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WO2025164514A1 - Initiateur de polymérisation latente thermique, composition de résine le contenant, adhésif, matériau d'étanchéité, film, produit durci de ceux-ci, procédé de production de produit durci, et dispositif à semi-conducteur ou composant électronique - Google Patents

Initiateur de polymérisation latente thermique, composition de résine le contenant, adhésif, matériau d'étanchéité, film, produit durci de ceux-ci, procédé de production de produit durci, et dispositif à semi-conducteur ou composant électronique

Info

Publication number
WO2025164514A1
WO2025164514A1 PCT/JP2025/002136 JP2025002136W WO2025164514A1 WO 2025164514 A1 WO2025164514 A1 WO 2025164514A1 JP 2025002136 W JP2025002136 W JP 2025002136W WO 2025164514 A1 WO2025164514 A1 WO 2025164514A1
Authority
WO
WIPO (PCT)
Prior art keywords
resin composition
thermal
polymerization initiator
acrylate
meth
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
PCT/JP2025/002136
Other languages
English (en)
Japanese (ja)
Inventor
修 下村
一希 岩谷
理恵子 永田
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Namics Corp
Original Assignee
Namics Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Namics Corp filed Critical Namics Corp
Publication of WO2025164514A1 publication Critical patent/WO2025164514A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F4/00—Polymerisation catalysts
    • C08F4/02—Carriers therefor
    • 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
    • C08F4/00—Polymerisation catalysts
    • C08F4/04—Azo-compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/02—Non-macromolecular additives
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J201/00—Adhesives based on unspecified macromolecular compounds

Definitions

  • the present invention relates to a thermal latent polymerization initiator and its production method, a resin composition containing the thermal latent polymerization initiator, an adhesive or sealant containing the same, a film, a cured product thereof, a method for producing the cured product, and a semiconductor device or electronic component containing the cured product.
  • Radical polymerization is the most common polymerization method, using highly active neutral radical species as propagating species to enable the polymerization of a variety of vinyl compounds, and is widely used industrially.
  • resin compositions containing radically polymerizable resins such as acrylates and radical polymerization initiators have been developed and are widely used as adhesives, sealants, coatings, paints, molding materials, and more.
  • Heat-induced radical polymerization is usually initiated using a radical generator such as an azo compound or organic peroxide as a polymerization initiator.
  • Organic peroxides have an -O-O- bond that is decomposed by heat into oxygen radicals.
  • radical generators are highly reactive to light and/or heat, and there is a risk of explosion if handled incorrectly, so they must be stored in a cool, dark place.
  • a radical generator when included in a resin composition as a polymerization initiator, its high reactivity causes it to gradually deactivate during storage of the resin composition, resulting in problems such as the polymerization reaction not proceeding when the composition is used, or an unintended polymerization reaction proceeding during storage, causing the resin composition to thicken.
  • a microencapsulated organic peroxide can be used as a latent catalyst to improve the storage stability of organic peroxides in resin compositions (see, for example, Patent Documents 1 and 2).
  • resin compositions containing radical initiators with high storage stability sometimes require high-temperature curing reactions.
  • the present invention aims to provide a novel latent polymerization initiator that has excellent storage stability and enables thermosetting of a resin composition at low temperatures, as well as to provide a resin composition, adhesive, or sealant that has excellent storage stability and enables thermosetting at low temperatures.
  • aspects of the present invention include the following thermal latent polymerization initiator and method for producing the same, a resin composition containing the thermal latent polymerization initiator, an adhesive or sealant containing the same, a film, a cured product thereof, a method for producing the cured product, and a semiconductor device or electronic component containing the cured product.
  • a method for producing a thermal latent polymerization initiator comprising mixing a thermal radical initiator and an inorganic ion exchanger in the presence of a medium at a temperature lower than the 10-hour half-life temperature of the thermal radical initiator.
  • One aspect of the present invention provides a novel thermal latent polymerization initiator that has excellent storage stability and enables thermal curing of a resin composition at low temperatures, and a method for producing the same.
  • Another aspect of the present invention provides a resin composition that has excellent storage stability and enables thermal curing at low temperatures, an adhesive or sealant containing the same, a film, a cured product thereof, a method for producing the cured product, and a semiconductor device or electronic component containing the cured product.
  • the term "resin,” which normally refers to a polymer (especially a synthetic polymer), may be used to refer to the components that make up a resin composition before curing, even if the component is not a polymer, such as a prepolymer compound before curing.
  • the thermal latent polymerization initiator is a thermal latent polymerization initiator in which a thermal radical initiator is supported on inorganic ion exchanger particles. According to this embodiment, a novel thermal latent polymerization initiator having excellent storage stability and capable of thermally curing a resin composition at low temperatures can be provided.
  • An inorganic ion exchanger is a substance whose skeleton is composed of inorganic atoms other than carbon atoms (e.g., zirconium, antimony, bismuth, magnesium, titanium, hafnium, germanium, tin, lead, aluminum, etc.) and has ion exchange capacity.
  • Inorganic ion exchangers have ion exchange sites that are negatively or positively charged, allowing them to exchange captured ions for other ions.
  • a thermal radical initiator can be supported on this inorganic ion exchanger, and (2) a substance in which a thermal radical initiator is supported on an inorganic ion exchanger has improved storage stability and enables low-temperature thermal curing of resin compositions without reducing the activity of the thermal radical initiator itself.
