WO2017090693A1 - 接着剤組成物及び構造体 - Google Patents

接着剤組成物及び構造体 Download PDF

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Publication number
WO2017090693A1
WO2017090693A1 PCT/JP2016/084853 JP2016084853W WO2017090693A1 WO 2017090693 A1 WO2017090693 A1 WO 2017090693A1 JP 2016084853 W JP2016084853 W JP 2016084853W WO 2017090693 A1 WO2017090693 A1 WO 2017090693A1
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WIPO (PCT)
Prior art keywords
component
mass
adhesive composition
parts
circuit
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PCT/JP2016/084853
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English (en)
French (fr)
Japanese (ja)
Inventor
智樹 森尻
潤 竹田津
田中　勝
立澤　貴
耕太郎 関
健太 菊地
Original Assignee
日立化成株式会社
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Application filed by 日立化成株式会社 filed Critical 日立化成株式会社
Priority to JP2017552705A priority Critical patent/JP6958359B2/ja
Priority to CN201680068878.6A priority patent/CN108291131B/zh
Priority to KR1020187017186A priority patent/KR102556357B1/ko
Publication of WO2017090693A1 publication Critical patent/WO2017090693A1/ja

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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
    • 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
    • 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
    • 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
    • C09J9/00—Adhesives characterised by their physical nature or the effects produced, e.g. glue sticks
    • C09J9/02—Electrically-conducting adhesives
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
    • H05K1/00—Printed circuits
    • H05K1/02—Details
    • H05K1/14—Structural association of two or more printed circuits
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
    • H05K3/00—Apparatus or processes for manufacturing printed circuits
    • H05K3/30—Assembling printed circuits with electric components, e.g. with resistor
    • H05K3/32—Assembling printed circuits with electric components, e.g. with resistor electrically connecting electric components or wires to printed circuits
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
    • H05K3/00—Apparatus or processes for manufacturing printed circuits
    • H05K3/30—Assembling printed circuits with electric components, e.g. with resistor
    • H05K3/32—Assembling printed circuits with electric components, e.g. with resistor electrically connecting electric components or wires to printed circuits
    • H05K3/321—Assembling printed circuits with electric components, e.g. with resistor electrically connecting electric components or wires to printed circuits by conductive adhesives

Definitions

  • the present invention relates to an adhesive composition and a structure.
  • adhesives are conventionally used in semiconductor elements and liquid crystal display elements (display display elements) for the purpose of bonding various members in the elements.
  • the properties required for adhesives are diverse, including adhesiveness, heat resistance, reliability in high temperature and high humidity conditions, and the like.
  • adherends used for bonding include printed wiring boards, organic substrates (eg, polyimide substrates), metals (titanium, copper, aluminum, etc.), ITO, IZO, IGZO, SiN x , SiO.
  • Substrates having various surface states such as 2 are used, and molecular design of an adhesive suitable for each adherend is required.
  • thermosetting resins epoxy resins, acrylic resins, etc.
  • a latent curing agent that generates an epoxy resin and a cationic or anionic species having reactivity with the epoxy resin by heat or light
  • the latent curing agent is an important factor for determining the curing temperature and the curing rate, and various compounds have been used from the viewpoints of storage stability at room temperature and curing rate during heating. In the actual process, for example, desired adhesiveness was obtained by curing under a curing condition of a temperature of 170 to 250 ° C. for 10 seconds to 3 hours.
  • radical curing adhesives using a (meth) acrylate derivative and a peroxide as a radical polymerization initiator in combination.
  • radicals that are reactive species are very reactive, so they can be cured for a short time, and the peroxide is stable below the decomposition temperature of the radical polymerization initiator.
  • a curing system that achieves both low-temperature short-time curing and storage stability (for example, storage stability near room temperature).
  • the above-mentioned radical curing adhesive has a problem that peeling occurs at the interface between the adherend and the adhesive after high-temperature and high-humidity treatment (high-temperature and high-humidity test) such as 85 ° C. and 85% RH. It has become.
  • the adhesive composition used as an adhesive it is required for the adhesive composition used as an adhesive to further enhance the effect of suppressing peeling after the high-temperature and high-humidity treatment.
  • This invention is made
  • the adhesive composition has a silane compound having a urethane bond and an alkoxysilyl group in the molecule, and the silane compound. It became clear that it is important to contain the compound which has a urethane bond other than these, and that the linear thermal expansion coefficient of the hardened
  • the adhesive composition contains a silane compound having a urethane bond and an alkoxysilyl group, and a compound having a urethane bond, which is different from the silane compound, the silane It has been found that the effect of improving peeling by the compound is greatly improved. Furthermore, the present inventors have found that by using these components, the linear thermal expansion coefficient of the cured product tends to decrease, and the average linear thermal expansion coefficient of the cured product at 30 to 90 ° C. is set to 800 ppm / It has been found that adjusting to K or less is effective in suppressing peeling after the high-temperature and high-humidity treatment.
  • the adhesive composition according to the present invention comprises (a) a thermoplastic resin (hereinafter also referred to as “component (a)” in some cases), (b) a silane compound having a urethane bond and an alkoxysilyl group in the molecule. (Hereinafter also referred to as “(b) component”), (c) radical polymerizable compound (hereinafter also referred to as “(c) component”), and (d) radical polymerization initiator (hereinafter referred to as case).
  • component (d) (Also referred to as “component (d)”), (a) component, (c) component, (d) component, or (a) component, (b) component, (c) component, and (d) component
  • component (e) a component other than (e) a compound having a urethane bond (hereinafter also referred to as “component (e)” in some cases), and the average linear thermal expansion coefficient of the cured product at 30 to 90 ° C. (hereinafter simply referred to as “average”).
  • average a compound having a urethane bond
  • linear thermal expansion coefficient is 800ppm / K or less A.
  • the adhesive composition according to the present invention can suppress peeling after high-temperature and high-humidity treatment. It is presumed that such an effect of suppressing peeling is obtained by improving the interfacial adhesion after the high-temperature and high-humidity treatment. Further, the present inventors have found that the effect of improving peeling is sustained in the adhesive composition according to the present invention. That is, the adhesive composition according to the present invention is excellent in storage stability.
  • the cause of peeling after high-temperature and high-humidity treatment is the cause of adhesion inhibition due to insufficient adhesive reaction (insufficient curing) due to the shorter temperature and shorter mounting, and commoditization of display members such as smartphones.
