WO2011105192A1 - Composition de résine assurant l'étanchéité d'un semi-conducteur optique et dispositif à semi-conducteurs optiques utilisant ladite composition de résine - Google Patents

Composition de résine assurant l'étanchéité d'un semi-conducteur optique et dispositif à semi-conducteurs optiques utilisant ladite composition de résine Download PDF

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Publication number
WO2011105192A1
WO2011105192A1 PCT/JP2011/052347 JP2011052347W WO2011105192A1 WO 2011105192 A1 WO2011105192 A1 WO 2011105192A1 JP 2011052347 W JP2011052347 W JP 2011052347W WO 2011105192 A1 WO2011105192 A1 WO 2011105192A1
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Prior art keywords
optical semiconductor
resin composition
group
epoxy
sealing
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Japanese (ja)
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木村伯子
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Daicel Corp
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Daicel Chemical Industries Ltd
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Priority to CN201180008555.5A priority Critical patent/CN102782000B/zh
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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
    • C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
    • C08G59/688—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used containing phosphorus
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
    • C08G59/22—Di-epoxy compounds
    • C08G59/24—Di-epoxy compounds carbocyclic
    • 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
    • C08G59/4215—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof cycloaliphatic
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10W—GENERIC PACKAGES, INTERCONNECTIONS, CONNECTORS OR OTHER CONSTRUCTIONAL DETAILS OF DEVICES COVERED BY CLASS H10
    • H10W74/00—Encapsulations, e.g. protective coatings
    • H10W74/40—Encapsulations, e.g. protective coatings characterised by their materials
    • H10W74/47—Encapsulations, e.g. protective coatings characterised by their materials comprising organic materials, e.g. plastics or resins
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10W—GENERIC PACKAGES, INTERCONNECTIONS, CONNECTORS OR OTHER CONSTRUCTIONAL DETAILS OF DEVICES COVERED BY CLASS H10
    • H10W74/00—Encapsulations, e.g. protective coatings
    • H10W74/40—Encapsulations, e.g. protective coatings characterised by their materials
    • H10W74/47—Encapsulations, e.g. protective coatings characterised by their materials comprising organic materials, e.g. plastics or resins
    • H10W74/473—Encapsulations, e.g. protective coatings characterised by their materials comprising organic materials, e.g. plastics or resins containing a filler
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10W—GENERIC PACKAGES, INTERCONNECTIONS, CONNECTORS OR OTHER CONSTRUCTIONAL DETAILS OF DEVICES COVERED BY CLASS H10
    • H10W74/00—Encapsulations, e.g. protective coatings
    • H10W74/40—Encapsulations, e.g. protective coatings characterised by their materials
    • H10W74/47—Encapsulations, e.g. protective coatings characterised by their materials comprising organic materials, e.g. plastics or resins
    • H10W74/476—Organic materials comprising silicon

Definitions

  • the present invention relates to a resin composition for sealing an optical semiconductor, a cured product obtained by curing the resin composition, and an optical semiconductor device using the same.
  • Patent Document 1 contains an epoxy-modified ester compound that is excellent in solubility in an organic solvent and can be easily mixed with an epoxy resin as an epoxy resin curing agent, and has low hygroscopicity, low dielectric constant, low dielectric loss tangent, etc.
  • curing agent (B), and a hardening accelerator (C) is disclosed.
  • Patent Document 3 hydrogenation is performed for the purpose of providing an epoxy resin composition that exhibits excellent translucency and ultraviolet resistance, does not discolor even when heated for a long time, and has low hygroscopicity.
  • An epoxy resin composition contained therein in an amount of 0.01 to 5% by weight is disclosed.
  • JP 2004-217869 A JP 2007-320974 A Japanese Patent Laid-Open No. 2005-126662
  • the objective of this invention is providing the resin composition for optical semiconductor sealing which can obtain the hardened
  • Another object of the present invention is to provide a cured product obtained by curing the above-mentioned resin composition for encapsulating an optical semiconductor and imparting excellent luminance stability while maintaining high heat resistance and transparency. It is in.
