Photocurable resin composition, adhesive, sealing material, coating agent, cured product, semiconductor device, electronic component, and curing, adhesion, sealing, and coating methods each using photocurable resin composition

Abstract

The present invention addresses the problem of providing a photocurable resin composition in which curing is completed without performing a curing treatment using heat and in which emission of volatile organic compounds is suppressed, an adhesive, a sealing material, or a coating agent containing the same, a cured product of the same, a semiconductor device or an electronic component containing said cured product, and a curing method, an adhesion method, a sealing method, and a coating method each using a curable resin composition.　Provided is a photocurable resin composition comprising a polymerizable compound (A) and a phosphor (B) that emits light at a wavelength of not more than 500 nm upon X-ray irradiation in a state in which the phosphor is mixed with the polymerizable compound, wherein at least one of the following characteristics (a) and (b) is satisfied: (a) the polymerizable compound (A) includes a maleimide compound; and (b) the photocurable resin composition contains an oxime ester-based photopolymerization initiator (C). Also provided are an adhesive, a sealing material, or a coating agent containing the same, a cured product of the same, a semiconductor device or an electronic component containing said cured product, and a curing method, an adhesion method, a sealing method, and a coating method each using a photocurable resin composition.

Description

Photocurable resin composition, adhesive, sealing material, coating agent, cured product, semiconductor device, electronic component, and curing, adhesion, sealing and coating methods using the photocurable resin composition

[0001] The present invention relates to a photocurable resin composition, an adhesive, a sealing material or a coating agent containing the same, a cured product thereof, a semiconductor device or electronic component containing the cured product, and a curing method, an adhesion method, a sealing method and a coating method using the photocurable resin composition.

[0002] Adhesives that are temporarily fixed by ultraviolet (UV) irradiation and then fully cured by heat are used in many fields (e.g., Patent Documents 1 and 2). If the adhesive contains a filler or the like, the filler or the like may act as a shield against UV irradiation light, or if the area where the adhesive is applied has a complex shape, the UV irradiation light may be blocked, resulting in areas in the adhesive that are not reached by UV irradiation light. In such cases, those areas remain uncured, making it difficult to achieve the desired degree of cure. For this reason, this type of adhesive is used in applications where there are areas that are not reached by UV irradiation light and remain uncured, with the aim of fully curing by heat.

[0003] JP 2009-51954 A International Publication No. 2005 / 052021

[0004] On the other hand, from the viewpoint of improving productivity, there is a demand for a curable resin composition that can be completely cured without a heat curing treatment.

[0005] The present inventors focused on phosphors that emit light when irradiated with X-rays. X-rays are uncharged electromagnetic waves that do not cause electrostatic interactions with materials. Furthermore, their short wavelengths (1 pm to 10 nm) result in minimal interaction with the atomic nuclei and electrons of materials, allowing them to penetrate materials with high penetrating power. By incorporating such phosphors into a resin composition and irradiating the resin composition with X-rays, the phosphors would generate light within the resin composition, activating a photopolymerization initiator, which would then proceed with the polymerization of the polymerizable compound in the resin composition, thereby promoting photocuring of the resin composition. Meanwhile, semiconductor devices and electronic components are exposed to high-temperature environments during post-assembly processes and during use. Therefore, photopolymerization initiators that are not incorporated into the cured matrix of the cured product may be released as volatile organic compounds (VOCs). VOCs pose concerns about corrosion of semiconductor devices and electronic components and environmental contamination. Furthermore, VOCs may also cause allergies in device users, particularly in the case of curable resin compositions used in the manufacture of wearable devices.

[0006] Therefore, an object of the present invention is to provide a photocurable resin composition that can be cured completely without a thermal curing treatment and that suppresses VOC emissions, an adhesive, a sealant or a coating agent containing the same, a cured product thereof, a semiconductor device or electronic component containing the cured product, and a curing method, an adhesion method, a sealing method and a coating method that use the curable resin composition.

[0007] Specific means for solving the above problems are as follows. Aspects of the present invention include the following photocurable resin composition, adhesive, encapsulant or coating agent, cured product, semiconductor device or electronic component, method for producing the cured product, method for curing the photocurable resin composition, use of the photocurable resin composition, bonding method, encapsulating method, and coating method. [1] A photocurable resin composition comprising (A) a polymerizable compound, and (B) a phosphor that, when mixed with the polymerizable compound, emits light having a wavelength of 500 nm or less when irradiated with X-rays, wherein the photocurable resin composition satisfies at least one of the following characteristics (a) and (b): (a) the polymerizable compound (A) comprises a maleimide compound; (b) the photocurable resin composition comprises (C) an oxime ester-based photopolymerization initiator. [2] The photocurable resin composition according to [1] above, wherein the content of the photoradical polymerization initiator comprising the oxime ester-based photopolymerization initiator (C) is less than 6 mass% relative to the total mass of the photocurable resin composition. [3] The photocurable resin composition according to [1] or [2] above, wherein the polymerizable compound (A) further comprises a radically polymerizable compound other than the maleimide compound. [4] The photocurable resin composition according to any one of [1] to [3] above, for use in a photocuring method including an X-ray irradiation step. [5] The photocurable resin composition according to any one of [1] to [4] above, for use as an adhesive, sealant, or coating agent for semiconductor devices or electronic components. [6] The photocurable resin composition according to any one of [1] to [5] above, wherein component (A) and component (B), or components (A) to (C), are contained in a single container. [7] The photocurable resin composition according to any one of [1] to [5] above, wherein component (A) and component (B), or components (A) to (C), are contained in two or more containers. [8] An adhesive, sealant, or coating agent comprising the photocurable resin composition according to any one of [1] to [7] above. [9] A cured product obtained by curing the photocurable resin composition according to any one of [1] to [7] above, or the adhesive, sealant, or coating agent according to [8] above.

[10] A semiconductor device or electronic component comprising the cured product according to [9] above.

[11] A method for producing a cured product, comprising irradiating the photocurable resin composition according to any one of [1] to [7] above, or the adhesive, sealant, or coating agent according to [8] above, with X-rays.

[12] A method for curing a photocurable resin composition, comprising irradiating the photocurable resin composition according to any one of [1] to [7] above with X-rays.

[13] Use of the photocurable resin composition according to any one of [1] to [7] above in a photocuring method comprising an X-ray irradiation step.

[14] A method for bonding at least two components with a photocurable resin composition, comprising the steps of: applying the photocurable resin composition according to any one of [1] to [7] above to at least one of the at least two components; and irradiating at least one of the at least two components, the photocurable resin composition, or both, with X-rays.

[15] A method for sealing gaps between or within components with a photocurable resin composition, comprising the steps of: applying or injecting the photocurable resin composition according to any one of [1] to [7] into the gaps between or within the components; and irradiating the photocurable resin composition with X-rays.

[16] A method for coating a surface of an object with a photocurable resin composition, comprising the steps of applying the photocurable resin composition according to any one of [1] to [7] to the object; and irradiating the photocurable resin composition with X-rays.

[0008] According to aspects of the present invention, there are provided a photocurable resin composition that can be cured completely without a thermal curing treatment and that suppresses VOC emissions, an adhesive, a sealant or a coating agent containing the same, a cured product thereof, a semiconductor device or electronic component containing the cured product, and a curing method, an adhesion method, a sealing method and a coating method that use the curable resin composition.

[0009] 1 shows the emission spectra of phosphors (B-1), (B-2), and (B-3) when irradiated with X-rays.

[0010] In this specification, following the convention in the field of synthetic resins, the term "resin," which usually refers to a polymer (especially a synthetic polymer), may be used to refer to the components constituting a curable resin composition before curing, even if the component is not a polymer, for example, a prepolymer compound before curing. In this specification, the term "(meth)acryloyl group" includes both a methacryloyl group and an acryloyl group. Furthermore, the term "(meth)acrylate compound" includes both an acrylate compound and a methacrylate compound. Furthermore, in this specification, a "photocurable resin composition" may be simply referred to as a "resin composition."

[0011] [Photocurable Resin Composition] The photocurable resin composition according to one embodiment of the present invention comprises (A) a polymerizable compound, and (B) a phosphor that, when mixed with the polymerizable compound, emits light having a wavelength of 500 nm or less upon exposure to X-rays, and satisfies at least one of the following characteristics (a) and (b): (a) the polymerizable compound (A) comprises a maleimide compound; (b) the photocurable resin composition comprises (C) an oxime ester-based photopolymerization initiator. According to this embodiment, a photocurable resin composition is provided that is cured completely without a thermal curing treatment and that suppresses VOC emissions.

[0012] The present inventors focused on phosphors that emit light when irradiated with X-rays. X-rays are uncharged electromagnetic waves that do not cause electrostatic interactions with materials, and their short wavelengths of 1 pm to 10 nm result in little interaction with the atomic nuclei or electrons of materials, allowing them to penetrate materials with high penetrating power. It was discovered that by incorporating such phosphors into a resin composition and irradiating the resin composition with X-rays, the phosphors generate light within the resin composition, activating a photopolymerization initiator, and promoting polymerization of the polymerizable compound in the resin composition, thereby promoting curing of the resin composition. Furthermore, it was discovered that even in applications where UV irradiation does not reach and leaves uncured portions, the resin composition continues to cure, completing the cure without a thermal curing process. However, ensuring a certain level of phosphor content to ensure the curability of the resin composition requires an increased photopolymerization initiator content, raising concerns about the release of volatile organic compounds (VOCs) from the photopolymerization initiator. It was discovered that this issue can be resolved by using a polymerizable compound containing a maleimide compound and / or an oxime ester-based photopolymerization initiator. According to the photocurable resin composition of this embodiment, since a thermal curing treatment is not required, productivity in applications using the photocurable resin composition is improved. Furthermore, since the photocurable resin composition of this embodiment does not require the inclusion of a thermal polymerization initiator, frozen storage is not essential and long-term storage at room temperature is possible.

[0013] (A) Polymerizable Compound The photocurable resin composition of this embodiment contains (A) a polymerizable compound (hereinafter also referred to as "component (A)"). The (A) polymerizable compound imparts curability and adhesiveness to the resin composition. The polymerizable compound can be appropriately selected from a radically polymerizable compound, a cationically polymerizable compound, an anionically polymerizable compound, or any combination thereof, but a radically polymerizable compound is preferred. In this embodiment, when the photocurable resin composition satisfies feature (a), the (A) polymerizable compound contains a maleimide compound. Regardless of whether the photocurable resin composition satisfies feature (a) or feature (b), the (A) polymerizable compound can further contain a radically polymerizable compound other than the maleimide compound. Examples of the radical polymerizable compound include, but are not limited to, compounds having an unsaturated double bond such as maleimide compounds, (meth)acrylate compounds, (meth)acrylamide compounds, cyanoacrylate compounds, vinyl ether compounds, styrene compounds, and methylene malonates (2-methylene-1,3-dicarbonyl compounds and derivatives thereof), or mixtures of compounds having an unsaturated double bond and thiol compounds (mixtures capable of ene-thiol reaction).

[0014] Maleimide compounds include monofunctional maleimide compounds having one maleimide group and polyfunctional maleimide compounds having two or more maleimide groups. Maleimide compounds having two maleimide groups are sometimes referred to as bismaleimide compounds. Regarding feature (a), when mixed with the (B) polymerizable compound described below, the maleimide compound is activated by light having a wavelength of 500 nm or less generated by a phosphor that emits light having a wavelength of 500 nm or less upon X-ray irradiation to generate radicals, which then promotes polymerization of the radically polymerizable compound containing the maleimide compound itself. Because the maleimide compound itself absorbs the light emitted by the (B) phosphor and generates radicals, the photocurable resin composition of this embodiment that satisfies feature (a) does not require the use of a photopolymerization initiator, or only requires the use of a small amount of one. The maleimide compound functions as a photoradical polymerization initiator while also being incorporated into the cured matrix of the cured product as a radically polymerizable compound, thereby suppressing VOC emissions from the photopolymerization initiator. From the viewpoint of workability under fluorescent lamps, the maleimide compound is preferably a maleimide compound having an absorption wavelength of 500 nm or less, more preferably a maleimide compound having an absorption wavelength of 475 nm or less, and even more preferably a maleimide compound having an absorption wavelength of 450 nm or less. By matching the absorption characteristics of the maleimide compound with the emission wavelength of the phosphor (B), the efficiency of the polymerization reaction can be increased.

[0015] Furthermore, since maleimide compounds have high polarity and high heat resistance, when used as a polymerizable compound in a photocurable resin composition, a cured product with high reliability can be obtained.

