Classifications

• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
  • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
  • C09J11/02—Non-macromolecular additives
  • C09J11/04—Non-macromolecular additives inorganic
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
  • C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
• • 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
  • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
  • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
  • C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
• • 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
  • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
  • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
  • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
  • C08G59/4007—Curing agents not provided for by the groups C08G59/42 - C08G59/66
• • 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
  • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
  • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
  • C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
• • 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
  • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
  • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
  • C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
  • C08G65/06—Cyclic ethers having no atoms other than carbon and hydrogen outside the ring
  • C08G65/16—Cyclic ethers having four or more ring atoms
  • C08G65/18—Oxetanes
• • 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
  • C08K3/10—Metal 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
  • C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
• • 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
  • C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
  • C08K3/24—Acids; Salts thereof
  • C08K3/26—Carbonates; Bicarbonates
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K5/00—Use of organic ingredients
  • C08K5/04—Oxygen-containing compounds
  • C08K5/14—Peroxides
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
  • C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
  • C09D171/00—Coating compositions based on polyethers obtained by reactions forming an ether link in the main chain; Coating compositions based on derivatives of such polymers
• • 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
  • C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
• • 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
  • C09J171/00—Adhesives based on polyethers obtained by reactions forming an ether link in the main chain; Adhesives based on derivatives of such polymers
• • H—ELECTRICITY
  • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
  • H10W—GENERIC PACKAGES, INTERCONNECTIONS, CONNECTORS OR OTHER CONSTRUCTIONAL DETAILS OF DEVICES COVERED BY CLASS H10
  • H10W74/00—Encapsulations, e.g. protective coatings
  • H10W74/40—Encapsulations, e.g. protective coatings characterised by their materials
  • H10W74/47—Encapsulations, e.g. protective coatings characterised by their materials comprising organic materials, e.g. plastics or resins
• • 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
  • C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
  • C08K3/24—Acids; Salts thereof
  • C08K3/26—Carbonates; Bicarbonates
  • C08K2003/267—Magnesium carbonate
• • 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
  • C08K2201/00—Specific properties of additives
  • C08K2201/011—Nanostructured additives
• • 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
  • C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
  • C08K3/20—Oxides; Hydroxides
  • C08K3/22—Oxides; Hydroxides of metals
• • 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
  • C09J2203/00—Applications of adhesives in processes or use of adhesives in the form of films or foils
  • C09J2203/326—Applications of adhesives in processes or use of adhesives in the form of films or foils for bonding electronic components such as wafers, chips or semiconductors
• • 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
  • C09J2463/00—Presence of epoxy resin