  • the other object of this invention is to provide the optical semiconductor device which sealed the optical semiconductor element using the said resin composition for optical semiconductor sealing.
  • a resin composition containing a specific structure alicyclic epoxy resin and using a specific curing accelerator has a high heat resistance.
  • it In the reliability test of the optical semiconductor device using transparency and its cured product, it has excellent luminance stability with small luminance fluctuation, and is useful as a resin composition for optical semiconductor encapsulation.
  • the inventors have found that the luminance stability has a causal relationship with the adhesion between the sealing resin and the frame, and have reached the present invention.
  • the present invention is an optical semiconductor sealing resin composition containing an epoxy resin, a curing agent (B), and a curing accelerator (C),
  • the alicyclic epoxy resin (A) (A1) the following formula (I) [In Formula (I), X represents a linking group, a single bond, a divalent hydrocarbon group, a carbonyl group, an ether bond, an ester bond, a carbonate group, an amide bond, or a group in which a plurality of these are linked]
  • A2 a compound in which an epoxy group is directly bonded to the alicyclic ring with a single bond
  • the curing agent (B) is an acid anhydride curing agent
  • the curing accelerator (C) the following formula (1) [R 1 , R 2 , R 3 , and R 4 in the formula (1) each represent a hydrocarbon group having 1 to 20 carbon atoms, and may be the same or different from each other].
  • An optical semiconductor encapsulating resin composition comprising an ionic combination of a phosphonium ion and a halogen anion capable of forming an ion pair with the phosphonium ion is provided.
  • the halogen anion is preferably bromine ion or iodine ion.
  • this invention provides the hardened
  • an optical semiconductor device that has high heat resistance and transparency, and has excellent luminance stability with small luminance fluctuations in a reliability test of an optical semiconductor device using the cured product.
  • the resin composition for optical semiconductor sealing obtained can be provided.
  • a cured product obtained by curing the resin composition for optical semiconductor encapsulation of the present invention has high heat resistance and transparency, and in a reliability test of an optical semiconductor device using the cured product, Luminance fluctuation is small and luminance stability is excellent.
  • an optical semiconductor device having high heat resistance and transparency, small luminance fluctuation, and excellent luminance stability can be obtained.
  • the resin composition for optical semiconductor encapsulation of the present invention is an optical semiconductor encapsulation resin composition containing an epoxy resin, a curing agent (B), and a curing accelerator (C), and an alicyclic epoxy resin ( As A), (A1) the following formula (I) [In Formula (I), X represents a linking group, a single bond, a divalent hydrocarbon group, a carbonyl group, an ether bond, an ester bond, a carbonate group, an amide bond, or a group in which a plurality of these are linked] (A2) a compound in which an epoxy group is directly bonded to the alicyclic ring with a single bond, and (A3) an epoxy group composed of two adjacent carbon atoms and oxygen atoms constituting the alicyclic ring.
  • A1 the following formula (I) [In Formula (I), X represents a linking group, a single bond, a divalent hydrocarbon group, a carbonyl group, an ether bond, an ester bond, a carbon
  • the curing agent (B) is an acid anhydride curing agent
  • the curing accelerator (C) the following formula (1) [R 1 , R 2 , R 3 , and R 4 in Formula (1) each represent a hydrocarbon group having 1 to 20 carbon atoms, and may be the same or different from each other] And an ion conjugate of a halogen anion capable of forming an ion pair with the phosphonium ion. Since the resin composition for sealing an optical semiconductor of the present invention contains an epoxy resin, it has high heat resistance and transparency.
  • the epoxy resin contained in the resin composition for encapsulating an optical semiconductor of the present invention is (A1) represented by the following formula (I) as the alicyclic epoxy resin (A).