[0016] Examples of bismaleimide compounds include N,N'-(4,4'-diphenylmethane)bismaleimide, bisphenol A diphenyl ether bismaleimide, 3,3'-dimethyl-5,5'-diethyl-4,4'-diphenylmethane bismaleimide, 4-methyl-1,3-phenylene bismaleimide, 1,6'-bismaleimide-(2,2,4-trimethyl)hexane, bis-(3-ethyl-5-methyl-4-maleimidophenyl)methane, m-phenylene bismaleimide (N,N'-1,3-phenylene bismaleimide), 1,6-bismaleimidehexane, 1,2-bismaleimideethane (N,N'-ethyl Examples of the dimaleimide include, but are not limited to, N,N'-(1,2-phenylene)bismaleimide, N,N-1,3-phenylenedimaleimide, N,N'-1,4-phenylenedimaleimide, N,N'-(sulfonyldi-p-phenylene)dimaleimide, N,N'-[3,3'-(1,3-phenylenedioxy)diphenyl]bismaleimide, N,N'-[4,4'-(1,3-phenylenedioxy)diphenyl]bismaleimide, and 4,4'-dimaleimide phenyl ether. These may be used alone or in combination of two or more.

[0017] When a low room temperature modulus is required for the cured resin composition, a bismaleimide compound having a hydrocarbon group derived from a dimer acid can be used. Such bismaleimides are described, for example, in JP 2015-193725 A. Commercially available bismaleimides having a hydrocarbon group derived from a dimer acid include, but are not limited to, products under the trade names "BMI-689," "BMI-1500," and "BMI-1700," which are liquid at 25°C, and "BMI-3000," which is solid at 25°C (all manufactured by Designer Molecules Inc.). These compounds may be used alone or in combination of two or more.

[0018] Examples of monofunctional maleimide compounds include, but are not limited to, monofunctional aliphatic maleimide compounds such as N-n-butylmaleimide, N-hexylmaleimide, 2-maleimidoethyl-ethyl carbonate, 2-maleimidoethyl-propyl carbonate, and N-ethyl-(2-maleimidoethyl)carbamate; alicyclic monofunctional maleimide compounds such as N-cyclohexylmaleimide; N-arylmaleimides such as N-phenylmaleimide; and N-aralkylmaleimides such as N-benzylmaleimide. The aliphatic maleimides and alicyclic maleimides may have a substituent, and examples of the substituent include a phenyl group, a benzyl group, and a hydroxy group. The N-arylmaleimides and N-aralkylmaleimides may have a substituent, and examples of the substituent include, but are not limited to, an alkyl group, a nitro group, a hydroxy group, an alkoxy group, a carboxyl group, and a halogeno group. These compounds may be used alone or in combination of two or more. Commercially available monofunctional maleimides include, for example, Imilex （Ｒ） -C, Imilex （Ｒ） -P (both manufactured by Nippon Shokubai Co., Ltd.), O-CPMI (manufactured by Daiwa Kasei Kogyo Co., Ltd.), etc., but are not limited to these.

[0019] From the viewpoint of reactivity, the maleimide group equivalent of the maleimide compound is preferably 2000 g / eq or less, more preferably 1800 g / eq or less, and even more preferably 1600 g / eq or less. From the viewpoint of suppressing volatilization, the maleimide group equivalent of the maleimide compound is preferably 100 g / eq or more, more preferably 120 g / eq or more, and even more preferably 150 g / eq or more.

[0020] From the viewpoint of polymerization rate, the maleimide compound is preferably in a liquid state at room temperature, or, if it is solid at room temperature, is preferably used by dissolving it in a liquid polymerizable compound (A) or the like.

[0021] In this specification, the (meth)acrylate compound refers to a compound having at least one (meth)acryloyl group in the molecule, and includes a monofunctional (meth)acrylate compound having one (meth)acryloyl group and a polyfunctional (meth)acrylate compound having two or more (meth)acryloyl groups. Examples of the monofunctional (meth)acrylate compound include: -ethyl (meth)acrylate, trifluoroethyl (meth)acrylate, diethylaminoethyl (meth)acrylate, dimethylaminoethyl (meth)acrylate, glycidyl (meth)acrylate, n-butyl (meth)acrylate, isobutyl (meth)acrylate, tert-butyl (meth)acrylate, isoamyl (meth)acrylate, cyclohexyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, isodecyl (meth)acrylate, isobornyl (meth)acrylate, stearyl (meth)acrylate, lauryl (meth)acrylate, phenoxyethyl (meth)acrylate, benzyl (meth)acrylate, tetrahydrofurfuryl (meth)acrylate, ethoxydiethylene glycol (meth)acrylate, phenoxydiethylene glycol (meth)acrylate, phenoxypolyethylene glycol (meth)acrylate, butoxydiethylene glycol (meth) Esters of monohydric alcohols and (meth)acrylic acid such as acrylate, methoxydipropylene glycol (meth)acrylate, methoxypolyethylene glycol (meth)acrylate, methoxytriethylene glycol (meth)acrylate, methoxypolyethylene glycol (meth)acrylate, 2-ethylhexyldiethylene glycol (meth)acrylate, 4-tert-butylcyclohexyl (meth)acrylate, and 3-phenoxybenzyl (meth)acrylate; 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, 2-hydroxy-3-phenoxypropyl (meth)acrylate, octyl acrylate, nonyl acrylate, isononyl acrylate, 3,3,5-trimethylcyclohexyl acrylate, cyclic trimethylolpropane formal acrylate, and 1-naphthalenemethyl (meth)acrylate.1-Ethylcyclohexyl (meth)acrylate, 1-methylcyclohexyl (meth)acrylate, 1-ethylcyclopentyl (meth)acrylate, 1-methylcyclopentyl (meth)acrylate, dicyclopentenyl (meth)acrylate, dicyclopentenyloxyethyl (meth)acrylate, dicyclopentanyl (meth)acrylate, nonylphenoxy polyethylene glycol (meth)acrylate, tetrahydrodicyclopentadienyl (meth)acrylate, 2-(o-phenylphenoxy)ethyl (meth)acrylate, isobornyl Cyclohexyl (meth)acrylate, (2-methyl-2-ethyl-1,3-dioxolan-4-yl)methyl (meth)acrylate, 1-adamantyl (meth)acrylate, 3-hydroxy-1-adamantyl (meth)acrylate, 2-methyl-2-adamantanyl (meth)acrylate, 2-ethyl-2-adamantanyl (meth)acrylate, 2-isopropyladamantan-2-yl (meth)acrylate, 3-hydroxy-1-adamantyl (meth)acrylate, (adamantan-1-yloxy)methyl (meth)acrylate, 2-isopropyladamantan-2-yl (meth)acrylate, Isopropyl-2-adamantyl (meth)acrylate, 1-methyl-1-ethyl-1-adamantylmethanol (meth)acrylate, 1,1-diethyl-1-adamantylmethanol (meth)acrylate, 2-cyclohexylpropan-2-yl (meth)acrylate, 1-isopropylcyclohexyl (meth)acrylate, 1-methylcyclohexyl (meth)acrylate, 1-ethylcyclopentyl (meth)acrylate, 1-methylcyclohexyl (meth)acrylate, tetrahydropyranyl (meth)acrylate, tetrahydro-2-furan Examples of the acrylic acid ester include mono(meth)acrylates of polyhydric alcohols or esters of monohydric alcohols and (meth)acrylic acid, such as 5-oxotetrahydrofuranyl(meth)acrylate, 2-oxotetrahydrofuran-3-yl(meth)acrylate, (5-oxotetrahydrofuran-2-yl)methyl(meth)acrylate, (2-oxo-1,3-dioxolan-4-yl)methyl(meth)acrylate, N-acryloyloxyethylhexahydrophthalimide, α-acryloyl-ω-methoxypoly(oxyethylene), and 1-ethoxyethyl(meth)acrylate.The polyfunctional (meth)acrylate compound is not limited to these. These may be used alone or in combination of two or more. Examples of the polyfunctional (meth)acrylate compound include di(meth)acrylate of tris(2-hydroxyethyl)isocyanurate, tris(2-hydroxyethyl)isocyanurate tri(meth)acrylate, trimethylolpropane tri(meth)acrylate, or an oligomer thereof; pentaerythritol tri(meth)acrylate, or an oligomer thereof; poly(meth)acrylate of dipentaerythritol; tris(acryloxyethyl)isocyanurate; caprolactone-modified tris((meth)acryloxyethyl)isocyanurate; poly(meth)acrylate of alkyl-modified dipentaerythritol; poly(meth)acrylate of caprolactone-modified dipentaerythritol; ethoxylated bisphenol A di(meth)acrylate; Examples of the (meth)acrylate include, but are not limited to, dihydrocyclopentadiethyl (meth)acrylate, polyester (meth)acrylate, dimethylol-tricyclodecane di(meth)acrylate, ditrimethylolpropane poly(meth)acrylate, polyurethane having two or more (meth)acryloyl groups in one molecule, polyester having two or more (meth)acryloyl groups in one molecule, phenoxyethyl (meth)acrylate, isobornyl (meth)acrylate, phenoxydiethylene glycol (meth)acrylate, 4-tert-butylcyclohexyl (meth)acrylate, epoxy resin half (meth)acrylate, and (meth)acrylate having an allyloxymethyl group (see JP 2024-009452 A). The (meth)acrylate compound may be any one of the above-mentioned (meth)acrylate compounds, or two or more may be used in combination. Commercially available (meth)acrylate compounds include, for example, polyester acrylate (product name: EBECRYL810) manufactured by Daicel-Allnex Corporation, ditrimethylolpropane tetraacrylate (product name: EBECRYL140) manufactured by Daicel-Allnex Corporation, polyester acrylate (product name: M7100) manufactured by Toagosei Co., Ltd., and dimethylol-tricyclodecane diacrylate (product name: Light Acrylate DCP-A) manufactured by Kyoeisha Chemical Co., Ltd.Examples include, but are not limited to, neopentyl glycol modified trimethylolpropane diacrylate (product name: Kayarad R-604) manufactured by Nippon Kayaku Co., Ltd.

[0022] The (meth)acrylamide compound has an acrylamide group (H ２ C=CHCONH-) or methacrylamide group ((H ２ C=C(CH ３ )CONH-) Examples of the (meth)acrylamide compound include, but are not limited to, N,N'-methylenebis(meth)acrylamide, N,N'-ethylenebis(meth)acrylamide, 1,2-di(meth)acrylamide ethylene glycol, and the like.

[0023] The cyanoacrylate compound is H ２Known groups represented by the formula C═C(CN)—COOR can be used. In this formula, R is an ester residue such as an alkyl group, cycloalkyl group, alkenyl group, cycloalkenyl group, alkynyl group, or aryl group. The number of carbon atoms in the ester residue is not particularly limited, but typically, those having 1 to 8 carbon atoms can be used. Ester residues consisting of substituted hydrocarbon groups such as alkoxyalkyl groups and trialkylsilylalkyl groups can also be used. Examples of cyanoacrylate compounds include alkyl and cycloalkyl cyanoacrylates such as methyl cyanoacrylate, ethyl cyanoacrylate, propyl cyanoacrylate, butyl cyanoacrylate, and cyclohexyl cyanoacrylate; alkenyl and cycloalkenyl cyanoacrylates such as allyl cyanoacrylate, methallyl cyanoacrylate, and cyclohexenyl cyanoacrylate; alkynyl cyanoacrylates such as propanegyl cyanoacrylate; aryl cyanoacrylates such as phenyl cyanoacrylate and toluyl cyanoacrylate; methoxyethyl cyanoacrylate, ethoxyethyl cyanoacrylate, and furfuryl cyanoacrylate containing heteroatoms; trimethylsilylmethyl cyanoacrylate, trimethylsilylethyl cyanoacrylate, trimethylsilylpropyl cyanoacrylate, and dimethylvinylsilylmethyl cyanoacrylate containing silicon; but are not limited thereto.These compounds may be used alone or in combination of two or more.

[0024] The vinyl ether compound has a vinyl ether group (H ２ C═CH—O—). Examples of vinyl ether compounds include, but are not limited to, ethyl vinyl ether, triethylene glycol divinyl ether, trimethylolpropane trivinyl ether, hydroxybutyl vinyl ether, dodecyl vinyl ether, cyclohexyl vinyl ether, 1,4-butanediol divinyl ether, nonanediol divinyl ether, cyclohexanediol divinyl ether, and cyclohexanedimethanol divinyl ether. These compounds may be used alone or in combination of two or more.

[0025] Styrene compounds contain a styrene group (H ２ C=CH-C ６ H ５ -). Examples of the styrene compound include styrene, α-methylstyrene, 2-methylstyrene, 3-methylstyrene, 4-methylstyrene, 4-propylstyrene, 4-t-butylstyrene, 4-cyclohexylstyrene, 4-dodecylstyrene, 2,4-dimethylstyrene, 2,4-diisopropylstyrene, 2,4,6-trimethylstyrene, 2-ethyl-4-benzylstyrene, 4-(phenylbutyl)styrene, N,N-diethyl-4-aminoethylstyrene, and 4-methoxystyrene, but are not limited to these. These may be used alone or in combination of two or more.

