WO2013146081A1 - Composition de résine, produit durci à base de celle-ci, et matière réfléchissante pour semi-conducteurs optiques utilisant ledit produit durci - Google Patents

Composition de résine, produit durci à base de celle-ci, et matière réfléchissante pour semi-conducteurs optiques utilisant ledit produit durci Download PDF

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Publication number
WO2013146081A1
WO2013146081A1 PCT/JP2013/055544 JP2013055544W WO2013146081A1 WO 2013146081 A1 WO2013146081 A1 WO 2013146081A1 JP 2013055544 W JP2013055544 W JP 2013055544W WO 2013146081 A1 WO2013146081 A1 WO 2013146081A1
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resin composition
component
cured product
group
mass
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PCT/JP2013/055544
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English (en)
Japanese (ja)
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岡田　保也
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出光興産株式会社
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Priority to JP2014507583A priority Critical patent/JP5841237B2/ja
Publication of WO2013146081A1 publication Critical patent/WO2013146081A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • 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
    • C08G59/42—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof
    • 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
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C08F220/1807—C7-(meth)acrylate, e.g. heptyl (meth)acrylate or benzyl (meth)acrylate
    • 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
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C08F220/1811—C10or C11-(Meth)acrylate, e.g. isodecyl (meth)acrylate, isobornyl (meth)acrylate or 2-naphthyl (meth)acrylate
    • 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
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
    • C08F220/32—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals
    • C08F220/325—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals containing glycidyl radical, e.g. glycidyl (meth)acrylate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L33/04—Homopolymers or copolymers of esters
    • C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
    • C08L33/062—Copolymers with monomers not covered by C08L33/06
    • C08L33/068—Copolymers with monomers not covered by C08L33/06 containing glycidyl groups
    • 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
    • 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
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2312/00—Crosslinking
    • 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
    • H01L33/58—Optical field-shaping elements
    • H01L33/60—Reflective elements

Definitions

  • the present invention relates to a resin composition suitably used as a raw material for a reflective material for optical semiconductors, a cured product thereof, and a reflective material for optical semiconductors using the same.
  • LEDs light emitting diodes
  • white LEDs are expected as next-generation light sources that replace conventional white light bulbs, halogen lamps, HID lamps, and the like.
  • LEDs have been evaluated for their features such as long life, power saving, temperature stability, low voltage drive, etc., and are applied to displays, destination display boards, in-vehicle lighting, signal lights, emergency lights, mobile phones, video cameras and the like.
  • Such a light emitting device is usually manufactured by fixing an LED to a concave reflecting material formed by integrally molding a synthetic resin with a lead frame and sealing with a sealing material such as an epoxy resin or a silicone resin.
  • Patent Documents 1 to 3 propose a reflective material using a silicone resin
  • Patent Document 4 proposes a reflective material using an epoxy resin. It has not been served.
  • a silicone resin when used, there are concerns that a low molecular siloxane volatilizes to cause a contact failure, and that water vapor penetrates into the light emitting device and causes a failure of the light emitting element.
  • Patent Documents 5 and 6 disclose a reflective material using a (meth) acrylate resin.
  • the reflecting material hollow particles are used as a filler from the viewpoint of improving the light reflectance in the ultraviolet region.
  • the visible light region it is disclosed that a high light reflectance can be obtained by stacking with a material having a high light reflectance for visible light.
  • Patent Document 7 discloses an adamantane copolymer resin that gives a cured product excellent in optical properties such as transparency and light resistance, durability such as long-term heat resistance, and electrical properties such as dielectric constant, and a resin composition containing the same And its use, and as the adamantane copolymer resin, a constitutional unit derived from a (meth) acrylic monomer having a cationic polymerizable functional group and a constitution derived from a (meth) acrylic monomer having an adamantane structure Copolymer resins containing units in specific proportions are disclosed.
  • Patent Document 8 proposes an adamantane-based copolymer resin that gives a cured product having a light transmittance of 75% or more and excellent transparency, a resin composition containing the same, and a molded body (optical component, lens) thereof.
  • the optical characteristics opposite to those of the present invention are obtained.
  • the present invention has been made under such circumstances, and it is suitable as a raw material for a reflective material for an optical semiconductor, in which the light reflectance does not decrease even when used for a long time and the light reflectance in the visible light region is high.
  • An object of the present invention is to provide a resin composition and a cured product thereof, and a reflective material for optical semiconductors using the cured product.
  • the present inventors have obtained a copolymer, a curing agent, a curing accelerator and a white pigment containing a specific (meth) acrylate unit and a glycidyl (meth) acrylate unit. It has been found that the problem can be solved by the resin composition containing the resin composition.
  • the present invention has been completed based on such findings.
