WO2023017752A1 - 樹脂組成物及び接着剤 - Google Patents
樹脂組成物及び接着剤 Download PDFInfo
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- WO2023017752A1 WO2023017752A1 PCT/JP2022/029484 JP2022029484W WO2023017752A1 WO 2023017752 A1 WO2023017752 A1 WO 2023017752A1 JP 2022029484 W JP2022029484 W JP 2022029484W WO 2023017752 A1 WO2023017752 A1 WO 2023017752A1
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- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- AJSTXXYNEIHPMD-UHFFFAOYSA-N triethyl borate Chemical compound CCOB(OCC)OCC AJSTXXYNEIHPMD-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- QYJYJTDXBIYRHH-UHFFFAOYSA-N trimethoxy-[8-(oxiran-2-ylmethoxy)octyl]silane Chemical compound C(C1CO1)OCCCCCCCC[Si](OC)(OC)OC QYJYJTDXBIYRHH-UHFFFAOYSA-N 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- 229940096522 trimethylolpropane triacrylate Drugs 0.000 description 1
- RMZAYIKUYWXQPB-UHFFFAOYSA-N trioctylphosphane Chemical compound CCCCCCCCP(CCCCCCCC)CCCCCCCC RMZAYIKUYWXQPB-UHFFFAOYSA-N 0.000 description 1
- 239000012953 triphenylsulfonium Substances 0.000 description 1
- 229940070710 valerate Drugs 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 125000001834 xanthenyl group Chemical class C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- 150000007964 xanthones Chemical class 0.000 description 1
- DIHAURBCYGTGCV-UHFFFAOYSA-N xi-4,5-Dihydro-2,4(5)-dimethyl-1H-imidazole Chemical compound CC1CN=C(C)N1 DIHAURBCYGTGCV-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
-
- 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
- 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
- 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
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
- H01L21/50—Assembly of semiconductor devices using processes or apparatus not provided for in a single one of the subgroups H01L21/06 - H01L21/326, e.g. sealing of a cap to a base of a container
- H01L21/52—Mounting semiconductor bodies in containers
Definitions
- the present invention relates to a resinous composition, an adhesive containing the same, a cured product thereof, a semiconductor device and an electronic component containing the cured product.
- Adhesives that are temporarily fixed by ultraviolet (UV) irradiation and fully cured by heat are used in many fields (for example, Patent Documents 1 and 2), and are particularly often used for image sensor modules.
- Image sensor modules are used as camera modules for mobile phones and smart phones.
- Adhesives used in the manufacture of image sensor modules are used, for example, in the process of aligning optical axes, such as bonding the sensor section and the lens section of the image sensor module, and are required to have high photocurability.
- a UV-curable adhesive using en-thiol reaction is known.
- Patent Document 3 describes (A) an acrylic resin, (B) a thiol compound, (C) a latent curing agent, (D) a radical polymerization inhibitor, (E ) A resin composition is disclosed which is characterized by containing an anionic polymerization inhibitor.
- High-energy 365 nm UV light is generally used for photo-curing of UV-curable adhesives.
- the part when bonding certain parts of the image sensor module (for example, an IR cut filter), the part itself absorbs UV light of 400 nm or less, so the adhesive under or around the part becomes uncured.
- Adhesives that cure with longer wavelength UV light are desired in order to adhere such components satisfactorily.
- the adhesive when used in the process of aligning the optical axis, such as bonding the sensor part and the lens part of the image sensor module, extremely high curing accuracy is required to prevent optical axis misalignment. It is required to prevent unintended hardening by irradiation of white light such as indoor light such as fluorescent light (hereinafter such light is called "environmental light”) at the time of aligning the parts before performing .
- an object of the present invention is to provide a resin composition and an adhesive that have high curability and photocuring adhesive strength with UV light having a longer wavelength (e.g., 405 nm) and are stable against ambient light.
- a first embodiment of the present invention is the following resin composition.
- (1) (A) (meth)acrylate compound, (B) a thiol compound, and (C) the following formula (1):
- R is hydrogen or an alkyl group.
- Ratio of the number of thiol group equivalents of component (B) to the number of (meth)acryloyl group equivalents of component (A) ([number of thiol group equivalents of component (B)]/[(meth)acryloyl of component (A) Group equivalent number]) is 0.5 to 1.8, the resin composition according to the above (1).
- (3) The resin composition according to (1) or (2) above, further comprising (D) a thermal polymerization initiator.
- a second embodiment of the present invention is the following adhesive.
- a third embodiment of the present invention provides (6) a resin composition according to any one of (1) to (3) above, or a cured adhesive according to (4) or (5) above. It is a thing.
- a fourth embodiment of the present invention is (7) a semiconductor device comprising the cured product according to (6) above.
- a fifth embodiment of the present invention is the following electronic component. (8) An electronic component including the semiconductor device according to (7) above. (9) The electronic component according to (8) above, which is an image sensor or a camera module.
- a resin composition that has high curability and photocuring adhesion strength with UV light of a longer wavelength (e.g., 405 nm) and is stable to ambient light can be done.
- an adhesive that has high curability with UV light of a longer wavelength (for example, 405 nm) and photocuring adhesive strength and is stable against ambient light is obtained. be able to.
- a cured product having high adhesive strength can be obtained.
- an electronic component including a semiconductor device having high adhesive strength can be obtained.
- FIG. 2 is a schematic side view of a jig for measuring the photocuring depth of a resin composition.
- FIG. 2 is a top plan view of a jig for measuring the photocuring depth of a resin composition.
- the resin composition which is the first embodiment of the present invention, (A) (meth)acrylate compound, (B) a thiol compound, and (C) the following formula (1): (In the formula, R is hydrogen or an alkyl group.) Including a photoinitiator represented by. According to the present embodiment, it is possible to obtain a resin composition that has high curability and photocuring adhesion strength with UV light having a longer wavelength (for example, 405 nm) and is stable against ambient light.
- the resin composition of the present embodiment contains (A) (meth)acrylate compound (hereinafter also referred to as “(A) component”).
- (A) The (meth)acrylate compound can impart transparency and appropriate hardness to the cured resin composition.
- the (meth)acrylate compound as component (A) is not particularly limited as long as it has one or more (meth)acryloyl groups. In consideration of ensuring heat resistance, compounds having two or more (meth)acryloyl groups are preferred, compounds having 2 to 6 (meth)acryloyl groups are more preferred, and two (meth)acryloyl groups.
