CN113292818A - Resin composition - Google Patents
Resin composition Download PDFInfo
- Publication number
- CN113292818A CN113292818A CN202110135632.9A CN202110135632A CN113292818A CN 113292818 A CN113292818 A CN 113292818A CN 202110135632 A CN202110135632 A CN 202110135632A CN 113292818 A CN113292818 A CN 113292818A
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- China
- Prior art keywords
- resin composition
- mass
- component
- resin
- composition according
- Prior art date
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- 239000011342 resin composition Substances 0.000 title claims abstract description 246
- 239000003822 epoxy resin Substances 0.000 claims abstract description 165
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 165
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 89
- 239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 52
- 229920000570 polyether Polymers 0.000 claims abstract description 52
- 239000011256 inorganic filler Substances 0.000 claims abstract description 49
- 229910003475 inorganic filler Inorganic materials 0.000 claims abstract description 49
- 150000001875 compounds Chemical class 0.000 claims abstract description 45
- 239000004593 Epoxy Substances 0.000 claims abstract description 42
- 239000000178 monomer Substances 0.000 claims abstract description 13
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims abstract description 10
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical group CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000004065 semiconductor Substances 0.000 claims description 108
- 229920005989 resin Polymers 0.000 claims description 74
- 239000011347 resin Substances 0.000 claims description 74
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 46
- 239000000758 substrate Substances 0.000 claims description 36
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 claims description 33
- 229920001296 polysiloxane Polymers 0.000 claims description 28
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 26
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 20
- 238000007789 sealing Methods 0.000 claims description 20
- 239000004850 liquid epoxy resins (LERs) Substances 0.000 claims description 17
- 150000001412 amines Chemical class 0.000 claims description 13
- 229920001515 polyalkylene glycol Polymers 0.000 claims description 12
- 239000000377 silicon dioxide Substances 0.000 claims description 11
- 150000008065 acid anhydrides Chemical class 0.000 claims description 10
- 238000011049 filling Methods 0.000 abstract description 11
- 239000010410 layer Substances 0.000 description 196
- 238000001723 curing Methods 0.000 description 120
- -1 glycidyl ester Chemical class 0.000 description 106
- 238000000034 method Methods 0.000 description 74
- 239000000463 material Substances 0.000 description 60
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 48
- 239000000126 substance Substances 0.000 description 45
- 239000004020 conductor Substances 0.000 description 32
- 239000000047 product Substances 0.000 description 31
- 229910052751 metal Inorganic materials 0.000 description 30
- 239000002184 metal Substances 0.000 description 30
- 229920003986 novolac Polymers 0.000 description 28
- 125000004432 carbon atom Chemical group C* 0.000 description 26
- 238000004519 manufacturing process Methods 0.000 description 20
- 230000008569 process Effects 0.000 description 20
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 18
- 230000015572 biosynthetic process Effects 0.000 description 18
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 18
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 17
- 239000002245 particle Substances 0.000 description 17
- 238000011282 treatment Methods 0.000 description 17
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 16
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 15
- 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 15
- 239000003960 organic solvent Substances 0.000 description 15
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 14
- 230000000052 comparative effect Effects 0.000 description 14
- 150000002148 esters Chemical group 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 229920001451 polypropylene glycol Polymers 0.000 description 14
- 238000012360 testing method Methods 0.000 description 14
- 238000005259 measurement Methods 0.000 description 13
- 238000007747 plating Methods 0.000 description 13
- 125000000217 alkyl group Chemical group 0.000 description 12
- 125000003118 aryl group Chemical group 0.000 description 12
- 238000010438 heat treatment Methods 0.000 description 12
- 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 11
- RVGRUAULSDPKGF-UHFFFAOYSA-N Poloxamer Chemical compound C1CO1.CC1CO1 RVGRUAULSDPKGF-UHFFFAOYSA-N 0.000 description 11
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 10
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 10
- 239000000654 additive Substances 0.000 description 9
- 239000000956 alloy Substances 0.000 description 9
- 238000000748 compression moulding Methods 0.000 description 9
- 239000004643 cyanate ester Substances 0.000 description 9
- 125000003700 epoxy group Chemical group 0.000 description 9
- 238000003475 lamination Methods 0.000 description 9
- 125000001624 naphthyl group Chemical group 0.000 description 9
- 229920001187 thermosetting polymer Polymers 0.000 description 9
- 229910045601 alloy Inorganic materials 0.000 description 8
- 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 8
- 229910052802 copper Inorganic materials 0.000 description 8
- 239000010949 copper Substances 0.000 description 8
- 239000011888 foil Substances 0.000 description 8
- 238000000465 moulding Methods 0.000 description 8
- 238000007788 roughening Methods 0.000 description 8
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 7
- 125000003710 aryl alkyl group Chemical group 0.000 description 7
- 238000013001 point bending Methods 0.000 description 7
- 229920001983 poloxamer Polymers 0.000 description 7
- 229910000679 solder Inorganic materials 0.000 description 7
- 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 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- 150000005215 alkyl ethers Chemical class 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 239000011889 copper foil Substances 0.000 description 6
- 229930003836 cresol Natural products 0.000 description 6
- 150000005690 diesters Chemical class 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- 238000009826 distribution Methods 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000000155 melt Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000002966 varnish Substances 0.000 description 6
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 5
- 239000002518 antifoaming agent Substances 0.000 description 5
- 229920001400 block copolymer Polymers 0.000 description 5
- 239000004205 dimethyl polysiloxane Substances 0.000 description 5
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 5
- 239000012530 fluid Substances 0.000 description 5
- 238000001879 gelation Methods 0.000 description 5
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 5
- 229910052737 gold Inorganic materials 0.000 description 5
- 239000010931 gold Substances 0.000 description 5
- 229910052742 iron Inorganic materials 0.000 description 5
- 238000010030 laminating Methods 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 229910052759 nickel Inorganic materials 0.000 description 5
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 5
- 230000001681 protective effect Effects 0.000 description 5
- 229910052719 titanium Inorganic materials 0.000 description 5
- 239000010936 titanium Substances 0.000 description 5
- XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical group OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-UHFFFAOYSA-N 0.000 description 4
- 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 4
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 4
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 4
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 150000003973 alkyl amines Chemical class 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- ZFVMWEVVKGLCIJ-UHFFFAOYSA-N bisphenol AF Chemical compound C1=CC(O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(O)C=C1 ZFVMWEVVKGLCIJ-UHFFFAOYSA-N 0.000 description 4
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 4
- 229910052804 chromium Inorganic materials 0.000 description 4
- 239000011651 chromium Substances 0.000 description 4
- 239000007822 coupling agent Substances 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 229940008099 dimethicone Drugs 0.000 description 4
- 239000003063 flame retardant Substances 0.000 description 4
- 238000005227 gel permeation chromatography Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 150000002334 glycols Chemical class 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- KBJFYLLAMSZSOG-UHFFFAOYSA-N n-(3-trimethoxysilylpropyl)aniline Chemical compound CO[Si](OC)(OC)CCCNC1=CC=CC=C1 KBJFYLLAMSZSOG-UHFFFAOYSA-N 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- 229920000139 polyethylene terephthalate Polymers 0.000 description 4
- 239000005020 polyethylene terephthalate Substances 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 239000003566 sealing material Substances 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- 239000010703 silicon Substances 0.000 description 4
- 229910052709 silver Inorganic materials 0.000 description 4
- 239000004332 silver Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000012756 surface treatment agent Substances 0.000 description 4
- 229910052718 tin Inorganic materials 0.000 description 4
- 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 4
- 229910052725 zinc Inorganic materials 0.000 description 4
- 239000011701 zinc Substances 0.000 description 4
- MEVBAGCIOOTPLF-UHFFFAOYSA-N 2-[[5-(oxiran-2-ylmethoxy)naphthalen-2-yl]oxymethyl]oxirane Chemical compound C1OC1COC(C=C1C=CC=2)=CC=C1C=2OCC1CO1 MEVBAGCIOOTPLF-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- 229930185605 Bisphenol Natural products 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 239000000853 adhesive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 239000005456 alcohol based solvent Substances 0.000 description 3
- 125000002723 alicyclic group Chemical group 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 150000001983 dialkylethers Chemical class 0.000 description 3
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000009713 electroplating Methods 0.000 description 3
- 238000005530 etching Methods 0.000 description 3
- 238000009499 grossing Methods 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910000623 nickel–chromium alloy Inorganic materials 0.000 description 3
- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical compound NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- 238000005498 polishing Methods 0.000 description 3
- 229920003207 poly(ethylene-2,6-naphthalate) Polymers 0.000 description 3
- 239000011112 polyethylene naphthalate Substances 0.000 description 3
- 238000003825 pressing Methods 0.000 description 3
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 3
- 239000000600 sorbitol Substances 0.000 description 3
- 238000004381 surface treatment Methods 0.000 description 3
- 239000011135 tin Substances 0.000 description 3
- LTVUCOSIZFEASK-MPXCPUAZSA-N (3ar,4s,7r,7as)-3a-methyl-3a,4,7,7a-tetrahydro-4,7-methano-2-benzofuran-1,3-dione Chemical compound C([C@H]1C=C2)[C@H]2[C@H]2[C@]1(C)C(=O)OC2=O LTVUCOSIZFEASK-MPXCPUAZSA-N 0.000 description 2
- YBBLOADPFWKNGS-UHFFFAOYSA-N 1,1-dimethylurea Chemical compound CN(C)C(N)=O YBBLOADPFWKNGS-UHFFFAOYSA-N 0.000 description 2
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 2
- LVEYOSJUKRVCCF-UHFFFAOYSA-N 1,3-bis(diphenylphosphino)propane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCP(C=1C=CC=CC=1)C1=CC=CC=C1 LVEYOSJUKRVCCF-UHFFFAOYSA-N 0.000 description 2
- OEBXWWBYZJNKRK-UHFFFAOYSA-N 1-methyl-2,3,4,6,7,8-hexahydropyrimido[1,2-a]pyrimidine Chemical compound C1CCN=C2N(C)CCCN21 OEBXWWBYZJNKRK-UHFFFAOYSA-N 0.000 description 2
- FPZWZCWUIYYYBU-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl acetate Chemical compound CCOCCOCCOC(C)=O FPZWZCWUIYYYBU-UHFFFAOYSA-N 0.000 description 2
- XOSCKTQMAZSFBZ-UHFFFAOYSA-N 2-[[1-[[2,7-bis(oxiran-2-ylmethoxy)naphthalen-1-yl]methyl]-7-(oxiran-2-ylmethoxy)naphthalen-2-yl]oxymethyl]oxirane Chemical compound C1OC1COC(C=C1C=2CC=3C4=CC(OCC5OC5)=CC=C4C=CC=3OCC3OC3)=CC=C1C=CC=2OCC1CO1 XOSCKTQMAZSFBZ-UHFFFAOYSA-N 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- CMLFRMDBDNHMRA-UHFFFAOYSA-N 2h-1,2-benzoxazine Chemical compound C1=CC=C2C=CNOC2=C1 CMLFRMDBDNHMRA-UHFFFAOYSA-N 0.000 description 2
- WVRNUXJQQFPNMN-VAWYXSNFSA-N 3-[(e)-dodec-1-enyl]oxolane-2,5-dione Chemical compound CCCCCCCCCC\C=C\C1CC(=O)OC1=O WVRNUXJQQFPNMN-VAWYXSNFSA-N 0.000 description 2
- UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 description 2
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 2
- YXCDZXGJZDGMEP-UHFFFAOYSA-N 4-hydroxy-3,3-bis(hydroxymethyl)butan-2-one Chemical compound CC(=O)C(CO)(CO)CO YXCDZXGJZDGMEP-UHFFFAOYSA-N 0.000 description 2
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- FZZQNEVOYIYFPF-UHFFFAOYSA-N naphthalene-1,6-diol Chemical compound OC1=CC=CC2=CC(O)=CC=C21 FZZQNEVOYIYFPF-UHFFFAOYSA-N 0.000 description 1
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- YTVNOVQHSGMMOV-UHFFFAOYSA-N naphthalenetetracarboxylic dianhydride Chemical compound C1=CC(C(=O)OC2=O)=C3C2=CC=C2C(=O)OC(=O)C1=C32 YTVNOVQHSGMMOV-UHFFFAOYSA-N 0.000 description 1
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- JFOJYGMDZRCSPA-UHFFFAOYSA-J octadecanoate;tin(4+) Chemical compound [Sn+4].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O JFOJYGMDZRCSPA-UHFFFAOYSA-J 0.000 description 1
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- GHPYAGKTTCKKDF-UHFFFAOYSA-M tetraphenylphosphanium;thiocyanate Chemical compound [S-]C#N.C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 GHPYAGKTTCKKDF-UHFFFAOYSA-M 0.000 description 1
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- XDHRVAHAGMMFMC-UHFFFAOYSA-N tris(2,4-dimethylphenyl)phosphane Chemical compound CC1=CC(C)=CC=C1P(C=1C(=CC(C)=CC=1)C)C1=CC=C(C)C=C1C XDHRVAHAGMMFMC-UHFFFAOYSA-N 0.000 description 1
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- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
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- RYXYUARTMQUYKV-UHFFFAOYSA-N tris(4-butylphenyl)phosphane Chemical compound C1=CC(CCCC)=CC=C1P(C=1C=CC(CCCC)=CC=1)C1=CC=C(CCCC)C=C1 RYXYUARTMQUYKV-UHFFFAOYSA-N 0.000 description 1
- SPNVODOGUAUMCA-UHFFFAOYSA-N tris(4-ethoxy-2,6-dimethylphenyl)phosphane Chemical compound CC1=CC(OCC)=CC(C)=C1P(C=1C(=CC(OCC)=CC=1C)C)C1=C(C)C=C(OCC)C=C1C SPNVODOGUAUMCA-UHFFFAOYSA-N 0.000 description 1
- LQEKTSMTEYLBLJ-UHFFFAOYSA-N tris(4-ethoxyphenyl)phosphane Chemical compound C1=CC(OCC)=CC=C1P(C=1C=CC(OCC)=CC=1)C1=CC=C(OCC)C=C1 LQEKTSMTEYLBLJ-UHFFFAOYSA-N 0.000 description 1
- PCCAGZSOGFNURV-UHFFFAOYSA-N tris(4-ethylphenyl)phosphane Chemical compound C1=CC(CC)=CC=C1P(C=1C=CC(CC)=CC=1)C1=CC=C(CC)C=C1 PCCAGZSOGFNURV-UHFFFAOYSA-N 0.000 description 1
- UYUUAUOYLFIRJG-UHFFFAOYSA-N tris(4-methoxyphenyl)phosphane Chemical compound C1=CC(OC)=CC=C1P(C=1C=CC(OC)=CC=1)C1=CC=C(OC)C=C1 UYUUAUOYLFIRJG-UHFFFAOYSA-N 0.000 description 1
- WXAZIUYTQHYBFW-UHFFFAOYSA-N tris(4-methylphenyl)phosphane Chemical compound C1=CC(C)=CC=C1P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 WXAZIUYTQHYBFW-UHFFFAOYSA-N 0.000 description 1
- NTUMNRFLAZXNBW-UHFFFAOYSA-N tris(4-propan-2-ylphenyl)phosphane Chemical compound C1=CC(C(C)C)=CC=C1P(C=1C=CC(=CC=1)C(C)C)C1=CC=C(C(C)C)C=C1 NTUMNRFLAZXNBW-UHFFFAOYSA-N 0.000 description 1
- JTOQWGJGVSYTTN-UHFFFAOYSA-N tris(4-propylphenyl)phosphane Chemical compound C1=CC(CCC)=CC=C1P(C=1C=CC(CCC)=CC=1)C1=CC=C(CCC)C=C1 JTOQWGJGVSYTTN-UHFFFAOYSA-N 0.000 description 1
- UGNAOCDIZFIEQK-UHFFFAOYSA-N tris[4-[(2-methylpropan-2-yl)oxy]phenyl]phosphane Chemical compound C1=CC(OC(C)(C)C)=CC=C1P(C=1C=CC(OC(C)(C)C)=CC=1)C1=CC=C(OC(C)(C)C)C=C1 UGNAOCDIZFIEQK-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 239000011800 void material Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 150000003752 zinc compounds Chemical class 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
- 229910000166 zirconium phosphate Inorganic materials 0.000 description 1
- LEHFSLREWWMLPU-UHFFFAOYSA-B zirconium(4+);tetraphosphate Chemical compound [Zr+4].[Zr+4].[Zr+4].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LEHFSLREWWMLPU-UHFFFAOYSA-B 0.000 description 1
Classifications
-
- 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
-
- 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
- C08G59/02—Polycondensates containing more than one epoxy group per molecule
- C08G59/022—Polycondensates containing more than one epoxy group per molecule characterised by the preparation process or apparatus used
-
- 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
- C08G59/182—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 using pre-adducts of epoxy compounds with curing agents
- C08G59/184—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 using pre-adducts of epoxy compounds with curing agents with amines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/28—Di-epoxy compounds containing acyclic nitrogen atoms
-
- 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
- C08G59/50—Amines
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- 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
- C08K3/34—Silicon-containing compounds
- C08K3/36—Silica
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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
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- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K1/00—Printed circuits
- H05K1/02—Details
- H05K1/03—Use of materials for the substrate
- H05K1/0313—Organic insulating material
- H05K1/0353—Organic insulating material consisting of two or more materials, e.g. two or more polymers, polymer + filler, + reinforcement
- H05K1/0373—Organic insulating material consisting of two or more materials, e.g. two or more polymers, polymer + filler, + reinforcement containing additives, e.g. fillers
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
- C08L2205/025—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group containing two or more polymers of the same hierarchy C08L, and differing only in parameters such as density, comonomer content, molecular weight, structure
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/03—Polymer mixtures characterised by other features containing three or more polymers in a blend
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Abstract
The present invention addresses the problem of providing a resin composition that has excellent filling properties, can suppress warping during curing, and can yield a cured product having excellent mechanical strength. The resin composition comprises (A) an epoxy resin, (B) an inorganic filler, (C) a curing agent, and (D) a non-epoxy compound having a polyether skeleton, wherein the polyether skeleton contained in the component (D) is a polyoxyalkylene skeleton composed of 1 or more monomer units selected from an ethylene oxide unit and a propylene oxide unit, the content of the component (B) is 70% by mass or more, and the content of the component (D) is 1% by mass or more and 30% by mass or less, when the total nonvolatile components in the resin composition are 100% by mass, the nonvolatile components other than the component (B) in the resin composition are 100% by mass.
