WO2019044046A1 - Adhésif transparent de type film et module de capteur infrarouge - Google Patents

Adhésif transparent de type film et module de capteur infrarouge Download PDF

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Publication number
WO2019044046A1
WO2019044046A1 PCT/JP2018/018093 JP2018018093W WO2019044046A1 WO 2019044046 A1 WO2019044046 A1 WO 2019044046A1 JP 2018018093 W JP2018018093 W JP 2018018093W WO 2019044046 A1 WO2019044046 A1 WO 2019044046A1
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WIPO (PCT)
Prior art keywords
meth
film
acrylate
transparent adhesive
group
Prior art date
Application number
PCT/JP2018/018093
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English (en)
Japanese (ja)
Inventor
さやか 土山
明徳 佐藤
陽輔 佐藤
Original Assignee
リンテック株式会社
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by リンテック株式会社 filed Critical リンテック株式会社
Priority to CN201880055290.6A priority Critical patent/CN111051455B/zh
Priority to SG11202001719RA priority patent/SG11202001719RA/en
Priority to JP2019538963A priority patent/JP7107946B2/ja
Publication of WO2019044046A1 publication Critical patent/WO2019044046A1/fr

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Classifications

    • 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
    • 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
    • C09J7/00—Adhesives in the form of films or foils
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01J—MEASUREMENT OF INTENSITY, VELOCITY, SPECTRAL CONTENT, POLARISATION, PHASE OR PULSE CHARACTERISTICS OF INFRARED, VISIBLE OR ULTRAVIOLET LIGHT; COLORIMETRY; RADIATION PYROMETRY
    • G01J1/00—Photometry, e.g. photographic exposure meter
    • G01J1/02—Details

Definitions

  • the present invention relates to a film-like transparent adhesive and an infrared sensor module.
  • Priority is claimed on Japanese Patent Application No. 2017-163632, filed Aug. 28, 2017, the content of which is incorporated herein by reference.
  • Patent Document 1 As a cover member for an infrared sensor such as a human sensor, a cover glass member having high light transmittance in the infrared region has been proposed (Patent Document 1).
  • the cover glass member is provided with a recess and fixed to the frame portion of the infrared sensor.
  • the infrared sensor can be further miniaturized if a glass wafer having infrared transparency can be directly bonded to the infrared light receiving element using a film adhesive having optical transparency in a wide infrared wavelength range.
  • the present invention has an object to provide a film-like transparent adhesive having optical transparency in a wide infrared wavelength range, capable of directly bonding a glass wafer to an infrared light receiving element, and an infrared sensor module using the same. I assume.
  • the present invention is a thermosetting or energy ray curable film-like transparent adhesive, wherein the film-like transparent adhesive has a light transmittance of 80% or more at a wavelength of 800 nm after curing. provide.
  • the film-like transparent adhesive of the present invention it is preferable that all light transmittances at a wavelength of 800 to 2000 nm after curing be 80% or more.
  • the light transmittance at a wavelength of 850 nm after curing is 90% or more.
  • the film-like transparent adhesive of the present invention preferably contains a filler, and the average particle diameter of the filler is preferably 450 nm or less.
  • an infrared ray receiving element having an infrared ray receiving portion and a glass wafer are cured and adhered by the film-like transparent adhesive, and the infrared ray receiving portion is the glass wafer and the film-like transparent adhesive after curing And an infrared sensor module provided to receive infrared light transmitted through the sensor.
  • a film-like transparent adhesive capable of bonding a glass wafer to an infrared light receiving element, and an infrared sensor module using the same.
  • the film-like transparent adhesive of the present invention is a thermosetting or energy ray-curable film-like transparent adhesive, and has a light transmittance of 80% or more at a wavelength of 800 nm after curing.
  • the film-like transparent adhesive of the present invention has light transmittance in a wide infrared wavelength range around a wavelength of 800 nm, since the light transmittance of the wavelength 800 nm of the transparent resin film after curing is 80% or more. can do.
  • the film-like transparent adhesive according to the present invention it is preferable that all the light transmittances at a wavelength of 800 to 2000 nm after curing be 80% or more, and that the light transmittance at a wavelength of 850 nm after curing be 90% or more preferable.
  • the infrared ray receiving element has a high infrared ray transmittance after curing of the film-like transparent adhesive according to the present invention, whereby the film-like transparent adhesive according to the present invention is cured to bond the glass wafer to the infrared ray receiving element. Infrared rays transmitted through the glass wafer can be efficiently received.
  • the upper limit of the light transmittance at a wavelength of 800 nm after curing of the transparent adhesive film is not limited, but may be 95% or 93%.
  • the upper limit of the light transmittance at a wavelength of 800 to 2000 nm after curing of the transparent adhesive film is not limited, but may be 95% or 93%.
  • the upper limit of the light transmittance at a wavelength of 850 nm after curing of the transparent adhesive film is not limited, but may be 95% or 93%.
  • the film-like transparent adhesive of the present invention is thermosetting or energy ray curable, and may have both thermosetting and energy ray curing properties.
  • a film-like transparent adhesive having a thermosetting property is referred to as "thermosetting film-like transparent adhesive”
  • a film-like transparent adhesive having energy ray curability as “an energy ray-curable film-like transparent adhesive” say.
  • the film-like transparent adhesive preferably has pressure-sensitive adhesiveness.
  • a film-like transparent adhesive having both curability and pressure-sensitive adhesiveness can be stuck by lightly pressing on various adherends in the uncured state.
  • the film-like transparent adhesive may be one that can be attached to various adherends by heating and softening.
  • the film-like transparent adhesive finally becomes a cured product having high impact resistance by curing, and the cured product can retain sufficient adhesive properties even under severe high temperature and high humidity conditions.
  • the film-like transparent adhesive of the present invention is in the form of a film, there is no possibility of liquid dripping when bonding the infrared ray receiving element and the glass wafer by curing, and the thermosetting film-like transparent adhesive is an infrared sensor module At the same time, it is possible to bond the infrared light receiving element and the glass wafer by the heat treatment for forming the.
  • the film-like transparent adhesive may be composed of a single layer (a single layer), or may be composed of a plurality of two or more layers.
  • the plurality of layers may be identical to or different from each other, and the combination of the plurality of layers is not particularly limited as long as the effects of the present invention are not impaired.
  • "a plurality of layers may be the same as or different from each other” means “all layers may be the same or all layers are It may be different, meaning that only some of the layers may be the same.
  • “a plurality of layers are different from each other” means “at least one of the constituent material and thickness of each layer is different from each other” It means that.
  • the thickness of the film-like transparent adhesive is not particularly limited, but is preferably 1 to 50 ⁇ m, and more preferably 3 to 40 ⁇ m.
  • the thickness of the film-like transparent adhesive is not less than the lower limit value, higher adhesion to an adherend (that is, a glass wafer and an infrared light receiving element) can be obtained.
  • the thickness of the film-like transparent adhesive means the thickness of the whole film-like transparent adhesive, for example, the thickness of the film-like transparent adhesive consisting of a plurality of layers means the film-like transparent adhesive Means the total thickness of all the layers that make up.
  • the term "energy beam” means an electromagnetic wave or charged particle beam having energy quantum, and examples thereof include ultraviolet light, radiation, electron beam and the like.
  • the ultraviolet light can be irradiated, for example, by using a high pressure mercury lamp, a fusion H lamp, a xenon lamp, a black light or an LED lamp as an ultraviolet light source.
  • the electron beam can irradiate what was generated by the electron beam accelerator or the like.
  • energy ray curable means the property of curing by energy ray irradiation
  • non energy ray curable means the property of not curing even when energy ray is irradiated. Do.
  • thermosetting film-like transparent adhesive contains, for example, a polymer component and a thermosetting component. Those containing a polymer component, a thermosetting component and a filler are more preferred.
  • the polymer component is a component that can be considered to be formed by the polymerization reaction of the polymerizable compound.
  • the thermosetting component is a component that can be cured (i.e., polymerized) and reactive using heat as a reaction trigger.
  • the polymerization reaction also includes a polycondensation reaction.
  • thermosetting film-like transparent adhesive can be formed using a thermosetting adhesive composition containing its constituent material. For example, by applying a thermosetting adhesive composition on the surface to be formed of the thermosetting film-like transparent adhesive and drying it as necessary, it is possible to form a film-like transparent adhesive on a target site.
  • the ratio of the contents of the components which do not evaporate at normal temperature in the thermosetting adhesive composition is usually the same as the ratio of the contents of the components of the thermosetting transparent adhesive film.
