Resin composition, cured product, and laminate
The resin composition with a styrene-based polymer and specific additives improves adhesion to insulating members, addressing the adhesion issues of cured products in diverse applications.
Patent Information
- Application Number
- JP2024063458
- Authority / Receiving Office
- JP · JP
- Patent Type
- Applications
- Current Assignee / Owner
- Filing Date
- 2024-04-10
- Publication Date
- 2025-10-23
AI Technical Summary
Cured products used in various applications often lack sufficient adhesion to insulating materials.
A resin composition comprising a styrene-based polymer, a polymerizable compound with an ethylenically unsaturated bond and an amide bond, a (meth)acrylic compound, and a polymerization initiator, which improves adhesion to insulating members.
Enhances the adhesion of cured products to insulating members, enabling their use in electronic devices, semiconductor packages, and other applications.
Smart Images

Figure 2025160716000001_ABST
Abstract
Description
[Technical Field]
[0001] The present disclosure relates to a resin composition, a cured product, a laminate, and the like. [Background technology]
[0002] Cured products of resin compositions are sometimes used as components for various applications, such as electronic devices, semiconductor packages, image display devices, automobiles, buildings, transparent antennas, etc. As such resin compositions, compositions containing various components have been investigated (see, for example, Patent Document 1 below). [Prior art documents] [Patent documents]
[0003] [Patent Document 1] Special Publication No. 2020-528471 Summary of the Invention [Problem to be solved by the invention]
[0004] Cured products that can be used as components for various applications may be required to have improved adhesion to adherends, such as insulating materials.
[0005] An object of one aspect of the present disclosure is to provide a resin composition capable of improving the adhesion of a cured product to an insulating member.An object of another aspect of the present disclosure is to provide a cured product of such a resin composition.An object of another aspect of the present disclosure is to provide a laminate using such a resin composition or a cured product thereof. [Means for solving the problem]
[0006] The present disclosure relates to the following [1] to
[14] etc. [1] A resin composition comprising a styrene-based polymer, a polymerizable compound having an ethylenically unsaturated bond and an amide bond, a (meth)acrylic compound (excluding the polymerizable compound), and a polymerization initiator. [2] The resin composition according to [1], wherein the styrene-based polymer comprises a copolymer having a styrene compound and butadiene as monomer units. [3] The resin composition according to [1] or [2], wherein the content of the styrene polymer is 50 mass % or more based on the total mass of the resin composition. [4] The resin composition according to any one of [1] to [3], wherein the polymerizable compound contains a lactam compound. [5] The resin composition according to any one of [1] to [4], wherein the polymerizable compound contains an N-vinyl lactam compound. [6] The resin composition according to any one of [1] to [5], wherein the (meth)acrylic compound contains an alkanediol di(meth)acrylate. [7] The resin composition according to any one of [1] to [6], wherein the (meth)acrylic compound comprises a compound represented by the following general formula (I): [ka] [In the formula, R 1 represents a group containing 9 or less carbon atoms and 2 or more oxygen atoms, and R 2a and R 2b each independently represents a hydrogen atom or a methyl group. [8] The resin composition according to any one of [1] to [7], wherein the (meth)acrylic compound contains nonanediol di(meth)acrylate. [9] The resin composition according to any one of [1] to [8], wherein the polymerization initiator includes a thermal polymerization initiator.
[10] The resin composition according to any one of [1] to [9], wherein the polymerization initiator includes a photopolymerization initiator.
[11] A cured product of the resin composition according to any one of [1] to
[10] .
[12] A laminate comprising a base film and a resin layer disposed on the base film, wherein the resin layer comprises at least one selected from the group consisting of the resin composition according to any one of [1] to
[10] and a cured product thereof.
[13] A laminate comprising the cured product according to
[11] and an insulating member on the cured product in contact with the cured product.
[14] The laminate according to
[13] , further comprising a conductive member on the cured product in contact with the cured product. [Effects of the Invention]
[0007] According to one aspect of the present disclosure, it is possible to provide a resin composition that can improve the adhesion of a cured product to an insulating member. According to another aspect of the present disclosure, it is possible to provide a cured product of such a resin composition. According to another aspect of the present disclosure, it is possible to provide a laminate using such a resin composition or a cured product thereof. [Brief explanation of the drawings]
[0008] [Figure 1] 5A to 5C are schematic cross-sectional views showing an example of a method for manufacturing a semiconductor package. [Figure 2] 5A to 5C are schematic cross-sectional views showing an example of a method for manufacturing a semiconductor package. [Figure 3] 5A to 5C are schematic cross-sectional views showing an example of a method for manufacturing a semiconductor package. DETAILED DESCRIPTION OF THE INVENTION
[0009] Hereinafter, embodiments of the present disclosure will be described in detail, but the present disclosure is not limited to the following embodiments.
[0010] In this specification, a numerical range indicated with "to" indicates a range that includes the numerical values before and after "to" as the minimum and maximum values, respectively. A numerical range "A or greater" means a range exceeding A and A. A numerical range "A or less" means a range less than A and A. In the numerical ranges described in stages in this specification, the upper or lower limit of a numerical range in one stage can be arbitrarily combined with the upper or lower limit of a numerical range in another stage. In the numerical ranges described in this specification, the upper or lower limit of the numerical range may be replaced with a value shown in the examples. "A or B" may include either A or B, or may include both. Unless otherwise specified, the materials exemplified in this specification can be used alone or in combination of two or more. In this specification, when multiple substances corresponding to each component are present in the composition, the content of each component in the composition refers to the total amount of those multiple substances present in the composition, unless otherwise specified. The term "layer" encompasses not only a structure with a shape formed over the entire surface when observed in a plan view, but also a structure with a shape formed on a portion of the surface. The term "process" includes not only an independent process, but also a process that cannot be clearly distinguished from other processes as long as the intended effect of the process is achieved. "(Meth)acrylate" means at least one of acrylate and its corresponding methacrylate. The same applies to other similar expressions such as "(meth)acrylic." The content of (meth)acrylic compounds refers to the total amount of acrylic compounds and methacrylic compounds.
[0011] The resin composition according to this embodiment contains a styrene-based polymer, a polymerizable compound having an ethylenically unsaturated bond and an amide bond (hereinafter referred to as "polymerizable compound A"), a (meth)acrylic compound (excluding polymerizable compound A: the same applies hereinafter), and a polymerization initiator.
[0012] The resin composition according to this embodiment can improve the adhesion of a cured product (a cured product of the resin composition) to an insulating member. For example, the resin composition according to this embodiment can improve the adhesion of a resin composition to be evaluated in the evaluation method described in the Examples below (a method for evaluating adhesion to a polyimide film) compared to the adhesion of a resin composition obtained by excluding polymerizable compound A from the composition of the resin composition to be evaluated. It is presumed that the adhesion of a cured product to an insulating member is improved by the action of the amide bond of polymerizable compound A in the presence of a styrene-based polymer and a (meth)acrylic compound. However, the factors that improve the adhesion of a cured product to an insulating member are not limited to these.
[0013] The resin composition according to the present embodiment can be used as a curable resin composition, and may be used as a thermosetting resin composition or a photocurable resin composition. The cured product according to the present embodiment is obtained by curing the resin composition according to the present embodiment, and is a cured product of the resin composition according to the present embodiment. The cured product according to the present embodiment may be in a semi-cured state or a completely cured state.
[0014] The resin composition according to the present embodiment and its cured product may be used in a manner that contacts an insulating member (for example, a member containing an insulating material such as polyimide). As described above, the resin composition according to the present embodiment and its cured product may have the property of improving the adhesion of the cured product to an insulating member, and may be used in a manner that contacts a conductive member (for example, a metal member containing a metal material such as copper, silver, gold, or titanium) without contacting an insulating member.
[0015] The resin composition and cured product according to this embodiment can be used in various applications such as electronic devices, semiconductor packages, image display devices, automobiles (windshields, rear windows, sunroofs, windows, etc.), buildings, transparent antennas, etc. The electronic devices, semiconductor packages, image display devices, automobiles, buildings, and transparent antennas according to this embodiment comprise at least one selected from the group consisting of the resin compositions and cured products according to this embodiment.