  • the mechanism behind this is thought to be, but is not limited to, that the ionized thermal radical initiator is supported and stabilized on the ion exchange sites of the inorganic ion exchanger, imparting latency, and that the thermal radical initiator is desorbed from the inorganic ion exchanger and activated under the thermal curing conditions of the resin composition.
  • the thermal latent polymerization initiator of this embodiment is a substance in which a thermal radical initiator is supported on inorganic ion exchanger particles.
  • the thermal radical initiator is a substance that generates radicals as active species by heat and promotes polymerization of a radically polymerizable compound.
  • the thermal radical initiator is preferably an azo radical initiator.
  • the azo radical initiator is preferably an azo compound having a basic group or an azo compound having an acidic group.
  • the type of inorganic ion exchanger that serves as the host is selected depending on whether the azo compound has a basic group or an acidic group.
  • an azo compound having a basic group refers to a compound having an azo group in its molecular structure and a group capable of accepting a proton (H + ).
  • the azo compound having a basic group is cationized by accepting a proton (H + ) and is supported at its ion exchange site on the inorganic cation exchanger described below.
  • Examples of azo compounds having a basic group include compounds having a heteroatom other than the azo group in their molecular structure.
  • the heteroatom other than the azo group may be contained in the compound in the form of a functional group containing a heteroatom.
  • Examples of such functional groups containing a heteroatom include, but are not limited to, a hydroxyl group, a carboxyl group, an ether group, an ester group, a phosphate ester group, an amino group, an imino group, a nitrile group, a thiol group, a sulfide group, a sulfoxide group, a disulfide group, a thioester group, and an amide group.
  • azo compounds having a basic group include 2,2'-azobis(N-cyclohexyl-2-methylpropionamide), 2,2'-azobis[N-(2-methylpropyl)-2-methylpropionamide], 2,2'-azobis(N-butyl-2-methylpropionamide) (for example, product name: VAm-110, Fujifilm Wako Pure Chemical Industries, Ltd.), 2,2'-azobis[N-(2-methylethyl)-2-methylpropionamide], and 2,2'-azobis(N-hexyl-2-methylpropionamide).
  • 2,2'-azobis(N-cyclohexyl-2-methylpropionamide) 2,2'-azobis[N-(2-methylpropyl)-2-methylpropionamide]
  • 2,2'-azobis(N-butyl-2-methylpropionamide) for example, product name: VAm-110, Fujifilm Wako Pure Chemical Industries, Ltd.
  • an azo compound having an acidic group refers to a compound having an azo group in its molecular structure and a group capable of donating a proton (H + ).
  • the azo compound having an acidic group is anionized by donating a proton (H + ) and is supported on the ion exchange site of the inorganic anion exchanger described below.
  • Examples of azo compounds having an acidic group include compounds having a heteroatom other than the azo group in their molecular structure.
  • the heteroatom other than the azo group may be contained in the compound in the form of a functional group containing a heteroatom, and examples of such functional groups containing a heteroatom include, but are not limited to, a hydroxyl group, a carboxyl group, a thiol group, a sulfo group, a phosphate group, and the like.
  • azo compounds having an acidic group include, but are not limited to, 4,4'-azobis(4-cyanovaleric acid) (e.g., product name: V-501, Fujifilm Wako Pure Chemical Industries, Ltd.), 2,2'-azobis[N-(2-carboxyethyl)-2-methylpropionamidine]tetrahydrate (e.g., product name: VA-057, Fujifilm Wako Pure Chemical Industries, Ltd.), etc.
  • 4,4'-azobis(4-cyanovaleric acid) e.g., product name: V-501, Fujifilm Wako Pure Chemical Industries, Ltd.
  • 2,2'-azobis[N-(2-carboxyethyl)-2-methylpropionamidine]tetrahydrate e.g., product name: VA-057, Fujifilm Wako Pure Chemical Industries, Ltd.
  • These azo compounds having an acidic group may be used alone or in combination of two or more.
  • the 10-hour half-life temperature (T10) of the thermal radical initiator is preferably 35 to 120°C, more preferably 40 to 115°C, and even more preferably 45 to 110°C.
  • the thermal latent polymerization initiator of this embodiment is a substance in which a thermal radical initiator is supported on inorganic ion exchanger particles.
  • the inorganic ion exchanger particles refer to particulate inorganic ion exchangers.
  • the inorganic ion exchanger refers to a substance whose skeleton is composed of inorganic atoms other than carbon atoms (e.g., zirconium, antimony, bismuth, magnesium, titanium, hafnium, germanium, tin, lead, aluminum, etc.) and has ion exchange capacity.
  • the inorganic ion exchanger has negatively or positively charged ion exchange sites and can exchange captured ions for other ions.
  • inorganic ion exchangers include clay minerals such as silicates, such as montmorillonite, vermiculite, beidellite, kaolinite, dickite, nacrite, halloysite, smectite, allophane, heractite, sepiolite, bentonite, pyrophyllite, muscovite, margarite, antigorite, chrysotile, talc, phlogopite, and xanthophyllite; hydrous sodium silicates such as kanemite, makatite, ailerite, magadiite, and Kenyaite; calcium silicates such as tobermorite;
  • inorganic ion exchanger particles include, but are not limited to, tetravalent metal phosphates such as zirconium phosphate and titanium phosphate; titanates such as potassium titanate, barium titanate, strontium titanate, calcium titanate, magnesium titanate,
  • an inorganic ion exchanger having negatively charged ion exchange sites and cation exchange capacity is referred to as an inorganic cation exchanger.
