WO2024058218A1 - Composition d'agent adhésif, film d'agent adhésif, corps de structure de connexion et procédé de fabrication associé - Google Patents

Composition d'agent adhésif, film d'agent adhésif, corps de structure de connexion et procédé de fabrication associé Download PDF

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WO2024058218A1
WO2024058218A1 PCT/JP2023/033398 JP2023033398W WO2024058218A1 WO 2024058218 A1 WO2024058218 A1 WO 2024058218A1 JP 2023033398 W JP2023033398 W JP 2023033398W WO 2024058218 A1 WO2024058218 A1 WO 2024058218A1
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adhesive composition
circuit member
mass
adhesive
electrode
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PCT/JP2023/033398
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English (en)
Japanese (ja)
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英樹 吉田
直 工藤
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株式会社レゾナック
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/02—Non-macromolecular additives
    • C09J11/04—Non-macromolecular additives inorganic
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/02—Non-macromolecular additives
    • C09J11/06—Non-macromolecular additives organic
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/10—Adhesives in the form of films or foils without carriers
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition

Definitions

  • the present invention relates to an adhesive composition, an adhesive film, a connected structure, and a method for manufacturing the same.
  • radical curing adhesives for example, radical curing adhesives that use a combination of (meth)acrylate derivatives and peroxides, which are radical polymerization initiators
  • Radical curing systems can be cured in a short time because the radicals that are active species are highly reactive, and the adhesive remains stable below the decomposition temperature of the radical polymerization initiator, so it can be cured at low temperatures. It is a curing system that achieves both short-time curing and storage stability (for example, storage stability near room temperature).
  • radical curing systems do not use ionic polymerization like cationic-epoxy curing systems, anionic-epoxy curing systems, etc., they have an advantage over epoxy curing systems in that they cannot be used in general high-temperature, high-humidity tests. It is characterized by excellent corrosion resistance when used.
  • the corrosion may be suppressed by adding metal hydroxides or metal oxides (for example, see Patent Documents 1 to 4 below). ).
  • circuit connection materials used in these terminal components are expected to be exposed to salt water such as sweat and seawater, and have excellent properties even when structures obtained using the circuit connection materials are exposed to salt water. connection reliability is required. That is, such circuit connection materials are required to have excellent salt water resistance (resistance to salt water).
  • An object of the present invention is to provide an adhesive composition capable of obtaining a connected structure with excellent salt water resistance, an adhesive film using the same, a connected structure, and a method for producing the same.
  • Methods for evaluating salt water resistance include JIS Z 2371 (2000 Salt Water Spray Test Method); ISO 9227 (2006 Corrosion Tests in Artificial Atmospheres-Salt Spray tests.); Method of soaking in 5% salt water; Methods such as soaking in salt water and then placing it in a high-temperature, high-humidity tank are used.
  • a radical curing adhesive composition is a cationic-epoxy curing adhesive composition.
  • peeling occurs more easily at the joints and has lower salt water resistance than anionic-epoxy curing adhesive compositions.
  • the present disclosure includes the following aspects.
  • the nitrogen-containing aromatic heterocycle is at least one member selected from the group consisting of a pyrazole ring, an imidazole ring, a triazole ring, a tetrazole ring, a thiazole ring, a thiadiazole ring, an oxazole ring, and a pyrimidine ring. adhesive composition.
  • the total content of the compound having a nitrogen-containing aromatic heterocycle and the content of the particles is 0.1 parts by mass or more and 5 parts by mass or less, based on 100 parts by mass of the total amount of the radically polymerizable compound.
  • An adhesive film comprising an adhesive layer containing the adhesive composition according to any one of [1] to [6].
  • the adhesive composition according to any one of [1] to [6] is applied between the first circuit member having the first electrode and the second circuit member having the second electrode.
  • a method for manufacturing a connected structure comprising the step of electrically connecting a first electrode and a second electrode to each other by interposing the first circuit member and the second circuit member by thermocompression bonding.
  • an adhesive composition that allows a bonded structure with excellent salt water resistance to be obtained.
  • the connection structure is resistant to peeling even under conditions that are more severe than conventional test conditions, such as spraying salt water for a longer period of time. You can get a body.
  • the present invention it is possible to provide a connected structure that suppresses peeling at the interface between a circuit member and a connecting portion when the connected structure is used in a high temperature and high humidity environment, and has low connection resistance. It also becomes possible.
  • an adhesive composition capable of obtaining a connected structure with excellent salt water resistance, an adhesive film using the same, a connected structure, and a method for manufacturing the same.
  • FIG. 1 is a schematic cross-sectional view showing an adhesive film according to one embodiment.
  • FIG. 7 is a schematic cross-sectional view showing an adhesive film according to another embodiment.
  • FIG. 2 is a schematic cross-sectional view showing one embodiment of a connected structure.
  • a numerical range indicated using "-" indicates a range that includes the numerical values written before and after "-" as the minimum and maximum values, respectively.
  • the upper limit or lower limit of the numerical range of one step may be replaced with the upper limit or lower limit of the numerical range of another step.
  • the upper limit or lower limit of the numerical range may be replaced with the value shown in the Examples.
  • the upper limit values and lower limit values described individually can be combined arbitrarily.
  • “(meth)acrylate” means at least one of an acrylate and a methacrylate corresponding thereto. The same applies to other similar expressions such as "(meth)acryloyl”.
  • (poly) means both with and without the prefix “poly”.
  • a or B may include either A or B, or both.
  • the materials exemplified below may be used alone or in combination of two or more, unless otherwise specified.
  • the content of each component in the composition means the total amount of the plurality of substances present in the composition, unless otherwise specified.
  • the adhesive composition of the present embodiment includes a radically polymerizable compound (also called a radically polymerizable substance or a radically reactive component), a radical polymerization initiator, a compound having a nitrogen-containing aromatic heterocycle, and a metal hydroxide. and particles containing at least one metal compound selected from the group consisting of metal oxides.
  • a radically polymerizable compound is a compound having a functional group capable of radical polymerization.
  • examples of such compounds include vinyl compounds having a vinyl group, (meth)acrylate compounds having a (meth)acryloyl group, and the like.