  • X represents a linking group, represented by a single bond, a divalent hydrocarbon group, a carbonyl group, an ether bond, an ester bond, a carbonate group, an amide bond, or a group in which a plurality of these are linked].
  • (A2) a compound in which an epoxy group is directly bonded to the alicyclic ring with a single bond, and (A3) an epoxy group composed of two adjacent carbon atoms and oxygen atoms constituting the alicyclic ring. At least one compound selected from the group consisting of the above compounds is contained in an amount of 55 to 100 wt% with respect to the total amount of the epoxy resin.
  • the alicyclic epoxy resin (A) contained in the resin composition for sealing an optical semiconductor of the present invention is (A1) represented by the following formula (I): [In formula (I), X represents a linking group, represented by a single bond, a divalent hydrocarbon group, a carbonyl group, an ether bond, an ester bond, a carbonate group, an amide bond, or a group in which a plurality of these are linked].
  • (A2) a compound in which an epoxy group is directly bonded to the alicyclic ring with a single bond, and (A3) an epoxy group composed of two adjacent carbon atoms and oxygen atoms constituting the alicyclic ring. It is at least one compound selected from the group consisting of the compounds as described above.
  • the divalent hydrocarbon group represented as the linking group X is a linear or branched alkylene group having 1 to 18 carbon atoms, divalent And an alicyclic hydrocarbon group (particularly a divalent cycloalkylene group).
  • Examples of the linear or branched alkylene group having 1 to 18 carbon atoms include methylene, methylmethylene, dimethylmethylene, ethylene, propylene, and trimethylene groups.
  • divalent alicyclic hydrocarbon group examples include 1,2-cyclopentylene, 1,3-cyclopentylene, cyclopentylidene, 1,2-cyclohexylene, 1,3-cyclohexylene, 1, And divalent cycloalkylene groups (including cycloalkylidene groups) such as 4-cyclohexylene and cyclohexylidene groups.
  • Representative examples of the alicyclic epoxy compound represented by the above formula (I) include compounds represented by the following formulas (I-1) to (I-7).
  • commercially available products such as Celoxide 2021P and Celoxide 2081 (manufactured by Daicel Chemical Industries, Ltd.) can also be used, where m represents an integer of 1 to 30.
  • Examples of the compound in which the epoxy group is directly bonded to the alicyclic ring with a single bond include compounds represented by the following formulas (I-8) and (I-9).
  • Examples of the compound (A3) having 3 or more epoxy groups composed of two adjacent carbon atoms and oxygen atoms constituting the alicyclic ring are represented by the following formulas (I-10) and (I-11). The compound which is made is mentioned.
  • R is a group obtained by dividing q-OH from q-valent alcohol, and represents an alkyl group having about 2 to 18 carbon atoms, which may be linear or branched, and cyclic. A skeleton may be included.
  • Q and n represent natural numbers.
  • Examples of the q-valent alcohol [R— (OH) q ] include polyhydric alcohols such as 2,2-bis (hydroxymethyl) -1-butanol (such as alcohols having 1 to 15 carbon atoms).
  • q is preferably 1 to 6, and p is preferably 1 to 30. When q is 2 or more, p in each group in () may be the same or different.
  • the compound (I-8) include 1,2-epoxy-4- (2-oxiranyl) cyclohexane adduct of 2,2-bis (hydroxymethyl) -1-butanol, EHPE3150 (Daicel Chemical). Kogyo Co., Ltd.).
  • a, b, c, d, e, and f are integers from 0 to 30.
  • the compounds (A1) to (A3) used as the alicyclic epoxy resin (A) can be used alone or in combination of two or more.
  • Celoxide 2021P, Celoxide 2081, EHPE3150, EHPE3150CE (Daicel) Commercial products such as Chemical Industry Co., Ltd. can be used.
  • the epoxy resin contained in the resin composition for encapsulating an optical semiconductor of the present invention may contain an epoxy resin other than the alicyclic epoxy resin (A).