  • the number of adherends (display members, liquid crystal panels, etc.) whose surfaces are contaminated with easy-to-use and inexpensive materials is increasing, and hydrophilicity is higher than silicon nitride used in conventional insulating films, and high-temperature and high-humidity treatment It is considered that the use of adherends having a surface that easily peels later (substrates such as raw glass) is increasing.
  • the adhesive composition according to the present invention even after such an adherend is used, peeling after the high-temperature and high-humidity treatment can be suppressed.
  • the component (b) preferably further has at least one selected from the group consisting of a (meth) acryloyl group and a vinyl group. Thereby, peeling after a high-temperature, high-humidity process can be further suppressed.
  • the component (e) preferably contains at least one selected from the group consisting of polyurethane, polyester urethane and urethane (meth) acrylate. Thereby, peeling after a high-temperature, high-humidity process can be further suppressed.
  • the content of the component is preferably 20% by mass or more based on the total mass of the solid content in the adhesive composition. Thereby, peeling after a high-temperature, high-humidity process can be further suppressed.
  • the adhesive composition according to the present invention preferably further contains an inorganic filler having a primary particle size of 100 nm or less. Thereby, peeling after a high-temperature, high-humidity process can be further suppressed.
  • the structure according to the present invention includes the adhesive composition or a cured product thereof.
  • the structure according to the present invention includes a first circuit member having a first circuit electrode, a second circuit member having a second circuit electrode, the first circuit member, and the second circuit member.
  • an adhesive composition capable of suppressing peeling after a high-temperature and high-humidity treatment, and a structure using the same.
  • an application of an adhesive composition or a cured product thereof to a structure or its production.
  • ADVANTAGE OF THE INVENTION According to this invention, the application of the adhesive composition or its hardened
  • ADVANTAGE OF THE INVENTION According to this invention, the application of the adhesive composition or its hardened
  • (meth) acrylate means at least one of acrylate and methacrylate corresponding thereto.
  • the materials exemplified below can be used singly 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 there is a specific notice when there are a plurality of substances corresponding to each component in the composition.
  • the numerical range indicated by using “to” indicates a range including the numerical values described before and after “to” as the minimum value and the maximum value, respectively. “A or B” only needs to include either A or B, and may include both.
  • “Room temperature” means 25 ° C.
  • the upper limit value or lower limit value of a numerical range of a certain step may be replaced with the upper limit value or lower limit value of the numerical range of another step. Further, in the numerical ranges described in this specification, the upper limit value or the lower limit value of the numerical range may be replaced with the values shown in the examples.
  • a high adhesive strength after high-temperature and high-humidity treatment means high interfacial adhesion after high-temperature and high-humidity treatment.
  • the total mass of the solid content in the adhesive composition means the total mass of the adhesive composition when the adhesive composition does not contain a solvent. When it contains a solvent, it means the mass after subtracting the mass of the solvent from the total mass of the adhesive composition.
  • the “total mass of solids in the adhesive composition” does not include the mass of conductive particles
  • the “total volume of solids in the adhesive composition” is Does not include the volume of the conductive particles (that is, “the total mass of the solid content in the adhesive composition” means “the total mass of the solid content in the adhesive composition (excluding the conductive particles)”
  • the “total volume of solid content in the adhesive composition” means “the total volume of solid content (excluding conductive particles) in the adhesive composition”).
  • the adhesive composition according to the present embodiment includes (a) a thermoplastic resin, (b) a silane compound having a urethane bond and an alkoxysilyl group in the molecule, (c) a radical polymerizable compound, and (d) a radical.
  • a component other than (a) component, (c) component, (d) component, or (a) component, (b) component, (c) component, and (d) component, containing a polymerization initiator (e) ) Contains a compound having a urethane bond.
  • the adhesive composition according to the present embodiment is, for example, a radical curable adhesive composition.
  • component (a) examples include at least one resin selected from the group consisting of polyimide, polyamide, phenoxy resin, (meth) acrylic resin, polyester, polyurethane, polyester urethane, polyether urethane, and polyvinyl butyral.
  • a component can be used individually by 1 type or in combination of 2 or more types.
  • the component (a) preferably contains a phenoxy resin from the viewpoint of further suppressing peeling after the high-temperature and high-humidity treatment.
  • the component (a) preferably contains a thermoplastic resin having a urethane bond from the viewpoint of further suppressing peeling after the high-temperature and high-humidity treatment.
  • thermoplastic resins include polyurethane, polyester urethane, polyether urethane, and the like.
  • a rubber component can be used for the purpose of stress relaxation and further improvement of the adhesiveness after the high temperature and high humidity treatment.
  • the rubber component include acrylic rubber, polyisoprene, polybutadiene, carboxyl group-terminated polybutadiene, hydroxyl group-terminated polybutadiene, 1,2-polybutadiene, carboxyl group-terminated 1,2-polybutadiene, hydroxyl group-terminated 1,2-polybutadiene, and styrene-butadiene.
  • Examples include rubber, hydroxyl-terminated styrene-butadiene rubber, carboxylated nitrile rubber, hydroxyl-terminated poly (oxypropylene), alkoxysilyl group-terminated poly (oxypropylene), poly (oxytetramethylene) glycol, polyolefin glycol, and poly- ⁇ -caprolactone. It is done.
  • the rubber component preferably has a cyano group or a carboxyl group, which is a highly polar group, as a side chain group or a terminal group from the viewpoint of further improving the adhesiveness after the high temperature and high humidity treatment.
  • a rubber component can be used individually by 1 type or in combination of 2 or more types.
  • the weight average molecular weight (Mw) of the component (a) is preferably 5000 or more and more preferably 10,000 or more from the viewpoint of further improving the adhesive strength of the adhesive composition.
  • the weight average molecular weight (Mw) of the component (a) tends to provide good compatibility with other components, and is preferably 1000000 or less from the viewpoint of easily obtaining suitable fluidity of the adhesive composition. 500,000 or less is more preferable, and 400,000 or less is still more preferable. From these viewpoints, the weight average molecular weight of the component (a) is preferably from 5,000 to 1,000,000, more preferably from 5,000 to 500,000, still more preferably from 10,000 to 400,000.
  • the weight average molecular weight can be measured, for example, by gel permeation chromatography (GPC) using a standard polystyrene calibration curve. More specifically, it can be measured under the conditions described in the examples.
  • GPC gel permeation chromatography
  • the content of the component (a) is a total amount of component (a) and component (c) 100. 20 mass parts or more are preferable with respect to mass parts, 30 mass parts or more are more preferable, and 35 mass parts or more are still more preferable.
