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WO2024162319A1 - Composition de résine, feuille de résine, carte de circuit imprimé multicouche et dispositif à semi-conducteur - Google Patents

Composition de résine, feuille de résine, carte de circuit imprimé multicouche et dispositif à semi-conducteur Download PDF

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Publication number
WO2024162319A1
WO2024162319A1 PCT/JP2024/002791 JP2024002791W WO2024162319A1 WO 2024162319 A1 WO2024162319 A1 WO 2024162319A1 JP 2024002791 W JP2024002791 W JP 2024002791W WO 2024162319 A1 WO2024162319 A1 WO 2024162319A1
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WIPO (PCT)
Prior art keywords
mass
parts
group
compound
formula
Prior art date
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PCT/JP2024/002791
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English (en)
Japanese (ja)
Inventor
優音 熊沢
卓也 鈴木
正志 岡庭
美穂 梅木
直也 岡本
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Mitsubishi Gas Chemical Co Inc
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Mitsubishi Gas Chemical Co Inc
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Priority to CN202480009701.3A priority Critical patent/CN120603869A/zh
Priority to KR1020257020790A priority patent/KR20250140509A/ko
Priority to JP2024574926A priority patent/JPWO2024162319A1/ja
Publication of WO2024162319A1 publication Critical patent/WO2024162319A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F299/00—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers
    • C08F299/02—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates
    • C08F299/022—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates from polycondensates with side or terminal unsaturations
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/28—Layered products comprising a layer of synthetic resin comprising synthetic resins not wholly covered by any one of the sub-groups B32B27/30 - B32B27/42
    • B32B27/281—Layered products comprising a layer of synthetic resin comprising synthetic resins not wholly covered by any one of the sub-groups B32B27/30 - B32B27/42 comprising polyimides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/46—Polymerisation initiated by wave energy or particle radiation
    • C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
    • C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
    • C08F222/36—Amides or imides
    • C08F222/40—Imides, e.g. cyclic imides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F299/00—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
    • H05K1/00—Printed circuits
    • H05K1/02—Details
    • H05K1/03—Use of materials for the substrate
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
    • H05K1/00—Printed circuits
    • H05K1/02—Details
    • H05K1/03—Use of materials for the substrate
    • H05K1/0313—Organic insulating material

Definitions

  • the present invention relates to a resin composition, a resin sheet, a multilayer printed wiring board, and a semiconductor device.
  • the properties required for the resin sheets and metal foil-clad plates used in the insulating layers are becoming more diverse and stricter.
  • One of the required properties is dielectric properties (low dielectric constant and low dielectric tangent).
  • the resin composition used to make the insulating layers is mainly thermosetting resin
  • holes to establish electrical continuity between insulating layers are generally made by laser processing.
  • the problem with laser processing is that the more holes there are in a high-density board, the longer the processing time becomes. For this reason, in recent years, there has been a demand for resin sheets that use resin compositions in which the exposed parts are hardened by irradiation with light (exposure process) and the unexposed parts can be removed (development process), making it possible to make high-density boards by simultaneously drilling holes in the exposure and development processes.
  • the exposure method used is to expose through a photomask using a mercury lamp as the light source, and there is a demand for materials that can be suitably exposed with this mercury lamp as a light source.
  • This exposure method using a mercury lamp as a light source uses ghi mixed lines (g-line wavelength 436 nm, h-line wavelength 405 nm, and i-line wavelength 365 nm), and a general-purpose photocuring initiator can be selected.
  • i-line wavelength 365 nm
  • Alkaline development is used as a development method because it allows for the production of highly detailed patterns.
  • Patent Document 1 describes a resin composition containing a bismaleimide compound (curable resin) and a photoradical curing initiator (curing agent) as a photosensitive resin composition used in laminates and resin sheets.
  • Patent Document 1 a bismaleimide compound is used as the curable resin.
  • maleimide compounds usually have poor light transmittance, when a maleimide compound is included, light does not reach the photocuring initiator sufficiently, and the photocuring initiator does not easily generate radicals, and its reactivity is very low.
  • the maleimide compound when photocuring is performed using active energy rays including i-rays with a wavelength of 365 nm, the maleimide compound has low i-ray transmittance, so there is a problem that the degree of curing is low. Therefore, in Patent Document 1, the maleimide compound is cured by additional heating before development, but since heating is involved, a high-definition insulating layer or resist pattern cannot be obtained.
  • Patent Document 1 the resin composition described in Patent Document 1 does not have sufficient alkaline developability to begin with, so unexposed resin composition remains even after development. Therefore, in Patent Document 1, a high-definition insulating layer or a high-definition resist pattern cannot be obtained while having a low dielectric constant and low dielectric tangent, and it cannot be used for manufacturing high-density printed wiring boards.
  • the present invention has been made in consideration of the problems of the conventional technology, and aims to provide a resin composition and a resin sheet that, in the exposure step when producing a multilayer printed wiring board, has excellent photocurability against various active energy rays, particularly against active energy rays including i-rays with a wavelength of 365 nm, and that can impart excellent alkaline developability in the development step, and by using these, a cured product with a low relative dielectric constant and dielectric dissipation factor can be obtained, and to provide a high-definition insulating layer with a low relative dielectric constant and dielectric dissipation factor, a high-density printed wiring board having a high-definition resist pattern, and a semiconductor device.
  • a resin composition and a resin sheet containing a specific maleimide compound (A), a dicyclopentadiene phenol type epoxy (meth)acrylate (B) containing one or more carboxy groups, and a photocuring initiator (C) have excellent photocurability against various active energy rays in the exposure step in the production of a multilayer printed wiring board, and in particular have excellent photocurability against active energy rays including i-rays with a wavelength of 365 nm, and can be imparted with excellent alkaline developability in the development step, and that by using these, a cured product with a lower relative dielectric constant and dielectric dissipation factor can be obtained, and a high-definition insulating layer with a low relative dielectric constant and dielectric dissipation factor, a high-density printed wiring board having a high-definition resist pattern, and a semiconductor device can be obtained, thereby completing the present invention.
  • A specific maleimide compound
  • B dicyclopen
  • a resin composition comprising: a bismaleimide compound (A) containing a structural unit represented by the following formula (1) and maleimide groups at both ends of the molecular chain; a dicyclopentadiene phenol type epoxy (meth)acrylate (B) containing one or more carboxy groups; and a photocuring initiator (C).
  • a resin composition comprising: a bismaleimide compound (A) containing a structural unit represented by the following formula (1) and maleimide groups at both ends of the molecular chain; a dicyclopentadiene phenol type epoxy (meth)acrylate (B) containing one or more carboxy groups; and a photocuring initiator (C).
  • R 1 represents a linear or branched alkylene group having 1 to 16 carbon atoms, or a linear or branched alkenylene group having 2 to 16 carbon atoms.
  • R 2 represents a linear or branched alkylene group having 1 to 16 carbon atoms, or a linear or branched alkenylene group having 2 to 16 carbon atoms.
  • Each R 3 independently represents a hydrogen atom, a linear or branched alkyl group having 1 to 16 carbon atoms, or a linear or branched alkenyl group having 2 to 16 carbon atoms.
  • Each n 1 independently represents an integer of 1 to 10.
  • one or more resins or compounds (E) selected from the group consisting of modified polyphenylene ether compounds, cyanate ester compounds, phenolic resins, oxetane resins, benzoxazine compounds, and epoxy resins
  • a resin sheet having a support and a resin layer disposed on one or both sides of the support, the resin layer including a resin composition according to any one of [1] to [5].
  • a multilayer printed wiring board having an insulating layer and a conductor layer formed on one or both sides of the insulating layer, the insulating layer containing a resin composition described in any one of [1] to [5].
  • a semiconductor device comprising the resin composition described in any one of [1] to [5].
  • the composition in the exposure step in the production of multilayer printed wiring boards, the composition has excellent photocurability against various active energy rays, particularly against active energy rays including i-rays with a wavelength of 365 nm, and in the development step, excellent alkaline developability can be imparted.
  • a cured product with a lower relative dielectric constant and dielectric dissipation factor can be obtained, and a high-definition insulating layer with a low relative dielectric constant and dielectric dissipation factor, a high-density printed wiring board having a high-definition resist pattern, and a semiconductor device can be provided.
  • present embodiment provides a detailed description of the form for carrying out the present invention (hereinafter referred to as the "present embodiment").
  • present embodiment is an example for explaining the present invention, and is not intended to limit the present invention to the following content.
  • present invention can be carried out with appropriate modifications within the scope of its gist.
  • (meth)acrylic means both “acrylic” and the corresponding "methacrylic".
  • resin solid content or "resin solid content in a resin composition” means, unless otherwise specified, the components in the resin composition excluding the photocuring initiator (C), filler (F), silane coupling agent, wetting and dispersing agent, crosslinking agent, additives listed under “Other Components", and organic solvents, and "100 parts by mass of resin solid content” means that the total components in the resin composition excluding the photocuring initiator (C), filler (F), silane coupling agent, wetting and dispersing agent, crosslinking agent, additives listed under “Other Components", and organic solvents is 100 parts by mass.
  • Mw indicates the mass average molecular weight
  • Mn indicates the number average molecular weight
  • Mw/Mn indicates the molecular weight distribution.
  • Mw, Mn, and Mw/Mn can be determined by gel permeation chromatography (GPC) using polystyrene standards.
  • the substituents are not particularly limited, but examples thereof include halogen atoms such as fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms, hydroxyl groups, cyano groups, nitro groups, thiol groups, heterocyclic groups, linear aliphatic hydrocarbon groups, branched aliphatic hydrocarbon groups, cyclic aliphatic hydrocarbon groups, aryl groups, aralkyl groups, alkoxy groups, alkenyl groups, acyl groups, alkoxycarbonyl groups, alkyloyloxy groups, aryloyloxy groups, and alkylsilyl groups. Specific examples of these substituents may be found in the examples of groups described in this specification.
  • the resin composition of the present embodiment includes a maleimide compound (A) (also referred to as component (A) or bismaleimide compound (A)) containing a structural unit represented by formula (1) and maleimide groups at both ends of the molecular chain, a dicyclopentadienephenol type epoxy (meth)acrylate (B) (also referred to as component (B) or epoxy (meth)acrylate (B)) containing one or more carboxy groups, and a photocuring initiator (C) (also referred to as component (C) or initiator (C)).
  • A maleimide compound
  • A bismaleimide compound
  • C photocuring initiator
  • the resin composition of the present embodiment includes a specific bismaleimide compound (A), a specific epoxy (meth)acrylate (B), and an initiator (C), and is preferably used for producing a multilayer printed wiring board.
  • A specific bismaleimide compound
  • B specific epoxy (meth)acrylate
  • C initiator
  • the resin composition in the exposure step in the production of a multilayer printed wiring board, it has excellent photocurability against various active energy rays, particularly excellent photocurability against active energy rays including i-rays with a wavelength of 365 nm, and in the development step, it can be imparted with excellent alkaline developability.
  • a cured product having a lower dielectric constant and dielectric dissipation factor can be obtained, and a high-definition insulating layer having a low dielectric constant and dielectric dissipation factor, a high-density printed wiring board having a high-definition resist pattern, and a semiconductor device can be obtained.
  • the resin composition of the present embodiment contains a maleimide compound (A) that contains a structural unit represented by formula (1) and maleimide groups at both ends of the molecular chain.
  • R 1 represents a linear or branched alkylene group having 1 to 16 carbon atoms, or a linear or branched alkenylene group having 2 to 16 carbon atoms.
  • R 2 represents a linear or branched alkylene group having 1 to 16 carbon atoms, or a linear or branched alkenylene group having 2 to 16 carbon atoms.
  • Each R 3 independently represents a hydrogen atom, a linear or branched alkyl group having 1 to 16 carbon atoms, or a linear or branched alkenyl group having 2 to 16 carbon atoms.
  • Each n 1 independently represents an integer of 1 to 10.
  • the resin composition has excellent photocurability against various active energy rays, and in particular, has excellent photocurability against active energy rays including i-rays with a wavelength of 365 nm.
  • the reason for this is unclear, but the inventors presume it is due to the following reasons. However, the reasons are not limited to these.
  • maleimide compounds have poor light transmittance, so when a resin composition contains a maleimide compound, light does not sufficiently reach the photocuring initiator dispersed in the resin composition, making it difficult for the photocuring initiator to generate radicals. Therefore, photoradical reactions of maleimide compounds generally do not proceed easily, and even if radical polymerization or dimerization reaction of the maleimide alone proceeds, the reactivity is very low.
  • the bismaleimide compound (A) has a structural unit represented by formula (1), i.e., an alicyclic skeleton with low light absorption, and therefore has very excellent light transmittance.
  • the epoxy (meth)acrylate (B) has an alicyclic skeleton with low light absorption in its structure, and therefore has very excellent light transmittance. Therefore, light reaches the photocuring initiator sufficiently, and the photoradical reaction of maleimide, the polymerization reaction of the ethylenically unsaturated group contained in the epoxy (meth)acrylate, and the reaction between the maleimide group and the ethylenically unsaturated group contained in the epoxy (meth)acrylate, etc., occur efficiently, and the bismaleimide compound (A), the epoxy (meth)acrylate (B), the photocuring initiator (C), and the maleimide compound (D) described below, which are blended as necessary, the resin or compound (E), the filler (F), etc.
  • a cured product having a lower dielectric constant and dielectric dissipation factor can be preferably obtained, and it becomes possible to preferably manufacture a high-definition insulating layer having a low dielectric constant and dielectric dissipation factor, a high-density printed wiring board having a high-definition resist pattern, and a semiconductor device.
  • the transmittance is 5% or more, which shows very excellent light transmittance. Therefore, photocuring can be suitably performed even using active energy rays having a wavelength of 365 nm (i-rays).
  • the transmittance at a wavelength of 365 nm (i-rays) is preferably 8% or more, more preferably 10% or more, in terms of showing better light transmittance.
  • the upper limit of the transmittance at a wavelength of 365 nm (i-rays) is, for example, 99.9% or less.
  • the cell length (path length during measurement) when measuring the transmittance and absorbance is 1 cm.
  • the photocuring initiator tends to have low absorbance for active energy rays including those with a wavelength of 365 nm (i-line). Therefore, it is preferable to use a photocuring initiator (C) that has an absorbance of 0.1 or more for light with a wavelength of 365 nm (i-line) when the absorbance of a chloroform solution containing 0.01% by mass of the photocuring initiator (C) is measured, and thus has excellent absorbance.
  • maleimide compounds usually have extremely low water solubility and no reactivity with the alkaline components in an alkaline developer, making it difficult to obtain alkaline developability.
  • the resin composition contains the epoxy (meth)acrylate (B) along with the bismaleimide compound (A), and thus has excellent photocurability and very good alkaline developability. The reason for this is unclear, but the inventors speculate as follows.
  • the epoxy (meth)acrylate (B) since the epoxy (meth)acrylate (B) has an alicyclic structure and a polymerizable ethylenically unsaturated group in its structure, it does not inhibit the photocuring reaction in the exposure process and has excellent photocurability.
  • the epoxy (meth)acrylate (B) together with the bismaleimide compound (A) the obtained cured product, insulating layer, resist pattern, etc. have a high crosslink density.
  • the epoxy (meth)acrylate (B) has a large number of polar groups such as carboxy groups, ester bonds, and ether bonds in its structure and has a highly flexible alicyclic structure, in the development process, the alkaline developer easily flows into the unexposed area (resin composition), and the resin composition can be given excellent alkaline developability, and the water solubility in the unexposed area can be suitably controlled.
  • the bismaleimide compound (A) has a relatively long chain and a flexible structure, and does not have a structure that causes an interaction with the alkaline component in the alkaline developer.
  • the alkaline component in the alkaline developer and the polar group in the epoxy (meth)acrylate (B) have high affinity without being inhibited by the bismaleimide compound (A), and the alkaline component and the carboxy group in the epoxy (meth)acrylate (B) can quickly and suitably form a salt. Therefore, the water solubility of the unexposed area (resin composition) is improved.
  • Both the bismaleimide compound (A) and the epoxy (meth)acrylate (B) have a highly flexible alicyclic skeleton, so that their compatibility is very high.
  • the bismaleimide compound (A) can be dissolved in the alkaline developer so as to be rolled up together with the epoxy (meth)acrylate (B) as the epoxy (meth)acrylate (B) dissolves in the alkaline developer. For this reason, it is presumed that the resin composition has excellent alkaline developability.
  • the resin composition has excellent photocurability and alkaline developability. Therefore, the resin composition can have excellent resolution, and a very high-definition insulating layer and resist pattern can be obtained.
  • the bismaleimide compound (A) has a relatively low dielectric constant and dielectric dissipation factor due to the maleimide skeleton.
  • the dicyclopentadiene skeleton which is the main skeleton of the epoxy (meth)acrylate (B), also has a relatively low dielectric constant and dielectric dissipation factor.
  • the bismaleimide compound (A) has a maleimide skeleton and the epoxy (meth)acrylate (B) has a polar group, these compounds have a relatively large molar polarization. Therefore, when these compounds are mixed, the influence of the molar polarization becomes large, and it is considered that the dielectric constant and dielectric dissipation factor of the mixture are higher than those of the bismaleimide compound (A) or the epoxy (meth)acrylate (B).
  • both of these compounds have a highly flexible alicyclic structure, they are highly compatible, and the cured product can have a high crosslink density.
  • the effect of molar polarization is reduced in the cured product, and the cured product can have excellent dielectric properties.
  • the cured product has excellent photocurability and alkaline development, while having a low dielectric constant and dielectric loss tangent.
  • a cured product with a lower dielectric constant and dielectric loss tangent can be suitably obtained, and a high-definition insulating layer with a low dielectric constant and dielectric loss tangent, a high-density printed wiring board having a high-definition resist pattern, and a semiconductor device can be obtained.
  • the reason is not limited to this.
  • the resulting cured product also has excellent heat resistance, insulation reliability, and thermal stability, so this embodiment can be used to suitably form protective films, insulating layers, and resist patterns in multilayer printed wiring boards and semiconductor devices.
  • the bismaleimide compound (A) is not particularly limited as long as it achieves the effects of the present invention, but the mass average molecular weight (Mw) is preferably 100 to 5000, more preferably 300 to 4500, in order to obtain a more suitable viscosity and to further suppress the increase in the viscosity of the varnish.
  • Mw mass average molecular weight
  • R 1 represents a linear or branched alkylene group having 1 to 16 carbon atoms, or a linear or branched alkenylene group having 2 to 16 carbon atoms.
  • R 1 is preferably a linear or branched alkylene group, and more preferably a linear alkylene group, from the viewpoints of obtaining a more suitable viscosity and enabling better control of the increase in the viscosity of the varnish.
  • the number of carbon atoms in the alkylene group is preferably 2 to 14, and more preferably 4 to 12, from the viewpoints of obtaining a more suitable viscosity and better control of the increase in the viscosity of the varnish.
  • linear or branched alkylene groups include methylene, ethylene, propylene, 2,2-dimethylpropylene, butylene, pentylene, hexylene, heptylene, octylene, nonylene, decylene, dodecylene, undecylene, tridecylene, tetradecylene, pentadecylene, hexadecylene, neopentylene, dimethylbutylene, methylhexylene, ethylhexylene, dimethylhexylene, trimethylhexylene, methylheptylene, dimethylheptylene, trimethylheptylene, tetramethylheptylene, ethylheptylene,
  • the number of carbon atoms in the alkenylene group is preferably 2 to 14, and more preferably 4 to 12, from the viewpoints of obtaining a more suitable viscosity and better control of the increase in the viscosity of the varnish.
  • linear or branched alkenylene groups include vinylene groups, 1-methylvinylene groups, allylene groups, propenylene groups, isopropenylene groups, 1-butenylene groups, 2-butenylene groups, 1-pentenylene groups, 2-pentenylene groups, isopentenylene groups, cyclopentenylene groups, cyclohexenylene groups, and dicyclopentadienylene groups.
  • R 2 represents a linear or branched alkylene group having 1 to 16 carbon atoms, or a linear or branched alkenylene group having 2 to 16 carbon atoms.
  • R 2 is preferably a linear or branched alkylene group, and more preferably a linear alkylene group, from the viewpoints of obtaining a more suitable viscosity and enabling better control of the increase in the viscosity of the varnish.
  • the number of carbon atoms in the alkylene group is preferably 2 to 14, and more preferably 4 to 12, from the viewpoints of obtaining a more suitable viscosity and better control of the increase in the viscosity of the varnish.
  • R 1 As the linear or branched alkylene group, reference can be made to the above-mentioned R 1 .
  • the number of carbon atoms in the alkenylene group is preferably 2 to 14, and more preferably 4 to 12, from the viewpoints of obtaining a more suitable viscosity and better control of the increase in the viscosity of the varnish.
  • R 1 As the linear or branched alkenylene group, reference can be made to the above-mentioned R 1 .
  • R 1 and R 2 may be the same or different, but are preferably the same in terms of facilitating the synthesis of the bismaleimide compound (A).
  • each R 3 independently represents a hydrogen atom, a linear or branched alkyl group having 1 to 16 carbon atoms, or a linear or branched alkenyl group having 2 to 16 carbon atoms. From the viewpoint of obtaining a more suitable viscosity and being able to better control the increase in the viscosity of the varnish, each R 3 is preferably independently a hydrogen atom or a linear or branched alkyl group having 1 to 16 carbon atoms, more preferably, among R 3 , groups 1 to 5 (R 3 ) are linear or branched alkyl groups having 1 to 16 carbon atoms and the remaining groups (R 3 ) are hydrogen atoms, and even more preferably, among R 3 , groups 1 to 3 (R 3 ) are linear or branched alkyl groups having 1 to 16 carbon atoms and the remaining groups (R 3 ) are hydrogen atoms.