- a compound having one (meth)acryloyl group can also be used to adjust the viscosity and physical properties of the cured product (adhesive strength, flexibility, etc.). can.
- (meth)acrylate compounds include tris(2-hydroxyethyl)isocyanurate diacrylate and/or dimethacrylate; tris(2-hydroxyethyl)isocyanurate triacrylate and/or trimethacrylate; trimethylol Propane triacrylate and/or trimethacrylate, or oligomers thereof; pentaerythritol triacrylate and/or trimethacrylate, or oligomers thereof; polyacrylates and/or polymethacrylates of dipentaerythritol; tris(acryloxyethyl)isocyanurate; caprolactone modification tris(acryloxyethyl) isocyanurate; caprolactone-modified tris(methacryloxyethyl) isocyanurate; alkyl-modified dipentaerythritol polyacrylate and/or polymethacrylate; caprolactone-modified dipentaerythritol polyacrylate and/or polymethacrylate
- the component (A) is preferably an acrylate compound and does not substantially contain a methacrylate compound.
- the (A) (meth)acrylate compound any one of the (meth)acrylate compounds described above may be used, or two or more thereof may be used in combination.
- the component (A) preferably has a viscosity of 0.01 to 80 Pa ⁇ s from the viewpoint of the preparation and dispensing properties of the resin composition.
- viscosity refers to a value measured at a measurement temperature of 25°C using an appropriate viscometer depending on the viscosity range.
- component (A) Commercially available products of component (A) include, for example, polyester acrylate (product name: EBECRYL810) manufactured by Daicel-Ornex Co., Ltd., polyester acrylate (product name: M7100) manufactured by Toagosei Co., Ltd., and dimethylol-tricyclodecanedi manufactured by Kyoeisha Chemical Co., Ltd. Acrylate (Product name: Light Acrylate DCP-A) can be mentioned.
- component may use any one type, and may use 2 or more types together.
- the content of component (A) is preferably 10 to 70% by mass, more preferably 20 to 60% by mass, based on the total mass of the resin composition.
- the resin composition of the present embodiment contains (B) a polythiol compound (hereinafter also referred to as "component (B)").
- component (B) The polythiol compound imparts high photocurability to the resin composition.
- Component (B) is not particularly limited as long as it has two or more thiol groups.
- polythiol compounds include pentaerythritol tetrakis (3-mercaptopropionate), trimethylolpropane tris (3-mercaptopropionate), dipentaerythritol hexakis (3-mercaptopropionate), 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, trimethylolpropane tris(3-mercaptobutyrate ), and trimethylolethane tris (3-mercaptobutyrate
- component (B) Commercially available products of component (B) include trimethylolpropane tris(3-mercaptopropionate) (manufactured by SC Organic Chemical Co., Ltd.: TMMP) and tris-[(3-mercaptopropionyloxy)-ethyl]-isocyanurate.
- TMMP trimethylolpropane tris(3-mercaptopropionate)
- TMMP tris-[(3-mercaptopropionyloxy)-ethyl]-isocyanurate.
- examples of (B) polythiol compounds include glycoluril compounds represented by the following general formula (2).
- 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 (B) component may be a compound represented by the following chemical formula (3) or chemical formula (4).
- the compound represented by chemical formula (3) or chemical formula (4) is a more preferable compound as component (B).
- polythiol compounds include polythiol compounds represented by general formula (5).
- 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).
- the polythiol compound (B) represented by the general formula (5) preferably has n of 2 to 4 from the viewpoint of curability. Moreover, it is more preferable that this polythiol compound is 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 (B) component represented by the general formula (5) itself has a sufficiently flexible skeleton, and is effective when it is desired to lower the elastic modulus of the cured product.
- the elastic modulus of the cured product can be controlled, so that the adhesive strength (especially peel strength) after curing can be increased.
- component (B) Commercially available products of component (B) include Shikoku Kasei Co., Ltd.'s thiol glycol uril derivative (product name: TS-G (corresponding to chemical formula (3), thiol equivalent: 100 g/eq), C3 TS-G (chemical formula (4) , thiol equivalent: 114 g/eq)), and SC Organic Chemical thiol compound (product name: PEPT (corresponding to general formula (5), thiol equivalent: 124 g/eq)).
- TS-G thiol glycol uril derivative
- C3 TS-G chemical formula (4) , thiol equivalent: 114 g/eq
- SC Organic Chemical thiol compound product name: PEPT (corresponding to general formula (5), thiol equivalent: 124 g/eq)
- any one type may be used, or two or more types may be used in combination.
- the ratio of the thiol group equivalent number of component (B) to the (meth) acryloyl group equivalent number of component (A) is preferably from 0.5 to 1.8, more preferably from 0.6 to 1.6, even more preferably from 0.7 to 1.4.
- functional group equivalents such as acryloyl equivalents and thiol equivalents represent the molecular weight of a compound per functional group
- functional group equivalents such as acryloyl group equivalents and thiol group equivalents are compounds It represents the number of functional groups (equivalent number) per mass (amount charged).
- the thiol equivalent of component (B) is theoretically the number obtained by dividing the molecular weight of component (B) by the number of thiol groups in one molecule.
- the actual thiol equivalent weight can be determined, for example, by potentiometrically determining the thiol number.
- (A) The (meth)acryloyl equivalent of a (meth)acrylate compound is theoretically equal to the molecular weight of the (meth)acrylate compound divided by the number of acryloyl groups (or methacryloyl groups) in one molecule.
- the actual (meth)acryloyl equivalent can be measured, for example, by NMR.
- the (meth)acryloyl group equivalent number of component (A) is the number (number of equivalents) of (meth)acryloyl groups per mass (amount charged) of component (A), and the mass of (A) (meth)acrylate compound (g) divided by the (meth)acryloyl equivalent of the (meth)acrylate compound (if more than one (meth)acrylate compound is involved, the sum of such quotients for each (meth)acrylate compound) be.
- the thiol group equivalent number of component (B) is the number of thiol groups (equivalent number) per mass (amount charged) of component (B), and the mass (g) of the thiol compound (B) is It is the quotient divided by the thiol equivalent (if more than one thiol compound is involved, the sum of such quotients for each thiol compound).