  • epoxy resins include glycidyl type epoxy resins such as bisphenol A type and F type having a liquid aromatic ring, and glycidyl type epoxy resins represented by the following formula.
  • the content of the alicyclic epoxy resin (A) relative to the total amount of the epoxy resin (compound having all epoxy groups) in the optical semiconductor sealing resin composition is 55 to 100 wt%, preferably 60 to 100 wt%, More preferably, it can be 70 to 100 wt%.
  • the content of the alicyclic epoxy resin (A) with respect to the total amount of the epoxy resin is less than 55%, the effect of the present application cannot be obtained.
  • the blending amount of the glycidyl type epoxy resin having an aromatic ring exceeds 30% by weight of the compound having all epoxy groups, desired performance cannot be obtained.
  • the content of the epoxy resin in the resin composition for sealing an optical semiconductor of the present invention is preferably 30 to 99.9 wt%.
  • the curing agent (B) contained in the optical semiconductor sealing resin composition of the present invention is an acid anhydride curing agent.
  • the acid anhydride curing agent can be arbitrarily selected from those generally used as curing agents for epoxy resins. Among these, those which are liquid at normal temperature are preferable, and specific examples include methyltetrahydrophthalic anhydride, methylhexahydrophthalic anhydride, dodecenyl succinic anhydride, methylendomethylenetetrahydrophthalic anhydride and the like.
  • acid anhydrides that are solid at room temperature such as phthalic anhydride, tetrahydrophthalic anhydride, hexahydrophthalic anhydride, and methylcyclohexene dicarboxylic acid anhydride, are dissolved in a liquid acid anhydride at room temperature to form a liquid mixture. Therefore, it can be used as the curing agent of the present invention.
  • the curing agent (B) commercially available products such as Jamaicacid MH-700 (manufactured by Shin Nippon Rika Co., Ltd.) and HN-5500 (manufactured by Hitachi Chemical Co., Ltd.) can also be used. .
  • the amount of the curing agent (B) used is, for example, 50 to 200 parts by weight, preferably 100 to 145 parts by weight with respect to 100 parts by weight of the compound having all epoxy groups contained in the resin composition for optical semiconductor encapsulation. Part, more specifically, it should be used at a ratio of 0.5 to 1.5 equivalents per 1 equivalent of epoxy group in the compound having all epoxy groups contained in the resin composition for optical semiconductor encapsulation. Is preferred.
  • the amount of the curing agent (B) used is less than 50 parts by weight, the effect becomes insufficient and the toughness of the cured product (B) tends to decrease, while the amount of the curing agent (B) used is 200 weights. When it exceeds the part, the cured product may be colored to deteriorate the hue.
  • the curing accelerator (C) contained in the optical semiconductor sealing resin composition of the present invention is represented by the following formula (1).
  • R 1 , R 2 , R 3 , and R 4 in Formula (1) each represent a hydrocarbon group having 1 to 20 carbon atoms, and may be the same or different from each other]
  • the ionic combination (quaternary organic phosphonium salt) of a phosphonium ion and a halogen anion represented by the above formula (1) is one in which the phosphonium ion and the halogen anion form at least one ion pair.
  • the ionic bond is quickly dissociated at the time of curing exposed to a high temperature, and phosphonium ions have a function of promoting curing. For this reason, when an optical semiconductor device is manufactured, it is considered that the halogen anion in the sealing material has an effect of improving luminance stability by lowering the adhesion with the lead frame.
  • Examples of the hydrocarbon group having 1 to 20 carbon atoms in R 1 , R 2 , R 3 , and R 4 represented by the hydrocarbon group having 1 to 20 carbon atoms in the formula (1) include, for example, 1 to And an alkyl group having 20 carbon atoms, an aralkyl group having 7 to 20 carbon atoms, and an aryl group having 6 to 20 carbon atoms.