  • the present invention provides the following [1] to [8], [1] (A) a copolymer comprising a (meth) acrylate unit represented by the following general formula (a1) and a glycidyl (meth) acrylate unit represented by the following general formula (a2); [Wherein, R 1 and R 3 each independently represent a hydrogen atom or a methyl group, and R 2 represents a cyclic aliphatic group] (B) a curing agent, (C) a curing accelerator, and (D) a resin composition containing a white pigment, [2] Component (A) is 3 to 40 parts by mass, Component (B) is 2 to 20 parts by mass, Component (C) is 0.01 to 3 parts by mass, and Component (D) is 50 to 95 parts by mass.
  • A a copolymer comprising a (meth) acrylate unit represented by the following general formula (a1) and a glycidyl (meth) acrylate unit represented by the following general
  • a resin composition according to any one of [7] The resin composition according to any one of [1] to [6], further comprising an epoxy resin or an epoxy compound other than the component (A) as the component (E), [8] A cured product obtained by heat-curing or photocuring the resin composition according to any one of [1] to [7], and [9] an optical semiconductor using the cured product according to [8].
  • the resin composition of the present invention is excellent in heat resistance and weather resistance (light resistance), and is suitably used as a raw material for a reflective material for optical semiconductors.
  • the reflective material for optical semiconductors using a cured product obtained by curing the resin composition of the present invention is excellent in heat resistance and weather resistance (light resistance), has high light reflectance in the visible light region, and is used for a long time. However, the light reflectance does not decrease.
  • the resin composition of the present invention comprises (A) a copolymer containing a (meth) acrylate unit represented by the following general formula (a1) and a glycidyl (meth) acrylate unit represented by the following general formula (a2): B) a curing agent, (C) a curing accelerator, and (D) a white pigment.
  • R 1 and R 3 each independently represent a hydrogen atom or a methyl group, and R 2 represents a cyclic aliphatic group
  • the copolymer of the component (A) used in the resin composition of the present invention is a (meth) acrylate unit represented by the general formula (a1) and a glycidyl (meth) acrylate represented by the general formula (a2).
  • “(meth) acrylate” means “acrylate” or “methacrylate” corresponding thereto.
  • R 2 in the general formula (a1) represents a cyclic aliphatic group.
  • the cycloaliphatic group preferably has 6 or more carbon atoms, and preferably has 2 or more rings. Moreover, it is preferable to have a bridged carbocycle.
  • cycloaliphatic group examples include a cyclohexyl group, 2-decahydronaphthyl group, adamantyl group, 1-methyladamantyl group, 2-methyladamantyl group, biadamantyl group, dimethyladamantyl group, norbornyl group, 1-methyl -Norbornyl group, 5,6-dimethyl-norbornyl group, isobornyl group, tetracyclo [4.4.0.12,5.17,10] dodecyl group, 9-methyl-tetracyclo [4.4.0.12,5 .17,10] dodecyl group, bornyl group, dicyclopentanyl group and the like.
  • a substituted or unsubstituted adamantyl group, dicyclopentanyl group or isobornyl group is preferable from the viewpoints of hardness, heat resistance and light resistance of the cured product.
  • the molar ratio of the (meth) acrylate unit represented by the general formula (a1) to the glycidyl (meth) acrylate unit represented by the general formula (a2) [(a1) / ( a2)] is preferably 5/95 to 95/5, more preferably 10/90 to 90/10, still more preferably 15/85 to 85/15, from the viewpoint of heat resistance and weather resistance of the resulting cured product. It is.
  • ⁇ Radical polymerization initiator As the radical polymerization initiator used in the copolymerization reaction, an azo initiator, a peroxide initiator, or the like can be used.
  • the azo initiator include 2,2′-azobisisobutyronitrile, 2,2′-azobis-methylbutyronitrile, 2,2′-azobis-2,4-dimethylvaleronitrile, 1'-azobis-cyclohexanecarbonitrile, dimethyl-2,2'-azobisisobutyrate, 4,4'-azobis-4-cyanovaleric acid, 2,2'-azobis- (2-amidinopropene) dihydrochloride Salt, 2-tert-butylazo-2-cyanopropane, 2,2'-azobis- (2-methyl-propionamide) dihydrate, 2,2'-azobis [2- (2-imidazolin-2-yl ) Propene], 2,2′-azobis (2,2,4-trimethylpentane) and the like.