[0016] The electronic device is not particularly limited, and examples thereof include a personal computer, a navigation system (e.g., a car navigation system), a mobile phone, a watch, and an electronic dictionary. The electronic device according to the present embodiment may include the image display device according to the present embodiment, and may also include the transparent antenna according to the present embodiment. The image display device may have an image display unit that displays an image and a bezel (frame) located around the image display unit, and the transparent antenna may be disposed in the image display unit.
[0017] The semiconductor package is not particularly limited, and examples thereof include a multi-chip package, a package-on-package, a wafer-level package, a panel-level package, a system-in-package, and various similar forms. The resin composition according to this embodiment can be used as a resin composition for a semiconductor package. The resin composition for a semiconductor package can be used to obtain a semiconductor package, a component of the semiconductor package, or an insulating member for the semiconductor package. The resin composition for a semiconductor package can be used to obtain a printed wiring board that constitutes a semiconductor package, and can be used to obtain an insulating member for the printed wiring board. The resin composition for a semiconductor package can be used to obtain an insulating member for forming a conductive member disposed on the insulating member. The resin composition for a semiconductor package can be used as a sheet-shaped material (e.g., resin sheet, prepreg), solder resist, underfill material, die bonding material, semiconductor encapsulant, hole-filling resin, component-embedding resin, etc. The resin composition and cured product according to this embodiment can be used as a component of a semiconductor package, and may be an insulating member or a transparent member.
[0018] The resin composition according to the present embodiment contains a styrene-based polymer. The styrene-based polymer is a polymer having a styrene compound as a monomer unit (a polymer having a monomer unit derived from a styrene compound). The styrene-based polymer may be a homopolymer of a styrene compound, a copolymer having a monomer unit of one styrene compound and a monomer unit of another styrene compound, or a copolymer having a monomer unit of a styrene compound and a monomer unit of a compound other than a styrene compound. From the viewpoint of easily improving the adhesion of the cured product to an insulating member, the styrene-based polymer may contain a copolymer, and may contain at least one selected from the group consisting of a block copolymer (a styrene-based block copolymer), a random copolymer (a styrene-based random copolymer), and a graft copolymer, or may contain at least one selected from the group consisting of a block copolymer and a random copolymer. The styrene-based polymer may be an elastomer.
[0019] Examples of styrene compounds include styrene, alkyl styrenes such as methylstyrene, dimethylstyrene, trimethylstyrene, ethylstyrene, diethylstyrene, triethylstyrene, propylstyrene, butylstyrene, hexylstyrene, heptylstyrene, and octylstyrene, halogenated styrenes such as fluorostyrene, chlorostyrene, bromostyrene, dibromostyrene, and iodostyrene, nitrostyrene, acetylstyrene, and methoxystyrene. The styrene-based polymer may have styrene as a monomer unit, from the viewpoint of easily improving the adhesion of the cured product to an insulating member.
[0020] Examples of styrene-based polymers include styrene-butadiene random copolymers, styrene-butadiene-styrene block copolymers, styrene-butylene-butadiene-styrene block copolymers, styrene-isoprene-styrene block copolymers, styrene-ethylene-butylene-styrene block copolymers, styrene-ethylene-propylene-styrene block copolymers, and hydrogenated copolymers thereof. From the viewpoint of easily improving the adhesion of the cured product to insulating members, the styrene-based polymer may include a copolymer having a styrene compound and butadiene as monomer units (a copolymer having monomer units derived from a styrene compound and monomer units derived from butadiene), and may include at least one selected from the group consisting of styrene-butadiene random copolymers and styrene-butadiene-styrene block copolymers.
[0021] The styrene-based polymer may be modified with a carboxylic acid anhydride, or may not be modified with a carboxylic acid anhydride. Examples of carboxylic acid anhydrides include dicarboxylic acid anhydrides such as maleic anhydride, phthalic anhydride, and itaconic anhydride. From the viewpoint of easily improving the adhesion of the cured product to insulating members, the styrene-based polymer may include a styrene-based polymer modified with a carboxylic acid anhydride (e.g., a styrene-based block copolymer), a styrene-based polymer modified with maleic anhydride (e.g., a styrene-based block copolymer), a styrene-butadiene-styrene block copolymer modified with a carboxylic acid anhydride, or a styrene-butadiene-styrene block copolymer modified with maleic anhydride. The styrene-based polymer may include a styrene-based polymer not modified with a carboxylic acid anhydride, or a styrene-based polymer not modified with maleic anhydride.
[0022] The content of the styrene compound monomer unit or the content of the styrene monomer unit may be within the following ranges based on the total mass of the styrene-based polymer, from the viewpoint of easily improving the adhesion of the cured product to insulating members. The content of the monomer unit may be 5% by mass or more, 10% by mass or more, 15% by mass or more, 20% by mass or more, 25% by mass or more, 30% by mass or more, 35% by mass or more, or 40% by mass or more. The content of the monomer unit may be 80% by mass or less, 75% by mass or less, 70% by mass or less, 65% by mass or less, 60% by mass or less, 55% by mass or less, 50% by mass or less, 45% by mass or less, 40% by mass or less, 35% by mass or less, 30% by mass or less, 25% by mass or less, or 20% by mass or less. From these viewpoints, the content of the monomer units may be 5 to 80 mass%, 5 to 50 mass%, 5 to 30 mass%, 10 to 80 mass%, 10 to 50 mass%, 10 to 30 mass%, 30 to 80 mass%, or 30 to 50 mass%.
[0023] From the viewpoint of easily improving the adhesion of the cured product to an insulating member, the content of the styrene polymer may be 50% by mass or more, more than 50% by mass, 70% by mass or more, 90% by mass or more, 95% by mass or more, or 99% by mass or more based on the total mass of the polymers (total amount of polymers contained in the resin composition). The polymer contained in the resin composition may be essentially composed of a styrene polymer (an embodiment in which the content of the styrene polymer is essentially 100% by mass based on the total mass of the polymers contained in the resin composition).
[0024] The content A of the polymer (polymer contained in the resin composition) or the styrene-based polymer may be in the following ranges based on the total mass of the resin composition (excluding the mass of the organic solvent), the total amount of the polymer (polymer contained in the resin composition), polymerizable compound A, (meth)acrylic compound, and polymerization initiator, the total amount of the styrene-based polymer, polymerizable compound A, (meth)acrylic compound, and polymerization initiator, the total amount of the polymer (polymer contained in the resin composition) and (meth)acrylic compound, or the total amount of the styrene-based polymer and (meth)acrylic compound, from the viewpoint of easily improving the adhesion of the cured product to the insulating member. The content A may be 20% by mass or more, more than 20% by mass, 30% by mass or more, more than 30% by mass, 40% by mass or more, more than 40% by mass, 50% by mass or more, more than 50% by mass, 60% by mass or more, 65% by mass or more, 70% by mass or more, 75% by mass or more, 78% by mass or more, or 80% by mass or more. The content A may be 99% by mass or less, 95% by mass or less, 90% by mass or less, 85% by mass or less, 82% by mass or less, or 80% by mass or less. From these viewpoints, the content A may be 20 to 99% by mass, 20 to 90% by mass, 20 to 85% by mass, 50 to 99% by mass, 50 to 90% by mass, 50 to 85% by mass, 70 to 99% by mass, 70 to 90% by mass, or 70 to 85% by mass.
[0025] The resin composition according to this embodiment contains a polymerizable compound A having an ethylenically unsaturated bond and an amide bond (-C(=O)-NH-). The "ethylenically unsaturated bond" refers to a carbon-carbon double bond capable of radical polymerization. The ethylenically unsaturated bond may be a vinyl group.
[0026] From the viewpoint of easily improving the adhesion of a cured product to an insulating member, the number of ethylenically unsaturated bonds in the polymerizable compound A may be 1 to 4, 1 to 3, or 1 to 2, or may be 1. From the viewpoint of easily improving the adhesion of a cured product to an insulating member, the number of amide bonds in the polymerizable compound A may be 1 to 4, 1 to 3, or 1 to 2, or may be 1.