  • the number of carbon atoms in the alkyl group is preferably 2 to 14, and more preferably 4 to 12, from the viewpoints of obtaining a more suitable viscosity and enabling better control of the increase in the viscosity of the varnish.
  • the linear or branched alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, a 1-ethylpropyl group, an n-butyl group, a 2-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a sec-pentyl group, a tert-pentyl group, a 2-methylbutyl group, a 3-methylbutyl group, a 2,2-dimethylpropyl group, an n-hexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group
  • the number of carbon atoms in the alkenyl group is preferably 2 to 14, and more preferably 4 to 12, from the viewpoints of obtaining a more suitable viscosity and enabling better control of the increase in the viscosity of the varnish.
  • Examples of linear or branched alkenyl groups include vinyl, allyl, 4-pentenyl, isopropenyl, isopentenyl, 2-heptenyl, 2-octenyl, and 2-nonenyl groups.
  • each n 1 independently represents an integer of 1 to 10.
  • the bismaleimide compound (A) has maleimide groups at both ends of the molecular chain. Both ends means both ends of the molecular chain of the bismaleimide compound (A), and for example, when the structural unit represented by formula (1) is at the end of the molecular chain of the bismaleimide compound (A), the maleimide group is at the end of the molecular chain of R1 , at the end of the molecular chain at the N atom of the maleimide ring, or at both ends.
  • the bismaleimide compound (A) may have maleimide groups in addition to both ends of the molecular chain.
  • the maleimide group is represented by the formula (2), and an N atom is bonded to the molecular chain of the bismaleimide compound (A).
  • the maleimide groups bonded to the bismaleimide compound (A) may all be the same or different, but it is preferable that the maleimide groups at both ends of the molecular chain are the same.
  • R 24 each independently represents a hydrogen atom or a linear or branched alkyl group having 1 to 4 carbon atoms. From the viewpoint of more suitable photocuring, it is preferable that both R 24 are hydrogen atoms.
  • the number of carbon atoms in the alkyl group is preferably 1 to 3, and more preferably 1 or 2, from the viewpoint of more suitable photocuring.
  • R3 As the linear or branched alkyl group, reference can be made to the above-mentioned R3 .
  • a bismaleimide compound (A) for example, there is a maleimide compound represented by formula (3). These can be used alone or in an appropriate mixture of two or more compounds having different numbers of repetitions of a in formula (3).
  • a represents an integer of 1 to 10.
  • a is preferably an integer of 1 to 6, since a more suitable viscosity can be obtained and the increase in the viscosity of the varnish can be more controlled.
  • the bismaleimide compound (A) may be a commercially available product.
  • An example of a commercially available product is MIZ-001 (trade name, containing a maleimide compound of formula (3), where a in formula (3) is a mixture of 1 to 6 (an integer)) manufactured by Nippon Kayaku Co., Ltd.
  • the content of the bismaleimide compound (A) is preferably 5.0 to 90 parts by mass, more preferably 10 to 80 parts by mass, even more preferably 15 to 70 parts by mass, and even more preferably 20 to 65 parts by mass, per 100 parts by mass of the resin solids in the resin composition.
  • the bismaleimide compound (A) can be used alone or in a suitable mixture of two or more types.
  • the bismaleimide compound (A) can be produced by a known method.
  • 1,2,4,5-cyclohexanetetracarboxylic dianhydride, a monomer containing a diamine such as dimer diamine, and maleic anhydride are subjected to a polyaddition reaction usually at a temperature of about 80 to 250° C., preferably about 100 to 200° C., usually for about 0.5 to 50 hours, preferably about 1 to 20 hours, to obtain a polyaddition product.
  • the polyaddition product is subjected to an imidization reaction, i.e., a dehydration ring-closing reaction, usually at a temperature of about 60 to 120° C., preferably about 80 to 100° C., usually for about 0.1 to 2 hours, preferably about 0.1 to 0.5 hours, to obtain the bismaleimide compound (A).
  • an imidization reaction i.e., a dehydration ring-closing reaction
  • Dimer diamines are obtained, for example, by reductive amination of dimer acids, and the amination reaction can be carried out by known methods (for example, the method described in JP-A-9-12712), such as a reduction method using ammonia and a catalyst.
  • Dimer acids are dibasic acids obtained by dimerizing unsaturated fatty acids through intermolecular polymerization reactions, etc. Although it depends on the synthesis and purification conditions, in addition to dimer acids, small amounts of monomer acids and trimer acids are usually included. After the reaction, double bonds remain in the obtained molecule, but in this embodiment, dimer acids also include those in which the double bonds present in the molecule are reduced by a hydrogenation reaction to become saturated dibasic acids.
  • Dimer acids are obtained, for example, by polymerizing unsaturated fatty acids using Lewis acids and Bronsted acids as catalysts. Dimer acids can be produced by known methods (for example, the method described in JP-A-9-12712).
  • unsaturated fatty acids include crotonic acid, myristoleic acid, palmitoleic acid, oleic acid, elaidic acid, vaccenic acid, gadoleic acid, eicosenoic acid, erucic acid, nervonic acid, linoleic acid, pinoleic acid, eleostearic acid, mead acid, dihomo- ⁇ -linolenic acid, eicosatrienoic acid, stearidonic acid, arachidonic acid, eicosatetraenoic acid, adrenic acid, bosseopentaenoic acid, osbondoic acid, sardine acid, tetracosapentaenoic acid, docos
  • the diamine-containing monomer is dissolved or dispersed in a slurry state in an organic solvent in advance in an inert atmosphere such as argon, nitrogen, etc. to prepare a diamine-containing monomer solution. Then, it is preferable that 1,2,4,5-cyclohexanetetracarboxylic dianhydride is added to the diamine-containing monomer solution after being dissolved or dispersed in a slurry state in an organic solvent, or in a solid state.
  • Any desired bismaleimide compound (A) can be obtained by adjusting the number of moles of 1,2,4,5-cyclohexanetetracarboxylic dianhydride and the total number of moles of the diamine-containing monomer and the maleimide compound.
  • solvents can be used in the polyaddition reaction and the imidization reaction.
  • the solvent include amides such as N,N-dimethylformamide, N,N-dimethylacetamide, and N-methyl-2-pyrrolidone; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, and isophorone; esters such as ⁇ -butyrolactone, ⁇ -valerolactone, ⁇ -valerolactone, ⁇ -caprolactone, ⁇ -caprolactone, ⁇ -methyl- ⁇ -butyrolactone, ethyl lactate, methyl acetate, ethyl acetate, and butyl acetate; aliphatic alcohols having 1 to 10 carbon atoms such as methanol, ethanol, and propanol; aromatic group-containing phenols such as phenol and cresol; benzyl alcohols such as phenyl alcohol
  • the solvent examples include aromatic group-containing alcohols such as alcohol; glycols such as ethylene glycol and propylene glycol, or monoethers or diethers of these glycols with methanol, ethanol, butanol, hexanol, octanol, benzyl alcohol, phenol, cresol, etc., or glycol ethers such as esters of these monoethers; cyclic ethers such as dioxane and tetrahydrofuran; carbonates such as ethylene carbonate and propylene carbonate; aliphatic and aromatic hydrocarbons such as toluene and xylene; and aprotic polar solvents such as dimethyl sulfoxide. These solvents can be used alone or in combination of two or more types as necessary.
  • aromatic group-containing alcohols such as alcohol
  • glycols such as ethylene glycol and propylene glycol
  • a catalyst for example, a tertiary amine and a dehydration catalyst can be used as the catalyst.
  • a tertiary amine a heterocyclic tertiary amine is preferable, and examples thereof include pyridine, picoline, quinoline, and isoquinoline.
  • the dehydration catalyst for example, acetic anhydride, propionic anhydride, n-butyric anhydride, benzoic anhydride, and trifluoroacetic anhydride can be used.
  • the amount of the tertiary amine to be added is preferably 0.5 to 5.0 molar equivalents relative to the amide group, and the amount of the dehydration catalyst to be added is preferably 0.5 to 10.0 molar equivalents relative to the amide group.
  • this solution may be used as a bismaleimide compound (A) solution, or a poor solvent may be added to the reaction solvent to turn the bismaleimide compound (A) into a solid.
  • poor solvents include water, methyl alcohol, ethyl alcohol, 2-propyl alcohol, ethylene glycol, triethylene glycol, 2-butyl alcohol, 2-pentyl alcohol, 2-hexyl alcohol, cyclopentyl alcohol, cyclohexyl alcohol, phenol, and t-butyl alcohol.
  • the resin composition of the present embodiment contains a dicyclopentadiene phenol type epoxy (meth)acrylate (B) containing one or more carboxy groups in its structure.
  • Epoxy (meth)acrylate (B) has a molecular structure in which dicyclopentadiene phenol type epoxy (meth)acrylate is acid-modified, and contains one or more carboxyl groups in the structure. Epoxy (meth)acrylate (B) can be used alone or in a suitable mixture of two or more types.
  • the molecule of the epoxy (meth)acrylate (B) may contain groups such as a hydroxy group, an alkyl group, an alkoxy group, an aryloxy group, an aryl group, an aminoalkyl group, a carboxyalkyl group, and a (meth)acryloyl group.
  • alkyl groups include methyl, ethyl, n-propyl, i-propyl, butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, and n-octyl.
  • alkoxy groups include methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, n-hexanoxy, and 2-methylpropoxy.
  • aryloxy groups include phenoxy and p-tolyloxy.
  • Examples of aryl groups include phenyl, tolyl, benzyl, methylbenzyl, xylyl, mesityl, naphthyl, and anthryl.
  • Examples of aminoalkyl groups include aminomethyl groups, aminoethyl groups, aminopropyl groups, aminodimethyl groups, aminodiethyl groups, aminodipropyl groups, aminobutyl groups, aminohexyl groups, and aminononyl groups.
  • Examples of carboxyalkyl groups include carboxymethyl groups, carboxyethyl groups, carboxypropyl groups, carboxybutyl groups, carboxyhexyl groups, and carboxynonyl groups.
  • the carboxy group in the epoxy (meth)acrylate (B) may be a salt such as a sodium salt or a potassium salt.
  • the carboxy group may be linked to another group such as a carboxymethyl group to form an acid anhydride.
  • the two or more carboxy groups may be linked to each other to form an acid anhydride, or the carboxy group may be linked to another group such as a carboxymethyl group to form an acid anhydride, or both of these acid anhydrides may be present.
  • the epoxy (meth)acrylate (B) contains two or more carboxyalkyl groups in the molecule, the two or more carboxyalkyl groups may be linked to each other to form an acid anhydride.
  • the transmittance is 40% or more, which shows very good light transmittance. Therefore, photocuring can be suitably performed even using active energy rays with a wavelength of 365 nm (i-rays).
  • the transmittance at a wavelength of 365 nm (i-rays) is preferably 45% or more, and more preferably 50% or more, in terms of showing better light transmittance.
  • the upper limit of the transmittance at a wavelength of 365 nm (i-rays) is, for example, 99.9% or less.
  • the epoxy (meth)acrylate (B) is not particularly limited as long as it achieves the effects of the present invention, but since a more suitable viscosity can be obtained, the increase in the viscosity of the varnish can be further suppressed, and a cured product with a lower dielectric constant and dielectric dissipation factor can be obtained, and an insulating layer with higher resolution and a lower dielectric constant and dielectric dissipation factor, a high-density printed wiring board having a higher resolution resist pattern, and a semiconductor device can be obtained, the mass average molecular weight (Mw) is preferably 300 to 50,000, more preferably 400 to 30,000, even more preferably 500 to 10,000, even more preferably 700 to 5,000, and even more preferably 1,000 to 3,000.
  • Mw mass average molecular weight
  • the acid value of the epoxy (meth)acrylate (B) is preferably 30 mgKOH/g or more, since the developability is further improved and a more highly detailed insulating layer or resist pattern can be obtained.
  • the acid value of the epoxy (meth)acrylate (B) is more preferably 50 mgKOH/g or more, since the developability is further improved and a more highly detailed insulating layer or resist pattern can be obtained.
  • the acid value of the epoxy (meth)acrylate (B) is preferably 160 mgKOH/g or less, since dissolution by a developer can be more suitably prevented after curing with active energy rays.
  • the acid value of the epoxy (meth)acrylate (B) is more preferably 150 mgKOH/g or less, and even more preferably 140 mgKOH/g or less, since dissolution by a developer can be more suitably prevented after curing with active energy rays.
  • the "acid value” refers to a value measured by a method conforming to JIS K 0070:1992.
  • Epoxy (meth)acrylate (B) can be obtained, for example, by the following method.
  • a dicyclopentadiene phenol type epoxy resin (i) (also referred to as epoxy resin (i)) having a structure represented by formula (30) is reacted with a carboxylic acid compound (ii) (also referred to as carboxylic acid compound (ii)) containing a polymerizable ethylenically unsaturated group and a carboxy group in the structure, and, if necessary, a compound (iii) (also referred to as compound (iii)) containing a hydroxy group and a carboxy group in the structure to obtain a compound (iv) (also referred to as compound (iv)) containing one or more hydroxy groups.
  • At least one of the hydroxy groups in compound (iv) is subjected to an addition reaction with one or more compounds (v) (also referred to as compound (v)) selected from the group consisting of carboxylic acid-containing compounds and anhydrides of carboxylic acid-containing compounds, thereby introducing one or more carboxy groups via an ester bond, thereby obtaining epoxy (meth)acrylate (B).
  • compounds (v) also referred to as compound (v)
  • Carboxylic acid compound (ii), compound (iii), and compound (v) may be the same or different.
  • each R 1 independently represents a hydrogen atom, a halogen atom, or a linear or branched alkyl group having 1 to 6 carbon atoms.
  • Each n 21 independently represents an integer of 1 to 4.
  • Each n 22 independently represents an integer of 1 to 3.
  • n 2 represents an integer of 1 to 20.
  • the epoxy resin (i) may be a mixture of compounds having different repeat numbers of n 2. In the case of a mixture, the repeat number of n 2 is the average value of the mixture, and is in the range of 1 to 20.
  • Halogen atoms include, for example, fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.
  • Examples of the linear or branched alkyl group having 1 to 6 carbon atoms for R 1 include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a 2-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a sec-pentyl group, a tert-pentyl group, a 2-methylbutyl group, a 3-methylbutyl group, a 2,2-dimethylpropyl group, an n-hexyl group, a sec-hexyl group, a tert-hexyl group, a 2-methylpentyl group, a 3-methylpentyl group, a 4-methylpentyl group, and a 2-methylpentan-3-yl group.
  • R 1 is preferably a hydrogen atom or a linear alkyl group having 1 to 6 carbon atoms, more preferably a hydrogen atom, a methyl group, an ethyl group, an n-propyl group, a 2-butyl group, an isobutyl group, a tert-butyl group, or an n-pentyl group, even more preferably a hydrogen atom, a methyl group, an ethyl group, or an n-propyl group, and still more preferably a hydrogen atom, from the viewpoint of obtaining a cured product having a lower dielectric constant and dielectric dissipation factor, and thus obtaining an insulating layer with higher definition and a lower dielectric constant and dielectric dissipation factor, a high-density printed wiring board having a higher definition resist pattern, and a semiconductor device.
  • the carboxylic acid compound (ii) is not particularly limited as long as it contains at least one polymerizable ethylenically unsaturated group and at least one carboxy group in the structure.
  • Examples of such carboxylic acid compounds (ii) include (meth)acrylic acids, crotonic acid, ⁇ -cyanocinnamic acid, cinnamic acid, and reaction products of saturated or unsaturated dibasic acids with unsaturated group-containing monoglycidyl compounds.
  • Examples of (meth)acrylic acids include monocarboxylic acid compounds containing one carboxy group per molecule, such as (meth)acrylic acid, ⁇ -styrylacrylic acid, ⁇ -furfurylacrylic acid, (meth)acrylic acid dimer, half esters which are equimolar reaction products of saturated or unsaturated dibasic acid anhydrides and (meth)acrylate derivatives having one hydroxyl group per molecule, and half esters which are equimolar reaction products of saturated or unsaturated dibasic acids and monoglycidyl (meth)acrylate derivatives, half esters which are equimolar reaction products of saturated or unsaturated dibasic acid anhydrides and (meth)acrylate derivatives having multiple hydroxyl groups per molecule, and polycarboxylic acid compounds having multiple carboxy groups per molecule, such as half esters which are equimolar reaction products of saturated or unsaturated dibasic acids and glycidyl (meth)acrylate derivatives having multiple
  • Compound (iii) is not particularly limited as long as it contains at least one hydroxy group and at least one carboxy group in the structure.
  • Examples of such compounds (iii) include hydroxypropionic acid, hydroxybutanoic acid, hydroxystearic acid, dimethylolacetic acid, dimethylolpropionic acid, dimethylolbutanoic acid, and hydroxyphthalic acid.
  • compound (v) examples include the following chain aliphatic polycarboxylic acids, alicyclic polycarboxylic acids, aromatic compounds containing two or more carboxy groups, and hetero compounds containing two or more carboxy groups. Specific examples of these compounds can be found below.
  • the reaction method between the epoxy resin (i), the carboxylic acid compound (ii), and, if necessary, the compound (iii) can be a known method.
  • the reaction temperature and reaction time are not particularly limited, but are usually 50 to 150°C and 5 minutes to 60 hours.
  • the amounts of epoxy resin (i), carboxylic acid compound (ii), and compound (iii) charged are usually 10 to 150 equivalent percent of the total of carboxylic acid compound (ii) and compound (iii) per equivalent of epoxy resin (i).
  • catalysts for the reaction.
  • the amount of catalyst used is usually 0.1 to 10 parts by mass per 100 parts by mass of the total reactants.
  • catalysts include triethylamine, benzyldimethylamine, triethylammonium chloride, benzyltrimethylammonium bromide, benzyltrimethylammonium iodide, triphenylphosphine, triphenylstibine, methyltriphenylstibine, chromium octanoate, and zirconium octanoate.
  • the reaction may be carried out in the absence or presence of a solvent.
  • a solvent examples include aromatic hydrocarbon solvents such as toluene, xylene, ethylbenzene, and tetramethylbenzene; aliphatic hydrocarbon solvents such as hexane, octane, and decane; and mixtures thereof such as petroleum ether, white gasoline, and solvent naphtha, as well as ester solvents, ether solvents, and ketone solvents.
  • Ester solvents include, for example, alkyl acetates such as ethyl acetate, propyl acetate, and butyl acetate; cyclic esters of gamma-butyrolactone; ethylene glycol monomethyl ether acetate, diethylene glycol monomethyl ether monoacetate, diethylene glycol monoethyl ether monoacetate, triethylene glycol monoethyl ether monoacetate, diethylene glycol monobutyl ether monoacetate, propylene glycol monomethyl ether monoacetate, butylene glycol monomethyl ether acetate, polyalkylene glycol monoalkyl ether monoacetates, polycarboxylic acid alkyl esters such as dialkyl glutarate, dialkyl succinate, and dialkyl adipate.
  • alkyl acetates such as ethyl acetate, propyl acetate, and butyl acetate
  • ether solvents include alkyl ethers such as diethyl ether and ethyl butyl ether; glycol ethers such as ethylene glycol dimethyl ether, ethylene glycol diethyl ether, dipropylene glycol dimethyl ether, dipropylene glycol diethyl ether, triethylene glycol dimethyl ether, and triethylene glycol diethyl ether; and cyclic ethers of tetrahydrofuran.
  • alkyl ethers such as diethyl ether and ethyl butyl ether
  • glycol ethers such as ethylene glycol dimethyl ether, ethylene glycol diethyl ether, dipropylene glycol dimethyl ether, dipropylene glycol diethyl ether, triethylene glycol dimethyl ether, and triethylene glycol diethyl ether
  • cyclic ethers of tetrahydrofuran examples include alkyl ethers such as diethyl ether and
  • Ketone solvents include, for example, acetone, methyl ethyl ketone, cyclohexanone, and isophorone.
  • the solvent is usually used so that the solids content is 30-90% by mass.
  • polymerization inhibitors include hydroquinone monomethyl ether, 2-methylhydroquinone, hydroquinone, diphenylpicrylhydrazine, diphenylamine, and 3,5-di-tert-butyl-4-hydroxytoluene.
  • a known method can be used for the addition reaction between compound (iv) and compound (v).
  • One such reaction method is, for example, adding compound (v) to a reaction solution containing compound (iv).
  • the amount of compound (v) added to the reaction solution containing compound (iv) is not particularly limited, but it is preferable to adjust it so that the acid value of epoxy (meth)acrylate (B) is within the above range.
  • the addition reaction temperature and addition reaction time are not particularly limited, but are usually 50 to 150°C and 5 minutes to 60 hours.
  • the amount of catalyst used is usually 0.1 to 10 parts by mass per 100 parts by mass of the total reactants.
  • the catalysts exemplified in the reaction of compound (iv) above may be referred to.
  • the reaction may be carried out without a solvent or in a solvent.
  • the solvent and the amount used may refer to the solvent and the amount used exemplified in the reaction of compound (iv) above.
  • An example of the epoxy (meth)acrylate (B) is an epoxy (meth)acrylate (B) having a structure represented by formula (31).
  • R 2 each independently represents a hydrogen atom or a linear or branched alkyl group having 1 to 6 carbon atoms.
  • R 3 represents a residue of a polyvalent carboxylic acid.
  • R 4 each independently represents a hydrogen atom, a halogen atom, or a linear or branched alkyl group having 1 to 6 carbon atoms.
  • R 5 represents a group represented by formula (32) or a group represented by formula (33).
  • n 3 each independently represents an integer of 1 to 3.
  • n 4 represents an integer of 1 to 20.
