WO2016143640A1 - 導電性構造体、及び導電性構造体の製造方法 - Google Patents

導電性構造体、及び導電性構造体の製造方法 Download PDF

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Publication number
WO2016143640A1
WO2016143640A1 PCT/JP2016/056484 JP2016056484W WO2016143640A1 WO 2016143640 A1 WO2016143640 A1 WO 2016143640A1 JP 2016056484 W JP2016056484 W JP 2016056484W WO 2016143640 A1 WO2016143640 A1 WO 2016143640A1
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conductive
meth
acrylate
conductive structure
composition
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PCT/JP2016/056484
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English (en)
French (fr)
Japanese (ja)
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祐輔 岡部
宏士 山家
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セメダイン株式会社
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Priority to JP2017505013A priority Critical patent/JPWO2016143640A1/ja
Priority to CN201680014123.8A priority patent/CN107408422A/zh
Priority to KR1020177023651A priority patent/KR20170126877A/ko
Publication of WO2016143640A1 publication Critical patent/WO2016143640A1/ja

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F292/00—Macromolecular compounds obtained by polymerising monomers on to inorganic materials
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00—Compositions of homopolymers or 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 of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L33/04—Homopolymers or copolymers of esters
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00—Compositions of homopolymers or 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 of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L33/24—Homopolymers or copolymers of amides or imides
    • C08L33/26—Homopolymers or copolymers of acrylamide or methacrylamide
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
    • H01B13/00—Apparatus or processes specially adapted for manufacturing conductors or cables
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
    • H01B13/00—Apparatus or processes specially adapted for manufacturing conductors or cables
    • H01B13/0026—Apparatus for manufacturing conducting or semi-conducting layers, e.g. deposition of metal
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
    • H01B5/00—Non-insulated conductors or conductive bodies characterised by their form
    • H01B5/16—Non-insulated conductors or conductive bodies characterised by their form comprising conductive material in insulating or poorly conductive material, e.g. conductive rubber

Definitions

  • the present invention relates to a conductive structure and a method for manufacturing the conductive structure.
  • the present invention relates to a conductive structure that is excellent in flexibility and can maintain the desired flexibility even when pressure is repeatedly applied, and a method for manufacturing the conductive structure.
  • the conductive particles described in Patent Document 1 not only the entire particle including the inside of the particle cannot be provided with conductivity, but also the shape is limited to the particle shape, and the degree of freedom in shape design is increased. There is a limit.
  • the electroconductive particle described in patent document 1 since the electroconductive material is made to adhere to the surface of the resin particle, it may not only damage a contact target object but pressure is applied from the outside. When the shape of the conductive particles is deformed, the conductive material attached to the surface may drop and the conductivity may decrease.
  • an object of the present invention is to provide a conductive structure capable of ensuring the degree of freedom of shape design and maintaining the desired flexibility even when repeatedly used, and a method for manufacturing the conductive structure Is to provide.
  • the present invention is a conductive structure having resilience, comprising a polymerizable oligomer, a conductive filler, and an initiator that initiates a polymerization reaction of the polymerizable oligomer.
  • a conductive structure obtained by curing the composition into a predetermined shape is provided.
  • the conductive filler is preferably mixed in an amount of 2.5 parts by weight to 7.5 parts by weight with respect to 1 part by weight of the polymerizable oligomer.
  • the conductive structure can be obtained by placing the conductive composition in a predetermined region of a predetermined base material and then curing the placed conductive composition.
  • the conductive structure can also be obtained by adding a cured conductive composition to a predetermined base material.
  • the polymerizable oligomer is preferably a compound having a radical polymerizable vinyl group.
  • the present invention provides a method for producing a conductive structure having resilience, comprising a polymerizable oligomer that ensures the restorability of the conductive structure, and the restorability of the conductive structure.
  • a method for producing a conductive structure which includes a molding step for molding a conductive composition into a predetermined shape and a curing step for curing the conductive composition by heating in an oxygen-blocking atmosphere.
  • the degree of freedom in shape design can be secured, and the desired flexibility can be maintained even when used repeatedly.
  • a conductive structure and a method for manufacturing the conductive structure can be provided.
  • the conductive structure according to the present embodiment is used for a member that requires electrical conductivity.
  • the conductive structure can be used as a substitute for conductive bumps and connectors.
  • the conductive structure can be used as an anisotropic conductive film by forming the conductive structure into a sheet (or thin film). Can do.
  • the conductive structure can be formed into the shape of a bump electrode.
  • the conductive structure can be used as a contact member that repeatedly contacts / detaches from the object. Specifically, in a test apparatus and / or inspection apparatus for electronic components such as semiconductor elements, it can be used as a contact member that ensures electrical continuity by contacting an electrode of the electronic component.
  • the conductive structure according to the present embodiment has flexibility that does not substantially damage the object to be contacted, and is difficult to be plastically deformed even when repeatedly contacting / separating the object, so that it can be restored. Excellent and usable for a long time.
  • the conductive structure according to the present embodiment is formed by curing a predetermined liquid conductive composition having viscosity. Therefore, the contact member corresponding to an electronic component having narrow pitch electrodes arranged at intervals of about 50 ⁇ m, for example, by arranging and curing the droplets of the conductive composition on a predetermined substrate or the like at predetermined intervals. As described above, the conductive structure according to this embodiment can also be configured.