  • an inorganic ion exchanger having positively charged ion exchange sites and anion exchange capacity is referred to as an inorganic anion exchanger.
  • the inorganic cation exchanger can support an azo compound having a basic group as a thermal radical initiator at its ion exchange sites.
  • the inorganic anion exchanger can support an azo compound having an acidic group as a thermal radical initiator at its ion exchange sites.
  • the inorganic ion exchanger is an inorganic cation exchanger.
  • the inorganic cation exchanger is preferably a phosphate-based inorganic cation exchanger, which is a phosphate of a tetravalent metal such as zirconium phosphate or titanium phosphate, a clay mineral such as smectite, a hydrous sodium silicate such as kanemite or magadiite, a niobate, or a titanate, and more preferably a phosphate-based inorganic cation exchanger such as zirconium phosphate or titanium phosphate.
  • the phosphate-based inorganic cation exchanger is zirconium phosphate.
  • the inorganic ion exchanger is an inorganic anion exchanger. In one embodiment, the inorganic anion exchanger is preferably hydrotalcite.
  • zirconium phosphates come in a variety of compositions (e.g., P/Zr molar ratios of 2.0 or more, 2.0, 1.5, 1.0, or less than 1.0) and structures (e.g., amorphous, two-dimensional layered structure, and three-dimensional network structure) (Katsuhiko, ITOHO, Yashushi NAKAJIMA, Journal of Ion Exchange, Vol. 4, No. 3 (1994)).
  • compositions e.g., P/Zr molar ratios of 2.0 or more, 2.0, 1.5, 1.0, or less than 1.0
  • structures e.g., amorphous, two-dimensional layered structure, and three-dimensional network structure
  • zirconium phosphates with either an amorphous or two-dimensional layered structure can be used.
  • the inorganic ion exchanger particles may have an average particle size of 1 nm to 100 ⁇ m. In one embodiment, the inorganic ion exchanger particles have an average particle size of, for example, 0.1 to 100 ⁇ m, for example, 0.5 to 50 ⁇ m, for example, 1 to 10 ⁇ m. In one embodiment, the inorganic ion exchanger particles have an average primary particle size of, for example, 1 nm to 500 nm, for example, 5 nm to 450 nm, for example, 10 nm to 400 nm.
  • a resin composition containing a thermal latent polymerization initiator obtained using inorganic ion exchanger particles having such a very small average particle size can penetrate narrow gaps and can be used for bonding or sealing narrow gaps.
  • inorganic ion exchanger particles having different average particle sizes may be used in combination.
  • the average particle size is the particle size at 50% of the cumulative value in the particle size distribution on a volume basis measured by laser diffraction/scattering.
  • the average particle size can be determined as the average value when the particle diameters (long axis length of the plate surface) of 20 random particles are measured using a transmission electron microscope (TEM), or the average value when the particle diameters (long axis length of the plate surface) of 20 random particles are measured using a scanning electron microscope (SEM) (magnification 5000x).
  • the average particle size is measured using a scanning electron microscope (SEM) (magnification 5000x) rather than a transmission electron microscope (TEM).
  • SEM scanning electron microscope
  • TEM transmission electron microscope
  • the shape of the inorganic ion exchanger particles is not particularly limited and may be spherical, flaky, needle-like, irregular, etc.
  • the method for producing the thermal latent polymerization initiator of this embodiment is not particularly limited, and may be, for example, a method comprising mixing a thermal radical initiator and an inorganic ion exchanger in the presence of a medium at a temperature lower than the 10-hour half-life temperature of the thermal radical initiator. By mixing at a temperature lower than the 10-hour half-life temperature of the thermal radical initiator, unintended decomposition of the thermal radical initiator can be suppressed.
  • the method for producing the thermal latent polymerization initiator is one embodiment of the present invention.
  • the medium may be any liquid medium that can dissolve and/or be miscible with the thermal radical initiator, and examples thereof include water; alcohols such as methanol, ethanol, propanol, and butanol; esters such as ethyl acetate and methyl acetate; ketones such as acetone and 2-butanone; ethers such as diethyl ether, dimethyl ether, diisopropyl ether, and tetrahydrofuran; amides such as dimethylformamide and dimethylacetamide; alkanes such as hexane and heptane; aromatic hydrocarbons such as benzene and toluene; dimethyl sulfoxide, N-methylpyrrolidone, acetonitrile, chloroform, and dichloromethane; and mixtures of these liquid media.
  • the mixing temperature is lower than the 10-hour half-life temperature of the thermal radical initiator, preferably a temperature that is 10°C or more lower than the 10-hour half-life temperature of the thermal radical initiator, and more preferably a temperature that is 20°C or more lower than the 10-hour half-life temperature of the thermal radical initiator.
  • the mixing can be carried out by stirring for, for example, 30 minutes to 48 hours. After the reaction is complete, the resulting mixture is separated from the liquid medium and washed with an appropriate washing medium to obtain a thermal latent polymerization initiator in which the thermal radical initiator is supported on inorganic ion exchanger particles.
  • the washing medium may be the same as the liquid medium used in the mixing, or a different liquid medium may be used.
  • the thermal latent polymerization initiator is a gel-like substance containing the liquid medium, and the liquid medium can be removed from the thermal latent polymerization initiator by drying as necessary.
  • the thermal latent polymerization initiator can be used either in a state containing the liquid medium or in a state from which the liquid medium has been removed.
  • the thermal latent polymerization initiator of this embodiment is believed to be able to support a thermal radical initiator depending on the spatial volume or surface area of the ion exchange sites of the inorganic ion exchanger.