  • the radically polymerizable compound may be used in the form of a monomer or an oligomer, or a combination of a monomer and an oligomer may be used.
  • the radically polymerizable compounds may be used alone or in combination of two or more.
  • the radically polymerizable compound is preferably a (meth)acrylate compound from the viewpoint of obtaining better salt water resistance.
  • (Meth)acrylate compounds include ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, trimethylolpropane tri(meth)acrylate, tetramethylolmethanetetra(meth)acrylate, 2-hydroxy-1,3-di(meth)acrylate, (meth)acryloxypropane, 2,2-bis[4-((meth)acryloxymethoxy)phenyl]propane, 2,2-bis[4-((meth)acryloxypolyethoxy)phenyl]propane, dicyclo Pentenyl (meth)acrylate, tricyclodecanyl (meth)acrylate, tris((meth)acryloyloxyethyl)isocyanurate, (poly)urethane (meth)acrylate, dimethyloltricyclodecane di(
  • the (meth)acrylate compound may be (poly)urethane (meth)acrylate from the viewpoint of balancing crosslinking density and curing shrinkage, further reducing connection resistance, and improving high temperature and high humidity resistant connection reliability.
  • the content of (poly)urethane (meth)acrylate may be 20% by mass or more, 40% by mass or more, or 60% by mass or more, and 90% by mass or less, or It may be 80% by mass or less.
  • the adhesive composition may contain only (poly)urethane (meth)acrylate as the radically polymerizable compound.
  • the (poly)urethane (meth)acrylate may have a weight average molecular weight of 1.0 ⁇ 10 4 or more, and from the viewpoint of miscibility, it is 1.0 ⁇ 10 4 or more and 1.0 ⁇ 10 6 or less. Good too.
  • the weight average molecular weight here is measured by gel permeation chromatography (GPC) according to the conditions described in Examples using a standard polystyrene calibration curve.
  • the (meth)acrylate compound one having at least one partial structure selected from the group consisting of a dicyclopentane skeleton, a tricyclodecane skeleton, and a triazine ring can also be used.
  • a (meth)acrylate compound having such a partial structure as a radically polymerizable compound, the cured product of the adhesive composition has excellent heat resistance.
  • the (meth)acrylate compound may be a (meth)acrylate compound having a tricyclodecane skeleton from the viewpoint of balancing crosslinking density and curing shrinkage and further reducing connection resistance.
  • the content of the (meth)acrylate compound having a tricyclodecane skeleton is 1% by mass or more, 5% by mass or more, based on the total mass of the radically polymerizable compound. Alternatively, it may be 10% by mass or more, and may be 90% by mass or less, 60% by mass or less, or 30% by mass or less.
  • the (meth)acrylate compound may be a compound represented by the following formula (1) (a (meth)acrylate compound having a phosphate ester structure).
  • a (meth)acrylate compound having a phosphate ester structure since the adhesive strength to the surface of the inorganic material (metal etc.) is improved, the adhesion between the electrodes (for example, between circuit electrodes) becomes more excellent.
  • n represents an integer of 1 to 3
  • R represents a hydrogen atom or a methyl group.
  • the (meth)acrylate compound represented by formula (1) can be obtained, for example, by reacting phosphoric anhydride and 2-hydroxyethyl (meth)acrylate.
  • Specific examples of the (meth)acrylate compound represented by formula (1) include mono(2-(meth)acryloyloxyethyl)acid phosphate, di(2-(meth)acryloyloxyethyl)acid phosphate, etc. Can be mentioned.
  • the content of the (meth)acrylate compound represented by formula (1) is determined from the viewpoint of reducing the connection resistance and making it easier to obtain the crosslinking density required to improve the connection reliability. Based on the mass, it may be 1% by mass or more, or 2% by mass or more, and 20% by mass or less, 10% by mass or less, or 5% by mass or less.
  • the radically polymerizable compound other than the (meth)acrylate compound for example, the compound described in Patent Document 5 (International Publication No. 2009/063827) can be used.
  • Radical polymerizable compounds include polyurethane, polystyrene, polyethylene, polyvinyl butyral, polyvinyl formal, polyimide, polyamide, polyester, polyvinyl chloride, polyphenylene oxide, urea resin, melamine resin, phenol resin, xylene resin, epoxy resin, polyisocyanate resin, It may also be a polymer such as phenoxy resin. These polymers have at least one radically polymerizable functional group in the molecule.
  • the adhesive composition has excellent handling properties and is excellent in stress relaxation during curing. Furthermore, when the polymer has a functional group such as a hydroxyl group, it also has excellent adhesive properties. From this point of view, it is more preferable to use each polymer modified with a radically polymerizable functional group.
  • the weight average molecular weight of the polymer may be 1.0 ⁇ 10 4 or more, and from the viewpoint of miscibility, it may be 1.0 ⁇ 10 4 or more and 1.0 ⁇ 10 6 or less.
  • the weight average molecular weight here is measured by gel permeation chromatography (GPC) according to the conditions described in Examples using a standard polystyrene calibration curve.
  • the content of the radically polymerizable compound is determined from the resin component (conductive particles and The content may be 5% by mass or more, 20% by mass or more, or 40% by mass or more, and 90% by mass or less, 75% by mass or less, based on the total mass of components other than fillers (details will be described later). It may be 60% by mass or less.
  • the radical polymerization initiator is a compound that generates free radicals, and examples thereof include compounds that generate free radicals when decomposed by heating, such as peroxide compounds and azo compounds.
  • the radical polymerization initiator is appropriately selected depending on the intended connection temperature, connection time, etc.
  • the radical polymerization initiators may be used alone or in combination of two or more.
  • radical polymerization initiator examples include diacyl peroxides, peroxydicarbonates, peroxyesters, peroxyketals, dialkyl peroxides, and hydroperoxides.
  • diacyl peroxides examples include 2,4-dichlorobenzoyl peroxide, 3,5,5-trimethylhexanoyl peroxide, octanoyl peroxide, lauroyl peroxide, stearoyl peroxide, succinic peroxide, and benzoyl peroxytoluene. , benzoyl peroxide, and the like.
