WO2019035411A1 - 湿気硬化型樹脂組成物、電子部品用接着剤、及び、表示素子用接着剤 - Google Patents

湿気硬化型樹脂組成物、電子部品用接着剤、及び、表示素子用接着剤 Download PDF

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WO2019035411A1
WO2019035411A1 PCT/JP2018/029943 JP2018029943W WO2019035411A1 WO 2019035411 A1 WO2019035411 A1 WO 2019035411A1 JP 2018029943 W JP2018029943 W JP 2018029943W WO 2019035411 A1 WO2019035411 A1 WO 2019035411A1
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moisture
curable resin
resin composition
meth
acrylate
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PCT/JP2018/029943
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English (en)
French (fr)
Japanese (ja)
Inventor
彰 結城
高橋　徹
拓身 木田
智一 玉川
坤 徐
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積水化学工業株式会社
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Priority to CN201880044533.6A priority Critical patent/CN110832034B/zh
Priority to JP2018546718A priority patent/JP7088838B2/ja
Priority to KR1020197022861A priority patent/KR102598369B1/ko
Publication of WO2019035411A1 publication Critical patent/WO2019035411A1/ja

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/0041—Optical brightening agents, organic pigments
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/17—Amines; Quaternary ammonium compounds
    • C08K5/18—Amines; Quaternary ammonium compounds with aromatically bound amino groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L101/00—Compositions of unspecified macromolecular compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L101/00—Compositions of unspecified macromolecular compounds
    • C08L101/02—Compositions of unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups
    • C08L101/10—Compositions of unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups containing hydrolysable silane groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
    • C08L75/04—Polyurethanes
    • 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
    • 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
    • C09J201/00—Adhesives based on unspecified macromolecular compounds
    • C09J201/02—Adhesives based on unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups
    • C09J201/10—Adhesives based on unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups containing hydrolysable silane groups

Definitions

  • the present invention relates to a moisture-curable resin composition which is excellent in colorability and curability and can suppress discoloration.
  • the present invention also relates to an adhesive for electronic parts and an adhesive for display elements, which are obtained by using the moisture-curable resin composition.
  • liquid crystal display elements organic EL display elements, and the like have been widely used as display elements having features such as thinness, light weight, and low power consumption.
  • an adhesive comprising a resin composition is usually used for sealing a liquid crystal or a light emitting layer, adhesion of various members such as a substrate, an optical film, a protective film and the like.
  • high integration and miniaturization are required for electronic components such as semiconductor chips, and for example, bonding of a plurality of thin semiconductor chips via an adhesive layer to form a laminate of semiconductor chips It has been done.
  • Patent Document 1 discloses a photocurable colored adhesive containing a colorant.
  • the photocurable colored adhesive disclosed in Patent Document 1 uses carbon black or the like as a coloring agent, and most of the active energy rays such as ultraviolet rays irradiated to photocure the curable resin. Is absorbed by the colorant such as the carbon black. Therefore, when the compounding amount of the coloring agent is increased in order to enhance the coloring property, there is a problem that the adhesive obtained is inferior in the curability (deep area curability).
  • Patent Document 2 discloses a photocurable resin composition using a leuco dye as a photosensitive colorant.
  • a photosensitive colorant is blended in the photocurable resin composition, there is a problem that even if it is colored once, the cured product may be faded.
  • the present invention is a moisture-curable resin composition containing a moisture-curable resin and a photosensitive colorant.
  • the present invention will be described in detail below.
  • the present inventors have surprisingly found that a moisture-curable resin composition containing a moisture-curable resin is excellent in colorability and curability by incorporating a photosensitive colorant as a colorant and that it is photosensitive.
  • the inventors have found that it is possible to obtain a moisture-curable resin composition capable of suppressing the color fading which is a problem when using a colorant, and the present invention has been completed.
  • the moisture curable resin composition of the present invention contains a photosensitive colorant.
  • the moisture-curable resin composition of the present invention is excellent in colorability and curability (in particular, deep part curability).
  • the moisture-curable resin composition of the present invention can suppress the color fading, which is a problem when the photosensitive colorant is used.
  • the above-mentioned "photosensitive colorant” means a material having a property of being discolored (colored) by light irradiation.
  • the photosensitive colorant is colored by changing the chemical structure of the photosensitive colorant as a reaction (coloring reaction) proceeds directly or indirectly by light irradiation.
  • the reverse reaction of this coloring reaction proceeds after coloring, fading will occur.
  • the reaction of the photosensitive colorant after coloring with the moisture-curable resin described later prevents the progress of the reverse reaction of the coloring reaction. As a result, it is considered that the effect of suppressing fading is exhibited.
  • the photosensitive colorant examples include leuco dyes and photochromic dyes.
  • leuco dyes are preferable from the viewpoint of increasing the optical density (OD value) and exhibiting further excellent light shielding properties.
  • leuco dye examples include crystal violet lactone, malachite green lactone, 3,3-bis (p-dimethylaminophenyl) -6-aminophthalide, and 3,3-bis (p-dimethylaminophenyl) -6- (p -Toluenesulfonamide) phthalide, 3,3-bis (2- (p-dimethylaminophenyl) -2- (4-methoxyphenyl) vinyl) -4,5,6,7-tetrachlorophthalide, 3-dimethyl Amino-6-methyl-7-chlorofluorane, 3-dimethylamino-6-methyl-7-anilinofluorane, 3-diethylamino-7-chlorofluorane, 3-diethylamino-7- (o-chloroanilino) fluoran , 3-diethylamino-7- (m-trifluoromethylanilino) fluoran, 3-diethylamide -7-phen
  • R 1 and R 2 each represent a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, a phenyl group, or a 3-trifluoromethylphenyl group, and may be identical to each other, It may be different.
  • R 3 is a hydrogen atom or an alkyl group having 1 or more and 3 or less carbon atoms.
  • the preferable lower limit of the content of the photosensitive colorant is 0.1 parts by weight and the preferable upper limit is 10 parts by weight with respect to 100 parts by weight of the curable resin component.
  • the content of the photosensitive colorant is 0.1 parts by weight or more, the resulting moisture-curable resin composition is more excellent in colorability.
  • the content of the photosensitive colorant is 10 parts by weight or less, the resulting moisture-curable resin composition is more excellent in curability.
  • the more preferable lower limit of the content of the photosensitive colorant is 0.3 parts by weight, and the more preferable upper limit is 3 parts by weight.
  • curable resin component means “moisture-curable resin” when the moisture-curable resin composition does not contain a photopolymerizable compound described later, and the photopolymerizable compound described later When it contains, it means “the total of the photopolymerizable compound and the moisture-curable resin”.
  • the moisture-curable resin composition of the present invention may contain a non-photosensitive colorant in addition to the above-mentioned photosensitive colorant as long as the object of the present invention is not impaired.
  • the non-photosensitive colorant include iron oxide, titanium black, aniline black, cyanine black, fullerene, carbon black, resin-coated carbon black and the like.
  • the non-photosensitive coloring agent may not have a black color, and as long as it is a material having the ability to hardly transmit light in the visible light region, titanium oxide and the like mentioned as a filler described later may also be used. It is contained in the said non-photosensitive coloring agent. Among them, titanium black is preferred.