  • “normal temperature” means a temperature which is not particularly cooled or heated, ie, a normal temperature, and includes, for example, a temperature of 15 to 25 ° C. and the like.
  • thermosetting adhesive composition may be applied by a known method, for example, an air knife coater, a blade coater, a bar coater, a gravure coater, a comma coater, a roll coater, a roll knife coater, a curtain coater, a die coater And methods using various coaters such as a knife coater, a screen coater, a Mayer bar coater, and a kiss coater.
  • a known method for example, an air knife coater, a blade coater, a bar coater, a gravure coater, a comma coater, a roll coater, a roll knife coater, a curtain coater, a die coater
  • various coaters such as a knife coater, a screen coater, a Mayer bar coater, and a kiss coater.
  • thermosetting adhesive composition contains a solvent described later
  • it is preferable to heat and dry and in this case, for example, 70 to It is preferable to dry at 130 ° C. for 10 seconds to 5 minutes.
  • thermosetting adhesive composition what contains a polymer component (a) and an epoxy-type thermosetting resin (b) is mentioned, for example. Each component will be described below.
  • the polymer component (a) is a component that can be considered to be formed by the polymerization reaction of the polymerizable compound, and imparts film forming ability, flexibility, and the like to the film-like transparent adhesive, and also adheres to a bonding object such as a glass wafer.
  • Polymer compound for improving the adhesion (stickability) of The polymer component (a) is also a component that does not correspond to the epoxy resin (b1) and the thermosetting agent (b2) described later.
  • thermosetting adhesive composition and the thermosetting film-like transparent adhesive may contain only one type, or two or more types, or a combination of two or more types of the polymer component (a). And the ratio can be selected arbitrarily.
  • polymer component (a) for example, acrylic resin (resin having a (meth) acryloyl group), polyester, urethane resin (that is, resin having a urethane bond), acrylic urethane resin, silicone resin (that is, The resin which has a siloxane bond, rubber-type resin (namely, resin which has a rubber structure), a phenoxy resin, a thermosetting polyimide etc. are mentioned, An acrylic resin is preferable.
  • the weight average molecular weight (Mw) of the acrylic resin is preferably 10,000 to 2,000,000, and more preferably 100,000 to 1,500,000.
  • Mw weight average molecular weight
  • the weight average molecular weight of the acrylic resin is at least the lower limit value, the shape stability of the film-like transparent adhesive (that is, the temporal stability during storage) is improved.
  • the weight average molecular weight of the acrylic resin is less than or equal to the upper limit value, the film-like transparent adhesive easily follows the uneven surface of the adherend, and voids etc. occur between the adherend and the film-like transparent adhesive Occurrence is more suppressed.
  • “weight-average molecular weight” is a polystyrene equivalent value measured by gel permeation chromatography (GPC) unless otherwise specified.
  • the glass transition temperature (Tg) of the acrylic resin is preferably ⁇ 60 to 70 ° C., and more preferably ⁇ 30 to 50 ° C.
  • the adhesive force of a film-like transparent adhesive and a support sheet is suppressed because Tg of acrylic resin is more than the above-mentioned lower limit, and separation from a support sheet of a glass wafer provided with a film-like transparent adhesive is more It becomes easy.
  • the adhesive force of a film-like transparent adhesive agent and a glass wafer improves because Tg of acrylic resin is below the said upper limit.
  • Examples of the (meth) acrylic acid ester constituting the acrylic resin include methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl (meth) acrylate, ) N-butyl acrylate, isobutyl (meth) acrylate, sec-butyl (meth) acrylate, tert-butyl (meth) acrylate, pentyl (meth) acrylate, hexyl (meth) acrylate, (meth) acrylic Heptyl acid, 2-ethylhexyl (meth) acrylate, isooctyl (meth) acrylate, n-octyl (meth) acrylate, n-nonyl (meth) acrylate, isononyl (meth) acrylate, decyl (meth) acrylate , (Meth) acrylic acid undecyl
  • (meth) acrylic acid is a concept including both “acrylic acid” and “methacrylic acid”.
  • (meth) acrylate is a concept including both “acrylate” and “methacrylate”
  • (meth) acryloyl group Is a concept including both "acryloyl group” and "methacryloyl group”.
  • the acrylic resin is, for example, one or more monomers selected from (meth) acrylic acid, itaconic acid, vinyl acetate, acrylonitrile, styrene, N-methylol acrylamide, etc. in addition to the (meth) acrylic acid ester. May be copolymerized.
  • the monomer constituting the acrylic resin may be only one type, or two or more types, and in the case of two or more types, the combination and ratio thereof can be arbitrarily selected.
  • the acrylic resin may have a functional group capable of binding to other compounds such as a vinyl group, a (meth) acryloyl group, an amino group, a carboxy group and an isocyanate group, in addition to the above-mentioned hydroxyl group.
  • These functional groups including the hydroxyl group of the acrylic resin may be bonded to another compound via a crosslinking agent (f) described later, or directly bonded to another compound without the crosslinking agent (f) It may be done.
  • a crosslinking agent (f) described later or directly bonded to another compound without the crosslinking agent (f) It may be done.
  • the reliability of the package obtained by using the film-like transparent adhesive improves by the acrylic resin being bonded to the other compound by the functional group.
  • thermoplastic resin other than an acrylic resin
  • thermoplastic resin may be used alone without using an acrylic resin. It may be used in combination with an acrylic resin.
  • thermoplastic resin it is easier to pull the glass wafer provided with the film-like transparent adhesive from the support sheet, or the film-like transparent adhesive can easily follow the uneven surface of the adherend, The occurrence of voids and the like may be further suppressed between the adherend and the film-like transparent adhesive.
  • the weight average molecular weight of the thermoplastic resin is preferably 1,000 to 100,000, and more preferably 3,000 to 80,000.
  • the glass transition temperature (Tg) of the thermoplastic resin is preferably ⁇ 30 to 150 ° C., and more preferably ⁇ 20 to 120 ° C.
  • thermoplastic resin examples include polyester, polyurethane, phenoxy resin, polybutene, polybutadiene, polystyrene and the like.
  • thermoplastic resin contained in the thermosetting adhesive composition and the film-like transparent adhesive may be only one type, or two or more types, and in the case of two or more types, the combination and ratio thereof are optionally It can be selected.
  • the ratio of the content of the polymer component (a) to the total content of all the components other than the solvent Is preferably 20 to 75% by mass, and more preferably 30 to 65% by mass, regardless of the type of the polymer component (a).
  • Epoxy-based thermosetting resin (b) The epoxy-based thermosetting resin (b) comprises an epoxy resin (b1) and a thermosetting agent (b2).
  • the epoxy-based thermosetting resin (b) contained in the thermosetting adhesive composition and the thermosetting transparent adhesive film may be only one type, or two or more types, and two or more types. Their combination and ratio can be selected arbitrarily.
  • Epoxy resin (b1) As an epoxy resin (b1), a well-known thing is mentioned, for example, a polyfunctional epoxy resin, a biphenyl compound, bisphenol A diglycidyl ether and its hydrogenated substance, an ortho cresol novolak epoxy resin, a dicyclopentadiene type epoxy resin, The bifunctional or more epoxy compound such as biphenyl type epoxy resin, bisphenol A type epoxy resin, bisphenol F type epoxy resin, phenylene skeleton type epoxy resin, etc. may be mentioned.
  • an epoxy resin having an unsaturated hydrocarbon group may be used as the epoxy resin (b1).
  • An epoxy resin having an unsaturated hydrocarbon group has higher compatibility with an acrylic resin than an epoxy resin having no unsaturated hydrocarbon group. Therefore, by using an epoxy resin having an unsaturated hydrocarbon group, the reliability of the package obtained using the film-like transparent adhesive is improved.
  • the compound formed by converting a part of epoxy group of polyfunctional epoxy resin into the group which has an unsaturated hydrocarbon group is mentioned, for example.
  • Such a compound can be obtained, for example, by addition reaction of (meth) acrylic acid or a derivative thereof to an epoxy group.
  • “derivative” means one in which one or more groups of the original compound are substituted with other groups (substituents).
  • the "group” includes not only an atomic group formed by combining a plurality of atoms, but also one atom.
  • the unsaturated hydrocarbon group is a polymerizable unsaturated group, and specific examples thereof include ethenyl group (vinyl group), 2-propenyl group (allyl group), (meth) acryloyl group, (meth) An acrylamide group etc. are mentioned and an acryloyl group is preferable.
  • the number average molecular weight of the epoxy resin (b1) is not particularly limited, it is 300 to 30000 in view of the curability of the film-like transparent adhesive and the strength and heat resistance of the film-like transparent adhesive after heat curing. Is preferable, 400 to 10000 is more preferable, and 500 to 3000 is particularly preferable.