  • the conductive structure having restorability includes a polymerizable oligomer that ensures the restorability of the conductive structure, and a polymerizable oligomer within a range that can secure the restorability of the conductive structure. It is obtained by curing a conductive composition containing a conductive filler mixed in and an initiator for initiating a polymerization reaction of a polymerizable oligomer into a predetermined shape.
  • the conductive composition further contains a monomer (hereinafter also referred to as “monomer”) for the purpose of adjusting workability in the coating step of the conductive structure, depending on the amount added. You can also Furthermore, the conductive composition can also contain other additives such as a diluent for adjusting the viscosity of the conductive composition.
  • the conductive structure according to the present embodiment is formed using a predetermined conductive composition.
  • the conductive structure according to the present embodiment will be described together with the conductive composition.
  • the polymerizable oligomer according to the present embodiment is a compound having a radical polymerizable vinyl group.
  • the compound having a radical polymerizable vinyl group is not particularly limited, and a known compound having a radical polymerizable vinyl group can be used.
  • a compound having a (meth) acryloyl group and / or an N-vinyl compound in which a vinyl group is directly bonded to a nitrogen atom can be used as the polymerizable oligomer.
  • examples of the compound having a (meth) acryloyl group include a compound having a (meth) acryloyloxy group, a compound having a (meth) acrylamide group, or a (meth) acrylimide group.
  • the compound which has a (meth) acryloyloxy group from a viewpoint of improving storage stability. From the viewpoint of improving the reactivity, it is preferable to use a compound having a (meth) acrylamide group or a (meth) acrylimide group.
  • the oligomer and the polymer are collectively referred to as a polymer.
  • Examples of monofunctional (meth) acrylates include (meth) acrylic acid, ethyl (meth) acrylate, 1-methoxyethyl (meth) acrylate, propyl (meth) acrylate, butyl (meth) acrylate, and pentyl (meth) acrylate.
  • polyfunctional acrylates examples include 1,3-butylene glycol di (meth) acrylate, 1,4-butylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, 1,6-hexane glycol di ( (Meth) acrylate, ethylene glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate, tripropylene glycol di (meth) acrylate, ethylene oxide modified neopentyl glycol di (meth) acrylate , Propylene oxide modified neopentyl glycol di (meth) acrylate, bisphenol A di (meth) acrylate, ethylene oxide modified bisphenol A di (meth) acrylate, epichloro Dorin-modified bisphenol A di (meth) acrylate, ethylene oxide-modified bisphenol S di (meth) acrylate, hydroxypivalate ester
  • Examples of the polymer having a (meth) acryloyloxy group include an acrylic polymer, a polyester (meth) acrylate polymer, an epoxy (meth) acrylate polymer, a urethane (meth) acrylate polymer, or a polyether (meta ) Acrylate polymers and the like.
  • the acrylic polymer a polymer whose main chain is a (meth) acrylic acid ester polymer and has a (meth) acryloyloxy group can be used.
  • a polymer is preferably produced by anionic polymerization or radical polymerization, and radical polymerization is more preferable because of the versatility of the monomer or ease of control.
  • radical polymerizations it is preferably produced by living radical polymerization or radical polymerization using a chain transfer agent, more preferably a living radical polymerization method, and particularly preferably an atom transfer radical polymerization method.
  • a living radical polymerization method is used, a polymer having a (meth) acryloyloxy group at the end of the polymer chain can be produced.
  • acrylic polymer examples include poly-n-butyl acrylate having an acryloyl group at both ends described in Production Example 1 of WO2012 / 008127 and a piece described in Production Example 2 of the same publication.
  • Use poly (2-ethylhexyl acrylate) with acryloyl groups at both ends Door can be.
  • acrylic polymers examples include macromonomers AA-6, AA-714, AB-6, AJ-7, AN-6, AS-6, AW-6, and AZ manufactured by Toa Gosei Co., Ltd. -8, HA-6, HN-6, HS-6, RC-100C, RC-200C, RC-300C manufactured by Kaneka Corporation.
  • polyester (meth) acrylate polymer examples include a dehydration condensate of polyester polyol and (meth) acrylic acid.
  • examples of the polyester polyol include a reaction product of a polyol and a carboxylic acid, or an anhydride thereof.
  • Polyols include ethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, polyethylene glycol, propylene glycol, dipropylene glycol, tripropylene glycol, polypropylene glycol, butylene glycol, polybutylene glycol, tetramethylene glycol, hexamethylene glycol, neo Low molecular weight polyols such as pentyl glycol, cyclohexanedimethanol, 3-methyl-1,5-pentanediol, 1,6-hexanediol, trimethylolpropane, glycerin, pentaerythritol and dipentaerythritol, and their alkylene oxide adducts Etc.
  • Low molecular weight polyols such as pentyl glycol, cyclohexanedimethanol, 3-methyl-1,5-pentanediol, 1,6-hexanedio
  • Carboxylic acid or anhydride thereof includes dibasic acids such as orthophthalic acid, isophthalic acid, terephthalic acid, adipic acid, succinic acid, fumaric acid, maleic acid, hexahydrophthalic acid, tetrahydrophthalic acid, and trimellitic acid or the like.
