WO2023042600A1 - 樹脂組成物、電子部品用接着剤、及びそれらの硬化物、並びに電子部品 - Google Patents

樹脂組成物、電子部品用接着剤、及びそれらの硬化物、並びに電子部品 Download PDF

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WO2023042600A1
WO2023042600A1 PCT/JP2022/031255 JP2022031255W WO2023042600A1 WO 2023042600 A1 WO2023042600 A1 WO 2023042600A1 JP 2022031255 W JP2022031255 W JP 2022031255W WO 2023042600 A1 WO2023042600 A1 WO 2023042600A1
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Prior art keywords
resin composition
component
compound
adhesive
total number
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English (en)
French (fr)
Japanese (ja)
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宏樹 上地
陽平 上杉
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Namics Corp
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Namics Corp
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Priority to CN202280060919.2A priority Critical patent/CN117940488A/zh
Priority to EP22869747.0A priority patent/EP4403596A4/en
Priority to JP2023548371A priority patent/JPWO2023042600A1/ja
Priority to KR1020247005799A priority patent/KR20240054979A/ko
Publication of WO2023042600A1 publication Critical patent/WO2023042600A1/ja
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
    • C08G75/02—Polythioethers
    • C08G75/04—Polythioethers from mercapto compounds or metallic derivatives thereof
    • C08G75/045—Polythioethers from mercapto compounds or metallic derivatives thereof from mercapto compounds and unsaturated compounds
    • 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
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
    • C08K3/013—Fillers, pigments or reinforcing additives
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/02—Non-macromolecular additives
    • C09J11/04—Non-macromolecular additives inorganic
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/02—Non-macromolecular additives
    • C09J11/06—Non-macromolecular additives organic
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/08—Macromolecular additives
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2170/00—Compositions for adhesives

Definitions

  • the present invention relates to resin compositions, adhesives for electronic parts, cured products thereof, and electronic parts.
  • UV and/or thermosetting adhesives for electronic parts In the process of applying UV and/or thermosetting adhesives for electronic parts, air dispensers are the mainstream, but there are challenges in reducing minute areas, minute applications, and production takt time.
  • UV and/or thermosetting adhesives for electronic parts may be collectively referred to simply as "adhesives for electronic parts.”
  • Patent Document 1 discloses a resin composition that uses acrylate and thiol and can be applied by jet dispensing as described above, but does not disclose any cases that were actually considered.
  • the present invention has been made in view of such problems of the prior art.
  • the present invention provides a resin composition excellent in jet-dispensability and curability, an adhesive for electronic parts, a cured product thereof, and an electronic part.
  • the following resin compositions, adhesives for electronic parts, cured products thereof, and electronic parts are provided.
  • the ratio of the total number of (meth)acryloyl groups for the (A) methacrylate compound and the (B) polyfunctional acrylate compound to the total number of thiol groups for the (C) polyfunctional thiol compound is 0.8.
  • a cured product comprising the resin composition according to any one of [1] to [5] above or the adhesive for electronic parts according to [6] above.
  • the resin composition and adhesive for electronic parts of the present invention contain a methacrylate compound as the component (A), they are excellent in workability and stability even if they contain a thiol compound with a high reaction rate.
  • the resin composition and adhesive for electronic parts of the present invention may or may not contain a polyfunctional acrylate compound as component (B), and the conventional (meth)acrylate-radical resin composition Optional acrylate compounds commonly used in products. Since the resin composition and the adhesive for electronic parts of the present invention contain a methacrylate compound as an essential component as described above, they can be continuously discharged by jet dispensing.
  • the resin composition and adhesive for electronic components of the present invention can also be applied to adhesives that only heat-cure without UV irradiation.
  • the resin composition of the present invention is not limited to use for electronic parts.
  • the resin composition and the adhesive for electronic parts of the present invention are used for bonding members constituting a camera module, and are mainly used for temporary fixing using curing by UV irradiation (e.g., active alignment process) and Suitable for use as a fixing adhesive. It is also applicable to adhesives that are only heat-cured without UV irradiation.
  • jet dispenser It is a cross-sectional schematic diagram of an example of a jet dispensing apparatus (jet dispenser).
  • Resin composition One embodiment of the resin composition of the present invention comprises (A) a methacrylate compound, (C) a polyfunctional thiol compound, (D) a radical polymerization initiator, and (E) an anionic polymerization initiator, It is a resin composition.
  • the resin composition of the present embodiment may contain (B) a polyfunctional acrylate compound or may contain (B) a polyfunctional acrylate compound.
  • the (A) methacrylate compound may be referred to as the (A) component.
  • the (B) polyfunctional acrylate compound is referred to as the (B) component
  • the (C) polyfunctional thiol compound is referred to as the (C) component
  • the (D) radical polymerization initiator is referred to as the (D) component
  • (E) The anionic polymerization initiator may be referred to as the (E) component.
  • the resin composition of the present embodiment contains (A) a methacrylate compound, it is excellent in workability and stability even if it contains (C) a polyfunctional thiol compound with a high reaction rate. Further, in the resin composition of the present embodiment, an acrylate compound generally used in conventional (meth)acrylate-radical resin compositions is used as an optional component. Thus, the resin composition of the present embodiment can be continuously discharged by jet dispensing by including (A) the methacrylate compound as an essential component.