- [Number of thiol group equivalents of component (B)]/[Number of (meth)acryloyl group equivalents of component (A)] is in the range of 0.5 to 1.8. reacts in a certain amount or more, sufficient molecular cross-linking is formed, and high adhesive strength can be easily developed.
- the resin composition of the present embodiment has (C) the following formula (1): (In the formula, R is hydrogen or an alkyl group, preferably hydrogen or an alkyl group having 1 to 6 carbon atoms, more preferably hydrogen or a methyl group.) A photopolymerization initiator represented by (hereinafter also referred to as "(C) component") is included.
- (C) component A photopolymerization initiator represented by (hereinafter also referred to as "(C) component"
- the resin composition containing the photopolymerization initiator of formula (1) exhibits photocurability even when irradiated with UV light of 365 nm or 385 nm, which is generally used for photocuring UV-curable adhesives.
- component (C) Commercially available products of component (C) include 2-dimethylamino-2-(4-methyl-benzyl)-1-(4-morpholin-4-yl-phenyl)-butan-1-one (IGM Resins B.V. product: Omnirad 379EG), 2-benzyl-2-(dimethylamino)-4'-morpholinobtyrophenone (manufactured by IGM Resins B.V.: Omnirad 369), and the like.
- IGM Resins B.V. product Omnirad 379EG
- 2-benzyl-2-(dimethylamino)-4'-morpholinobtyrophenone manufactured by IGM Resins B.V.: Omnirad 369
- the content of the photopolymerization initiator is preferably 0.3% by mass to 10% by mass with respect to the total mass of the resin composition from the viewpoint of the curing speed of the resin composition and the stability against ambient light. , more preferably 0.5% by mass to 7% by mass, and still more preferably 0.5% by mass to 5% by mass.
- the resin composition of the present embodiment further contains (D) a thermal polymerization initiator (hereinafter also referred to as "(D) component") within a range that does not impair the effects of the present invention.
- the thermal polymerization initiator is a compound that generates active species such as radicals, anions, or cations by heating. initiators.
- the resin composition of the present embodiment is both photocurable and thermosetting, and thermosetting can be accelerated by containing (D) a thermal polymerization initiator.
- a thermal radical polymerization initiator and a thermal anionic polymerization initiator may be used in combination.
- thermal radical polymerization initiators include methyl ethyl ketone peroxide, methylcyclohexanone peroxide, methyl acetoacetate peroxide, acetylacetone peroxide, 1,1-bis(t-butylperoxy)3,3,5-trimethylcyclohexane, 1,1-bis(t-hexylperoxy)cyclohexane, 1,1-bis(t-hexylperoxy)3,3,5-trimethylcyclohexane, 1,1-bis(t-butylperoxy)cyclohexane, 2 , 2-bis(4,4-di-t-butylperoxycyclohexyl)propane, 1,1-bis(t-butylperoxy)cyclododecane, n-butyl 4,4-bis(t-butylperoxy) valerate, 2,2-bis(t-butylperoxy)butane, 1,1-bis(t-butylperoxy)-2
- thermal anionic polymerization initiators include 2-methylimidazole, 2-ethylimidazole, 2-phenylimidazole, 2-ethyl-4-methylimidazole, 2-undecylimidazole, 1-cyanoethyl-2-ethyl-4- imidazoles such as methylimidazole, triethylamine, triethylenediamine, 2-(dimethylaminomethyl)phenol, 1,8-diaza-bicyclo[5,4,0]undecene-7, tris(dimethylaminomethyl)phenol, benzyldimethylamine and phosphines such as triphenylphosphine, tributylphosphine and trioctylphosphine.
- thermal anionic polymerization initiators include, in addition to the above examples, imidazole compounds that are solid at room temperature; solid-dispersed amine adduct latent curing such as reaction products of amine compounds and epoxy compounds (amine-epoxy adduct system). Catalyst; a reaction product of an amine compound and an isocyanate compound or a urea compound (urea-type adduct system), and the like.
- Examples of the epoxy compound used as one of raw materials for producing the solid-dispersed amine adduct-based latent curing catalyst include bisphenol A, bisphenol F, catechol, polyhydric phenols such as resorcinol, or glycerin.
- Polyglycidyl ethers obtained by reacting polyhydric alcohols such as polyhydric alcohols and polyethylene glycol with epichlorohydrin; reaction of epichlorohydrin with hydroxycarboxylic acids such as p-hydroxybenzoic acid and ⁇ -hydroxynaphthoic acid polyglycidyl esters obtained by reacting polycarboxylic acids such as phthalic acid and terephthalic acid with epichlorohydrin; 4,4'-diaminodiphenylmethane, m-aminophenol, etc.
- An amine compound used as another raw material for producing a solid-dispersed amine adduct-based latent curing catalyst has in its molecule one or more active hydrogens capable of undergoing an addition reaction with an epoxy group, and has a primary amino group, a secondary Any compound having at least one functional group selected from an 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, for example, diethylenetriamine, triethylenetetramine, n-propylamine, 2-hydroxyethylaminopropylamine, cyclohexylamine, 4,4'-diamino-dicyclohexylmethane; 4,4'-diaminodiphenylmethane, 2 -aromatic amine compounds such as methylaniline; nitrogen atom-containing heterocyclic compounds such as 2-ethyl-4-methylimidazole, 2-ethyl-4-methylimidazoline, 2,4-dimethylimidazoline, piperidine and piperazine; etc., but not limited to these.
- compounds having a tertiary amino group in the molecule are particularly raw materials that provide latent curing catalysts having excellent curing accelerating ability.
- examples of such compounds include, for example, dimethylaminopropylamine , diethylaminopropylamine, di-n-propylaminopropylamine, dibutylaminopropylamine, dimethylaminoethylamine, diethylaminoethylamine, N-methylpiperazine and other amine compounds, 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-dimethylamin
- isocyanate compounds used as solid-dispersed amine adduct-based latent curing catalysts and as another manufacturing raw material include monofunctional isocyanate compounds such as n-butyl isocyanate, isopropyl isocyanate, phenyl isocyanate, and benzyl isocyanate; methylene diisocyanate, toluylene diisocyanate, 1,5-naphthalene diisocyanate, diphenylmethane-4,4'-diisocyanate, isophorone diisocyanate, xylylene diisocyanate, paraphenylene diisocyanate, 1,3,6-hexamethylene triisocyanate, bicycloheptane triisocyanate, etc.