  • dibasic acids such as orthophthalic acid, isophthalic acid, terephthalic acid, adipic acid, succinic acid, fumaric acid, maleic acid, hexahydrophthalic acid, tetrahydrophthalic acid, and trimellitic acid or the like.
  • An anhydride etc. are mentioned.
  • Examples of the epoxy (meth) acrylate polymer include compounds obtained by addition reaction of (meth) acrylic acid to an epoxy resin.
  • Examples of the epoxy resin include aromatic epoxy resins and aliphatic epoxy resins.
  • aromatic epoxy resin examples include resorcinol diglycidyl ether; di- or polyglycidyl ether of bisphenol A, bisphenol F, bisphenol S, bisphenol fluorene or an alkylene oxide adduct thereof; phenol novolac type epoxy resin and cresol novolac type Examples thereof include novolak-type epoxy resins such as epoxy resins; glycidyl phthalimide; o-phthalic acid diglycidyl ester and the like.
  • the document “Epoxy Resin-Recent Advances” (Shojodo, published in 1990), Chapter 2 and the document “Polymer Processing”, Vol. 9, Volume 22, Epoxy Resin [Polymer Press, Compounds published on pages 4 to 6 and 9 to 16 of "published in 1973” can be used as the aromatic epoxy resin.
  • aliphatic epoxy resin examples include diglycidyl ethers of alkylene glycols such as ethylene glycol, propylene glycol, 1,4-butanediol and 1,6-hexanediol; diglycidyl ethers of polyethylene glycol and polypropylene glycol, etc.
  • Diglycidyl ethers of polyalkylene glycols diglycidyl ethers of neopentyl glycol, dibromoneopentyl glycol and alkylene oxide adducts thereof; di- or triglycidyl ethers of trimethylolethane, trimethylolpropane, glycerin and alkylene oxide adducts thereof; And polyglycols of polyhydric alcohols such as di-, tri- or tetraglycidyl ethers of pentaerythritol and its alkylene oxide adducts.
  • Examples of the urethane (meth) acrylate polymer include a reaction product obtained by further reacting a hydroxyl group-containing (meth) acrylate with a polyol and an organic polyisocyanate reaction product.
  • examples of the polyol include a low molecular weight polyol, polyethylene glycol, polyester polyol, and polycarbonate polyol.
  • examples of the low molecular weight polyol include ethylene glycol, propylene glycol, cyclohexanedimethanol and 3-methyl-1,5-pentanediol
  • examples of the polyether polyol include polyethylene glycol and polypropylene glycol.
  • the organic polyisocyanate include tolylene diisocyanate, 4,4'-diphenylmethane diisocyanate, 4,4'-dicyclohexylmethane diisocyanate, hexamethylene diisocyanate, and isophorone diisocyanate.
  • hydroxyl group-containing (meth) acrylate examples include hydroxyalkyl (meth) acrylates such as 2-hydroxyethyl (meth) acrylate and 2-hydroxypropyl (meth) acrylate.
  • hydroxyalkyl (meth) acrylates such as 2-hydroxyethyl (meth) acrylate and 2-hydroxypropyl (meth) acrylate.
  • These urethane (meth) acrylate polymers may be produced based on a known synthesis method. For example, in the presence of an addition catalyst such as dibutyltin dilaurate, an organic isocyanate and a polyol component to be used are heated and stirred to cause an addition reaction, and further, a hydroxyalkyl (meth) acrylate is added, followed by heating and stirring to cause an addition reaction.
  • Polyether (meth) acrylate polymers include polyalkylene glycol (meth) diacrylate, diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate, dipropylene glycol Examples include di (meth) acrylate, tripropylene glycol di (meth) acrylate, polypropylene glycol di (meth) acrylate, and polytetramethylene glycol di (meth) acrylate.
  • Examples of the compound having a (meth) acrylamide group include a compound represented by the following formula (1) and a compound represented by the following formula (2).
  • R 1 represents a hydrogen atom or a methyl group
  • R 2 and R 3 represents a hydrogen atom or a hydrocarbon group having a carbon number of 1 ⁇ 20, R 2 and R 3 in one molecule, They may be the same group or different groups, and may have a cyclic structure.
  • the hydrocarbon group having 1 to 20 carbon atoms is preferably an alkyl group from the viewpoint of availability, more preferably an alkyl group having 1 to 3 carbon atoms, which may be linear or branched.
  • the alkyl group may be an alkyl group further having a hydroxyl group, an aromatic group, and a diaminoalkyl group. Specific examples of the alkyl group include a methyl group, a propyl group, a butyl group, a butyl group, and a hexyl group.
  • examples of the alkyl group having a hydroxyl group include a hydroxymethyl group, a hydroxyethyl group, and a hydroxypropyl group. And as an alkyl group which has an aromatic group, a benzyl group etc. can be mentioned. Further, examples of the dialkylaminoalkyl group include N, N-dimethylaminoethyl group and N, N-dimethylaminopropyl group.
  • R 1 is the same as R 1 of formula (1).