Description
Technical Field
The present invention relates to a resin composition containing an epoxy resin. The present invention also relates to a cured product, a resin sheet, a circuit board, a semiconductor chip package, and a semiconductor device obtained using the resin composition.
Background
In recent years, there has been an increasing demand for small and high-function electronic devices such as smartphones and tablet devices, and along with this, further improvement in functionality has been demanded for sealing materials for semiconductor chip packages used for these small electronic devices. As such a sealing material, a sealing material formed by curing a resin composition is known (patent document 1).
In addition, a resin composition containing an "epoxy compound containing a polyether skeleton" has been known so far (patent document 2). Further, a resin composition containing "a non-epoxy compound containing a butylene oxide unit and having a polyether skeleton" is known (patent document 3).
Documents of the prior art
Patent document
Patent document 1: japanese patent laid-open publication No. 2017-008312
Patent document 2: international publication No. 2018/221681
Patent document 3: japanese patent laid-open publication No. 2018-168354.
Disclosure of Invention
Problems to be solved by the invention
As a sealing material for semiconductor chip packaging, a material having a low linear thermal expansion coefficient and excellent dimensional stability is required. As a method for suppressing the linear thermal expansion coefficient to a low value, a method of filling a large amount of an inorganic filler into a resin composition is known.
However, when a large amount of an inorganic filler is filled in a resin material, the resin composition is generally likely to become brittle, so that the mechanical strength is reduced, the melt viscosity is increased, voids (void) are likely to be generated during filling, the filling property is likely to be reduced, and the elastic modulus is increased, so that warpage is sometimes difficult to suppress.
Accordingly, an object of the present invention is to provide a resin composition which has excellent filling properties, can suppress warpage during curing, and can give a cured product having excellent mechanical strength.
Means for solving the problems
As a result of intensive studies to achieve the object of the present invention, the present inventors have found that even a resin composition filled with a large amount of (B) an inorganic filler is excellent in filling properties, can suppress warpage during curing, and can obtain a cured product excellent in mechanical strength by using a resin composition containing (D) a polyether skeleton-containing non-epoxy compound composed of a predetermined monomer unit and satisfying predetermined other conditions, and have completed the present invention.
Namely, the present invention includes the following;
[1] a resin composition comprising (A) an epoxy resin, (B) an inorganic filler, (C) a curing agent, and (D) a non-epoxy compound having a polyether skeleton,
wherein the polyether skeleton contained in the component (D) is a polyoxyalkylene skeleton composed of 1 or more monomer units selected from ethylene oxide (ethylene oxide) units and propylene oxide (propylene oxide) units,
the content of component (B) is 70% by mass or more when the total nonvolatile components in the resin composition are taken as 100% by mass, and the content of component (D) is 1% by mass or more and 30% by mass or less when the nonvolatile components other than component (B) in the resin composition are taken as 100% by mass;
[2] the resin composition according to the above [1], wherein the component (D) is at least 1 compound selected from polyalkylene glycols and polyoxyalkylene-modified silicones;
[3] the resin composition according to the above [2], wherein the polyalkylene glycol is polyoxyethylene polyoxypropylene glycol;
[4] the resin composition according to any one of the above [1] to [3], wherein the number average molecular weight of the component (D) is 500 to 10000;
[5] the resin composition according to any one of the above [1] to [4], wherein the viscosity of the component (D) at 25 ℃ is 3000 mPas or less;
[6] the resin composition according to any one of the above [1] to [5], wherein the content of the component (B) is 78% by mass or more, assuming that all nonvolatile components in the resin composition are 100% by mass;
[7] the resin composition according to any one of the above [1] to [6], wherein the component (B) is silica;
[8] the resin composition according to any one of the above [1] to [7], wherein the component (A) comprises: epoxy resins containing a condensed ring structure;
[9] the resin composition according to the above [8], wherein the content of the epoxy resin having a condensed ring structure in the component (A) is 50% by mass or more, assuming that the total amount of the component (A) is 100% by mass;
[10] the resin composition according to any one of the above [1] to [9], wherein the component (A) comprises a glycidylamine-type epoxy resin;
[11] the resin composition according to any one of the above [1] to [10], wherein the component (A) contains a liquid epoxy resin;
[12] the resin composition according to the above [11], wherein the content of the liquid epoxy resin in the component (A) is 50% by mass or more, assuming that the total amount of the component (A) is 100% by mass;
[13] the resin composition according to any one of the above [1] to [12], wherein the content of the component (A) is 40% by mass or more, assuming that nonvolatile components other than the component (B) in the resin composition are 100% by mass;
[14] the resin composition according to any one of the above [1] to [13], wherein the component (C) comprises 1 or more curing agents selected from an acid anhydride curing agent and an amine curing agent;
[15] the resin composition according to any one of the above [1] to [14], which is used for forming an insulating layer for encapsulating a semiconductor chip;
[16] the resin composition according to any one of the above [1] to [14], which is used for forming an insulating layer of a circuit board;
[17] the resin composition according to any one of the above [1] to [14], which is used for sealing a semiconductor chip encapsulated by a semiconductor chip;
[18] a cured product of the resin composition according to any one of the above [1] to [17 ];
[19] a resin sheet comprising a support and, provided on the support, a resin composition layer comprising the resin composition according to any one of the above [1] to [17 ];
[20] a circuit board comprising an insulating layer formed from a cured product of the resin composition according to any one of [1] to [17 ];
[21] a semiconductor chip package comprising the circuit board according to [20] above, and a semiconductor chip mounted on the circuit board;
[22] a semiconductor chip package comprising a semiconductor chip and a cured product of the resin composition according to any one of the above [1] to [17] sealing the semiconductor chip;
[23] a semiconductor device comprising the semiconductor chip package according to [21] or [22 ].
ADVANTAGEOUS EFFECTS OF INVENTION
The present invention provides a resin composition which has excellent filling properties, can suppress warpage during curing, and can give a cured product having excellent mechanical strength.
Detailed Description
The present invention will be described in detail below with reference to preferred embodiments thereof. However, the present invention is not limited to the following embodiments and examples, and can be implemented by arbitrarily changing the embodiments without departing from the scope of the claims and the equivalent scope thereof.
< resin composition >
The resin composition of the present invention comprises (a) an epoxy resin, (B) an inorganic filler, (C) a curing agent, and (D) a non-epoxy compound having a polyether skeleton, wherein the polyether skeleton contained in the component (D) is a polyoxyalkylene skeleton composed of 1 or more monomer units selected from an ethylene oxide unit and a propylene oxide unit, and the content of the component (B) is 70% by mass or more, and the content of the component (D) is 1% by mass or more and 30% by mass or less, when the total nonvolatile components in the resin composition is 100% by mass, and the nonvolatile components other than the component (B) in the resin composition are 100% by mass.
Such a resin composition has excellent filling properties, can suppress warpage during curing, and can provide a cured product having excellent mechanical strength.
The resin composition of the present invention may further contain (E) a curing accelerator, (F) other additives, and (G) an organic solvent, in addition to (a) an epoxy resin, (B) an inorganic filler, (C) a curing agent, and (D) a polyether skeleton-containing non-epoxy compound. Hereinafter, each component contained in the resin composition will be described in detail.
(A) epoxy resin
The resin composition of the present invention contains (a) an epoxy resin. The epoxy resin (a) is a resin having an epoxy group.
Examples of the epoxy resin (a) include: a biscresol (bixylenol) type epoxy resin, a bisphenol a type epoxy resin, a bisphenol F type epoxy resin, a bisphenol S type epoxy resin, a bisphenol AF type epoxy resin, a dicyclopentadiene type epoxy resin, a trisphenol type epoxy resin, a naphthol novolac (naphthol novolac) type epoxy resin, a phenol novolac (phenol novolac) type epoxy resin, a tert-butyl-catechol type epoxy resin, a naphthalene type epoxy resin, a naphthol type epoxy resin, an anthracene type epoxy resin, a glycidylamine type epoxy resin, a glycidyl ester type epoxy resin, a cresol novolac (cresol novolac) type epoxy resin, a biphenyl type epoxy resin, a linear aliphatic epoxy resin, an epoxy resin having a butadiene structure, an alicyclic epoxy resin, a heterocyclic type epoxy resin, a spiro ring-containing epoxy resin, a cyclohexane type epoxy resin, a cyclohexane dimethanol type epoxy resin, a naphthylene ether type epoxy resin, a bisphenol S type epoxy resin, a bisphenol AF type epoxy resin, a dicyclopentadiene type epoxy resin, a trisphenol type epoxy resin, a naphthol novolac type epoxy resin, a naphthol type epoxy resin, a styrene type, Trimethylol epoxy resins, tetraphenylethane epoxy resins, isocyanurate epoxy resins, and the like. (A) The epoxy resin may be used alone in 1 kind, or may be used in combination with 2 or more kinds.
From the viewpoint of further improving the heat resistance and copper adhesion of the cured product, the epoxy resin (a) preferably contains a glycidylamine-type epoxy resin.
In addition, from the viewpoint of imparting excellent heat resistance, the (a) epoxy resin preferably includes "an epoxy resin containing a condensed ring structure". Examples of the condensed ring in the epoxy resin having a condensed ring structure include naphthalene rings, anthracene rings, phenanthrene rings, and the like, and naphthalene rings are particularly preferable. Therefore, (a) the epoxy resin particularly preferably contains "an epoxy resin containing a naphthalene ring structure". Examples of the epoxy resin having a naphthalene ring structure include: epoxy resins having 1 naphthalene ring structure in 1 molecule, such as 1, 6-bis (glycidyloxy) naphthalene, 1, 5-bis (glycidyloxy) naphthalene, and 2, 7-bis (glycidyloxy) naphthalene; epoxy resins having 2 naphthalene ring structures in 1 molecule, such as bis [2- (glycidyloxy) -1-naphthyl ] methane, bis [2, 7-bis (glycidyloxy) -1-naphthyl ] methane, [2, 7-bis (glycidyloxy) -1-naphthyl ] [2- (glycidyloxy) -1-naphthyl ] methane, and the like; a polymer type epoxy resin having 2 or 3 or more naphthalene ring structures in 1 molecule, such as a naphthol novolac type epoxy resin, a naphthol-phenol co-novolac type epoxy resin, a naphthol-cresol co-novolac type epoxy resin, a naphthol aralkyl type epoxy resin, a naphthalenediol aralkyl type epoxy resin, or a naphthylene ether type epoxy resin. Among them, an epoxy resin having 1 naphthalene ring structure in 1 molecule is preferable. (A) The content of the epoxy resin having a condensed ring structure in the epoxy resin is not particularly limited, and the content of the epoxy resin having a condensed ring structure is preferably 20% by mass or more, more preferably 40% by mass or more, and particularly preferably 50% by mass or more, assuming that the total amount of the (a) epoxy resins is 100% by mass.
As the (a) epoxy resin, the resin composition preferably contains an epoxy resin having 2 or more epoxy groups in 1 molecule. The proportion of the epoxy resin having 2 or more epoxy groups in 1 molecule is preferably 50% by mass or more, more preferably 60% by mass or more, and particularly preferably 70% by mass or more, relative to 100% by mass of the nonvolatile component of the epoxy resin (a).
The epoxy resin includes an epoxy resin that is liquid at a temperature of 20 ℃ (hereinafter sometimes referred to as "liquid epoxy resin") and an epoxy resin that is solid at a temperature of 20 ℃ (hereinafter sometimes referred to as "solid epoxy resin"). For the resin composition of the present invention, as the epoxy resin, only a liquid epoxy resin may be contained, or only a solid epoxy resin may be contained, or a liquid epoxy resin and a solid epoxy resin may be contained in combination, but only a liquid epoxy resin is preferably contained.
As the liquid epoxy resin, a liquid epoxy resin having 2 or more epoxy groups in 1 molecule is preferable.
As the liquid epoxy resin, bisphenol a type epoxy resin, bisphenol F type epoxy resin, bisphenol AF type epoxy resin, naphthalene type epoxy resin, glycidyl ester type epoxy resin, glycidyl amine type epoxy resin, phenol novolac type epoxy resin, alicyclic epoxy resin having an ester skeleton, cyclohexane type epoxy resin, cyclohexane dimethanol type epoxy resin, and epoxy resin having a butadiene structure are preferable.
Specific examples of the liquid epoxy resin include: "HP 4032", "HP 4032D" and "HP 4032 SS" (naphthalene epoxy resins) manufactured by DIC; "828 US", "828 EL", "jER 828 EL", "825", "EPIKOTE 828 EL" (bisphenol A type epoxy resin) manufactured by Mitsubishi chemical company; "jER 807" and "1750" (bisphenol F type epoxy resin) manufactured by Mitsubishi chemical corporation; "jER 152" (phenol novolac type epoxy resin) manufactured by mitsubishi chemical corporation; "630", "630 LSD" and "604" (glycidyl amine type epoxy resins) manufactured by Mitsubishi chemical company; "ED-523T" (glycidyl epoxy resin) manufactured by ADEKA corporation; "EP-3950L" and "EP-3980S" (glycidylamine-type epoxy resins) manufactured by ADEKA; EP-4088S (dicyclopentadiene type epoxy resin) manufactured by ADEKA Co; "ZX 1059" (a mixture of bisphenol A type epoxy resin and bisphenol F type epoxy resin) manufactured by Nissian Ciki Kaisha; "EX-721" (glycidyl ester type epoxy resin) manufactured by Nagase ChemteX; "Celloxide 2021P" (alicyclic epoxy resin having an ester skeleton) manufactured by Dailuo corporation; "PB-3600" manufactured by Daxylonite, JP-100 "and JP-200" manufactured by Nippon Caoda (a butadiene-structured epoxy resin); "ZX 1658" and "ZX 1658 GS" (liquid 1, 4-glycidylcyclohexane-type epoxy resins) manufactured by Nippon iron and Japan chemical Co., Ltd. These can be used alone in 1 kind, also can be combined with more than 2 kinds and use.
The solid epoxy resin is preferably a solid epoxy resin having 3 or more epoxy groups in 1 molecule, and more preferably an aromatic solid epoxy resin having 3 or more epoxy groups in 1 molecule.
As the solid epoxy resin, a biphenol-type epoxy resin, a naphthalene-type tetrafunctional epoxy resin, a cresol novolak-type epoxy resin, a dicyclopentadiene-type epoxy resin, a triphenol (trisphenols) -type epoxy resin, a naphthol-type epoxy resin, a biphenyl-type epoxy resin, a naphthylene ether-type epoxy resin, an anthracene-type epoxy resin, a bisphenol a-type epoxy resin, a bisphenol AF-type epoxy resin, and a tetraphenylethane-type epoxy resin are preferable.
