SCOR 61 , OCSR 61 , COSR 62 , CSOR 61 , a hydroxyl group, a nitro group, CN or a halogen atom.
- R 61 , R 62 , R 63 , R 64 and R 65 are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms or represents a heterocyclic group having 2 to 20 carbon atoms.
- R 83 and R 84 , R 84 and R 85 , and R 85 and R 86 may each combine to form a ring. * represents a bond with the first molecular structure of the oxime compound (1).
- an alkyl group having 1 to 20 carbon atoms represented by R 81 , R 21 , R 22 , R 23 , R 24 , R 61 , R 62 , R 63 , R 64 and R 65 in formula (5);
- Examples of the aryl group having 6 to 30 carbon atoms, the aralkyl group having 7 to 30 carbon atoms, and the heterocyclic group having 2 to 20 carbon atoms are R 11 , R 12 , R 13 , R 21 , R 22 , Similar to the examples for R 23 and R 24 .
- R 22 and R 23 in formula (5) may together form a ring means that R 22 and R 23 together form a ring together with the connecting nitrogen atom, carbon atom or oxygen atom. It means that it may be formed.
- Examples of rings that can be formed together by R 22 and R 23 in formula (5) are rings that can be formed together by Ra 12 and Ra 13 and Ra 22 and Ra 23 in formula (1) Similar to the example for
- the method for producing the oxime compound (1) having the second molecular structure represented by formula (5) is not particularly limited, for example, the methods described in WO 2017/051680 and WO 2020/004601. can be manufactured in
- R 91 , R 92 , R 93 , R 94 , R 95 , R 96 and R 97 are each independently R 61 , OR 61 , SR 61 , COR 62 , CONR 63 R 64 , NR 65 COR 61 , OCOR 61 , COOR 62 , SCOR 61 , OCSR 61 , COSR 62 , CSOR 61 , hydroxyl group, nitro group, CN or halogen atom;
- R 61 , R 62 , R 63 , R 64 and R 65 are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms or represents a heterocyclic group having 2 to 20 carbon atoms.
- R 21 , R 22 and R 23 have the same meanings as above.
- R 92 and R 93 , R 94 and R 95 , R 95 and R 96 and R 96 and R 97 may each combine to form a ring. * represents a bond with the first molecular structure of the oxime compound (1).
- Alkyl groups having 1 to 20 carbon atoms and aryl groups having 6 to 30 carbon atoms represented by R 21 , R 22 , R 23 , R 61 , R 62 , R 63 , R 64 and R 65 in formula (6) , an aralkyl group having 7 to 30 carbon atoms, and a heterocyclic group having 2 to 20 carbon atoms are the examples of R 11 , R 12 , R 13 , R 21 , R 22 and R 23 in formula (1) and It is the same.
- R 22 and R 23 in formula (6) may together form a ring means that R 22 and R 23 together form a ring together with the connecting nitrogen atom, carbon atom or oxygen atom. It means that it may be formed.
- Examples of rings that can be formed together by R 22 and R 23 in formula (6) are rings that can be formed together by Ra 12 and Ra 13 and Ra 22 and Ra 23 in formula (1) Similar to the example for
- the method for producing the oxime compound (1) having the second molecular structure represented by formula (6) is not particularly limited, for example, the methods described in WO 2017/051680 and WO 2020/004601. can be manufactured in
- the photopolymerization initiator (C) can further contain photopolymerization initiators other than the oxime compound (1).
- Other photopolymerization initiators include oxime compounds other than oxime compound (1), alkylphenone compounds, biimidazole compounds, triazine compounds and acylphosphine compounds.
- oxime compounds other than oxime compound (1) include oxime compounds having a partial structure represented by the following formula (d1). * represents a bond.
- Examples of the oxime compound having a partial structure represented by formula (d1) include N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, N-benzoyloxy-1- (4-phenylsulfanylphenyl) octan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropan-1-one-2-imine, N-acetoxy-1 -[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethan-1-imine, N-acetoxy-1-[9-ethyl-6- ⁇ 2-methyl-4-( 3,3-dimethyl-2,4-dioxacyclopentanylmethyloxy)benzoyl ⁇ -9H-carbazol-3-yl]ethan-1-imine, N-acetoxy-1-[9-ethy
- oxime compounds having a partial structure represented by formula (d1) include N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, N-benzoyloxy-1-( At least selected from the group consisting of 4-phenylsulfanylphenyl)octan-1-one-2-imine and N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropan-1-one-2-imine One is preferred, and N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine is more preferred.
- An alkylphenone compound is a compound having a partial structure represented by the following formula (d4) or a partial structure represented by the following formula (d5).
- the benzene ring may have a substituent.
- Examples of compounds having a structure represented by formula (d4) include 2-methyl-2-morpholino-1-(4-methylsulfanylphenyl)propan-1-one, 2-dimethylamino-1-(4-morpholinophenyl )-2-benzylbutan-1-one, 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]butan-1-one and the like be done.
- Commercially available products such as OMNIRAD 369, OMNIRAD 907, and OMNIRAD 379 (manufactured by IGM Resins) may also be used.
- Compounds having a structure represented by formula (d5) include 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-hydroxy-2-methyl-1-[4-(2-hydroxyethoxy ) Phenyl]propan-1-one, 1-hydroxycyclohexylphenyl ketone, oligomers of 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propan-1-one, ⁇ , ⁇ -diethoxyacetophenone, benzyl dimethyl ketal and the like.
- the alkylphenone compound is preferably a compound having a structure represented by formula (d4).
- biimidazole compounds examples include compounds represented by formula (d6).
- R E to R J represent an aryl group having 6 to 10 carbon atoms which may have a substituent.
- the aryl group having 6 to 10 carbon atoms includes, for example, phenyl group, toluyl group, xylyl group, ethylphenyl group and naphthyl group, preferably phenyl group.
- substituents include halogen atoms and alkoxy groups having 1 to 4 carbon atoms.
- the halogen atom includes, for example, a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, preferably a chlorine atom.
- Examples of the alkoxy group having 1 to 4 carbon atoms include methoxy group, ethoxy group, propoxy group, butoxy group and the like, preferably methoxy group.
- Biimidazole compounds include, for example, 2,2′-bis(2-chlorophenyl)-4,4′,5,5′-tetraphenylbiimidazole, 2,2′-bis(2,3-dichlorophenyl)-4 ,4′,5,5′-tetraphenylbiimidazole (see, for example, JP-A-06-75372 and JP-A-06-75373), 2,2′-bis(2-chlorophenyl)-4, 4′,5,5′-tetraphenylbiimidazole, 2,2′-bis(2-chlorophenyl)-4,4′,5,5′-tetra(alkoxyphenyl)biimidazole, 2,2′-bis( 2-chlorophenyl)-4,4',5,5'-tetra(dialkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-t
- triazine compounds examples include 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxy naphthyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-piperonyl-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxystyryl )-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(5-methylfuran-2-yl)ethenyl]-1,3,5-triazine, 2,4- Bis(trichloromethyl)-6-[2-(furan-2-yl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(furan-2-yl)ethenyl]-1,3,5-tri
- acylphosphine compounds include bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide and (2,4,6-trimethylbenzoyl)diphenylphosphine oxide.
- photopolymerization initiators other than the oxime compound (1) include benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether; benzophenone, o-benzoyl benzoin.
- methyl acid 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenylsulfide, 3,3',4,4'-tetra(tert-butylperoxycarbonyl)benzophenone, 2,4,6-trimethylbenzophenone, 4 benzophenone compounds such as ,4'-bis(diethylamino)benzophenone; quinone compounds such as 9,10-phenanthrenequinone, 2-ethylanthraquinone and camphorquinone; 10-butyl-2-chloroacridone, benzyl, phenylglyoxylic acid Examples include methyl and titanocene compounds.
- a photopolymerization initiator other than the oxime compound (1) may be used alone, or two or more photopolymerization initiators may be used in combination.
- the other photopolymerization initiator includes an oxime compound other than the oxime compound (1) described above, an alkylphenone compound, Biimidazole compounds, triazine compounds, acylphosphine compounds, and the like.
- the content of the photopolymerization initiator (C) in the curable composition is preferably 0 with respect to 100 parts by mass of the photopolymerizable compound (B). .1 parts by mass or more and 300 parts by mass or less, more preferably 0.1 parts by mass or more and 200 parts by mass or less.
- the productivity of the cured film tends to improve.
- Resin (D) The curable composition can further contain a resin (D).
- the resin (D) can further contain one or more resins.
- the resin (D) include the following resins [K1] to [K4].
- Resin [K1] at least one (a) selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic acid anhydrides (hereinafter also referred to as "(a)"), and copolymerizable with (a) A copolymer with a monomer (c) (but different from (a)) (hereinafter also referred to as "(c)”);
- (a) includes, for example, (meth)acrylic acid, crotonic acid, and unsaturated monocarboxylic acids such as o-, m-, and p-vinylbenzoic acid; Maleic acid, fumaric acid, citraconic acid, mesaconic acid, itaconic acid, 3-vinyl phthalic acid, 4-vinyl phthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3,6-tetrahydrophthalic acid, dimethyl Unsaturated dicarboxylic acids such as tetrahydrophthalic acid and 1,4-cyclohexenedicarboxylic acid; methyl-5-norbornene-2,3-dicarboxylic acid, 5-carboxybicyclo[2.2.1]hept-2-ene, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene, 5-carboxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-carboxy-5-eth
- (b) is, for example, a monomer having a cyclic ether structure having 2 to 4 carbon atoms (eg, at least one selected from the group consisting of an oxirane ring, an oxetane ring and a tetrahydrofuran ring) and an ethylenically unsaturated bond; be.
- (b) is preferably a monomer having a cyclic ether structure with 2 to 4 carbon atoms and a (meth)acryloyloxy group.
- Examples of (b) include glycidyl (meth)acrylate, ⁇ -methylglycidyl (meth)acrylate, ⁇ -ethylglycidyl (meth)acrylate, glycidyl vinyl ether, o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, p -vinylbenzyl glycidyl ether, ⁇ -methyl-o-vinylbenzyl glycidyl ether, ⁇ -methyl-m-vinylbenzyl glycidyl ether, ⁇ -methyl-p-vinylbenzyl glycidyl ether, 2,3-bis(glycidyloxymethyl)styrene , 2,4-bis(glycidyloxymethyl)styrene, 2,5-bis(glycidyloxymethyl)styrene, 2,6-bis(glycidyloxy
- (c) includes, for example, methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, sec-butyl (meth)acrylate, tert-butyl (meth)acrylate, 2-ethylhexyl (meth) Acrylate, dodecyl (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, cyclopentyl (meth)acrylate, cyclohexyl (meth)acrylate, 2-methylcyclohexyl (meth)acrylate, tricyclo[5.2.1.0 2,6 ]decane-8-yl (meth)acrylate (in the technical field, it is commonly referred to as "dicyclopentanyl (meth)acrylate”.
- tricyclodecyl (meth)acrylate tricyclo[5.2.1.0 2,6 ]decen-8-yl (meth)acrylate (in the art, it is commonly called “dicyclopentenyl (meth)acrylate”.
- dicyclopentanyloxyethyl (meth)acrylate isobornyl (meth)acrylate, adamantyl (meth)acrylate, allyl (meth)acrylate, propargyl (meth)acrylate, phenyl (meth)acrylate, naphthyl (meth)acrylate, benzyl (meth)acrylic acid ester such as (meth)acrylate; Hydroxy group-containing (meth)acrylic acid esters such as 2-hydroxyethyl (meth)acrylate and 2-hydroxypropyl (meth)acrylate; Dicarboxylic acid diesters such as diethyl maleate, diethyl fumarate, and diethyl itaconate; bicyclo[2.2.1]hept-2-ene, 5-methylbicyclo[2.2.1]hept-2-ene, 5-ethylbicyclo[2.2.1]hept-2-ene, 5- Hydroxybicyclo[2.2.1]hept-2-ene, 5-
- styrene vinyltoluene
- N-phenylmaleimide N-cyclohexylmaleimide
- N-benzylmaleimide bicyclo[2.2.1]hept- 2-ene and the like are preferred.
