JPWO2021039111A1 - 樹脂組成物及びそれを用いた半導体封止材料、含侵基材、回路基板、ビルドアップフィルム、プリプレグ、炭素繊維複合材料、ソルダーレジスト、ドライフィルム、プリント配線板 - Google Patents
樹脂組成物及びそれを用いた半導体封止材料、含侵基材、回路基板、ビルドアップフィルム、プリプレグ、炭素繊維複合材料、ソルダーレジスト、ドライフィルム、プリント配線板 Download PDFInfo
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- JPWO2021039111A1 JPWO2021039111A1 JP2021521542A JP2021521542A JPWO2021039111A1 JP WO2021039111 A1 JPWO2021039111 A1 JP WO2021039111A1 JP 2021521542 A JP2021521542 A JP 2021521542A JP 2021521542 A JP2021521542 A JP 2021521542A JP WO2021039111 A1 JPWO2021039111 A1 JP WO2021039111A1
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- 239000011342 resin composition Substances 0.000 title claims abstract description 62
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 title claims description 33
- 239000000463 material Substances 0.000 title claims description 21
- 229910000679 solder Inorganic materials 0.000 title claims description 10
- 229920000049 Carbon (fiber) Polymers 0.000 title claims description 8
- 239000004917 carbon fiber Substances 0.000 title claims description 8
- 239000004065 semiconductor Substances 0.000 title claims description 7
- 239000002131 composite material Substances 0.000 title claims description 5
- 238000005538 encapsulation Methods 0.000 title description 2
- 229920005989 resin Polymers 0.000 claims abstract description 204
- 239000011347 resin Substances 0.000 claims abstract description 204
- -1 polysiloxane unit Polymers 0.000 claims abstract description 107
- 229920000642 polymer Polymers 0.000 claims abstract description 104
- 239000000203 mixture Substances 0.000 claims abstract description 67
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims abstract description 22
- 239000011889 copper foil Substances 0.000 claims abstract description 21
- 150000001993 dienes Chemical class 0.000 claims abstract description 12
- 239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 8
- 229920000570 polyether Polymers 0.000 claims abstract description 7
- 229920001187 thermosetting polymer Polymers 0.000 claims description 45
- 239000003795 chemical substances by application Substances 0.000 claims description 30
- 230000009477 glass transition Effects 0.000 claims description 19
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- 230000003014 reinforcing effect Effects 0.000 claims 1
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- 229920000647 polyepoxide Polymers 0.000 abstract description 155
- 238000010586 diagram Methods 0.000 abstract 1
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 67
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- 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 42
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 38
- 239000004643 cyanate ester Substances 0.000 description 34
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 33
