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WO2023195398A1 - Composition adhésive, film adhésif pour connexion de circuit, structure de connexion de circuit et son procédé de production - Google Patents

Composition adhésive, film adhésif pour connexion de circuit, structure de connexion de circuit et son procédé de production Download PDF

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Publication number
WO2023195398A1
WO2023195398A1 PCT/JP2023/012839 JP2023012839W WO2023195398A1 WO 2023195398 A1 WO2023195398 A1 WO 2023195398A1 JP 2023012839 W JP2023012839 W JP 2023012839W WO 2023195398 A1 WO2023195398 A1 WO 2023195398A1
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WIPO (PCT)
Prior art keywords
circuit
electrode
circuit connection
mass
adhesive film
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Ceased
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PCT/JP2023/012839
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English (en)
Japanese (ja)
Inventor
槙之介 岩元
直 工藤
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Resonac Corp
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Resonac Corp
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Priority to CN202380031280.XA priority Critical patent/CN118974194A/zh
Publication of WO2023195398A1 publication Critical patent/WO2023195398A1/fr
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • 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
    • C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
    • C09J175/04—Polyurethanes
    • C09J175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
    • 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
    • C09J201/00—Adhesives based on unspecified macromolecular compounds
    • 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
    • C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J9/00—Adhesives characterised by their physical nature or the effects produced, e.g. glue sticks
    • C09J9/02—Electrically-conducting adhesives
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01R—ELECTRICALLY-CONDUCTIVE CONNECTIONS; STRUCTURAL ASSOCIATIONS OF A PLURALITY OF MUTUALLY-INSULATED ELECTRICAL CONNECTING ELEMENTS; COUPLING DEVICES; CURRENT COLLECTORS
    • H01R11/00—Individual connecting elements providing two or more spaced connecting locations for conductive members which are, or may be, thereby interconnected, e.g. end pieces for wires or cables supported by the wire or cable and having means for facilitating electrical connection to some other wire, terminal, or conductive member, blocks of binding posts
    • H01R11/01—Individual connecting elements providing two or more spaced connecting locations for conductive members which are, or may be, thereby interconnected, e.g. end pieces for wires or cables supported by the wire or cable and having means for facilitating electrical connection to some other wire, terminal, or conductive member, blocks of binding posts characterised by the form or arrangement of the conductive interconnection between the connecting locations

Definitions

  • the present disclosure relates to an adhesive composition, an adhesive film for circuit connection, a circuit connection structure, and a method for manufacturing the same.
  • thermosetting resins using epoxy resins that exhibit high adhesiveness and high reliability are known (see, for example, Patent Document 1).
  • epoxy resins As constituent components of the resin, epoxy resins, curing agents such as phenolic resins that are reactive with the epoxy resins, and latent curing agents that promote the reaction between the epoxy resins and the curing agents are generally used.
  • the latent curing agent is an important factor in determining the curing temperature and curing rate, and various compounds are used from the viewpoints of storage stability at room temperature and curing rate when heated.
  • radical curing adhesives that use a combination of acrylate derivatives and/or methacrylate derivatives (hereinafter collectively referred to as "(meth)acrylate derivatives") and peroxide, which is a radical polymerization initiator, have recently attracted attention. has been done.
  • radical curing since radicals, which are reactive species, are highly reactive, short-time curing is possible (see, for example, Patent Documents 2 and 3).
  • an adhesive film having anisotropic conductivity in which conductive particles are dispersed in the adhesive is used to connect circuit members.
  • the connection resistance between opposing electrodes tends to increase after a high-temperature, high-humidity test.
  • the present disclosure provides an adhesive composition and an adhesive film for circuit connection that can obtain a circuit connection structure in which the connection resistance between opposing electrodes is unlikely to increase even under high temperature and high humidity conditions, and It is an object of the present invention to provide a circuit connection structure in which connection resistance between opposing electrodes is unlikely to increase even under high humidity conditions, and a method for manufacturing the same.
  • the gist of the present disclosure is the following [1] to [8].
  • An adhesive composition comprising a resin component containing a thermoplastic resin, a radical polymerizable compound, and a radical polymerization initiator, conductive particles, and a cyclization polymerizable monomer as the radical polymerizable compound.
  • the circuit connection has a property that the connection resistance between opposing electrodes does not easily increase even under high temperature and high humidity conditions (hereinafter also referred to as "high temperature and high humidity connection reliability"). You can get a structure.
  • [3] Further contains a (poly)urethane (meth)acrylate compound as a radically polymerizable compound, and the content of the (poly)urethane (meth)acrylate compound is 100 parts by mass based on 100 parts by mass of the cyclization polymerizable monomer.