- the ratio of structural units derived from each of the total structural units constituting the resin [K1] is Structural units derived from (a); 2 mol% or more and 60 mol% or less Structural units derived from (c); preferably 40 mol% or more and 98 mol% or less, Structural units derived from (a): 10 mol % or more and 50 mol % or less Structural units derived from (c): More preferably 50 mol % or more and 90 mol % or less.
- the ratio of the constituent units of the resin [K1] is within the above range, the storage stability of the curable composition and the developability and solvent resistance of the cured film tend to be excellent.
- the resin [K1] is, for example, the method described in the document "Experimental Methods for Polymer Synthesis” (written by Takayuki Otsu, Published by Kagaku Dojin, 1st Edition, 1st Edition, March 1, 1972) and the document It can be manufactured with reference to the cited document described in .
- a polymerization initiator e.g., a polymerization initiator, a solvent, and the like are placed in a reaction vessel, and, for example, by replacing oxygen with nitrogen, a deoxygenated atmosphere is created, and while stirring, A method of heating and keeping warm can be mentioned.
- the polymerization initiator, solvent, and the like used here are not particularly limited, and those commonly used in the field can be used.
- polymerization initiators include azo compounds (2,2′-azobisisobutyronitrile, 2,2′-azobis(2,4-dimethylvaleronitrile), etc.) and organic peroxides (benzoyl peroxide, etc.).
- the solvent any solvent can be used as long as it dissolves each monomer, and examples of the solvent (G) contained in the curable composition include the solvents described later.
- the obtained copolymer may be used as a solution after the reaction as it is, may be used as a concentrated or diluted solution, or may be obtained as a solid (powder) by a method such as reprecipitation. may be used. If the solvent (G) described below is used as a solvent for polymerization, the solution after the reaction can be used as it is for the preparation of the curable composition, thus simplifying the production process of the curable composition. can.
- Resin [K2] is a copolymer of (a) and (c), and the cyclic ether having 2 to 4 carbon atoms of (b) is added to the carboxylic acid and/or carboxylic anhydride of (a). It can be manufactured by First, a copolymer of (a) and (c) is produced in the same manner as the method for producing resin [K1]. In this case, the ratio of structural units derived from each is preferably the same as the ratio described for resin [K1].
- part of the carboxylic acid and/or carboxylic anhydride derived from (a) in the copolymer is reacted with the cyclic ether having 2 to 4 carbon atoms of (b).
- the atmosphere in the flask was replaced from nitrogen to air, and (b) a reaction catalyst (e.g., organic phosphorus compound, metal complex, amine compound, etc.) and a polymerization inhibitor (e.g., hydroquinone, etc.), for example, at 60° C. or higher and 130° C. or lower for 1 to 10 hours, to produce the resin [K2].
- a reaction catalyst e.g., organic phosphorus compound, metal complex, amine compound, etc.
- a polymerization inhibitor e.g., hydroquinone, etc.
- the amount of (b) used is preferably 5 mol or more and 80 mol or less, more preferably 10 mol or more and 75 mol or less, relative to 100 mol of (a). Within this range, the storage stability of the curable composition, the developability of the cured film, and the solvent resistance, heat resistance and mechanical strength of the cured film tend to be well balanced.
- the amine compound as the reaction catalyst for example, an aliphatic tertiary amine compound or an aliphatic quaternary ammonium salt compound can be used. Specific examples thereof include tris(dimethylaminomethyl)phenol, triethylamine, tetrabutylammonium bromide, tetrabutylammonium chloride and the like.
- the reaction catalyst is preferably an organic phosphorus compound.
- the amount of the reaction catalyst used is preferably 0.001 parts by mass or more and 5 parts by mass or less with respect to 100 parts by mass of the total amount of (a), (b) and (c).
- the amount of the polymerization inhibitor used is preferably 0.001 parts by mass or more and 5 parts by mass or less with respect to 100 parts by mass of the total amount of (a), (b) and (c).
- Reaction conditions such as the preparation method, reaction temperature and time can be appropriately adjusted in consideration of the production equipment and the amount of heat generated by polymerization.
- the charging method and the reaction temperature can be appropriately adjusted in consideration of the production equipment, the amount of heat generated by the polymerization, and the like.
- a copolymer of (b) and (c) is obtained in the same manner as in the method for producing resin [K1] described above.
- the obtained copolymer may be used as a solution after the reaction as it is, may be used as a concentrated or diluted solution, or may be converted into a solid (powder) by a method such as reprecipitation. You may use what was taken out as.
- Resin [K3] is prepared by adding a carboxylic acid or It can be obtained by reacting a carboxylic acid anhydride.
- the amount of (a) to be reacted with the copolymer is preferably 5 mol or more and 80 mol or less per 100 mol of (b).
- Resin [K4] is a resin obtained by reacting resin [K3] with a carboxylic acid anhydride.
- the hydroxy group generated by the reaction of the cyclic ether with the carboxylic acid or carboxylic anhydride is reacted with the carboxylic anhydride.
- carboxylic anhydrides include maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinyl phthalic anhydride, 4-vinyl phthalic anhydride, and 3,4,5,6-tetrahydrophthalic anhydride.
- the amount of the carboxylic anhydride used is preferably 0.5 mol or more and 1 mol or less per 1 mol of the amount of (a) used.
- resin [K1], resin [K2], resin [K3] and resin [K4] include benzyl (meth)acrylate/(meth)acrylic acid copolymer, styrene/(meth)acrylic acid copolymer, etc.
- the alkali-soluble resin has a double bond in the side chain and has a structural unit ( ⁇ ) represented by the following formula (I) and a structural unit ( ⁇ ) and further containing an acid group (hereinafter also referred to as “resin (Da)”).
- the acid group is, for example, a resin (Da) that is introduced into the resin by including a structural unit ( ⁇ ) derived from an acid group-containing monomer (for example, (meth)acrylic acid, etc.). can.
- the resin (Da) preferably contains structural units ( ⁇ ), ( ⁇ ) and ( ⁇ ) in its main chain skeleton.
- R A and R B are the same or different and represent a hydrogen atom or a hydrocarbon group having 1 to 25 carbon atoms.
- n represents the average number of repeating units of the structural unit represented by formula (I), and is a number of 1 or more.
- R 2 C is the same or different and represents a hydrogen atom or a methyl group.
- RD which may be the same or different, represents a linear or branched hydrocarbon group having 4 to 20 carbon atoms.
- m represents the average number of repeating units of the structural unit represented by formula (II), and is a number of 1 or more.
- the content of the structural unit ( ⁇ ) is 100 mass of the total amount of all monomer units that provide the main chain skeleton of the resin (Da). %, for example, 0.5% by mass or more and 50% by mass or less, preferably 1% by mass or more and 40% by mass or less, more preferably 5% by mass or more and 30% by mass or less.
- n in formula (I) represents the average number of repeating units of the structural unit ( ⁇ ) in the resin (Da), and n can be set so that the content of the structural unit ( ⁇ ) is within the above range. can.
- the content of the structural unit ( ⁇ ) is, for example, 10% by mass or more and 90% by mass with respect to 100% by mass of the total amount of all monomer units that provide the main chain skeleton of the resin (Da). %, preferably 20% by mass or more and 80% by mass or less, more preferably 30% by mass or more and 75% by mass or less.
- m in the formula (II) represents the average number of repeating units of the structural unit ( ⁇ ) in the resin (Da), and is set so that the content of the structural unit ( ⁇ ) is within the range described above. can be done.
- the content of the structural unit ( ⁇ ) is determined from the viewpoint of the solubility of the resin (Da) in alkaline substances and the solubility of the resin (Da) in the solvent (G). For example, it is 0.5% by mass or more and 50% by mass or less, preferably 2% by mass or more and 50% by mass or less, more preferably 5% by mass or more and 45% by mass or less, relative to 100% by mass of the total amount of the units.
- the resin (D) is one or more selected from the group consisting of the above resin [K1], resin [K2], resin [K3], resin [K4] and alkali-soluble resins described in JP-A-2018-123274. can include
- resin (D) examples include polyalkylene glycol compounds.
- polyalkylene glycol compounds include polyethylene glycol and polypropylene glycol.
- a polyalkylene glycol compound is advantageous in enhancing the dispersibility of the light scattering agent (A) in the curable composition.
- the resin (D) preferably has a weight average molecular weight (Mw) in terms of standard polystyrene measured by gel permeation chromatography (GPC) of 9000 or less.
- Mw of the resin (D) in terms of standard polystyrene is, for example, 1000 or more and 9000 or less, preferably 2000 or more and 8500 or less, more preferably 3000 or more and 8500 or less, from the viewpoint of the development speed of the cured film and the emitted light intensity.
- reaction conditions such as selection of raw materials to be used, charging method, reaction temperature and time can be appropriately combined and adjusted.
- the molecular weight distribution [weight average molecular weight (Mw)/number average molecular weight (Mn)] of the resin (D) measured by GPC is, for example, 1.0 or more and 6.0 or less. It is preferably 1.2 or more and 4.0 or less.
- the acid value of the resin (D) is preferably 90 mgKOH/g or more and 150 mgKOH/g or less based on the solid content. If the acid value is less than 90 mgKOH/g, the solubility of the cured film in an alkaline developer may be low and may leave a residue on the substrate. There is a high possibility that pattern peeling will occur.
- the acid value of the resin (D) is preferably 95 mgKOH/g or more and 140 mgKOH/g or less, more preferably 100 mgKOH/g or more and 130 mgKOH/g or less, from the viewpoint of the developability of the cured film.
- the acid value is a value measured as the amount (mg) of potassium hydroxide required to neutralize 1 g of the resin (D), and can be determined by titration with an aqueous potassium hydroxide solution, for example.
- the resin (D) may contain a resin having a double bond equivalent of, for example, 300 g/eq or more and 2000 g/eq or less, preferably 500 g/eq or more and 1500 g/eq or less.
- the resin (D) contains a resin having a double bond equivalent of 300 g/eq or more and 2000 g/eq or less
- the phenomenon of quenching during the process of producing a cured pattern tends to be easily prevented.
- the resin (D) contains a resin having a double bond equivalent weight of less than 300 g/eq
- the cured pattern tends to peel off without being dissolved during development.
- Resins having a double bond equivalent of 300 g/eq or more and 2000 g/eq or less include (meth)acrylic resins.
- the resin (D) preferably consists of a (meth)acrylic resin.
- the content of the resin (D) in the curable composition is, for example, 5% by mass or more, preferably 10%, based on the total solid content of the curable composition. % by mass or more, more preferably 15% by mass or more, more preferably 30% by mass or more, particularly preferably 45% by mass, for example 80% by mass or less, preferably 75% by mass or less, more preferably 65% by mass or less be.
- the content of the resin (D) is within the above range, it tends to be easy to maintain a high emitted light intensity during the process of producing a cured pattern.
- the mass ratio (solid content ratio) of the resin (D) to the photopolymerizable compound (B) is, for example, 1 or more, and from the viewpoint of the developability of the cured film , preferably 1.2 or more and 7.0 or less, more preferably 1.5 or more and 6.0 or less, and still more preferably 2.5 or more and 5.5 or less.
- the curable composition may further comprise one or more antioxidants (E).
- the antioxidant (E) is not particularly limited as long as it is an antioxidant that is commonly used industrially, and includes phenol antioxidants, phosphorus antioxidants, phosphorus/phenol composite antioxidants and sulfur antioxidants. An antioxidant or the like can be used.
