KR20150032179A - Epoxy resin composition, use thereof, and filler for epoxy resin composition - Google Patents
Epoxy resin composition, use thereof, and filler for epoxy resin composition Download PDFInfo
- Publication number
- KR20150032179A KR20150032179A KR20140120334A KR20140120334A KR20150032179A KR 20150032179 A KR20150032179 A KR 20150032179A KR 20140120334 A KR20140120334 A KR 20140120334A KR 20140120334 A KR20140120334 A KR 20140120334A KR 20150032179 A KR20150032179 A KR 20150032179A
- Authority
- KR
- South Korea
- Prior art keywords
- epoxy resin
- resin composition
- magnesium oxide
- oxide powder
- thermally conductive
- Prior art date
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- 239000003822 epoxy resin Substances 0.000 title claims abstract description 92
- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 92
- 239000000203 mixture Substances 0.000 title claims abstract description 72
- 239000000945 filler Substances 0.000 title description 5
- -1 use thereof Substances 0.000 title description 5
- 239000000395 magnesium oxide Substances 0.000 claims abstract description 82
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims abstract description 82
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 claims abstract description 82
- 239000000843 powder Substances 0.000 claims abstract description 71
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 33
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 13
- 125000003277 amino group Chemical group 0.000 claims abstract description 12
- 239000000853 adhesive Substances 0.000 claims abstract description 11
- 239000003566 sealing material Substances 0.000 claims abstract description 11
- 230000001070 adhesive effect Effects 0.000 claims abstract description 10
- 239000005011 phenolic resin Substances 0.000 claims description 35
- 239000000126 substance Substances 0.000 claims description 13
- 229920001568 phenolic resin Polymers 0.000 claims description 12
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 7
- 238000004898 kneading Methods 0.000 abstract description 17
- 238000002485 combustion reaction Methods 0.000 abstract description 6
- 238000002156 mixing Methods 0.000 abstract description 6
- 238000000034 method Methods 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 230000000052 comparative effect Effects 0.000 description 14
- 238000011156 evaluation Methods 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 238000010521 absorption reaction Methods 0.000 description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 7
- 239000002245 particle Substances 0.000 description 7
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 6
- 229920003986 novolac Polymers 0.000 description 6
- 238000001721 transfer moulding Methods 0.000 description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
- 239000004305 biphenyl Substances 0.000 description 5
- 235000010290 biphenyl Nutrition 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 239000011256 inorganic filler Substances 0.000 description 5
- 229910003475 inorganic filler Inorganic materials 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 4
- 238000004381 surface treatment Methods 0.000 description 4
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 229930003836 cresol Natural products 0.000 description 3
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 3
- 239000000347 magnesium hydroxide Substances 0.000 description 3
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 3
- 239000004848 polyfunctional curative Substances 0.000 description 3
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
- 239000006087 Silane Coupling Agent Substances 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 238000001354 calcination Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- PHQOGHDTIVQXHL-UHFFFAOYSA-N n'-(3-trimethoxysilylpropyl)ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCCNCCN PHQOGHDTIVQXHL-UHFFFAOYSA-N 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 239000011342 resin composition Substances 0.000 description 2
- 229910000077 silane Inorganic materials 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 2
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 2
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- 229910052581 Si3N4 Inorganic materials 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 1
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 239000011247 coating layer Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- PMHQVHHXPFUNSP-UHFFFAOYSA-M copper(1+);methylsulfanylmethane;bromide Chemical compound Br[Cu].CSC PMHQVHHXPFUNSP-UHFFFAOYSA-M 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 229960002887 deanol Drugs 0.000 description 1
- 238000005202 decontamination Methods 0.000 description 1
- 230000003588 decontaminative effect Effects 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 238000009775 high-speed stirring Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- UJNZOIKQAUQOCN-UHFFFAOYSA-N methyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(C)C1=CC=CC=C1 UJNZOIKQAUQOCN-UHFFFAOYSA-N 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000003595 mist Substances 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—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
- C08G59/62—Alcohols or phenols
- C08G59/621—Phenols
-
- 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
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
- C08K5/541—Silicon-containing compounds containing oxygen
- C08K5/5415—Silicon-containing compounds containing oxygen containing at least one Si—O bond
-
- 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
- C08K9/00—Use of pretreated ingredients
- C08K9/04—Ingredients treated with organic substances
- C08K9/06—Ingredients treated with organic substances with silicon-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
- C09K3/10—Materials in mouldable or extrudable form for sealing or packing joints or covers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
- C09K5/08—Materials not undergoing a change of physical state when used
- C09K5/14—Solid materials, e.g. powdery or granular
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
- H01L21/50—Assembly of semiconductor devices using processes or apparatus not provided for in a single one of the subgroups H01L21/06 - H01L21/326, e.g. sealing of a cap to a base of a container
- H01L21/56—Encapsulations, e.g. encapsulation layers, coatings
-
- 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
-
- 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
- H01L23/31—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the arrangement or shape
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/34—Arrangements for cooling, heating, ventilating or temperature compensation ; Temperature sensing arrangements
- H01L23/36—Selection of materials, or shaping, to facilitate cooling or heating, e.g. heatsinks
- H01L23/373—Cooling facilitated by selection of materials for the device or materials for thermal expansion adaptation, e.g. carbon
-
- 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
- C08K2003/2217—Oxides; Hydroxides of metals of magnesium
- C08K2003/222—Magnesia, i.e. magnesium oxide
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Physics & Mathematics (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Power Engineering (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- General Physics & Mathematics (AREA)
- Computer Hardware Design (AREA)
- Materials Engineering (AREA)
- Combustion & Propulsion (AREA)
- Thermal Sciences (AREA)
- Manufacturing & Machinery (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Epoxy Resins (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Structures Or Materials For Encapsulating Or Coating Semiconductor Devices Or Solid State Devices (AREA)
- Cooling Or The Like Of Semiconductors Or Solid State Devices (AREA)
Abstract
Description
본 발명은, 산화마그네슘 분말을 함유하는 열전도성의 에폭시 수지 조성물, 및 그것으로 이루어진 열전도성 밀봉재, 열전도성 시트, 열전도성 접착제, 경화물, 그리고 산화마그네슘 분말을 함유하는 에폭시 수지 조성물용 충전재에 관한 것이다. 특히, 혼련에 의해서 용이하게 조제하는 것이 가능하며, 유동성이 개량되어서 성형성이 우수하고, 흡수성이 양호(저흡수성)하며, 바람직하게는 더욱 내연소성이 우수한 열전도성의 에폭시 수지 조성물에 관한 것이다.The present invention relates to a thermally conductive epoxy resin composition containing a magnesium oxide powder and a filler for an epoxy resin composition containing the thermally conductive sealing material, the thermally conductive sheet, the thermally conductive adhesive, the cured product, and the magnesium oxide powder thereof . In particular, the present invention relates to a thermally conductive epoxy resin composition which can be easily prepared by kneading, has improved fluidity, is excellent in moldability, has excellent water absorbability (low water absorption), and is more excellent in resistance to combustion.
에폭시 수지 조성물은 많은 분야에서 각종 용도에 이용되고 있다.BACKGROUND ART Epoxy resin compositions are used in various fields in various fields.
특히 전자부품에서는, 기판 재료, 밀봉 재료, 열전도성 시트 재료, 접착제 등으로서 적합하게 사용되고 있다. 이 용도에서는, 소형화, 고집적화, 고용량화, 고속화 등의 진전과 함께, 전자부품으로부터의 발열량이 증가하는 경향이 있다. 발열량이 증가하면 온도나 습도의 영향에 의해서 전자부품의 신뢰성이 저하한다. 이 때문에, 에폭시 수지 조성물에 대해서, 내열성이나 저흡수성(내습성)에 부가해서, 방열성을 향상하기 위하여 열전도성을 부여하는 것이 요구되고 있다.Particularly, electronic components are suitably used as a substrate material, a sealing material, a thermally conductive sheet material, an adhesive, and the like. In this application, the amount of heat generated from the electronic component tends to increase with advances such as miniaturization, high integration, high capacity and high speed. When the amount of heat generated increases, the reliability of the electronic component deteriorates due to the influence of temperature and humidity. For this reason, it is required to impart heat conductivity to the epoxy resin composition in order to improve the heat radiation property in addition to heat resistance and low water absorption (moisture resistance).