  • the titanium black is a substance having a high transmittance to light in the vicinity of the ultraviolet region, particularly to light of 370 to 450 nm, as compared with the average transmittance to light of 300 to 800 nm. That is, while the titanium black sufficiently imparts a light shielding property to the moisture-curable resin composition of the present invention by sufficiently shielding light having a wavelength in the visible light region, it has a property of transmitting light having a wavelength near the ultraviolet region. It is a non-photosensitive colorant having.
  • the light of the moisture-curable resin composition of the present invention can be obtained by using, as a photopolymerization initiator described later, a reaction that can be initiated by light of a wavelength (370 to 450 nm) at which the transmittance of titanium black increases. Hardening can be made difficult to inhibit.
  • a substance having a high insulating property is preferable, and titanium black is also preferable as a non-photosensitive colorant having a high insulating property. .
  • the titanium black preferably has an optical density (OD value) of 3 or more, and more preferably 4 or more. The higher the light shielding property of the titanium black, the better. There is no particular upper limit to the OD value of the titanium black, but it is usually 5 or less.
  • the titanium black preferably has a degree of blackness (L value) of 9 or more, more preferably 11 or more.
  • the above-mentioned titanium black exhibits sufficient effects even if it is not surface-treated, but the surface is treated with an organic component such as a coupling agent, silicon oxide, titanium oxide, germanium oxide, aluminum oxide, zirconium oxide
  • an organic component such as a coupling agent, silicon oxide, titanium oxide, germanium oxide, aluminum oxide, zirconium oxide
  • Surface-treated titanium black such as those coated with an inorganic component such as magnesium oxide, can also be used.
  • what is processed by the organic component is preferable at the point which can improve insulation more.
  • the lower limit of the specific surface area of the titanium black is preferably 5 m 2 / g, preferably 40 m 2 / g, more preferably 10 m 2 / g, and still more preferably 25 m 2 / g.
  • a preferable lower limit of the sheet resistance of the above-mentioned titanium black is 10 9 ⁇ / ⁇ when it is mixed with a resin (70% blending), and a more preferable lower limit is 10 11 ⁇ / ⁇ .
  • titanium blacks commercially available ones include 12S, 13M, 13M-C, 13R-N (all manufactured by Mitsubishi Materials Corporation), Tilac D (manufactured by Akao Kasei Co., Ltd.), and the like.
  • the primary particle diameter of the non-photosensitive colorant is appropriately selected according to the application, such as the distance between the substrates of the display element or less. Is 500 nm.
  • the primary particle diameter of the non-photosensitive colorant is in this range, the resulting moisture-curable resin composition is excellent in coating property and workability on a substrate without largely increasing viscosity and thixotropy.
  • a more preferable lower limit of the primary particle diameter of the non-photosensitive colorant is 50 nm, and a more preferable upper limit is 200 nm.
  • the primary particle diameter of the non-photosensitive colorant may be measured by dispersing the non-photosensitive colorant in a solvent (water, organic solvent, etc.) using NICOMP 380 ZLS (manufactured by PARTICLE SIZING SYSTEMS). it can.
  • the lower limit of the content of the non-photosensitive colorant is preferably 0.05 parts by weight and the upper limit is 0.5 parts by weight with respect to 100 parts by weight of the curable resin component.
  • the content of the non-photosensitive colorant is in this range, the resulting moisture-curable resin composition is colored while maintaining excellent drawability, adhesion to a substrate, and strength after curing. It becomes excellent by the nature.
  • a more preferable lower limit of the content of the non-photosensitive colorant is 0.1 parts by weight.
  • the moisture-curable resin composition of the present invention contains a moisture-curable resin.
  • the moisture-curable resin is preferably at least one of a moisture-curable urethane resin and a hydrolyzable silyl group-containing resin.
  • a moisture curable urethane resin is more preferable because it is excellent in quick curing property at the time of moisture curing.
  • the moisture-curable urethane resin has a urethane bond and an isocyanate group, and the isocyanate group in the molecule reacts with the moisture in the air or in the adherend to be cured.
  • the moisture-curable urethane resin may have only one isocyanate group in one molecule, or may have two or more isocyanate groups. Among them, it is preferable to have an isocyanate group at both ends of the main chain of the molecule.
  • the moisture-curable urethane resin can be obtained by reacting a polyol compound having two or more hydroxyl groups in one molecule with a polyisocyanate compound having two or more isocyanate groups in one molecule.
  • polyol compound the well-known polyol compound normally used for manufacture of a polyurethane can be used, For example, polyester polyol, polyether polyol, polyalkylene polyol, polycarbonate polyol etc. are mentioned. These polyol compounds may be used alone or in combination of two or more.
  • polyester polyol examples include polyester polyols obtained by the reaction of a polyvalent carboxylic acid and a polyol, and poly- ⁇ -caprolactone polyols obtained by ring-opening polymerization of ⁇ -caprolactone.
  • polyvalent carboxylic acid as a raw material of the polyester polyol examples include terephthalic acid, isophthalic acid, 1,5-naphthalic acid, 2,6-naphthalic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberin Acids, azelaic acids, sebacic acids, decamethylene dicarboxylic acids, dodecamethylene dicarboxylic acids and the like can be mentioned.
  • polyester polyol used as the raw material of said polyester polyol
  • polyether polyols examples include ethylene glycol, propylene glycol, ring-opening polymers of tetrahydrofuran, ring-opening polymers of 3-methyltetrahydrofuran, and random copolymers or block copolymers of these or their derivatives, bisphenol Type polyoxyalkylene modified products and the like.
  • the bisphenol-type polyoxyalkylene modified substance is a polyether polyol obtained by addition reaction of an alkylene oxide (for example, ethylene oxide, propylene oxide, butylene oxide, etc.) to an active hydrogen portion of a bisphenol-type molecular skeleton, and random coweight It may be united or may be a block copolymer. It is preferable that the said bisphenol type polyoxyalkylene modified body is 1 type or 2 types or more of alkylene oxides being added to the both terminal of bisphenol type molecular frame. It does not specifically limit as said bisphenol type, A type, F type, S type etc. are mentioned, Preferably it is bisphenol A type.
  • polystyrene polystyrene polystyrene polystyrene resin As said polyalkylene polyol, a polybutadiene polyol, a hydrogenated polybutadiene polyol, a hydrogenated polyisoprene polyol etc. are mentioned, for example.
  • polycarbonate polyol examples include polyhexamethylene carbonate polyol and polycyclohexane dimethylene carbonate polyol.
  • an aromatic polyisocyanate compound and an aliphatic polyisocyanate compound are used suitably.
  • the aromatic polyisocyanate compound include diphenylmethane diisocyanate, liquid modified products of diphenylmethane diisocyanate, polymeric MDI, tolylene diisocyanate and naphthalene-1,5-diisocyanate.
  • aliphatic polyisocyanate compound examples include hexamethylene diisocyanate, trimethylhexamethylene diisocyanate, lysine diisocyanate, norbornane diisocyanate, transcyclohexane-1,4-diisocyanate, isophorone diisocyanate, hydrogenated xylylene diisocyanate, hydrogenated diphenylmethane diisocyanate, and cyclohexane.