- the phosphorus/phenol composite antioxidant can be a compound having one or more phosphorus atoms and one or more phenol structures in the molecule. From the viewpoint of the developability of the cured film and the intensity of emitted light, the antioxidant (E) preferably contains a phosphorus/phenol composite antioxidant.
- Phenolic antioxidants include, for example, Irganox (registered trademark) 1010 (Irganox 1010: pentaerythritol tetrakis [3-(3,5-di-tert-butyl-4-hydroxyphenyl) propionate], BASF Corporation) ), 1076 (Irganox 1076: octadecyl-3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate, manufactured by BASF), 1330 (Irganox 1330: 3,3',3 '',5,5',5''-hexa-tert-butyl-a,a',a''-(mesitylene-2,4,6-triyl)tri-p-cresol, manufactured by BASF Corporation) , 3114 (Irganox 3114: 1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)-1,3,5-triazine
- Phosphorus-based antioxidants include, for example, Irgafos (registered trademark) 168 (Irgafos 168: Tris (2,4-di-tert-butylphenyl) phosphite, manufactured by BASF Corporation), Irgafos 12 (Irgafos 12: Tris [2-[[2,4,8,10-tetra-tert-butyldibenzo[d,f][1,3,2]dioxaphosphine-6-yl]oxy]ethyl]amine, BASF Corporation ), Irgafos 38 (Irgafos 38: bis(2,4-bis(1,1-dimethylethyl)-6-methylphenyl)ethyl ester phosphorous acid, manufactured by BASF Corporation), Adekastab (registered trademark) 329K, PEP36, PEP-8 (manufactured by ADEKA Co., Ltd.), Sandstab P-EP
- Phosphorus/phenol composite antioxidants include, for example, Sumilizer (registered trademark) GP (6-[3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propoxy]-2,4,8, 10-tetra-tert-butyldibenz[d,f][1.3.2]dioxaphosphepin) (manufactured by Sumitomo Chemical Co., Ltd.) and the like.
- sulfur-based antioxidants include dialkylthiodipropionate compounds such as dilauryl thiodipropionate, dimyristyl or distearyl, and ⁇ -alkylmercaptopropionate esters of polyols such as tetrakis[methylene(3-dodecylthio)propionate]methane. compounds and the like.
- the content of the antioxidant (E) in the curable composition is, for example, 1 part by mass or more with respect to 100 parts by mass of the resin (D), From the viewpoint of easily increasing the heat resistance of the cured film, it is preferably 2 parts by mass or more, more preferably 3 parts by mass or more, even more preferably 5 parts by mass or more, particularly preferably 7 parts by mass or more, for example 50 parts by mass or less. From the viewpoint of easily increasing the mechanical strength of the cured film, it is preferably 40 parts by mass or less, more preferably 30 parts by mass or less, and even more preferably 25 parts by mass or less.
- Leveling agent (F) The curable composition can further comprise one or more leveling agents (F).
- leveling agent (F) By containing the leveling agent (F), the flatness of the cured film can be improved.
- the leveling agent (F) include silicone-based surfactants, fluorine-based surfactants, and silicone-based surfactants having fluorine atoms. These may have a polymerizable group in the side chain.
- the leveling agent (F) is preferably a fluorosurfactant from the viewpoint of the developability of the cured film and the intensity of emitted light.
- silicone-based surfactants include surfactants that have siloxane bonds in their molecules.
- Toray Silicone DC3PA, Toray SH7PA, Toray DC11PA, Toray SH21PA, Toray SH28PA, Toray SH29PA, Toray SH30PA, Toray SH8400 (trade name: Dow Corning Toray Co., Ltd.), KP321, KP322, KP323, KP324 , KP326, KP340, KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452 and TSF4460 (manufactured by Momentive Performance Materials Japan LLC), etc. .
- fluorine-based surfactants include surfactants that have a fluorocarbon chain in the molecule.
- Florard registered trademark
- FC430 Florard FC431 (manufactured by Sumitomo 3M Co., Ltd.)
- Megafac registered trademark
- F142D Florado F171, Flora F172, Flora F173, Flora F177, Flora F183, Flora F554 F575, R30, RS-718-K
- F-top registered trademark
- EF301 EF303
- EF351, EF352 manufactured by Mitsubishi Materials Electronic Chemicals Co., Ltd.
- Surflon registered trademark
- silicone-based surfactants having fluorine atoms include surfactants having siloxane bonds and fluorocarbon chains in the molecule.
- Megafac registered trademark
- Megafac BL20 Megafac F475, F477 and F443 (manufactured by DIC Corporation) and the like can be mentioned.
- the content of the leveling agent (F) in the curable composition is, for example, 0.001% by mass or more and 1.0% by mass with respect to the total amount of the curable composition % or less, preferably 0.005% by mass or more and 0.75% by mass or less, more preferably 0.01% by mass or more and 0.5% by mass or less, still more preferably 0.05% by mass or more and 0.5% by mass or less It is below.
- the content of the leveling agent (F) is within the above range, the flatness of the cured film can be improved.
- the curable composition may optionally contain photopolymerization initiation aids, polymerization inhibitors, fillers, other polymer compounds, adhesion promoters, light stabilizers, chain transfer agents, etc. known in the art. Additives may also be included. From the viewpoint of enhancing the dispersibility of the light scattering agent (A), the curable composition contains at least one selected from the group consisting of a thiol group (—SH), a carboxyl group (—COOH) and an amino group (—NH 2 ). It may contain an organic compound with a seed group.
- the curable composition can further contain one or more solvents (G).
- the solvent (G) is not particularly limited as long as it dissolves the photopolymerizable compound (B), and solvents commonly used in the art can be used.
- ester solvent solvent (solvent containing -COO- in the molecule but not containing -O-)
- ether solvent solvent containing -O- in the molecule but not containing -COO-
- ether ester solvent solvent containing -COO- in the molecule solvent containing -COO- and -O-
- ketone solvent solvent containing -CO- in the molecule and not containing -COO-
- alcohol solvent containing OH in the molecule, -O-, - solvents containing no CO- and COO-
- aromatic hydrocarbon solvents amide solvents, dimethyl sulfoxide and the like.
- Ester solvents include methyl lactate, ethyl lactate, n-butyl lactate, methyl 2-hydroxyisobutanoate, ethyl acetate, n-butyl acetate, isobutyl acetate, n-pentyl formate, isopentyl acetate, n-butyl propionate, and isopropyl butyrate.
- ethyl butyrate n-butyl butyrate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, cyclohexanol acetate and ⁇ -butyrolactone.
- Ether solvents include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, and propylene glycol monoethyl ether.
- propylene glycol monopropyl ether propylene glycol monobutyl ether, 3-methoxy-1-butanol, 3-methoxy-3-methylbutanol, tetrahydrofuran, tetrahydropyran, 1,4-dioxane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenetol, methylanisole and the like.
- Ether ester solvents include methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, 3-ethoxy ethyl propionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methylpropionate, Ethyl 2-ethoxy-2-methylpropionate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether a
- Ketone solvents include 4-hydroxy-4-methyl-2-pentanone, acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, cyclopentanone, cyclohexanone and isophorone. etc.
- Alcohol solvents include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol and glycerin.
- Aromatic hydrocarbon solvents include benzene, toluene, xylene and mesitylene.
- Amide solvents include N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, and the like.
- Examples of the solvent (G) include propylene glycol monomethyl ether acetate, ethyl lactate, propylene glycol monomethyl ether, ethyl 3-ethoxypropionate, ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, 4-hydroxy-4- Methyl-2-pentanone, toluene, or mixtures of two or more thereof are preferred, more preferably propylene glycol monomethyl ether acetate.
- the solvent (G) is a component other than the solid content of the curable composition, and the solvent (G) includes the solvent contained in the light scattering agent (A), the resin (D), and the like.
- the curable composition can be prepared by a process that includes mixing the given ingredients, as well as other optional ingredients.
- the method for producing the curable composition can further include the step of preparing resin (D).
- the curable composition according to the first embodiment contains a resin (D).
- the curable composition M contains a light scattering agent (A), a photopolymerizable compound (B) and a resin (D), and preferably further contains a photopolymerization initiator (C).
- the curable composition M preferably contains a solvent (G) in order to improve the coatability of the composition and the flatness of the composition layer during coating.
- the content of the photopolymerizable compound (B) in the curable composition M is, for example, 5% by mass or more and 50% by mass or less, preferably 7% by mass or more and 45% by mass, based on the total solid content of the curable composition. Below, it is more preferably 10% by mass or more and 40% by mass or less, still more preferably 13% by mass or more and 35% by mass or less, and even more preferably 15% by mass or more and 35% by mass or less.
- the content of the solvent (G) in the curable composition M is, with respect to the total amount of the curable composition M, for example 40% by mass or more and 95% by mass or less, preferably 45% by mass or more and 90% by mass or less, more preferably It is 50 mass % or more and 80 mass % or less.
- the curable composition according to the second embodiment does not contain resin (D).
- the curable composition N contains a light scattering agent (A) and a photopolymerizable compound (B), and preferably further contains a photopolymerization initiator (C).
- the curable composition N may contain a solvent (G), it preferably does not contain the solvent (G) or contains a small amount of the solvent (G).
- the content of the photopolymerizable compound (B) in the curable composition N is, for example, 10% by mass or more and 90% by mass or less, preferably 20% by mass or more and 80% by mass, based on the total solid content of the curable composition. Below, it is more preferably 30% by mass or more and 75% by mass or less, still more preferably 40% by mass or more and 70% by mass or less, and even more preferably 50% by mass or more and 70% by mass or less.
- the content of the solvent (G) in the curable composition N is preferably 10% by mass or less, more preferably 5% by mass or less, still more preferably 3% by mass or less, and more preferably 3% by mass or less, relative to the total amount of the curable composition N. It is preferably 2% by mass or less, particularly preferably 1% by mass or less, and may be 0% by mass or 0.5% by mass or more.
- the curable composition N can be suitably used as an ink for inkjet printers.
- the production method according to the present invention is a method for producing a cured film of a curable composition, and the curable composition contains at least a light scattering agent (A) and a photopolymerizable compound (B).
- the production method according to the present invention is suitable as a method for producing a cured film having a high Martens hardness, and a cured film of a curable composition containing a light scattering agent (A) and a photopolymerizable compound (B). and is suitable as a method for producing a cured film having a Martens hardness of 0.10 GPa or more.
- the description in the above ⁇ cured film>> is cited.
- a manufacturing method includes the following steps.
- the method for producing a cured film can include other steps than the above steps.
- Other steps include, for example, a coating step of applying the curable composition to the substrate, a discharging step of discharging the curable composition onto regions of the substrate formed with banks and partitioned by the banks, a coating step, or a discharging step.
- Examples include a drying step of drying the composition layer that has been exposed, and a developing step that is performed on the composition layer after the exposure step.
- the cured film may be formed on the entire surface of the substrate, or may be formed as a cured pattern on a part of the substrate surface.
- the curable composition used for forming the cured film contains a light scattering agent (A) and a photopolymerizable compound (B), examples of which include the curable composition described in ⁇ Curable composition> above. It is a thing.
- the application step is a step of applying a curable composition to a substrate to form a composition layer.
- the coating method includes a spin coating method, a slit coating method, a slit and spin coating method, and the like.
- the ejection step may be a step of selectively ejecting and adhering the curable composition to regions defined by the banks by, for example, an inkjet method.
- the substrate examples include glass plates such as quartz glass, borosilicate glass, alumina silicate glass, and soda-lime glass whose surface is coated with silica; resin plates such as polycarbonate, polymethyl methacrylate, and polyethylene terephthalate; and aluminum, silver, silver/copper/palladium alloy thin films, and the like.
- the substrate is preferably a glass plate, a silicon substrate, or the like.
- the substrate may be pretreated to adjust the wettability of the substrate surface.
