US20230002661A1 - Curable composition and article - Google Patents

Curable composition and article Download PDF

Info

Publication number
US20230002661A1
US20230002661A1 US17/779,129 US202017779129A US2023002661A1 US 20230002661 A1 US20230002661 A1 US 20230002661A1 US 202017779129 A US202017779129 A US 202017779129A US 2023002661 A1 US2023002661 A1 US 2023002661A1
Authority
US
United States
Prior art keywords
curable composition
meth
acrylate
cured product
mass
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
US17/779,129
Other languages
English (en)
Inventor
Yuki Nakamura
Naoki Furukawa
Hiroshi Yokota
Tsuyoshi Morimoto
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.)
Resonac Corp
Original Assignee
Resonac 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 Resonac Corp filed Critical Resonac Corp
Assigned to SHOWA DENKO MATERIALS CO., LTD. reassignment SHOWA DENKO MATERIALS CO., LTD. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: MORIMOTO, TSUYOSHI, YOKOTA, HIROSHI, FURUKAWA, NAOKI, NAKAMURA, YUKI
Publication of US20230002661A1 publication Critical patent/US20230002661A1/en
Assigned to RESONAC CORPORATION reassignment RESONAC CORPORATION CHANGE OF NAME (SEE DOCUMENT FOR DETAILS). Assignors: SHOWA DENKO MATERIALS CO., LTD.
Assigned to RESONAC CORPORATION reassignment RESONAC CORPORATION CHANGE OF ADDRESS Assignors: RESONAC CORPORATION
Pending legal-status Critical Current

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L51/00—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
    • C08L51/08—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers grafted on to macromolecular compounds obtained otherwise than by reactions only involving unsaturated carbon-to-carbon bonds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
    • C09K5/08—Materials not undergoing a change of physical state when used
    • C09K5/14—Solid materials, e.g. powdery or granular
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/14—Preparation of carboxylic acid esters from carboxylic acid halides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
    • C07C69/602—Dicarboxylic acid esters having at least two carbon-to-carbon double bonds
    • 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
    • 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
    • C08F222/10—Esters
    • C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
    • C08F222/106—Esters of polycondensation macromers
    • C08F222/1063—Esters of polycondensation macromers of alcohol terminated polyethers
    • 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
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
    • C08F290/06—Polymers provided for in subclass C08G
    • C08F290/062—Polyethers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32—Polymers modified by chemical after-treatment
    • C08G65/329—Polymers modified by chemical after-treatment with organic compounds
    • C08G65/331—Polymers modified by chemical after-treatment with organic compounds containing oxygen
    • C08G65/332—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K13/00—Use of mixtures of ingredients not covered by one single of the preceding main groups, each of these compounds being essential
    • C08K13/02—Organic and inorganic ingredients
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
    • C08K3/013—Fillers, pigments or reinforcing additives
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/02—Elements
    • C08K3/08—Metals
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
    • C08K3/20—Oxides; Hydroxides
    • C08K3/22—Oxides; Hydroxides of metals
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/13—Phenols; Phenolates
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/02—Elements
    • C08K3/08—Metals
    • C08K2003/0812—Aluminium
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
    • C08K3/20—Oxides; Hydroxides
    • C08K3/22—Oxides; Hydroxides of metals
    • C08K2003/2227—Oxides; Hydroxides of metals of aluminium
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K2201/00—Specific properties of additives
    • C08K2201/001—Conductive additives
    • 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
    • H05K7/00—Constructional details common to different types of electric apparatus
    • H05K7/20—Modifications to facilitate cooling, ventilating, or heating
    • H05K7/2039—Modifications to facilitate cooling, ventilating, or heating characterised by the heat transfer by conduction from the heat generating element to a dissipating body