- monofunctional isocyanate compounds such as n-butyl isocyanate, isopropyl isocyanate, phenyl isocyanate, and benzyl isocyanate
- terminal isocyanate group-containing compounds obtained by reacting these polyfunctional isocyanate compounds with active hydrogen compounds can also be used.
- Examples of such terminal isocyanate group-containing compounds 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-dispersed latent curing catalyst that can be used in the present embodiment includes, for example, the above (a) two components of an amine compound and an epoxy compound, (b) three components of these two components and an active hydrogen compound, or (c ) Binary or ternary combinations of amine compounds and isocyanate compounds and/or urea compounds. These components are mixed and reacted at a temperature from room temperature to 200° C., then solidified by cooling and pulverized, or reacted in a solvent such as methyl ethyl ketone, dioxane, tetrahydrofuran, etc., and after removing the solvent, , can be easily produced by pulverizing the solid content.
- a solvent such as methyl ethyl ketone, dioxane, tetrahydrofuran, etc.
- Typical examples of commercially available solid dispersion type latent curing catalysts include amine-epoxy adduct system (amine adduct system) such as "Amicure PN-23” (product name of Ajinomoto Fine-Techno Co., Ltd.), “Amicure PN-40” (Ajinomoto Fine-Techno Co., Ltd. product name), “Amicure PN-50” (Ajinomoto Fine-Techno Co., Ltd. product name), “Hardner X-3661S” (ACR Co., Ltd. product name), “Hardener X-3670S” ” (ACR Co., Ltd.
- urea-type adducts include "Fujicure FXE-1000" (T&K TOKA Co., Ltd. product name), "Fujicure FXR- 1030” (product name of T&K TOKA Co., Ltd.), etc., but not limited to these.
- Component (D) may be used either singly or in combination of two or more.
- thermal cationic polymerization initiators include (4-methylphenyl)[4-(2-methylpropyl)phenyl]iodonium cation, (4-methylphenyl)(4-isopropylphenyl)iodonium cation, (4-methylphenyl ) (4-isobutyl)iodonium cation, bis(4-tert-butyl)iodonium cation, bis(4-dodecylphenyl)iodonium cation, (2,4,6-trimethylphenyl)[4-(1-methylacetic acid ethyl ether ) aromatic iodonium salts such as phenyl]iodonium cations, aromatic sulfonium salts such as diphenyl[4-(phenylthio)phenyl]sulfonium cations, triphenylsulfonium cations and alkyltriphenylsulfonium cations.
- the resin composition contains a thermal radical polymerization initiator or a thermal anionic polymerization initiator. In one embodiment, the resin composition contains a thermal radical polymerization initiator and a thermal anionic polymerization initiator.
- the content of the thermal polymerization initiator is preferably 0.1 to 40% by mass relative to the total mass of the resin composition, from the viewpoint of the curing speed and pot life of the resin composition. It is more preferably 3 to 20% by mass, and even more preferably 0.5 to 10% by mass.
- the resin composition of the present embodiment may contain (E) a radical polymerization inhibitor (hereinafter also referred to as "(E) component") within a range that does not impair the effects of the present invention. good.
- (E) The radical polymerization inhibitor is added to enhance the stability of the resin composition during storage, and is added to suppress the occurrence of unintended radical polymerization reactions.
- a (meth)acrylate compound may generate a radical by itself with a low probability, and an unintended radical polymerization reaction may occur with the radical as a starting point. By adding a radical polymerization inhibitor, occurrence of such an unintended radical polymerization reaction can be suppressed.
- a known radical polymerization inhibitor can be used.
- at least one selected from N-nitroso-N-phenylhydroxylamine aluminum, triphenylphosphine, p-methoxyphenol, and hydroquinone can be used.
- known radical polymerization inhibitors disclosed in JP-A-2010-117545, JP-A-2008-184514, etc. can also be used.
- the content of the radical polymerization inhibitor is preferably 0.0001 to 5% by mass, more preferably 0.001 to 3% by mass, relative to the total mass of the resin composition from the viewpoint of pot life. is more preferable.
- the resin composition of the present embodiment may contain (F) a coupling agent (hereinafter also referred to as “(F) component”) within a range that does not impair the effects of the present invention.
- the coupling agent has two or more different functional groups in the molecule, one of which is a functional group that chemically bonds with the inorganic material, and the other of which chemically bonds with the organic material. It is a functional group.
- coupling agents include, but are not limited to, silane coupling agents, aluminum coupling agents, titanium coupling agents, etc., depending on the type of functional group that chemically bonds with the inorganic material.
- Examples of coupling agents include various types of coupling agents such as epoxy, amino, vinyl, methacrylic, acrylic, and mercapto, depending on the type of functional group that chemically bonds with the organic material. It is not limited to these. Among these, an epoxy-based coupling agent containing an epoxy group is preferable for reasons such as improved humidity resistance reliability.
- epoxy-based silane coupling agents include 3-glycidoxypropyltrimethoxysilane (product name: KBM403, manufactured by Shin-Etsu Chemical Co., Ltd.), 3-glycidoxypropyltriethoxysilane (product name: KBE-403, Shin-Etsu Chemical Co., Ltd.), 3-glycidoxypropylmethyldiethoxysilane (product name: KBE-402, manufactured by Shin-Etsu Chemical Co., Ltd.), 3-glycidoxypropylmethyldimethoxysilane (product name: KBM402, manufactured by Shin-Etsu Chemical Co., Ltd.) , 8-glycidoxyoctyltrimethoxysilane (product name: KBM-4803, Shin-Etsu Chemical Co., Ltd.), 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane (product name: Sila Ace S530, JNC Corporation), etc. mentioned.
- methacrylic silane coupling agents include 3-methacryloxypropyltrimethoxysilane (product name: KBM503, manufactured by Shin-Etsu Chemical Co., Ltd.), 3-methacryloxypropylmethyldimethoxysilane (product name: KBM502, manufactured by Shin-Etsu Chemical Co., Ltd.). ), 3-methacryloxypropylmethyldiethoxysilane (product name: KBE502, manufactured by Shin-Etsu Chemical Co., Ltd.), 3-methacryloxypropyltriethoxysilane (product name: KBE503, manufactured by Shin-Etsu Chemical Co., Ltd.), and the like.
