WO2020115914A1 - Composition de résine, feuille de résine, substrat métallique, dispositif semi-conducteur de puissance et procédé de fabrication de substrat métallique - Google Patents

Composition de résine, feuille de résine, substrat métallique, dispositif semi-conducteur de puissance et procédé de fabrication de substrat métallique Download PDF

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Publication number
WO2020115914A1
WO2020115914A1 PCT/JP2018/045188 JP2018045188W WO2020115914A1 WO 2020115914 A1 WO2020115914 A1 WO 2020115914A1 JP 2018045188 W JP2018045188 W JP 2018045188W WO 2020115914 A1 WO2020115914 A1 WO 2020115914A1
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Prior art keywords
resin sheet
metal
resin composition
meth
resin
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PCT/JP2018/045188
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English (en)
Japanese (ja)
Inventor
一也 木口
古川　直樹
森本　剛
智彦 小竹
藤本　大輔
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日立化成株式会社
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Priority to PCT/JP2018/045188 priority Critical patent/WO2020115914A1/fr
Publication of WO2020115914A1 publication Critical patent/WO2020115914A1/fr

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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B15/00—Layered products comprising a layer of metal
    • B32B15/04—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material
    • B32B15/08—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F299/00—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/18—Manufacture of films or sheets
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L23/00—Details of semiconductor or other solid state devices
    • H01L23/34—Arrangements for cooling, heating, ventilating or temperature compensation ; Temperature sensing arrangements
    • H01L23/36—Selection of materials, or shaping, to facilitate cooling or heating, e.g. heatsinks
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L23/00—Details of semiconductor or other solid state devices
    • H01L23/34—Arrangements for cooling, heating, ventilating or temperature compensation ; Temperature sensing arrangements
    • H01L23/36—Selection of materials, or shaping, to facilitate cooling or heating, e.g. heatsinks
    • H01L23/373—Cooling facilitated by selection of materials for the device or materials for thermal expansion adaptation, e.g. carbon
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L25/00—Assemblies consisting of a plurality of individual semiconductor or other solid state devices ; Multistep manufacturing processes thereof
    • H01L25/03—Assemblies consisting of a plurality of individual semiconductor or other solid state devices ; Multistep manufacturing processes thereof all the devices being of a type provided for in the same subgroup of groups H01L27/00 - H01L33/00, or in a single subclass of H10K, H10N, e.g. assemblies of rectifier diodes
    • H01L25/04—Assemblies consisting of a plurality of individual semiconductor or other solid state devices ; Multistep manufacturing processes thereof all the devices being of a type provided for in the same subgroup of groups H01L27/00 - H01L33/00, or in a single subclass of H10K, H10N, e.g. assemblies of rectifier diodes the devices not having separate containers
    • H01L25/07—Assemblies consisting of a plurality of individual semiconductor or other solid state devices ; Multistep manufacturing processes thereof all the devices being of a type provided for in the same subgroup of groups H01L27/00 - H01L33/00, or in a single subclass of H10K, H10N, e.g. assemblies of rectifier diodes the devices not having separate containers the devices being of a type provided for in group H01L29/00
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L25/00—Assemblies consisting of a plurality of individual semiconductor or other solid state devices ; Multistep manufacturing processes thereof
    • H01L25/18—Assemblies consisting of a plurality of individual semiconductor or other solid state devices ; Multistep manufacturing processes thereof the devices being of types provided for in two or more different subgroups of the same main group of groups H01L27/00 - H01L33/00, or in a single subclass of H10K, H10N

Definitions

  • the present invention relates to a resin composition, a resin sheet, a metal substrate, a power semiconductor device, and a method for manufacturing a metal substrate.
  • a laminated body in which a resin layer for insulation or the like is arranged between a pair of members is used for various purposes (see, for example, Patent Document 1).
  • Such a laminate has been manufactured by attaching both members via a resin sheet.
  • the cured product of the resin sheet described in Patent Document 1 has high thermal conductivity, it is necessary to apply heat of 100° C. or higher when the resin sheet is cured and manufactured, and thus a heating device or the like for curing the resin sheet is used. Will be needed. Further, even when it is assumed that a resin sheet or the like that is cured by light, moisture or the like is supposed to be cured, a device, equipment, etc. for curing the resin sheet are required separately. Therefore, it is desirable to use a resin sheet that can be cured under room temperature conditions or conditions close to room temperature without requiring any special device or equipment.
  • One form of the present invention has been made in view of the above, can be cured under room temperature conditions or conditions close to room temperature, a resin composition and a resin sheet excellent in pot life, and using this resin sheet
  • An object is to provide a metal substrate, a power semiconductor device, and a method for manufacturing a metal substrate.
  • the present inventors have accomplished the present invention as a result of extensive studies to solve the above problems. That is, the present invention includes the following aspects.
  • ⁇ 4> The resin composition according to ⁇ 3>, wherein the content of the inorganic filler is 40% by volume to 90% by volume based on the total solid content.
  • the two main surfaces are respectively adhered to an adherend, and at least one main surface is used by being adhered to a surface of the adherend containing at least one of metal and metal ions.
  • ⁇ 7> The resin sheet according to ⁇ 5> or ⁇ 6>, wherein at least one of the two main surfaces is used by being bonded to a metal-containing layer containing at least one of a metal and a metal ion.
  • ⁇ 8> The resin sheet according to any one of ⁇ 5> to ⁇ 7>, wherein the resin sheet has a thickness of 30 ⁇ m to 400 ⁇ m.