  • alkyl group having 1 to 20 carbon atoms examples include methyl, ethyl, propyl, butyl, isobutyl, sec-butyl, pentyl, isopentyl, hexyl, isohexyl, cyclohexyl, methylcyclohexyl, heptyl, octyl, isooctyl, nonyl, isononyl, Examples include linear, branched or cyclic alkyl groups such as decyl and isodecyl groups.
  • Examples of the aralkyl group having 7 to 20 carbon atoms include benzyl group, methylbenzyl, ethylbenzyl, dimethylbenzyl, diethylbenzyl, phenethyl, methylphenethyl, ethylphenethyl, methylphenethyl, ethylphenethyl, and aryl groups having 6 to 20 carbon atoms. Examples thereof include a phenyl group; a substituted phenyl group such as methylphenyl, dimethylphenyl, and ethylphenyl; a naphthyl group, and the like.
  • alkyl groups having 2 to 4 carbon atoms such as ethyl, propyl and butyl
  • aralkyl groups having 7 to 10 carbon atoms such as benzyl, ethylbenzyl, phenethyl and ethylphenethyl groups
  • carbons such as phenyl and methylphenyl groups
  • An aryl group of 6 to 8 is preferable, and a phenyl group, a butyl group, and an ethyl group are particularly preferable.
  • halogen anion capable of forming an ion pair with the phosphonium ion represented by the above formula (1) examples include chlorine ion, bromine ion and iodine ion. Of these, bromine ion and iodine ion are preferable.
  • the phosphonium compound as an ion conjugate of the phosphonium ion represented by the above formula (1) and the halogen anion capable of forming an ion pair with the phosphonium ion include, for example, tetrabutylphosphonium chloride, tetrabutylphosphonium bromide , Tetrabutylphosphonium iodide, tetraphenylphosphonium chloride, tetraphenylphosphonium bromide, tetraphenylphosphonium iodide, ethyltriphenylphosphonium chloride, ethyltriphenylphosphonium bromide, ethyltriphenylphosphonium iodide, propyltriphenylphosphonium chloride, propyltriphenyl Phenylphosphonium bromide, propyltriphenylphosphonium iodide, butyltriphenylphosphonium chloride,
  • tetraethyl phosphonium bromide tetraethyl phosphonium bromide.
  • tetraphenylphosphonium bromide, tetrabutylphosphonium bromide, tetraphenylphosphonium iodide, and ethyltriphenylphosphonium iodide are preferable.
  • a commercial product such as U-CAT 5003 (manufactured by Sun Apro Co., Ltd.) can also be used as the curing accelerator (C).
  • the blending amount of these phosphonium compounds is such that the bromine or iodine content contained in the optical semiconductor sealing resin composition is 200 mg / kg or more (for example, 200 to 8000 mg / kg), preferably 200 to 5000 mg / kg, more preferably. Is preferably blended so as to be 300 to 4000 mg / kg. If the bromine or iodine content is less than 200 mg / kg, luminance stability is difficult to obtain.
  • the curing accelerator may be a phosphonium compound alone or a mixture with a commonly used amine-based curing accelerator or phosphorus-based curing accelerator.
  • amine curing accelerator examples include tertiary amines such as benzyldimethylamine, 2,4,6-tris (dimethylaminomethyl) phenol, N, N-dimethylcyclohexylamine and the like.
  • phosphorus curing accelerator include phosphines such as phosphate esters and triphenylphosphine.
  • the amount of the curing accelerator (C) used is, for example, 0.05 to 5 parts by weight, preferably 0 with respect to 100 parts by weight of the compound having all epoxy groups contained in the optical semiconductor sealing resin composition. .About.1 to 3 parts by weight, particularly preferably about 0.2 to 3 parts by weight, and most preferably about 0.25 to 2.5 parts by weight.
  • the amount of the curing accelerator (C) used is less than 0.05 parts by weight, the curing acceleration effect may be insufficient.