  • the content of the component (a) is preferably 80 parts by mass or less with respect to 100 parts by mass of the total amount of the component (a) and the component (c), from the viewpoint that suitable fluidity of the adhesive composition is easily obtained. 70 mass parts or less are more preferable, and 65 mass parts or less are still more preferable. From these viewpoints, the content of the component (a) is preferably 20 to 80 parts by mass, more preferably 30 to 70 parts by mass with respect to 100 parts by mass of the total amount of the components (a) and (c), More preferred is ⁇ 65 parts by mass.
  • the component (a) may contain a thermoplastic resin having a urethane bond.
  • the component (a) may include the component (e).
  • the content C a1 of the component (a) having a urethane bond is selected from the viewpoint of further suppressing peeling after the high-temperature and high-humidity treatment.
  • the following ranges are preferred with respect to 100 parts by mass of the total component.
  • the content C a1 is preferably 20 parts by mass or more, more preferably 30 parts by mass or more, and still more preferably 35 parts by mass or more.
  • the content C a1 is preferably 80 parts by mass or less, more preferably 70 parts by mass or less, and still more preferably 65 parts by mass or less. From these viewpoints, the content C a1 is preferably 20 to 80 parts by mass, more preferably 30 to 70 parts by mass, and still more preferably 35 to 65 parts by mass.
  • the adhesive composition according to this embodiment contains a silane compound having a urethane bond and an alkoxysilyl group in the molecule as the component (b).
  • a component can be used individually by 1 type or in combination of 2 or more types.
  • the component (b) may be a compound having a urethane bond and a hydrolyzable C 1 -C 2 alkoxysilyl group in the molecule.
  • a compound represented by the following formula (1) is preferable from the viewpoint of further suppressing peeling after the high temperature and high humidity treatment.
  • m represents an integer of 1 to 3
  • R 11 represents a hydrogen atom, a methyl group or an ethyl group
  • R 12 represents an arbitrary monovalent organic group
  • R 13 represents an arbitrary 2 A valent organic group.
  • a plurality of R 11 in the same molecule may be the same or different.
  • the component (b) preferably further has a reactive functional group from the viewpoint of further suppressing peeling after the high-temperature and high-humidity treatment. That is, as the component (b), an alkoxysilane compound having a reactive functional group and a urethane bond in the molecule is preferable.
  • R 12 is preferably an organic group having a reactive functional group.
  • the reactive functional group may be at least one functional group selected from the group consisting of a (meth) acryloyl group and a vinyl group from the viewpoint of further suppressing peeling after the high-temperature and high-humidity treatment.
  • R 13 may be a group represented by the following formula.
  • n represents an arbitrary integer.
  • M is preferably 2 or 3, more preferably 3, from the viewpoint of further suppressing peeling after the high-temperature and high-humidity treatment.
  • n is preferably from 0 to 15, more preferably from 1 to 10, and even more preferably from 1 to 5 from the viewpoint of further suppressing peeling after the high-temperature and high-humidity treatment.
  • Specific examples of the compound represented by the formula (1) include compounds represented by the following formulas (1a) to (1k). These compounds can be used individually by 1 type or in combination of 2 or more types.
  • a compound in which R 1b is a hydrogen atom in the formula (1b) is preferable from the viewpoint of further suppressing peeling after the high temperature and high humidity treatment.
  • R 1a represents an alkyl group having 1 to 10 carbon atoms or a cyclic alkyl group.
  • R 1b , R 1c and R 1d represents a hydrogen atom or a methyl group.
  • R 1e , R 11f , R 1g , R 1h , R 1i, and R 1j represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a cyclic alkyl group, an alkoxy group, an acyl group, or an acyloxy group.
  • R 12f represents an alkylene group having 1 to 3 carbon atoms.
  • Et represents an ethyl group
  • Me represents a methyl group.
  • p represents an integer of 1 to 5.
  • the content of the component (b) is the adhesive composition from the viewpoint that peeling after the high-temperature and high-humidity treatment is further suppressed (for example, generation of peeling bubbles at the interface between the circuit member and the circuit connecting material is further suppressed).
  • the following ranges are preferred based on the total mass of solids in the product.
  • (B) 0.2 mass part or more is preferable, as for content of a component, 0.5 mass part or more is more preferable, 1 mass part or more is further more preferable, and 5 mass part or more is especially preferable.
  • (B) 30 mass parts or less are preferable, as for content of a component, 20 mass parts or less are more preferable, 15 mass parts or less are still more preferable, and 10 mass parts or less are especially preferable. From these viewpoints, the content of the component (b) is preferably 0.2 to 30 parts by mass, more preferably 0.5 to 20 parts by mass, further preferably 1 to 15 parts by mass, and 5 to 10 parts by mass. Particularly preferred.
  • the content of the component (b) is preferably in the following range with respect to 100 parts by mass of the component (a) from the viewpoint of further suppressing peeling after the high temperature and high humidity treatment.
  • content of a component exceeds 5 mass parts, 7.5 mass parts or more are more preferable, 10 mass parts or more are further more preferable, and 15 mass parts or more are especially preferable.
  • 100 mass parts or less are preferable, as for content of a component, 80 mass parts or less are more preferable, 60 mass parts or less are more preferable, 40 mass parts or less are especially preferable, and 30 mass parts or less are very preferable.
  • the content of the component (b) is preferably more than 5 parts by mass and 100 parts by mass or less, more preferably 7.5 to 80 parts by mass, further preferably 10 to 60 parts by mass, and 15 to 40 parts by mass. Parts are particularly preferred, and 15 to 30 parts by weight are very particularly preferred.
  • the adhesive composition according to the present embodiment may contain a radical polymerizable compound (excluding a compound corresponding to the component (b)) as the component (c).
  • a radical polymerizable compound excluding a compound corresponding to the component (b)
  • a monomer and / or an oligomer can be used as the component (c).
  • the component may be a radical polymerizable compound having two or more (meth) acryloyl groups in the molecule.
  • a polyfunctional (meth) acrylate compound having two or more (meth) acryloyloxy groups in the molecule is preferable. In this case, the cohesive force after curing is sufficiently exhibited and the shrinkage due to curing can be suppressed, whereby the adhesiveness is further improved and the peeling after the high-temperature and high-humidity treatment tends to be further suppressed.
  • Examples of such (meth) acrylate compounds include epoxy (meth) acrylate, urethane (meth) acrylate, polyether (meth) acrylate, polyester (meth) acrylate, trimethylolpropane tri (meth) acrylate, polyalkylene glycol di ( (Meth) acrylate (polyethylene glycol di (meth) acrylate, etc.), neopentyl glycol di (meth) acrylate, dipentaerythritol hexa (meth) acrylate, isocyanuric acid modified bifunctional (meth) acrylate, isocyanuric acid modified trifunctional (meth) An acrylate etc. are mentioned.