Definitions

  • the present invention relates to a curable composition and an article.
  • a thermally conductive material (may also be referred to as thermal dissipation material) called a thermal interface material (TIM) is a material provided between a heat source and a thermal dissipation member such as a heat sink, and the thermally conductive material reduces the heat resistance between the heat source and the thermal dissipation member and promotes thermal conduction from the heat source. Since the heat generated from the heat source is efficiently conducted to a cooling member via the TIM, the heat is easily dissipated from the thermal dissipation member.
  • TIM thermal interface material
  • thermally conductive material a large number of liquid materials are known, and they are also referred to as thermal dissipation greases or thermally conductive greases.
  • a thermally conductive grease composition containing predetermined amounts of a liquid hydrocarbon oil and/or a fluorinated hydrocarbon oil and a thermally conductive inorganic filler is disclosed.
  • Patent Literature 2 a thermally conductive grease containing a specific phenyl ether-based base oil, a specific phenol-based oxidation inhibitor, and an inorganic powder filler is disclosed.
  • liquid dripping or a pump-out phenomenon in which the grease is pushed out from between the members due to deformation of the member on which the thermally conductive grease is applied, may occur.
  • Liquid dripping or the pump-out phenomenon generates voids between the grease and the member, decreases the adhesiveness of the grease to the member, and causes an increase in heat resistance between the thermal dissipation grease and the member. Due to liquid dripping or the pump-out phenomenon, other members may be contaminated by the grease, and insulation failure may occur.
  • a thermally conductive material formed into a solid form such as a sheet may be used. Liquid dripping or the pump-out phenomenon can be suppressed by using a solid-form thermally conductive material.
  • a solid-form thermally conductive material in an electronic component containing a member that generates heat and a thermal dissipation member, deformation such as warpage of the members may occur when cooling and heating is repeated. Accordingly, the solid-form thermally conductive material is required to be a material having excellent elongation so that the material can follow deformation of the members.
  • an object of the present invention is to provide a curable composition capable of giving a cured product having excellent elongation.
  • the inventors of the present invention conducted a thorough study, and as a result, the inventors found that a cured product of a curable composition containing a specific compound having a polyoxyalkylene chain and having two (meth)acryloyl groups has excellent elongation. Furthermore, the inventors found that since this curable composition contains a thermally conductive filler, the curable composition is suitably used as a thermally conductive material, thus the inventors completing the present invention. According to some aspects, the present invention provides the following [1] to [11].
  • R 11 and R 12 each independently represent a hydrogen atom or a methyl group, and R 13 represents a divalent group having a polyoxyalkylene chain; and a thermally conductive filler.
  • a curable composition capable of giving a cured product having excellent elongation can be provided.
  • a curable composition capable of giving a cured product having excellent elongation as well as low elasticity can be provided.
  • FIG. 1 is a schematic cross-sectional view illustrating an embodiment of an article containing a cured product of a curable composition.
  • FIG. 2 is a schematic cross-sectional view illustrating another embodiment of an article containing a cured product of a curable composition.
  • (meth)acryloyl means “acryloyl” and “methacryloyl” corresponding thereto, and the same also applies to similar expressions such as “(meth)acrylate” and “(meth)acryl”.
  • the weight average molecular weight (Mw) means a value measured using gel permeation chromatography (GPC) under the following conditions and determined by using polystyrene as a standard substance.
  • a curable composition according to an embodiment contains a compound represented by the following formula (1):
  • R 11 and R 12 each independently represent a hydrogen atom or a methyl group
  • R 13 represents a divalent group having a polyoxyalkylene chain, and a thermally conductive filler.
  • any one of R 11 and R 12 may be a hydrogen atom, while the other may be a methyl group; according to another embodiment, both R 11 and R 12 may be a hydrogen atom; and according to still another embodiment, both R 11 and R 12 may be a methyl group.
  • the polyoxyalkylene chain contains a structural unit represented by the following formula (2).
  • the strength of the cured product can be increased while suppressing an excessive increase of the viscosity of the curable composition.
  • R 13 may be a divalent group having a polyoxyethylene chain
  • the compound represented by the formula (1) is preferably a compound represented by the following formula (1-2) (polyethylene glycol di(meth)acrylate):
  • R 11 and R 12 have the same meanings as R 11 and R 12 in the formula (1), respectively; and in represents an integer of 2 or more.
  • the polyoxyalkylene chain contains a structural unit represented by the following formula (3).
  • R 13 may be a divalent group having a polyoxypropylene chain
  • the compound represented by the formula (1) is preferably a compound represented by the following formula (1-3) (polypropylene glycol di(meth)acrylate):
  • R 11 and R 12 have the same meanings as R 11 and R 12 in the formula (1), respectively, and n represents an integer of 2 or more.
  • the polyoxyalkylene chain is preferably a copolymer chain containing the above-mentioned structural unit represented by the formula (2) and the above-mentioned structural unit represented by the formula (3).
  • the copolymer chain may be any one of an alternating copolymer chain, a block copolymer chain, or a random copolymer chain.
  • the copolymer chain is preferably a random copolymer chain.
  • the polyoxyalkylene chain may have an oxyalkylene group having 4 or 5 carbon atoms, such as an oxytetramethylene group, an oxybutylene group, or an oxypentylene group, as a structural unit in addition to the structural unit represented by the formula (2) and the structural unit represented by the formula (3).
  • R 13 may also be a divalent group further having an additional organic group in addition to the above-mentioned polyoxyalkylene chain.
  • the additional organic group may be a chain-like group other than the polyoxyalkylene chain, and the additional organic group may be, for example, a methylene chain (chain having —CH 2 — as a structural unit), a polyester chain (chain containing —COO— in a structural unit), or a polyurethane chain (chain containing —OCON— in a structural unit).
  • the compound represented by the formula (1) may be a compound represented by the following formula (1-4):
  • R 11 and R 12 have the same meanings as R 11 and R 12 in the formula (1), respectively;
  • R 14 and R 15 each independently represent an alkylene group having 2 to 5 carbon atoms;
  • k1, k2, and k3 each independently represent an integer of 2 or more.
  • k2 may be, for example, an integer of 16 or less.
  • Each of R 14 and R 15 which are present in plurality, may be identical with each other or may be different from each other.
  • Each of R 14 and R 15 , which are present in plurality preferably contains an ethylene group and a propylene group. That is, a polyoxyalkylene chain represented by (R 14 O) k1 and a polyoxyalkylene chain represented by (R 15 O) k3 are each preferably a copolymer chain containing an oxyethylene group (the above-described structural unit represented by the formula (2)) and an oxypropylene group (the above-described structural unit represented by the formula (3)).
