JP6402860B2 - 特定の末端構造を有する重合体を含む熱硬化性樹脂組成物 - Google Patents
特定の末端構造を有する重合体を含む熱硬化性樹脂組成物 Download PDFInfo
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- JP6402860B2 JP6402860B2 JP2015522734A JP2015522734A JP6402860B2 JP 6402860 B2 JP6402860 B2 JP 6402860B2 JP 2015522734 A JP2015522734 A JP 2015522734A JP 2015522734 A JP2015522734 A JP 2015522734A JP 6402860 B2 JP6402860 B2 JP 6402860B2
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- PMHQVHHXPFUNSP-UHFFFAOYSA-M copper(1+);methylsulfanylmethane;bromide Chemical compound Br[Cu].CSC PMHQVHHXPFUNSP-UHFFFAOYSA-M 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000000593 degrading effect Effects 0.000 description 1
- JBSLOWBPDRZSMB-FPLPWBNLSA-N dibutyl (z)-but-2-enedioate Chemical compound CCCCOC(=O)\C=C/C(=O)OCCCC JBSLOWBPDRZSMB-FPLPWBNLSA-N 0.000 description 1
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 description 1
- FBSAITBEAPNWJG-UHFFFAOYSA-N dimethyl phthalate Natural products CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 description 1
- 229960001826 dimethylphthalate Drugs 0.000 description 1
- PQJYOOFQDXGDDS-ZCXUNETKSA-N dinonyl (z)-but-2-enedioate Chemical compound CCCCCCCCCOC(=O)\C=C/C(=O)OCCCCCCCCC PQJYOOFQDXGDDS-ZCXUNETKSA-N 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- ODQWQRRAPPTVAG-GZTJUZNOSA-N doxepin Chemical compound C1OC2=CC=CC=C2C(=C/CCN(C)C)/C2=CC=CC=C21 ODQWQRRAPPTVAG-GZTJUZNOSA-N 0.000 description 1
- QYDYPVFESGNLHU-UHFFFAOYSA-N elaidic acid methyl ester Natural products CCCCCCCCC=CCCCCCCCC(=O)OC QYDYPVFESGNLHU-UHFFFAOYSA-N 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000006735 epoxidation reaction Methods 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- AZDCYKCDXXPQIK-UHFFFAOYSA-N ethenoxymethylbenzene Chemical compound C=COCC1=CC=CC=C1 AZDCYKCDXXPQIK-UHFFFAOYSA-N 0.000 description 1
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 1
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
- UHKJHMOIRYZSTH-UHFFFAOYSA-N ethyl 2-ethoxypropanoate Chemical compound CCOC(C)C(=O)OCC UHKJHMOIRYZSTH-UHFFFAOYSA-N 0.000 description 1
- 229940116333 ethyl lactate Drugs 0.000 description 1
- 229940117360 ethyl pyruvate Drugs 0.000 description 1
- 230000006355 external stress Effects 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 229940075529 glyceryl stearate Drugs 0.000 description 1
- VPVSTMAPERLKKM-UHFFFAOYSA-N glycoluril Chemical compound N1C(=O)NC2NC(=O)NC21 VPVSTMAPERLKKM-UHFFFAOYSA-N 0.000 description 1
- 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 1