  • n 5 represents an integer of 0 to 19. However, the total number of n 4 and n 5 (n 4 +n 5 ) represents an integer of 1 to 20.
  • the epoxy (meth)acrylate (B) having a structure represented by formula (31) may be a mixture of compounds in which the number of repetitions of n 4 and n 5 are different from each other.
  • the repeat numbers of n4 and n5 are the average values of the mixture, n4 is in the range of 1 to 20, n5 is in the range of 0 to 19, and the total number of n4 and n5 ( n4 + n5 ) is in the range of 1 to 20.
  • R 2 , R 3 , R 4 , and n 3 have the same meanings as R 2 , R 3 , R 4 , and n 3 in formula (31).
  • -* represents a bond to the carbon atom directly bonded to R 5 in formula (31).
  • R 2 , R 3 , R 4 , and n 3 have the same meanings as R 2 , R 3 , R 4 , and n 3 in formula (31).
  • -* represents a bond to the carbon atom directly bonded to R 5 in formula (31).
  • the epoxy (meth)acrylate (B) may further contain a structural unit in which any one or more of R 2 , R 3 , R 4 , and n 3 in the structural units in n 4 and/or n 5 is different from R 2 , R 3 , R 4 , and n 3.
  • the structural unit in n 4 may contain a structural unit in which the residue of R 3 is different, in which case the repeat number of n 4 is the sum of the average value of the repeat numbers of the structural units in n 4 and the average value of the repeat numbers of the different structural units, and this sum is an integer from 1 to 20.
  • the linear or branched alkyl group having 1 to 6 carbon atoms in R 2 may refer to, for example, the examples of groups described in this specification.
  • R 2 is preferably a hydrogen atom or a linear alkyl group having 1 to 6 carbon atoms, more preferably a hydrogen atom, a methyl group, an ethyl group, an n-propyl group, a 2-butyl group, an isobutyl group, a tert-butyl group, or an n-pentyl group, and even more preferably a hydrogen atom, a methyl group, an ethyl group, or an n-propyl group, and even more preferably a hydrogen atom.
  • R 2 is the above group
  • the reactivity of photocuring can be further improved, and therefore, there is a tendency that a cured product having a lower relative dielectric constant and dielectric loss tangent can be obtained.
  • an insulating layer having a higher resolution and a lower relative dielectric constant and dielectric loss tangent, a high-density printed wiring board having a higher resolution resist pattern, and a semiconductor device can be obtained.
  • R 3 in formulas (31) and (32) represents a residue of a polycarboxylic acid.
  • the residue of a polycarboxylic acid refers to an organic group obtained by removing one carboxy group from a polycarboxylic acid, and the organic group includes a carboxylic acid that is equal to the total number of carboxylic acids contained in the polycarboxylic acid minus 1.
  • R 3 is a carboxylic acid (-COOH).
  • R 3 can also be expressed as -Z-(COOH) m .
  • Z is an organic group obtained by removing the carboxylic acid and the carboxy group from the residue of a polycarboxylic acid
  • m is the total number of carboxylic acids that is equal to the total number of carboxylic acids contained in the polycarboxylic acid minus 1.
  • the polycarboxylic acid is propanedioic acid (malonic acid)
  • Z represents a methyl group
  • m is 1.
  • the polycarboxylic acid is ethanoic acid
  • Z is a single bond
  • m is 1.
  • the polyvalent carboxylic acid may have groups such as a hydroxy group, an alkyl group, an alkoxy group, an aryloxy group, an aryl group, an aminoalkyl group, an amino group, a carboxyalkyl group, and a (meth)acryloyl group. Specific examples of these groups may refer to the examples of groups described in this specification.
  • the polycarboxylic acid may be an acid anhydride formed by two carboxy groups in the molecule being linked to each other.
  • the polycarboxylic acid may be an acid anhydride formed by a carboxyalkyl group and a carboxy group being linked to each other.
  • the polycarboxylic acid may be an acid anhydride formed by them being linked to each other.
  • polycarboxylic acids examples include linear aliphatic polycarboxylic acids, alicyclic polycarboxylic acids, aromatic compounds containing two or more carboxy groups, and hetero compounds containing two or more carboxy groups.
  • chain aliphatic polycarboxylic acids examples include ethanedioic acid (oxalic acid), propanedioic acid (malonic acid), methylpropanedioic acid, butanedioic acid (succinic acid), methylbutanedioic acid, 2-hydroxybutanedioic acid (malic acid), methylhydroxybutanedioic acid, pentanedioic acid (glutaric acid), methylpentanedioic acid, methylhydroxypentanedioic acid, hexanedioic acid (adipic acid), heptanedioic acid (pimelic acid), octanedioic acid (suberic acid), nonanedioic acid (azelaic acid), ), decanedioic acid (sebacic acid), dodecanedioic acid, tetradecanedioic acid, hexadecane
  • alicyclic polycarboxylic acids include cyclopropane dicarboxylic acid, hydroxycyclopropane dicarboxylic acid, cyclopropene dicarboxylic acid, cyclopropane tricarboxylic acid, hydroxycyclopropane tricarboxylic acid, cyclopropene tricarboxylic acid, cyclobutane dicarboxylic acid, hydroxycyclobutane dicarboxylic acid, cyclobutene dicarboxylic acid, cyclobutane tricarboxylic acid, cyclobutene tricarboxylic acid, cyclobutane tetracarboxylic acid, cyclobutene tetracarboxylic acid, cyclopentane dicarboxylic acid, cyclopentene dicarboxylic acid, cyclopentane tricarboxylic acid, cyclopentene tricarboxylic acid, cyclopentane tric
  • dicarboxylic acid examples include monocyclic carboxylic acids such as cyclohexene dicarboxylic acid, cyclohexane tricarboxylic acid, cyclohexene tricarboxylic acid, cyclohexane tetracarboxylic acid, cyclohexene tetracarboxylic acid, cyclohexane pentacarboxylic acid, cyclohexene pentacarboxylic acid, cyclohexane hexacarboxylic acid, cyclohexene hexacarboxylic acid, cycloheptane dicarboxylic acid, cycloheptene dicarboxylic acid, cyclooctane dicarboxylic acid, and cyclooctene dicarboxylic acid; and polycyclic or bridged alicyclic dicarboxylic acids such as norbornane dicarboxylic acid, hydroxynoride
  • aromatic compounds containing two or more carboxy groups include phenylene acetic acid, hydroxyphenylene acetic acid, phthalic acid, trimellitic acid, pyromellitic acid, pentacarboxybenzene, hexacarboxybenzene, naphthalene dicarboxylic acid, benzophenone tetracarboxylic acid, biphenyl tetracarboxylic acid, oxydiphthalic acid, diphenylmethane tetracarboxylic acid, hydroxynaphthalene dicarboxylic acid, naphthalene tricarboxylic acid, naphthalene tetracarboxylic acid, benzene pentacarboxylic acid, benzene hexacarboxylic acid, anthracene dicarboxylic acid, anthracene dicarboxylic acid, anthracene tricarboxylic acid, anthracene tetracar
  • Aromatic compounds may have, for example, a hydrogen atom, as well as groups such as alkyl groups, alkoxy groups, aryloxy groups, aryl groups, amino alkyl groups, hydroxy groups, amino groups, and carboxy alkyl groups on the aromatic rings of the parent skeleton.
  • these compounds when these compounds have two or more carboxy groups in the molecule, they may be acid anhydrides formed by linking two carboxy groups in the molecule to each other.
  • these compounds may have a carboxyalkyl group in the molecule, they may be acid anhydrides formed by linking the carboxyalkyl group and the carboxy group to each other.
  • these compounds have two or more carboxyalkyl groups in the molecule, they may be acid anhydrides formed by linking them to each other.
  • these groups see, for example, the examples of groups described in this specification.
  • Hetero compounds containing two or more carboxy groups include, for example, compounds containing two or more carboxy groups in a hetero ring such as furan, thiophene, pyrrole, imidazole, pyran, pyridine, pyrimidine, pyrazine, pyrrolidine, piperidine, piperazine, morpholine, indole, purine, quinoline, isoquinoline, quinuclidine, chromene, thianthrene, phenothiazine, phenoxazine, xanthene, acridine, phenazine, and carbazole.
  • a hetero ring such as furan, thiophene, pyrrole, imidazole, pyran, pyridine, pyrimidine, pyrazine, pyrrolidine, piperidine, piperazine, morpholine, indole, purine, quinoline, isoquinoline, quinuclidine, chromen
  • Hetero compounds may have, on their parent skeletons, for example, hydrogen atoms, and substituents such as alkyl groups, alkoxy groups, aryloxy groups, aryl groups, aminoalkyl groups, hydroxy groups, amino groups, and carboxyalkyl groups.
  • substituents such as alkyl groups, alkoxy groups, aryloxy groups, aryl groups, aminoalkyl groups, hydroxy groups, amino groups, and carboxyalkyl groups.
  • these compounds may be acid anhydrides formed by linking two carboxy groups in the molecule to each other.
  • they may be acid anhydrides formed by linking a carboxyalkyl group and a carboxy group to each other.
  • these compounds may be bonded to each other to form an acid anhydride. Specific examples of these groups may refer to the examples of groups described in this specification.
  • polycarboxylic acid cyclohexene dicarboxylic acid, cyclohexane tricarboxylic acid, cyclohexane tetracarboxylic acid, trimellitic acid, naphthalene tricarboxylic acid, benzophenone tetracarboxylic acid, biphenyl tetracarboxylic acid, oxydiphthalic acid, diphenylmethane tetracarboxylic acid, naphthalene tetracarboxylic acid, anthracene tetracarboxylic acid, benzene pentacarboxylic acid, and benzene hexacarboxylic acid, or an acid anhydride thereof, are preferred, and cyclohexene dicarboxylic acid or cyclohexene dicarboxylic anhydride are more preferred.
  • R 3 is a residue of these polycarboxylic acids, so that a cured product having a lower dielectric constant and dielectric dissipation factor can be obtained, and a high-density printed wiring board and a semiconductor device having a higher-definition insulating layer with a lower dielectric constant and dielectric dissipation factor, a higher-definition resist pattern, and a higher-density resist pattern can be obtained.
  • the entire unexposed area becomes more easily crumbled, and in addition, the alkaline developer flows in more easily, so that the resin composition can be given better alkaline developability, and the peelability after development tends to be improved.
  • R 3 is more preferably a group represented by formula (34).
  • the group represented by formula (34) is a residue of cyclohexene-1,2-dicarboxylic acid or a residue of cyclohexene-1,2-dicarboxylic anhydride.
  • R 3 is a group represented by formula (34)
  • a cured product having a lower dielectric constant and dielectric dissipation factor can be obtained, and an insulating layer having a higher resolution and a lower dielectric constant and dielectric dissipation factor, a high-density printed wiring board having a higher resolution resist pattern, and a semiconductor device can be obtained.
  • the entire unexposed area becomes more likely to crumble, and in addition, the alkaline developer flows in more easily, so that the resin composition can be given better alkaline developability, and the peelability after development tends to be further improved.
  • -* represents a bond to the carbon atom directly bonded to R 3 in formula (31) and/or (32).
  • R 4 is preferably a hydrogen atom or a linear alkyl group having 1 to 6 carbon atoms, more preferably a hydrogen atom, a methyl group, an ethyl group, an n-propyl group, a 2-butyl group, an isobutyl group, a tert-butyl group, or an n-pentyl group, more preferably a hydrogen atom, a methyl group, an ethyl group, or an n-propyl group, and even more preferably a hydrogen atom, a methyl group, an ethyl group, or an n-propyl group, and even more preferably a hydrogen atom, a hydrogen atom, a methyl group, a ethyl group, or an n-propyl group, and even more preferably a hydrogen atom, a hydrogen atom, a methyl group, a ethyl group, or an n-propyl group, and even more preferably
  • R 5 is preferably a group represented by formula (32).
  • R 5 is this group, a cured product having a lower dielectric constant and dielectric loss tangent can be obtained, and a high-definition insulating layer having a lower dielectric constant and dielectric loss tangent, a high-density printed wiring board having a higher-definition resist pattern, and a semiconductor device can be obtained.
  • the entire unexposed area becomes more easily crumbled, and the alkaline developer flows in more easily, so that the resin composition can be given better alkaline developability, and the peelability after development tends to be improved.
  • the epoxy (meth)acrylate (B) preferably contains a structural unit in n5 .
  • n4 is an integer from 1 to 19
  • n5 is an integer from 1 to 19
  • the total number of n4 and n5 is an integer from 2 to 20.
  • the epoxy (meth)acrylate (B) containing the structural unit in n5 is a mixture of compounds having different repeat numbers of n4 and n5 .
  • the repeat numbers of n4 and n5 are the average values of the mixture, n4 is in the range of 1 to 19, n5 is in the range of 1 to 19, and the total number of n4 and n5 (the number of n4 + n5 ) is in the range of 2 to 20.
  • B epoxy (meth)acrylate
  • a cured product having a lower dielectric constant and dielectric loss tangent can be obtained, and there is a tendency that an insulating layer having a higher resolution and a lower dielectric constant and dielectric loss tangent, a high-density printed wiring board having a higher resolution resist pattern, and a semiconductor device can be obtained.
  • the unexposed portion as a whole becomes more likely to crumble, and in addition, an alkaline developer flows in more easily, so that the resin composition can be given superior alkaline developability, and the peelability after development tends to be improved.
  • the epoxy (meth)acrylate (B) preferably contains an epoxy (meth)acrylate represented by formula (35), and more preferably contains an epoxy (meth)acrylate represented by formula (36).
  • R 6 each independently represents a hydrogen atom, a methyl group, an ethyl group, or an n-propyl group.
  • R 7 each independently represents a residue of cyclohexene dicarboxylic acid, a residue of cyclohexane tetracarboxylic acid, a residue of trimellitic acid, a residue of naphthalene tricarboxylic acid, a residue of benzophenone tetracarboxylic acid, a residue of biphenyl tetracarboxylic acid, a residue of oxydiphthalic acid, a residue of diphenylmethane tetracarboxylic acid, a residue of naphthalene tetracarboxylic acid, a residue of anthracene tetracarboxylic acid, a residue of benzene pentacarboxylic acid, or a residue of benzene hexacarboxylic acid.
  • n 6 represents an integer of 1 to 19.
  • n 7 represents an integer of 1 to 19.
  • the total number of n 6 and n 7 (n 6 +n 7 ) represents an integer of 2 to 20.
  • the epoxy (meth)acrylate represented by formula (35) may be a mixture of compounds in which the number of repetitions of n 6 and n 7 are different from each other. In the case of a mixture, the number of repetitions of n6 and n7 is the average value of the mixture, n6 is in the range of 1 to 19, n7 is in the range of 1 to 19, and the total number of n6 and n7 ( n6 + n7 ) is in the range of 2 to 20.
  • R7 preferably contains a residue of cyclohexenedicarboxylic acid.
  • R 6 , R 7 , n 6 , and n 7 may refer to R 2 , R 3 , n 4 , and n 5 in formula (31), respectively.
  • n8 represents an integer of 1 to 19.
  • n9 represents an integer of 1 to 19.
  • the total number of n8 and n9 represents an integer of 2 to 20.
  • the epoxy (meth)acrylate represented by formula (36) may be a mixture of compounds having different repeat numbers of n8 and n9 .
  • the repeat numbers of n8 and n9 are the average values of the mixture, n8 is in the range of 1 to 19, n9 is in the range of 1 to 19, and the total number of n8 and n9 (the number of n8 + n9 ) is in the range of 2 to 20.
  • n 8 is in the range of 1 to 19
  • n 9 is in the range of 1 to 19
  • the total number of n 8 and n 9 is in the range of 2 to 20
  • the mass average molecular weight (Mw) is 2250
  • the acid value is 111 mgKOH/g) manufactured by Nippon Kayaku Co., Ltd.
  • ZXR-1807H trade name, a mixture of compounds in which the repeat numbers of n 8 and n 9 are different, n 8 is in the range of 1 to 19, n 9 is in the range of 1 to 19, the total number of n 8 and n 9 is in the range of 2 to 20, the mass average molecular weight (Mw) is 2270, and the acid value is 100 mgKOH/g).
  • the content of epoxy (meth)acrylate (B) is preferably 5.0 to 90 parts by mass, more preferably 10 to 80 parts by mass, even more preferably 15 to 70 parts by mass, and even more preferably 20 to 65 parts by mass, based on 100 parts by mass of the resin solid content in the resin composition.
  • the mass ratio ((A)/(B)) of the bismaleimide compound (A) to the epoxy (meth)acrylate (B) is preferably 0.1 to 1.5, more preferably 0.5 to 1.4, even more preferably 0.6 to 1.3, and even more preferably 0.7 to 1.2.
  • the resin composition of the present embodiment includes a photocuring initiator (C).
  • the photocuring initiator (C) is not particularly limited, and may be one known in the field of photocurable resin compositions.
  • the photocuring initiator (C) is used to photocure the bismaleimide compound (A), the epoxy (meth)acrylate (B), the maleimide compound (D) described below, the resin or compound (E), the filler (F), and the like, which are blended as necessary, using various active energy rays.
  • photocuring initiator (C) examples include benzoins such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin propyl ether, and benzoin isobutyl ether; organic peroxides such as benzoyl peroxide, lauroyl peroxide, acetyl peroxide, parachlorobenzoyl peroxide, and di-tert-butyl-di-perphthalate; acylphosphine oxides such as 2,4,6-trimethylbenzoyl-diphenyl-phosphine oxide, bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide, benzoyl-diphenyl-phosphine oxide, and bisbenzoyl-phenylphosphine oxide; acetophenone, 2,2-diethoxy-2-phenylacetophenone, 1,1-dichloroacetophenone, 2-hydroxy-2-methyl-phenylpropan-1
  • acetophenones such as 2-phenyl]-2-morpholinopropan-1-one and 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butanone-1; anthraquinones such as 2-ethylanthraquinone, 2-t-butylanthraquinone, 2-chloroanthraquinone, and 2-amylanthraquinone; thioxanthones such as 2,4-diethylthioxanthone, 2-isopropylthioxanthone, and 2-chlorothioxanthone; acetophenone dimethyl ketal and benzyl ketals such as benzyl dimethyl ketal; benzophenones such as benzophenone, 4-benzoyl-4'-methyldiphenyl sulfide, and 4,4'-bismethylaminobenzophenone; radical-type photocuring initiators such as oxime esters such as
  • the photocuring initiator (C) may be a commercially available product, and examples of such products include Omnirad (registered trademark) 369 (trade name) manufactured by IGM Resins B.V., Omnirad (registered trademark) 819 (trade name) manufactured by IGM Resins B.V., Omnirad (registered trademark) 819DW (trade name) manufactured by IGM Resins B.V., Omnirad (registered trademark) 907 (trade name) manufactured by IGM Resins B.V., Omnirad (registered trademark) TPO (trade name) manufactured by IGM Resins B.V., Omnirad (registered trademark) TPO-G (trade name) manufactured by IGM Resins B.V., and Omnirad (registered trademark) 907 (trade name) manufactured by IGM Resins B.V.
  • Examples of such an additive include Omnirad (registered trademark) 784 (product name) manufactured by BASF Corporation, Irgacure (registered trademark) OXE01 (product name) manufactured by BASF Japan Ltd., Irgacure (registered trademark) OXE02 (product name) manufactured by BASF Japan Ltd., Irgacure (registered trademark) OXE03 (product name) manufactured by BASF Japan Ltd., and Irgacure (registered trademark) OXE04 (product name) manufactured by BASF Japan Ltd.
  • These photocuring initiators (C) may be used alone or in a suitable mixture of two or more.
  • the absorbance is preferably 0.1 or more.
  • Such a photocuring initiator (C) exhibits very excellent absorbance. Since a resin composition having superior photocurability can be obtained, the absorbance at a wavelength of 365 nm (i-line) is more preferably 0.15 or more, and even more preferably 0.2 or more.
  • the upper limit of the absorbance at a wavelength of 365 nm (i-line) is, for example, 99.9 or less.
  • oxime esters and acylphosphine oxides are preferred, and oxime esters are more preferred, because they have higher sensitivity to various actinic radiation.
  • 1,2-octanedione and 1-[4-(phenylthio)phenyl-, 2-(O-benzoyloxime)] are preferred, since they have higher sensitivity to various active energy rays, have better solvent solubility, and give cured products with lower dielectric constants and dielectric dissipation tangents, as well as insulating layers with lower dielectric constants and dielectric dissipation tangents.
  • the compound represented by formula (4) is preferred because it has a higher absorbance for various active energy rays, particularly active energy rays including i-rays with a wavelength of 365 nm.
  • each R 23 independently represents a group represented by formula (5) or a phenyl group.
  • R 24 each independently represents a hydrogen atom or a methyl group
  • -* represents a bond to the phosphorus atom (P) directly bonded to R 23 in formula (4).
  • the absorbance is 0.1 or more, which shows very good absorbance for light with a wavelength of 365 nm (i-line). Therefore, this compound generates radicals favorably for light with a wavelength of 365 nm (i-line).
  • the absorbance is preferably 0.15 or more, and more preferably 0.2 or more.
  • the upper limit is, for example, 10.0 or less, and may be 5.0 or less, or 2.0 or less.
  • each R 23 independently represents a group represented by formula (5) or a phenyl group. It is preferable that one or more of R 23 is a group represented by formula (5).
  • each R 24 independently represents a hydrogen atom or a methyl group. It is preferable that one or more of R 24 is a methyl group, and it is more preferable that all of R 24 are methyl groups.
  • Examples of the compound represented by formula (4) include acylphosphine oxides such as 2,4,6-trimethylbenzoyl-diphenyl-phosphine oxide and bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide.
  • acylphosphine oxides such as 2,4,6-trimethylbenzoyl-diphenyl-phosphine oxide and bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide.
  • bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide is preferred because it has superior light transmittance.
  • These compounds can be used alone or in a suitable mixture of two or more types.
  • the content of the photocuring initiator (C) is preferably 0.1 to 50 parts by mass, more preferably 0.2 to 30 parts by mass, even more preferably 0.3 to 10 parts by mass, even more preferably 0.5 to 9.0 parts by mass, and even more preferably 1.0 to 8.0 parts by mass, relative to 100 parts by mass of the resin solid content in the resin composition.
  • the resin composition of the present embodiment can give a cured product having a lower dielectric constant and dielectric dissipation factor, and can give an insulating layer with higher resolution and a lower dielectric constant and dielectric dissipation factor, as well as a high-density printed wiring board and semiconductor device having a higher resolution resist pattern. Therefore, it is preferable that the resin composition of the present embodiment further contains a maleimide compound (D) (also referred to as component (D) or compound (D)) other than the bismaleimide compound (A) of the present embodiment.
  • a maleimide compound (D) also referred to as component (D) or compound (D)
  • maleimide compound (D) there is no particular limitation on the maleimide compound (D), so long as it is a compound having one or more maleimide groups in the molecule, unlike the bismaleimide compound (A).
  • maleimide compounds (D) include compounds represented by formula (6), compounds represented by formula (7), compounds represented by formula (8), compounds represented by formula (9), compounds represented by formula (10), compounds represented by formula (11), compounds represented by formula (12), N-phenylmaleimide, N-cyclohexylmaleimide, N-hydroxyphenylmaleimide, N-anilinophenylmaleimide, N-carboxyphenylmaleimide, N-(4-carboxy-3-hydroxyphenyl)maleimide, 6-maleimidohexanoic acid, 4-maleimidobutyric acid, bis(4-maleimidophenyl)methane, 2,2-bis(4-(4-maleimidophenoxy)- phenyl)propane, 4,4-diphenyl
  • the maleimide compound (D) it is preferable to use a compound with excellent light transmittance. It is more preferable that the maleimide compound (D) is a compound that the resin composition is photosensitive to and photocured when exposed to various types of active energy rays, particularly active energy rays having a wavelength of 365 nm (i-rays).
  • a chloroform solution containing 1% by mass of maleimide compound (D) is prepared, and the transmittance of the chloroform solution containing 1% by mass of maleimide compound (D) is measured using active energy rays having a wavelength of 365 nm (i-rays).
  • the transmittance is preferably 0.5% or more. In terms of exhibiting better light transmittance, the transmittance is more preferably 0.8% or more, and even more preferably 1.0% or more.
  • the upper limit of the transmittance at a wavelength of 365 nm (i-rays) is, for example, 99.9% or less.
  • the content of the maleimide compound (D) is preferably 1.0 to 25 parts by mass, more preferably 3.0 to 20 parts by mass, and even more preferably 5.0 to 15 parts by mass, based on 100 parts by mass of the resin solid content in the resin composition.
  • the maleimide compound (D) it is possible to obtain a cured product having a lower dielectric constant and dielectric loss tangent, and it is possible to obtain an insulating layer with higher resolution and a lower dielectric constant and dielectric loss tangent, a high-density printed wiring board having a higher resolution resist pattern, and a semiconductor device.
  • the maleimide compound (D) contains at least one selected from the group consisting of the compound represented by formula (6), the compound represented by formula (7), the compound represented by formula (8), the compound represented by formula (9), the compound represented by formula (10), the compound represented by formula (11), and the compound represented by formula (12), and it is more preferable that the maleimide compound (D) contains at least one selected from the group consisting of the compound represented by formula (6), the compound represented by formula (7), and the compound represented by formula (8), and it is even ).
  • the resin composition of the present embodiment preferably further contains a compound represented by formula (6), since a cured product having an even lower dielectric constant and dielectric dissipation factor can be obtained, and an insulating layer having even higher resolution and an even lower dielectric constant and dielectric dissipation factor, a high-density printed wiring board having an even higher resolution resist pattern, and a semiconductor device can be obtained.
  • each Ra independently represents an alkyl group, alkyloxy group, or alkylthio group having 1 to 10 carbon atoms, an aryl group, aryloxy group, or arylthio group having 6 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a halogen atom, a nitro group, a hydroxy group, or a mercapto group.
  • q represents an integer from 0 to 4. When q is an integer from 2 to 4, each Ra may be the same or different within the same ring.
  • Each Rb independently represents an alkyl group, alkyloxy group, or alkylthio group having 1 to 10 carbon atoms, an aryl group, aryloxy group, or arylthio group having 6 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a halogen atom, a hydroxy group, or a mercapto group.
  • r represents an integer from 0 to 3. When r is 2 or 3, each Rb may be the same or different within the same ring.
  • n is the average number of repeating units, and represents a value of 0.95 to 10.0.
  • the resin composition of the present embodiment further contains the compound represented by formula (6) and thereby can obtain a cured product having an even lower dielectric constant and dielectric tangent is not clear, but the inventors presume as follows. That is, the compound represented by formula (6) has a relatively low dielectric constant and dielectric loss tangent due to the maleimide skeleton. In addition, the compound represented by formula (6) has a relatively rigid structure due to the benzene ring, and on the other hand, it has flexibility due to the isopropylidene group. And, the compound represented by formula (6) has excellent photocurability due to the cyclopentane ring and the isopropylidene group in the structure.
  • the compound represented by formula (6) has a very high compatibility with the bismaleimide compound (A) and the epoxy (meth)acrylate (B), and can be suitably photocured together with the photocuring initiator (C), and the obtained cured product can have a higher crosslink density.
  • the relatively rigid structure due to the benzene ring and the bulky indane skeleton can impart a bulky structure to the cured product, so that the dielectric constant and dielectric loss tangent of the cured product can be made lower. From this, it is presumed that if the resin composition further contains the compound represented by formula (6), a cured product with an even lower dielectric constant and dielectric constant can be obtained. However, the reason is not limited to this.
  • the content of the compound represented by formula (6) is preferably 1.0 to 25 parts by mass, more preferably 3.0 to 20 parts by mass, and even more preferably 5.0 to 15 parts by mass, per 100 parts by mass of the total resin solids in the resin composition.
  • alkyl groups having 1 to 10 carbon atoms include methyl, ethyl, n-propyl, isopropyl, 1-ethylpropyl, n-butyl, 2-butyl, isobutyl, tert-butyl, n-pentyl, sec-pentyl, tert-pentyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, n-hexyl, sec-hexyl, tert-hexyl, n-heptyl, n-octyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 2-methylpentan-3-yl, n-nonyl, isononyl, and n-decyl.
  • alkyloxy groups having 1 to 10 carbon atoms examples include methoxy groups, ethoxy groups, n-propoxy groups, n-butoxy groups, n-pentyloxy groups, and n-hexyloxy groups.
  • alkylthio groups having 1 to 10 carbon atoms examples include methylthio and ethylthio groups.
  • aryl groups having 6 to 10 carbon atoms include phenyl groups, cyclohexylphenyl groups, phenol groups, cyanophenyl groups, nitrophenyl groups, naphthalene groups, biphenyl groups, anthracene groups, naphthacene groups, anthracyl groups, pyrenyl groups, perylene groups, pentacene groups, benzopyrene groups, chrysene groups, pyrene groups, and triphenylene groups.
  • aryloxy groups having 6 to 10 carbon atoms include phenoxy and p-tolyloxy groups.
  • arylthio groups having 6 to 10 carbon atoms include phenylthio and p-tolylthio groups.
  • cycloalkyl groups having 3 to 10 carbon atoms include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cycloheptyl groups.
  • Halogen atoms include, for example, fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.
  • each Ra is preferably independently an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or an aryl group having 6 to 10 carbon atoms.
  • q is preferably 2 or 3, and more preferably 2.
  • the groups other than Ra that are directly bonded to the benzene ring are hydrogen atoms. That is, for example, when q is 0, it indicates that all of Ra are hydrogen atoms. It is preferable that all of Ra are hydrogen atoms.
  • Rb's are hydrogen atoms. It is also preferable that r is an integer of 1 to 3, and each Rb is independently an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or an aryl group having 6 to 10 carbon atoms.
  • the groups other than Rb that are directly bonded to the benzene ring are hydrogen atoms. That is, for example, when r is 0, it indicates that all Rb's are hydrogen atoms.
  • the compound represented by formula (6) may be produced according to a known method. Specific examples of the production method include the method described in WO2020/217679.
  • R 12 , R 13 and R 14 each independently represent a hydrogen atom or a linear or branched alkyl group having 1 to 8 carbon atoms which may have a substituent.
  • the linear or branched alkyl group having 1 to 8 carbon atoms, which may have a substituent include a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a 1-ethylpropyl group, a 2,2-dimethylpropyl group, a cyclopentyl group, a hexyl group, and a heptyl group.
  • the hydrogen atoms in these alkyl groups may be substituted with a halogen atom such as a fluorine atom or a chlorine atom, and a cyano group.
  • a halogen atom such as a fluorine atom or a chlorine atom
  • the substituent include a halogen atom, a hydroxy group, a cyano group, a nitro group, a thiol group, a heterocyclic group, a linear aliphatic hydrocarbon group, a branched aliphatic hydrocarbon group, a cyclic aliphatic hydrocarbon group, an aryl group, an aralkyl group, an alkoxy group, an alkenyl group, an acyl group, an alkoxycarbonyl group, an alkyloyloxy group, an aryloyloxy group, and an alkylsilyl group.
  • alkyl groups from the viewpoints of exhibiting superior photocurability, heat resistance, and thermal stability, as well as favorable solubility in solvents, a low melting point, low water absorbency, and better compatibility with other resins, preferred are methyl groups, ethyl groups, and isopropyl groups, more preferred are methyl groups, and even more preferred is methyl groups.
  • the compound represented by formula (7) is even more preferably a compound represented by formula (13).
  • R 15 , R 16 , and R 17 each independently represent a hydrogen atom, a hydroxyl group, or a linear or branched alkyl group having 1 to 6 carbon atoms which may have a substituent.
  • n 3 represents an integer of 1 to 10.
  • the linear or branched alkyl group having 1 to 6 carbon atoms for example, the examples of groups described in this specification may be referred to.
  • the alkyl group a methyl group, an ethyl group, an n-propyl group, and an isopropyl group are preferred, and a methyl group is more preferred, in terms of exhibiting better solubility in a solvent, a low melting point, low water absorption, and better compatibility with other resins.
  • substituents examples include a halogen atom, a hydroxy group, a cyano group, a nitro group, a thiol group, a heterocyclic group, a linear aliphatic hydrocarbon group, a branched aliphatic hydrocarbon group, a cyclic aliphatic hydrocarbon group, an aryl group, an aralkyl group, an alkoxy group, an alkenyl group, an acyl group, an alkoxycarbonyl group, an alkyloyloxy group, an aryloyloxy group, and an alkylsilyl group.
  • R 15 and R 17 are linear or branched alkyl groups having 1 to 6 carbon atoms, and R 16 is a hydrogen atom.
  • the preferred alkyl groups are as described above.
  • n3 is preferably an integer from 1 to 10, and more preferably an integer from 1 to 6, from the viewpoints of providing better solubility in the solvent, obtaining a more suitable viscosity, and enabling better control of the increase in the viscosity of the varnish.
  • BMCX426 trade name manufactured by Gun-ei Chemical Industry Co., Ltd.
  • n 21 is an integer from 1 to 5.
  • n 22 is an integer from 1 to 10.
  • each R 18 independently represents a hydrogen atom, a methyl group, or an ethyl group
  • each R 19 independently represents a hydrogen atom or a methyl group.
  • R 18 is preferably a methyl group or an ethyl group, from the viewpoints of exhibiting better solubility in a solvent, a low melting point, low water absorbency, and better compatibility with other resins.
  • R 19 is preferably a hydrogen atom in that it exhibits better solubility in a solvent, a low melting point, low water absorbency, and better compatibility with other resins.
  • maleimide compound represented by formula (9) a commercially available product may be used, for example, BMI-70 (product name) manufactured by K.I. Chemicals Co., Ltd., represented by formula (16).
  • R 20 each independently represents a hydrogen atom or a methyl group, and n 4 represents an integer of 1 to 10.
  • a commercially available product may be used, and an example thereof is MIR-3000 (trade name) manufactured by Nippon Kayaku Co., Ltd., represented by formula (17).
  • n 31 is an integer from 1 to 10.
  • each R 21 independently represents a hydrogen atom, a methyl group, or an ethyl group.
  • R 21 is preferably a methyl group or an ethyl group, from the viewpoints of exhibiting better solubility in a solvent, a low melting point, low water absorbency, and better compatibility with other resins.
  • the maleimide compound represented by formula (11) a commercially available product may be used, and an example thereof is BMI-80 (trade name) manufactured by K.I. Chemicals Co., Ltd., represented by formula (18).
  • R 22 each independently represents a hydrogen atom or a methyl group, and n 5 represents an integer of 1 to 10.
  • R 22 is preferably a hydrogen atom from the viewpoints of exhibiting better solubility in a solvent, a low melting point, low water absorbency, and better compatibility with other resins.
  • n5 is more preferably an integer of 1 to 5, since this provides better solubility in the solvent, a more suitable viscosity, and allows better control of the increase in the viscosity of the varnish.
  • maleimide compound represented by formula (12) a commercially available product may be used, for example, BMI-2300 (product name) manufactured by Daiwa Kasei Kogyo Co., Ltd., represented by formula (19).
  • n 41 is an integer of 1 to 4.
  • the resin composition of the present embodiment can obtain a cured product having a lower dielectric constant and dielectric loss tangent, and can obtain an insulating layer having a higher resolution and a lower dielectric constant and dielectric loss tangent, a high-density printed wiring board having a higher resolution resist pattern, and a semiconductor device. Therefore, it is preferable to further contain one or more resins or compounds (E) (also referred to as component (E) or "resin or compound (E)”) selected from the group consisting of modified polyphenylene ether compounds, cyanate ester compounds, phenolic resins, oxetane resins, benzoxazine compounds, and epoxy resins.
  • the resin or compound (E) can be used alone or in a suitable mixture of two or more types.
  • the resin or compound (E) is different from the bismaleimide compound (A), the epoxy (meth)acrylate (B), the photocuring initiator (C), and the maleimide compound (D).
  • the resin composition of this embodiment preferably contains a modified polyphenylene ether compound.
  • a cured product having an even lower dielectric constant and dielectric dissipation factor can be obtained, and there is a tendency to obtain an insulating layer with even higher resolution and an even lower dielectric constant and dielectric dissipation factor, and a high-density printed wiring board and semiconductor device having an even higher resolution resist pattern.
  • a cured product, insulating layer, and resist pattern with better flame retardancy, heat resistance, and thermal expansion properties.
  • the resin or compound (E) it is preferable to use a resin or compound with excellent light transmittance. It is more preferable that the resin or compound (E) is a resin or compound that is photosensitive to the resin composition and photocured when exposed to various types of active energy rays, particularly active energy rays having a wavelength of 365 nm (i-rays).
  • a chloroform solution containing 1% by mass of resin or compound (E) is prepared, and the transmittance of the chloroform solution containing 1% by mass of resin or compound (E) is measured using active energy rays having a wavelength of 365 nm (i-rays).
  • the transmittance is preferably 10% or more. In terms of exhibiting better light transmittance, the transmittance is more preferably 15% or more, and even more preferably 20% or more.
  • the upper limit of the transmittance at a wavelength of 365 nm (i-rays) is, for example, 99.9% or less.
  • the total content of the resin or compound (E) is preferably 1.0 to 25 parts by mass, more preferably 3.0 to 20 parts by mass, and even more preferably 5.0 to 15 parts by mass, based on 100 parts by mass of the resin solids in the resin composition.
  • the resin composition of the present embodiment preferably further contains a modified polyphenylene ether compound, since a cured product having an even lower dielectric constant and dielectric dissipation factor can be obtained, and an insulating layer with even higher resolution and an even lower dielectric constant and dielectric dissipation factor, and a high-density printed wiring board and semiconductor device having an even higher resolution resist pattern can be obtained.
  • the modified polyphenylene ether compound is not particularly limited, and any known compound may be appropriately used as long as the terminals of the polyphenylene ether compound are partially or entirely modified.
  • modified polyphenylene ether compound means that the terminals of the polyphenylene ether compound are partially or entirely substituted with reactive functional groups such as carbon-carbon unsaturated double bonds.
  • the modified polyphenylene ether compound may be used alone or in a suitable mixture of two or more types.
  • the resin composition of the present embodiment can obtain a cured product having an even lower dielectric constant and dielectric tangent by further containing a modified polyphenylene ether compound
  • the modified polyphenylene ether compound has a relatively low dielectric constant and dielectric loss tangent due to the polyphenylene ether skeleton.
  • the modified polyphenylene ether compound has a highly planar and rigid structure due to the presence of phenylene, while it also has rotational flexibility due to the presence of ether bonds.
  • a part or all of the ends of the polyphenylene ether compound have a reactive functional group such as a carbon-carbon unsaturated double bond that is highly reactive to light.
  • the modified polyphenylene ether compound has a very high compatibility with the bismaleimide compound (A) and the epoxy (meth)acrylate (B), and can be suitably photocured together with the photocuring initiator (C), and the obtained cured product can have a higher crosslink density.
  • the bulky polyphenylene ether skeleton due to the bulky polyphenylene ether skeleton, a bulky structure can be imparted to the cured product, so that the dielectric constant and dielectric loss tangent of the cured product can be further reduced. From this, it is presumed that if the resin composition further contains a modified polyphenylene ether compound, a cured product with an even lower dielectric constant and dielectric constant can be obtained. However, the reason is not limited to this.
  • the polyphenylene ether compound related to the modified polyphenylene ether compound may be, for example, a polymer containing one or more structural units selected from the group consisting of a structural unit represented by formula (20), a structural unit represented by formula (21), and a structural unit represented by formula (22).
  • R 8 , R 9 , R 10 , and R 11 each independently represent an alkyl group having 6 or less carbon atoms, an aryl group, a halogen atom, or a hydrogen atom.
  • R12 , R13 , R14 , R18 , and R19 each independently represent an alkyl group having 6 or less carbon atoms or a phenyl group.
  • R15 , R16 , and R17 each independently represent a hydrogen atom, an alkyl group having 6 or less carbon atoms, or a phenyl group.
  • R , R , R , R , R , R , R , and R each independently represent a hydrogen atom, an alkyl group having 6 or less carbon atoms, or a phenyl group, and -A- represents a linear, branched, or cyclic divalent hydrocarbon group having 20 or less carbon atoms.
  • -A- in formula (22) may be, for example, a divalent organic group such as a methylene group, an ethylidene group, a 1-methylethylidene group, a 1,1-propylidene group, a 1,4-phenylenebis(1-methylethylidene) group, a 1,3-phenylenebis(1-methylethylidene) group, a cyclohexylidene group, a phenylmethylene group, a naphthylmethylene group, or a 1-phenylethylidene group, but is not limited to these.
  • a divalent organic group such as a methylene group, an ethylidene group, a 1-methylethylidene group, a 1,1-propylidene group, a 1,4-phenylenebis(1-methylethylidene) group, a 1,3-phenylenebis(1-methylethylidene
  • modified polyphenylene ether compounds include those in which some or all of the terminals of the polyphenylene ether compound are modified with groups such as ethylenically unsaturated groups such as vinylbenzyl groups, epoxy groups, amino groups, hydroxyl groups, mercapto groups, carboxy groups, methacryl groups, and silyl groups.
  • groups such as ethylenically unsaturated groups such as vinylbenzyl groups, epoxy groups, amino groups, hydroxyl groups, mercapto groups, carboxy groups, methacryl groups, and silyl groups.
  • An example of a modified polyphenylene ether compound having a hydroxyl group at the end is SA90 (trade name, SABIC Innovative Plastics).
  • An example of a modified polyphenylene ether compound having a methacryl group at the end is SA9000 (product name, SABIC Innovative Plastics).
  • the method for producing the modified polyphenylene ether compound is not particularly limited as long as it can obtain the effects of the present invention.
  • the compound can be produced by the method described in Japanese Patent No. 4,591,665.
  • the modified polyphenylene ether compound more preferably contains a modified polyphenylene ether compound having an ethylenically unsaturated group at its end.
  • the ethylenically unsaturated group may include alkenyl groups such as ethenyl, allyl, acryl, methacryl, propenyl, butenyl, hexenyl, and octenyl; cycloalkenyl groups such as cyclopentenyl and cyclohexenyl; and alkenylaryl groups such as vinylbenzyl and vinylnaphthyl.Among them, vinylbenzyl is preferred.
  • the terminal ethylenically unsaturated groups may be single or multiple and may be the same or different groups.
  • the compound represented by formula (23) is preferred as the modified polyphenylene ether compound having an ethylenically unsaturated group at the end, since it is possible to obtain a cured product having a lower dielectric constant and dielectric dissipation factor, and thus to obtain an insulating layer with higher resolution and a lower dielectric constant and dielectric dissipation factor, a high-density printed wiring board having a higher resolution resist pattern, and a semiconductor device.
  • X represents an aromatic group
  • -(Y-O) m - represents a polyphenylene ether moiety
  • R 1 , R 2 , and R 3 each independently represent a hydrogen atom, an alkyl group, an alkenyl group, or an alkynyl group
  • m represents an integer of 1 to 100
  • n represents an integer of 1 to 6
  • q represents an integer of 1 to 4.
  • m is preferably an integer of 1 to 50, more preferably an integer of 1 to 30.
  • n is preferably an integer of 1 to 4, more preferably 1 or 2, and ideally 1.
  • q is preferably an integer of 1 to 3, more preferably 1 or 2, and ideally 2.