  • ⁇ 9> The resin sheet according to any one of ⁇ 5> to ⁇ 8>, which is cured at a temperature of 5° C. to 70° C.
  • a method of manufacturing a metal substrate comprising: ⁇ 13> The method for producing a metal substrate according to ⁇ 12>, wherein in the curing step, the resin sheet is cured at a temperature of 5°C to 70°C.
  • a resin composition and a resin sheet that can be cured under room temperature conditions or conditions close to room temperature and have an excellent pot life, and a metal substrate, a power semiconductor device and a metal using the resin sheet.
  • a method for manufacturing a substrate can be provided.
  • the present invention is not limited to the following embodiments.
  • the constituent elements including element steps and the like
  • the term “process” includes not only a process independent of other processes but also the process even if the process is not clearly distinguishable from the other processes as long as the purpose of the process is achieved. ..
  • the numerical range indicated by using "to” includes the numerical values before and after "to" as the minimum value and the maximum value, respectively.
  • each component may include a plurality of types of applicable substances.
  • the content rate or content of each component is the total content rate or content of the multiple types of substances present in the composition unless otherwise specified. Means quantity.
  • a plurality of types of particles corresponding to each component may be included.
  • the particle size of each component means a value for a mixture of the plurality of types of particles present in the composition unless otherwise specified.
  • the term “layer” may include not only the case where the layer is formed over the entire area when the area where the layer is present is observed, but also the case where the layer is formed only in a part of the area. included.
  • the term “laminate” refers to stacking layers, two or more layers may be combined and two or more layers may be removable.
  • (meth)acrylic means acrylic or methacrylic
  • (meth)acryloyl means acryloyl or methacryloyl
  • (meth)acrylate means acrylate or methacrylate
  • the resin composition of the present disclosure includes a multimer having an anaerobic curable functional group in its side chain, and is used under anaerobic conditions in which oxygen supply is suppressed.
  • the above resin composition is used to obtain a cured product obtained by curing under anaerobic conditions, and more specifically, a resin sheet that is a sheet-shaped molded product of this resin composition is anaerobic. It is used to obtain a cured product that is cured under the conditions.
  • the above-mentioned resin composition can be cured under room temperature conditions or conditions close to room temperature, and is cured under anaerobic conditions, so that unintentional curing hardly occurs and the pot life is excellent.
  • the resin composition of the present disclosure includes a multimer having an anaerobic curable functional group in the side chain. This makes it possible to increase the strength of the resin composition before and after curing, and when the resin composition containing a monomer having an anaerobic curable functional group and not containing the above-described polymer is cured. In comparison, the generation of volatile components can be suppressed.
  • the anaerobic conditions in which the supply of oxygen is suppressed means that a molded product of a resin composition such as a resin sheet formed by molding the resin composition into a sheet from the outside (hereinafter, "resin sheet”). It is also referred to as “etc.”) in which the oxygen is not supplied to the resin sheet or the like from the outside.
  • the environment where it is difficult to supply oxygen to the resin sheet or the like from the outside means that the two main surfaces of the resin sheet or the like are in contact with members each having an oxygen permeability of 0.5 mL/(m 2 ⁇ 24 h ⁇ atm) or less. Means that.
  • the oxygen permeability of the two metal members when the two main surfaces of a resin sheet or the like are respectively brought into contact with a metal member, the oxygen permeability of the two metal members may be 0.5 mL/(m 2 ⁇ 24h ⁇ atm) or less, When the two main surfaces are brought into contact with the metal member and the resin member, respectively, the oxygen permeability of the metal member and the resin member may be 0.5 mL/(m 2 ⁇ 24 h ⁇ atm) or less.
  • the oxygen permeability of the member can be measured under the conditions of a temperature of 23° C. and a relative humidity of 65% using an oxygen permeability measuring device (for example, MOCON, OX-TRAN).
  • the resin composition of the present disclosure includes a multimer having an anaerobic curable functional group in its side chain (hereinafter, also referred to as “specific multimer”).
  • the anaerobic curable functional group may be any functional group capable of initiating a curing reaction under anaerobic conditions, and at least one of the two main surfaces of the resin sheet or the like under anaerobic conditions is a metal or a metal ion. It is preferably a functional group that initiates a curing reaction under the condition of being in contact with at least one.
  • the anaerobic curable functional group (meth)acryloyl group, vinyl group, allyl group and the like can be mentioned.
  • the multimer preferably has two or more anaerobic curable functional groups in one molecule.
  • the multimer may or may not have an anaerobic curable functional group in the main chain.
  • the specific multimer preferably has an anaerobic curable functional group at the side chain terminal from the viewpoint of strength when the resin composition is used as a cured product.
  • the specific multimer may have an anaerobic curable functional group at the main chain terminal, or may have each at the main chain terminal and the side chain terminal.
  • the main chain of the specific multimer includes olefins such as ethylene and propylene, styrene, vinyl chloride, vinylidene chloride, acrylonitrile, vinylcarbazole, (meth)acrylic acid, methyl (meth)acrylate, ethyl (meth)acrylate, It may have a structure in which a monomer such as a monofunctional (meth)acrylic compound having a polyalkylene structure such as (meth)acrylate or methacrylate is homopolymerized or copolymerized.
  • olefins such as ethylene and propylene, styrene, vinyl chloride, vinylidene chloride, acrylonitrile, vinylcarbazole, (meth)acrylic acid, methyl (meth)acrylate, ethyl (meth)acrylate, It may have a structure in which a monomer such as a monofunctional (meth)acrylic compound having a polyalkylene structure such as (
  • the specific multimer may include, for example, a multimer represented by the following general formula (I).