  • the polyoxyalkylene chain preferably has 100 or more of oxyalkylene groups.
  • the number of oxyalkylene groups in the polyoxyalkylene chain is 100 or more, as the main chain of the compound represented by the formula (1) becomes longer, the elongation of the cured product is superior, and the strength of the cured product can also be increased.
  • the number of oxyalkylene groups corresponds to each of in in the formula (1-2), n in the formula (1-3), and k1 and k3 in the formula (1-4).
  • the number of oxyalkylene groups in the polyoxyalkylene chain is more preferably 130 or more, 180 or more, 200 or more, 220 or more, 250 or more, 270 or more, 300 or more, or 320 or more.
  • the number of oxyalkylene groups in the polyoxyalkylene chain may be 600 or less, 570 or less, or 530 or less.
  • the weight average molecular weight of the compound represented by the formula (1) is preferably 5000 or more, 6000 or more, 7000 or more, 8000 or more, 9000 or more, 10000 or more, 11000 or more, 12000 or more, 13000 or more, 14000 or more, or 15000 or more.
  • the weight average molecular weight of the compound represented by the formula (1) is preferably 100000 or less, 80000 or less, 60000 or less, 34000 or less, 31000 or less, or 28000 or less.
  • the compound represented by the formula (1) may be liquid at 25° C.
  • the viscosity at 25° C. of the compound represented by the formula (1) is preferably 1000 Pa ⁇ s or less, 800 Pa ⁇ s or less, 600 Pa ⁇ s or less, 500 Pa ⁇ s or less, 350 Pas or less, 300 Pa ⁇ s or less, or 200 Pa ⁇ s or less.
  • the viscosity at 25° C. of the compound represented by the formula (1) may be 0.1 Pa ⁇ s or more, 0.2 Pa ⁇ s or more, 0.3 Pa ⁇ s or more, 1 Pa ⁇ s or more, 2 Pa ⁇ s or more, or 3 Pas or more.
  • the compound represented by the formula (1) may be solid at 25° C.
  • the compound represented by the formula (1) is preferably liquid at 50° C.
  • the viscosity at 50° C. of the compound represented by the formula (1) is preferably 100 Pa ⁇ s or less, more preferably 50 Pa ⁇ s or less, even more preferably 30 Pa s or less, and particularly preferably 20 Pa ⁇ s or less.
  • the viscosity at 50° C. of the compound represented by the formula (1) may be 0.1 Pa ⁇ s or more, 0.2 Pa ⁇ s or more, or 0.3 Pa ⁇ s or more.
  • the viscosity means a value measured based on JIS Z 8803, and specifically, the viscosity means a value measured by using an E type viscometer (for example, manufactured by Toki Sangyo Co., Ltd., PE-80L). Incidentally, compensation of the viscometer can be carried out based on JIS Z 8809-JS14000.
  • the viscosity of the compound represented by the formula (1) can be adjusted by adjusting the weight average molecular weight of the compound.
  • the content of the compound represented by the formula (1) is preferably 1% by mass or more, more preferably 1.5% by mass or more, and even more preferably 2% by mass or more, based on the total amount of the curable composition.
  • the content of the compound represented by the formula (1) may be 20% by mass or less, 17% by mass or less, or 15% by mass or less, based on the total amount of the curable composition.
  • the curable composition may contain an additional polymerizable compound (the details will be described below) other than the compound represented by the formula (1).
  • the content of the compound represented by the formula (1) is preferably 10 parts by mass or more, 20 parts by mass or more, 25 parts by mass or more, 30 parts by mass or more, or 35 parts by mass or more, with respect to 100 parts by mass of the sum of the compound represented by the formula (1) and the additional polymerizable compound (hereinafter, referred to as “sum of the contents of the polymerizable components”).
  • the content of the compound represented by the formula (1) may be 80 parts by mass or less, 60 parts by mass or less, or 50 parts by mass or less, with respect to 100 parts by mass of the sum of the contents of the polymerizable components.
  • the curable composition contains a thermally conductive filler.
  • a thermally conductive filler refers to a filler having a thermal conductivity of 10 W/m ⁇ K or higher.
  • the thermally conductive filler may be insulative or may be electrically conductive, and the thermally conductive filler is preferably an insulative filler.
  • the material that constitutes an insulative thermally conductive filler include aluminum oxide, aluminum hydroxide, magnesium oxide, beryllium oxide, boron nitride, aluminum nitride, silicon nitride, silicon carbide, silicon dioxide, aluminum fluoride, calcium fluoride, and zinc oxide.
  • Examples of the material that constitutes an electrically conductive thermally conductive filler include aluminum, silver, and copper.
  • the shape of the thermally conductive filler may be spherical or may be polyhedral.
  • the average particle size of the thermally conductive filler is preferably 50 ⁇ m or less, more preferably 40 ⁇ m or less, even more preferably 30 ⁇ m or less, and may be 0.05 ⁇ m or more, 0.1 ⁇ m or more, or 0.3 ⁇ m or more.
  • the average particle size of the thermally conductive filler means the particle size (D50) at which the volume cumulative particle size distribution is 50%, and the average particle size is measured using a laser diffraction type particle size distribution analyzer (for example, SALD-2300 (manufactured by SHIMADZU CORPORATION)).
  • the content of the thermally conductive filler is preferably 60% by mass or more, more preferably 70% by mass or more, and even more preferably 80% by mass or more, and may be 97% by mass or less, 95% by mass or less, or 93% by mass or less, based on the total amount of the curable composition.
  • the content of the thermally conductive filler is preferably 70% by volume or more, more preferably 75% by volume or more, and even more preferably 80% by volume or more, and may be 90% by volume or less, 88% by volume or less, or 85% by volume or less, based on the total volume of the curable composition.
  • the curable composition may further contain an additional polymerizable compound that can be copolymerized with the above-mentioned compound represented by the formula (1).
  • the additional polymerizable compound may be, for example, a compound having one (meth)acryloyl group.
  • This compound may be, for example, an alkyl (meth)acrylate.
  • the additional polymerizable compound may also be a compound having an aromatic hydrocarbon group, a group containing a polyoxyalkylene chain, a group containing a heterocyclic ring, an alkoxy group, a phenoxy group, a group containing a silane group, a group containing a siloxane bond, a halogen atom, a hydroxyl group, a carboxyl group, an amino group, or an epoxy group, in addition to the one (meth)acryloyl group.
  • the viscosity of the curable composition can be adjusted.
  • the curable composition contains a compound having a hydroxyl group, a carboxyl group, an amino group, or an epoxy group in addition to the (meth)acryloyl group, the adhesiveness of the curable composition and a cured product thereof to a member can be further enhanced.
  • the alkyl group in the alkyl (meth)acrylate (alkyl group moiety other than the (meth)acryloyl group) may be linear, branched, or alicyclic.
  • the number of carbon atoms of the alkyl group may be, for example, 1 to 30.
  • the number of carbon atoms of the alkyl group may be 1 to 11, 1 to 8, 1 to 6, or 1 to 4, and may be 12 to 30, 12 to 28, 12 to 24, 12 to 22, 12 to 18, or 12 to 14.
  • alkyl (meth)acrylate having a linear alkyl group examples include an alkyl (meth)acrylate having a linear alkyl group having 1 to 11 carbon atoms, such as methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, butyl (meth)acrylate, pentyl (meth)acrylate, n-hexyl (meth)acrylate, n-heptyl (meth)acrylate, octyl (meth)acrylate, nonyl (meth)acrylate, decyl (meth)acrylate, or undecyl (meth)acrylate; and an alkyl (meth)acrylate having a linear alkyl group having 12 to 30 carbon atoms, such as dodecyl (meth)acrylate (lauryl (meth)acrylate), tetradecyl (meth)acrylate, hexadecyl (meth)acrylate