[0027] The polymerizable compound A may contain a lactam compound (a compound having a lactam structure (a cyclic structure having a cyclic amide bond: a lactam ring)) or a lactam compound having a five-membered lactam structure (a five-membered ring having a cyclic amide bond), from the viewpoint of easily improving the adhesion of the cured product to the insulating member.
[0028] The hydrogen atom of the amide bond (for example, the hydrogen atom of the amide bond constituting the lactam structure) may be substituted with a substituent that does not correspond to a hydrogen atom. The substituent bonded to the nitrogen atom of the amide bond may be a hydrocarbon group, a group containing an ethylenically unsaturated bond, or a vinyl group, from the viewpoint of easily improving the adhesion of the cured product to an insulating member. The polymerizable compound A may have a tertiary amide bond, from the viewpoint of easily improving the adhesion of the cured product to an insulating member.
[0029] Examples of the polymerizable compound A include N-vinyl lactam compounds such as N-vinyl-2-pyrrolidone and N-vinyl-2-caprolactam; (meth)acrylamide compounds such as (meth)acrylamide and alkyl(meth)acrylamide; etc. The polymerizable compound A may contain an N-vinyl lactam compound or N-vinyl-2-pyrrolidone, from the viewpoint of easily improving the adhesion of the cured product to the insulating member.
[0030] The content of the polymerizable compound A may be in the following ranges relative to 100 parts by mass of the polymer (polymer contained in the resin composition) or 100 parts by mass of the styrene-based polymer. From the viewpoint of easily improving the adhesion of the cured product to the insulating member, the content of the polymerizable compound A may be 0.1 parts by mass or more, 0.5 parts by mass or more, 1 part by mass or more, 3 parts by mass or more, 5 parts by mass or more, 8 parts by mass or more, 10 parts by mass or more, or 12 parts by mass or more. From the viewpoint of adjusting the adhesion of the cured product to the insulating member, the content of the polymerizable compound A may be 50 parts by mass or less, 40 parts by mass or less, 30 parts by mass or less, 20 parts by mass or less, 15 parts by mass or less, 12 parts by mass or less, 10 parts by mass or less, 8 parts by mass or less, 5 parts by mass or less, or 3 parts by mass or less. From these viewpoints, the content of the polymerizable compound A may be 0.1 to 50 parts by mass, 0.1 to 15 parts by mass, 0.1 to 10 parts by mass, 1 to 50 parts by mass, 1 to 15 parts by mass, 1 to 10 parts by mass, 3 to 50 parts by mass, 3 to 15 parts by mass, 3 to 10 parts by mass, 10 to 50 parts by mass, or 10 to 15 parts by mass.
[0031] The content of the polymerizable compound A may be within the following ranges based on the total mass of the resin composition (excluding the mass of the organic solvent), the total amount of the polymer (polymer contained in the resin composition), the polymerizable compound A, the (meth)acrylic compound, and the polymerization initiator, the total amount of the styrene-based polymer, the polymerizable compound A, the (meth)acrylic compound, and the polymerization initiator, the total amount of the polymer (polymer contained in the resin composition) and the (meth)acrylic compound, or the total amount of the styrene-based polymer and the (meth)acrylic compound. From the viewpoint of easily improving the adhesion of the cured product to insulating members, the content of the polymerizable compound A may be 0.1% by mass or more, 0.5% by mass or more, 1% by mass or more, 3% by mass or more, 5% by mass or more, 8% by mass or more, or 10% by mass or more. From the viewpoint of adjusting the adhesion of the cured product to insulating members, the content of the polymerizable compound A may be 30% by mass or less, 20% by mass or less, 15% by mass or less, 10% by mass or less, 8% by mass or less, 5% by mass or less, 3% by mass or less, or 1% by mass or less. From these viewpoints, the content of polymerizable compound A may be 0.1 to 30 mass%, 0.1 to 15 mass%, 0.1 to 8 mass%, 1 to 30 mass%, 1 to 15 mass%, 1 to 8 mass%, 5 to 30 mass%, 5 to 15 mass%, or 5 to 8 mass%.
[0032] The resin composition according to this embodiment contains a (meth)acrylic compound (excluding polymerizable compound A). The (meth)acrylic compound is a compound having a (meth)acryloyl group. The (meth)acrylic compound may or may not have an epoxy group. The (meth)acrylic compound may not have an amide bond.
[0033] The (meth)acrylic compound may contain at least one selected from the group consisting of monofunctional (meth)acrylic compounds and polyfunctional (meth)acrylic compounds (difunctional (meth)acrylic compounds, or trifunctional or higher functional (meth)acrylic compounds). For example, a "difunctional (meth)acrylic compound" refers to a compound in which the total number of acryloyl groups and methacryloyl groups in one molecule is two. The (meth)acrylic compound may contain a bifunctional (meth)acrylic compound, from the viewpoint of easily improving the adhesion of the cured product to insulating members.
[0034] Examples of monofunctional (meth)acrylic compounds include methyl (meth)acrylate, ethyl (meth)acrylate, butyl (meth)acrylate, isobutyl (meth)acrylate, tert-butyl (meth)acrylate, butoxyethyl (meth)acrylate, isoamyl (meth)acrylate, hexyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, heptyl (meth)acrylate, octylheptyl (meth)acrylate, nonyl (meth)acrylate, decyl (meth)acrylate, undecyl (meth)acrylate, lauryl (meth)acrylate, tridecyl (meth)acrylate, tetradecyl (meth)acrylate, pentadecyl (meth)acrylate, hexadecyl (meth)acrylate, stearyl (meth)acrylate, behenyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, and 2-hydroxypropyl (meth)acrylate. aliphatic (meth)acrylates such as acrylate, 3-chloro-2-hydroxypropyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, methoxypolyethylene glycol (meth)acrylate, ethoxypolyethylene glycol (meth)acrylate, methoxypolypropylene glycol (meth)acrylate, ethoxypolypropylene glycol (meth)acrylate, and mono(2-(meth)acryloyloxyethyl)succinate; alicyclic (meth)acrylates such as cyclopentyl (meth)acrylate, cyclohexyl (meth)acrylate, cyclopentyl (meth)acrylate, dicyclopentanyl (meth)acrylate, dicyclopentenyl (meth)acrylate, isobornyl (meth)acrylate, mono(2-(meth)acryloyloxyethyl)tetrahydrophthalate, and mono(2-(meth)acryloyloxyethyl)hexahydrophthalate;Benzyl (meth)acrylate, phenyl (meth)acrylate, o-biphenyl (meth)acrylate, 1-naphthyl (meth)acrylate, 2-naphthyl (meth)acrylate, phenoxyethyl (meth)acrylate, p-cumylphenoxyethyl (meth)acrylate, o-phenylphenoxyethyl (meth)acrylate, 1-naphthoxyethyl (meth)acrylate, 2-naphthoxyethyl (meth)acrylate, phenoxypolyethylene glycol (meth)acrylate, nonylphenoxypolyethylene glycol (meth)acrylate, phenoxypolypropylene glycol (meth)acrylate, 2-hydroxy-3-phenoxypropyl (meth)acrylate aromatic (meth)acrylates such as 2-hydroxy-3-(o-phenylphenoxy)propyl (meth)acrylate, 2-hydroxy-3-(1-naphthoxy)propyl (meth)acrylate, and 2-hydroxy-3-(2-naphthoxy)propyl (meth)acrylate; heterocyclic (meth)acrylates such as 2-tetrahydrofurfuryl (meth)acrylate, N-(meth)acryloyloxyethylhexahydrophthalimide, and 2-(meth)acryloyloxyethyl-N-carbazole; (meth)acryloyl group-containing phosphates (for example, (meth)acryloyloxyethyl acid phosphate); and caprolactone-modified versions of these.
