WO2014021090A1 - Feuille adhésive thermoconductrice - Google Patents

Feuille adhésive thermoconductrice Download PDF

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WO2014021090A1
WO2014021090A1 PCT/JP2013/069219 JP2013069219W WO2014021090A1 WO 2014021090 A1 WO2014021090 A1 WO 2014021090A1 JP 2013069219 W JP2013069219 W JP 2013069219W WO 2014021090 A1 WO2014021090 A1 WO 2014021090A1
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meth
heat conductive
conductive adhesive
acrylate
heat
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PCT/JP2013/069219
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English (en)
Japanese (ja)
Inventor
好夫 寺田
憲司 古田
中山　純一
翠 東城
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日東電工株式会社
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Priority to KR20147035723A priority Critical patent/KR20150040253A/ko
Priority to CN201380038685.2A priority patent/CN104487531A/zh
Publication of WO2014021090A1 publication Critical patent/WO2014021090A1/fr

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    • 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
    • C09J133/00—Adhesives based on homopolymers or 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 only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
    • C09J133/04—Homopolymers or copolymers of esters
    • C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • C09J133/10—Homopolymers or copolymers of methacrylic acid esters
    • 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
    • C09J133/00—Adhesives based on homopolymers or 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 only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
    • C09J133/04—Homopolymers or copolymers of esters
    • C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • 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
    • C09J133/00—Adhesives based on homopolymers or 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 only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
    • C09J133/04—Homopolymers or copolymers of esters
    • C09J133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
    • 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
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/20—Adhesives in the form of films or foils characterised by their carriers
    • C09J7/22—Plastics; Metallised plastics
    • 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
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/20—Adhesives in the form of films or foils characterised by their carriers
    • C09J7/28—Metal sheet
    • 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
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
    • 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
    • C09J9/00—Adhesives characterised by their physical nature or the effects produced, e.g. glue sticks
    • 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
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C08F220/1808—C8-(meth)acrylate, e.g. isooctyl (meth)acrylate or 2-ethylhexyl (meth)acrylate
    • 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
    • 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
    • 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
    • C09J2301/00—Additional features of adhesives in the form of films or foils
    • C09J2301/40—Additional features of adhesives in the form of films or foils characterized by the presence of essential components
    • C09J2301/408—Additional features of adhesives in the form of films or foils characterized by the presence of essential components additives as essential feature of the adhesive layer
    • 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
    • C09J2400/00—Presence of inorganic and organic materials
    • C09J2400/10—Presence of inorganic materials
    • C09J2400/16—Metal
    • C09J2400/163—Metal in the substrate
    • 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
    • C09J2433/00—Presence of (meth)acrylic polymer