  • R 4's each independently represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a hydroxyalkyl group having 1 to 4 carbon atoms, or a hydroxyalkyl group having 1 to 4 carbon atoms.
  • a group in which one hydrogen atom is replaced with an anaerobic curable functional group is shown.
  • R 5's each independently represent a hydrogen atom or a methyl group.
  • R 6 represents a hydrogen atom, a hydroxy group, or a group in which one hydrogen atom of a hydroxyalkyl group having 1 to 4 carbon atoms is substituted with an anaerobic curable functional group.
  • m is 1 to 8
  • v is 0 or 1
  • n is 2 to 20.
  • the group in which one hydrogen atom of the hydroxyalkyl group having 1 to 4 carbon atoms is substituted with the anaerobic curable functional group is preferably a group in which the hydrogen atom of the hydroxy group is substituted with the anaerobic curable functional group.
  • the specific multimer includes, for example, a multimer having a reactive functional group such as a hydroxy group, an amino group, a carboxy group, an isocyanate group, a thiol group, an epoxy group in a side chain, and a reactive functional group contained in the multimer.
  • a reactive functional group such as a hydroxy group, an amino group, a carboxy group, an isocyanate group, a thiol group, an epoxy group in a side chain, and a reactive functional group contained in the multimer.
  • It may be a reaction product of a monomer having a reactive functional group and an anaerobic curable functional group that react.
  • This reaction product has a structure in which the reactive functional group in the multimer reacts with the reactive functional group in the monomer, and has an anaerobic curable functional group in the side chain.
  • the specific multimer has an anaerobic curable functional group at the main chain terminal, and has a side chain having a reactive functional group such as a hydroxy group, an amino group, a carboxy group, an isocyanate group, a thiol group, and an epoxy group.
  • This reaction product has a structure in which the reactive functional group in the multimer reacts with the reactive functional group in the monomer, and has an anaerobic curable functional group at the side chain and main chain terminal.
  • reaction product obtained by reacting a monomer having an anaerobic curable functional group at the terminal with a polymer having an anaerobic curable functional group at the main chain terminal and having the above-mentioned reactive functional group in the side chain It has an anaerobic curable functional group at the main chain end and side chain end.
  • the specific multimer may be a reaction product of a multimer having a hydroxy group in a side chain and a monomer having an isocyanate group and an anaerobic curable functional group.
  • This reaction product has a urethane bond formed by the reaction of a hydroxy group and an isocyanate group, and has an anaerobic curable functional group in its side chain.
  • the specific multimer may have the following structure (I) in the side chain.
  • R 1 and R 2 each independently represent a substituted or unsubstituted alkylene group having 1 to 6 carbon atoms
  • R 3 represents a hydrogen atom or a methyl group
  • * represents a bonding site. ..
  • R 1 and R 2 are each independently a methylene group, ethylene group, n-propylene group, isopropylene group, n-butylene group, isobutylene group, sec-butylene group, tert-butylene group, n -Pentylene group, isopentylene group, neopentylene group, tert-pentylene group and the like.
  • * is preferably bonded to a carbon atom in the main chain.
  • the weight average molecular weight (Mw) of the specific multimer is preferably 5,000 to 800,000, more preferably 10,000 to 500,000.
  • the weight average molecular weight refers to a value measured by gel permeation chromatography (GPC).
  • the content of the specific multimer in the resin composition is not particularly limited.
  • the content of the specific multimer is preferably 5% by mass to 40% by mass, more preferably 7% by mass to 36% by mass, and further preferably 9% by mass to 32% by mass.
  • the resin composition of the present disclosure together with a specific multimer, a monomer having an anaerobic curable functional group, a multimer having no anaerobic curable functional group in its side chain and having an anaerobic curable functional group in its main chain.
  • Etc. (hereinafter, also referred to as “other compound”) may be included.
  • the compound include monofunctional (meth)acrylic compounds and polyfunctional (meth)acrylic compounds. Other compounds may be used alone or in combination of two or more.
  • the monofunctional (meth)acrylic compound examples include (meth)acrylic acid; methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, isobutyl (meth)acrylate, 2-ethylhexyl (meth).
  • polyfunctional (meth)acrylic compound examples include 1,4-butanediol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, 1,9-nonanediol di(meth)acrylate, and ethoxy.
  • the content of other compounds in the resin composition may be 10% by mass or less, 5% by mass or less, or 3% by mass or less. Further, the resin composition may not contain any other compound, and may contain 1% by mass or more.
  • the resin composition of the present disclosure preferably contains an inorganic filler.
  • the inorganic filler may be non-conductive or conductive.
  • the use of the non-conductive inorganic filler tends to suppress the decrease in insulation. Further, the thermal conductivity tends to be further improved by using the conductive inorganic filler.
  • non-conductive inorganic filler examples include aluminum oxide (alumina), magnesium oxide, aluminum nitride, boron nitride, silicon nitride, silica (silicon dioxide), silicon oxide, aluminum hydroxide, barium sulfate and the like. ..
  • the conductive inorganic filler examples include gold, silver, nickel, copper, graphite and the like. Among them, graphite is preferable from the viewpoint of suppressing the curing of the resin composition before adhering to the adherend.
  • the inorganic filler is at least one selected from the group consisting of aluminum oxide (alumina), boron nitride, magnesium oxide, aluminum nitride, silica (silicon oxide) and graphite. It is more preferably at least one selected from the group consisting of boron nitride and aluminum oxide (alumina). These inorganic fillers may be used alone or in combination of two or more.