- acrylic silane coupling agents include 3-acryloxypropyltrimethoxysilane (product name: KBM-5103, manufactured by Shin-Etsu Chemical Co., Ltd.).
- mercapto-based silane coupling agents include 3-mercaptopropyltrimethoxysilane (product name KBM803, manufactured by Shin-Etsu Chemical Co., Ltd.) and 3-mercaptopropylmethyldimethoxysilane (product name KBM802, manufactured by Shin-Etsu Chemical Co., Ltd.). mentioned.
- any one of the coupling agents may be used, or two or more may be used in combination.
- the content of component (F) is preferably 0.1 to 10% by mass, more preferably 0.2 to 7% by mass, and still more preferably 0.3 to 5% by mass, relative to the total mass of the resin composition. is.
- the resin composition of the present embodiment may contain (G) an inorganic filler (hereinafter also referred to as "(G) component") within a range that does not impair the effects of the present invention.
- An inorganic filler consists of a granular body formed of an inorganic material.
- Inorganic materials include silica, alumina, aluminum nitride, calcium carbonate, aluminum silicate, magnesium silicate, magnesium carbonate, barium sulfate, barium carbonate, lime sulfate, aluminum hydroxide, calcium silicate, potassium titanate, titanium oxide, Zinc oxide, silicon carbide, silicon nitride, boron nitride and the like can be used. Any one of the inorganic fillers may be used, or two or more thereof may be used in combination.
- a silica filler is preferably used as the inorganic filler.
- Silica is preferably amorphous silica.
- the shape of the inorganic filler is not particularly limited, and may be spherical, scaly, acicular, irregular, and the like. A spherical shape is preferable from the viewpoint of fluidity.
- the average particle size of the inorganic filler is preferably 0.01-15 ⁇ m, more preferably 0.01-10 ⁇ m.
- the maximum particle size of the inorganic filler is preferably 50 ⁇ m or less, more preferably 30 ⁇ m or less.
- the average particle size is the particle size at 50% of the integrated value in the volume-based particle size distribution measured by the laser diffraction/scattering method.
- the maximum particle size is the maximum particle size in a volume-based particle size distribution measured by a laser diffraction/scattering method.
- the content of the inorganic filler is preferably 0.5 to 80% by mass, more preferably 1 to 70% by mass, relative to the total mass of the resin composition.
- the resin composition of the present embodiment may contain (H) an anionic polymerization inhibitor (hereinafter also referred to as "(H) component") within a range that does not impair the effects of the present invention.
- (H) component an anionic polymerization inhibitor
- 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.
- the anionic polymerization inhibitor can be a known one, and for example, a boric acid ester compound and a strong acid can be used.
- Specific examples of (H) 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, dichloroacetic acid, and the like.
- the preferred (H) anionic polymerization inhibitor is at least one selected from tri-n-propylborate, triisopropylborate and barbituric acid.
- (H) 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 (H) 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 may optionally contain a solvent, carbon black, titanium black, an ion trapping agent, a leveling agent, an antioxidant, an antifoaming agent, a thixotropic agent, and a viscosity modifier as long as the object of the present embodiment is not impaired. , flame retardants, and/or other additives.
- the resin composition preferably does not substantially contain a sensitizer from the viewpoint of stability against ambient light and prevention of curing of only the surface layer.
- Sensitizers include chalcone derivatives, unsaturated ketones such as dibenzalacetone, 1,2-diketone derivatives such as benzyl and camphorquinone, benzoin derivatives, fluorene derivatives, naphthoquinone derivatives, and anthraquinone derivatives.
- xanthene derivatives thioxanthene derivatives, xanthone derivatives, thioxanthone derivatives, coumarin derivatives, ketocoumarin derivatives, cyanine derivatives, merocyanine derivatives, polymethine dyes such as oxonol derivatives, acridine derivatives, azine derivatives, thiazine derivatives, oxazine derivatives, indoline derivatives, Azulene derivatives, azulenium derivatives, squarylium derivatives, porphyrin derivatives, tetraphenylporphyrin derivatives, triarylmethane derivatives, tetrabenzoporphyrin derivatives, tetrapyrazinoporphyrazine derivatives, phthalocyanine derivatives, tetraazaporphyrazine derivatives, tetraquinoxalyloporphyrazine derivatives , naphthalocyanine derivatives, subphthalo
- the resin composition includes, for example, components (A) to (C), optionally components (D), (E), (F), (G) and/or (H), and if necessary Other additives and the like can be obtained by stirring, melting, mixing and/or dispersing them simultaneously or separately while applying heat treatment if necessary.
- Devices for mixing, stirring, dispersing, etc. are not particularly limited. As this device, a Laikai machine, a Henschel mixer, a three-roll mill, a ball mill, a planetary mixer, a bead mill, etc., equipped with a stirring and heating device can be used. Also, these devices may be used in combination as appropriate.
- the resin composition thus obtained has photocurability and thermosetting properties, and in particular has high curability and photocuring adhesive strength with UV light of a longer wavelength (eg, 405 nm). On the other hand, the resin composition of this embodiment is stable against ambient light.
- the light to be irradiated is, for example, ultraviolet rays (UV).
- UV light means light having a wavelength in the range of 200 nm or more and 410 nm or less.
- the resin composition of the present embodiment can be cured by irradiation with any wavelength of 365 nm, 385 nm, and 405 nm, for example.
- the irradiation amount of light to be irradiated is preferably 50 mJ/cm 2 to 2000 mJ/cm 2 .
- the thermal curing temperature of the resin composition is preferably 70 to 90°C when the resin composition is used in an image sensor module.
- the resin composition of the present embodiment can be used, for example, as an adhesive for joining parts together or as a raw material thereof.
- the adhesive which is the second embodiment of the present invention, contains the resin composition of the first embodiment described above. This adhesive allows good bonding to engineering plastics, ceramics and metals.
- the adhesive of the present embodiment is preferably used for bonding parts constituting an image sensor or camera module. Since the adhesive of the present embodiment has high curability and photocuring adhesion strength with UV light of a longer wavelength (e.g., 405 nm), when bonding parts that absorb UV light of 400 nm or less, such as IR cut filters, effectively used for
- the cured product of the third embodiment of the present invention is a cured product obtained by curing the resin composition of the first embodiment or the adhesive of the second embodiment.