Specific examples of the solid epoxy resin include: HP4032H (naphthalene epoxy resin) manufactured by DIC; "HP-4700" and "HP-4710" (naphthalene type tetrafunctional epoxy resins) manufactured by DIC; "N-690" (cresol novolac type epoxy resin) manufactured by DIC; "N-695" (cresol novolac type epoxy resin) manufactured by DIC; "HP-7200", "HP-7200 HH" and "HP-7200H" (dicyclopentadiene type epoxy resins) manufactured by DIC; "EXA-7311", "EXA-7311-G3", "EXA-7311-G4", "EXA-7311-G4S" and "HP 6000" (naphthylene ether type epoxy resins) manufactured by DIC corporation; EPPN-502H (trisphenol type epoxy resin) manufactured by Nippon chemical Co., Ltd.; "NC 7000L" (naphthol novolac type epoxy resin) manufactured by japan chemicals); "NC 3000H", "NC 3000L" and "NC 3100" (biphenyl type epoxy resin) manufactured by japan chemical company; ESN475V (naphthol type epoxy resin) manufactured by Nippon iron and gold Chemicals; ESN485 (naphthol novolac type epoxy resin) manufactured by Nippon iron and gold Chemicals, Ltd; "YX 4000H", "YX 4000", "YL 6121" (biphenyl type epoxy resin) manufactured by Mitsubishi chemical company; "YX 4000 HK" (bisphenol type epoxy resin) manufactured by Mitsubishi chemical corporation; YX8800 (anthracene-based epoxy resin) available from Mitsubishi chemical corporation; "YX 7700" (novolac-type epoxy resin containing a xylene structure) manufactured by mitsubishi chemical corporation; PG-100 and CG-500 manufactured by Osaka gas chemical company; "YL 7760" (bisphenol AF type epoxy resin) manufactured by Mitsubishi chemical corporation; "YL 7800" (fluorene-based epoxy resin) manufactured by Mitsubishi chemical corporation; "jER 1010" (solid bisphenol a type epoxy resin) manufactured by mitsubishi chemical corporation; "jER 1031S" (tetraphenylethane-type epoxy resin) manufactured by Mitsubishi chemical corporation, and the like. These can be used alone in 1 kind, also can be combined with more than 2 kinds and use.
In one embodiment, (a) the epoxy resin particularly preferably contains a liquid epoxy resin containing a condensed ring structure, and particularly preferably contains a liquid epoxy resin containing a naphthalene ring structure. Examples of the liquid epoxy resin having a condensed ring (particularly naphthalene ring) structure include, for example, those having a condensed ring (particularly naphthalene ring) structure as exemplified as the liquid epoxy resin.
(A) The content of the liquid epoxy resin in the epoxy resin is not particularly limited, and when the total amount of the epoxy resin (a) is 100% by mass, it is preferably 50% by mass or more and 60% by mass or more, more preferably 70% by mass or more and 75% by mass or more, further preferably 80% by mass or more and 85% by mass or more, further more preferably 90% by mass or more, 95% by mass or more and 98% by mass or more, and particularly preferably 100% by mass.
(A) The epoxy equivalent of the epoxy resin is preferably 50g/eq to 5000g/eq, more preferably 50g/eq to 2000g/eq, even more preferably 80g/eq to 1000g/eq, and even more preferably 80g/eq to 500g/eq. The epoxy equivalent is the mass of the resin containing 1 equivalent of epoxy group. The epoxy equivalent can be measured according to JIS K7236.
(A) The weight average molecular weight (Mw) of the epoxy resin is preferably 100 to 5000, more preferably 200 to 3000, and further preferably 250 to 1500. The weight average molecular weight of the resin can be measured as a value in terms of polystyrene by Gel Permeation Chromatography (GPC).
The content of the epoxy resin (a) in the resin composition is not particularly limited, and is preferably 10% by mass or more, more preferably 30% by mass or more, further preferably 40% by mass or more, and particularly preferably 50% by mass or more, when the nonvolatile components other than the inorganic filler (B) in the resin composition are taken as 100% by mass. The upper limit of the content of the epoxy resin (a) in the resin composition is not particularly limited, and when the nonvolatile component other than the inorganic filler (B) in the resin composition is 100 mass%, it may be, for example, 98 mass% or less, 95 mass% or less, 90 mass% or less, or the like.
(B) inorganic filler
The resin composition of the present invention contains (B) an inorganic filler.
(B) The material of the inorganic filler is not particularly limited, and examples thereof include: silica, alumina, glass, cordierite, silicon oxide, barium sulfate, barium carbonate, talc, clay, mica powder, zinc oxide, hydrotalcite, boehmite, aluminum hydroxide, magnesium hydroxide, calcium carbonate, magnesium oxide, boron nitride, aluminum nitride, manganese nitride, aluminum borate, strontium carbonate, strontium titanate, calcium titanate, magnesium titanate, bismuth titanate, titanium oxide, zirconium oxide, barium titanate, barium zirconate, zirconium phosphate, zirconium phosphotungstate, and the like. Silica and alumina are particularly preferred. Examples of the silica include amorphous silica, fused silica, crystalline silica, synthetic silica, hollow silica and the like. In addition, as the silica, spherical silica is preferable. (B) The inorganic filler may be used alone in 1 kind, or may be used in combination in 2 or more kinds.
Examples of commercially available products of the inorganic filler (B) include: UFP-30 manufactured by electrochemical chemical industry; "SP 60-05" and "SP 507-05" manufactured by Nissi iron-alloy materials Corp; "YC 100C", "YA 050C", "YA 050C-MJE", "YA 010C" manufactured by Admatech (Admatech); "UFP-30" manufactured by Denka corporation; "Silfil (シルフィル) NSS-3N", "Silfil NSS-4N" and "Silfil NSS-5N" manufactured by Deshan, Kuyama, K.K.; "SC 2500 SQ", "SO-C4", "SO-C2", "SO-C1" manufactured by Yadama corporation, "DAW-03" manufactured by Denka corporation, and "FB-105 FD" manufactured by Denka corporation.
(B) The average particle size of the inorganic filler is not particularly limited, but is preferably 40 μm or less, more preferably 20 μm or less, still more preferably 10 μm or less, still more preferably 5 μm or less, and particularly preferably 3 μm or less. The lower limit of the average particle size of the inorganic filler is not particularly limited, but is preferably 0.01 μm or more, more preferably 0.05 μm or more, further preferably 0.1 μm or more, further preferably 0.5 μm or more, further more preferably 1 μm or more, and particularly preferably 1.5 μm or more. The average particle diameter of the inorganic filler can be measured by a laser diffraction scattering method based on Mie scattering theory. Specifically, it can be determined by: the particle size distribution of the inorganic filler was prepared on a volume basis by using a laser diffraction scattering particle size distribution measuring apparatus, and the median particle size was defined as an average particle size. As the measurement sample, a sample obtained by: 100mg of the inorganic filler and 10g of methyl ethyl ketone were weighed into a vial, and dispersed for 10 minutes by ultrasonic waves. For the measurement sample, the volume-based particle size distribution of the inorganic filler was measured by a flow cell method using a laser diffraction type particle size distribution measuring apparatus with the wavelength of the light source used being blue and red, and the average particle size was calculated from the obtained particle size distribution as the median particle size. Examples of the laser diffraction type particle size distribution measuring apparatus include "LA-960" manufactured by horiba, Ltd.
(B) The specific surface area of the inorganic filler is not particularly limited, but is preferably 0.01m20.1 m/g or more20.5 m/g or more2A value of 1m or more, more preferably 1m2A total of 2m or more, preferably2A total of 3m or more, particularly 3m2More than g. The upper limit is not particularly limited, but is preferably 50m2A ratio of 20m or less per gram210m below/g2Less than or equal to 5 m/g2The ratio of the carbon atoms to the carbon atoms is less than g. The specific surface area of the inorganic filler material can be obtained by: according to the BET method, a BET full-automatic specific surface area measuring apparatus (Macsorb HM-1210, Mountech corporation) was used to adsorb nitrogen gas to the sample surface, and the specific surface area was calculated by the BET multipoint method.
From the viewpoint of improving moisture resistance and dispersibility, the inorganic filler (B) is preferably treated with 1 or more surface-treating agents such as an aminosilane-based coupling agent, an epoxysilane-based coupling agent, a mercaptosilane-based coupling agent, an alkoxysilane compound, an organosilazane compound, and a titanate-based coupling agent. Examples of commercially available surface treatment agents include: "KBM 403" (3-glycidoxypropyltrimethoxysilane) manufactured by shin-Etsu chemical industries, "KBM 803" (3-mercaptopropyltrimethoxysilane) manufactured by shin-Etsu chemical industries, "KBE 903" (3-aminopropyltriethoxysilane) manufactured by shin-Etsu chemical industries, "KBM 573" (N-phenyl-3-aminopropyltrimethoxysilane) manufactured by shin-Etsu chemical industries, "SZ-31" (hexamethyldisilazane) manufactured by shin-Etsu chemical industries, and "KBM 103" (phenyltrimethoxysilane) manufactured by shin-Etsu chemical industries, and "KBM-4803" (long-chain epoxy-type silane coupling agent) manufactured by shin-Etsu chemical industries, and "KBM-7103" (3,3, 3-trifluoropropyltrimethoxysilane) manufactured by shin-Etsu chemical industries, and "KBM 503" (3-methacryloxypropyltrimethoxysilane) manufactured by shin-Etsu chemical industries, KBM5783 manufactured by shin-Etsu chemical industries, Ltd.
From the viewpoint of improving the dispersibility of the inorganic filler, the degree of surface treatment by the surface treatment agent is preferably limited to a predetermined range. Specifically, the inorganic filler is preferably surface-treated with 0.2 to 5 mass%, preferably 0.2 to 3 mass%, and preferably 0.3 to 2 mass% of a surface treating agent with respect to 100 mass% of the inorganic filler.
The degree of surface treatment based on the surface treatment agent can be evaluated by the amount of carbon per unit surface area of the inorganic filler material. The amount of carbon per unit surface area of the inorganic filler is preferably 0.02mg/m from the viewpoint of improving dispersibility of the inorganic filler2Above, more preferably 0.1mg/m2Above, more preferably 0.2mg/m2The above. On the other hand, from the viewpoint of preventing the melt viscosity of the resin composition and the melt viscosity in the form of a sheet from increasing, it is preferably 1.0mg/m2The concentration is more preferably 0.8mg/m or less2The concentration is more preferably 0.5mg/m or less2The following.
(B) The amount of carbon per unit surface area of the inorganic filler can be measured after the inorganic filler after the surface treatment is washed with a solvent such as Methyl Ethyl Ketone (MEK). Specifically, a sufficient amount of MEK as a solvent may be added to the inorganic filler surface-treated with the surface treatment agent, and ultrasonic washing may be performed at 25 ℃ for 5 minutes. The supernatant liquid was removed, the solid content was dried, and then the amount of carbon per unit surface area of the inorganic filler was measured using a carbon analyzer. As the carbon analyzer, there may be used "EMIA-320V" manufactured by horiba, Ltd.
The content of the inorganic filler (B) in the resin composition is 70 mass% or more, preferably 72 mass% or more and 73 mass% or more, more preferably 74 mass% or more and 75 mass% or more, further preferably 76 mass% or more and 77 mass% or more, and particularly preferably 78 mass% or more, 79 mass% or more, or 80 mass% or more, when the total nonvolatile components in the resin composition are taken as 100 mass%. The upper limit of the content of the inorganic filler (B) in the resin composition is not particularly limited, and when the nonvolatile content of the whole resin composition is 100 mass%, the content may be, for example, 98 mass% or less, 95 mass% or less, 90 mass% or less, 85 mass% or less, or the like.
(C) curing agent
The resin composition of the present invention contains (C) a curing agent. (C) The curing agent has a function of curing the epoxy resin (A). The curing agent (C) is not a component of the non-epoxy compound (D) having a polyether skeleton.
The curing agent (C) is not particularly limited, and examples thereof include phenol curing agents, naphthol curing agents, acid anhydride curing agents, amine curing agents, active ester curing agents, benzoxazine curing agents, and cyanate curing agents. The curing agent may be used alone in 1 kind, or in combination of 2 or more kinds.
In one embodiment, the curing agent (C) preferably contains 1 or more curing agents selected from an acid anhydride curing agent and an amine curing agent.
As the phenol curing agent and the naphthol curing agent, a phenol curing agent having a phenol resin (novolac) structure or a naphthol curing agent having a phenol resin structure is preferable from the viewpoint of heat resistance and water resistance. From the viewpoint of adhesion to an adherend, a nitrogen-containing phenol curing agent or a nitrogen-containing naphthol curing agent is preferable, and a triazine skeleton-containing phenol curing agent or a triazine skeleton-containing naphthol curing agent is more preferable. Among them, a phenol novolac resin containing a triazine skeleton is preferable from the viewpoint of satisfying heat resistance, water resistance, and adhesion at a high level. Specific examples of the phenol-based curing agent and the naphthol-based curing agent include: "MEH-7700", "MEH-7810", "MEH-7851" manufactured by Minghe Kaisha, "NHN", "CBN", "GPH" manufactured by Nippon Steel Chemical Co., Ltd., "SN-170", "SN-180", "SN-190", "SN-475", "SN-485", "SN-495", "SN-375", "SN-395", "LA-7052", "LA-7054", "LA-3018-50P", "LA-1356", "TD 2090", "TD-2090-60M" manufactured by Nippon Steel Chemical Co., Ltd., "manufactured by Nippon Chemical Co., Ltd".
Examples of the acid anhydride-based curing agent include a curing agent having 1 or more acid anhydride groups in 1 molecule, and preferably a curing agent having 2 or more acid anhydride groups in 1 molecule. Specific examples of the acid anhydride-based curing agent include: phthalic anhydride, tetrahydrophthalic anhydride, hexahydrophthalic anhydride, methyltetrahydrophthalic anhydride, methylhexahydrophthalic anhydride, methylnadic anhydride, hydrogenated methylnadic anhydride, trialkyltetrahydrophthalic anhydride, dodecenylsuccinic anhydride, 5- (2, 5-dioxotetrahydro-3-furanyl) -3-methyl-3-cyclohexene-1, 2-dicarboxylic anhydride, trimellitic anhydride, pyromellitic anhydride, benzophenone tetracarboxylic dianhydride, biphenyl tetracarboxylic dianhydride, naphthalene tetracarboxylic dianhydride, oxydiphthalic dianhydride, 3,3'-4,4' -diphenylsulfone tetracarboxylic dianhydride, 1,3,3a,4,5,9 b-hexahydro-5- (tetrahydro-2, 5-dioxo-3-furanyl) -naphtho [1,2-C furan-1, 3-dione, ethylene glycol bis (trimellitic anhydride ester), styrene-maleic acid resin obtained by copolymerizing styrene with maleic acid, and other polymer type acid anhydrides. Examples of commercially available acid anhydride-based curing agents include "HNA-100", "MH-700", "MTA-15", "DDSA", "OSA" manufactured by Nippon chemical Co., Ltd "," YH-306 "," YH-307 "manufactured by Mitsubishi chemical Co., Ltd", "HN-2200" and "HN-5500" manufactured by Hitachi chemical Co., Ltd.
Examples of the amine-based curing agent include those having 1 or more, preferably 2 or more, amino groups in 1 molecule, and examples thereof include aliphatic amines, polyether amines, alicyclic amines, aromatic amines, and the like, and among them, aromatic amines are preferable from the viewpoint of exhibiting the desired effect of the present invention. The amine-based curing agent is preferably a primary amine or a secondary amine, and more preferably a primary amine. Specific examples of the amine-based curing agent include: 4,4' -methylenebis (2, 6-dimethylaniline), 4' -diaminodiphenylmethane, 4' -diaminodiphenylsulfone, 3' -diaminodiphenylsulfone, m-phenylenediamine, m-xylylenediamine, diethyltoluenediamine, 4' -diaminodiphenyl ether, 3' -dimethyl-4, 4' -diaminobiphenyl, 2' -dimethyl-4, 4' -diaminobiphenyl, 3' -dihydroxybenzidine, 2-bis (3-amino-4-hydroxyphenyl) propane, 3-dimethyl-5, 5-diethyl-4, 4-diphenylmethanediamine, 2-bis (4-aminophenyl) propane, 2, 4' -diaminodiphenylmethanediamine, 4-diaminodiphenylmethanediamine, and mixtures thereof, 2, 2-bis (4- (4-aminophenoxy) phenyl) propane, 1, 3-bis (3-aminophenoxy) benzene, 1, 3-bis (4-aminophenoxy) benzene, 1, 4-bis (4-aminophenoxy) benzene, 4' -bis (4-aminophenoxy) biphenyl, bis (4- (4-aminophenoxy) phenyl) sulfone, bis (4- (3-aminophenoxy) phenyl) sulfone and the like. As the amine-based curing agent, commercially available ones can be used, and examples thereof include: "SEIKACURE-S" manufactured by SEIKA, KAYABOND C-200S "manufactured by Japan Chemicals, KAYABOND C-100", KAYAHARD A-A ", KAYAHARD A-B", KAYAHARD A-S "manufactured by Mitsubishi chemical, and" Epicure (エピキュア) W "manufactured by Mitsubishi chemical.