Definitions

• the present invention relates to a curable resin composition, an adhesive, a sealing material, a cured product, a semiconductor device, and an electronic device.
• Curable resin compositions containing cationically polymerizable compounds are used as adhesives in the electronics field because the cured products have excellent properties such as adhesion, electrical insulation, chemical resistance, and mechanical strength.
• Patent Document 1 describes a thermal polymerization initiator system that can be cured by low-temperature heating, and contains an iodonium salt compound containing, for example, an aryl group for initiating the polymerization reaction of a cationic polymerizable compound, and a radical polymerization initiator that is an organic peroxide.
• Patent Document 1 describes an adhesive composition to which a corrosion inhibitor made of a metal hydroxide or metal oxide can be added or mixed for the purpose of preventing corrosion of the adherend.
• a corrosion inhibitor may reduce the curing properties of the adhesive.
• a composition that can be cured by heating at or below 100°C and/or by exposure to ultraviolet light, for example, to bond dissimilar materials may be required.
• the present invention therefore aims to provide a curable resin composition that can be cured, for example, by heating at 100°C or less and/or by UV irradiation, and that inhibits corrosion of the adherend, an adhesive, a sealant, a cured product obtained by curing these, and a semiconductor device and an electronic device that include the cured product.
• the means for solving the above problems are as follows, and the present invention includes the following aspects.
• (C) The curable resin composition according to [1], wherein the component (C) is 0.1 to 15 parts by mass per 1 part by mass of the component (B).
• the iodonium salt is decomposed by heating to generate a protonic acid H + X - .
• This protonic acid is coordinated to the functional group of the cationic curable resin, and the functional group to which the protonic acid is coordinated is attacked by the functional group of another cationic curable resin to generate a cation that becomes an active species, and a polymerization reaction proceeds.
• the aryl iodide generated by the decomposition of the iodonium salt by heating reacts with water vapor in the air to generate a corrosive gas (hydrogen iodide).
• Aliphatic epoxy resins include polyglycidyl ethers of polyhydric alcohols or their alkylene oxide adducts.
• Specific examples of aliphatic epoxy compounds contained in aliphatic epoxy resins include ethylene glycol diglycidyl ether, diethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, 1,4-butanediol diglycidyl ether, neopentyl glycol diglycidyl ether, 1,6-hexanediol diglycidyl ether, glycerin diglycidyl ether, trimethylolpropane triglycidyl ether (such as Epolite 100MF manufactured by Kyoeisha Chemical Co., Ltd.), and polyethylene glycol diglycidyl ether.
• examples of aliphatic cyclic epoxy resins include hydrogenated bisphenol A diglycidyl ether (such as jER YX8000 manufactured by Mitsubishi Chemical Corporation).
• the oxetane group equivalent of the oxetane resin is preferably 100 g/eq to 500 g/eq, and may be 110 g/eq to 300 g/eq.
• a cured product can be obtained by curing, for example, by heating at a low temperature of 100°C or less, preferably 80°C or less, and/or by ultraviolet irradiation.
• the oxetane group equivalent of the oxetane resin may be 250 g/eq or less.
• component (B) include diphenyliodonium hexafluoroarsenate, di(4-chlorophenyl)iodonium hexafluoroarsenate, di(4-bromophenyl)iodonium hexafluoroarsenate, phenyl(4-methoxyphenyl)iodonium hexafluoroarsenate, 4-methylphenyl-4-(1-methylethyl)phenyliodonium hexafluorophosphate, 4-methylphenyl-4-(1-methylethyl)phenyliodonium tri(pentafluoroethyl)trifluorophosphate (e.g., IK-1 manufactured by San-Apro Co., Ltd.), 4-methylphenyl-4-(1-methylethyl)phenyliodonium tetrakis(pentafluorophenyl)borate, 4-methylphenyl-4-((1
• ion trapping agents containing Bi or Sb that are not layered compounds cannot trap iodide ions with a large ionic radius.
• the ion trapping agent of component (C) is a layered compound containing at least one atom selected from the group consisting of Zr, Mg and Al, the interlayer distance is preferably about 4 ⁇ to 13 ⁇ .
• the curing reaction of the cationic curable resin can be rapidly advanced, and a cured product can be obtained by heating at a low temperature, for example, below 100°C, preferably below 80°C.
• Component (D) is a radical source, and when component (D) is a peroxydicarbonate-type organic peroxide, it is easy to generate carbonate radicals without decarboxylation.
• the organic peroxide of component (D) preferably has a one-hour half-life temperature of 50°C to 80°C, or may be 55°C to 75°C, and preferably 55°C to 70°C.
• component (D) is a peroxydicarbonate-type organic peroxide
• examples of the organic peroxide include di(secondary butyl) peroxydicarbonate (e.g., Luperox 225 manufactured by Arkema Yoshitomi Co., Ltd.), dicetyl peroxydicarbonate (e.g., Perkadox 24L manufactured by Nouryon), and di(4-tert-butylcyclohexyl) peroxydicarbonate (e.g., Peroyl TCP manufactured by NOF Corp.).
• Examples of component (D) include 1,1,3,3-tetramethylbutylperoxy-2-ethylhexanoate (e.g., Perocta O manufactured by NOF Corp.).
• the curable resin composition may contain at least one selected from the group consisting of (E) a photosensitizer, (F) a photoradical generator, and (G) a filler (hereinafter also referred to as “component (E)", “component (F)", and “component (G)", respectively).