  • peroxide initiator examples include ketone peroxides such as benzoyl peroxide, methyl ethyl ketone peroxide, methyl isobutyl ketone peroxide, acetylacetone peroxide, cyclohexanone peroxide, and methylcyclohexanone peroxide; 1, 1, 3, 3 -Hydroperoxides such as tetramethylbutyl hydroperoxide, cumene hydroperoxide, t-butyl hydroperoxide; diisobutyryl peroxide, bis-3,5,5-trimethylhexanol peroxide, lauroyl peroxide, benzoyl peroxide Diacyl peroxides such as oxide and m-toluylbenzoyl peroxide; dicumyl peroxide, 2,5-dimethyl-2,5-di (t-butyl) Ruperoxy) hexane, 1,3-bis (t-butylperoxyiso
  • the amount of the radical polymerization initiator used is usually 0.01 to 50 parts by mass, preferably 0.01 to 30 parts per 100 parts by mass in total of the monomers (a1) and (a2) and the radical polymerization initiator. Part by mass. By setting it as the said range, reaction time, a yield, etc. become favorable, the target weight average molecular weight is obtained, and also physical properties, such as an optical characteristic, can be expressed.
  • the reaction temperature varies depending on the reaction molar ratio of the monomer (a1) and the monomer (a2), the type and amount of the solvent used, the type and amount of the radical polymerization initiator used, and is generally not fixed, but usually 30 to It is performed at about 200 ° C.
  • the reaction time is usually 0.1 to 30 hours, more preferably 0.5 to 15 hours. If the reaction time is within this range, the amount of unreacted raw materials can be suppressed, so that the yield can be improved and the production efficiency can be improved.
  • the reaction is usually performed in the presence of a solvent.
  • Solvents include halogenated hydrocarbons (eg, carbon tetrachloride, chloroform, dichloroethane), aromatics (eg, benzene, toluene, xylene, chlorobenzene, dichlorobenzene), ketones (eg, acetone, methyl isobutyl ketone, methyl ethyl ketone), Ethers (eg, diethyl ether, tetrahydrofuran, dioxane, monoglyme), alcohols (eg, methyl alcohol, ethyl alcohol, ethylene glycol) and aprotic polar solvents (eg, dimethyl sulfoxide, N, N-dimethylformamide, acetonitrile), carboxylic acids (For example, acetic acid, trifluoroacetic acid) and water.
  • the reaction is carried out in a ketone solvent.
  • the amount of the solvent used is such that the concentration of the mixture of the mono
  • the copolymer (A ) can be obtained. Moreover, as long as the performance of the resin composition obtained is not impaired, it is good also considering another monomer as a copolymerization component.
  • the weight average molecular weight Mw of the copolymer (A) is preferably 1,000 to 1,000,000, more preferably 2,000 to 100,000 from the viewpoint of the preparation of the resin composition and the performance of the resulting cured product. 000.
  • said Mw is the value of standard polystyrene conversion by the gel permeation chromatography method (GPC method).
  • the copolymer (A) Since the copolymer (A) has a glycidyl group as represented by the general formula (a2), it is thermally cured by the curing agent (B) and the curing accelerator (C). That is, the resin composition of the present invention is a thermosetting resin, and hence the resin composition of the present invention may be hereinafter referred to as a thermosetting resin composition.
  • the curing agent (B) is an acid anhydride and is preferably a non-aromatic compound.
  • the acid anhydride include compounds represented by the following formulas (1) to (6), respectively.
  • thermosetting resin composition of the present invention comprises succinic anhydride represented by the above formula (1), hydrogenated pyromellitic anhydride represented by the above formula (2), and hydrogen represented by the above formula (3).
  • Biphenyl dianhydride, tetrahydrophthalic anhydride represented by the above formula (4), hexahydrophthalic anhydride represented by the above formula (5), methylhexahydrophthalic anhydride represented by the above formula (6) By using at least one acid anhydride among the acids as a curing agent, the above effect can be obtained with certainty.
  • the curing agent (B) may contain a polyvalent carboxylic acid condensation condensate obtained by condensing two or more polyvalent carboxylic acids.
  • “Polyvalent carboxylic acid condensate” means a polymer formed by condensing one or more polycarboxylic acids having two or more carboxyl groups between molecules. More specifically, the polyvalent carboxylic acid condensate has an acid anhydride group (an acid anhydride bond) formed by dehydration condensation between carboxy groups of two or more monomers having two or more carboxy groups. ) And each monomer unit is linked in a chain or cyclic manner by the generated acid anhydride group.
  • the polycarboxylic acid condensate is usually composed of a plurality of components having different degrees of polymerization, and the constitution of repeating units and terminal groups is different.
  • the polycarboxylic acid condensate is a condensate of two molecules of monocarboxylic acid, a condensate of polycarboxylic acid and monocarboxylic acid, an unreacted product of polycarboxylic acid and monocarboxylic acid, and acetic anhydride and There may be cases where a by-product such as an acid anhydride formed by a condensation reaction between a reaction reagent such as propionic anhydride and a polyvalent carboxylic acid or monocarboxylic acid is included. These by-products may be removed by purification, or may be used as a curing agent in a mixture.