Definitions

  • the present invention relates to a heat conductive pressure-sensitive adhesive sheet, and more particularly to a heat conductive pressure-sensitive adhesive sheet suitably used in industrial fields where both heat conductivity and pressure-sensitive adhesiveness are required.
  • Patent Document 1 has a problem that the thermal conductivity in the plane direction (the direction orthogonal to the thickness direction) is insufficient.
  • An object of the present invention is to provide a heat conductive pressure-sensitive adhesive sheet that is excellent in workability and handleability but also in appearance and in the direction perpendicular to the thickness direction.
  • the heat conductive adhesive sheet of this invention is equipped with the metal layer and the heat conductive adhesive layer laminated
  • the said heat conductive adhesive layer is a (meth) acrylic-acid alkylester. It contains an adhesive component obtained by polymerizing a monomer component containing, and thermally conductive particles, and the monomer component does not substantially contain a carboxyl group-containing monomer.
  • the monomer component further contains an amide group-containing monomer.
  • the heat conductive adhesive sheet of the present invention has a thermal conductivity in the direction perpendicular to the thickness direction of 20 W / m ⁇ K or more.
  • the heat conductive adhesive sheet of the present invention does not cause corrosion on the one surface of the metal layer when stored for 1000 hours in an atmosphere at a temperature of 85 ° C. and a relative humidity of 85%.
  • the heat conductive pressure-sensitive adhesive sheet of the present invention includes a metal layer, it is excellent in workability and handleability.
  • the heat conductive pressure-sensitive adhesive sheet further includes a heat conductive pressure-sensitive adhesive layer laminated on at least one side of the metal layer, and the heat conductive pressure-sensitive adhesive layer includes a monomer component containing (meth) acrylic acid alkyl ester. It contains a pressure-sensitive adhesive component obtained by polymerization and thermally conductive particles. Therefore, when the heat conductive pressure-sensitive adhesive layer is attached to the heat dissipation target, the heat generated from the heat dissipation target is conducted to the metal layer through the heat conductive pressure-sensitive adhesive layer containing the heat conductive particles, and subsequently It is conducted efficiently along the metal layer, that is, in the direction perpendicular to the thickness direction. In the heat conductive adhesive layer as well as the heat conduction in the metal layer described above, the heat generated from the heat dissipation target is efficiently conducted along the heat conductive adhesive layer, that is, in the direction orthogonal to the thickness direction. .
  • the heat conductive adhesive sheet is excellent in the heat conductivity in the orthogonal direction described above.
  • the monomer component does not substantially contain a carboxyl group-containing monomer, it is possible to prevent the occurrence of corrosion due to the carboxyl group on at least one surface of the metal layer. Therefore, it is possible to ensure a good appearance and prevent a reduction in the reliability of the arranged equipment.
  • FIG. 1 shows a cross-sectional view of one embodiment of the thermally conductive pressure-sensitive adhesive sheet of the present invention.
  • FIG. 1 shows a cross-sectional view of an embodiment of the thermally conductive adhesive sheet of the present invention.
  • a heat conductive pressure-sensitive adhesive sheet 1 includes a metal layer 2 and a heat conductive pressure-sensitive adhesive layer 3.
  • the metal layer 2 is formed in a flat plate shape (foil shape) that is the same shape as the outer shape of the heat conductive adhesive sheet 1.
  • the metal forming the metal layer 2 include copper, silver, gold, iron, chromium, nickel, aluminum, iron, and alloys thereof (stainless steel, copper-beryllium, phosphor bronze, iron-nickel, etc.). Can be mentioned.
  • copper and aluminum are used.
  • the thickness of the metal layer 2 is, for example, 1 ⁇ m or more, preferably 10 ⁇ m or more, and for example, 1000 ⁇ m or less, preferably 100 ⁇ m or less.
  • the thermal conductivity in the plane direction PD of the metal layer 2 is, for example, 50 W / m ⁇ K or more, preferably 100 W / m ⁇ K or more, more preferably 200 W / m ⁇ K or more, and 1000 W / M ⁇ K or less.
  • the thermal conductivity will be detailed in the evaluation of later examples.
  • the heat conductive adhesive layer 3 has both heat conductivity and adhesiveness (pressure-sensitive adhesiveness), and is laminated on the entire back surface (one surface in the thickness direction) of the metal layer 2.
  • the heat conductive adhesive layer 3 contains an adhesive component and heat conductive particles.
  • the adhesive component is obtained by polymerizing the monomer component.
  • the monomer component contains (meth) acrylic acid alkyl ester as a main component.
  • the (meth) acrylic acid alkyl ester is a methacrylic acid alkyl ester and / or an acrylic acid alkyl ester.
  • (meth) acrylic acid alkyl esters in view of easy balance of adhesive properties, (meth) acrylic acid C2-12 alkyl ester is preferred, and (meth) acrylic acid C4-9 is more preferred.
  • Examples include alkyl esters.
  • (Meth) acrylic acid alkyl ester is blended in the monomer component in a proportion of, for example, 60% by mass or more, preferably 80% by mass or more, for example, 99% by mass or less.
  • Examples of the monomer component further include an amide group-containing monomer and a copolymerizable monomer.