또한, 접착제나 코팅재의 경우에는 반드시 난연성이 요구되지 않지만, 반도체 밀봉재와 같은 발열원을 직접 밀봉하는 바와 같은 경우에는, 안전성을 고려해서 전자부품용으로서의 고도한 내연소성이 요구되고 있다.In the case of an adhesive or a coating material, flame resistance is not necessarily required. However, in the case where a heat source such as a semiconductor sealing material is sealed directly, a high degree of resistance to burning for electronic parts is required in consideration of safety.
에폭시 수지 조성물에 열전도성을 부여하기 위하여, 산화마그네슘을 배합하는 것이 이미 제안되어 있다. 산화마그네슘에 의해서 열전도성은 향상된다. 그러나, 배합량이 증대하면 유동성이 저하하여 성형성이 충분하지 않게 되므로, 특히 소형화(박막화, 미세화, 복잡화)한 전자부품에서는 성형성에 문제가 생긴다.In order to impart thermal conductivity to the epoxy resin composition, it has already been proposed to blend magnesium oxide. The thermal conductivity is improved by magnesium oxide. However, when the compounding amount is increased, the fluidity is lowered and the formability is not sufficient, so that there is a problem in the formability particularly in an electronic component which is miniaturized (thinned, refined, complicated).
특허문헌 1에는, 내습성 및 열전도성이 우수한 산화마그네슘 분말을 함유하는 수지 조성물이 제안되어 있다. 여기에서는, 산화마그네슘을 실란 등의 무기계 커플링제에 의해 표면처리하면, 수지와의 혼련 작업 공정에서 표면처리한 처리제가 산화마그네슘의 표면으로부터 박리하기 쉬워, 기계적 강도가 결여되고, 표면이 수화반응해서 수산화마그네슘으로 변화되어서 백화 현상이 생기므로 실용화에 이르지 못한다는 취지의 기재가 있다. 여기에서는, 표면에 규소와 마그네슘의 복산화물 및/또는 알루미늄과 마그네슘의 복산화물을 함유하는 피복층을 지니는 피복 산화마그네슘이 이용되고 있다.Patent Document 1 proposes a resin composition containing magnesium oxide powder excellent in moisture resistance and thermal conductivity. Here, when the magnesium oxide is surface-treated with an inorganic coupling agent such as silane, the treatment agent surface-treated in the kneading work step with resin tends to peel off from the surface of magnesium oxide, lacks mechanical strength, There is a description of the fact that it can not be put to practical use because it is converted into magnesium hydroxide to cause bleaching phenomenon. Here, magnesium oxide coated with a coating layer containing a double oxide of silicon and magnesium and / or a double oxide of aluminum and magnesium is used on the surface.
특허문헌 2에는, 산화마그네슘 분말과 이산화 규소분말을 특정 용적비로 배합한 열전도성(방열성)을 개량한 에폭시 수지 조성물이 제안되어 있다. 여기에는, 산화마그네슘의 표면을 실란 커플링제로 처리하는 것이 기재되고, 실시예에서는, 올리고머 형태의 반응성 실록산에 의해서 처리된 산화마그네슘이 이용되고 있다. 그러나, 통상의 (화합물 타입의) 실란 커플링제에 대해서는 반드시 상세한 검토가 이루어져 있지 않았다.Patent Document 2 proposes an epoxy resin composition improved in thermal conductivity (heat radiation property) by mixing magnesium oxide powder and silicon dioxide powder at a specific volume ratio. It is described herein that the surface of magnesium oxide is treated with a silane coupling agent, and in the examples magnesium oxide treated with an oligomeric reactive siloxane is used. However, the conventional (compound type) silane coupling agent has not been thoroughly examined in detail.
본 발명의 목적은, 혼련에 의해서 용이하게 조제하는 것이 가능하며, 유동성이 개량되어서 성형성이 우수하고, 흡수성이 양호(저흡수성)한, 산화마그네슘 분말을 함유한 열전도성의 에폭시 수지 조성물을 제공하는 것이다. 또, 본 발명의 목적은, 바람직하게는 더욱 내연소성이 우수한 산화마그네슘 분말을 함유한 열전도성의 에폭시 수지 조성물을 제공하는 것이다. 본 발명의 에폭시 수지 조성물은, 열전도성 밀봉재, 열전도성 시트, 열전도성 접착제 및 경화물로서 적합하게 사용할 수 있다.An object of the present invention is to provide a thermally conductive epoxy resin composition containing magnesium oxide powder which can be easily prepared by kneading, has improved fluidity, and is excellent in moldability and water absorbability (low water absorption) will be. It is also an object of the present invention to provide a thermally conductive epoxy resin composition containing magnesium oxide powder which is more excellent in resistance to combustion. The epoxy resin composition of the present invention can be suitably used as a thermally conductive sealing material, a thermally conductive sheet, a thermally conductive adhesive, and a cured product.
본 발명은, 이하의 사항에 관한 것이다.The present invention relates to the following.
1. 에폭시 수지, 경화제, 그리고 페닐기 및 아미노기 중 적어도 한쪽을 지니는 알콕시실란으로 표면처리된 산화마그네슘 분말을 함유하는 것을 특징으로 하는 에폭시 수지 조성물.1. An epoxy resin composition comprising an epoxy resin, a curing agent, and a magnesium oxide powder surface-treated with an alkoxysilane having at least one of a phenyl group and an amino group.
2. 상기 알콕시실란이 하기 화학식 1로 표시되는 화합물인 것을 특징으로 하는 상기 1항에 기재된 에폭시 수지 조성물:2. The epoxy resin composition according to the above 1, wherein the alkoxysilane is a compound represented by the following formula 1:
[화학식 1][Chemical Formula 1]
화학식 1에 있어서, l은 1 내지 3의 정수이고, R은 각각 동일 또는 상이해도 되는 알킬기이며, R'는 각각 동일 또는 상이해도 되는 페닐기 및 아미노기 중 적어도 한쪽을 함유하는 1가의 기이다.In formula (1), l is an integer of 1 to 3, R is an alkyl group which may be the same or different, and R 'is a monovalent group containing at least one of a phenyl group and an amino group which may be the same or different.
3. 상기 경화제가 페놀 수지인 것을 특징으로 하는 상기 1항 또는 2항에 기재된 에폭시 수지 조성물.3. The epoxy resin composition according to claim 1 or 2, wherein the curing agent is a phenol resin.
4. 상기 페놀 수지가 페닐아르알킬형 페놀 수지 및 바이페닐아르알킬형 페놀 수지로 이루어진 군으로부터 선택된 1종 이상의 페놀 수지인 것을 특징으로 하는 상기 3항에 기재된 에폭시 수지 조성물.4. The epoxy resin composition according to item 3 above, wherein the phenol resin is at least one phenol resin selected from the group consisting of phenylaralkyl type phenol resins and biphenylaralkyl type phenol resins.
5. 상기 1항 내지 4항 중 어느 한 항에 기재된 에폭시 수지 조성물로 이루어진 열전도성 밀봉재.5. A thermally conductive sealing material comprising the epoxy resin composition according to any one of claims 1 to 4.
6. 상기 1항 내지 4항 중 어느 한 항에 기재된 에폭시 수지 조성물로 이루어진 열전도성 시트.6. A thermally conductive sheet comprising the epoxy resin composition according to any one of claims 1 to 4.
7. 상기 1항 내지 4항 중 어느 한 항에 기재된 에폭시 수지 조성물로 이루어진 열전도성 접착제.7. A thermally conductive adhesive comprising the epoxy resin composition according to any one of claims 1 to 4.
8. 상기 1항 내지 4항 중 어느 한 항에 기재된 에폭시 수지 조성물을 경화시킨 경화물.8. A cured product obtained by curing the epoxy resin composition according to any one of claims 1 to 4.