  • the content of the curing agent (B) in the thermosetting resin composition of the present invention is preferably 1 to 150 parts by mass with respect to 100 parts by mass of the copolymer (A), and the thermosetting resin composition From the viewpoint of suppressing soiling of the cured product, it is more preferably 20 to 120 parts by mass.
  • curing agent (B) in the thermosetting resin composition of this invention is the said with respect to 1 equivalent of epoxy groups in a copolymer (A) from a viewpoint of the elasticity modulus and intensity
  • the active group (acid anhydride group or hydroxyl group) in the curing agent (B) capable of reacting with an epoxy group is preferably 0.5 to 1.5 equivalents, more preferably 0.7 to 1.3 equivalents. .
  • a curing accelerator is used as the component (C).
  • the curing accelerator (C) is not particularly limited as long as it has a catalytic function that promotes the curing reaction between the copolymer (A) and the curing agent (B).
  • Specific examples of the curing accelerator include amine compounds, imidazole compounds, organic phosphorus compounds, alkali metal compounds, alkaline earth metal compounds, quaternary ammonium salts, and the like.
  • amine compound examples include 1,8-diaza-bicyclo (5,4,0) undecene-7, triethylenediamine, tri-2,4,6-dimethylaminomethylphenol and the like.
  • imidazole compound examples include 2-ethyl-4-methylimidazole.
  • organic phosphorus compound examples include triphenylphosphine, methyltributylphosphonium dimethyl phosphate, tetraphenylphosphonium tetraphenylborate, tetra-n-butylphosphonium-O, O-diethylphosphorodithioate, tetra-n-butylphosphonium- Examples thereof include tetrafluoroborate, tetra-n-butylphosphonium-tetraphenylborate and the like. These curing accelerators may be used alone or in combination of two or more.
  • the content of the curing accelerator (C) in the resin composition of the present invention is preferably 0.01 to 8 parts by mass with respect to 100 parts by mass of the copolymer (A), from the viewpoint of curing acceleration effect and coloring. More preferred is 0.1 to 3 parts by mass, and still more preferred is 0.5 to 1.5 parts by mass.
  • the resin composition of the present invention contains a white pigment as the component (D).
  • the white pigment (D) in the resin composition of the present invention, the cured product can be whitened and the light reflectance in the visible light region can be increased.
  • the white pigment examples include titanium dioxide, alumina, zirconium oxide, zinc sulfide, zinc oxide, magnesium oxide, antimony oxide, silica, potassium titanate, barium sulfate, calcium carbonate, silicone particles, inorganic hollow particles, and the like. .
  • the rutile type and the anatase type exist in the crystal form of titanium dioxide, since the anatase type has a photocatalytic function, there is a concern that the resin may be deteriorated.
  • the rutile type is used when titanium dioxide is used. Is preferred.
  • the average particle size of the white pigment (D) is preferably 0.01 to 0.5 ⁇ m, more preferably 0.1 to 0.4 ⁇ m. More preferably, the thickness is 0.15 to 0.3 ⁇ m.
  • the white pigment when the white pigment is a hollow particle, visible light that has passed through the outer shell of the hollow particle is reflected by the hollow part. Therefore, in order to increase the light reflectivity at the hollow part, It is preferable that the difference in refractive index from the gas existing inside the particle is large.
  • the gas present inside the hollow particles is usually air, but may be an inert gas such as nitrogen or argon, or may be a vacuum.
  • the white pigment may be appropriately subjected to a surface treatment with a silicon compound, an aluminum compound, an organic substance, etc., and examples thereof include alkylation treatment, trimethylsilylation treatment, silicone treatment, treatment with a coupling agent, and the like.
  • the white pigment (D) can be used alone or in combination of two or more.
  • the content of the white pigment (D) in the resin composition of the present invention is based on a total of 100 parts by mass of the component (A), the component (B), and the component (C) from the viewpoints of light reflectance and mechanical strength.
  • the amount is preferably 50 to 1500 parts by mass, more preferably 100 to 1200 parts by mass, and still more preferably 120 to 1000 parts by mass.
  • the preferable blending ratio of the components (A) to (D) is as follows.
  • Component (C) 0.01 to 3 parts by weight
  • Component (D) 50 to 95 parts by weight
  • the reflective material obtained by curing the composition exhibits good reflective properties.
  • the resin composition of the present invention preferably contains an inorganic filler in order to adjust moldability.
  • the inorganic filler include silica, antimony oxide, titanium oxide, aluminum hydroxide, magnesium hydroxide, barium sulfate, magnesium carbonate, barium carbonate, alumina, mica, beryllia, barium titanate, potassium titanate, titanate
  • Examples include strontium, calcium titanate, aluminum carbonate, aluminum silicate, calcium carbonate, calcium silicate, magnesium silicate, silicon nitride, boron nitride, clay such as baked clay, talc, aluminum borate, silicon carbide and the like.