• the curable resin composition may further contain at least one selected from the group consisting of (H) a coupling agent and (I) a colorant such as a pigment (hereinafter also referred to as “component (H)” and “component (I)", respectively).
• At least one component selected from the group consisting of (H) a coupling agent and (I) a colorant may be included as an optional component.
• the photosensitizer is a component for increasing the sensitivity of the iodonium salt to light.
• the photosensitizer include thioxanthone derivatives, carbonyl compounds, organic sulfur compounds, persulfides, redox compounds, azo and diazo compounds, halogen compounds, photoreducible dyes, and the like, with thioxanthone derivatives being preferred.
• the photoradical generator is a radical source together with the organic peroxide of component (D), and generates an alkyl radical by irradiation with light, reductively decomposes the iodonium salt, generates an acid (cation: H + ) by light, and promotes the polymerization reaction.
• the curable resin composition of the present invention contains a peroxydicarbonate-type organic peroxide as the organic peroxide of component (D), it is not necessary to contain the photoradical generator (F).
• the average particle size of the filler is not particularly limited, but in order to improve fluidity, injectability, coatability, adhesion, etc., it is preferably 0.01 ⁇ m or more and less than 10 ⁇ m, and particularly preferably 0.012 ⁇ m or more and 5 ⁇ m or less.
• the average particle size of the filler can be measured using a laser diffraction particle size distribution measuring device, a dynamic light scattering nanotrack particle size distribution meter, etc.
• the average particle size may be the 50% cumulative particle size in the volume-based particle size distribution, or the 50% cumulative particle size in the number-based particle size distribution.
• the coupling agent has two or more different functional groups in the molecule, one of which is a functional group that chemically bonds with an inorganic material, and the other is a functional group that chemically bonds with an organic material.
• the adhesion of the curable resin composition can be improved when bonding different materials such as a camera module or a sensor module.
• silane coupling agents examples include vinyl groups, epoxy groups, styryl groups, methacryl groups, acrylic groups, amino groups, isocyanurate groups, ureido groups, mercapto groups, sulfide groups, and isocyanate groups.
• the colorant can be used for the purpose of coloring the curable resin composition.
• the colorant include pigments, dyes, and pigments. Known colorants such as red, blue, green, yellow, black, and white can be used as the colorant.
• the pigment include black colorants such as carbon black, graphite, iron oxide, titanium black, anthraquinone, cobalt oxide, copper oxide, manganese, antimony oxide, nickel oxide, perylene, aniline, molybdenum sulfide, and bismuth sulfide.
• black colorants such as carbon black, graphite, iron oxide, titanium black, anthraquinone, cobalt oxide, copper oxide, manganese, antimony oxide, nickel oxide, perylene, aniline, molybdenum sulfide, and bismuth sulfide.
• commercially available pigments include titanium black 13M, 13M-C, and 13M-T manufactured by Mitsubishi Materials Electronic Chemicals Co., Ltd.
• the content of component (A) in the curable resin composition is preferably 40 to 95 mass%, more preferably 45 to 90 mass%, and even more preferably 50 to 85 mass%, based on 100 mass% of the total amount of the curable resin composition. If the content of component (A) in the curable resin composition is 40 to 90 mass%, based on 100 mass% of the total amount of the curable resin composition, a cured product can be obtained by heating at a low temperature of, for example, 100°C or less, preferably 80°C or less, and/or by irradiating with ultraviolet light.
• the curable resin composition contains, as component (A), at least one selected from the group consisting of component (A1) an epoxy resin having a ring skeleton in the molecule with an epoxy group equivalent of 100 g/eq to 1000 g/eq and component (A2) an oxetane resin
• component (A1) an epoxy resin having a ring skeleton in the molecule with an epoxy group equivalent of 100 g/eq to 1000 g/eq
• component (A2) an oxetane resin when the total amount of component (A) is taken as 100 mass%, the total amount of components (A1) and (A2) is preferably 20 to 100 mass%, more preferably 30 to 90 mass%, and even more preferably 30 to 70 mass%.
• component (A) when the total amount of component (A) is taken as 100 mass%, component (A) may be at least one component selected from the group consisting of components (A1) and (A2) (the total amount of components (A1) and (A2) is 100 mass%).
• component (A) when the total amount of components (A1) and (A2) is less than 100% by mass, the remainder excluding components (A1) and (A2) may be at least one selected from the group consisting of epoxy resins not having a ring structure in the molecule (e.g., aliphatic epoxy resins, etc.), polystyrene compounds, and vinyl ether compounds.
• component (A) in the curable resin composition contains an epoxy resin having a ring skeleton with an epoxy group equivalent of 100 g/eq to 1000 g/eq in the molecule of component (A1)