9. 에폭시 수지, 페닐아르알킬형 페놀 수지 및 바이페닐아르알킬형 페놀 수지로 이루어진 군으로부터 선택된 1종 이상의 페놀 수지로 이루어진 경화제, 및 산화마그네슘 분말을 함유하는 것을 특징으로 하는 에폭시 수지 조성물.9. An epoxy resin composition comprising a curing agent comprising at least one phenol resin selected from the group consisting of an epoxy resin, a phenylaralkyl type phenol resin and a biphenylaralkyl type phenol resin, and a magnesium oxide powder.
10. 페닐기 및 아미노기 중 적어도 한쪽을 지니는 알콕시실란으로 표면처리된 산화마그네슘 분말로 이루어진 것을 특징으로 하는 에폭시 수지 조성물용 충전재.10. A filler for an epoxy resin composition, which comprises magnesium oxide powder surface-treated with an alkoxysilane having at least one of a phenyl group and an amino group.
본 발명에 따르면, 혼련에 의해서 용이하게 조제하는 것이 가능하며, 유동성이 개량되어서 성형성이 우수하고, 흡수성이 양호(저흡수성)한, 산화마그네슘 분말을 함유한 열전도성의 에폭시 수지 조성물을 제공할 수 있다. 또한, 본 발명에 의해, 바람직하게는 더욱 내연소성이 우수한 산화마그네슘 분말을 함유한 열전도성의 에폭시 수지 조성물을 제공할 수 있다. 본 발명의 에폭시 수지 조성물은, 열전도성 밀봉재, 열전도성 시트, 열전도성 접착제 및 경화물로서 적합하게 사용할 수 있다.According to the present invention, it is possible to provide a thermally conductive epoxy resin composition containing magnesium oxide powder which can be easily prepared by kneading, has improved fluidity, and is excellent in moldability and water absorption (low water absorption) have. Further, according to the present invention, it is possible to provide a thermally conductive epoxy resin composition containing magnesium oxide powder which is more excellent in resistance to burning. The epoxy resin composition of the present invention can be suitably used as a thermally conductive sealing material, a thermally conductive sheet, a thermally conductive adhesive, and a cured product.
본 발명은, 에폭시 수지, 경화제, 그리고 페닐기 및 아미노기 중 적어도 한쪽을 지니는 알콕시실란으로 표면처리된 산화마그네슘 분말을 함유하는 것을 특징 으로 하는 에폭시 수지 조성물에 관한 것이다.The present invention relates to an epoxy resin composition comprising an epoxy resin, a curing agent, and a magnesium oxide powder surface-treated with an alkoxysilane having at least one of a phenyl group and an amino group.
본 발명의 에폭시 수지 조성물의 에폭시 수지는, 분자 내에 2개 이상의 에폭시기를 함유하는 것이면 되고, 특별히 한정은 없지만, 예를 들어, 비스페놀형, 페놀노볼락형, 크레졸노볼락형, 바이페닐형, 트라이페닐메탄형, 다이사이클로펜타다이엔형, 나프톨형 등의 에폭시 수지를 적합하게 들 수 있다. 이들 에폭시 수지는 단독으로 이용해도, 복수종을 혼합해서 이용해도 상관없다. 이들 에폭시 수지 중에서는, 특히 크레졸 노볼락형 에폭시 수지, 바이페닐형 에폭시 수지가 적절하다.The epoxy resin of the epoxy resin composition of the present invention is not particularly limited as long as it contains two or more epoxy groups in the molecule, and examples thereof include bisphenol type, phenol novolak type, cresol novolak type, And epoxy resins such as phenylmethane type, dicyclopentadiene type and naphthol type. These epoxy resins may be used alone or in combination of plural kinds. Of these epoxy resins, cresol novolak type epoxy resins and biphenyl type epoxy resins are particularly suitable.
본 발명의 에폭시 수지 조성물의 경화제는, 에폭시 수지와 반응해서 경화물을 얻을 수 있는 것이면 특별히 한정은 없고, 에폭시 수지의 경화제로서 통상 이용되는 아민 화합물, 산무수물, 페놀 수지 등을 적합하게 사용할 수 있다.The curing agent of the epoxy resin composition of the present invention is not particularly limited as long as it is capable of reacting with the epoxy resin to obtain a cured product, and amine compounds, acid anhydrides, phenol resins and the like which are generally used as curing agents for epoxy resins can be suitably used .
본 발명의 에폭시 수지 조성물의 경화제는, 바람직하게는 페놀 수지이다. 페놀 수지로서는, 특별히 한정되는 것은 아니고, 예를 들어, 페놀 노볼락형, 크레졸노볼락형, 페닐아르알킬형, 바이페닐아르알킬형, 트라이페닐메탄형, 다이사이클로펜타다이엔형, 나프톨형 등의 노볼락형 페놀 수지를 적합하게 들 수 있지만, 그들 중에서는, 특히 페닐아르알킬형 페놀 수지 및 바이페닐아르알킬형 페놀 수지가, 흡수성이 낮고, 더욱 내연소성(난연성)을 향상시킬 수 있는 점으로부터 특히 적합하게 사용할 수 있다.The curing agent of the epoxy resin composition of the present invention is preferably a phenolic resin. Examples of the phenol resin include, but are not limited to, phenol novolak type, cresol novolak type, phenyl aralkyl type, biphenyl aralkyl type, triphenyl methane type, dicyclopentadiene type, naphthol type, etc. Among them, phenol aralkyl-type phenol resin and biphenylaralkyl-type phenol resin are particularly preferred because of their low water absorbency and further improved resistance to flammability (flame retardancy) Can be suitably used.
페닐아르알킬형 페놀 수지 및 바이페닐아르알킬형 페놀 수지는, 페놀류를, 대표적으로는 -CH2-Bz-CH2- 혹은 -CH2-Bz-Bz-CH2-(Bz: 벤젠고리)와 같은 페닐렌 골격 혹은 바이페닐렌 골격을 기 중에 함유하는 2가의 가교기(페닐아르알킬기 혹은 바이페닐아르알킬기)로 결합한 화학구조를 지니는 노볼락형 페놀 수지이며, 바람직하게는 하기 화학식 2 내지 5, 보다 바람직하게는 하기 화학식 4 내지 5의 화학구조를 지닌다.The phenylaralkyl-type phenol resin and the biphenylaralkyl-type phenol resin can be produced by reacting phenols with typically -CH 2 -Bz-CH 2 - or -CH 2 -Bz-Bz-CH 2 - (Bz: benzene ring) Is a novolak type phenolic resin having a chemical structure bonded with a divalent crosslinking group (phenylaralkyl group or biphenylaralkyl group) containing the same phenylene skeleton or biphenylene skeleton in the group, More preferably have the chemical structures of the following formulas (4) to (5).
[화학식 2](2)
상기 화학식 2에 있어서, n은 1 이상의 정수(바람직하게는 1 내지 20의 정수)이고, R1은 탄소수가 1 내지 6인 알킬기 또는 수산기 중 어느 한쪽이며, p는 0 내지 2의 정수이다.In the general formula (2), n is an integer of 1 or more (preferably an integer of 1 to 20), R 1 is either an alkyl group having 1 to 6 carbon atoms or a hydroxyl group, and p is an integer of 0 to 2.
[화학식 3](3)
상기 화학식 3에 있어서, m은 1 이상의 정수(바람직하게는 1 내지 20의 정수)이고, n은 1 이상의 정수(바람직하게는 1 내지 20의 정수)이며, R1은 탄소수가 1 내지 6인 알킬기 또는 수산기 중 어느 한쪽이고, p는 0 내지 2의 정수이다.M is an integer of 1 or more (preferably an integer of 1 to 20), n is an integer of 1 or more (preferably an integer of 1 to 20), and R 1 is an alkyl group having 1 to 6 carbon atoms Or a hydroxyl group, and p is an integer of 0 to 2.
[화학식 4][Chemical Formula 4]
상기 화학식 4에 있어서, n은 1 이상의 정수(바람직하게는 1 내지 20의 정수)이고, R1은 탄소수가 1 내지 6인 알킬기 또는 수산기 중 어느 한쪽이며, p는 0 내지 2의 정수이다.In the general formula (4), n is an integer of 1 or more (preferably an integer of 1 to 20), R 1 is either an alkyl group having 1 to 6 carbon atoms or a hydroxyl group, and p is an integer of 0 to 2.