  • An adhesive film for circuit connection which contains a thermoplastic resin, a radical polymerizable compound, a radical polymerization initiator, and conductive particles, and contains a cyclization polymerizable monomer as the radical polymerizable compound.
  • [6] Further contains a (poly)urethane (meth)acrylate compound as a radically polymerizable compound, and the content of the (poly)urethane (meth)acrylate compound is 100 parts by mass based on 100 parts by mass of the cyclization polymerizable monomer.
  • the above circuit connection structure can have sufficient high temperature and high humidity connection reliability.
  • an adhesive composition and an adhesive film for circuit connection which can provide a circuit connection structure in which connection resistance between opposing electrodes is unlikely to increase even under high temperature and high humidity conditions; It is possible to provide a circuit connection structure in which connection resistance between opposing electrodes is unlikely to increase even under high humidity conditions, and a method for manufacturing the same.
  • FIG. 1 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) a thermoplastic resin (hereinafter also referred to as “component (A)”), and (B) a radically polymerizable compound (hereinafter also referred to as “component (B)”). , and (C) a resin component containing a radical polymerization initiator (hereinafter also referred to as “(C) component”), and (G) conductive particles (hereinafter also referred to as "(G) component”). be able to.
  • component (A) a thermoplastic resin
  • component (B) a radically polymerizable compound
  • component (C) component) a resin component containing a radical polymerization initiator
  • G conductive particles
  • Component (A): Thermoplastic resin As component (A), 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 can be used alone or in combination of two or more.
  • the weight average molecular weight of the above-mentioned thermoplastic resin may be 1.0 ⁇ 10 4 or more from the viewpoint of film formability, etc., and 1.0 ⁇ 10 4 or more and less than 1.0 ⁇ 10 6 from the viewpoint of mixability. It may be.
  • the weight average molecular weight of a thermoplastic resin is one measured by gel permeation chromatography (GPC) according to the following conditions using a standard polystyrene calibration curve.
  • GPC conditions Equipment used: Hitachi L-6000 model [Hitachi, Ltd.], Column: Gelpack GL-R420 + Gelpack GL-R430 + Gelpack GL-R440 (3 columns in total) [manufactured by Hitachi Chemical Co., Ltd.], Eluent: Tetrahydrofuran, Measurement temperature: 40°C, flow rate: 1.75ml/min, detector: L-3300RI [Hitachi, Ltd.]
  • a hydroxyl group-containing resin eg, phenoxy resin
  • Tg glass transition temperature
  • weight average molecular weight 1.0 ⁇ 10 4 or higher
  • the hydroxyl group-containing resin may be modified with an epoxy group-containing elastomer.
  • thermoplastic resin having a radically polymerizable functional group is blended as the (B) radically polymerizable compound.
  • 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 component (A).
  • the content of component (A) in the adhesive composition is 5% by mass based on the resin component (for example, components other than conductive particles and fillers) of the adhesive composition, from the viewpoint of further improving the effect of suppressing peeling. % or more or 30% by weight or more, and 80% by weight or less or 60% by weight or less, and 5 to 80% by weight or 30 to 60% by weight.
  • Component (B): Radical polymerizable compound As component (B), a compound having a radically polymerizable functional group can be used. Examples of the radically polymerizable functional group include a vinyl group, an acryloyl group, a methacryloyl group, and the like. Among these, compounds having an acryloyl group and/or a methacryloyl group are more preferred. Component (B) can be used alone or in combination of two or more.
  • the adhesive composition of this embodiment can contain a cyclization polymerizable monomer (hereinafter also referred to as "component (B1)") as component (B).
  • component (B1) a cyclization polymerizable monomer
  • a diene structure-containing monomer can be used as the component (B1).
  • the diene structure-containing monomer include a 1,5-diene structure-containing monomer that may contain a hetero atom, a 1,6-diene structure-containing monomer that may contain a hetero atom, and the like.
  • Component (B1) can be used alone or in combination of two or more.
  • an acrylic diene structure-containing monomer represented by the following general formula (1) can be used as the component (B1).
  • R 1 represents a hydrogen atom or an organic group having 1 to 30 carbon atoms
  • R 2 represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a phenyl group, a carboxyl group, an ester group, or represents a cyano group
  • X and Y each independently represent a methylene group, an imino group, a carbonyl group, an oxygen atom or a sulfur atom which may have an alkyl group having 1 to 4 carbon atoms
  • Z represents a direct bond , a methylene group, an imino group, a carbonyl group, an oxygen atom or a sulfur atom which may have an alkyl group having 1 to 4 carbon atoms
  • at least one group among X, Y and Z is an oxygen atom
  • a sulfur atom or an imino group (provided that heteroatoms are
  • R 1 is an organic group having 1 to 30 carbon atoms
  • the organic group includes, for example, a chain saturated hydrocarbon group having 1 to 30 carbon atoms, and a chain unsaturated hydrocarbon group having 2 to 30 carbon atoms. , an alicyclic hydrocarbon group having 3 to 30 carbon atoms, an aromatic hydrocarbon group having 6 to 30 carbon atoms, and a cyclic ether group having 2 to 30 carbon atoms.
