WO2011087008A1 - Composition de résine durcissable, substance résultant du durcissement de ladite composition, et élément optique - Google Patents

Composition de résine durcissable, substance résultant du durcissement de ladite composition, et élément optique Download PDF

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Publication number
WO2011087008A1
WO2011087008A1 PCT/JP2011/050330 JP2011050330W WO2011087008A1 WO 2011087008 A1 WO2011087008 A1 WO 2011087008A1 JP 2011050330 W JP2011050330 W JP 2011050330W WO 2011087008 A1 WO2011087008 A1 WO 2011087008A1
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meth
resin composition
curable resin
mass
polymerizable monomer
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PCT/JP2011/050330
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English (en)
Japanese (ja)
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一成 松村
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三菱レイヨン株式会社
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    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L23/00—Details of semiconductor or other solid state devices
    • H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
    • H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
    • H01L23/293—Organic, e.g. plastic
    • H01L23/296—Organo-silicon compounds
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/02—Details
    • H05B33/04—Sealing arrangements, e.g. against humidity
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
    • H10K59/80—Constructional details
    • H10K59/87—Passivation; Containers; Encapsulations
    • H10K59/873—Encapsulations
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F230/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
    • C08F230/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal
    • C08F230/08—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon
    • C08F230/085—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon the monomer being a polymerisable silane, e.g. (meth)acryloyloxy trialkoxy silanes or vinyl trialkoxysilanes
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2224/00—Indexing scheme for arrangements for connecting or disconnecting semiconductor or solid-state bodies and methods related thereto as covered by H01L24/00
    • H01L2224/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
    • H01L2224/42—Wire connectors; Manufacturing methods related thereto
    • H01L2224/47—Structure, shape, material or disposition of the wire connectors after the connecting process
    • H01L2224/48—Structure, shape, material or disposition of the wire connectors after the connecting process of an individual wire connector
    • H01L2224/4805—Shape
    • H01L2224/4809—Loop shape
    • H01L2224/48091—Arched
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2224/00—Indexing scheme for arrangements for connecting or disconnecting semiconductor or solid-state bodies and methods related thereto as covered by H01L24/00
    • H01L2224/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
    • H01L2224/42—Wire connectors; Manufacturing methods related thereto
    • H01L2224/47—Structure, shape, material or disposition of the wire connectors after the connecting process
    • H01L2224/48—Structure, shape, material or disposition of the wire connectors after the connecting process of an individual wire connector
    • H01L2224/481—Disposition
    • H01L2224/48151—Connecting between a semiconductor or solid-state body and an item not being a semiconductor or solid-state body, e.g. chip-to-substrate, chip-to-passive
    • H01L2224/48221—Connecting between a semiconductor or solid-state body and an item not being a semiconductor or solid-state body, e.g. chip-to-substrate, chip-to-passive the body and the item being stacked
    • H01L2224/48245—Connecting between a semiconductor or solid-state body and an item not being a semiconductor or solid-state body, e.g. chip-to-substrate, chip-to-passive the body and the item being stacked the item being metallic
    • H01L2224/48247—Connecting between a semiconductor or solid-state body and an item not being a semiconductor or solid-state body, e.g. chip-to-substrate, chip-to-passive the body and the item being stacked the item being metallic connecting the wire to a bond pad of the item
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2224/00—Indexing scheme for arrangements for connecting or disconnecting semiconductor or solid-state bodies and methods related thereto as covered by H01L24/00
    • H01L2224/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
    • H01L2224/42—Wire connectors; Manufacturing methods related thereto
    • H01L2224/47—Structure, shape, material or disposition of the wire connectors after the connecting process
    • H01L2224/49—Structure, shape, material or disposition of the wire connectors after the connecting process of a plurality of wire connectors
    • H01L2224/491—Disposition
    • H01L2224/49105—Connecting at different heights
    • H01L2224/49107—Connecting at different heights on the semiconductor or solid-state body
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2224/00—Indexing scheme for arrangements for connecting or disconnecting semiconductor or solid-state bodies and methods related thereto as covered by H01L24/00
    • H01L2224/73—Means for bonding being of different types provided for in two or more of groups H01L2224/10, H01L2224/18, H01L2224/26, H01L2224/34, H01L2224/42, H01L2224/50, H01L2224/63, H01L2224/71
    • H01L2224/732—Location after the connecting process
    • H01L2224/73251—Location after the connecting process on different surfaces
    • H01L2224/73265—Layer and wire connectors
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
    • H01L2924/10—Details of semiconductor or other solid state devices to be connected
    • H01L2924/11—Device type
    • H01L2924/12—Passive devices, e.g. 2 terminal devices
    • H01L2924/1204—Optical Diode
    • H01L2924/12044—OLED
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
    • H01L2924/15—Details of package parts other than the semiconductor or other solid state devices to be connected
    • H01L2924/181—Encapsulation
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L33/00—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
    • H01L33/48—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof characterised by the semiconductor body packages
    • H01L33/52—Encapsulations
    • H01L33/56—Materials, e.g. epoxy or silicone resin
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
    • H10K59/80—Constructional details
    • H10K59/87—Passivation; Containers; Encapsulations
    • H10K59/871—Self-supporting sealing arrangements
    • H10K59/8722—Peripheral sealing arrangements, e.g. adhesives, sealants

Definitions

  • the present invention relates to a curable resin composition, an optical member made of the cured product, a sealing material for a light emitting diode, and a filling material for an organic electroluminescence (EL) display panel.
  • EL organic electroluminescence
  • Light-emitting diodes have long life and energy saving, and can be reduced in size and weight, and thus have been put to practical use as various light sources.