  • the (meth) acrylamide represented by the formula (1) include N-methyl (meth) acrylamide, Nn-propyl (meth) acrylamide, N-isopropyl (meth) acrylamide, Nn-butyl (meth) ) Acrylamide, N-sec-butyl (meth) acrylamide, Nt-butyl (meth) acrylamide, Nn-hexyl (meth) acrylamide, N-benzyl (meth) acrylamide, N-hydroxyethyl (meth) acrylamide, N, N-dimethylaminoethyl (meth) acrylamide, N, N-dimethylaminopropyl (meth) acrylamide, N, N-dimethyl (meth) acrylamide, N, N-diethyl (meth) acrylamide, N, N-di- n-propyl (meth) acrylamide, N, N-diisopropyl (Meth)
  • (meth) acrylimide represented by the formula (2) examples include phthalimide represented by the following formula (3).
  • a compound having a (meth) acrylimide group can be suitably used because of its excellent curability and stability.
  • N-vinyl compound examples include N-vinyl pyrrolidone and N-vinyl caprolactam.
  • Conductive filler As the conductive filler according to the present embodiment, carbon particles, metal particles such as silver, copper, nickel, gold, tin, zinc, platinum, palladium, iron, tungsten, morbden, solder, or alloy particles, or these particles Conductive particles such as particles prepared by covering the particle surface with a conductive coating such as metal can be used.
  • the shape of the conductive filler various shapes (for example, a spherical shape, an ellipse, a cylindrical shape, a flake, a needle shape, a resin shape, a whisker, a flat plate, a granule, a crystal, an acicular shape, etc.) can be adopted.
  • the conductive filler can also have a slightly rough or jagged surface.
  • the shape of the conductive filler is not particularly limited.
  • the conductive filler according to the present embodiment can be used in combination with the particle shape, size, and / or hardness of the conductive filler.
  • the conductive filler to combine is not restricted to two types, Three or more types may be sufficient.
  • the size of the conductive filler is equal to or less than the size of the conductive structure to be manufactured, or the conductive filler is placed inside the conductive structure due to the arrangement of the conductive filler inside the conductive structure. It is preferable that the shape and size are within the range (for example, when the conductive structure is a thin film and the conductive filler is needle-shaped, the length direction of the conductive filler is arranged in a direction along the surface of the thin film. As long as the length of the acicular conductive filler may be equal to or longer than the length corresponding to the film thickness of the thin film.
  • the conductive filler is used in accordance with the interval at which the plurality of contactors are arranged and / or the size of each contactor. It is preferable to have a size smaller than the size.
  • the conductive filler ensures the flexibility of the conductive structure and makes it difficult to lose the flexibility of the conductive structure even when the contact object is repeatedly contacted or detached (increases the resilience).
  • the purpose is 2.5 to 7.5 parts by mass, preferably 3.1 to 6.3 parts by mass, more preferably 3.7 to 5 parts by mass with respect to 1 part by mass of the polymerizable oligomer. .6 parts by mass or less are mixed.
  • the service life of the conductive structure can be increased by setting the mixing ratio of the conductive filler to the polymerizable oligomer to a predetermined ratio or more, and by reducing the mixing ratio to a predetermined ratio or less, the conductive structure Flexibility can be ensured, and the resilience when repeatedly contacting / leaving the object is also excellent.
  • the initiator according to the present embodiment is a radical polymerization initiator.
  • radical polymerization initiators include organic peroxides such as diacyl peroxides, ketone peroxides, hydroperoxides, dialkyl peroxides, peroxyketals, alkyl peresters, and peroxycarbonates. be able to. Moreover, you may use another radical polymerization initiator as an initiator.
  • radical polymerization initiator examples include benzoyl peroxide, methyl ethyl ketone peroxide, lauryl peroxide, dicumyl peroxide, cumene hydroperoxide and the like. Most commonly, benzoyl peroxide is used.
  • Radical polymerization initiators are generally diluted with inorganic substances such as calcium sulfate and calcium carbonate, dimethyl phthalate, dibutyl phthalate, dicyclohexyl phthalate, aliphatic hydrocarbons, aromatic hydrocarbons, silicone oil, liquid paraffin, polymerizable monomers, water, etc. Diluted with an agent.
  • the initiator is 0.05 parts by mass or more and 20 parts by mass or less, preferably 0.5 parts by mass or more and 15 parts by mass or less, more preferably 1 part by mass or more and 10 parts by mass or less with respect to 1 part by mass of the polymerizable oligomer. It is preferable to use it in an amount.
  • the conductive composition can further contain various monomers such as the monofunctional monomer and / or the polyfunctional monomer described in the polymerizable oligomer.
  • the monomer not only one type of monomer but also a mixture of a plurality of types of monomers can be used.
  • the compound which has the (meth) acryloyloxy group demonstrated in the polymerizable oligomer can be used also as a monomer, and can also be used as a polymer. From the viewpoint of reducing the viscosity of the conductive composition, it is preferable to use a monomer having a (meth) acryloyloxy group.
  • the monomer having a (meth) acryloyloxy group is not particularly limited as long as it is a compound having one or more (meth) acryloyloxy groups, and examples thereof include monofunctional (meth) acrylates and polyfunctional (meth) acrylates. Etc. can be used.