[0035] Examples of bifunctional (meth)acrylic compounds include ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, tetraethylene glycol di(meth)acrylate, polyethylene glycol di(meth)acrylate, propylene glycol di(meth)acrylate, dipropylene glycol di(meth)acrylate, tripropylene glycol di(meth)acrylate, tetrapropylene glycol di(meth)acrylate, polypropylene glycol di(meth)acrylate, ethoxylated polypropylene glycol di(meth)acrylate, 1,3-butanediol di(meth)acrylate, 1,4-butanediol di(meth)acrylate, neopentyl glycol aliphatic (meth)acrylates (e.g., alkanediol di(meth)acrylates) such as butyl di(meth)acrylate, 3-methyl-1,5-pentanediol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, 2-butyl-2-ethyl-1,3-propanediol di(meth)acrylate, nonanediol di(meth)acrylate (e.g., 1,9-nonanediol di(meth)acrylate), decanediol di(meth)acrylate (e.g., 1,10-decanediol di(meth)acrylate), dodecanediol di(meth)acrylate (e.g., 1,12-dodecanediol di(meth)acrylate), glycerin di(meth)acrylate, and ethoxylated 2-methyl-1,3-propanediol di(meth)acrylate;Cyclohexanedimethanol di(meth)acrylate, ethoxylated cyclohexanedimethanol di(meth)acrylate, propoxylated cyclohexanedimethanol di(meth)acrylate, ethoxylated propoxylated cyclohexanedimethanol di(meth)acrylate, tricyclodecane dimethanol di(meth)acrylate, ethoxylated tricyclodecane dimethanol di(meth)acrylate, propoxylated tricyclodecane dimethanol di(meth)acrylate, ethoxylated propoxylated tricyclodecane dimethanol di(meth)acrylate p) Alicyclic (meth)acrylates such as acrylate, ethoxylated hydrogenated bisphenol A di(meth)acrylate, propoxylated hydrogenated bisphenol A di(meth)acrylate, ethoxylated propoxylated hydrogenated bisphenol A di(meth)acrylate, ethoxylated hydrogenated bisphenol F di(meth)acrylate, propoxylated hydrogenated bisphenol F di(meth)acrylate, and ethoxylated propoxylated hydrogenated bisphenol F di(meth)acrylate; ethoxylated bisphenol A di(meth)acrylate, propoxylated bisphenol A Di(meth)acrylate, ethoxylated propoxylated bisphenol A di(meth)acrylate, ethoxylated bisphenol F di(meth)acrylate, propoxylated bisphenol F di(meth)acrylate, ethoxylated propoxylated bisphenol F di(meth)acrylate, ethoxylated bisphenol AF di(meth)acrylate, propoxylated bisphenol AF di(meth)acrylate, ethoxylated propoxylated bisphenol AF di(meth)acrylate, ethoxylated fluorene type di(meth)acrylate, propoxylated Aromatic (meth)acrylates such as fluorene-type di(meth)acrylate and ethoxylated propoxylated fluorene-type di(meth)acrylate; heterocyclic (meth)acrylates such as dioxane glycol di(meth)acrylate, ethoxylated isocyanuric acid di(meth)acrylate, propoxylated isocyanuric acid di(meth)acrylate, and ethoxylated propoxylated isocyanuric acid di(meth)acrylate; caprolactone-modified versions of these; aliphatic epoxy (meth)acrylates such as neopentyl glycol-type epoxy (meth)acrylate;Examples of the epoxy (meth)acrylate include alicyclic epoxy (meth)acrylates such as cyclohexanedimethanol-type epoxy (meth)acrylate, hydrogenated bisphenol A-type epoxy (meth)acrylate, and hydrogenated bisphenol F-type epoxy (meth)acrylate; and aromatic epoxy (meth)acrylates such as resorcinol-type epoxy (meth)acrylate, bisphenol A-type epoxy (meth)acrylate, bisphenol F-type epoxy (meth)acrylate, bisphenol AF-type epoxy (meth)acrylate, and fluorene-type epoxy (meth)acrylate.
[0036] Examples of the trifunctional or higher (meth)acrylic compound include trimethylolpropane tri(meth)acrylate, ethoxylated trimethylolpropane tri(meth)acrylate, propoxylated trimethylolpropane tri(meth)acrylate, ethoxylated propoxylated trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, ethoxylated pentaerythritol tri(meth)acrylate, propoxylated pentaerythritol tri(meth)acrylate, ethoxylated propoxylated pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, ethoxylated pentaerythritol tetra(meth)acrylate, propoxylated pentaerythritol tetra(meth)acrylate, ethoxylated propoxylated pentaerythritol tri(meth)acrylate, Examples of the epoxy (meth)acrylate include aliphatic (meth)acrylates such as ethoxylated pentaerythritol tetra(meth)acrylate, ditrimethylolpropane tetra(meth)acrylate, dipentaerythritol hexa(meth)acrylate, ethoxylated dipentaerythritol hexa(meth)acrylate, and propoxylated dipentaerythritol hexa(meth)acrylate; heterocyclic (meth)acrylates such as ethoxylated isocyanuric acid tri(meth)acrylate, propoxylated isocyanuric acid tri(meth)acrylate, and ethoxylated propoxylated isocyanuric acid tri(meth)acrylate; caprolactone-modified versions of these; and aromatic epoxy (meth)acrylates such as phenol novolac epoxy (meth)acrylate and cresol novolac epoxy (meth)acrylate.
[0037] The (meth)acrylic compound may contain an aliphatic (meth)acrylate, from the viewpoint of easily improving the adhesion of the cured product to insulating members. The (meth)acrylic compound may contain an alkanediol di(meth)acrylate, or may contain at least one selected from the group consisting of nonanediol di(meth)acrylate and dodecanediol di(meth)acrylate, or may contain nonanediol di(meth)acrylate, from the viewpoint of easily improving the adhesion of the cured product to insulating members. The (meth)acrylic compound may contain an acrylic compound, from the viewpoint of easily improving the adhesion of the cured product to insulating members.
[0038] The (meth)acrylic compound may contain a compound represented by the following general formula (I), from the viewpoint of easily improving the adhesion of the cured product to an insulating member.
[0039] [ka] [In the formula, R 1 represents a group containing 9 or less carbon atoms and 2 or more oxygen atoms, and R 2a and R 2b each independently represents a hydrogen atom or a methyl group.
[0040] R 1 The number of carbon atoms in R is 1 to 9. 1 The number of carbon atoms in R may be 2 or more, 3 or more, 4 or more, 5 or more, 6 or more, 7 or more, or 8 or more, from the viewpoint of easily improving the adhesion of the cured product to the insulating member. 1 The number of oxygen atoms in R may be 6 or less, 5 or less, 4 or less, 3 or less, or 2 or less, from the viewpoint of easily improving the adhesion of the cured product to the insulating member. 1 may be a hydrocarbon group with oxygen atoms attached to both ends, such as "-OC n H 2n In view of the tendency of improving the adhesion of the cured product to insulating members, the (meth)acrylic compound may be a -O- group (n=1 to 9). 1may include compounds that do not have a cyclic structure, and in general formula (I), R 1 may contain a compound that does not have an alicyclic ring.
[0041] From the viewpoint of easily improving the adhesion of the cured product to the insulating member, the content of the compound represented by general formula (I) may be 50% by mass or more, more than 50% by mass, 70% by mass or more, 90% by mass or more, 95% by mass or more, 99% by mass or more, or more than 99% by mass, based on the total mass of the (meth)acrylic compounds (excluding polymerizable compound A). The (meth)acrylic compounds (excluding polymerizable compound A) contained in the resin composition may be essentially composed of the compound represented by general formula (I) (the content of the compound represented by general formula (I) is essentially 100% by mass, based on the total mass of the (meth)acrylic compounds (excluding polymerizable compound A) contained in the resin composition).
[0042] The (meth)acrylic compound may include a (meth)acrylic compound having a hydroxy group, or may not include a (meth)acrylic compound having a hydroxy group. The content of the (meth)acrylic compound having a hydroxy group may be 5% by mass or less, less than 5% by mass, 1% by mass or less, 0.1% by mass or less, 0.01% by mass or less, or substantially 0% by mass, based on the total mass of the (meth)acrylic compounds.