  • the epoxy equivalent of the epoxy resin (b1) is preferably 100 to 1000 g / eq, and more preferably 150 to 800 g / eq.
  • the epoxy resin (b1) contained in the thermosetting adhesive composition and the thermosetting transparent adhesive film may be only one type, or two or more types, and in the case of two or more types, a combination thereof and The ratio can be selected arbitrarily.
  • Heat curing agent (b2) functions as a curing agent for the epoxy resin (b1).
  • a thermosetting agent (b2) the compound which has 2 or more of functional groups which can react with an epoxy group in 1 molecule is mentioned, for example.
  • the functional group include a phenolic hydroxyl group, an alcoholic hydroxyl group, an amino group, a carboxy group, and a group in which an acid group is anhydrated, and the phenolic hydroxyl group, an amino group, or an acid group is anhydrated. It is preferably a group, more preferably a phenolic hydroxyl group or an amino group.
  • thermosetting agents (b2) examples of amine-based curing agents having an amino group include dicyandiamide (DICY) and the like.
  • the thermosetting agent (b2) may have an unsaturated hydrocarbon group.
  • the thermosetting agent (b2) having an unsaturated hydrocarbon group for example, a compound obtained by substituting a part of hydroxyl groups of a phenol resin with a group having an unsaturated hydrocarbon group, an aromatic ring of a phenol resin, The compound etc. which a group which has a saturated hydrocarbon group directly couple
  • bonds are mentioned.
  • the unsaturated hydrocarbon group in the thermosetting agent (b2) is the same as the unsaturated hydrocarbon group in the above-mentioned epoxy resin having an unsaturated hydrocarbon group.
  • the heat curing agent (b2) When a phenol-based curing agent is used as the heat curing agent (b2), the heat curing agent (b2) preferably has a high softening point or glass transition temperature.
  • thermosetting agents (b2) for example, the number average molecular weight of resin components such as polyfunctional phenol resin, novolak type phenol resin, dicyclopentadiene type phenol resin, and aralkyl type phenol resin is preferably 300 to 30,000. And 400 to 10000 are more preferable, and 500 to 3000 are particularly preferable.
  • the molecular weight of the non-resin component such as biphenol and dicyandiamide is not particularly limited, but is preferably 60 to 500, for example.
  • thermosetting adhesive (b2) contained in the thermosetting adhesive composition and the thermosetting transparent adhesive film may be only one type, or two or more types, and in the case of two or more types, a combination thereof. And the ratio can be selected arbitrarily.
  • the content of the thermosetting agent (b2) is 0.1 to 500 parts by mass with respect to 100 parts by mass of the epoxy resin (b1). It is preferably part, and more preferably 1 to 200 parts by mass.
  • the content of the thermosetting agent (b2) is equal to or more than the lower limit value, curing of the film-like transparent adhesive can be more easily progressed.
  • the content of the thermosetting agent (b2) is less than or equal to the upper limit value, the moisture absorption rate of the film-like transparent adhesive is reduced, and the reliability of the package obtained using the film-like transparent adhesive is more improves.
  • the content of the epoxy-based thermosetting resin (b) (total content of the epoxy resin (b1) and the thermosetting agent (b2)) is The content is preferably 5 to 100 parts by mass, more preferably 6 to 90 parts by mass, and particularly preferably 7 to 80 parts by mass with respect to 100 parts by mass of the polymer component (a). .
  • thermosetting transparent adhesive film other than the polymer component (a) and the epoxy-based thermosetting resin (b), if necessary, other non-thermosetting transparent adhesives may be used. You may contain the component.
  • the other components contained in the thermosetting transparent adhesive film preferred are, for example, a curing accelerator (c), a filler (d), a coupling agent (e), a crosslinking agent (f), an energy ray A curable resin (g), a photoinitiator (h), a general purpose additive (i), etc. are mentioned.
  • the curing accelerator (c) is a component for adjusting the curing rate of the thermosetting adhesive composition.
  • Preferred curing accelerators (c) include, for example, tertiary amines such as triethylenediamine, benzyldimethylamine, triethanolamine, dimethylaminoethanol and tris (dimethylaminomethyl) phenol; 2-methylimidazole, 2-phenylimidazole Imidazoles such as 2-phenyl-4-methylimidazole, 2-phenyl-4,5-dihydroxymethylimidazole, 2-phenyl-4-methyl-5-hydroxymethylimidazole (one or more hydrogen atoms are not hydrogen atoms Imidazoles substituted with the following groups: organic phosphines such as tributyl phosphine, diphenyl phosphine, triphenyl phosphine (phosphines in which one or more hydrogen atoms are substituted with an organic group); tetrapheny
  • the curing accelerator (c) contained in the thermosetting adhesive composition and the thermosetting transparent adhesive film may be only one type, or two or more types, and in the case of two or more types, a combination thereof. And the ratio can be selected arbitrarily.
  • the content of the curing accelerator (c) is the content of the epoxy-based thermosetting resin (b)
  • the amount is preferably 0.01 to 10 parts by mass, and more preferably 0.1 to 5 parts by mass with respect to 100 parts by mass.
  • the effect by using a hardening accelerator (c) is acquired more notably by the said content of a hardening accelerator (c) being more than the said lower limit.
  • a high-polarity curing accelerator (c) may form an adherend in a film-like transparent adhesive under high temperature and high humidity conditions. The effect of suppressing migration and segregation to the adhesive interface side is enhanced, and the reliability of the infrared sensor module obtained using the film-like transparent adhesive is further improved.
  • thermosetting film-like transparent adhesive containing the filler (d) makes it easy to adjust the coefficient of thermal expansion, and the coefficient of thermal expansion relative to the object to which the thermosetting film-like transparent adhesive is attached By optimizing the structure, the reliability of the package obtained by using the thermosetting film-like transparent adhesive is further improved.
  • the thermosetting film-like transparent adhesive contains the filler (d)
  • the moisture absorption of the film-like transparent adhesive after curing can be reduced, or the heat dissipation can be improved.
  • the filler (d) may be either an organic filler or an inorganic filler.
  • an organic filler an acryl particle, a silicone particle, etc. are mentioned, for example. Among them, acrylic particles are preferable from the viewpoint of light transparency and compatibility with other materials.
  • Preferred inorganic fillers include, for example, powders of silica, alumina, talc, calcium carbonate, titanium white, bengala, silicon carbide, boron nitride, etc .; spherical beads of these inorganic fillers; surface modification of these inorganic fillers Articles: single crystal fibers of these inorganic fillers; glass fibers and the like.
  • the inorganic filler is preferably silica or alumina, and more preferably spherical silica.
  • thermosetting adhesive composition and the thermosetting film-like transparent adhesive may contain only one filler, or two or more fillers, and in the case of two or more, a combination thereof and The ratio can be selected arbitrarily.
  • the average particle diameter of the acrylic fine particles is preferably 1 to 450 nm, and more preferably 1 to 400 nm.
  • the average particle diameter of the spherical silica is preferably 1 to 250 nm, and more preferably 5 to 200 nm.
  • the ratio of the content of the filler (d) to the total content of all components other than the solvent in the thermosetting adhesive composition that is, the filler of the film-like transparent adhesive
  • the content of (d) is preferably 5 to 80% by mass, and more preferably 7 to 60% by mass. When the content of the filler (d) is in such a range, the adjustment of the thermal expansion coefficient becomes easier.
  • the film-like transparent adhesive improves the adhesion and adhesion to the adherend by containing the coupling agent (e).
  • the film-like transparent adhesive contains the coupling agent (e)
  • the cured product is improved in water resistance without impairing the heat resistance.
  • the coupling agent (e) is one having a functional group capable of reacting with an inorganic compound or an organic compound.
  • the coupling agent (e) is preferably a compound having a functional group capable of reacting with the functional group possessed by the polymer component (a), the epoxy thermosetting resin (b), etc., and is a silane coupling agent. Is more preferred.
  • Preferred examples of the silane coupling agent include 3-glycidyloxypropyltrimethoxysilane, 3-glycidyloxypropylmethyldiethoxysilane, 3-glycidyloxypropyltriethoxysilane, 3-glycidyloxymethyldiethoxysilane, 2- (3,4-Epoxycyclohexyl) ethyltrimethoxysilane, 3-methacryloyloxypropyltrimethoxysilane, 3-aminopropyltrimethoxysilane, 3- (2-aminoethylamino) propyltrimethoxysilane, 3- (2-amino) Ethylamino) propylmethyldiethoxysilane
  • thermosetting adhesive composition and the thermosetting film-like transparent adhesive may contain only one type of coupling agent, or two or more types, or a combination of two or more types. And the ratio can be selected arbitrarily.