- 239000002904 solvent Substances 0.000 description 30
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 29
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 28
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 21
- 239000003063 flame retardant Substances 0.000 description 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 19
- 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 18
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 18
- 150000004678 hydrides Chemical class 0.000 description 18
- 239000010410 layer Substances 0.000 description 18
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 17
- 239000005011 phenolic resin Substances 0.000 description 16
- 150000008064 anhydrides Chemical class 0.000 description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 15
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 14
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 14
- 125000003118 aryl group Chemical group 0.000 description 14
- 230000000052 comparative effect Effects 0.000 description 14
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- 239000005056 polyisocyanate Substances 0.000 description 14
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- 229910052751 metal Inorganic materials 0.000 description 13
- 239000002184 metal Substances 0.000 description 13
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 238000000034 method Methods 0.000 description 12
- 229920005862 polyol Polymers 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 11
- 125000002723 alicyclic group Chemical group 0.000 description 11
- 239000011248 coating agent Substances 0.000 description 11
- 238000000576 coating method Methods 0.000 description 11
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 10
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 10
- 239000011521 glass Substances 0.000 description 10
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 10
- 238000005259 measurement Methods 0.000 description 10
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 10
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000004305 biphenyl Substances 0.000 description 9
- 235000010290 biphenyl Nutrition 0.000 description 9
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 9
- 238000002156 mixing Methods 0.000 description 9
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 9
- 150000003077 polyols Chemical class 0.000 description 9
- 239000000377 silicon dioxide Substances 0.000 description 9
- 238000003860 storage Methods 0.000 description 9
- 239000000758 substrate Substances 0.000 description 9
- 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 8
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 8
- 125000001931 aliphatic group Chemical group 0.000 description 8