- a semiconductor device includes the cured product of the third embodiment described above.
- An electronic component according to the fifth embodiment of the present invention includes the semiconductor device according to the fourth embodiment.
- the electronic component can be an image sensor or camera module.
- FIG. 1 (schematic diagram viewed from the side) and FIG. 2 (schematic diagram viewed from the top)
- the photocuring depth of the resin composition was measured.
- two heat-resistant tapes 20 (150 ⁇ m thick) were pasted on a black resin plate 10a (50 mm wide ⁇ 25 mm long ⁇ 1.5 mm thick) at intervals of 10 mm.
- the resin composition 30 was applied in the same thickness as the heat-resistant tape 20.
- Two heat-resistant tapes 20 and a resin composition 30 were sandwiched between a resin plate 10a and another resin plate 10b, and both ends of the resin plate were fastened with clips (not shown).
- the resin composition protruding from the top of the resin plate was wiped off.
- the resin composition 30 was irradiated with UV from above the jig thus produced.
- the UV irradiation conditions at this time are: (1) UV irradiation doses of 100 mJ/cm 2 and 1000 mJ/cm 2 at a UV wavelength of 365 nm (LED lamp), and (2) UV irradiation dose at a UV wavelength of 405 nm (LED lamp). Two types of 100 mJ/cm 2 and 1000 mJ/cm 2 were used.
- the UV irradiation conditions at this time are: (1) UV irradiation doses of 100 mJ/cm 2 and 1000 mJ/cm 2 at a UV wavelength of 365 nm (LED lamp), and (2) UV irradiation dose at a UV wavelength of 405 nm (LED lamp). Two types of 100 mJ/cm 2 and 1000 mJ/cm 2 were used.
- the resin composition on this glass plate was poked from the side with a Universal Bond Tester Series 4000 manufactured by Nordson Advanced Technologies, Inc., and the shear strength was calculated from the value when the resin composition was peeled off. Table 1 shows the results. Under the curing conditions at a UV irradiation dose of 100 mJ/cm 2 , if the shear strength is 1N or more, the photocuring adhesive strength (share strength) is considered to be good ( ⁇ ), and if the shear strength is less than 1N, the photocuring adhesive strength (Shear strength) was determined to be poor ( ⁇ ).
- the photocuring adhesive strength (share strength) is considered to be good ( ⁇ ), and when the shear strength is less than 3N, the photocuring adhesive strength ( Shear strength) was determined to be poor ( ⁇ ).
- the length of the cured portion L ( ⁇ m ) is less than 250 ⁇ m (Comparative Examples 3 and 4), and the length L ( ⁇ m) of the cured portion is less than 450 ⁇ m (Comparative Example 3) under the curing conditions with a UV dose of 1000 mJ/cm 2 . It can be seen that the photocurability of the resin composition of is very high.
- the resin composition of Comparative Example 2 containing a photopolymerization initiator other than Formula (1) had high curability with UV light of a longer wavelength (405 nm), but was unstable to ambient light.
- the resin compositions of Comparative Examples 3 and 4 containing photopolymerization initiators other than formula (1) are stable to ambient light, but are not sufficiently cured by UV light with a longer wavelength (405 nm), resulting in poor adhesion. The strength was also insufficient.