  • the development of organic EL devices as displays that can be made thin and flexible, and surface-emitting illumination that saves energy has become active. These devices are expected to be in great demand in the future as next-generation lighting, displays, or display members.
  • the light emitting diode has a structure in which the light emitting element is sealed with a sealing material made of a transparent resin for the purpose of protecting the light emitting element from dust, impact, and the like and increasing light extraction efficiency.
  • solid adhesive sealing filled with transparent resin from a panel with a hollow sealing structure for the purpose of improving the light extraction efficiency and visibility and improving the deflection of the glass substrate accompanying the enlargement of the panel Conversion of the structure to a panel is being considered.
  • the transparent resin used in these materials not only exhibits high transmittance in the visible light region or the emission wavelength of the light-emitting diode, but also has heat resistance and light resistance to such an extent that coloring is not caused by heat generation or light emission during device operation.
  • Many properties are required, such as adhesion to inorganic materials.
  • (Meth) acrylic resin typified by polymethylmethacrylate has been used in optical members such as flat panel display members, lenses, and optical waveguides because of its excellent optical properties such as high transmittance in a wide wavelength range. Development to light emitting diodes and organic EL display members is also expected.
  • the (meth) acrylic resin is used in these devices, there are problems such as high water absorption, insufficient adhesion, and heat resistance.
  • Patent Document 1 discloses (meth) acrylic acid ester having an alicyclic hydrocarbon group for improving heat resistance, for improving adhesiveness
  • a technique using a composition containing a (meth) acrylic acid ester having a polyethylene glycol structure is disclosed.
  • the blending of the highly polar oligomer promotes an increase in water absorption and a decrease in heat resistance, which may cause a problem when used in the above device.
  • the present invention has been made in view of the above circumstances, and the cured product obtained has high heat resistance and low water absorption, as well as an optical member made of the cured product, and sealing for a light emitting diode.
  • An object is to provide a material, a filling material for an organic EL display panel, a light emitting diode provided with the sealing material for a light emitting diode, and an organic EL display panel provided with the filling material for an organic EL display panel.
  • the first aspect of the present invention for solving the above problems is (A) a (meth) acrylic polymerizable monomer having an alkoxysilane structure, and (B) a (meth) acrylic polymerizable monomer having a carboxyl group. It is a curable resin composition containing a body (however, a silicon atom is not included in the structure) and (C) a (meth) acrylic polymerizable monomer represented by the following general formula (1).
  • R 1 or R 3 is independently an acryloyl group or a methacryloyl group
  • R 2 is an alkylene group having 3 to 6 carbon atoms
  • n is an integer of 2 to 30.
  • the (meth) acrylic polymerizable monomer represented by the general formula (1) is a polybutylene glycol di (meth) acrylate. Is a curable resin composition.
  • (D) a (meth) acrylic polymerizable monomer in which the substituent of the ester moiety has an alicyclic hydrocarbon structure Is a curable resin composition.
  • the (E) ester moiety substituent is a linear or branched alkyl group
  • It is a curable resin composition containing a (meth) acrylic polymerizable monomer.
  • a curable resin composition further comprising (F) an antioxidant in addition to the constitution of any one of the first to fourth aspects.
  • a sixth aspect of the present invention is a curable resin composition that further comprises (G) a polymerization initiator in addition to the structure of any one of the first to fifth aspects.
  • a seventh aspect of the present invention is a curable resin composition further containing a (H) (meth) acrylic polymer in addition to the structure of any one of the first to sixth aspects.
  • the (A) alkoxysilane structure is included with respect to 100% by mass of the total polymerizable component.
  • the (A) alkoxysilane structure is included with respect to 100% by mass of the total polymerizable component.
  • a tenth aspect of the present invention is an optical member comprising a cured product of the curable resin composition according to any one of the first to ninth aspects.
  • An eleventh aspect of the present invention is a light-emitting diode encapsulant comprising a cured product of the curable resin composition according to any one of the first to ninth aspects.
  • a twelfth aspect of the present invention is a filler for an organic EL display panel comprising a cured product of the curable resin composition according to any one of the first to ninth aspects.
  • a thirteenth aspect of the present invention is a light emitting diode comprising the light emitting diode sealing material according to the eleventh aspect.
  • a fourteenth aspect of the present invention is an organic EL display panel comprising the organic EL display panel filler according to the twelfth aspect.
  • cured material obtained has high heat resistance and low water absorption, curable resin composition, the optical member which consists of the hardened
  • a light-emitting diode including the light-emitting diode sealing material and an organic EL display panel including the organic EL display panel filler can be provided.
  • the curable resin composition of the present invention comprises (A) a (meth) acrylic polymerizable monomer having an alkoxysilane structure (hereinafter referred to as (A) component), and (B) a carboxyl group-containing (meth).
  • Acrylic polymerizable monomer (however, silicon atom is not included in the structure) (hereinafter referred to as (B) component) and (C) (meth) acrylic polymerizable represented by the following general formula (1)
  • a curable resin composition containing a monomer hereinafter referred to as component (C)).
  • R 1 or R 3 is independently an acryloyl group or a methacryloyl group
  • R 2 is an alkylene group having 3 to 6 carbon atoms
  • n is an integer of 2 to 30.
  • (meth) acryl is a general term for acrylic and methacrylic.
  • (Meth) acrylate” is a general term for acrylate and methacrylate.
  • (Meth) acryloxy” described later is a general term for acryloxy and methacryloxy.
  • the “(meth) acryloyl group” is a general term for a methacryloyl group and an acryloyl group.
  • the (meth) acrylic polymerizable monomer represented by the general formula (1) is preferably polybutylene glycol (meth) acrylate.
  • the curable resin composition of the present invention further contains (D) a (meth) acrylic polymerizable monomer (hereinafter referred to as (D) component) in which the substituent of the ester moiety has an alicyclic hydrocarbon structure. It is preferable to do.