[0026] Methylene malonates are malonates having at least one methylene group in the molecule, including monofunctional methylene malonates having one methylene group and polyfunctional methylene malonates having two or more methylene groups. The methylene malonates preferably have a molecular weight of 220 or more. There are no particular limitations on the type of methylene malonate that can be used, and various disclosed methylene malonates can be used, including compounds described in WO 2018 / 212330 A1 and the like. Methylene malonates may be used alone or in combination of two or more.

[0027] The thiol compound in the mixture of a compound having an unsaturated double bond and a thiol compound is a compound containing at least one thiol group, and the thiol group can undergo a radical addition reaction (ene-thiol reaction) with the unsaturated double bond of the compound having an unsaturated double bond. Examples of thiol compounds include monofunctional thiol compounds having one thiol group and polyfunctional thiol compounds having two or more thiol groups. In one embodiment, the thiol compound contains at least a polyfunctional thiol compound. In one embodiment, the thiol compound contains a combination of a bifunctional thiol compound and a trifunctional or higher functional thiol compound. In one embodiment, the thiol compound contains a combination of a monofunctional thiol compound and a polyfunctional thiol compound. Thiol compounds can also be divided into thiol compounds having a hydrolyzable partial structure such as an ester bond in the molecule (i.e., hydrolyzable) and thiol compounds not having such a partial structure (i.e., non-hydrolyzable). Examples of hydrolyzable thiol compounds include trimethylolpropane tris(3-mercaptopropionate) (manufactured by SC Organic Chemical Co., Ltd.: TMMP), tris-[(3-mercaptopropionyloxy)-ethyl]-isocyanurate (manufactured by SC Organic Chemical Co., Ltd.: TEMPIC), pentaerythritol tetrakis(3-mercaptopropionate) (manufactured by SC Organic Chemical Co., Ltd.: PEMP), and tetraethylene glycol bis(3-mercaptopropionate) (manufactured by SC Organic Chemical Co., Ltd.: EGMP- 4), dipentaerythritol hexakis(3-mercaptopropionate) (manufactured by SC Organic Chemical Co., Ltd.: DPMP), pentaerythritol tetrakis(3-mercaptobutyrate) (manufactured by Resonac Co., Ltd.: Karenz MT (registered trademark) PE1), 1,3,5-tris(3-mercaptobutyryloxyethyl)-1,3,5-triazine-2,4,6(1H,3H,5H)-trione (manufactured by Resonac Co., Ltd.: Karenz MT (registered trademark) NR1), and the like can be mentioned, but are not limited to these. These may be used alone or in combination of two or more. Examples of non-hydrolyzable polyfunctional thiol compounds include 1,3,4,6-tetrakis(2-mercaptoethyl)glycoluril (manufactured by Shikoku Chemical Industry Co., Ltd.: TS-G), (1,3,4,6-Tetrakis(3-mercaptopropyl)glycoluril (Shikoku Chemical Industry Co., Ltd.: C3 TS-G), 1,3,4,6-tetrakis(mercaptomethyl)glycoluril, 1,3,4,6-tetrakis(mercaptomethyl)-3a-methylglycoluril, 1,3,4,6-tetrakis(2-mercaptoethyl)-3a-methylglycoluril, 1,3,4,6-tetrakis(3-mercaptopropyl)-3a-methylglycoluril, 1,3,4,6-tetrakis(mercaptomethyl)-3a,6a-dimethylglycoluril, 1,3,4,6-tetrakis(2-mercaptoethyl)-3a,6a-di Methyl glycoluril, 1,3,4,6-tetrakis(3-mercaptopropyl)-3a,6a-dimethyl glycoluril, 1,3,4,6-tetrakis(mercaptomethyl)-3a,6a-diphenyl glycoluril, 1,3,4,6-tetrakis(2-mercaptoethyl)-3a,6a-diphenyl glycoluril, 1,3,4,6-tetrakis(3-mercaptopropyl)-3a,6a-diphenyl glycoluril, tris(3-mercaptopropyl) isocyanurate, 1,3,5-tris[3-(2-mercaptopropyl)methyl]-3a,6a-diphenyl glycoluril, 1,3,5-tris[2-(3-mercaptoethylsulfanyl)propyl]isocyanurate, 1,3,5-tris[2-(3-mercaptopropoxy)ethyl]isocyanurate, pentaerythritol trippropanethiol (manufactured by SC Organic Chemical Co., Ltd.: PEPT), 3-[2,3-bis(3-sulfanylpropoxy)propoxy]propane-1-thiol, 1,2,3-tris(3-mercaptopropoxy)propane, 3-[2,2-bis[(3-mercaptopropoxy)methyl]butoxy]-1-propanethiol, pentaerythritol tetrapropane thiol, 1,2,3-tris(mercaptomethylthio)propane, 1,2,3-tris(2-mercaptoethylthio)propane, 1,2,3-tris(3-mercaptopropylthio)propane, 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, tetrakis(mercaptomethylthiomethyl)methane, tetrakis(2-mercaptoethylthiomethyl)methane, tetrakis(3-mercaptopropylthiomethyl)methane, 1,1,3,3-tetrakis(mercaptomethylthio)propane, 1,1,2,2-tetrakis(mercaptomethylthio)ethane, 1,1,5,5-tetrakis(mercaptomethylthio)-3-thiapentane, 1,1,6,6-tetrakis(mercaptomethylthio)-3,4-dithiahexane, 2,2-bis(mercaptomethylthio)ethanethiol, 3-mercaptomethylthio-1,7-dimercapto-2,6-dithiaheptane, 3,6-bis(mercaptomethylthio)-1,9-dimercapto-2,5,8-trithianonane, 3-mercaptomethylthio-1,6-dimercapto-2,5-dithiahexane, 1,1,9,9-tetrakis(mercaptomethylthio)-5-(3,3-bis(mercaptomethylthio)-1-thiapropyl)3,7-dithianonane, tris(2,2-bis(mercaptomethylthio)ethyl)methane, tris(4,4-bis(mercaptomethylthio)-2-thiabutyl)methane , tetrakis(2,2-bis(mercaptomethylthio)ethyl)methane, tetrakis(4,4-bis(mercaptomethylthio)-2-thiabutyl)methane, 3,5,9,11-tetrakis(mercaptomethylthio)-1,13-dimercapto-2,6,8,12-tetrathiatridecane, 3,5,9,11,15,17-hexakis(mercaptomethylthio)-1,19-dimercapto-2,6,8,12,14,18-hexathianonadecane, 9-(2,2-bis(mercaptomethylthio)ethyl)-3,5,13,15-tetrakis(mercapto 3,4,8,9-tetrakis(mercaptomethylthio)-1,11-dimercapto-2,5,7,10-tetrathiaundecane, 3,4,8,9,13,14-hexakis(mercaptomethylthio)-1,16-dimercapto-2,5,7,10,12,15-hexathiahexadecane, 8-[bis(mercaptomethylthio)methyl]-3,4,12,13-tetrakis(mercaptomethylthio)-1,15-dimercapto-2,5,7,9,11,14-Hexathiapentadecane, 4,6-bis[3,5-bis(mercaptomethylthio)-7-mercapto-2,6-dithiaheptylthio]-1,3-dithiane, 4-[3,5-bis(mercaptomethylthio)-7-mercapto-2,6-dithiaheptylthio]-6-mercaptomethylthio-1,3-dithiane, 1,1-bis[4-(6-mercaptomethylthio)-1,3-dithianylthio]-1,3-bis(mercaptomethylthio)propane, 1-[4-(6-mercaptomethylthio)-1,3-dithianylthio]-3-[2,2-bis(mercaptomethylthio) methylthio)ethyl]-7,9-bis(mercaptomethylthio)-2,4,6,10-tetrathiaundecane, 3-[2-(1,3-dithietanyl)]methyl-7,9-bis(mercaptomethylthio)-1,11-dimercapto-2,4,6,10-tetrathiaundecane, 9-[2-(1,3-dithietanyl)]methyl-3,5,13,15-tetrakis(mercaptomethylthio)-1,17-dimercapto-2,6,8,10,12,16-hexathiaheptadecane, 3-[2-(1,3-dithietanyl)]methyl-7,9,13,15-tetrakis bis(mercaptomethylthio)-1,17-dimercapto-2,4,6,10,12,16-hexathiaheptadecane, 4,6-bis[4-(6-mercaptomethylthio)-1,3-dithianylthio]-6-[4-(6-mercaptomethylthio)-1,3-dithianylthio]-1,3-dithiane, 4-[3,4,8,9-tetrakis(mercaptomethylthio)-11-mercapto-2,5,7,10-tetrathiaundecyl]-5-mercaptomethylthio-1,3-dithiolane, 4,5-bis[3,4-bis(mercaptomethylthio)-6-mercapto- 2,5-dithiahexylthio]-1,3-dithiolane, 4-[3,4-bis(mercaptomethylthio)-6-mercapto-2,5-dithiahexylthio]-5-mercaptomethylthio-1,3-dithiolane, 4-[3-bis(mercaptomethylthio)methyl-5,6-bis(mercaptomethylthio)-8-mercapto-2,4,7-trithiaoctyl]-5-mercaptomethylthio-1,3-dithiolane, 2-{bis[3,4-bis(mercaptomethylthio)-6-mercapto-2,5-dithiahexylthio]methyl}-1,3-dithietane, 2-[3,4-bis(mercaptomethylthio)-6-mercapto-2,5-dithiahexylthio]mercaptomethylthiomethyl-1,3-dithietane, 2-[3,4,8,9-tetrakis(mercaptomethylthio)-11-mercapto-2,5,7,10-tetrathiaundecylthio]mercaptomethylthiomethyl-1,3-dithietane, 2-[3-bis(mercaptomethylthio)methyl-5,6-bis(mercaptomethylthio)-8-mercapto-2,4,7-trithiaoctyl]mercaptomethylthiomethyl-1,3-dithietane, 4-{1-[2-(1,3 -dithietanyl)]-3-mercapto-2-thiapropylthio}-5-[1,2-bis(mercaptomethylthio)-4-mercapto-3-thiabutylthio]-1,3-dithiolane, 2,2'-[cyclohexylidenebis(thio-2,1-ethanediylthio)]bis[ethanethiol], 4,4'-[(1,3-phenylene)bis(oxy)]bis[1-butanethiol], and the various bifunctional thiol compounds disclosed in WO 2019 / 082962, as well as dimers, trimers, and tetramers of the above thiol compounds, can be mentioned, but are not limited to these. These may be used alone or in combination of two or more.

[0028] The polymerizable compound (A) may contain a cationically polymerizable compound. The cationically polymerizable compound is a compound having one or more cationically polymerizable groups in the molecule. Examples of the cationically polymerizable compound include, but are not limited to, compounds having an epoxy group, compounds having an oxetanyl group, compounds having a vinyl ether group, compounds having other cationically polymerizable groups, and compounds having any combination of these cationically polymerizable groups.

[0029] In this specification, a compound having an epoxy group refers to a compound having at least one epoxy group in the molecule, and is also referred to as an epoxy compound. Examples include monofunctional epoxy compounds having one epoxy group and polyfunctional epoxy compounds having two or more epoxy groups. In one embodiment, the epoxy compound preferably contains at least a polyfunctional epoxy compound, and may contain a combination of a polyfunctional epoxy compound and a monofunctional epoxy compound. Epoxy compounds can be broadly classified into epoxy compounds having an aromatic ring skeleton, aliphatic epoxy compounds, and alicyclic epoxy compounds depending on the type of skeleton.

[0030] In this specification, a compound having an oxetanyl group is a compound having at least one oxetane ring (e.g., a 3-oxetanyl group) in the molecule, and is also referred to as an oxetane compound. In one embodiment, the oxetane compound preferably has 1 to 6 oxetanyl groups in the molecule, and more preferably has 1 to 2 oxetanyl groups in the molecule.

[0031] In this specification, a compound having a vinyl ether group is a compound having at least one vinyl ether group in the molecule.