  • the compounding ratio of component (A) and component (B) is controlled by the total number of (meth)acryloyl groups of both, and by setting the numerical range as described above, extremely excellent jet dispensing properties can be achieved. .
  • (A):(B) is desirably 10:0 to 5:5.
  • (A):(B) is preferably 5:5 to 2:8 because more acrylate compound is desirable when high UV and/or thermal reactivity is required. desirable.
  • the resin composition of the present embodiment is used for bonding members constituting a camera module, and is preferably used as an adhesive for temporary fixing (for example, active alignment process) and fixing mainly using UV. be. It is also applicable to adhesives that are only heat-cured without UV irradiation. When the adhesive is applied by jet dispensing, impact and heat are applied to the adhesive supplied to the nozzle portion. Therefore, if the resin composition used as the adhesive has good reactivity, the adhesive gels and cannot be discharged. By controlling this reactivity, the resin composition of the present embodiment has improved jet dispensing properties.
  • the resin composition of this embodiment can also be applied to adhesives that only heat-cure without UV irradiation.
  • the resin composition of the present embodiment includes (F) a polymerization inhibitor, (G ) fillers and (H) other components such as black pigments.
  • a polymerization inhibitor such as acrylic acid
  • G polymerization inhibitor
  • H other components such as black pigments.
  • the components described above may be referred to as components (F) to (H) as appropriate.
  • FIG. 1 shows a schematic cross-sectional view of an example of a jet dispensing device (jet dispenser 50).
  • the jet dispenser 50 includes a needle 52 capable of reciprocating motion like a piston, a seal 54 (sealing member) for preventing the resin composition 20 from leaking to the outside even when the needle 52 reciprocates, and a resin composition. and a nozzle 56 for jetting 20 .
  • a syringe (not shown) filled with the resin composition is pushed out by air pressure and the needle 52 reciprocates with the length of the stroke S, whereby the resin composition 20 is It is supplied to the chamber 58 in the jet dispenser 50 and jet dispensed from the nozzle 56 .
  • the nozzle 56 has an inner diameter of 50 to 200 ⁇ m.
  • the resin composition 20 jet-dispensed from the nozzle 56 is supplied to a predetermined target.
  • the resin composition of the present embodiment effectively suppresses gelling in the chamber 58 in the jet dispenser 50, and thus has excellent jet dispenseability and excellent curability after jet dispense.
  • a range indicated by reference numeral 61 in FIG. 1B is a sliding portion 61 in which the needle 52 slides against the seal 54 as the needle 52 reciprocates. It depends on the resin composition 20 .
  • a range indicated by reference numeral 62 in FIG. 1B is a collision portion 62 where the tip of the needle 52 collides with the nozzle 56 as the needle 52 reciprocates. It depends on the resin composition 20 .
  • Component is a methacrylate compound.
  • Component (A) is not particularly limited as long as it has a methacryloyl group.
  • the number of functional groups (that is, the number of methacryloyl groups) in the methacrylate compound (A) is not particularly limited.
  • the methacrylate compound preferably has a functional group equivalent weight of 100 or more and 500 or less, more preferably 100 or more and 400 or less, and 100 or more and 250 or less, from the viewpoint of reactivity, dispersibility and workability. is more preferred.
  • the number of functional groups in one molecule is preferably 1-6, more preferably 1-4, and even more preferably 2 or 3.
  • the component (A) preferably contains a benzene ring in the molecule for the purpose of providing high heat resistance and high reliability to the cured physical properties of the resin composition.
  • the resin composition does not contain a benzene ring in order to make the physical properties of the resin composition after curing low in elasticity.
  • methacrylate compounds include 2-hydroxypropyl methacrylate, 2-hydroxy-1,3-dimethacryloxypropane, 4-hydroxybutyl methacrylate, cyclohexane-1,4-dimethanol monomethacrylate, tetrahydro furfuryl methacrylate, phenoxyethyl methacrylate, phenyl polyethoxy methacrylate, 2-hydroxy-3-phenyloxypropyl methacrylate, o-phenylphenol monoethoxy methacrylate, o-phenylphenol polyethoxy methacrylate, p-cumylphenoxyethyl methacrylate, isobonyl methacrylate, tribromophenyloxyethyl methacrylate, dicyclopentanyl methacrylate, dicyclopentenyl methacrylate, dicyclopentenyloxyethyl methacrylate, 1,4-butanediol dimethacrylate, 1,6
  • ((B) component) (B) Component is a polyfunctional acrylate compound.
  • the resin composition of the present embodiment may further contain an acrylate compound as component (B) in addition to the methacrylate compound as component (A).
  • the polyfunctional acrylate compound is a polyfunctional acrylate compound having two or more acryloyl groups.
  • the polyfunctional acrylate compound is more preferably bifunctional from the viewpoint of jet dispensing properties. If it is trifunctional or more, the jet dispensing property may become disadvantageous.