[화학식 5][Chemical Formula 5]
상기 화학식 5에 있어서, m은 1 이상의 정수(바람직하게는 1 내지 20의 정수)이고, n은 1 이상의 정수(바람직하게는 1 내지 20의 정수)이며, R1은 탄소수가 1 내지 6인 알킬기 또는 수산기 중 어느 한쪽이고, p는 0 내지 2의 정수이다.In Formula 5, m is an integer of 1 or more (preferably an integer of 1 to 20), n is an integer of 1 or more (preferably an integer of 1 to 20), and R 1 is an alkyl group having 1 to 6 carbon atoms Or a hydroxyl group, and p is an integer of 0 to 2.
본 발명의 에폭시 수지 조성물에 있어서, 에폭시 수지와 경화제의 배합 비율은, 특별히 한정되는 것은 아니지만, 에폭시 수지의 배합량을 100질량부로 했을 때, 경화제는 50 내지 120질량부의 범위인 것이 바람직하다.In the epoxy resin composition of the present invention, the blending ratio of the epoxy resin and the curing agent is not particularly limited, but when the blending amount of the epoxy resin is 100 parts by mass, the curing agent is preferably in the range of 50 to 120 parts by mass.
본 발명의 에폭시 수지 조성물에서 이용되는 산화마그네슘 분말은, 페닐기 및 아미노기 중 적어도 한쪽을 지니는 알콕시실란으로 표면처리된 것이다.The magnesium oxide powder used in the epoxy resin composition of the present invention is surface-treated with an alkoxysilane having at least one of a phenyl group and an amino group.
산화마그네슘 분말은, 특별히 한정되는 것은 아니지만, 예를 들어, 수산화마그네슘을 약 14000℃ 이상 내지 약 2800℃(용융 온도) 미만으로 가열 처리함으로써 적합하게 얻을 수 있다. 본 발명에 있어서는, 바람직하게는 1600℃ 이상 내지 2600℃ 미만, 보다 바람직하게는 2000 내지 2400℃의 온도에서 소성해서 얻어진 산화마그네슘 분말을 적합하게 사용할 수 있다. 또한, 본 발명의 산화마그네슘 분말은, 특별히 한정되는 것은 아니지만, 평균 입자 직경이, 바람직하게는 O.5 내지 100㎛, 보다 바람직하게는 1 내지 80㎛의 범위에 있고, 순도가, 바람직하게는 94.0질량% 이상, 보다 바람직하게는 96.0 내지 99.7질량%의 범위인 것이다.The magnesium oxide powder is not particularly limited, and can be suitably obtained, for example, by heat-treating magnesium hydroxide at a temperature of from about 14000 DEG C to about 2800 DEG C (melting temperature). In the present invention, magnesium oxide powder obtained by calcining at a temperature of preferably 1600 DEG C or more to less than 2600 DEG C, more preferably 2000 to 2400 DEG C, may be suitably used. The magnesium oxide powder of the present invention is not particularly limited, but the average particle diameter is preferably in the range of 0.5 to 100 탆, more preferably 1 to 80 탆, and the purity is preferably Is 94.0 mass% or more, and more preferably 96.0 to 99.7 mass%.
본 발명에서 사용하는 산화마그네슘의 표면처리에 사용하는 알콕시실란은, 분자 내에 적어도 페닐기 및 아미노기 중 어느 것인가를 포함하는 화학구조를 지니는 알콕시실란(화합물에 있어서, 올리고머는 아님)이며, 바람직하게는 하기 화학식 1로 표시되는 알콕시실란이다. 특히, 알콕시실란은, 유동성의 관점에서는 페닐기를 함유하는 것이 바람직하다.The alkoxysilane used in the surface treatment of magnesium oxide used in the present invention is an alkoxysilane (not an oligomer in the compound) having a chemical structure containing at least either a phenyl group or an amino group in the molecule, Is an alkoxysilane represented by the general formula (1). In particular, it is preferable that the alkoxysilane contains a phenyl group in terms of fluidity.
[화학식 1][Chemical Formula 1]
화학식 1에 있어서, 1은 1 내지 3의 정수이고, R은 각각 동일 또는 상이해도 되는 알킬기(바람직하게는 탄소수가 1 내지 6인 알킬기, 보다 바람직하게는 메틸기 또는 에틸기)이며, R'는 각각 동일 또는 상이해도 되는 페닐기 및 아미노기 중 적어도 한쪽을 함유하는 1가의 기이다.In formula (1), 1 is an integer of 1 to 3, R is an alkyl group (preferably an alkyl group having 1 to 6 carbon atoms, more preferably a methyl group or an ethyl group) which may be the same or different, and R ' Or a monovalent group containing at least one of a phenyl group and an amino group which may be different.
이러한 알콕시실란의 구체예로서는, 하기 화학식 6으로 표시되는 각 화합물을 적합하게 들 수 있다:As specific examples of such alkoxysilane, each of the compounds represented by the following formula (6) is suitably used:
[화학식 6][Chemical Formula 6]
또, 알콕시실란의 처리량은, 특별히 한정되는 것은 아니지만, 산화마그네슘 분말에 대해서, 바람직하게는 O.01 내지 10질량%, 보다 바람직하게는 O.05 내지 5질량%의 비율이다.The treatment amount of the alkoxysilane is not particularly limited, but it is preferably 0.01 to 10% by mass, more preferably 0.05 to 5% by mass, based on the magnesium oxide powder.
본 발명에 있어서는, 표면을 페닐기 및 아미노기 중 적어도 한쪽을 지니는 알콕시실란으로 처리한 산화마그네슘을 이용함으로써, 혼련에 의해서 용이하게 조제하는 것이 가능하여, 성형 시의 유동성(나선형 흐름)이 개량되어서 성형성이 우수하고, 또한 저흡수성의, 열전도성 에폭시 수지 조성물을 얻을 수 있다.In the present invention, magnesium oxide treated with an alkoxysilane having at least one of a phenyl group and an amino group on the surface thereof can be easily prepared by kneading, and the fluidity (spiral flow) at the time of molding is improved, It is possible to obtain a thermally conductive epoxy resin composition which is excellent in heat resistance and low in water absorption.
산화마그네슘 분말의 표면 처리 방법은, 특별히 한정되는 것은 아니지만, 예를 들어, 건식 반응법이나 습식 반응법 등을 이용해서 표면처리할 수 있다. 건식 반응법은, 헨셸 믹서 등의 고속 교반 가능한 장치에 산화마그네슘 분말을 주입하고, 교반하면서 알콕시실란 또는 알콕시실란의 가수분해액을 첨가하는 방법이다. 그 첨가 방법으로서는, 균일하게 알콕시실란을 반응시키는 것이 가능한 방법이 바람직하고, 공지의 방법, 예를 들어, 서서히 적하하는 방법, 연무 상태로 분무하는 방법 및 기체 상태의 실란을 도입하는 방법 등을 이용할 수 있다. 습식 반응법은, 산화마그네슘 분말을 알콕시실란의 용액에 분산시킨 상태에서 반응시키고, 필요에 따라서 그 후 건조시키는 방법이다. 사용하는 용제로서는, 물, 알코올 또는 그들의 혼합물이 바람직하다.The surface treatment method of the magnesium oxide powder is not particularly limited. For example, surface treatment can be performed using a dry reaction method, a wet reaction method, or the like. The dry reaction method is a method in which magnesium oxide powder is injected into a device capable of high-speed stirring such as a Henschel mixer, and a hydrolysis solution of alkoxysilane or alkoxysilane is added while stirring. As the addition method, a method capable of uniformly reacting an alkoxysilane is preferable, and a known method such as a method of slowly dropping, a method of spraying in a mist state, a method of introducing a silane in a gaseous state, or the like . The wet reaction method is a method in which magnesium oxide powder is reacted in a state in which it is dispersed in a solution of alkoxysilane and, if necessary, dried. As the solvent to be used, water, an alcohol or a mixture thereof is preferable.