  • the thermal radical initiator can be supported in an amount of 1 to 50 mass%, preferably 10 to 50 mass%, relative to the total mass of the thermal latent polymerization initiator.
  • the thermal radical initiator is an azo-based radical initiator
  • the amount of thermal radical initiator (mass%) in the thermal latent polymerization initiator can be calculated by determining the mass of nitrogen atoms contained in the thermal latent polymerization initiator using an elemental analyzer.
  • the content of thermal radical initiator in the thermal latent polymerization initiator (mass fraction of nitrogen atoms (mass%) from elemental analysis results / (atomic weight of nitrogen [g/mol] ⁇ number of nitrogen atoms [number] per molecule of thermal radical initiator)) ⁇ molecular weight of the thermal radical initiator [g/mol].
  • the present invention provides a resin composition that has excellent storage stability and can be thermally cured at low temperatures, comprising (A) a radically polymerizable compound and (B) the thermal latent polymerization initiator of the above-described embodiment.
  • the resin composition of this embodiment contains (A) a radically polymerizable compound (hereinafter also referred to as "component (A)").
  • a radically polymerizable compound hereinafter also referred to as "component (A)”
  • the radically polymerizable compound include, but are not limited to, compounds having an unsaturated double bond such as (meth)acrylate compounds, cyanoacrylate compounds, maleimide compounds, and methylene malonates (2-methylene-1,3-dicarbonyl compounds and derivatives thereof), and mixtures of compounds having an unsaturated double bond and thiol compounds (mixtures capable of undergoing an ene-thiol reaction).
  • the (meth)acrylate compound refers to a compound having at least one (meth)acryloyl group in the molecule, and examples thereof include monofunctional (meth)acrylate compounds having one (meth)acryloyl group and polyfunctional (meth)acrylate compounds having two or more (meth)acryloyl groups.
  • the term "(meth)acryloyl group” includes both methacryloyl groups and acryloyl groups.
  • the term "(meth)acrylate compound” includes both acrylate compounds and methacrylate compounds.
  • Examples of the monofunctional (meth)acrylate compound include: -ethyl (meth)acrylate, trifluoroethyl (meth)acrylate, diethylaminoethyl (meth)acrylate, dimethylaminoethyl (meth)acrylate, glycidyl (meth)acrylate, n-butyl (meth)acrylate, isobutyl (meth)acrylate, tert-butyl (meth)acrylate, isoamyl (meth)acrylate, cyclohexyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, isodecyl (meth)acrylate, isobornyl (meth)acrylate, stearyl (meth)acrylate, lauryl (meth)acrylate, phenoxyethyl (meth)acrylate, benzyl (meth)acrylate, tetrahydrofurfuryl (meth)
  • polyfunctional (meth)acrylate compounds include diacrylate and/or dimethacrylate of tris(2-hydroxyethyl)isocyanurate; tris(2-hydroxyethyl)isocyanurate triacrylate and/or trimethacrylate; trimethylolpropane triacrylate and/or trimethacrylate, or oligomers thereof; pentaerythritol triacrylate and/or trimethacrylate, or oligomers thereof; polyacrylate and/or polymethacrylate of dipentaerythritol; tris(acryloxyethyl)isocyanurate; caprolactone-modified tris(acryloxyethyl)isocyanurate; caprolactone-modified tris(methacryloxyethyl)isocyanurate; polyacrylate and/or polymethacrylate of alkyl-modified dipentaerythritol; caprolactone-modified
  • any one of the above-mentioned (meth)acrylate compounds may be used alone, or two or more of them may be used in combination.
  • Examples of commercially available (meth)acrylate compounds include, but are not limited to, polyester acrylate (product name: EBECRYL810) manufactured by Daicel-Allnex Corporation, ditrimethylolpropane tetraacrylate (product name: EBECRYL140) manufactured by Daicel-Allnex Corporation, polyester acrylate (product name: M7100) manufactured by Toagosei Co., Ltd., dimethylol-tricyclodecane diacrylate (product name: Light Acrylate DCP-A) manufactured by Kyoeisha Chemical Co., Ltd., and neopentyl glycol-modified trimethylolpropane diacrylate (product name: Kayarad R-604) manufactured by Nippon Kayaku Co., Ltd.
  • the cyanoacrylate compound can be a known compound represented by the formula H 2 C ⁇ C(CN)—COOR.
  • R is an ester residue such as an alkyl group, cycloalkyl group, alkenyl group, cycloalkenyl group, alkynyl group, or aryl group.
  • the number of carbon atoms in the ester residue is not particularly limited, but typically, one having 1 to 8 carbon atoms can be used.
  • Ester residues consisting of substituted hydrocarbon groups such as alkoxyalkyl groups and trialkylsilylalkyl groups can also be used.