  • the polyfunctional acrylate compound (B) preferably has a functional group equivalent weight of 100 to 500, more preferably 100 to 400, and 100 to 250. More preferably: The number of functional groups is preferably 1-6, more preferably 1-4, and even more preferably 2 or 3.
  • the component (B) preferably contains a benzene ring in the molecule for the purpose of making the physical properties of the cured resin composition highly heat-resistant and highly reliable. In another aspect, it is preferable that the resin composition does not contain a benzene ring in order to make the physical properties of the resin composition after curing low in elasticity.
  • polyfunctional acrylate compounds include N-acryloyloxyethylhexahydrophthalimide, acryloylmorpholine, 2-hydroxypropyl acrylate, 4-hydroxybutyl acrylate, cyclohexane-1,4-dimethanol monoacrylate, Tetrahydrofurofuryl acrylate, phenoxyethyl acrylate, phenylpolyethoxyacrylate, 2-hydroxy-3-phenyloxypropyl acrylate, o-phenylphenol monoethoxy acrylate, o-phenylphenol polyethoxyacrylate, p-cumylphenoxyethyl acrylate, iso Bonyl acrylate, tribromophenyloxyethyl acrylate, dicyclopentanyl acrylate, dicyclopentenyl acrylate, dicyclopentenyloxyethyl acrylate, 1,4-butanediol diacrylate, 1,6-hexaned
  • the resin composition of the present embodiment has a ratio of the total number of (meth)acryloyl groups for (A) the methacrylate compound and (B) the polyfunctional acrylate compound to the total number of thiol groups for the (C) polyfunctional thiol compound. is preferably 0.8 to 1.2.
  • the reactivity of the resin composition can be improved by adjusting the total number of functional groups of each component to the above ratio.
  • the total number of (meth)acryloyl groups for (A) the methacrylate compound and (B) the polyfunctional acrylate compound means the total number of methacryloyl groups for (A) the methacrylate compound and (B) the acryloyl group for the polyfunctional acrylate compound. It means the sum with the total number of groups.
  • (A) the total number of methacryloyl groups for methacrylate compounds, (B) the total number of acryloyl groups for polyfunctional acrylate compounds, and (C) the total number of thiol groups for polyfunctional thiol compounds will be described.
  • the methacryloyl groups are counted as the total number of methacryloyl groups for (A) methacrylate compounds, and the acryloyl groups are counted as the total number of acryloyl groups for (B) polyfunctional acrylate compounds.
  • a silane coupling agent having a thiol group or (meth)acryloyl group is not counted in the total number of components (A), (B) and (C).
  • the ratio of the total number of methacryloyl groups for (A) the methacrylate compound to the total number of thiol groups for the (C) polyfunctional thiol compound may be 0.1 to 1.2.
  • component ((C) component) (C) A component is a polyfunctional thiol compound.
  • the polyfunctional thiol compound as component (C) imparts thermosetting properties to the resin composition of the present embodiment, and also has the effect of improving UV curability.
  • Component (C) is not particularly limited as long as it has two or more functional groups. However, from the viewpoint of moisture resistance, the component (C) is preferably a non-hydrolyzable thiol that does not contain an ester bond in its molecule because it suppresses hydrolysis.
  • the polyfunctional thiol compound preferably has a molecular weight of 500 or less and is liquid at room temperature.
  • (C) component includes a glycoluril compound represented by the following general formula (1).
  • R 1 and R 2 are each independently hydrogen, an alkyl group having 1 to 10 carbon atoms, or a phenyl group.
  • n is an integer from 0 to 10;
  • the component (C) may be a compound represented by the following chemical formula (2) or chemical formula (3).
  • the compound represented by chemical formula (2) or chemical formula (3) is more preferable as the component (C).
  • polyfunctional thiol resins having no ester bond in the molecule include polyfunctional thiol resins represented by general formula (4).
  • R 3 , R 4 , R 5 and R 6 are each independently hydrogen or C n H 2n SH (n is 2 to 6). Further, at least one of R 3 , R 4 , R 5 and R 6 is C n H 2n SH (n is 2-6). 2 to 4 of R 3 , R 4 , R 5 and R 6 are preferably C n H 2n SH (n is 2 to 6), and 3 of R 3 , R 4 , R 5 and R 6 More preferably, one or four are C n H 2n SH (n is 2-6). Further, n of the polyfunctional thiol compound (C) component represented by the general formula (4) is preferably 2 to 4 from the viewpoint of curability.
  • the thiol compound is more preferably a mercaptopropyl group in which n is 3 from the viewpoint of the balance between the physical properties of the cured product and the curing speed.
  • the (C) component represented by the general formula (4) itself has a sufficiently flexible skeleton, and is effective when it is desired to lower the elastic modulus of the cured product. By adding the component (C) represented by the general formula (4), the elastic modulus of the cured product can be controlled, so that the adhesive strength (especially peel strength) after curing can be increased.