- VBZWSGALLODQNC-UHFFFAOYSA-N hexafluoroacetone Chemical compound FC(F)(F)C(=O)C(F)(F)F VBZWSGALLODQNC-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229940018564 m-phenylenediamine Drugs 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- BDJSOPWXYLFTNW-UHFFFAOYSA-N methyl 3-methoxypropanoate Chemical compound COCCC(=O)OC BDJSOPWXYLFTNW-UHFFFAOYSA-N 0.000 description 1
- 229940057867 methyl lactate Drugs 0.000 description 1
- QYDYPVFESGNLHU-KHPPLWFESA-N methyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC QYDYPVFESGNLHU-KHPPLWFESA-N 0.000 description 1
- 229940073769 methyl oleate Drugs 0.000 description 1
- CWKLZLBVOJRSOM-UHFFFAOYSA-N methyl pyruvate Chemical compound COC(=O)C(C)=O CWKLZLBVOJRSOM-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- JESXATFQYMPTNL-UHFFFAOYSA-N mono-hydroxyphenyl-ethylene Natural products OC1=CC=CC=C1C=C JESXATFQYMPTNL-UHFFFAOYSA-N 0.000 description 1
- KBJFYLLAMSZSOG-UHFFFAOYSA-N n-(3-trimethoxysilylpropyl)aniline Chemical compound CO[Si](OC)(OC)CCCNC1=CC=CC=C1 KBJFYLLAMSZSOG-UHFFFAOYSA-N 0.000 description 1
- WIBFFTLQMKKBLZ-SEYXRHQNSA-N n-butyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCCCC WIBFFTLQMKKBLZ-SEYXRHQNSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 150000002829 nitrogen Chemical group 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- GSGDTSDELPUTKU-UHFFFAOYSA-N nonoxybenzene Chemical compound CCCCCCCCCOC1=CC=CC=C1 GSGDTSDELPUTKU-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical class CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 229920002114 octoxynol-9 Polymers 0.000 description 1
- 150000002888 oleic acid derivatives Chemical class 0.000 description 1
- 125000005375 organosiloxane group Chemical group 0.000 description 1
- GIPDEPRRXIBGNF-KTKRTIGZSA-N oxolan-2-ylmethyl (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC1CCCO1 GIPDEPRRXIBGNF-KTKRTIGZSA-N 0.000 description 1
- QUBQYFYWUJJAAK-UHFFFAOYSA-N oxymethurea Chemical compound OCNC(=O)NCO QUBQYFYWUJJAAK-UHFFFAOYSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 229960004624 perflexane Drugs 0.000 description 1
- ZJIJAJXFLBMLCK-UHFFFAOYSA-N perfluorohexane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F ZJIJAJXFLBMLCK-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- WRAQQYDMVSCOTE-UHFFFAOYSA-N phenyl prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC=C1 WRAQQYDMVSCOTE-UHFFFAOYSA-N 0.000 description 1
- IGALFTFNPPBUDN-UHFFFAOYSA-N phenyl-[2,3,4,5-tetrakis(oxiran-2-ylmethyl)phenyl]methanediamine Chemical compound C=1C(CC2OC2)=C(CC2OC2)C(CC2OC2)=C(CC2OC2)C=1C(N)(N)C1=CC=CC=C1 IGALFTFNPPBUDN-UHFFFAOYSA-N 0.000 description 1