  • the inorganic filler it is preferable to use a mixture of two or more kinds having different volume average particle diameters.
  • the small-particle-diameter inorganic filler is packed in the voids of the large-particle-diameter inorganic filler, so that the inorganic-filler is packed more densely than when using only the single-particle-diameter inorganic filler. It becomes possible to exhibit higher thermal conductivity.
  • aluminum oxide is used as the inorganic filler, 60% by volume to 75% by volume of aluminum oxide having a volume average particle diameter of 16 ⁇ m to 20 ⁇ m and an average volume average particle diameter of 2 ⁇ m to 4 ⁇ m are oxidized in the inorganic filler.
  • the volume average particle diameter (D50) of the inorganic filler can be measured using a laser diffraction method.
  • the inorganic filler in the resin composition is extracted and measured using a laser diffraction/scattering particle size distribution analyzer (for example, Beckman Coulter, Inc., trade name: LS230).
  • a laser diffraction/scattering particle size distribution analyzer for example, Beckman Coulter, Inc., trade name: LS230.
  • the inorganic filler component is extracted from the resin composition and sufficiently dispersed with an ultrasonic disperser or the like, and the weight cumulative particle size distribution curve of this dispersion liquid is calculated. taking measurement.
  • the volume average particle diameter (D50) refers to a particle diameter at which the cumulative value becomes 50% from the smaller diameter side in the volume cumulative particle size distribution curve obtained by the above measurement.
  • the content of the inorganic filler is not particularly limited.
  • the content of the inorganic filler in the resin composition is preferably 40% by volume or more, more preferably more than 40% by volume, and more preferably 50% by volume from the viewpoint of thermal conductivity. It is more preferably more than 90% by volume and particularly preferably 55% by volume to 80% by volume.
  • the content of the inorganic filler is 40% by volume or more, it tends to be possible to achieve higher thermal conductivity.
  • the content of the inorganic filler is 90% by volume or less, it tends to be possible to suppress deterioration in flexibility and insulation of the cured product of the resin sheet.
  • the content of the inorganic filler in the resin composition is preferably 40% by mass to 95% by mass, more preferably 50% by mass to 95% by mass, and 60% by mass to 95% by mass based on the total solid content.
  • the content is more preferably mass%, particularly preferably 65 mass% to 95 mass%, and even more preferably 65 mass% to 93 mass%.
  • the resin composition of the present disclosure may contain a polymerization initiator.
  • the metal ion and the polymerization initiator react with each other to generate a radical, and the generated radical reacts with the anaerobic curable functional group to suitably proceed the curing reaction.
  • the polymerization initiator may be an organic peroxide.
  • the organic peroxide include ketone peroxides such as methyl ethyl ketone peroxide, cyclohexanone peroxide, 3,3,5-trimethylcyclohexanone peroxide, methyl cyclohexanone peroxide, methyl acetoacetate peroxide, and acetylacetone peroxide; 1 ,1-bis(t-butylperoxy)-3,3,5-trimethylcyclohexane, 1,1-bis(t-butylperoxy)cyclohexane, 2,2-bis(t-butylperoxy)octane, n -Butyl-4,4-bis(t-butylperoxy)valerate, peroxyketals such as 2,2-bis(t-butylperoxy)butane; t-butyl hydroperoxide, cumene hydroperoxide, diisopropyl Hydroperoxides such as
  • diisopropyl peroxydicarbonate di2-ethylhexyl peroxydicarbonate, di-n-propyl peroxydicarbonate, bis-(4-t-butylcyclohexyl) peroxydicarbonate, dimyristyl peroxydicarbonate, di-2 -Peroxydicarbonates such as ethoxyethyl peroxydicarbonate, dimethoxyisopropyl peroxydicarbonate, di(3-methyl-3-methoxybutyl)peroxydicarbonate, diallyl peroxydicarbonate; t-butyl peroxydiamine Cetate, t-butylperoxyisobutyrate, t-butylperoxypivalate, t-butylperoxyneodecanoate, cumylperoxyneodecanoate, t-butylperoxy-2-ethylhexanoate, t-butylperoxy
  • the content of the polymerization initiator in the resin composition is 0.01 parts by mass with respect to 100 parts by mass of the specific multimer in terms of storage stability and curability. It is preferably from 10 to 10 parts by mass, more preferably from 0.1 to 5 parts by mass.
  • the resin composition of the present disclosure contains a polymerization accelerator.
  • the polymerization accelerator is not particularly limited, and examples thereof include a hydrazine compound, an amine compound, a mercaptan compound, and a transition metal-containing compound. These polymerization accelerators may be used alone or in combination of two or more.
  • the hydrazine compound is not particularly limited, 1-acetyl-2-phenylhydrazine, 1-acetyl-2(p-tolyl)hydrazine, 1-benzoyl-2-phenylhydrazine, 1-(1′,1′, 1'-trifluoro)acetyl-2-phenylhydrazine, 1,5-diphenyl-carbohydrazine, 1-formyl-2-phenylhydrazine, 1-acetyl-2-(p-bromophenyl)hydrazine, 1-acetyl-2 Examples include -(p-nitrophenyl)hydrazine, 1-acetyl-2-(2'-phenylethylhydrazine), ethylcarbazate, p-nitrophenylhydrazine, p-trisulfonylhydrazide and the like.
  • the amine compound is not particularly limited, and is a heterocyclic secondary amine such as 2-ethylhexylamine, 1,2,3,4-tetrahydroquinone, 1,2,3,4-tetrahydroquinaldine; quinoline, methylquinoline.