  • component (C) Commercially available products of component (C) include Shikoku Kasei Co., Ltd. thiol glycol uril derivative (product name: TS-G (corresponding to chemical formula (2), thiol equivalent: 100 g / eq), equivalent, thiol equivalent: 114 g/eq)), and a thiol compound manufactured by SC Organic Chemical Co., Ltd. (product name: Multithiol Y-3 (in general formula (4), the main component corresponds to trifunctional thiol)).
  • a single component may be used, or two or more components may be used in combination.
  • the component (C) contains 50 to 100 parts by mass of a glycoluril compound with respect to 100 parts by mass of the component (C), from the viewpoint of maintaining the shear strength after curing of the resin composition.
  • the content of the glycoluril compound in component (C) is more preferably 60 to 100 parts by mass, even more preferably 70 to 100 parts by mass.
  • a polyfunctional thiol resin having an ester bond in the molecule can also be used as the (C) component.
  • the content of the polyfunctional thiol resin is preferably 50 to 100 parts by mass per 100 parts by mass of the component (C) from the viewpoint that the ester bond can impart flexibility to the cured product.
  • the content of the polyfunctional thiol resin having an ester bond in the molecule is 50 parts by mass with respect to 100 parts by mass of the component (C). part, more preferably less than 40 parts by mass, and even more preferably less than 30 parts by mass.
  • Polyfunctional thiol resins having an ester bond in the molecule include, for example, pentaerythritol tetrakis (3-mercaptopropionate), trimethylolpropane tris (3-mercaptopropionate), dipentaerythritol hexakis (3-mercapto propionate), pentaerythritol tetrakis(3-mercaptobutyrate), tris-[(3-mercaptopropionyloxy)-ethyl]-isocyanurate, pentaerythritol tetrakis(3-mercaptobutyrate), 1,4-bis( 3-mercaptobutyryloxy)butane, 1,3,5-tris(3-mercaptobutyryloxyethyl)-1,3,5-triazine-2,4,6(1H,3H,5H)-trione, tri Methylolpropane tris (3-mercaptobutyrate), tri
  • ((D) component) (D) Component is a radical polymerization initiator. Since the resin composition of the present embodiment contains a radical polymerization initiator as the component (D), the resin composition can be cured by short-time heating or UV irradiation.
  • the radical polymerization initiator of component (D) may be a thermal radical polymerization initiator alone, a photoradical polymerization initiator alone, or a combination of these two.
  • the (D) component radical polymerization initiator is more preferably a radical photopolymerization initiator.
  • radical polymerization initiator that can be used in the resin composition of this embodiment is not particularly limited, and known materials can be used.
  • Specific examples of radical polymerization initiators include dicumyl peroxide, t-butylcumyl peroxide, 1,3-bis(2-t-butylperoxyisopropyl)benzene, or 2,5-dimethyl-2,5-bis( Dialkyl peroxides such as t-butylperoxy)hexane; 1,1-bis(t-butylperoxy)cyclohexane, 1,1-bis(t-butylperoxy)-3,3,5-trimethylcyclohexane, 1,1- bis(t-amylperoxy)cyclohexane, 2,2-bis(t-butylperoxy)butane, n-butyl 4,4-bis(t-butylperoxy)valerate, or ethyl 3,3-(t-butylperoxy) Peroxyketals such as buty
  • Examples include 1-hydroxycyclohexyl-phenylketone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, diethoxyacetophenone, 1-(4-isopropylphenyl)-2-hydroxy-2 -methylpropan-1-one, 1-(4-dodecylphenyl)-2-hydroxy-2-methylpropan-1-one, 4-(2-hydroxyethoxy)-phenyl(2-hydroxy-2-propyl)ketone , 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one, benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin n-butyl ether, benzoin phenyl ether, benzyl dimethyl ketal, benzophenone, benzoylbenzoic acid, methyl benzoylbenzoate, 4-phenylbenzophenone, hydroxybenzophenone, acrylated
  • the content of the radical polymerization initiator of component (D) is not particularly limited.
  • the radical polymerization initiator of component (D) is preferably contained in the resin composition at a ratio of 0.01 to 20% by mass, more preferably 0.03 to 10% by mass. More preferably, it is contained in an amount of 0.05 to 5% by mass.
  • good curability was confirmed even when the content ratio of component (D) in the resin composition was 2% by mass or less.
  • ((E) component) (E) Component is an anionic polymerization initiator.
  • the resin composition of the present embodiment further contains an anionic polymerization initiator as component (E) in addition to the radical polymerization initiator as component (D).
  • Such an anionic polymerization initiator is a polymerization initiator that initiates polymerization when heated. For example, when the resin composition is used as an adhesive for electronic parts, it is effectively used during main curing after temporary fixing. .
  • anionic polymerization initiator that can be used in the resin composition of this embodiment is not particularly limited, and known materials can be used.
  • Specific examples of anionic polymerization initiators include imidazole compounds that are solid at room temperature, solid-dispersed amine adduct-based latent curing accelerators such as reaction products of amine compounds and epoxy compounds (amine-epoxy adduct systems), A reaction product (urea-type adduct system) of an amine compound and an isocyanate compound or a urea compound is included.