- 150000003021 phthalic acid derivatives Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920002454 poly(glycidyl methacrylate) polymer Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920000259 polyoxyethylene lauryl ether Polymers 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 239000001818 polyoxyethylene sorbitan monostearate Substances 0.000 description 1
- 235000010989 polyoxyethylene sorbitan monostearate Nutrition 0.000 description 1
- 239000001816 polyoxyethylene sorbitan tristearate Substances 0.000 description 1
- 235000010988 polyoxyethylene sorbitan tristearate Nutrition 0.000 description 1
- 229920001289 polyvinyl ether Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
- ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 229940100515 sorbitan Drugs 0.000 description 1
- 229940035044 sorbitan monolaurate Drugs 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 239000001570 sorbitan monopalmitate Substances 0.000 description 1
- 235000011071 sorbitan monopalmitate Nutrition 0.000 description 1
- 229940031953 sorbitan monopalmitate Drugs 0.000 description 1
- 239000001587 sorbitan monostearate Substances 0.000 description 1
- 235000011076 sorbitan monostearate Nutrition 0.000 description 1
- 229940035048 sorbitan monostearate Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 229940072958 tetrahydrofurfuryl oleate Drugs 0.000 description 1
- 230000000930 thermomechanical effect Effects 0.000 description 1
- CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 description 1
- UDUKMRHNZZLJRB-UHFFFAOYSA-N triethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OCC)(OCC)OCC)CCC2OC21 UDUKMRHNZZLJRB-UHFFFAOYSA-N 0.000 description 1
- SQAZDQFHAOTWGX-UHFFFAOYSA-N triethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)propyl]silane Chemical compound C1C(C(C)C[Si](OCC)(OCC)OCC)CCC2OC21 SQAZDQFHAOTWGX-UHFFFAOYSA-N 0.000 description 1
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- LQZHZFUSFHLGHE-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)propyl]silane Chemical compound C1C(C(C)C[Si](OC)(OC)OC)CCC2OC21 LQZHZFUSFHLGHE-UHFFFAOYSA-N 0.000 description 1
- LTOKKZDSYQQAHL-UHFFFAOYSA-N trimethoxy-[4-(oxiran-2-yl)butyl]silane Chemical compound CO[Si](OC)(OC)CCCCC1CO1 LTOKKZDSYQQAHL-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
Classifications
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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
- C08G14/00—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00