  • the curable resin composition of the present invention preferably further comprises (E) a (meth) acrylic polymerizable monomer (hereinafter referred to as (E) component) in which the substituent of the ester moiety is an alkyl group. .
  • the curable resin composition of the present invention preferably further contains (F) an antioxidant.
  • the curable resin composition of the present invention preferably further contains (G) a polymerization initiator.
  • the curable resin composition of the present invention preferably further contains a (H) (meth) acrylic polymer.
  • the components (A) to (E) are polymerizable components.
  • Component (A) A component is a component which contributes mainly to the heat resistance of the hardened
  • the component (A) include compounds represented by the following general formula (a1). CH 2 ⁇ C (R) —COO—R 1 —Si (R 2 ) (R 3 ) (R 4 ) (a1)
  • R is a hydrogen atom or a methyl group
  • R 1 is an alkylene group
  • R 2 to R 4 are each independently an alkoxy group or an alkyl group, and at least one of R 2 to R 4 One is an alkoxy group.
  • R may be a hydrogen atom or a methyl group.
  • a methyl group is preferable in terms of heat resistance.
  • the alkylene group for R 1 may be linear or branched, and is preferably linear.
  • the alkylene group preferably has 1 to 5 carbon atoms, particularly preferably 3.
  • the alkoxy group of R 2 to R 4 may be either linear or branched, and is preferably linear.
  • the alkoxy group preferably has 1 to 4 carbon atoms, particularly preferably 1 or 2.
  • the alkyl group of R 2 to R 4 may be either linear or branched, and is preferably linear.
  • the alkyl group preferably has 1 to 4 carbon atoms, more preferably 1 or 2, and particularly preferably 1.
  • at least one is preferably an alkoxy group, and two or three are preferably alkoxy groups.
  • component (A) examples include 3- (meth) acryloxypropylmethyldimethoxysilane, 3- (meth) acryloxypropyltrimethoxysilane, 3- (meth) acryloxypropylmethyldiethoxysilane, 3- (meth) (Meth) acryloxypropyltriethoxysilane, 3- (meth) acryloxypropylmethyldipropoxysilane, 3- (meth) acryloxypropyltripropoxysilane, 3- (meth) acryloxypropylmethyldibutoxysilane, 3- ( And (meth) acryloxypropyltributoxysilane. These may be used alone or in combination of two or more.
  • the curable resin composition of the present invention contains only the components (A) to (C) as polymerizable components (when it does not contain the components (D) and (E)), the curable resin composition (
  • the amount of component A) is preferably 1 to 70% by weight, more preferably 5 to 65% by weight, and more preferably 10 to 60% by weight when the total amount of components (A) to (C) is 100% by weight. Is more preferable.
  • the amount of component A) is preferably 1 to 70% by weight, more preferably 5 to 65% by weight, and more preferably 10 to 60% by weight when the total amount of components (A) to (C) is 100% by weight. Is more preferable.
  • cured material obtained and the adhesiveness to an inorganic material become favorable.
  • the curable resin composition of the present invention contains any one or both of the component (D) and the component (E) in addition to the components (A) to (C) as the polymerizable component
  • the curable resin composition The amount of component (A) in the product is preferably 1 to 35% by weight, more preferably 5 to 30% by weight, with the total amount of components (A) to (E) being 100% by weight. 25 mass% is further more preferable.
  • (A) By making the compounding quantity of a component into 1 mass% or more, the heat resistance of the hardened
  • a component is a component which contributes mainly to the adhesive improvement to the inorganic material of the hardened
  • the component (B) include compounds represented by the following general formula (b1).
  • CH 2 C (R) -COO-X (b1)
  • R is a hydrogen atom or a methyl group
  • X is a hydrogen atom or —R 5 —O—CO—R 6 —COOH
  • the R 5 is an alkylene group
  • the R 6 is carbonized. It is a hydrogen group.
  • the compound in which X is —R 5 —O—CO—R 6 —COOH is a so-called (meth) acryloyloxyalkyl ester of a dicarboxylic acid.
  • the alkylene group for R 5 an alkylene group having 1 to 3 carbon atoms is preferable, and an ethylene group is particularly preferable.
  • the hydrocarbon group for R 6 may be an aromatic hydrocarbon group or an aliphatic hydrocarbon group. From the viewpoint of transparency, an aliphatic hydrocarbon group is preferred. Examples of the aromatic hydrocarbon group include an arylene group such as a phenylene group.
  • the aliphatic hydrocarbon group may be linear, branched or cyclic, and is preferably cyclic from the viewpoint of heat resistance.
  • the aliphatic hydrocarbon group may be saturated or unsaturated, and is preferably saturated.
  • the aliphatic hydrocarbon group preferably has 1 to 5 carbon atoms, and more preferably 2 to 4 carbon atoms.
  • the aliphatic hydrocarbon group is cyclic, the aliphatic hydrocarbon group preferably has 5 to 20 carbon atoms, and more preferably 6 to 10 carbon atoms.
  • component (B) examples include (meth) acrylic acid, 2- (meth) acryloyloxyethyl succinate, 2- (meth) acryloyloxyethyl maleate, 2- (meth) acryloyloxyethyl phthalate, hexa And 2- (meth) acryloyloxyethyl hydrophthalate. These may be used alone or in combination of two or more. From the viewpoint of heat resistance, at least one selected from the group consisting of methacrylic acid and 2-methacryloyloxyethyl hexahydrophthalate is preferable, and methacrylic acid is particularly preferable.