  • the inorganic filler is selected from silica, alumina, magnesium oxide, antimony oxide, titanium oxide, zirconium oxide, aluminum hydroxide, and magnesium hydroxide from the viewpoints of thermal conductivity, light reflection characteristics, moldability, and flame retardancy. It is preferable that it is a mixture of 2 or more types.
  • the average particle size of the inorganic filler is preferably 1 to 100 ⁇ m and more preferably 1 to 40 ⁇ m from the viewpoint of improving packing properties with the white pigment.
  • the blending amount of the inorganic filler in the resin composition of the present invention is preferably 1 to 1000 parts by mass with respect to 100 parts by mass of the total amount of the component (A) and the component (B), and 1 to 800 parts by mass. It is more preferable that
  • the inorganic filler may be appropriately subjected to a surface treatment with a silicon compound, an aluminum compound, an organic substance, etc., for example, alkylation treatment, trimethylsilylation treatment, silicone treatment, Examples include treatment with a coupling agent.
  • the resin composition of the present invention may contain a general-purpose epoxy resin or epoxy (glycidyl) compound other than the component (A) as long as the effects of the present invention are not impaired.
  • the epoxy resin include bisphenol A type epoxy resin, bisphenol F type epoxy resin, phenol novolac type epoxy resin, hydrogenated bisphenol type epoxy resin, and the like.
  • the epoxy compound include alicyclic epoxy compounds such as 3,4-epoxycyclohexenylmethyl-3 ′, 4′-epoxycyclohexenecarboxylate, and 1,2-bis (hydroxymethyl) -1-butanol.
  • the resin composition of the present invention may appropriately contain additives such as an antioxidant, a release agent, and an ion scavenger as necessary.
  • the resin composition of the present invention is curable and can be prepared by uniformly dispersing and mixing the above-described components, and means and conditions thereof are not particularly limited.
  • a general method for preparing the resin composition includes a method in which each component is kneaded by an extruder, a kneader, a roll, an extruder, etc., and then the kneaded product is cooled and pulverized.
  • When kneading each component it is preferably performed in a molten state from the viewpoint of improving dispersibility.
  • the kneading conditions may be appropriately determined depending on the type and blending amount of each component in consideration of dispersibility and curability. For example, kneading is preferably performed at 15 to 100 ° C. for 5 to 40 minutes, preferably 20 to 100 More preferably, the mixture is kneaded at a temperature of 10 to 30 minutes.
  • the resin composition of the present invention is manufactured by adding the other components after kneading with a roll mill or an extruder after passing through a premixing step in which the copolymer (A) and the curing agent (B) are mixed in advance. You can also. For example, if at least one of the copolymer (A) and the curing agent (B) is liquid at 0 to 35 ° C. or has a low viscosity of less than 10 mPa ⁇ s at 100 to 200 ° C., the preliminary It is preferable to perform a mixing step.
  • the thermosetting resin composition obtained by premixing using such a copolymer (A) and a curing agent (B) has improved storage stability and more excellent moldability during transfer molding. It will be a thing.
  • the viscosity of the premix in the premixing step is preferably 10 to 10,000 mPa ⁇ s at 100 to 150 ° C., and more preferably 10 to 10,000 mPa ⁇ s at 100 ° C. .
  • a cured product can be obtained by curing the resin composition of the present invention by heating or light irradiation.
  • the thermosetting temperature is usually 30 to 200 ° C., preferably 50 to 150 ° C., and the curing time is about 30 seconds to 10 hours depending on the temperature.
  • a cationic polymerization initiator such as a diazonium salt, iodonium salt or sulfonium salt, which is usually used when photocuring an epoxy resin, is used.
  • the amount of the cationic polymerization initiator used is about 0.01 to 50% by mass, preferably about 0.1 to 20% by mass, based on the total mass of the copolymer (A) and the optionally used epoxy resin or epoxy compound. .
  • the reflecting material for optical semiconductors of the present invention uses a cured product obtained by curing the resin composition of the present invention.
  • the reflective material of the present invention can be produced by transfer molding or compression molding of the resin composition of the present invention.
  • thermosetting by transfer molding using a transfer molding machine, for example, molding is performed at a molding pressure of 5 to 20 N / mm 2 , a molding temperature of 120 to 190 ° C., a molding time of 30 to 500 seconds, preferably a molding temperature of 150 to 185 ° C. It can be molded and cured in a time of 30 to 180 seconds.
  • molding and curing may be performed using a compression molding machine at a molding temperature of 120 to 190 ° C. for a molding time of 30 to 600 seconds, preferably at a molding temperature of 130 to 160 ° C. for a molding time of 30 to 300 seconds. it can.
  • post-curing may be performed, for example, at 150 to 185 ° C. for 0.5 to 24 hours.
  • the reflective material of the present invention is excellent in adhesion with peripheral members such as a lead frame and a sealing material.