  • peroxydicarbonates include di-n-propyl peroxydicarbonate, diisopropyl peroxydicarbonate, bis(4-t-butylcyclohexyl) peroxydicarbonate, di-2-ethoxymethoxyperoxydicarbonate, and di-2-ethoxymethoxyperoxydicarbonate.
  • Examples include (2-ethylhexylperoxy) dicarbonate, dimethoxybutylperoxydicarbonate, di(3-methyl-3-methoxybutylperoxy)dicarbonate, and the like.
  • Peroxy esters include 1,1,3,3-tetramethylbutyl peroxyneodecanoate, 1-cyclohexyl-1-methylethyl peroxyneodecanoate, t-hexylperoxyneodecanoate, t-Butyl peroxypivalate, 1,1,3,3-tetramethylbutylperoxy-2-ethylhexanoate, 2,5-dimethyl-2,5-di(2-ethylhexanoylperoxy)hexane , 1-cyclohexyl-1-methylethylperoxy-2-ethylhexanonate, t-hexylperoxy-2-ethylhexanoate, t-butylperoxy-2-ethylhexanoate, t-butylperoxy Isobutyrate, 1,1-bis(t-butylperoxy)cyclohexane, t-hexylperoxyiso
  • dialkyl peroxides examples include ⁇ , ⁇ '-bis(t-butylperoxy)diisopropylbenzene, dicumyl peroxide, 2,5-dimethyl-2,5-di(t-butylperoxy)hexane, and t- Examples include butylcumyl peroxide.
  • hydroperoxides examples include diisopropylbenzene hydroperoxide and cumene hydroperoxide.
  • radical polymerization initiators may be used in combination with decomposition accelerators, inhibitors, and the like.
  • the content of the radical polymerization initiator is 0.1% by mass or more, 0.5% by mass or more, or 1% by mass or more based on the total mass of the resin components of the adhesive composition. Often it may be up to 20% by weight, up to 10% by weight or up to 5% by weight.
  • a compound having a nitrogen-containing aromatic heterocycle is a compound having an aromatic heterocycle containing one or more nitrogen atoms in the ring.
  • a nitrogen-containing aromatic heterocycle is composed of at least two types of atoms, a carbon atom and a nitrogen atom, and in addition to carbon atoms and nitrogen atoms, three or more types of atoms include other atoms such as sulfur atoms and oxygen atoms. It may be composed of.
  • the nitrogen-containing aromatic heterocycle contains, for example, 1 to 4 nitrogen atoms, preferably 2 to 4 nitrogen atoms. When the nitrogen-containing aromatic heterocycle contains one nitrogen atom, the nitrogen-containing aromatic heterocycle preferably further contains the above-mentioned other atoms in addition to the carbon atom and the nitrogen atom.
  • the nitrogen-containing aromatic heterocycle is preferably a compound having a 5-membered ring or a 6-membered ring, more preferably a compound having a 5-membered ring (azole).
  • the 5-membered ring include a pyrazole ring, an imidazole ring, a triazole ring, a tetrazole ring, a thiazole ring, a thiadiazole ring, and an oxazole ring.
  • Examples of the 6-membered ring include a pyrimidine ring.
  • the nitrogen-containing aromatic heterocycle is preferably a pyrazole ring, an imidazole ring, a triazole ring, a tetrazole ring, a thiazole ring, a thiadiazole ring, an oxazole ring, or At least one member selected from the group consisting of pyrimidine rings, more preferably at least one member selected from the group consisting of pyrazole rings, imidazole rings, triazole rings, tetrazole rings, thiazole rings, thiadiazole rings, and oxazole rings, still more preferably is at least one member selected from the group consisting of a triazole ring, a tetrazole ring, and a thiadiazole ring.
  • the nitrogen-containing aromatic heterocycle may be unsubstituted or may have a substituent (hydrogen atoms bonded to atoms constituting the nitrogen-containing aromatic heterocycle are substituted).
  • the substituent may be a hydrocarbon group or an organic group containing a sulfur atom, an oxygen atom, or the like.
  • the hydrocarbon group may be an alkyl group or the like.
  • the organic group containing a nitrogen atom may be an amino group or the like.
  • the organic group containing a sulfur atom may be a mercapto group or the like.
  • the compound having a nitrogen-containing aromatic heterocycle may have a monocyclic nitrogen-containing aromatic heterocycle, or, for example, an aromatic ring composed only of hydrocarbons (e.g., substituted or unsubstituted benzene). ring) and the above-mentioned nitrogen-containing aromatic heterocycle may have a condensed polycycle.
  • Such polycycles may be, for example, benzimidazole rings, benzotriazole rings, benzothiazole rings, benzoxazole rings, and the like.
  • the compound having a nitrogen-containing aromatic heterocycle includes 1H-1,2,4-triazole, 3-amino-1H-1,2,4-triazole, 3-mercapto-1,2,4 -triazole, 1H-tetrazole, 5-methyl-1H-tetrazole, 5-amino-1H-tetrazole, 2-amino-5-mercapto-1,3,4-thiadiazole, 2-aminopyrimidine, 2-mercaptopyrimidine, 5 , 6-dimethylbenzimidazole, 2-mercaptobenzimidazole, benzotriazole, 2-mercaptobenzothiazole, 2-mercaptobenzoxazole, and the like.
  • the content of the compound having a nitrogen-containing aromatic heterocycle is 0.1% by mass or more and 0.25% by mass based on the total mass of the resin component of the adhesive composition, from the viewpoint of obtaining even better salt water resistance. or more, or 0.5% by mass or more, and 5% by mass or less, 3% by mass or less, or 1% by mass or less.
  • the content of the compound having a nitrogen-containing aromatic heterocycle is 0.1 parts by mass or more, 0.5 parts by mass or more with respect to 100 parts by mass of the total amount of radically polymerizable compounds, from the viewpoint of obtaining even better salt water resistance. , 1 part by weight or more, or 3 parts by weight or more, and may be 5 parts by weight or less, 3 parts by weight or less, or 1 part by weight or less.