  • the curable resin composition of the present invention contains only the components (A) to (C) as polymerizable components (when it does not contain the components (D) and (E)), the curable resin composition (
  • the blending amount of component B) is preferably 0.05 to 20% by weight, more preferably 0.1 to 15% by weight, assuming that the total blending amount of components (A) to (C) is 100% by weight. More preferably, the content is 5 to 10% by mass.
  • cured material obtained becomes favorable.
  • the curable resin composition of the present invention contains any one or both of the component (D) and the component (E) in addition to the components (A) to (C) as the polymerizable component
  • the curable resin composition The amount of component (B) in the product is preferably 0.05 to 10% by weight, more preferably 0.1 to 5% by weight, with the total amount of components (A) to (E) being 100% by weight. Preferably, 0.3 to 3% by mass is more preferable.
  • B) By making the compounding quantity of a component 0.05 mass% or more, the adhesiveness to the inorganic material of the hardened
  • the component (C) mainly contributes to the suppression of the curing shrinkage of the curable resin composition of the present invention and the decrease in the elastic modulus and water absorption of the cured product obtained by polymerizing the curable resin composition. It is an ingredient.
  • the component (C) is obtained by sealing both ends of polyalkylene glycol with (meth) acrylic acid.
  • the polyalkylene glycol di (meth) acrylate represented by the following general formula (1) is used. is there.
  • R 1 or R 3 is independently an acryloyl group or a methacryloyl group
  • R 2 is an alkylene group having 3 to 6 carbon atoms
  • n is the degree of polymerization of the oxyalkylene group.
  • the polymerization degree n is preferably 3 to 25, more preferably 5 to 20, and further preferably 7 to 15.
  • the degree of polymerization n here means a median value.
  • the degree of polymerization is 3 or more, the curing shrinkage and the elastic modulus of the resulting cured product are good.
  • the degree of polymerization is 30 or less, the heat resistance is good.
  • component (C) examples include polypropylene glycol di (meth) acrylate, polybutylene glycol di (meth) acrylate, polypentylene glycol di (meth) acrylate, polyhexylene glycol di (meth) acrylate and the like. From the viewpoint of heat resistance, polybutylene glycol di (meth) acrylate is particularly preferable.
  • the curable resin composition of the present invention contains only the components (A) to (C) as polymerizable components (when it does not contain the components (D) and (E))
  • the curable resin composition ( Component C) is preferably 10 to 90% by mass, more preferably 20 to 85% by mass, and 30 to 80% by mass when the total amount of components (A) to (C) is 100% by mass. Is more preferable.
  • the curable resin composition of the present invention contains any one or both of the component (D) and the component (E) in addition to the components (A) to (C) as the polymerizable component
  • the curable resin composition The amount of component (C) in the product is preferably 10 to 60% by weight, more preferably 20 to 55% by weight, with the total amount of components (A) to (E) being 100% by weight, more preferably 30 to 50 mass% is more preferable.
  • the curable resin composition of the present invention can further contain a component (D) for the purpose of suppressing the curing shrinkage rate, improving the heat resistance of the resulting cured product, and reducing the water absorption rate.
  • a component (D) for the purpose of suppressing the curing shrinkage rate, improving the heat resistance of the resulting cured product, and reducing the water absorption rate.
  • the component (D) include compounds represented by the following general formula (d1).
  • CH 2 C (R) —COO—R 7 (d1)
  • R is a hydrogen atom or a methyl group
  • R 7 is a monovalent alicyclic hydrocarbon group.
  • the alicyclic hydrocarbon group for R 7 may be saturated or unsaturated, and is preferably saturated.
  • the alicyclic hydrocarbon group may be monocyclic or polycyclic.
  • the alicyclic hydrocarbon group preferably has 5 to 20 carbon atoms, more preferably 6 to 12 carbon atoms.
  • Specific examples of the component (D) include cyclopentyl (meth) acrylate, cyclohexyl (meth) acrylate, 4-t-butylcyclohexyl (meth) acrylate, isobornyl (meth) acrylate, adamantyl (meth) acrylate, 2-methyl-2 -Adamantyl (meth) acrylate, 2-ethyl-2-adamantyl (meth) acrylate, dicyclopentanyl (meth) acrylate, dicyclopentenyl (meth) acrylate, dicyclopentanyloxyethyl (meth) acrylate, dicyclopentenyl Oxyethyl (meth) acrylate, (1R) -fentyl (meth) acrylate, 1,4-cyclohexanedimethanol di (me
  • the curable resin composition of the present invention contains the component (D), the blending amount thereof is preferably 10 to 60% by weight when the total blending amount of the components (A) to (E) is 100% by weight, It is more preferably 20 to 55% by mass, and further preferably 30 to 50% by mass.
  • the curable resin composition of the present invention can further contain a component (E) for the purpose of improving the heat resistance of a cured product obtained by polymerizing the curable resin composition of the present invention.
  • a component (E) for the purpose of improving the heat resistance of a cured product obtained by polymerizing the curable resin composition of the present invention.
  • the component (E) include compounds represented by the following general formula (e1).
  • CH 2 C (R) -COO-R 8 (e1)
  • R is a hydrogen atom or a methyl group
  • R 8 is an alkyl group.
  • the alkyl group for R 8 may be linear or branched, and is preferably linear from the viewpoints of transparency and heat resistance.
  • the alkyl group preferably has 1 to 12 carbon atoms, and more preferably 1 to 4 carbon atoms.
  • component (E) examples include methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, n-butyl (meth) acrylate, i-butyl (meth) acrylate, and t-butyl (meth).
  • the curable resin composition of the present invention includes the component (E), the blending amount thereof is preferably 5 to 40% by weight when the total blending amount of the components (A) to (E) is 100% by weight, 5 to 30% by mass is more preferable, and 5 to 20% by mass is more preferable.