  • the amide group-containing monomer is an amide monomer containing an amide moiety (—CO—NR—, R represents a hydrogen atom or a hydrocarbon group) in the molecule, for example, N- (meth) acryloyl Cyclic (meth) acrylamides such as morpholine and N- (meth) acryloylpyrrolidine, such as (meth) acrylamide, N-substituted (meth) acrylamide (eg, N-ethyl (meth) acrylamide, Nn-butyl (meth) N-alkyl (meth) acrylamides such as acrylamide, for example, N, N-dimethyl (meth) acrylamide, N, N-diethyl (meth) acrylamide, N, N-dipropyl (meth) acrylamide, N, N-diisopropyl (meta) ) Acrylamide, N, N-di (n-butyl) (meth)
  • N-vinyl cyclic amide and N-hydroxyalkyl (meth) acrylamide are preferable.
  • the amide group-containing monomers can be used alone or in combination of two or more, preferably in combination. Specifically, the combined use of N-vinyl cyclic amide and N-hydroxyalkyl (meth) acrylamide is exemplified.
  • the amide group-containing monomer is blended in the monomer component, for example, in a proportion of 20% by mass or less, preferably 15% by mass or less, more preferably 10% by mass or less, and for example, 1% by mass or more.
  • the N-vinyl cyclic amide is, for example, 15% by mass or less, preferably 10% by mass or less in the monomer component. More preferably, it is blended at a ratio of 8% by mass or less, for example, 5% by mass or more, and N-hydroxyalkyl (meth) acrylamide is contained in the monomer component, for example, 5% by mass or less, preferably 4 mass% or less, More preferably, it is 3 mass% or less, for example, is mix
  • the copolymerizable monomer is a monomer copolymerizable with the above-described monomer ((meth) acrylic acid alkyl ester and / or amide group-containing monomer).
  • copolymerizable monomers include epoxy group-containing monomers such as glycidyl (meth) acrylate and allyl glycidyl ether, such as 2-methoxyethyl (meth) acrylate, 3-methoxypropyl (meth) acrylate, Alkoxy group-containing monomers such as (meth) acrylic acid methoxyethylene glycol and (meth) acrylic acid methoxypolypropylene glycol, for example, (meth) acrylic acid alkali metal salts such as sodium (meth) acrylate, such as acrylonitrile, methacrylonitrile Cyano group-containing monomers such as styrene, styrene monomers such as styrene and ⁇ -methylstyrene,
  • Heterocycle-containing (meth) acrylic acid esters such as acrylate, halogen atom-containing monomers such as fluoroalkyl (meth) acrylate, for example, alkoxysilyl such as 3- (meth) acryloxypropyltrimethoxysilane, vinyltrimethoxysilane Group-containing monomers, for example, siloxane skeleton-containing monomers such as (meth) acrylic group-containing silicones, such as cyclopropyl (meth) acrylate, cyclobutyl (meth) acrylate Cyclopentyl (meth) acrylate, cyclohexyl (meth) acrylate, cycloheptyl (meth) acrylate, cyclooctyl (meth) acrylate, bornyl (meth) acrylate, isobornyl (meth) acrylate and other alicyclic hydrocarbon group-containing (meta ) Acrylates such as phenyl (
  • the copolymerizable monomers can be used alone or in combination.
  • an alkoxy group-containing monomer is preferable.
  • the copolymerizable monomer is, for example, 30% by mass or less, preferably 20% by mass or less, more preferably 15% by mass or less, and, for example, 5% by mass or more, preferably 10% by mass in the monomer component. It mix
  • the monomer component includes, for example, a polar group-containing monomer (excluding a carboxyl group-containing monomer described later) such as a sulfo group-containing monomer, a nitrogen / sulfo group combined monomer, and a hydroxyl group / phosphate group combined monomer at an appropriate ratio. It can also be included.
  • a polar group-containing monomer excluding a carboxyl group-containing monomer described later
  • a sulfo group-containing monomer such as a sulfo group-containing monomer, a nitrogen / sulfo group combined monomer, and a hydroxyl group / phosphate group combined monomer at an appropriate ratio. It can also be included.
  • Examples of the sulfo group-containing monomer include styrene sulfonic acid, allyl sulfonic acid, sulfopropyl (meth) acrylate, (meth) acryloyloxynaphthalene sulfonic acid, and the like.
  • Examples of the nitrogen / sulfo group-containing monomer include 2- (meth) acrylamide-2-methylpropanesulfonic acid, (meth) acrylamidepropanesulfonic acid, and the like.
  • Examples of the monomer having a hydroxyl group and a phosphate group include 2-hydroxyethyl (meth) acryloyl phosphate.
  • the monomer component does not contain a carboxyl group-containing monomer. That is, the polar group-containing monomer does not contain a carboxyl group-containing monomer.
  • carboxyl group-containing monomer examples include (meth) acrylic acid (MA / AA), itaconic acid, maleic acid, fumaric acid, crotonic acid, isocrotonic acid, and the like, and carboxylic acids such as maleic anhydride and itaconic anhydride. Also included are anhydride acids such as carboxyalkyl (meth) acrylates such as carboxyethyl (meth) acrylate and carboxypentyl (meth) acrylate.
  • the monomer component contains a carboxyl group-containing monomer, the back surface of the metal layer 2 is corroded by the carboxyl group (acid group), and the appearance is deteriorated.
  • the content ratio of the adhesive component is, for example, 50% by mass or less, preferably 35% by mass or less, more preferably 30% by mass or less with respect to the heat conductive adhesive layer 3, and for example, 10% by mass. % Or more, preferably 20% by mass or more.
  • the heat conductive particles are formed into a particle shape from a heat conductive material, and examples of such a heat conductive material include a hydrated metal compound.