  • a component can be used individually by 1 type or in combination of 2 or more types.
  • epoxy (meth) acrylate obtained by adding (meth) acrylic acid to two glycidyl groups of bisphenol fluorenediglycidyl ether, ethylene glycol and / or two glycidyl groups of bisphenol fluorenediglycidyl ether
  • examples include epoxy (meth) acrylates in which a (meth) acryloyloxy group is introduced into a compound to which propylene glycol has been added.
  • the component (c) preferably contains a radical polymerizable compound having two or more (meth) acryloyl groups in the molecule and having a urethane bond.
  • a radical polymerizable compound having two or more (meth) acryloyl groups in the molecule and having a urethane bond.
  • the compatibility between the component (b) and the component (c) is improved, and the peeling after the high-temperature and high-humidity treatment tends to be further suppressed.
  • radically polymerizable compounds include urethane (meth) acrylate.
  • the adhesive composition according to this embodiment may contain a monofunctional (meth) acrylate compound as the component (c) for the purpose of adjusting fluidity.
  • Examples of monofunctional (meth) acrylate compounds include pentaerythritol (meth) acrylate, 2-cyanoethyl (meth) acrylate, cyclohexyl (meth) acrylate, dicyclopentenyl (meth) acrylate, and dicyclopentenyloxyethyl (meth).
  • the adhesive composition according to this embodiment contains a compound having a radical polymerizable functional group such as an allyl group, a maleimide group, and a vinyl group as the component (c) for the purpose of improving the crosslinking rate. Also good.
  • a compound having a radical polymerizable functional group such as an allyl group, a maleimide group, and a vinyl group as the component (c) for the purpose of improving the crosslinking rate.
  • examples of such compounds include N-vinylimidazole, N-vinylpyridine, N-vinylpyrrolidone, N-vinylformamide, N-vinylcaprolactam, 4,4′-vinylidenebis (N, N-dimethylaniline), Examples include N-vinylacetamide, N, N-dimethylacrylamide, N-isopropylacrylamide and N, N-diethylacrylamide.
  • the adhesive composition according to the present embodiment contains a radical polymerizable compound having a phosphate group (hereinafter, also referred to as “(c1) component” in some cases) as the component (c) for the purpose of improving adhesive strength. It is preferable to do.
  • the component (c1) include compounds represented by the following formula (2a), formula (2b), or formula (2c).
  • R 21a represents a hydrogen atom or a methyl group
  • R 22a represents a (meth) acryloyloxy group
  • w and x each independently represents an integer of 1 to 8.
  • a plurality of R 21a , R 22a , w and x in the same molecule may be the same or different.
  • R 2b represents a (meth) acryloyloxy group
  • y and z each independently represents an integer of 1 to 8.
  • a plurality of R 2b , y and z in the same molecule may be the same or different.
  • R 21c represents a hydrogen atom or a methyl group
  • R 22c represents a (meth) acryloyloxy group
  • b and c each independently represents an integer of 1 to 8.
  • a plurality of R 21c and b in the same molecule may be the same or different.
  • Examples of the component (c1) include 2,2′-di (meth) acryloyloxydiethyl phosphate, EO (ethylene oxide) -modified di (meth) acrylate, acid phosphooxyethyl (meth) acrylate, and acid phosphooxy.
  • Examples include propyl (meth) acrylate, acid phosphooxypolyoxyethylene glycol mono (meth) acrylate, acid phosphooxypolyoxypropylene glycol mono (meth) acrylate, phosphoric acid-modified epoxy (meth) acrylate, and vinyl phosphate.
  • the content of the component (c) is preferably 20 parts by mass or more, more preferably 30 parts by mass or more, with respect to 100 parts by mass of the total amount of the component (a) and the component (c). 35 parts by mass or more is more preferable, 40 parts by mass or more is particularly preferable, and 45 parts by mass or more is extremely preferable.
  • the content of the component (c) is preferably 80 parts by mass or less with respect to 100 parts by mass of the total amount of the component (a) and the component (c) from the viewpoint that the effect of suppressing peeling after the high-temperature and high-humidity treatment is greater.
  • the content of the component (c) is preferably 20 to 80 parts by mass, more preferably 30 to 70 parts by mass with respect to 100 parts by mass of the total amount of the components (a) and (c). Is more preferably from 65 to 65 parts by weight, particularly preferably from 40 to 60 parts by weight, and particularly preferably from 45 to 55 parts by weight.
  • the content of the component (c1) is preferably 0.1 parts by mass or more with respect to 100 parts by mass of the total amount of the component (a) and the component (c) from the viewpoint that high adhesive strength is easily obtained, and 0.5 mass Part or more is more preferable, 1 part by mass or more is more preferable, and 2 parts by mass or more is particularly preferable.
  • the content of the component (c1) is such that the physical properties of the cured product of the adhesive composition are not easily lowered, and the total amount of the component (a) and the component (c) is 100 from the viewpoint of obtaining an excellent effect of improving connection reliability.
  • the amount is preferably 15 parts by mass or less, more preferably 10 parts by mass or less, still more preferably 5 parts by mass or less, and particularly preferably 3 parts by mass or less.
  • the content of the component (c1) is preferably 0.1 to 15 parts by mass, and 0.5 to 10 parts by mass with respect to 100 parts by mass of the total amount of the components (a) and (c). More preferred is 1 to 5 parts by mass, still more preferred is 2 to 3 parts by mass.
  • the content of the component (c) is preferably 20% by mass or more, preferably 30% by mass or more based on the total mass of the solid content in the adhesive composition from the viewpoint of further suppressing peeling after the high-temperature and high-humidity treatment. Is more preferable, and 40 mass% or more is still more preferable.
  • the content of the component (c) is preferably 90% by mass or less, preferably 80% by mass or less, based on the total mass of the solid content in the adhesive composition, from the viewpoint of further suppressing peeling after the high-temperature and high-humidity treatment. Is more preferable, 70 mass% or less is still more preferable, and 60 mass% or less is especially preferable.
  • the content of the component (c) is preferably 20 to 90% by mass, more preferably 30 to 80% by mass, and more preferably 40 to 70% by mass based on the total mass of the solid content in the adhesive composition. % Is more preferable, and 40 to 60% by mass is particularly preferable.