  • the curable resin composition of the present invention further comprises (F) an antioxidant (hereinafter referred to as (F) component) for the purpose of improving the heat resistance of a cured product obtained by polymerizing the curable resin composition of the present invention. .) Can be contained.
  • an antioxidant hereinafter referred to as (F) component
  • component (F) examples include 2,6-di-t-butylphenol, 2,6-di-t-butyl-p-cresol, n-octadecyl-3- (3 ′, 5′-di-t -Butyl-4'-hydroxyphenyl) propionate, tetrakis- [methylene-3- (3 ', 5'-di-t-butyl-4'-hydroxyphenyl) propionate] methane, triethylene glycol bis [3- (3 -T-butyl-5-methyl-4-hydroxyphenyl) propionate], 1,6-hexanediol bis [3- (3,5-di-t-butyl-4-hydroxyphenyl) propionate], etc.
  • Inhibitors triphenyl phosphite, trisisodecyl phosphite, tristridecyl phosphite, tris (2,4-di-t-butylphenyl) phosphite It includes phosphorus-based antioxidant or the like is. These may be used alone or in combination of two or more. Of these, phenolic antioxidants are preferred, and of these, n-octadecyl-3- (3 ′, 5′-di-t-butyl-4′-hydroxyphenyl) propionate is preferred because of its excellent effect of improving heat resistance.
  • the blending amount of the component (F) in the curable resin composition of the present invention is preferably 0.01 to 3 parts by weight when the total blending amount of the components (A) to (E) is 100 parts by weight.
  • the curable resin composition of the present invention can be made into a cured product by further adding (G) a polymerization initiator (hereinafter referred to as (G) component) and carrying out polymerization.
  • the kind of the polymerization initiator is not particularly limited, and may be appropriately selected from known polymerization initiators according to the polymerization method.
  • examples of the thermal polymerization initiator used in the case of thermal polymerization include organic peroxides and azo compounds.
  • organic peroxides include ketone peroxides such as methyl ketone peroxide; 1,1-di (t-hexylperoxy) -3,3,5-trimethylcyclohexane, 1,1-di (t- Peroxyketals such as hexylperoxy) cyclohexane and 1,1-di (t-butylperoxy) cyclohexane; 1,1,3,3, -tetramethylbutyl hydroperoxide, cumene hydroperoxide, p-menthane hydro Hydroperoxides such as peroxides; diacyl peroxides such as dicumyl peroxide, di-t-butyl peroxide, dilauroyl peroxide, dibenzoyl peroxide; bis (4-t-butylcyclohexyl) peroxydicarbonate, Di (2-ethylhexyl) peroxy Peroxydicarbonate such as carbonate; t-butyl peroxid
  • azo compound examples include 2,2′-azobisisobutyronitrile, 2,2′-azobis (2-methylbutyronitrile), 2,2′-azobis (2,4-dimethylvaleronitrile). 1,1′-azobis-1-cyclohexanecarbonitrile, dimethyl-2,2′-azobisisobutyrate, 4,4′-azobis-4-cyanovaleric acid, 2,2′-azobis- (2 -Amidinopropane) dihydrochloride and the like. These may be used alone or in combination of two or more.
  • At least one selected from the group selected from dilauroyl peroxide and bis (4-t-butylcyclohexyl) peroxydicarbonate Is preferred.
  • the blending amount of the component (G) in the curable resin composition of the present invention is preferably 0.05 to 3 parts by weight when the total blending amount of the components (A) to (E) is 100 parts by weight. 1 to 2 parts by mass is more preferable, and 0.3 to 1.5 parts by mass is even more preferable.
  • the curable resin composition of the present invention is a (H) (meth) acrylic polymer (hereinafter referred to as (H)) for the purpose of improving the curability and heat resistance of the curable resin composition of the present invention. Component)).
  • (H) component By containing (H) component, the polymerization rate in an oxygen contact surface improves. Thereby, the heat resistance of the cured product of the curable resin composition can be improved.
  • the component (H) is preferably dissolved in the components (A) to (E) in the curable resin composition of the present invention.
  • the dissolution method is not particularly limited, but may be stirred and dissolved at room temperature, or may be stirred and dissolved while heating at about 40 ° C. to 100 ° C.
  • the “(meth) acrylic polymer” means a polymer containing 50% by mass or more of (meth) acrylic monomer units in the composition.
  • (Meth) acrylic monomer means a monomer having a (meth) acryloyl group.
  • “Unit” means a repeating unit constituting a polymer.
  • the (meth) acrylic monomer may be a monofunctional monomer or a polyfunctional monomer.
  • “monofunctional monomer” means a monomer having one polymerizable group such as a (meth) acryloyl group
  • “polyfunctional monomer” means a monomer having two or more polymerizable groups.
  • the (meth) acrylic monomer used for the component (H) a monofunctional monomer having one (meth) acryloyl group is particularly preferable.
  • (meth) acrylic monomers include (meth) acrylic acid, methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, n-butyl (meth) acrylate, i-butyl (meth) Acrylate, t-butyl (meth) acrylate, heptyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, n-octyl (meth) acrylate, isooctyl (meth) acrylate, n-nonyl (meth) acrylate, isononyl (meth) Acrylate, decyl (meth) acrylate, lauryl (meth) acrylate, tridecyl (meth) acrylate, stearyl (meth) acrylate, cyclohexyl (meth) acrylate, benzyl (meth) acrylic acid,
  • the (meth) acrylic monomer unit contained in the component (H) may be one type or two or more types.
  • the proportion of the (meth) acrylic monomer unit is preferably 70% by mass or more, and more preferably 80% by mass or more.
  • the upper limit of the said ratio is not specifically limited, 100 mass% may be sufficient.