  • Quinaldine, quinoxalinephenazine and other heterocyclic tertiary amines N,N-dimethyl-para-toluidine, N,N-dimethyl-anisidine, N,N-dimethylaniline and other aromatic tertiary amines; 1,2 Examples include azole compounds such as 1,4-triazole, oxazole, oxadiazole, thiadiazole, benzotriazole, hydroxybenzotriazole, benzoxazole, 1,2,3-benzothiadiazole, and 3-mercaptobenzotrizole.
  • the mercaptan compound is not particularly limited, and examples thereof include linear mercaptans such as n-dodecyl mercaptan, ethyl mercaptan, and butyl mercaptan.
  • transition metal-containing compounds include metal chelate complex salts.
  • the metal chelate complex salt is not particularly limited, pentadione iron, pentadione cobalt, pentadione copper, propylenediamine copper, ethylenediamine copper, iron naphthate, nickel naphthate, cobalt naphthate, copper naphthate, copper octate, iron hexoate, iron propionate. , Vanadium acetylacetone and the like.
  • the content of the polymerization accelerator in the resin composition is 0.05 parts by mass with respect to 100 parts by mass of the specific polymer in terms of storage stability and curing accelerating property. It is preferably from 5 to 5 parts by mass, more preferably from 0.1 to 3 parts by mass.
  • the resin composition may contain at least one silane coupling agent.
  • the silane coupling agent plays a role of forming a covalent bond between the surface of the inorganic filler and the resin that surrounds it (corresponding to a binder agent), improves the thermal conductivity, and prevents moisture from penetrating to insulate the insulation. It can be considered to play a role of improving sex.
  • silane coupling agent is not particularly limited, and a commercially available one may be used. In the present disclosure, it is preferable to use a silane coupling agent having an acryloyl group, an epoxy group, an amino group, a mercapto group, a ureido group or a hydroxyl group at the terminal.
  • silane coupling agent examples include 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropyltriethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, and 3-glycidoxypropylmethyldimethoxysilane.
  • silane 3-aminopropyltrimethoxysilane, N-phenyl-3-aminopropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, 3-mercaptopropyltriethoxysilane, and 3-ureidopropyltriethoxysilane.
  • a silane coupling agent oligomer represented by trade name: SC-6000KS2 (Hitachi Chemical Techno Service Co., Ltd.) and the like can also be mentioned. These silane coupling agents may be used alone or in combination of two or more.
  • the content of the silane coupling agent in the resin composition is not particularly limited.
  • the content of the silane coupling agent is preferably 0.01% by mass to 0.2% by mass, more preferably 0.03% by mass to 0.1% by mass.
  • the resin composition may contain other components in addition to the above components, if necessary.
  • the resin composition of the present disclosure may be a varnish-shaped resin composition prepared by adding an organic solvent such as methyl ethyl ketone or cyclohexanone.
  • the resin sheet of the present disclosure is a sheet-shaped molded product of the resin composition of the present disclosure described above.
  • the above-mentioned resin sheet is used to obtain a cured product after being cured under anaerobic conditions in which the supply of oxygen is suppressed.
  • the two main surfaces of the resin sheet may be in contact with a member having an oxygen permeability of 0.5 mL/(m 2 ⁇ 24 h ⁇ atm) or less, respectively. .3mL / (m 2 ⁇ 24h ⁇ atm) may be in contact with at a member or less, may be in contact with 0.1mL / (m 2 ⁇ 24h ⁇ atm) or less is member.
  • the member that comes into contact with the resin sheet may be an adherend that is adhered to the resin sheet.
  • the resin sheet of the present disclosure has two main surfaces bonded to an adherend, and at least one main surface bonded to a surface of the adherend containing at least one of metal and metal ions. Is preferred, and it is more preferred that the two main surfaces are used by being adhered to the surface of the adherend containing at least one of metal and metal ions. At least one main surface of the resin sheet is covered under anaerobic conditions in which the supply of oxygen is suppressed, for example, under the condition that the two main surfaces of the resin sheet are in contact with the adherend and the supply of oxygen is suppressed.
  • the polymerization reaction of the specific multimer contained in the resin sheet suitably proceeds, and the resin sheet can be suitably cured.
  • At least one of the two main surfaces may be used by being bonded to a metal-containing layer containing at least one of a metal and metal ions, and the two main surfaces may be bonded to the metal-containing layer. It may be used.
  • another layer may be laminated on the surface of the metal-containing layer that is not bonded to the resin sheet, and this other layer may or may not include at least one of a metal and a metal ion. You don't have to.
  • metals include iron, aluminum, zinc, titanium, chromium, manganese, cobalt, nickel, tin, lead, copper, silver and gold, and examples of metal ions include these ions.
  • the metal may be an alloy such as stainless steel.
  • the thickness of the resin sheet is not particularly limited and can be appropriately selected according to the purpose.
  • the thickness of the resin sheet may be 30 ⁇ m to 400 ⁇ m, or may be 50 ⁇ m to 300 ⁇ m from the viewpoint of high thermal conductivity, insulation and curability.
  • the thickness of the resin sheet or the like can be measured by a known method, and is the number average value of the values measured at 5 points.
  • the resin sheet may be cured at a temperature of 5°C to 70°C, preferably 10°C to 40°C.
  • the use of the resin sheet of the present disclosure is not particularly limited.
  • a semiconductor device can be given.
  • semiconductor devices it is preferably used for parts having a particularly high heat generation density.
  • the method for producing the resin sheet of the present disclosure is not particularly limited.