  • the hydrated metal compound has a decomposition start temperature in the range of 150 to 500 ° C., and has a general formula M x O y ⁇ nH 2 O (M is a metal atom, x and y are integers of 1 or more determined by the valence of the metal, n is a compound represented by the number of contained crystal water) or a double salt containing the above compound.
  • Examples of the hydrated metal compound include aluminum hydroxide [Al 2 O 3 .3H 2 O; or Al (OH) 3 ], boehmite [Al 2 O 3 .H 2 O; or AlOOH], magnesium hydroxide [MgO H 2 O; or Mg (OH) 2 ], calcium hydroxide [CaO ⁇ H 2 O; or Ca (OH) 2 ], zinc hydroxide [Zn (OH) 2 ], silicic acid [H 4 SiO 4 ; H 2 SiO 3 ; or H 2 Si 2 O 5 ], iron hydroxide [Fe 2 O 3 .H 2 O or 2FeO (OH)], copper hydroxide [Cu (OH) 2 ], barium hydroxide [BaO.
  • thermally conductive material examples include boron nitride, aluminum nitride, silicon nitride, gallium nitride, silicon carbide, silicon dioxide, aluminum oxide, magnesium oxide, titanium oxide, and zinc oxide. , Tin oxide, copper oxide, nickel oxide, antimonic acid doped tin oxide, calcium carbonate, barium titanate, potassium titanate, copper, silver, gold, nickel, aluminum, platinum, carbon (including diamond) and the like.
  • the heat conductive material is preferably a hydrated metal compound, more preferably aluminum hydroxide, because it imparts high heat conductivity and flame retardancy to the heat conductive pressure-sensitive adhesive layer 3.
  • the shape of the heat conductive particles is not particularly limited as long as it is particulate (powder), and may be, for example, a bulk shape, a needle shape, a plate shape, or a layer shape.
  • the bulk shape includes, for example, a spherical shape, a rectangular parallelepiped shape, a crushed shape, or a deformed shape thereof.
  • the size of the heat conductive particles is not particularly limited.
  • the primary average particle diameter is, for example, 0.1 ⁇ m or more, preferably 0.5 ⁇ m or more, more preferably 0.7 ⁇ m or more, and further preferably, For example, it is 1000 ⁇ m or less, preferably 200 ⁇ m or less, more preferably 100 ⁇ m or less, and further preferably 80 ⁇ m or less.
  • the primary particle size of the thermally conductive particles is determined based on the particle size distribution measured by the particle size distribution measurement method in the laser scattering method, more specifically, the volume-based average particle size, more specifically, the D50 value (cumulative 50% median diameter). ).
  • heat conductive particles are commercially available.
  • the heat conductive particles made of aluminum hydroxide the trade name “Hijilite H-100-ME” (manufactured by Showa Denko KK), the trade name “Heidilite H— 10 "(manufactured by Showa Denko KK), trade name” Hijilite H-32 "(manufactured by Showa Denko KK), trade name”
  • Heidilite H-31 “(manufactured by Showa Denko KK), trade name”
  • Heidilite H-42 trade name
  • trade name “Hijilite H-43M” manufactured by Showa Denko KK
  • trade name “B103ST” trade name (manufactured by Nippon Light Metal Co., Ltd.), etc.
  • thermally conductive particles made of magnesium hydroxide The product name “KISUMA 5A” (manufactured by Kyowa Chemical Industry Co., Ltd.) and the like can be mentioned.
  • thermally conductive particles made of boron nitride examples include trade name “HP-40” (manufactured by Mizushima Alloy Iron Co., Ltd.), trade name “PT620” (manufactured by Momentive), and the like.
  • Examples of the conductive particles include trade name “AS-50” (manufactured by Showa Denko KK), trade name “AS-10” (manufactured by Showa Denko KK), and the like, for example, as thermally conductive particles made of antimonic acid-doped tin oxide , Product name “SN-100S” (Ishihara Sangyo Co., Ltd.), product name “SN-100P” (Ishihara Sangyo Co., Ltd.), product name “SN-100D (water dispersion)” (Ishihara Sangyo Co., Ltd.)
  • Examples of the thermally conductive particles made of titanium oxide include the trade name “TTO series” (manufactured by Ishihara Sangyo Co., Ltd.).
  • the thermally conductive particles made of zinc oxide have the trade name “SnO— 10 "(manufactured by Sumitomo Osaka Cement Co., Ltd.) (manufactured by Sumitomo Osaka Cement Co., Ltd.) the trade name of" SnO-350 "(manufactured by Sumitomo Osaka Cement Co., Ltd.) the trade name of" SnO-410 "and the like.
  • These heat conductive particles can be used alone or in combination with a plurality of different types.
  • the content ratio of the heat conductive particles is, for example, less than 500 parts by weight with respect to 100 parts by weight of the adhesive component, preferably 450 parts by weight or less, more preferably 400 parts by weight or less, and further preferably 350 parts by weight. In addition, for example, 1 part by mass or more, preferably 10 parts by mass or more, more preferably 100 parts by mass or more, and further preferably 200 parts by mass or more.
  • the content ratio of the heat conductive particles is, for example, 50% by mass or more, preferably 65% by mass or more, more preferably 70% by mass or more with respect to the heat conductive pressure-sensitive adhesive layer 3. It is also 90% by mass or less, preferably 80% by mass or less.
  • the heat conductive pressure-sensitive adhesive layer 3 can be provided with excellent heat conductivity and excellent pressure-sensitive adhesiveness (pressure-sensitive adhesiveness).
  • the heat conductive adhesive layer 3 for example, first, an adhesive component is prepared, and the prepared adhesive component and thermally conductive particles are blended. Further, the adhesive component and the heat conductive particles can be blended at once.
  • the monomer component can be polymerized after blending the monomer composition containing the monomer component for forming the adhesive component and the thermally conductive particles.
  • the monomer component is polymerized.