• the ratio 1 of the number of epoxy group equivalents in the epoxy resin of component (A1) to the number of functional group equivalents contained in component (A) is preferably 0.01 to 1.0, more preferably 0.2 to 0.9, and even more preferably 0.4 to 0.8.
• the oxetane resin of component (A2) is preferably 0 to 40 mass%, more preferably 0 to 30 mass%, and even more preferably 0 to 20 mass%, when the total amount of component (A) is taken as 100 mass%.
• a cured product can be obtained by heating at a low temperature of, for example, 100°C or less, preferably 80°C or less, and/or by irradiation with ultraviolet light.
• the ratio 2 of the number of oxetane group equivalents in the oxetane resin of component (A2) to the number of functional group equivalents contained in component (A) is preferably 0.01 to 0.8, more preferably 0.1 to 0.6, and even more preferably 0.1 to 0.4.
• the blending ratio of component (A1) to component (A2) in component (A) in the curable resin composition (component (A1):component (A2)) is preferably 100:0 to 60:40 by mass, more preferably 99:1 to 70:30, and even more preferably 98:2 to 80:20. If the blending ratio of component (A1) to component (A2) in component (A) is 100:0 to 60:40, a cured product can be obtained by heating at a low temperature of, for example, 100°C or less, preferably 80°C or less, and/or by UV irradiation.
• the amount of component (B) in the curable resin composition is preferably 0.1 to 10.0 parts by mass, more preferably 0.5 to 8 parts by mass, and even more preferably 1.0 to 5 parts by mass, per 100 parts by mass of component (A), in order to cure the composition by heating at a low temperature, for example, below 100°C, preferably below 80°C, and/or by exposure to ultraviolet light.
• the amount of component (C) in the curable resin composition is preferably 0.1 to 15 parts by mass, more preferably 0.2 to 10 parts by mass, and even more preferably 0.25 to 5 parts by mass, per part by mass of component (B).
• the content of component (C) is preferably 0.1 to 15% by mass, more preferably 0.1 to 10% by mass, and may be 0.5 to 10% by mass, per 100% by mass of the total amount of the curable resin composition.
• the amount of component (D) in the thermosetting resin composition is preferably 0 to 10.0 parts by mass, more preferably 0.1 to 8 parts by mass, and even more preferably 0.5 to 5 parts by mass, per 100 parts by mass of component (A).
• thermosetting resin composition contains component (D)
• the blending ratio of components (B) and (D) is preferably approximately equal, and may be 25:75 to 75:25 by mass, 30:70 to 70:30, 40:60 to 60:40, or 50:50 by mass.
• the amount of the photoradical generator of component (F) in the curable resin composition may be 0 to 3.0 mass%, 0.05 to 3.0 mass%, 0.05 to 2.0 mass%, or 0.1 to 1.0 mass%, relative to 100 mass% of the total amount of the curable resin composition.
• the amount of the filler of component (G) in the curable resin composition may be 0 to 50 mass%, 1 to 45 mass%, or 3 to 40 mass%, relative to 100 mass% of the total amount of the curable resin composition.
• the curable resin composition can be produced by mixing component (A), component (B) and component (C).
• the curable resin composition can be produced by further mixing component (D), component (E), component (F), component (G), component (H), component (I) and other optional components as necessary.
• the curable resin composition may be produced by mixing each component together with an additive as necessary. Each component is introduced simultaneously or separately into an appropriate mixer, and if necessary, the components are stirred and mixed while melting by heating to obtain a curable resin composition.
• the method for producing the curable resin composition is not particularly limited.
• the curable resin composition is preferably liquid or paste-like at room temperature, for example, 20°C to 30°C.
• the viscosity of the curable resin composition is preferably 200 Pa ⁇ s or less, or may be 190 Pa ⁇ s or less, or preferably 1 Pa ⁇ s or more, measured using a Brookfield rotational viscometer (HBDV-I type or RVDV-I type, spindle: SC4-14 spindle, rotation speed: 50 rpm, measurement temperature: 25°C) immediately after the resin composition is prepared (for example, within 30 minutes) and after the curable resin composition is left to stand for a predetermined time at room temperature, for example, 20°C to 30°C.
• the viscosity of the curable resin composition at 20°C to 30°C measured by the above-mentioned method may be 3 Pa ⁇ s to 10 Pa ⁇ s.
• Adhesive or sealant The curable resin composition can be used as an adhesive or sealant for fixing, joining or protecting components constituting an electronic device, a camera module or a sensor module, and can also be used as an adhesive or sealant containing the curable resin composition.
• the curable resin composition can be supplied using a jet dispenser, an air dispenser, etc. Also, it can be supplied by a known coating method (dip coating, spray coating, bar coater coating, gravure coating, reverse gravure coating, spin coater coating, etc.) and a known printing method (lithographic printing, carton printing, metal printing, offset printing, screen printing, gravure printing, flexographic printing, inkjet printing, etc.).
• a known coating method dip coating, spray coating, bar coater coating, gravure coating, reverse gravure coating, spin coater coating, etc.
• a known printing method lithographic printing, carton printing, metal printing, offset printing, screen printing, gravure printing, flexographic printing, inkjet printing, etc.