  • the aromatic group represented by X in formula (23) includes a group in which q hydrogen atoms have been removed from one ring structure selected from the group consisting of a benzene ring structure, a biphenyl ring structure, an indenyl ring structure, and a naphthalene ring structure (e.g., a phenylene group, a biphenylene group, an indenylene group, and a naphthylene group).
  • a biphenylene group is preferable.
  • the aromatic group represented by X may include a diphenyl ether group in which an aryl group is bonded via an oxygen atom, a benzophenone group in which an aryl group is bonded via a carbonyl group, or a 2,2-diphenylpropane group in which an alkylene group is bonded.
  • the aromatic group may be substituted with a general group such as an alkyl group (preferably an alkyl group having 1 to 6 carbon atoms, particularly a methyl group), an alkenyl group, an alkynyl group, a halogen atom, etc.
  • the aromatic group is substituted on the polyphenylene ether moiety via an oxygen atom, the limit on the number of general groups depends on the number of polyphenylene ether moieties.
  • the structural unit represented by formula (20), the structural unit represented by formula (21), and the structural unit represented by formula (22) can be used. Among them, it is more preferable to include the structural unit represented by formula (20).
  • the modified polyphenylene ether compound represented by formula (23) preferably has a number average molecular weight (Mn) of 500 to 7000.
  • Mn number average molecular weight
  • a cured product having a lower dielectric constant and dielectric dissipation factor can be obtained, and an insulating layer with higher resolution and a lower dielectric constant and dielectric dissipation factor, a high-density printed wiring board having a higher resolution resist pattern, and a semiconductor device can be obtained. Therefore, in formula (23), the number average molecular weight (Mn) is more preferably 700 to 7000. The number average molecular weight (Mn) is even more preferably 1000 to 3000.
  • modified polyphenylene ether compound among those represented by formula (23), it is preferable to use a compound represented by formula (24).
  • X is an aromatic group
  • -(Y-O) m - and -(O-Y) m - each represent a polyphenylene ether moiety
  • m represents an integer of 1 to 100.
  • m is preferably an integer of 1 to 50, and more preferably an integer of 1 to 30.
  • X, -(Y-O) m -, and m have the same definitions as those in formula (23).
  • -(O-Y) m - in formula (24) has the same definition as -(Y-O) m - in formula (23).
  • X in formula (23) and formula (24) is formula (25), formula (26), or formula (27), and -(Y-O) m - and -(O-Y) m - in formula (23) and formula (24) are a structure in which formula (28) or formula (29) is arranged, or a structure in which formula (28) and formula (29) are arranged in a block or random manner.
  • R 28 , R 29 , R 30 and R 31 each independently represent a hydrogen atom or a methyl group
  • -B- represents a linear, branched or cyclic divalent hydrocarbon group having up to 20 carbon atoms.
  • Specific examples of -B- include the same as the specific examples of -A- in formula (22).
  • -B- is a linear, branched or cyclic divalent hydrocarbon group having 20 or less carbon atoms.
  • Specific examples of -B- include the same as the specific examples of -A- in formula (22).
  • the method for producing a modified polyphenylene ether compound having a structure represented by formula (24) is not particularly limited, and the compound can be produced, for example, by subjecting a bifunctional phenol compound and a monofunctional phenol compound to oxidative coupling to obtain a bifunctional phenylene ether oligomer, and then converting the terminal phenolic hydroxyl group of the bifunctional phenylene ether oligomer into a vinylbenzyl ether.
  • the modified polyphenylene ether compound having a structure represented by formula (24) commercially available products can be used.
  • OPE registered trademark
  • OPE registered trademark-2st2200
  • the content of the modified polyphenylene ether compound is preferably 1.0 to 25 parts by mass, more preferably 3.0 to 20 parts by mass, and even more preferably 5.0 to 15 parts by mass, per 100 parts by mass of the total resin solids in the resin composition.
  • the cyanate ester compound is not particularly limited as long as it is a resin having an aromatic moiety in the molecule substituted with at least one cyanato group (cyanate ester group).
  • Ar 1 represents a benzene ring, a naphthalene ring, or two benzene rings bonded together. When there are a plurality of Ar 1s, they may be the same or different.
  • Each of Ra's independently represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an aryl group having 6 to 12 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, and a group in which an alkyl group having 1 to 6 carbon atoms and an aryl group having 6 to 12 carbon atoms are bonded together.
  • the aromatic ring in Ra may have a substituent, and the positions of the substituents in Ar 1 and Ra can be selected at any position.
  • p represents the number of cyanato groups bonded to Ar 1 , and each of p's is an integer of 1 to 3.
  • q represents the number of Ra's bonded to Ar 1 , and is 4-p when Ar 1 is a benzene ring, 6-p when Ar 1 is a naphthalene ring, and 8-p when two benzene rings are bonded together.
  • t represents the average number of repetitions and is an integer from 0 to 50, and the cyanate ester compound may be a mixture of compounds with different t's.
  • the alkyl group for Ra in formula (37) may have either a straight or branched chain structure or a cyclic structure (for example, a cycloalkyl group, etc.).
  • the hydrogen atoms in the alkyl group in formula (37) and the aryl group in Ra may be substituted with halogen atoms such as fluorine atoms and chlorine atoms, alkoxy groups such as methoxy groups and phenoxy groups, or cyano groups.
  • alkyl group examples include a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a 1-ethylpropyl group, a 2,2-dimethylpropyl group, a cyclopentyl group, a hexyl group, a cyclohexyl group, and a trifluoromethyl group.
  • alkenyl group examples include a vinyl group, a (meth)allyl group, an isopropenyl group, a 1-propenyl group, a 2-butenyl group, a 3-butenyl group, a 1,3-butadienyl group, a 2-methyl-2-propenyl group, a 2-pentenyl group, and a 2-hexenyl group.
  • the aryl group include a phenyl group, a xylyl group, a mesityl group, a naphthyl group, a phenoxyphenyl group, an ethylphenyl group, an o-, m- or p-fluorophenyl group, a dichlorophenyl group, a dicyanophenyl group, a trifluorophenyl group, a methoxyphenyl group, and an o-, m- or p-tolyl group.
  • the alkoxy group include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, an n-butoxy group, an isobutoxy group, and a tert-butoxy group.
  • divalent organic group having 1 to 50 carbon atoms for X in formula (37) include a methylene group, an ethylene group, a trimethylene group, a cyclopentylene group, a cyclohexylene group, a trimethylcyclohexylene group, a biphenylylmethylene group, a dimethylmethylene-phenylene-dimethylmethylene group, a fluorenediyl group, and a phthalidodiyl group, etc.
  • the hydrogen atom in the divalent organic group may be substituted with a halogen atom such as a fluorine atom or a chlorine atom, an alkoxy group such as a methoxy group or a phenoxy group, a cyano group, etc.
  • a halogen atom such as a fluorine atom or a chlorine atom
  • an alkoxy group such as a methoxy group or a phenoxy group
  • a cyano group etc.
  • Examples of the divalent organic group having 1 to 10 nitrogen atoms for X in the formula (37) include an imino group and a polyimide group.
  • the organic group X in formula (37) may, for example, have a structure represented by formula (38) or a structure represented by formula (39).
  • Ar 2 represents a benzenediyl group, a naphthalenediyl group, or a biphenyldiyl group, and when u is an integer of 2 or more, they may be the same or different from each other.
  • Rb, Rc, Rf, and Rg each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 12 carbon atoms, a trifluoromethyl group, or an aryl group having at least one phenolic hydroxy group.
  • Rd and Re each independently represent one of a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 12 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, and a hydroxy group.
  • u represents an integer of 0 to 5.
  • Ar3 represents a benzenediyl group, a naphthalenediyl group, or a biphenyldiyl group, and may be the same or different when v is an integer of 2 or more.
  • Ri and Rj each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 12 carbon atoms, a benzyl group, an alkoxy group having 1 to 4 carbon atoms, a hydroxy group, a trifluoromethyl group, or an aryl group substituted with at least one cyanato group.
  • v represents an integer of 0 to 5, but may be a mixture of compounds having different v's.
  • X in formula (37) can be a divalent group represented by the following formula:
  • z represents an integer of 4 to 7.
  • Rk independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
  • Ar2 in formula (38) and Ar3 in formula (39) include a benzenediyl group in which two carbon atoms shown in formula (38) or two oxygen atoms shown in formula (39) are bonded to the 1,4-positions or the 1,3-positions, a biphenyldiyl group in which two carbon atoms or two oxygen atoms are bonded to the 4,4'-positions, 2,4'-positions, 2,2'-positions, 2,3'-positions, 3,3'-positions, or 3,4'-positions, and a naphthalenediyl group in which two carbon atoms or two oxygen atoms are bonded to the 2,6-positions, 1,5-positions, 1,6-positions, 1,8-positions, 1,3-positions, 1,4-positions, or 2,7-positions.
  • cyanato-substituted aromatic compounds represented by formula (37) include cyanatobenzene, 1-cyanato-2-, 1-cyanato-3-, or 1-cyanato-4-methylbenzene, 1-cyanato-2-, 1-cyanato-3-, or 1-cyanato-4-methoxybenzene, 1-cyanato-2,3-, 1-cyanato-2,4-, 1-cyanato-2,5-, 1-cyanato-2,6-, 1-cyanato-3,4-, or 1-cyanato-3,5-dimethylbenzene, cyanatoethylbenzene, Cyanatobutylbenzene, cyanatooctylbenzene, cyanatononylbenzene, 2-(4-cyanatophenyl)-2-phenylpropane (cyanate of 4- ⁇ -cumylphenol), 1-cyanato-4-cyclohexylbenzene, 1-cyanato-4-vinylbenzene, 1-cyanato-2
  • cyanate ester compounds can be used alone or in a suitable mixture of two or more.
  • cyanate ester compound represented by formula (37) examples include phenol novolak resins and cresol novolak resins (produced by reacting phenol, alkyl-substituted phenol or halogen-substituted phenol with a formaldehyde compound such as formalin or paraformaldehyde in an acidic solution by a known method), trisphenol novolak resins (produced by reacting hydroxybenzaldehyde with phenol in the presence of an acidic catalyst), fluorene novolak resins (produced by reacting a fluorenone compound with 9,9-bis(hydroxyaryl)fluorenes in the presence of an acidic catalyst), phenol aralkyl resins, cresol aralkyl resins, naphthol aralkyl resins and biphenyl aralkyl resins (produced by reacting a bishalogenomethyl compound represented by Ar4- ( CH2Y ) 2 ( Ar4 represents a phenyl group and Y
  • the method for producing these cyanate ester compounds is not particularly limited, and known methods can be used.
  • a specific example is a method in which a hydroxyl group-containing compound having a desired skeleton is obtained or synthesized, and the hydroxyl group is modified by a known method to form a cyanate.
  • An example of a method for forming a cyanate from a hydroxyl group is the method described in Ian Hamerton, "Chemistry and Technology of Cyanate Ester Resins," Blackie Academic & Professional.
  • Cured products using these cyanate ester compounds tend to have excellent properties such as glass transition temperature, low thermal expansion, and plating adhesion.
  • phenolic resin any known phenolic resin can be used as long as it has two or more hydroxyl groups in one molecule.
  • phenolic resin any known phenolic resin can be used as long as it has two or more hydroxyl groups in one molecule.
  • bisphenol A type phenolic resin bisphenol E type phenolic resin, bisphenol F type phenolic resin, bisphenol S type phenolic resin, phenol novolac resin, bisphenol A novolac type phenolic resin, glycidyl ester type phenolic resin, aralkyl novolac type phenolic resin, biphenyl aralkyl type phenolic resin, cresol novolac type phenolic resin, multifunctional phenolic resin, naphthol resin, naphthol novolac resin, multifunctional naphthol resin, anthracene type phenolic resin, naphthalene skeleton modified novolac type phenolic resin, phenol aralkyl type phenolic resin, naphthol aralkyl
  • oxetane resin As the oxetane resin, generally known ones can be used. For example, alkyl oxetanes such as oxetane, 2-methyl oxetane, 2,2-dimethyl oxetane, 3-methyl oxetane, and 3,3-dimethyl oxetane, 3-methyl-3-methoxymethyl oxetane, 3,3-di(trifluoromethyl)perfluorooxetane, 2-chloromethyl oxetane, 3,3-bis(chloromethyl)oxetane, biphenyl type oxetane, OXT-101 (manufactured by Toagosei Co., Ltd., product name), OXT-121 (manufactured by Toagosei Co., Ltd., product name), and OXT-221 (manufactured by Toagosei Co
  • benzoxazine compound generally known compounds can be used as long as they have two or more dihydrobenzoxazine rings in one molecule.
  • bisphenol A type benzoxazine BA-BXZ (trade name, manufactured by Konishi Chemical Industry Co., Ltd.)
  • bisphenol F type benzoxazine BF-BXZ (trade name, manufactured by Konishi Chemical Industry Co., Ltd.)
  • bisphenol S type benzoxazine BS-BXZ trade name, manufactured by Konishi Chemical Industry Co., Ltd.
  • P-d type benzoxazine trade name, manufactured by Shikoku Chemical Industry Co., Ltd.
  • F-a type benzoxazine (trade name, manufactured by Shikoku Chemical Industry Co., Ltd.)
  • phenolphthalein type benzoxazine can be mentioned.
  • These benzoxazine compounds can be used alone or in a suitable mixture of two or more types.
  • the epoxy resin is not particularly limited, and generally known epoxy resins can be used.
  • epoxy resins can be used.
  • bisphenol A type epoxy resins bisphenol E type epoxy resins, bisphenol F type epoxy resins, bisphenol S type epoxy resins, bisphenol A novolac type epoxy resins, biphenyl type epoxy resins, phenol novolac type epoxy resins, cresol novolac type epoxy resins, xylene novolac type epoxy resins, multifunctional phenol type epoxy resins, naphthalene type epoxy resins, naphthalene skeleton modified novolac type epoxy resins, naphthylene ether type epoxy resins, phenol aralkyl type epoxy resins, anthracene type epoxy resins, trifunctional phenol type epoxy resins, tetrafunctional phenol type epoxy resins, triglyceride type epoxy resins, etc.
  • epoxy resins examples include diisocyanurate, glycidyl ester type epoxy resins, alicyclic epoxy resins, dicyclopentadiene novolac type epoxy resins, biphenyl novolac type epoxy resins, phenol aralkyl novolac type epoxy resins, naphthol aralkyl novolac type epoxy resins, aralkyl novolac type epoxy resins, naphthol aralkyl type epoxy resins, dicyclopentadiene type epoxy resins, polyol type epoxy resins, phosphorus-containing epoxy resins, glycidylamine, compounds in which the double bonds of butadiene, etc. are epoxidized, compounds obtained by reacting hydroxyl group-containing silicone resins with epichlorohydrin, and halides thereof.
  • epoxy resins can be used alone or in a suitable mixture of two or more.
  • epoxy resin commercially available products can be used. Examples thereof include an epoxy resin represented by formula (40) (NC-3000FH (trade name) manufactured by Nippon Kayaku Co., Ltd., in which n5 is about 4) and a naphthalene-type epoxy resin represented by formula (41) (HP-4710 (trade name) manufactured by DIC Corporation).
  • epoxy resins can be used alone or in a suitable mixture of two or more types.
  • the resin composition of the present embodiment may contain other compounds different from the bismaleimide compound (A), the epoxy (meth)acrylate (B), the photocuring initiator (C), the maleimide compound (D), and the resin or compound (E), as long as the effects of the present invention are achieved.
  • Examples of such other compounds include vinyl ethers such as ethyl vinyl ether, propyl vinyl ether, hydroxyethyl vinyl ether, and ethylene glycol divinyl ether; styrenes such as styrene, methylstyrene, ethylstyrene, and divinylbenzene; triallyl isocyanurate, trimethallyl isocyanurate, and bisallylnadimide. These other compounds can be used alone or in combination of two or more.
  • the content of other compounds is usually 1.0 to 25 parts by mass per 100 parts by mass of the total resin solids in the resin composition.
  • the resin composition of the present embodiment can obtain a cured product having a lower dielectric constant and dielectric loss tangent, and can obtain a high-definition insulating layer having a lower dielectric constant and dielectric loss tangent, a high-density printed wiring board having a higher-definition resist pattern, and a semiconductor device, and various properties such as coating property and heat resistance are further improved, so it is preferable to further include a filler (F).
  • the filler (F) it is preferable that it has insulating properties and does not inhibit the permeability to various active energy rays used for photocuring.
  • the filler (F) is different from the bismaleimide compound (A), the epoxy (meth)acrylate (B), the photocuring initiator (C), the maleimide compound (D), and the resin or compound (E).
  • the filler (F) can be used alone or in a suitable mixture of two or more types.
  • the average particle diameter of the filler (F) is not particularly limited, but is usually 0.005 to 10 ⁇ m, and preferably 0.01 to 1.0 ⁇ m, in order to obtain a resin composition with better ultraviolet light transmittance.
  • the "average particle diameter" of the filler (F) refers to the median diameter of the filler (F).
  • the median diameter refers to a particle diameter such that, when the particle size distribution of a powder is divided into two based on a certain particle diameter, the volume of the particles on the larger particle diameter side and the volume of the particles on the smaller particle diameter side each account for 50% of the total powder.
  • the average particle diameter (median diameter) of the filler (F) is measured by a wet laser diffraction/scattering method.
  • Examples of the filler (F) include silica (e.g., natural silica, fused silica, amorphous silica, hollow silica, etc.), aluminum compounds (e.g., boehmite, aluminum hydroxide, alumina, aluminum nitride, etc.), boron compounds (e.g., boron nitride, etc.), magnesium compounds (e.g., magnesium oxide, magnesium hydroxide, etc.), calcium compounds (e.g., calcium carbonate, etc.), molybdenum compounds (e.g., molybdenum oxide, zinc molybdate, etc.), barium compounds (e.g., barium sulfate, barium silicate, etc.), talc (e.g., natural talc, calcined talc, etc.), mica, glass (e.g., short fiber glass, spherical glass, fine powder glass, E glass, T glass, D glass, etc.), silicone powder, fluorores
  • the filler (F) preferably contains one or more selected from the group consisting of silica, boehmite, barium sulfate, silicone powder, fluororesin-based fillers, urethane resin-based fillers, (meth)acrylic resin-based fillers, polyethylene-based fillers, styrene-butadiene rubber, and silicone rubber, more preferably contains one or more selected from the group consisting of silica, styrene-butadiene rubber, and silicone rubber, and even more preferably contains silica.
  • a cured product with an even lower relative dielectric constant and dielectric dissipation factor can be obtained, and an insulating layer with even higher resolution and even lower relative dielectric constant and dielectric dissipation factor, a high-density printed wiring board having an even higher resolution resist pattern, and a semiconductor device can be obtained, and various properties such as coating properties and heat resistance tend to be further improved.
  • fillers (F) may be surface-treated with a silane coupling agent, etc., as described below.
  • the silane coupling agent used for the surface treatment of the filler (F) is not particularly limited as long as it is a silane coupling agent generally used for the surface treatment of inorganic or organic substances.
  • aminosilanes such as ⁇ -glycidoxypropyltrimethoxysilane, 3-glycidoxypropyltriethoxysilane, 3-glycidoxypropyldimethoxymethylsilane, 3-glycidoxypropyldiethoxymethylsilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, and [8-(glycidyloxy)-n-octyl]trimethoxysilane; epoxysilanes such as vinyltris(2-methoxyethoxy)silane, vinyltrimethoxysilane, vinyltriethoxysilane, dimethoxymethylvinylsilane, diethoxymethylvinylsilane, trimethoxy(7-octen-1-yl)silane, and trimethoxy(4 vinyl silanes such as 3-methacryloxypropyltrimethoxysilane, 3-methacryloxypropyltriethoxy
  • the silane coupling agent preferably contains at least one selected from the group consisting of epoxy silane-based silane coupling agents, vinyl silane-based silane coupling agents, phenylamino silane-based silane coupling agents, and phenyl silane-based silane coupling agents, and more preferably contains an epoxy silane-based silane coupling agent.
  • epoxy silane-based silane coupling agents ⁇ -glycidoxypropyltrimethoxysilane is more preferable.
  • the bismaleimide compound (A) and the epoxy (meth)acrylate (B) react well with the maleimide compound (D) and the resin or compound (E) that are blended as necessary, and a cured product with an even lower dielectric constant and dielectric loss tangent can be obtained, and an insulating layer with even higher resolution and even lower dielectric constant and dielectric loss tangent, a high-density printed wiring board having an even higher resolution resist pattern, and a semiconductor device can be obtained, and various properties such as coating properties and heat resistance tend to be further improved.
  • Fused silica is more preferable as the silica because it can obtain a cured product with an even lower dielectric constant and dielectric dissipation factor, and can provide an insulating layer with even higher resolution and an even lower dielectric constant and dielectric dissipation factor, a high-density printed wiring board with an even higher resolution resist pattern, and a semiconductor device, and further improves the coating properties and heat resistance.
  • silica examples include SFP-120MC (trade name) and SFP-130MC (trade name) manufactured by Denka Co., Ltd.; 3SE-CM1 (trade name), 3SM-CM4 (trade name), K180SE-CM1 (trade name), 5SM-CM2 (trade name), 0.3 ⁇ m SX-CM1 (trade name), 0.3 ⁇ m SX-EM1 (trade name), 0.3 ⁇ m SV-EM1 (trade name), SC1050-MLQ (trade name), and SC2050-M manufactured by Admatechs Co., Ltd.