[0043] From the viewpoint of easily improving the adhesion of the cured product to an insulating member, the molecular weight of the (meth)acrylic compound may be in the following range: The molecular weight of the (meth)acrylic compound may be 80 or more, 100 or more, 120 or more, 150 or more, 180 or more, 200 or more, 220 or more, 250 or more, 260 or more, 280 or more, 290 or more, 300 or more, or 320 or more. The molecular weight of the (meth)acrylic compound may be 1000 or less, 800 or less, 600 or less, 550 or less, 500 or less, 450 or less, 400 or less, 350 or less, 320 or less, 300 or less, or 280 or less. From these viewpoints, the molecular weight of the (meth)acrylic compound may be 80 to 1000, 80 to 500, 80 to 400, 80 to 300, 200 to 1000, 200 to 500, 200 to 400, 200 to 300, 250 to 1000, 250 to 500, 250 to 400, 250 to 300, 300 to 1000, 300 to 500, or 300 to 400.
[0044] From the viewpoint of easily improving adhesion of the cured product to insulating members, the content of the (meth)acrylic compound may be in the following ranges relative to 100 parts by mass of the polymer (the polymer contained in the resin composition) or 100 parts by mass of the styrene-based polymer. The content of the (meth)acrylic compound may be 1 part by mass or more, 5 parts by mass or more, 10 parts by mass or more, 15 parts by mass or more, 20 parts by mass or more, or 25 parts by mass or more. The content of the (meth)acrylic compound may be 300 parts by mass or less, 200 parts by mass or less, 100 parts by mass or less, 80 parts by mass or less, 60 parts by mass or less, 50 parts by mass or less, 40 parts by mass or less, 30 parts by mass or less, or 25 parts by mass or less. From these viewpoints, the content of the (meth)acrylic compound may be 1 to 300 parts by mass, 10 to 300 parts by mass, 20 to 300 parts by mass, 1 to 100 parts by mass, 10 to 100 parts by mass, 20 to 100 parts by mass, 1 to 50 parts by mass, 10 to 50 parts by mass, or 20 to 50 parts by mass.
[0045] The content of the (meth)acrylic compound may be in the following ranges relative to 100 parts by mass of polymerizable compound A. From the viewpoint of adjusting the adhesion of the cured product to an insulating member, the content of the (meth)acrylic compound may be 10 parts by mass or more, 50 parts by mass or more, 100 parts by mass or more, 150 parts by mass or more, 200 parts by mass or more, 250 parts by mass or more, 300 parts by mass or more, 350 parts by mass or more, 400 parts by mass or more, 450 parts by mass or more, 500 parts by mass or more, 1000 parts by mass or more, 1500 parts by mass or more, or 2000 parts by mass or more. From the viewpoint of easily improving the adhesion of the cured product to the insulating member, the content of the (meth)acrylic compound may be 5,000 parts by mass or less, 4,000 parts by mass or less, 3,000 parts by mass or less, 2,000 parts by mass or less, 1,500 parts by mass or less, 1,000 parts by mass or less, 500 parts by mass or less, 450 parts by mass or less, 400 parts by mass or less, 350 parts by mass or less, 300 parts by mass or less, 250 parts by mass or less, or 200 parts by mass or less. From these viewpoints, the content of the (meth)acrylic compound may be 10 to 5,000 parts by mass, 10 to 3,000 parts by mass, 10 to 500 parts by mass, 10 to 300 parts by mass, 100 to 5,000 parts by mass, 100 to 3,000 parts by mass, 100 to 500 parts by mass, 100 to 3000 parts by mass, 300 to 5,000 parts by mass, 300 to 3,000 parts by mass, 300 to 500 parts by mass, 500 to 5,000 parts by mass, or 500 to 3,000 parts by mass.
[0046] From the viewpoint of easily improving the adhesion of the cured product to insulating members, the content of the (meth)acrylic compound may be within the following ranges based on the total mass of the resin composition (excluding the mass of the organic solvent), the total amount of the polymer (the polymer contained in the resin composition), polymerizable compound A, the (meth)acrylic compound, and the polymerization initiator, the total amount of the styrene-based polymer, polymerizable compound A, the (meth)acrylic compound, and the polymerization initiator, the total amount of the polymer (the polymer contained in the resin composition) and the (meth)acrylic compound, or the total amount of the styrene-based polymer and the (meth)acrylic compound. The content of the (meth)acrylic compound may be 1% by mass or more, 5% by mass or more, 10% by mass or more, 15% by mass or more, 18% by mass or more, or 20% by mass or more. The content of the (meth)acrylic compound may be 80% by mass or less, less than 80% by mass, 70% by mass or less, less than 70% by mass, 60% by mass or less, less than 60% by mass, 50% by mass or less, less than 50% by mass, 40% by mass or less, 35% by mass or less, 30% by mass or less, 25% by mass or less, or 20% by mass or less. From these viewpoints, the content of the (meth)acrylic compound may be 1 to 80% by mass, 1 to 50% by mass, 1 to 30% by mass, 10 to 80% by mass, 10 to 50% by mass, 10 to 30% by mass, 15 to 80% by mass, 15 to 50% by mass, or 15 to 30% by mass.
[0047] The resin composition according to the present embodiment contains a polymerization initiator. The polymerization initiator is not particularly limited as long as it is a compound that initiates polymerization by heating, irradiation with actinic rays (such as ultraviolet rays), or the like, and examples thereof include thermal polymerization initiators and photopolymerization initiators (excluding compounds that fall under the category of thermal polymerization initiators).
[0048] Examples of thermal polymerization initiators include ketone peroxides such as methyl ethyl ketone peroxide, cyclohexanone peroxide, and methylcyclohexanone peroxide; 1,1-bis(tert-butylperoxy)cyclohexane, 1,1-bis(tert-butylperoxy)-2-methylcyclohexane, 1,1-bis(tert-butylperoxy)-3,3,5-trimethylcyclohexane, 1,1-bis(tert-hexylperoxy)cyclohexane, and 1,1-bis(tert-hexylperoxy)-3,3,5-trimethylcyclohexane. peroxyketals; hydroperoxides such as p-menthane hydroperoxide; dialkyl peroxides such as α,α'-bis(tert-butylperoxy)diisopropylbenzene, dicumyl peroxide, tert-butylcumyl peroxide, and di-tert-butyl peroxide; diacyl peroxides such as octanoyl peroxide, lauroyl peroxide, stearyl peroxide, and benzoyl peroxide; bis(4-tert-butylcyclohexyl) peroxydicarbonate, di-2-ethoxyethyl peroxydicarbonate peroxycarbonates such as di-2-ethylhexyl peroxydicarbonate and di-3-methoxybutyl peroxycarbonate; tert-butyl peroxypivalate, tert-hexyl peroxypivalate, 1,1,3,3-tetramethylbutylperoxy-2-ethylhexanoate, 2,5-dimethyl-2,5-bis(2-ethylhexanoylperoxy)hexane, tert-hexylperoxy-2-ethylhexanoate, tert-butylperoxy-2-ethylhexanoate, tert-butylperoxyisobutyl peroxyesters such as tert-butyl peroxyisopropyl monocarbonate, tert-butyl peroxy-3,5,5-trimethylhexanoate, tert-butyl peroxylaurate, tert-butyl peroxyisopropyl monocarbonate, tert-butyl peroxy-2-ethylhexyl monocarbonate, tert-butyl peroxybenzoate, tert-hexyl peroxybenzoate, 2,5-dimethyl-2,5-bis(benzoylperoxy)hexane, and tert-butyl peroxyacetate;Phthalic anhydride, maleic anhydride, trimellitic anhydride, hexahydrophthalic anhydride, tetrahydrophthalic anhydride, methylnadic anhydride, nadic anhydride, glutaric anhydride, dimethylglutaric anhydride, diethylglutaric anhydride, succinic anhydride, methylhexahydrophthalic anhydride, methyltetrahydrophthalic anhydride, 1,2,3,4-cyclobutanetetracarboxylic dianhydride, 4,4'-biphthalic anhydride, 4,4'-carbonyldiphthalic anhydride, 4,4'-sulfonyldiphthalic anhydride Examples of suitable azo compounds include phthalic anhydride, 4,4'-(hexafluoroisopropylidene)diphthalic anhydride, 4,4'-oxydiphthalic anhydride, 9,9-bis(3,4-dicarboxyphenyl)fluorene dianhydride, and 2,3,6,7-naphthalenetetracarboxylic dianhydride; and azo compounds such as 2,2'-azobisisobutyronitrile, 2,2'-azobis(2,4-dimethylvaleronitrile), and 2,2'-azobis(4-methoxy-2'-dimethylvaleronitrile).