- the pretreatment include washing with a solvent such as alcohol or acetone, acid treatment, alkali treatment, plasma treatment, corona treatment, and the like.
- the drying step may include heat drying (pre-baking) treatment, may include vacuum drying treatment, or may include both of them.
- the temperature for heat drying is preferably 30° C. or higher and 120° C. or lower, more preferably 50° C. or higher and 110° C. or lower.
- the heating time is preferably 10 seconds or more and 60 minutes or less, more preferably 30 seconds or more and 30 minutes or less.
- the thickness of the composition layer after the coating step, after the discharging step, or after the drying step is not particularly limited, and may be appropriately selected according to the desired thickness of the cured film. It is preferably 1.5 ⁇ m or more and 18 ⁇ m or less, more preferably 2 ⁇ m or more and 14 ⁇ m or less, and still more preferably 2 ⁇ m or more and 12 ⁇ m or less.
- the film thickness of the finally obtained cured film may also be the same as described above.
- a light source used for exposure is preferably a light source that emits light having a wavelength of 250 nm or more and 450 nm or less.
- the curable composition contains the photoinitiator (C), from the light of the above wavelengths, bandpass light around 436 nm, around 408 nm, or around 365 nm, depending on the absorption wavelength of the photoinitiator (C). It may be selectively taken out by a filter.
- Specific examples of light sources include mercury lamps, light-emitting diodes, metal halide lamps, and halogen lamps.
- the exposure dose X in the exposure step is preferably 50 mJ/cm 2 or more, more preferably 80 mJ/cm 2 or more, still more preferably 100 mJ/cm 2 or more, from the viewpoint of increasing the Martens hardness of the resulting cured film. It is preferably 150 mJ/cm 2 or more.
- the exposure dose X is usually 1000 mJ/cm 2 or less, preferably 800 mJ/cm 2 or less, more preferably 700 mJ/cm 2 or less.
- the exposure dose X in the exposure step is 1000 mJ/cm 2 or less, excessive shrinkage of the cured film can be prevented, and aggregation and proximity of the light scattering agent (A) in the film due to shrinkage of the cured film can be prevented. , it is possible to prevent a decrease in the emitted light intensity.
- the amount of exposure X is the amount of exposure based on a wavelength of 365 nm, and can be measured using an ultraviolet integrating photometer (UIT-250, manufactured by Ushio Inc.).
- a photolithography method is an example of a method for forming a cured pattern, which is one aspect of a cured film.
- Photolithography is a method of exposing and developing a composition layer through a photomask for forming a desired cured pattern. In this case, it is possible to uniformly irradiate the entire exposure surface with parallel light rays, and to perform accurate alignment between the photomask and the substrate on which the composition layer is formed. is preferably used.
- the unexposed portion of the composition layer is dissolved in the developer and removed, thereby imparting a pattern to the composition layer.
- the developer include aqueous solutions of alkaline compounds such as potassium hydroxide, sodium hydrogen carbonate, sodium carbonate, tetramethylammonium hydroxide, and organic solvents.
- the concentration of the alkaline compound in the aqueous solution is preferably 0.01% by mass or more and 10% by mass or less, more preferably 0.03% by mass or more and 5% by mass or less.
- the organic solvent include those similar to the solvent (G) described above.
- the developer may contain a surfactant.
- the developing method may be any of a puddle method, a dipping method, a spray method, and the like.
- the substrate may be tilted at any angle during development.
- composition layer after the exposure process or the development process is thermally cured (post-baked) in the thermal curing process.
- Polymerization of the photopolymerizable compound (B) and the like can be further advanced by the heat curing step.
- the thermosetting temperature Y in the thermosetting step is preferably 80° C. or higher, more preferably 90° C. or higher, still more preferably 100° C. or higher, still more preferably 120° C., from the viewpoint of increasing the Martens hardness of the resulting cured film.
- 150° C. or higher and particularly preferably 150° C. or higher.
- the thermosetting temperature Y is usually 250° C. or lower, preferably 240° C. or lower, more preferably 235° C. or lower. If the thermosetting temperature Y in the thermosetting step is 250° C. or less, excessive shrinkage of the cured film can be prevented, and aggregation and proximity of the light scattering agent (A) in the film due to shrinkage of the cured film can be prevented. , it is possible to prevent a decrease in the emitted light intensity.
- thermosetting time Z in the thermosetting step is preferably 0.1 hr or longer, more preferably 0.2 hr or longer, still more preferably 0.4 hr or longer, and even more preferably, from the viewpoint of increasing the Martens hardness of the resulting cured film. is 0.5 hr or more.
- the heat curing time Z is usually 2 hours or less, preferably 1.5 hours or less, more preferably 1.2 hours or less.
- the thermosetting process can be performed under an air atmosphere or under a vacuum atmosphere.
- the heat curing step is preferably performed in a vacuum atmosphere.
- a vacuum atmosphere refers to a pressure range of 150 Pa or less, preferably 120 Pa or less, more preferably 100 Pa or less, and may be 50 Pa or more.
- methods for forming a cured pattern include an inkjet method and a printing method.
- a method for forming a cured pattern by an inkjet method for example, after forming a bank on a substrate, a curable composition is selectively adhered to the regions of the substrate defined by the bank by an inkjet method, followed by an exposure step.
- a method of curing the curable composition by heat-curing in the exposure and/or heat-curing step As a method for forming the bank, a photolithographic method, an inkjet method, and the like can be mentioned, and the bank is preferably formed by the inkjet method.
- the exposure amount X (mJ/cm 2 ) in the exposure step, the thermosetting temperature Y (° C.) in the thermosetting step, and the thermosetting time Z (hr) are given by the following formula (1): X ⁇ Y ⁇ Z 2 ⁇ 3000 (1) meet.
- X ⁇ Y ⁇ Z 2 ⁇ 3000 (1) meet.
- the P value is preferably 4000 or more, more preferably 5000 or more, even more preferably 6000 or more, even more preferably 7000 or more, and particularly preferably 8000 or more.
- the P-value is preferably 10,000 or more, more preferably 15,000 or more, 18,000 or more, or 20,000 or more.
- the P value is preferably 150,000 or less, more preferably 140,000 or less, still more preferably 120,000 or less, and 100,000 or less, 30,000 or less, 22,000 or less, or 20,000 or less. There may be. Further, when the P value is within the above range, the dispersibility of the light scattering agent (A) in the cured film is enhanced, so that it is easy to obtain a cured film with small variations in emitted light intensity.
- a display device includes at least a light source and the cured film.
- Examples of the display device include a liquid crystal display device, an organic EL display device, or an inorganic EL display device. JP-A-2009-251129, JP-A-2014-2363, and the like.
- the cured film according to the present invention is used as the above white (transparent, achromatic) pattern, and is usually combined with a chromatic pattern to form a pixel.
- This chromatic pattern has a function of converting the wavelength of incident light and emitting it, and may be a cured pattern of a curable composition containing a coloring agent (quantum dots, pigments, dyes, etc.).
- a display device according to one embodiment of the present invention includes a backlight that is a blue light source and a plurality of patterns provided on the viewing side of the backlight, the patterns being a red pattern, a green pattern, and a cured film according to the present invention. , and the white pattern emits light of the wavelength emitted from the blue light source.
- the backlight was turned on, and the emitted light intensity (unit: ⁇ W) over the wavelength range of 400 nm to 500 nm was measured for the light transmitted through the reference, and the maximum value was defined as I0.
- a spectrometer Spectrum meter manufactured by Ocean Optics was used to measure the emitted light intensity.
- a substrate having a cured film was placed on the surface of the reference glass substrate.
- the backlight was turned on, and the emitted light intensity (unit: ⁇ W) over the wavelength range of 400 nm to 500 nm was measured for the light emitted from the cured film.
- a value (OD value/T) was obtained by dividing the OD value by the film thickness T ( ⁇ m) of the cured film.
- the film thickness T of the cured film was measured using a film thickness measuring device (“DEKTAK XT” manufactured by BLUKER).
- the weight average molecular weight (Mw) of resin (D1) was measured by GPC under the following conditions. Apparatus; K2479 (manufactured by Shimadzu Corporation) Column; SHIMADZU Shim-pack GPC-80M Column temperature; 40°C Solvent; Tetrahydrofuran Flow rate; 1.0 mL/min detector; RI Calibration standard material; TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-2500, A-500 (manufactured by Tosoh Corporation)
- [Acid value] Accurately weigh 3 g of the resin (D1) solution, dissolve it in a mixed solvent of 90 g of acetone and 10 g of water, and use a 0.1 N KOH aqueous solution as a titrant. COM-555), the acid value of the resin (D1) solution was measured, and the acid value (AV) per 1 g of solid content was obtained from the acid value of the solution and the solid content of the solution.
- Solid content About 1 g of the resin (D1) solution was weighed into an aluminum cup, dried at 180° C. for 1 hour, and then weighed. The solid content (% by mass) of the resin (D1) solution was calculated from the mass decrease amount.
- the resin (D1) had a standard polystyrene-equivalent weight average molecular weight of 7600, a molecular weight distribution of 2.1, an acid value of 100 mgKOH/g, and a solid content in the resin (D1) solution of 40% by mass.
- Table 1 shows the composition of the obtained curable composition.
- the contents of the components other than the solvent (G) are in terms of solid content (unit: parts by mass).
- the unit for the content of the solvent (G) is parts by mass.
- Solvent (G) in Table 1 includes the solvent contained in the dispersion or solution used for preparing the curable composition.
- Photopolymerizable compound (B1) M-510 (carboxy group-containing polyfunctional (meth)acrylate, trade name "Aronix M-510" manufactured by Toagosei Co., Ltd., solid content 100%). This compound corresponds to the photopolymerizable compound (B-3a) described above.
- Photopolymerizable compound (B3) VEEA (registered trademark) (2-(2-vinyloxyethoxy)ethyl acrylate, manufactured by Nippon Shokubai Co., Ltd.). This compound corresponds to the photopolymerizable compound (B-4) described above.
- Photopolymerizable compound (B4) Light ester E (ethyl methacrylate, manufactured by Kyoeisha Chemical Co., Ltd.). This compound corresponds to the photopolymerizable compound (B-1) described above.
- Photopolymerization initiator (C1) a compound represented by the following formula. It was produced by the method described in JP-A-2011-132215 (solid content 100%).
- Example 1 On a 5 cm square glass substrate (Eagle 2000; manufactured by Corning), the curable composition 1 obtained in Production Example 3 was applied by spin coating to a thickness of about 10 ⁇ m, and then heated at 100° C. 3 A film of curable composition 1 was formed by performing a drying step (pre-baking) for 1 minute. The film is exposed to light at an exposure dose of 100 mJ/cm 2 (365 nm standard) using an exposure machine (TME-150RSK; manufactured by Topcon Corporation) in an air atmosphere. After development, a thermal curing process (post-baking) was performed at 80° C. for 1 hour in an air atmosphere to obtain a substrate having a cured film.
- thermosetting temperature Y °C
- thermosetting time Z hr
- thermosetting atmosphere a pressure of 100 kPa.
- Table 2 also shows the measurement results of P value, Martens hardness, pencil hardness, film thickness, OD value, and OD value/T.
- Examples 6 to 9> Using the curable composition shown in Table 3, the exposure amount X (mJ/cm 2 ) in the exposure step, the thermosetting temperature Y (°C) in the thermosetting step, the thermosetting time Z (hr), and the thermosetting atmosphere were adjusted. A substrate having a cured film was obtained by carrying out the drying process, the exposure process and the thermal curing process in the same manner as in Example 1 except that the conditions were as shown in Table 3.
- Table 3 also shows the measurement results of P value, Martens hardness, pencil hardness, film thickness, OD value, and OD value/T.