  • Diisocyanate, bis (isocyanatomethyl) cyclohexane, dicyclohexylmethane diisocyanate and the like can be mentioned.
  • diphenylmethane diisocyanate and modified products thereof are preferable in view of low vapor pressure, low toxicity and ease of handling.
  • the said polyisocyanate compound may be used independently, and may be used in combination of 2 or more type.
  • the said moisture curing type urethane resin is a thing obtained using the polyol compound which has a structure represented by following formula (2).
  • a polyol compound having a structure represented by the following formula (2) it is possible to obtain a composition having excellent adhesion and a cured product which is flexible and has a good elongation, and a phase with a photopolymerizable compound described later It becomes excellent in solubility.
  • a polyether polyol comprising a ring opening polymerization compound of propylene glycol, a tetrahydrofuran (THF) compound, or a ring opening polymerization compound of a tetrahydrofuran compound having a substituent such as a methyl group are preferable.
  • R represents a hydrogen atom, a methyl group or an ethyl group
  • l is an integer of 0 to 5
  • m is an integer of 1 to 500
  • n is an integer of 1 to 10
  • l is preferably 0 to 4
  • m is preferably 50 to 200
  • n is preferably 1 to 5.
  • the case where l is 0 means that the carbon bonded to R is directly bonded to oxygen.
  • the hydrolyzable silyl group-containing resin is cured by the reaction of the hydrolyzable silyl group in the molecule with the moisture in the air or the adherend.
  • the hydrolyzable silyl group-containing resin may have only one hydrolyzable silyl group in one molecule, or may have two or more hydrolyzable silyl groups. Among them, it is preferable to have hydrolyzable silyl groups at both ends of the main chain of the molecule.
  • the hydrolyzable silyl group is represented by the following formula (3).
  • R 4 is each independently an alkyl group having 1 to 20 carbon atoms, which may be substituted, an aryl group having 6 to 20 carbon atoms, an aralkyl group having 7 to 20 carbon atoms, or Or —OSiR 5 3 (wherein R 5 is each independently a hydrocarbon group having 1 or more and 20 or less carbon atoms).
  • X is a hydroxy group or a hydrolysable group each independently.
  • a is an integer of 1 to 3.
  • the hydrolyzable group is not particularly limited, and examples thereof include a hydrogen atom, a halogen atom, an alkoxy group, an alkenyloxy group, an aryloxy group, an acyloxy group, a ketoximate group, an amino group, an amido group, an acid amide group, an aminooxy group, A mercapto group etc. are mentioned.
  • a halogen atom, an alkoxy group, an alkenyloxy group and an acyloxy group are preferable because of high activity, and an alkoxy group such as a methoxy group and an ethoxy group is more preferable, since a hydrolyzability is mild and easy to handle.
  • ethoxy groups are more preferred.
  • an ethoxy group and an isopropenoxy group are preferable in which the compounds to be eliminated by the reaction are ethanol and acetone, respectively.
  • the above hydroxy group or the above hydrolyzable group can be bonded in the range of 1 to 3 to one silicon atom.
  • those groups may be identical or different.
  • a in the formula (3) is preferably 2 or 3, and particularly preferably 3. Further, in terms of storage stability, a is preferably 2.
  • R 4 in the above formula (3) is, for example, an alkyl group such as methyl group or ethyl group, a cycloalkyl group such as cyclohexyl group, an aryl group such as phenyl group, an aralkyl group such as benzyl group, a trimethylsiloxy group , Chloromethyl group, methoxymethyl group and the like. Among them, methyl group is preferable.
  • hydrolyzable silyl group examples include methyldimethoxysilyl group, trimethoxysilyl group, triethoxysilyl group, tris (2-propenyloxy) silyl group, triacetoxysilyl group, (chloromethyl) dimethoxysilyl group, Chloromethyl) diethoxysilyl group, (dichloromethyl) dimethoxysilyl group, (1-chloroethyl) dimethoxysilyl group, (1-chloropropyl) dimethoxysilyl group, (methoxymethyl) dimethoxysilyl group, (methoxymethyl) diethoxysilyl group Groups, (ethoxymethyl) dimethoxysilyl group, (1-methoxyethyl) dimethoxysilyl group, (aminomethyl) dimethoxysilyl group, (N, N-dimethylaminomethyl) dimethoxysilyl group, (N, N-diethoxy
  • hydrolyzable silyl group-containing resin for example, a hydrolyzable silyl group-containing (meth) acrylic resin, an organic polymer having a hydrolyzable silyl group at a molecular chain terminal or a molecular chain terminal site, a hydrolyzable silyl group Containing polyurethane resin etc. are mentioned.
  • the hydrolyzable silyl group-containing (meth) acrylic resin preferably has a repeating structural unit derived from a hydrolyzable silyl group-containing (meth) acrylic acid ester and a (meth) acrylic acid alkyl ester in the main chain.
  • hydrolyzable silyl group-containing (meth) acrylic acid ester examples include 3- (trimethoxysilyl) propyl (meth) acrylate, 3- (triethoxysilyl) propyl (meth) acrylate, and (meth) acrylic acid.
  • 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, tert-butyl (meth) acrylate, n-pentyl (meth) acrylate, n-hexyl (meth) acrylate, cyclohexyl (meth) acrylate, n- (meth) acrylate Heptyl, n-octyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, n-nonyl (meth) acrylate, n-decyl (meth) acrylate, n-dodecyl (meth) acrylate (meth) Examples include ste
  • hydrolysable silyl group containing (meth) acrylic resin the hydrolysable silicon group containing (meth) acrylic acid ester system described in, for example, WO 2016/035718
  • the synthesis method of a polymer etc. are mentioned.
  • the organic polymer having a hydrolyzable silyl group at the molecular chain terminal or at the molecular chain terminal site has a hydrolyzable silyl group at least either of the terminal of the main chain and the terminal of the side chain.
  • the skeleton structure of the main chain is not particularly limited, and examples thereof include saturated hydrocarbon polymers, polyoxyalkylene polymers, (meth) acrylic acid ester polymers and the like.
  • polyoxyalkylene polymer examples include a polyoxyethylene structure, a polyoxypropylene structure, a polyoxybutylene structure, a polyoxytetramethylene structure, a polyoxyethylene-polyoxypropylene copolymer structure, a polyoxypropylene-poly.
  • the polymer etc. which have an oxybutylene copolymer structure are mentioned.
  • Specific examples of the method for producing an organic polymer having a hydrolyzable silyl group at the molecular chain terminal or at the molecular chain terminal site include the molecular chain terminal or the molecular chain terminal or the molecular chain terminal described in WO 2016/035718.
  • the synthesis method of the organic polymer which has a crosslinkable silyl group only in the molecular chain terminal part is mentioned.
  • a reactive silicon group-containing compound described in WO 2012/117902 The synthesis method of a polyoxyalkylene type polymer etc. are mentioned.
  • hydrolyzable silyl group-containing polyurethane resin for example, when producing a polyurethane resin by reacting a polyol compound and a polyisocyanate compound, a silyl group-containing compound such as a silane coupling agent is further added.