  • a resin composition in which a varnish-shaped resin composition prepared by adding an organic solvent such as methyl ethyl ketone or cyclohexanone (hereinafter, also referred to as “resin varnish”) on a resin support is applied by a dispenser or the like. After forming the layer of the product, it can be produced by removing at least a part of the organic solvent from the layer of the resin composition by drying.
  • the drying method is not particularly limited as long as at least a part of the organic solvent contained in the resin varnish can be removed, and from the commonly used drying methods, the type of the organic solvent contained in the resin varnish, the content may be appropriately selected depending on the content. You can
  • the metal substrate of the present disclosure includes a metal support, a cured product of the resin sheet of the present disclosure disposed on the metal support, and a metal foil disposed on the cured product.
  • the metal substrate of the present disclosure can be manufactured by curing a resin sheet under room temperature conditions or conditions close to room temperature.
  • the material, thickness, etc. of the metal support can be appropriately selected according to the purpose. Specifically, a metal such as aluminum or iron can be used and the thickness can be set to 0.5 mm to 5 mm.
  • the metal foil in the metal substrate is not particularly limited, and examples thereof include gold foil, copper foil, aluminum foil, and the like, and generally copper foil is used.
  • the thickness of the metal foil is, for example, 1 ⁇ m to 200 ⁇ m, and is preferably 120 ⁇ m or less from the viewpoint of flexibility.
  • nickel, nickel-phosphorus alloy, nickel-tin alloy, nickel-iron alloy, lead, lead-tin alloy, etc. are used as an intermediate layer, and a copper foil layer is provided on both surfaces of the foil to form a composite foil having a three-layer structure. Examples include a composite foil having a two-layer structure in which an aluminum foil and a copper foil are combined.
  • one copper layer has a thickness of 0.5 ⁇ m to 15 ⁇ m and the other copper layer has a thickness of 10 ⁇ m to 300 ⁇ m.
  • the method for producing a metal substrate of the present disclosure includes a step of laminating a metal support, a resin sheet of the present disclosure, and a metal foil in this order, and curing the resin sheet under anaerobic conditions in which oxygen supply is suppressed. And a step of
  • a resin sheet is formed by placing the resin composition on the metal support or the metal foil and drying the resin sheet or disposing the resin sheet, and further, the metal foil or the metal support is placed on the resin sheet.
  • the metal support, the resin sheet of the present disclosure, and the metal foil may be laminated in this order.
  • the two main surfaces of the resin sheet may be in an anaerobic condition in which the supply of oxygen to the resin sheet is suppressed by contacting the metal support and the metal foil.
  • the resin sheet may be cured at a temperature of 5°C to 70°C, preferably 10°C to 40°C.
  • the resin sheet may be cured while being pressurized, for example, 0.05 MPa to 20 MPa may be pressurized, preferably 0.2 MPa to 15 MPa.
  • the power semiconductor device of the present disclosure includes a semiconductor module in which a metal plate, a solder layer, and a semiconductor chip are laminated in this order, a heat dissipation member containing a metal, and the present disclosure disposed between the metal plate and the heat dissipation member of the semiconductor module. And a cured product of the resin sheet.
  • the semiconductor module portion may be sealed with a sealing material or the like, or the entire power semiconductor module may be molded with a molding resin or the like.
  • FIG. 1 is a schematic sectional view showing an example of the configuration of a power semiconductor device.
  • a cured product 102 of a resin sheet is arranged between a metal plate 106 in a semiconductor module in which a metal plate 106, a solder layer 110, and a semiconductor chip 108 are laminated in this order, and a heat dissipation base substrate 104. Is sealed with a sealing material 114.
  • the heat dissipation base substrate 104 can be configured by using copper or aluminum having thermal conductivity.
  • FIG. 2 is a schematic sectional view showing another example of the configuration of the power semiconductor device. In FIG.
  • a cured product 102 of a resin sheet is arranged between a metal plate 106 in a semiconductor module in which a metal plate 106, a solder layer 110, and a semiconductor chip 108 are laminated in this order, and a heat dissipation base substrate 104.
  • the heat dissipation base substrate 104 is molded with the mold resin 112.
  • the cured product of the resin sheet of the present disclosure can be used as a heat dissipation adhesive layer between a semiconductor module and a heat dissipation base substrate as shown in FIG. Further, even when the entire power semiconductor device is molded as shown in FIG. 2, it can be used as a heat dissipation material between the heat dissipation base substrate and the metal plate.
  • the multimer A has a urethane bond formed by the reaction of the hydroxy group derived from 2-hydroxyethyl acrylate in the acrylic intermediate A with the isocyanate group in MOI, and has (meth)acryloyl at the side chain end. It is a multimer having a group.
  • (Multimer B) Using a 100-mL eggplant-shaped flask as a reactor, 30 g of acrylic intermediate B, 4 g of MOI, and 0.002 g of dibutyltin dilaurate were mixed, and the mixture was stirred at 75° C. for 1 hour at a stirring rotation number of 400 times/minute to obtain an acrylic intermediate polymer. MOI modified to obtain MOI modified acrylic resin B (multimer B).
  • the weight average molecular weight (Mw) of MOI modified acrylic resin B was 20000.
  • the multimer B has a urethane bond formed by the reaction between the hydroxy group derived from 2-hydroxyethyl acrylate in the acrylic intermediate B and the isocyanate group in the MOI, and has (meth)acryloyl at the side chain terminal. It is a multimer having a group.
  • ⁇ Polymerization initiator Cumene hydroperoxide (Tokyo Chemical Industry Co., Ltd.)
  • ⁇ Polymerization accelerator Cobalt naphthenate (Tokyo Chemical Industry Co., Ltd.)