[0032] Specific examples of the cationic polymerizable compound include glycidyl ethers of tetra(hydrophenyl)alkanes, glycidyl ethers of tetrahydroxybenzophenone, epoxidized polyvinylphenol, p-tert-butylphenyl glycidyl ether, ethylene glycol diglycidyl ether, diethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, 1,4-butanediol diglycidyl ether, neopentyl glycol diglycidyl ether, 1,6-hexanediol diglycidyl ether, glycerin diglycidyl ether, trimethylolpropane triglycidyl ether, polyethylene glycol diglycidyl ether, hydrogenated bisphenol A diglycidyl ether, n-butyl glycidyl ether, 2-ethylhexyl glycidyl ether, 1,2-epoxytetradecane, 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate, 3,4-epoxy-1-methylcyclohexyl-3,4-epoxy-1-methylhexanecarboxylate, 6-methyl-3,4-eth ... 3,4-epoxy-5-methylcyclohexylmethyl-3,4-epoxy-5-methylcyclohexanecarboxylate, bis(3,4-epoxycyclohexylmethyl)adipate, 3,4-epoxy-6-methylcyclohexanecarboxylate, methylenebis(3,4-epoxycyclohexane), propanediol Pan-2,2-diyl-bis(3,4-epoxycyclohexane), 2,2-bis(3,4-epoxycyclohexyl)propane, dicyclopentadiene diepoxide, ethylene bis(3,4-epoxycyclohexanecarboxylate), limonene dioxide (1,2:8,9-diepoxylimonene), (3,3',4,4'-diepoxy)bicyclohexyl, dioctyl epoxyhexahydrophthalate, di-2-ethylhexyl epoxyhexahydrophthalate, 1-epoxyethyl-3,4-epoxycyclohexane, 1,2-epoxy-2-epoxyethylcyclohexane, 1,2-epoxy-4-vinylcyclohexane, α-pinene oxide, 1,2-epoxy-4-(2-oxiranyl)cyclohexane adduct of 2,2-bis(hydroxymethyl)-1-butanol, epoxidized polybutadiene, styrene-butadiene copolymer compounds in which some or all of the double bonds have been epoxidized, polyalkylene oxide-modified bisphenol A type epoxy, lauryl alcohol polyethylene glycol glycidyl ether, diglycidyl ether of alicyclic diol, diglycidyl ether of alicyclic diol Diglycidyl ether of polyalkylene oxide adduct, bis[1-ethyl(3-oxetanyl)]methyl ether (also known as (3-ethyl-3{[(3-ethyloxetan-3-yl)methoxy]methyl}oxetane)), xylylene bisoxetane, 4,4'-bis[3-ethyl-(3-oxetanyl)methoxymethyl]biphenyl, 1,4-bis(3-ethyl-3-oxetanylmethoxy)methylbenzene, (bis[(3-ethyl-3-oxetanyl)methyl]isophthalate), 3-ethyl-3-hydroxymethyloxetane, 2-ethylhexyl Xyloxetane, (3-ethyloxetan-3-yl)methyl methacrylate, 3-ethyl-3-[(2-ethylhexyloxy)methyl]oxetane, 3-ethyl-3-(4-hydroxybutyl)oxymethyloxetane, 3-ethyl-3-phenoxymethyloxetane, oxetanyl silsesquioxetane, 3-ethyl-3{[(3-ethyloxetan-3-yl)methoxy]methyl}oxetane, phenol novolac oxetane, 1,4-butanediol divinyl ether, diethylene glycol divinyl ether, triethylene glycol divinyl ether, tetraethylene glycol divinyl ether, normal propyl vinyl ether, isopropyl vinyl ether, normal butyl vinyl ether, isobutyl vinyl ether, 2-ethylhexyl vinyl ether, cyclohexyl vinyl ether, 2-hydroxyethyl vinyl ether, diethylene glycol monovinyl ether, 4-hydroxybutyl vinyl ether, 2-(2-vinyloxyethoxy)ethyl acrylate, 2-(2-vinyloxyethoxy)ethyl methacrylate, 1,4-cyclohexanedimethanol monovinyl ether, 1,Examples include, but are not limited to, 4-cyclohexanedimethanol divinyl ether.

[0033] Commercially available cationically polymerizable compounds include EPICLON (registered trademark) 850, 850-S, EXA-850CRP, and EXA-8067 manufactured by DIC Corporation; AER9000 manufactured by Asahi Kasei Corporation; EP-4000S, EP-4003S, EP-4005, EP-4010S, EP-4088S, and EP-4088L manufactured by ADEKA Corporation; Rikaresin BEO-60E manufactured by New Japan Chemical Co., Ltd.; EX-171 manufactured by Nagase ChemteX Corporation; EPICLON (registered trademark) 830-S, EXA-830LVP, and E manufactured by DIC Corporation. XA-835LV; EPICLON (registered trademark) HP-4032D, HP-720H manufactured by DIC Corporation; EPICLON (registered trademark) N-740, N-770 manufactured by DIC Corporation; EPICLON (registered trademark) N-660, N-670, N-655-EXP-S manufactured by DIC Corporation; ADEKA GLYCIROL (registered trademark) ED-509E, ED-509S manufactured by ADEKA Corporation; OPP-G manufactured by Sanko Co., Ltd.; Epolite 100MF manufactured by Kyoeisha Chemical Co., Ltd.; AER-9000 manufactured by Asahi Kasei Corporation; jER manufactured by Mitsubishi Chemical Corporation YX7400N; jER YX8000 manufactured by Mitsubishi Chemical Corporation; CELLOXIDE (registered trademark) 2021P manufactured by Daicel Corporation; CELLOXIDE (registered trademark) 8010 manufactured by Daicel Corporation; EHPE3150 manufactured by Daicel Corporation; EPOLEAD PB manufactured by Daicel Corporation; EPOFRIEND manufactured by Daicel Corporation; HiREM-1 and HiREM-2 manufactured by Shikoku Chemicals Corporation; OXT-191 manufactured by Toagosei Co., Ltd.; OXT-221 manufactured by Toagosei Co., Ltd.; PHOX manufactured by Toagosei Co., Ltd., and the like, but are not limited to these.

[0034] The cationically polymerizable compounds may be used alone or in combination of two or more.

[0035] The polymerizable compound (A) may contain an anionic polymerizable compound. Examples of anionic polymerizable compounds include the compounds having an epoxy group listed above as examples of cationic polymerizable compounds, and their curing agents, such as thiol-based curing agents, phenol-based curing agents, acid anhydride-based curing agents, and amine-based curing agents. Methylene malonates listed above as examples of radical polymerizable compounds are also included as anionic polymerizable compounds. Furthermore, (meth)acrylate compounds listed above as examples of radical polymerizable compounds are also included as anionic polymerizable compounds when used in combination with a thiol compound. These compounds may be used alone or in combination of two or more. The thiol compounds listed above can be used as thiol-based curing agents. Examples of phenolic curing agents refer to monomers, oligomers, and polymers in general that have a phenolic hydroxyl group, and include, but are not limited to, phenol novolac resins and their alkylated or allylated products, cresol novolac resins, phenol aralkyl (including phenylene and biphenylene skeleton) resins, naphthol aralkyl resins, triphenolmethane resins, dicyclopentadiene-type phenolic resins, etc. Examples of acid anhydride curing agents include, but are not limited to, alkylated tetrahydrophthalic anhydrides such as methyltetrahydrophthalic anhydride, methylhexahydrophthalic anhydride, and methyltetrahydrophthalic anhydride, hexahydrophthalic anhydride, methylhimic anhydride, alkenyl-substituted succinic anhydride, methylnadic anhydride, and glutaric anhydride.Examples of the amine-based curing agent include, but are not limited to, aliphatic polyamines such as triethylenetetraamine, tetraethylenepentamine, m-xylenediamine, trimethylhexamethylenediamine, and 2-methylpentamethylenediamine; alicyclic polyamines such as isophoronediamine, 1,3-bisaminomethylcyclohexane, bis(4-aminocyclohexyl)methane, norbornenediamine, and 1,2-diaminocyclohexane; piperazine-type polyamines such as N-aminoethylpiperazine and 1,4-bis(2-amino-2-methylpropyl)piperazine; and aromatic polyamines such as diethyltoluenediamine, dimethylthiotoluenediamine, 4,4'-diamino-3,3'-diethyldiphenylmethane, bis(methylthio)toluenediamine, diaminodiphenylmethane, m-phenylenediamine, diaminodiphenylsulfone, diethyltoluenediamine, trimethylenebis(4-aminobenzoate), and polytetramethyleneoxide-di-p-aminobenzoate. Commercially available products include Epicure-W and Epicure-Z (Yuka Shell Epoxy Co., Ltd., trade names), jER Cure (registered trademark)-W and jER Cure (registered trademark)-Z (Mitsubishi Chemical Corporation, trade names), Kayahard A-A, Kayahard A-B, and Kayahard A-S (Nippon Kayaku Co., Ltd., trade names), Thothamine HM-205 (Nippon Steel Sumikin Chemical Co., Ltd., trade names), Adeka Hardener EH-101 (ADEKA Corporation, trade names), Epomic Q-640 and Epomic Q-643 (Mitsui Chemicals, Inc., trade names), DETDA80 (Lonza, trade names), and Thothamine HM-205 (Nippon Steel Sumikin Chemical Co., Ltd., trade names), but are not limited to these.

[0036] The amount of the radical polymerizable compound in all of the (A) polymerizable compounds is preferably 70 to 100 parts by mass, more preferably 80 to 100 parts by mass, even more preferably 90 to 100 parts by mass, and particularly preferably 95 to 100 parts by mass, relative to 100 parts by mass of the total of the (A) polymerizable compounds. In one embodiment, the amount of the radical polymerizable compound in all of the (A) polymerizable compounds is 100 parts by mass, relative to 100 parts by mass of the total of the (A) polymerizable compounds. When the photocurable resin composition satisfies characteristic (a), the amount of the maleimide compound is preferably 0.1 to 100 parts by mass, more preferably 0.2 to 100 parts by mass, relative to 100 parts by mass of the total of the radical polymerizable compounds (i.e., the sum of the maleimide compound and the radical polymerizable compounds other than the maleimide compound).

[0037] The content of the polymerizable compound (A) in the photocurable resin composition may be 1 to 99 parts by mass per 100 parts by mass of the total photocurable resin composition. In some embodiments, the content of the polymerizable compound (A) in the photocurable resin composition is preferably 5 to 50 parts by mass, more preferably 7 to 30 parts by mass, per 100 parts by mass of the total photocurable resin composition. The photocurable resin composition of this embodiment can be cured by photocuring alone even in the presence of a large amount of a shielding material such as a filler. In another embodiment, the content of the polymerizable compound (A) in the photocurable resin composition is preferably 30 to 99 parts by mass, more preferably 50 to 99 parts by mass, and even more preferably 60 to 99 parts by mass, per 100 parts by mass of the total photocurable resin composition. The content of the polymerizable compound (A) in the photocurable resin composition is preferably 75 to 99 parts by mass, more preferably 80 to 99.5 parts by mass, and even more preferably 85 to 98 parts by mass, relative to 100 parts by mass of the total amount of all organic substances (excluding low-stress-imparting materials such as organic fillers and elastomers) contained in the photocurable resin composition.

[0038] (B) Phosphor that Emits Light with a Wavelength of 500 nm or Less When Irradiated with X-Rays in a Mixed State with a Polymerizable Compound The photocurable resin composition of this embodiment contains a phosphor that emits light with a wavelength of 500 nm or less when irradiated with X-rays in a mixed state with a polymerizable compound (B) (hereinafter also referred to as "(B) phosphor" or "component (B)"). X-rays are uncharged electromagnetic waves that do not cause electrostatic interactions with substances, and because of their short wavelengths of 1 pm to 10 nm, they have little interaction with the atomic nuclei or electrons of substances and have high penetrating power through substances. It has been discovered that by incorporating such a phosphor that emits light with a wavelength of 500 nm or less when irradiated with X-rays in a mixed state with a polymerizable compound (B) into a resin composition and irradiating the resin composition with X-rays, the phosphor generates light with a wavelength of 500 nm or less within the resin composition, activating the maleimide compound and / or photopolymerization initiator, and thereby progressing the polymerization of the polymerizable compound in the resin composition, thereby progressing the curing of the resin composition. Furthermore, it has been found that even in applications where UV irradiation does not reach and there are uncured portions, the curing of the resin composition proceeds and is completed without a thermal curing treatment. In this embodiment, the phosphor (B) is a phosphor that does not decompose, dissolve, or deliquesce when mixed with a polymerizable compound, and maintains its crystallinity and particle shape. Phosphors that emit light as a single phosphor but decompose, dissolve, or deliquesce when mixed with a polymerizable compound either do not emit light in the resin composition, or, even if they do emit light, the emission intensity is significantly reduced, and therefore are not suitable as the phosphor (B) in this embodiment.