• the resin composition is thermosetting and can be cured by heating at a temperature of 100°C or less, preferably 80°C or less, more preferably 75°C or less, even more preferably 70°C or more, preferably 45°C or more, and more preferably 55°C or more.
• the heating time for curing the curable resin composition is preferably 15 minutes to 4 hours, more preferably 30 minutes to 2 hours, and even more preferably 30 minutes to 60 minutes.
• the resin composition is ultraviolet curable and can be cured with an integrated light amount of 500 to 5000 mJ/ cm2 , preferably at a wavelength of 300 to 500 nm.
• Cured product A cured product is obtained by curing the curable resin composition, adhesive or sealant containing the curable resin composition.
• the cured product obtained by curing the curable resin composition at 80°C for 60 minutes has a glass transition temperature (Tg) measured using a dynamic viscoelasticity measuring device (e.g., DMA7100 manufactured by Hitachi High-Tech Science Corporation) of preferably 0°C to 150°C, more preferably 1°C to 120°C, even more preferably 2°C to 90°C, and even more preferably 3°C to 70°C.
• Tg glass transition temperature measured using a dynamic viscoelasticity measuring device
• a cured product with a low Tg is likely to react with aryl iodide in the resin composition and water vapor, and is likely to generate corrosive gas.
• the curable resin composition, adhesive or sealant containing the curable resin composition is considered to have a more significant corrosive gas capture effect by component (C) as the ion trapping agent captures the generated corrosive gas.
• the glass transition temperature can be measured by referring to the method in the examples described below.
• the curable resin composition When the curable resin composition is used as an adhesive or a sealant containing the curable resin composition for fixing, bonding or protecting an electronic component, an electronic device containing a cured product obtained by curing the curable resin composition, the adhesive or the sealant containing the curable resin composition is obtained.
• the electronic device may be a semiconductor device containing a semiconductor element. Examples of the electronic device include a mobile phone, a smartphone, a notebook computer, a tablet terminal, a camera module, and the like.
• the curable resin composition, the adhesive or the sealant containing the curable resin composition is used for fixing, bonding or protecting an electronic component, and can be cured by heating at a low temperature of 100 ° C. or less, preferably 80 ° C. or less, and a highly reliable electronic device in which corrosion to the adherend is suppressed can be provided.
• A1-3 ADEKA GLYCIROL (registered trademark) ED-509S (manufactured by ADEKA Corporation) p-tert-butylphenyl glycidyl ether, molecular weight of 206, epoxy group equivalent of 206/eq.
• A1-4 jER YX8000 (manufactured by Mitsubishi Chemical Corporation), hydrogenated bisphenol A diglycidyl ether, molecular weight 410, epoxy group equivalent 205 g/eq.
• A1-5) Celloxide (registered trademark) 2021P (manufactured by Daicel Corporation), 3',4'-epoxycyclomethyl 3,4-epoxycyclohexane carboxylate, molecular weight of 260, epoxy group equivalent of 130 g/eq.
• A2-2 OXT-101 (manufactured by Toagosei Co., Ltd.), 3-ethyl-3-hydroxymethyloxetane (oxetane alcohol), molecular weight 116, oxetane group equivalent 116 g/eq.
• C-2) IXEPLAS (registered trademark)-A2 (manufactured by Toagosei Co., Ltd.), components: Zr, Mg, Al-based, average particle size of primary particles (primary particle size): 200 nm (catalog value) (C-3): Hydrotalcite (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.), average particle size of primary particles: 20 ⁇ m (C-4): IXE (registered trademark)-700F (manufactured by Toagosei Co., Ltd.), components: Mg, Al-based, anion exchange-based, average particle size (median diameter) of primary particles: 1.5 ⁇ m (1500 nm) (catalog value) (C-5): SWMNA-010-1 (manufactured by Toda Kogyo Co., Ltd.), components: Mg, Al-based, anion exchange-based, average particle size of primary particles (primary particle size): 300 nm (C-2)
• D-3) Perocta O (manufactured by NOF Corporation), 1,1,3,3-tetramethylbutylperoxy-2-ethylhexanoate, 1-hour half-life temperature of 84°C, molecular weight of 272.4, SADT of 40°C.
• Photoradical generator (F-1) Omnirad (registered trademark) 184 (manufactured by IGM Resins), 1-hydroxycyclohexyl phenyl ketone
• G Filler
• G-1 SE5200SEE (manufactured by Admatechs Co., Ltd.), high-purity synthetic spherical silica.
• G-2) Cabosil (registered trademark) TS720 (manufactured by Cabot Japan Co., Ltd.), hydrophobic silica.
• Discoloration evaluation heating The resin composition was applied by stencil printing to a size of 6 mm ⁇ (diameter: 6 mm) and a thickness of 600 ⁇ m on a copper-plated glass epoxy board (NEMA or ANSI standard FR4 board) with a width of 3 cm, a height of 3 cm, and a thickness of 1 mm. Then, it was thermally cured at 80°C for 60 minutes in a blower dryer. The obtained test piece was left in a constant temperature and high humidity chamber for 500 hours under conditions of a temperature of 85°C and a humidity of 85%. The test piece was removed from the constant temperature and humidity chamber, and it was visually confirmed whether the copper around the cured resin composition had discolored.
• NEMA copper-plated glass epoxy board