  • NU product name
  • SC2050-MTX product name
  • SC2050-MB product name
  • SC1050-MLE product name
  • 2.2 ⁇ mSC6103-SQ product name
  • SE2053-SQ product name
  • Y50SZ-AM1 product name
  • YA010C-MFN product name
  • YA050C - MJE product name
  • YA050C-MJM product name
  • YA050C-MJF product name
  • YA050C-MJA product name
  • the content of the filler (F) is preferably 5.0 to 100 parts by mass, more preferably 10 to 70 parts by mass, even more preferably 15 to 50 parts by mass, and even more preferably 20 to 35 parts by mass, per 100 parts by mass of the total resin solids in the resin composition.
  • the resin composition of the present embodiment may contain one or more selected from the group consisting of a silane coupling agent and a wetting dispersant in order to further improve the dispersibility of the filler (F) and the adhesive strength between the bismaleimide compound (A) and the epoxy (meth)acrylate (B), and between the maleimide compound (D), resin or compound (E), and the filler (F), etc., which are blended as necessary.
  • a silane coupling agent and a wetting dispersant in order to further improve the dispersibility of the filler (F) and the adhesive strength between the bismaleimide compound (A) and the epoxy (meth)acrylate (B), and between the maleimide compound (D), resin or compound (E), and the filler (F), etc., which are blended as necessary.
  • silane coupling agents are not particularly limited as long as they are silane coupling agents that are generally used for surface treatment of inorganic or organic substances.
  • silane coupling agents that are generally used for surface treatment of inorganic or organic substances.
  • the content of the silane coupling agent is usually 0.1 to 10 parts by mass per 100 parts by mass of resin solids in the resin composition.
  • the wetting and dispersing agent is not particularly limited as long as it is a dispersion stabilizer used for paints. Specific examples include DISPERBYK (registered trademark)-110 (trade name), 111 (trade name), 118 (trade name), 180 (trade name), 161 (trade name), BYK (registered trademark)-W996 (trade name), W9010 (trade name), and W903 (trade name) manufactured by BYK-Chemie Japan Co., Ltd. These wetting and dispersing agents can be used alone or in an appropriate mixture of two or more types.
  • the content of the wetting and dispersing agent is usually 0.1 to 10 parts by mass per 100 parts by mass of resin solids in the resin composition.
  • the resin composition of the present embodiment can obtain a cured product having a lower dielectric constant and dielectric loss tangent, and can obtain a high-definition insulating layer having a lower dielectric constant and dielectric loss tangent, a high-density printed wiring board having a higher-definition resist pattern, and a semiconductor device, so it is preferable to further include a crosslinking agent.
  • the crosslinking agent is different from the bismaleimide compound (A), the epoxy (meth)acrylate (B), the photocuring initiator (C), the maleimide compound (D), the resin or compound (E), and the filler (F).
  • the crosslinking agent can be used alone or in a suitable mixture of two or more types.
  • the crosslinking agent preferably contains one or more compounds selected from the group consisting of melamine compounds, allyl compounds, and urea compounds, and more preferably contains a melamine compound, since a cured product with an even lower dielectric constant and dielectric dissipation factor can be obtained, and an insulating layer with even higher resolution and an even lower dielectric constant and dielectric dissipation factor, a high-density printed wiring board having an even higher resolution resist pattern, and a semiconductor device can be obtained.
  • melamine compounds include hexamethylol melamine, hexamethoxymethyl melamine, hexamethylol melamine compounds in which 1 to 6 methylol groups have been methoxymethylated, and mixtures thereof.
  • melamine compounds can also be used.
  • Examples of commercially available products include the compound represented by formula (a) (Nicalac (registered trademark) MW-100LM (product name), manufactured by Sanwa Chemical Co., Ltd.) and the compound represented by formula (b) (Nicalac (registered trademark) MX270 (product name), manufactured by Sanwa Chemical Co., Ltd.).
  • allyl compounds examples include diallyl isocyanurate, triallyl isocyanurate, and tetraallyl isocyanurate. Commercially available allyl compounds can also be used. Examples of commercially available products include triallyl isocyanurate (TAIC (registered trademark), TAIC (registered trademark), Mitsubishi Chemical Corporation).
  • urea compounds examples include tetramethylurea and tetramethoxymethylurea.
  • the content of the crosslinking agent is usually 0.1 to 10 parts by mass, and preferably 1.0 to 8.0 parts by mass, per 100 parts by mass of the resin solids in the resin composition.
  • the resin composition of the present embodiment may contain a compound containing one or more carboxy groups as long as the effect of the present invention is exhibited.
  • the compound containing one or more carboxy groups contains one or more carboxy groups in its structure.
  • the compound containing one or more carboxy groups is different from the bismaleimide compound (A), the epoxy (meth)acrylate (B), the photocuring initiator (C), the maleimide compound (D), the resin or compound (E), the filler (F), and the crosslinking agent.
  • the carboxy group may be a salt such as a sodium salt and a potassium salt. When two or more carboxy groups are contained in the molecule, two of the two or more carboxy groups may be linked to each other to form an acid anhydride.
  • the compound containing one or more carboxy groups can be used alone or in a suitable mixture of two or more.
  • the compound containing one or more carboxy groups contains an integer of 2 to 20 carboxy groups in the molecule.
  • the molecular weight of the compound containing one or more carboxy groups is preferably 50 to 10,000, more preferably 100 to 8,000, even more preferably 130 to 6,000, and even more preferably 150 to 5,000, in order to further improve developability.
  • the mass average molecular weight (Mw) of the compound containing one or more carboxy groups is preferably 50 to 10,000, more preferably 100 to 8,000, and even more preferably 150 to 5,000, in order to further improve developability.
  • the content of the compound containing one or more carboxy groups is usually 0.1 to 30 parts by mass per 100 parts by mass of the resin solids in the resin composition, since this can impart better alkaline developability and allow the resin composition to exhibit good curing properties without inhibiting the photocuring reaction.
  • the resin composition of the present embodiment may contain an organic solvent as necessary.
  • an organic solvent By using an organic solvent, the viscosity during preparation of the resin composition can be adjusted to a more suitable range.
  • the type of organic solvent is not particularly limited as long as it can dissolve a part or all of the resin in the resin composition.
  • the organic solvent can be used alone or in a suitable mixture of two or more kinds.
  • organic solvents include halogenated solvents such as dichloromethane, chloroform, dichloroethane, and chlorobenzene; aprotic polar solvents such as dimethylformamide, dimethylacetamide, dimethylsulfoxide, tetrahydrofuran, dioxane, and acetonitrile; ketone solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclopentanone, and cyclohexanone; cellosolve solvents such as 2-ethoxyethanol and propylene glycol monomethyl ether; aliphatic alcohol solvents such as methanol, ethanol, propanol, isopropanol, and butanol; aromatic group-containing phenol solvents such as phenol and cresol; ester solvents such as ethyl lactate, methyl acetate, ethyl acetate, butyl acetate, isoamyl a
  • the bismaleimide compound (A), the epoxy (meth)acrylate (B), the initiator (C), the compound (D) blended as necessary, the resin or compound (E), the filler (F), the silane coupling agent, the wetting and dispersing agent, the crosslinking agent, and the compound containing one or more carboxyl groups, as well as other resins and compounds are preferred from the viewpoint of exhibiting superior solubility, and the aprotic polar solvent, the ketone solvent, the cellosolve solvent, and the ester solvent are even more preferred from the viewpoint of exhibiting even superior solubility.
  • aprotic polar solvent dimethylacetamide is preferred.
  • ketone solvent methyl ethyl ketone is preferred.
  • cellosolve solvent propylene glycol monomethyl ether is preferred.
  • ester solvent butyl acetate, gamma-butyrolactone, and propylene glycol monomethyl ether acetate are preferred.
  • flame-retardant compounds such as additives, which have not been mentioned so far, can be used in combination, as long as the characteristics of this embodiment are not impaired. These are not particularly limited as long as they are commonly used.
  • flame-retardant compounds include nitrogen-containing compounds such as melamine and benzoguanamine; oxazine ring-containing compounds; phosphorus-based compounds such as phosphate compounds of phosphorus-based compounds, aromatic condensed phosphate esters, and halogen-containing condensed phosphate esters.
  • additives include ultraviolet absorbers, antioxidants, fluorescent brighteners, photosensitizers, dyes, pigments, thickeners, lubricants, defoamers, surface conditioners, gloss agents, polymerization inhibitors, and heat curing accelerators such as imidazole compounds. These components can be used alone or in a suitable mixture of two or more types. Commercially available products can also be used as imidazole. An example of a commercially available product is 2-phenyl-4-methylimidazole (Curezol (registered trademark) 2P4MZ (product name, Shikoku Chemical Industry Co., Ltd.)).
  • the content of the other components other than the additives is usually 0.01 to 10 parts by mass each per 100 parts by mass of the resin solids in the resin composition.
  • the content of the additives in the other components is usually 0.01 to 10 parts by mass each per 100 parts by mass of the resin solids in the resin composition.
  • the resin composition of the present embodiment can be prepared by appropriately mixing the bismaleimide compound (A), the epoxy (meth)acrylate (B), and the photocuring initiator (C) with, as necessary, the maleimide compound (D), the resin or compound (E), the filler (F), the crosslinking agent, the compound containing one or more carboxy groups, and other compounds, an organic solvent, and additives, etc.
  • the method for producing the resin composition include a method in which the above-mentioned components are sequentially mixed in a solvent and thoroughly stirred.
  • known processes such as stirring, mixing, and kneading
  • the dispersibility of each component in the resin composition can be improved by performing the stirring and dispersion process using a stirring tank equipped with a stirrer having appropriate stirring capacity.
  • the stirring, mixing, and kneading processes can be appropriately performed using known devices such as a stirring device for dispersion such as an ultrasonic homogenizer, a device for mixing such as a three-roll mill, a ball mill, a bead mill, and a sand mill, or a revolving or rotating type mixer.
  • an organic solvent can be used as necessary when preparing the resin composition.
  • the type of organic solvent is not particularly limited as long as it can dissolve the resin in the resin composition, and specific examples are as described above.
  • the resin composition can be suitably used as a varnish when producing the resin sheet of this embodiment described below.
  • the varnish can be obtained by a known method.
  • the varnish can be obtained by adding 10 to 900 parts by mass, preferably 30 to 500 parts by mass, of an organic solvent to 100 parts by mass of the components in the resin composition excluding the organic solvent, and carrying out the known treatments (stirring, mixing, kneading, etc.) described above.
  • the organic solvent used to prepare the varnish is not particularly limited, and specific examples are as described above.
  • the resin composition of the present embodiment can be suitably used for the preparation of a multilayer printed wiring board, and can be preferably used in applications requiring an insulating resin composition.
  • it can be used for photosensitive films, photosensitive films with a support, prepregs, resin sheets, circuit boards (for laminates, multilayer printed wiring boards, etc.), solder resists, underfill materials, die bonding materials, semiconductor encapsulants, hole-filling resins, and component-embedding resins.
  • the resin composition can obtain a cured product with a lower relative dielectric constant and dielectric loss tangent, and has excellent photocurability and alkaline developability, so it can be suitably used for the insulating layer of a multilayer printed wiring board or for the solder resist.
  • the cured product is obtained by curing the resin composition.
  • the resin composition is melted or dissolved in a solvent, poured into a mold, and cured under normal conditions using light.
  • the light wavelength range is preferably 100 to 500 nm, which allows efficient curing by a photocuring initiator, etc.
  • the resin sheet of the present embodiment is a resin sheet with a support, which has a support and a resin layer disposed on one or both sides of the support, and the resin layer contains the resin composition of the present embodiment.
  • the resin sheet can be produced by applying the resin composition onto the support and drying it.
  • the resin layer in the resin sheet has excellent photocurability and alkaline developability.
  • the support may be any known material, and is not particularly limited, but is preferably a resin film.
  • resin films include polyimide film, polyamide film, polyester film, polyethylene terephthalate (PET) film, polybutylene terephthalate (PBT) film, polypropylene (PP) film, polyethylene (PE) film, polyethylene naphthalate film, polyvinyl alcohol film, and triacetyl acetate film.
  • PET film is preferred.
  • the resin film is preferably coated with a release agent on its surface to facilitate peeling from the resin layer.
  • the thickness of the resin film is preferably 5 to 100 ⁇ m, more preferably 10 to 50 ⁇ m. If the thickness is 5 ⁇ m or more, the support tends to be less likely to break when peeled off before alkaline development. If the thickness is 100 ⁇ m or less, the resolution tends to be less likely to decrease when exposed from above the support. Therefore, if the thickness is within the above range, a better resin film tends to be obtained. In this specification, the thickness can be measured using, for example, a micrometer.
  • the resin film to have excellent transparency.
  • the resin layer may be protected with a protective film.
  • a protective film By protecting the resin layer side with a protective film, adhesion of dirt and the like to the resin layer surface and scratches can be more effectively prevented.
  • the protective film a film made of the same material as the resin film can be used.
  • the thickness of the protective film is preferably 1 to 50 ⁇ m, more preferably 5 to 40 ⁇ m. When the thickness is 1 ⁇ m or more, the handleability of the protective film tends not to decrease. When the thickness is 50 ⁇ m or less, it tends to be advantageous in terms of cost.
  • the adhesive strength between the resin layer and the protective film is smaller than the adhesive strength between the resin layer and the support.
  • Examples of the method for producing a resin sheet include a method in which a resin composition is applied to a support such as a PET film, and the resin composition is dried to remove the organic solvent, thereby producing a resin sheet.
  • the coating method can be a known method using, for example, a roll coater, a comma coater, a gravure coater, a die coater, a bar coater, a lip coater, a knife coater, a squeeze coater, etc. Drying can be performed, for example, by a method of heating in a dryer at 60 to 200° C. for 1 to 60 minutes.
  • the amount of organic solvent remaining in the resin layer is preferably 5% by mass or less relative to the total mass of the resin layer, in order to better prevent the diffusion of the organic solvent in subsequent steps.
  • the thickness of the resin layer is preferably 1 to 50 ⁇ m, in order to further improve handleability.
  • the resin sheet can be preferably used for manufacturing insulating layers for multilayer printed wiring boards.
  • the multilayer printed wiring board of the present embodiment has an insulating layer and a conductor layer formed on one or both sides of the insulating layer, and the insulating layer contains the resin composition of the present embodiment.
  • the insulating layer can be obtained, for example, by stacking one or more resin sheets and curing them.
  • the number of layers of the insulating layer and the conductor layer can be appropriately set according to the intended use.
  • the order of the insulating layer and the conductor layer is not particularly limited.
  • the conductor layer may be a metal foil used in various printed wiring board materials, for example, a metal foil such as copper and aluminum.
  • the copper metal foil can be a copper foil such as rolled copper foil and electrolytic copper foil.
  • the thickness of the conductor layer is usually 1 to 100 ⁇ m. Specifically, it can be manufactured by the following method.
  • the resin layer side of the resin sheet is laminated on one or both sides of the circuit board using a vacuum laminator.
  • circuit boards include glass epoxy boards, metal boards, ceramic boards, silicon boards, semiconductor sealing resin boards, polyester boards, polyimide boards, BT resin boards, and thermosetting polyphenylene ether boards.
  • the circuit board refers to a board on which a patterned conductor layer (circuit) is formed on one or both sides of the board as described above.
  • a board in which one or both sides of the outermost layer of the multilayer printed wiring board are patterned conductor layers (circuits) is also included in the circuit board.
  • the insulating layer laminated on the multilayer printed wiring board may be an insulating layer obtained by stacking and curing one or more resin sheets of the present embodiment, or may be an insulating layer obtained by stacking one or more resin sheets of the present embodiment and one or more known resin sheets different from the resin sheet of the present embodiment.
  • the method of stacking the resin sheet of the present embodiment and the known resin sheet different from the resin sheet of the present embodiment is not particularly limited.
  • the surface of the conductor layer may be roughened in advance by blackening and/or copper etching.
  • the resin sheet has a protective film
  • the protective film is peeled off and then the resin sheet and the circuit board are preheated as necessary, and the resin layer of the resin sheet is pressure-bonded to the circuit board while being pressurized and heated.
  • a method of laminating the resin layer of the resin sheet to the circuit board under reduced pressure by a vacuum lamination method is preferably used.
  • the pressure bonding temperature (lamination temperature) is preferably 50 to 140°C.
  • the pressure bonding pressure is preferably 1 to 15 kgf/ cm2 .
  • the pressure bonding time is preferably 5 to 300 seconds.
  • the air pressure is preferably reduced pressure, more preferably 20 mmHg or less.
  • the lamination process may be a batch process or a continuous process using a roll.
  • the vacuum lamination method may be carried out using a commercially available vacuum laminator. Examples of commercially available vacuum laminators include a two-stage build-up laminator manufactured by Nikko Materials Co., Ltd.
  • a predetermined portion of the resin layer is irradiated with various active energy rays from a light source to cure the irradiated portion of the resin layer.
  • the bismaleimide compound (A) does not inhibit the photocuring reaction in the exposure step.
  • the irradiation may be performed through a mask pattern, or a direct writing method may be used for direct irradiation.
  • active energy rays include ultraviolet rays, visible light rays, electron beams, and X-rays.
  • the wavelength of the active energy rays is, for example, in the range of 200 to 600 nm.
  • the dose is approximately 5 to 1000 mJ/cm 2.
  • a printed wiring board having a high-density and high-definition wiring formation is manufactured using a stepper that performs projection exposure in a step-and-repeat manner, it is preferable to use an active energy ray having a wavelength of 365 nm (i-line) as the active energy ray.
  • the dose is approximately 5 to 10,000 mJ/cm 2.
  • an active energy ray having a wavelength of 365 nm (i-line) can also be used.
  • the exposure method through a mask pattern includes a contact exposure method in which the mask pattern is closely attached to the multilayer printed wiring board, and a non-contact exposure method in which projection exposure is performed using a lens or a mirror without closely attaching the mask pattern to the multilayer printed wiring board, and either method can be used.
  • the exposure may be performed from above the support, or after peeling off the support.
  • the unexposed resin layer containing the resin composition of the present embodiment contains the bismaleimide compound (A) and the epoxy (meth)acrylate (B), and therefore has excellent alkaline developability and allows the unexposed resin composition to be quickly removed, thereby making it possible to obtain a printed wiring board having a high-resolution pattern.
  • the developer is not particularly limited as long as it selectively dissolves the unexposed portions, but alkaline developers such as an aqueous tetramethylammonium hydroxide solution, an aqueous sodium carbonate solution, an aqueous potassium carbonate solution, an aqueous sodium hydroxide solution, and an aqueous potassium hydroxide solution are used. In this embodiment, it is more preferable to use an aqueous tetramethylammonium hydroxide solution.
  • alkaline developers can be used alone or in an appropriate mixture of two or more types.
  • Alkaline development can be performed by known methods such as dipping, paddle, spray, oscillating immersion, brushing, and scraping. In forming a pattern, these development methods may be used in combination as necessary. As a development method, it is preferable to use a high-pressure spray, as this further improves the resolution. When using a spray method, the spray pressure is preferably 0.02 to 0.5 MPa.
  • a post-baking step is performed to form an insulating layer (cured product).
  • the post-baking step include an ultraviolet irradiation step using a high-pressure mercury lamp and a heating step using a clean oven, and these steps can be used in combination.
  • the amount of irradiation can be adjusted as needed, and irradiation can be performed at an amount of irradiation of, for example, about 0.05 to 10 J/cm2.
  • the heating conditions can be appropriately selected as needed, but are preferably in the range of 150 to 220°C for 20 to 180 minutes, and more preferably in the range of 160 to 200°C for 30 to 150 minutes.
  • a conductor layer is formed on the surface of the insulating layer by dry plating.
  • the surface of the insulating layer may be subjected to a surface modification treatment before dry plating.
  • a known method such as a plasma etching treatment, a reverse sputtering treatment, or a corona treatment can be used.
  • the dry plating known methods such as vapor deposition, sputtering, and ion plating can be used.
  • a multilayer printed wiring board is placed in a vacuum chamber, and a metal is heated and evaporated to form a metal film on an insulating layer.
  • a metal is heated and evaporated to form a metal film on an insulating layer.
  • a multilayer printed wiring board is placed in a vacuum chamber, an inert gas such as argon is introduced, and a direct current voltage is applied to cause the ionized inert gas to collide with a target metal, and a metal film can be formed on an insulating layer by the metal that is knocked out.
  • a conductor layer is formed by electroless plating or electrolytic plating.
  • Subsequent pattern formation methods include, for example, subtractive and semi-additive methods.
  • the semiconductor device of this embodiment includes the resin composition of this embodiment. Specifically, it can be manufactured by the following method.
  • the semiconductor device can be manufactured by mounting a semiconductor chip on a conductive portion of a multilayer printed wiring board.
  • the conductive portion refers to a portion of the multilayer printed wiring board that transmits an electric signal, and the conductive portion may be located on the surface or embedded.
  • the semiconductor chip is not particularly limited as long as it is an electric circuit element made of a semiconductor material.
  • the method of mounting semiconductor chips when manufacturing semiconductor devices is not particularly limited as long as the semiconductor chips function effectively. Specific examples include wire bonding mounting methods, flip chip mounting methods, bumpless build-up layer (BBUL) mounting methods, anisotropic conductive film (ACF) mounting methods, and non-conductive film (NCF) mounting methods.
  • a semiconductor device can also be manufactured by forming an insulating layer containing a resin composition on a semiconductor chip or a substrate on which a semiconductor chip is mounted.
  • the substrate on which the semiconductor chip is mounted may be in the form of a wafer or a panel. After formation, it can be manufactured using the same method as the multilayer printed wiring board described above.
  • MIZ-001 (trade name, mass average molecular weight (Mw): 3000) manufactured by Nippon Kayaku Co., Ltd. was used, and a chloroform solution containing 1 mass % of this MIZ-001 (trade name) was prepared, and the transmittance at a wavelength of 365 nm was measured using a UV-vis measurement device (Hitachi Spectrophotometer U-4100 (trade name) manufactured by Hitachi High-Technologies Corporation). Note that when measuring the transmittance, a quartz cell with a cell length (passage path length during measurement) of 1 cm was used.