  • a silyl group-containing compound such as a silane coupling agent
  • the method of making it react etc. are mentioned.
  • a synthesis method of a urethane oligomer having a hydrolyzable silyl group described in JP-A-2017-48345 can be mentioned.
  • silane coupling agent for example, vinyltrichlorosilane, vinyltriethoxysilane, vinyltris ( ⁇ -methoxy-ethoxy) silane, ⁇ - (3,4-epoxycyclohexyl) -ethyltrimethoxysilane, ⁇ -glycidoxy Propyltrimethoxysilane, ⁇ -glycidoxypropylmethyldiethoxysilane, ⁇ -methacryloxypropyltrimethoxysilane, N- ( ⁇ -aminoethyl) - ⁇ -aminopropyltrimethoxysilane, N- ( ⁇ -aminoethyl) - ⁇ -aminopropyltrimethyldimethoxysilane, N-phenyl- ⁇ -aminopropyltrimethoxysilane, ⁇ -chloropropyltrimethoxysilane, ⁇ -mercaptopropyltrimethoxysi
  • silane coupling agents may be used alone or in combination of two or more.
  • hydrolyzable silyl group-containing resins commercially available resins include, for example, Exester S 2410, Exester S 2420, Exester S 3430 (all manufactured by AGC), XMAP SA-100 S, and Cyryl MA 440 (all are Kaneka). Company) and the like.
  • the moisture-curable resin may have a radically polymerizable functional group.
  • a radically polymerizable functional group which the said moisture-curable resin may have the group which has an unsaturated double bond is preferable, and the (meth) acryloyl group is more preferable especially from the reactive surface.
  • the moisture-curable resin having a radically polymerizable functional group is not included in the radically polymerizable compound described later, and is treated as a moisture-curable resin.
  • the weight average molecular weight of the moisture-curable resin is not particularly limited, but a preferable lower limit is 800 and a preferable upper limit is 10,000. When the weight-average molecular weight of the moisture-curable resin is in this range, the resulting moisture-curable resin composition becomes more excellent in flexibility without becoming too high in crosslink density during curing, and is more excellent in coating property It becomes.
  • the lower limit of the weight average molecular weight of the moisture-curable resin is more preferably 2,000, more preferably 8,000, still more preferably 2,500, still more preferably 6,000.
  • the above-mentioned weight average molecular weight is a value obtained by gel permeation chromatography (GPC) using tetrahydrofuran as a solvent and measuring in terms of polystyrene.
  • GPC gel permeation chromatography
  • Shodex LF-804 made by Showa Denko
  • tetrahydrofuran etc. are mentioned as a solvent used by GPC.
  • the content of the moisture-curable resin is relative to 100 parts by weight in total of the photopolymerizable compound and the moisture-curable resin.
  • the preferred lower limit is 20 parts by weight, and the preferred upper limit is 90 parts by weight.
  • the lower limit of the content of the moisture-curable resin is preferably 30 parts by weight, more preferably 75 parts by weight, still more preferably 41 parts by weight, and still more preferably 70 parts by weight.
  • the moisture curable resin composition of the present invention may contain a photopolymerizable compound.
  • the moisture curable resin composition can be preferably used not only for adhesion of semiconductor chips, but also for adhesion of narrow frames in electronic parts and cases.
  • a radically polymerizable compound is suitably used as the photopolymerizable compound.
  • the radically polymerizable compound is not particularly limited as long as it is a radically polymerizable compound having photopolymerizability, and any compound having a radically polymerizable functional group in the molecule, but the unsaturated difunctional compound as a radically polymerizable functional group Compounds having a heavy bond are preferred, and from the viewpoint of reactivity, (meth) acrylic compounds are preferred.
  • (meth) acryloyl means acryloyl or methacryloyl
  • the above “(meth) acryl” means acryl or methacryl
  • the above “(meth) acrylic compound” is It means a compound having a meta) acryloyl group.
  • (meth) acrylic compound a (meth) acrylic acid ester compound, an epoxy (meth) acrylate, urethane (meth) acrylate etc. are mentioned, for example.
  • the above "(meth) acrylate” means acrylate or methacrylate.
  • all the isocyanate groups of the isocyanate compound used as the raw material of the said urethane (meth) acrylate are used for formation of a urethane bond, and the said urethane (meth) acrylate does not have a residual isocyanate group.
  • Examples of monofunctional compounds among the above (meth) acrylic acid ester compounds include N-acryloyloxyethyl hexahydrophthalimide, various imide (meth) acrylates, methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth ) Acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, t-butyl (meth) acrylate, n-octyl (meth) acrylate, isooctyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, isononyl (meth) ) Acrylate, isodecyl (meth) acrylate, lauryl (meth) acrylate, isomyristyl (meth) acrylate, stearyl (meth) acrylate, cyclohexyl (meth) acryl
  • epoxy (meth) acrylate what is obtained by making an epoxy compound and (meth) acrylic acid react in presence of a basic catalyst according to a conventional method etc. are mentioned, for example.
  • the epoxy compound examples include bisphenol A epoxy resin, bisphenol F epoxy resin, bisphenol S epoxy resin, 2,2′-diallyl bisphenol A epoxy resin, hydrogenated bisphenol epoxy resin, propylene oxide-added bisphenol A Type epoxy resin, resorcinol type epoxy resin, biphenyl type epoxy resin, sulfide type epoxy resin, diphenyl ether type epoxy resin, dicyclopentadiene type epoxy resin, naphthalene type epoxy resin, phenol novolac type epoxy resin, ortho cresol novolac type epoxy resin, di Cyclopentadiene novolac epoxy resin, biphenyl novolac epoxy resin, naphthalene phenol novolac epoxy resin, glycidyl ether Emission type epoxy resin, alkyl polyol type epoxy resin, rubber modified epoxy resin, glycidyl ester compounds, bisphenol A type episulfide resins.
  • epoxy (meth) acrylates for example, epoxy (meth) acrylate manufactured by Daicel Ornex, epoxy (meth) acrylate manufactured by Shin-Nakamura Chemical Co., Ltd., epoxy manufactured by Kyoeisha Chemical Examples thereof include meta) acrylates and epoxy (meth) acrylates manufactured by Nagase ChemteX Corporation. Examples of the epoxy (meth) acrylates manufactured by Daicel Ornex Co., Ltd.
  • Examples of the epoxy (meth) acrylate manufactured by Shin-Nakamura Chemical Co., Ltd. include EA-1010, EA-1020, EA-5323, EA-5520, EA-CHD, EMA-1020 and the like. Examples of epoxy (meth) acrylates manufactured by Kyoeisha Chemical Co., Ltd.
  • epoxy ester M-600A examples include epoxy ester M-600A, epoxy ester 40EM, epoxy ester 70PA, epoxy ester 200PA, epoxy ester 80MFA, epoxy ester 3002M, epoxy ester 3002A, epoxy ester 1600A, Epoxy ester 3000 M, epoxy ester 3000 A, epoxy ester 200 EA, epoxy ester 400 EA, etc. may be mentioned.