  • cyanoacrylate compounds include, but are not limited to, alkyl and cycloalkyl cyanoacrylates such as methyl cyanoacrylate, ethyl cyanoacrylate, propyl cyanoacrylate, butyl cyanoacrylate, and cyclohexyl cyanoacrylate; alkenyl and cycloalkenyl cyanoacrylates such as allyl cyanoacrylate, methallyl cyanoacrylate, and cyclohexenyl cyanoacrylate; alkynyl cyanoacrylates such as propangyl cyanoacrylate; aryl cyanoacrylates such as phenyl cyanoacrylate and toluyl cyanoacrylate; heteroatom-containing methoxyethyl cyanoacrylate, ethoxyethyl cyanoacrylate, and furfuryl cyanoacrylate; silicon-containing trimethylsilylmethyl cyanoacrylate, trimethylsilylethyl
  • maleimide compounds include N,N'-(4,4'-diphenylmethane) bismaleimide, bisphenol A diphenyl ether bismaleimide, 3,3'-dimethyl-5,5'-diethyl-4,4'-diphenylmethane bismaleimide, 4-methyl-1,3-phenylene bismaleimide, 1,6'-bismaleimide-(2,2,4-trimethyl)hexane, bis-(3-ethyl-5-methyl-4-maleimidophenyl)methane, and m-phenylene bis Examples include, but are not limited to, maleimide (N,N'-1,3-phenylene bismaleimide), 1,6-bismaleimidehexane, 1,2-bismaleimideethane (N,N'-ethylene dimaleimide), N,N'-(1,2-phenylene) bismaleimide, N,N'-1,4-phenylene dimaleimide, N,N'-(sulfonyld
  • the maleimide compound is preferably a maleimide compound having a hydrocarbon group derived from a dimer acid.
  • a maleimide compound having a hydrocarbon group derived from a dimer acid are described, for example, in JP 2015-193725 A.
  • Commercially available maleimide compounds having a hydrocarbon group derived from a dimer acid include, but are not limited to, products named "BMI-689,” “BMI-1500,” and “BMI-1700,” which are liquid at 25°C, and “BMI-3000,” which is solid at 25°C (all manufactured by Designer Molecules Inc.). These compounds may be used alone or in combination of two or more.
  • Methylene malonates are malonates having at least one methylene group in the molecule, including monofunctional methylene malonates having one methylene group and polyfunctional methylene malonates having two or more methylene groups. Methylene malonates preferably have a molecular weight of 220 or greater. There are no particular restrictions on the types of methylene malonates that can be used, and in addition to compounds described in WO 2018/212330 A1 and the like, various disclosed methylene malonates can be used. Methylene malonates may be used alone or in combination of two or more types.
  • the thiol compound in the mixture of a compound having an unsaturated double bond and a thiol compound is a compound containing at least one thiol group, and the thiol group can undergo a radical addition reaction (ene-thiol reaction) with the unsaturated double bond of the compound having an unsaturated double bond.
  • Thiol compounds are broadly classified into thiol compounds that have a hydrolyzable partial structure such as an ester bond in the molecule (i.e., hydrolyzable) and thiol compounds that do not have such a partial structure (i.e., non-hydrolyzable).
  • hydrolyzable thiol compounds include trimethylolpropane tris(3-mercaptopropionate) (e.g., TMMP manufactured by SC Organic Chemical Co., Ltd.), tris-[(3-mercaptopropionyloxy)-ethyl]-isocyanurate (e.g., TEMPIC manufactured by SC Organic Chemical Co., Ltd.), pentaerythritol tetrakis(3-mercaptopropionate) (e.g., PEMP manufactured by SC Organic Chemical Co., Ltd.), tetraethylene glycol bis(3-mercaptopropionate) (e.g., EG
  • the dimer include, but are not limited to, dipentaerythritol hexakis(3-mercaptopropionate) (for example, DPMP manufactured by SC Organic Chemical Co., Ltd.), pentaerythritol tetrakis(3-mercaptobutyrate) (for example, Karen
  • non-hydrolyzable polyfunctional thiol compound examples include 1,3,4,6-tetrakis(2-mercaptoethyl)glycoluril (e.g., TS-G manufactured by Shikoku Chemical Industry Co., Ltd.), 1,3,4,6-tetrakis(3-mercaptopropyl)glycoluril (e.g., C3 TS-G manufactured by Shikoku Chemical Industry Co., Ltd.), 1,3,4,6-tetrakis(mercaptomethyl)glycoluril, 1,3,4,6-tetrakis(mercaptomethyl)-3a-methylglycoluril, 1,3,4,6-tetrakis(2-mercaptoethyl)-3a-methylglycoluril, 1,3,4,6-tetrakis(3-mercaptopropyl)-3a-methylglycoluril, 1,3,4,6-tetrakis(mercaptomethyl)-3a-methylglycoluril, 1,3,4,6-t
  • the content of the (A) radical polymerizable compound in the resin composition is preferably 1 to 99 parts by mass, more preferably 5 to 50 parts by mass, and even more preferably 7 to 30 parts by mass, per 100 parts by mass of the total resin composition.
  • the content of the (A) radical polymerizable compound in the resin composition is preferably 30 to 99 parts by mass, more preferably 50 to 99 parts by mass, and even more preferably 60 to 99 parts by mass, per 100 parts by mass of the total resin composition.
  • the content of the (A) radical polymerizable compound in the resin composition is preferably 40 to 99 parts by mass, more preferably 45 to 99.5 parts by mass, and even more preferably 50 to 98 parts by mass, per 100 parts by mass of all organic substances (excluding low-stress-imparting materials such as organic fillers and elastomers) contained in the resin composition.
  • the resin composition of this aspect contains (B) the thermal latent polymerization initiator of the above embodiment (hereinafter also referred to as "component (B)"). This makes it possible to provide a resin composition that has excellent storage stability and can be thermally cured at low temperatures. Any one of the thermal latent polymerization initiators may be used alone, or two or more may be used in combination.