  • the amount of the curing accelerator (C) used exceeds 5 parts by weight, The cured product may be colored to deteriorate the hue.
  • the resin composition for optical semiconductor encapsulation of the present invention may contain a solvent.
  • the solvent include glycol (ethylene glycol; polyalkylene glycol; neopentyl alcohol, etc.), ether (diethyl ether; ethylene glycol mono- or dialkyl ether, diethylene glycol mono- or dialkyl ether, propylene glycol mono- or dialkyl ether, propylene glycol mono- or diaryl.
  • Ether dipropylene glycol mono or dialkyl ether, tripropylene glycol mono or dialkyl ether, 1,3-propanediol mono or dialkyl ether, 1,3-butanediol mono or dialkyl ether, 1,4-butanediol mono or dialkyl ether Chain ethers such as glycol ethers such as glycerin mono, di or trialkyl ethers; Tetrahydrofuran, and cyclic ethers such as dioxane), esters (methyl acetate, ethyl acetate, butyl acetate, isoamyl acetate, ethyl lactate, methyl 3-methoxypropionate, ethyl 3-ethoxypropionate, 3-methoxybutyl acetate, C 5-6 cycloalkanediol mono or diacetate, carboxylic acid esters such as C 5-6 cycloalkane dimethanol mono or diacetate;
  • the resin composition for optical semiconductor sealing concerning this invention can use various additives in the range which does not impair the effect of this invention besides the above.
  • a compound having a hydroxyl group such as ethylene glycol, diethylene glycol, propylene glycol, or glycerin
  • the reaction can be allowed to proceed slowly.
  • Conventional additives such as inorganic fillers, organic rubber particles, flame retardants, colorants, antioxidants, ultraviolet absorbers, ion adsorbents, pigments, phosphors, mold release agents and the like can be used. .
  • the resin composition for encapsulating an optical semiconductor of the present invention has a temperature of 45 to 200 ° C., preferably 100 to 190 ° C., more preferably 100 to 180 ° C., and a curing time of 30 to 600 minutes, preferably 45 to 540. Minutes, more preferably 60 to 480 minutes.
  • the curing temperature and the curing time are lower than the lower limit of the range, curing is insufficient, and when the curing temperature and the curing time are higher than the upper limit of the range, the resin component may be decomposed.
  • the curing conditions depend on various conditions, when the curing temperature is high, the curing time is short, and when the curing temperature is low, the curing time is long and can be adjusted as appropriate.
  • the optical semiconductor device of the present invention can be obtained by sealing an optical semiconductor element with the resin composition for optical semiconductor encapsulation of the present invention.
  • the optical semiconductor element is sealed by injecting the resin composition for optical semiconductor sealing prepared by the above-described method into a predetermined mold and heating and curing under predetermined conditions.
  • an optical semiconductor device excellent in various physical properties such as luminance stability, heat resistance, and transparency, in which the optical semiconductor element is sealed with the resin composition for optical semiconductor sealing, is obtained.
  • the curing temperature and the curing time can be the same as described above.
  • Example 1 As an alicyclic epoxy resin, 50 parts by weight of Daicel Chemical Industries, trade name “Celoxide 2021P”, 50 parts by weight of Daicel Chemical Industries, trade name “EHPE3150CE” were used.
  • the curing agent is 100 parts by weight of methylhexahydrophthalic anhydride (manufactured by Shin Nippon Rika Co., Ltd., trade name “Licacid MH-700”), and the curing accelerator is tetraphenylphosphonium bromide (Wako Pure Chemical Industries, Ltd.) 1 part by weight was used. Furthermore, 1.5 parts by weight of ethylene glycol (manufactured by Wako Pure Chemical Industries, Ltd.) was used. These were uniformly mixed (2000 rpm, 5 minutes) using “Awatori Rentaro” manufactured by Shinky Corp. to obtain a resin composition for optical semiconductor encapsulation.