  • some or all of the hydrogen atoms may be substituted with at least one substituent selected from the group consisting of an alkoxy group having 1 to 30 carbon atoms, a hydroxyl group, and a halogen atom.
  • halogen atom examples include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
  • R 1 may be a methyl group, an ethyl group, an isopropyl group, a phenoxyethyl group, a cyclohexyl group, an isobornyl group, a benzyl group, or a tetrahydrofurfuryl group, or may be a methyl group or a cyclohexyl group.
  • R 2 is an ester group
  • examples of the ester group include -COOR 3 (wherein R 3 represents an organic group having 1 to 30 carbon atoms).
  • R 3 may be the same group as R 1 described above.
  • the adhesive composition of this embodiment contains the above-mentioned acrylic diene structure-containing monomer as the component (B), the connection resistance between opposing electrodes is unlikely to increase even under high temperature and high humidity conditions. It becomes easy to obtain a circuit connection structure having characteristics.
  • the present inventors speculate as follows about the reason why such an effect is obtained.
  • the radical polymerization reaction system containing the above-mentioned acrylic diene structure-containing monomer it is thought that the non-cyclization reaction and the cyclization reaction proceed due to heating when connecting the circuit members.
  • These reactions result in the formation of polymers with high crosslink density, polymers with a ring structure in the polymer main chain, and polymers with a crosslink structure and a ring structure, which reduce the shrinkage stress during connection. It is presumed that the above effects were obtained as a result of the reduction in interfacial peeling and the imparting of heat resistance and moisture resistance to the cured product constituting the connection portion.
  • 1,6-diene structure-containing monomers represented by the following general formulas (1a) to (1c) can be used as component (B1).
  • the shrinkage stress generated during connection can be reduced to further suppress interfacial peeling, thereby further improving high temperature and high humidity connection reliability.
  • R 1 has the same meaning as above.
  • R 1 has the same meaning as above.
  • R 1 has the same meaning as above, and two R 1s may be the same or different. ]
  • the adhesive composition of the present embodiment contains the above-mentioned 1,6-diene structure-containing monomer, it becomes easier to obtain a circuit-connected structure with excellent high-temperature, high-humidity connection reliability. Such an effect is thought to be due to the fact that the formation of a THF ring structure in the polymer makes it possible to further alleviate the shrinkage stress during connection.
  • Examples of the 1,6-diene structure-containing monomer represented by general formula (1a) include ⁇ -allyloxymethylacrylic acid, methyl ⁇ -allyloxymethylacrylate, ⁇ -allyloxymethylethyl acrylate, ⁇ - Propyl allyloxymethyl acrylate, isopropyl ⁇ -allyloxymethyl acrylate, butyl ⁇ -allyloxymethyl acrylate, tert-butyl ⁇ -allyloxymethyl acrylate, phenoxyethyl ⁇ -allyloxymethyl acrylate, ⁇ -allyloxy Cyclohexyl methyl acrylate, dicyclopentadienyl ⁇ -allyloxymethyl acrylate, isobornyl ⁇ -allyloxymethyl acrylate, adamantyl ⁇ -allyloxymethyl acrylate, benzyl ⁇ -allyloxymethyl acrylate, ⁇ -allyloxymethyl
  • Examples include allyloxymethyl acrylates such as tetrahydrofur
  • Examples of the 1,6-diene structure-containing monomer represented by the general formula (1b) include ⁇ -methallyloxymethylacrylic acid, methyl ⁇ -methallyloxymethylacrylate, and ethyl ⁇ -methallyloxymethylacrylate.
  • ⁇ -methallyloxymethyl acrylate propyl ⁇ -methallyloxymethyl acrylate isopropyl, ⁇ -methallyloxymethyl acrylate butyl, ⁇ -methallyloxymethyl acrylate tert-butyl, ⁇ -methallyloxymethyl acrylate phenoxyethyl acid, cyclohexyl ⁇ -methallyloxymethyl acrylate, dicyclopentadienyl ⁇ -methallyloxymethyl acrylate, isobornyl ⁇ -methallyloxymethyl acrylate, adamantyl ⁇ -methallyloxymethyl acrylate, ⁇ - Examples include methallyloxymethyl acrylic esters such as benzyl methallyloxymethyl acrylate and tetrahydrofurfuryl ⁇ -methallyloxymethyl acrylate.