  • the content of the coupling agent (e) is the polymer component (a) and an epoxy-based thermosetting resin Is preferably 0.03 to 20 parts by mass, more preferably 0.05 to 10 parts by mass, and 0.1 to 5 parts by mass with respect to 100 parts by mass of the total content of the hydrophobic resin (b) Is particularly preferred.
  • the content of the coupling agent (e) is equal to or more than the lower limit value, the dispersibility of the filler (d) in the resin is improved, and the adhesion of the thermosetting film transparent adhesive to the adherend
  • the effect by using the coupling agent (e) such as the improvement of the property can be more significantly obtained.
  • the content of the coupling agent (e) being equal to or less than the upper limit value, generation of outgassing is further suppressed.
  • thermosetting adhesive composition and the thermosetting transparent adhesive film may contain a crosslinking agent (f) for binding the above-mentioned functional group to another compound and crosslinking the same.
  • crosslinking agent (f) examples include organic polyvalent isocyanate compounds, organic polyvalent imine compounds, metal chelate type crosslinking agents (crosslinking agents having a metal chelate structure), aziridine type crosslinking agents (crosslinking agents having an aziridinyl group), etc. Can be mentioned.
  • organic polyvalent isocyanate compound for example, an aromatic polyvalent isocyanate compound, an aliphatic polyvalent isocyanate compound and an alicyclic polyvalent isocyanate compound (hereinafter, these compounds are collectively referred to as “aromatic polyvalent isocyanate compound etc.” Abbreviated in some cases); trimers such as the above-mentioned aromatic polyvalent isocyanate compounds, isocyanurates and adducts; terminal isocyanate urethane prepolymers obtained by reacting the above-mentioned aromatic polyvalent isocyanate compounds and the like with a polyol compound Etc.
  • aromatic polyvalent isocyanate compound etc Abbreviated in some cases
  • trimers such as the above-mentioned aromatic polyvalent isocyanate compounds, isocyanurates and adducts
  • terminal isocyanate urethane prepolymers obtained by reacting the above-mentioned aromatic polyvalent isocyanate compounds and the like with a polyol compound Et
  • the “adduct” includes the above-mentioned aromatic polyvalent isocyanate compound, aliphatic polyvalent isocyanate compound or alicyclic polyvalent isocyanate compound, and low contents such as ethylene glycol, propylene glycol, neopentyl glycol, trimethylolpropane or castor oil It means a reaction product with a molecule active hydrogen-containing compound, and examples thereof include xylylene diisocyanate adduct of trimethylolpropane as described later, and the like.
  • the "terminal isocyanate urethane prepolymer" is as described above.
  • organic polyvalent isocyanate compound for example, 2,4-tolylene diisocyanate; 2,6-tolylene diisocyanate; 1,3-xylylene diisocyanate; 1,4-xylene diisocyanate; diphenylmethane-4 Diphenylmethane-2,4'-diisocyanate; 3-methyldiphenylmethane diisocyanate; hexamethylene diisocyanate; isophorone diisocyanate; dicyclohexylmethane-4,4'-diisocyanate; dicyclohexylmethane-2,4'-diisocyanate; trimethylol Any one of tolylene diisocyanate, hexamethylene diisocyanate and xylylene diisocyanate in the hydroxyl groups of all or part of a polyol such as propane Or two or more compounds are added; lysine diisocyanate.
  • a polyol such as propane Or two or
  • organic polyhydric imine compound examples include N, N′-diphenylmethane-4,4′-bis (1-aziridinecarboxamide), trimethylolpropane-tri- ⁇ -aziridinyl propionate, and tetramethylolmethane.
  • an organic polyhydric isocyanate compound as a crosslinking agent (f)
  • a hydroxyl-containing polymer as a polymer component (a).
  • the crosslinker (f) has an isocyanate group and the polymer component (a) has a hydroxyl group
  • the crosslinker (f) reacts with the polymer component (a) to form a crosslinked structure in the transparent adhesive film. It can be introduced easily.
  • the crosslinking agent (f) contained in the thermosetting adhesive composition and the thermosetting transparent adhesive film may be only one type, or two or more types, and in the case of two or more types, a combination thereof and The ratio can be selected arbitrarily.
  • the content of the crosslinking agent (f) in the thermosetting adhesive composition is 0.01 to 20 parts by mass with respect to 100 parts by mass of the polymer component (a). It is preferably part, more preferably 0.1 to 10 parts by mass, and particularly preferably 0.3 to 5 parts by mass.
  • the content of the crosslinking agent (f) is equal to or more than the lower limit value, the effect of using the crosslinking agent (f) can be more remarkably obtained.
  • the said content of a crosslinking agent (f) being below the said upper limit, the excess use of a crosslinking agent (f) is suppressed.
  • the film-like transparent adhesive contains the energy ray-curable resin (g), so that the characteristics can be changed by the irradiation of energy rays.
  • the energy ray-curable resin (g) is obtained by polymerizing (curing) an energy ray-curable compound.
  • the energy ray curable compound include a compound having at least one polymerizable double bond in the molecule, and an acrylate compound having a (meth) acryloyl group is preferable.
  • acrylate compound examples include trimethylolpropane tri (meth) acrylate, tetramethylolmethane tetra (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, and dipentaerythritol monohydroxy penta
  • Linear aliphatic skeleton-containing (meth) acrylates such as meta) acrylate, dipentaerythritol hexa (meth) acrylate, 1,4-butylene glycol di (meth) acrylate, 1,6-hexanediol di (meth) acrylate; Cycloaliphatic skeleton-containing (meth) acrylates such as cyclopentanyl di (meth) acrylate; polyalkylene glycol (meth) acrylates such as polyethylene glycol di (meth) acrylate Oligoester (meth)
  • the weight average molecular weight of the energy ray curable resin (g) is preferably 100 to 30,000, and more preferably 300 to 10,000.
  • the energy ray-curable resin (g) contained in the thermosetting adhesive composition may be only one type, or two or more types, and in the case of two or more types, the combination and ratio thereof can be arbitrarily selected. .
  • the content of the energy ray-curable resin (g) in the thermosetting adhesive composition is preferably 1 to 95% by mass, and 1.5 to 90 The content is more preferably in the range of 2% to 85% by mass.
  • thermosetting adhesive composition contains the energy ray-curable resin (g), it contains a photopolymerization initiator (h) in order to efficiently promote the polymerization reaction of the energy ray-curable resin (g) It may be
  • thermosetting adhesive composition for example, benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, benzoin benzoic acid, methyl benzoin benzoate, benzoin dimethyl ketal Benzoin compounds such as acetophenone; acetophenone compounds such as acetophenone, 2-hydroxy-2-methyl-1-phenyl-propan-1-one, 2,2-dimethoxy-1,2-diphenylethan-1-one; bis (2,2, Acyl phosphine oxide compounds such as 4,6-trimethyl benzoyl) phenyl phosphine oxide, 2,4,6-trimethyl benzoyl diphenyl phosphine oxide; benzyl phenyl sulfide, tetramethyl thiuram Sulfide compounds such as nosulfide; ⁇ -ketol compounds such as
  • the photopolymerization initiator (h) contained in the thermosetting adhesive composition may be only one type, or two or more types, and in the case of two or more types, the combination and ratio thereof can be arbitrarily selected.
  • the content of the photopolymerization initiator (h) in the thermosetting adhesive composition is 100 parts by mass of the content of the energy ray-curable resin (g),
  • the amount is preferably 0.1 to 20 parts by mass, more preferably 1 to 10 parts by mass, and particularly preferably 2 to 5 parts by mass.
  • the general-purpose additive (I) may be a known one, can be optionally selected according to the purpose, and is not particularly limited. Preferred examples thereof include a plasticizer, an antistatic agent, an antioxidant, and a colorant (dye , Pigments), gettering agents and the like.
  • the heat-curable adhesive composition and the general-purpose additive (i) contained in the heat-curable film-like transparent adhesive may be only one type, or two or more types, and in the case of two or more types, a combination thereof And the ratio can be selected arbitrarily.
  • the content of the thermosetting adhesive composition and the thermosetting film-like transparent adhesive is not particularly limited, and may be appropriately selected according to the purpose.
  • the content of the polymer component (a) is improved in that the film forming property is improved, for example, the surface condition of the film-like transparent adhesive is improved.