  • Example 2 Except for using 0.5 parts by weight of ethyltriphenylphosphonium iodide (manufactured by Wako Pure Chemical Industries, Ltd.) and 0.5 parts by weight of triphenylphosphine (manufactured by Kishida Chemical Co., Ltd.) as a curing accelerator. In the same manner as in Example 1, a resin composition for sealing an optical semiconductor was obtained.
  • ethyltriphenylphosphonium iodide manufactured by Wako Pure Chemical Industries, Ltd.
  • triphenylphosphine manufactured by Kishida Chemical Co., Ltd.
  • Example 3 Example 1 except that 70 parts by weight of Daicel Chemical Industries, Ltd., trade name “EHPE3150CE”, and 30 parts by weight of trade name “YD-128”, manufactured by Toto Kasei Co., Ltd. were used as the epoxy resin. Similarly, a resin composition for optical semiconductor encapsulation was obtained.
  • Comparative Example 1 For sealing an optical semiconductor in the same manner as in Example 1, except that tetrabutylphosphonium diethyl phosphorodithioate (trade name “Hishicolin PX-4ET” manufactured by Nippon Chemical Industry Co., Ltd.) was used as a curing accelerator. A resin composition was obtained.
  • tetrabutylphosphonium diethyl phosphorodithioate trade name “Hishicolin PX-4ET” manufactured by Nippon Chemical Industry Co., Ltd.
  • Comparative Example 2 Example 1 except that Daicel Chemical Industries, Ltd., trade name “EHPE3150CE” 50 parts by weight and Toto Kasei Co., Ltd., trade name “YD-128” 50 parts by weight were used as the epoxy resin. Similarly, a resin composition for optical semiconductor encapsulation was obtained.
  • Comparative Example 3 A resin composition for encapsulating an optical semiconductor was obtained in the same manner as in Example 1 except that 100 parts by weight of a trade name “YD-128” manufactured by Toto Kasei Co., Ltd. was used as the epoxy resin.
  • the resin compositions for sealing an optical semiconductor obtained in Examples and Comparative Examples were heated at 110 ° C. for 2 hours, and then heated at 130 ° C. for 3 hours to obtain a cured product.
  • the obtained resin composition for encapsulating an optical semiconductor was evaluated by the following method. In the following evaluation tests, the optical semiconductor sealing resin composition was cured under the same conditions as described above.
  • the obtained resin composition for encapsulating an optical semiconductor was cast into a lead frame with an optical semiconductor element (InGaN) and cured by heating to produce an optical semiconductor device.
  • the manufactured optical semiconductor device was subjected to low-temperature energization ( ⁇ 40 ° C./20 mA) and normal temperature energization (23 ° C./60 mA), and the current-carrying luminance stability under each condition was measured using the following measuring device.
  • Measuring apparatus OL771 manufactured by OPTRONIC LABORATORIES
  • the luminance after 150, 300, 500, and 1000 hours was measured, and the luminance retention rate from the initial (100%) was calculated.
  • the variation rate of the luminance retention rate indicates the maximum width from the initial stage.
  • the luminance after 300 hours was measured, and the luminance retention rate from the initial (100%) was calculated. The results are shown in Table 2.
  • the low-temperature energization characteristics were evaluated as ⁇ when the variation rate of the luminance retention rate was ⁇ 3% or more: x, and less than ⁇ 3%: ⁇ .
  • the normal temperature energization characteristics were evaluated as “X” when the luminance deterioration rate (brightness reduction rate from the initial stage) was 20% or more: “X”, and less than 20%: “ ⁇ ”.
  • X luminance deterioration rate
  • Epoxy resin Celoxide 2021P 3,4-epoxycyclohexenylmethyl-3 ′, 4′-epoxycyclohexenecarboxylate, manufactured by Daicel Chemical Industries, Ltd.