- C08G14/02—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes
- C08G14/04—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes with phenols
- C08G14/06—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes with phenols and monomers containing hydrogen attached to nitrogen
-
- 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
-
- 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
- C08G14/00—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00
- C08G14/02—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes
- C08G14/04—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes with phenols
- C08G14/12—Chemically modified polycondensates
-
- 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
- C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
- C08K3/013—Fillers, pigments or reinforcing additives
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
- C08L61/34—Condensation polymers of aldehydes or ketones with monomers covered by at least two of the groups C08L61/04, C08L61/18 and C08L61/20
-
- 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
- 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
- C09J161/00—Adhesives based on condensation polymers of aldehydes or ketones; Adhesives based on derivatives of such polymers
- C09J161/34—Condensation polymers of aldehydes or ketones with monomers covered by at least two of the groups C09J161/04, C09J161/18 and C09J161/20
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- 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
- C09J179/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen, with or without oxygen, or carbon only, not provided for in groups C09J161/00 - C09J177/00
- C09J179/02—Polyamines
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
- H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
- H01L23/293—Organic, e.g. plastic
- H01L23/295—Organic, e.g. plastic containing a filler
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
- H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
- H01L23/293—Organic, e.g. plastic
- H01L23/296—Organo-silicon compounds
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
- H01L23/31—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the arrangement or shape
- H01L23/3107—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the arrangement or shape the device being completely enclosed
- H01L23/3142—Sealing arrangements between parts, e.g. adhesion promotors
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
- H01L2924/0001—Technical content checked by a classifier