  • the component (H) may contain other monomer units other than the (meth) acrylic monomer units.
  • what is copolymerizable with a (meth) acrylic-type monomer should just be mentioned, for example, vinyl-type monomers, such as styrene, are mentioned.
  • the component (H) include homopolymers such as polymethyl methacrylate, polyethyl methacrylate, and polybutyl methacrylate; a copolymer comprising methyl methacrylate units and n-butyl methacrylate units, methyl methacrylate units and n -Copolymers such as copolymers comprising butyl acrylate units.
  • those containing a methyl methacrylate unit are preferable from the viewpoint of transparency of the cured product, and are composed of a methyl methacrylate unit and an n-butyl methacrylate unit from the viewpoint of solubility in the components (A) to (E).
  • a copolymer is particularly preferred.
  • the blending amount of the component (H) in the curable resin composition of the present invention is preferably 0.1 to 15 parts by weight when the total blending amount of the components (A) to (E) is 100 parts by weight. 5 to 10 parts by mass is more preferable, and 1 to 8 parts by mass is further preferable.
  • the curability and heat resistance are improved without impairing the transparency of the cured product of the curable resin composition. can do.
  • the curable resin composition of the present invention includes, for example, a plasticizer, an ultraviolet absorber, an antistatic agent, a lubricant, in order to improve various properties as long as the effects of the present invention are not impaired.
  • Various additives such as release agents, dyes, pigments, antifoaming agents, polymerization inhibitors, fillers, conductive agents, and phosphors may be added.
  • the curable resin composition of the present invention is preferably produced by adding (G) component at room temperature to a mixture of components (A) to (F) and (H) in advance and mixing them.
  • the temperature conditions at the time of mixing the components (A) to (F) and the component (H) are not particularly limited, but may be heated if necessary. When heating, it is preferable to heat at 40 to 100 ° C.
  • the curable resin composition of the present invention is preferably made into a cured product by polymerization in a state containing the component (G).
  • the polymerization method include polymerization by redox reaction, thermal polymerization, and photopolymerization, and thermal polymerization is preferable because the transparency and heat resistance of the cured product are improved.
  • the polymerization conditions in the case of thermal polymerization vary depending on the use of the cured product and are not particularly limited, but the heating temperature should be sufficiently lower than the boiling point of the monomer contained in the curable resin composition. It is effective for obtaining a cured product containing no bubbles. Therefore, the heating temperature is preferably 30 to 160 ° C., more preferably 50 ° C.
  • the heating time varies depending on the heating temperature, but is preferably 0.5 to 5 hours, more preferably 1 to 3 hours.
  • After the polymerization it is preferable to further carry out after cure. As a result, the amount of residual monomer in the cured product can be reduced, which is effective in improving heat resistance.
  • heating at 90 ° C. to 150 ° C. for 0.5 to 3 hours is preferable, and heating at 100 ° C. to 130 ° C. for 1 to 2 hours is more preferable.
  • the curable resin composition of the present invention has high heat resistance and low water absorption of the obtained cured product. Therefore, it is useful for an optical member, and particularly useful for a sealing material for light emitting diodes of each color or a filling material for organic EL display panels. Moreover, since the curable resin composition of the present invention can be polymerized by heating at a relatively low temperature to form a cured product, it is suitable for the curing conditions of the filler for organic EL panels described later.
  • the optical member of the present invention comprises a cured product of the curable resin composition of the present invention.
  • optical members include films and sheets used in light emitting diodes, organic EL display panels, flat panel displays, touch panels, electronic paper, photodiodes, phototransistors, solar cells, lenses, coatings, optical waveguides, sealings. Examples thereof include a stopping material, a filler, an adhesive, a pressure-sensitive adhesive, fine particles, and a pigment dispersion binder.
  • the optical member of the present invention is particularly useful for a light-emitting diode encapsulant and an organic EL display panel filler that require high transparency, heat resistance, and adhesion to an inorganic material.
  • the sealing material for light emitting diodes of this invention consists of hardened
  • FIG. 1 sectional drawing of one Embodiment of the light emitting diode provided with the sealing material for light emitting diodes of this invention is shown.
  • a light-emitting diode 100 shown in FIG. 1 includes a light-emitting diode element 2, a package substrate 7 having an electrode (anode) 5 and an electrode (cathode) 6 formed on its surface, and reflectors 4a and 4b provided on the package substrate 7. .
  • the light emitting diode element 2 is disposed via a die bonding material 8 at the bottom of a recess formed by the package substrate 7 and the reflectors 4a and 4b, and an electrode (anode) 5 and an electrode (cathode) 6 by bonding wires 3a and 3b. Connected to form a package.
  • a light emitting diode sealing material 1 of the present invention is filled in the recess of the package, and the light emitting diode element 2 is sealed.
  • a method for molding the light-emitting diode encapsulant a method similar to a general method for molding a light-emitting diode encapsulant can be used.
  • the curable resin composition of the present invention is injected into a light emitting diode package and then heated at 50 to 160 ° C. for 1 to 5 hours.
  • a composition can be hardened and it can be set as the sealing material for light emitting diodes.
  • the filler for organic EL display panels of this invention consists of hardened
  • FIG. 2 sectional drawing of one Embodiment of the organic electroluminescent display panel provided with the filler for organic electroluminescent display panels of this invention is shown.
  • An organic EL display panel 200 shown in FIG. 2 includes two glass substrates 13a and 13b that are spaced apart from each other, an organic EL light-emitting element 11 formed on the glass substrate 13b, and a passivation 12 that covers the surface of the organic EL element 11. And comprising.
  • the peripheral edges of the glass substrates 13a and 13b are sealed with sealing materials 10a and 10b.