  • the total amount of the polymer component (a), the epoxy-based thermosetting resin (b) and the filler (d) (polymer component (a), epoxy resin (b1), thermosetting agent (b2) and It is preferable that it is 30 mass parts or more with respect to 100 mass parts of total content of a filler (d), and it is more preferable that it is 38 mass parts or more.
  • the upper limit of the said content of a polymer component (a) is not specifically limited by the above-mentioned point, It is preferable that it is 65 mass parts.
  • the content of the polymer component (a) is the polymer component (a) in that the reliability of the film-like transparent adhesive is improved.
  • a) Total content of epoxy-based thermosetting resin (b) and filler (d) that is, polymer component (a), epoxy resin (b1), thermosetting agent (b2) and filler (d) It is preferable that it is 45 mass parts or more with respect to 100 mass parts of (total content of).
  • the upper limit of the said content of a polymer component (a) is not specifically limited by the above-mentioned point, It is preferable that it is 65 mass parts.
  • the thermosetting adhesive composition preferably further contains a solvent.
  • the thermosetting adhesive composition containing a solvent has good handleability.
  • the solvent is not particularly limited, but preferred examples thereof include hydrocarbons such as toluene and xylene; alcohols such as methanol, ethanol, 2-propanol, isobutyl alcohol (2-methylpropan-1-ol), 1-butanol and the like Esters such as ethyl acetate; ketones such as acetone and methyl ethyl ketone; ethers such as tetrahydrofuran; and amides such as dimethylformamide and N-methyl pyrrolidone (that is, compounds having an amide bond).
  • the solvent contained in the adhesive composition may be only one type, or two or more types, and in the case of two or more types, the combination and ratio thereof can be arbitrarily selected.
  • the solvent contained in the thermosetting adhesive composition is preferably methyl ethyl ketone or the like in that the components contained in the thermosetting adhesive composition can be mixed more uniformly.
  • thermosetting adhesive composition is obtained by blending each component for constituting this. There is no particular limitation on the order of addition of each component at the time of blending, and two or more components may be added simultaneously.
  • a solvent it may be used by mixing the solvent with any compounding component other than the solvent and diluting this compounding component in advance, or by previously diluting any compounding component other than the solvent A solvent may be used by mixing with these compounding ingredients without storage.
  • the method of mixing each component at the time of compounding is not particularly limited, and a method of mixing by rotating a stirrer or a stirring blade, etc .; a method of mixing using a mixer; a method of adding ultrasonic waves and mixing, etc. It may be selected as appropriate.
  • the temperature and time of addition and mixing of the respective components are not particularly limited as long as the respective blended components do not deteriorate, and may be appropriately adjusted, but the temperature is preferably 15 to 30 ° C.
  • the energy ray-curable film-like transparent adhesive contains an energy ray-curable component (a).
  • the thing containing an energy ray curable component (a) and a filler is preferable.
  • the energy ray-curable component (a) is preferably uncured, preferably has tackiness, and is more preferably uncured and tacky.
  • energy ray and “energy ray curability" are as described above.
  • the curing conditions for curing are such that the cured product has a curing degree sufficient to exhibit its function.
  • the illuminance of energy rays at the time of curing of the energy ray-curable film-like transparent adhesive is preferably 120 to 280 mW / cm 2 .
  • the light quantity of the energy ray at the time of curing is preferably 100 to 1000 mJ / cm 2 .
  • the energy ray-curable film-like transparent adhesive can be formed using an energy ray-curable adhesive composition containing its constituent material.
  • the energy beam curable adhesive composition is applied to the surface to be formed of the energy beam curable film transparent adhesive, and dried if necessary, the energy beam curable film transparent on the target site It can form an adhesive.
  • the application of the energy ray-curable adhesive composition can be performed, for example, in the same manner as in the case of the application of the thermosetting adhesive composition described above.
  • the drying conditions of the energy ray-curable adhesive composition are not particularly limited, but when the energy ray-curable adhesive composition contains a solvent described later, it is preferable to heat and dry.
  • the solvent-containing energy ray curable adhesive composition is preferably dried, for example, at 70 to 130 ° C. for 10 seconds to 5 minutes. However, in the present invention, it is preferable to dry the energy ray-curable adhesive composition so that the formed energy ray-curable film-like transparent adhesive does not thermally cure.
  • an energy ray-curable adhesive composition (IV-1) containing the energy ray-curable component (a) and a filler which may be abbreviated as “Composition (IV-1)”.
  • the energy ray curable component (a) is a component that cures upon irradiation with energy rays, and imparts film forming ability, flexibility, etc. to the energy ray curable film-like transparent adhesive, and it is hard and transparent after curing. It is also a component for forming a resin film.
  • the energy ray curable component (a) includes, for example, an energy ray curable group, a polymer (a1) having a weight average molecular weight of 80000 to 2,000,000, and an energy ray curable group having a molecular weight of 100 to 80,000. Compound (a2) is mentioned.
  • the polymer (a1) may be at least partially crosslinked by a crosslinking agent, or may be non-crosslinked.
  • the polymer (a1) having an energy ray curable group and having a weight average molecular weight of 80,000 to 2,000,000 include an acrylic polymer (a11) having a functional group capable of reacting with a group possessed by another compound, Acrylic resin (a1-1) formed by reaction of an energy ray curable compound (a12) having a group reactive with a functional group and an energy ray curable group such as an energy ray curable double bond .
  • Examples of the functional group capable of reacting with a group contained in another compound include, for example, a hydroxyl group, a carboxy group, an amino group, and a substituted amino group (that is, one or two hydrogen atoms of the amino group are groups other than a hydrogen atom).
  • a substituted group an epoxy group and the like.
  • the functional group is preferably a group other than a carboxy group.
  • the functional group is preferably a hydroxyl group.
  • Acrylic polymers having functional groups (a11) examples include those obtained by copolymerizing an acrylic monomer having the functional group and an acrylic monomer having no functional group. In addition to the monomers, monomers other than acrylic monomers (that is, non-acrylic monomers) may be copolymerized.
  • the acrylic polymer (a11) may be a random copolymer or a block copolymer, and any known polymerization method may be employed.
  • a hydroxyl-containing monomer a carboxy-group containing monomer, an amino-group containing monomer, a substituted amino-group containing monomer, an epoxy-group containing monomer etc. are mentioned, for example.
  • hydroxyl group-containing monomer examples include hydroxymethyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 3-hydroxypropyl (meth) acrylate, (meth) Hydroxyalkyl (meth) acrylates such as 2-hydroxybutyl acrylate, 3-hydroxybutyl (meth) acrylate and 4-hydroxybutyl (meth) acrylate; non (meth) acrylics such as vinyl alcohol and allyl alcohol A saturated alcohol (unsaturated alcohol which does not have a (meth) acryloyl frame) etc. are mentioned.
  • carboxy group-containing monomer examples include ethylenically unsaturated monocarboxylic acids such as (meth) acrylic acid and crotonic acid (that is, monocarboxylic acids having an ethylenically unsaturated bond); fumaric acid, itaconic acid and maleic acid And ethylenically unsaturated dicarboxylic acids such as citraconic acid (dicarboxylic acids having an ethylenically unsaturated bond); anhydrides of the above ethylenically unsaturated dicarboxylic acids; (meth) acrylic acid carboxyalkyl esters such as 2-carboxyethyl methacrylate and the like Can be mentioned.
  • monocarboxylic acids such as (meth) acrylic acid and crotonic acid (that is, monocarboxylic acids having an ethylenically unsaturated bond); fumaric acid, itaconic acid and maleic acid
  • the acrylic monomer having a functional group is preferably a hydroxyl group-containing monomer.
  • the acrylic monomer having the functional group constituting the acrylic polymer (a11) may be only one type, or two or more types, and in the case of two or more types, the combination and ratio thereof are optionally It can be selected.
  • acrylic monomer having no functional group examples include methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl (meth) acrylate and n (meth) acrylate -Butyl, isobutyl (meth) acrylate, sec-butyl (meth) acrylate, tert-butyl (meth) acrylate, pentyl (meth) acrylate, hexyl (meth) acrylate, heptyl (meth) acrylate ( 2-ethylhexyl acrylate, isooctyl (meth) acrylate, n-octyl (meth) acrylate, n-nonyl (meth) acrylate, isononyl (meth) acrylate, decyl (meth) acrylate, (meth) Undecyl acrylate, dodec
  • acrylic monomer having no functional group examples include alkoxyalkyl groups such as methoxymethyl (meth) acrylate, methoxyethyl (meth) acrylate, ethoxymethyl (meth) acrylate, and ethoxyethyl (meth) acrylate.