  • alkyl (meth)acrylate having a branched alkyl group examples include an alkyl (meth)acrylate having a branched alkyl group having 1 to 11 carbon atoms, such as s-butyl (meth)acrylate, t-butyl (meth)acrylate, isobutyl (meth)acrylate, isopentyl (meth)acrylate, isoamyl (meth)acrylate, isooctyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, isononyl (meth)acrylate, or isodecyl (meth)acrylate; and an alkyl (meth)acrylate having a branched alkyl group having 12 to 30 carbon atoms, such as isomyristyl (meth)acrylate, 2-propylheptyl (meth)acrylate, isoundecyl (meth)acrylate, isododecyl
  • alkyl (meth)acrylate having an alicyclic alkyl group examples include cyclohexyl (meth)acrylate, 3,3,5-trimethylcyclohexyl (meth)acrylate, isobornyl (meth)acrylate, terpene (meth)acrylate, and dicyclopentanyl (meth)acrylate.
  • the compound having a (meth)acryloyl group and an aromatic hydrocarbon group may be benzyl (meth)acrylate or the like.
  • Examples of the compound having a group containing a (meth)acryloyl group and a group containing a polyoxyalkylene chain include polyethylene glycol (meth)acrylate, methoxy polyethylene glycol (meth)acrylate, polypropylene glycol (meth)acrylate, methoxy polypropylene glycol (meth)acrylate, polybutylene glycol (meth)acrylate, and methoxy polybutylene glycol (meth)acrylate.
  • Examples of the compound having a (meth)acryloyl group and a group containing a heterocyclic ring include tetrahydrofurfuryl (meth)acrylate.
  • Examples of the compound having a (meth)acryloyl group and an alkoxy group include 2-methoxyethyl acrylate.
  • Examples of the compound having a (meth)acryloyl group and a phenoxy group include phenoxyethyl (meth)acrylate.
  • Examples of the compound having a (meth)acryloyl group and a group containing a silane group include 3-acryloxypropyltriethoxysilane, 10-methacryloyloxydecyltrimethoxysilane, 10-acryloyloxydecyltrimethoxysilane, 10-methacryloyloxydecyltriethoxysilane, and 10-acryloyloxydecyltriethoxysilane.
  • Examples of the compound having a (meth)acryloyl group and a group containing a siloxane bond include silicone (meth)acrylate.
  • Examples of the compound having a (meth)acryloyl group and a halogen atom include (meth)acrylates having fluorine atoms, such as trifluoromethyl (meth)acrylate, 2,2,2-trifluoroethyl (meth)acrylate, 1,1,1,3,3,3-hexafluoro-2-propyl (meth)acrylate, perfluoroethylmethyl (meth)acrylate, perfluoropropylmethyl (meth)acrylate, perfluorobutylmethyl (meth)acrylate, perfluoropentylmethyl (meth)acrylate, perfluorohexylmethyl (meth)acrylate, perfluoroheptylmethyl (meth)acrylate, perfluorooctylmethyl (meth)acrylate, perfluorononylmethyl (meth)acrylate, perfluorodecylmethyl (meth)acrylate, perfluoroundecylmethyl (meth)acrylate, per
  • Examples of the compound having a (meth)acryloyl group and a hydroxyl group include a hydroxyalkyl (meth)acrylate such as 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, 6-hydroxyhexyl (meth)acrylate, 8-hydroxyoctyl (meth)acrylate, 10-hydroxydecyl (meth)acrylate, or 12-hydroxylauryl (meth)acrylate; and a hydroxyalkylcycloalkane (meth)acrylate such as (4-hydroxymethylcyclohexyl)methyl (meth)acrylate.
  • a hydroxyalkyl (meth)acrylate such as 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, 2-hydroxybutyl (
  • Examples of the compound having a (meth)acryloyl group and a carboxyl group include (meth)acrylic acid, carboxyethyl (meth)acrylate, carboxypentyl (meth)acrylate, phthalic acid monohydroxyethyl acrylate (for example, “ARONIX M5400” manufactured by Toagosei Co., Ltd.), and 2-acryloyloxyethyl succinate (for example, “NK ESTER A-SA” manufactured by Shin-Nakamura Chemical Co., Ltd.).
  • Examples of the compound having a (meth)acryloyl group and an amino group include N,N-dimethylaminoethyl (meth)acrylate, N,N-diethylaminoethyl (meth)acrylate, N,N-dimethylaminopropyl (meth)acrylate, and N,N-diethylaminopropyl (meth)acrylate.
  • Examples of the compound having a (meth)acryloyl group and an epoxy group include glycidyl (meth)acrylate, glycidyl ⁇ -ethyl (meth)acrylate, glycidyl ⁇ -n-propyl (meth)acrylate, glycidyl ⁇ -n-butyl (meth)acrylate, 3,4-epoxybutyl (meth)acrylate, 4,5-epoxypentyl (meth)acrylate, 6,7-epoxyheptyl (meth)acrylate, 6,7-epoxyheptyl ⁇ -ethyl (meth)acrylate, 3-methyl-3,4-epoxybutyl (meth)acrylate, 4-methyl-4,5-epoxypentyl (meth)acrylate, 5-methyl-5,6-epoxyhexyl (meth)acrylate, ⁇ -methylglycidyl (meth)acrylate, and ⁇ -methylglycidyl
  • the content of the additional polymerizable compound is preferably 1% by mass or more, more preferably 3% by mass or more, and even more preferably 5% by mass or more, and may be 20% by mass or less, 15% by mass or less, or 10% by mass or less, based on the total amount of the curable composition.
  • the content of the additional polymerizable compound is preferably 30 parts by mass or more, more preferably 40 parts by mass or more, and even more preferably 50 parts by mass or more, and may be 90 parts by mass or less, 80 parts by mass or less, or 70 parts by mass or less, based on 100 parts by mass of the sum of the contents of the polymerizable components.
  • the curable composition may further contain a polymerization initiator.
  • the polymerization initiator may be, for example, a thermal polymerization initiator that generates radicals by heat, a photopolymerization initiator that generates radicals by light, or the like.
  • the polymerization initiator is preferably a thermal polymerization initiator.
  • the curable composition contains a thermal polymerization initiator
  • a cured product of the curable composition can be obtained by applying heat to the curable composition.
  • the curable composition may be a curable composition that is cured by heating at preferably 105° C. or higher, more preferably 110° C. or higher, and even more preferably 115° C. or higher, and may be a curable composition that is cured by heating at, for example, 200° C. or lower, 190° C. or lower, or 180° C. or lower.
  • the heating time at the time of heating the curable composition may be appropriately selected according to the composition of the curable composition so that the curable composition is suitably cured.
  • thermal polymerization initiator examples include azo compounds such as azobisisobutyronitrile, azobis-4-methoxy-2,4-dimethylvaleronitrile, asobiscyclohexanone-1-carbonitrile, and azodibenzoyl; and organic peroxides such as benzoyl peroxide, lauroyl peroxide, di-t-butyl peroxide, di-t-hexyl peroxide, di-t-butyl peroxy hexahydroterephthalate, t-butyl peroxy-2-ethylhexanoate, 1,1-t-butylperoxy-3,3,5-trimethylcyclohexane, t-butylperoxyisopropyl carbonate. Regarding the thermal polymerization initiator, these may be used singly or in combination of two or more kinds thereof.
  • a cured product of the curable composition can be obtained by, for example, irradiating the curable composition with light (for example, light containing at least a portion of wavelengths of 200 to 400 nm (ultraviolet light)).
  • light for example, light containing at least a portion of wavelengths of 200 to 400 nm (ultraviolet light)
  • the conditions for light irradiation may be appropriately set according to the type of the photopolymerization initiator.
  • the photopolymerization initiator may be, for example, a benzoin ether-based photopolymerization initiator, an acetophenone-based photopolymerization initiator, an ⁇ -ketol-based photopolymerization initiator, an aromatic sulfonyl chloride-based photopolymerization initiator, a photoactive oxime-based photopolymerization initiator, a benzoin-based photopolymerization initiator, a benzyl-based photopolymerization initiator, a benzophenone-based photopolymerization initiator, a ketal-based photopolymerization initiator, a thioxanthone-based photopolymerization initiator, or an acylphosphine oxide-based photopolymerization initiator.
  • a benzoin ether-based photopolymerization initiator an acetophenone-based photopolymerization initiator, an ⁇ -ketol-based photopolymerization initiator,