  • the component (c) may contain a radical polymerizable compound having a urethane bond.
  • the component (c) may include the component (e).
  • the content Cb1 of the component (c) having a urethane bond is selected from the viewpoint of further suppressing peeling after the high-temperature and high-humidity treatment.
  • the following ranges are preferred with respect to 100 parts by mass of the total component.
  • the content Cb1 is preferably 20 parts by mass or more, more preferably 30 parts by mass or more, and still more preferably 40 parts by mass or more.
  • the content Cb1 is preferably 90 parts by mass or less, more preferably 80 parts by mass or less, still more preferably 70 parts by mass or less, particularly preferably 60 parts by mass or less, and extremely preferably 50 parts by mass or less. From these viewpoints, the content Cb1 is preferably 20 to 90 parts by mass, more preferably 30 to 80 parts by mass, further preferably 40 to 70 parts by mass, particularly preferably 40 to 60 parts by mass, and 40 to 50 parts by mass. Part is very preferred.
  • the mass ratio C b1 / C b2 of the content C b1 to the content C b2 of the component (c) that does not have a urethane bond indicates that peeling after the high-temperature and high-humidity treatment From the viewpoint of further suppression, the following ranges are preferable.
  • the mass ratio C b1 / C b2 is preferably 0.01 or more, more preferably 0.1 or more, still more preferably 1 or more, particularly preferably 2 or more, and extremely preferably 3 or more.
  • the mass ratio C b1 / C b2 may be 50 or less.
  • the adhesive composition according to this embodiment contains a radical polymerization initiator as the component (d).
  • the component (d) can be arbitrarily selected from compounds such as peroxides and azo compounds.
  • a peroxide having a 1 minute half-life temperature of 90 to 175 ° C. and a molecular weight of 180 to 1000 is preferable from the viewpoint of excellent stability, reactivity and compatibility.
  • “1 minute half-life temperature” refers to a temperature at which the half-life of the peroxide is 1 minute.
  • “Half-life” refers to the time taken for the concentration of a compound to decrease to half of its initial value at a given temperature.
  • a component can be used individually by 1 type or in combination of 2 or more types.
  • the component (d) is, for example, 1,1,3,3-tetramethylbutylperoxyneodecanoate, di (4-t-butylcyclohexyl) peroxydicarbonate, di (2-ethylhexyl) peroxydicarbonate , Cumylperoxyneodecanoate, dilauroyl peroxide, 1-cyclohexyl-1-methylethylperoxyneodecanoate, t-hexylperoxyneodecanoate, t-butylperoxyneodecanoate, t -Butyl peroxypivalate, 1,1,3,3-tetramethylbutylperoxy-2-ethylhexanoate, 2,5-dimethyl-2,5-di (2-ethylhexanoylperoxy) hexane, t-hexylperoxy-2-ethylhexanoate, t-butylper
  • the component may contain the radical polymerization initiator which has a urethane bond.
  • the component (d) may include the component (e).
  • the amount of chlorine ions or organic acid contained in the radical polymerization initiator is preferably 5000 ppm or less from the viewpoint of suppressing corrosion of electrodes (for example, connection terminals (circuit electrodes) of circuit members). Furthermore, from the same viewpoint, the radical polymerization initiator is more preferably a compound with less organic acid generated after decomposition. Further, from the viewpoint of further improving the storage stability of the adhesive composition, a radical polymerization initiator having a mass retention of 20% by mass or more after being left open at room temperature and normal pressure for 24 hours is preferably used.
  • the content of the component (d) is preferably 1 part by mass or more with respect to 100 parts by mass of the total amount of the component (a) and the component (c), and 2.5 masses. Part or more is more preferable, 3 parts by weight or more is more preferable, and 4 parts by weight or more is particularly preferable.
  • the content of the component (d) is preferably 15 parts by mass or less and more preferably 10 parts by mass or less with respect to 100 parts by mass of the total amount of the component (a) and the component (c), from the viewpoint of further excellent storage stability. 5 parts by mass or less is more preferable.
  • the content of the component (d) is preferably 1 to 15 parts by mass, more preferably 2.5 to 10 parts by mass with respect to 100 parts by mass of the total amount of the components (a) and (c). 3 to 10 parts by mass is further preferable, and 4 to 5 parts by mass is particularly preferable.
  • the adhesive composition according to the present embodiment may contain the component (e) as the component (a), the component (c), or the component (d), the component (a), the component (b), ( The component (e) may be contained as a component other than the component c) and the component (d). Examples of components other than the component (a), the component (b), the component (c), and the component (d) include urethane beads.
  • the component (e) is preferably at least one component selected from the group consisting of polyurethane, polyester urethane and urethane (meth) acrylate from the viewpoint of further suppressing peeling after the high temperature and high humidity treatment.
  • a component can be used individually by 1 type or in combination of 2 or more types.
  • the adhesive composition according to the present embodiment may contain two or more components (a) having a urethane bond, (a) component having a urethane bond, and (c) component having a urethane bond. May be included.
  • the adhesive composition according to the present embodiment may contain a component (a) having a urethane bond and a component (c) having a urethane bond from the viewpoint of further suppressing peeling after the high-temperature and high-humidity treatment. preferable.
  • the content of the component (e) is preferably in the following range on the basis of the total solid content in the adhesive composition from the viewpoint of further suppressing peeling after the high-temperature and high-humidity treatment.
  • the content of the component (e) is preferably 5% by mass or more, more preferably 10% by mass or more, and further preferably 15% by mass or more.
  • the content of the component (e) is preferably 95% by mass or less, more preferably 90% by mass or less, and still more preferably 85% by mass or less. From these viewpoints, the content of the component (e) is preferably 5 to 95% by mass, more preferably 10 to 90% by mass, and still more preferably 15 to 85% by mass.
  • the content of the component (e) is preferably in the following range with respect to 100 parts by mass of the component (b) from the viewpoint of further suppressing peeling after the high-temperature and high-humidity treatment.
  • content of a component 10 mass parts or more are preferable, 100 mass parts or more are more preferable, 200 mass parts or more are still more preferable, 300 mass parts or more are especially preferable.
  • the content of the component (e) is preferably 2000 parts by mass or less, more preferably 1000 parts by mass or less, further preferably 750 parts by mass or less, and particularly preferably 500 parts by mass or less. From these viewpoints, the content of the component (e) is preferably 10 to 2000 parts by mass, more preferably 100 to 1000 parts by mass, further preferably 200 to 750 parts by mass, and particularly preferably 300 to 500 parts by mass.