  • the content of the thermal latent polymerization initiator (B) in the resin composition of this embodiment is preferably 0.5 to 60 parts by mass, more preferably 1 to 50 parts by mass, and even more preferably 1 to 40 parts by mass, per 100 parts by mass of the resin composition.
  • the resin composition of this aspect may further include (C) a thermal radical initiator desorption accelerator (hereinafter also referred to as “component (C)”).
  • component (C) a thermal radical initiator desorption accelerator
  • component (C) refers to a substance that can replace the thermal radical initiator supported on the inorganic ion exchanger in the thermal latent polymerization initiator, thereby promoting the desorption of the thermal radical initiator from the inorganic ion exchanger.
  • the (C) desorption accelerator may be a Lewis basic substance or a Lewis acidic substance.
  • the inorganic ion exchanger in the thermal latent polymerization initiator is an inorganic cation exchanger
  • a Lewis basic substance can be used as the (C) desorption accelerator.
  • the inorganic ion exchanger in the thermal latent polymerization initiator is an inorganic anion exchanger
  • a Lewis acidic substance can be used as the (C) desorption accelerator.
  • the (C) desorption accelerator is a Lewis basic substance. Examples of Lewis basic substances include, but are not limited to, water, amines, and imidazoles.
  • the desorption promoter (C) is a Lewis acidic substance. Examples of Lewis acidic substances include, but are not limited to, water and fatty acids.
  • the content of the (C) detachment promoter in the resin composition of this embodiment is preferably 0.001 to 60 parts by mass, more preferably 0.01 to 50 parts by mass, and even more preferably 0.1 to 40 parts by mass, per 100 parts by mass of the resin composition.
  • the content of the (C) elimination accelerator in the resin composition of this embodiment is preferably 0.01 to 100 parts by mass, more preferably 0.1 to 90 parts by mass, and even more preferably 1 to 80 parts by mass, relative to 100 parts by mass of the (B) thermal latent polymerization initiator.
  • the resin composition of this embodiment may contain optional components other than the above components (A) to (C), such as those described below.
  • the resin composition of this embodiment may contain a polymerization inhibitor.
  • the polymerization inhibitor is a compound having radical scavenging ability. By containing a polymerization inhibitor, the progress of unintended radical polymerization reactions can be suppressed, and the storage stability of the resin composition can be further improved.
  • the polymerization inhibitor may be a known polymerization inhibitor, including, but not limited to, N-nitroso-N-phenylhydroxylamine aluminum, triphenylphosphine, p-methoxyphenol, hydroquinone, p-benzoquinone, etc. Also, known polymerization inhibitors disclosed in JP 2010-117545 A and JP 2008-184514 A, etc., may be used. Any one of the polymerization inhibitors may be used, or two or more may be used in combination.
  • the content of the polymerization inhibitor is preferably 0.1 to 5.0 parts by mass, more preferably 0.2 to 4.0 parts by mass, and even more preferably 0.3 to 3.0 parts by mass, per 100 parts by mass of (B) the thermal latent polymerization initiator.
  • the resin composition of this embodiment may contain a filler to the extent that the object of this embodiment is not impaired.
  • a filler in the resin composition, the linear expansion coefficient of the cured product obtained by curing the resin composition can be reduced, and thermal cycle resistance can be improved.
  • the filler has a low elastic modulus, stress generated in the cured product can be alleviated, and long-term reliability can be improved.
  • Fillers are broadly classified into inorganic fillers and organic fillers.
  • the inorganic filler is not particularly limited as long as it is made of granular material and has the effect of lowering the linear expansion coefficient when added.
  • examples of inorganic materials that can be used include silica, talc, zeolite, alumina, aluminum nitride, calcium carbonate, aluminum silicate, magnesium silicate, magnesium carbonate, barium sulfate, barium carbonate, lime sulfate, aluminum hydroxide, calcium silicate, potassium titanate, titanium oxide, zinc oxide, silicon carbide, silicon nitride, and boron nitride. Any one of these inorganic fillers may be used alone, or two or more may be used in combination.
  • Silica filler is preferred as the inorganic filler, as it allows for a high loading amount.
  • Amorphous silica is preferred as the silica.
  • the surface of the inorganic filler be treated with a coupling agent such as a silane coupling agent. This allows the thixotropic index (TI) of the resin composition to fall within an appropriate range.
  • a coupling agent such as a silane coupling agent.
  • Conductive fillers can also be used as inorganic fillers.
  • Conductive fillers can be formed from conductive materials molded into particles, or core particles coated with a conductive material (coated powder).
  • the cores contained in the conductive filler can be made of a non-conductive material, as long as they are partially coated with a conductive material.
  • the conductive material in the conductive filler is not particularly limited as long as it imparts thermal conductivity and/or electrical conductivity to the resin composition.
  • Examples include, but are not limited to, gold, silver, nickel, copper, palladium, platinum, bismuth, tin, and alloys thereof (particularly bismuth-tin alloys, solder, etc.), aluminum, indium tin oxide, silver-coated copper, silver-coated aluminum, metal-coated glass spheres, silver-coated fibers, silver-coated resin, antimony-doped tin, tin oxide, carbon fibers, graphite, carbon black, and mixtures thereof.
  • organic fillers examples include polytetrafluoroethylene (PTFE) fillers, silicone fillers, acrylic fillers, and styrene fillers.
  • PTFE polytetrafluoroethylene
  • silicone fillers examples include silicone fillers, acrylic fillers, and styrene fillers.
  • the organic fillers may be surface-treated.
  • the shape of the filler is not particularly limited and may be spherical, flaky, needle-like, irregular, etc.