  • a polymerization initiator is blended with the above-described monomer component.
  • polymerization initiator examples include a photopolymerization initiator and a thermal polymerization initiator.
  • the photopolymerization initiator examples include a benzoin ether photopolymerization initiator, an acetophenone photopolymerization initiator, an ⁇ -ketol photopolymerization initiator, an aromatic sulfonyl chloride photopolymerization initiator, and a photoactive oxime photopolymerization initiator.
  • Agents benzoin photopolymerization initiators, benzyl photopolymerization initiators, benzophenone photopolymerization initiators, thioxanthone photopolymerization initiators, and the like.
  • benzoin ether photopolymerization initiator examples include benzoin methyl ether, benzoin ethyl ether, benzoin propyl ether, benzoin isopropyl ether, benzoin isobutyl ether, 2,2-dimethoxy-1,2-diphenylethane-1-one, and anisole.
  • examples include methyl ether.
  • acetophenone photopolymerization initiator examples include 2,2-diethoxyacetophenone, 2,2-dimethoxy-2-phenylacetophenone, 4-phenoxydichloroacetophenone, 4- (t-butyl) dichloroacetophenone, and the like.
  • Examples of ⁇ -ketol photopolymerization initiators include 2-methyl-2-hydroxypropiophenone, 1- [4- (2-hydroxyethyl) phenyl] -2-methylpropan-1-one, and 1-hydroxy. Examples include cyclohexyl phenyl ketone.
  • aromatic sulfonyl chloride photopolymerization initiator examples include 2-naphthalene sulfonyl chloride.
  • Examples of the photoactive oxime photopolymerization initiator include 1-phenyl-1,1-propanedione-2- (o-ethoxycarbonyl) -oxime.
  • benzoin photopolymerization initiator examples include benzoin.
  • benzyl photopolymerization initiator examples include benzyl.
  • benzophenone photopolymerization initiator examples include benzophenone, benzoylbenzoic acid, 3,3′-dimethyl-4-methoxybenzophenone, and polyvinylbenzophenone.
  • thioxanthone photopolymerization initiator examples include thioxanthone, 2-chlorothioxanthone, 2-methylthioxanthone, 2,4-dimethylthioxanthone, isopropylthioxanthone, 2,4-diisopropylthioxanthone, decylthioxanthone, and the like.
  • thermal polymerization initiator examples include 2,2′-azobisisobutyronitrile, 2,2′-azobis-2-methylbutyronitrile, 2,2′-azobis (2-methylpropionic acid) dimethyl, 4,4'-azobis-4-cyanovaleric acid, azobisisovaleronitrile, 2,2'-azobis (2-amidinopropane) dihydrochloride, 2,2'-azobis [2- (5-methyl-2- Imidazolin-2-yl) propane] dihydrochloride, 2,2'-azobis (2-methylpropionamidine) disulfate, 2,2'-azobis (N, N'-dimethyleneisobutylamidine) hydrochloride, 2, Azo polymerization initiators such as 2′-azobis [N- (2-carboxyethyl) -2-methylpropionamidine] hydrate, Peroxide polymerization such as zoyl peroxide, t-butylpermaleate, di-tt-hexyl
  • These polymerization initiators can be used alone (only one kind) or in combination of two or more kinds.
  • a photopolymerization initiator is preferable because of the advantage that the polymerization time can be shortened. More preferred are benzoin ether photopolymerization initiators and ⁇ -ketol photopolymerization initiators.
  • the photopolymerization initiator When blending a photopolymerization initiator as a polymerization initiator, the photopolymerization initiator is, for example, 0.01 parts by mass or more, preferably 0.05 parts by mass or more, with respect to 100 parts by mass of the monomer component. Further, for example, it is blended at a ratio of 5 parts by mass or less, preferably 3 parts by mass or less.
  • thermal polymerization initiator when a thermal polymerization initiator is blended as a polymerization initiator, the thermal polymerization initiator is not particularly limited and is blended in an available ratio.
  • the monomer component is partially polymerized as necessary.
  • the mixture of the monomer component and the photopolymerization initiator is irradiated with ultraviolet rays.
  • the monomer composition has a viscosity (BH viscometer, No. 5 rotor, 10 rpm, measurement temperature 30 ° C.) with irradiation energy that excites the photopolymerization initiator, for example, 5 Pa ⁇ s.
  • irradiation is preferably performed until the pressure is 10 Pa ⁇ s or more, for example, 30 Pa ⁇ s or less, and preferably 20 Pa ⁇ s or less.
  • the mixture of the monomer component and the thermal polymerization initiator is polymerized at, for example, a temperature higher than the decomposition temperature of the thermal polymerization initiator, specifically about 20 to 100 ° C.
  • the viscosity of the monomer composition is, for example, 5 Pa ⁇ s or more, preferably Heating is performed until the pressure reaches 10 Pa ⁇ s or higher, for example, 30 Pa ⁇ s or lower, preferably 20 Pa ⁇ s or lower.
  • a monomer component selected from (meth) acrylic acid alkyl ester, amide group-containing monomer and copolymerizable monomer, and polymerization initiation
  • a monomer component can be polymerized and then a crosslinking agent can be blended.
  • the crosslinking agent is a polyfunctional compound having a plurality of ethylenically unsaturated hydrocarbon groups.
  • the crosslinking agent can be used alone or in combination.
  • dipentaerythritol hexa (meth) acrylate is preferable.
  • the content of the crosslinking agent is, for example, 0.001 part by mass or more, preferably 0.01 part by mass or more, for example, 10 parts by mass or less, preferably 1 part by mass with respect to 100 parts by mass of the monomer component. It is also below mass parts.
  • the monomer composition is prepared as a syrup having the above-described viscosity when the monomer component is partially polymerized.
  • heat conductive particles are then blended into the prepared monomer composition.
  • the thermally conductive particles are blended into the monomer composition so as to have the blending ratio described above.