  • (meth) acrylic acid ester Containing (meth) acrylic acid ester; (meth) acrylic acid aryl ester such as phenyl (meth) acrylate etc., (meth) acrylic acid ester having an aromatic group; non-crosslinkable (meth) acrylamide and derivatives thereof And (meth) acrylic acid esters having a non-crosslinkable tertiary amino group such as N, N-dimethylaminoethyl (meth) acrylate and N, N-dimethylaminopropyl (meth) acrylate.
  • the acrylic monomer having no functional group constituting the acrylic polymer (a11) may be only one type, or two or more types, and in the case of two or more types, the combination and ratio thereof are arbitrary. Can be selected.
  • non-acrylic monomers examples include olefins such as ethylene and norbornene; vinyl acetate; styrene and the like.
  • the non-acrylic monomer constituting the acrylic polymer (a11) may be only one type, or two or more types, and in the case of two or more types, the combination and ratio thereof can be arbitrarily selected.
  • the ratio (content) of the amount of the structural unit derived from the acrylic monomer having the functional group to the total amount of the structural units constituting the same is 0.1 to 50 mass % Is preferable, 1 to 40% by mass is more preferable, and 3 to 30% by mass is particularly preferable.
  • the ratio is in such a range, in the acrylic resin (a1-1) obtained by the copolymerization of the acrylic polymer (a11) and the energy ray curable compound (a12), energy The content of the linear curable group can be easily adjusted to the preferable range of the degree of curing of the transparent resin film.
  • the acrylic polymer (a11) constituting the acrylic resin (a1-1) may be only one type, or two or more types, and in the case of two or more types, the combination and ratio thereof are optionally It can be selected.
  • the ratio of the content of the acrylic resin (a1-1) to the total content of the components other than the solvent is preferably 1 to 70% by mass, more preferably 5 to 60% by mass, and particularly preferably 10 to 50% by mass.
  • the energy ray curable compound (a12) is one or two selected from the group consisting of an isocyanate group, an epoxy group and a carboxy group as a group capable of reacting with the functional group possessed by the acrylic polymer (a11) What has the above is preferable, and what has an isocyanate group as said group is more preferable.
  • the energy beam curable compound (a12) has, for example, an isocyanate group as the group, the isocyanate group easily reacts with the hydroxyl group of the acrylic polymer (a11) having a hydroxyl group as the functional group.
  • the energy ray curable compound (a12) preferably has 1 to 5, and more preferably 1 to 3 of the energy ray curable groups in one molecule.
  • Examples of the energy ray curable compound (a12) include 2-methacryloyloxyethyl isocyanate, meta-isopropenyl- ⁇ , ⁇ -dimethylbenzyl isocyanate, methacryloyl isocyanate, allyl isocyanate, 1,1- (bisacryloyloxymethyl) Ethyl isocyanate; Acryloyl monoisocyanate compounds obtained by the reaction of diisocyanate compounds or polyisocyanate compounds with hydroxyethyl (meth) acrylate; The acryloyl monoisocyanate compound etc.
  • the energy ray curable compound (a12) is preferably 2-methacryloyloxyethyl isocyanate.
  • the energy beam curable compound (a12) constituting the acrylic resin (a1-1) may be only one type, or two or more types, and in the case of two or more types, the combination and ratio thereof are arbitrary. Can be selected.
  • the content of the energy ray curable group derived from the energy ray curable compound (a12) relative to the content of the functional group derived from the acrylic polymer (a11) The proportion of is preferably 20 to 120 mol%, more preferably 35 to 100 mol%, and particularly preferably 50 to 100 mol%.
  • the adhesive force of the transparent resin film after hardening becomes larger because the ratio of the said content is such a range.
  • the upper limit of the content ratio is 100 mol%, but the energy ray In the case where the curable compound (a12) is a polyfunctional compound (having two or more of the groups in one molecule), the upper limit of the content ratio may exceed 100 mol%.
  • the weight average molecular weight (Mw) of the polymer (a1) is preferably 100,000 to 2,000,000, and more preferably 300,000 to 1,500,000.
  • the "weight average molecular weight” is as described above.
  • the polymer (a1) is at least a part of which is crosslinked by a crosslinking agent
  • the monomer which does not correspond to any of the monomers and which has a group reactive with the crosslinking agent may be polymerized to be crosslinked in the group reactive with the crosslinking agent, or the energy ray curable compound ( The group derived from a12), which is reactive with the functional group, may be crosslinked.
  • the polymer (a1) contained in the composition (IV-1) and the energy ray-curable film-like transparent adhesive may be only one type, or two or more types, and in the case of two or more types, Combinations and ratios can be selected arbitrarily.
  • Compound (a2) having a molecular weight of 100 to 80,000, having an energy ray-curable group examples include a group containing an energy ray curable double bond, and preferred are (meth) An acryloyl group, a vinyl group, etc. are mentioned.
  • the compound (a2) is not particularly limited as long as it satisfies the above conditions, but a low molecular weight compound having an energy ray curable group, an epoxy resin having an energy ray curable group, and an energy ray curable group A phenol resin etc. are mentioned.
  • a low molecular weight compound which has an energy ray curable group among the said compounds (a2) a polyfunctional monomer, an oligomer, etc. are mentioned, for example,
  • the acrylate type compound which has a (meth) acryloyl group is preferable.
  • the acrylate compound examples include 2-hydroxy-3- (meth) acryloyloxypropyl methacrylate, polyethylene glycol di (meth) acrylate, propoxylated ethoxylated bisphenol A di (meth) acrylate, and 2,2-bis [4 -((Meth) acryloxypolyethoxy) phenyl] propane, ethoxylated bisphenol A di (meth) acrylate, 2,2-bis [4-((meth) acryloxydiethoxy) phenyl] propane, 9,9-bis [4- (2- (Meth) acryloyloxyethoxy) phenyl] fluorene, 2,2-bis [4-((meth) acryloxypolypropoxy) phenyl] propane, tricyclodecanedimethanol di (meth) acrylate, 1 , 10-Decanediol di (meth) acrylate 1,6-hexanediol di (meth) acrylate, 1,9
  • an epoxy resin having an energy ray-curable group and a phenol resin having an energy ray-curable group are described, for example, in paragraph 0043 of "JP-A-2013-194102" and the like. The thing can be used.
  • Such a resin also corresponds to a resin constituting a thermosetting component described later, but in the present invention, it is treated as the compound (a2).
  • the weight average molecular weight of the compound (a2) is preferably 100 to 30,000, and more preferably 300 to 10,000.
  • the compound (a2) contained in the composition (IV-1) and the energy ray-curable film-like transparent adhesive may be only one type, or two or more types, and in the case of two or more types, a combination thereof And the ratio can be selected arbitrarily.
  • composition (IV-1) and the energy ray-curable film-like transparent adhesive contain the compound (a2) as the energy ray-curable component (a), a polymer having no energy ray-curable group is further contained. It is preferable to also contain (b).
  • the polymer (b) may be at least partially crosslinked by a crosslinking agent, or may be non-crosslinked.
  • polymer (b) having no energy ray curable group examples include acrylic polymers, phenoxy resins, urethane resins, polyesters, rubber resins, acrylic urethane resins, and the like.
  • the polymer (b) is preferably an acrylic polymer (hereinafter sometimes abbreviated as “acrylic polymer (b-1)”).
  • the acrylic polymer (b-1) may be a known one, for example, may be a homopolymer of one acrylic monomer, or a copolymer of two or more acrylic monomers, It may also be a copolymer of one or more acrylic monomers and a monomer (non-acrylic monomer) other than one or more acrylic monomers.
  • acrylic monomer constituting the acrylic polymer (b-1) examples include (meth) acrylic acid alkyl ester, (meth) acrylic acid ester having a cyclic skeleton, glycidyl group-containing (meth) acrylic acid ester, Examples thereof include hydroxyl group-containing (meth) acrylic acid esters and substituted amino group-containing (meth) acrylic acid esters.
  • substituted amino group is as described above.
  • Examples of the (meth) acrylic acid alkyl ester include methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl (meth) acrylate, n- (meth) acrylate Butyl, isobutyl (meth) acrylate, sec-butyl (meth) acrylate, tert-butyl (meth) acrylate, pentyl (meth) acrylate, hexyl (meth) acrylate, heptyl (meth) acrylate, (meth) acrylate ) 2-ethylhexyl acrylate, isooctyl (meth) acrylate, n-octyl (meth) acrylate, n-nonyl (meth) acrylate, isononyl (meth) acrylate, decyl (meth) acrylate, (meth
  • Examples of the (meth) acrylic acid ester having a cyclic skeleton include (meth) acrylic acid cycloalkyl esters such as (meth) acrylic acid isobornyl and (meth) acrylic acid dicyclopentanyl; (Meth) acrylic acid aralkyl esters such as benzyl (meth) acrylate; (Meth) acrylic acid cycloalkenyl esters such as (meth) acrylic acid dicyclopentenyl ester; Examples include (meth) acrylic acid cycloalkenyloxyalkyl esters such as (meth) acrylic acid dicyclopentenyl oxyethyl ester and the like.