  • the reflecting material of the present invention has a breaking stress of preferably 5.0 MPa or more, more preferably 5.5 MPa or more, and still more preferably 7.0 MPa or more. Further, after the reflecting material of the present invention is molded, when the surface of the molded product is activated by a method such as ultraviolet irradiation treatment, ozone treatment, plasma treatment, corona discharge treatment, high pressure discharge treatment, etc., the adhesion to the sealing material is improved. Further improvement can be achieved.
  • the reflective material of the present invention has a high light reflectance in the visible light region, and the decrease in light reflectance is small even when used for a long time.
  • the light reflectance at a wavelength of 450 nm of the reflective material of the present invention is an initial value, preferably 85% or more, more preferably 90% or more, still more preferably 95% or more, after a deterioration test at 150 ° C. for 1000 hours.
  • the light reflectance is preferably 80% or more, more preferably 85% or more, and still more preferably 90% or more.
  • the reflector of the present invention can be used as a lamp reflector for liquid crystal displays, a reflector for showcases, various reflectors for illumination, a reflector for LEDs, and the like, and can be suitably used particularly as a reflector for optical semiconductors such as LEDs. .
  • Synthesis example 1 A 1000 mL round bottom flask equipped with a reflux condenser, a stirrer, a thermometer, a dropping funnel, and a nitrogen inlet tube was charged with 98.7 g of methyl isobutyl ketone and heated to 100 ° C. by bubbling with nitrogen for 30 minutes.
  • a dropping funnel was prepared by dissolving 80.0 g (0.36 mol) of 1-adamantyl methacrylate, 51.6 g (0.36 mol) of glycidyl methacrylate and 7.2 g of azobisisobutyronitrile in 98.7 g of methyl isobutyl ketone. The polymerization reaction was started by adding dropwise over 2 hours.
  • a copolymer A (Mw: 5) comprising a 1-adamantyl methacrylate unit represented by the following formula (a1-A) and a glycidyl methacrylate unit represented by the following formula (a2-M). 1,000, epoxy equivalent: 396).
  • the molar ratio of the 1-adamantyl methacrylate unit represented by the following formula (a1-A) to the glycidyl methacrylate unit represented by the following formula (a2-M) [(a1-A) / (A2-M)] is 50/50.
  • Synthesis example 2 In Synthesis Example 1, the amounts of raw materials used were as follows: methyl isobutyl ketone 95.7 g, 1-adamantyl methacrylate 100.0 g (0.45 mol), glycidyl methacrylate 27.6 g (0.19 mol), azobisisobutyronitrile From the 1-adamantyl methacrylate unit represented by the above formula (a1-A) and the glycidyl methacrylate unit represented by the above formula (a2-M), in the same manner as in Synthesis Example 1, except that each was changed to 6.4 g. Copolymer B (Mw: 6,300, epoxy equivalent: 691) was obtained.
  • the molar ratio of the 1-adamantyl methacrylate unit represented by the above formula (a1-A) to the glycidyl methacrylate unit represented by the above formula (a2-M) [(a1-A) / (A2-M)] is 70/30.
  • Synthesis example 3 In Synthesis Example 1, the amounts of raw materials used were 94.0 g of methyl isobutyl ketone, 50.0 g (0.23 mol) of 1-adamantyl methacrylate, 75.2 g (0.53 mol) of glycidyl methacrylate, azobisisobutyronitrile. From the 1-adamantyl methacrylate unit represented by the above formula (a1-A) and the glycidyl methacrylate unit represented by the above formula (a2-M), in the same manner as in Synthesis Example 1 except that each was changed to 7.4 g. Copolymer C (Mw: 5,800, epoxy equivalent: 247) was obtained.
  • the molar ratio of the 1-adamantyl methacrylate unit represented by the above formula (a1-A) to the glycidyl methacrylate unit represented by the above formula (a2-M) [(a1-A) / (A2-M)] is 30/70.
  • Synthesis example 4 In Synthesis Example 1, the same procedure as in Synthesis Example 1 was conducted except that the amount of azobisisobutyronitrile used as the polymerization initiator was changed to 3.6 g.
  • a copolymer D (Mw: 10,000, epoxy equivalent: 381) composed of an adamantyl methacrylate unit and a glycidyl methacrylate unit represented by the above formula (a2-M) was obtained.
  • the molar ratio of the 1-adamantyl methacrylate unit represented by the above formula (a1-A) to the glycidyl methacrylate unit represented by the above formula (a2-M) [(a1-A) / (A2-M)] is 50/50.
  • Synthesis example 5 In the same manner as in Synthesis Example 1 except that 80.0 g of 1-adamantyl methacrylate was changed to 80.0 g of dicyclopentanyl methacrylate in Synthesis Example 1, dicyclopentanyl represented by the following formula (a1-B) A copolymer E (Mw 5,300, epoxy equivalent: 372) comprising a methacrylate unit and a glycidyl methacrylate unit represented by the following formula (a2-M) was obtained.