- H01L2924/0002—Not covered by any one of groups H01L24/00, H01L24/00 and H01L2224/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Physics & Mathematics (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Computer Hardware Design (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Power Engineering (AREA)
- General Chemical & Material Sciences (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Epoxy Resins (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Phenolic Resins Or Amino Resins (AREA)
- Wire Bonding (AREA)
Description
また、特許文献4に記載されているWOW(ウェハーオンウェハー)構造では、ウェハーとウェハーをボイドが全く発生することなく接着する必要があるため、ボイドの原因となる低分子成分や耐熱性が低く分解する成分の適用は困難であった。
さらに、公知の技術として、ベンゾオキサジン樹脂にエポキシ樹脂を混合し、架橋密度を向上させることが知られている。しかし、上記の混合樹脂は架橋反応が遅く、十分な架橋密度が得られない。そのため、イミダゾール系の化合物に代表される、エポキシ樹脂硬化剤を添加することが広く知られているが、エポキシ樹脂硬化剤は耐熱性が低いため、ボイドの発生に起因する信頼性の低下が懸念される。
で表される繰り返し構造単位及び下記式(1−b):
で表される末端構造を有する重合体を含む熱硬化性樹脂組成物である。
で表される。
で表される2価の有機基を表す。
本明細書においてビスフェノール化合物とは、1分子に2つのヒドロキシフェニル基を有する化合物であり、例えば、2,2−ビス(4−ヒドロキシフェニル)プロパン〔ビスフェノールA〕、ビス(4−ヒドロキシフェニル)スルホン〔ビスフェノールS〕、2,2−ビス(4−ヒドロキシフェニル)ヘキサフルオロプロパン〔ビスフェノールAF〕、ビス(4−ヒドロキシフェニル)メタン〔ビスフェノールF〕、1,1−ビス(4−ヒドロキシフェニル)エタン〔ビスフェノールE〕、1,3−ビス[2−(4−ヒドロキシフェニル)−2−プロピル]ベンゼン〔ビスフェノールM〕、1,4−ビス[2−(4−ヒドロキシフェニル)−2−プロピル]ベンゼン〔ビスフェノールP〕、2,2’−ビス(4−ヒドロキシ−3−メチルフェニル)プロパン、フェノールフタレイン、4,4’−ビフェノール、1,1−ビス(4−ヒドロキシフェニル)シクロヘキサン、1,1−ビス(4−ヒドロキシ−3−メチルフェニル)シクロヘキサン、9,9−ビス(4−ヒドロキシフェニル)フルオレン、9,9−ビス(4−ヒドロキシ−3−メチルフェニル)フルオレン、1,1−ビス(3−シクロヘキシル−4−ヒドロキシフェニル)シクロヘキサン、2,2−ビス(3−シクロヘキシル−4−ヒドロキシフェニル)プロパン、及び2,2−ビス(2−ヒドロキシ−5−ビフェニルイル)プロパンを挙げることができる。
ジアミン化合物としては、例えば、4,4’−ジアミノ−3,3’−ジメチルジフェニルメタン、4,4’−ジアミノ−3,3’−ジエチルジフェニルメタン、4,4’−ジアミノ−3,3’,5,5’−テトラメチルジフェニルメタン、o−ジアニシジン、o−フェニレンジアミン、m−フェニレンジアミン、p−フェニレンジアミン、ビス[4−(3−アミノフェノキシ)フェニル]スルホン、3,3’−スルホニルジアニリン、及び4,4’−スルホニルジアニリンを挙げることができる。
アルデヒド化合物としては、例えば、パラホルムアルデヒド及びホルムアルデヒドを挙げることができる。
上記化合物を溶解させる溶媒としては、例えば、トルエン、キシレン、ジオキサン、テトラヒドロフラン、クロロホルム、ジクロロメタン、シクロヘキサノン、シクロペンタノン、メチルエチルケトン、及びN−メチル−2−ピロリドンを挙げることができる。
1分子に1つのアミノ基又はヒドロキシフェニル基を有するイミダゾール化合物としては、例えば、1−(3−アミノプロピル)イミダゾール、4−(2−メチル−1−イミダゾリル)フェニルアミン、4−(1−イミダゾリル)アニリン、3−クロロ−4−(1−イミダゾリル)アニリン、及びp−(1−イミダゾリル)フェノールを挙げることができる。
装置:一体型高速GPCシステム HLC−8220GPC 東ソー(株)製
カラム:KF−G,KF−804L
カラム温度:40℃
溶媒:テトラヒドロフラン(THF)
流量:1.0mL/分
標準試料:ポリスチレン
ディテクター:RI
4,4’−ジアミノ−3,3’−ジエチルジフェニルメタン(日本化薬(株)製、KAYAHARD A−A)45.79g、ビスフェノールM(三井化学ファイン(株)製)69.29g、パラホルムアルデヒド(東京化成工業(株)製)22.81g及びトリエチルアミン4.05gをN−メチル−2−ピロリドン331.18gに溶解させた後、窒素置換し90℃で20時間反応させポリマーを含む溶液を得た。その後、室温まで冷却し、得られた溶液に、1−(3−アミノプロピル)イミダゾール(東京化成工業(株)製)6.26g、パラホルムアルデヒド(東京化成工業(株)製)6.34g、トリエチルアミン0.40g及び、N−メチル−2−ピロリドン30.33gを加えた後、窒素置換し90℃で8時間反応させた。更に得られた溶液をメタノールに滴下し、再沈殿させた。その後、ブフナーロートで吸引ろ過し、メタノールにて2回洗浄し、得られた粉体を減圧乾燥機で12時間乾燥させ重合体を得た。得られた重合体のGPC分析を行ったところ、標準ポリスチレン換算にて重量平均分子量は4,000であった。なお、得られた重合体は、下記式(6−a)で表される繰り返し構造単位及び下記式(6−b)で表される末端構造を有し、当該重合体の末端が下記式(6−b)で表される末端構造である割合は、原料化合物であるビスフェノールMのモル数に対して、20mol%であると推定される。