- 229930003836 cresol Natural products 0.000 description 8
- 229920001971 elastomer Polymers 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 8
- 239000003999 initiator Substances 0.000 description 8
- 239000003960 organic solvent Substances 0.000 description 8
- 150000002989 phenols Chemical class 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 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 8
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 7
- GSKNLOOGBYYDHV-UHFFFAOYSA-N 2-methylphenol;naphthalen-1-ol Chemical compound CC1=CC=CC=C1O.C1=CC=C2C(O)=CC=CC2=C1 GSKNLOOGBYYDHV-UHFFFAOYSA-N 0.000 description 7
- FVCSARBUZVPSQF-UHFFFAOYSA-N 5-(2,4-dioxooxolan-3-yl)-7-methyl-3a,4,5,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C(C(OC2=O)=O)C2C(C)=CC1C1C(=O)COC1=O FVCSARBUZVPSQF-UHFFFAOYSA-N 0.000 description 7
- 229930185605 Bisphenol Natural products 0.000 description 7
- 239000004805 Cyclohexane-1,2-dicarboxylic acid Substances 0.000 description 7
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 7
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical group CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 7
- 239000011256 inorganic filler Substances 0.000 description 7
- 229910003475 inorganic filler Inorganic materials 0.000 description 7
- 229910001507 metal halide Inorganic materials 0.000 description 7
- 150000005309 metal halides Chemical class 0.000 description 7
- 239000000178 monomer Substances 0.000 description 7
- 229910052698 phosphorus Inorganic materials 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
- 229920000877 Melamine resin Polymers 0.000 description 6
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 150000008065 acid anhydrides Chemical class 0.000 description 6
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 6
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 6
- 125000003700 epoxy group Chemical group 0.000 description 6
- 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
- 150000002430 hydrocarbons Chemical group 0.000 description 6
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 6
- 239000000347 magnesium hydroxide Substances 0.000 description 6
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 6
- VSWALKINGSNVAR-UHFFFAOYSA-N naphthalen-1-ol;phenol Chemical compound OC1=CC=CC=C1.C1=CC=C2C(O)=CC=CC2=C1 VSWALKINGSNVAR-UHFFFAOYSA-N 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 229920001721 polyimide Polymers 0.000 description 6
- 239000005060 rubber Substances 0.000 description 6
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 6
- FPZWZCWUIYYYBU-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl acetate Chemical compound CCOCCOCCOC(C)=O FPZWZCWUIYYYBU-UHFFFAOYSA-N 0.000 description 5
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 5