[0049] The polymerization initiator may contain a thermal polymerization initiator or a thermal radical polymerization initiator, from the viewpoint of easily improving the adhesion of the cured product to the insulating member. The polymerization initiator may contain a peroxide, a peroxyester, or 2,5-dimethyl-2,5-bis(2-ethylhexanoylperoxy)hexane, from the viewpoint of easily improving the adhesion of the cured product to the insulating member.
[0050] Examples of photopolymerization initiators include acylphosphine oxide compounds such as bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide, bis(2,6-dimethoxybenzoyl)-2,4,4-trimethyl-pentylphosphine oxide, and 2,4,6-trimethylbenzoyldiphenylphosphine oxide; benzoin compounds such as benzoin, benzoin methyl ether, and benzoin isopropyl ether; acetophenone, 2,2-dimethoxy-2-phenylacetophenone, and 2,2-diethoxy-2-phenyl Acetophenone compounds such as acetophenone, 1,1-dichloroacetophenone, 1-hydroxycyclohexyl phenyl ketone, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butanone-1, 2-methyl-[4-(methylthio)phenyl]-2-morpholino-1-propane, and N,N-dimethylaminoacetophenone; 2-methylanthraquinone, 2-ethylanthraquinone, 2-tert-butylanthraquinone, 1-chloroanthraquinone, 2-amylanthraquinone, and 2-aminoanthraquinone; anthraquinone compounds such as acetophenone dimethyl ketal, benzil dimethyl ketal, and other ketal compounds; benzophenone compounds such as benzophenone, methylbenzophenone, 4,4'-dichlorobenzophenone, 4,4'-bis(diethylamino)benzophenone, Michler's ketone, and 4-benzoyl-4'-methyldiphenyl sulfide; 2-(o-chlorophenyl)-4,5-diphenylimidazole dimer, 2-(o-chlorophenyl)-4,5-di(m-methoxyphenyl)imidazole dimer, and other benzophenone compounds. imidazole compounds such as 2-(o-fluorophenyl)-4,5-diphenylimidazole dimer, 2-(o-methoxyphenyl)-4,5-diphenylimidazole dimer, 2-(p-methoxyphenyl)-4,5-diphenylimidazole dimer, 2,4-di(p-methoxyphenyl)-5-phenylimidazole dimer, and 2-(2,4-dimethoxyphenyl)-4,5-diphenylimidazole dimer; acridine compounds such as 9-phenylacridine and 1,7-bis(9,9'-acridinyl)heptane;Examples of suitable oxime ester compounds include 1,2-octanedione-1-[4-(phenylthio)phenyl]-2-(O-benzoyloxime), 1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethanone-1-(O-acetyloxime), and 1-phenyl-1,2-propanedione-2-[O-(ethoxycarbonyl)oxime]; and tertiary amine compounds such as N,N-dimethylaminobenzoic acid ethyl ester, N,N-dimethylaminobenzoic acid isoamyl ester, pentyl-4-dimethylaminobenzoate, triethylamine, and triethanolamine.
[0051] The polymerization initiator may include a photopolymerization initiator or a photoradical polymerization initiator, from the viewpoint of easily improving the adhesion of the cured product to the insulating member. The polymerization initiator may include an acylphosphine oxide, a bisacylphosphine oxide, at least one selected from the group consisting of bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide and bis(2,6-dimethoxybenzoyl)-2,4,4-trimethyl-pentylphosphine oxide, or bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide, from the viewpoint of easily improving the adhesion of the cured product to the insulating member.
[0052] The content B of the polymerization initiator, thermal polymerization initiator, or photopolymerization initiator may be in the following ranges based on the total mass of the resin composition (excluding the mass of the organic solvent), the total amount of the polymer (polymer contained in the resin composition), polymerizable compound A, (meth)acrylic compound, and polymerization initiator, the total amount of the styrene-based polymer, polymerizable compound A, (meth)acrylic compound, and polymerization initiator, the total amount of the polymer (polymer contained in the resin composition) and (meth)acrylic compound, or the total amount of the styrene-based polymer and (meth)acrylic compound, from the viewpoint of easily improving the adhesion of the cured product to the insulating member and easily obtaining excellent curing properties. The content B may be 0.01% by mass or more, 0.05% by mass or more, 0.1% by mass or more, more than 0.1% by mass, 0.2% by mass or more, 0.3% by mass or more, 0.5% by mass or more, 0.8% by mass or more, 1% by mass or more, 1.2% by mass or more, or 1.5% by mass or more. The content B may be 10% by mass or less, 8% by mass or less, 5% by mass or less, 3% by mass or less, 2% by mass or less, 1.5% by mass or less, 1.2% by mass or less, 1% by mass or less, 0.8% by mass or less, 0.5% by mass or less, 0.3% by mass or less, or 0.2% by mass or less. From these viewpoints, the content B may be 0.01 to 10% by mass, 0.01 to 2% by mass, 0.01 to 1.2% by mass, 0.01 to 0.5% by mass, 0.1 to 10% by mass, 0.1 to 2% by mass, 0.1 to 1.2% by mass, 0.1 to 0.5% by mass, 0.5 to 10% by mass, 0.5 to 2% by mass, 0.5 to 1.2% by mass, 1.2 to 10% by mass, or 1.2 to 2% by mass.
[0053] The resin composition according to the present embodiment may contain additives other than the styrene polymer, polymerizable compound A, (meth)acrylic compound, and polymerization initiator. Examples of such additives include polymers (excluding compounds corresponding to the styrene polymer), polymerizable compounds (excluding compounds corresponding to the polymerizable compound A or the (meth)acrylic compound), surfactants (surface modifiers), curing accelerators, antioxidants, ultraviolet absorbers, visible light absorbers, colorants, plasticizers, stabilizers, fillers, reducing agents, and bicarbonates.
[0054] Examples of the polymerizable compound include a vinylidene halide compound, a vinyl ether compound, a vinyl ester compound, an aromatic vinyl compound (e.g., a vinylpyridine compound), an allyl compound, an epoxy compound, etc. Examples of the reducing agent include vanadyl acetylacetonate, vanadium acetylacetonate, cobalt acetylacetonate, copper acetylacetonate, vanadyl naphthenate, vanadyl stearate, copper naphthenate, copper acetate, and cobalt octylate.
[0055] The content of the filler may be 100% by mass or less, less than 100% by mass, 50% by mass or less, 20% by mass or less, 10% by mass or less, 1% by mass or less, 0.1% by mass or less, or substantially 0% by mass, based on the total amount of the polymer (polymer contained in the resin composition) and the (meth)acrylic compound, or the total amount of the styrene-based polymer and the (meth)acrylic compound. The content of the reducing agent may be 0.01 parts by mass or less, less than 0.01 parts by mass, 0.001 parts by mass or less, or substantially 0 parts by mass, based on 100 parts by mass of the (meth)acrylic compound. The content of the bicarbonate may be 0.1 parts by mass or less, less than 0.1 parts by mass, 0.01 parts by mass or less, 0.001 parts by mass or less, or substantially 0 parts by mass, based on 100 parts by mass of the (meth)acrylic compound.