  • the effect of improving the interfacial adhesion by the silane compound is greatly improved, and it is estimated that superior interfacial adhesion can be obtained as compared with the conventional adhesive composition.
  • the reason why such an effect is obtained is not clear, but the component (b) having a urethane bond is compatible with the component (e), and the component (b) is localized in the adhesive composition or a cured product thereof.
  • the phenomenon that the component (b) bleeds to the surface of the adhesive composition or the cured product thereof is suppressed, and the deactivation of the component (b) is suppressed.
  • the adhesive composition according to this embodiment may include an arbitrary silane compound different from the component (b).
  • silane compounds include vinyltrimethoxysilane, vinyltriethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, and 3- (meth) acryloxypropylmethyl.
  • Dimethoxysilane 3- (meth) acryloxypropyltrimethoxysilane, 3- (meth) acryloxypropylmethyldiethoxysilane, 3- (meth) acryloxypropyltriethoxysilane, N- (2-aminoethyl) -3 -Aminopropylmethyldimethoxysilane, N-phenyl-3-aminopropyltrimethoxysilane, 3-ureidopropyltriethoxysilane, 3-mercaptopropyltrimethoxysilane, 3-isocyanatopropyltriethoxysilane, and condensation thereof And the like.
  • the content of such a silane compound is preferably 0.1 to 30% by mass, and more preferably 0.25 to 20% by mass, based on the total mass of the solid content in the adhesive composition.
  • peeling after the high temperature and high humidity treatment is further suppressed (for example, generation of peeling bubbles at the interface between the circuit member and the circuit connecting material is further suppressed).
  • the content of the silane compound in the adhesive composition according to this embodiment (the total amount of the silane compound including the component (b)) is from the viewpoint of further suppressing peeling after the high-temperature and high-humidity treatment. 0.1% by mass or more, 1% by mass or more, or 5% by mass or more may be used based on the total mass of the solid content. As the content of the silane compound increases, the average linear thermal expansion coefficient of the cured product tends to decrease.
  • the content of the silane compound in the adhesive composition according to this embodiment may be 30% by mass or less, 20% by mass or less, or 15% by mass or less from the viewpoint of excellent film formability. It may be.
  • the adhesive composition according to the present embodiment may include at least one selected from the group consisting of an inorganic filler and an organic filler as an insulating filler.
  • the inorganic filler include metal oxide fine particles such as silica fine particles, alumina fine particles, silica-alumina fine particles, titania fine particles and zirconia fine particles; and inorganic fine particles such as nitride fine particles.
  • the organic filler include organic fine particles such as silicone fine particles, methacrylate-butadiene-styrene fine particles, acryl-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 adhesive composition according to this embodiment preferably contains an inorganic filler from the viewpoint of further suppressing peeling after the high-temperature and high-humidity treatment.
  • an organic filler consists of (a) component
  • the said organic filler shall be classified into (a) component.
  • the content of each of the organic filler and the inorganic filler is preferably in the following ranges with respect to 100 parts by mass of the total amount of the component (a) and the component (c) from the viewpoint of further suppressing peeling after the high temperature and high humidity treatment.
  • the content is preferably 1 part by mass or more, and more preferably 5 parts by mass or more. From the viewpoint of reducing the linear thermal expansion coefficient, the larger the content of the inorganic filler, the better.
  • the content may be 50 parts by mass or less.
  • the primary particle diameter of the inorganic filler is preferably 100 nm or less, more preferably 75 nm or less, and still more preferably 50 nm or less, from the viewpoint of further suppressing peeling after the high-temperature and high-humidity treatment.
  • the smaller the primary particle size of the inorganic filler the larger the total area of the interface between the inorganic filler and the resin (for example, the component (a)) when the same amount is used, and the linear thermal expansion coefficient tends to decrease.
  • the primary particle size of the inorganic filler may be 5 nm or more.
  • the primary particle size of the inorganic filler can be measured with a scanning electron microscope.
  • the adhesive composition according to the present embodiment may contain conductive particles.
  • the adhesive composition containing conductive particles can be particularly suitably used as an anisotropic conductive adhesive.
  • the conductive particles include metal particles such as Au, Ag, Pd, Ni, Cu, and solder; and carbon particles.
  • the metal particles may be metal particles obtained by combining a plurality of metals.
  • the metal particles may be particles having copper particles and a silver layer covering the copper particles.
  • the conductive particles are composite particles having core particles made of a non-conductive material such as glass, ceramic, plastic, and a conductive layer such as metal, metal particles, and carbon covering the core particles. Also good.
  • the core particle of the composite particle is preferably a plastic particle.
  • the composite particles using the plastic particles as core particles have a deformability that deforms when heated and pressurized. Therefore, when the composite particles are used, for example, when the circuit members are bonded to each other, the contact area between the circuit electrodes and the conductive particles of the circuit members can be increased as compared with the case where other conductive particles are used. . Therefore, according to the adhesive composition containing the composite particles as conductive particles, a circuit connection structure that is further excellent in connection reliability can be obtained.
  • the adhesive composition according to the present embodiment may contain insulating coated conductive particles having the conductive particles and an insulating layer or insulating particles covering at least a part of the surface of the conductive particles. That is, at least a part of the surface of the conductive particles may be covered with an insulating layer or insulating particles.
  • the insulating layer can be provided by a method such as hybridization.
  • the insulating layer or the insulating particles are formed from an insulating material such as a polymer resin.
  • the insulating particles may be the organic filler or inorganic filler described above.
  • the average particle diameter of the conductive particles is preferably 1 to 30 ⁇ m from the viewpoint of obtaining good dispersibility and conductivity.
  • the average particle size of the conductive particles can be measured with a laser diffraction particle size distribution meter.
  • the content of the conductive particles is preferably 0.1 to 30% by volume, more preferably 0.1 to 10% by volume, and 0.5 to 7.5, based on the total volume of the solid content in the adhesive composition. Volume% is more preferable. If content of electroconductive particle is 0.1 volume% or more, there exists a tendency for electroconductivity to improve. If content of electroconductive particle is 30 volume% or less, there exists a tendency for the short circuit between electrodes (circuit electrodes etc.) to become difficult to produce.
  • the content (% by volume) of the conductive particles is determined based on the volume at 23 ° C. of each component constituting the adhesive composition before curing. The volume of each component can be determined by converting mass to volume using specific gravity.
  • the volume of each component can also be measured using an appropriate solvent (water, alcohol, etc.) that does not dissolve or swell the component whose volume is to be measured and that can wet the component well. .
  • an appropriate solvent water, alcohol, etc.