  • imidazole compounds that are solid at room temperature examples include 2-heptadecylimidazole, 2-phenyl-4,5-dihydroxymethylimidazole, 2-undecylimidazole, 2-phenyl-4-methyl- 5-hydroxymethylimidazole, 2-phenyl-4-benzyl-5-hydroxymethylimidazole, 2,4-diamino-6-(2-methylimidazolyl-(1))-ethyl-S-triazine, 2,4-diamino -6-(2'-methylimidazolyl-(1)')-ethyl-S-triazine isocyanuric acid adduct, 2-methylimidazole, 2-phenylimidazole, 2-phenyl-4-methylimidazole, 1-cyanoethyl -2-phenylimidazole, 1-cyanoethyl-2-methylimidazole-trimellitate, 1-cyanoethyl-2-pheny
  • Examples of the epoxy compound used as one of raw materials for producing the solid-dispersed amine adduct-based latent curing accelerator (amine-epoxy adduct-based) that can be used in the present invention include bisphenol A, bisphenol F, catechol, and resorcinol.
  • Polyglycidyl ether obtained by reacting polyhydric phenol such as polyhydric phenol, or polyhydric alcohol such as glycerin or polyethylene glycol with epichlorohydrin; p-hydroxybenzoic acid, hydroxycarboxylic acid such as ⁇ -hydroxynaphthoic acid glycidyl ether esters obtained by reacting with epichlorohydrin; polyglycidyl esters obtained by reacting polycarboxylic acids such as phthalic acid and terephthalic acid with epichlorohydrin; 4,4'-diaminodiphenylmethane and glycidylamine compounds obtained by reacting m-aminophenol or the like with epichlorohydrin; further polyfunctional epoxy compounds such as epoxidized phenol novolak resins, epoxidized cresol novolak resins, and epoxidized polyolefins; butyl glycidyl ether; monofunctional epoxy compounds such as phen
  • the amine compound used as another raw material for producing the solid-dispersed amine adduct-based latent curing accelerator has one or more active hydrogens in the molecule capable of undergoing an addition reaction with an epoxy group, and a primary amino group, Any compound having at least one functional group selected from a secondary amino group and a tertiary amino group in the molecule may be used. Examples of such amine compounds are shown below, but are not limited thereto.
  • aliphatic amines such as diethylenetriamine, triethylenetetramine, n-propylamine, 2-hydroxyethylaminopropylamine, cyclohexylamine, 4,4'-diamino-dicyclohexylmethane; 4,4'-diaminodiphenylmethane; , aromatic amine compounds such as 2-methylaniline; nitrogen atom-containing heterocycles such as 2-ethyl-4-methylimidazole, 2-ethyl-4-methylimidazoline, 2,4-dimethylimidazoline, piperidine, piperazine compounds; and the like.
  • compounds having a tertiary amino group in the molecule in particular are raw materials that provide latent curing accelerators having excellent curing accelerating ability.
  • examples of such compounds include, for example, dimethylaminopropyl Amine compounds such as amine, diethylaminopropylamine, di-n-propylaminopropylamine, dibutylaminopropylamine, dimethylaminoethylamine, diethylaminoethylamine, N-methylpiperazine, 2-methylimidazole, 2-ethylimidazole, 2-ethyl - Primary or secondary amines having a tertiary amino group in the molecule, such as imidazole compounds such as 4-methylimidazole and 2-phenylimidazole; 2-dimethylaminoethanol, 1-methyl-2-dimethylaminoethanol , 1-phenoxymethyl-2-dimethylaminoethanol, 2-diethylaminoethanol, 1-butoxymethyl-2-dimethyl
  • Examples of the isocyanate compound used as another production raw material for the solid-dispersed amine adduct latent curing accelerator include monofunctional isocyanate compounds such as n-butyl isocyanate, isopropyl isocyanate, phenyl isocyanate, and benzyl isocyanate.
  • terminal isocyanate group-containing compounds examples include an addition compound having a terminal isocyanate group obtained by the reaction of toluylene diisocyanate and trimethylolpropane, and a terminal isocyanate group obtained by the reaction of toluylene diisocyanate and pentaerythritol. but not limited thereto.
  • urea compounds include urea and thiourea, but are not limited to these.
  • the solid dispersion type latent curing accelerator that can be used in the present invention can be obtained, for example, by the following method. First, the two components of (a) the amine compound and the epoxy compound, (b) the three components of the two components and the active hydrogen compound, or (c) at least one of the amine compound and the isocyanate compound and the urea compound. Each component is taken and mixed in a combination of two or three components. The resulting mixture is then reacted at a temperature between room temperature and 200°C.
  • the obtained reactant is solidified by cooling and pulverized, or reacted in a solvent such as methyl ethyl ketone, dioxane, tetrahydrofuran, etc., and after removal of the solvent, the solid content is pulverized to obtain the above-mentioned solid dispersion type latent.
  • a hardening accelerator can be easily obtained.