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical class C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 238000007259 addition reaction Methods 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
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- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 5
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- 239000003504 photosensitizing agent Substances 0.000 description 5
- 229920006122 polyamide resin Polymers 0.000 description 5
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 4
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- 150000001408 amides Chemical class 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 238000005266 casting Methods 0.000 description 4
- 150000007973 cyanuric acids Chemical class 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
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- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 4
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 4
- 150000004820 halides Chemical class 0.000 description 4
- 150000003949 imides Chemical class 0.000 description 4
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 4
- 150000007524 organic acids Chemical class 0.000 description 4
- 229920002312 polyamide-imide Polymers 0.000 description 4
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- 239000001294 propane Substances 0.000 description 4
- 125000006850 spacer group Chemical group 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- HCNHNBLSNVSJTJ-UHFFFAOYSA-N 1,1-Bis(4-hydroxyphenyl)ethane Chemical compound C=1C=C(O)C=CC=1C(C)C1=CC=C(O)C=C1 HCNHNBLSNVSJTJ-UHFFFAOYSA-N 0.000 description 3
- XQUPVDVFXZDTLT-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C(C=C1)=CC=C1CC1=CC=C(N2C(C=CC2=O)=O)C=C1 XQUPVDVFXZDTLT-UHFFFAOYSA-N 0.000 description 3
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 3
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- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 description 3
- GZVHEAJQGPRDLQ-UHFFFAOYSA-N 6-phenyl-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=CC=CC=2)=N1 GZVHEAJQGPRDLQ-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000004925 Acrylic resin Substances 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 240000007594 Oryza sativa Species 0.000 description 3
- 235000007164 Oryza sativa Nutrition 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 229910052581 Si3N4 Inorganic materials 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 239000002313 adhesive film Substances 0.000 description 3
- 239000001361 adipic acid Substances 0.000 description 3
- 235000011037 adipic acid Nutrition 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical class C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 3
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 3