  • glycidyl group containing (meth) acrylic acid ester glycidyl (meth) acrylate etc.
  • hydroxyl group-containing (meth) acrylic acid ester examples include hydroxymethyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 3-hydroxy (meth) acrylate Propyl, 2-hydroxybutyl (meth) acrylate, 3-hydroxybutyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate and the like can be mentioned.
  • substituted amino group-containing (meth) acrylic acid ester examples include N-methylaminoethyl (meth) acrylate and the like.
  • non-acrylic monomer constituting the acrylic polymer (b-1) examples include olefins such as ethylene and norbornene; vinyl acetate; styrene and the like.
  • the polymer (b) having no energy ray-curable group at least partially crosslinked by a crosslinking agent for example, one having a reactive functional group in the polymer (b) reacted with the crosslinking agent
  • the reactive functional group may be appropriately selected depending on the type of the crosslinking agent and the like, and is not particularly limited.
  • the crosslinking agent is a polyisocyanate compound
  • examples of the reactive functional group include a hydroxyl group, a carboxy group and an amino group. Among these, a hydroxyl group having high reactivity with the isocyanate group is preferable.
  • the crosslinking agent is an epoxy compound
  • examples of the reactive functional group include a carboxy group, an amino group and an amide group. Among these, a carboxy group having high reactivity with the epoxy group is preferable.
  • the reactive functional group is a group other than a carboxy group in terms of preventing corrosion of the circuit of the semiconductor wafer or the semiconductor chip.
  • the thing obtained by polymerizing the monomer which has at least the said reactive functional group is mentioned, for example.
  • the acrylic polymer (b-1) those having the reactive functional group as one or both of the acrylic monomer and the non-acrylic monomer mentioned as the monomer constituting the polymer It may be used.
  • the polymer (b) having a hydroxyl group as a reactive functional group include, for example, those obtained by polymerizing a hydroxyl group-containing (meth) acrylic acid ester.
  • acrylic monomers or non-acrylic monomers those obtained by polymerizing monomers in which one or more hydrogen atoms are substituted by the reactive functional group are mentioned.
  • the ratio (content) of the amount of the structural unit derived from the monomer having the reactive functional group to the total amount of the constituent units constituting the polymer is 1 to 20 It is preferably mass%, more preferably 2 to 10 mass%.
  • the ratio is in such a range, in the polymer (b), the degree of crosslinking becomes a more preferable range.
  • the weight average molecular weight (Mw) of the polymer (b) having no energy ray-curable group is preferably 10,000 to 2,000,000 from the viewpoint that the film forming property of the composition (IV-1) is further improved. More preferably, it is 100000 to 1.500000.
  • the "weight average molecular weight" is as described above.
  • the polymer (b) having no energy ray-curable group, which is contained in the composition (IV-1) and the energy ray-curable film-like transparent adhesive may be only one type or two or more types; When it is species or more, their combination and ratio can be arbitrarily selected.
  • composition (IV-1) those containing one or both of the polymer (a1) and the compound (a2) can be mentioned. And when it contains the said compound (a2), it is preferable that a composition (IV-1) also contains the polymer (b) which does not have an energy ray curable group, and, in this case, it further contains the said (a1) It is also preferable to contain
  • the composition (IV-1) may contain neither the compound (a2) but the polymer (a1) and the polymer (b) having no energy ray curable group.
  • the composition (IV-1) contains the polymer (a1), the compound (a2) and the polymer (b) having no energy ray curable group
  • the composition (IV-1) contains the polymer
  • the content of the compound (a2) is preferably 10 to 400 parts by mass with respect to 100 parts by mass of the total content of the polymer (a1) and the polymer (b) having no energy ray curable group. And 30 to 350 parts by mass are more preferable.
  • the ratio of the total content of the energy ray-curable component (a) and the polymer (b) having no energy ray-curable group to the total content of components other than the solvent is 5 to 90% by mass
  • the content is preferably 10 to 80% by mass, and particularly preferably 20 to 70% by mass.
  • the energy ray-curable film-like transparent adhesive containing the filler exhibits the same effect as the thermosetting film-like transparent adhesive containing the filler (d).
  • the filler contained in the composition (IV-1) and the energy ray-curable film-like transparent adhesive includes the filler (d) contained in the thermosetting adhesive composition and the thermosetting film-like transparent adhesive The same thing is mentioned.
  • the filler contained in the composition (IV-1) and the energy ray-curable film-like transparent adhesive may be only one type, or two or more types, and in the case of two or more types, the combination and ratio thereof are It can be selected arbitrarily.
  • the ratio of the content of the filler to the total content of all the components other than the solvent is 25 to The content is preferably 75% by mass, and more preferably 28 to 72% by mass. Since the filler is significantly less likely to absorb water than the other components, when the ratio is at least the lower limit, it is easier to make the water absorption coefficient 0.55% or less, and the transparent resin film is small in size. When picking up the attached glass wafer from the support sheet, the effect of suppressing the remaining of the transparent resin film on the support sheet is further enhanced.
  • cured material improves more because the said ratio is below the said upper limit.
  • Composition (IV-1) is a group consisting of a thermosetting component, a coupling agent, a crosslinking agent, a photopolymerization initiator, and a general-purpose additive, in addition to the energy ray-curable component and the filler, according to the purpose. You may contain 1 type, or 2 or more types selected from more.
  • thermosetting component As the thermosetting component, the coupling agent, the crosslinking agent, the photopolymerization initiator and the general-purpose additive in the composition (IV-1), an epoxy-based thermosetting resin in a thermosetting adhesive composition ( b), the same as the coupling agent (e), the crosslinking agent (f), the photopolymerization initiator (h), and the general purpose additive (i).
  • the energy ray-curable film-like transparent adhesive formed by using the composition (IV-1) containing the energy ray-curable component and the thermosetting component has an adhesive strength to an adherend by heating.
  • the strength of the transparent resin film formed from the energy ray-curable film-like transparent adhesive is also improved.
  • thermosetting component the coupling agent, the crosslinking agent, the photopolymerization initiator, and the general-purpose additive may be used alone or in combination of two or more. It may be used in combination, and in the case of using two or more kinds in combination, their combination and ratio can be arbitrarily selected.
  • thermosetting component The content of the thermosetting component, the coupling agent, the crosslinking agent, the photopolymerization initiator, and the general-purpose additive in the composition (IV-1) may be appropriately adjusted depending on the purpose and is not particularly limited.
  • the composition (IV-1) preferably further contains a solvent because the handling thereof is improved by dilution.
  • the solvent contained in the composition (IV-1) include the same as the solvent in the thermosetting adhesive composition.
  • the solvent contained in the composition (IV-1) may be only one, or two or more.
  • An energy ray curable adhesive composition such as the composition (IV-1) can be obtained by blending the respective components for constituting the composition. There is no particular limitation on the order of addition of each component at the time of blending, and two or more components may be added simultaneously.
  • a solvent it may be used by mixing the solvent with any compounding component other than the solvent and diluting this compounding component in advance, or by previously diluting any compounding component other than the solvent A solvent may be used by mixing with these compounding ingredients without storage.
  • the method of mixing each component at the time of compounding is not particularly limited, and a method of mixing by rotating a stirrer or a stirring blade, etc .; a method of mixing using a mixer; a method of adding ultrasonic waves and mixing, etc. It may be selected as appropriate.
  • the temperature and time of addition and mixing of the respective components are not particularly limited as long as the respective blended components do not deteriorate, and may be appropriately adjusted, but the temperature is preferably 15 to 30 ° C.
  • the infrared sensor module of the present invention is obtained by curing and bonding an infrared light receiving element and a glass wafer with the film-like transparent adhesive of the present invention. Since the glass wafer with high infrared transmittance and the film-like transparent adhesive after curing have high infrared light transmittance, the infrared light-receiving element transmits the infrared rays transmitted through the glass wafer and the film-like transparent adhesive after curing. It is possible to receive light efficiently. Since the glass wafer is firmly adhered to the infrared light receiving element by the film-like transparent adhesive, the infrared light receiving element is protected, and a highly reliable infrared sensor module can be obtained.