  • the average particle size of the filler is preferably 0.01 to 15 ⁇ m, more preferably 0.01 to 10 ⁇ m.
  • the maximum particle size of the filler is preferably 50 ⁇ m or less, more preferably 30 ⁇ m or less.
  • the average particle size of a filler is the particle size at 50% of the cumulative value in the particle size distribution on a volume basis, measured by laser diffraction/scattering.
  • the maximum particle size is the largest particle size in the particle size distribution on a volume basis, measured by laser diffraction/scattering.
  • the resin composition of this embodiment may further contain other additives, such as carbon black, titanium black, a thixotropic agent, a coupling agent, an ion trapping agent, a leveling agent, an antioxidant, an antifoaming agent, a viscosity modifier, a flame retardant, a colorant, a plasticizer, etc., within the scope of the present embodiment.
  • additives such as carbon black, titanium black, a thixotropic agent, a coupling agent, an ion trapping agent, a leveling agent, an antioxidant, an antifoaming agent, a viscosity modifier, a flame retardant, a colorant, a plasticizer, etc.
  • the viscosity of the resin composition of this embodiment is preferably 0.1 to 100 Pa ⁇ s.
  • the viscosity can be adjusted appropriately depending on the intended use and application location of the resin composition.
  • viscosity is expressed as a value measured in accordance with Japanese Industrial Standard JIS K6833, unless otherwise specified. Specifically, it can be determined by measuring using an E-type viscometer at a rotation speed of 10 rpm. There are no particular restrictions on the equipment, rotor, or measurement range used.
  • the method for producing the resin composition of this embodiment is not particularly limited.
  • the resin composition of this embodiment can be obtained by simultaneously or separately introducing component (A), component (B), and, if necessary, component (C) and other optional components into an appropriate mixer and mixing them by stirring to form a uniform composition.
  • the mixer is not particularly limited, but examples that can be used include a Raikai mixer, Henschel mixer, three-roll mill, ball mill, planetary mixer, and bead mill equipped with a stirring device and a heating device. These devices may also be used in appropriate combinations.
  • the resin composition obtained in this manner is thermosetting and can be cured at low temperatures, for example, 40 to 120°C, preferably 50 to 100°C, more preferably 60 to 90°C, and even more preferably 60 to 80°C. At a temperature of 80°C, it can be cured within 30 hours, for example, within 20 hours, preferably within 4 hours, more preferably within 3 hours, and even more preferably within 1 hour.
  • the resin composition of this embodiment is used to manufacture a semiconductor module containing components that deteriorate under high-temperature conditions, it is preferable to thermally cure the composition at a temperature of 50 to 100°C for 15 minutes to 4 hours, preferably 30 minutes to 2 hours.
  • the resin composition of this embodiment can be used, for example, as an adhesive or sealant for fixing, joining, or protecting components that make up a semiconductor device or electronic component, or as a raw material for such adhesives or sealants.
  • the method for applying the resin composition of this embodiment is not particularly limited, and can be applied to the desired portion of a substrate or the like by a known printing method, dispensing method, or coating method, for example.
  • Printing methods include, but are not limited to, inkjet printing, screen printing, lithographic printing, carton printing, metal printing, offset printing, gravure printing, and flexographic printing.
  • Dispensing methods include, but are not limited to, methods using a jet dispenser or air dispenser.
  • Coating methods include, but are not limited to, dip coating, spray coating, bar coater coating, gravure coating, reverse gravure coating, and spin coater coating.
  • Adhesive or sealant Another aspect of the present invention is an adhesive or sealant containing the resin composition of the above-described aspect.
  • This adhesive or sealant enables good fixation, bonding, or protection of engineering plastics (e.g., LCP (liquid crystal polymer), polyamide, polycarbonate, etc.), ceramics, and metals (e.g., copper, nickel, etc.), and can be used to fix, bond, or protect components constituting a semiconductor device or electronic component.
  • engineering plastics e.g., LCP (liquid crystal polymer), polyamide, polycarbonate, etc.
  • ceramics e.g., copper, nickel, etc.
  • metals e.g., copper, nickel, etc.
  • semiconductor devices or electronic components include, but are not limited to, HDDs, semiconductor elements, sensor modules such as image sensor modules, other semiconductor modules, and integrated circuits.
  • the adhesive or sealant of this embodiment can be cured under low temperature conditions, and therefore has high productivity and is suitable for use in the manufacture of semiconductor devices and
  • the film of this embodiment can be obtained from the resin composition of the above embodiment by a known method.
  • the resin composition of the above embodiment can be diluted with a solvent to form a varnish, which can be applied to at least one surface of a support, dried, and then provided as a film attached to the support or a film peeled from the support.
  • Prepregs can be produced by known methods, such as the hot melt method and solvent method.
  • the hot melt method the resin composition of the above embodiment is first coated onto a release paper with good peelability without being dissolved in an organic solvent, and then the coated paper is laminated onto a sheet-like fiber substrate, or the prepreg can be produced by directly applying the resin composition using a die coater.
  • the prepreg can be produced by first immersing the sheet-like fiber substrate in a resin composition varnish prepared by dissolving the resin composition of the above embodiment in an organic solvent, thereby impregnating the sheet-like fiber substrate with the resin composition varnish, and then drying the sheet-like fiber substrate.
  • Another aspect of the present invention is a cured product obtained by curing the resin composition of the above aspect.
  • a cured product can be produced by heating the resin composition of the above aspect.