  • benzoin ether-based photopolymerization initiator examples include benzoin methyl ether, benzoin ethyl ether, benzoin propyl ether, benzoin isopropyl ether, benzoin isobutyl ether, 2,2-dimethoxy-1,2-diphenylethan-1-one (for example, “IRGACURE 651” manufactured by BASF SE), and anisole methyl ether.
  • acetophenone-based photopolymerization initiator examples include 1-hydroxycyclohexyl phenyl ketone (for example, “IRGACURE 184” manufactured by BASF SE), 4-phenoxydichloroacetophenone, 4-t-butyldichloroacetophenone, 1-[4-(2-hydroxyethoxy)-phenyl]-2-hydroxy-2-methyl-1-propan-1-one (for example, “IRGACURE 2959” manufactured by BASF SE), 2-hydroxy-2-methyl-1-phenylpropan-1-one (for example, “IRGACURE 1173” manufactured by BASF SE), and methoxyacetophenone.
  • 1-hydroxycyclohexyl phenyl ketone for example, “IRGACURE 184” manufactured by BASF SE
  • 4-phenoxydichloroacetophenone 4-t-butyldichloroacetophenone
  • Examples of the ⁇ -ketol-based photopolymerization initiator include 2-methyl-2-hydroxypropiophenone and 1-[4-(2-hydroxyethyl)-phenyl]-2-hydroxy-2-methylpropan-1-one.
  • Examples of the aromatic sulfonyl chloride-based photopolymerization initiator include 2-naphthalenesulfonyl chloride.
  • Examples of the photoactive oxime-based photopolymerization initiator include 1-phenyl-1,1-propanedione-2-(o-ethoxycarbonyl)-oxime.
  • Examples of the benzoin-based photopolymerization initiator include benzoin.
  • Examples of the benzyl-based photopolymerization initiator include benzyl.
  • Examples of the benzophenone-based photopolymerization initiator include benzophenone, benzoyl benzoate, 3,3′-dimethyl-4-methoxybenzophenone, polyvinylbenzophenone, and ⁇ -hydroxycyclohexyl phenyl ketone.
  • Examples of the ketal-based photopolymerization initiator include benzyl dimethyl ketal.
  • thioxanthone-based photopolymerization initiator examples include thioxanthone, 2-chlorothioxanthone, 2-methylthioxanthone, 2,4-dimethylthioxanthone, isopropylthioxanthone, 2,4-dichlorothioxanthone, 2,4-diethylthioxanthone, isopropylthioxanthone, 2,4-diisopropylthioxanthone, and dodecylthioxanthone.
  • acylphosphine-based photopolymerization initiator examples include bis(2,6-dimethoxybenzoyl)phenylphosphine oxide, bis(2,6-dimethoxybenzoyl)(2,4,4-trimethylpenyl)phosphine oxide, bis(2,6-dimethoxybenzoyl)-n-butylphosphine oxide, bis(2,6-dimethoxybenzoyl)-(2-methylpropan-1-yl)phosphine oxide, bis(2,6-dimethoxybenzoyl)-(1-methylpropan-1-yl)phosphine oxide, bis(2,6-dimethoxybenzoyl)-t-butylphosphine oxide, bis(2,6-dimethoxybenzoyl)cyclohexylphosphine oxide, bis(2,6-dimethoxybenzoyl)octylphosphine oxide, bis(2-methoxybenzoyl)(2-methylpropy
  • the above-mentioned photopolymerization initiator may be used singly or in combination of two or more kinds thereof.
  • the content of the polymerization initiator is preferably 0.01 parts by mass or more, more preferably 0.02 parts by mass or more, and even more preferably 0.05 parts by mass or more, with respect to 100 parts by mass of the sum of the contents of the polymerizable components.
  • the content of the polymerization initiator is preferably 10 parts by mass or less, more preferably 5 parts by mass or less, even more preferably 3 parts by mass or less, and particularly preferably 1 part by mass or less, with respect to 100 parts by mass of the sum of the contents of the polymerizable components.
  • the curable composition can further contain a plasticizer.
  • a plasticizer As the curable composition contains a plasticizer, the adhesiveness of the curable composition and the elongation of the cured product can be further enhanced.
  • the plasticizer include tackifiers such as a butadiene rubber, an isoprene rubber, a silicone rubber, a styrene-butadiene rubber, a chloroprene rubber, a nitrile rubber, a butyl rubber, an ethylene-propylene rubber, a urethane rubber, an acrylic resin, a rosin-based resin, and a terpene-based resin; and a polyalkylene glycol.
  • tackifiers such as a butadiene rubber, an isoprene rubber, a silicone rubber, a styrene-butadiene rubber, a chloroprene rubber, a nitrile rubber, a butyl rubber, an ethylene-propylene rubber
  • the content of the plasticizer may be 0.1 parts by mass or more, 1 part by mass or more, or 3 parts by mass or more, and may be 20 parts by mass or less, 15 parts by mass or less, 12 parts by mass or less, or 10 parts by mass or less, with respect to 100 parts by mass of the sum of the contents of the polymerizable components.
  • the curable composition may further contain an oxidation inhibitor.
  • the oxidation inhibitor may be, for example, a phenol-based oxidation inhibitor, a benzophenone-based oxidation inhibitor, a benzoate-based oxidation inhibitor, a hindered amine-based oxidation inhibitor, or a benzotriazole-based oxidation inhibitor, and the oxidation inhibitor is preferably a phenol-based oxidation inhibitor.
  • the phenol-based oxidation inhibitor has, for example, a hindered phenol structure (hindered phenol ring).
  • the hindered phenol structure (hindered phenol ring) may be, for example, a structure in which a t-butyl group is bonded to any one position or both positions of the ortho-position with respect to the hydroxyl group in a phenol ring.
  • the phenol-based oxidation inhibitor has one or more, preferably two or more, more preferably three or more, and even more preferably four or more of such a hindered phenol ring.
  • the content of the oxidation inhibitor may be 0.1% by mass or more, 0.2% by mass or more, or 0.3% by mass or more, and may be 10% by mass or less, 9% by mass or less, 8% by mass or less, or 7% by mass or less, based on the total amount of the curable composition.
  • the curable composition can further contain additional additives as necessary.
  • additional additives include a surface treatment agent (for example, a silane coupling agent), a dispersant, a curing accelerator, a colorant, a crystal nucleating agent, a thermal stabilizer, a foaming agent, a flame retardant, a vibration damping agent, a dehydrating agent, and a flame retardant aid (for example, a metal oxide).
  • the content of the additional additives may be 0.1% by mass or more and may be 30% by mass or less, based on the total amount of the curable composition.
  • the curable composition is preferably liquid at 25° C.
  • the curable composition can be suitably applied on the surface of an object such as a member that serves as a heat source or a cooling member, and the adhesiveness on the surface to be coated can also be increased.
  • the curable composition may be solid at 25° C., and in that case, it is preferable that the curable composition becomes liquid as a result of heating (for example, at 50° C. or higher).
  • the curable composition may be applied in a liquid state and then cured, and as a result, the curable composition can be suppressed from causing liquid dripping and the pump-out phenomenon.
  • a multi-liquid type curable composition set can be provided.
  • the curable composition set according to an embodiment is a curable composition set containing a first liquid containing an oxidizing agent and a second liquid containing a reducing agent. At least one of the first liquid and the second liquid contains the above-mentioned compound represented by the formula (1). Furthermore, at least one of the first liquid and the second liquid contains the above-mentioned thermally conductive filler.
  • a cured product of a mixture of the first liquid and the second liquid is immediately obtained by mixing the first liquid and the second liquid. That is, according to the curable composition set, a cured product of the curable composition is obtained at a high speed.
  • the first liquid contains the oxidizing agent, the compound represented by the formula (1), and the thermally conductive filler
  • the second liquid contains the reducing agent, the compound represented by the formula (1), and the thermally conductive filler