[0039] In this aspect, the (B) phosphor is a phosphor that emits light with a wavelength of 500 nm or less when irradiated with X-rays in a mixed state with a polymerizable compound, more preferably a phosphor that emits light with a wavelength of 450 nm or less when irradiated with X-rays in a mixed state with a polymerizable compound, and even more preferably a phosphor that emits light with a wavelength of 430 nm or less when irradiated with X-rays in a mixed state with a polymerizable compound. In one embodiment, the (B) phosphor is a phosphor that emits ultraviolet light (wavelength 200 nm to 380 nm) when irradiated with X-rays in a mixed state with a polymerizable compound.

[0040] (B) The phosphor that emits light with a wavelength of 500 nm or less when irradiated with X-rays in a mixed state with a polymerizable compound can be appropriately selected based on the peak intensity of the emission, the peak wavelength of the emission, crystallinity, stability, ease of handling, etc. Examples of the phosphor that emits light with a wavelength of 500 nm or less when irradiated with X-rays in a mixed state with a polymerizable compound (B) include inorganic phosphors such as metal oxides, metal sulfides, metal halides, or those doped with impurity elements. Metal oxides, metal sulfides, metal halides, or those doped with impurity elements may contain nonmetallic or semimetallic elements such as nitrogen (N), phosphorus (P), silicon (Si), or boron (B). The impurity elements doped into the metal oxides, metal sulfides, or metal halides may be rare earth elements or transition metal elements, and may exist as ions. (B) The phosphor that emits light with a wavelength of 500 nm or less when irradiated with X-rays in a mixed state with a polymerizable compound (B) may also be an organic phosphor.

[0041] (B) Specific examples of phosphors that emit light with a wavelength of 500 nm or less when irradiated with X-rays in a state mixed with a polymerizable compound include sialon (SiAlON) phosphors, Y ２ SiO ５ :Ce, BaFCl:Eu, BaSO ４ :Eu, LaOBr:Tm, YTaO ４ , YTaO ４ : Nb, CaWO ４ , LaOBr:Tb, Y ２ O ２ S:Tb, ZnS:Ag, (Zn,Cd):Ag,Cd ２ O ２ S: Tb, La ２ O ２ S: Tb, Zn ３ (P.O. ４ ) ２ :TI, CsI, Ca ３ (P.O. ４ ) ２ : TI, BaSi ２ O ５ : Pb, borosilicate, LaCl ３ (Ce), SrB ４ O ７ F: Eu, RbBr: TI, (Ba, Sr, Mg) ３ Si２ O ７ : Pb, YaIO ３ Examples of suitable phosphors include, but are not limited to, inorganic phosphors such as BaFBr:Ce and BaFBr:Eu, and organic phosphors such as those under the product names BC-420 and BC-422 (both manufactured by Luxium Solutions).

[0042] (B) The phosphor that emits light with a wavelength of 500 nm or less when irradiated with X-rays in a mixed state with a polymerizable compound is preferably in a particulate form, and its average particle size may be 1 nm to 50 μm. By setting the average particle size of the phosphor that emits light with a wavelength of 500 nm or less when irradiated with X-rays in a mixed state with a polymerizable compound within the above-mentioned range, sedimentation of the phosphor can be suppressed, and the formation of coarse particles can be suppressed, which can prevent wear on the nozzle of the jet dispenser and scattering of the resin composition ejected from the nozzle of the jet dispenser outside the desired area. Furthermore, the amount of light emitted and the light-emitting area can be controlled, making it easier to control the curability of the photocurable resin composition.

[0043] (B) A phosphor that emits light having a wavelength of 500 nm or less when irradiated with X-rays in a mixed state with a polymerizable compound can be produced by a known method, for example, in the case of an inorganic phosphor, by a solid-phase reaction method, a coprecipitation method, a sol-gel method (complex polymerization method), a solvothermal method (hydrothermal method), etc. (B) A phosphor that emits light having a wavelength of 500 nm or less when irradiated with X-rays in a mixed state with a polymerizable compound may be a commercially available product.

[0044] (B) The phosphor that emits light having a wavelength of 500 nm or less when irradiated with X-rays in a mixed state with a polymerizable compound may be used alone or in combination of two or more.

[0045] From the viewpoint of the degree of photocuring, the content of the (B) phosphor in the photocurable resin composition is preferably 1 to 100 parts by mass, and more preferably 5 to 90 parts by mass, relative to 100 parts by mass of the total amount of the (A) polymerizable compound.

[0046] The photocurable resin composition of this embodiment satisfies at least one of the following characteristics (a) and (b): (a) (A) the polymerizable compound contains a maleimide compound; (b) the photocurable resin composition contains (C) an oxime ester-based photopolymerization initiator.

[0047] In the feature (a), the maleimide compound, when mixed with the polymerizable compound (B), is activated by light having a wavelength of 500 nm or less, particularly 450 nm or less, generated by a phosphor that emits light having a wavelength of 500 nm or less upon X-ray irradiation to generate radicals, thereby promoting polymerization of the radically polymerizable compound. That is, the maleimide compound is not only a polymerizable compound but also functions as a photoradical polymerization initiator, promoting polymerization of the radically polymerizable compound containing the maleimide compound itself without the need for a separate (C) oxime ester-based photopolymerization initiator or other photopolymerization initiators. The maleimide compound functions as a photoradical polymerization initiator while being incorporated into the cured matrix of the cured product as a radically polymerizable compound, thereby suppressing VOC emissions from the photopolymerization initiator. When the feature (a) is satisfied, the polymerizable compound (A) can contain a radically polymerizable compound other than the maleimide compound. Furthermore, when the feature (a) is satisfied, the photocurable resin composition may further contain an oxime ester-based photopolymerization initiator (C) (the feature (b)).

[0048] (C) Oxime Ester Photopolymerization Initiator The photocurable resin composition of this embodiment that satisfies the characteristic (b) contains (C) an oxime ester photopolymerization initiator (hereinafter also referred to as "component (C)"). The oxime ester photopolymerization initiator is a photopolymerization initiator having an oxime ester group (C═N—O—CO—), and is a reactant that absorbs light, cleaves the N—O bond, generates radicals as active species, and promotes polymerization of a polymerizable compound. Oxime ester photopolymerization initiators are known as highly sensitive photopolymerization initiators with a quantum yield close to 1, and even when used in small amounts, they easily initiate polymerization of a polymerizable compound. In addition, the gas by-produced during radical generation from oxime ester photopolymerization initiators is mainly CO ２Since there is no adhesion or contamination to surrounding components, it is unlikely to lead to corrosion of semiconductor devices or electronic components or contamination of the surrounding area. Furthermore, the photosensitive moiety generated by decomposition of the oxime ester photopolymerization initiator has a relatively large molecular weight and may be incorporated into the cured matrix of the cured product, making it unlikely to be released as a VOC. From the viewpoint of radical transfer rate, the oxime ester photopolymerization initiator preferably has a structure that generates an aryl radical or a methyl radical, and more preferably a structure that generates a methyl radical.

[0049] Examples of oxime ester photopolymerization initiators include, but are not limited to, 1,2-octanedione, 1-[4-(phenylthio)-, 2-(O-benzoyloxime)] (trade name: Irgacure OXE-01, manufactured by BASF), ethanone, 1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-, 1-(O-acetyloxime) (trade name: Irgacure OXE-02, manufactured by BASF), methanone, ethanone, 1-[9-ethyl-6-(1,3-dioxolane, 4-(2-methoxyphenoxy)-9H-carbazol-3-yl]-, 1-(O-acetyloxime) (trade name: ADEKA OPT-N-1919, manufactured by ADEKA Corporation). These may be used alone or in combination of two or more.

[0050] In the feature (b), the content of the oxime ester photopolymerization initiator (C) in the photocurable resin composition is 0.01 to 30 parts by mass, preferably 0.05 to 30 parts by mass, more preferably 0.1 to 30 parts by mass, and even more preferably 0.5 to 20 parts by mass, relative to 100 parts by mass of the total of the radical polymerizable compounds.

[0051] (D) Photopolymerization Initiators Other Than Oxime Ester-Based Photopolymerization Initiators The photocurable resin composition of this embodiment may contain (D) a photopolymerization initiator other than an oxime ester-based photopolymerization initiator. However, the content of the photoradical polymerization initiator (C) including the oxime ester-based photopolymerization initiator is preferably less than 6% by mass, more preferably 5% by mass or less, and even more preferably 3% by mass or less, relative to the total mass of the photocurable resin composition. Photoradical polymerization initiators other than oxime ester-based photopolymerization initiators may be released as volatile organic compounds (VOCs) upon decomposition upon exposure to light, or during subsequent assembly processes or use of semiconductor devices or electronic components. Therefore, the photocurable resin composition of this embodiment preferably does not contain any photoradical polymerization initiators other than oxime ester-based photopolymerization initiators, or, if it does contain any, it preferably contains only a small amount of such initiators. In this specification, the photopolymerization initiator other than an oxime ester-based photopolymerization initiator refers to a photoradical polymerization initiator other than an oxime ester-based photopolymerization initiator, a photoacid generator, a photobase generator, or any combination thereof.

[0052] Examples of photoradical polymerization initiators other than oxime ester-based photopolymerization initiators include, but are not limited to, alkylphenone-based compounds, acylphosphine oxide-based compounds, and compounds having a photosensitive moiety and a peroxide structure.

[0053] Examples of alkylphenone compounds include benzyl dimethyl ketals such as 2,2-dimethoxy-1,2-diphenylethan-1-one (commercially available as Omnirad 651 from IGM Resins B.V.); α-aminoalkylphenones such as 2-methyl-2-morpholino(4-thiomethylphenyl)propan-1-one (commercially available as Omnirad 907 from IGM Resins B.V.); α-hydroxyalkylphenones such as 1-hydroxy-cyclohexyl-phenyl-ketone (commercially available as Omnirad 184 from IGM Resins B.V.); 2-dimethylamino-2-(4-methyl-benzyl)-1-(4-morpholin-4-yl-phenyl)-butan-1-one (commercially available as Omnirad 184 from IGM Resins B.V.); 379EG), 2-benzyl-2-(dimethylamino)-4'-morpholinobutyrophenone (commercially available as Omnirad 369, manufactured by IGM Resins BV), and the like.

[0054] Examples of the acylphosphine oxide compound include, but are not limited to, 2,4,6-trimethylbenzoyl-diphenyl-phosphine oxide (commercially available as Omnirad TPO H manufactured by IGM Resins B.V.), bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide (commercially available as Omnirad 819 manufactured by IGM Resins B.V.), and the like.

[0055] Examples of compounds having a photosensitive moiety and a peroxide structure or commercially available products thereof include 3,3′,4,4′-tetrakis(tert-butylperoxycarbonyl)benzophenone (BTTB), Perdual TA, and Perdual TX (all manufactured by NOF Corporation), but are not limited to these.

[0056] In addition to the above-mentioned photoradical polymerization initiators, examples of the photoradical polymerization initiator include 2-hydroxy-2-methyl-1-phenylpropan-1-one, diethoxyacetophenone, 1-(4-isopropylphenyl)-2-hydroxy-2-methylpropan-1-one, 1-(4-dodecylphenyl)-2-hydroxy-2-methylpropan-1-one, 4-(2-hydroxyethoxy)-phenyl(2-hydroxy-2-propyl)ketone, 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one, benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin n-butyl ether, benzoin phenyl ether, and benzyl dimethyl Examples of the benzoxanthone include, but are not limited to, ketals, benzophenone, benzoylbenzoic acid, methyl benzoylbenzoate, 4-phenylbenzophenone, hydroxybenzophenone, acrylated benzophenone, 4-benzoyl-4'-methyldiphenyl sulfide, 3,3'-dimethyl-4-methoxybenzophenone, thioxanthone, 2-chlorothioxanthone, 2-methylthioxanthone, 2,4-dimethylthioxanthone, isopropylthioxanthone, 2,4-dichlorothioxanthone, 2,4-diethylthioxanthone, 2,4-diisopropylthioxanthone, 2,4,6-trimethylbenzoyldiphenylphosphine oxide, methylphenyl glyoxylate, benzil, camphorquinone, and the like.

[0057] The photoacid generator absorbs light to generate an acid as an active species, which promotes the polymerization of the cationic polymerizable compound. ４ － , SbF ６ -, AsF ６ － , B(C ６ F ５ ) ４ － , Ga(C ６ F ５ ) ４ － , C(CF ３ SO ２ ) ３ － , [P(R １) ａ F ６－ａ ] － , [C(R １ SO ２ ) ３ ] － , or [N(R １ SO ２ ) ２ ] － (In the formula, R １ are each independently an alkyl group in which at least a portion of the hydrogen atoms is substituted with a fluorine atom, a is an integer of 0 to 5, and when a is an integer of 2 or more, a plurality of R １ may be the same or different.) as a counter anion, and an iodonium cation, a sulfonium cation, an ammonium cation, a phosphonium cation, or the like as a cation moiety.