1,3−フェニレンジアミン(東京化成工業(株)製)1.95g、4,4’−ジアミノ−3,3’−ジエチルジフェニルメタン(日本化薬(株)製、KAYAHARD A−A)41.20g、ビスフェノールM(三井化学ファイン(株)製)69.30g、パラホルムアルデヒド(東京化成工業(株)製)22.87g及びトリエチルアミン4.05gをN−メチル−2−ピロリドン320.48gに溶解させた後、窒素置換し90℃で20時間反応させポリマーを含む溶液を得た。その後、得られた溶液をメタノールに滴下し、再沈殿させた。その後、ブフナーロートで吸引ろ過し、メタノールにて2回洗浄し、得られた粉体を減圧乾燥機で12時間乾燥させ重合体を得た。得られた重合体のGPC分析を行ったところ、標準ポリスチレン換算にて重量平均分子量は9,900であった。なお、得られた重合体は、下記式(6−a)で表される繰り返し構造単位及び下記式(7)で表される繰り返し構造単位、並びに下記式(8)で表される末端を有すると推定され、上記式(6−b)で表されるようなイミダゾール環を含む末端構造を有さない。
エポキシ樹脂硬化剤である1−シアノエチル−2−ウンデシルイミダゾール(東京化成工業(株)製)を用意した。
エポキシ樹脂硬化剤である2−エチル−4−メチルイミダゾール(東京化成工業(株)製)を用意した。
エポキシ樹脂硬化剤である4−メチル−2−フェニルイミダゾール(東京化成工業(株)製)を用意した。
合成例1で得られた重合体、並びに比較例1乃至比較例3で用意されたイミダゾール系のエポキシ樹脂硬化剤の耐熱性について、TG−DTA(NETZSCH社製、TG/DTA2010SR)にて、試料を10℃/分で昇温し5質量%の重量減少を生ずる温度(以下、本明細書では5質量%重量減温度と略称する。)を測定した結果から評価した。5質量%重量減温度の測定結果を下記表1に示す。
<実施例1>
合成例1で得られた重合体10gをテトラヒドロフラン40gに溶解させ、その後、孔径0.2μmのポリテトラフルオロエチレン(以下、本明細書ではPTFEと略称する。)製ミクロフィルターを用いてろ過し、固形分を20質量%含有する組成物を調製した。
合成例1で得られた重合体5gとエポキシ樹脂であるエポリードGT401(株式会社ダイセル製)5gをテトラヒドロフラン40gに溶解させ、その後、孔径0.2μmのPTFE製ミクロフィルターを用いてろ過し、固形分を20質量%含有する組成物を調製した。
合成例1で得られた重合体50gをシクロペンタノン50gに溶解させ、その後、孔径5.0μmのPTFE製ミクロフィルターを用いてろ過し、固形分を50質量%含有する組成物を調製した。
合成例1で得られた重合体25gとエポキシ樹脂であるエポリードGT401(株式会社ダイセル製)25gをシクロペンタノン50gに溶解させ、その後、孔径5.0μmのPTFE製ミクロフィルターを用いてろ過し、固形分を50質量%含有する組成物を調製した。
合成例1で得られた重合体3g、フェノールノボラック樹脂であるKAYAHARD GPH−65(日本化薬(株)製)2g、エポキシ樹脂であるエポリードGT401(株式会社ダイセル製)5g及び3−フェニルアミノプロピルトリメトキシシラン(東京化成工業(株)製)2gをテトラヒドロフラン65.5gに溶解させ、その後、無機フィラーであるオルガノシリカゾル[3−メタクリロキシプロピルトリメトキシシランで表面処理したシリカのメチルエチルケトン分散液、前記シリカの一次粒子径40nm乃至50nm、固形分30.8質量%、比重(20℃)1.007、粘度(20℃)2.5mPa・s、水分0.08質量%]32.5gを混和させ、固形分を20質量%含有する組成物を調製した。
合成例1で得られた重合体3g、フェノールノボラック樹脂であるKAYAHARD GPH−65(日本化薬(株)製)2g、エポキシ樹脂であるエポリードGT401(株式会社ダイセル製)5g、3−フェニルアミノプロピルトリメトキシシラン(東京化成工業(株)製)2gをシクロペンタノン22gに溶解させ、その後、無機フィラーであるオルガノシリカゾル[3−メタクリロキシプロピルトリメトキシシランで表面処理したシリカのメチルエチルケトン分散液、前記シリカの一次粒子径40nm乃至50nm、固形分30.8質量%、比重(20℃)1.007、粘度(20℃)2.5mPa・s、水分0.08質量%]32.5gを混和させた。その後エバポレーターを用いて濃縮を行い、固形分を50質量%含有する組成物を調製した。
合成例2で得られた重合体5gとエポキシ樹脂であるエポリードGT401(株式会社ダイセル製)5gをテトラヒドロフラン40gに溶解させ、その後、孔径0.2μmのPTFE製ミクロフィルターを用いてろ過し、固形分を20質量%含有する組成物を調製した。
合成例2で得られた重合体25gとエポキシ樹脂であるエポリードGT401(株式会社ダイセル製)25gをシクロペンタノン50gに溶解させ、その後、孔径5.0μmのPTFE製ミクロフィルターを用いてろ過し、固形分を50質量%含有する組成物を調製した。
合成例2で得られた重合体25g、比較例1の1−シアノエチル−2−ウンデシルイミダゾール0.5g及びエポキシ樹脂であるエポリードGT401(株式会社ダイセル製)25.5gをシクロペンタノン51.0gに溶解させ、その後、孔径5.0μmのPTFE製ミクロフィルターを用いてろ過し、固形分を50質量%含有する組成物を調製した。