산화마그네슘 분말은 단독으로 이용해도, 다른 무기 충전재와 병용해도 무방하다. 산화마그네슘 분말을 함유하는 무기 충전재의 배합 비율은, 전체 에폭시 수지 조성물에 대해서, 용량%로, 10 내지 95%, 바람직하게는 30 내지 90%, 보다 바람직하게는 60 내지 75%의 범위이다. 병용하는 산화마그네슘 분말 이외의 다른 무기충전재로서는, 이산화규소, 알루미나, 질화알루미늄, 질화규소, 탄산칼슘, 탤크, 운모, 황산바륨 등을 들 수 있고, 그 중에서도 이산화규소 분말을 이용하는 것이 바람직하다. 산화마그네슘 분말과 병용하는 다른 무기 충전재와의 배합 비율은, 용량비[산화마그네슘 분말:병용하는 다른 무기 충전재]로, 바람직하게는 100:0 내지 5:95, 보다 바람직하게는 60:40 내지 5:95, 더욱 바람직하게는 40:60 내지 25:75의 범위다.The magnesium oxide powder may be used alone or in combination with other inorganic fillers. The mixing ratio of the inorganic filler containing the magnesium oxide powder is in the range of 10 to 95%, preferably 30 to 90%, more preferably 60 to 75% in terms of the volume percentage with respect to the entire epoxy resin composition. Examples of the inorganic filler other than the magnesium oxide powder to be used in combination include silicon dioxide, alumina, aluminum nitride, silicon nitride, calcium carbonate, talc, mica, barium sulfate and the like. Among them, silicon dioxide powder is preferably used. Magnesium oxide powder and other inorganic fillers used in combination with magnesium oxide powder are preferably 100: 0 to 5:95, more preferably 60: 40 to 5: 95, and more preferably from 40:60 to 25:75.
본 발명의 에폭시 수지 조성물에 있어서는, 에폭시 수지, 경화제, 산화마그네슘 분말을 포함하는 무기 충전재 이외에, 용도에 따라서 통상의 에폭시 수지 조성물에서 이용되는 각종 성분을 배합할 수 있다.In the epoxy resin composition of the present invention, in addition to an inorganic filler including an epoxy resin, a curing agent, and a magnesium oxide powder, various components used in a conventional epoxy resin composition may be blended depending on the application.
예를 들어, 경화 촉진제도 적합하게 이용할 수 있다. 경화 촉진제로서는, 통상의 에폭시 수지 조성물에서 이용되는 경화 촉진제를 이용할 수 있지만, 경화제에 페놀 수지를 이용한 경우에는, 페놀 수지의 수산기를 활성화하는 화합물인 것이 바람직하다. 경화 촉진제의 예로서는, 벤질다이메틸아민, 트라이에탄올아민, 다이메틸아미노에탄올 등의 아민 화합물, 트라이뷰틸포스핀, 메틸다이페닐포스핀, 트라이페닐포스핀, 다이페닐포스핀 등의 유기 인화합물을 적합하게 들 수 있다. 경화 촉진제의 배합량은, 에폭시 수지의 배합량을 100질량부에 대해서, 바람직하게는 O.1 내지 10질량부, 보다 바람직하게는 1 내지 7질량부의 범위이다.For example, a hardening accelerator may be suitably used. As the curing accelerator, a curing accelerator used in a conventional epoxy resin composition can be used. When a phenol resin is used for the curing agent, it is preferable that the compound is a compound that activates the hydroxyl group of the phenolic resin. Examples of the curing accelerator include organic compounds such as amine compounds such as benzyldimethylamine, triethanolamine and dimethylaminoethanol, organic phosphorus compounds such as tributylphosphine, methyldiphenylphosphine, triphenylphosphine and diphenylphosphine, . The blending amount of the curing accelerator is preferably in the range of 0.1 to 10 parts by mass, and more preferably 1 to 7 parts by mass based on 100 parts by mass of the epoxy resin.
또한, 본 발명의 에폭시 수지 조성물에 있어서는, 용도에 따라서, 그 밖의 각종 첨가제를 이용할 수 있다. 예를 들어, 열전도성 밀봉재 용도에서는, 이형제, 착색제, 난연제, 저응력제 등을 이용할 수 있고, 열전도성 시트 용도에서는, 점착부여제, 노화 방지제, 연화제(예를 들어, 나프텐계 오일, 파라핀계 오일 등), 요변제(thixotropic agent)(예를 들어, 몬모릴로나이트 등), 활제(예를 들어 스테아르산 등), 안료, 스코치 방지제(antiscorching agent), 안정제, 산화 방지제, 자외선 흡수제, 착색제, 방곰팡이제, 발포제 등을 이용하는 것이 가능하고, 열전도성 접착제 용도에서는, 안료, 자외선 흡수제 등을 이용할 수 있다.In the epoxy resin composition of the present invention, various other additives may be used depending on the application. For example, in the use of a thermally conductive sealing material, a releasing agent, a coloring agent, a flame retardant, a low stress agent and the like can be used. In the case of a thermally conductive sheet, a tackifier, an antioxidant, a softener (for example, Oil, etc.), thixotropic agents (e.g. montmorillonite etc.), lubricants (e.g. stearic acid), pigments, antiscorching agents, stabilizers, antioxidants, ultraviolet absorbers, A foaming agent and the like can be used. In the use of the thermally conductive adhesive agent, a pigment, an ultraviolet absorber and the like can be used.
즉, 본 발명의 에폭시 수지 조성물은, 열전도성 밀봉재, 열전도성 시트, 열전도성 접착제로서 적합하게 이용할 수 있다.That is, the epoxy resin composition of the present invention can be suitably used as a thermally conductive sealing material, a thermally conductive sheet, and a thermally conductive adhesive.
또한, 본 발명의 에폭시 수지 조성물은, 가열 처리함으로써 경화 반응을 일으켜, 경화물을 형성하는 것이 가능하다. 본 발명의 에폭시 수지 조성물을 경화시키는 조건은, 적절하게 선택할 수 있다. 예를 들어, 50 내지 300℃, 바람직하게는 130 내지 250℃에서, O.01 내지 20시간, 바람직하게는 O.1 내지 10시간, 가열 처리함으로써 경화물을 얻을 수 있다.Further, the epoxy resin composition of the present invention can be cured by heat treatment to form a cured product. The conditions for curing the epoxy resin composition of the present invention can be appropriately selected. For example, a cured product can be obtained by heat treatment at 50 to 300 ° C, preferably 130 to 250 ° C, for 0.01 to 20 hours, preferably 0.1 to 10 hours.
[실시예][Example]
이하, 본 발명을 실시예 및 비교예에 의해 더욱 구체적으로 설명하지만, 본 발명은, 이들 실시예로 한정되는 것은 아니다.Hereinafter, the present invention will be described in more detail with reference to examples and comparative examples, but the present invention is not limited to these examples.
에폭시 수지 조성물을 조제할 때의 혼련공정에 대해서 다음 방법으로 평가하였다.The kneading process for preparing the epoxy resin composition was evaluated by the following method.
(1) 혼련성(1) Kneadability
소정량의 에폭시 수지와 경화제의 페놀 수지와 충전재의 산화마그네슘 분말 및 이산화 규소분말을 2축 혼련기를 이용해서 소정의 온도에서 혼련을 행하고, 2축 혼련기의 토출구로부터 토출된 혼련물을 육안에 의해서 평가하였다. 평가 기준으로서, ○: 문제 없이 혼련 가능, △: 혼련할 수 있지만 혼련물이 불균일, ×: 혼련할 수 없음으로 하였다.A predetermined amount of phenol resin of epoxy resin and curing agent, magnesium oxide powder of a filler and silicon dioxide powder were kneaded at a predetermined temperature using a twin-screw kneader, and the kneaded material discharged from the discharge port of the biaxial kneader was visually Respectively. As the evaluation criterion,?: Capable of kneading without problems,?: Capable of kneading, but unevenness of kneaded product, and?: Not kneading.