  • the content of the compound represented by the formula (1) based on the total liquid amount constituting the curable composition set may be similar to the range of the above-mentioned content of the compound represented by the formula (1) based on the total amount of the curable composition.
  • the same also applies to the content of the thermally conductive filler contained in the curable composition set.
  • the oxidizing agent contained in the first liquid plays the role as a polymerization initiator (radical polymerization initiator).
  • the oxidizing agent may be, for example, an organic peroxide or an azo compound.
  • the organic peroxide may be, for example, a hydroperoxide, a peroxydicarbonate, a peroxy ester, a peroxy ketal, a dialkyl peroxide, or a diacyl peroxide.
  • the azo compound may be AIBN (2,2′-azobisisobutyronitrile), ⁇ -65 (azobisdimethylvaleronitrile), or the like.
  • AIBN 2,2′-azobisisobutyronitrile
  • ⁇ -65 azobisdimethylvaleronitrile
  • hydroperoxide examples include diisopropylbenzene hydroperoxide and cumene hydroperoxide.
  • peroxydicarbonate examples include di-n-propyl peroxydicarbonate, diisopropyl peroxydicarbonate, bis(4-t-butylcyclohexyl) peroxydicarbonate, di-2-ethoxymethoxy peroxydicarbonate, di(2-ethylhexylperoxy) dicarbonate, dimethoxybutyl peroxydicarbonate, and di(3-methyl-3-methoxybutyl peroxy) dicarbonate.
  • peroxy ester examples include cumyl peroxyneodecanoate, 1,1,3,3-tetramethylbutyl peroxyneodecanoate, 1-cyclohexyl-1-methylethyl peroxyneodecanoate, t-hexyl peroxyneodecanoate, t-butyl peroxypivalate, 1,1,3,3-tetramethylbutyl peroxy-2-ethylhexanoate, 2,5-dimethyl-2,5-di(2-ethylhexanoylperoxy)hexane, 1-cyclohexyl-1-methylethyl peroxy-2-ethylhexanoate, t-hexyl peroxy-2-ethylhexanoate, t-butyl peroxy-2-ethylhexanoate, t-butyl peroxyisobutyrate, 1,1-bis(t-butylperoxy)cyclohexan
  • peroxy ketal examples include 1,1-bis(t-hexylperoxy)-3,3,5-trimethylcyclohexane, 1,1-bis(t-hexylperoxy)cyclohexane, 1,1-bis(t-butylperoxy)-3,3,5-trimethylcyclohexane, 1,1-bis(t-butylperoxy)cyclododecane, and 2,2-bis(t-butylperoxy)decane.
  • dialkyl peroxide examples include ⁇ , ⁇ ′-bis(t-butylperoxy)diisopropylbenzene, dicumyl peroxide, 2,5-dimethyl-2,5-di(t-butylperoxy)hexane, and t-butyl cumyl peroxide.
  • diacyl peroxide examples include isobutyl peroxide, 2,4-dichlorobenzoyl peroxide, 3,5,5-trimethylhexanoyl peroxide, octanoyl peroxide, lauroyl peroxide, stearoyl peroxide, succinic peroxide, benzoyl peroxytoluene, and benzoyl peroxide.
  • the oxidizing agent is preferably a peroxide, more preferably a hydroperoxide, and even more preferably cumene hydroperoxide.
  • the content of the oxidizing agent may be 0.1% by mass or more, 0.5% by mass or more, or 1% by mass or more, and may be 10% by mass or less, 5% by mass or less, or 3% by mass or less, based on the total liquid amount constituting the curable composition set.
  • the reducing agent contained in the second liquid may be, for example, a tertiary amine, a thiourea derivative, or a transition metal salt.
  • a tertiary amine include triethylamine, tripropylamine, tributylamine, and N,N-dimethyl-para-toluidine.
  • the thiourea derivative include 2-mercaptobenzimidazole, methylthiourea, dibutylthiourea, tetramethylthiourea, and ethylenethiourea.
  • the transition metal salt include cobalt naphthenate, copper naphthenate, and vanadyl acetylacetonate.
  • the reducing agent is preferably a thiourea derivative or a transition metal salt.
  • the thiourea derivative may be, for example, ethylenethiourea.
  • the transition metal salt is preferably vanadyl acetylacetonate.
  • the content of the reducing agent may be 0.05% by mass or more, 0.1% by mass or more, or 0.3% by mass or more, and may be 5% by mass or less, 3% by mass or less, or 1% by mass or less, based on the total liquid amount constituting the curable composition set.
  • the curable composition set may further contain additional polymerizable compounds and additives that can be used in the above-mentioned curable composition. These components may be contained in any one or both of the first liquid and the second liquid or may be contained in a third liquid, which is different from the first liquid and the second liquid. The content of these components based on the total liquid amount constituting the curable composition set may be similar to the range of the content of these components based on the total amount of the above-mentioned curable composition.
  • a cured product of the above-mentioned curable composition or a cured product of a mixture of the curable composition set has thermal conductivity and excellent elongation (depending on cases, also having low elasticity)
  • the cured product is suitably used as a thermally conductive material (also referred to as thermal dissipation material) in electronic components such as power modules, CPUs, and ECUs; batteries, LED lightings, and LED backlights. That is, an embodiment of the present invention provides a thermally conductive material containing the above-mentioned compound represented by the formula (1) and a thermally conductive filler.
  • FIG. 1 is a schematic cross-sectional view illustrating an embodiment of an electronic component containing a cured product of the curable composition.
  • the electronic component 1 A shown in FIG. 1 contains a semiconductor chip 21 as a heat source and a heat sink 22 as a thermal dissipation part.
  • the electronic component 1 A contains a cured product 11 of the above-mentioned curable composition, the cured product being provided between the semiconductor chip 21 and the heat sink 22 .
  • the cured product 11 may be a cured product of a mixture of the above-mentioned curable composition set.
  • the cured product 11 Since the cured product 11 has thermal conductivity, the cured product 11 works as a thermally conductive material (thermal interface material) in the electronic component 1 A, and heat is conducted from the semiconductor chip 21 to the heat sink 22 . Then, heat is dissipated from the heat sink 22 to the outside.
  • thermally conductive material thermal interface material
  • the cured product 11 has excellent elongation (depending on cases, also having low elasticity) by using the above-mentioned curable composition. Therefore, the cured product 11 has high followability to the deformation of the electronic component 1 A occurring due to heat or the like. Accordingly, the heat generated from the semiconductor chip 21 can be effectively conducted to the heat sink 22 . Furthermore, since the cured product 11 is a cured product of the above-mentioned curable composition, the cured product 11 also has excellent strength (for example, breaking strength).
  • the cured product 11 can also be obtained by disposing a liquid curable composition between the semiconductor chip 21 and the heat sink 22 and then curing the curable composition. Therefore, the generation of voids by liquid dripping and the pump-out phenomenon can be suppressed, and consequently, the adhesiveness of the cured product 11 (adhesiveness to the surface of the semiconductor chip 21 and the heat sink 22 ) can be made excellent.
  • the curing means and the curing conditions for the curable composition may be adjusted according to the composition of the curable composition or the type of the polymerization initiator.
  • the cured product 11 is disposed to be in direct contact with the semiconductor chip 21 and the heat sink 22 ; however, the cured product 11 may be thermally in contact with a heat source, or according to another embodiment, the cured product 11 may be disposed to be in contact with a heat source (semiconductor chip), with another member interposed therebetween.
  • FIG. 2 is a schematic cross-sectional view illustrating another embodiment of an electronic component containing a cured product of the curable composition.
  • the electronic component 1 B shown in FIG. 1 is a processor containing, on one surface of a substrate 23 , a semiconductor chip 21 as a heat source disposed with an underfill 24 interposed therebetween, a heat sink 22 as a thermal dissipation part, and a heat spreader 25 provided between the semiconductor chip 21 and the heat sink 22 .