  • Examples of the epoxy (meth) acrylate manufactured by Nagase ChemteX Corporation examples include Denacol acrylate DA-141, Denacol acrylate DA-314, Denacol acrylate DA-911 and the like.
  • the urethane (meth) acrylate can be obtained, for example, by reacting a (meth) acrylic acid derivative having a hydroxyl group with an isocyanate compound in the presence of a catalytic amount of a tin-based compound.
  • isocyanate compound examples include isophorone diisocyanate, 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, hexamethylene diisocyanate, trimethylhexamethylene diisocyanate, diphenylmethane-4,4'-diisocyanate (MDI), and hydrogenation.
  • MDI polymeric MDI, 1,5-naphthalene diisocyanate, norbornane diisocyanate, tolidine diisocyanate, xylylene diisocyanate (XDI), hydrogenated XDI, lysine diisocyanate, triphenylmethane triisocyanate, tris (isocyanatophenyl) thiophosphate, tetramethyl xylylene And isocyanate, 1,6,11-undecanetriisocyanate, etc.
  • a chain-extended isocyanate compound obtained by the reaction of a polyol and an excess of an isocyanate compound can also be used.
  • the polyol include ethylene glycol, propylene glycol, glycerin, sorbitol, trimethylolpropane, carbonate diol, polyether diol, polyester diol, polycaprolactone diol and the like.
  • the (meth) acrylic acid derivative having a hydroxyl group for example, mono (meth) acrylate of dihydric alcohol, mono (meth) acrylate or di (meth) acrylate of trihydric alcohol, epoxy (meth) acrylate, etc.
  • dihydric alcohol include ethylene glycol, propylene glycol, 1,3-propanediol, 1,3-butanediol, 1,4-butanediol, polyethylene glycol and the like.
  • the trihydric alcohol include trimethylol ethane, trimethylol propane and glycerin.
  • epoxy (meth) acrylate bisphenol-A epoxy (meth) acrylate etc. are mentioned, for example.
  • urethane (meta) acrylates for example, urethane (meta) acrylate by Toagosei Co., Ltd., urethane (meta) acrylate by Daicel Ornex, urethane (meta) by Negami Kogyo Co., Ltd. Acrylate, urethane (meth) acrylate manufactured by Shin-Nakamura Chemical Co., Ltd., urethane (meth) acrylate manufactured by Kyoeisha Chemical Co., Ltd., and the like. Examples of the urethane (meth) acrylate manufactured by Toagosei Co., Ltd.
  • urethane (meth) acrylates manufactured by Daicel Ornex Co., Ltd. include, for example, EBECRYL230, EBECRYL270, EBECRYL4858, EBECRYL8402, EBECRYL8411, EBECRYL8412, EBECRYL8413, EBECRYL8804 and EBECLYL EH7 EBECRYL220, EBECRYL2220, KRM7735, KRM-8295 and the like.
  • Examples of the urethane (meth) acrylate manufactured by Shin-Nakamura Chemical Co., Ltd. include U-2HA, U-2PHA, U-3HA, U-4HA, U-6H, U-6LPA, U-6HA, U-10H, and the like.
  • urethane (meth) acrylates manufactured by Kyoeisha Chemical Co., Ltd. include AI-600, AH-600, AT-600, UA-101I, UA-101T, UA-306H, UA-306I, UA-306T, etc.
  • radically polymerizable compounds other than those described above can also be used appropriately.
  • a (meth) acrylamide compound, a vinyl compound etc. are mentioned, for example.
  • the (meth) acrylamide compound include N, N-dimethyl (meth) acrylamide, N- (meth) acryloyl morpholine, N-hydroxyethyl (meth) acrylamide, N, N-diethyl (meth) acrylamide, N- Isopropyl (meth) acrylamide, N, N-dimethylaminopropyl (meth) acrylamide and the like can be mentioned.
  • the vinyl compound include styrene, ⁇ -methylstyrene, N-vinyl-2-pyrrolidone, N-vinyl- ⁇ -caprolactam and the like.
  • the said radically polymerizable compound contains a monofunctional radically polymerizable compound and a polyfunctional radically polymerizable compound from a viewpoint of adjusting curability.
  • the moisture curable resin composition obtained becomes what is excellent by curability and tackiness.
  • urethane (meth) acrylate is preferably used in combination with the monofunctional radically polymerizable compound as the polyfunctional radically polymerizable compound.
  • the content of the polyfunctional radically polymerizable compound is the same as that of the monofunctional radically polymerizable compound and the polybasic radically polymerizable compound.
  • the preferable lower limit is 2 parts by weight and the preferable upper limit is 45 parts by weight with respect to 100 parts by weight in total with the functional radically polymerizable compound.
  • the content of the polyfunctional radically polymerizable compound is in this range, the resulting moisture-curable resin composition is more excellent in curability and tackiness.
  • a more preferable lower limit of the content of the polyfunctional radically polymerizable compound is 5 parts by weight, and a more preferable upper limit is 35 parts by weight.
  • the preferable lower limit of the content of the photopolymerizable compound is 10 parts by weight and the preferable upper limit is 80 parts by weight with respect to 100 parts by weight in total of the photopolymerizable compound and the moisture-curable resin.
  • the lower limit of the content of the photopolymerizable compound is preferably 25 parts by weight, more preferably 70 parts by weight, still more preferably 30 parts by weight, and still more preferably 59 parts by weight.
  • the moisture curable resin composition of the present invention may contain a photopolymerization initiator.
  • a photoinitiator a radical photopolymerization initiator is used suitably.
  • the photo radical polymerization initiator include benzophenone compounds, acetophenone compounds, acyl phosphine oxide compounds, titanocene compounds, oxime ester compounds, benzoin ether compounds, thioxanthone and the like.
  • the radical photopolymerization initiator by BASF AG As what is marketed among the said radical photopolymerization initiators, the radical photopolymerization initiator by BASF AG, the radical photopolymerization initiator by Tokyo Chemical Industry Co., Ltd., etc. are mentioned, for example.
  • the radical photopolymerization initiators manufactured by BASF include IRGACURE 184, IRGACURE 369, IRGACURE 379, IRGACURE 651, IRGACURE 784, IRGACURE 819, IRGACURE 907, IRGACURE 2959, IRGACURE OXE01, IRGACURE TPO and the like.
  • the radical photopolymerization initiator manufactured by Tokyo Chemical Industry Co., Ltd. include benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether and the like.
  • the preferable lower limit of the content of the photopolymerization initiator is 0.01 parts by weight and the upper limit is 10 parts by weight with respect to 100 parts by weight in total of the photopolymerizable compound and the moisture-curable resin.
  • the content of the photopolymerization initiator is in this range, the resulting moisture-curable resin composition is more excellent in photocurability and storage stability.
  • a more preferable lower limit of the content of the photopolymerization initiator is 0.1 parts by weight, and a more preferable upper limit is 5 parts by weight.
  • the moisture-curable resin composition of the present invention preferably contains a photoacid generator.
  • a photoacid generator By containing the photoacid generator, the coloring reaction of the photosensitive colorant can be promoted.