  • the amount of the monomer added with respect to the unit amount of the polymerizable oligomer is not more than a predetermined amount.
  • the addition amount of the monomer with respect to the unit amount of the polymerizable oligomer not more than a predetermined amount, the flexibility of the conductive structure can be secured, and the resilience when repeatedly contacting / leaving the object can be improved.
  • paintability and printability of an electroconductive composition can be controlled.
  • the monomer is added in an amount of 0 to 50 parts by weight, preferably 5 to 40 parts by weight, more preferably 10 to 35 parts by weight with respect to 1 part by weight of the polymerizable oligomer. It is preferable to use it in the quantity.
  • the conductive composition according to the present embodiment includes a dehydrating agent, a filler, a plasticizer, an antioxidant, an ultraviolet absorber, and an adhesion improver as necessary depending on the purpose and application of the conductive structure.
  • Various additives such as thixotropic agents, coupling agents, solvents, diluents, reactive diluents, pigments, dispersants, flame retardants, conductivity imparting agents, and / or thickeners. .
  • plasticizers include phthalate esters such as diisodecyl phthalate, diundecyl phthalate, diisoundecyl phthalate, dioctyl phthalate, dibutyl phthalate, and butyl benzyl phthalate; dimethyl adipate, dioctyl adipate, isodecyl succinate, dibutyl sebacate, etc.
  • Aliphatic dibasic acid esters such as diethylene glycol dibenzoate and pentaerythritol ester; aliphatic esters such as butyl oleate and methyl acetylricinoleate; epoxidized soybean oil, epoxidized linseed oil, and epoxy benzyl stearate Epoxy plasticizers such as; polyester-based plasticizers such as polyesters of dibasic acids and dihydric alcohols; polyethers such as polypropylene glycol and its derivatives; Poly (meth) acrylate plasticizers such as alkyl methacrylates; polystyrenes such as poly- ⁇ -methylstyrene and polystyrene; polybutadiene, butadiene-acrylonitrile copolymers, polychloroprene, polyisoprene, polyisobutene, paraffinic Hydrocarbons, naphthenic hydrocarbons, paraffin-naphthen
  • Adhesion improvers include ⁇ -aminopropyltrimethoxysilane, ⁇ -aminopropyltriethoxysilane, ⁇ -aminopropylmethyldimethoxysilane, N- ( ⁇ -aminoethyl) - ⁇ -aminopropyltrimethoxysilane, N- Amino group-containing silanes such as ( ⁇ -aminoethyl) - ⁇ -aminopropyltriethoxysilane, N- ( ⁇ -aminoethyl) - ⁇ -aminopropylmethyldimethoxysilane, 1,3-diaminoisopropyltrimethoxysilane; N -(1,3-dimethylbutylidene) -3- (triethoxysilyl) -1-propanamine, N- (1,3-dimethylbutylidene) -3- (trimethoxysilyl) -1-propanamine, etc
  • Ketimine type silanes ⁇ -glycidoxypropyltrimethoxysilane, ⁇ -glycidoxypropyltrie Epoxy group-containing silanes such as toxisilane, ⁇ -glycidoxypropylmethyldimethoxysilane, ⁇ - (3,4-epoxycyclohexyl) ethyltrimethoxysilane; ⁇ -mercaptopropyltrimethoxysilane, ⁇ -mercaptopropylmethyldimethoxysilane, etc.
  • Mercapto group-containing silanes include vinyl-type unsaturated group-containing silanes such as vinyltrimethoxysilane, vinyltriethoxysilane, ⁇ -methacryloyloxypropyltrimethoxysilane, and ⁇ -acryloyloxypropylmethyldimethoxysilane; ⁇ -chloropropyltri Chlorine atom-containing silanes such as methoxysilane; Isocyanate-containing silanes such as ⁇ -isocyanatopropyltriethoxysilane and ⁇ -isocyanatopropylmethyldimethoxysilane; methyldimethoxysilane, Silane, hydrosilane and the like, such as methyl diethoxy silane can be specifically exemplified, but not limited thereto.
  • Modified amino group-containing silanes modified by reacting amino group-containing silanes with epoxy group-containing compounds containing silanes, isocyanate group-containing compounds, and (meth) acryloyl group-containing compounds may be used.
  • the adhesion improver is used, for example, to improve the adhesion to a base material (for example, a predetermined film) used when forming a conductive structure (for example, a bump electrode) from a conductive composition. Can do.
  • Fillers include reinforcing silica such as fumed silica, precipitated silica, crystalline silica, fused silica, dolomite, anhydrous silicic acid, hydrous silicic acid, and carbon black; heavy calcium carbonate, colloidal calcium carbonate, carbonic acid Magnesium, diatomaceous earth, calcined clay, clay, talc, titanium oxide, bentonite, organic bentonite, ferric oxide, flint powder, zinc oxide, activated zinc white, shirasu balloon, glass microballoon, phenol resin and vinylidene chloride resin organic Examples thereof include fillers such as resin powders such as microballoons, PVC powders, and PMMA powders; fibrous fillers such as asbestos, glass fibers, and filaments. These fillers can be used alone or in combination of two or more.