  • the heat conductive adhesive raw material containing a monomer composition and a heat conductive particle is prepared.
  • the monomer composition and / or the heat conductive adhesive raw material include a crosslinking agent, a dispersant (for example, a nonionic surfactant), a tackifier, a silane coupling agent, a plasticizer, and a filler as necessary.
  • a dispersant for example, a nonionic surfactant
  • a tackifier for example, a silane coupling agent
  • a plasticizer for example, a tackifier
  • a filler as necessary.
  • additives such as an anti-aging agent and a coloring agent can be blended at an appropriate ratio.
  • the viscosity (BM viscometer, No. 4 rotor, 12 rpm, measurement temperature 23 ° C.) of the obtained heat conductive adhesive raw material is, for example, 50 Pa ⁇ s or less, preferably 40 Pa ⁇ s or less, more preferably 35 Pa. S or less, and for example, 5 Pa ⁇ s or more, preferably 10 Pa ⁇ s or more.
  • a base film 4 indicated by an imaginary line in FIG. 1 is prepared, and a heat conductive adhesive raw material is applied to the surface of the base film 4 that has been subjected to the peeling treatment.
  • the base film 4 includes a release liner.
  • a polyester film polyethylene terephthalate film or the like
  • a fluorine-based polymer for example, polytetrafluoroethylene, polychlorotrifluoroethylene, polyvinyl fluoride, polyvinyl fluoride, or the like.
  • Fluorine-containing films made of vinylidene fluoride, tetrafluoroethylene-hexafluoropropylene copolymer, chlorofluoroethylene-vinylidene fluoride copolymer, etc.
  • olefin-based resin films made of olefin-based resins (polyethylene, polypropylene, etc.)
  • transmits an ultraviolet-ray is used so that irradiation of the ultraviolet rays with respect to a heat conductive adhesive raw material may not be prevented.
  • Examples of the method for applying the heat conductive adhesive raw material to the base film 4 include roll coating, kiss roll coating, gravure coating, reverse coating, roll brush, spray coating, dip roll coating, bar coating, knife coating, and air knife. Examples thereof include an extrusion coating method using a coat, a curtain coat, a lip coat, a die coater, and the like.
  • the coating thickness of the heat conductive adhesive raw material is, for example, 10 ⁇ m or more, preferably 50 ⁇ m or more, more preferably 100 ⁇ m or more, and for example, 10,000 ⁇ m or less, preferably 5000 ⁇ m or less, more preferably, It is also less than 3000 ⁇ m.
  • a cover film (not shown) is then placed on the thermal conductive adhesive material coating.
  • the cover film is arranged so that the surface on which the cover film is peeled is in contact with the coating film.
  • cover film examples include the same film as the base film 4 described above. Moreover, when the heat conductive adhesive raw material contains the photoinitiator, the cover film which permeate
  • the monomer component in the heat conductive adhesive raw material is then polymerized.
  • the heat conductive adhesive raw material is irradiated with ultraviolet light, or heat polymerization is performed.
  • the initiator is blended, the heat conductive adhesive raw material is heated.
  • the heat conductive adhesive layer 3 is formed from a heat conductive adhesive raw material, the base film 4 is laminated
  • the thickness of the heat conductive adhesive layer 3 is, for example, 10 ⁇ m or more, preferably 50 ⁇ m or more, more preferably 100 ⁇ m or more, and for example, 10,000 ⁇ m or less, preferably 5000 ⁇ m or less, more preferably 3000 ⁇ m or less. But there is.
  • the heat conductive adhesive layer 3 is laminated on the back surface of the metal layer 2.
  • the cover film is peeled off from the surface of the heat conductive pressure-sensitive adhesive layer 3, and then the surface of the heat conductive pressure-sensitive adhesive layer 3 is attached to the back surface of the metal layer 2.
  • stacked on the back surface is obtained.
  • the base film 4 is laminated on the back surface of the heat conductive pressure-sensitive adhesive layer 3, and the base film 4 is peeled off from the heat conductive pressure-sensitive adhesive layer 3 when the heat conductive pressure-sensitive adhesive sheet 1 is used.
  • the thickness of the obtained heat conductive adhesive sheet 1 is, for example, 15 ⁇ m or more, preferably 50 ⁇ m or more, more preferably 100 ⁇ m or more, and for example, 10,000 ⁇ m or less, preferably 5000 ⁇ m or less, more preferably, It is also less than 3000 ⁇ m.
  • the thermal conductivity of the surface direction PD of the heat conductive adhesive sheet 1 is, for example, 20 W / m ⁇ K or more, preferably 50 W / m ⁇ K or more, more preferably 100 W / m ⁇ K or more, It is also 500 W / m ⁇ K or less.
  • the thermal conductivity will be detailed in the evaluation of later examples.
  • the heat conductivity of the surface direction PD of the heat conductive adhesive sheet 1 is more than the said minimum, it can be used suitably for the apparatus (after-mentioned) in which high heat dissipation is required.
  • the heat conductive adhesive sheet 1 obtained in this way is used as a heat radiating sheet for various devices.
  • this heat conductive adhesive sheet 1 is excellent in heat conductivity and adhesiveness (pressure-sensitive adhesiveness), it is used after being attached (pressure-sensitive adhesive) to a heat radiation target of various devices. Specifically, the heat conductive pressure-sensitive adhesive layer 3 of the heat conductive pressure-sensitive adhesive sheet 1 is used by being attached (pressure-sensitive adhesion) to a heat dissipation target.
  • the device is a device that requires high heat dissipation.