  • the space formed by the glass substrates 13a and 13b and the sealing materials 10a and 10b is filled with a filling material 9 for an organic EL display panel.
  • a thermal polymerization initiator included as the component (G)
  • cure by heating is mentioned. If UV irradiation or high-temperature treatment is performed at the time of curing the filler, the organic EL element may be lost, and thus it is preferable to perform heat curing at a relatively low temperature.
  • the heating temperature at the time of curing is preferably 30 to 100 ° C., more preferably 40 to 80 ° C. Since the curable resin composition of the present invention can be polymerized and cured by such a relatively low temperature heating, it is suitable for the curing conditions of the filler for organic EL panels.
  • the obtained aqueous suspension was filtered through a nylon filter cloth having an opening of 45 ⁇ m, and the filtrate was washed with deionized water. After dehydration, the filtrate was dried at 40 ° C. for 20 hours to obtain a granular (meth) acrylic polymer (hereinafter referred to as polymer A).
  • the obtained polymer A had a weight average molecular weight (Mw) of 60,000.
  • the weight average molecular weight was determined by dissolving the polymer A in a solvent (tetrahydrofuran) and converting the molecular weight measured using gel permeation chromatography into polystyrene.
  • Examples 1 to 19 Each component was blended in the proportions shown in Tables 1 and 2, and stirred at room temperature to obtain a curable resin composition.
  • the defoamed curable resin composition was poured into a mold prepared using a tempered glass covered with a polyethylene terephthalate (PET) film and a tube gasket made of vinyl chloride, and the mold was sealed. Thereafter, heat curing was performed at 70 ° C. for 2 hours, and after-curing was further performed at 120 ° C. for 1 hour. The mold was removed to obtain a cured plate-like resin having a thickness of 3 mm. The following physical property evaluation was performed about the obtained curable resin composition and plate-shaped resin cured material of thickness 3mm.
  • PET polyethylene terephthalate
  • Example 20 Add components (A) to (F) to a reaction vessel equipped with a stirrer, a condenser, and a thermometer in the proportions shown in Table 2, and then add component (H) (polymer A) while stirring. It was. (H) After adding all the components, it heated up at 60 degreeC and stirred for 2 hours, maintaining temperature. After confirming that the polymer A was completely dissolved, the polymer A was cooled to room temperature, and the component (G) (paroyl TCP) was further blended to obtain a curable resin composition. Using this curable resin composition, a plate-shaped village fat cured product having a thickness of 3 mm was prepared and evaluated in the same manner as in Examples 1 to 19.
  • the water absorption was measured and evaluated.
  • a plate-shaped resin cured product having a thickness of 3 mm was used.
  • the plate-shaped resin cured product was dried at 50 ° C. for 24 hours, and the mass after drying was measured. This mass was defined as the pre-test mass.
  • This cured resin sheet was immersed in pure water at 70 ° C. for 24 hours. Then, this plate-shaped resin cured product was pulled up from pure water, and after thoroughly wiping off water droplets on the surface, the mass of the plate-shaped resin cured product was measured. This mass was taken as the post-test mass.
  • the water absorption was calculated using the following formula (1), and the water absorption was evaluated from the water absorption according to the following criteria.
  • Water absorption rate (mass after test ⁇ mass before test) / mass before test ⁇ 100 (1) [Evaluation criteria] ⁇ : Water absorption is less than 1% ⁇ : Water absorption is 1% or more and less than 2% ⁇ : Water absorption is 2% or more and less than 3% ⁇ : Water absorption is 3% or more
  • Heat resistance evaluation A heat resistance test was performed using a plate-shaped resin cured product having a thickness of 3 mm, which was allowed to stand for 100 hours in an air atmosphere at 150 ° C.
  • the yellowness index (YI) of the resin plate before and after the test was measured using a color difference meter (SE2000, manufactured by Nippon Denshoku Industries Co., Ltd.), and the heat resistance was evaluated from the difference ( ⁇ YI) according to the following criteria.
  • YI was measured in the transmission mode. [Evaluation criteria] :: ⁇ YI is less than 2 ⁇ : ⁇ YI is 2 or more and less than 4 ⁇ : ⁇ YI is 4 or more and less than 6 ⁇ : ⁇ YI is 6 or more.
  • Examples 1 to 20 all had good water absorption and heat resistance evaluations, and none of the results was x. In particular, in terms of water absorption, the evaluation was good or better in all examples. On the other hand, as shown in Table 2, Comparative Example 1 was evaluated as x for water absorption and heat resistance.
  • KBM-503 3-methacryloxypropyltrimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd.).
  • KBE-503 3-methacryloxypropyltriethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd.).
  • MAA Methacrylic acid (manufactured by Mitsubishi Rayon Co., Ltd.).
  • PA 2-methacryloyloxyethyl phthalate (Mitsubishi Rayon Co., Ltd.).
  • HH 2-methacryloyloxyethyl hexahydrophthalate (Mitsubishi Rayon Co., Ltd.).
  • PEOM Polyethylene glycol dimethacrylate, polymerization degree n ⁇ 14 (manufactured by Shin-Nakamura Chemical Co., Ltd., trade name: NK ester 14G).
  • CHMA cyclohexyl methacrylate (Mitsubishi Rayon Co., Ltd.).
  • IBXMA Isobornyl methacrylate (manufactured by Mitsubishi Rayon Co., Ltd.).
  • FA-513M dicyclopentanyl methacrylate (manufactured by Hitachi Chemical Co., Ltd., trade name: FA-513M).
  • MMA Methyl methacrylate (manufactured by Mitsubishi Rayon Co., Ltd.).
  • n-BMA normal butyl methacrylate (manufactured by Mitsubishi Rayon Co., Ltd.).