  • the amine-epoxy adduct system includes "Amicure PN-23" (manufactured by Ajinomoto Co., Ltd., trade name), "Amicure PN-40” (manufactured by Ajinomoto Co., Ltd., trade name), "Amicure PN -50" (manufactured by Ajinomoto Co., Ltd., trade name), "Hardner X-3661S” (manufactured by ACR, trade name), “Hardner X-3670S” (manufactured by ACR, trade name), "Novacure HX-3742” (manufactured by Asahi Kasei, trade name), “Novacure HX-3721” (manufactured by Asahi Kasei, trade name), "Novacure HX
  • the content of the anionic polymerization initiator of component (E) is not particularly limited.
  • the component (E) anionic polymerization initiator is preferably contained in the resin composition in an amount of 0.5 to 10% by mass, more preferably 1 to 5% by mass, and 1 to 3% by mass. It is more preferable that the content is % by mass.
  • ((F) component) (F) Component is a polymerization inhibitor.
  • the polymerization inhibitor of component (F) is added to enhance the stability of the resin composition during storage.
  • polymerization inhibitors include radical polymerization inhibitors.
  • the component (F), the radical polymerization inhibitor is added to suppress the progress of an unintended radical polymerization reaction.
  • the methacrylate compound (A) component and the polyfunctional acrylate compound (B) component may generate radicals by themselves with a low probability. At this time, an unintended radical polymerization reaction may proceed from the radical as a starting point.
  • a radical polymerization inhibitor progress of such unintended radical polymerization reaction of the components (A) and (B) can be suppressed.
  • a known polymerization inhibitor can be used as the component (F).
  • Component (F) used is preferably at least one selected from the group consisting of, for example, N-nitroso-N-phenylhydroxylamine aluminum, triphenylphosphine, p-methoxyphenol, and hydroquinone.
  • known radical polymerization inhibitors disclosed in JP-A-2010-117545 and JP-A-2008-184514 can also be used as the component (F).
  • a single component may be used, or two or more components may be used in combination.
  • a component is a filler.
  • a filler As the component (G), it is possible to improve the moisture resistance and the ability to drain liquid during jet dispensing.
  • the content of the filler is not particularly limited, but for example, the resin composition of the present embodiment preferably contains 0 to 65% by mass of the filler of component (G), more preferably 5 to 50% by mass. Preferably, it is more preferably contained in an amount of 10 to 30% by mass.
  • a known filler can be used as the component (G).
  • an inorganic filler and an organic filler are mentioned, for example.
  • inorganic fillers include glass, silica, alumina, aluminum nitride, boron nitride, titanium oxide, calcium carbonate, talc, and silver fillers.
  • organic fillers include silicone rubber, PTFE, polystyrene, polyacrylate, polyurethane, and polydivinylbenzene fillers.
  • the average particle size of the filler is preferably 0.1 to 10 ⁇ m, more preferably 0.3 to 5 ⁇ m, even more preferably 0.5 to 5 ⁇ m.
  • the (H) component is a black pigment.
  • the black pigment as component (H) is a particularly effective component when the resin composition of the present embodiment is used as an adhesive that requires light blocking properties, such as an adhesive for camera modules.
  • an adhesive for camera modules For example, when a resin composition is used as an adhesive for a camera module, light may enter the camera module from a portion coated with the resin composition. For this reason, it is preferable to contain a black pigment as the (H) component in order to provide a light shielding property to prevent light from entering the camera module.
  • the (H) component used includes, for example, carbon black, graphite, titanium nitride, titanium oxide, zirconia, and titanium black.
  • the resin composition of the present embodiment may contain (I) an anionic polymerization inhibitor (hereinafter also referred to as "(I) component") within a range that does not impair the effects of the present invention.
  • the anionic polymerization inhibitor is for enhancing the stability of the resin composition during storage, and is added to suppress the occurrence of polymerization reaction due to unintended basic components.
  • anionic polymerization inhibitors can be used.
  • boric acid ester compounds and strong acids can be used.
  • Specific examples of (I) anionic polymerization inhibitors include trimethylborate, triethylborate, tri-n-propylborate, triisopropylborate, trifluoromethanesulfonic acid, maleic acid, methanesulfonic acid, barbituric acid, and difluoroacetic acid. , trichloroacetic acid, phosphoric acid, and dichloroacetic acid.
  • the preferred (I) anionic polymerization inhibitor is at least one selected from tri-n-propylborate, triisopropylborate and barbituric acid.
  • an anionic polymerization inhibitor known ones disclosed in JP-A-2010-117545, JP-A-2008-184514, JP-A-2017-171804, etc. can also be used.
  • the anionic polymerization inhibitor may be used alone or in combination of two or more.
  • the content of component (I) is preferably 0.1 to 10% by mass, more preferably 0.3 to 7% by mass, relative to the total mass of the resin composition.
  • the resin composition of the present embodiment may further contain components other than components (A) to (I) described above, if necessary.
  • Specific examples of such components include antifoaming agents, silane coupling agents, dispersants, thixotropic agents, and epoxy resins.
  • the type and amount of each compounding agent are as per usual methods.
  • the resin composition of the present embodiment preferably has, for example, the following properties.
  • the viscosity of the resin composition of the present embodiment is preferably 0.2 to 80 Pa s, more preferably 1 to 60 Pa s, even more preferably 1 to 50 Pa s, 20 Pa ⁇ s is particularly preferred. By configuring in this way, the handling property as a product is good, and the workability can be kept good and high.