  • the volume increased by putting the solvent into a measuring cylinder or the like and introducing the component to be measured therein can be obtained as the volume of the component.
  • the adhesive composition according to the present embodiment may contain a thiol compound.
  • the adhesive composition according to this embodiment includes an adhesion improver (excluding the component (b) and a silane compound other than the component (b)), a thickener, a leveling agent, a colorant, a weather resistance improver, and the like. These additives may be appropriately contained.
  • the adhesive composition according to this embodiment may contain a solvent.
  • the solvent is not particularly limited as long as it is not reactive with the components in the adhesive composition and exhibits sufficient solubility.
  • the solvent is preferably a solvent having a boiling point of 50 to 150 ° C. at normal pressure. If the boiling point is 50 ° C. or higher, the solvent is poorly volatile at room temperature, and can be used in an open system. When the boiling point is 150 ° C. or lower, it is easy to volatilize the solvent, and thus good reliability can be obtained after bonding.
  • the average linear thermal expansion coefficient at 30 to 90 ° C. of the cured product of the adhesive composition according to this embodiment is 800 ppm / K or less.
  • the average linear thermal expansion coefficient is preferably 750 ppm / K or less, more preferably 700 ppm / K or less, from the viewpoint of further suppressing peeling after the high-temperature and high-humidity treatment.
  • the lower limit of the average linear thermal expansion coefficient may be, for example, 10 ppm / K or more.
  • the average linear thermal expansion coefficient of the cured product can be measured using, for example, a thermomechanical analyzer (manufactured by Shimadzu Corporation). Specifically, it can be measured by the method described in the examples.
  • the average linear thermal expansion coefficient for example, (1) a higher Tg thermoplastic resin is used, (2) the content of the low molecular weight reactive component is reduced, and the low molecular weight reactive component is reduced.
  • there are methods such as using relatively large amounts of oligomer-sized reactive components in the mass ratio of solids, (3) using inorganic fillers, and (4) increasing the content of silane compounds.
  • the low molecular weight reactive component include isocyanuric acid EO-modified di (meth) acrylate.
  • the oligomer-size reactive component include urethane (meth) acrylate.
  • the linear thermal expansion coefficients of glass and polyimide which are the main materials of the liquid crystal panel and FPC (flexible circuit board), respectively, are generally around 10 ppm / K, whereas the lines of conventional radical polymerization system circuit connection materials.
  • the thermal expansion coefficient is 1000 ppm / K or more. Therefore, when a structure is manufactured by connecting a liquid crystal panel and an FPC with a conventional radical polymerization system circuit connection material (that is, in the case of FOG (Flex on Glass) connection), the structure is heated to a high temperature of 85 ° C. and 85% RH.
  • the cured product is 800 ppm / K or less, so that the structure is subjected to a high temperature and high humidity condition of 85 ° C. and 85% RH. Even if it is a case where it processes, it is estimated that the distortion in the said interface does not generate
  • the adhesive composition according to this embodiment can be used in a paste form when it is liquid at room temperature.
  • the adhesive composition When the adhesive composition is solid at room temperature, it may be heated and used, or may be made into a paste using the above-mentioned solvent.
  • the adhesive composition according to this embodiment may be in the form of a film. If necessary, a solution of an adhesive composition containing a solvent or the like is applied onto a fluororesin film, a polyethylene terephthalate film, a peelable substrate (release paper, etc.), and then the solvent is removed to remove the solvent. An adhesive composition can be obtained. Moreover, after making a base material, such as a nonwoven fabric, impregnate the above solution and placing it on a peelable base material, a film-like adhesive composition can be obtained by removing the solvent and the like. Use of the adhesive composition in the form of a film is more convenient from the viewpoint of excellent handleability.
  • the thickness of the film adhesive composition may be 1 to 100 ⁇ m or 5 to 50 ⁇ m.
  • the adhesive composition according to this embodiment can be adhered by applying pressure together with heating or light irradiation. By using heating and light irradiation in combination, it can be bonded at a lower temperature in a shorter time.
  • the light irradiation is preferably performed in the wavelength region of 150 to 750 nm.
  • As the light source a low-pressure mercury lamp, a medium-pressure mercury lamp, a high-pressure mercury lamp (extra-high-pressure mercury lamp, etc.), a xenon lamp, a metal halide lamp, or the like can be used.
  • the irradiation dose may be 0.1 to 10 J / cm 2 .
  • the heating temperature is not particularly limited, but a temperature of 50 to 170 ° C. is preferable.
  • the pressure is not particularly limited as long as it does not damage the adherend, but is preferably 0.1 to 10 MPa. Heating and pressurization are preferably performed in the range of 0.5 seconds to 3 hours.
  • the adhesive composition according to the present embodiment may be used as an adhesive for the same type of adherend, or as an adhesive for different types of adherends having different thermal expansion coefficients. Specifically, it is used as a circuit connecting material represented by anisotropic conductive adhesive, silver paste, silver film, etc .; semiconductor device adhesive material represented by CSP elastomer, CSP underfill material, LOC tape, etc. be able to.
  • the structure according to this embodiment includes the adhesive composition according to this embodiment or a cured product thereof.
  • the structure according to the present embodiment is, for example, a semiconductor device such as a circuit connection structure.
  • the circuit connection structure includes a first circuit member having a first circuit electrode, a second circuit member having a second circuit electrode, and a first circuit.
  • the first circuit member includes, for example, a first substrate and a first circuit electrode disposed on the first substrate.
  • the second circuit member includes, for example, a second substrate and a second circuit electrode disposed on the second substrate. The first circuit electrode and the second circuit electrode face each other and are electrically connected.
  • the circuit connection member includes the adhesive composition according to this embodiment or a cured product thereof.
  • the structure which concerns on this embodiment should just be equipped with the adhesive composition which concerns on this embodiment, or its hardened
  • the manufacturing method of the structure according to the present embodiment includes a step of curing the adhesive composition according to the present embodiment.
  • the circuit connection structure manufacturing method includes a first circuit member having a first circuit electrode and a second circuit member having a second circuit electrode. Between the first circuit electrode and the second circuit electrode by pressing the first circuit member and the second circuit member by placing the adhesive composition according to this embodiment between A heating and pressing step of electrically connecting and curing the adhesive composition by heating.
  • the first circuit electrode and the second circuit electrode can be arranged to face each other.
  • the heating and pressurizing step the first circuit member and the second circuit member can be pressurized in the opposite directions.
  • FIG. 1 is a schematic cross-sectional view showing an embodiment of a structure.