  • Examples of the 1,6-diene structure-containing monomer represented by the general formula (1c) include bis( ⁇ -hydroxymethylacrylic acid) ether, bis( ⁇ -hydroxymethylmethylacrylate) ether, and bis( ⁇ -hydroxymethylacrylate) ether. ethyl methyl acrylate) ether, bis( ⁇ -hydroxymethyl acrylate propyl) ether, bis( ⁇ -hydroxymethyl acrylate isopropyl) ether, bis( ⁇ -hydroxymethyl acrylate butyl) ether, bis( ⁇ -hydroxymethyl acrylate) ether tert-butyl acrylate) ether, bis(phenoxyethyl ⁇ -hydroxymethylacrylate) ether, bis(cyclohexyl ⁇ -hydroxymethylacrylate) ether, bis(dicyclopentadienyl ⁇ -hydroxymethylacrylate) ether, bis( ⁇ -hydroxymethylacrylic acid isobornyl) ether, bis( ⁇ -hydroxymethyladamantyl acrylate) ether, bis( ⁇ -hydroxy
  • the above monomers can be prepared, for example, by the methods described in JP-A-10-226669 and JP-A-2012-184402. Additionally, commercially available products such as "FX-AO-MA” (manufactured by Nippon Shokubai Co., Ltd., trade name) can be used.
  • FX-AO-MA manufactured by Nippon Shokubai Co., Ltd., trade name
  • 1,5-diene structure-containing monomer which may contain a hetero atom
  • 1,5-diene structure-containing monomers represented by the following general formulas (1d) to (1e) can be used.
  • R 1 has the same meaning as above.
  • R 1 has the same meaning as above.
  • the content of component (B1) in the adhesive composition is 3% by mass or more or 7% by mass based on the total mass of component (B), from the viewpoint of further suppressing interfacial peeling by reducing shrinkage stress generated during connection. It may be greater than or equal to 50% by weight or less than 45% by weight, and may be from 3 to 50% by weight, from 7 to 45% by weight, from 10 to 40% by weight, or from 13 to 37% by weight.
  • the content of component (B1) in the adhesive composition is determined from the viewpoint of reducing shrinkage stress generated during connection and further suppressing interfacial peeling. It may be 1% by mass or more, or 4% by mass or more, and 35% by mass or less, or 30% by mass or less, 1 to 35% by mass, 4 to 30% by mass, based on the total mass of components (other than components). , 7 to 25% by weight, or 10 to 20% by weight.
  • the adhesive composition of the present embodiment can contain component (B1) and a radically polymerizable compound other than the above-mentioned (B1) (hereinafter also referred to as “component (B2)").
  • Components 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. Polymers such as phenoxy resins can also be used. Note that the polymer used as component (B2) has at least one radically polymerizable functional group in the molecule.
  • a polymer as the component (B2) because it provides good handling and excellent stress relaxation during curing, and it is more preferable when the polymer has a functional group such as a hydroxyl group because it improves adhesiveness.
  • the weight average molecular weight of the above polymer may be 1.0 ⁇ 10 4 or more, and may be 1.0 ⁇ 10 4 or more and 1.0 ⁇ 10 6 or less from the viewpoint of miscibility.
  • 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.
  • (B2) component is (poly)urethane (poly)urethane ( Meth)acrylate compounds can be used.
  • the content of the (poly)urethane (meth)acrylate compound is 40 to 95% by mass, 50 to 90% by mass, or 55% by mass based on the total mass of component (B) from the viewpoint of the balance between crosslinking density and curing shrinkage. It may be up to 85% by weight.
  • the content of the (poly)urethane (meth)acrylate compound is 100 to 1000 parts by mass per 100 parts by mass of component (B1) from the viewpoint of balancing crosslinking density and curing shrinkage and further reducing connection resistance. parts by weight, 130 to 800 parts by weight, or 150 to 650 parts by weight.
  • Component (B2) is ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, trimethylolpropane tri(meth)acrylate, tetramethylolmethanetetra(meth)acrylate, 2-hydroxy-1,3-di(meth)acrylate, ) acryloxypropane, 2,2-bis[4-((meth)acryloxymethoxy)phenyl]propane, 2,2-bis[4-((meth)acryloxypolyethoxy)phenyl]propane, dicyclopentenyl( meth)acrylate, tricyclodecanyl(meth)acrylate, tris((meth)acryloyloxyethyl)isocyanurate, urethane(meth)acrylate, dimethyloltricyclodecane di(meth)acrylate, isocyanuric acid modified with EO (ethylene oxide) Diacrylate, 2-methacryloyloxyethyl acid phosphate
  • component (B2) one having at least one partial structure selected from the group consisting of a dicyclopentane skeleton, a tricyclodecane skeleton, and a triazine ring can be used.