- the present invention is a photo- and thermosetting resin composition that has high curability and photo-curing adhesive strength with longer wavelength (e.g., 405 nm) UV light and is stable to ambient light, particularly , IR cut filters, etc., are effectively used when bonding parts that absorb UV light of 400 nm or less.
- longer wavelength e.g. 405 nm
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Abstract
Description
本発明の第一の実施形態は、以下の樹脂組成物である。
(1)(A)(メタ)アクリレート化合物、
(B)チオール化合物、及び
(C)下記式(1):
(式中、Rは、水素又はアルキル基である。)
で表される光重合開始剤
を含む樹脂組成物。
(2)(A)成分の(メタ)アクリロイル基当量数に対する(B)成分のチオール基当量数の比([(B)成分のチオール基当量数]/[(A)成分の(メタ)アクリロイル基当量数])が、0.5~1.8である、上記(1)に記載の樹脂組成物。
(3)さらに、(D)熱重合開始剤を含む、上記(1)又は(2)に記載の樹脂組成物。
(4)上記(1)~(3)のいずれかに記載の樹脂組成物を含む接着剤。
(5)イメージセンサー又はカメラモジュールを構成する部品の接着に用いられる、上記(4)に記載の接着剤。
本発明の第四の実施形態は、(7)上記(6)に記載の硬化物を含む半導体装置である。
本発明の第五の実施形態は、以下の電子部品である。
(8)上記(7)に記載の半導体装置を含む電子部品。
(9)イメージセンサー又はカメラモジュールである、上記(8)に記載の電子部品。
本発明の第一の実施形態である樹脂組成物は、
(A)(メタ)アクリレート化合物、
(B)チオール化合物、及び
(C)下記式(1):
(式中、Rは、水素又はアルキル基である。)
で表される光重合開始剤
を含む。本実施形態によれば、より長波長(例えば、405nm)のUV光で高い硬化性及び光硬化接着強度を有するとともに、環境光に対して安定である樹脂組成物を得ることができる。
本実施形態の樹脂組成物は、(A)(メタ)アクリレート化合物(以下、「(A)成分」とも言う)を含む。(A)(メタ)アクリレート化合物は、硬化後の樹脂組成物に透明性や適度な硬度を付与することができる。(A)成分である(メタ)アクリレート化合物は、1以上の(メタ)アクリロイル基を有していれば、特に限定されない。耐熱性を確保する点を考慮すると、2個以上の(メタ)アクリロイル基を持つ化合物が好ましく、2~6個の(メタ)アクリロイル基を持つ化合物がより好ましく、2個の(メタ)アクリロイル基を持つ化合物がさらに好ましい。また、粘度や硬化物物性(接着強度や柔軟性など)の調整のため、2個の(メタ)アクリロイル基を持つ化合物に加えて、1個の(メタ)アクリロイル基を持つ化合物を用いることもできる。
(A)(メタ)アクリレート化合物は、上述した(メタ)アクリレート化合物のうち、いずれか1種を用いてもよいし、2種以上を併用してもよい。
本実施形態の樹脂組成物は、(B)ポリチオール化合物(以下、「(B)成分」とも言う)を含む。(B)ポリチオール化合物は、樹脂組成物に、高い光硬化性を付与する。(B)成分は、2以上のチオール基を有していれば、特に限定されない。
本実施形態の樹脂組成物は、(C)下記式(1):
(式中、Rは、水素又はアルキル基であり、好ましくは水素又は炭素数が1~6のアルキル基であり、より好ましくは水素又はメチル基である。)
で表される光重合開始剤(以下、「(C)成分」とも言う)を含む。式(1)の光重合開始剤を用いることにより、より長波長(例えば、405nm)のUV光で高い硬化性及び光硬化接着強度を有するとともに、環境光に対し安定である樹脂組成物を得ることができる。なお、式(1)の光重合開始剤を含む樹脂組成物は、一般的にUV硬化性接着剤の光硬化に使用される365nmや385nmのUV光を照射した場合も光硬化性を示す。
本実施形態の樹脂組成物は、本発明の効果を損なわない範囲で、さらに、(D)熱重合開始剤(以下、「(D)成分」とも言う)を含んでいてもよい。(D)熱重合開始剤は、加熱によってラジカル、アニオン又はカチオンなどの活性種を発生する化合物であり、活性種の種類に応じて、熱ラジカル重合開始剤、熱アニオン重合開始剤及び熱カチオン重合開始剤が挙げられる。本実施形態の樹脂組成物は、光硬化性とともに熱硬化性でもあり、(D)熱重合開始剤を含むことにより、熱硬化を促進することができる。本実施形態において、熱ラジカル重合開始剤と熱アニオン重合開始剤とを組み合わせて用いてもよい。
本実施形態の樹脂組成物は、本発明の効果を損なわない範囲で、(E)ラジカル重合禁止剤(以下、「(E)成分」とも言う)を含んでいてもよい。(E)ラジカル重合禁止剤は、樹脂組成物の保存時の安定性を高めるために添加されるものであり、意図しないラジカル重合反応の発生を抑制するために添加されるものである。(メタ)アクリレート化合物は、低い確率で自分からラジカルを発生することがあり、そのラジカルを基点として意図しないラジカル重合反応が発生する場合がある。ラジカル重合禁止剤を添加することによって、このような意図しないラジカル重合反応の発生を抑制することができる。
本実施形態の樹脂組成物は、本発明の効果を損なわない範囲で、(F)カップリング剤(以下、「(F)成分」とも言う)を含んでいてもよい。カップリング剤は、分子中に2つ以上の異なった官能基を有しており、その一つは、無機質材料と化学結合する官能基であり、他の一つは、有機質材料と化学結合する官能基である。樹脂組成物がカップリング剤を含有することによって、樹脂組成物の基板等への密着性が向上する。
本実施形態の樹脂組成物は、本発明の効果を損なわない範囲で、(G)無機フィラー(以下、「(G)成分」とも言う)を含有していてもよい。
無機フィラーは、無機材料によって形成された粒状体からなる。無機材料としては、シリカ、アルミナ、窒化アルミニウム、炭酸カルシウム、ケイ酸アルミニウム、ケイ酸マグネシウム、炭酸マグネシウム、硫酸バリウム、炭酸バリウム、硫酸石灰、水酸化アルミニウム、ケイ酸カルシウム、チタン酸カリウム、酸化チタン、酸化亜鉛、炭化ケイ素、窒化ケイ素、窒化ホウ素等を用いることができる。無機フィラーは、いずれか1種を用いてもよいし、2種以上を併用してもよい。無機フィラーとしては、シリカフィラーを用いることが好ましい。シリカは、非晶質シリカが好ましい。
本実施形態の樹脂組成物は、本発明の効果を損なわない範囲で、(H)アニオン重合抑制剤(以下、「(H)成分」とも言う)を含んでもよい。(H)アニオン重合抑制剤は、樹脂組成物の保存時の安定性を高めるためのものであり、意図しない塩基性成分による重合反応の発生を抑制するために添加される。
(H)アニオン重合抑制剤は、いずれか1種を用いてもよいし、2種以上を併用してもよい。
本発明の第二の実施形態である接着剤は、上述の第一の実施形態の樹脂組成物を含む。この接着剤は、エンジニアリングプラスチック、セラミックス、及び金属に対して、良好な接合を可能にする。本実施形態の接着剤は、好ましくは、イメージセンサー又はカメラモジュールを構成する部品の接着に用いられる。本実施形態の接着剤は、より長波長(例えば、405nm)のUV光で高い硬化性及び光硬化接着強度を有するので、IRカットフィルター等の400nm以下のUV光を吸収する部品を接着する際に有効に用いられる。