  • a semiconductor device for example, a semiconductor device, a hard disk, an LED device (television, illumination, display, etc.), an EL device (organic EL display, organic EL illumination) Etc.), capacitors (capacitors etc.), batteries (lithium ion batteries etc.), power modules and the like.
  • the heat conductive pressure-sensitive adhesive sheet 1 has greatly improved thermal conductivity in the surface direction, and therefore, with lighter and smaller size, devices that require even higher heat dissipation, specifically, for example, It is used for a mobile phone (so-called smart phone) having functions of a personal computer and a PDA (personal digital assistant), for example, a portable personal computer (so-called tablet PC) having a touch panel display / input unit.
  • the heat conductive adhesive sheet 1 can also be used for a digital camera, a projector, etc., for example.
  • the heat conductive adhesive sheet 1 is affixed on heat radiating members, such as a chip
  • the heat conductive adhesive sheet 1 when arrange
  • this heat conductive adhesive sheet 1 is equipped with the metal layer 2, it is excellent in workability and handleability.
  • the heat conductive adhesive sheet 1 is further provided with the heat conductive adhesive layer 3 laminated
  • the heat conductive adhesive sheet 1 is excellent in the heat conductivity of the surface direction PD.
  • the monomer component does not substantially contain a carboxyl group-containing monomer, it is possible to prevent the occurrence of corrosion due to the carboxyl group on the back surface of the metal layer 2. Specifically, no corrosion occurs on the back surface of the metal layer 2 in the corrosion test described in detail in the following examples. Therefore, it is possible to ensure a good appearance and prevent a reduction in the reliability of the arranged equipment.
  • the heat conductive adhesive layer 3 is provided only in the back surface of the metal layer 2, as shown by the broken line and the continuous line of FIG.
  • the pressure-sensitive adhesive layer 3 can be further provided on the surface of the metal layer 2.
  • the heat conductive adhesive layer 3 is provided on both the front and back surfaces of the metal layer 2.
  • Example 1 As monomer components, 80 parts by weight of 2-ethylhexyl acrylate as a main component, 11.5 parts by weight of 2-methoxyethyl acrylate as a copolymerizable monomer, and N-vinyl-2- as an amide group-containing monomer A mixture in which 7 parts by weight of pyrrolidone (NVP) and 1.5 parts by weight of hydroxyethyl acrylamide (HEAA) as an amide group-containing monomer were mixed was prepared.
  • NDP pyrrolidone
  • HEAA hydroxyethyl acrylamide
  • the mixture was irradiated with ultraviolet rays and polymerized until the viscosity (BH viscometer, No. 5 rotor, 10 rpm, measurement temperature 30 ° C.) reached about 20 Pa ⁇ s, and the monomer component was partially polymerized.
  • a partial polymer (syrup) was prepared.
  • the product name “KAYARAD DPHA-40H” dipentaerythritol hexaacrylate, Nippon Kayaku Co., Ltd.) 0.05 parts by weight as a crosslinking agent to 100 parts by weight of the prepared syrup, and the product name “Plisurf A212E” (No. A monomer composition was prepared by mixing and mixing 2 parts by weight of Ichiko Pharmaceutical Co., Ltd.
  • the prepared heat conductive adhesive raw material was used for the release treatment surface of a base film (trade name “Diafoil MRF38”, manufactured by Mitsubishi Chemical Polyester Film Co., Ltd.), which is a release liner made of polyethylene terephthalate.
  • a cover film (trade name “Diafoil MRF38”, Mitsubishi) is a release liner made of polyethylene terephthalate that has been subjected to a release treatment on one side of the coating film of the heat conductive adhesive material. Chemical polyester film) was laminated so that the release-treated surface was in contact with the coating film.
  • the heat conductive adhesive material was irradiated with ultraviolet rays (illuminance of about 5 mW / cm 2 ) from both sides (both release liners) for 3 minutes.
  • the monomer component in the heat conductive adhesive material was polymerized to form a heat conductive adhesive layer having a thickness of 200 ⁇ m.
  • the cover film is peeled off from the heat conductive adhesive layer, and the heat conductive adhesive layer is made of a 50 ⁇ m thick aluminum foil (surface direction thermal conductivity 237 W / m ⁇ K, manufactured by Sumi Light Metal Foil Co., Ltd.).
  • a heat conductive pressure-sensitive adhesive sheet was prepared by bonding to one side (see FIG. 1).
  • Example 2 A heat conductive pressure-sensitive adhesive sheet was prepared in the same manner as in Example 1 except that the metal foil was changed to a copper foil having a thickness of 35 ⁇ m (surface direction thermal conductivity 398 W / m ⁇ K).
  • Example 1 Comparative Example 1 In Example 1, the amount of syrup was set to 95 parts by weight, and further, 5 parts by weight of acrylic acid (AA) was added as a monomer component. Produced.
  • AA acrylic acid
  • Comparative Example 2 A heat conductive adhesive sheet was prepared in the same manner as in Example 1 except that the heat conductive adhesive raw material was prepared without adding the heat conductive particles.
  • Thermal conductivity density ⁇ specific heat ⁇ thermal diffusivity
  • the specific heat of the thermally conductive adhesive sheet was determined by a DSC (Differential Scanning Calorimeter) method. Specifically, it was determined by a DSC method using a differential scanning calorimeter DSC-7 manufactured by Perkin-Elmer. 2. Corrosion of the back side of the metal layer (corrosion test) The heat conductive adhesive sheet was preserve
  • the heat conductive adhesive sheet is used as a heat dissipation sheet for various devices.