Abstract
Description
本発明の1つの目的は、光散乱剤を含む硬化性組成物の硬化膜であって、変形及び破損に強い硬化膜及び該硬化膜を製造可能な方法を提供することにある。本発明の他の目的は、上記硬化膜を含む表示装置を提供することにある。
[1] 光散乱剤(A)及び光重合性化合物(B)を含む硬化性組成物の硬化膜であって、
前記硬化膜のマルテンス硬さが0.10GPa以上である、硬化膜。
[2] 前記硬化性組成物が光重合開始剤(C)をさらに含む、[1]に記載の硬化膜。
[3] 前記硬化性組成物が樹脂(D)をさらに含む、[1]又は[2]に記載の硬化膜。
[4] 前記光散乱剤(A)がTiO2の粒子を含む、[1]~[3]のいずれかに記載の硬化膜。
[5] 光散乱剤(A)及び光重合性化合物(B)を含む硬化性組成物の硬化膜の製造方法であって、
前記硬化性組成物の膜に対して光を照射する露光工程と、
前記硬化性組成物の膜を熱硬化させる熱硬化工程と、
を含み、
前記露光工程における露光量をX(mJ/cm2)、前記熱硬化工程における熱硬化温度をY(℃)、熱硬化時間をZ(hr)とするとき、下記式(1):
X×Y×Z2≧3000 (1)
を満たす、硬化膜の製造方法。
[6] 前記熱硬化工程が真空雰囲気下で行われる、[5]に記載の製造方法。
[7] [1]~[4]のいずれかに記載の硬化膜を含む表示装置。
本発明に係る硬化膜(以下、単に「硬化膜」ともいう。)は硬化性組成物の硬化膜であり、該硬化性組成物を硬化させることによって形成できる。該硬化性組成物は、光散乱剤(A)及び光重合性化合物(B)を少なくとも含有する。
本発明に係る硬化膜は、白色(透明、無彩色)の硬化膜、例えば硬化パターンとなり得るものであり、光源(例えば青色光源)からの光が入射されたときに赤色、緑色等の有彩色の光を出射させることを可能にする着色剤(量子ドット、顔料、染料等)を含まない。すなわち、本発明に係る硬化膜は、通常、入射光と同一又はほぼ同一の波長の光を散乱させつつ出射するものである。
本明細書において硬化パターンとは、硬化膜の一態様であり、パターン状に形成された硬化膜をいう。
本発明によれば、鉛筆硬度がB以上であり、かつ、出射光強度が高い硬化膜を提供することも可能である。
硬化性組成物は、光散乱剤(A)及び光重合性化合物(B)を含む。
光散乱剤(A)を含む硬化性組成物から形成される硬化膜は、該硬化膜に入射される光と同一又はほぼ同一の波長の光を散乱させつつ出射することができる。また、硬化膜に光散乱剤(A)を含有させることにより、該硬化膜の光透過率や視野角特性を制御したり、硬化膜の出射光強度を向上させたりすることができる。
市販品の例としては、
ビックケミー・ジャパン社製のDISPERBYK-101、102、103、106、107、108、109、110、111、116、118、130、140、154、161、162、163、164、165、166、170、171、174、180、181、182、183、184、185、190、192、2000、2001、2020、2025、2050、2070、2095、2150、2155;ANTI-TERRA-U、U100、203、204、250、;BYK-P104、P104S、P105、220S、6919;BYK-LPN6919、21116;LACTIMON、LACTIMON-WS;Bykumen等;
日本ルーブリゾール社製のSOLSPERSE-3000、9000、13000、13240、13650、13940、16000、17000、18000、20000、21000、24000、26000、27000、28000、31845、32000、32500、32550、33500、32600、34750、35100、36600、38500、41000、41090、53095、55000、76500等;
BASF社製のEFKA-46、47、48、452、4008、4009、4010、4015、4020、4047、4050、4055、4060、4080、4400、4401、4402、4403、4406、4408、4300、4310、4320、4330、4340、450、451、453、4540、4550、4560、4800、5010、5065、5066、5070、7500、7554、1101、120、150、1501、1502、1503等;
味の素ファインテクノ社製のアジスパーPA111、PB711、PB821、PB822、PB824等が挙げられる。
硬化性組成物は、1種又は2種以上の光重合性化合物(B)を含む。光重合性化合物(B)は、後述する光重合開始剤(C)から発生した活性ラジカル、酸等によって重合し得る化合物である。光重合性化合物(B)としては、光の照射によって、ラジカル重合反応により硬化する光ラジカル重合性化合物、並びに光の照射によってカチオン重合反応により硬化する光カチオン重合性化合物等が挙げられる。光重合性化合物(B)は、光ラジカル重合性化合物であることが好ましい。
本明細書において「(メタ)アクリレート」とは、アクリレート及び/又はメタクリレートを意味する。「(メタ)アクリロイル」、「(メタ)アクリル酸」等についても同様である。
一つの実施形態において、硬化性組成物の現像速度を向上させる観点から、光重合性化合物(B)は、硬化性組成物中に含まれる光重合性化合物(B)の総量に対して、化合物(B-3b)を50質量%以上含む。他の実施形態において、硬化膜の耐溶剤性(残膜率)を向上させる観点から、光重合性化合物(B)は、化合物(B-3a)及び化合物(B-3b)を含む。
アルミカップの上に光重合性化合物(B)を5g秤量し、その後、80℃のホットプレート上に1h設置する。初期の重量(W0)と1h後の重量(W1)から、下記式に従って揮発量(質量%)を算出する。
揮発量(質量%)=100×(W0-W1)/W0
硬化性組成物は、1種又は2種以上の光重合開始剤(C)をさらに含むことができる。光重合開始剤(C)は、光や熱の作用により活性ラジカル、酸等を発生し、重合を開始し得る化合物である。
R11、R12及びR13は、それぞれ独立に、水素原子、炭素数1~20のアルキル基、炭素数6~30のアリール基、炭素数7~30のアラルキル基又は炭素数2~20の複素環基を表す。
R11、R12又はR13で表わされる基の水素原子は、OR21、COR21、SR21、NR22Ra23、CONR22R23、-NR22-OR23、-N(COR22)-OCOR23、-C(=N-OR21)-R22、-C(=N-OCOR21)-R22、CN、ハロゲン原子、又はCOOR21で置換されていてもよい。
R21、R22及びR23は、それぞれ独立に、水素原子、炭素数1~20のアルキル基、炭素数6~30のアリール基、炭素数7~30のアラルキル基又は炭素数2~20の複素環基を表す。
R21、R22又はR23で表される基の水素原子は、CN、ハロゲン原子、ヒドロキシ基又はカルボキシ基で置換されていてもよい。
R11、R12、R13、R21、R22又はR23で表される基がアルキレン部分を有する場合、該アルキレン部分は、-O-、-S-、-COO-、-OCO-、-NR24-、-NR24CO-、-NR24COO-、-OCONR24-、-SCO-、-COS-、-OCS-又は-CSO-により1~5回中断されていてもよい。
R24は、水素原子、炭素数1~20のアルキル基、炭素数6~30のアリール基、炭素数7~30のアラルキル基又は炭素数2~20の複素環基を表す。
R11、R12、R13、R21、R22又はR23で表される基がアルキル部分を有する場合、該アルキル部分は、分枝鎖状であってもよく、環状であってもよく、また、R12とR13及びR22とR23はそれぞれ一緒になって環を形成していてもよい。
*は、オキシム化合物(1)が有する第1分子構造以外の他の分子構造である第2分子構造との結合手を表す。
式(1)中のRa12とRa13及びRa22とRa23が一緒になって形成し得る環としては、例えば、シクロペンタン環、シクロヘキサン環、シクロペンテン環、ベンゼン環、ピペリジン環、モルホリン環、ラクトン環、ラクタム環等が挙げられ、好ましくは5~7員環である。
式(2)において「*」で表される結合手は、式(1)において「*」で表される結合手と直接結合している。すなわち、第2分子構造が式(2)で表される構造である場合、式(2)中の「-*」を有するベンゼン環と式(1)中の「-*」を有するカルボニル基とは直接結合している。
R2が複数存在するとき、それらは同じであっても異なっていてもよい。
R3が複数存在するとき、それらは同じであっても異なっていてもよい。
R11、R12及びR13は、上記と同じ意味を表す。
s及びtは、それぞれ独立に、0~4の整数を表す。
Lは、硫黄原子、CR31R32、CO又はNR33を表す。
R31、R32及びR33は、それぞれ独立に、水素原子、炭素数1~20のアルキル基、炭素数6~30のアリール基又は炭素数7~30のアラルキル基を表す。
R31、R32又はR33で表される基がアルキル部分を有する場合、該アルキル部分は、分枝鎖状であってもよく、環状であってもよく、R31、R32及びR33は、それぞれ独立に、隣接するどちらかのベンゼン環と一緒になって環を形成していてもよい。
R4は、ヒドロキシ基、カルボキシ基又は下記式(2-1)
R22は、上記と同じ意味を表す。
L2は、炭素数1~20のアルキル基からv個の水素原子を除いた基、炭素数6~30のアリール基からv個の水素原子を除いた基、炭素数7~30のアラルキル基からv個の水素原子を除いた基又は炭素数2~20の複素環基からv個の水素原子を除いた基を表す。
L2で表される基がアルキレン部分を有する場合、該アルキレン部分は、-O-、-S-、-COO-、-OCO-、-NR22-、-NR22COO-、-OCONR22-、-SCO-、-COS-、-OCS-又は-CSO-により1~5回中断されていてもよく、該アルキレン部分は分枝鎖状であってもよく、環状であってもよい。
R4aは、OR41、SR41、CONR42R43、NR42COR43、OCOR41、COOR41、SCOR41、OCSR41、COSR41、CSOR41、CN又はハロゲン原子を表す。
R4aが複数存在するとき、それらは同じであっても異なっていてもよい。
R41、R42及びR43は、それぞれ独立に、水素原子、炭素数1~20のアルキル基、炭素数6~30のアリール基又は炭素数7~30のアラルキル基を表し、R41、R42及びR43で表される基がアルキル部分を有する場合、該アルキル部分は分枝鎖状であってもよく、環状であってもよく、R42とR43は、一緒になって環を形成していてもよい。
vは1~3の整数を表す。)
で表される基を表す。
*は、オキシム化合物(1)が有する第1分子構造との結合手を表す。
式(2)中のR31、R32及びR33が隣接するどちらかのベンゼン環と一緒になって形成し得る環の例は、式(1)中のRa12とRa13及びRa22とRa23が一緒になって形成し得る環についての例と同様である。
で表される基を表す。]
R44aは、好ましくはヒドロキシ基又はカルボキシ基であり、より好ましくはヒドロキシ基である。
式(3)において「*」で表される結合手は、式(1)において「*」で表される結合手と直接結合している。すなわち、第2分子構造が式(3)で表される構造である場合、式(3)中の「-*」を有するベンゼン環と式(1)中の「-*」を有するカルボニル基とは直接結合している。
R5で表される基がアルキル部分を有する場合、該アルキル部分は、分枝鎖状であってもよく、環状であってもよい。