  • the infrared sensor module of the present invention can be manufactured by curing and bonding an infrared light receiving element and a glass wafer using the film-like transparent adhesive of the present invention.
  • Acrylic resin (1) methyl acrylate (hereinafter abbreviated as “MA”) (85 parts by mass), and 2-hydroxyethyl acrylate (hereinafter abbreviated as “HEA”) (15 parts by mass) Acrylic resin copolymerized (weight average molecular weight (Mw) 600,000).
  • MA methyl acrylate
  • HOA 2-hydroxyethyl acrylate
  • Acrylic resin (2) methyl acrylate (hereinafter abbreviated as “MA”) (85 parts by mass), and 2-hydroxyethyl acrylate (hereinafter abbreviated as “HEA”) (15 parts by mass) Acrylic resin copolymerized (weight average molecular weight (Mw) 700,000).
  • MA methyl acrylate
  • HOA 2-hydroxyethyl acrylate
  • Acrylic resin (3) butyl acrylate (hereinafter abbreviated as “BA”) (55 parts by mass), methyl acrylate (hereinafter abbreviated as “MA”) (15 parts by mass), glycidyl methacrylate (below ,
  • An acrylic resin weight average molecular weight (abbreviated as “GMA”) (20 parts by mass) and acrylic acid 2-hydroxyethyl (hereinafter abbreviated as “HEA”) (10 parts by mass) Mw) 800,000).
  • the obtained adhesive composition is applied to the release-treated surface of a release film of which a single surface of a polyethylene terephthalate film (thickness 38 ⁇ m) is release-treated by silicone treatment, dried at 100 ° C. for 2 minutes, and the thickness is A film-like transparent adhesive of 10 ⁇ m was obtained.
  • the obtained adhesive composition is applied to the release-treated surface of a release film of which a single surface of a polyethylene terephthalate film (thickness 38 ⁇ m) is release-treated by silicone treatment, dried at 100 ° C. for 2 minutes, and the thickness is A film-like transparent adhesive of 20 ⁇ m was obtained.
  • an adhesive composition having a solid content concentration of 30% by mass is prepared.
  • the obtained adhesive composition is applied to the release-treated surface of a release film of which a single surface of a polyethylene terephthalate film (thickness 38 ⁇ m) is release-treated by silicone treatment, dried at 100 ° C. for 2 minutes, and the thickness is A film-like transparent adhesive of 20 ⁇ m was obtained.
  • the obtained adhesive composition is applied to the release-treated surface of a release film of which a single surface of a polyethylene terephthalate film (thickness 38 ⁇ m) is release-treated by silicone treatment, dried at 100 ° C. for 2 minutes, and the thickness is A film-like transparent adhesive of 20 ⁇ m was obtained.
  • the obtained adhesive composition is applied to the release-treated surface of a release film of which a single surface of a polyethylene terephthalate film (thickness 38 ⁇ m) is release-treated by silicone treatment, dried at 100 ° C. for 2 minutes, and the thickness is A film-like transparent adhesive of 20 ⁇ m was obtained.
  • energy ray curing property Resin (trade name "Seika Seven SS 02-242" manufactured by Dainichi Seika Kogyo Co., Ltd.): 150 parts by mass
  • crosslinking agent (trade name "BHS 8515” manufactured by Toyochem Co., Ltd .: 1 part by mass dissolved or dispersed in methyl ethyl ketone, 23
  • the adhesive composition having a solid content concentration of 40% by mass was prepared by stirring at ° C.
  • the obtained adhesive composition is applied to the release-treated surface of a release film of which a single surface of a polyethylene terephthalate film (thickness 38 ⁇ m) is release-treated by silicone treatment, dried at 100 ° C. for 2 minutes, and the thickness is A film-like transparent adhesive of 20 ⁇ m was obtained.
  • an adhesive composition having a solid content concentration of 60% by mass was prepared.
  • the obtained adhesive composition is applied to the release-treated surface of a release film of which a single surface of a polyethylene terephthalate film (thickness 38 ⁇ m) is release-treated by silicone treatment, dried at 100 ° C. for 2 minutes, and the thickness is A film-like transparent adhesive of 20 ⁇ m was obtained.
  • energy ray curing Resin (trade name "Seika Seven SS 02-242" manufactured by Dainichi Seika Kogyo Co., Ltd.): 1200 parts by mass
  • crosslinking agent (trade name "BHS 8515” manufactured by Toyochem Co., Ltd .: 1 part by mass dissolved or dispersed in methyl ethyl ketone, By stirring at 23 ° C., an adhesive composition having a solid content concentration of 40% by mass was prepared.
  • the obtained adhesive composition is applied to the release-treated surface of a release film of which a single surface of a polyethylene terephthalate film (thickness 38 ⁇ m) is release-treated by silicone treatment, dried at 100 ° C. for 2 minutes, and the thickness is A film-like transparent adhesive of 20 ⁇ m was obtained.
  • the obtained adhesive composition is applied to the release-treated surface of a release film of which a single surface of a polyethylene terephthalate film (thickness 38 ⁇ m) is release-treated by silicone treatment, dried at 100 ° C. for 2 minutes, and the thickness is A film-like transparent adhesive of 20 ⁇ m was obtained.
  • compositions of the film transparent adhesives of Examples 1 to 6 and Comparative Examples 1 to 3 are summarized in Table 1.
  • the film-like transparent adhesive with a release film obtained above is bonded at 70 ° C. to a 100 ⁇ m-thick glass wafer (D263 T eco manufactured by SCHOTT), and the glass film and the film-like transparent are removed by removing the release film.
  • An adhesive laminate was prepared, and then the film-like transparent adhesive was cured in an oven at 175 ° C. for 5 h.
  • the ultraviolet radiation device RAD-2000 m
  • the film transparent adhesive was cured at 175 ° C. for 5 h in an oven.
  • the following items were evaluated about the laminated body of the glass wafer and film-form transparent adhesive agent after thermosetting, respectively.
  • the light transmittance (%) at a wavelength of 800 to 2000 nm of the subsequent laminate was measured, and the light transmittance at a wavelength of 850 nm was determined. In the wavelength region of 800 to 2000 nm, the light transmittance was always evaluated as 80% or more as ⁇ , and the other as X.
  • the wavelength 850 nm transmittance of the film adhesive after heat curing is as good as 90% or more, and the transmittance as the wavelength of 800 to 2000 nm is as good as 80% or more.
  • the infrared ray transmittance at a wavelength of 850 nm of the film adhesive after heat curing is 5 to 42%, and the transmittance at a wavelength of 800 to 2000 nm is less than 80%. Because of its low infrared transparency, it can not be used for bonding infrared light receiving elements to glass wafers.
  • the film-like transparent adhesive of the present invention can be suitably used for bonding an infrared ray receiving element having an infrared ray receiving portion of an infrared sensor module to a glass wafer.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Adhesive Tapes (AREA)
  • Photometry And Measurement Of Optical Pulse Characteristics (AREA)

Abstract

L'invention concerne un adhésif transparent de type film qui est un adhésif transparent de type film thermodurcissable ou durcissable par rayonnement d'énergie, et qui a une transmittance de lumière à une longueur d'onde de 800 nm après durcissement de 80 % ou plus. De préférence, les transmittances de lumière à des longueurs d'onde de 800 à 2 000 nm après durcissement sont toutes de 80 % ou plus, et de préférence la transmittance de lumière à une longueur d'onde de 850 nm après durcissement est de 90 % ou plus.
PCT/JP2018/018093 2017-08-28 2018-05-10 Adhésif transparent de type film et module de capteur infrarouge WO2019044046A1 (fr)

Priority Applications (3)

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CN201880055290.6A CN111051455B (zh) 2017-08-28 2018-05-10 膜状透明粘合剂及红外线传感器模块
SG11202001719RA SG11202001719RA (en) 2017-08-28 2018-05-10 Film-like transparent adhesive and infrared sensor module
JP2019538963A JP7107946B2 (ja) 2017-08-28 2018-05-10 赤外線センサーモジュール

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JP2006321832A (ja) * 2005-05-17 2006-11-30 Konishi Kagaku Ind Co Ltd 光半導体封止用樹脂組成物及びこれを用いた光半導体装置
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JP7107946B2 (ja) 2022-07-27
TWI758479B (zh) 2022-03-21
SG11202001719RA (en) 2020-03-30
JPWO2019044046A1 (ja) 2020-08-13
CN111051455B (zh) 2022-05-03
TW201913982A (zh) 2019-04-01

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