  • the adhesive composition contains particles containing at least one metal compound selected from the group consisting of metal hydroxides and metal oxides. These particles are different in type from the conductive particles described below.
  • the particles may include metal hydroxides or metal oxides.
  • the cured product of the adhesive composition that becomes the connection section One example is that the polarity is low.
  • a polymer of a radically polymerizable compound has a carbon-carbon bond (CC) as a main skeleton, it tends to have low polarity.
  • CC carbon-carbon bond
  • the adherend has an insulating material part containing an insulating material such as SiO 2 or SiN x
  • the insulating material part has many hydroxyl groups on the surface and is easily wetted by water (salt water, etc.).
  • water salt water, etc.
  • the inclusion of metal oxide and/or metal hydroxide increases the polarity of the adhesive composition itself, and furthermore, the ionic component that causes adhesion inhibition. It is considered that the salt water resistance of the connected structure can be improved by being captured by the metal oxide and/or metal hydroxide and inhibiting adhesion.
  • a compound having a nitrogen-containing aromatic heterocycle is used in combination, so that connection can be achieved even under conditions where salt water is sprayed for a longer period of time. Peeling of parts can be suppressed.
  • the metal compound contains at least one metal element selected from the group consisting of aluminum, magnesium, zirconium, bismuth, calcium, tin, manganese, antimony, titanium, and silicon as a metal element constituting the metal hydroxide or metal oxide. Good too.
  • the metal compound may be a metal compound containing a trivalent or tetravalent metal.
  • metal hydroxides include aluminum hydroxide, magnesium hydroxide, calcium hydroxide, magnesium aluminum hydrotalcite, and the like.
  • metal oxides include aluminum oxide, magnesium oxide, antimony oxide, tin oxide, titanium oxide, manganese oxide, zirconium oxide, and silicon oxide.
  • particles containing metal compounds these compounds may be used alone or in combination of two or more. Particles containing a metal hydroxide and particles containing a metal oxide may be used in combination.
  • the average primary particle size of the particles containing the metal compound is determined from the viewpoints of obtaining excellent dispersibility in the adhesive composition and high adhesion to the adherend, preventing corrosion of the adherend, and the ionic component. From the viewpoint of obtaining trapping ability and suppressing short circuits due to large particles (short circuits when particles containing a metal compound become foreign substances), the diameter may be 10 ⁇ m or less, 5 ⁇ m or less, or 1 ⁇ m or less. As the average primary particle size of the particles containing the metal compound becomes smaller, the specific surface area of the entire particles in the adhesive composition increases, resulting in the effect of obtaining high adhesion to the adherend and reducing corrosion of the adherend.
  • the average primary particle size of the particles containing the metal compound may be 0.5 ⁇ m or more, or 1 ⁇ m or more.
  • the average primary particle size of particles containing a metal compound can be measured using, for example, a scanning electron microscope.
  • the content of particles containing the metal compound may be 0.1% by mass or more, 0.25% by mass or more, or 0.5% by mass or more, based on the total mass of the resin component of the adhesive composition. It may be 5% by weight or less, 3% by weight or less, or 1% by weight or less.
  • the content of the particles containing the metal compound is 0.1 parts by mass or more, 0.5 parts by mass or more, 1 part by mass or more, 2 parts by mass or more, or 3 parts by mass, based on 100 parts by mass of the total amount of the radically polymerizable compound.
  • the amount may be 7 parts by weight or less, 5 parts by weight or less, 3 parts by weight or less, or 1 part by weight or less.
  • the total content of the compound having a nitrogen-containing aromatic heterocycle and the content of particles containing a metal compound as described above should be set to 100 parts by mass of the total amount of radically polymerizable compounds, from the viewpoint of obtaining even better salt water resistance. , 0.1 parts by weight or more, 0.5 parts by weight or more, or 3 parts by weight or more, and may be 5 parts by weight or less, 3 parts by weight or less, or 1 part by weight or less.
  • the adhesive composition may contain a thermoplastic resin.
  • the adhesive composition may contain a thermoplastic resin, the adhesive composition can be easily handled when molded into a film.
  • thermoplastic resin polyvinyl butyral resin, polyvinyl formal resin, polyamide resin, polyester resin, phenol resin, epoxy resin, phenoxy resin, polystyrene resin, xylene resin, polyurethane resin, polyester urethane resin, etc. can be used. These may be used alone or in combination of two or more.
  • the weight average molecular weight of the thermoplastic resin may be 1.0 ⁇ 10 4 or more from the viewpoint of excellent film forming properties of the adhesive composition, and 1.0 ⁇ 10 4 or more from the viewpoint of mixability. It may be less than 1.0 ⁇ 10 6 .
  • the weight average molecular weight here is measured by gel permeation chromatography (GPC) according to the conditions described in Examples using a standard polystyrene calibration curve.
  • thermoplastic resin a hydroxyl group-containing resin (eg, phenoxy resin) having a Tg (glass transition temperature) of 40° C. or higher and a weight average molecular weight of 1.0 ⁇ 10 4 or higher can be used.
  • the hydroxyl group-containing resin may be modified with an epoxy group-containing elastomer.
  • Phenoxy resin can be obtained by reacting bifunctional phenols and epihalohydrin to a high molecular weight, or by polyaddition reaction of bifunctional epoxy resins and difunctional phenols.
  • a polyester urethane resin may be used as the thermoplastic resin.
  • thermoplastic resin having a radically polymerizable functional group is blended as the above-mentioned radically polymerizable compound.
  • the content of the thermoplastic resin may be 5% by mass or more or 30% by mass or more, and 80% by mass or less or 60% by mass or less, based on the total mass of the resin components of the adhesive composition.
  • the adhesive composition may contain conductive particles.
  • the conductive particles may be metal particles such as Au, Ag, Ni, Cu, or solder, or conductive carbon particles made of conductive carbon.
  • the conductive particles may be made by coating the surface of a transition metal such as Ni with a noble metal such as Au. From the viewpoint of obtaining a sufficient pot life, the surface layer may be made of Au, Ag, or a noble metal of the platinum group, or may be Au.