R5で表される基の水素原子は、R21、OR21、COR21、SR21、NR22R23、CONR22R23、-NR22-OR23、-N(COR22)-OCOR23、NR22COR21、OCOR21、COOR21、-C(=N-OR21)-R22、-C(=N-OCOR21)-R22、SCOR21、OCSR21、COSR21、CSOR21、水酸基、ニトロ基、CN、ハロゲン原子、又はCOOR21で置換されていてもよい。
R21、R22及びR23は、上記と同じ意味を表す。
R21、R22又はR23で表される基の水素原子は、CN、ハロゲン原子、ヒドロキシ基又はカルボキシ基で置換されていてもよい。
R21、R22及びR23で表される基がアルキレン部分を有する場合、該アルキレン部分は、-O-、-S-、-COO-、-OCO-、-NR24-、-NR24CO-、-NR24COO-、-OCONR24-、-SCO-、-COS-、-OCS-又は-CSO-により1~5回中断されていてもよい。
R24は、上記と同じ意味を表す。
R21、R22及びR23で表される基がアルキル部分を有する場合、該アルキル部分は、分枝鎖状であってもよく、環状であってもよく、また、R22とR23は一緒になって環を形成していてもよい。
R6、R7、R8及びR9は、それぞれ独立に、R61、OR61、SR61、COR62、CONR63R64、NR65COR61、OCOR61、COOR62、SCOR61、OCSR61、COSR62、CSOR61、水酸基、ニトロ基、CN又はハロゲン原子を表す。
R61、R62、R63、R64及びR65は、それぞれ独立に、水素原子、炭素数1~20のアルキル基、炭素数6~30のアリール基、炭素数7~30のアリールアルキル基又は炭素数2~20の複素環基を表す。
R61、R62、R63、R64又はR65で表わされる基の水素原子は、OR21、COR21、SR21、NR22Ra23、CONR22R23、-NR22-OR23、-N(COR22)-OCOR23、-C(=N-OR21)-R22、-C(=N-OCOR21)-R22、CN、ハロゲン原子、又はCOOR21で置換されていてもよい。
R6とR7、R7とR8及びR8とR9はそれぞれ一緒になって環を形成していてもよい。
*は、オキシム化合物(1)が有する第1分子構造との結合手を表す。
式(3)中のR22とR23が一緒になって形成し得る環の例は、式(1)中のRa12とRa13及びRa22とRa23が一緒になって形成し得る環についての例と同様である。
Zで表される基がアルキレン部分を有する場合、該アルキレン部分は、-O-、-S-、-COO-、-OCO-、-NR24-、-NR24COO-、-OCONR24-、-SCO-、-COS-、-OCS-又は-CSO-により1~5回中断されていてもよく、該アルキレン部分は分枝鎖状であってもよく、環状であってもよく、
R21、R22及びR24は、前記と同じ意味を表す。]
式(3-1)中のR21及びR22は、上記と同様の観点から、好ましくは、炭素数1~20のアルキル基又は炭素数6~30のアリール基であり、より好ましくは、メチル基、エチル基又はフェニル基である。
式(4)において「*」で表される結合手は、式(1)において「*」で表される結合手と直接結合している。すなわち、第2分子構造が式(4)で表される構造である場合、式(4)中の「-*」を有するベンゼン環と式(1)中の「-*」を有するカルボニル基とは直接結合している。
R71で表される基がアルキル部分を有する場合、該アルキル部分は、分枝鎖状であってもよく、環状であってもよい。
R71で表される基の水素原子は、R21、OR21、COR21、SR21、NR22R23、CONR22R23、-NR22-OR23、-N(COR22)-OCOR23、NR22COR21、OCOR21、COOR21、-C(=N-OR21)-R22、-C(=N-OCOR21)-R22、SCOR21、OCSR21、COSR21、CSOR21、水酸基、ニトロ基、CN、ハロゲン原子、又はCOOR21で置換されていてもよい。
R21、R22及びR23は、前記と同じ意味を表す。
R21、R22又はR23で表される基の水素原子は、CN、ハロゲン原子、ヒドロキシ基又はカルボキシ基で置換されていてもよい。
R21、R22及びR23で表される基がアルキレン部分を有する場合、該アルキレン部分は、-O-、-S-、-COO-、-OCO-、-NR24-、-NR24CO-、-NR24COO-、-OCONR24-、-SCO-、-COS-、-OCS-又は-CSO-により1~5回中断されていてもよい。
R24は、上記と同じ意味を表す。
R21、R22及びR23で表される基がアルキル部分を有する場合、該アルキル部分は、分枝鎖状であってもよく、環状であってもよく、また、R22とR23は一緒になって環を形成していてもよい。
R72、R73及び3個のR74は、それぞれ独立に、R61、OR61、SR61、COR62、CONR63R64、NR65COR61、OCOR61、COOR62、SCOR61、OCSR61、COSR62、CSOR61、水酸基、ニトロ基、CN又はハロゲン原子を表す。
R61、R62、R63、R64及びR65は、それぞれ独立に、水素原子、炭素数1~20のアルキル基、炭素数6~30のアリール基、炭素数7~30のアリールアルキル基又は炭素数2~20の複素環基を表す。
R61、R62、R63、R64又はR65で表わされる基の水素原子は、OR21、COR21、SR21、NR22Ra23、CONR22R23、-NR22-OR23、-N(COR22)-OCOR23、-C(=N-OR21)-R22、-C(=N-OCOR21)-R22、CN、ハロゲン原子、又はCOOR21で置換されていてもよい。
R72とR73及び2個のR74はそれぞれ一緒になって環を形成していてもよい。
*は、オキシム化合物(1)が有する第1分子構造との結合手を表す。
式(4)中のR22とR23が一緒になって形成し得る環の例は、式(1)中のRa12とRa13及びRa22とRa23が一緒になって形成し得る環についての例と同様である。
式(5)において「*」で表される結合手は、式(1)において「*」で表される結合手と直接結合している。すなわち、第2分子構造が式(5)で表される構造である場合、式(5)中の「-*」を有するピロール環と式(1)中の「-*」を有するカルボニル基とは直接結合している。
R81で表される基がアルキル部分を有する場合、該アルキル部分は、分枝鎖状であってもよく、環状であってもよい。
R81で表される基の水素原子は、R21、OR21、COR21、SR21、NR22R23、CONR22R23、-NR22-OR23、-N(COR22)-OCOR23、NR22COR21、OCOR21、COOR21、-C(=N-OR21)-R22、-C(=N-OCOR21)-R22、SCOR21、OCSR21、COSR21、CSOR21、水酸基、ニトロ基、CN、ハロゲン原子、又はCOOR21で置換されていてもよい。
R21、R22及びR23は、上記と同じ意味を表す。
R21、R22又はR23で表される基の水素原子は、CN、ハロゲン原子、ヒドロキシ基又はカルボキシ基で置換されていてもよい。
R21、R22及びR23で表される基がアルキレン部分を有する場合、該アルキレン部分は、-O-、-S-、-COO-、-OCO-、-NR24-、-NR24CO-、-NR24COO-、-OCONR24-、-SCO-、-COS-、-OCS-又は-CSO-により1~5回中断されていてもよい。
R24は、上記と同じ意味を表す。
R21、R22及びR23で表される基がアルキル部分を有する場合、該アルキル部分は、分枝鎖状であってもよく、環状であってもよく、また、R22とR23は一緒になって環を形成していてもよい。
R82、R83、R84、R85及びR86は、それぞれ独立に、R61、OR61、SR61、COR62、CONR63R64、NR65COR61、OCOR61、COOR62、SCOR61、OCSR61、COSR62、CSOR61、水酸基、ニトロ基、CN又はハロゲン原子を表す。
R61、R62、R63、R64及びR65は、それぞれ独立に、水素原子、炭素数1~20のアルキル基、炭素数6~30のアリール基、炭素数7~30のアリールアルキル基又は炭素数2~20の複素環基を表す。
R61、R62、R63、R64又はR65で表わされる基の水素原子は、OR21、COR21、SR21、NR22Ra23、CONR22R23、-NR22-OR23、-N(COR22)-OCOR23、-C(=N-OR21)-R22、-C(=N-OCOR21)-R22、CN、ハロゲン原子、又はCOOR21で置換されていてもよい。
R83とR84、R84とR85及びR85とR86はそれぞれ一緒になって環を形成していてもよい。
*は、オキシム化合物(1)が有する第1分子構造との結合手を表す。
式(5)中のR22とR23が一緒になって形成し得る環の例は、式(1)中のRa12とRa13及びRa22とRa23が一緒になって形成し得る環についての例と同様である。
式(6)において「*」で表される結合手は、式(1)において「*」で表される結合手と直接結合している。すなわち、第2分子構造が式(6)で表される構造である場合、式(6)中の「-*」を有するベンゼン環と式(1)中の「-*」を有するカルボニル基とは直接結合している。
R61、R62、R63、R64及びR65は、それぞれ独立に、水素原子、炭素数1~20のアルキル基、炭素数6~30のアリール基、炭素数7~30のアリールアルキル基又は炭素数2~20の複素環基を表す。
R61、R62、R63、R64又はR65で表わされる基の水素原子は、OR21、COR21、SR21、NR22Ra23、CONR22R23、-NR22-OR23、-N(COR22)-OCOR23、-C(=N-OR21)-R22、-C(=N-OCOR21)-R22、CN、ハロゲン原子、又はCOOR21で置換されていてもよい。
R21、R22及びR23は、上記と同じ意味を表す。
R92とR93、R94とR95、R95とR96及びR96とR97はそれぞれ一緒になって環を形成していてもよい。
*は、オキシム化合物(1)が有する第1分子構造との結合手を表す。
式(6)中のR22とR23が一緒になって形成し得る環の例は、式(1)中のRa12とRa13及びRa22とRa23が一緒になって形成し得る環についての例と同様である。
他の光重合開始剤としては、オキシム化合物(1)以外のオキシム化合物、アルキルフェノン化合物、ビイミダゾール化合物、トリアジン化合物及びアシルホスフィン化合物が挙げられる。
感度の点で、アルキルフェノン化合物としては、式(d4)で表される構造を有する化合物が好ましい。
置換基としては、例えば、ハロゲン原子、炭素数1~4のアルコキシ基等が挙げられる。ハロゲン原子としては、例えば、フッ素原子、塩素原子、臭素原子、ヨウ素原子が挙げられ、好ましくは塩素原子である。炭素数1~4のアルコキシ基としては、例えば、メトキシ基、エトキシ基、プロポキシ基、ブトキシ基等挙げられ、好ましくはメトキシ基である。
硬化性組成物は、樹脂(D)をさらに含むことができる。樹脂(D)は、1種又は2種以上の樹脂をさらに含むことができる。樹脂(D)としては、以下の樹脂[K1]~[K4]等が挙げられる。
樹脂[K1];不飽和カルボン酸及び不飽和カルボン酸無水物からなる群より選ばれる少なくとも1種(a)(以下、「(a)」ともいう。)と、(a)と共重合可能な単量体(c)(ただし、(a)とは異なる。)(以下、「(c)」ともいう。)との共重合体;
樹脂[K2];(a)と(c)との共重合体に炭素数2~4の環状エーテル構造とエチレン性不飽和結合とを有する単量体(b)(以下、「(b)」ともいう。)を反応させた樹脂;