The active ester-based curing agent is not particularly limited, and compounds having 2 or more ester groups having high reactivity in 1 molecule, such as phenol esters, thiophenol esters, N-hydroxylamine esters, and esters of heterocyclic hydroxy compounds, can be preferably used. The active ester curing agent is preferably obtained by a condensation reaction of a carboxylic acid compound and/or a thiocarboxylic acid compound with a hydroxyl compound and/or a thiol compound. In particular, from the viewpoint of improving heat resistance, an active ester-based curing agent obtained from a carboxylic acid compound and a hydroxyl compound is preferable, and an active ester-based curing agent obtained from a carboxylic acid compound and a phenol compound and/or a naphthol compound is more preferable. Examples of the carboxylic acid compound include benzoic acid, acetic acid, succinic acid, maleic acid, itaconic acid, phthalic acid, isophthalic acid, terephthalic acid, and pyromellitic acid. Examples of the phenol compound or naphthol compound include hydroquinone, resorcinol, bisphenol a, bisphenol F, bisphenol S, phenolphthalin, methylated bisphenol a, methylated bisphenol F, methylated bisphenol S, phenol, o-cresol, m-cresol, p-cresol, catechol, α -naphthol, β -naphthol, 1, 5-dihydroxynaphthalene, 1, 6-dihydroxynaphthalene, 2, 6-dihydroxynaphthalene, dihydroxybenzophenone, trihydroxybenzophenone, tetrahydroxybenzophenone, phloroglucinol, benzenetriol, dicyclopentadiene type diphenol compound, phenol novolac resin (phenol novolac), and the like. Here, the "dicyclopentadiene type diphenol compound" refers to a diphenol compound obtained by condensing 1 molecule of dicyclopentadiene with 2 molecules of phenol.
Specifically, it is preferable that: an active ester compound containing a dicyclopentadiene type diphenol structure, an active ester compound containing a naphthalene structure, an active ester compound containing an acetyl compound of a phenol novolac resin, an active ester compound containing a benzoyl compound of a phenol novolac resin, and among them, an active ester compound containing a naphthalene structure, an active ester compound containing a dicyclopentadiene type diphenol structure are more preferable. The "dicyclopentadiene type diphenol structure" refers to a divalent structural unit formed from phenylene-dicyclopentanalene-phenylene.
Commercially available products of the active ester-based curing agent include: "EXB 9451", "EXB 9460S", "HPC-8000H", "HPC-8000-65T", "HPC-8000H-65 TM", "EXB-8000L-65L", "EXB-8000L-65 TM" (manufactured by DIC) as an active ester compound having a dicyclopentadiene type diphenol structure; "EXB-9416-70 BK", "EXB-8150-65T", "EXB-8100L-65T", "EXB-8150L-65T" (manufactured by DIC) as an active ester compound having a naphthalene structure; "DC 808" (manufactured by mitsubishi chemical corporation) as an active ester-based curing agent which is an acetylated product of a phenol novolac resin; "YLH 1026" (manufactured by mitsubishi chemical corporation), "YLH 1030" (manufactured by mitsubishi chemical corporation), and "YLH 1048" (manufactured by mitsubishi chemical corporation), which are active ester-based curing agents that are benzoylates of phenol novolac resins; and so on.
Specific examples of the benzoxazine-based curing agent include: "JBZ-OP 100D" and "ODA-BOZ" manufactured by JFE chemical company; "HFB 2006M" available from Showa Polymer Co; "P-d" and "F-a" manufactured by four national chemical industries, Inc.
Examples of the cyanate ester-based curing agent include: bifunctional cyanate ester resins such as bisphenol a dicyanate, polyphenol cyanate ester (oligo (3-methylene-1, 5-phenylene cyanate)), 4 '-methylenebis (2, 6-dimethylphenyl cyanate), 4' -ethylenediphenyldicyanate, hexafluorobisphenol a dicyanate, 2-bis (4-cyanate ester) phenylpropane, 1-bis (4-cyanate ester phenylmethane), bis (4-cyanate ester-3, 5-dimethylphenyl) methane, 1, 3-bis (4-cyanate ester-phenyl-1- (methylethylidene)) benzene, bis (4-cyanate ester-phenyl) sulfide, and bis (4-cyanate ester-phenyl) ether; polyfunctional cyanate ester resins derived from phenol novolac resins, cresol novolac resins, and the like; prepolymers obtained by partially triazinating these cyanate ester resins; and so on. Specific examples of the cyanate ester-based curing agent include "PT 30" and "PT 60" (both of which are phenol novolac type polyfunctional cyanate ester resins), "BA 230" and "BA 230S 75" (prepolymers obtained by triazinating a part or all of bisphenol a dicyanate ester to form a trimer), which are manufactured by Lonza Japan.
When the resin composition contains (a) an epoxy resin and (C) a curing agent, the amount ratio of (a) the epoxy resin to (C) the curing agent is represented by [ (a) the number of epoxy groups of the epoxy resin ]: the ratio of [ (number of reaction of C) curing agent ], is preferably 1: 0.2-1: 2, more preferably 1: 0.3-1: 1.5, more preferably 1: 0.4-1: 1.4. here, the reactive group of the (C) curing agent differs depending on the type of the curing agent, and for example, if the curing agent is a phenol-based curing agent or a naphthol-based curing agent, the reactive group of the (C) curing agent is an aromatic hydroxyl group, and if the curing agent is an active ester-based curing agent, the reactive group of the (C) curing agent is an active ester group.
(C) The reaction group equivalent of the curing agent is preferably 50g/eq to 3000g/eq, more preferably 100g/eq to 1000g/eq, even more preferably 100g/eq to 500g/eq, and particularly preferably 100g/eq to 300g/eq. The reactive group equivalent is the mass of the curing agent relative to 1 equivalent of the reactive group.
The content of the curing agent (C) in the resin composition is not particularly limited, and is preferably 80% by mass or less, more preferably 60% by mass or less, further preferably 50% by mass or less, and particularly preferably 40% by mass or less, when the nonvolatile components other than the inorganic filler (B) in the resin composition are assumed to be 100% by mass. The lower limit of the content of the curing agent (C) in the resin composition is not particularly limited, and is, for example, 0.001 mass% or more, 0.01 mass% or more, 0.1 mass% or more, 1 mass% or more, or 2 mass% or more, where 100 mass% is a nonvolatile component other than the inorganic filler (B) in the resin composition.
< (D) a non-epoxy compound having a polyether skeleton
The resin composition of the present invention contains (D) a non-epoxy compound having a polyether skeleton.
(D) The non-epoxy compound having a polyether skeleton means a polymer compound having a polyether skeleton which does not contain an epoxy group, and (D) the polyether skeleton contained in the non-epoxy compound having a polyether skeleton is a polyoxyalkylene skeleton composed of 1 or more monomer units selected from an ethylene oxide unit and a propylene oxide unit, and does not include a polyether skeleton containing a monomer unit having 4 or more carbon atoms such as a butylene oxide unit and a phenylene oxide unit. (D) The polyether skeleton contained in the non-epoxy compound having a polyether skeleton is particularly preferably a polyoxyalkylene skeleton composed of an ethylene oxide unit or a polyoxyalkylene skeleton composed of two monomer units of an ethylene oxide unit and a propylene oxide unit.
(D) The average polymerization degree of the monomer unit in the polyether skeleton contained in the non-epoxy compound having a polyether skeleton is preferably 300 or less, more preferably 200 or less, further preferably 100 or less, and particularly preferably 80 or less.
In one embodiment, (D) the non-epoxy compound having a polyether skeleton may have an organosilicon (silicone) skeleton. The silicone skeleton is not particularly limited, and examples thereof include: a polydialkylsiloxane skeleton such as a polydimethylsiloxane skeleton; polydiarylsiloxane backbones such as polydiphenylsiloxane backbones; polyalkylaryl siloxane skeletons such as polymethylphenylsiloxane skeletons; a polydialkyl-diarylsiloxane skeleton such as a polydimethyl-diphenylsiloxane skeleton; a polydialkyl-alkylaryl siloxane backbone such as a polydimethyl-methylphenyl siloxane backbone; polydiaryl-alkylaryl siloxane backbone such as polydiphenyl-methylphenyl siloxane backbone, etc., polydialkylsiloxane backbone is preferred, and polydimethylsiloxane backbone is particularly preferred. The component (D) having a silicone skeleton may be a polyoxyalkylene-modified silicone, an alkyl etherified polyoxyalkylene-modified silicone (a polyoxyalkylene-modified silicone in which at least a part of the terminal of a polyether skeleton is an alkoxy group), or the like. In one embodiment, (D) the non-epoxy compound having a polyether skeleton may have a hydroxyl group.
Examples of the non-epoxy compound having a polyether skeleton (D) include: linear polyoxyalkylene glycols (linear polyalkylene glycols) such as polyethylene glycol, polypropylene glycol, and polyoxyethylene polyoxypropylene glycol; polyoxyalkylene glycols (polyalkylene glycols) such as multi-chain polyoxyalkylene glycols (multi-chain polyalkylene glycols) such as polyoxyethylene glyceryl ether, polyoxypropylene glyceryl ether, polyoxyethylene trimethylolpropane ether, polyoxyethylene polyoxypropylene trimethylolpropane ether, polyoxyethylene diglyceryl ether, polyoxypropylene diglyceryl ether, polyoxyethylene pentaerythritol ether, polyoxypropylene pentaerythritol ether, polyoxyethylene sorbitol (ソルビット), polyoxypropylene sorbitol, and polyoxyethylene polyoxypropylene sorbitol; polyoxyalkylene alkyl ethers such as polyoxyethylene monoalkyl ether, polyoxyethylene dialkyl ether, polyoxypropylene monoalkyl ether, polyoxypropylene dialkyl ether, polyoxyethylene polyoxypropylene monoalkyl ether, and polyoxyethylene polyoxypropylene dialkyl ether; polyoxyalkylene esters (including acetate, propionate, butyrate, (meth) acrylate, and the like) such as polyoxyethylene monoester, polyoxyethylene diester, polypropylene glycol monoester, polypropylene glycol diester, polyoxyethylene polyoxypropylene monoester, and polyoxyethylene polyoxypropylene diester; polyoxyalkylene alkyl ether esters (including acetate, propionate, butyrate, (meth) acrylate, and the like) such as polyoxyethylene monoester, polyoxyethylene diester, polyoxypropylene monoester, polyoxypropylene diester, polyoxyethylene polyoxypropylene monoester, polyoxyethylene polyoxypropylene diester, polyoxyethylene alkyl ether ester, polyoxypropylene alkyl ether ester, and polyoxyethylene polyoxypropylene alkyl ether ester; polyoxyalkylene alkylamines such as polyoxyethylene alkylamine, polyoxypropylene alkylamine, and polyoxyethylene polyoxypropylene alkylamine; polyoxyalkylene alkylamides such as polyoxyethylene alkylamides, polyoxypropylene alkylamides and polyoxyethylene polyoxypropylene alkylamides; polyoxyalkylene-modified silicones such as polyoxyethylene dimethylsilicone (dimethicone), polyoxypropylene dimethylsilicone, polyoxyethylene polydimethylsiloxy (siloxy) alkyldimethylsilicone, polyoxypropylene polydimethylsiloxy alkyldimethylsilicone, polyoxyethylene polyoxypropylene polydimethylsiloxy alkyldimethylsilicone and the like; and alkyl ether polyoxyalkylene-modified silicones (polyoxyalkylene-modified silicones wherein at least a part of the terminal of the polyether skeleton is an alkoxy group), such as polyoxyethylene alkyl ether dimethylsilicone fluids, polyoxypropylene alkyl ether dimethylsilicone fluids, polyoxyethylene polyoxypropylene alkyl ether dimethylsiloxane fluids, polyoxyethylene polyoxypropylene alkyl ether polydimethylsiloxyalkyl dimethylsilicone fluids, and polyoxyethylene polyoxypropylene alkyl ether polydimethylsiloxyalkyl dimethylsilicone fluids.
(D) The non-epoxy compound having a polyether skeleton is preferably at least 1 compound selected from the group consisting of polyoxyalkylene glycol (polyalkylene glycol) and polyoxyalkylene-modified silicone.
In one embodiment, the polyoxyalkylene glycol (polyalkylene glycol) is preferably a linear type polyoxyalkylene glycol (linear type polyalkylene glycol).
The average degree of polymerization of the monomer unit in the polyoxyalkylene glycol (polyalkylene glycol) is preferably 300 or less, more preferably 200 or less, still more preferably 100 or less, and particularly preferably 80 or less. The lower limit is preferably 5 or more, more preferably 10 or more, further preferably 20 or more, and particularly preferably 30 or more.
The polyoxyalkylene glycol (polyalkylene glycol) is particularly preferably polyoxyethylene polyoxypropylene glycol. Polyoxyethylene polyoxypropylene glycols include: polyoxyethylene-polyoxypropylene block copolymers, polyoxyethylene-polyoxypropylene-polyoxyethylene block copolymers, polyoxypropylene-polyoxyethylene-polyoxypropylene block copolymers, and the like.
The average polymerization degree of the oxyethylene unit in the polyoxyethylene polyoxypropylene glycol is preferably 200 or less, more preferably 100 or less, still more preferably 50 or less, and particularly preferably 30 or less. The lower limit is preferably 3 or more, more preferably 5 or more, further preferably 10 or more, and particularly preferably 15 or more. The average polymerization degree of the propylene oxide unit in the polyoxyethylene polyoxypropylene glycol is preferably 200 or less, more preferably 100 or less, still more preferably 50 or less, and particularly preferably 40 or less. The lower limit is preferably 3 or more, more preferably 5 or more, further preferably 10 or more, and particularly preferably 15 or more.
In one embodiment, the (D) non-epoxy compound having a polyether skeleton is preferably a compound represented by formula (1).
[ chemical formula 1]
Particularly preferred is a compound represented by the formula (1').
[ chemical formula 2]
I.e., a block copolymer of x1 units, x2 units, and x3 units.
In the formula (1), 2R1Each independently represents a hydrogen atom, an alkyl group (preferably having 1 to 6 carbon atoms), an alkenyl group (preferably having 2 to 6 carbon atoms), an alkyl-carbonyl group (preferably having 2 to 7 carbon atoms), or an alkenyl-carbonyl group (preferably having 3 to 7 carbon atoms). 2R1Particularly preferred is a hydrogen atom. The alkyl group means a linear, branched and/or cyclic monovalent aliphatic saturated hydrocarbon group. Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, an isopentyl group, a neopentyl group, a sec-pentyl group, a tert-pentyl group, a cyclopentyl group, and a cyclohexyl group. The alkenyl group means a straight-chain, branched-chain and/or cyclic monovalent aliphatic unsaturated hydrocarbon group having at least 1 carbon-carbon double bond. Examples of the alkenyl group include a vinyl group, a 1-propenyl group, and a 2-propenyl group.
In the formula (1), n is each independently 2 or 3.
In the formula (1), x represents an integer of 5 to 300. x is preferably an integer of 5 to 200, and particularly preferably an integer of 10 to 100.
In the formula (1'), x1 and x3 are each independently an integer of 3 to 200. x1 and x3 are preferably each independently an integer of 3 to 100.
In the formula (1'), x2 is an integer of 3 to 200. x2 is preferably an integer of 5 to 100.
In one embodiment, the polyoxyalkylene-modified silicone is, for example, a linear or branched dimethylpolysiloxane (dimethicone) having 1 or 2 or more polyoxyalkylene chains, and is preferably polyoxyethylene dimethicone or polyoxyethylene polydimethylsiloxyalkyl dimethicone.
The average polymerization degree of the monomer units having 1 polyoxyalkylene chain in the polyoxyalkylene-modified silicone is preferably 30 or less, more preferably 20 or less, still more preferably 15 or less, and particularly preferably 10 or less. The lower limit is preferably 2 or more.
In one embodiment, the (D) non-epoxy compound having a polyether skeleton is preferably a polyoxyalkylene-modified silicone represented by formula (2).
[ chemical formula 3]
In the formula (2), a represents an integer of 2 to 10000.
a is preferably an integer of 2 to 5000, more preferably an integer of 2 to 1000, further preferably an integer of 2 to 500, and particularly preferably an integer of 2 to 200.