  • a1-B A copolymer E (Mw 5,300, epoxy equivalent: 372) comprising a methacrylate unit and a glycidyl methacrylate unit represented by the following formula (a2-M) was obtained.
  • the molar ratio of the dicyclopentanyl methacrylate unit represented by the following formula (a1-B) to the glycidyl methacrylate unit represented by the following formula (a2-M) [(a1-B) / (A2-M)] is 50/50.
  • Synthesis Example 6 A 1000 mL round bottom flask equipped with a reflux condenser, a stirrer, a thermometer, a dropping funnel, and a nitrogen inlet tube was charged with 95.6 g of methyl isobutyl ketone and heated to 100 ° C. with nitrogen bubbling for 30 minutes. A solution prepared by dissolving 100.0 g of isobornyl methacrylate, 27.4 g of glycidyl methacrylate, and 6.3 g of azobisisobutyronitrile in 95.6 g of methyl isobutyl ketone was dropped from the dropping funnel over 2 hours to initiate the polymerization reaction. It was.
  • the reaction was allowed to proceed for 5 hours to complete the polymerization reaction. Thereafter, it is reprecipitated in heptane, and is a copolymer F (Mw: 5) comprising an isobornyl methacrylate unit represented by the following formula (a1-C) and a glycidyl methacrylate unit represented by the following formula (a2-M). 800).
  • the molar ratio of the isobornyl methacrylate unit represented by the following formula (a1-C) to the glycidyl methacrylate unit represented by the following formula (a2-M) [(a1-C) / (A2-M)] is 50/50.
  • Synthesis example 7 In a 1000 mL round bottom flask equipped with a reflux condenser, a stirrer, a thermometer, a dropping funnel, and a nitrogen introduction tube, 95.0 g of methyl isobutyl ketone was placed, and nitrogen bubbling was performed for 30 minutes to raise the temperature to 100 ° C. A solution prepared by dissolving 70.0 g of benzyl methacrylate, 56.5 g of glycidyl methacrylate, and 7.8 g of azobisisobutyronitrile in 95.0 g of methyl isobutyl ketone was dropped from the dropping funnel over 2 hours to initiate the polymerization reaction.
  • the copolymer G was reprecipitated in heptane and composed of a benzyl methacrylate unit represented by the following formula (a1-D) and a glycidyl methacrylate unit represented by the following formula (a2-M) (Mw: 5,200). )
  • the molar ratio of the benzyl methacrylate unit represented by the following formula (a1-D) to the glycidyl methacrylate unit represented by the following formula (a2-M) [(a1-D) / (a2 -M)] is 50/50.
  • Example 1 As component (A), 30.0 g of copolymer A obtained in Synthesis Example 1, and as component (B), a mixture of 4-methylhexahydrophthalic anhydride / hexahydrophthalic anhydride [manufactured by Shin Nippon Rika Co., Ltd., Product name: “Licacid MH-700G”, molar ratio: 70/30] 12.4 g, as component (C), methyltributylphosphonium dimethyl phosphate [manufactured by Nippon Chemical Industry Co., Ltd., product name: “Hishicolin PX-4MP” ] 0.2 g, as component (D), titanium dioxide [manufactured by Ishihara Sangyo Co., Ltd., trade name: “Taipeke PC-3”, average particle size: 0.21 ⁇ m] 63.5 g, 2,6 as antioxidant -Mix and stir 0.06 g of di-t-butyl-4-methylphenol (BHT) using a rotating / revol
  • Example 2 to 11 and Comparative Examples 1 to 4 Reference Example 1 After obtaining a resin composition with the composition shown in Table 1 in the same manner as in Example 1, a cured test piece was prepared, and in the same manner as in Example 1, the light reflectance measurement and the LED current test were performed. The results are shown in Table 1.
  • the filler used in Example 7 is silica [manufactured by Tatsumori Co., Ltd., trade name: “CRS1015 MSR35TS”, average particle size: 30 ⁇ m].
  • the epoxy compound used in Example 8 and Comparative Example 3 is triglycidyl isocyanurate [manufactured by Nissan Chemical Industries, Ltd., trade name: “TEPIC-S”], and used in Example 9 and Comparative Example 4.
  • the epoxy compound used was 3,4-epoxycyclohexenylmethyl-3 ′, 4′-epoxycyclohexenecarboxylate [manufactured by Daicel Corporation, trade name: “Celoxide 2021P”].
  • the copolymer H used in Comparative Example 2 is a methyl methacrylate / glycidyl methacrylate copolymer [manufactured by NOF Corporation, trade name: “Malproof G-0150M”].