  • the component (B2) may contain a (meth)acrylate compound represented by the following formula (2) (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 an inorganic substance (metal etc.) is improved, it is suitable for adhering electrodes (for example, circuit electrodes).
  • n represents an integer of 1 to 3
  • R represents a hydrogen atom or a methyl group.
  • the (meth)acrylate compound represented by formula (2) 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 (2) is, for example, component (B) in that it becomes easier to obtain the crosslinking density necessary to reduce connection resistance and improve connection reliability.
  • component (B) may be from 1 to 10% by weight, from 2 to 5% by weight, or from 2.5 to 4% by weight, based on the total weight of.
  • the content of component (B) in the adhesive film for circuit connection is determined by the adhesive composition in that it becomes easier to obtain the crosslinking density necessary for reducing connection resistance and improving high temperature and high humidity resistant connection reliability.
  • component (C) a compound that generates free radicals can be used, 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.
  • Component (C) can 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 component (C) in the adhesive composition is 0.1 mass based on the total mass of the resin components (for example, components other than conductive particles and fillers) of the adhesive composition. % or more, 0.5% by mass or more, or 1% by mass or more, and 20% by mass or less, 10% by mass or less, or 5% by mass or less, 0.1 to 20% by mass, 0.5 to It may be 10% by weight or 1-5% by weight.
  • the component (G) may be metal particles such as Au, Ag, Ni, Cu, or solder, or conductive carbon particles made of conductive carbon. Furthermore, the component (G) may be one in which the surface of a transition metal such as Ni is coated 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. In addition, the component (G) is obtained by forming a conductive layer on the surface of the non-conductive particle by coating the surface of the non-conductive particle such as glass, ceramic, plastic, etc. with the above-mentioned conductive substance, and then forming the outermost layer. The conductive particles may be coated conductive particles made of noble metals. 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.
  • Component (G) may be insulating coated conductive particles comprising the metal particles, conductive carbon particles, or coated conductive particles described above, and an insulating layer that includes an insulating material such as a resin and covers the surface of the particles. good.
  • component (G) is an insulating-coated conductive particle, even if the content of component (G) is high, the surface of the particle is coated with resin, so short circuits due to contact between components (G) occur. This can be suppressed and the insulation between adjacent electrode circuits can be improved.
  • one type of the above-mentioned various conductive particles may be used alone or in combination of two or more types.
  • the maximum particle size of component (G) needs to be smaller than the minimum distance between electrodes (the shortest distance between adjacent electrodes).
  • the maximum particle size of component (G) 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 component (G) may be 50 ⁇ m or less, 30 ⁇ m or less, or 20 ⁇ m or less from the viewpoint of excellent dispersibility and conductivity. From these viewpoints, the maximum particle size of component (G) may be 1.0 to 50 ⁇ m, 2.0 to 30 ⁇ m, or 2.5 to 20 ⁇ m.
  • 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 component (G). shall be.
  • the particle size of the (G) component is the diameter of a circle circumscribing the conductive particle in the SEM image.
  • the average particle size of component (G) 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 size of component (G) may be 50 ⁇ m or less, 30 ⁇ m or less, or 20 ⁇ m or less from the viewpoint of excellent dispersibility and conductivity. From these viewpoints, the average particle size of component (G) may be 1.0 to 50 ⁇ m, 2.0 to 30 ⁇ m, or 2.5 to 20 ⁇ m.
  • 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 component (G) in the adhesive composition is determined based on 100 parts by volume of the resin component (for example, components other than conductive particles and fillers) of the adhesive composition, in that stable connection resistance is easily obtained.
  • the amount may be in the range of 0.1 to 30 parts by volume.
  • the content of component (G) may be 0.1 to 10 parts by volume from the viewpoint of preventing short-circuiting of adjacent circuits due to excessive conductive particles.
  • component (G) is set to 0 based on the total mass of the resin components (for example, components other than conductive particles and fillers) of the adhesive composition, in that stable connection resistance is easily obtained. .5 to 60% by weight, 3 to 45% by weight or 6 to 30% by weight.
  • the adhesive composition of this embodiment may further contain components other than those mentioned above.
  • Other components include, for example, a thiol compound (hereinafter also referred to as component (D)), a coupling agent (hereinafter also referred to as component (E)), and a filler (hereinafter also referred to as component (F)). etc. These components can be used alone or in combination of two or more.
  • the thiol compound that is component (D) 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 component (D) 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 component (D) is determined 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.
  • the amount 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.
  • the content of component (D) is determined 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 resin component of the adhesive composition. (For example, based on the total mass of components other than conductive particles and fillers), it 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 .
  • the coupling agent (E) a compound having at least one of a vinyl group, an acrylic group (acryloyl group), an amino group, an epoxy group, or an isocyanate group can be used from the viewpoint of improving adhesiveness.