[0056] The resin composition according to this embodiment may contain an organic solvent. The resin composition according to this embodiment may be used as a resin varnish by diluting it with an organic solvent. Examples of organic solvents include aromatic hydrocarbons such as toluene, xylene, mesitylene, cumene, and p-cymene; cyclic ethers such as tetrahydrofuran and 1,4-dioxane; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, and 4-hydroxy-4-methyl-2-pentanone; esters such as methyl acetate, ethyl acetate, butyl acetate, methyl lactate, ethyl lactate, and γ-butyrolactone; carbonates such as ethylene carbonate and propylene carbonate; and amides such as N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone.
[0057] The laminate according to the first embodiment includes a substrate film (support film) and a resin layer disposed on the substrate film, the resin layer including at least one selected from the group consisting of the resin composition according to the present embodiment and a cured product thereof. The resin layer may be an insulating layer or a transparent resin layer. The laminate according to the first embodiment may include a protective film disposed on the resin layer.
[0058] Examples of materials for the substrate film include polyesters (polyethylene terephthalate (PET), polybutylene terephthalate, polyethylene naphthalate, etc.), polyolefins (polyethylene, polypropylene, cycloolefin polymer, etc.), polycarbonate, polyamide, polyimide, polyamideimide, polyetherimide, polyethersulfide, polyethersulfone, polyetherketone, polyphenylene ether, polyphenylene sulfide, etc. The thickness of the substrate film may be 1 to 200 μm, 10 to 100 μm, or 20 to 80 μm.
[0059] The thickness of the resin layer may be 1000 μm or less, 800 μm or less, 500 μm or less, 300 μm or less, 250 μm or less, 200 μm or less, 150 μm or less, or 100 μm or less. The thickness of the resin layer may be 1 μm or more, 5 μm or more, 10 μm or more, 20 μm or more, 30 μm or more, 40 μm or more, 50 μm or more, 80 μm or more, or 100 μm or more. From these viewpoints, the thickness of the resin layer may be 1 to 1000 μm, 10 to 500 μm, 20 to 200 μm, or 50 to 200 μm.
[0060] The protective film may be made of the same material as that of the base film. The protective film may be the same as or different from the base film. The thickness of the protective film may be 1 to 200 μm, 10 to 100 μm, or 20 to 50 μm.
[0061] The laminate according to the second embodiment includes a cured product according to the present embodiment and an insulating member in contact with the cured product. The insulating member may be an insulating pattern on the cured product. The laminate according to the second embodiment may further include a conductive member in contact with the cured product. The conductive member may be an insulating pattern on the cured product in contact with the cured product. The conductive member may be a conductive pattern and may be disposed in a space between the insulating patterns.
[0062] Examples of the constituent material (insulating material) of the insulating member include polyimide, maleimide resin, epoxy resin, phenoxy resin, polybenzoxazole, acrylic resin, PET, glass, etc. The insulating member may contain an organic insulating material, may contain at least one selected from the group consisting of photosensitive materials and cured products thereof, or may contain at least one selected from the group consisting of polyimide and cured products thereof.
[0063] Examples of the constituent material (conductive material) of the conductive member include metal materials, carbon materials (e.g., graphene), conductive polymers, etc. Examples of metal materials include copper, silver, gold, and titanium. The conductive member may contain copper from the viewpoint of easily obtaining excellent conductivity and easily reducing manufacturing costs. The conductive member may be a metal member (a member containing a metal material). The conductive member may be a multi-layered member, and may have a titanium layer and a copper layer disposed on the titanium layer.
[0064] The thickness of the conductive member may be 50 μm or less, 45 μm or less, 40 μm or less, 35 μm or less, 30 μm or less, 25 μm or less, 20 μm or less, 18 μm or less, 15 μm or less, 10 μm or less, 8 μm or less, 5 μm or less, 3 μm or less, or 2 μm or less. The thickness of the conductive member may be 0.1 μm or more, 0.3 μm or more, 0.5 μm or more, 0.8 μm or more, 1 μm or more, 1.2 μm or more, 1.5 μm or more, or 2 μm or more. From these viewpoints, the thickness of the conductive member may be 0.1 to 50 μm, 0.1 to 30 μm, 0.1 to 20 μm, 0.1 to 10 μm, 0.5 to 5 μm, or 1 to 3 μm.
[0065] As an example of an application to which the resin composition and cured product according to this embodiment can be applied, the semiconductor package according to this embodiment includes the laminate according to the second embodiment. The method for producing a semiconductor package according to this embodiment may include a curing step of curing the resin composition according to this embodiment to obtain a cured product. The method for producing a semiconductor package according to this embodiment may include an insulating member-forming step of obtaining an insulating member in contact with a resin layer (hereinafter referred to as "resin layer A") containing at least one resin selected from the group consisting of the resin composition according to this embodiment and its cured product. The insulating member in the insulating member-forming step may be on the resin layer A and in contact with the resin layer A. The insulating member may be an insulating layer. The insulating member-forming step can be performed before the curing step, after the curing step, or before or after the curing step. The insulating member-forming step may include a step of obtaining a photosensitive resin layer (a layer containing a photosensitive material) as an insulating layer on the resin layer A and in contact with the resin layer A, and a step of exposing and developing the photosensitive resin layer to obtain an insulating pattern as the insulating member.
[0066] The method for manufacturing a semiconductor package according to this embodiment may include a conductive member forming step for obtaining a conductive member in contact with the resin layer A. The conductive member in the conductive member forming step may be on the resin layer A and in contact with the resin layer A. The conductive member may be a conductive layer. The conductive member forming step may be performed before the curing step, after the curing step, or both before and after the curing step. The conductive member forming step may be a step of forming a conductive member (e.g., a conductive pattern) on the resin layer A in a space between the insulating patterns in contact with the resin layer A. In this case, the conductive member may extend outside the space between the insulating patterns in contact with the resin layer A (e.g., vertically above the space between the insulating patterns). The conductive member may be formed by sputtering, plating, etc.
[0067] An example of a method for manufacturing a semiconductor package will be described with reference to Figures 1 to 3. First, as shown in Figure 1(a), a cured product 10 according to this embodiment is prepared. Next, as shown in Figure 1(b), a liquid photosensitive material is applied to the cured product 10 and then dried, thereby forming a photosensitive resin layer 20 on the cured product 10 in contact with the cured product 10. Next, as shown in Figure 1(c), the photosensitive resin layer 20 is exposed to light and developed to obtain an insulating pattern 20a.
[0068] Next, as shown in FIG. 2(a), a conductive layer 30 is formed on the cured product 10 and the insulating pattern 20a. The conductive layer 30 can be obtained, for example, by forming a titanium film and a copper film in sequence by sputtering. The conductive layer 30 is formed on the surfaces (top and side surfaces) of the insulating pattern 20a and on the bottom surfaces of the spaces between the insulating patterns 20a. Next, as shown in FIG. 2(b), a photosensitive resin film is laminated on the laminate obtained in FIG. 2(a), thereby forming a photosensitive resin layer 40 on the conductive layer 30. Next, as shown in FIG. 2(c), the photosensitive resin layer 40 is exposed and developed to obtain an insulating pattern 40a so that the spaces between the insulating patterns 20a are exposed.
[0069] Next, as shown in FIG. 3(a), portions of the conductive layer 30 located in the spaces between the insulating patterns 20a are used as a seed layer to form plated portions 50 spanning the spaces between the insulating patterns 20a and the spaces between the insulating patterns 40a by plating. Next, as shown in FIG. 3(b), the insulating pattern 40a is removed. Then, as shown in FIG. 3(c), portions of the conductive layer 30 exposed from the plated portions 50 are removed to obtain remaining portions 30a of the conductive layer 30 located between the insulating patterns 20a. This forms a conductive pattern 60 composed of the remaining portions 30a of the conductive layer 30 and the plated portions 50, and a semiconductor package 100 is obtained on the cured product 10, including the insulating patterns 20a and the conductive pattern 60 that contact the cured product 10. [Example]
[0070] The present disclosure will be further described below using examples, but the present disclosure is not limited to the following examples.