樹脂[K3];(b)と(c)との共重合体に(a)を反応させた樹脂;
樹脂[K4];(b)と(c)との共重合体に(a)を反応させ、さらにカルボン酸無水物を反応させた樹脂。
マレイン酸、フマル酸、シトラコン酸、メサコン酸、イタコン酸、3-ビニルフタル酸、4-ビニルフタル酸、3,4,5,6-テトラヒドロフタル酸、1,2,3,6-テトラヒドロフタル酸、ジメチルテトラヒドロフタル酸、1,4-シクロヘキセンジカルボン酸等の不飽和ジカルボン酸;
メチル-5-ノルボルネン-2,3-ジカルボン酸、5-カルボキシビシクロ[2.2.1]ヘプト-2-エン、5,6-ジカルボキシビシクロ[2.2.1]ヘプト-2-エン、5-カルボキシ-5-メチルビシクロ[2.2.1]ヘプト-2-エン、5-カルボキシ-5-エチルビシクロ[2.2.1]ヘプト-2-エン、5-カルボキシ-6-メチルビシクロ[2.2.1]ヘプト-2-エン、5-カルボキシ-6-エチルビシクロ[2.2.1]ヘプト-2-エン等のカルボキシ基を含有するビシクロ不飽和化合物;
無水マレイン酸、シトラコン酸無水物、イタコン酸無水物、3-ビニルフタル酸無水物、4-ビニルフタル酸無水物、3,4,5,6-テトラヒドロフタル酸無水物、1,2,3,6-テトラヒドロフタル酸無水物、ジメチルテトラヒドロフタル酸無水物、5,6-ジカルボキシビシクロ[2.2.1]ヘプト-2-エン無水物等の不飽和ジカルボン酸無水物;
こはく酸モノ〔2-(メタ)アクリロイルオキシエチル〕、フタル酸モノ〔2-(メタ)アクリロイルオキシエチル〕等の2価以上の多価カルボン酸の不飽和モノ〔(メタ)アクリロイルオキシアルキル〕エステル;
α-(ヒドロキシメチル)(メタ)アクリル酸のような、同一分子中にヒドロキシ基及びカルボキシ基を含有する不飽和(メタ)アクリレート
等が挙げられる。
これらのうち、共重合反応性の点や得られる樹脂(D)のアルカリ水溶液への溶解性の点から、(メタ)アクリル酸、無水マレイン酸等が好ましい。
3-メチル-3-メタクリルロイルオキシメチルオキセタン、3-メチル-3-アクリロイルオキシメチルオキセタン、3-エチル-3-メタクリロイルオキシメチルオキセタン、3-エチル-3-アクリロイルオキシメチルオキセタン、3-メチル-3-メタクリロイルオキシエチルオキセタン、3-メチル-3-アクリロイルオキシエチルオキセタン、3-エチル-3-メタクリロイルオキシエチルオキセタン、3-エチル-3-アクリロイルオキシエチルオキセタン等のオキセタン環とエチレン性不飽和結合とを有する単量体;
テトラヒドロフルフリルアクリレート(例えば、ビスコートV#150、大阪有機化学工業(株)製)、テトラヒドロフルフリルメタクリレート等のテトラヒドロフラン環とエチレン性不飽和結合とを有する単量体
等が挙げられる。
樹脂[K2]~[K4]の製造時の反応性が高く、未反応の(b)が残存しにくいことから、(b)としては、オキシラン環とエチレン性不飽和結合とを有する単量体が好ましい。
2-ヒドロキシエチル(メタ)アクリレート、2-ヒドロキシプロピル(メタ)アクリレート等のヒドロキシ基含有(メタ)アクリル酸エステル;
マレイン酸ジエチル、フマル酸ジエチル、イタコン酸ジエチル等のジカルボン酸ジエステル;
ビシクロ[2.2.1]ヘプト-2-エン、5-メチルビシクロ[2.2.1]ヘプト-2-エン、5-エチルビシクロ[2.2.1]ヘプト-2-エン、5-ヒドロキシビシクロ[2.2.1]ヘプト-2-エン、5-ヒドロキシメチルビシクロ[2.2.1]ヘプト-2-エン、5-(2’-ヒドロキシエチル)ビシクロ[2.2.1]ヘプト-2-エン、5-メトキシビシクロ[2.2.1]ヘプト-2-エン、5-エトキシビシクロ[2.2.1]ヘプト-2-エン、5,6-ジヒドロキシビシクロ[2.2.1]ヘプト-2-エン、5,6-ジ(ヒドロキシメチル)ビシクロ[2.2.1]ヘプト-2-エン、5,6-ジ(2’-ヒドロキシエチル)ビシクロ[2.2.1]ヘプト-2-エン、5,6-ジメトキシビシクロ[2.2.1]ヘプト-2-エン、5,6-ジエトキシビシクロ[2.2.1]ヘプト-2-エン、5-ヒドロキシ-5-メチルビシクロ[2.2.1]ヘプト-2-エン、5-ヒドロキシ-5-エチルビシクロ[2.2.1]ヘプト-2-エン、5-ヒドロキシメチル-5-メチルビシクロ[2.2.1]ヘプト-2-エン、5-tert-ブトキシカルボニルビシクロ[2.2.1]ヘプト-2-エン、5-シクロヘキシルオキシカルボニルビシクロ[2.2.1]ヘプト-2-エン、5-フェノキシカルボニルビシクロ[2.2.1]ヘプト-2-エン、5,6-ビス(tert-ブトキシカルボニル)ビシクロ[2.2.1]ヘプト-2-エン、5,6-ビス(シクロヘキシルオキシカルボニル)ビシクロ[2.2.1]ヘプト-2-エン等のビシクロ不飽和化合物;
N-フェニルマレイミド、N-シクロヘキシルマレイミド、N-ベンジルマレイミド、N-スクシンイミジル-3-マレイミドベンゾエート、N-スクシンイミジル-4-マレイミドブチレート、N-スクシンイミジル-6-マレイミドカプロエート、N-スクシンイミジル-3-マレイミドプロピオネート、N-(9-アクリジニル)マレイミド等のジカルボニルイミド誘導体;
スチレン、α-メチルスチレン、m-メチルスチレン、p-メチルスチレン、ビニルトルエン、p-メトキシスチレン、アクリロニトリル、メタクリロニトリル、塩化ビニル、塩化ビニリデン、アクリルアミド、メタクリルアミド、酢酸ビニル、1,3-ブタジエンイソプレン、2,3-ジメチル-1,3-ブタジエン
等が挙げられる。
これらのうち、共重合反応性及び樹脂(D)の耐熱性の点から、スチレン、ビニルトルエン、N-フェニルマレイミド、N-シクロヘキシルマレイミド、N-ベンジルマレイミド、ビシクロ[2.2.1]ヘプト-2-エン等が好ましい。
(a)に由来する構成単位;2モル%以上60モル%以下
(c)に由来する構成単位;40モル%以上98モル%以下
であることが好ましく、
(a)に由来する構成単位;10モル%以上50モル%以下
(c)に由来する構成単位;50モル%以上90モル%以下
であることがより好ましい。
樹脂[K1]の構成単位の比率が上記の範囲にあると、硬化性組成物の保存安定性、硬化膜の現像性及び耐溶剤性に優れる傾向がある。
ここで用いられる重合開始剤及び溶剤等は、特に限定されず、当該分野で通常使用されているものを使用することができる。例えば、重合開始剤としては、アゾ化合物(2,2’-アゾビスイソブチロニトリル、2,2’-アゾビス(2,4-ジメチルバレロニトリル)等)や有機過酸化物(ベンゾイルペルオキシド等)が挙げられ、溶剤としては、各モノマーを溶解するものであればよく、硬化性組成物に含まれる溶剤(G)として後述する溶剤等が挙げられる。
まず(a)と(c)との共重合体を、樹脂[K1]の製造方法として記載した方法と同様にして製造する。この場合、それぞれに由来する構成単位の比率は、樹脂[K1]について述べた比率と同じであることが好ましい。
(a)と(c)との共重合体の製造に引き続き、フラスコ内雰囲気を窒素から空気に置換し、(b)、カルボン酸又はカルボン酸無水物と環状エーテルとの反応触媒(例えば有機リン化合物、金属錯体、アミン化合物等)及び重合禁止剤(例えばハイドロキノン等)等の存在下、例えば60℃以上130℃以下で、1~10時間反応することにより、樹脂[K2]を製造することができる。
重合禁止剤の使用量は、(a)、(b)及び(c)の合計量100質量部に対して、好ましくは0.001質量部以上5質量部以下である。
(b)に由来する構成単位;5モル%以上95モル%以下
(c)に由来する構成単位;5モル%以上95モル%以下
であることが好ましく、
(b)に由来する構成単位;10モル%以上90モル%以下
(c)に由来する構成単位;10モル%以上90モル%以下
であることがより好ましい。
上記共重合体に反応させる(a)の使用量は、(b)100モルに対して、5モル以上80モル以下が好ましい。
カルボン酸無水物としては、例えば、無水マレイン酸、シトラコン酸無水物、イタコン酸無水物、3-ビニルフタル酸無水物、4-ビニルフタル酸無水物、3,4,5,6-テトラヒドロフタル酸無水物、1,2,3,6-テトラヒドロフタル酸無水物、ジメチルテトラヒドロフタル酸無水物、5,6-ジカルボキシビシクロ[2.2.1]ヘプト-2-エン無水物等が挙げられる。
カルボン酸無水物の使用量は、(a)の使用量1モルに対して、0.5モル以上1モル以下が好ましい。
ベンジル(メタ)アクリレート/(メタ)アクリル酸共重合体にグリシジル(メタ)アクリレートを付加させた樹脂、トリシクロデシル(メタ)アクリレート/スチレン/(メタ)アクリル酸共重合体にグリシジル(メタ)アクリレートを付加させた樹脂、トリシクロデシル(メタ)アクリレート/ベンジル(メタ)アクリレート/(メタ)アクリル酸共重合体にグリシジル(メタ)アクリレートを付加させた樹脂等の樹脂[K2];トリシクロデシル(メタ)アクリレート/グリシジル(メタ)アクリレートの共重合体に(メタ)アクリル酸を反応させた樹脂、トリシクロデシル(メタ)アクリレート/スチレン/グリシジル(メタ)アクリレートの共重合体に(メタ)アクリル酸を反応させた樹脂等の樹脂[K3];トリシクロデシル(メタ)アクリレート/グリシジル(メタ)アクリレートの共重合体に(メタ)アクリル酸を反応させた樹脂にさらにテトラヒドロフタル酸無水物を反応させた樹脂等の樹脂[K4]等が挙げられる。
中でも、樹脂(D)は、樹脂[K2]、樹脂[K3]及び樹脂[K4]からなる群より選ばれる少なくとも1種を含むことが好ましい。
酸基は、例えば樹脂(Da)が、酸基含有単量体(例えば(メタ)アクリル酸等)に由来する構成単位(γ)を含むことで、樹脂中に導入されたものであることができる。樹脂(Da)は、好ましくは、主鎖骨格に構成単位(α)、(β)及び(γ)を含む。
樹脂(D)の標準ポリスチレン換算のMwは、例えば1000以上9000以下であり、硬化膜の現像速度及び出射光強度の観点から、好ましくは2000以上8500以下、より好ましくは3000以上8500以下である。
樹脂(D)のMwを上記範囲とするために、用いる原料の選択、仕込方法、反応温度及び時間等の反応条件を適宜組み合わせて調整することができる。
300g/eq以上2000g/eq以下の二重結合当量を有する樹脂としては、(メタ)アクリル系樹脂が挙げられる。樹脂(D)は、好ましくは(メタ)アクリル系樹脂からなる。
硬化性組成物は、1種又は2種以上の酸化防止剤(E)をさらに含むことができる。
酸化防止剤(E)としては、工業的に一般に使用される酸化防止剤であれば特に限定はなく、フェノール系酸化防止剤、リン系酸化防止剤、リン/フェノール複合型酸化防止剤及び硫黄系酸化防止剤等を用いることができる。
硬化性組成物は、1種又は2種以上のレベリング剤(F)をさらに含むことができる。レベリング剤(F)を含有させることにより、硬化膜の平坦性をより良好にすることができる。
レベリング剤(F)としては、シリコーン系界面活性剤、フッ素系界面活性剤及びフッ素原子を有するシリコーン系界面活性剤等が挙げられる。これらは、側鎖に重合性基を有していてもよい。レベリング剤(F)は、硬化膜の現像性及び出射光強度の観点から、好ましくはフッ素系界面活性剤である。