  • the viscosity of the resin composition can be measured at room temperature (25° C.) at a rotational speed of 50 rpm using, for example, a Brookfield (B-type) viscometer.
  • the TI (thixotropy index) of the resin composition of the present embodiment is preferably 0.7 to 7 at room temperature (25° C.), more preferably 0.9 to 6.5, and 1 to 6.5. 5 is more preferred.
  • the thixotropy index of the resin composition is obtained by dividing the value measured at a rotational speed of 5 rpm at room temperature (25° C.) using a (B-type) viscometer manufactured by Brookfield Co. by the value measured at a rotational speed of 50 rpm. can be measured by
  • the resin composition of this embodiment can be produced by a conventional method.
  • the resin composition of the present embodiment can be produced by mixing each component described above using, for example, a Laikai machine, a pot mill, a three-roll mill, a rotary mixer, a twin-screw mixer, or the like. .
  • the resin composition of this embodiment can be used as an adhesive for electronic parts. Moreover, the resin composition of the present embodiment can be suitably applied to engineering plastics.
  • the resin composition of the present embodiment is used as an adhesive for electronic parts, the electronic parts to be adhered are not particularly limited, and examples thereof include ceramic substrates, organic substrates, and semiconductor chips.
  • the resin composition is used in the step of applying an adhesive for electronic parts with a jet dispenser 50 as shown in FIG.
  • the resin composition of the present embodiment can be effectively used, for example, as an adhesive for camera modules. That is, it can be used for bonding members constituting a camera module to each other, and can be mainly used for fixing members to each other using UV. As for the fixation of the members, it can be used for temporary fixation in the active alignment process and permanent fixation for finally fixing the camera module.
  • the resin composition of the present embodiment can meet the requirement of fluidity required when fixing the camera module.
  • the jet dispenser 50 as shown in FIG. 1 can jet several hundred shots per second by reciprocating the needle 52 . Therefore, a large impact is applied to the resin composition 20 (for example, adhesive) for jet dispensing. Even after being subjected to such a large impact, the resin composition of the present embodiment (resin composition 20) can maintain fluidity.
  • the resin composition 20 for example, adhesive
  • a jet dispenser is used to supply the adhesive for fixing the components of the camera module.
  • the width of the minute area or gap to which the adhesive is supplied is several hundred ⁇ m (for example, 300 ⁇ m). If the resin composition of the present embodiment is jet-dispensed, the adhesive can be supplied to small-sized areas and gaps.
  • Adhesive for electronic parts Next, embodiments of the adhesive for electronic components of the present invention will be described.
  • the adhesive for electronic parts of this embodiment is an adhesive for electronic parts using the resin composition of this embodiment described above.
  • the cured product of the embodiment is a cured product made of the resin composition of the present embodiment described above. Further, the cured product of the embodiment may be a cured product of an adhesive for electronic parts using the resin composition of the present embodiment described above.
  • the electronic component of the present invention has high productivity because it contains a cured product of the resin composition described above or a cured product of an adhesive for electronic components using the resin composition. Moreover, it is highly reliable.
  • Example preparation After weighing and blending each component shown in Tables 1 to 4, they were mixed to prepare resin compositions of Examples and Comparative Examples. Specifically, each component shown in Tables 1 to 4 was dispersed by a three-roll mill and made into a paste to prepare a resin composition. Details of each component shown in Tables 1 to 4 are as follows.
  • (A) component; methacrylate compound] (A1): Phenoxyethyl methacrylate, manufactured by Kyoeisha Chemical Co., Ltd. (trade name: Light Ester PO, methacrylate equivalent: 206 g/eq, number of methacryloyl groups per molecule: 1).
  • (B) component; polyfunctional acrylate compound] (B1): Polyester acrylate (polyfunctional acrylic compound), manufactured by Toagosei Co., Ltd. (trade name: M7100, acrylate equivalent: 188 g/eq, number of acryloyl groups per molecule: 3 or more).
  • (C) component; polyfunctional thiol compound] (C1): 1,3,4,6-tetrakis(2-mercaptoethyl)glycoluril, manufactured by Shikoku Kasei Kogyo Co., Ltd. (trade name: TS-G, thiol equivalent: 94 g/eq, number of thiol groups in one molecule : 4).
  • C3 Pentaerythritol tetrakis(3-mercaptopropionate), manufactured by SC Organic Chemical (trade name: PEMP-LV, thiol equivalent: 122 g/eq, number of thiol groups per molecule: 4).
  • C4 3-(3-mercapto-propoxy)-2,2-bis-(3-mercapto-propoxymethyl)-propan-1-ol, manufactured by SC Organic Chemical Co., Ltd. (trade name: Multiiol Y-3, thiol Equivalent weight: 124 g/eq, number of thiol groups in one molecule: 3).
  • (D) component; radical polymerization initiator (D1): 1,1,3,3-tetramethylbutylperoxy-2-ethylhexanoate, manufactured by NOF Corporation (trade name: Perocta O, thermal radical polymerization initiator).