  • These fillers include fumed silica, precipitated silica, crystalline silica, fused silica, dolomite, anhydrous silicic acid, hydrous silicic acid, carbon black, surface treated fine calcium carbonate, calcined clay, clay, activated zinc white, oxidized Calcium carbonate such as titanium and heavy calcium carbonate, magnesium carbonate, talc, ferric oxide, zinc oxide, and / or shirasu balloon can be used.
  • An organic balloon and / or an inorganic balloon can be added for the purpose of improving the workability (such as sharpness) of the composition.
  • These fillers can also be subjected to a surface treatment.
  • a filler may be used only by 1 type and can also mix and use 2 or more types of fillers.
  • the balloon particle size is preferably 0.1 mm or less.
  • silica when it is intended to prevent bleed while ensuring flowability without increasing the viscosity, it is preferable to add silica to the conductive composition.
  • Silica can be subjected to a surface treatment on its surface, and may be used alone or in combination of two or more kinds of silica. From the viewpoint of preventing bleeding, it is preferable to use hydrophilic silica or hydrophobic silica hydrophobized with a specific surface treatment agent.
  • the hydrophobic silica is one or more surface treatment agents selected from the group consisting of dimethyldichlorosilane, hexamethyldisilazane, (meth) acrylsilane, octylsilane (for example, trimethoxyoctylsilane), and aminosilane. Hydrophobic silica that has been subjected to a hydrophobization treatment by is preferred.
  • a solvent and / or a diluent is blended.
  • the solvent include aromatic hydrocarbon solvents such as toluene and xylene; ester solvents such as ethyl acetate, butyl acetate, amyl acetate, and cellosolve; ketone solvents such as methyl ethyl ketone and methyl isobutyl ketone.
  • the diluent include normal paraffin and isoparaffin.
  • a tackifier may be added to the conductive composition in order to improve the wettability to the adherend and increase the peel strength.
  • the tackifier include petroleum resin, rosin / rosin ester, acrylic resin, terpene resin, hydrogenated terpene resin and its phenol resin copolymer, phenol / phenol novolac resin, and the like.
  • the conductive composition according to the present embodiment can be a one-component type or a two-component type as required, and can be suitably used particularly as a one-component type.
  • the conductive composition according to this embodiment is a viscous liquid composition, it has excellent workability.
  • the conductive composition according to the present embodiment preferably has a viscosity at 23 ° C. in the range of 50 Pa ⁇ s to 200 Pa ⁇ s.
  • the conductive composition according to the present embodiment can have the same performance as that of a solvent system even without a solvent.
  • a solvent system even without a solvent.
  • no solvent since there is no volatile component during coating or printing, the viscosity does not change, the stability and reproducibility are excellent, and there is no variation in products. Further, when no solvent is used, there is an effect that there is little shrinkage of the cured product and stress is not substantially generated even in a large area.
  • the conductive composition according to the present embodiment has high conductivity and can be used as a bump by being applied or printed on a substrate and cured.
  • the conductive composition according to the present embodiment is suitable for use as a conductive contact member that repeatedly contacts / releases an electrode of an electronic component in a test and / or inspection of an electronic component such as a semiconductor element chip component or a discrete component. Used.
  • the conductive composition according to the present embodiment is a device such as a mesh screen plate, a stencil plate, a gravure, an offset, a flexo, an ink jet, a roller coater, a dispenser, and a dipping on an organic and / or inorganic base material. The method can be used for coating, printing, or filling.
  • composition preparing step a liquid conductive composition having viscosity according to the present embodiment is prepared (composition preparing step). That is, a predetermined amount of polymerizable oligomer, a predetermined amount of conductive filler, a predetermined amount of initiator, a predetermined amount of monomer, and / or other predetermined amount of additives are weighed and mixed to obtain a viscous liquid conductive material. A sex composition is prepared.
  • the prepared conductive composition is molded into a predetermined shape (molding process). Then, the conductive composition in a molded state is heated and cured under an oxygen-blocking atmosphere (for example, under a nitrogen atmosphere) to produce a conductive structure (curing step). For example, a mask pattern is provided on a predetermined substrate (for example, a metal mask is superimposed on the predetermined substrate or a mask pattern is formed on the substrate surface using a photoresist), and the mask opening according to the present embodiment A liquid conductive composition having viscosity is filled. Next, the mask is removed. Thereby, a conductive composition is shape
  • the conductive composition molded in an oxygen-blocking atmosphere is subjected to heat treatment.
  • the heat treatment is performed, for example, in a nitrogen atmosphere at a temperature of about 120 ° C. to 130 ° C. for a period of 30 minutes to 60 minutes.
  • the conductive structure according to the present embodiment having a desired shape is formed.
  • the shape of the conductive structure may be any of spherical, elliptical, cylindrical, flake, needle, resin, whisker, flat plate (sheet), agglomerate, or other shapes. Good.
  • FIG. 1 shows an example of the form of the conductive structure according to the present embodiment. Specifically, FIG. 1A shows an example of a sheet-like conductive structure, and FIG. 1B shows an example in which a plurality of conductive structures are provided on a predetermined substrate.