  • Conductive particles are made by forming a conductive layer on the surface of non-conductive particles such as glass, ceramic, plastic, etc. by coating the surface with the above-mentioned conductive substance, and then coating the outermost layer with noble metals. It may be a coated conductive particle having a structure. When such particles or heat-melting metal particles are used, they have deformability when heated and pressurized, so the contact area with the electrode increases during connection, and reliability can be improved.
  • the conductive particles may be insulating coated conductive particles that include the above metal particles, conductive carbon particles, or coated conductive particles and an insulating layer that includes an insulating material such as a resin and covers the surface of the particles.
  • the conductive particles are insulation-coated conductive particles, even if the content of the conductive particles is large, the surface of the particles is coated with resin, so it is possible to suppress the occurrence of short circuits due to contact between the conductive particles, and , it is also possible to improve the insulation between adjacent electrode circuits.
  • the various conductive particles described above may be used alone or in combination of two or more types.
  • the maximum particle size of the conductive particles needs to be smaller than the minimum distance between electrodes (the shortest distance between adjacent electrodes).
  • the maximum particle size of the conductive particles may be 1.0 ⁇ m or more, 2.0 ⁇ m or more, or 2.5 ⁇ m or more from the viewpoint of excellent dispersibility and conductivity.
  • the maximum particle size of the conductive particles may be 50 ⁇ m or less, 30 ⁇ m or less, or 20 ⁇ m or less from the viewpoint of excellent dispersibility and conductivity.
  • the particle size of 300 arbitrary conductive particles (pcs) is measured by observation using a scanning electron microscope (SEM), and the largest value obtained is defined as the maximum particle size of the conductive particles. .
  • SEM scanning electron microscope
  • the average particle diameter of the conductive particles may be 1.0 ⁇ m or more, 2.0 ⁇ m or more, or 2.5 ⁇ m or more from the viewpoint of excellent dispersibility and conductivity.
  • the average particle diameter of the conductive particles may be 50 ⁇ m or less, 30 ⁇ m or less, or 20 ⁇ m or less from the viewpoint of excellent dispersibility and conductivity.
  • the particle size of 300 arbitrary conductive particles (pcs) is measured by observation using a scanning electron microscope (SEM), and the average value of the obtained particle sizes is defined as the average particle size.
  • the content of the conductive particles may be in the range of 0.1 to 30 parts by volume based on 100 parts by volume of the resin component of the adhesive composition, since stable connection resistance can be easily obtained.
  • the content of the conductive particles may be 0.1 to 10 parts by volume from the viewpoint of preventing short-circuiting of adjacent circuits due to excessive conductive particles.
  • the content of the conductive particles is such that stable connection resistance can be easily obtained, and the content of the conductive particles is determined by adjusting the content of the adhesive composition, such as particles containing a radically polymerizable compound, a radical polymerization initiator, a compound having a nitrogen-containing aromatic heterocycle, a metal compound,
  • the amount may be 0.5 to 60% by weight, 3 to 45% by weight, or 6 to 30% by weight, based on the total weight of the thermoplastic resin and the thermoplastic resin.
  • the adhesive composition may further contain other components in addition to the components mentioned above.
  • other components include thiol compounds, coupling agents, fillers, and the like. These components may be used alone or in combination of two or more.
  • the thiol compound may be a thiol compound having one thiol group (monofunctional thiol compound) or a thiol compound having multiple thiol groups (polyfunctional thiol compound).
  • the thiol group that the thiol compound has may be a primary thiol group, a secondary thiol group, or a tertiary thiol group.
  • Examples of monofunctional thiol compounds include 2-mercaptobenzothiazole, 2-methyl-4,5-dihydrofuran-3-thiol, 3-mercapto-1-hexanol, mercaptomethylbutanol, and 3-mercapto-2-methylpene.
  • polyfunctional thiol compounds include pentaerythritol tetrakis (3-mercaptobutyrate), ethanedithiol, 1,3-propanethiol, 1,4-butanethiol, trimethylolpropane tris (3-mercaptopropionate), Examples include tris-[(3-mercaptopropionyloxy)-ethyl]-isocyanurate, tetraethylene glycol bis(3-mercaptopropionate), and the like.
  • the content of the thiol compound is determined based on the total mass of the resin component of the adhesive composition, from the viewpoint of suppressing peeling at the interface between the adhesive composition and the circuit member after curing and suppressing an increase in connection resistance of the circuit connection structure. As a standard, it may be 0.05% by mass or more, 0.5% by mass or more, 1.0% by mass or more, or 1.5% by mass or more, and suppresses peeling at the interface between the adhesive composition and the circuit member after curing. , and from the viewpoint of suppressing an increase in connection resistance of the circuit connection structure, the content may be 5.0% by mass or less, 3.0% by mass or less, 2.5% by mass or less, or 2.0% by mass or less.
  • a compound having at least one of a vinyl group, an acryloyl group, an amino group, an epoxy group, or an isocyanate group can be used from the viewpoint of improving adhesiveness.
  • the filler examples include non-conductive fillers (for example, non-conductive particles).
  • the filler may be either an inorganic filler or an organic filler.
  • the inorganic filler include metal oxide particles such as silica particles, alumina particles, silica-alumina particles, titania particles, and zirconia particles; inorganic particles such as nitride particles.
  • the organic filler include organic fine particles such as silicone fine particles, methacrylate-butadiene-styrene fine particles, acrylic-silicone fine particles, polyamide fine particles, and polyimide fine particles. These fine particles may have a uniform structure or a core-shell type structure. The maximum diameter of the filler may be less than the minimum particle diameter of the conductive particles.
  • the content of the filler may be 4 to 60 volume %, 5 to 50 volume %, or 6 to 30 volume % based on the total volume of the adhesive composition.
  • the content of the filler is determined from the viewpoint of improving connection reliability, including the radically polymerizable compound of the adhesive composition, a radical polymerization initiator, a compound having a nitrogen-containing aromatic heterocycle, particles containing a metal compound, and a thermoplastic resin.
  • the adhesive composition may further contain other additives such as softeners, accelerators, anti-aging agents, colorants, flame retardants, thixotropic agents, and polymerization inhibitors.