  • the transmittance at a wavelength of 365 nm was measured for epoxy (meth)acrylate (B), ZXR-1889H (product name) manufactured by Nippon Kayaku Co., Ltd. and ZXR-1807H (product name) manufactured by Nippon Kayaku Co., Ltd.
  • the transmittance at a wavelength of 365 nm was measured for maleimide compound (D) NE-X-9470S (product name) manufactured by DIC Corporation.
  • the transmittance at a wavelength of 365 nm was measured for the resin or compound (E) OPE (registered trademark)-2St1200 (product name) manufactured by Mitsubishi Gas Chemical Co., Ltd.
  • Irgacure (registered trademark) OXE01 (product name) manufactured by BASF Japan Ltd. was used as the photocuring initiator (C), and a chloroform solution containing 0.01% by mass of this Irgacure (registered trademark) OXE01 (product name) was prepared, and the absorbance at a wavelength of 365 nm was measured using a UV-vis measurement device (U-4100 (product name)). Note that when measuring the absorbance, a quartz cell with a cell length (path length during measurement) of 1 cm was used.
  • Example 1 (Preparation of resin composition and resin sheet)
  • the bismaleimide compound (A) 40 parts by mass of MIZ-001 (trade name, mass average molecular weight (Mw): 3000, containing a maleimide compound of formula (3), in which a is 1 to 6 (integer)) manufactured by Nippon Kayaku Co., Ltd., and as the epoxy (meth)acrylate (B), ZXR-1889H (trade name, a mixture of compounds represented by formula (36), in which the repeating numbers of n 8 and n 9 are different, n 8 is in the range of 1 to 19 and n 9 is in the range of 1 to 19, and n 8 and n
  • epoxy (meth)acrylate (B) 30.3 parts by mass (20 parts by mass calculated as non-volatile content) of ZXR -1807H (trade name, a compound represented by formula (36), a mixture of compounds having different repeating numbers of n 8 and n 9 , n 8 being in the range of 1 to 19 and
  • a filler (F) 41.3 parts by mass (25 parts by mass in terms of non-volatile content) of a MEK (methyl ethyl ketone) solution (non-volatile content 60.5%) of Admatechs 3SE-CM1 (product name, epoxy silane surface-treated slurry (fused) silica, average particle size: 300 nm) manufactured by Admatechs Co., Ltd. was mixed with 5.0 parts by mass of Nikalac (registered trademark) MW-100LM (product name, compound represented by formula (a)) manufactured by Sanwa Chemical Co., Ltd. as a crosslinking agent, and 42 parts by mass of MEK was added to obtain a varnish (resin composition).
  • a MEK methyl ethyl ketone
  • the mass ratio ((A)/(B)) of the bismaleimide compound (A) to the epoxy (meth)acrylate (B) was 1.
  • This varnish was dropped onto a 25 ⁇ m thick PET film (UNIPEEL (registered trademark) TR1-25 (product name) manufactured by Unitika Ltd.), and a coating film was formed by bar coating (desktop printing tester K Control Coater (product name) manufactured by Matsuo Sangyo Co., Ltd.).
  • the resulting coating film was dried at 80° C. for 5 minutes to obtain a resin sheet having a PET film as a support and a resin layer having a thickness of 15 ⁇ m.
  • the resin sheet was placed on a substrate having both sides roughened with CZ8101 (trade name) manufactured by MEC Co., Ltd., and the resin side of the resin sheet was placed facing the substrate.
  • the substrate was then evacuated for 30 seconds (5.0 hPa or less) using a vacuum laminator (manufactured by Nikko Materials Co., Ltd.). Thereafter, lamination molding was performed for 30 seconds at a pressure of 10 kgf/cm 2 and a temperature of 70° C. Further, lamination molding was performed for 60 seconds at a pressure of 7 kgf/cm 2 and a temperature of 70° C. to obtain an evaluation laminate in which the copper foil laminate, the resin layer, and the support were laminated.
  • the laminate (a) was folded in half so that the resin surfaces from which the support was peeled faced each other, the resin surfaces were laminated together, and a vacuum laminator (manufactured by Nikko Materials Co., Ltd.) was used to draw a vacuum (5.0 hPa or less) for 30 seconds. Thereafter, laminate molding was performed at a pressure of 10 kgf/cm 2 and a temperature of 70° C. for 30 seconds, and then laminate molding was performed at a pressure of 7 kgf/cm 2 and a temperature of 70° C. for 60 seconds to obtain a laminate (b).
  • a vacuum laminator manufactured by Nikko Materials Co., Ltd.
  • the laminate (b) was folded in half so that the resin surfaces from which the support was peeled faced each other, and the resin surfaces were bonded together, and a vacuum was drawn for 30 seconds (5.0 hPa or less) using a vacuum laminator (manufactured by Nikko Materials Co., Ltd.). Thereafter, lamination molding was performed for 30 seconds at a pressure of 10 kgf/cm 2 and a temperature of 70° C., and further, lamination molding was performed for 60 seconds at a pressure of 7 kgf/cm 2 and a temperature of 70° C., to obtain an evaluation laminate resin sheet having supports on both sides. The thickness of the resin layer in the obtained evaluation laminate resin sheet was 80 ⁇ m or more.
  • Example 2 As the bismaleimide compound (A), 20 parts by mass of MIZ-001 (trade name, mass average molecular weight (Mw): 3000, containing a maleimide compound of formula (3), where a in formula (3) is a mixture of 1 to 6 (integer)) manufactured by Nippon Kayaku Co., Ltd., and as the epoxy (meth)acrylate (B), 15.15 parts by mass (10 parts by mass in terms of nonvolatile content) of ZXR-1889H (trade name, compound represented by formula (36)) (nonvolatile content 66.0%) manufactured by Nippon Kayaku Co., Ltd.
  • a resin or compound (E) 15.3 parts by mass (10 parts by mass of OPE (registered trademark)-2St1200 (trade name, modified polyphenylene ether compound having a structure represented by formula (24)) (65.0% non-volatile content) manufactured by Mitsubishi Gas Chemical Co., Ltd. was used.
  • a filler (F) 15.3 parts by mass (10 parts by mass of OPE (registered trademark)-2St1200 (trade name, modified polyphenylene ether compound having a structure represented by formula (24)) (65.0% non-volatile content) manufactured by Admatechs Co., Ltd. was used.
  • the mass ratio ((A)/(B)) of the bismaleimide compound (A) to the epoxy (meth)acrylate (B) was 0.67.
  • Example 3 As the bismaleimide compound (A), 60 parts by mass of MIZ-001 (trade name, mass average molecular weight (Mw): 3000, containing a maleimide compound of formula (3), where a in formula (3) is a mixture of 1 to 6 (integer)) manufactured by Nippon Kayaku Co., Ltd., and as the epoxy (meth)acrylate (B), 45.45 parts by mass (30 parts by mass in terms of nonvolatile content) of ZXR-1889H (trade name, compound represented by formula (36)) (nonvolatile content 66.0%) manufactured by Nippon Kayaku Co., Ltd.
  • MIZ-001 trade name, mass average molecular weight (Mw): 3000
  • MIZ-001 mass average molecular weight (Mw): 3000
  • a maleimide compound of formula (3) where a in formula (3) is a mixture of 1 to 6 (integer) manufactured by Nippon Kayaku Co., Ltd.
  • the epoxy (meth)acrylate (B) 45.45 parts
  • a resin or compound (E) 15.3 parts by mass (10 parts by mass of OPE (registered trademark)-2St1200 (trade name, modified polyphenylene ether compound having a structure represented by formula (24)) (65.0% non-volatile content) manufactured by Mitsubishi Gas Chemical Co., Ltd. was used.
  • a filler (F) 15.3 parts by mass (10 parts by mass of OPE (registered trademark)-2St1200 (trade name, modified polyphenylene ether compound having a structure represented by formula (24)) (65.0% non-volatile content) manufactured by Admatechs Co., Ltd. was used.
  • the mass ratio ((A)/(B)) of the bismaleimide compound (A) to the epoxy (meth)acrylate (B) was 1.2.
  • a resin sheet, a laminate for evaluation, and a laminate resin sheet for evaluation were obtained in the same manner as in Example 1.
  • Example 4 As the bismaleimide compound (A), 40 parts by mass of MIZ-001 (trade name, mass average molecular weight (Mw): 3000, containing a maleimide compound of formula (3), where a in formula (3) is a mixture of 1 to 6 (integer)) manufactured by Nippon Kayaku Co., Ltd., and as the epoxy (meth)acrylate (B), 30.3 parts by mass (20 parts by mass in terms of nonvolatile content) of ZXR-1889H (trade name, compound represented by formula (36)) (nonvolatile content 66.0%) manufactured by Nippon Kayaku Co., Ltd., and ) acrylate (B), 30.3 parts by mass (20 parts by mass in terms of non-volatile content) of ZXR-1807H (trade name, compound represented by formula (36)) (non-volatile content 66.0%) manufactured by Nippon Kayaku Co., Ltd., and 5.0 parts by mass of Irgacure (registered trademark) OXE01 (trade name, 1,2-
  • the mass ratio ((A)/(B)) of the bismaleimide compound (A) to the epoxy (meth)acrylate (B) was 1.
  • a resin sheet, a laminate for evaluation, and a laminate resin sheet for evaluation were obtained in the same manner as in Example 1.
  • Example 5 As the bismaleimide compound (A), 40 parts by mass of MIZ-001 (trade name, mass average molecular weight (Mw): 3000, containing a maleimide compound of formula (3), where a in formula (3) is a mixture of 1 to 6 (integer)) manufactured by Nippon Kayaku Co., Ltd., and as the epoxy (meth)acrylate (B), 30.3 parts by mass (20 parts by mass in terms of nonvolatile content) of ZXR-1889H (trade name, compound represented by formula (36)) (nonvolatile content 66.0%) manufactured by Nippon Kayaku Co., Ltd. were used.
  • NE-X-9470S (trade name, compound represented by formula (6)) (non-volatile content 61.0%) manufactured by DIC Corporation as a maleimide compound (D) (16.3 parts by mass (10 parts by mass in terms of non-volatile content) and OPE (registered trademark)-2St1200 (trade name, modified polyphenylene ether compound having a structure represented by formula (24)) (non-volatile content 65.0%) manufactured by Mitsubishi Gas Chemical Company, Inc.
  • Example 6 As the bismaleimide compound (A), 40 parts by mass of MIZ-001 (trade name, mass average molecular weight (Mw): 3000, containing a maleimide compound of formula (3), where a in formula (3) is a mixture of 1 to 6 (integer)) manufactured by Nippon Kayaku Co., Ltd., and as the epoxy (meth)acrylate (B), 30.3 parts by mass (20 parts by mass in terms of nonvolatile content) of ZXR-1889H (trade name, compound represented by formula (36)) (nonvolatile content 66.0%) manufactured by Nippon Kayaku Co., Ltd., and As the acrylate (B), 30.3 parts by mass (20 parts by mass in terms of non-volatile content) of ZXR-1807H (trade name, compound represented by formula (36)) (non-volatile content 66.0%) manufactured by Nippon Kayaku Co., Ltd., and 4.0 parts by mass of Irgacure (registered trademark) OXE03 (trade name, oxi
  • the filler (F) 41.3 parts by mass (25 parts by mass in terms of non-volatile content) of MEK (methyl ethyl ketone) solution (non-volatile content 60.5%) of Admatechs 3SE-CM1 (trade name, epoxy silane surface-treated slurry (fused) silica, average particle size: 300 nm) manufactured by Admatechs Co., Ltd. was mixed with 5.0 parts by mass of Nikalac (registered trademark) MW-100LM (trade name, compound represented by formula (a)) manufactured by Sanwa Chemical Co., Ltd. as a crosslinking agent, and 42 parts by mass of MEK was added to obtain a varnish (resin composition).
  • MEK methyl ethyl ketone
  • Admatechs 3SE-CM1 trade name, epoxy silane surface-treated slurry (fused) silica, average particle size: 300 nm
  • Nikalac registered trademark
  • MW-100LM trade name, compound represented by formula (
  • the mass ratio ((A)/(B)) of the bismaleimide compound (A) to the epoxy (meth)acrylate (B) was 1.
  • a resin sheet, a laminate for evaluation, and a laminate resin sheet for evaluation were obtained in the same manner as in Example 1.
  • Example 7 As the bismaleimide compound (A), 40 parts by mass of MIZ-001 (trade name, mass average molecular weight (Mw): 3000, containing a maleimide compound of formula (3), where a in formula (3) is a mixture of 1 to 6 (integer)) manufactured by Nippon Kayaku Co., Ltd., and as the epoxy (meth)acrylate (B), 30.3 parts by mass (20 parts by mass in terms of nonvolatile content) of ZXR-1889H (trade name, compound represented by formula (36)) (nonvolatile content 66.0%) manufactured by Nippon Kayaku Co., Ltd.
  • a resin or compound (E) 15.3 parts by mass (10 parts by mass of OPE (registered trademark)-2St1200 (trade name, modified polyphenylene ether compound having a structure represented by formula (24)) (65.0% non-volatile content) manufactured by Mitsubishi Gas Chemical Co., Ltd. was used.
  • a filler (F) 15.3 parts by mass (10 parts by mass of OPE (registered trademark)-2St1200 (trade name, modified polyphenylene ether compound having a structure represented by formula (24)) (65.0% non-volatile content) manufactured by Admatechs Co., Ltd. was used.
  • the mass ratio ((A)/(B)) of the bismaleimide compound (A) to the epoxy (meth)acrylate (B) was 1.
  • a resin sheet, a laminate for evaluation, and a laminate resin sheet for evaluation were obtained in the same manner as in Example 1.
  • Example 8 As the bismaleimide compound (A), 40 parts by mass of MIZ-001 (trade name, mass average molecular weight (Mw): 3000, containing a maleimide compound of formula (3), where a in formula (3) is a mixture of 1 to 6 (integer)) manufactured by Nippon Kayaku Co., Ltd., and as the epoxy (meth)acrylate (B), 30.3 parts by mass (20 parts by mass in terms of nonvolatile content) of ZXR-1889H (trade name, compound represented by formula (36)) (nonvolatile content 66.0%) manufactured by Nippon Kayaku Co., Ltd.
  • the mass ratio ((A)/(B)) of the bismaleimide compound (A) to the epoxy (meth)acrylate (B) was 1.
  • a resin sheet, a laminate for evaluation, and a laminate resin sheet for evaluation were obtained in the same manner as in Example 1.
  • Example 9 As the bismaleimide compound (A), 25 parts by mass of MIZ-001 (trade name, mass average molecular weight (Mw): 3000, containing a maleimide compound of formula (3), where a in formula (3) is a mixture of 1 to 6 (integer)) manufactured by Nippon Kayaku Co., Ltd., and as the epoxy (meth)acrylate (B), ZXR-1807H (trade name, compound represented by formula (36)) (non-volatile content 66.
  • MIZ-001 trade name, mass average molecular weight (Mw): 3000
  • MIZ-001 mass average molecular weight (Mw): 3000
  • a maleimide compound of formula (3) where a in formula (3) is a mixture of 1 to 6 (integer) manufactured by Nippon Kayaku Co., Ltd.
  • the epoxy (meth)acrylate (B), ZXR-1807H trade name, compound represented by formula (36)
  • photocuring initiator (C) 5 parts by mass of Irgacure (registered trademark) OXE03 (product name, oxime esters) manufactured by BASF Japan Ltd., and as the maleimide compound (D), 16.3 parts by mass of NE-X-9470S (product name, compound represented by formula (6)) (non-volatile content 61.0%) manufactured by DIC Corporation (16.3 parts by mass of NE-X-9470S) (product name, compound represented by formula (6)) (non-volatile content 61.0%) was used.
  • Irgacure registered trademark
  • OXE03 product name, oxime esters
  • maleimide compound (D) 16.3 parts by mass of NE-X-9470S (product name, compound represented by formula (6)) (non-volatile content 61.0%) manufactured by DIC Corporation (16.3 parts by mass of NE-X-9470S) (product name, compound represented by formula (6)) (non-volatile content 61.0%) was used.
  • a varnish (resin composition) As a filler (F), and 5.0 parts by mass of Nikalac (registered trademark) MW-100LM (trade name, compound represented by formula (a)) manufactured by Sanwa Chemical Co., Ltd. as a crosslinking agent were mixed, and 40 parts by mass of MEK was added to obtain a varnish (resin composition).
  • the mass ratio ((A)/(B)) of the bismaleimide compound (A) to the epoxy (meth)acrylate (B) was 0.56.
  • a resin sheet, a laminate for evaluation, and a laminate resin sheet for evaluation were obtained in the same manner as in Example 1.
  • Example 10 As the bismaleimide compound (A), 40 parts by mass of MIZ-001 (trade name, mass average molecular weight (Mw): 3000, containing a maleimide compound of formula (3), where a in formula (3) is a mixture of 1 to 6 (integer)) manufactured by Nippon Kayaku Co., Ltd., and as the epoxy (meth)acrylate (B), ZXR-1889H (trade name, compound represented by formula (36)) (non-volatile content 66.0 %), 60.6 parts by mass (40 parts by mass in terms of non-volatile content), 5.0 parts by mass of Irgacure (registered trademark) OXE03 (product name, oxime esters) manufactured by BASF Japan Ltd.
  • MIZ-001 trade name, mass average molecular weight (Mw): 3000
  • MIZ-001 mass average molecular weight (Mw): 3000
  • a maleimide compound of formula (3) where a in formula (3) is a mixture of 1 to 6 (integer
  • the resin or compound (E) 41.3 parts by mass (25 parts by mass in terms of non-volatile content) of MEK (methyl ethyl ketone) solution (non-volatile content 60.5%) of Admatechs 3SE-CM1 (trade name, epoxy silane surface-treated slurry (fused) silica, average particle size: 300 nm) manufactured by Admatechs Co., Ltd. as the filler (F), and 5.0 parts by mass of Nikalac (registered trademark) MW-100LM (trade name, compound represented by formula (a)) manufactured by Sanwa Chemical Co., Ltd. as the crosslinking agent were mixed, and 42 parts by mass of MEK was added to obtain a varnish (resin composition).
  • MEK methyl ethyl ketone
  • Admatechs 3SE-CM1 trade name, epoxy silane surface-treated slurry (fused) silica, average particle size: 300 nm
  • Nikalac registered trademark
  • MW-100LM trade
  • the mass ratio ((A)/(B)) of the bismaleimide compound (A) to the epoxy (meth)acrylate (B) was 1.
  • a resin sheet, a laminate for evaluation, and a laminate resin sheet for evaluation were obtained in the same manner as in Example 1.
  • Example 11 As the bismaleimide compound (A), 40 parts by mass of MIZ-001 (trade name, mass average molecular weight (Mw): 3000, containing a maleimide compound of formula (3), where a in formula (3) is a mixture of 1 to 6 (integer)) manufactured by Nippon Kayaku Co., Ltd., and as the epoxy (meth)acrylate (B), ZXR-1889H (trade name, compound represented by formula (36)) (non-volatile content 66.0%) manufactured by Nippon Kayaku Co., Ltd.
  • the resin or compound (E) 15.3 parts by mass (10 parts by mass in terms of non-volatile content) of OPE (registered trademark)-2St1200 (trade name, modified polyphenylene ether compound having a structure represented by formula (24)) (non-volatile content 65.0%) manufactured by Mitsubishi Gas Chemical Co., Ltd., as the filler (F), 41.3 parts by mass (25 parts by mass in terms of non-volatile content) of MEK (methyl ethyl ketone) solution (non-volatile content 60.5%) of Admatechs 3SE-CM1 (trade name, epoxy silane surface-treated slurry (fused) silica, average particle size: 300 nm) manufactured by Admatechs Co., Ltd.
  • Example 1 Using the obtained varnish, a resin sheet, a laminate for evaluation, and a laminate resin sheet for evaluation were obtained in the same manner as in Example 1.
  • Example 12 As the bismaleimide compound (A), 40 parts by mass of MIZ-001 (trade name, mass average molecular weight (Mw): 3000, containing a maleimide compound of formula (3), where a in formula (3) is a mixture of 1 to 6 (integer)) manufactured by Nippon Kayaku Co., Ltd., as well as 30.3 parts by mass (20 parts by mass in terms of non-volatile content) of ZXR-1889H (trade name, compound represented by formula (36)) (non-volatile content 66.0%) manufactured by Nippon Kayaku Co., Ltd.
  • MIZ-001 trade name, mass average molecular weight (Mw): 3000
  • a maleimide compound of formula (3) where a in formula (3) is a mixture of 1 to 6 (integer) manufactured by Nippon Kayaku Co., Ltd.
  • ZXR-1889H trade name, compound represented by formula (36)
  • the epoxy (meth)acrylate (B) 30.3 parts by mass (20 parts by mass in terms of non-volatile content) of ZXR-1807H (trade name, compound represented by formula (36)) (non-volatile content 66.0%) manufactured by Nippon Kayaku Co., Ltd. as the epoxy (meth)acrylate (B), and 30.3 parts by mass (20 parts by mass in terms of non-volatile content) of Irgacure (registered trademark) O manufactured by BASF Japan Ltd. as the photocuring initiator (C).
  • a varnish (resin composition) As a crosslinking agent were mixed, and 40 parts by mass of MEK was added to obtain a varnish (resin composition).
  • the mass ratio ((A)/(B)) of the bismaleimide compound (A) to the epoxy (meth)acrylate (B) was 1.
  • a resin sheet, a laminate for evaluation, and a laminate resin sheet for evaluation were obtained in the same manner as in Example 1.