  • Inorganic filler Inorganic filler 1: AA-18 (alumina particles, Sumitomo Chemical Co., Ltd., D50: 18 ⁇ m) Inorganic filler 2: AA-3 (alumina particles, Sumitomo Chemical Co., Ltd., D50: 3 ⁇ m) Inorganic filler 3: AA-04 (alumina particles, Sumitomo Chemical Co., Ltd., D50: 0.4 ⁇ m) Inorganic filler 4: HP-40 (boron nitride particles, Mizushima Iron & Iron Co., Ltd., D50: 40 ⁇ m)
  • Example 1> (Preparation of resin composition) 9.76% by mass of the polymer A, 0.1% by mass of the polymerization initiator, 0.01% by mass of the polymerization accelerator, 50.34% by mass of the inorganic filler 1, and 2 of the inorganic filler 2. 18.30% by mass, 7.63% by mass of the inorganic filler 3, 0.08% by mass of the additive, and 13.78% by mass of the solvent are mixed to prepare a varnish-like resin composition. did.
  • the density of the inorganic filler 1 is 3.98 g/cm 3
  • the density of the inorganic filler 2 is 3.98 g/cm 3
  • the density of the inorganic filler 3 is 3.98 g/cm 3
  • the polymer A the polymerization initiator
  • the density of the polymerization accelerator was 1.2 g/cm 3 and the ratio of the inorganic filler to the total volume of the total solid content of the resin composition was calculated, it was 70% by volume.
  • B stage sheet curability To evaluate the curability of the B stage sheet, the above varnish-shaped resin composition was applied onto a PET film using an applicator so that the thickness after drying was 200 ⁇ m, and then dried at 70° C. for 10 minutes. A sample before being B-staged was prepared. Furthermore, the PET film was peeled off from the PET film and the B stage sheet with the copper foil, and after the B stage, a sample was prepared. Using a differential scanning calorimeter (manufactured by Perkin Elmer, model number DSC8500), the sample before and after the B stage was heated from 20°C to 300°C at 10°C/min, and the calorific value was measured. The curing rate A was calculated by the following formula.
  • Curing rate A (%) (heat generation amount of sample after B stage conversion/heat generation amount of sample before B stage conversion) x 100 ⁇ Evaluation of curability> The curability was evaluated based on the following criteria. A: Curing rate 50% or more B: Curing rate less than 50%
  • Curing rate B (%) (calorific value of sample after curing/calorific value of sample before B stage conversion) ⁇ 100 ⁇ Evaluation of curability> The curability was evaluated based on the following criteria. A: Curing rate less than 20% B: Curing rate 20% or more
  • the copper foil of the cured resin sheet was removed by etching to obtain a resin sheet for evaluating thermal conductivity.
  • the obtained resin sheet was cut into a length of 10 mm and a width of 10 mm to obtain a sample.
  • the thermal diffusivity was evaluated by the xenon flash method (trade name: LFA447 nanoflash of NETZSCH).
  • the thermal conductivity of the cured resin sheet was obtained from the product of this value, the density measured by the Archimedes method, and the specific heat measured by DSC (differential scanning calorimeter; product name of Perkin Elmer: DSC Pyris1). ..
  • the results are shown in Table 1.
  • Example 2> Preparation of resin composition 9.76% by mass of the polymer B, 0.1% by mass of the polymerization initiator, 0.01% by mass of the polymerization accelerator, 50.34% by mass of the inorganic filler 1, and 2 of the inorganic filler. 18.30% by mass, 7.63% by mass of the inorganic filler 3, 0.08% by mass of the additive, and 13.78% by mass of the solvent are mixed to prepare a varnish-like resin composition. did.
  • the density of the inorganic filler 1 is 3.98 g/cm 3
  • the density of the inorganic filler 2 is 3.98 g/cm 3
  • the density of the inorganic filler 3 is 3.98 g/cm 3
  • the polymer A the polymerization initiator
  • the density of the polymerization accelerator was 1.2 g/cm 3 and the ratio of the inorganic filler to the total volume of the total solid content of the resin composition was calculated, it was 70% by volume.
  • Example 3> (Preparation of resin composition) Polymer A 15.00 mass %, polymerization initiator 0.15 mass %, polymerization accelerator 0.01 mass %, inorganic filler 4 33.34 mass %, inorganic filler 2 7.54% by mass, 7.54% by mass of the inorganic filler 3, 0.05% by mass of the additive, and 36.37% by mass of the solvent are mixed to prepare a varnish-like resin composition. did.
  • the density of the inorganic filler 4 is 2.20 g/cm 3
  • the density of the inorganic filler 2 is 3.98 g/cm 3
  • the density of the inorganic filler 3 is 3.98 g/cm 3
  • the polymer A the polymerization initiator
  • the density of the polymerization accelerator was 1.2 g/cm 3 and the ratio of the inorganic filler to the total volume of the total solid content of the resin composition was calculated, it was 60% by volume.
  • ⁇ Comparative Example 1> (Preparation of resin composition)
  • the resin A is 5.53% by mass
  • the curing agent A is 4.30% by mass
  • the curing accelerator is 0.2% by mass
  • the inorganic filler 1 is 50.24% by mass
  • the inorganic filler 2 is 18%.
  • a varnish-like resin composition was prepared by mixing 0.27% by mass, 7.61% by mass of the inorganic filler 3, 0.08% by mass of the additive, and 13.77% by mass of the solvent. ..