  • additives such as softeners, accelerators, anti-aging agents, colorants, flame retardants, thixotropic agents, and polymerization inhibitors.
  • the polymerization inhibitor include hydroquinone and methyl ether hydroquinones.
  • the adhesive composition described above is suitably used as a circuit connecting adhesive composition for connecting circuit members having electrodes with the electrodes facing each other, and for connecting circuit members to each other. It is particularly suitable for use as an anisotropically conductive adhesive composition.
  • FIG. 1 is a schematic cross-sectional view showing an adhesive film according to one embodiment.
  • An adhesive film 1A shown in FIG. 1 includes an adhesive layer 2 containing the above-described adhesive composition.
  • the adhesive layer 2 contains an adhesive component (components other than conductive particles in the adhesive composition) 3 and conductive particles 4 dispersed in the adhesive component 3.
  • the thickness of the adhesive film 1A may be 10 ⁇ m or more and 50 ⁇ m or less.
  • the adhesive film may include multiple adhesive layers.
  • FIG. 2 is a schematic cross-sectional view of an adhesive film according to another embodiment.
  • the adhesive film 1B shown in FIG. 2 includes a first adhesive layer 5 and a second adhesive layer 6 laminated on the first adhesive layer 5.
  • the first adhesive layer 5 contains the adhesive composition described above. That is, the first adhesive layer 5 contains the adhesive component 3 and the conductive particles 4 dispersed in the adhesive component 3.
  • the second adhesive layer 6 contains, for example, a radical polymerizable compound and a radical polymerization initiator.
  • a radical polymerization initiator and the radical polymerization initiator those used in the adhesive composition described above can be used.
  • the second adhesive layer 6 may further contain the above-mentioned thermoplastic resin and the components exemplified as other components in the adhesive composition.
  • the second adhesive layer 6 does not need to contain conductive particles.
  • the thickness of the first adhesive layer 5 and the second adhesive layer 6 may be set as appropriate depending on the height of the electrode of the circuit member to be bonded.
  • the thickness of the first adhesive layer 5 may be, for example, 0.5 ⁇ m or more and 20 ⁇ m or less.
  • the thickness of the second adhesive layer 6 may be, for example, 5 ⁇ m or more and 200 ⁇ m or less.
  • the thickness of the adhesive film 1B (the total thickness of the first adhesive layer 5 and the second adhesive layer 6) may be, for example, 5 ⁇ m or more and 200 ⁇ m or less.
  • the adhesive film is not limited to the above embodiments, and may be an adhesive film that includes one adhesive layer that does not contain conductive particles, for example.
  • the adhesive film may be a three-layer film composed of an adhesive layer containing conductive particles and adhesive layers not containing conductive particles provided on both sides of the adhesive layer.
  • the adhesive film described above can be suitably used as a circuit connection adhesive film for connecting circuit members having electrodes with the electrodes facing each other.
  • the adhesive film of this embodiment can be produced by the following method. Specifically, first, each component contained in the adhesive layer (for example, adhesive component and conductive particles) is added to a solvent such as an organic solvent, and dissolved or dispersed by stirring, mixing, kneading, etc. to form a varnish. A composition (varnish-like adhesive composition) is prepared. After that, the varnish composition is applied onto the base material that has been subjected to mold release treatment using a knife coater, roll coater, applicator, comma coater, die coater, etc., and then the solvent is evaporated by heating and applied onto the base material. An adhesive film can be formed.
  • a solvent such as an organic solvent
  • a solvent having the property of uniformly dissolving or dispersing each component may be used.
  • solvents include toluene, acetone, methyl ethyl ketone, methyl isobutyl ketone, ethyl acetate, propyl acetate, butyl acetate, and the like. These solvents may be used alone or in combination of two or more.
  • Stirring, mixing and kneading during the preparation of the varnish composition can be carried out using, for example, a stirrer, a miller, a three-roll mill, a ball mill, a bead mill, or a homodisper.
  • the base material is not particularly limited as long as it has heat resistance that can withstand the heating conditions used to volatilize the solvent, such as oriented polypropylene (OPP), polyethylene terephthalate (PET), polyethylene naphthalate, and polyethylene isophthalate.
  • OPP oriented polypropylene
  • PET polyethylene terephthalate
  • PET polyethylene naphthalate
  • polyethylene isophthalate polybutylene terephthalate
  • polyolefin polyacetate
  • polycarbonate polyphenylene sulfide
  • polyamide polyimide
  • cellulose ethylene/vinyl acetate copolymer
  • polyvinyl chloride polyvinylidene chloride
  • synthetic rubber liquid crystal polymer, etc.
  • the heating conditions for volatilizing the solvent from the varnish composition applied to the substrate may be such that the solvent is sufficiently volatilized.
  • the heating conditions may be, for example, at 40° C. or higher and 120° C. or lower for 0.1 minutes or more and 10 minutes or less.
  • part of the solvent may remain without being removed.
  • the content of the solvent in the adhesive film for circuit connection of the present embodiment may be, for example, 10% by mass or less, or 5% by mass or less, based on the total mass of the adhesive film.
  • connection structure of this embodiment includes a first circuit member having a first electrode, a second circuit member having a second electrode, and a second circuit member disposed between the first circuit member and the second circuit member. and a connection part that electrically connects the first electrode and the second electrode to each other, and the connection part contains a cured product of the adhesive composition of the present embodiment.
  • FIG. 3 is a schematic cross-sectional view showing one embodiment of the connected structure.
  • the connection structure 10 shown in FIG. a second circuit member 16 having a substrate 14 and a second electrode (second connection terminal) 15 formed on the main surface 14a thereof; a first circuit member 13 and a second circuit member 16; and a connecting portion 17 that is interposed between them and adheres them.
  • the second circuit member 16 is arranged to face the first circuit member 13 such that the second electrode 15 faces the first electrode 12.
  • the connecting portion 17 includes a cured product of the adhesive composition, and is composed of a cured product 18 of the adhesive component and conductive particles 4 dispersed in the cured product 18.
  • the first electrode 12 and the second electrode 15 facing each other are electrically connected via the conductive particles 4.