[0058] Examples of iodonium cations include iodonium ions such as diphenyliodonium, di-p-tolyliodonium, bis(4-dodecylphenyl)iodonium, bis(4-methoxyphenyl)iodonium, (4-octyloxyphenyl)phenyliodonium, bis(4-decyloxy)phenyliodonium, 4-(2-hydroxytetradecyloxy)phenylphenyliodonium, 4-isopropylphenyl(p-tolyl)iodonium, and 4-isobutylphenyl(p-tolyl)iodonium.

[0059] Examples of sulfonium ions include triphenylsulfonium, tri-p-tolylsulfonium, tri-o-tolylsulfonium, tris(4-methoxyphenyl)sulfonium, 1-naphthyldiphenylsulfonium, 2-naphthyldiphenylsulfonium, tris(4-fluorophenyl)sulfonium, tri-1-naphthylsulfonium, tri-2-naphthylsulfonium, tris(4-hydroxyphenyl)sulfonium, 4-(phenylthio)phenyldiphenylsulfonium, 4-(p-tolylthio)phenyldi-p-tolylsulfonium, 4-(4-methoxyphenylthio)phenylbis(4-methoxyphenyl)sulfonium, 4-(phenylthio)phenylbis(4-fluorophenyl)sulfonium, phenyl)sulfonium, 4-(phenylthio)phenylbis(4-methoxyphenyl)sulfonium, 4-(phenylthio)phenyldi-p-tolylsulfonium, [4-(4-biphenylylthio)phenyl]-4-biphenylylphenylsulfonium, [4-(2-thioxanthonylthio)phenyl]diphenylsulfonium, bis[4-(diphenylsulfonio)phenyl]sulfide, bis[4-{bis[4-(2-hydroxyethoxy)phenyl]sulfonio}phenyl]sulfide, bis{4-[bis(4-fluorophenyl)sulfonio]phenyl}sulfide, bis{4-[bis(4-methylphenyl)sulfonio]phenyl}sulfide, bis{4-[bis(4-methoxyphenyl)sulfonio] phenyl} sulfide, 4-(4-benzoyl-2-chlorophenylthio)phenylbis(4-fluorophenyl)sulfonium, 4-(4-benzoyl-2-chlorophenylthio)phenyldiphenylsulfonium, 4-(4-benzoylphenylthio)phenylbis(4-fluorophenyl)sulfonium, 4-(4-benzoylphenylthio)phenyldiphenylsulfonium, 7-isopropyl-9-oxo-10-thia-9,10-dihydroanthracen-2-yldi-p-tolylsulfonium, 7-isopropyl-9-oxo-10-thia-9,10-dihydroanthracen-2-yldi-p-tolylsulfonium,10-Dihydroanthracen-2-yldiphenylsulfonium, 2-[(di-p-tolyl)sulfonio]thioxanthone, 2-[(diphenyl)sulfonio]thioxanthone, 4-(9-oxo-9H-thioxanthen-2-yl)thiophenyl-9-oxo-9H-thioxanthen-2-ylphenylsulfonium, 4-[4-(4-t-butylbenzoyl)phenylthio]phenyldi-p-tolylsulfonium, 4-[4-(4-t-butylbenzoyl)phenylthio]phenyl triarylsulfoniums such as 4-[4-(benzoylphenylthio)]phenyldi-p-tolylsulfonium, 4-[4-(benzoylphenylthio)]phenyldiphenylsulfonium, 5-(4-methoxyphenyl)thiaanthrenenium, 5-phenylthiaanthrenenium, 5-tolylthiaanthrenenium, 5-(4-ethoxyphenyl)thiaanthrenenium, and 5-(2,4,6-trimethylphenyl)thiaanthrenenium.

[0060] Examples of ammonium cations include pyrrolidiniums such as N,N-dimethylpyrrolidinium, N-ethyl-N-methylpyrrolidinium, and N,N-diethylpyrrolidinium; imidazoliniums such as N,N'-dimethylimidazolinium, N,N'-diethylimidazolinium, N-ethyl-N'-methylimidazolinium, 1,3,4-trimethylimidazolinium, and 1,2,3,4-tetramethylimidazolinium; tetrahydropyrimidiniums such as N,N'-dimethyltetrahydropyrimidinium; and morpholiniums such as N,N'-dimethylmorpholinium. pyridinium such as N-methylpyridinium, N-benzylpyridinium, and N-phenacylpyridinium; imidazolium such as N,N'-dimethylimidazolium; quinolium such as N-methylquinolium, N-benzylquinolium, and N-phenacylquinolium; isoquinolium such as N-methylisoquinolium; thiazonium such as benzylbenzothiazonium and phenacylbenzothiazonium; and acridium such as benzylacridium and phenacylacridium.

[0061] Examples of the phosphonium cation include tetraarylphosphoniums such as tetraphenylphosphonium, tetra-p-tolylphosphonium, tetrakis(2-methoxyphenyl)phosphonium, tetrakis(3-methoxyphenyl)phosphonium, and tetrakis(4-methoxyphenyl)phosphonium; triarylphosphoniums such as triphenylbenzylphosphonium, triphenylphenacylphosphonium, triphenylmethylphosphonium, and triphenylbutylphosphonium; and tetraalkylphosphoniums such as triethylbenzylphosphonium, tributylbenzylphosphonium, tetraethylphosphonium, tetrabutylphosphonium, tetrahexylphosphonium, triethylphenacylphosphonium, and tributylphenacylphosphonium.

[0062] Specific examples of the iodonium salt-based photoacid generator include arsenate-based iodonium salt photoacid generators such as diphenyliodonium hexafluoroarsenate, di(4-chlorophenyl)iodonium hexafluoroarsenate, di(4-bromophenyl)iodonium hexafluoroarsenate, and phenyl(4-methoxyphenyl)iodonium hexafluoroarsenate; 4-methylphenyl-4-(1-methylethyl)phenyliodonium hexafluorophosphate, 4-methylphenyl-4-(1-methylethyl)phenyliodonium tri(pentafluoroethyl)trifluorophosphate (e.g., IK-1 manufactured by San-Apro Co., Ltd.), 4-methylphenyl-4-(2-methylpropyl)phenyliodonium hexafluorophosphate (e.g., IRGACURE (registered trademark) 250 manufactured by BASF), and bis(C １０～１４photoacid generators which are phosphate-based iodonium salts such as 4-methylphenyl-4-(1-methylethyl)phenyliodonium hexafluorophosphate (for example, WPI-113 manufactured by FUJIFILM Wako Pure Chemical Industries, Ltd.); photoacid generators which are antimonate-based iodonium salts such as 4-methylphenyl-4-(1-methylethyl)phenyliodonium hexafluoroantimonate (for example, WPI-116 manufactured by FUJIFILM Wako Pure Chemical Industries, Ltd.); photoacid generators which are gallate-based iodonium salts such as IK-1FG (manufactured by San-Apro Co., Ltd.); photoacid generators which are gallate-based iodonium salts such as 4-methylphenyl-4-(1-methylethyl)phenyliodonium tetrakis(pentafluorophenyl)borate and 4-isopropyl-4'-methyldiphenyliodonium tetrakis(pentafluorophenyl)borate (for example, BLUESIL (registered trademark) PI manufactured by ELKEM SILICONES); Photoacid generators which are borate-based iodonium salts such as 2074, etc., but are not limited to these.

[0063] Specific examples of sulfonium salt-based photoacid generators include, but are not limited to, borate-based sulfonium salt photoacid generators (for example, San-Apro Ltd.'s product names: CPI-110B, CPI-310B, CPI-410B, etc., and IGM Resins B.V.'s product Omnirad 290, etc.), phosphate-based sulfonium salt photoacid generators (San-Apro Ltd.'s product names: CPI-210S, VC-1S, CPI-410S, etc.), and gallate-based sulfonium salt photoacid generators (San-Apro Ltd.'s product names: CPI-310FG, VC-1FG, etc.).

[0064] The photobase generator absorbs light to generate a base as an active species, thereby promoting the polymerization of the anionically polymerizable compound. Examples of the photobase generator include, but are not limited to, various compounds that generate a base such as an amine, amidine, guanidine, phosphazene, or carbene.Specific examples of the photobase generator include 2-benzyl-2-(dimethylamino)-1-[4-(morpholino)phenyl]-1-butanone, 2-(dimethylamino)-2-(4-methylbenzyl)-1-(4-morpholinophenyl)butan-1-one, 2-nitrobenzyl 4-hydroxypiperidine-1-carboxylate, 4,5-dimethoxy-2-nitrobenzyl 2,6-dimethylpiperidine-1-carboxylate, 1-(9,10-dioxo-9,10-dihydroanthracen-2-yl)ethyl cyclohexylcarbamate, 1-(9,10-dioxo-9,10-dihydroanthracen-2-yl)ethyl 1H-imidazole-1-carboxylate, 3,4,6,7,8,9-hexahydro-2H-pyrimido[1,2-a]pyrimidine-1- ammonium 2-(3-benzoylphenyl)propanoate, diaminomethaniminium 2-(3-benzoylphenyl)propanoate, (Z)-N-(((bis(dimethylamino)methylene)amino)(isopropylamino)methylene)propan-2-aminium 2-(3-benzoylphenyl)propanoate, 1,2-dicyclohexyl-4,4,5,5-tetramethylbiguanidinium n-butyltriphenylborate, (Z)-{[bis(dimethylamino)methylidene]amino}-N-cyclohexyl(cyclohexylamino)methaniminium tetrakis(3-fluorophenyl)borate, 1,2-diisopropyl-3-[bis(dimethylamino)methylene]guanidinium 2-(3-benzoylphenyl)propionate, 9-anthrylmethyl Examples of suitable DBU derivatives include, but are not limited to, N,N-diethylcarbamate, (E)-1-piperidino-3-(2-hydroxyphenyl)-2-propen-1-one, 2-nitrophenylmethyl 4-methacryloyloxypiperidine-1-carboxylate, tetramethylguanidium tetrakis(3-fluorophenyl)borate, tetramethylguanidium tetrakis(4-fluorophenyl)borate, salts containing protonated DBU and tetrakis(3-fluorophenyl)borate anions, benzylated DBU and salts containing tetrakis(3-fluorophenyl)borate anions, and the like.

[0065] If desired, the photocurable resin composition of this embodiment may contain optional components other than the component (A) and the component (B) or the components (A) to (C), such as those described below, as necessary.

[0066] Filler The photocurable resin composition of this embodiment may contain a filler to the extent that the object of this embodiment is not impaired. By containing a filler in the photocurable resin composition, the linear expansion coefficient of the cured product obtained by curing the photocurable resin composition can be reduced, and thermal cycle resistance can be improved. Furthermore, if the filler has a low elastic modulus, stress generated in the cured product can be alleviated, and long-term reliability can be improved. Fillers are broadly classified into inorganic fillers and organic fillers.

[0067] The inorganic filler is not particularly limited as long as it is made of granular material formed from an inorganic material and has the effect of lowering the linear expansion coefficient when added. Examples of inorganic materials that can be used include silica, talc, alumina, aluminum nitride, calcium carbonate, aluminum silicate, magnesium silicate, magnesium carbonate, barium sulfate, barium carbonate, lime sulfate, aluminum hydroxide, calcium silicate, potassium titanate, titanium oxide, zinc oxide, silicon carbide, silicon nitride, and boron nitride. One type of inorganic filler may be used, or two or more types may be used in combination. In one embodiment, the inorganic filler may be a silica filler, as this allows for a high loading amount. The silica may be, for example, amorphous silica.

[0068] The inorganic filler may be surface-treated with a coupling agent such as a silane coupling agent, thereby allowing the thixotropic index (TI) of the resin composition to fall within an appropriate range.

[0069] Examples of the organic filler include polytetrafluoroethylene (PTFE) filler, silicone filler, acrylic filler, styrene filler, etc. The organic filler may be surface-treated.

[0070] The shape of the filler is not particularly limited, and may be any of spherical, flaky, needle-like, irregular, etc.

[0071] The average particle size of the filler is preferably 0.01 to 15 μm, more preferably 0.01 to 10 μm. From the viewpoint of the transmittance of X-rays irradiated to the photocurable resin composition, the maximum particle size of the filler is preferably 50 μm or less, more preferably 30 μm or less.

[0072] In this specification, the average particle size is the particle size at an integrated value of 50% in the particle size distribution on a volume basis measured by a laser diffraction / scattering method, and the maximum particle size is the maximum particle size in the particle size distribution on a volume basis measured by a laser diffraction / scattering method.

[0073] When a filler is contained, the content of the filler is preferably 0.5 to 80% by mass, more preferably 1 to 70% by mass, based on the total mass of the photocurable resin composition.