  • the density of the inorganic filler 1 is 3.98 g/cm 3
  • the density of the inorganic filler 2 is 3.98 g/cm 3
  • the density of the inorganic filler 3 is 3.98 g/cm 3
  • the polymer A the polymerization initiator
  • the density of the polymerization accelerator was 1.2 g/cm 3 and the ratio of the inorganic filler to the total volume of the total solid content of the resin composition was calculated, it was 70% by volume.
  • ⁇ Comparative example 2> (Preparation of resin composition) 6.57% by mass of the resin A, 3.29% by mass of the curing agent B, 50.34% by mass of the inorganic filler 1, 18.30% by mass of the inorganic filler 2 and 3 of the inorganic filler 3. 7.63% by mass, 0.08% by mass of the additive, and 13.79% by mass of the solvent were mixed to prepare a varnish-shaped resin composition.
  • the density of the inorganic filler 1 is 3.98 g/cm 3
  • the density of the inorganic filler 2 is 3.98 g/cm 3
  • the density of the inorganic filler 3 is 3.98 g/cm 3
  • the polymer A the polymerization initiator
  • the density of the polymerization accelerator was 1.2 g/cm 3 and the ratio of the inorganic filler to the total volume of the total solid content of the resin composition was calculated, it was 70% by volume.
  • the density of the inorganic filler 1 is 3.98 g/cm 3
  • the density of the inorganic filler 2 is 3.98 g/cm 3
  • the density of the inorganic filler 3 is 3.98 g/cm 3
  • butyl acrylate and ethyl acrylate was calculated by setting the densities of the 2-hydroxyethyl acrylate, the polymerization initiator and the polymerization accelerator to be 1.2 g/cm 3 and found to be 70% by volume. there were.
  • Examples 1 to 3 regarding the curability of the B stage, it is presumed that the value of the curing rate A increased because the curing of the resin sheet proceeded without the heat treatment. Furthermore, in Examples 1 to 3, the curing progressed sufficiently even without heat treatment, so it is presumed that the value of the curing rate B became low. From the above, it was found that in Examples 1 to 3, the resin sheet could be cured under room temperature conditions. Furthermore, since it is cured under anaerobic conditions, unintentional curing is unlikely to occur and the pot life is presumed to be excellent.
  • Comparative Example 1 regarding the curability of the B stage, it is presumed that the value of the curing rate A increased because the curing of the resin sheet proceeded without heat treatment. However, in Comparative Example 1, it is presumed that the value of the curing rate B became high because the curing did not proceed sufficiently when the same operation as in Example 1 in which the curing was performed without the heat treatment was performed. In Comparative Example 2, regarding the curability of the B-stage sheet, the varnish-shaped resin composition was applied to a PET film and then cured when dried, and the value of the curing rate A was low. From the above, in Comparative Examples 1 and 2, it was found that unintended curing of the resin sheet proceeded before being attached to the adherend, and the pot life was poor.
  • Comparative Example 3 since the monomer having the anaerobic curable functional group was used, the resin was likely to remain on the PET film, and the PET film releasability was insufficient.
  • 102 cured product of resin sheet
  • 104 heat dissipation base substrate
  • 106 metal plate
  • 108 semiconductor chip
  • 110 solder layer
  • 112 mold resin
  • 114 sealing material

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Abstract

L'invention concerne une composition de résine, laquelle contient un multimère possédant un groupe fonctionnel durcissable en milieu anaérobie à l'extrémité de sa chaîne latérale, et laquelle résine est utilisée en conditions anaérobies dans lesquelles l'apport d'oxygène est limité.
PCT/JP2018/045188 2018-12-07 2018-12-07 Composition de résine, feuille de résine, substrat métallique, dispositif semi-conducteur de puissance et procédé de fabrication de substrat métallique WO2020115914A1 (fr)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2022114101A1 (fr) * 2020-11-27 2022-06-02 大阪有機化学工業株式会社 Composition de formation d'elastomère, élastomère, stratifié, dispositif d'armature, actionneur, capteur et procédé de fabrication d'une composition de formation d'elastomère

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2010204199A (ja) * 2009-02-27 2010-09-16 Tokyo Ohka Kogyo Co Ltd 感光性樹脂組成物
WO2013141314A1 (fr) * 2012-03-22 2013-09-26 日立化成株式会社 Composition de résine photodurcissable, dispositif d'affichage d'images et leur procédé de production
JP2015001591A (ja) * 2013-06-14 2015-01-05 日立化成株式会社 感光性樹脂組成物、感光性エレメント、サンドブラスト用マスク材、及び被処理体の表面加工方法
JP2017179002A (ja) * 2016-03-28 2017-10-05 日立化成株式会社 硬化性樹脂組成物、硬化物及び樹脂シート

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2010204199A (ja) * 2009-02-27 2010-09-16 Tokyo Ohka Kogyo Co Ltd 感光性樹脂組成物
WO2013141314A1 (fr) * 2012-03-22 2013-09-26 日立化成株式会社 Composition de résine photodurcissable, dispositif d'affichage d'images et leur procédé de production
JP2015001591A (ja) * 2013-06-14 2015-01-05 日立化成株式会社 感光性樹脂組成物、感光性エレメント、サンドブラスト用マスク材、及び被処理体の表面加工方法
JP2017179002A (ja) * 2016-03-28 2017-10-05 日立化成株式会社 硬化性樹脂組成物、硬化物及び樹脂シート

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2022114101A1 (fr) * 2020-11-27 2022-06-02 大阪有機化学工業株式会社 Composition de formation d'elastomère, élastomère, stratifié, dispositif d'armature, actionneur, capteur et procédé de fabrication d'une composition de formation d'elastomère

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