  • the coupling agent may be a silane coupling agent, such as vinyltrimethoxysilane, vinyltriethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, 3-( meth)acryloxypropylmethyldimethoxysilane, 3-(meth)acryloxypropyltrimethoxysilane, 3-(meth)acryloxypropylmethyldiethoxysilane, 3-(meth)acryloxypropyltriethoxysilane, N-2- (aminoethyl)-3-aminopropylmethyldimethoxysilane, N-phenyl-3-aminopropyltrimethoxysilane, 3-ureidopropy
  • the content of component (E) is 0.5% by mass or more, 1% by mass or more, or 2% by mass based on the total mass of the resin components (for example, components other than conductive particles and fillers) of the adhesive composition. % or more, and may be 15% by mass or less, 10% by mass or less, or 5% by mass or less.
  • Examples of the filler that is component (F) include non-conductive fillers (for example, non-conductive particles).
  • the filler may be either an inorganic filler or an organic filler.
  • Examples of 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.
  • Examples of 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 component (F) may be 4 to 60 volume%, 5 to 50 volume%, or 6 to 30 volume% based on the total volume of the adhesive composition. good.
  • the content of the filler is 3 to 60% by mass, 4% by mass, based on the total mass of the resin components (for example, components other than the conductive particles and filler) of the adhesive composition. It may be ⁇ 40% by weight or 5-20% by weight.
  • the adhesive composition of this embodiment may contain other additives such as a softener, an accelerator, an anti-aging agent, a colorant, a flame retardant, a thixotropic agent, and a polymerization inhibitor.
  • a softener such as a hardener, an accelerator, an anti-aging agent, a colorant, a flame retardant, a thixotropic agent, and a polymerization inhibitor.
  • the polymerization inhibitor include hydroquinone and methyl ether hydroquinones.
  • the circuit connection adhesive film of this embodiment includes (A) a thermoplastic resin, (B) a radically polymerizable compound, and (C) a resin component containing a radical polymerization initiator, and (G) conductive particles. It can have the same structure as the adhesive composition of this embodiment described above.
  • the particle density of the conductive particles in the circuit connection adhesive film is 100 particles/mm 2 or more and 1000 particles/mm 2 from the viewpoint of obtaining stable connection resistance. or more, or 3000 pieces/mm 2 or more. From the viewpoint of ensuring insulation between adjacent electrodes, the particle density of conductive particles in the circuit connection adhesive film should be 100,000 particles/mm 2 or less, 50,000 particles/mm 2 or less, or 30,000 particles/mm 2 or less. It's fine. From these viewpoints, the particle density of the conductive particles in the adhesive film for circuit connection may be 100 to 100,000 particles/mm 2 , 1,000 to 50,000 particles/mm 2 , or 3,000 to 30,000 particles/mm 2 .
  • the thickness of the adhesive film for circuit connection may be, for example, 3 ⁇ m or more or 10 ⁇ m or more, and 30 ⁇ m or less or 20 ⁇ m or less.
  • the circuit connection adhesive film of this embodiment is a first circuit member having a first electrode (for example, a first circuit member in which a first circuit electrode is formed on the main surface of a first substrate). and a second circuit member having a second electrode (for example, a second circuit member having a second circuit electrode formed on the main surface of a second substrate). It can be suitably used as a circuit connection adhesive film for connecting electrodes (a first circuit electrode and a second circuit electrode) facing each other.
  • the adhesive film for circuit connection may have a multilayer structure of two or more layers in that stable connection resistance is easily obtained.
  • the circuit connection adhesive film may be a circuit connection adhesive film that does not contain conductive particles.
  • the circuit connection adhesive film of this embodiment can be produced by the following method. Specifically, first, components (A), (B), and (C), as well as other components added as necessary, are added to a solvent (organic solvent), and mixed by stirring, kneading, etc.
  • a varnish composition (varnish-like adhesive composition) is prepared by dissolving or dispersing the adhesive composition. 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 for circuit connection can be formed.
  • 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 can 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.
  • 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.
  • the circuit connection structure of this embodiment includes a first circuit member having a first electrode, a second circuit member having a second electrode, and a space between the first circuit member and the second circuit member. and a connecting portion that electrically connects the first electrode and the second electrode to each other, and the connecting portion is formed by curing the adhesive composition of the present embodiment or the adhesive film for circuit connection of the present embodiment. Including things.
  • the method for manufacturing a circuit connection structure according to the present embodiment includes: a first circuit member having a first electrode; a second circuit member having a second electrode; and a circuit connection adhesive film according to the present embodiment. , is heated and pressurized in a state where the first electrode and the second electrode are arranged to face each other with the circuit connecting adhesive film interposed therebetween, so that the first electrode and the second electrode are connected to each other.