  • the sheet-shaped conductive composition is cured. Thereby, as shown to Fig.1 (a), the sheet-like electroconductive structure 20 is formed.
  • the thickness of the sheet-like conductive structure 20 can be appropriately adjusted according to the application.
  • the sheet-like conductive structure 20 can be wound into a roll shape. In this case, a release sheet can be attached to one surface of the sheet-like conductive structure 20.
  • the conductive composition is disposed in a predetermined region of a predetermined base material (for example, a polymer resin or the like).
  • the conductive composition is disposed in a predetermined region of the insulating substrate 10.
  • interval on the insulated substrate 10 can be formed.
  • the conductive structure is formed on the surface of the insulating substrate 10 or is formed so as to fill a through hole provided in the insulating substrate 10 in advance.
  • a predetermined amount of the conductive composition that has been molded and cured in a predetermined shape (for example, a particle shape, a rod shape, etc.) in advance is added to a predetermined base material (for example, insulating resin, epoxy resin, etc.).
  • a predetermined base material for example, insulating resin, epoxy resin, etc.
  • the conductive structure according to this embodiment can also be formed by curing the base material.
  • a conductive structure is formed by adding a cured conductive composition to a liquid substrate having viscosity or a substrate having a predetermined viscoelasticity (for example, an epoxy resin). .
  • FIG. 2 shows another example of the form of the conductive structure according to the present embodiment.
  • the conductive structure according to the present embodiment can be formed as a conductive structure 20 having a plurality of bump electrode shapes on the surface of the insulating substrate 14.
  • each bump electrode is electrically connected to a circuit pattern (not shown).
  • a bump electrode as the conductive structure 20 can be formed in the through hole 16 penetrating the insulating substrate 14.
  • the through hole 16 is filled with a conductive composition.
  • the electroconductive composition with which the through-hole 16 was filled is hardened. Thereby, the conductive structure filled in the through-hole 16 constitutes a bump electrode.
  • the conductive structure according to the present embodiment contains a conductive filler inside the conductive structure, and its shape can be designed freely. Therefore, according to the electroconductive structure which concerns on this Embodiment, the electroconductive structure which has a suitable shape according to the use condition can be provided. For example, even when a thin-film conductive structure is formed, the distance between the plurality of conductive fillers existing in the conductive structure is closer or closer than before the thin film is formed. The conductive structure can maintain good electrical conductivity. Furthermore, the conductive structure can maintain good electrical conductivity regardless of the position of the conductive structure even when the shape changes due to pressure applied from the outside.
  • the conductive composition according to the present embodiment is obtained by mixing a conductive filler with a polymerizable oligomer and appropriately controlling the ratio of the conductive filler to the polymerizable oligomer in this case, thereby curing the conductive structure. Flexibility and reaction force can be controlled within an optimum range. Therefore, according to the present embodiment, the conductive structure obtained by curing the conductive composition damages the contact object even when the contact object is repeatedly contacted and detached. The long-term flexibility can be maintained.
  • the shape of the conductive structure obtained by curing the conductive composition can be freely designed by forming the conductive composition into a predetermined shape. be able to. For example, a sheet-like or thin-film conductive structure can be manufactured.
  • the conductive composition is a viscous liquid
  • the conductive composition droplets can be arranged at a narrow pitch. Therefore, according to the present embodiment, for example, a plurality of bump electrodes arranged with a narrow pitch of about 50 ⁇ m can be realized.
  • Example 1 The conductive composition according to Example 1 was manufactured as follows. First, 80 parts by mass of an acrylic polymer (manufactured by Kaneka Corporation, RC200C) was weighed as a compound having a radical polymerizable vinyl group which is a polymerizable oligomer. Moreover, the filler made from Ag was weighed as a conductive filler.
  • an acrylic polymer manufactured by Kaneka Corporation, RC200C
  • the filler made from Ag was weighed as a conductive filler.
  • the obtained conductive composition was sandwiched between 100 ⁇ m-thick Teflon (registered trademark) sheets, and further sandwiched between glass plates, and then fixed by applying pressure with clips.
  • the conductive composition was cured by placing the conductive composition in this state for 60 minutes in a hot-air circulating drier whose temperature was adjusted to 120 ° C. Thereby, the conductive structure for volume resistivity measurement according to Example 1 was obtained.
  • FIG. 3 shows an outline of a sample for reaction force measurement.
  • a Kapton tape 50 (thickness: 50 ⁇ m) was pasted on both ends of the glass plate 15, and the conductive composition according to Example 1 was applied between the Kapton tapes 50. And the glass plate 15 of this state was installed in the airtight container substituted by nitrogen. Next, the inside of the sealed container was adjusted to 120 ° C., and the glass plate 15 coated with the conductive composition according to Example 1 was subjected to heat treatment for 60 minutes. Thereby, the conductive structure 1 for reaction force measurement according to Example 1 was obtained. As will be described later, the reaction force was measured by pushing a rod 60 of a push gauge into the conductive structure 1 on the glass plate 15.
  • Example 2 The conductive composition according to Example 2 was manufactured in the same process using the same components except that the conductive filler was different from that in Example 1. Therefore, a detailed description is omitted except for differences.