[0074] Thixotropic Agent The photocurable resin composition of this embodiment may contain a thixotropic agent to the extent that the effects of this embodiment are not impaired. Examples of thixotropic agents include silica such as colloidal silica, hydrophobic silica, fine silica, and nanosilica, as well as bentonite, acetylene black, and ketjen black. Nanosilica is preferred from the viewpoint of shape retention after application. Furthermore, from the viewpoints of preventing the resin composition from biting during bonding and moisture-resistant adhesion, the thixotropic agent is more preferably nanosilica having an average particle size of 10 to 750 nm, and even more preferably nanosilica having an average particle size of 20 to 600 nm. Commercially available products include hydrophobic fumed silica manufactured by CABOT Corporation (product name: CAB-O-SIL (registered trademark) TS720, average particle size: 12 nm), hydrophobic fumed silica manufactured by Nippon Aerosil (product name: R805, average particle size: 20 nm), and amorphous silica manufactured by Nippon Shokubai (product name: Seahoster KE-P10, average particle size 100 nm), but are not limited to these. Here, the average particle size of the nanosilica particles is measured using a dynamic light scattering Nanotrac particle size analyzer. The thixotropic agent may be used alone or in combination of two or more types.

[0075] When a thixotropic agent is contained, the content of the thixotropic agent is preferably 0.01 to 30 mass %, more preferably 0.05 to 25 mass %, and even more preferably 0.1 to 20 mass %, relative to the total mass of the photocurable resin composition.

[0076] Light-shielding agent The photocurable resin composition of this embodiment may contain a light-shielding agent to the extent that the effect of this embodiment is not impaired. Light-shielding properties may be required depending on the application of the cured resin composition. In such cases, the photocurable resin composition of this embodiment may contain a light-shielding agent. X-rays can pass through light-shielding agents that block ultraviolet rays. The photocurable resin composition of this embodiment can be photocured by irradiating X-rays without or with minimal influence from the light-shielding agent. Examples of light-shielding agents include, but are not limited to, carbon black and titanium black. These light-shielding agents can also be used as light-to-heat conversion materials that convert long-wavelength light into heat.

[0077] Other Additives The photocurable resin composition of this embodiment may further contain other additives, such as photosensitizers, conductive fillers, stabilizers, radical polymerization inhibitors, anionic polymerization inhibitors, silane coupling agents, ion trapping agents, leveling agents, antioxidants, antifoaming agents, viscosity modifiers, flame retardants, colorants, plasticizers, and solvents, if desired, within the scope of this embodiment. The type and amount of each additive are conventional. From the viewpoints of reducing the curing strength and adhesion upon photocuring and preventing outgassing and bleeding, the resin composition of this embodiment is substantially free of liquid components such as water, solvents, and ionic liquids (excluding liquid components (A) to (C)). For example, the content of liquid components is preferably 3% by mass or less, and more preferably 1% by mass or less, relative to the total mass of the resin composition. Examples of the solvent include organic solvents commonly used in the field of curable compositions, such as hydrocarbons (benzene, toluene, xylene, cyclohexane, etc.), aprotic polar solvents (N,N-dimethylformamide, dimethyl sulfoxide, N-methyl-2-pyrrolidone, etc.), nitriles (acetonitrile, etc.), ketones (acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, etc.), esters (ethyl acetate, butyl acetate, etc.), ethers (cyclopentyl methyl ether, diethyl ether, tetrahydrofuran, dimethoxyethane, etc.), alcohols (methanol, ethanol, propanol, butanol, etc.), terpenes (turpentine, terpineol, isobornyl acetate, etc.), and halogenated solvents (dichloromethane, chloroform, etc.).

[0078] The viscosity of the photocurable resin composition of this embodiment is preferably 0.1 to 100 Pa·s. The viscosity can be adjusted appropriately depending on the application and application location of the resin composition. The photocurable resin composition of this embodiment is excellent for application to areas with complex shapes that are difficult to irradiate with UV light, or for application to narrow areas. In this specification, viscosity is expressed as a value measured in accordance with Japanese Industrial Standard JIS K6833, unless otherwise specified. Specifically, it can be determined by measuring using an E-type viscometer at a rotation speed of 10 rpm. There are no particular limitations on the equipment, rotor, or measurement range used.

[0079] The photocurable resin composition of this embodiment can be a one-component resin composition contained in a single container, or a two-component (or multi-component) resin composition divided into two or more containers, depending on the intended use. When using a two-component (or multi-component) resin composition, the two components (or multiple components) are mixed to form the photocurable resin composition in use. When using a two-component (or multi-component) resin composition, the components (A) and (B) or components (A) to (C), and other optional components as needed, can be selected in the same manner as for a one-component resin composition. Furthermore, when using a two-component (or multi-component) resin composition, the components (A) and (B) or components (A) to (C), and other optional components as needed, can be divided into two or multiple components in any manner without particular limitations. However, from the viewpoint of preventing curing due to unintended radiation exposure (e.g., X-ray exposure for security inspections), it is preferable to separate the maleimide compound and / or photopolymerization initiator from the phosphor (B). When the mixture is separated into two or more liquids by any separation method, each liquid may contain one or more components selected from the group consisting of component (A) and component (B) or components (A) to (C) and other optional components as required, or the group consisting of component (A) and component (B) or components (A) to (C) and other optional components as required may be contained in a single liquid, or a liquid may consist solely of component (A) and component (B) or components (A) to (C) and / or other optional components as required. For example, when the mixture is separated into liquids A and B, the separation may be as follows: liquid A: component (A), liquid B: component (B), or liquid A: component (A) (excluding the maleimide compound) and component (B), or liquid B: component (C), or liquid A: component (A) and component (C), or liquid B: component (B), or liquid A: component (A) and component (C), or liquid B: component (B), or liquid A: component (A) and component (C), or liquid B: component (A) (excluding the maleimide compound) and component (B). When component (A) and component (B) or components (A) to (C) are contained in solution A, solution B may contain one or more components selected from component (A) and component (B) or components (A) to (C). In addition, components other than component (A) and component (B) or components (A) to (C) may be contained in both or either solution A and solution B in the above combination.When component (A) and component (B) or component (A) to component (C) are contained in liquid A and the other components are contained in liquid B, liquid A alone or liquid A and liquid B together can be considered the resin composition of this embodiment. On the other hand, when component (A) and component (B) or component (A) to component (C) are each contained in separate liquids, the respective liquids together can be considered the resin composition of this embodiment. Examples of when component (A) and component (B) or component (A) to component (C) are each contained in separate liquids include, for example, a resin composition in which component (A) and component (B) or component (A) to component (C) are separated into two or more containers, specifically, a kit composed of multiple liquids containing component (A) and component (B) or component (A) to component (C).

[0080] The method for producing the photocurable resin composition of this embodiment is not particularly limited. For example, the resin composition of this embodiment can be obtained by simultaneously or separately introducing component (A), component (B), and, if necessary, component (C) and other optional components into an appropriate mixer and mixing them by stirring to form a uniform composition. The mixer is not particularly limited, but examples of the mixer that can be used include a Raikai mixer, a Henschel mixer, a three-roll mill, a ball mill, a planetary mixer, and a bead mill equipped with a stirring device and a heating device. These devices may also be used in appropriate combination.

[0081] The photocurable resin composition obtained in this manner is cured by light through an X-ray irradiation process, completing the curing, and no heat curing treatment is required. Conventionally, UV light (e.g., 365 nm UV light) is generally used to photocure UV-curable adhesives. Therefore, if the adhesive contains a filler or the like, the penetration distance of the light into the UV-curable adhesive when irradiated with UV light is short, and curing does not proceed in areas where the light cannot reach due to obstructions or the like. On the other hand, X-rays are uncharged electromagnetic waves that do not cause electrostatic interactions with materials, and because of their short wavelengths of 1 pm to 10 nm, they have little interaction with the atomic nuclei or electrons of materials and have high penetrating power through materials. Due to the penetration depth of X-rays into the resin composition, photocuring via an X-ray irradiation process can be said to be useful as a method for increasing the degree of cure of photocurable resin compositions.

[0082] The photocurable resin composition of this embodiment can be used, for example, as an adhesive, sealant, or coating agent for fixing, joining, or protecting semiconductor devices or electronic components, or components constituting these, or as a raw material thereof. In one embodiment, the photocurable resin composition of this embodiment can be used in a photocuring method including an X-ray irradiation step. In one embodiment, the photocurable resin composition of this embodiment can be used as an adhesive, sealant, or coating agent for semiconductor devices or electronic components.

[0083] [Bonding Method] Another aspect of the present invention is a method for bonding at least two components with a photocurable resin composition, the bonding method including the steps of: applying the photocurable resin composition of the above aspect to at least one of the at least two components; and irradiating X-rays to at least one of the at least two components, the photocurable resin composition, or both of them.

[0084] In the first step, the photocurable resin composition of the above embodiment is applied to at least one of at least two components. The components are preferably components constituting a semiconductor device or electronic component, such as, but not limited to, a semiconductor element or a substrate. The material of the component may be any of general-purpose plastics (e.g., PE, PS, PP, etc.), engineering plastics (e.g., LCP (liquid crystal polymer), polyamide, polycarbonate, etc.), ceramics, or metals (e.g., copper, nickel). The method for applying the resin composition is not particularly limited, and the resin composition can be applied to a desired portion of a component, such as a substrate, by a known printing method, dispensing method, or coating method. Printing methods include, but are not limited to, inkjet printing, screen printing, lithographic printing, carton printing, metal printing, offset printing, gravure printing, flexographic printing, etc. Dispensing methods include, but are not limited to, methods using a jet dispenser, an air dispenser, etc. Examples of coating methods include, but are not limited to, dip coating, spray coating, bar coater coating, gravure coating, reverse gravure coating, and spin coater coating.

[0085] Next, another part is attached to the part coated with the photocurable resin composition via the photocurable resin composition, or the part coated with the photocurable resin composition is attached to the other part via the photocurable resin composition. Any known method may be used for the attachment. If necessary, after attachment, the parts may be pressed together while applying a load.

[0086] Next, X-rays are irradiated onto at least one of the at least two components, the photocurable resin composition, or both. As a result, the phosphor emitting light with a wavelength of 500 nm or less upon X-ray irradiation in a mixed state with the polymerizable compound (B) within the resin composition generates light with a wavelength of 500 nm or less, preferably light with a wavelength of 450 nm or less, more preferably light with a wavelength of 430 nm or less, and even more preferably light with a wavelength of 400 nm or less, activating the maleimide compound and / or photopolymerization initiator, curing the polymerizable compound, and bonding at least two components. The integrated X-ray dose and irradiation intensity can be adjusted appropriately depending on the desired degree of cure. For example, the X-ray irradiation time can be 1 second to 24 hours. In this embodiment, either spot laser irradiation, which irradiates a localized region with X-rays, or area laser irradiation, which irradiates a wide region with X-rays, can be used. The photocurable resin composition used in this embodiment can be cured even in the shadowed areas of the components. Therefore, in the bonding method of this embodiment, X-rays can be irradiated not only directly onto the photocurable resin composition, but also through the components.

[0087] [Sealing Method] Another aspect of the present invention is a method for sealing gaps between or within components with a curable resin composition, the sealing method comprising the steps of: applying or injecting the photocurable resin composition of the above-described embodiment into the gap between or within the components; and irradiating the photocurable resin composition with X-rays. The components and X-ray irradiation are the same as those in the bonding method. Examples of application or injection methods include the application method in the bonding method and potting, but are not limited to these. The photocurable resin composition used in this embodiment achieves a high cure depth, so the sealing method of this embodiment can cure the resin composition present deep in gaps that are difficult for ultraviolet light to reach, thereby achieving suitable sealing.

[0088] [Coating Method] Another aspect of the present invention is a method for coating the surface of an object with a curable composition, the method comprising: applying the photocurable resin composition of the above-described embodiment to the object; and irradiating the photocurable resin composition with X-rays. The object may be a semiconductor device or electronic component, or a component constituting the same. Examples of semiconductor devices or electronic components include, but are not limited to, HDDs, semiconductor elements, optical sensor modules such as image sensor modules and time-of-flight (TOF) sensor modules, other semiconductor modules, and integrated circuits. Components constituting the semiconductor device or electronic component include, but are not limited to, semiconductor elements, substrates, etc. The material of the component may be any of general-purpose plastics (e.g., PE, PS, PP, etc.), engineering plastics (e.g., LCP (liquid crystal polymer), polyamide, polycarbonate, etc.), ceramics, or metals (e.g., copper, nickel). The application method is the same as that in the bonding method. The X-ray irradiation method is the same as that in the bonding method.