  • the first electrodes 12 and the second electrodes 15 formed on the same substrate are insulated from each other.
  • first substrate 11 and the second substrate 14 examples include chip components such as semiconductor chips, resistor chips, and capacitor chips, and substrates such as printed circuit boards.
  • a circuit member is provided with a large number of connection terminals, but there may be a single connection terminal depending on the case.
  • substrates of semiconductors, inorganic materials such as glass and ceramics, plastic substrates, or glass/epoxy substrates are used.
  • Plastic substrates include polyimide films, polycarbonate films, and polyester films.
  • the first electrode 12 and the second electrode 15 are made of metal such as copper.
  • a surface layer containing a metal selected from gold, silver, tin, and the platinum group on at least one of the first electrode 12 and the second electrode 15.
  • the surface layer is selected from gold, silver, platinum group metals, or tin, and may be used in combination.
  • a multilayer structure may be formed by combining a plurality of metals such as copper/nickel/gold.
  • One of the first circuit member 13 and the second circuit member 16 may be a liquid crystal display panel that has a glass substrate or a plastic substrate as a circuit board and has connection terminals made of ITO or the like. Further, one of the first circuit member 13 and the second circuit member 16 may be a flexible printed wiring board (FPC), a tape cure package (TCP), or a chip-on-film (COF) having a polyimide film as a circuit board, or It may also be a semiconductor silicon chip having a semiconductor substrate as a circuit board.
  • FPC flexible printed wiring board
  • TCP tape cure package
  • COF chip-on-film
  • a connection structure is constructed by appropriately combining these various circuit members as necessary.
  • the substrate provided with the electrodes is preferably heat-treated in advance before connection with the adhesive composition in order to eliminate the influence of volatile components on the connection due to heating during connection.
  • the method for manufacturing a connected structure according to the present embodiment includes applying the adhesive composition of the present embodiment between a first circuit member having a first electrode and a second circuit member having a second electrode.
  • the method includes a step of electrically connecting the first electrode and the second electrode to each other by thermocompression bonding the first circuit member and the second circuit member with the intervening step.
  • first circuit member 13 having a first substrate 11 and a first electrode (first connection terminal) 12 formed on the main surface 11a thereof, and a second substrate 14 and a second circuit member 16 having a second electrode (second connection terminal) 15 formed on the main surface 14a thereof. Then, the first circuit member 13 and the second circuit member 16 are arranged so that the first electrode 12 and the second electrode 15 face each other, and the first circuit member 13 and the second circuit member 16, an adhesive composition is placed between them.
  • the adhesive composition disposed between the first circuit member 13 and the second circuit member 16 may include the above-mentioned adhesive film 1A or 1B, or a varnish composition (a varnish-like adhesive composition). may be applied onto the first circuit member 13 or the second circuit member 16, or both.
  • the first adhesive layer 5 side containing conductive particles faces the first circuit member 13, and the second adhesive layer 5 side containing conductive particles faces the first circuit member 13.
  • the adhesive film 1B may be arranged such that the adhesive layer 6 side faces the second circuit member 16, and the first adhesive layer 5 side faces the second circuit member 16, and the second adhesive layer
  • the adhesive film 1B may be arranged so that the 6th side faces the first circuit member 13.
  • first circuit member 13 and the second circuit member 16 are pressed in the thickness direction while heating the first circuit member 13, the adhesive film 1A, and the second circuit member 16.
  • the first circuit member 13 and the second circuit member 16 are bonded together by thermocompression.
  • the adhesive component of the adhesive composition is cured by heating, and as a result, the first circuit member 13 and the second circuit member 16 are pressure-bonded via the cured product of the adhesive composition.
  • the pressure during pressurization is not particularly limited as long as it does not damage the adherend, but is generally preferably 0.1 to 10 MPa.
  • the heating temperature is not particularly limited, but is preferably 100 to 200°C. These pressurization and heating are preferably performed in the range of 0.5 seconds to 100 seconds, and bonding can also be achieved by heating at 130 to 180° C., 3 MPa, and 10 seconds.
  • the weight average molecular weight was measured using a standard polystyrene calibration curve using gel permeation chromatography (GPC) under the following conditions.
  • GPC gel permeation chromatography
  • Equipment used GPC-8020 manufactured by Tosoh Corporation Detector: Tosoh Corporation RI-8020 Column: Gelpack GLA160S+GLA150S manufactured by Hitachi Chemical Co., Ltd. Sample concentration: 120mg/3mL Solvent: Tetrahydrofuran Injection volume: 60 ⁇ L Pressure: 2.94 ⁇ 10 6 Pa (30 kgf/cm 2 ) Flow rate: 1.00mL/min
  • conductive particles having an average particle size of 4 ⁇ m, a maximum particle size of 4.5 ⁇ m, and a specific gravity of 2.5 were obtained.
  • Thermoplastic resin A1: 40% by mass solution prepared by dissolving 40g of bisphenol A type phenoxy resin (trade name: PKHC, manufactured by Union Carbide) in 60g of methyl ethyl ketone (the amount in the table indicates the amount of bisphenol A type phenoxy resin) .)
  • E1 Zirconium oxide (ZrO 2 )
  • E2 Aluminum hydroxide (Al(OH) 3 )
  • F1 Conductive particles prepared as described above
  • G1 Thiol compound (pentaerythritol tetrakis (3-mercaptobutyrate), trade name: Karenz MT PE-1 ("Karenz MT" is a registered trademark), manufactured by Showa Denko K.K.), Viscosity (@25°C): 1 Pa ⁇ s, molecular weight: 544.8)
  • H1 Coupling agent (3-methacryloxypropyltrimethoxysilane (trade name: KBM503, manufactured by Shin-Etsu Chemical Co., Ltd.))
  • I1 Filler (silica fine particles (product name: R104, manufactured by Nippon Aerosil Co., Ltd., average particle size (primary particle size): 12 nm))
  • the above varnish composition was applied onto a 50 ⁇ m thick base material (PET film) using a coating device. Next, hot air drying was performed at 70° C. for 3 minutes to form an adhesive layer on the base material to produce an adhesive film. Note that the thickness of the adhesive layer (thickness after drying) was 10 ⁇ m.