[0071] <Preparation of Resin Varnish> (Comparative Example A1) A resin varnish was obtained by mixing, with stirring, 80.0 parts by mass of styrene-based polymer 1 (hydrogenated styrene-butadiene random copolymer, manufactured by JSR Corporation, trade name: Dynaron 2324P, styrene content: 16% by mass), 20.0 parts by mass of an acrylic compound (1,9-nonanediol diacrylate, manufactured by Resonac Inc., trade name: FA-129AS), 1.5 parts by mass of a photopolymerization initiator (photoradical generator, bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide, manufactured by BASF, trade name: Irgacure 819), and 152.3 parts by mass of a solvent (toluene).
[0072] (Examples A1 to A3) A resin varnish was obtained by mixing, with stirring, 80.0 parts by mass of styrene-based polymer 1, polymerizable compound A (N-vinyl-2-pyrrolidone, manufactured by Nippon Shokubai Co., Ltd., product name: N-vinylpyrrolidone) in the mixing amount (unit: parts by mass) shown in Table 1, 20.0 parts by mass of an acrylic compound (same as in Comparative Example A1), 1.5 parts by mass of a photopolymerization initiator (same as in Comparative Example A1), and 152.3 parts by mass of a solvent (toluene).
[0073] (Comparative Example B1) A resin varnish was obtained by mixing, with stirring, 80.0 parts by mass of styrene-based polymer 1, 20.0 parts by mass of an acrylic compound (same as in Comparative Example A1), 0.2 parts by mass of a thermal polymerization initiator (2,5-dimethyl-2,5-bis(2-ethylhexanoylperoxy)hexane, manufactured by NOF Corporation, trade name: Perhexa 25O), and 150.3 parts by mass of a solvent (toluene).
[0074] (Examples B1 to B3) A resin varnish was obtained by mixing, with stirring, 80.0 parts by mass of styrene-based polymer 1, polymerizable compound A (same as in Examples A1 to A3) in the mixing amount (unit: parts by mass) shown in Table 2, 20.0 parts by mass of an acrylic compound (same as in Comparative Example B1), 0.2 parts by mass of a thermal polymerization initiator (same as in Comparative Example B1), and 150.3 parts by mass of a solvent (toluene).
[0075] (Comparative Example C1) A resin varnish was obtained by mixing, with stirring, 80.0 parts by mass of styrene-based polymer 2 (maleic anhydride-modified styrene-butadiene-styrene block copolymer, manufactured by Asahi Kasei Corporation, product name: Tufprene 912, styrene content: 40% by mass), 20.0 parts by mass of an acrylic compound (same as in Comparative Example A1), 1.0 part by mass of a thermal polymerization initiator (same as in Comparative Example B1), and 151.5 parts by mass of a solvent (toluene).
[0076] (Examples C1 to C2) A resin varnish was obtained by mixing, with stirring, 80.0 parts by mass of styrene-based polymer 2, polymerizable compound A (same as in Examples A1 to A3) in the mixing amount (unit: parts by mass) shown in Table 3, 20.0 parts by mass of an acrylic compound (same as in Comparative Example C1), 1.0 part by mass of a thermal polymerization initiator (same as in Comparative Example C1), and 151.5 parts by mass of a solvent (toluene).
[0077] <Preparation of laminated film> A surface-release-treated PET film (manufactured by Fujimori Kogyo Co., Ltd., product name: HTA, thickness: 75 μm) was prepared as the base film. The above-mentioned resin varnish was applied to the release-treated surface of this PET film using a knife coater (manufactured by Yasui Seiki Co., Ltd., product name: SNC-300). The resin film was then dried at 100°C for 10 minutes in a dryer (manufactured by Futaba Scientific Co., Ltd., product name: MSO-80TPS) to form a resin film. The thickness of the dried resin film was adjusted to 100 μm by adjusting the gap of the coater. A surface-release-treated PET film (manufactured by Fujimori Kogyo Co., Ltd., product name: BD, thickness: 75 μm) was prepared as the protective film, and the release-treated surface of the protective film was attached to the resin film to obtain laminate film A.
[0078] <Evaluation: Adhesion> A polyimide film (UPILEX 50S, manufactured by UBE Corporation) was prepared. After removing the protective film from the laminated film A, the exposed resin film (resin film of laminated film A) was bonded to the polyimide film using a pressure-type vacuum laminator (V130, manufactured by Nikko Materials Co., Ltd.) under conditions of a pressure of 0.5 MPa, vacuuming for 10 seconds, and pressure bonding for 30 seconds, thereby obtaining laminate B.
[0079] The above-mentioned laminate B was subjected to heat treatment at 120°C for 30 minutes in a dryer (manufactured by Futaba Scientific Co., Ltd., product name: MSO-80TPS) to thermally cure the resin film, thereby obtaining laminate C comprising a polyimide film, a cured film, and a substrate film (the substrate film of laminate film A).
[0080] After removing the base film from the above-mentioned laminate C, the cured film was bonded to a glass plate (manufactured by Matsunami Glass Industry Co., Ltd., product name: MICLO SLIDE GLASS S9112) using double-sided tape (manufactured by 3M Japan Ltd., product name: Super Multi-Purpose Ultra-Strong Double-Sided Tape for Smooth Surfaces, Premier Gold SPS-12, width 12 mm x length 4 m, Scotch) to obtain a laminate for evaluation comprising a polyimide film, cured film, double-sided tape, and glass plate.
[0081] A linear incision was made in the polyimide film of the evaluation laminate described above to obtain a test section (width: 5 mm) for measuring tensile stress. At 25°C, the polyimide film obtained as the test section was peeled from the cured film at a speed of 50 mm / min in a direction at an angle of 90° to the cured film using an autograph (Shimadzu Corporation, product name: EZ-S). The tensile stress per unit width (unit: kN / m) was then measured. The results are shown in Table 1.
[0082] [Table 1]
[0083] [Table 2]
[0084] [Table 3] [Explanation of symbols]
[0085] 10...cured product, 20, 40...photosensitive resin layer, 20a, 40a...insulating pattern, 30...conductive layer, 30a...remaining portion of conductive layer, 50...plated portion, 60...conductive pattern, 100...semiconductor package.
Claims
1. A resin composition comprising a styrene-based polymer, a polymerizable compound having an ethylenically unsaturated bond and an amide bond, a (meth)acrylic compound (excluding the polymerizable compound), and a polymerization initiator.
2. The resin composition according to claim 1 , wherein the styrene-based polymer comprises a copolymer having a styrene compound and butadiene as monomer units.
3. The resin composition according to claim 1, wherein the content of the styrene polymer is 50 mass % or more based on the total mass of the resin composition.
4. The resin composition according to claim 1 , wherein the polymerizable compound comprises a lactam compound.
5. The resin composition according to claim 1, wherein the polymerizable compound comprises an N-vinyl lactam compound.
6. The resin composition according to claim 1 , wherein the (meth)acrylic compound comprises an alkanediol di(meth)acrylate.
7. The resin composition according to claim 1 , wherein the (meth)acrylic compound comprises a compound represented by the following general formula (I): 【Chemical 1】 [In the formula, R 1 represents a group containing 9 or less carbon atoms and 2 or more oxygen atoms, R 2a and R 2b each independently represents a hydrogen atom or a methyl group.
8. The resin composition according to claim 1 , wherein the (meth)acrylic compound comprises nonanediol di(meth)acrylate.
9. The resin composition according to claim 1 , wherein the polymerization initiator comprises a thermal polymerization initiator.
10. The resin composition according to claim 1 , wherein the polymerization initiator comprises a photopolymerization initiator.
11. A cured product of the resin composition according to any one of claims 1 to 10.
12. A substrate film and a resin layer disposed on the substrate film, A laminate, wherein the resin layer comprises at least one selected from the group consisting of the resin composition according to any one of claims 1 to 10 and a cured product thereof.
13. A laminate comprising the cured product according to claim 11 and an insulating member on the cured product and in contact with the cured product.
14. The laminate according to claim 13 , further comprising a conductive member on the cured product in contact with the cured product.
Citation Information
Patent Citations
Thermosetting resin composition for semiconductor packaging and prepreg using the same
JP2020528471A