- 239000012965 benzophenone Substances 0.000 description 3
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Classifications
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- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
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- H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2363/00—Characterised by the use of epoxy resins; Derivatives of epoxy resins
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2467/00—Characterised by the use of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Derivatives of such polymers
- C08J2467/04—Polyesters derived from hydroxy carboxylic acids, e.g. lactones
-
- 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
- C08K7/00—Use of ingredients characterised by shape
- C08K7/02—Fibres or whiskers
- C08K7/04—Fibres or whiskers inorganic
- C08K7/06—Elements
Abstract
Description
前記特定エポキシ樹脂に含まれるノボラック型エポキシ樹脂及びクレゾールノボラック型エポキシ樹脂の合計の含有率は、前記特定エポキシ樹脂100質量%中、好ましくは90質量%以上、より好ましくは95質量%以上であり、上限は100質量%である。
本明細書において、重量平均分子量は、ゲルパーミエーションクロマトグラフィにより測定した値を意味するものとする。
前記硬化促進剤(A4)の含有量は、前記硬化剤(A3)100質量部に対して、好ましくは1質量部以上10質量部以下である。
上限は100質量%である。
前記光増感剤(F)を用いる場合、その含有量は、前記光重合開始剤(E)100質量部に対して、好ましくは1質量部以上、より好ましくは3質量部以上、さらに好ましくは5質量部以上であり、好ましくは20質量部以下、より好ましくは15質量部以下、さらに好ましくは12質量部以下である。
特に、本発明の組成物を半導体封止材(好ましくはパワートランジスタ、パワーIC用高熱伝導半導体封止材)に用いる場合、シリカ(溶融シリカ、結晶シリカが挙げられ、好ましくは結晶シリカ)、アルミナ、窒化ケイ素が好ましい。
反応装置に、ポリプロピレングリコール(AGC株式会社製、『EXCENOL(登録商標) 3020』)を300質量部と、ε−カプロラクトン(ダイセル株式会社製、『プラクセル(登録商標) M』)を600質量部仕込み、昇温と撹拌を開始した。次いで、内温を190℃に上昇した後、TiPTを0.009質量部仕込み、190℃で10時間反応させブロックポリマーAを合成した。
得られたブロックポリマーAの水酸基価は12.7、数平均分子量は8,840であった。
反応装置に、ポリテトラメチレングリコール(三菱ケミカル株式会社、『PTMG3000』)を300質量部と、ε−カプロラクトン(ダイセル株式会社製、『プラクセル(登録商標) M』)を600質量部仕込み、昇温と撹拌を開始した。次いで、内温を190℃に上昇した後、TiPTを0.009質量部仕込み、190℃で10時間反応させブロックポリマーBを合成した。
得られたブロックポリマーBの水酸基価は13.8、数平均分子量は8,130であった。
反応装置に、ポリブタジエンポリオール(日本曹達株式会社、『G−3000』)を300質量部と、ε−カプロラクトン(ダイセル株式会社製、『プラクセル(登録商標) M』)を600質量部仕込み、昇温と撹拌を開始した。次いで、内温を150℃に上昇した後、TiPTを0.045質量部仕込み、150℃で10時間反応させ樹脂Cを合成した。
得られたブロックポリマーCの水酸基価は11.4、数平均分子量は9,840であった。
反応装置に、水添ポリブタジエンポリオール(日本曹達株式会社、『GI−1000』)を250質量部と、ε−カプロラクトン(ダイセル株式会社製、『プラクセル(登録商標) M』)を750質量部仕込み、昇温と撹拌を開始した。次いで、内温を190℃に上昇した後、TiPTを0.009質量部仕込み、190℃で10時間反応させ樹脂Dを合成した。
得られたブロックポリマーDの水酸基価は17.2、数平均分子量は6,520であった。
フラスコにエポキシ樹脂としてビスフェノールA型エポキシ樹脂(DIC株式会社製、『EPICLON(登録商標) 850−S』)を50質量部、硬化剤として活性エステル樹脂(DIC株式会社製、『EPICLON(登録商標) HPC−8000−65T』)90.8質量部を配合し、130℃で1時間、減圧乾燥することで溶剤を留去した。そこに合成例1で得られたブロックポリマーA10.9質量部配合し、内温130℃で相溶するまで撹拌した。硬化促進剤としてN,N−ジメチルアミノピリジンを0.6質量部添加し、20秒撹拌したあと、真空脱泡することで本発明の樹脂組成物(熱硬化性組成物)であるエポキシ樹脂組成物(X1)を得た。得られた硬化物の破断面を原子間力顕微鏡(AFM)により観察したところ、弾性率の異なる2相が、海部と島部とを形成していることが確認された。
合成例1で得られたブロックポリマーAの代わりに、ブロックポリマーBを用いること以外は、実施例1と同様にして、本発明の樹脂組成物(熱硬化性組成物)であるエポキシ樹脂組成物(X2)を得た。得られた硬化物の破断面を原子間力顕微鏡(AFM)により観察したところ、弾性率の異なる2相が、海部と島部とを形成していることが確認された。