  • a circuit connection structure 100 a shown in FIG. 1 includes a circuit member (first circuit member) 20 and a circuit member (second circuit member) 30 that are opposed to each other, and between the circuit member 20 and the circuit member 30.
  • the circuit connection member 10 which connects these is arrange
  • the circuit connection member 10 includes a cured product of the adhesive composition according to this embodiment.
  • the circuit member 20 includes a substrate (first substrate) 21 and a circuit electrode (first circuit electrode) 22 disposed on the main surface 21 a of the substrate 21.
  • An insulating layer (not shown) may be disposed on the main surface 21a of the substrate 21 as the case may be.
  • the circuit member 30 includes a substrate (second substrate) 31 and a circuit electrode (second circuit electrode) 32 disposed on the main surface 31 a of the substrate 31.
  • An insulating layer (not shown) may be disposed on the main surface 31a of the substrate 31 in some cases.
  • the circuit connecting member 10 contains an insulating substance (cured product of components excluding conductive particles) 10a and conductive particles 10b.
  • the conductive particles 10b are disposed at least between the circuit electrode 22 and the circuit electrode 32 facing each other. In the circuit connection structure 100a, the circuit electrode 22 and the circuit electrode 32 are electrically connected via the conductive particles 10b.
  • the circuit members 20 and 30 have one or a plurality of circuit electrodes (connection terminals).
  • a chip component such as a semiconductor chip (IC chip), a resistor chip, or a capacitor chip; a substrate such as a printed board or a semiconductor mounting board can be used.
  • Examples of the combination of the circuit members 20 and 30 include a semiconductor chip and a semiconductor mounting substrate.
  • the material of the substrate include inorganic substances such as semiconductor, glass, and ceramic; organic substances such as polyimide, polyethylene terephthalate, polycarbonate, (meth) acrylic resin, and cyclic olefin resin; and composites of glass and epoxy.
  • the substrate may be a plastic substrate.
  • FIG. 2 is a schematic cross-sectional view showing another embodiment of the structure.
  • the circuit connection structure 100b shown in FIG. 2 has the same configuration as the circuit connection structure 100a except that the circuit connection member 10 does not contain the conductive particles 10b.
  • the circuit electrode 22 and the circuit electrode 32 are in direct contact and are electrically connected without interposing conductive particles.
  • the circuit connection structures 100a and 100b can be manufactured, for example, by the following method. First, when the adhesive composition is in a paste form, the resin layer containing the adhesive composition is disposed on the circuit member 20 by applying and drying the adhesive composition. When the adhesive composition is in the form of a film, the resin layer containing the adhesive composition is disposed on the circuit member 20 by sticking the film-like adhesive composition to the circuit member 20. Subsequently, the circuit member 30 is placed on the resin layer disposed on the circuit member 20 so that the circuit electrode 22 and the circuit electrode 32 are opposed to each other. And a heat treatment or light irradiation is performed to the resin layer containing an adhesive composition, an adhesive composition hardens
  • a nickel layer having a thickness of 0.2 ⁇ m was formed on the surface of the polystyrene particles. Further, a gold layer having a thickness of 0.04 ⁇ m was formed outside the nickel layer. Thereby, conductive particles having an average particle diameter of 4 ⁇ m were produced.
  • Examples 1 to 6 and Comparative Examples 1 to 6) The components shown in Table 2 were mixed at a mass ratio shown in Table 2.
  • This coating solution was applied to a polyethylene terephthalate (PET) film having a thickness of 50 ⁇ m using a coating apparatus.
  • PET polyethylene terephthalate
  • the coating film was dried with hot air at 70 ° C. for 10 minutes to prepare a film adhesive (film adhesive composition) having a thickness of 18 ⁇ m.
  • the content of each component of the film adhesive shown in Table 2 is the solid content.
  • PKHC is a phenoxy resin (trade name: PKHC, manufactured by Union Carbide, weight average molecular weight 45000). PKHC was used in the form of a 40% by mass solution prepared by dissolving 40 g of PKHC in 60 g of methyl ethyl ketone.
  • KBM503 is 3-methacryloxypropyltrimethoxysilane (trade name: KBM-503, manufactured by Shin-Etsu Chemical Co., Ltd.).
  • EBECRYL436 is a polyester acrylate (radical polymerizable compound, trade name: EBECRYL436, manufactured by Daicel Ornex Co., Ltd.).
  • M-215 is an isocyanuric acid EO-modified diacrylate (radical polymerizable compound, trade name: M-215, manufactured by Toa Gosei Co., Ltd.).
  • P-2M is 2-methacryloyloxyethyl acid phosphate (phosphate ester, trade name: Light Ester P-2M, manufactured by Kyoeisha Chemical Co., Ltd.).
  • “Parroyl L” is dilauroyl peroxide (trade name: Parroyl L, manufactured by NOF Corporation, molecular weight 398.6, 1 minute half-life temperature: 116 ° C.).
  • “R104” is silica particles (inorganic fine particles, trade name: R104, manufactured by Nippon Aerosil Co., Ltd., primary particle size: 12 nm). R104 was used in the form of a 10% by mass dispersion prepared by dispersing 10 g of R104 in a mixed solvent of 45 g of toluene and 45 g of ethyl acetate.
  • ⁇ Measurement of average linear thermal expansion coefficient> A plurality of the film adhesives were prepared. After laminating these film adhesives to a thickness of 100 ⁇ 20 ⁇ m, a cured product sample was prepared by treating in an oven at 180 ° C. for 1 hour. The average linear thermal expansion coefficient of the produced sample at 30 to 90 ° C. was measured with a thermomechanical analyzer (manufactured by Shimadzu Corporation). The measurement was performed on a sample having a length of 10 mm and a width of 4 mm under conditions of a load of 5 gf (per cross-sectional area of 0.4 mm 2 ) and a temperature increase rate of 5 ° C./min. The results are shown in Table 2.
  • Connection (adhesion) was performed by heating and pressurizing at 140 ° C. and 3 MPa for 5 seconds using a thermocompression bonding apparatus (heating method: constant heat type, manufactured by Toray Engineering Co., Ltd.). Thereby, the connection body by which FPC and the glass substrate were connected by the hardened
  • Examples 1 to 6 can maintain a good appearance without peeling at the interface between the glass substrate and the cured product even after the high temperature and high humidity treatment as compared with Comparative Examples 1 to 6. It was done.
PCT/JP2016/084853 2015-11-25 2016-11-24 接着剤組成物及び構造体 WO2017090693A1 (ja)

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