  • the method includes a step of electrically connecting.
  • FIG. 1 is a schematic cross-sectional view showing one embodiment of a circuit connection structure.
  • the circuit connection structure 1 shown in FIG. 1 includes a first circuit member 20 having a first circuit board 21 and a first circuit electrode (first connection terminal) 22 formed on the main surface 21a of the first circuit board 21. , a second circuit member 30 having a second circuit board 31 and a second circuit electrode (second connection terminal) 32 formed on its main surface 31a;
  • the connecting portion 10 is interposed between the circuit member 30 and the connecting portion 10 and the circuit member 30 is bonded thereto.
  • the second circuit member 30 is arranged to face the first circuit member 20 such that the second circuit electrode 32 faces the first circuit electrode 22.
  • the connecting portion 10 is formed by interposing the circuit connecting adhesive film of the present embodiment between the first circuit member 20 and the second circuit member 30 and applying pressure in that state, Contains cured adhesive film for circuit connections.
  • the connection part 10 is formed using a circuit connection adhesive film containing conductive particles, and the connection part 10 includes an insulating layer 11 and an adhesive film for circuit connection containing conductive particles. It is composed of dispersed conductive particles 7.
  • the insulating layer 11 is derived from components other than the conductive particles in the adhesive film and includes a cured product formed by radical polymerization of a radically polymerizable compound.
  • the opposing first circuit electrode 22 and second circuit electrode 32 are electrically connected via the conductive particles 7.
  • the first circuit electrodes 22 and the second circuit electrodes 32 formed on the same circuit board are insulated from each other.
  • Examples of the first circuit board 21 and the second circuit board 31 include chip components such as semiconductor chips, resistor chips, and capacitor chips, and substrates such as printed circuit boards.
  • chip components such as semiconductor chips, resistor chips, and capacitor chips
  • 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.
  • a semiconductor a substrate made of inorganic materials such as glass and ceramic, a plastic substrate, or a glass/epoxy substrate is used.
  • Plastic substrates include polyimide films, polycarbonate films, and polyester films.
  • the first circuit electrode and the second circuit electrode are formed from metal such as copper.
  • the surface of at least one of the first circuit electrode and the second circuit electrode is preferably made of a metal selected from gold, silver, tin, and the platinum group.
  • 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 20 and the second circuit member 30 may be a liquid crystal display panel having a glass substrate or a plastic substrate as a circuit board and having connection terminals made of ITO or the like.
  • one of the first circuit member 20 and the second circuit member 30 is 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 circuit connection structure is constructed by appropriately combining these various circuit members as necessary.
  • the substrate provided with the circuit electrodes is preferably heat-treated in advance before the connection process using the circuit connection adhesive film in order to eliminate the influence of volatile components on the connection due to heating during connection.
  • the circuit connection structure 1 includes, for example, a first circuit member 20, a circuit connection adhesive film, and a second circuit member 30, in this order, and a first connection terminal 22 and a second connection terminal 32 that are connected to each other. It is formed by stacking them so that they face each other and applying pressure or further heating in that state.
  • the pressure 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 carried out 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 of polyurethane acrylate (UA1) was 15,000.
  • 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
  • conductive particles By forming a layer made of nickel on the surface of polystyrene particles so that the layer thickness is 0.2 ⁇ m, conductive particles with an average particle size of 4 ⁇ m, a maximum particle size of 4.5 ⁇ m, and a specific gravity of 2.5 are obtained. Ta.
  • thermoplastic resin A1 Use a 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 blending amount in the table is the blending amount of bisphenol A type phenoxy resin) )
  • B1-1 Cyclopolymerizable monomer (product name: FX-AO-MA, manufactured by Nippon Shokubai Co., Ltd.)
  • B2-1 Polyurethane acrylate (UA1) synthesized as described above
  • B2-2 2-methacryloyloxyethyl acid phosphate (trade name: Light Ester P-2M, manufactured by Kyoeisha Chemical Co., Ltd.)
  • B2-3 Diacrylate having a tricyclodecane skeleton (dicyclopentadiene type diacrylate) (trade name: DCP-A, manufactured by Kyoeisha Chemical Co., Ltd.)
  • B2-4 Isobornyl acrylate (product name: IBXA, manufactured by Osaka Organic Chemical Industry Co., Ltd.) (radical polymerization initiator)
  • C1 Benzoyl peroxide (product name: Niper BMT-K40, manufactured by NOF Corporation) (thiol compound)
  • D1 Pentaerythyl peroxide
  • the varnish composition obtained above was applied onto a 50 ⁇ m thick PET film using a coating device. Next, hot air drying was performed at 70° C. for 3 minutes to form an adhesive film having a thickness (thickness after drying) of 10 ⁇ m on the PET film.