Landscapes

• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Polymers & Plastics (AREA)
• Health & Medical Sciences (AREA)
• Medicinal Chemistry (AREA)
• Inorganic Chemistry (AREA)
• Life Sciences & Earth Sciences (AREA)
• Engineering & Computer Science (AREA)
• Materials Engineering (AREA)
• Wood Science & Technology (AREA)
• Epoxy Resins (AREA)
• Structures Or Materials For Encapsulating Or Coating Semiconductor Devices Or Solid State Devices (AREA)

Priority Applications (4)

Applications Claiming Priority (2)

Publications (1)

Family

ID=91717033

Family Applications (1)

Country Status (6)

Cited By (2)

Citations (5)

Family Cites Families (1)

• 2023
  • 2023-07-27 KR KR1020257011194A patent/KR20250128290A/ko active Pending
  • 2023-07-27 CN CN202380080555.9A patent/CN120225586A/zh active Pending
  • 2023-07-27 EP EP23911230.3A patent/EP4644456A4/en active Pending
  • 2023-07-27 WO PCT/JP2023/027618 patent/WO2024142446A1/ja not_active Ceased
  • 2023-07-27 JP JP2024567192A patent/JPWO2024142446A1/ja active Pending
  • 2023-08-08 TW TW112129672A patent/TW202426595A/zh unknown

Patent Citations (5)

Non-Patent Citations (1)

Also Published As

Similar Documents

Legal Events