  • the cured products of the resin compositions of Examples 1 to 11 are excellent in heat resistance and light resistance, have high light reflectance in the visible light region, and decrease in light reflectance even after long-term use. do not do.
  • a cured product of the resin composition of Comparative Examples 1 and 2 using a copolymer containing a methacrylate unit having an aromatic ring or a methyl ester methacrylate unit without containing a (meth) acrylate unit having a cyclic aliphatic group In both cases, the light irradiation surface turned brown in the LED current test, and the light reflectance after heating for 1000 hours was greatly reduced as compared to before heating.
  • the cured product of the resin compositions of Comparative Examples 3 and 4 using an epoxy compound other than the component (A) without using the component (A) also changed the light irradiation surface to brown in the LED current test. Also, the light reflectance after heating for 1000 hours was greatly reduced as compared to before heating. No cured product was obtained from the resin composition of Reference Example 1.
  • the resin composition of the present invention is excellent in heat resistance and weather resistance (light resistance), has a high light reflectance in the visible light region, and does not decrease the light reflectance even when used for a long time. It can be suitably used as a raw material.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Epoxy Resins (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

L'invention concerne une composition de résine qui contient (A) un copolymère qui contient une unité (méth)acrylate spécifique et une unité (méth)acrylate de glycidyle spécifique, (B) un agent durcisseur, (C) un accélérateur de durcissement et (D) un pigment blanc ; un produit durci de la composition de résine ; et une matière réfléchissante pour semi-conducteurs optiques, qui utilise le produit durci.
PCT/JP2013/055544 2012-03-30 2013-02-28 Composition de résine, produit durci à base de celle-ci, et matière réfléchissante pour semi-conducteurs optiques utilisant ledit produit durci WO2013146081A1 (fr)

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WO2015170773A1 (fr) * 2014-05-09 2015-11-12 京セラ株式会社 Substrat de montage d'élément électroluminescent et dispositif électroluminescent
JP2016008230A (ja) * 2014-06-23 2016-01-18 出光興産株式会社 熱硬化性組成物、及び当該熱硬化性樹脂の製造方法
KR20160122117A (ko) 2014-02-14 2016-10-21 미츠비시 가스 가가쿠 가부시키가이샤 (메트)아크릴산에스테르 화합물 및 그 제조 방법
CN112166039A (zh) * 2018-04-06 2021-01-01 聚合-医药有限公司 用于光致聚合增材制造的方法和组合物
US12065539B2 (en) 2018-04-19 2024-08-20 Poly-Med, Inc. Macromers and compositions for photocuring processes
JP7567317B2 (ja) 2020-09-24 2024-10-16 株式会社レゾナック 光反射用熱硬化性樹脂組成物、光半導体素子搭載用基板及び光半導体装置

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JP2014037480A (ja) * 2012-08-15 2014-02-27 Idemitsu Kosan Co Ltd エポキシ系共重合体
KR101820196B1 (ko) 2013-10-16 2018-01-18 타이완 다이요 잉크 컴퍼니 리미티드 백색 열경화성 수지 조성물, 그의 경화물 및 그것을 사용한 디스플레이용 부재
JP5670534B1 (ja) * 2013-10-16 2015-02-18 台湾太陽油▲墨▼股▲分▼有限公司 白色熱硬化性樹脂組成物、その硬化物、及びそれを用いたディスプレイ用部材
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KR20160122117A (ko) 2014-02-14 2016-10-21 미츠비시 가스 가가쿠 가부시키가이샤 (메트)아크릴산에스테르 화합물 및 그 제조 방법
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CN106463595A (zh) * 2014-05-09 2017-02-22 京瓷株式会社 发光元件搭载用基板以及发光装置
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WO2015170773A1 (fr) * 2014-05-09 2015-11-12 京セラ株式会社 Substrat de montage d'élément électroluminescent et dispositif électroluminescent
JP2016008230A (ja) * 2014-06-23 2016-01-18 出光興産株式会社 熱硬化性組成物、及び当該熱硬化性樹脂の製造方法
KR101930148B1 (ko) 2014-06-23 2018-12-17 이데미쓰 고산 가부시키가이샤 열경화성 조성물 및 당해 열경화 수지의 제조 방법
CN112166039A (zh) * 2018-04-06 2021-01-01 聚合-医药有限公司 用于光致聚合增材制造的方法和组合物
CN112166039B (zh) * 2018-04-06 2023-09-05 聚合-医药有限公司 用于光致聚合增材制造的方法和组合物
US12065539B2 (en) 2018-04-19 2024-08-20 Poly-Med, Inc. Macromers and compositions for photocuring processes
JP7567317B2 (ja) 2020-09-24 2024-10-16 株式会社レゾナック 光反射用熱硬化性樹脂組成物、光半導体素子搭載用基板及び光半導体装置

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