  • Example 13 As the bismaleimide compound (A), 40 parts by mass of MIZ-001 (trade name, mass average molecular weight (Mw): 3000, containing a maleimide compound of formula (3), where a in formula (3) is a mixture of 1 to 6 (integer)) manufactured by Nippon Kayaku Co., Ltd., and 30.3 parts by mass of ZXR-1889H (trade name, compound represented by formula (36)) (non-volatile content 66.0%) manufactured by Nippon Kayaku Co., Ltd., as the epoxy (meth)acrylate (B), parts by mass (20 parts by mass in terms of non-volatile content), 30.3 parts by mass (20 parts by mass in terms of non-volatile content) of ZXR-1807H (trade name, compound represented by formula (36)) (non-volatile content 66.0%) manufactured by Nippon Kayaku Co., Ltd.
  • MIZ-001 trade name, mass average molecular weight (Mw): 3000
  • ZXR-1889H trade name, compound
  • the mass ratio ((A)/(B)) of the bismaleimide compound (A) to the epoxy (meth)acrylate (B) was 1.
  • a resin sheet, a laminate for evaluation, and a laminate resin sheet for evaluation were obtained in the same manner as in Example 1.
  • Example 14 As the bismaleimide compound (A), 40 parts by mass of MIZ-001 (trade name, mass average molecular weight (Mw): 3000, containing a maleimide compound of formula (3), where a in formula (3) is a mixture of 1 to 6 (integer)) manufactured by Nippon Kayaku Co., Ltd., and 30.3 parts by mass of ZXR-1889H (trade name, compound represented by formula (36)) (non-volatile content 66.0%) manufactured by Nippon Kayaku Co., Ltd., as the epoxy (meth)acrylate (B), parts by mass (20 parts by mass in terms of non-volatile content), 30.3 parts by mass (20 parts by mass in terms of non-volatile content) of ZXR-1807H (trade name, compound represented by formula (36)) (non-volatile content 66.0%) manufactured by Nippon Kayaku Co., Ltd.
  • MIZ-001 trade name, mass average molecular weight (Mw): 3000
  • ZXR-1889H trade name, compound
  • the maleimide compound (D) 16.3 parts by mass (10 parts by mass in terms of non-volatile content) of NE-X-9470S (trade name, compound represented by formula (6)) (non-volatile content 61.0%) manufactured by DIC Corporation, and as the resin or compound (E), 1 5.3 parts by mass (10 parts by mass in terms of non-volatile content) of the bismaleimide compound (A) and 82.6 parts by mass (50 parts by mass in terms of non-volatile content) of a MEK (methyl ethyl ketone) solution (60.5% non-volatile content) of Admatechs 3SE-CM1 (product name, epoxy silane surface-treated slurry (fused) silica, average particle size: 300 nm) as a
  • the mass ratio ((A)/(B)) of the bismaleimide compound (A) to the epoxy (meth)acrylate (B) was 1.
  • a resin sheet, a laminate for evaluation, and a laminate resin sheet for evaluation were obtained in the same manner as in Example 1.
  • Example 15 As the bismaleimide compound (A), 40 parts by mass of MIZ-001 (trade name, mass average molecular weight (Mw): 3000, containing a maleimide compound of formula (3), where a in formula (3) is a mixture of 1 to 6 (integer)) manufactured by Nippon Kayaku Co., Ltd., and 30.3 parts by mass of ZXR-1889H (trade name, compound represented by formula (36)) (non-volatile content 66.0%) manufactured by Nippon Kayaku Co., Ltd., as the epoxy (meth)acrylate (B), parts by mass (20 parts by mass in terms of non-volatile content), 30.3 parts by mass (20 parts by mass in terms of non-volatile content) of ZXR-1807H (trade name, compound represented by formula (36)) (non-volatile content 66.0%) manufactured by Nippon Kayaku Co., Ltd.
  • MIZ-001 trade name, mass average molecular weight (Mw): 3000, containing a maleimide compound of formula (3)
  • Irgacure registered trademark
  • OXE03 trade name, oxime esters manufactured by BASF Japan Ltd.
  • photocuring initiator (C) As the maleimide compound (D), 16.3 parts by mass (10 parts by mass in terms of non-volatile content) of NE-X-9470S (trade name, compound represented by formula (6)) (non-volatile content 61.0%) manufactured by DIC Corporation was used, and as the resin or compound (E), 15 parts by mass of OPE (registered trademark)-2St1200 (trade name, modified polyphenylene ether compound having a structure represented by formula (24)) (non-volatile content 65.0%) manufactured by Mitsubishi Gas Chemical Company, Inc.
  • OPE registered trademark
  • -2St1200 trade name, modified polypheny
  • Example 16 As the bismaleimide compound (A), 40 parts by mass of MIZ-001 (trade name, mass average molecular weight (Mw): 3000, containing a maleimide compound of formula (3), where a in formula (3) is a mixture of 1 to 6 (integer)) manufactured by Nippon Kayaku Co., Ltd., and as the epoxy (meth)acrylate (B), 30.3 parts by mass (20 parts in terms of nonvolatile content) of ZXR-1889H (trade name, compound represented by formula (36)) (nonvolatile content 66.0%) manufactured by Nippon Kayaku Co., Ltd.
  • Example 17 As the bismaleimide compound (A), 40 parts by mass of MIZ-001 (trade name, mass average molecular weight (Mw): 3000, containing a maleimide compound of formula (3), where a in formula (3) is a mixture of 1 to 6 (integer)) manufactured by Nippon Kayaku Co., Ltd., and as the epoxy (meth)acrylate (B), 30.3 parts by mass (20 parts by mass in terms of nonvolatile content) of ZXR-1889H (trade name, compound represented by formula (36)) (nonvolatile content 66.0%) manufactured by Nippon Kayaku Co., Ltd., and As the photopolymerization initiator (B), 30.3 parts by mass (20 parts by mass in terms of non-volatile content) of ZXR-1807H (trade name, compound represented by formula (36)) manufactured by Nippon Kayaku Co., Ltd.
  • MIZ-001 trade name, mass average molecular weight (Mw): 3000, containing a maleimide compound of formula (3), where
  • non-volatile content 66.0%) was used; as the photopolymerization initiator (C), 5.0 parts by mass of Irgacure (registered trademark) OXE03 (trade name, oxime esters) manufactured by BASF Japan Ltd. was used; and as the maleimide compound (D), NE-X-9470S (trade name, compound represented by formula (6)) (non-volatile content 61.
  • the photopolymerization initiator (C) 5.0 parts by mass of Irgacure (registered trademark) OXE03 (trade name, oxime esters) manufactured by BASF Japan Ltd. was used; and as the maleimide compound (D), NE-X-9470S (trade name, compound represented by formula (6)) (non-volatile content 61.
  • Admatechs 3SE-CM1 (trade name, epoxysilane surface-treated slurry (fused) silica, average particle size: 30 41.3 parts by mass (25 parts by mass calculated as nonvolatile content) of MEK (methyl ethyl ketone) solution (nonvolatile content 60.5%) of 1.0 nm was mixed with 4.0 parts by mass of Taiku (registered trademark) (triallyl isocyanurate) from Mitsubishi Chemical Corporation as a crosslinking agent, and 0.50 parts by mass of Curesol (registered trademark) 2P4MZ (product name, 2-phenyl-4-methylimidazole) from Shikoku Chemical Industry Co., Ltd.
  • Curesol registered trademark
  • 2P4MZ product name, 2-phenyl-4-methylimidazole
  • Example 18 As the bismaleimide compound (A), 40 parts by mass of MIZ-001 (trade name, mass average molecular weight (Mw): 3000, containing a maleimide compound of formula (3), where a in formula (3) is a mixture of 1 to 6 (integer)) manufactured by Nippon Kayaku Co., Ltd., and as the epoxy (meth)acrylate (B), 30.3 parts by mass (20 parts by mass in terms of nonvolatile content) of ZXR-1889H (trade name, compound represented by formula (36)) (nonvolatile content 66.0%) manufactured by Nippon Kayaku Co., Ltd., and As the photopolymerization initiator (B), 30.3 parts by mass (20 parts by mass in terms of non-volatile content) of ZXR-1807H (trade name, compound represented by formula (36)) manufactured by Nippon Kayaku Co., Ltd.
  • MIZ-001 trade name, mass average molecular weight (Mw): 3000, containing a maleimide compound of formula (3), where
  • non-volatile content 66.0%) was used; as the photopolymerization initiator (C), 5.0 parts by mass of Irgacure (registered trademark) OXE03 (trade name, oxime esters) manufactured by BASF Japan Ltd. was used; and as the maleimide compound (D), NE-X-9470S (trade name, compound represented by formula (6)) (non-volatile content 61.
  • the photopolymerization initiator (C) 5.0 parts by mass of Irgacure (registered trademark) OXE03 (trade name, oxime esters) manufactured by BASF Japan Ltd. was used; and as the maleimide compound (D), NE-X-9470S (trade name, compound represented by formula (6)) (non-volatile content 61.
  • Admatechs 3SE-CM1 (trade name, epoxysilane surface-treated slurry (fused) silica, average particle size: 30 41.3 parts by mass (25 parts by mass calculated as nonvolatile content) of MEK (methyl ethyl ketone) solution (nonvolatile content 60.5%) of 1.0 nm was mixed with 5.0 parts by mass of Taiku (registered trademark) (triallyl isocyanurate) from Mitsubishi Chemical Corporation as a crosslinking agent, and 0.50 parts by mass of Curesol (registered trademark) 2P4MZ (product name, 2-phenyl-4-methylimidazole) from Shikoku Chemical Industry Co., Ltd.
  • Curesol registered trademark
  • 2P4MZ product name, 2-phenyl-4-methylimidazole
  • Example 19 As the bismaleimide compound (A), 40 parts by mass of MIZ-001 (trade name, mass average molecular weight (Mw): 3000, containing a maleimide compound of formula (3), where a in formula (3) is a mixture of 1 to 6 (integer)) manufactured by Nippon Kayaku Co., Ltd., and as the epoxy (meth)acrylate (B), 30.3 parts by mass (20 parts by mass in terms of nonvolatile content) of ZXR-1889H (trade name, compound represented by formula (36)) (nonvolatile content 66.0%) manufactured by Nippon Kayaku Co., Ltd., and as the epoxy (meth)acrylate (B), 30.3 parts by mass (20 parts by mass in terms of non-volatile content) of ZXR-1807H (trade name, compound represented by formula (36)) (non-volatile content 66.0%) manufactured by Nippon Kayaku Co., Ltd., 5.0 parts by mass of Irgacure (registered trademark) OXE01 (trade name
  • the mass ratio ((A)/(B)) of the bismaleimide compound (A) to the epoxy (meth)acrylate (B) was 1.
  • a resin sheet, a laminate for evaluation, and a laminate resin sheet for evaluation were obtained in the same manner as in Example 1.
  • Example 20 As the bismaleimide compound (A), 40 parts by mass of MIZ-001 (trade name, mass average molecular weight (Mw): 3000, containing a maleimide compound of formula (3), where a in formula (3) is a mixture of 1 to 6 (integer)) manufactured by Nippon Kayaku Co., Ltd., and as the epoxy (meth)acrylate (B), 30.3 parts by mass (20 parts by mass in terms of nonvolatile content) of ZXR-1889H (trade name, compound represented by formula (36)) (nonvolatile content 66.0%) manufactured by Nippon Kayaku Co., Ltd. were used.
  • MIZ-001 trade name, mass average molecular weight (Mw): 3000
  • MIZ-001 mass average molecular weight (Mw): 3000
  • a maleimide compound of formula (3) where a in formula (3) is a mixture of 1 to 6 (integer) manufactured by Nippon Kayaku Co., Ltd.
  • epoxy (meth)acrylate (B) 30.3 parts
  • ZXR-1807H (trade name, compound represented by formula (36)) manufactured by IGM Resins (non-volatile content 66.0%
  • Irgacure registered trademark
  • OXE01 trade name, 1,2-octanedione, 1-[4-(phenylthio)phenyl-, 2-(O-benzoyloxime)]
  • maleimide compound (D) 16.3 parts by mass (10 parts by mass in terms of non-volatile content) of NE-X-9470S (trade name, compound represented by formula (6)) (non-volatile content 61.0%) manufactured by DIC Corporation was used, as the resin or compound (E), 15.3 parts by mass (10 parts by mass) of OPE (trade name)-2St1200 (trade name, modified polyphenylene ether compound having a structure represented by formula (24)) (non-volatile content 65.0%) manufactured by Mitsubishi Gas Chemical Co., Ltd.
  • OPE trade name
  • -2St1200 trade name, modified polyphenylene ether compound having a structure represented by formula (24)
  • the mass ratio ((A)/(B)) of the bismaleimide compound (A) to the epoxy (meth)acrylate (B) was 1.
  • a resin sheet, a laminate for evaluation, and a laminate resin sheet for evaluation were obtained in the same manner as in Example 1.
  • Comparative Example 1 As the bismaleimide compound (A), 60 parts by mass of MIZ-001 (trade name, mass average molecular weight (Mw): 3000, containing a maleimide compound of formula (3), where a in formula (3) is a mixture of 1 to 6 (integer)) manufactured by Nippon Kayaku Co., Ltd., 5.0 parts by mass of Irgacure (registered trademark) OXE03 (trade name, oxime esters) manufactured by BASF Japan Ltd.
  • MIZ-001 trade name, mass average molecular weight (Mw): 3000
  • a maleimide compound of formula (3) where a in formula (3) is a mixture of 1 to 6 (integer) manufactured by Nippon Kayaku Co., Ltd.
  • Irgacure registered trademark
  • OXE03 trade name, oxime esters
  • the photocuring initiator (C) 16.3 parts by mass (10 parts by mass in terms of nonvolatile content) of NE-X-9470S (trade name, compound represented by formula (6)) (nonvolatile content 61.0%) manufactured by DIC Corporation as the maleimide compound (D), and 10 parts by mass of OPE (registered trademark)-2St1 manufactured by Mitsubishi Gas Chemical Co., Ltd. as the resin or compound (E).
  • Example 1 Using the obtained varnish, a resin sheet, a laminate for evaluation, and a laminate resin sheet for evaluation were obtained in the same manner as in Example 1.
  • a varnish (resin composition) was obtained by mixing 15.3 parts by mass (10 parts by mass in terms of non-volatile content) of a modified polyphenylene ether compound having a structure represented by formula (24) (product name, non-volatile content 65.0%), 41.3 parts by mass (25 parts by mass in terms of non-volatile content) of an MEK (methyl ethyl ketone) solution (non-volatile content 60.5%) of Admatechs 3SE-CM1 (product name, epoxy silane surface-treated slurry (fused) silica, average particle size: 300 nm) manufactured by Admatechs Co., Ltd.
  • Example 1 Using the obtained varnish, a resin sheet, a laminate for evaluation, and a laminate resin sheet for evaluation were obtained in the same manner as in Example 1.
  • Photocurability 200-600nm
  • a photo DSC (TA Instruments Japan, Ltd.) equipped with a light source capable of irradiating active energy rays with wavelengths of 200 to 600 nm (Omnicure (registered trademark) S2000 (product name) manufactured by U-VIX Corporation) was used.
  • the resin sheet was irradiated with active energy rays having a wavelength of 200 to 600 nm at an illuminance of 30 mW for an exposure time of 3.5 minutes using a DSC-2500 (product name) manufactured by Epson Corporation.
  • a graph was obtained with the vertical axis representing heat flow (mW).
  • a horizontal line was drawn from the end point of the graph, and the peak area was taken as the enthalpy (J/g).
  • the curability was evaluated according to the following criteria. "AA”: Enthalpy was 1 (J/g) or more. "CC”: The enthalpy was less than 1 (J/g). Incidentally, an enthalpy of 1 (J/g) or more means that curing of the resin proceeds sufficiently by exposure to light of a predetermined wavelength.
  • the support was peeled off from the cured product, and the cured product after peeling was shaken in a 1% aqueous sodium carbonate solution at 33 ° C. for 180 seconds. Thereafter, the via pattern was observed using an optical microscope to evaluate the alkaline developability according to the following criteria.
  • AA After development, a via of ⁇ 30 ⁇ m or less can be formed.
  • CC After development, a via of ⁇ 30 ⁇ m or less cannot be formed.
  • Dielectric constant (Dk) and dielectric loss tangent (Df) Using a light source (MA-20 (product name) manufactured by Mikasa Co., Ltd.) capable of irradiating active energy rays having a wavelength of 200 to 600 nm, and an optical filter (manufactured by Mikasa Co., Ltd., extraction wavelength 346 nm to 384 nm), active energy rays having a wavelength of 365 nm were irradiated from above the support (PET film) of the obtained laminated resin sheet for evaluation at an illuminance of 5 mW and an exposure dose of 50 mJ/ cm2 to obtain a cured product.
  • a light source MA-20 (product name) manufactured by Mikasa Co., Ltd.
  • an optical filter manufactured by Mikasa Co., Ltd., extraction wavelength 346 nm to 384 nm
  • the dielectric constant (Dk) and dielectric loss tangent (Df) at 10 GHz of this evaluation sample were measured using a network analyzer (Agilent (registered trademark) 8722ES (product name), manufactured by Agilent Technologies, Inc.)
  • the measurement of the dielectric constant (Dk) and dielectric loss tangent (Df) was performed in an environment of a temperature of 23° C. ⁇ 1° C. and a humidity of 50% RH ⁇ 5% RH.
  • the dielectric constant (Dk) and the dielectric loss tangent (Df) were evaluated according to the following criteria.
  • ⁇ Dielectric constant (Dk) "AA”: The dielectric constant was 2.6 or less. "BB”: The relative dielectric constant was greater than 2.6 and less than or equal to 2.7. "CC”: The dielectric constant exceeded 2.7. If the dielectric constant is 2.7 or less, a cured product (insulating layer) having a low dielectric constant tends to be obtained.
  • ⁇ Dielectric tangent (Df) "AA”: The dielectric tangent was 0.007 or less. "BB”: The dielectric tangent was greater than 0.007 and was 0.008 or less. "CC”: The dielectric tangent exceeded 0.008. If the dielectric loss tangent is 0.008 or less, a cured product (insulating layer) having a low dielectric loss tangent tends to be obtained.
  • the composition when exposed to various types of active energy rays, particularly active energy rays having a wavelength of 365 nm (i-line), the composition is well sensitized and photocured. Furthermore, according to this embodiment, a cured product having excellent alkaline developability is obtained. Furthermore, according to this embodiment, a cured product having a low relative dielectric constant and dielectric dissipation factor is obtained. Therefore, by using the resin composition of this embodiment, a high-definition insulating layer having a low relative dielectric constant and dielectric dissipation factor, a high-density printed wiring board having a high-definition resist pattern, and a semiconductor device can be obtained.
  • the resin composition of this embodiment has excellent photocurability against various active energy rays, particularly 365 nm (i-line) in the exposure process when producing a multilayer printed wiring board, and can impart excellent alkaline developability in the development process.
  • a cured product with a low dielectric constant and dielectric tangent can be obtained. Therefore, it is industrially useful and can be used, for example, for photosensitive films, photosensitive films with supports, prepregs, resin sheets, circuit boards (for laminates, multilayer printed wiring boards, etc.), solder resists, underfill materials, die bonding materials, semiconductor encapsulants, hole filling resins, and component embedding resins.
  • the resin composition can obtain a cured product with a lower dielectric constant and dielectric tangent, and has excellent photocurability and alkaline developability, so it can be suitably used as an insulating layer for multilayer printed wiring boards or as a solder resist.

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  • Chemical & Material Sciences (AREA)
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  • Chemical Kinetics & Catalysis (AREA)
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  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
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Abstract

Cette composition de résine contient : un composé bismaléimide (A) qui contient une unité constitutive représentée par la formule (1) et des groupes maléimide aux deux extrémités de la chaîne moléculaire; un (méth)acrylate époxy de dicyclopentadiène phénol (B) qui contient un ou plusieurs groupes carboxyle; et un initiateur de photopolymérisation (C).
PCT/JP2024/002791 2023-01-30 2024-01-30 Composition de résine, feuille de résine, carte de circuit imprimé multicouche et dispositif à semi-conducteur Ceased WO2024162319A1 (fr)

Priority Applications (3)

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CN202480009701.3A CN120603869A (zh) 2023-01-30 2024-01-30 树脂组合物、树脂片、多层印刷电路板和半导体装置
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WO2020262579A1 (fr) * 2019-06-28 2020-12-30 三菱瓦斯化学株式会社 Composition de résine, couche de résine, circuit imprimé multicouche et dispositif à semi-conducteur
JP2022099579A (ja) * 2020-12-23 2022-07-05 三菱瓦斯化学株式会社 多層プリント配線板の絶縁層用樹脂組成物、樹脂シート、多層プリント配線板、半導体装置、及び硬化物
WO2022264994A1 (fr) * 2021-06-15 2022-12-22 三菱瓦斯化学株式会社 Composition de résine, feuille de résine, carte de circuit imprimé multicouche, et dispositif à semi-conducteurs

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WO2020262579A1 (fr) * 2019-06-28 2020-12-30 三菱瓦斯化学株式会社 Composition de résine, couche de résine, circuit imprimé multicouche et dispositif à semi-conducteur
JP2022099579A (ja) * 2020-12-23 2022-07-05 三菱瓦斯化学株式会社 多層プリント配線板の絶縁層用樹脂組成物、樹脂シート、多層プリント配線板、半導体装置、及び硬化物
WO2022264994A1 (fr) * 2021-06-15 2022-12-22 三菱瓦斯化学株式会社 Composition de résine, feuille de résine, carte de circuit imprimé multicouche, et dispositif à semi-conducteurs

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