In the formula (2), 4+ a of R2Each independently represents an alkyl group (preferably having 1 to 6 carbon atoms), an aralkyl group (preferably having 7 to 15 carbon atoms), or an aryl group (preferably having 6 to 14 carbon atoms). 4+ a R2Each independently is preferably an alkyl group (preferably having 1 to 6 carbon atoms), and particularly preferably a methyl group. The aryl group means a monovalent aromatic hydrocarbon group. Examples of the aryl group include a phenyl group, a 1-naphthyl group, and a 2-naphthyl group, and a phenyl group is preferable. The aralkyl group means an alkyl group substituted with 1 or 2 or more aryl groups. Examples of the aralkyl group include a benzyl group, a phenethyl group, and a 2-naphthylmethyl group.
In the formula (2), 2R3And a R4Each independently represents an alkyl group (preferably having 1 to 6 carbon atoms), an aralkyl group (preferably having 7 to 15 carbon atoms), an aryl group (preferably having 6 to 14 carbon atoms), a group represented by the formula (X), or a group represented by the formula (Y), and 2R3And a R4At least 1 of them is a group represented by the formula (X).
[ chemical formula 4]
[ chemical formula 5]
Preferably, 2R3Each independently is an alkyl group (preferably having 1 to 6 carbon atoms), an aralkyl group (preferably having 7 to 15 carbon atoms), or an aryl group (preferably having 6 to 14 carbon atoms), a R4Each independently is an alkyl group (preferably having 1 to 6 carbon atoms), an aralkyl group (preferably having 7 to 15 carbon atoms), an aryl group (preferably having 6 to 14 carbon atoms), a group represented by the formula (X), or a group represented by the formula (Y), and a R4At least 1 of them is a group represented by the formula (X).
More preferably, 2R3Each independently of the other being methyl, a R4Each independently is methyl, a group represented by formula (X), or a group represented by formula (Y), and a R4At least 1 of them is a group represented by the formula (X).
In the formula (2), the group represented by the formula (X) is preferably present in 1 to 20, more preferably 1 to 10, and particularly preferably 1 to 5. In the formula (2), the number of the groups represented by the formula (Y) is preferably 0 to 20, more preferably 0 to 10, and particularly preferably 0 to 5.
In the formulae (X) and (Y), a represents a bonding portion.
In the formula (X), R1And n is independently from R in formula (1)1And n is as defined.
In the formula (X), X represents a single bond or an alkylene group (preferably having 1 to 6 carbon atoms). The alkylene group means a linear, branched and/or cyclic divalent aliphatic saturated hydrocarbon group. Examples of the alkylene group include a methylene group, an ethylene group, a1, 3-propylene group, a1, 4-butylene group, a1, 5-pentylene group, and a1, 6-hexylene group.
In the formula (X), y represents an integer of 2 to 300. y is preferably an integer of 2 to 100, more preferably an integer of 2 to 50, and particularly preferably an integer of 2 to 20.
In the formula (Y), b represents an integer of 1 to 10000. b is preferably an integer of 1 to 1000, more preferably an integer of 1 to 500, further preferably an integer of 1 to 200, and particularly preferably an integer of 1 to 100.
In the formula (Y), 3+2b R5Each independently represents an alkyl group (preferably having 1 to 6 carbon atoms), an aralkyl group (preferably having 7 to 15 carbon atoms), or an aryl group (preferably having 6 to 14 carbon atoms). 3+2b R5Each independently is preferably an alkyl group (preferably having 1 to 6 carbon atoms), and particularly preferably a methyl group.
In the formula (Y), Y represents an alkylene group (preferably having 1 to 6 carbon atoms).
(D) The number average molecular weight of the non-epoxy compound having a polyether skeleton is preferably 500 to 40000, more preferably 500 to 20000, and still more preferably 500 to 10000. (D) The weight average molecular weight of the non-epoxy compound containing a polyether skeleton is preferably 500 to 40000, more preferably 500 to 20000, and further preferably 500 to 10000. The number average molecular weight and the weight average molecular weight can be measured as values in terms of polystyrene by Gel Permeation Chromatography (GPC).
(D) The non-epoxy compound containing a polyether backbone is preferably liquid at 25 ℃. (D) The viscosity of the non-epoxy compound having a polyether skeleton at 25 ℃ is preferably 100000 mPas or less, more preferably 50000 mPas or less, further preferably 10000 mPas or less, further preferably 5000 mPas or less, further preferably 4000 mPas or less, or 3000 mPas or less, particularly preferably 2000 mPas or less, or 1500 mPas or less. (D) The lower limit of the viscosity at 25 ℃ of the non-epoxy compound having a polyether skeleton is preferably 10 mPas or more, more preferably 20 mPas or more, further preferably 30 mPas or more, further more preferably 40 mPas or more, and particularly preferably 50 mPas or more. The viscosity can be measured with a B-type viscometer (mPa · s).
Examples of the non-epoxy compound having a polyether skeleton (D) include: "PLONON # 102", "PLONON # 104", "PLONON # 201", "PLONON # 202B", "PLONON # 204", "PLONON # 208", "UNILUBE 70 DP-600B", "UNILUBE 70 DP-950B" (polyoxyethylene polyoxypropylene glycol) manufactured by Nichigan; "PLURONIC (プルロニック) L-23", "PLURONIC L-31", "PLURONIC L-44", "PLURONIC L-61", "ADEKA PLURONIC L-62", "PLURONIC L-64", "PLURONIC L-71", "PLURONIC L-72", "PLURONIC L-101", "PLURONIC L-121", "PLURONIC P-84", "PLURONIC P-85", "PLURONIC P-103", "PLURONIC F-68", "PLURONIC F-88", "PLURONIC F-108", "PLURONIC 25R-1", "PLURONIC 25R-2", "PLURONIC 17R-3", "PLURONIC 17R-4" (polyoxyethylene polyoxypropylene glycol) manufactured by ADEKA; "KF-6011", "KF-6011P", "KF-6012", "KF-6013", "KF-6015", "KF-6016", "KF-6017P", "KF-6043", "KF-6004", "KF 351A", "KF 352A", "KF 353", "KF 354L", "KF 355A", "KF 615A", "KF 945", "KF-640", "KF-642", "KF-643", "KF-644", "KF-6020", "KF-6204", "X22-4515", "KF-6028P", "KF-6038", "KF-6048" and "KF-6025" (polyoxyalkylene modified silicone) manufactured by shin-Etsu Silicones.
The content of the polyether skeleton-containing non-epoxy compound (D) in the resin composition is 1 mass% or more, preferably 2 mass% or more, more preferably 3 mass% or more, further preferably 4 mass% or more, and particularly preferably 5 mass% or more, assuming that the nonvolatile components other than the inorganic filler (B) in the resin composition are 100 mass%. The upper limit of the content of the polyether skeleton-containing non-epoxy compound (D) in the resin composition is 30% by mass or less, preferably 27% by mass or less, more preferably 25% by mass or less, further preferably 23% by mass or less, and particularly preferably 22% by mass or less, assuming that the nonvolatile components other than the inorganic filler (B) in the resin composition are 100% by mass.
(E) curing Accelerator
The resin composition of the present invention may contain (E) a curing accelerator as an optional nonvolatile component. (E) The curing accelerator has a function of accelerating curing of the epoxy resin (a). The curing accelerator (E) is a component which is not a non-epoxy compound having a polyether skeleton (D).
(E) The curing accelerator preferably contains at least 1 selected from the group consisting of a phosphorus-based curing accelerator, a urea-based curing accelerator, a guanidine-based curing accelerator, an imidazole-based curing accelerator, a metal-based curing accelerator, and an amine-based curing accelerator, and more preferably contains an imidazole-based curing accelerator.
Examples of the phosphorus-based curing accelerator include: aliphatic phosphonium salts such as tetrabutylphosphonium bromide, tetrabutylphosphonium chloride, tetrabutylphosphonium acetate, tetrabutylphosphonium decanoate, tetrabutylphosphonium laurate, bis (tetrabutylphosphonium) pyromellitate, tetrabutylphosphonium hexahydrophthalate, tetrabutylphosphonium 2, 6-bis [ (2-hydroxy-5-methylphenyl) methyl ] -4-methylphenolate, di-t-butylmethylphosphonium tetraphenylborate and the like; aromatic phosphonium salts such as methyltriphenylphosphonium bromide, ethyltriphenylphosphonium bromide, propyltriphenylphosphonium bromide, butyltriphenylphosphonium bromide, benzyltriphenylphosphonium chloride, tetraphenylphosphonium bromide, p-tolyltriphenylphosphonium tetra-p-tolylborate, tetraphenylphosphonium tetraphenylborate, tetraphenylphosphonium tetra-p-tolylborate, triphenylethylphosphonium tetraphenylborate, tris (3-methylphenyl) ethylphosphonium tetraphenylborate, tris (2-methoxyphenyl) ethylphosphonium tetraphenylborate, (4-methylphenyl) triphenylphosphonium thiocyanate, tetraphenylphosphonium thiocyanate, butyltriphenylphosphonium thiocyanate and the like; aromatic phosphine-borane complexes such as triphenylphosphine-triphenylborane; an aromatic phosphine-quinone addition reaction product such as a triphenylphosphine-p-benzoquinone addition reaction product; aliphatic phosphines such as tributylphosphine, tri-tert-butylphosphine, trioctylphosphine, di-tert-butyl (2-butenyl) phosphine, di-tert-butyl (3-methyl-2-butenyl) phosphine, and tricyclohexylphosphine; dibutylphenylphosphine, di-t-butylphenyl phosphine, methyldiphenylphosphine, ethyldiphenylphosphine, butyldiphenylphosphine, diphenylcyclohexylphosphine, triphenylphosphine, tri-o-tolylphosphine, tri-m-tolylphosphine, tri-p-tolylphosphine, tri (4-ethylphenyl) phosphine, tri (4-propylphenyl) phosphine, tri (4-isopropylphenyl) phosphine, tri (4-butylphenyl) phosphine, tri (4-t-butylphenyl) phosphine, tri (2, 4-dimethylphenyl) phosphine, tri (2, 5-dimethylphenyl) phosphine, tri (2, 6-dimethylphenyl) phosphine, tri (3, 5-dimethylphenyl) phosphine, tri (2,4, 6-trimethylphenyl) phosphine, tri (2, 6-dimethyl-4-ethoxyphenyl) phosphine, tri (2-methoxyphenyl) phosphine, triphenylphosphine, tri (4-t-butylphenyl) phosphine, tri (4-methylphenyl), And aromatic phosphines such as tris (4-methoxyphenyl) phosphine, tris (4-ethoxyphenyl) phosphine, tris (4-tert-butoxyphenyl) phosphine, diphenyl-2-pyridylphosphine, 1, 2-bis (diphenylphosphino) ethane, 1, 3-bis (diphenylphosphino) propane, 1, 4-bis (diphenylphosphino) butane, 1, 2-bis (diphenylphosphino) acetylene, and 2,2' -bis (diphenylphosphino) diphenyl ether.
Examples of the urea-based curing accelerator include: 1, 1-dimethylurea; aliphatic dimethylureas such as 1,1, 3-trimethylurea, 3-ethyl-1, 1-dimethylurea, 3-cyclohexyl-1, 1-dimethylurea, and 3-cyclooctyl-1, 1-dimethylurea; 3-phenyl-1, 1-dimethylurea, 3- (4-chlorophenyl) -1, 1-dimethylurea, 3- (3, 4-dichlorophenyl) -1, 1-dimethylurea, 3- (3-chloro-4-methylphenyl) -1, 1-dimethylurea, 3- (2-methylphenyl) -1, 1-dimethylurea, 3- (4-methylphenyl) -1, 1-dimethylurea, 3- (3, 4-dimethylphenyl) -1, 1-dimethylurea, 3- (4-isopropylphenyl) -1, 1-dimethylurea, 3- (4-methoxyphenyl) -1, 1-dimethylurea, methyl-3-hydroxyurea, methyl-3-methyl-1-dimethylurea, methyl-3-methyl-4-methylphenyl-1-dimethylurea, methyl-3-methyl-1-dimethylurea, methyl-3-methyl-1-dimethylurea, methyl-3-1-methyl-1-dimethylurea, methyl-3-methyl-1-dimethylurea, methyl-1-methyl-urea, methyl-2-methyl-urea, and mixtures thereof, Aromatic dimethylureas such as 3- (4-nitrophenyl) -1, 1-dimethylurea, 3- [4- (4-methoxyphenoxy) phenyl ] -1, 1-dimethylurea, 3- [4- (4-chlorophenoxy) phenyl ] -1, 1-dimethylurea, 3- [3- (trifluoromethyl) phenyl ] -1, 1-dimethylurea, N- (1, 4-phenylene) bis (N ', N' -dimethylurea), and N, N- (4-methyl-1, 3-phenylene) bis (N ', N' -dimethylurea) [ tolylbisdimethylurea ].
Examples of the guanidine-based curing accelerator include: dicyandiamide, 1-methylguanidine, 1-ethylguanidine, 1-cyclohexylguanidine, 1-phenylguanidine, 1- (o-tolyl) guanidine, dimethylguanidine, diphenylguanidine, trimethylguanidine, tetramethylguanidine, pentamethylguanidine, 1,5, 7-triazabicyclo [4.4.0] dec-5-ene, 7-methyl-1, 5, 7-triazabicyclo [4.4.0] dec-5-ene, 1-methylbiguanide, 1-ethylbiguanide, 1-n-butylbiguanide, 1-n-octadecyl biguanide, 1-dimethylbiguanide, 1-diethylbiguanide, 1-cyclohexylbiguanide, 1-allylbiguanide, 1-phenylbiguanide, 1- (o-tolyl) biguanide and the like.
Examples of the imidazole-based curing accelerator include: 2-methylimidazole, 2-undecylimidazole, 2-heptadecylimidazole, 1, 2-dimethylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole, 2-phenyl-4-methylimidazole, 1-benzyl-2-phenylimidazole, 1-cyanoethyl-2-methylimidazole, 1-cyanoethyl-2-undecylimidazole, 1-cyanoethyl-2-ethyl-4-methylimidazole, 1-cyanoethyl-2-phenylimidazole, 1-cyanoethyl-2-undecylimidazolium trimellitate, tris (meth) acrylate ester, or a mixture thereof, 1-cyanoethyl-2-phenylimidazolium trimellitate, 2, 4-diamino-6- [2' -methylimidazolyl- (1') ] -ethyl-s-triazine, 2, 4-diamino-6- [2' -undecylimidazolyl- (1') ] -ethyl-s-triazine, 2, 4-diamino-6- [2' -ethyl-4 ' -methylimidazolyl- (1') ] -ethyl-s-triazine, 2, 4-diamino-6- [2' -methylimidazolyl- (1') ] -ethyl-s-triazine isocyanuric acid adduct, 2-phenylimidazole isocyanuric acid adduct, 2-phenyl-4, imidazole compounds such as 5-dihydroxymethylimidazole, 2-phenyl-4-methyl-5-hydroxymethylimidazole, 2, 3-dihydro-1H-pyrrolo [1,2-a ] benzimidazole, 1-dodecyl-2-methyl-3-benzylimidazolium chloride, 2-methylimidazoline and 2-phenylimidazoline, and adducts of imidazole compounds with epoxy resins.
The molecular weight of the imidazole-based curing accelerator is not particularly limited, but is preferably 1,000 or less, more preferably 600 or less, further preferably 400 or less, and particularly preferably 300 or less, from the viewpoints of improving the workability (flowability) and suppressing undissolved matter (け in solution and り in solution) during thermoforming.
Examples of the metal-based curing accelerator include organometallic complexes or organometallic salts of metals such as cobalt, copper, zinc, iron, nickel, manganese, and tin. Specific examples of the organic metal complex include organic cobalt complexes such as cobalt (II) acetylacetonate and cobalt (III) acetylacetonate, organic copper complexes such as copper (II) acetylacetonate, organic zinc complexes such as zinc (II) acetylacetonate, organic iron complexes such as iron (III) acetylacetonate, organic nickel complexes such as nickel (II) acetylacetonate, and organic manganese complexes such as manganese (II) acetylacetonate. Examples of the organic metal salt include zinc octylate, tin octylate, zinc naphthenate, cobalt naphthenate, tin stearate, and zinc stearate.
Examples of the amine-based curing accelerator include: trialkylamines such as triethylamine and tributylamine, 4-Dimethylaminopyridine (DMAP), benzyldimethylamine, 2,4, 6-tris (dimethylaminomethyl) phenol, and 1, 8-diazabicyclo (5,4,0) -undecene.