合成例1で得られたブロックポリマーAの代わりに、ブロックポリマーCを用いること以外は、実施例1と同様にして、本発明の樹脂組成物(熱硬化性組成物)であるエポキシ樹脂組成物(X3)を得た。得られた硬化物の破断面を原子間力顕微鏡(AFM)により観察したところ、弾性率の異なる2相が、海部と島部とを形成していることが確認された。
合成例1で得られたブロックポリマーAの代わりに、ブロックポリマーDを用いること以外は、実施例1と同様にして、本発明の樹脂組成物(熱硬化性組成物)であるエポキシ樹脂組成物(X4)を得た。得られた硬化物の破断面を原子間力顕微鏡(AFM)により観察したところ、弾性率の異なる2相が、海部と島部とを形成していることが確認された。
フラスコにエポキシ樹脂としてビスフェノールA型エポキシ樹脂(DIC株式会社製、『EPICLON(商標) 850−S』)を50質量部、硬化剤として活性エステル樹脂(DIC株式会社製、『EPICLON(登録商標) HPC−8000−65T』)90.8質量部を配合し、130℃で1時間減圧乾燥することで溶剤を留去した。硬化促進剤としてN,N−ジメチルアミノピリジンを0.6質量部添加し、20秒撹拌したあと、真空脱泡することで本発明の熱硬化性組成物であるエポキシ樹脂組成物(X5)を得た。得られた硬化物の破断面を原子間力顕微鏡(AFM)により観察したが、相分離構造は観察されなかった。
実施例及び比較例で得たエポキシ樹脂組成物を130℃で2mm厚のゴム製スペーサーをガラス板で挟んだ注型板に流し込み、175℃で5時間熱硬化させた。得られた硬化物を幅5mm×長さ55mmの大きさに切り出し、下記の条件にて、貯蔵弾性率(E')及び損失弾性率(E”)を測定した。
E'/E”をtanδとした場合、tanδが最大となる温度をガラス転移温度(Tg、単位;℃)とし、測定した。
また、25℃での貯蔵弾性率(E')を測定した。
測定機器 :動的粘弾性測定機(エスアイアイ・ナノテクノロジー株式会社製)
型式 :DMA6100
測定温度範囲:0℃〜300℃
昇温速度 :5℃/分
周波数 :1Hz
測定モード :曲げ
◎:4,100MPa以下
○:4,100MPa超4,500MPa以下
×:4,500MPa超
◎:ガラス転移温度160℃以上
○:ガラス転移温度150℃以上160℃未満
×:ガラス転移温度150℃未満
実施例及び比較例で得たエポキシ樹脂組成物を130℃で2mm厚のゴム製スペーサーを片面に銅箔を張ったガラス板で挟んだ注型板に流し込み、175℃で5時間熱硬化させた。得られた硬化物を幅10mm×長さ60mmの大きさに切り出し、剥離試験機を用いて90°ピール強度を測定した。
測定機器 :島津オートグラフ(株式会社島津製作所製)
型式 :AG−1
試験速度 :50mm/m
◎:ピール強度8.0N/cm以上
○:ピール強度7.0N/cm以上8.0N/cm未満
×:ピール強度7.0N/cm未満
混合容器にエポキシ樹脂としてビスフェノールA型エポキシ樹脂(DIC株式会社製、『EPICLON(登録商標) 850−S』)を50質量部、硬化剤としてノボラック型フェノール樹脂(DIC株式会社製、『フェノライト(登録商標) TD−2131』)を27.7質量部、合成例1で得られたブロックポリマー7.8質量部配合し、内温130℃で相溶するまで撹拌した。硬化促進剤としてトリフェニルホスフィンを0.8質量部添加し、20秒撹拌したあと、真空脱泡することで本発明の熱硬化性組成物であるエポキシ樹脂組成物(Y1)を得た。得られた硬化物の破断面を原子間力顕微鏡(AFM)により観察したところ、弾性率の異なる2相が、海部と島部とを形成していることが確認された。
合成例1で得られたブロックポリマーAの代わりに、ブロックポリマーBを用いること以外は、実施例1と同様にして、本発明の熱硬化性組成物であるエポキシ樹脂組成物(Y2)を得た。得られた硬化物の破断面を原子間力顕微鏡(AFM)により観察したところ、弾性率の異なる2相が、海部と島部とを形成していることが確認された。
合成例1で得られたブロックポリマーAの代わりに、ブロックポリマーCを用いること以外は、実施例1と同様にして、本発明の熱硬化性組成物であるエポキシ樹脂組成物(Y3)を得た。得られた硬化物の破断面を原子間力顕微鏡(AFM)により観察したところ、弾性率の異なる2相が、海部と島部とを形成していることが確認された。
合成例1で得られたブロックポリマーAの代わりに、ブロックポリマーDを用いること以外は、実施例1と同様にして、本発明の熱硬化性組成物であるエポキシ樹脂組成物(Y4)を得た。得られた硬化物の破断面を原子間力顕微鏡(AFM)により観察したところ、弾性率の異なる2相が、海部と島部とを形成していることが確認された。
混合容器にエポキシ樹脂としてビスフェノールA型エポキシ樹脂(DIC株式会社製、『EPICLON(登録商標) 850−S』)を50質量部、硬化剤としてノボラック型フェノール樹脂(DIC株式会社製、『フェノライト(登録商標) TD−2131』)を27.7質量部配合し、内温130℃で相溶するまで撹拌した。硬化促進剤としてトリフェニルホスフィンを0.8質量部添加し、20秒撹拌したあと、真空脱泡することで本発明の熱硬化性組成物であるエポキシ樹脂組成物(Y5)を得た。得られた硬化物の破断面を原子間力顕微鏡(AFM)により観察したが、相分離構造は観察されなかった。
実施例及び比較例で得たエポキシ樹脂組成物を130℃で2mm厚のゴム製スペーサーをガラス板で挟んだ注型板に流し込み、175℃で5時間熱硬化させた。得られた硬化物を幅5mm×長さ55mmの大きさに切り出し、下記の条件にて、貯蔵弾性率(E')及び損失弾性率(E”)を測定した。
型式 :DMA6100
測定温度範囲:0℃〜300℃
昇温速度 :5℃/分
周波数 :1Hz
測定モード :曲げ
◎:ガラス転移温度140℃以上
○:ガラス転移温度130℃以上140℃未満
×:ガラス転移温度130℃未満
実施例及び比較例で得たエポキシ樹脂組成物を130℃で4mm厚のゴム製スペーサー
をガラス板で挟んだ注型板に流し込み、175℃で5時間熱硬化させた。
得られた硬化物を幅13mm×長さ80mm×厚さ4mmの大きさに切削し試験片とし
て、ASTM D5045−93(ISO 13586)に従い加工し、破壊靱性(単位
;MPa・m0.5)の測定を行った。
試験前における試験片へのノッチ(刻み目)の作成は、剃刀の刃を試験片にあて、ハン
マーで剃刀の刃に衝撃を与えることで行った。
測定機器 :島津オートグラフ(株式会社島津製作所製)
型式 :AG−X plus
試験速度 :10mm/分
標線間距離 :50mm