本発明の第三の実施形態の硬化物は、上述の第一実施形態の樹脂組成物又は第二実施形態の接着剤が硬化された硬化物である。
本発明の第四の実施形態の半導体装置は、上述の第三実施形態の硬化物を含む。本発明の第五の実施形態の電子部品は、この第四実施形態の半導体装置を含む。電子部品は、イメージセンサー又はカメラモジュールであり得る。
表1に示す配合に従って、3本ロールミルを用いて所定の量の各成分を混合することにより、樹脂組成物を調製した。表1において、各成分の量は質量部(単位:g)で表されている。実施例及び比較例において用いた成分は、以下の通りである。
ジメチロール-トリシクロデカンジアクリレート(品名:ライトアクリレートDCP-A、共栄社化学社製、アクリロイル当量:188g/eq)
・(B)ポリチオール化合物(成分(B))
下記式で表されるペンタエリスリトールテトラキス(3-メルカプトプロピオネート)(品名:PEMP、SC有機化学製、チオール当量:122g/eq)
・(C)式(1)の光重合開始剤(成分(C))
(C1):下記式で表される2-ジメチルアミノ-2-(4-メチル-ベンジル)-1-(4-モルフォリン-4-イル-フェニル)-ブタン-1-オン(品名:Omnirad 379EG、IGM Resins B.V.社製)
(C2):下記式で表される2-ベンジル-2-(ジメチルアミノ)-4’-モルホリノブチロフェノン(品名:Omnirad 369、IGM Resins B.V.社製)
・(C’)式(1)以外の光重合開始剤
(C’3):下記式で表される2,4,6-トリメチルベンゾイル-ジフェニルホスフィンオキシド(品名:Omnirad TPO H、IGM Resins B.V.社製)
(C’4):下記式で表される1-ヒドロキシシクロヘキシル-フェニルケトン(品名:Omnirad 184、IGM Resins B.V.社製)
(C’5):下記式で表される2-メチル-1-[4-(メチルチオ)フェニル]-2-モルホリノプロパン-1-オン(品名:Omnirad 907、IGM Resins B.V.社製)
・(E)ラジカル重合禁止剤(成分(E))
N-ニトロソ-N-フェニルヒドロキシルアミンアルミニウム(和光純薬工業株式会社製、分子量:488.33)
図1(側面から見た模式図)及び図2(上面から見た模式図)に示すような治具を用いて、樹脂組成物の光硬化深度を測定した。具体的には、黒色の樹脂板10a(横50mm×縦25mm×厚さ1.5mm)上に、2本の耐熱テープ20(厚さ150μm)を、10mmの間隔で貼った。その2本の耐熱テープ20の間に、樹脂組成物30を耐熱テープ20と同一の厚さで塗布した。樹脂板10aと、もう1つの樹脂板10bとで、2本の耐熱テープ20及び樹脂組成物30を挟み、樹脂板の両端をクリップ(図示せず)で留めた。樹脂板の上からはみ出た樹脂組成物は拭き取った。このように作製した治具の上部から、樹脂組成物30に対し、UV照射を行った。このときのUV照射条件は、(1)UV波長365nm(LEDランプ)においてUV照射量100mJ/cm2及び1000mJ/cm2の2種類、並びに(2)UV波長405nm(LEDランプ)においてUV照射量100mJ/cm2及び1000mJ/cm2の2種類とした。挟んでいた樹脂板の片方10bを剥がし、硬化物に付着した未硬化部分を取り除き、硬化部分の長さL(μm)を測定顕微鏡を用いて測定した。結果を表1に示す。UV照射量100mJ/cm2での硬化条件において、硬化部分の長さL(μm)が250μm以上の場合、光硬化性(硬化深度)が良好である(〇)とし、硬化部分の長さL(μm)が250μm未満の場合、光硬化性(硬化深度)が不良である(×)とした。UV照射量1000mJ/cm2での硬化条件において、硬化部分の長さL(μm)が450μm以上の場合、光硬化性(硬化深度)が良好である(〇)とし、硬化部分の長さL(μm)が450μm未満の場合、光硬化性(硬化深度)が不良である(×)とした。
ガラス板上に、樹脂組成物をφ3.0mmの大きさ、0.3mmの厚さで孔版印刷し、印刷した樹脂組成物をUV硬化させて、試験片を作製した(n=3)。このときのUV照射条件は、(1)UV波長365nm(LEDランプ)においてUV照射量100mJ/cm2及び1000mJ/cm2の2種類、並びに(2)UV波長405nm(LEDランプ)においてUV照射量100mJ/cm2及び1000mJ/cm2の2種類とした。このガラス板上の樹脂組成物を、ノードソン・アドバンスト・テクノロジー社製万能型ボンドテスター シリーズ4000で側面から突き、樹脂組成物が剥がれた時の数値からシェア強度を算出した。結果を表1に示す。UV照射量100mJ/cm2での硬化条件において、シェア強度が1N以上の場合、光硬化接着強度(シェア強度)が良好である(〇)とし、シェア強度が1N未満の場合、光硬化接着強度(シェア強度)が不良である(×)とした。紫外線量1000mJ/cm2での硬化条件において、シェア強度が3N以上の場合、光硬化接着強度(シェア強度)が良好である(〇)とし、シェア強度が3N未満の場合、光硬化接着強度(シェア強度)が不良である(×)とした。
実施例及び比較例の各試料をガラス片上に厚み約0.15mmで印刷した。印刷した試料に対し、光源に15W蛍光灯(品名:FL15WL、パナソニック製)を用い、1.5mの距離で蛍光灯の光を照射した。照射開始から所定時間経過した後、印刷した試料の状態を指触(ピンセット)により、硬化の有無を確認した。結果を表1に示す。照射開始から24時間以上経過後も試料が硬化していない場合、環境光に対する安定性が良好である(〇)とし、照射開始から24時間以内に試料が硬化した場合、環境光に対する安定性が不良である(×)とした。
式(1)以外の光重合開始剤を含む比較例2の樹脂組成物は、より長波長(405nm)のUV光で高い硬化性を有するものの、環境光に対して不安定であった。
式(1)以外の光重合開始剤を含む比較例3及び4の樹脂組成物は、環境光に対して安定であるものの、より長波長(405nm)のUV光では十分に硬化せず、接着強度も不十分であった。
本明細書に記載された全ての文献、特許出願、および技術規格は、個々の文献、特許出願、および技術規格が参照により取り込まれることが具体的かつ個々に記された場合と同程度に、本明細書に参照により取り込まれる。
10b 樹脂板
20 耐熱テープ
30 樹脂組成物
Claims (9)
- (A)成分の(メタ)アクリロイル基当量数に対する(B)成分のチオール基当量数の比([(B)成分チオール基当量数]/[(A)成分の(メタ)アクリロイル基当量数])が、0.5~1.8である、請求項1に記載の樹脂組成物。
- さらに、(D)熱重合開始剤を含む、請求項1又は2に記載の樹脂組成物。
- 請求項1~3のいずれか1項に記載の樹脂組成物を含む接着剤。
- イメージセンサー又はカメラモジュールを構成する部品の接着に用いられる、請求項4に記載の接着剤。
- 請求項1~3のいずれか1項に記載の樹脂組成物、もしくは請求項4又は5に記載の接着剤が硬化された硬化物。
- 請求項6に記載の硬化物を含む半導体装置。
- 請求項7に記載の半導体装置を含む電子部品。
- イメージセンサー又はカメラモジュールである、請求項8に記載の電子部品。
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WO2017221620A1 (ja) * | 2016-06-22 | 2017-12-28 | 富士フイルム株式会社 | 硬化性組成物、硬化膜、カラーフィルタ、遮光膜、固体撮像素子、画像表示装置、硬化膜の製造方法、及び、多官能チオール化合物 |
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