The content of the curing accelerator (E) in the resin composition is not particularly limited, and is preferably 10% by mass or less, more preferably 5% by mass or less, further preferably 3% by mass or less, and particularly preferably 1% by mass or less, when the nonvolatile components other than the component (B) in the resin composition are assumed to be 100% by mass. The lower limit of the content of the curing accelerator (E) in the resin composition is not particularly limited, and when the nonvolatile components other than the component (B) in the resin composition are taken as 100 mass%, they may be, for example, 0 mass% or more, 0.001 mass% or more, 0.01 mass% or more, 0.1 mass% or more, 0.2 mass% or more, 0.3 mass% or more, 0.4 mass% or more, or the like.
< (F) other additives
The resin composition of the present invention may further contain any additive as a nonvolatile component. Examples of such additives include: organic fillers such as rubber particles, polyamide fine particles, and silicone particles; thermoplastic resins such as polycarbonate resin, phenoxy resin, polyvinyl acetal resin, polyolefin resin, polysulfone resin, and polyester resin; organic metal compounds such as organic copper compounds, organic zinc compounds, and organic cobalt compounds; colorants such as phthalocyanine blue, phthalocyanine green, iodine green, diazo yellow, crystal violet, titanium oxide, and carbon black; polymerization inhibitors such as hydroquinone, catechol, pyrogallol, phenothiazine, and the like; leveling agents such as silicone leveling agents and acrylic polymer leveling agents; thickeners such as bentonite (Benton) and montmorillonite; defoaming agents such as silicone defoaming agents, acrylic defoaming agents, fluorine defoaming agents, and vinyl resin defoaming agents; ultraviolet absorbers such as benzotriazole-based ultraviolet absorbers; adhesion improving agents such as urea silane; adhesion imparting agents such as triazole-based adhesion imparting agents, tetrazole-based adhesion imparting agents, and triazine-based adhesion imparting agents; antioxidants such as hindered phenol antioxidants and hindered amine antioxidants; fluorescent whitening agents such as stilbene derivatives; surfactants such as fluorine-based surfactants; flame retardants such as phosphorus flame retardants (e.g., phosphate ester compounds, phosphazene compounds, phosphinic acid compounds, red phosphorus), nitrogen flame retardants (e.g., melamine sulfate), halogen flame retardants, and inorganic flame retardants (e.g., antimony trioxide). The additive may be used alone in 1 kind, or may be used in combination in 2 or more kinds at an arbitrary ratio. (F) The content of other additives can be appropriately set by those skilled in the art.
(G) organic solvent
The resin composition of the present invention may further contain an optional organic solvent as a volatile component in addition to the nonvolatile component. As the organic solvent (G), known organic solvents can be suitably used, and the kind thereof is not particularly limited. Examples of the organic solvent (G) include: ketone solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone; ester solvents such as methyl acetate, ethyl acetate, butyl acetate, isobutyl acetate, isoamyl acetate, methyl propionate, ethyl propionate, and γ -butyrolactone; ether solvents such as tetrahydropyran, tetrahydrofuran, 1, 4-dioxane, diethyl ether, diisopropyl ether, dibutyl ether, and diphenyl ether; alcohol solvents such as methanol, ethanol, propanol, butanol, and ethylene glycol; ether ester solvents such as 2-ethoxyethyl acetate, propylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether acetate, carbitol acetate, gamma-butyrolactone, and methyl methoxypropionate; ester alcohol solvents such as methyl lactate, ethyl lactate, and methyl 2-hydroxyisobutyrate; ether alcohol solvents such as 2-methoxypropanol, 2-methoxyethanol, 2-ethoxyethanol, propylene glycol monomethyl ether, and diethylene glycol monobutyl ether (butyl carbitol); amide solvents such as N, N-dimethylformamide, N-dimethylacetamide, and N-methyl-2-pyrrolidone; sulfoxide solvents such as dimethyl sulfoxide; nitrile solvents such as acetonitrile and propionitrile; aliphatic hydrocarbon solvents such as hexane, cyclopentane, cyclohexane, and methylcyclohexane; aromatic solvents such as benzene, toluene, xylene, ethylbenzene and trimethylbenzene. (G) The organic solvent may be used alone in 1 kind, or may be used in combination in 2 or more kinds at an arbitrary ratio. In one embodiment, the smaller the amount of the (G) organic solvent, the better (for example, 3 mass% or less, 1 mass% or less, 0.5 mass% or less, 0.1 mass% or less, 0.01 mass% or less, when the nonvolatile component in the resin composition is 100 mass%), and particularly preferably not contained.
< method for producing resin composition >
The resin composition of the present invention can be produced, for example, by: to an arbitrary reaction vessel, (a) an epoxy resin, (B) an inorganic filler, (C) a curing agent, (D) a polyether skeleton-containing non-epoxy compound, (E) a curing accelerator as required, (F) other additives as required, and (G) an organic solvent as required are added and mixed in an arbitrary order and/or partially or entirely at the same time. In addition, the temperature may be appropriately set during the addition and mixing of the components, and heating and/or cooling may be performed temporarily or continuously. In addition, stirring or shaking may be performed during the addition and mixing of the components. In addition, when the components are added and mixed or subsequently, the resin composition can be stirred and uniformly dispersed using a stirring device such as a mixer, for example.
< Property of resin composition >
The resin composition of the present invention comprises (a) an epoxy resin, (B) an inorganic filler, (C) a curing agent, and (D) a non-epoxy compound having a polyether skeleton, wherein the polyether skeleton contained in the component (D) is a polyoxyalkylene skeleton composed of 1 or more monomer units selected from ethylene oxide units and propylene oxide units, and the content of the inorganic filler (B) is 70% by mass or more, and the content of the non-epoxy compound having a polyether skeleton (D) is 1% by mass or more and 30% by mass or less, when the nonvolatile components other than the inorganic filler (B) in the resin composition are 100% by mass, the resin composition has excellent embeddability, and can suppress warpage during curing, thereby obtaining a cured product having excellent mechanical strength.
In one embodiment, the resin composition of the present invention has a minimum melt viscosity of preferably 100 poise or less, more preferably 50 poise or less, still more preferably 20 poise or less, and particularly preferably 10 poise or less, when the melt viscosity is measured as in test example 5 below, for example, from the viewpoint of excellent landfill properties.
In one embodiment, the resin composition of the present invention can have a warpage amount of preferably less than 20mm, more preferably less than 10mm, further preferably less than 5mm, and particularly preferably less than 3mm, when the warpage is measured according to JEITA EDX-7311-24, for example, as described in test example 1 below, from the viewpoint that the warpage during curing can be suppressed.
In one embodiment, in order to obtain a cured product having excellent mechanical strength, the resin composition of the present invention may have a three-point bending strength of preferably more than 10MPa, more preferably more than 30MPa, still more preferably more than 40MPa, and particularly preferably more than 50MPa, when the three-point bending strength of the cured product at 23 ℃.
In one embodiment, as described in test example 2 below, when the elastic modulus at 25 ℃ of a cured product of the resin composition of the present invention is measured in accordance with JIS K7127, the elastic modulus may be particularly preferably 25GPa or less, more preferably 20GPa or less, still more preferably 17GPa or less, and particularly preferably 15GPa or less.
In one embodiment, the gelation time of the resin composition of the present invention can be preferably 500 seconds or less, more preferably 400 seconds or less, further preferably 350 seconds or less, and particularly preferably 300 seconds or less, as measured in accordance with JIS C6521, for example, as in test example 4 described below.
< use of resin composition >
The cured product of the resin composition of the present invention is particularly useful for a sealing layer and an insulating layer of a semiconductor because of the above-mentioned advantages. Therefore, the resin composition can be used as a resin composition for sealing a semiconductor or for an insulating layer.
For example, the resin composition of the present invention can be suitably used as: a resin composition for forming an insulating layer of a semiconductor chip package (resin composition for an insulating layer of a semiconductor chip package), and a resin composition for forming an insulating layer of a circuit board (including a printed wiring board) (resin composition for an insulating layer of a circuit board).
In addition, for example, the resin composition of the present invention can be suitably used as: a resin composition for sealing a semiconductor chip encapsulated by a semiconductor chip (resin composition for sealing a semiconductor chip).
Examples of the semiconductor chip package to which the sealing layer or the insulating layer formed from the cured product of the resin composition of the present invention can be applied include: FC-CSP, MIS-BGA Package, ETS-BGA Package, Fan-out (Fan-out) WLP (Wafer Level Package), Fan-in (Fan-in) WLP, Fan-out PLP (Panel Level Package), Fan-in PLP.
The resin composition of the present invention can be used as an underfill material, for example, a material of MUF (Molding Under Filling) used after a semiconductor chip is connected to a substrate.
Further, the resin composition of the present invention can be used in a wide range of applications where resin compositions can be used, such as resin sheets, sheet-like laminates such as prepregs, liquid materials such as resin inks used for solder resists, die bonding materials, hole filling resins, and component embedding resins.
< resin sheet >
The resin sheet of the present invention includes a support and a resin composition layer provided on the support. The resin composition layer is a layer containing the resin composition of the present invention, and is usually formed of a resin composition.
From the viewpoint of thinning, the thickness of the resin composition layer is preferably 600 μm or less, and more preferably 500 μm or less. The lower limit of the thickness of the resin composition layer may be preferably 1 μm or more and 5 μm or more, more preferably 10 μm or more, further preferably 50 μm or more, and particularly preferably 100 μm or more.
The thickness of the cured product obtained by curing the resin composition layer is preferably 600 μm or less, and more preferably 500 μm or less. The lower limit of the thickness of the cured product is preferably 1 μm or more and 5 μm or more, more preferably 10 μm or more, further preferably 50 μm or more, and particularly preferably 100 μm or more.
Examples of the support include a film made of a plastic material, a metal foil, and a release paper, and preferably a film made of a plastic material and a metal foil.
When a film made of a plastic material is used as the support, examples of the plastic material include: polyesters such as polyethylene terephthalate (hereinafter sometimes referred to simply as "PET") and polyethylene naphthalate (hereinafter sometimes referred to simply as "PEN"); polycarbonate (hereinafter sometimes simply referred to as "PC"); acrylic polymers such as polymethyl methacrylate (hereinafter, may be abbreviated as "PMMA"); a cyclic polyolefin; triacetyl cellulose (hereinafter sometimes simply referred to as "TAC"); polyether sulfide (hereinafter sometimes simply referred to as "PES"); a polyether ketone; a polyimide; and so on. Among them, polyethylene terephthalate and polyethylene naphthalate are preferable, and particularly, inexpensive polyethylene terephthalate is preferable.
When a metal foil is used as the support, examples of the metal foil include a copper foil and an aluminum foil. Among them, copper foil is preferable. As the copper foil, a foil formed of a single metal of copper may be used, and a foil formed of an alloy of copper and another metal (for example, tin, chromium, silver, magnesium, nickel, zirconium, silicon, titanium, or the like) may also be used.
The surface of the support to be bonded to the resin composition layer may be subjected to a matte treatment, a corona treatment, an antistatic treatment, or the like.
In addition, as the support, a support with a release layer having a release layer on a surface to be bonded to the resin composition layer can be used. Examples of the release agent used for the release layer of the support having a release layer include 1 or more release agents selected from alkyd resins, polyolefin resins, polyurethane resins, and silicone resins. As commercially available products of the mold release agent, there may be mentioned, for example, "SK-1", "AL-5" and "AL-7" manufactured by Linekaceae as alkyd resin-based mold release agents. Examples of the support having a release layer include "lumiror T60" manufactured by dongli corporation; "Purex" manufactured by Imperial corporation; unipel manufactured by UNITIKA corporation; and so on.
The thickness of the support is preferably in the range of 5 to 75 μm, and more preferably in the range of 10 to 60 μm. When a support with a release layer is used, the thickness of the entire support with a release layer is preferably in the above range.
The resin sheet can be produced by applying a resin composition to a support using an application device such as a die coater. Further, if necessary, the resin composition may be dissolved in an organic solvent to prepare a resin varnish, and the resin varnish may be applied to prepare a resin sheet. By using an organic solvent, the viscosity can be adjusted and the coatability can be improved. In the case of using a resin composition or a resin varnish containing an organic solvent, generally, the resin composition or the resin varnish is dried after coating to form a resin composition layer.
The drying can be carried out by a known method such as heating or blowing hot air. The drying conditions are such that the content of the organic solvent in the resin composition layer is usually 10% by mass or less, preferably 5% by mass or less. Although the boiling point of the organic solvent in the resin composition or the resin varnish varies, for example, in the case of using a resin composition or a resin varnish containing 30 to 60 mass% of an organic solvent, the resin composition layer can be formed by drying at 50 to 150 ℃ for 3 to 10 minutes.
The resin sheet may contain any layer other than the support and the resin composition layer as necessary. For example, in the resin sheet, a protective film selected for the support may be provided on the surface of the resin composition layer that is not bonded to the support (i.e., the surface on the side opposite to the support). The thickness of the protective film is, for example, 1 μm to 40 μm. The protective film can prevent dust or the like from adhering to the surface of the resin composition layer and prevent the surface of the resin composition layer from being damaged. When the resin sheet has a protective film, the protective film is peeled off, whereby the resin sheet can be used. Alternatively, the resin sheet may be wound in a roll shape and stored.
The resin sheet can be suitably used for forming an insulating layer (insulating resin sheet for semiconductor chip package) in the manufacture of semiconductor chip packages. For example, the resin sheet can be used for forming an insulating layer of a circuit board (resin sheet for an insulating layer of a circuit board). Examples of packages using such a substrate include FC-CSP, MIS-BGA, and ETS-BGA packages.
In addition, the resin sheet can be suitably used for sealing a semiconductor chip (semiconductor chip sealing resin sheet). Examples of applicable semiconductor chip packages include fan-out WLP, fan-in WLP, fan-out PLP, and fan-in PLP.
In addition, the resin sheet may be used as a material of the MUF used after the semiconductor chip is connected to the substrate.
Further, the resin sheet can be used for other wide uses requiring high insulation reliability. For example, the resin sheet can be suitably used for forming an insulating layer of a circuit substrate of a printed wiring board or the like.
< Circuit Board >
The circuit board of the present invention includes an insulating layer formed from a cured product of the resin composition of the present invention. The circuit board can be manufactured by a manufacturing method including, for example, the following steps (1) and (2),
(1) a step of forming a resin composition layer on a base material;
(2) and a step of forming an insulating layer by thermally curing the resin composition layer.
In step (1), a substrate is prepared. Examples of the base material include substrates such as a glass epoxy substrate, a metal substrate (stainless steel, cold-rolled steel Sheet (SPCC), etc.), a polyester substrate, a polyimide substrate, a BT resin substrate, and a thermosetting polyphenylene ether substrate. The substrate may have a metal layer such as a copper foil on the surface thereof as a part of the substrate. For example, a substrate having a first metal layer and a second metal layer which can be peeled off on both surfaces may be used. When such a base material is used, a conductor layer, which is a wiring layer capable of functioning as a circuit wiring, is usually formed on the surface of the second metal layer opposite to the first metal layer. As a substrate having such a metal layer, for example, an ultra-Thin copper foil with a carrier copper foil "Micro Thin" manufactured by mitsui metal mining corporation can be cited.
In addition, a conductor layer may be formed on one or both surfaces of the substrate. In the following description, a member including a base material and a conductor layer formed on a surface of the base material is sometimes referred to as a "base material with a wiring layer" as appropriate. Examples of the conductor material included in the conductor layer include materials containing 1 or more metals selected from gold, platinum, palladium, silver, copper, aluminum, cobalt, chromium, zinc, nickel, titanium, tungsten, iron, tin, and indium. As the conductor material, a single metal may be used, and an alloy may be used. Examples of the alloy include alloys of 2 or more metals selected from the above metals (for example, nickel-chromium alloys, copper-nickel alloys, and copper-titanium alloys). Among them, chromium, nickel, titanium, aluminum, zinc, gold, palladium, silver, or copper as a single metal is preferable from the viewpoint of versatility of forming a conductor layer, cost, and easiness of patterning; and alloys of nickel-chromium alloy, copper-nickel alloy, and copper-titanium alloy as alloys. Among them, a single metal of chromium, nickel, titanium, aluminum, zinc, gold, palladium, silver, or copper is more preferable; and nickel-chromium alloys, with copper being particularly preferred.
The conductor layer may be patterned, for example, in order to function as a wiring layer. In this case, the ratio of the line width (circuit width)/line pitch (width between circuits) of the conductor layer is not particularly limited, but is preferably 20/20 μm or less (i.e., the pitch (pitch) is 40 μm or less), more preferably 10/10 μm or less, still more preferably 5/5 μm or less, still more preferably 1/1 μm or less, and particularly preferably 0.5/0.5 μm or more. The pitch need not be the same across the entire conductor layer. The minimum pitch of the conductor layers may be, for example, 40 μm or less, 36 μm or less, or 30 μm or less.