또, 에폭시 수지 조성물에 대해서 다음 방법으로 평가하였다. 또한, 평가는, 에폭시 수지 조성물 분말을 정제(tablet)로 성형하고, 그 정제를 시료로서 행하였다. 정제는, 핸드 프레스를 이용해서 압력 450㎫로 1분간 가압해서 성형하였다.The epoxy resin composition was evaluated by the following method. In the evaluation, the epoxy resin composition powder was formed into tablets, and the tablets were used as samples. The tablets were pressed by using a hand press at a pressure of 450 MPa for one minute.
(2) 성형성(2) Moldability
시료를, 트랜스퍼 성형기에서, 금형온도는 175℃, 주입 압력은 6.9㎫로 해서, 30초간 가압한 후, 3.0㎫로 70초간 가압하는 조건에서 성형체를 성형하였다. 성형성의 평가의 기준으로서, ○: 문제 없이 성형 가능, ×: 성형할 수 없음으로 하였다.The sample was molded in a transfer molding machine under the conditions of a mold temperature of 175 ° C and an injection pressure of 6.9 MPa, a pressure of 30 seconds, and a pressure of 3.0 MPa for 70 seconds. As a criterion for evaluating the moldability,?: Can be molded without problems, and X: can not be molded.
(3) 유동성(나선형 흐름)(3) Fluidity (spiral flow)
시료의 나선형 흐름값을, 트랜스퍼 성형기, 나선형 흐름 측정용 금형(EMMI-1-66로 준거)을 이용해서 측정하였다. 또, 금형 온도는 175℃, 주입 압력은 6.9㎫로 해서, 60초간 가압한 후, 40초간 보유하는 조건에서 유동성을 평가하였다.The spiral flow value of the sample was measured using a transfer molding machine and a spiral flow measuring mold (as in EMMI-1-66). The fluidity was evaluated under the conditions that the mold temperature was 175 캜, the injection pressure was 6.9 MPa, the pressure was maintained for 60 seconds, and then the pressure was maintained for 40 seconds.
또한, 에폭시 수지 조성물의 경화물에 대해서, 다음 방법으로 평가하였다.The cured product of the epoxy resin composition was evaluated by the following method.
(4) 흡수성(흡수량)(4) Absorbency (Absorbency)
시료를 트랜스퍼 성형기에서 두께 3㎜×직경 50㎜의 원반 형상으로 성형하고, 이어서 180℃에서 8시간 경화시켜서 시험편(경화물)을 얻었다. 얻어진 시험편에 대해서, 질량(W1)을 측정하고, 95℃의 온도로 가열한 순수 중에서 24시간 보유하고, 이어서 순수 중에서 꺼내서 수분을 닦아낸 후, 그 질량(W2)을 측정하였다. 흡수량은 하기의 식으로부터 산출하였다.The specimen was molded into a disc shape having a thickness of 3 mm and a diameter of 50 mm by a transfer molding machine and then cured at 180 DEG C for 8 hours to obtain a test piece (cured product). The weight (W 1 ) of the obtained test piece was measured and held in pure water heated to a temperature of 95 캜 for 24 hours. Then, the test piece was taken out from pure water and wiped off, and its mass (W 2 ) was measured. The amount of water absorption was calculated from the following equation.
흡수량(g/㎤) = {W2(g) - W1(g)}/시험편의 체적(㎤)Absorption amount (g / ㎤) = {W 2 (g) - W 1 (g)} / volume (㎤) of the test piece
(5) 난연성(내연소성)(5) Flammability (flammability)
시료를 트랜스퍼 성형기에서 두께 1㎜ × 폭 13㎜ × 길이 127㎜의 형상으로 성형하고, 이어서 180℃에서 8시간 경화시켜서 시험편(경화물)을 얻었다. 얻어진 시험편에 대해서, UL-94 시험법에 따라서 난연성을 평가하였다.The specimen was molded into a shape having a thickness of 1 mm, a width of 13 mm and a length of 127 mm by a transfer molding machine, followed by curing at 180 DEG C for 8 hours to obtain a test piece (cured product). The obtained test pieces were evaluated for flame retardancy according to the UL-94 test method.
(6) 열전도율(6) Thermal conductivity
시료를 트랜스퍼 성형기에서 두께 4㎜ × 폭 50㎜ × 길이 100㎜의 형상으로 성형하고, 이어서 180℃에서 8시간 경화시켜서 경화물을 얻었다. 얻어진 경화물을 두께 4㎜ × 폭 25㎜ × 길이 25㎜의 형상으로 절삭가공해서 시험편으로 하였다. 시험편의 열전도율을, 알박(주)(ULVAC, Inc) 제품인 열전도율 측정 장치 GH-1을 이용해서 측정하였다.The sample was molded into a shape having a thickness of 4 mm, a width of 50 mm and a length of 100 mm by a transfer molding machine, followed by curing at 180 DEG C for 8 hours to obtain a cured product. The obtained cured product was cut into a shape having a thickness of 4 mm, a width of 25 mm, and a length of 25 mm to obtain a test piece. The thermal conductivity of the test piece was measured using a thermal conductivity measuring device GH-1 manufactured by ULVAC, Inc. (ULVAC, Inc.).
이하의 예에서 이용한 재료는 다음과 같다.The materials used in the following examples are as follows.
(a) 에폭시 수지(a) an epoxy resin
바이페닐형 에폭시 수지 YX-4000(미츠비시카가쿠(주) 제품), 에폭시 당량 186g/eq, 점도: O.2 P/150℃, 융점: 105℃(DSC법)An epoxy equivalent of 186 g / eq, a viscosity of 0.2 P / 150 deg. C, a melting point of 105 deg. C (DSC method), and a biphenyl type epoxy resin YX-4000 (manufactured by Mitsubishi Chemical Corp.)
(b) 경화제(b) Curing agent
(b1) 경화제 1(b1) Curing agent 1
하기 화학식 7로 표시되는 페놀폼알데하이드형 페놀 수지, 수산기 당량: 107g/eq, 점도: 2.O P/15O℃, 연화점: 84℃Phenol formaldehyde type phenolic resin represented by the following formula (7), hydroxyl equivalent: 107 g / eq, viscosity: 2.O P / 150 deg. C, softening point: 84 deg.
[화학식 7](7)
상기 화학식 7에 있어서, n은 1 이상의 정수이다.In Formula 7, n is an integer of 1 or more.
(b2) 경화제 2(b2) Curing agent 2
하기 화학식 8로 표시되는 바이페닐아르알킬형 페놀 수지, 수산기 당량: 201g/eq, 점도: O.8 P/150℃, 연화점: 67℃A biphenyl aralkyl type phenolic resin represented by the following formula (8), a hydroxyl group equivalent: 201 g / eq, a viscosity: 0.8 P / 150 캜, a softening point: 67 캜
[화학식 8][Chemical Formula 8]
상기 화학식 8에 있어서, n은 1 이상의 정수이다.In Formula 8, n is an integer of 1 or more.
(b3) 경화제 3(b3) Curing agent 3
하기 화학식 9로 표시되는 바이페닐아르알킬형 페놀 수지, 수산기 당량: 166g/eq, 점도: 0.5 P/150℃, 연화점: 62℃A biphenyl aralkyl type phenolic resin represented by the following formula (9), a hydroxyl equivalent weight of 166 g / eq, a viscosity of 0.5 P / 150 DEG C, a softening point of 62 DEG C
[화학식 9][Chemical Formula 9]
상기 화학식 9에 있어서, m은 1 이상의 정수이고, n은 1 이상의 정수이다.In Formula 9, m is an integer of 1 or more, and n is an integer of 1 or more.
(c) 경화 촉진제(c) Curing accelerator
트라이페닐포스핀(혹코카가쿠(北興化學)(주) 제품)Triphenylphosphine (manufactured by Hokko Chemical Industry Co., Ltd.)