  • a filler made of Ag 200 parts by mass of Sylbest TCG-7 (manufactured by Tokoku Chemical Laboratories, Inc., flaky silver), 70 parts by mass of Sylbest AgS-050 (Tokuriki Chemical Research) Sokaku AgC-G (manufactured by Fukuda Metal Foil Powder Co., Ltd., microcrystalline silver) was weighed.
  • Example 3 The conductive composition according to Example 3 was manufactured in the same process using the same components except that the conductive filler was different from that in Example 1. Therefore, a detailed description is omitted except for differences.
  • Ag filler 140 parts by mass of Sylbest TCG-7 (manufactured by Tokoku Chemical Laboratories, Inc., flaky silver), 50 parts by mass of Sylbest AgS-050 (Tokuriki Chemical Research Co., Ltd.) Sokaku AgC-G (manufactured by Fukuda Metal Foil Powder Co., Ltd., microcrystalline silver) was weighed.
  • Example 4 The conductive composition according to Example 4 was manufactured in the same process using the same components except that the conductive filler was different from that in Example 1. Therefore, a detailed description is omitted except for differences.
  • a filler made of Ag 300 parts by mass of Sylbest TCG-7 (manufactured by Tokiki Chemical Laboratory Co., Ltd., flaky silver), and 200 parts by mass of Silcote AgC-G (Fukuda Metal Foil Powder Industry) Co., Ltd., microcrystalline silver was weighed.
  • Example 5 The conductive composition according to Example 5 was manufactured in the same process using the same components except that the conductive filler was different from that in Example 1. Therefore, a detailed description is omitted except for differences.
  • a filler made of Ag 300 parts by mass of Sylbest TCG-7 (manufactured by Tokoku Chemical Laboratories, Inc., flaky silver), 100 parts by weight of Sylbest AgS-050 (Tokuriki Chemical Research) Sokaku AgC-G (Fukuda Metal Foil Powder Co., Ltd., microcrystalline silver) was weighed.
  • Example 6 The conductive composition according to Example 6 was manufactured in the same process using the same components except that the conductive filler was different from that in Example 1. Therefore, a detailed description is omitted except for differences.
  • a filler made of Ag 100 parts by mass of Sylbest TCG-7 (manufactured by Tokoku Chemical Laboratories, Inc., flaky silver), 35 parts by mass of Sylbest AgS-050 (Tokuriki Chemical Research Co., Ltd.) Sokaku AgC-G (manufactured by Fukuda Metal Foil Powder Co., Ltd., microcrystalline silver) was weighed.
  • Test method volume resistivity
  • the volume resistivity was measured by a four-end needle method measurement for a conductive structure manufactured for volume resistivity measurement.
  • Lorester MCP-T360 manufactured by Mitsubishi Chemical Analytech Co., Ltd. was used.
  • each reaction force was measured.
  • a push gauge digital push-pull gauge RX-1 manufactured by Aiko Engineering Co., Ltd.
  • a rod gauge with a cylindrical attachment of 2 mm in diameter attached to the tip of a push gauge is brought into contact with the surface of the conductive member, and the strain when the rod is pushed vertically into the conductive member from this state ( That is, the measurement was performed by measuring the indentation ratio) and the reaction force against the distortion.
  • the strain was measured based on the size (that is, thickness) of the conductive member before the rod was brought into contact with the surface of the conductive member. Therefore, the strain “X%” indicates a state where the rod is pushed in by an amount corresponding to “X%” of the thickness of the conductive member before the rod contact. Further, “the rate of change in height” after repeated pushing indicates the rate of change in height after rod removal with respect to the height (that is, thickness) of the conductive member before pushing the rod. Therefore, the rate of change in height “Y%” means that the thickness of the conductive member has changed from the initial thickness by an amount corresponding to “Y%” of the thickness of the conductive member before the rod contact. Show.
  • each reaction force was measured.
  • the reaction force was measured in the same manner as “Test method: Reaction force after 10 repetitions”. However, the number of measurements of strain and reaction force against the strain was 1000.
  • each conductive member was evaluated based on the following criteria.
  • Within% ⁇ Reaction force is 2.0 g or less at 30% strain, but the rate of change in height exceeds 10%, or reaction force exceeds 4.0 g.
  • ⁇ Reaction force is 2.0 g or less at 30% strain However, the rate of change in height exceeds 20%, or the reaction force exceeds 5.0 g.
  • Table 1 shows the raw material compositions of the conductive compositions according to Examples 1 to 6 and the test results of the conductive structures.
  • the conductive structures according to Examples 1 to 6 do not substantially lose flexibility even after being repeatedly pushed 1000 times with a push gauge. It was shown that. In particular, it was shown that the conductive structures according to Examples 1 to 3 substantially maintain the flexibility before the test even after 1000 times of repeated pressing. In addition, the conductive structures according to Examples 1 to 6 have a volume resistivity of 2.20 ⁇ 10 ⁇ 4 ( ⁇ ⁇ cm) or more and 1.50 ⁇ 10 ⁇ 2 ( ⁇ ⁇ cm) or less. It was shown that the conductivity is also good.

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PCT/JP2016/056484 2015-03-11 2016-03-02 導電性構造体、及び導電性構造体の製造方法 WO2016143640A1 (ja)

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