  • connection structure was subjected to a salt spray test in accordance with JIS Z 2371 using a salt spray tester (manufactured by Suga Test Instruments Co., Ltd.) for 24 hours and 96 hours.
  • the appearance of the connection part (cured product of the adhesive composition) in the connection structure before and after the test was observed using an optical microscope. It was visually confirmed from the glass substrate with thin-film electrodes whether peeling had occurred at the interface between the glass substrate and the connection part. If peeling had occurred, the peeled area was calculated and evaluated on a 5-point scale according to the following criteria. The results are shown in Tables 1 to 3.
  • S The percentage of peeled area is less than 5%.
  • A The percentage of peeled area is 5% or more and less than 10%.
  • B The percentage of peeled area is 10% or more and less than 30%.
  • C The percentage of peeled area is 30% or more and less than 60%.
  • D The percentage of peeled area is 60% or more.
  • connection resistance, adhesive strength, and peeling area immediately after connection and after the high temperature and high humidity test were evaluated by the following methods.
  • the high temperature and high humidity test was conducted by leaving the connected structure in a constant temperature and humidity chamber at 85° C. and 85% RH for 100 hours. The results are shown in Table 4.
  • connection resistance The connection resistance value between opposing electrodes in the connected structure was measured using a multimeter. The connection resistance value was determined as the average value of resistances at 16 points between opposing electrodes, and the connection resistance was evaluated in four stages according to the following criteria. A: 3.0 ⁇ or less B: More than 3.0 ⁇ and 6.0 ⁇ or less C: More than 6.0 ⁇ and less than 10.0 ⁇ D: More than 10.0 ⁇
  • Adhesive strength The adhesive strength (N/cm) at room temperature in the connected structure was measured using a universal tensile tester (Tensilon UTM-4, manufactured by Toyo Baldwin Co., Ltd., peel strength 50 mm/min). Adhesive strength was evaluated in four stages according to the following criteria. A: 10.0 N/cm or more B: 8.0 N/cm or more and less than 10.0 N/cm C: 6.0 N/cm or more and less than 8.0 N/cm D: Less than 6.0 N/cm
  • 1A, 1B ...adhesive film, 2...adhesive layer, 3...adhesive component, 4...conductive particles, 5...first adhesive layer, 6...second adhesive layer, 10...connected structure, 11 ...first substrate, 12...first electrode, 13...first circuit member, 14...second substrate, 15...second electrode, 16...second circuit member, 17...connection section.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Adhesive Tapes (AREA)

Abstract

L'invention concerne une composition d'agent adhésif comprenant : un composé polymérisable par voie radicalaire ; un initiateur de polymérisation radicalaire ; un composé ayant un noyau hétérocyclique aromatique contenant de l'azote ; et des particules contenant au moins un composé métallique choisi dans le groupe constitué par les hydroxydes métalliques et les oxydes métalliques.
PCT/JP2023/033398 2022-09-15 2023-09-13 Composition d'agent adhésif, film d'agent adhésif, corps de structure de connexion et procédé de fabrication associé WO2024058218A1 (fr)

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Citations (8)

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Publication number Priority date Publication date Assignee Title
JP2002167569A (ja) * 2000-11-29 2002-06-11 Hitachi Chem Co Ltd 接着剤組成物、回路接続用接着剤組成物、接続体及び半導体装置
WO2007046189A1 (fr) * 2005-10-18 2007-04-26 Hitachi Chemical Company, Ltd. Composition adhesive, materiau de connexion de circuit, structure de connexion de connecteur de circuit et dispositifs a semi-conducteurs
JP2012160546A (ja) * 2011-01-31 2012-08-23 Hitachi Chem Co Ltd 回路接続用接着フィルム及び回路接続構造体
JP2014074139A (ja) * 2012-10-05 2014-04-24 Dexerials Corp 回路接続材料及びその製造方法、並びにそれを用いた実装体の製造方法
WO2017090659A1 (fr) * 2015-11-25 2017-06-01 日立化成株式会社 Composition d'adhésif pour connexion de circuit, et structure
WO2019142791A1 (fr) * 2018-01-17 2019-07-25 日立化成株式会社 Composition adhésive, structure de liaison et son procédé de production
JP2021123655A (ja) * 2020-02-05 2021-08-30 高圧ガス工業株式会社 一液型アクリル系接着剤
WO2022025207A1 (fr) * 2020-07-31 2022-02-03 昭和電工マテリアルズ株式会社 Film adhésif pour connexion de circuits, composition adhésive pour connexion de circuits et structure de connexion de circuits et son procédé de fabrication

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002167569A (ja) * 2000-11-29 2002-06-11 Hitachi Chem Co Ltd 接着剤組成物、回路接続用接着剤組成物、接続体及び半導体装置
WO2007046189A1 (fr) * 2005-10-18 2007-04-26 Hitachi Chemical Company, Ltd. Composition adhesive, materiau de connexion de circuit, structure de connexion de connecteur de circuit et dispositifs a semi-conducteurs
JP2012160546A (ja) * 2011-01-31 2012-08-23 Hitachi Chem Co Ltd 回路接続用接着フィルム及び回路接続構造体
JP2014074139A (ja) * 2012-10-05 2014-04-24 Dexerials Corp 回路接続材料及びその製造方法、並びにそれを用いた実装体の製造方法
WO2017090659A1 (fr) * 2015-11-25 2017-06-01 日立化成株式会社 Composition d'adhésif pour connexion de circuit, et structure
WO2019142791A1 (fr) * 2018-01-17 2019-07-25 日立化成株式会社 Composition adhésive, structure de liaison et son procédé de production
JP2021123655A (ja) * 2020-02-05 2021-08-30 高圧ガス工業株式会社 一液型アクリル系接着剤
WO2022025207A1 (fr) * 2020-07-31 2022-02-03 昭和電工マテリアルズ株式会社 Film adhésif pour connexion de circuits, composition adhésive pour connexion de circuits et structure de connexion de circuits et son procédé de fabrication

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