硬化性組成物は、1種又は2種以上の溶剤(G)をさらに含むことができる。溶剤(G)は、光重合性化合物(B)を溶解するものであれば特に限定されず、当該分野で通常使用される溶剤を用いることができる。例えば、エステル溶剤(分子内に-COO-を含み、-O-を含まない溶剤)、エーテル溶剤(分子内に-O-を含み、-COO-を含まない溶剤)、エーテルエステル溶剤(分子内に-COO-と-O-とを含む溶剤)、ケトン溶剤(分子内に-CO-を含み、-COO-を含まない溶剤)、アルコール溶剤(分子内にOHを含み、-O-、-CO-及びCOO-を含まない溶剤)、芳香族炭化水素溶剤、アミド溶剤、ジメチルスルホキシド等が挙げられる。
硬化性組成物が光重合開始剤(C)及び/又は樹脂(D)をさらに含む場合、溶剤(G)は、これらを溶解するものであることが好ましい。
硬化性組成物は、所定の成分、並びに必要に応じて使用される他の成分を混合する工程を含む方法によって製造することができる。硬化性組成物の製造方法は、樹脂(D)を調製する工程をさらに含むことができる。
本発明に係る製造方法は硬化性組成物の硬化膜の製造方法であり、該硬化性組成物は、光散乱剤(A)及び光重合性化合物(B)を少なくとも含有する。
本発明に係る製造方法は、高いマルテンス硬さを有する硬化膜を製造するための方法として好適であり、光散乱剤(A)及び光重合性化合物(B)を含む硬化性組成物の硬化膜であってマルテンス硬さが0.10GPa以上である硬化膜を製造するための方法として好適である。本発明に係る製造方法により得られる硬化膜がマルテンス硬さの好ましい範囲については、上記<<硬化膜>>における記載が引用される。
光散乱剤(A)及び光重合性化合物(B)を含む硬化性組成物の膜(以下、「組成物層」ともいう。)に対して光を照射する露光工程、並びに
組成物層を熱硬化させる熱硬化工程。
露光工程の後に熱硬化工程を実施することが好ましい。
加熱乾燥を行う場合の温度は、30℃以上120℃以下が好ましく、50℃以上110℃以下がより好ましい。加熱時間は、10秒間以上60分間以下であることが好ましく、30秒間以上30分間以下であることがより好ましい。
減圧乾燥を行う場合は、50Pa以上150Pa以下の圧力下、20℃以上25℃以下の温度範囲で行うことが好ましい。
現像方法は、パドル法、ディッピング法及びスプレー法等のいずれでもよい。さらに現像時に基板を任意の角度に傾けてもよい。
X×Y×Z2≧3000 (1)
を満たす。
式(1)を満たすように露光工程及び熱硬化工程を実施することにより、高いマルテンス硬さを有する硬化膜を製造することができ、マルテンス硬さが0.10GPa以上である硬化膜を製造することが可能となる。以下、X×Y×Z2をP値ともいう。
本発明に係る表示装置は、光源と上記硬化膜とを少なくとも備える。表示装置としては、例えば、液晶表示装置、有機EL表示装置又は無機EL表示装置が挙げられ、具体的には、特開2006-309219号公報、特開2006-310303号公報、特開2013-15812号公報、特開2009-251129号公報、特開2014-2363号公報等に記載される表示装置が挙げられる。
本発明の一実施形態に係る表示装置は、青色光源であるバックライトと、バックライトの視認側に設けられる複数のパターンとを備え、該パターンは赤色パターン、緑色パターン及び本発明に係る硬化膜である白色(透明、無彩色)のパターンを備えており、白色のパターンからは青色光源から発せられる波長の光が放出される。
基板上に形成された硬化膜について、超微小硬さ試験機(エリオニクス社製、ENT-2100)にバーコビッチ角錐圧子を装着し、負荷-除荷試験を行い、荷重/押し込み曲線を測定した。測定温度は室温とした。ここで、最大試験荷重は6mNとし、保持時間なしで0mNまで除荷した。測定データをENT-Win ver.7.50(エリオニクス社製)により処理し、押し込み硬さ及びマルテンス硬さ(GPa)を求めた。
発光波長が444nmであるLEDランプ及び耐擦傷カバーを具備する狭指向角タイプのセンシングバックライト照明(OPFシリーズ;オプテックス・エフエー社製)をバックライトとして用意した。耐擦傷カバーを上に向けてバックライトを載置し、耐擦傷カバーの表面から高さ4cmの位置に、下記分光計に接続された発光を検出するための光ファイバーを設置した。バックライトの耐擦傷カバーの表面にリファレンスとしてのガラス基板(イーグル2000;コーニング社製)を配置した。この状態でバックライトを点灯させ、リファレンスを透過した光について、波長400nm以上500nm以下の範囲にわたる出射光強度(単位:μW)を測定し、極大値をI0とした。出射光強度の測定には、分光計Spectrum meter(Ocean Optics社製)を用いた。
OD値=-Log(I/I0)
トライボギア往復摩耗試験機(TYPE:30、HEIDON社製)を使用し、JIS
K5600-5-4:1999「塗料一般試験方法-第5部:塗膜の機械的性質-第4節:引っかき硬度(鉛筆法)」に規定される鉛筆硬度試験に従って、基板上に形成された硬化膜の表面の鉛筆硬度を測定した。測定における荷重は500g、速度は40mm/secとした。
樹脂(D1)の重量平均分子量(Mw)の測定は、GPC法により以下の条件で行った。
装置;K2479((株)島津製作所製)
カラム;SHIMADZU Shim-pack GPC-80M
カラム温度;40℃
溶媒;テトラヒドロフラン
流速;1.0mL/min
検出器;RI
校正用標準物質 ;TSK STANDARD POLYSTYRENE F-40、F-4、F-288、A-2500、A-500(東ソー(株)製)
樹脂(D1)溶液3gを精秤し、アセトン90gと水10gとの混合溶剤に溶解し、0.1規定のKOH水溶液を滴定液として用いて、自動滴定装置(平沼産業社製、商品名:COM-555)により、樹脂(D1)溶液の酸価を測定し、溶液の酸価と溶液の固形分とから固形分1g当たりの酸価(AV)を求めた。
樹脂(D1)溶液をアルミカップに約1gはかり取り、180℃で1時間乾燥した後、質量を測定した。その質量減少量から、樹脂(D1)溶液の固形分(質量%)を計算した。
TiO2ナノ粒子70部に、DISPERBYK21116(ビックケミー・ジャパン製)を固形分で3部、プロピレングリコールモノメチルエーテルアセテート(以下、「PGMEA」という。)を全量が100部になるように加えた後、ペイントシェイカーで十分に分散するまで撹拌して、散乱剤(A1)の分散液(固形分73%)を得た。
撹拌器、温度計付き還流冷却管、滴下ロート及び窒素導入管を具備したフラスコに、PGMEAを110部投入した後、窒素置換しながら撹拌し、80℃に昇温した。ジシクロペンタニルメタクリレート25部、メチルメタクリレート26部、メタクリル酸16部、2,2’-アゾビス(2,4-ジメチルバレロニトリル)11部をPGMEA110部に溶解した溶液を、滴下ロートからフラスコ中に滴下した後、80℃で3時間撹拌した。
次に、グリシジルメタクリレート16部、2、2’-メチレンビス(4-メチル-6-tert-ブチルフェノール)0.4部、トリフェニルホスフィン0.8部をフラスコ内に投入して110℃まで昇温、8時間撹拌することで重合体中のカルボン酸とエポキシ基とを反応させて、重合性不飽和結合を導入した。次いで、1,2,3,6-テトラヒドロフタル酸無水物17部を加え3時間反応を続けて、側鎖にカルボン酸基を導入した。反応液を室温まで冷却することで樹脂(D1)溶液を得た。
樹脂(D1)は、標準ポリスチレン換算の重量平均分子量が7600、分子量分布が2.1、酸価が100mgKOH/gであり、樹脂(D1)溶液中の固形分は40質量%であった。
製造例1で得られた光散乱剤(A1)の分散液、製造例2で得られた樹脂(D1)溶液、並びに、表1に示される他の成分をそれぞれ所定量混合して、硬化性組成物1~4をそれぞれ調製した。
製造例1で得られた光散乱剤(A1)の分散液、並びに、表1に示される他の成分をそれぞれ所定量混合して、硬化性組成物5を調製した。
〔1〕光重合性化合物(B1):M-510(カルボキシ基含有多官能(メタ)アクリレート、東亞合成(株)製の商品名「アロニックス M-510」、固形分100%)。この化合物は、上述の光重合性化合物(B-3a)に該当する。
〔2〕光重合性化合物(B2):A-9550(ジペンタエリスリトールポリアクリレート、新中村化学社製、固形分100%)。この化合物は、上述の光重合性化合物(B-3b)に該当する。
〔3〕光重合性化合物(B3):VEEA(登録商標)(2-(2-ビニロキシエトキシ)エチルアクリレート、株式会社日本触媒製)。この化合物は、上述の光重合性化合物(B-4)に該当する。
〔4〕光重合性化合物(B4):ライトエステルE(エチルメタクリレート、共栄社化学株式会社製)。この化合物は、上述の光重合性化合物(B-1)に該当する。
〔5〕光重合開始剤(C1):下記式で表される化合物。特開2011-132215号公報に記載される方法により製造した(固形分100%)。
〔7〕レベリング剤(F1):F-554(フッ素系レベリング剤、DIC社製、固形分100%)
〔8〕添加剤(X1):3-メルカプトプロピオン酸(東京化成工業株式会社製、固形分100%)
〔9〕溶剤(G1):PGMEA(プロピレングリコールモノメチルエーテルアセテート)
〔10〕溶剤(G2):シクロヘキシルアセテート
5cm角のガラス基板(イーグル2000;コーニング社製)上に、製造例3で得られた硬化性組成物1を、スピンコート法で膜厚が約10μmになるように塗布した後、100℃3分間の乾燥工程(プリベーク)を行って硬化性組成物1の膜を形成した。この膜に対して、大気雰囲気下、露光機(TME-150RSK;トプコン(株)製)を用いて、100mJ/cm2の露光量(365nm基準)で光照射することによって露光工程を実施し、現像後、大気雰囲気下、80℃1時間の熱硬化処理(ポストベーク)を行うことによって熱硬化工程を実施して、硬化膜を有する基板を得た。
露光工程における露光量X(mJ/cm2)、熱硬化工程における熱硬化温度Y(℃)、熱硬化時間Z(hr)、熱硬化雰囲気を表2に示されるとおりとしたこと以外は実施例1と同様にして乾燥工程、露光工程及び熱硬化工程を実施することにより、硬化膜を有する基板を得た。表2中、熱硬化雰囲気における「真空」とは、圧力100kPaを意味する。
表3に示される硬化性組成物を使用し、露光工程における露光量X(mJ/cm2)、熱硬化工程における熱硬化温度Y(℃)、熱硬化時間Z(hr)、熱硬化雰囲気を表3に示されるとおりとしたこと以外は実施例1と同様にして乾燥工程、露光工程及び熱硬化工程を実施することにより、硬化膜を有する基板を得た。
Claims (7)
- 光散乱剤(A)及び光重合性化合物(B)を含む硬化性組成物の硬化膜であって、
前記硬化膜のマルテンス硬さが0.10GPa以上である、硬化膜。 - 前記硬化性組成物が光重合開始剤(C)をさらに含む、請求項1に記載の硬化膜。
- 前記硬化性組成物が樹脂(D)をさらに含む、請求項1又は2に記載の硬化膜。
- 前記光散乱剤(A)がTiO2の粒子を含む、請求項1~3のいずれか1項に記載の硬化膜。
- 光散乱剤(A)及び光重合性化合物(B)を含む硬化性組成物の硬化膜の製造方法であって、
前記硬化性組成物の膜に対して光を照射する露光工程と、
前記硬化性組成物の膜を熱硬化させる熱硬化工程と、
を含み、
前記露光工程における露光量をX(mJ/cm2)、前記熱硬化工程における熱硬化温度をY(℃)、熱硬化時間をZ(hr)とするとき、下記式(1):
X×Y×Z2≧3000 (1)
を満たす、硬化膜の製造方法。 - 前記熱硬化工程が真空雰囲気下で行われる、請求項5に記載の製造方法。
- 請求項1~4のいずれか1項に記載の硬化膜を含む表示装置。
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