  • (E) component; anionic polymerization initiator (E1): A mixture of a microencapsulated amine-based curing agent and bisphenol A-type and F-type epoxy resins, in which 33% by mass of the amine-based curing agent is microencapsulated, manufactured by Asahi Kasei Corporation (trade name: HXA9322HP). . (E2): Modified alicyclic polyamine, manufactured by T&K TOKA (trade name: FXR-1121).
  • (F) component; polymerization inhibitor (F1): N-nitroso-N-phenylhydroxylamine aluminum, manufactured by Fuji Film Wako Pure Chemical Industries, Ltd. (trade name: Q-1301).
  • G1 Spherical silica, manufactured by Admatechs (trade name: SE5200 SEE).
  • G2 Spherical silica, manufactured by Admatechs (trade name: SE2200 SEE).
  • G3 Silicone composite powder, manufactured by Shin-Etsu Chemical Co., Ltd. (trade name: KMP-600T).
  • G4 Fumed silica, manufactured by Cabot Corporation (trade name: TS-720).
  • H1 Carbon black, manufactured by Evonik Degussa Japan (trade name: Black 4).
  • H2 Titanium nitride, titanium dioxide, manufactured by Mitsubishi Materials Electronic Chemicals (trade name: Titanium Black 13M).
  • (J) component; other components Silane coupling agent, manufactured by Shin-Etsu Chemical Co., Ltd. (trade name: KBM403; 3-glycidoxypropyltrimethoxysilane).
  • the functional group ratio (1) is the ratio of the total number of methacryloyl groups in component (A) to the total number of acryloyl groups in component (B) (that is, the total number of methacryloyl groups in component (A)/(B) total number of acryloyl groups in the component).
  • the functional group ratio (2) is the ratio of the total number of methacryloyl groups of component (A) and the total number of acryloyl groups of component (B) to the total number of thiol groups of component (C) (i.e. ⁇ component (A) total number of methacryloyl groups + total number of acryloyl groups in component (B) ⁇ /total number of thiol groups in component (C)).
  • the results of functional group ratio (1) and ratio (2) for each component are shown in Tables 1-4.
  • the jet-dispensed resin composition was subjected to UV curing or heat curing, and the UV curing depth or the strength at the time of heat curing was measured.
  • ⁇ UV curing depth> Two heat-resistant tapes (thickness: 100 ⁇ m) were pasted on a black resin plate A (width: 50 mm ⁇ length: 25 mm ⁇ thickness: 1.5 mm) at intervals of 10 mm. Next, the resin composition was applied between the two heat-resistant tapes on the resin plate A so as to have the same thickness of 100 ⁇ m as the heat-resistant tape.
  • the integrated amount of light was measured by connecting a receiver "UVD-365 (trade name)" of "UIT-250 (trade name)” manufactured by Ushio Inc.. Peel off one of the sandwiched resin plates A and B, remove the uncured portion attached to the cured product of the resin composition, measure the distance of the cured portion from the UV irradiation surface with a microscope, and measure the UV curing depth. and ⁇ Strength> A 2 mm ⁇ 3 mm ceramic chip was placed on each of the resin compositions of Examples and Comparative Examples that were jet-dispensed onto a ceramic substrate.
  • UV curing was performed by UV irradiation with an integrated light amount of 2000 mJ/cm 2 using a UV LED irradiation device “AC475 (trade name)” manufactured by Excelitas Technologies.
  • the integrated amount of light was measured by connecting a receiver "UVD-365 (trade name)” of "UIT-250 (trade name)” manufactured by Ushio Inc..
  • the UV-cured curable resin composition was thermally cured at 80° C. for 60 minutes in a blower dryer.
  • DAGE4000 universal bond tester
  • the cured product cured as described above was evaluated according to the following evaluation criteria. In the following evaluation criteria, the evaluation of "A" is the best, and the evaluation is inferior in the order of "O", " ⁇ ", and "X".
  • the UV curing depth is more than 350 ⁇ m and less than 450 ⁇ m, or the strength at the time of heat curing is more than 60 N and less than 130 N.
  • the resin compositions of Examples 1 to 23 containing a methacrylate compound as component (A) showed good results in both curability and jet dispensing properties. Moreover, it was confirmed that the resin compositions of Examples 1 to 23 exhibited curability when the content of the radical polymerization initiator as the component (C) was 2% by mass or less.
  • the resin composition of Comparative Example 1 did not contain a methacrylate compound as the component (A), the number of shots that could be discharged continuously was less than 500 in the evaluation of jet dispense properties. Compared to the resin compositions of Examples 1 to 23, the resin composition of Comparative Example 1 was found to readily undergo gelation in a jet dispenser and was not suitable for application by jet dispensing.
  • the resin composition of the present invention can be used as a resin composition that can be applied by jet dispensing, and can be effectively used as an adhesive, for example, an adhesive for electronic parts.
  • the resin composition, the adhesive for electronic parts, and the cured product thereof of the present invention can be used for the production of electronic parts.
  • the resin composition of the present invention can be suitably used for engineering plastics.

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