  • the photoacid generator is not particularly limited as long as it generates a protonic acid or a Lewis acid upon irradiation with light, and may be an ionic photoacid generation type or a nonionic photoacid generation type. It is also good.
  • Examples of the anionic moiety of the above-mentioned ionic photoacid generating photoacid generator include an anion moiety of BF 4 ⁇ , PF 6 ⁇ , SbF 6 ⁇ , (BX 4 ) ⁇ (where X is at least 2 or more). And a phenyl group substituted with a trifluoromethyl group or the like) and the like.
  • Examples of the above-mentioned photoacid generator of the ionic photoacid generation type include aromatic sulfonium salts, aromatic iodonium salts, aromatic diazonium salts, aromatic ammonium salts, (2,4-cyclopentadiene, etc.) having the above-mentioned anion moiety. -1-yl) ((1-methylethyl) benzene) -Fe salt and the like.
  • aromatic sulfonium salt examples include bis (4- (diphenylsulfonio) phenyl) sulfide bishexafluorophosphate, bis (4- (diphenylsulfonio) phenyl) sulfide bishexafluoroantimonate, bis (4- (diphenyl) Diphenylsulfonio) phenyl) sulfide bis tetrafluoroborate, bis (4- (diphenylsulfonio) phenyl) sulfide tetrakis (pentafluorophenyl) borate, diphenyl-4- (phenylthio) phenylsulfonium hexafluorophosphate, diphenyl-4- (4) Phenylthio) phenylsulfonium hexafluoroantimonate, diphenyl-4- (phenylthio) phenylsulfon
  • aromatic iodonium salt examples include diphenyliodonium hexafluorophosphate, diphenyliodonium hexafluoroantimonate, diphenyliodonium tetrafluoroborate, diphenyliodonium tetrakis (pentafluorophenyl) borate, bis (dodecylphenyl) iodonium hexafluorophosphate, bis (Dodecylphenyl) iodonium hexafluoroantimonate, bis (dodecylphenyl) iodonium tetrafluoroborate, bis (dodecylphenyl) iodonium tetrakis (pentafluorophenyl) borate, 4-methylphenyl-4- (1-methylethyl) phenyliodonium hexa Fluorophosphate, 4-methylphenyl-4- (1-methylethy
  • aromatic diazonium salt examples include phenyl diazonium hexafluorophosphate, phenyl diazonium hexafluoro antimonate, phenyl diazonium tetrafluoroborate, phenyl diazonium tetrakis (pentafluorophenyl) borate and the like.
  • aromatic ammonium salt examples include 1-benzyl-2-cyanopyridinium hexafluorophosphate, 1-benzyl 2-cyanopyridinium hexafluoroantimonate, 1-benzyl 2-cyanopyridinium tetrafluoroborate, 1-benzyl 2-Cyanopyridinium tetrakis (pentafluorophenyl) borate, 1- (naphthylmethyl) -2-cyanopyridinium hexafluorophosphate, 1- (naphthylmethyl) -2-cyanopyridinium hexafluoroantimonate, 1- (naphthylmethyl) Examples thereof include -2-cyanopyridinium tetrafluoroborate, 1- (naphthylmethyl) -2-cyanopyridinium tetrakis (pentafluorophenyl) borate and the like.
  • Examples of the (2,4-cyclopentadien-1-yl) ((1-methylethyl) benzene) -Fe salt include, for example, (2,4-cyclopentadien-1-yl) ((1-methylethyl) benzene ) -Fe (II) hexafluorophosphate, (2,4-cyclopentadien-1-yl) ((1-methylethyl) benzene) -Fe (II) hexafluoroantimonate, (2,4-cyclopentadiene-1) -Yl) ((1-methylethyl) benzene) -Fe (II) tetrafluoroborate, (2,4-cyclopentadien-1-yl) ((1-methylethyl) benzene) -Fe (II) tetrakis (penta) And fluorophenyl) borate and the like.
  • non-ionic photoacid generating photoacid generator examples include nitrobenzyl ester, sulfonic acid derivative, phosphoric acid ester, phenol sulfonic acid ester, diazonaphthoquinone, N-hydroxyimidosulfonate and the like.
  • photo acid generators commercially available ones include, for example, a photo acid generator manufactured by San-Apro, a photo acid generator manufactured by Midori Chemical, a photo acid generator manufactured by Union Carbide, a product manufactured by ADEKA A photoacid generator, a photoacid generator manufactured by 3M, a photoacid generator manufactured by BASF, a photoacid generator manufactured by Rhodia, etc. may be mentioned.
  • Examples of the photoacid generator manufactured by San-Apro include CPI-100P, CPI-200K, CPI-210S, and the like.
  • Examples of the photoacid generator manufactured by Midori Kagaku Co., Ltd. include DTS-200.
  • UVI6990, UVI6974 etc. are mentioned, for example.
  • examples of the photoacid generator manufactured by ADEKA Corporation include SP-150 and SP-170.
  • Examples of the photoacid generator manufactured by 3M include FC-508 and FC-512.
  • IRGACURE261, IRGACURE290 etc. are mentioned, for example.
  • Examples of the photoacid generator manufactured by Rhodia include PI 2074 and the like.
  • the preferable lower limit of the content of the photoacid generator is 0.1 parts by weight, and the preferable upper limit is 10 parts by weight with respect to 100 parts by weight of the curable resin component.
  • the content of the photoacid generator is in this range, the resulting moisture-curable resin composition is more excellent in colorability and adhesiveness.
  • the more preferable lower limit of the content of the photoacid generator is 1 part by weight, and the more preferable upper limit is 4 parts by weight.
  • the moisture-curable resin composition of the present invention preferably contains a sensitizer.
  • the sensitizer has a role of further enhancing the promoting effect of the coloring reaction of the photosensitive colorant by the photoacid generator.
  • sensitizer examples include 2- (4-methylphenylsulfonyl) phenol, fatty acid amide, ethers, oxalic acid esters, naphthoic acid esters, p-hydroxybenzoic acid esters, phthalic acid diesters, sulfone Amides, hydrocarbon compounds, bisphenol S derivatives, bisphenol A derivatives, various waxes, condensates of aromatic carboxylic acids and amines, higher linear glycols, higher ketones and the like can be mentioned.
  • the fatty acid amide examples include stearic acid amide, stearic acid methylolamide, oleic acid amide, palmitic acid amide, coconut oil fatty acid amide and the like.
  • ethers examples include 1,2-bisphenoxyethane, 1,2-di (3-methylphenoxy) ethane, 1,4-dimethoxynaphthalene, 1,4-dibenzyloxynaphthalene, benzyloxythiophenyl ether And 2-benzyloxynaphthalene, 1,2-bis (phenoxymethyl) benzene, 9,10-dibutoxyanthracene, 9,10-diethoxyanthracene and the like.
  • oxalic acid esters examples include dibenzyl oxalate, di (p-methylbenzyl) oxalate, and di (p-chlorobenzyl) oxalate.
  • Examples of the naphthoic acid esters include 1-hydroxy-2-naphthoic acid phenyl ester and the like.
  • Examples of the p-hydroxybenzoic acid esters include benzyloxybenzoic acid benzyl ester, benzyl p-hydroxybenzoic acid and the like.