  • a first cured product 11 provided to be in contact with the semiconductor chip 21 .
  • a second cured product 11 Provided between the heat spreader 25 and the heat sink 22 is a second cured product 11 .
  • the substrate 23 , the underfill 24 , and the heat spreader 25 may be formed from materials that are generally used in the art.
  • the substrate 23 may be a laminated substrate or the like
  • the underfill 24 may be formed from a resin such as an epoxy resin or the like
  • the heat spreader 25 may be a metal plate or the like.
  • the first cured product 11 and the second cured product 11 are each a cured product of the above-mentioned curable composition or a cured product of a mixture of the above-mentioned curable composition set.
  • the first cured product 11 is in direct contact with the semiconductor chip 21 as a heat source; however, the second cured product 11 is thermally in contact with the semiconductor chip 21 as a heat source, with the first cured product 11 and the heat spreader 25 interposed therebetween.
  • the cured products work as thermally conductive materials (thermal interface materials) for the electronic component 1 B. That is, the first cured product 11 promotes thermal conduction from the semiconductor chip 21 to the heat spreader 25 . Furthermore, the second cured product 11 promotes thermal conduction from the heat spreader 25 to the heat sink 22 . Then, heat is dissipated from the heat sink 22 to the outside.
  • the first cured product 11 and the second cured product 11 have excellent elongation (depending on cases, also having low elasticity) by using the above-mentioned curable composition. Therefore, the first cured product 11 and the second cured product 11 have high followability to the deformation of the electronic component 1 B occurring due to heat. Therefore, the heat generated from the semiconductor chip 21 can be more effectively conducted to the heat spreader 25 , and in addition, the heat can be more effectively conducted to the heat sink 22 . Furthermore, since the first cured product 11 and the second cured product 11 are cured products of the above-mentioned curable composition, the cured products also have excellent strength (for example, breaking strength).
  • the first cured product 11 and the second cured product 11 can also be obtained by disposing a liquid curable composition between the semiconductor chip 21 and the heat spreader 25 , or between the heat spreader 25 and the heat sink 22 , and then curing the curable composition. Therefore, even in the electronic component 1 B, the generation of voids caused by liquid dripping and the pump-out phenomenon of the curable composition can be suppressed, and consequently, excellent adhesiveness of the first cured product 11 and the second cured product 11 (adhesiveness to the surface of the semiconductor chip 21 , the heat spreader 25 , and/or the heat sink 22 ) can be obtained.
  • -r- is a reference symbol representing random copolymerization, which was synthesized by the procedure shown below (weight average molecular weight: 15000, mixture in which m1+m2 in the formula (1-7) is approximately 252 ⁇ 5 and n1+n2 is approximately an integer of 63 ⁇ 5 (provided that m1, m2, n1, and n2 each independently represent an integer of 2 or more, m1+n1 ⁇ 100, m2+n2 ⁇ 100), viscosity at 25° C.: 50 Pa ⁇ s)
  • -r- is a reference symbol representing random copolymerization, which was synthesized by the procedure shown below (weight average molecular weight: 16000, mixture in which in in the formula (1-8) is an integer of approximately 246 ⁇ 5 and n is an integer of approximately 105 ⁇ 5, viscosity at 25° C.: 55 Pa ⁇ s)
  • C-2 Plasticizer (glycol having a polyoxyalkylene chain, “NEWPOL 75H-90000” manufactured by Sanyo Chemical Co., Ltd.)
  • F-6 Filler made of aluminum (“TOYAL TECFILLER TFH-A05P” manufactured by Toyo Aluminum K.K.)
  • a 500-mL flask configured to contain a stirrer, a thermometer, a nitrogen gas inlet tube, a discharge tube, and a heating jacket was used as a reactor, 120 g of polyethylene glycol #6000 and 300 g of toluene were added to the reactor, the mixture was stirred at 45° C. and a speed of stirring rotation of 250 times/min, nitrogen was caused to flow at a rate of 100 mL/min, and the mixture was stirred for 30 minutes. Subsequently, the temperature was decreased to 25° C., after completion of temperature decrease, 2.9 g of acryloyl chloride was added dropwise to the reactor, and the mixture was stirred for 30 minutes.
  • the compound represented by the formula (1-6) was obtained by the same method as the method for synthesizing the compound represented by the formula (1-5), except that polyethylene glycol #6000 was changed to polyoxyethylene polyoxypropylene glycol (141 g of “NEWPOL PE78” manufactured by Sanyo Chemical Industries, Ltd.).
  • the compound represented by the formula (1-7) was obtained by the same method as the method for synthesizing the compound represented by the formula (1-5), except that polyethylene glycol #6000 was changed to a glycol having a polyoxyalkylene chain (225 g of “NEWPOL 75H-90000” manufactured by Sanyo Chemical Industries, Ltd.).
  • the compound represented by the formula (1-8) was obtained by the same method as the method for synthesizing the compound represented by the formula (1-5), except that polyethylene glycol #6000 was changed to 240 g of polyoxyethylene polyoxypropylene glycol (molecular weight 16000).
  • Various components were mixed at the blending ratio shown in Table 1, and a curable composition was obtained.
  • the curable composition was charged into a mold (formed from SUS plates) having a size of 10 cm ⁇ 10 cm ⁇ 0.2 mm, the mold was covered with a SUS plate as a top lid, and then the curable composition was cured by heating for 15 minutes under the conditions of 135° C., to obtain a cured product of each of the curable compositions according to Examples 1 to 19 and Comparative Example 1, each cured product having a thickness of 0.2 mm.
  • the produced cured product was cut into a square having a size of 10 mm ⁇ 10 mm ⁇ 0.2 mm and was subjected to a blackening treatment by graphite spraying, and then the diffusivity of heat was measured by a xenon flash method (“LFA447 nanoflash” manufactured by NETZSCH-Geratebau GmbH, Selb/Bayern) under the conditions of 25° C. From the product of this value, the density measured by the Archimedean method, and the specific heat at 25° C. measured with a differential scanning calorimeter (“DSC250” manufactured by TA Instruments, Inc.), the thermal conductivity in the thickness direction of the cured product was determined based on the following formula.
  • the elongation at break, tensile modulus, and breaking strength of the cured product at 25° C. were measured using a tensile tester (“Autograph EZ-TEST EZ-S” manufactured by SHIMADZU CORPORATION). Regarding the measurement, measurement was performed for the cured product having a shape of 0.2 mm (film thickness) ⁇ 5 mm (width) ⁇ 30 mm (length) based on JIS K7161 under the conditions of a distance between chucks of 20 mm and a tensile rate of 5 mm/min.
  • 1 A, 1 B electronic component
  • 11 cured product of curable composition
  • 21 semiconductor chip (heat source)
  • 22 heat sink
  • 23 substrate
  • 24 underfill
  • 25 heat spreader.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Physics & Mathematics (AREA)
  • Thermal Sciences (AREA)
  • Materials Engineering (AREA)
  • Combustion & Propulsion (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Macromonomer-Based Addition Polymer (AREA)
  • Polymerisation Methods In General (AREA)
US17/779,129 2019-11-29 2020-11-26 Curable composition and article Pending US20230002661A1 (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
JP2019216616 2019-11-29
JP2019-216616 2019-11-29
JP2020019070 2020-02-06
JP2020-019070 2020-02-06
PCT/JP2020/043999 WO2021107001A1 (fr) 2019-11-29 2020-11-26 Composition durcissable et article