(d) 산화마그네슘 분말(d) Magnesium oxide powder
산화마그네슘 분말은, 수산화마그네슘을 로터리 킬른(Rotary kiln)에 의해 2000℃에서 소성한 후에, 분쇄, 분급함으로써 제조하였다. 알콕시실란에 의한 표면처리는, 고속유동교반기를 이용해서 산화마그네슘에 대해서 O.5질량% 첨가하고, 120℃에서 10분간 가열 교반함으로써 행하였다.Magnesium oxide powder was produced by calcining magnesium hydroxide at 2000 占 폚 by a rotary kiln, followed by pulverization and classification. The surface treatment with alkoxysilane was carried out by adding 0.5% by mass of magnesium oxide to the magnesium oxide using a high-speed flow stirrer and heating and stirring at 120 占 폚 for 10 minutes.
(d1) 산화마그네슘 분말 1(d1) Magnesium oxide powder 1
표면이 페닐트라이메톡시실란으로 처리된 산화마그네슘 분말, 평균 입자 직경: 5.5㎛Magnesium oxide powder whose surface was treated with phenyltrimethoxysilane, average particle diameter: 5.5 占 퐉
(d2) 산화마그네슘 분말 2(d2) Magnesium oxide powder 2
표면이 N-2-아미노에틸-3-아미노프로필트라이메톡시실란으로 처리된 산화마그네슘 분말, 평균 입자 직경: 6.1㎛Magnesium oxide powder whose surface was treated with N-2-aminoethyl-3-aminopropyltrimethoxysilane, average particle diameter: 6.1 mu m
(d3) 산화마그네슘 분말 3(d3) Magnesium oxide powder 3
표면이 3-글라이시독시프로필트라이메톡시실란으로 처리된 산화마그네슘 분말, 평균 입자 직경: 6.8㎛Magnesium oxide powder whose surface was treated with 3-glycidoxypropyl trimethoxysilane, average particle diameter: 6.8 mu m
(d4) 산화마그네슘 분말 4(d4) Magnesium oxide powder 4
표면이 비닐트라이메톡시실란으로 처리된 산화마그네슘, 평균 입자 직경: 6.2㎛Magnesium oxide whose surface is treated with vinyltrimethoxysilane, average particle diameter: 6.2 mu m
(d5) 산화마그네슘 분말 5(d5) Magnesium oxide powder 5
표면이 처리되어 있지 않은 산화마그네슘 분말, 평균 입자 직경: 6.5㎛Magnesium oxide powder whose surface has not been treated, average particle diameter: 6.5 탆
(e) 이산화규소 분말(e) a silicon dioxide powder
MSR-2212((주)타츠모리 제품, 평균 입자 직경: 25㎛MSR-2212 (product of Tatsumori Co., Ltd., average particle diameter: 25 占 퐉
[실시예 1][Example 1]
표 1에 표시된 바와 같이, 에폭시 수지의 YX-4000 100g(100질량부), 경화제인 경화제 1(페놀폼알데하이드형 페놀 수지) 57g(57질량부), 경화 촉진제인 트라이페닐포스핀 2.7g(2.7질량부), 충전재인 이산화규소 분말(MSR-2212) 532g(532질량부)과, 표면이 페닐트라이메톡시실란으로 처리된 산화마그네슘 분말 1 424g(424질량부)을, 2축 혼련기를 이용해서 표 1에 표시된 온도 조건에서 혼련하여, 에폭시 수지 조성물의 혼련물을 얻었다. 그 때의 혼련공정을 관찰하였다.As shown in Table 1, 57 g (57 parts by mass) of curing agent 1 (phenol formaldehyde type phenolic resin) as a curing agent, 2.7 g (2.7 mass parts) of triphenylphosphine as a curing accelerator, 100 g (100 mass parts) of YX- 532 g (532 parts by mass) of silicon dioxide powder (MSR-2212) as a filler and 424 g (424 parts by mass) of magnesium oxide powder 1 whose surface was treated with phenyltrimethoxysilane were placed in a twin-screw kneader 1, and kneaded to obtain a kneaded product of the epoxy resin composition. The kneading process at that time was observed.
얻어진 혼련물을 실온까지 냉각시킨 후, 분쇄기를 이용해서 분쇄하여, 분말화하였다. 이 분말을 소정의 금형에서 가압 성형해서 에폭시 수지 조성물로 이루어진 정제를 성형하였다. 이 정제를 시료로 해서, 유동성(나선형 흐름)을 평가하였다. 또한 시료를 트랜스퍼 성형기에 의해 소정의 치수로 성형하고, 180℃에서 8시간 경화시켜서 소정 치수의 시험편(경화물)을 제작하였다.The obtained kneaded product was cooled to room temperature, and then pulverized using a pulverizer to obtain a powder. This powder was pressure-molded in a predetermined mold to form a tablet made of an epoxy resin composition. Using this tablet as a sample, fluidity (spiral flow) was evaluated. The specimen was molded into a predetermined size by a transfer molding machine and cured at 180 DEG C for 8 hours to prepare a test piece (cured product) having a predetermined dimension.
[실시예 2][Example 2]
표 1에 표시된 바와 같이, 경화제인 경화제 1(페놀폼알데하이드형 페놀 수지) 대신에, 경화제 2(바이페닐아르알킬형페놀 수지)를 사용하여, 실시예 1과 마찬가지로 해서 에폭시 수지 조성물의 혼련물을 얻었다. 또, 그 평가를 행하였다.As shown in Table 1, a kneaded product of an epoxy resin composition was obtained in the same manner as in Example 1 except that the curing agent 2 (biphenylaralkyl type phenol resin) was used instead of the curing agent 1 (phenol formaldehyde type phenol resin) . In addition, the evaluation was carried out.
[실시예 3][Example 3]
표 1에 표시된 바와 같이, 산화마그네슘 분말 1 대신에, 표면이 N-2-아미노에틸-3-아미노프로필트라이메톡시실란으로 처리된 산화마그네슘 분말 2를 사용하여, 실시예 2와 마찬가지로 해서 에폭시 수지 조성물의 혼련물을 얻었다. 또한, 그 평가를 행하였다.As shown in Table 1, using magnesium oxide powder 2 whose surface was treated with N-2-aminoethyl-3-aminopropyltrimethoxysilane instead of magnesium oxide powder 1, an epoxy resin A kneaded product of the composition was obtained. The evaluation was also performed.
[실시예 4][Example 4]
표 1에 표시된 바와 같이, 경화제의 경화제 1(페놀폼알데하이드형 페놀 수지) 대신에, 경화제 3(바이페닐아르알킬형 페놀 수지)을 사용하여, 실시예 1과 마찬가지로 해서 에폭시 수지 조성물의 혼련물을 얻었다. 또한, 그 평가를 행하였다.As shown in Table 1, a kneaded product of an epoxy resin composition was obtained in the same manner as in Example 1, except that the curing agent 3 (biphenylaralkyl type phenol resin) was used in place of the curing agent 1 (phenol formaldehyde type phenol resin) . The evaluation was also performed.
[비교예 1][Comparative Example 1]
표 1에 표시된 바와 같이, 이산화규소 분말만을 사용하여, 실시예 1과 마찬가지로 해서 에폭시 수지 조성물의 혼련물을 얻었다. 또한, 그 평가를 행하였다.As shown in Table 1, a kneaded product of the epoxy resin composition was obtained in the same manner as in Example 1, using only the silicon dioxide powder. The evaluation was also performed.
[비교예 2][Comparative Example 2]
표 1에 표시된 바와 같이, 산화마그네슘 분말 1 대신에, 표면이 3-글라이시독시프로필 트라이메톡시실란으로 처리된 산화마그네슘 분말 3을 사용하여, 실시예 1과 마찬가지로 해서 에폭시 수지 조성물의 혼련물을 얻었다. 또한, 그 평가를 행하였다.As shown in Table 1, the magnesium oxide powder 3 whose surface was treated with 3-glycidoxypropyltrimethoxysilane was used instead of the magnesium oxide powder 1, and a kneaded product of the epoxy resin composition was obtained in the same manner as in Example 1 . The evaluation was also performed.