  • IR1076 n-octadecyl-3- (3 ′, 5′-di-t-butyl-4′-hydroxyphenyl) propionate (manufactured by Ciba Japan, trade name: IRGANOX1076).
  • BHT 2,6-di-t-butyl-p-cresol (manufactured by Honshu Chemical Industry Co., Ltd.).
  • TCP bis (4-t-butylcyclohexyl) peroxydicarbonate (manufactured by NOF Corporation, trade name: Parroyl TCP).
  • cured material obtained has high heat resistance and low water absorption, curable resin composition, the optical member which consists of the hardened
  • SYMBOLS 1 Light emitting diode sealing material, 2 ... Light emitting diode element, 3a ... Bonding wire, 3b ... Bonding wire, 4a ... Reflector, 4b ... Reflector, 5 ... Electrode (anode), 6 ... Electrode (cathode), 7 ... Package Substrate, 8 ... Die bond material, 9 ... Filler for organic EL display panel, 10a ... Sealing material, 10b ... Sealing material, 11 ... Organic EL element, 12 ... Passivation, 13a ... Glass substrate, 13b ... Glass substrate, 100 ... light-emitting diode, 200 ... organic EL display panel

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  • Physics & Mathematics (AREA)
  • Condensed Matter Physics & Semiconductors (AREA)
  • General Physics & Mathematics (AREA)
  • Engineering & Computer Science (AREA)
  • Computer Hardware Design (AREA)
  • Microelectronics & Electronic Packaging (AREA)
  • Power Engineering (AREA)
  • Polymerisation Methods In General (AREA)
  • Graft Or Block Polymers (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne une composition de résine durcissable qui contient : (A) un monomère (méth)acrylique polymérisable ayant une structure alcoxysilane ; (B) un monomère (méth)acrylique polymérisable qui contient un groupe carboxyle mais pas d'atomes de silicium ; et (C) un monomère (méth)acrylique polymérisable représenté par la formule générale (1) (dans laquelle R1 et R3 représentent chacun indépendamment un groupe acryloyle ou un groupe méthacryloyle ; R2 représente un groupe alkylène en C3-6 ; et n représente un entier compris entre 2 et 30).
PCT/JP2011/050330 2010-01-14 2011-01-12 Composition de résine durcissable, substance résultant du durcissement de ladite composition, et élément optique WO2011087008A1 (fr)

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WO2013154165A1 (fr) * 2012-04-12 2013-10-17 三菱レイヨン株式会社 Résine liante d'électrode de batterie secondaire, composition d'électrode de batterie secondaire, électrode de batterie secondaire, et batterie secondaire
JP2015038188A (ja) * 2013-06-06 2015-02-26 東洋合成工業株式会社 組成物
JP2016092299A (ja) * 2014-11-07 2016-05-23 日立化成株式会社 電子部品の製造方法、光半導体素子封止用フィルム状硬化性樹脂組成物及び電子部品
JP2017075198A (ja) * 2014-02-25 2017-04-20 日立化成株式会社 アクリル樹脂組成物及び電子部品
KR20180087247A (ko) * 2015-11-26 2018-08-01 가부시끼가이샤 쓰리본드 열경화성 조성물 및 그를 이용한 도전성 접착제
JP2019108548A (ja) * 2019-02-06 2019-07-04 日立化成株式会社 アクリル樹脂組成物及び電子部品
JP2020007449A (ja) * 2018-07-06 2020-01-16 株式会社コバヤシ 光硬化性組成物

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WO1999055633A1 (fr) * 1998-04-28 1999-11-04 Mitsubishi Rayon Co., Ltd. Premix acrylique, faux marbre acrylique et leur production

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JPH0297439A (ja) * 1988-10-03 1990-04-10 Mitsubishi Rayon Co Ltd 合わせ硝子用樹脂組成物
JPH04164910A (ja) * 1990-10-26 1992-06-10 Mitsubishi Rayon Co Ltd ポリブチレングリコールジ（メタ）アクリレート及びそれを含む注型重合用樹脂組成物
JPH093145A (ja) * 1995-06-15 1997-01-07 Kyoeisha Chem Co Ltd 硬化性樹脂組成物
WO1999055633A1 (fr) * 1998-04-28 1999-11-04 Mitsubishi Rayon Co., Ltd. Premix acrylique, faux marbre acrylique et leur production

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013154165A1 (fr) * 2012-04-12 2013-10-17 三菱レイヨン株式会社 Résine liante d'électrode de batterie secondaire, composition d'électrode de batterie secondaire, électrode de batterie secondaire, et batterie secondaire
JP2015038188A (ja) * 2013-06-06 2015-02-26 東洋合成工業株式会社 組成物
JP2017075198A (ja) * 2014-02-25 2017-04-20 日立化成株式会社 アクリル樹脂組成物及び電子部品
JP2016092299A (ja) * 2014-11-07 2016-05-23 日立化成株式会社 電子部品の製造方法、光半導体素子封止用フィルム状硬化性樹脂組成物及び電子部品
KR20180087247A (ko) * 2015-11-26 2018-08-01 가부시끼가이샤 쓰리본드 열경화성 조성물 및 그를 이용한 도전성 접착제
JPWO2017090759A1 (ja) * 2015-11-26 2018-09-20 株式会社スリーボンド 熱硬化性組成物およびそれを用いた導電性接着剤
KR102526024B1 (ko) * 2015-11-26 2023-04-25 가부시끼가이샤 쓰리본드 열경화성 조성물 및 그를 이용한 도전성 접착제
JP2020007449A (ja) * 2018-07-06 2020-01-16 株式会社コバヤシ 光硬化性組成物
JP2019108548A (ja) * 2019-02-06 2019-07-04 日立化成株式会社 アクリル樹脂組成物及び電子部品

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