Publications (1)

Publication Number Publication Date
US20230002661A1 true US20230002661A1 (en) 2023-01-05

Family

ID=76130535

Family Applications (2)

Application Number Title Priority Date Filing Date
US17/779,130 Pending US20230016868A1 (en) 2019-11-29 2020-11-26 Curable composition set and article
US17/779,129 Pending US20230002661A1 (en) 2019-11-29 2020-11-26 Curable composition and article

Family Applications Before (1)

Application Number Title Priority Date Filing Date
US17/779,130 Pending US20230016868A1 (en) 2019-11-29 2020-11-26 Curable composition set and article

Country Status (7)

Country Link
US (2) US20230016868A1 (fr)
EP (2) EP4056610A4 (fr)
JP (2) JPWO2021107001A1 (fr)
KR (2) KR20220108080A (fr)
CN (2) CN114729091A (fr)
TW (2) TW202128951A (fr)
WO (2) WO2021106992A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20220403081A1 (en) * 2019-11-29 2022-12-22 Showa Denko Materials Co., Ltd. Composition containing compound having polyoxyalkylene chain

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2023223978A1 (fr) * 2022-05-19 2023-11-23 株式会社レゾナック Composition qui contient un composé ayant une chaîne polyoxyalkylène et un agent à base d'ester conférant une thixotropie
WO2024019001A1 (fr) * 2022-07-19 2024-01-25 東亞合成株式会社 Composition thermoconductrice photodurcissable

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP3198285B2 (ja) * 1992-04-20 2001-08-13 ジェイエスアール株式会社 液状硬化性樹脂組成物
JP2938428B1 (ja) 1998-02-27 1999-08-23 信越化学工業株式会社 熱伝導性グリース組成物
JP2006022163A (ja) * 2004-07-06 2006-01-26 Kyocera Chemical Corp 熱硬化性樹脂成形材料
JP2009263542A (ja) * 2008-04-25 2009-11-12 Three M Innovative Properties Co （メタ）アクリル系粘着性発泡体及びその製造方法
JP5318733B2 (ja) 2009-11-26 2013-10-16 コスモ石油ルブリカンツ株式会社 熱伝導性グリース
KR101838533B1 (ko) * 2010-01-19 2018-04-26 카네카 코포레이션 경화성 조성물
JP5565176B2 (ja) * 2010-08-02 2014-08-06 Ｊｓｒ株式会社 組成物、その硬化物、および電子デバイス
JP2012188507A (ja) * 2011-03-09 2012-10-04 Kaneka Corp 放熱シート用組成物、および、これを硬化させてなる放熱シート
WO2020149193A1 (fr) * 2019-01-15 2020-07-23 コスモ石油ルブリカンツ株式会社 Composition durcissable, et produit durci

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20220403081A1 (en) * 2019-11-29 2022-12-22 Showa Denko Materials Co., Ltd. Composition containing compound having polyoxyalkylene chain

Also Published As

Publication number Publication date
CN114729091A (zh) 2022-07-08
TW202124520A (zh) 2021-07-01
KR20220108081A (ko) 2022-08-02
US20230016868A1 (en) 2023-01-19
TW202128951A (zh) 2021-08-01
JPWO2021106992A1 (fr) 2021-06-03
KR20220108080A (ko) 2022-08-02
EP4056611A1 (fr) 2022-09-14
JPWO2021107001A1 (fr) 2021-06-03
EP4056611A4 (fr) 2023-01-18
WO2021106992A1 (fr) 2021-06-03
WO2021107001A1 (fr) 2021-06-03
EP4056610A4 (fr) 2023-01-18
CN114651021A (zh) 2022-06-21
EP4056610A1 (fr) 2022-09-14

Similar Documents

Publication Publication Date Title
US20230002661A1 (en) Curable composition and article
US20240132645A1 (en) Composition containing compound having polyoxyalkylene chain and compound having poly(meth)acrylate chain
US20240132646A1 (en) Composition containing (meth)acrylamide compound and compound having polyoxyalkylene chain
JP7501225B2 (ja) メソゲン骨格を有する（メタ）アクリレートを含有する組成物
EP4056609A1 (fr) Composition contenant un composé ayant une chaîne polyoxyalkylène
JP2023062580A (ja) ポリオキシアルキレン鎖を有する化合物及び熱伝導性フィラーを含有する組成物
US20240043597A1 (en) Composition and sheet
WO2023223979A1 (fr) Composition qui contient un composé ayant une chaîne polyoxyalkylène et un copolymère acrylique
WO2023223978A1 (fr) Composition qui contient un composé ayant une chaîne polyoxyalkylène et un agent à base d'ester conférant une thixotropie
WO2024009895A1 (fr) Composition comprenant un polymère (méth)acrylique et des particules métalliques
CN116917363A (zh) 含有具有聚氧亚烷基链的化合物及具有聚（甲基）丙烯酸酯链的化合物的组合物
CN116917361A (zh) 含有具有聚氧亚烷基链的化合物及（甲基）丙烯酰胺化合物的组合物
US20240043648A1 (en) Composition and sheet containing cured product of same

Legal Events

Date Code Title Description
AS Assignment

Owner name: SHOWA DENKO MATERIALS CO., LTD., JAPAN

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:NAKAMURA, YUKI;FURUKAWA, NAOKI;YOKOTA, HIROSHI;AND OTHERS;SIGNING DATES FROM 20220602 TO 20220603;REEL/FRAME:060128/0836

STPP Information on status: patent application and granting procedure in general

Free format text: DOCKETED NEW CASE - READY FOR EXAMINATION

AS Assignment

Owner name: RESONAC CORPORATION, JAPAN

Free format text: CHANGE OF NAME;ASSIGNOR:SHOWA DENKO MATERIALS CO., LTD.;REEL/FRAME:063284/0307

Effective date: 20230101

AS Assignment

Owner name: RESONAC CORPORATION, JAPAN

Free format text: CHANGE OF ADDRESS;ASSIGNOR:RESONAC CORPORATION;REEL/FRAME:066547/0677

Effective date: 20231001