[비교예 3][Comparative Example 3]
표 1에 표시된 바와 같이, 산화마그네슘 분말 1 대신에, 표면이 비닐트라이메톡시실란으로 처리된 산화마그네슘 분말 4를 사용하여, 실시예 1과 마찬가지로 해서 에폭시 수지 조성물의 혼련물을 얻었다. 또한, 그 평가를 행하였다.As shown in Table 1, a kneaded product of an epoxy resin composition was obtained in the same manner as in Example 1, except that magnesium oxide powder 4 whose surface was treated with vinyltrimethoxysilane was used instead of magnesium oxide powder 1. The evaluation was also performed.
[비교예 4][Comparative Example 4]
표 1에 표시된 바와 같이, 산화마그네슘 분말 1 대신에, 표면이 처리되어 있지 않은 산화마그네슘 분말 5를 사용하여, 실시예 1과 마찬가지로 해서 에폭시 수지 조성물의 혼련물을 얻고자 시도하였지만, 얻는 것이 가능하지 않았다.As shown in Table 1, attempts were made to obtain a kneaded product of an epoxy resin composition in the same manner as in Example 1, except that magnesium oxide powder 5 whose surface had not been treated was used instead of magnesium oxide powder 1, I did.
[참고예 1][Referential Example 1]
표 1에 표시된 바와 같이, 산화마그네슘 분말 1 대신에, 표면이 비닐트라이메톡시실란으로 처리된 산화마그네슘 분말 4를 사용하여, 실시예 2와 마찬가지로 해서 에폭시 수지 조성물의 혼련물을 얻었다. 또한, 그 평가를 행하였다.As shown in Table 1, a kneaded product of an epoxy resin composition was obtained in the same manner as in Example 2, except that magnesium oxide powder 4 whose surface was treated with vinyltrimethoxysilane was used instead of magnesium oxide powder 1. The evaluation was also performed.
[참고예 2][Reference Example 2]
표 1에 표시된 바와 같이, 산화마그네슘 분말 1 대신에, 표면이 처리되어 있지 않은 산화마그네슘 분말 5를 사용하여, 실시예 2와 마찬가지로 해서 에폭시 수지 조성물의 혼련물을 얻었다. 또한, 그 평가를 행하였다.As shown in Table 1, a kneaded product of an epoxy resin composition was obtained in the same manner as in Example 2, except that magnesium oxide powder 5 whose surface had not been treated was used in place of magnesium oxide powder 1. The evaluation was also performed.
표 1에 실시예 및 비교예의 조성이나 평가 결과 등을 나타내었다.Table 1 shows compositions and evaluation results of the examples and comparative examples.
조
성
(
질
량
부
)
article
castle
(
quality
Amount
part
)
평
가
결
과
Flat
end
texture
and
연소all
Combustion
연소all
Combustion
표 2에 표시된 바와 같이, 산화마그네슘 분말 1을 이용한 실시예 1은, 산화마그네슘 분말 3 내지 5를 이용한 비교예 2 내지 4와 비교해서 혼련성이 개선되고, 특히 유동성이 개선되어 성형성이 우수한 에폭시 수지 조성물이 얻어지는 것을 알 수 있다.As shown in Table 2, in Example 1 using magnesium oxide powder 1, the kneadability was improved as compared with Comparative Examples 2 to 4 using magnesium oxide powders 3 to 5, and in particular, the flowability was improved, A resin composition can be obtained.
표 3에 표시된 바와 같이, 산화마그네슘 분말 1, 2를 이용한 실시예 2, 3은, 산화마그네슘 분말 4, 5를 이용한 참고예 1, 2와 비교해서 혼련성이 개선되고, 또한 유동성이 개선되어 성형성이 우수한 에폭시 수지 조성물이 얻어지는 것을 알 수 있다. 이 효과는, 경화제 3에 있어서도 유효하다는 것을 실시예 4로부터 알 수 있다.As shown in Table 3, in Examples 2 and 3 using magnesium oxide powders 1 and 2, the kneadability was improved and fluidity was improved as compared with Reference Examples 1 and 2 using magnesium oxide powders 4 and 5, An epoxy resin composition having excellent properties can be obtained. It can be seen from Example 4 that this effect is also effective for the curing agent 3.
표 4에 표시된 바와 같이, 실시예 1 내지 4에 있어서, 산화마그네슘을 이용하지 않은 비교예 1보다 열전도율이 개선되어 있는 것을 알 수 있다. 난연성에 대해서는, 경화제 1을 이용한 실시예 1과 비교예 1로부터 알 수 있는 바와 같이, 산화마그네슘 분말을 이용함으로써 난연성이 저하한다. 그렇지만, 경화제 2, 3을 이용함으로써 난연성이 개량되어서 V-0을 달성할 수 있는 것을 알 수 있다.As shown in Table 4, it can be seen that the thermal conductivity is improved in Examples 1 to 4 as compared with Comparative Example 1 in which magnesium oxide is not used. With respect to flame retardancy, as can be seen from Example 1 and Comparative Example 1 using the curing agent 1, the flame retardancy is lowered by using the magnesium oxide powder. However, by using the curing agents 2 and 3, the flame retardancy is improved and V-0 can be attained.
본 발명에 의해, 혼련에 의해 용이하게 조제하는 것이 가능하며, 특히 유동성이 개량되어서 성형성이 우수하고, 흡수성이 양호(저흡수성)한, 산화마그네슘 분말을 함유한 열전도성의 에폭시 수지 조성물을 제공할 수 있다. 또한, 본 발명에 의해, 바람직하게는 더욱 내연소성이 우수한 산화마그네슘 분말을 함유한 열전도성의 에폭시 수지 조성물을 제공할 수 있다. 본 발명의 에폭시 수지 조성물은, 열전도성 밀봉재료, 열전도성 시트, 열전도성 접착제 및 경화물으로서 적합하게 사용할 수 있다.According to the present invention, there is provided a thermally conductive epoxy resin composition containing magnesium oxide powder which can be easily prepared by kneading, has excellent fluidity and is excellent in moldability and water absorbability (low water absorption) . Further, according to the present invention, it is possible to provide a thermally conductive epoxy resin composition containing magnesium oxide powder which is more excellent in resistance to burning. The epoxy resin composition of the present invention can be suitably used as a thermally conductive sealing material, a thermally conductive sheet, a thermally conductive adhesive, and a cured product.
Claims (10)
[화학식 1]
상기 화학식 1에 있어서, l은 1 내지 3의 정수이고, R은 각각 동일 또는 상이해도 되는 알킬기이며, R'는 각각 동일 또는 상이해도 되는 페닐기 및 아미노기 중 적어도 한쪽을 함유하는 1가의 기이다.The epoxy resin composition according to claim 1, wherein the alkoxysilane is a compound represented by the following formula (1): < EMI ID =
[Chemical Formula 1]
In Formula 1, 1 is an integer of 1 to 3, R is an alkyl group which may be the same or different, and R 'is a monovalent group containing at least one of a phenyl group and an amino group which may be the same or different.
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| CN106047249A (en) * | 2016-06-08 | 2016-10-26 | 蚌埠高华电子股份有限公司 | Composite nano-magnesia filling modified composite epoxy pouring sealant for LED displays |
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| JP2004027177A (en) | 2001-12-25 | 2004-01-29 | Tateho Chem Ind Co Ltd | Resin composition containing magnesium oxide powder |
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| JP3836649B2 (en) * | 1999-11-22 | 2006-10-25 | 協和化学工業株式会社 | Semiconductor sealing resin composition and molded product thereof |
| JP2001158853A (en) * | 1999-12-02 | 2001-06-12 | Shin Kobe Electric Mach Co Ltd | Epoxy resin composition and prepreg and printed wiring board using the same |
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| US20090152491A1 (en) * | 2007-11-16 | 2009-06-18 | E. I. Du Pont De Nemours And Company | Thermally conductive resin compositions |
| JP5602650B2 (en) * | 2011-01-25 | 2014-10-08 | 宇部マテリアルズ株式会社 | Magnesium oxide powder |
| EP2966106A4 (en) * | 2013-03-06 | 2016-11-09 | Dainippon Ink & Chemicals | Epoxy resin composition, cured product, heat radiating material, and electronic member |
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| JP2012162650A (en) | 2011-02-07 | 2012-08-30 | Meiwa Kasei Kk | Thermoconductive resin composition, and semiconductor package |
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