  • Examples of the phthalic acid diesters include dibenzyl terephthalate and the like.
  • Examples of the sulfonamides include N-dibenzyltoluenesulfonamide, N-benzyltoluenesulfonamide, p-toluenesulfonamide and the like.
  • Examples of the hydrocarbon compound include m-terphenyl and p-benzylbiphenyl.
  • Examples of the bisphenol S derivatives include 4,4′-di (allyloxy) diphenyl sulfone and the like.
  • the lower limit of the content of the sensitizer is preferably 0.001 parts by weight and the upper limit is 0.1 parts by weight with respect to 100 parts by weight of the curable resin component.
  • the content of the sensitizer is 0.001 parts by weight or more, the sensitizing effect is more exhibited.
  • the content of the sensitizer is 0.1 parts by weight or less, light can be transmitted to the deep part without the absorption becoming too large.
  • the more preferable lower limit of the content of the sensitizer is 0.005 parts by weight, and the more preferable upper limit is 0.05 parts by weight.
  • the moisture-curable resin composition of the present invention preferably contains a filler.
  • the moisture-curable resin composition of the present invention has suitable thixotropy, and the shape after application can be sufficiently maintained.
  • the preferable lower limit of the primary particle diameter of the filler is 1 nm, and the preferable upper limit is 50 nm.
  • the primary particle diameter of the filler is in this range, the resulting moisture-curable resin composition is excellent in coating properties and shape retention after coating, and is particularly suitable for display elements having a narrow frame design. It becomes.
  • a more preferable lower limit of the primary particle diameter of the filler is 5 nm, a more preferable upper limit is 30 nm, a still more preferable lower limit is 10 nm, and a still more preferable upper limit is 20 nm.
  • the primary particle diameter of the above-mentioned filler can be measured by dispersing the above-mentioned filler in a solvent (water, organic solvent, etc.) using NICOMP 380 ZLS (manufactured by PARTICLE SIZING SYSTEMS).
  • the filler may be present as secondary particles (a collection of a plurality of primary particles) in the moisture-curable resin composition of the present invention, and the preferred lower limit of the particle diameter of such secondary particles is The upper limit is 5 nm, preferably 500 nm, more preferably 10 nm, and more preferably 100 nm.
  • the particle diameter of the secondary particles of the filler can be measured by observing the moisture-curable resin composition or the cured product of the present invention using a transmission electron microscope (TEM).
  • TEM transmission electron microscope
  • the filler is preferably an inorganic filler, and examples thereof include silica, talc, titanium oxide, zinc oxide, calcium carbonate and the like. Among them, silica is preferable because of its excellent ultraviolet ray permeability. These fillers may be used alone or in combination of two or more.
  • the filler is preferably subjected to hydrophobic surface treatment.
  • the moisture curable resin composition obtained becomes excellent by the shape-retaining property after application
  • the hydrophobic surface treatment include silylation treatment, alkylation treatment, epoxidation treatment and the like. Among them, silylation treatment is preferable, and trimethylsilylation treatment is more preferable, because it is excellent in the effect of improving shape retention.
  • the method etc. of processing the surface of a filler using surface treatment agents such as hexamethyldisilazane, are mentioned, for example.
  • the above-mentioned trimethylsilylation-treated silica is a method of synthesizing silica by a sol-gel method and spraying a surface treatment agent in a state of flowing silica, or silica in an organic solvent such as alcohol or toluene. Further, after adding a surface treatment agent and water, it can be produced by a method such as evaporating and drying water and an organic solvent with an evaporator.
  • the preferable lower limit of the content of the filler in 100 parts by weight of the moisture-curable resin composition of the present invention is 1 part by weight, and the preferable upper limit is 20 parts by weight.
  • the lower limit of the content of the filler is preferably 2 parts by weight, more preferably 15 parts by weight, still more preferably 3 parts by weight, still more preferably 10 parts by weight, particularly preferably 4 parts by weight. .
  • the moisture-curable resin composition of the present invention may further contain additives such as an ionic liquid, a solvent, metal-containing particles, a reactive diluent and the like, if necessary.
  • a moisture-curable resin composition of the present invention for example, a moisture-curable resin using a mixer such as a homodisper, a homomixer, a universal mixer, a planetary mixer, a kneader, and a 3-roll mill, The method etc. which mix a photosensitive coloring agent and the additive added as needed are mentioned.
  • a mixer such as a homodisper, a homomixer, a universal mixer, a planetary mixer, a kneader, and a 3-roll mill
  • the moisture-curable resin composition of the present invention preferably contains 100 ppm or less of water.
  • the water content is more preferably 80 ppm or less.
  • the water content can be measured by a Karl-Fisher water measuring apparatus.
  • the moisture curable resin composition of the present invention is not solid at 25 ° C.
  • the preferable lower limit of the viscosity measured under the conditions of 25 ° C. and 1 rpm using a cone-plate viscometer is 30 Pa ⁇ s
  • the preferable upper limit is 500 Pa ⁇ s.
  • the more preferable lower limit of the viscosity is 40 Pa ⁇ s
  • the more preferable upper limit is 300 Pa ⁇ s.
  • the preferable lower limit of the thixotropic index of the moisture-curable resin composition of the present invention is 1.3, and the preferable upper limit is 5.0.
  • the resulting moisture-curable resin composition is excellent in coating property and shape retention after coating.
  • This shape retentivity is, for example, technically significant in that a coating width can be maintained in a display device with a narrow frame design.
  • technical significance is significant in that it can maintain a state where it does not protrude from the bonding surface.
  • a more preferable upper limit of the thixotropic index is 4.0.
  • the above-mentioned thixotropic index is a viscosity measured at 25 ° C. and 1 rpm using a cone and plate viscometer, and was measured at 25 ° C. and 10 rpm using a cone and plate viscometer It means the value divided by the viscosity.
  • the optical density (OD value) of a cured product having a thickness of 500 ⁇ m is preferably 1 or more.
  • the moisture-curable resin composition of the present invention is excellent in easiness, concealability, workability, etc. when checking the adhesion state.
  • the OD value is more preferably 2 or more.
  • the OD value of the cured product of the moisture curable resin composition can be measured using an optical densitometer.
  • adherends to be preferably adhered using the moisture-curable resin composition of the present invention include various adherends such as metal, glass, and plastic.
  • adherends such as metal, glass, and plastic.
  • shape of the adherend include a film, a sheet, a plate, a panel, a tray, a rod (rod), a box, and a housing.
  • metal steel, stainless steel, aluminum, copper, nickel, chromium, or its alloy etc. are mentioned, for example.
  • an alkali glass As said glass, an alkali glass, an alkali free glass, quartz glass etc. are mentioned, for example.
  • plastic examples include polyolefin resins, polyamide resins, aromatic polyester resins, polynitrile resins, polymethacrylate resins, polyvinyl resins, and polycarbonates.
  • polyolefin resin examples include high density polyethylene, ultrahigh molecular weight polyethylene, isotactic polypropylene, syndiotactic polypropylene, ethylene propylene copolymer resin and the like.