[0089] [Adhesive, Sealant, or Coating Agent] Another embodiment of the present invention is an adhesive, sealant, or coating agent that includes the photocurable resin composition of the above embodiment. This adhesive, sealant, or coating agent provides excellent fixation, bonding, or protection for general-purpose plastics (e.g., PE, PS, PP, etc.), engineering plastics (e.g., LCP (liquid crystal polymer), polyamide, polycarbonate, etc.), ceramics, and metals (e.g., copper, nickel, etc.), and can be used to fix, bond, or protect semiconductor devices or electronic components, or components that constitute these. Examples of semiconductor devices or electronic components include, but are not limited to, HDDs, semiconductor elements, optical sensor modules such as image sensor modules and time-of-flight (TOF) sensor modules, other semiconductor modules, and integrated circuits. The adhesive, sealant, or coating agent of this embodiment can be cured by light via an X-ray irradiation process, which allows for high productivity and makes it suitable for use, for example, in the manufacture of semiconductor devices and electronic components.

[0090] [Cured Product of Resin Composition, Adhesive, Sealant, or Coating Agent] A cured product according to another embodiment of the present invention is a cured product obtained by curing the photocurable resin composition, adhesive, sealant, or coating agent according to the above-described embodiment.

[0091] [Semiconductor Device, Electronic Component] A semiconductor device or electronic component according to another embodiment of the present invention includes the cured product of the above embodiment, and therefore has high reliability. Here, the term "semiconductor device" refers to any device that can function by utilizing semiconductor properties, including electronic components, semiconductor circuits, modules incorporating these, electronic devices, etc. Examples of semiconductor devices or electronic components include, but are not limited to, HDDs, semiconductor elements, optical sensor modules such as image sensor modules and time-of-flight (TOF) sensor modules, other semiconductor modules, and integrated circuits.

[0092] [Curing Method, Manufacturing Method of Cured Product] Another aspect of the present invention is a method for manufacturing a cured product, comprising irradiating the photocurable resin composition of the above aspect, or the adhesive, sealant, or coating agent of the above aspect, with X-rays. Yet another aspect of the present invention is a method for photocuring a photocurable resin composition, comprising irradiating the photocurable resin composition of the above aspect with X-rays. Yet another aspect of the present invention is use of the photocurable resin composition of the above aspect in a photocuring method comprising an X-ray irradiation step. By irradiating with X-rays, a phosphor that emits light with a wavelength of 500 nm or less when irradiated with X-rays in a mixed state with the polymerizable compound (B) within the photocurable resin composition generates light with a wavelength of 500 nm or less, preferably light with a wavelength of 450 nm or less, more preferably light with a wavelength of 430 nm or less, and particularly preferably light with a wavelength of 400 nm or less, thereby activating the maleimide compound and / or photopolymerization initiator and curing the polymerizable compound. The details of X-ray irradiation in these methods are the same as those in the bonding method, sealing method, and coating method. In this embodiment, either spot laser irradiation, in which a local region is irradiated with X-rays, or area laser irradiation, in which a wide region is irradiated with X-rays, can be performed.

[0093] The present invention will be described in more detail below with reference to examples and comparative examples, but the present invention is not limited to these examples. In the following examples, parts and % represent parts by mass and % by mass unless otherwise specified.

[0094] [Production of One-Component Photocurable Resin Compositions] One-component photocurable resin compositions of Examples 1 to 16 and Comparative Examples 1 to 4 were prepared by mixing predetermined amounts of each component according to the formulations shown in Table 1. In Table 1, the amount of each component is expressed in mass %.

[0095] [Preparation of Two-Part Photocurable Resin Compositions] Liquid A, containing a maleimide compound and / or an oxime ester-based photopolymerization initiator and other optional components as needed, was prepared by mixing the prescribed amounts of each component according to the formulations shown in Table 2, and Liquid B, containing a radically polymerizable compound other than a maleimide compound, a phosphor that emits light with a wavelength of 500 nm or less when irradiated with X-rays, and other optional components as needed. Liquid A and Liquid B were then mixed to prepare the two-part photocurable resin compositions of Examples 17 to 21. In Table 2, the amount of each component is expressed in mass %.

[0096] The components used in the examples and comparative examples are as follows: (A) Polymerizable compound (A-1): Bismaleimide 1 having a hydrocarbon group derived from a dimer acid (product name: BMI-689, manufactured by Designer Molecules Inc., absorption edge wavelength: up to 390 nm) In this specification, the absorption edge wavelength refers to the wavelength at which the transmittance starts to decrease in transmittance measurement. (A-2): N-phenylmaleimide (product name: Imilex （Ｒ） -P, Nippon Shokubai Co., Ltd., absorption edge wavelength: up to 480 nm) (B) Phosphor that emits light with a wavelength of 500 nm or less when irradiated with X-rays in a state mixed with a polymerizable compound (B-1): YTaO ４ Yttrium oxide Y ２ O ３ (Fujifilm Wako Pure Chemical Industries, Ltd., 99.99%) and tantalum oxide Ta ２ O ５(FUJIFILM Wako Pure Chemical Corporation, 99.9%) were weighed out so that the molar ratio was 1:1, mixed, and thoroughly ground in an agate mortar. This powder was placed in an alumina crucible and fired in air at a temperature of 1300°C for 5 hours. X-ray diffraction (XRD) analysis revealed that the obtained powder was yttrium tantalate (YTaO ４ (B-2): CaWO ４ Calcium chloride CaCl ２ (Fujifilm Wako Pure Chemical Industries, Ltd., 99.9%) and sodium tungstate dihydrate Na ２ WO ４ ・2H ２ Two types of raw material aqueous solutions were prepared by weighing out calcium tungstate (CaWO) and calcium chloride (Fujifilm Wako Pure Chemical Industries, Ltd., 99.0%) at a molar ratio of 1:1 and dissolving each in distilled water. A calcium chloride aqueous solution was slowly added to the sodium tungstate aqueous solution to obtain a precipitate. The precipitate was recovered by centrifugation and thoroughly washed with distilled water. The precipitate was placed in an alumina crucible and fired in air at 1200°C for 5 hours. X-ray diffraction (XRD) analysis revealed that the resulting powder was calcium tungstate (CaWO). ４ (B-3): Y ２ SiO ５ : Ce (Phosphor Technology Ltd, Model No. QBK58 / N-A2) The emission spectra of phosphors (B-1), (B-2), and (B-3) upon X-ray irradiation are shown in Figure 1. (B') Phosphors other than component (B) (other phosphors) (B'-1): CeBr ３ (Fujifilm Wako Pure Chemical Industries, Ltd., 99.9%-Ce) CeBr ３When irradiated with X-rays, this compound alone emits light with a wavelength of 500 nm or less, but when mixed with a polymerizable compound, its crystallinity decreases due to dissolution and deliquescence, resulting in it no longer emitting light with a wavelength of 500 nm or less when irradiated with X-rays. - (C) Oxime ester photopolymerization initiator (C-1): Ethanone, 1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-, 1-(O-acetyloxime) (trade name: Irgacure OXE-02, manufactured by BASF) (C-1) is an oxime ester photopolymerization initiator that generates methyl radicals. (D) Photopolymerization initiator other than oxime ester-based photopolymerization initiator (D-1): 2-dimethylamino-2-(4-methyl-benzyl)-1-(4-morpholin-4-yl-phenyl)-butan-1-one (product name: Omnirad 379EG, manufactured by IGM Resins B.V., photoradical polymerization initiator)

[0097] In the examples and comparative examples, the properties of the resin compositions were measured as follows.

[0098] [Evaluation of Resin Composition Curability] In a dark place at a temperature of 22°C ± 5°C and a humidity of 50% ± 10%, a drop (approximately 0.02 g) of the photocurable resin composition was placed on a glass slide and inserted with a transparent acrylic plate to prepare a test piece, which was then subjected to X-ray irradiation. X-ray irradiation was performed for 5 hours using an X-ray diffractometer (Rigaku Ultima 4, X-ray source CuKα, tube voltage 40 kV, tube voltage 40 mA, irradiation angle 50°, no divergence slit). The acrylic plate was peeled off from the test piece, and the photocurability was evaluated on a two-point scale by appearance and palpation with a toothpick, with "Good" indicating cured and "Poor" indicating not cured. The results are shown in Tables 1 and 2.

[0099] [Evaluation of VOC Emissions During Curing] 1.0 g of the photocurable resin composition was placed in a 1 cm deep, 2 cm diameter plastic cap in a dark place at a temperature of 22°C ± 5°C and a humidity of 50% ± 10%. The cap was filled to the bottom, the surface was smoothed evenly, and then a transparent acrylic plate was placed over the cap to completely cover the opening, creating a test specimen, which was then subjected to X-ray irradiation. X-ray irradiation was performed for 5 hours using an X-ray diffractometer (Rigaku Ultima 4, CuKα X-ray source, 40 kV tube voltage, 40 mA tube voltage, 50° irradiation angle, no divergence slit). The transparent acrylic plate covering the opening was observed. If no cloudiness was observed, the absence of volatiles was evaluated as "absent," and if cloudiness was observed, the presence of volatiles was evaluated as "present." The results are shown in Tables 1 and 2.

[0100] In Tables 1 and 2, the overall evaluation was given as "Good" when the result of the curability evaluation was "Good" and the result of the VOC emission evaluation was "None", and "Poor" when at least one of the evaluation of curability and the evaluation of VOC emission was not satisfied.

[0101]

[0102]

[0103] The photocurable resin compositions of Examples 1 to 21, which satisfied the constitution of the present invention, were cured by X-ray irradiation and VOC emission was suppressed. On the other hand, the photocurable resin compositions of Comparative Examples 1 to 4, which did not satisfy the constitution of the present invention, were not cured by X-ray irradiation or VOC emission was confirmed.

[0104] The disclosure of Japanese Patent Application No. 2024-112697 (filing date: July 12, 2024) is incorporated herein by reference in its entirety. All documents, patent applications, and technical standards mentioned herein are incorporated herein by reference to the same extent as if each individual document, patent application, and technical standard was specifically and individually indicated to be incorporated by reference.

Claims

1. A photocurable resin composition comprising (A) a polymerizable compound, and (B) a phosphor that, when mixed with the polymerizable compound, emits light with a wavelength of 500 nm or less upon exposure to X-rays, and which satisfies at least one of the following characteristics (a) and (b): (a) (A) the polymerizable compound comprises a maleimide compound; (b) the photocurable resin composition comprises (C) an oxime ester-based photopolymerization initiator.

2. The photocurable resin composition according to claim 1, wherein the content of the photoradical polymerization initiator including the (C) oxime ester-based photopolymerization initiator is less than 6 mass % relative to the total mass of the photocurable resin composition.

3. A photocurable resin composition according to claim 1 or 2, wherein the polymerizable compound (A) further contains a radically polymerizable compound other than the maleimide compound.

4. The photocurable resin composition according to any one of claims 1 to 3, for use in a photocuring method including an X-ray irradiation step.

5. The photocurable resin composition according to any one of claims 1 to 4, which is used as an adhesive, sealant or coating agent for semiconductor devices or electronic parts.

6. The photocurable resin composition according to any one of claims 1 to 5, wherein component (A) and component (B) or components (A) to (C) are contained in a single container.

7. The photocurable resin composition according to any one of claims 1 to 5, wherein component (A) and component (B), or components (A) to (C), are separated into two or more containers.

8. An adhesive, sealant or coating agent comprising the photocurable resin composition according to any one of claims 1 to 7.

9. A cured product obtained by curing the photocurable resin composition according to any one of claims 1 to 7, or the adhesive, sealant or coating agent according to claim 8.

10. A semiconductor device or electronic component comprising the cured product according to claim 9.

11. A method for producing a cured product, comprising irradiating the photocurable resin composition according to any one of claims 1 to 7, or the adhesive, sealant or coating agent according to claim 8, with X-rays.

12. A method for curing a photocurable resin composition, comprising irradiating the photocurable resin composition according to any one of claims 1 to 7 with X-rays.

13. Use of the photocurable resin composition according to any one of claims 1 to 7 in a photocuring method including an X-ray irradiation step.

14. A method for bonding at least two components with a photocurable resin composition, comprising the steps of: applying the photocurable resin composition according to any one of claims 1 to 7 to at least one of the at least two components; and irradiating X-rays to at least one of the at least two components, the photocurable resin composition, or both.

15. A method for sealing gaps between or within components with a photocurable resin composition, comprising the steps of: applying or injecting the photocurable resin composition according to any one of claims 1 to 7 into the gaps between or within the components; and irradiating the photocurable resin composition with X-rays.

16. A method for coating the surface of an object with a photocurable resin composition, comprising the steps of: applying the photocurable resin composition according to any one of claims 1 to 7 to the object; and irradiating the photocurable resin composition with X-rays.

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