  • a COF with a pitch of 25 ⁇ m (manufactured by FLEXSEED) and a glass substrate with a thin film electrode (height: 1200 ⁇ ) made of silicon nitride (SiNx) were placed on the glass substrate (manufactured by Geomatec) through the prepared adhesive film. (manufactured by) were connected over a width of 1 mm using a thermocompression bonding device (heating method: constant heat type, manufactured by Taiyo Kikai Seisakusho Co., Ltd.) under the conditions of 180 ° C. and 4.5 MPa for 4 seconds. , a circuit connection structure (connection structure) was produced.
  • connection resistance value between opposing electrodes was measured with a multimeter immediately after connection and after a high temperature and high humidity test.
  • the high temperature and high humidity test was conducted by leaving the sample in a constant temperature and humidity chamber at 85° C. and 85% RH for 100 hours.
  • the connection resistance value was determined as the average value of resistances at 16 points between opposing electrodes.
  • the circuit connection was such that the connection resistance between opposing electrodes could be maintained sufficiently low even after the high temperature and high humidity test. I was able to get the structure.
  • SYMBOLS 1 Circuit connection structure, 7... Conductive particles, 10... Connection part, 11... Insulating layer, 20... First circuit member, 21... First circuit board, 22... First circuit electrode (first connection terminal), 30... second circuit member, 31... second circuit board, 32... second circuit electrode (second connection terminal).

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

Abstract

Un film adhésif pour connexion de circuit comprend : une composition de résine contenant une résine thermoplastique, un composé polymérisable par voie radicalaire et un initiateur de polymérisation radicalaire ; et des particules conductrices, un monomère cyclopolymérisable y étant contenu en tant que composé polymérisable par voie radicalaire.
PCT/JP2023/012839 2022-04-06 2023-03-29 Composition adhésive, film adhésif pour connexion de circuit, structure de connexion de circuit et son procédé de production Ceased WO2023195398A1 (fr)

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WO2024185743A1 (fr) * 2023-03-07 2024-09-12 三井化学株式会社 Agent d'étanchéité pour cristaux liquides, panneau d'affichage à cristaux liquides l'utilisant, et procédé de fabrication de panneau d'affichage à cristaux liquides

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WO2005121266A1 (fr) * 2004-06-09 2005-12-22 Hitachi Chemical Co., Ltd. Composition adhésive, matériau de connexion de circuit, structure de connexion pour élément de circuit, et dispositif semi-conducteur
KR20090059319A (ko) * 2007-12-06 2009-06-11 제일모직주식회사 2-스텝 열경화형 이방 도전성 접착 조성물 및 이방 도전성접착 필름
JP2022003367A (ja) * 2020-06-23 2022-01-11 三星エスディアイ株式会社Samsung SDI Co., Ltd. 光学部材用硬化性樹脂組成物、その硬化物、偏光板、および画像表示装置
JP2022050067A (ja) * 2020-09-17 2022-03-30 日東電工株式会社 画像表示装置に用いる粘着剤組成物、粘着剤層付き光学フィルム及び画像表示装置
WO2023276889A1 (fr) * 2021-07-01 2023-01-05 昭和電工マテリアルズ株式会社 Film adhésif pour circuit de connexion, structure de connexion de circuit et son procédé de fabrication

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WO2005121266A1 (fr) * 2004-06-09 2005-12-22 Hitachi Chemical Co., Ltd. Composition adhésive, matériau de connexion de circuit, structure de connexion pour élément de circuit, et dispositif semi-conducteur
KR20090059319A (ko) * 2007-12-06 2009-06-11 제일모직주식회사 2-스텝 열경화형 이방 도전성 접착 조성물 및 이방 도전성접착 필름
JP2022003367A (ja) * 2020-06-23 2022-01-11 三星エスディアイ株式会社Samsung SDI Co., Ltd. 光学部材用硬化性樹脂組成物、その硬化物、偏光板、および画像表示装置
JP2022050067A (ja) * 2020-09-17 2022-03-30 日東電工株式会社 画像表示装置に用いる粘着剤組成物、粘着剤層付き光学フィルム及び画像表示装置
WO2023276889A1 (fr) * 2021-07-01 2023-01-05 昭和電工マテリアルズ株式会社 Film adhésif pour circuit de connexion, structure de connexion de circuit et son procédé de fabrication

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2024185743A1 (fr) * 2023-03-07 2024-09-12 三井化学株式会社 Agent d'étanchéité pour cristaux liquides, panneau d'affichage à cristaux liquides l'utilisant, et procédé de fabrication de panneau d'affichage à cristaux liquides

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