実施例1、実施例2及び実施例5で調製した組成物1g並びに比較例4で調製した組成物1gを直径40mmの金属製カップにいれ、50℃で60分間ベーク後、65℃で60分間ベークし、更に80℃で30分間ベークしてテトラヒドロフランを蒸発させ、熱硬化性の樹脂膜を形成した。その後、前記樹脂膜の硬化温度を、レオメーター(アントンパール社製、MCR102)を用いて5℃/分で昇温して評価し、硬化温度が190℃未満なら○、190℃以上なら×と判断した。なお、ここで示す硬化温度とは、樹脂膜の硬化反応によって複素粘度が10,000Pa・sとなる温度である。その硬化温度の結果を下記表2に示す。
実施例3、実施例4及び実施例6で調製した組成物及び比較例6で調製した組成物を、4インチのシリコンウェハー上に、ベーク後の厚みが15μm乃至25μmとなるよう100℃で5分間ベーク後、130℃で5分間ベークしてシクロペンタノンを蒸発させ、熱硬化性の樹脂膜を形成した。その後、貼り合せ装置(アユミ工業(株)製、VJ−300)を使用して、真空度10Pa以下、温度140℃、印加荷重300kgの条件下で、前記樹脂膜を形成したシリコンウェハーを他の4インチガラスウェハーと接着させ、その後、180℃で60分間加熱して樹脂を硬化させた。ボイド無く良好に接着できた場合を○、ボイドが存在し接着不良が見られた場合を×と評価した。その結果を下記表3に示す。
上記接着性の評価で良好に接着できたサンプルについて、200℃で5分間の加熱後、250℃のホットプレートに載せ、剥離発生の有無を確認した。前記ホットプレートにそのサンプルを載せてから1時間以上経過しても剥離が発生しない場合を○、1時間未満にて剥離が発生する場合を×と評価した。その結果を下記表3に示す。
実施例4及び実施例6で調製した組成物並びに比較例5及び比較例6で調製した組成物を、アルミ箔をラミネートしたシリコンウェハー上に、ベーク後の厚みが15μm乃至25μmとなるようスピンコートし、100℃で5分間ベーク後、130℃で5分間ベークしてシクロペンタノンを蒸発させ、アルミ箔に積層された熱硬化性の樹脂膜を得た。その後、窒素雰囲気中でさらに180℃で60分間ベークして樹脂膜を硬化させた後、6mol/Lの塩酸水溶液に投入してアルミ箔を溶解させ、硬化膜を得た。得られた硬化膜を幅5mmにカットし、Tgと、Tg前温度及びTg後温度の線膨張係数(CTE)を、熱機械分析(TMA)装置(NETZSCH社製、TMA4000SA)で5℃/分で室温から200℃まで昇温したときの硬化膜の伸びを測定することにより評価した。Tgは140℃以上を○、140℃未満を×と判断し、Tg前温度のCTEは70ppm/℃未満を○、70ppm/℃以上を×と判断し、Tg後温度のCTEは1000ppm/℃未満を○、1000ppm/℃以上を×と判断した。ここでいうTgは、硬化膜の伸び量の変曲する温度である。測定結果を下記表4に示す。
実施例3、実施例4及び実施例6で調製した組成物に、シクロペンタノンを加えて希釈し、シリコンウェハー上にスピンコーターを用いて塗布し、ホットプレート上において100℃で2分間ベーク後、130℃で2分間ベークを行い、さらに、窒素置換されたオーブン中で、180℃で60分間ベークを行い、膜厚500nmの硬化膜を形成した。作製したサンプルに対し、CVmap 92B (Four Dimensions社製)にて1MV/cmの電界強度を印加したときのリーク電流密度、及び誘電率を測定した。その結果を下記表5に示す。
Claims (14)
- 前記式(1)においてQは炭素原子数1乃至5のアルキレン基を表す、請求項1に記載の熱硬化性樹脂組成物。
- 前記式(1)においてXは、水素原子の少なくとも1つがハロゲン原子で置換されていてもよい炭素原子数1乃至6のアルキレン基、環状アルキレン基、水素原子の少なくとも
1つがハロゲン原子で置換されていてもよいアリーレン基、スルホニル基、カルボニル基、−O−基又は−COO−基を含む2価の有機基を表す、請求項1又は請求項2のいずれか一項に記載の熱硬化性樹脂組成物。 - 前記重合体の重量平均分子量は1,000乃至100,000である請求項1乃至請求項7のいずれか一項に記載の熱硬化性樹脂組成物。
- エポキシ樹脂をさらに含む請求項1乃至請求項8のいずれか一項に記載の熱硬化性樹脂組成物。
- フェノール樹脂をさらに含む請求項1乃至請求項9のいずれか一項に記載の熱硬化性樹脂組成物。
- 溶剤をさらに含む請求項1乃至請求項10のいずれか一項に記載の熱硬化性樹脂組成物。
- シランカップリング剤をさらに含む請求項1乃至請求項11のいずれか一項に記載の熱硬化性樹脂組成物。
- 無機フィラーをさらに含む請求項1乃至請求項12のいずれか一項に記載の熱硬化性樹脂組成物。
- 接着剤組成物又はアンダーフィル組成物である請求項1乃至請求項13のいずれか一項に記載の熱硬化性樹脂組成物。
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2014
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KR101981788B1 (ko) | 2019-05-27 |
CN105324402B (zh) | 2018-01-09 |
SG11201510498WA (en) | 2016-01-28 |
TWI636095B (zh) | 2018-09-21 |
JPWO2014203735A1 (ja) | 2017-02-23 |
WO2014203735A1 (ja) | 2014-12-24 |
US9657128B2 (en) | 2017-05-23 |
TW201510077A (zh) | 2015-03-16 |
US20160152759A1 (en) | 2016-06-02 |
KR20160023672A (ko) | 2016-03-03 |
CN105324402A (zh) | 2016-02-10 |
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