  • EHPE3150CE 1,2-bis (hydroxymethyl) -1-butanol 2-epoxy-4- (2-oxiranyl) cyclosexane adduct and 3,4-epoxycyclohexenylmethyl-3 ′, 4′-epoxycyclohexenecarboxylate, manufactured by Daicel Chemical Industries, Ltd.
  • YD-128 Bisphenol A type Epoxy resin, hardener (B) manufactured by Tohto Kasei Co., Ltd.
  • a lower adhesiveness between the cured product of the resin composition for encapsulating an optical semiconductor and the lead frame according to the present invention is preferable in terms of luminance stability, and an adhesive strength is 18 N / mm 2 or less (for example, 0 to 18 N / mm). 2 ), preferably 15 N / mm 2 or less (for example, 0 to 15 N / mm 2 ), more preferably 7 N / mm 2 or less (for example, 0 to 7 N / mm 2 ). is there. Note that there is no problem even if the adhesive strength is zero.
  • an optical semiconductor device that has high heat resistance and transparency, and has excellent luminance stability with small luminance fluctuations in a reliability test of an optical semiconductor device using the cured product.
  • the resin composition for optical semiconductor sealing obtained can be provided.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Epoxy Resins (AREA)
  • Structures Or Materials For Encapsulating Or Coating Semiconductor Devices Or Solid State Devices (AREA)

Abstract

La présente invention concerne une composition de résine permettant d'assurer l'étanchéité d'un semi-conducteur optique, ladite composition de résine contenant une résine époxy, un durcisseur, et un accélérateur de durcissement. Entre 55 % et 100 % du poids total de la résine époxy dans la composition de résine de l'invention est une résine époxy alicyclique (A) constituée d'au moins un composé choisi parmi des composés représentés par la formule (I), des composés dans lesquels un groupe époxy est lié à un alicycle via une liaison unique directe, et des composés ayant au moins trois groupes époxy comprenant chacun deux atomes de carbone adjacents et un atome d'oxygène qui font partie d'un alicycle. Le durcisseur dans la composition de résine de l'invention est un durcisseur à base d'anhydride acide, et l'accélérateur de durcissement est un conjugué ionique de l'ion phosphonium représenté par la formule (1), un anion halogène pouvant former une paire d'ions avec l'ion phosphonium.
PCT/JP2011/052347 2010-02-25 2011-02-04 Composition de résine assurant l'étanchéité d'un semi-conducteur optique et dispositif à semi-conducteurs optiques utilisant ladite composition de résine Ceased WO2011105192A1 (fr)

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WO2012020625A1 (fr) * 2010-08-10 2012-02-16 ダイセル化学工業株式会社 Composition de résine durcissable et article durci de celle-ci
JP2016191031A (ja) * 2015-03-30 2016-11-10 ペルノックス株式会社 半導体封止用一液性エポキシ樹脂組成物、硬化物、半導体部品の製造方法及び半導体部品
CN111500015A (zh) * 2016-11-28 2020-08-07 联茂(无锡)电子科技有限公司 无卤素树脂组成物
EP3696231A4 (fr) * 2018-01-11 2020-12-30 Lg Chem, Ltd. Composition de résine époxy pour le moulage de semi-conducteur, et film de moulage et boîtier de semi-conducteur l'utilisant

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TWI494339B (zh) 2012-10-23 2015-08-01 Ind Tech Res Inst 部分酯化環氧樹脂及應用其製成之環氧樹脂組成物及其製法
JP6332907B2 (ja) 2013-02-14 2018-05-30 東京応化工業株式会社 封止用樹脂組成物、表示装置、及び光半導体装置
JP6523780B2 (ja) 2014-09-29 2019-06-05 東京応化工業株式会社 膜形成性組成物、及びそれを用いた硬化被膜の製造方法

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CN102782000A (zh) 2012-11-14
JP5606752B2 (ja) 2014-10-15
MY160200A (en) 2017-02-28

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