The thickness of the conductor layer depends on the design of the circuit board, and is preferably 3 μm to 35 μm, more preferably 5 μm to 30 μm, still more preferably 10 μm to 20 μm, and particularly preferably 15 μm to 20 μm.
The conductor layer can be formed, for example, by a method including the steps of: a step of laminating a dry film (photosensitive resist film) on a substrate; a step of obtaining a dry film pattern by exposing and developing the dry film under a predetermined condition using a photomask to form a pattern; forming a conductor layer by a plating method such as electrolytic plating using the developed pattern dry film as a plating mask; and a step of peeling off the pattern dry film. As the dry film, a photosensitive dry film formed from a photoresist composition can be used, and for example, a dry film formed from a resin such as a novolac resin or an acrylic resin can be used. The lamination conditions of the base material and the dry film may be the same as those of the base material and the resin sheet described later. The dry film can be peeled off using an alkaline peeling solution such as a sodium hydroxide solution.
After preparing the base material, a resin composition layer is formed on the base material. When the conductive layer is formed on the surface of the base material, the resin composition layer is preferably formed so that the conductive layer is embedded in the resin composition layer.
The resin composition layer can be formed, for example, by laminating a resin sheet and a base material. The lamination can be performed, for example, by bonding the resin composition layer to the base material by heat-crimping the resin sheet to the base material from the support side. Examples of the member for heat-pressure bonding the resin sheet to the base material (hereinafter, sometimes referred to as "heat-pressure bonded member") include a heated metal plate (e.g., SUS end plate) and a metal roll (e.g., SUS roll). It is preferable that the heating and pressure-bonding member is not directly pressed against the resin sheet, but is pressed via an elastic material such as heat-resistant rubber so that the resin sheet sufficiently follows the surface irregularities of the base material.
The lamination of the substrate and the resin sheet can be performed by, for example, a vacuum lamination method. In the vacuum lamination method, the heat-pressure bonding temperature is preferably in the range of 60 to 160 ℃, and more preferably in the range of 80 to 140 ℃. The pressure of the heat-pressure bonding is preferably in the range of 0.098MPa to 1.77MPa, more preferably in the range of 0.29MPa to 1.47 MPa. The heat and pressure bonding time is preferably in the range of 20 seconds to 400 seconds, and more preferably in the range of 30 seconds to 300 seconds. The lamination is preferably performed under a reduced pressure of 13hPa or less.
After the lamination, the smoothing treatment of the laminated resin sheets can be performed under normal pressure (atmospheric pressure), for example, by pressing the heat-pressure bonding member from the support side. The pressing conditions for the smoothing treatment may be set to the same conditions as the above-described conditions for the heat and pressure bonding of the laminate. The lamination and smoothing processes may be performed continuously using a vacuum laminator.
The formation of the resin composition layer can be performed by, for example, compression molding. The molding conditions may be the same as those of the method for forming the resin composition layer in the step of forming the sealing layer of the semiconductor chip package, which will be described later.
After the resin composition layer is formed on the base material, the resin composition layer is thermally cured to form the insulating layer. The heat curing conditions of the resin composition layer vary depending on the type of the resin composition, and the curing temperature is usually in the range of 120 to 240 ℃ (preferably in the range of 150 to 220 ℃, and more preferably in the range of 170 to 200 ℃), and the curing time is in the range of 5 to 120 minutes (preferably in the range of 10 to 100 minutes, and more preferably in the range of 15 to 90 minutes).
The resin composition layer may be subjected to a preliminary heat treatment of heating at a temperature lower than the curing temperature before the resin composition layer is thermally cured. For example, before the resin composition layer is thermally cured, the resin composition layer may be preheated at a temperature of 50 ℃ or higher and lower than 120 ℃ (preferably 60 ℃ or higher and 110 ℃ or lower, more preferably 70 ℃ or higher and 100 ℃ or lower) for usually 5 minutes or longer (preferably 5 minutes to 150 minutes, more preferably 15 minutes to 120 minutes).
By performing the above operation, a circuit substrate having an insulating layer can be manufactured. The method of manufacturing the circuit board may further include any process. For example, in the case of manufacturing a circuit board using a resin sheet, the method for manufacturing a circuit board may include a step of peeling off the support of the resin sheet. The support may be peeled off before the thermal curing of the resin composition layer or may be peeled off after the thermal curing of the resin composition layer.
The method for manufacturing a circuit board may include, for example: and polishing the surface of the insulating layer after the insulating layer is formed. The polishing method is not particularly limited. For example, the surface of the insulating layer may be polished using a surface grinder.
The method for manufacturing the circuit board may include, for example, a step (3) of connecting the conductive layers between layers, for example, a step of forming a hole in the insulating layer. Thus, a via hole (via hole), a through hole (through hole), or the like can be formed in the insulating layer. Examples of the method for forming the through hole include laser irradiation, etching, and mechanical drilling. The size and shape of the through-hole can be determined as appropriate according to the design of the circuit substrate. In the step (3), the interlayer connection may be performed by polishing or grinding the insulating layer.
After the formation of the through-hole, a step of removing the contamination in the through-hole is preferably performed. This process is sometimes also referred to as desmear (desmear) process. For example, in the case where the formation of the conductor layer on the insulating layer is performed by the plating process, the through-hole may be subjected to wet desmear treatment. In the case where the conductive layer is formed on the insulating layer by a sputtering process, a dry desmear process such as a plasma treatment process may be performed. Further, the insulating layer can be subjected to roughening treatment by the desmear process.
In addition, the insulating layer may be subjected to roughening treatment before the conductor layer is formed on the insulating layer. By this roughening treatment, in general, the surface of the insulating layer including inside the through-hole can be roughened. As the roughening treatment, any of dry and wet roughening treatments can be performed. Examples of the dry roughening treatment include plasma treatment. In addition, as an example of the wet roughening treatment, a method of sequentially performing a swelling treatment with a swelling liquid, a roughening treatment with an oxidizing agent, and a neutralizing treatment with a neutralizing liquid may be mentioned.
After the via hole is formed, a conductor layer may be formed on the insulating layer. By forming a conductor layer at the position where the via hole is formed, the newly formed conductor layer is electrically connected to the conductor layer on the surface of the base material, and interlayer connection can be performed. Examples of the method for forming the conductor layer include plating, sputtering, and vapor deposition, and among them, plating is preferred. In a preferred embodiment, plating is performed on the surface of the insulating layer by an appropriate method such as a semi-additive method or a full-additive method, thereby forming a conductor layer having a desired wiring pattern. In the case where the support in the resin sheet is a metal foil, a conductor layer having a desired wiring pattern can be formed by a subtractive method. The material of the conductor layer to be formed may be a single metal or an alloy. In addition, the conductor layer may have a single-layer structure or a multilayer structure including two or more layers of different kinds of materials.
Here, an example of an embodiment in which a conductor layer is formed over an insulating layer will be described in detail. A plating seed layer (seed layer) is formed on the surface of the insulating layer by electroless plating. Next, a mask pattern is formed on the plating seed layer so as to expose a part of the plating seed layer in accordance with a desired wiring pattern. An electrolytic plating layer is formed on the exposed plating seed layer by electrolytic plating, and then the mask pattern is removed. Then, the unnecessary plating seed layer is removed by etching or the like, whereby a conductor layer having a desired wiring pattern can be formed. In the formation of the conductor layer, the dry film used for the formation of the mask pattern is the same as the dry film described above.
The method for manufacturing a circuit board may include a step (4) of removing the base material. By removing the base material, a circuit board having an insulating layer and a conductor layer embedded in the insulating layer can be obtained. This step (4) can be performed, for example, when a substrate having a peelable metal layer is used.
< semiconductor chip Package >
A semiconductor chip package according to a first embodiment of the present invention includes: the circuit board and a semiconductor chip mounted on the circuit board. The semiconductor chip package can be manufactured by bonding a semiconductor chip to a circuit substrate.
The conditions for bonding the circuit board and the semiconductor chip may be any conditions under which the terminal electrodes of the semiconductor chip and the circuit wiring of the circuit board can be electrically connected to each other. For example, conditions used in flip-chip mounting of a semiconductor chip can be employed. For example, the semiconductor chip and the circuit board may be bonded to each other with an insulating adhesive interposed therebetween.
As an example of the bonding method, a method of pressure-bonding a semiconductor chip to a circuit board is given. The pressure bonding temperature is usually in the range of 120 to 240 ℃ (preferably in the range of 130 to 200 ℃, and more preferably in the range of 140 to 180 ℃), and the pressure bonding time is usually in the range of 1 to 60 seconds (preferably in the range of 5 to 30 seconds), as the pressure bonding conditions.
In addition, as another example of the bonding method, a method of bonding a semiconductor chip to a circuit board by reflow soldering is given. The reflow conditions may be set to a range of 120 ℃ to 300 ℃.
After the semiconductor chip is bonded to the circuit substrate, the semiconductor chip may be filled with a mold underfill material. The resin composition described above can be used as the molding underfill material, and the resin sheet described above can also be used.
A semiconductor chip package according to a second embodiment of the present invention includes: a semiconductor chip and a cured product of the resin composition for sealing the semiconductor chip. In such a semiconductor chip package, a cured product of the resin composition generally functions as a sealing layer. As the semiconductor chip package according to the second embodiment, for example, a fan-out WLP is given.
The method for manufacturing the semiconductor chip package includes the steps of:
(A) a step of laminating a temporary fixing film on a base material;
(B) temporarily fixing the semiconductor chip on the temporary fixing film;
(C) forming a sealing layer on the semiconductor chip;
(D) a step of peeling the base material and the temporary fixing film from the semiconductor chip;
(E) forming a rewiring formation layer as an insulating layer on a surface of the semiconductor chip from which the base material and the temporary fixing film are peeled;
(F) forming a rewiring layer as a conductor layer on the rewiring-forming layer; and
(G) and forming a solder resist layer on the rewiring layer. In addition, the method for manufacturing the semiconductor chip package may include the steps of:
(H) and a step of dicing the plurality of semiconductor chip packages into individual semiconductor chip packages and singulating the individual semiconductor chip packages.
(Process (A))
The step (a) is a step of laminating a temporary fixing film on a base material. The lamination conditions of the base material and the temporary fixing film may be the same as those of the base material and the resin sheet in the manufacturing method of the circuit board.
Examples of the substrate include: a silicon wafer; a glass wafer; a glass substrate; metal substrates such as copper, titanium, stainless steel, and cold-rolled steel Sheet (SPCC); a substrate such as an FR-4 substrate obtained by impregnating glass fibers with an epoxy resin or the like and thermally curing the resin; a substrate made of bismaleimide triazine resin such as BT resin; and so on.
Any material that can be peeled off from the semiconductor chip and can temporarily fix the semiconductor chip can be used for the temporary fixing film. Examples of commercially available products include "REVALPHA" manufactured by ritonary electric corporation.
(Process (B))
The step (B) is a step of temporarily fixing the semiconductor chip to the temporary fixing film. The temporary fixing of the semiconductor chip can be performed by using a flip chip bonder (flip chip bonder), a die bonder (die bonder) or the like. The layout (layout) and the number of semiconductor chips to be arranged may be appropriately set according to the shape and size of the temporary fixing film, the number of production processes of a target semiconductor chip package, and the like, and for example, the semiconductor chips may be arranged in a matrix of a plurality of rows and a plurality of columns to be temporarily fixed.
(Process (C))
The step (C) is a step of forming a sealing layer on the semiconductor chip. The sealing layer is formed from a cured product of the resin composition. The sealing layer is generally formed by a method including a step of forming a resin composition layer on a semiconductor chip and a step of forming a sealing layer by thermally curing the resin composition layer.
The formation of the resin composition layer is preferably performed by compression molding. In the compression molding method, generally, the semiconductor chip and the resin composition are placed in a mold, and the resin composition is heated as necessary while applying pressure to the resin composition in the mold to form a resin composition layer covering the semiconductor chip.
The specific operation of the compression molding method can be performed, for example, in the following manner. An upper mold and a lower mold were prepared as a mold for compression molding. Further, the resin composition is applied to the semiconductor chip temporarily fixed on the temporary fixing film as described above. The semiconductor chip coated with the resin composition is mounted on a lower mold together with a base material and a temporary fixing film. Then, the upper mold and the lower mold are closed, and heat and pressure are applied to the resin composition to perform compression molding.
The specific operation of the compression molding method can be performed, for example, as follows. An upper mold and a lower mold were prepared as a mold for compression molding. The resin composition is placed on the lower mold. In addition, the semiconductor chip is mounted on the upper mold together with the base material and the temporary fixing film. Then, the upper mold and the lower mold are closed so that the resin composition placed on the lower mold contacts the semiconductor chip mounted on the upper mold, and heat and pressure are applied to the mold to perform compression molding.
The molding conditions vary depending on the composition of the resin composition, and suitable conditions can be adopted to achieve good sealing. For example, the temperature of the mold at the time of molding is preferably 70 ℃ or higher, more preferably 80 ℃ or higher, particularly preferably 90 ℃ or higher, preferably 200 ℃ or lower, more preferably 170 ℃ or lower, and particularly preferably 150 ℃ or lower. The pressure applied during molding is preferably 1MPa or more, more preferably 3MPa or more, particularly preferably 5MPa or more, preferably 50MPa or less, more preferably 30MPa or less, and particularly preferably 20MPa or less. The curing time (cure time) is preferably 1 minute or more, more preferably 2 minutes or more, particularly preferably 3 minutes or more, preferably 60 minutes or less, more preferably 30 minutes or less, and particularly preferably 20 minutes or less. Generally, after the resin composition layer is formed, the mold is disassembled. The detachment of the mold may be performed before or after the thermosetting of the resin composition layer.
The resin composition layer can be formed by laminating a resin sheet and a semiconductor chip. For example, the resin composition layer of the resin sheet is thermally and pressure-bonded to the semiconductor chip, whereby the resin composition layer can be formed on the semiconductor chip. The resin sheet and the semiconductor chip are generally laminated using a semiconductor chip instead of the base material, in the same manner as the resin sheet and the base material are laminated in the manufacturing method of the circuit board.
After a resin composition layer is formed on a semiconductor chip, the resin composition layer is thermally cured to obtain a sealing layer covering the semiconductor chip. Thus, the semiconductor chip is sealed with the cured product of the resin composition. The conditions for the thermosetting of the resin composition layer may be the same as those for the thermosetting of the resin composition layer in the method for producing a circuit board. Further, before the resin composition layer is thermally cured, a preliminary heat treatment may be performed to heat the resin composition layer at a temperature lower than the curing temperature. The same conditions as the preliminary heating process in the circuit board manufacturing method can be adopted as the process conditions of the preliminary heating process.
(Process (D))
The step (D) is a step of peeling the base material and the temporary securing film from the semiconductor chip. The peeling method is preferably an appropriate method in accordance with the material of the temporary fixing film. Examples of the peeling method include a method in which the temporary fixing film is heated, foamed, or expanded to be peeled. In addition, as a peeling method, for example, a method of irradiating ultraviolet rays to the temporary fixing film through the base material to lower the adhesive force of the temporary fixing film and peeling the film is exemplified.
In the method of peeling the temporary fixing film by heating, foaming or expanding, the heating condition is usually from 1 second to 90 seconds or from 5 minutes to 15 minutes at 100 ℃ to 250 ℃. In the method of peeling the temporary fixing film by irradiating ultraviolet rays to decrease the adhesive force of the temporary fixing film, the irradiation amount of ultraviolet rays is usually 10mJ/cm2~1000mJ/cm2。
(Process (E))
The step (E) is a step of forming a rewiring formation layer as an insulating layer on the surface of the semiconductor chip from which the base material and the temporary fixing film are peeled.
Any insulating material can be used as the material of the rewiring formation layer. Among them, a photosensitive resin and a thermosetting resin are preferable from the viewpoint of ease of manufacturing a semiconductor chip package. The resin composition of the present invention can be used as the thermosetting resin.
After the rewiring layer is formed, a through hole may be formed in the rewiring layer in order to connect the semiconductor chip and the rewiring layer.
In the method of forming a through hole in the case where the material of the rewiring formation layer is a photosensitive resin, the surface of the rewiring formation layer is usually irradiated with an active energy ray through a mask pattern to photocure the rewiring formation layer at the irradiated portion. Examples of the active energy ray include ultraviolet rays, visible rays, electron beams, and X-rays, and ultraviolet rays are particularly preferable. The irradiation amount and the irradiation time of the ultraviolet ray can be appropriately set according to the photosensitive resin. Examples of the exposure method include: a contact exposure method in which the mask pattern is allowed to adhere to the rewiring formation layer and exposure is performed, a non-contact exposure method in which exposure is performed using parallel light rays without allowing the mask pattern to adhere to the rewiring formation layer, and the like.