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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)
  • Adhesive Tapes (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Laminated Bodies (AREA)

Abstract

L'invention concerne une feuille adhésive thermoconductrice qui comprend une couche métallique et une couche d'agent adhésif thermoconductrice stratifiée sur au moins une surface de la couche métallique. La couche d'agent adhésif thermoconductrice contient : un composant adhésif qui est fabriqué par polymérisation d'un composant monomère comprenant un ester alkylique d'acide (méth)acrylique ; et des particules thermoconductrices. Le composant monomère ne contient sensiblement pas de monomère contenant un groupe carboxyle.
PCT/JP2013/069219 2012-07-30 2013-07-12 Feuille adhésive thermoconductrice WO2014021090A1 (fr)

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KR20147035723A KR20150040253A (ko) 2012-07-30 2013-07-12 열전도성 점착 시트
CN201380038685.2A CN104487531A (zh) 2012-07-30 2013-07-12 导热性粘合片

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WO2015156258A1 (fr) * 2014-04-07 2015-10-15 日本ゼオン株式会社 Procédé de production d'une feuille stratifiée, adhésive, sensible à la pression, thermoconductrice, feuille stratifiée, adhésive, sensible à la pression, thermoconductrice et dispositif électronique

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KR101828644B1 (ko) * 2014-03-25 2018-02-14 주식회사 엘지화학 방열 점착 테이프용 점착제 조성물 및 방열 점착 테이프
JP6623474B2 (ja) 2016-03-28 2019-12-25 北川工業株式会社 熱伝導部材、熱伝導部材の製造方法、及び熱伝導構造体
KR102539196B1 (ko) * 2016-08-18 2023-06-02 삼성디스플레이 주식회사 플렉서블 표시 장치
JP2021001266A (ja) * 2019-06-21 2021-01-07 日東電工株式会社 粘着シート

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WO1998023700A1 (fr) * 1996-11-29 1998-06-04 Nitto Denko Corporation Adhesif autocollant thermoconducteur et feuille adhesive comportant cet adhesif
WO1998024860A1 (fr) * 1996-12-04 1998-06-11 Nitto Denko Corporation Adhesif autocollant conducteur thermique, feuille adhesive contenant cet adhesif, et procede de fixation d'une piece electronique a un element emettant un rayonnement thermique au moyen de cet adhesif
JPH10316953A (ja) * 1997-05-16 1998-12-02 Nitto Denko Corp 剥離可能な熱伝導性感圧接着剤とその接着シ―ト類
JPH10324853A (ja) * 1997-05-23 1998-12-08 Nitto Denko Corp 剥離可能な熱伝導性感圧接着剤とその接着シ―ト類
JPH10330692A (ja) * 1997-06-03 1998-12-15 Nitto Denko Corp 熱伝導性感圧接着剤とその接着シ―ト類
JP2005325250A (ja) * 2004-05-14 2005-11-24 Nitto Denko Corp 金属面貼付用感圧性粘着シート類および金属面を有する物品
JP2009280729A (ja) * 2008-05-23 2009-12-03 Nitto Denko Corp 粘着剤組成物および金属面貼付用粘着シート
JP2012036366A (ja) * 2010-01-29 2012-02-23 Nitto Denko Corp 熱伝導性接着シート

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WO1998023700A1 (fr) * 1996-11-29 1998-06-04 Nitto Denko Corporation Adhesif autocollant thermoconducteur et feuille adhesive comportant cet adhesif
WO1998024860A1 (fr) * 1996-12-04 1998-06-11 Nitto Denko Corporation Adhesif autocollant conducteur thermique, feuille adhesive contenant cet adhesif, et procede de fixation d'une piece electronique a un element emettant un rayonnement thermique au moyen de cet adhesif
JPH10316953A (ja) * 1997-05-16 1998-12-02 Nitto Denko Corp 剥離可能な熱伝導性感圧接着剤とその接着シ―ト類
JPH10324853A (ja) * 1997-05-23 1998-12-08 Nitto Denko Corp 剥離可能な熱伝導性感圧接着剤とその接着シ―ト類
JPH10330692A (ja) * 1997-06-03 1998-12-15 Nitto Denko Corp 熱伝導性感圧接着剤とその接着シ―ト類
JP2005325250A (ja) * 2004-05-14 2005-11-24 Nitto Denko Corp 金属面貼付用感圧性粘着シート類および金属面を有する物品
JP2009280729A (ja) * 2008-05-23 2009-12-03 Nitto Denko Corp 粘着剤組成物および金属面貼付用粘着シート
JP2012036366A (ja) * 2010-01-29 2012-02-23 Nitto Denko Corp 熱伝導性接着シート

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Publication number Priority date Publication date Assignee Title
WO2015156258A1 (fr) * 2014-04-07 2015-10-15 日本ゼオン株式会社 Procédé de production d'une feuille stratifiée, adhésive, sensible à la pression, thermoconductrice, feuille stratifiée, adhésive, sensible à la pression, thermoconductrice et dispositif électronique

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CN104487531A (zh) 2015-04-01
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KR20150040253A (ko) 2015-04-14

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