◎:1.50MPa・m0.5以上
〇:1.00MPa・m0.5以上1.50MPa・m0.5未満
×:1.00MPa・m0.5未満
混合容器に酸変性ビニル基含有エポキシ樹脂としてオルソクレゾール型エポキシアクリレート樹脂(DIC株式会社製、『DICLITE(登録商標) UE−9000』、不揮発分63.4質量%)を100質量部、合成例1で得られたブロックポリマーAを3.2質量部、光重合開始剤として2−メチル−1−(4−メチルチオフェニル)−2−モルフォリノプロパン−1−オン(BASF社製、『イルガキュア(登録商標)907』)を3.2質量部、多官能アクリレートとしてジペンタエリスリトールヘキサアクリレート(新中村化学工業株式会社製、『A−DPH(登録商標)』)を1.9質量部、硬化剤としてオルソクレゾールノボラック型エポキシ樹脂(DIC株式会社製、『EPICLON(登録商標) N−680』を24.4質量部、硬化促進剤として2−エチル−4−メチルイミダゾール0.3質量部、有機溶剤としてジエチレングリコールモノエチルエーテルアセテート13.3質量部を配合し、攪拌することで本発明のエポキシ樹脂組成物(X9)を得た。
合成例1で得られたブロックポリマーAを3.2質量部用いる代わりに、合成例2〜4で得られたブロックポリマーB,C,又はDを3.2質量部用いること以外は、実施例1と同様にして、エポキシ樹脂組成物(X10)〜(X12)を得た。
混合容器に酸変性ビニル基含有エポキシ樹脂としてオルソクレゾール型エポキシアクリレート樹脂(DIC株式会社製、『DICLITE(登録商標) UE−9000』)を100質量部、(他社添加剤等添加)、光重合開始剤として2−メチル−1−(4−メチルチオフェニル)−2−モルフォリノプロパン−1−オン(BASF社製、『イルガキュア(登録商標)907』)を3.2質量部、多官能アクリレートとしてジペンタエリスリトールヘキサアクリレート(新中村化学工業株式会社製、『A−DPH(登録商標)』)を1.9質量部、硬化剤としてオルソクレゾールノボラック型エポキシ樹脂(DIC株式会社製、『EPICLON(登録商標) N−680』)を37.7質量部、硬化促進剤として2−エチル−4−メチルイミダゾール0.3質量部配合し、相溶するまで攪拌することで本発明のエポキシ樹脂組成物(Y3)を得た。
合成例1で得られたブロックポリマーAを3.2質量部用いる代わりに、水添ブタジエンポリオール(日本曹達株式会社製、『GI−3000』)3.2質量部を用いること以外は、実施例1と同様にして、エポキシ樹脂組成物(Y4)を得た。
実施例及び比較例で得たエポキシ樹脂組成物を76μmのアプリケーターで塗布し、80℃で30分乾燥させた。メタルハライドランプを用いて1,000mJ/cm2の紫外線を照射し、更に160℃で1時間熱硬化させた。得られた硬化物を幅10mm×長さ50mmの大きさに切り出し、下記の条件にて、貯蔵弾性率(E')及び損失弾性率(E”)を測定した。E'/E”をtanδとした場合、tanδが最大となる温度をガラス転移温度(Tg、単位;℃)とし、測定した。また、25℃での貯蔵弾性率(E')を測定した。
測定機器 :動的粘弾性測定機(エスアイアイ・ナノテクノロジー株式会社製)
型式 :DMA6100
測定温度範囲:−100℃〜250℃
昇温速度 :5℃/分
周波数 :1Hz
測定モード :引張モード
◎:3,000MPa以下
〇:3,000MPa超4,000MPa以下
×:4,000MPa超
◎:ガラス転移温度130℃以上
○:ガラス転移温度125℃以上130℃未満
×:ガラス転移温度125℃未満
実施例及び比較例で得たエポキシ樹脂組成物を銅箔上に76μmのアプリケーターで塗布し、80℃で30分乾燥させた。メタルハライドランプを用いて1,000mJ/cm2の紫外線を照射し、更に160℃で1時間熱硬化させた。得られた硬化物を幅10mm×長さ100mmの大きさに切り出し、剥離試験機を用いて90°ピール強度を測定した。
測定機器 :島津オートグラフ(株式会社島津製作所製)
型式 :AG−1
試験速度 :50mm/min
◎:ピール強度0.5N/cm以上
○:ピール強度0.2N/cm以上0.5N/cm未満
×:ピール強度0.2N/cm未満
Claims (15)
- 樹脂及び改質樹脂を含み、前記樹脂が、熱硬化性樹脂;又はアルカリ可溶性樹脂とエポキシ硬化剤との組合せを含むものであり、前記改質樹脂が、n個のポリマーAブロックと、n価のポリマーBブロックとが結合したものであるブロックポリマーを含むものであり、前記nが、2以上の整数である樹脂組成物。
- 前記ポリマーAブロックが、ポリエステル単位を含むものである請求項1記載の樹脂組成物。
- 前記ポリマーBブロックが、ポリエーテル単位、共役ジエン重合体単位、水添共役ジエン重合体単位及びポリシロキサン単位からなる群より選ばれる1種以上を含むものである請求項1又は2記載の樹脂組成物。
- 前記ブロックポリマーの数平均分子量が、1,500以上20,000以下である請求項1〜3のいずれか1項記載の樹脂組成物。
- 前記樹脂が、熱硬化性樹脂を含むものであり、
前記ポリマーBブロック中、ポリエーテル単位、共役ジエン重合体単位、水添共役ジエン重合体単位及びポリシロキサン単位の合計の含有率が、70質量%以上である請求項1〜4のいずれか1項記載の樹脂組成物。 - 前記樹脂が、アルカリ可溶性樹脂とエポキシ硬化剤との組合せを含むものであり、
前記ポリマーAブロックが、ポリエステル単位を含むものであり、
前記ポリマーBブロックが、ガラス転移温度0℃以下のポリマーブロックである請求項1〜4のいずれか1項記載の樹脂組成物。 - 請求項5記載の樹脂組成物からなる半導体封止材料。
- 請求項5記載の樹脂組成物と補強基材とを有する含浸基材の半硬化物であるプリプレグ。
- 請求項5記載の樹脂組成物の板状賦形物と銅箔とを含む回路基板。
- 請求項5記載の樹脂組成物の硬化物と基材フィルムとを含むビルドアップフィルム。
- 請求項5記載の樹脂組成物と、炭素繊維とを有するプリプレグ。
- 請求項11記載のプリプレグの硬化物である炭素繊維複合材料。
- 請求項6記載の活性エネルギー線硬化性組成物からなるソルダーレジスト。
- 請求項6記載の活性エネルギー線硬化性組成物からなるドライフィルム。
- 請求項13記載のソルダーレジストから形成される樹脂層の硬化物を有するプリント配線板。
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