After photocuring the rewiring-forming layer, the rewiring-forming layer is developed to remove the unexposed portions and form through holes. For development, either wet development or dry development may be performed. Examples of the developing method include a dipping method, a spin immersion (paddle) method, a spraying method, a brush coating method, and a doctor blade (squeegee) method, and the spin immersion method is preferable from the viewpoint of resolution.
Examples of a method for forming a through hole in the case where the material of the rewiring formation layer is a thermosetting resin include laser irradiation, etching, and mechanical drilling. Among them, laser irradiation is preferable. The laser irradiation can be performed by an appropriate laser processing machine using a light source such as a carbon dioxide laser, a UV-YAG laser, or an excimer laser.
The shape of the through hole is not particularly limited, and may be generally circular (substantially circular). The diameter of the top of the through hole is preferably 50 μm or less, more preferably 30 μm or less, and still more preferably 20 μm or less. Here, the top diameter of the via hole means the opening diameter of the via hole at the surface of the rewiring formation layer.
(Process (F))
The step (F) is a step of forming a rewiring layer as a conductor layer on the rewiring formation layer. The method of forming the rewiring layer on the rewiring-forming layer may be the same as the method of forming the conductor layer on the insulating layer in the manufacturing method of the circuit substrate. Further, the step (E) and the step (F) may be repeated to alternately stack (stack) the rewiring layer and the rewiring-forming layer.
(Process (G))
The step (G) is a step of forming a solder resist layer on the rewiring layer. Any material having insulating properties can be used as the material of the solder resist layer. Among them, a photosensitive resin and a thermosetting resin are preferable from the viewpoint of ease of manufacturing a semiconductor chip package. In addition, as the thermosetting resin, the resin composition of the present invention can be used.
In the step (G), a bump process for forming a bump may be performed as necessary. The bumping process may be performed by solder ball, solder plating (solder plating), and the like. The formation of the through hole in the bump processing can be performed in the same manner as in the step (E).
(Process (H))
The method for manufacturing a semiconductor chip package may include the step (H) in addition to the steps (a) to (G). The step (H) is a step of dicing the plurality of semiconductor chip packages into individual semiconductor chip packages and singulating the individual semiconductor chip packages. The method of cutting the semiconductor chip packages into the semiconductor chip packages one by one is not particularly limited.
< semiconductor device >
The semiconductor device includes a semiconductor chip package. Examples of the semiconductor device include various semiconductor devices used in electric products (for example, a personal computer, a mobile phone, a smartphone, a tablet-type device, a wearable device, a digital camera, a medical device, a television, and the like), vehicles (for example, a motorcycle, an automobile, a train, a ship, an aircraft, and the like), and the like.
Examples
The present invention will be described in detail with reference to examples. The present invention is not limited by these examples. In the following, the terms "part" and "%" as used herein mean "part by mass" and "% by mass", respectively, unless otherwise explicitly stated.
< example 1 >
0.5 parts of an amine curing agent (SeIKACURE-S manufactured by SEIKA corporation), 7 parts of a glycidylamine-type epoxy resin (630% epoxy equivalent of 95g/eq. manufactured by Mitsubishi chemical corporation), 8 parts of a naphthalene-type epoxy resin (HP-4032D% manufactured by DIC corporation), 0.1 part of an imidazole-based curing accelerator (2E 4-MZ manufactured by Sichuan chemical corporation), 2 parts of a polyoxyethylene polyoxypropylene glycol (L-44% manufactured by ADEKA corporation), and an inorganic filler (average particle diameter: 1.8 μm, specific surface area: 3.6 m) were mixed by a mixer2(g), spherical silica treated with KBM573 (N-phenyl-3-aminopropyltrimethoxysilane, manufactured by shin-Etsu chemical Co., Ltd.) in an amount of 70 parts by weight was uniformly dispersed to prepare a resin composition.
< example 2 >
A resin composition was prepared in the same manner as in example 1 except that 2 parts of polyoxyethylene polyoxypropylene glycol (L-64, manufactured by ADEKA) was used in place of 2 parts of polyoxyethylene polyoxypropylene glycol (L-44, manufactured by ADEKA).
< example 3 >
A resin composition was prepared in the same manner as in example 1 except that 4 parts of polyoxyethylene polyoxypropylene glycol (L-64, manufactured by ADEKA) was used in place of 2 parts of polyoxyethylene polyoxypropylene glycol (L-44, manufactured by ADEKA).
< example 4 >
7 parts of an acid anhydride curing agent ("MH-700" manufactured by Nippon chemical Co., Ltd., acid anhydride equivalent of 163g/eq.), 5 parts of a glycidylamine-type epoxy resin ("630" manufactured by Mitsubishi chemical Co., Ltd., epoxy equivalent of 95g/eq.), 6 parts of a naphthalene-type epoxy resin ("HP-4032D" manufactured by DIC Co., Ltd., epoxy equivalent of 143g/eq.), 0.1 part of an imidazole-based curing accelerator ("2 MA-OK-PW" manufactured by Sichuan chemical Co., Ltd.), 3 parts of a polyoxyalkylene-modified silicone ("KF-6028" manufactured by shin chemical industry Co., Ltd.), and 3 parts of an inorganic filler (average particle diameter of 1.8 μm, specific surface area of 3.6 m) were mixed by a mixer2(g), 85 parts of spherical silica treated with KBM573 (N-phenyl-3-aminopropyltrimethoxysilane, manufactured by shin-Etsu chemical Co., Ltd.) was uniformly dispersed to prepare a resin composition.
< example 5 >
A resin composition was prepared in the same manner as in example 4 except that 3 parts of polyoxyalkylene-modified silicone (KF-6015, manufactured by shin-Etsu chemical Co., Ltd.) was used instead of 3 parts of polyoxyalkylene-modified silicone (KF-6028, manufactured by shin-Etsu chemical Co., Ltd.).
< example 6 >
A resin composition was prepared in the same manner as in example 4 except that 1 part of polyoxyalkylene-modified silicone (KF-6015, manufactured by shin-Etsu chemical Co., Ltd.) was used in place of 3 parts of polyoxyalkylene-modified silicone (KF-6028, manufactured by shin-Etsu chemical Co., Ltd.).
< comparative example 1 >
A resin composition was prepared in the same manner as in example 1, except that polyoxyethylene polyoxypropylene glycol ("L-44" manufactured by ADEKA) was not used.
< comparative example 2 >
A resin composition was prepared in the same manner as in example 1 except that the amount of polyoxyethylene polyoxypropylene glycol ("L-44" manufactured by ADEKA) used was changed from 2 parts to 7 parts.
< comparative example 3 >
A resin composition was prepared in the same manner as in example 4, except that the polyoxyalkylene-modified silicone ("KF-6028" manufactured by shin-Etsu chemical Co., Ltd.) was not used.
< comparative example 4 >
A resin composition was prepared in the same manner as in example 4, except that the amount of the polyoxyalkylene-modified silicone ("KF-6028", manufactured by shin-Etsu chemical Co., Ltd.) was changed from 3 parts to 8 parts.
< comparative example 5 >
A resin composition was prepared in the same manner as in comparative example 4 except that 8 parts of the polyoxyalkylene modified silicone (KF-6028, manufactured by shin-Etsu chemical Co., Ltd.) in comparative example 4 was changed to 8 parts of an amphiphilic polyether block copolymer (Fortegra 100, manufactured by Takara chemical Co., Ltd., polyether compound containing a polyoxybutylene block).
< test example 1: evaluation of warpage
The resin compositions prepared in examples and comparative examples were compression-molded on a 12-inch silicon wafer using a compression mold apparatus (mold temperature: 130 ℃, pressure: 6MPa, curing time: 10 minutes) to form a resin composition layer having a thickness of 300 μm. Then, the resin composition layer was heated at 180 ℃ for 90 minutes to thermally cure the resin composition layer. Thus, a sample substrate including a silicon wafer and a cured product layer of the resin composition was obtained. The warpage amount at 25 ℃ was measured with respect to the aforementioned sample substrate using a video Moire (Shadow Moire) measurement device ("thermohreaxp" manufactured by Akorometrix corporation). The measurement was carried out according to the Japanese electronic information technology industry Association standard JEITA EDX-7311-24. Specifically, a fitting plane calculated by the least square method is used as a reference plane for all data on the substrate surface of the measurement area, and the difference between the minimum value and the maximum value in the vertical direction from the reference plane is obtained as a warping amount, and the following criteria are used for evaluation;
". o": the warping amount is less than 3mm
"×": the warping amount is more than 3 mm.
< test example 2: measurement of elastic modulus (GPa)
The resin compositions prepared in examples and comparative examples were compression-molded on SUS plates whose surfaces had been subjected to a releasing treatment using a press molding apparatus (mold temperature: 130 ℃, pressure: 6MPa, curing time: 10 minutes) to form resin composition layers having a thickness of 300 μm. The SUS plate was peeled off, and the resin composition layer was thermally cured by heating at 180 ℃ for 90 minutes to obtain a cured layer of the resin composition. The cured product layer was cut into a dumbbell No. 1 shape to obtain a test piece. The tensile strength of the test piece was measured using a tensile tester "RTC-1250A" manufactured by Orientec, and the elastic modulus (GPa) at 25 ℃ was determined. Measurement was carried out in accordance with JIS K7127. This operation was carried out 3 times, and the average value thereof is shown in the table.
< test example 3: evaluation of three-Point bending Strength
The resin compositions prepared in examples and comparative examples were compression-molded on a SUS plate subjected to a mold release treatment using a press molding apparatus (mold temperature: 130 ℃, pressure: 6MPa, curing time: 10 minutes) to form a resin composition layer having a thickness of 300. mu.m. Then, the resin composition was peeled off from the SUS plate and heat-cured at 150 ℃ for 60 minutes to obtain a test piece for measuring three-point bending strength. The three-point bending strength (MPa) at 23 ℃ was determined using a tensile tester "RTC-1250A" manufactured by Orientec corporation. 5 tests were carried out, and the average value thereof was used. The case where the three-point bending strength was 50MPa or less was evaluated as "poor", and the case where the three-point bending strength was more than 50MPa was evaluated as "good".
< test example 4: measurement of gel time (gelation time) (second)
With respect to the resin compositions prepared in examples and comparative examples, the gel time (gelation time) was measured in accordance with JIS C6521. Specifically, first, the time (seconds) for which the resin compositions of examples and comparative examples were not drawn out at 130 ℃ was measured by a heated plate gelation tester (GT-D: manufactured by Nisshin scientific Co.). More specifically, about 0.5g of the sample (resin composition) was set on a hot plate gelation tester. The resin composition was repeatedly subjected to an osculating circular motion (1 rotation per 1 second) using a spatula having a tip width of 5mm so that the resin composition was held on a hot plate within a range of 25mm in diameter from the time when the resin composition reached 130 ℃ (gel time at 130 ℃). The resin composition was vertically lifted up by 30mm from the hot plate, and the time from the start point to the end point was measured as the time to gel, with the end point being the time at which the filament was broken. The doctor blade is not lifted during the period when the viscosity of the resin is low, and is often lifted vertically by about 30mm from the heating plate after the viscosity is increased, and this up-and-down movement is repeated until the filament is broken. The measurement was repeated 2 times, and the average value was used as the result.
< test example 5: evaluation of minimum melt viscosity
The melt viscosities of the resin compositions prepared in examples and comparative examples were measured using a dynamic viscoelasticity measuring apparatus ("Rheosol-G3000" manufactured by UBM corporation). This measurement was performed using parallel plates having a diameter of 18mm for a 1g sample taken from the resin composition. The measurement conditions were: from an initial temperature of 60 ℃ to 200 ℃, the temperature rise rate is 5 ℃/min, the measurement temperature interval is 2.5 ℃, and the vibration is 1 Hz/deg. From the measured values of the melt viscosities, the lowest melt viscosity was determined. The case where the lowest melt viscosity was 10 poise or less was evaluated as "good", the case where it was more than 10 poise and 100 poise or less was evaluated as "Δ", and the case where it was more than 100 poise was evaluated as "x".
The nonvolatile components and the amounts of the nonvolatile components of the resin compositions of examples and comparative examples, and the measurement results and evaluation results of the test examples are shown in table 1 below.
[ Table 1]
[ Table 1]
From the above results, it is understood that when the resin composition used is the following resin composition, excellent filling properties are provided, warpage during curing can be suppressed, and a cured product having excellent mechanical strength can be obtained; the resin composition comprises (A) an epoxy resin, (B) an inorganic filler, (C) a curing agent, and (D) a non-epoxy compound having a polyether skeleton, wherein the polyether skeleton contained in the component (D) is a polyoxyalkylene skeleton composed of 1 or more monomer units selected from the group consisting of an ethylene oxide unit and a propylene oxide unit, and the content of the inorganic filler (B) is 70% by mass or more, and the content of the non-epoxy compound having a polyether skeleton (D) is 1% by mass or more and 30% by mass or less, when the nonvolatile components other than the inorganic filler (B) in the resin composition are 100% by mass, the total nonvolatile components in the resin composition are 100% by mass.
Claims (24)
1. A resin composition comprising (A) an epoxy resin, (B) an inorganic filler, (C) a curing agent, and (D) a non-epoxy compound having a polyether skeleton,
wherein the polyether skeleton contained in the component (D) is a polyoxyalkylene skeleton composed of 1 or more monomer units selected from ethylene oxide units and propylene oxide units,
the content of the component (B) is 70% by mass or more based on 100% by mass of the total nonvolatile components in the resin composition,
the content of the component (D) is 1 to 30% by mass, based on 100% by mass of nonvolatile components other than the component (B) in the resin composition.
2. The resin composition according to claim 1, wherein the component (D) is at least 1 compound selected from the group consisting of polyalkylene glycols and polyoxyalkylene-modified silicones.
3. The resin composition according to claim 2, wherein the polyalkylene glycol is polyoxyethylene polyoxypropylene glycol.
4. The resin composition according to claim 1, wherein the number average molecular weight of the component (D) is 500 to 10000.
5. The resin composition according to claim 1, wherein the viscosity of component (D) at 25 ℃ is 3000mPa or less.
6. The resin composition according to claim 1, wherein the content of the component (B) is 78% by mass or more, assuming that all nonvolatile components in the resin composition are 100% by mass.
7. The resin composition according to claim 1, wherein the component (B) is silica.
8. The resin composition according to claim 1, wherein the (a) component comprises: an epoxy resin having a condensed ring structure.
9. The resin composition according to claim 8, wherein the content of the epoxy resin having a condensed ring structure in the component (A) is 50% by mass or more, based on 100% by mass of the total amount of the component (A).
10. The resin composition according to claim 1, wherein the component (A) comprises a glycidylamine-type epoxy resin.
11. The resin composition according to claim 1, wherein the component (a) comprises a liquid epoxy resin.
12. The resin composition according to claim 11, wherein the content of the liquid epoxy resin in the component (A) is 50% by mass or more, assuming that the total amount of the component (A) is 100% by mass.
13. The resin composition according to claim 1, wherein the content of the component (A) is 40% by mass or more, based on 100% by mass of nonvolatile components other than the component (B).
14. The resin composition according to claim 1, wherein the component (C) comprises 1 or more curing agents selected from an acid anhydride curing agent and an amine curing agent.
15. The resin composition according to claim 1, which is used for forming an insulating layer of a semiconductor chip package.
16. The resin composition according to claim 1, which is used for forming an insulating layer of a circuit substrate.
17. The resin composition according to claim 1, which is used for sealing a semiconductor chip of a semiconductor chip package.
18. A cured product of the resin composition according to any one of claims 1 to 17.
19. A resin sheet having:
a support, and
a resin composition layer comprising the resin composition according to any one of claims 1 to 17 provided on the support.
20. A circuit board comprising an insulating layer formed from a cured product of the resin composition according to any one of claims 1 to 17.
21. A semiconductor chip package, comprising:
the circuit substrate of claim 20, and
and a semiconductor chip mounted on the circuit board.
22. A semiconductor device provided with the semiconductor chip package according to claim 21.
23. A semiconductor chip package, comprising:
semiconductor chip, and
a cured product of the resin composition according to any one of claims 1 to 17, which encapsulates the semiconductor chip.
24. A semiconductor device provided with the semiconductor chip package according to claim 23.
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US20240262994A1 (en) * | 2021-11-26 | 2024-08-08 | Lg Chem, Ltd | Composition for Encapsulant Film and Encapsulant Film Comprising the Same |
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JP2021123647A (en) | 2021-08-30 |
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