  • a method for producing a cured product comprising heating the resin composition of the above aspect is also an aspect of the present invention.
  • the heating temperature may be as low as 40 to 120°C, preferably 50 to 100°C, more preferably 60 to 90°C, and even more preferably 60 to 80°C.
  • the heating time is, for example, within 30 hours, for example, within 20 hours, preferably 4 hours, more preferably within 3 hours, and even more preferably within 1 hour.
  • the heating conditions may be a temperature of 50 to 100°C and a heating time of 15 minutes to 4 hours, preferably 30 minutes to 2 hours.
  • semiconductor devices electronic components
  • the semiconductor device or electronic component according to one embodiment of the present invention includes the cured product according to the above-described embodiment, and therefore has high reliability.
  • semiconductor device refers to any device that can function by utilizing semiconductor properties, including electronic components, semiconductor circuits, modules incorporating these, electronic devices, etc.
  • semiconductor devices or electronic components include, but are not limited to, HDDs, semiconductor elements, sensor modules such as image sensor modules, other semiconductor modules, and integrated circuits.
  • thermal latent polymerization initiator 1 ZrP-VA-061. Elemental analysis revealed C: 8.87, H: 2.13, and N: 4.41, and the composition was estimated to be Zr(HPO 4 ) 2 0.18C 12 H 22 N 6 0.63H 2 O. Based on the amount of N, 0.53 mmol/g (13.1 wt %) of thermal radical initiator (VA-061) was incorporated.
  • NanoZrP nanoparticulate zirconium phosphate
  • dry weight 10.05% 82.0 g was placed in an empty eggplant flask, and 6.65 g of 2,2'-azobis[2-(2-imidazolin-2-yl)propane] (product name: VA-061, Fujifilm Wako Pure Chemical Industries, Ltd.) dissolved in 50 mL of ethanol was added and stirred at room temperature for 1 hour. The product was then centrifuged three times with ethanol (4000 rpm, 3 min, 0°C) to obtain thermal latent polymerization initiator 2 (NanoZrP-VA- 061 ).
  • A Radically polymerizable compound
  • A-1 2-hydroxyethyl methacrylate (manufactured by Tokyo Chemical Industry Co., Ltd.)
  • A-2) Dimethylol-tricyclodecane diacrylate (Kyoeisha Chemical Co., Ltd.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

L'objet de la présente invention est de mettre à disposition un nouvel initiateur de polymérisation latente qui est excellent en termes de stabilité au stockage et permet le durcissement thermique d'une composition de résine à basse température. L'objet de la présente invention est également de mettre à disposition une composition de résine et un adhésif ou un matériau d'étanchéité, qui sont excellents en termes de stabilité au stockage et qui peuvent être durcis thermiquement à basse température.　La présente invention concerne : un initiateur de polymérisation latente thermique dans lequel un initiateur radicalaire thermique est supporté par des particules d'échangeur d'ions inorganiques ; une composition de résine qui contient (A) un composé polymérisable par voie radicalaire et (B) l'initiateur de polymérisation latente thermique ; et un adhésif ou un matériau d'étanchéité qui contient la composition de résine.
PCT/JP2025/002136 2024-01-29 2025-01-24 Initiateur de polymérisation latente thermique, composition de résine le contenant, adhésif, matériau d'étanchéité, film, produit durci de ceux-ci, procédé de production de produit durci, et dispositif à semi-conducteur ou composant électronique Pending WO2025164514A1 (fr)

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JP2024010832 2024-01-29

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH10501729A (ja) * 1994-03-17 1998-02-17 エクソン・ケミカル・パテンツ・インク 触媒担持体用の噴霧乾燥ポリマー
JPH11279228A (ja) * 1998-02-09 1999-10-12 Bayer Ag 懸濁または気相法による共役ジエンの遊離基重合及びこれと更なる単量体との共重合に対する新規な、重合を開始する担持系
JP2000026525A (ja) * 1998-05-08 2000-01-25 Tosoh Corp オレフィン重合体製造用触媒およびオレフィン重合体の製造方法
JP2007326892A (ja) * 2006-06-06 2007-12-20 Daito Kasei Kogyo Kk ラジカル重合開始剤固定化粉体、高分子量化合物固定化粉体並びにそれを用いる塗料、インキ、化粧料および充填剤
JP2019510859A (ja) * 2016-03-24 2019-04-18 シーカ テクノロジー アクチェンゲゼルシャフト ヒドロゲルを製造するための単一剤系又は多剤系組成物

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH10501729A (ja) * 1994-03-17 1998-02-17 エクソン・ケミカル・パテンツ・インク 触媒担持体用の噴霧乾燥ポリマー
JPH11279228A (ja) * 1998-02-09 1999-10-12 Bayer Ag 懸濁または気相法による共役ジエンの遊離基重合及びこれと更なる単量体との共重合に対する新規な、重合を開始する担持系
JP2000026525A (ja) * 1998-05-08 2000-01-25 Tosoh Corp オレフィン重合体製造用触媒およびオレフィン重合体の製造方法
JP2007326892A (ja) * 2006-06-06 2007-12-20 Daito Kasei Kogyo Kk ラジカル重合開始剤固定化粉体、高分子量化合物固定化粉体並びにそれを用いる塗料、インキ、化粧料および充填剤
JP2019510859A (ja) * 2016-03-24 2019-04-18 シーカ テクノロジー アクチェンゲゼルシャフト ヒドロゲルを製造するための単一剤系又は多剤系組成物

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