  • polyamide resin include nylon 6 (N6), nylon 66 (N66), nylon 46 (N46), nylon 11 (N11), nylon 12 (N12), nylon 610 (N610) and nylon 612 (N612).
  • Nylon 6/66 copolymer N6 / 66
  • nylon 6/66/610 copolymer N6 / 66/610
  • nylon MXD6 MXD6
  • nylon 6T nylon 6 / 6T copolymer
  • nylon 66 / PP copolymer
  • nylon 66 / PPS copolymer and the like.
  • aromatic polyester resin examples include polybutylene terephthalate (PBT), polyethylene terephthalate (PET), polyethylene isophthalate (PEI), PET / PEI copolymer, polyarylate (PAR), polybutylene naphthalate (PBN) And liquid crystal polyesters, polyoxyalkylene diimidodidic acid / polybutylene terephthalate copolymers, and the like.
  • PBT polybutylene terephthalate
  • PET polyethylene terephthalate
  • PEI polyethylene isophthalate
  • PET / PEI copolymer PET / PEI copolymer
  • PAR polyarylate
  • PBN polybutylene naphthalate
  • liquid crystal polyesters polyoxyalkylene diimidodidic acid / polybutylene terephthalate copolymers, and the like.
  • polynitrile resin examples include polyacrylonitrile (PAN), polymethacrylonitrile, acrylonitrile / styrene copolymer (AS), methacrylonitrile / styrene copolymer, methacrylonitrile / styrene / butadiene copolymer, etc. Can be mentioned.
  • polymethacrylate resin examples include poly (methyl methacrylate) (PMMA) and poly (ethyl methacrylate).
  • ethylene / vinyl acetate copolymer EVA
  • polyvinyl alcohol PVA
  • vinyl alcohol / ethylene copolymer EVOH
  • PVDC polyvinylidene chloride
  • PVC polyvinyl chloride
  • a composite material having a metal plating layer on the surface can also be mentioned, and as a base material for plating of the composite material, for example, the above-mentioned metals, glass, plastics and the like can be mentioned.
  • materials in which a passivation film is formed by passivating the metal surface can also be mentioned, and as the passivation treatment, for example, heat treatment, anodizing treatment, etc. can be mentioned. .
  • the adhesiveness can be improved by performing a sulfuric acid alumite treatment or a phosphoric acid alumite treatment as the passivation treatment.
  • the method of adhering a to-be-adhered body using the moisture-curable resin composition of this invention the method of having the following processes etc. are mentioned, for example. That is, first, the step of applying the moisture-curable resin composition of the present invention to the first member is performed. Next, a step (bonding step) of bonding the first member and the second member via the moisture-curable resin composition is performed. A method of performing a step (moisture curing step) in which the first member and the second member are bonded by moisture curing of the moisture curable resin in the moisture curable resin composition of the present invention after the laminating step Etc.
  • the moisture-curable resin composition of the present invention contains a photopolymerizable compound
  • the moisture-curable resin composition of the present invention is applied after the moisture-curable resin composition of the present invention is applied to the first member. It is preferable to perform the process (photo-curing process) of irradiating light to the object and curing the photopolymerizable compound in the moisture-curable resin composition of the present invention. In this case, it is preferable to include a step of irradiating light after the bonding step. By including the step of irradiating light after the bonding step, the adhesiveness (initial adhesiveness) immediately after bonding with the adherend can be improved.
  • the first member and / or the second member is made of a material that transmits light, it is preferable to emit light through the first member and / or the second member that transmits light. .
  • the first member and the second member may be intervened by the moisture-curable resin composition. It is preferable to irradiate light to the side surface of the bonded structure, that is, the portion where the moisture curable resin composition is exposed.
  • the moisture-curable resin composition of the present invention can be suitably used as an adhesive for electronic components or an adhesive for display elements.
  • the adhesive for electronic parts which uses the moisture-curable resin composition of the present invention, and the adhesive for display element which uses the moisture-curable resin composition of the present invention are also each one of the present invention. .
  • the present invention it is possible to provide a moisture-curable resin composition which is excellent in colorability and curability and which can suppress fading. Further, according to the present invention, it is possible to provide an adhesive for electronic parts and an adhesive for display elements, which are obtained by using the moisture-curable resin composition.
  • (A) is a schematic diagram which shows the case where the sample for adhesive evaluation is seen from the top
  • (b) is a schematic diagram which shows the case where the sample for adhesive evaluation is seen from the side.
  • Synthesis Example 1 (Preparation of Moisture-Curable Urethane Resin A) 100 parts by weight of polytetramethylene ether glycol ("PTMG-2000" manufactured by Mitsubishi Chemical Corp.) and 0.01 parts by weight of dibutyltin dilaurate as a polyol compound are placed in a 500 mL separable flask, and the pressure is reduced to 20 mmHg. Below, it stirred for 30 minutes at 100 degreeC, and mixed.
  • PTMG-2000 polytetramethylene ether glycol
  • dibutyltin dilaurate dibutyltin dilaurate
  • Synthesis Example 2 (Preparation of Moisture-Curable Urethane Resin B)
  • 100 parts by weight of polypropylene glycol manufactured by AGC, "EXCENOL 2020"
  • 0.01 parts by weight of dibutyltin dilaurate are placed under vacuum (20 mmHg or less) at 100.degree. The mixture was stirred for 30 minutes and mixed.
  • Synthesis Example 3 (Preparation of Moisture-Curable Urethane Resin C)
  • a reaction vessel containing 100 parts by weight of a moisture-curable urethane resin A obtained in the same manner as in Synthesis Example 1 9.8 parts by weight of 3-mercaptopropyltrimethoxysilane ("KBM-803" manufactured by Shin-Etsu Chemical Co., Ltd.) was added. Thereafter, the mixture was stirred and mixed at 80 ° C. for 1 hour to obtain a moisture-curable urethane resin C (weight-average molecular weight: 3100) having an isocyanate group and a trimethoxysilyl group at molecular ends.
  • KBM-803 3-mercaptopropyltrimethoxysilane
  • Example 1 to 10 Comparative Examples 1 and 2
  • a planetary stirrer (“Awatori Neritaro" manufactured by Shinky Co., Ltd.)
  • Example 1 Moisture curable resin compositions of ⁇ 10 and Comparative Examples 1 and 2 were obtained.
  • FIG. 1 is a schematic view showing the case of the adhesion evaluation sample viewed from above (FIG. 1 (a)), and a schematic view showing the case of the adhesion evaluation sample viewed from the side (FIG. 1 (b)) showed that.
  • the obtained samples for evaluation of adhesion were placed in a constant temperature and humidity oven at 85 ° C.
  • a moisture-curable resin composition is defined as “ ⁇ ” when the displacement after standing for 24 hours is 1 mm or less as “ ⁇ ”, “ ⁇ ” when it is more than 1 mm and 3 mm or less as “ ⁇ ” when it exceeds 3 mm.
  • the present invention it is possible to provide a moisture-curable resin composition which is excellent in colorability and curability and which can suppress fading. Further, according to the present invention, it is possible to provide an adhesive for electronic parts and an adhesive for display elements, which are obtained by using the moisture-curable resin composition.

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