CN111748175A - Resin composition - Google Patents
Resin composition Download PDFInfo
- Publication number
- CN111748175A CN111748175A CN202010223164.6A CN202010223164A CN111748175A CN 111748175 A CN111748175 A CN 111748175A CN 202010223164 A CN202010223164 A CN 202010223164A CN 111748175 A CN111748175 A CN 111748175A
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- China
- Prior art keywords
- resin composition
- resin
- mass
- composition according
- manufactured
- Prior art date
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- 239000011342 resin composition Substances 0.000 title claims abstract description 191
- 229920005989 resin Polymers 0.000 claims abstract description 148
- 239000011347 resin Substances 0.000 claims abstract description 148
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 81
- 239000011256 inorganic filler Substances 0.000 claims abstract description 40
- 229910003475 inorganic filler Inorganic materials 0.000 claims abstract description 40
- 229920001187 thermosetting polymer Polymers 0.000 claims abstract description 27
- 239000012766 organic filler Substances 0.000 claims abstract description 23
- 239000000853 adhesive Substances 0.000 claims abstract description 21
- 230000001070 adhesive effect Effects 0.000 claims abstract description 21
- 239000003822 epoxy resin Substances 0.000 claims description 112
- 229920000647 polyepoxide Polymers 0.000 claims description 112
- 229920002857 polybutadiene Polymers 0.000 claims description 54
- 239000005062 Polybutadiene Substances 0.000 claims description 48
- 239000002245 particle Substances 0.000 claims description 47
- 229920001721 polyimide Polymers 0.000 claims description 41
- 239000000758 substrate Substances 0.000 claims description 41
- 239000002253 acid Substances 0.000 claims description 25
- 239000009719 polyimide resin Substances 0.000 claims description 23
- 239000000539 dimer Substances 0.000 claims description 21
- 239000007787 solid Substances 0.000 claims description 19
- 150000002148 esters Chemical class 0.000 claims description 18
- 229920006033 core shell type graft co-polymer Polymers 0.000 claims description 15
- 239000004065 semiconductor Substances 0.000 claims description 15
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 12
- 239000007771 core particle Substances 0.000 claims description 10
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 claims description 8
- 239000011258 core-shell material Substances 0.000 claims description 6
- 239000000178 monomer Substances 0.000 claims description 5
- 229920002725 thermoplastic elastomer Polymers 0.000 claims description 4
- 229920000578 graft copolymer Polymers 0.000 claims description 2
- 239000010410 layer Substances 0.000 description 163
- 238000001723 curing Methods 0.000 description 105
- -1 glycidyl ester Chemical class 0.000 description 101
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 62
- 239000000126 substance Substances 0.000 description 48
- 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 46
- 238000000034 method Methods 0.000 description 35
- 125000004122 cyclic group Chemical group 0.000 description 32
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 32
- 239000000243 solution Substances 0.000 description 30
- 239000000047 product Substances 0.000 description 27
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 26
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 24
- 239000004020 conductor Substances 0.000 description 24
- 229920003986 novolac Polymers 0.000 description 24
- 230000015572 biosynthetic process Effects 0.000 description 22
- 229910052751 metal Inorganic materials 0.000 description 22
- 239000002184 metal Substances 0.000 description 22
- 229920001971 elastomer Polymers 0.000 description 21
- 239000000463 material Substances 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 19
- 238000003786 synthesis reaction Methods 0.000 description 19
- 239000005060 rubber Substances 0.000 description 18
- 239000003960 organic solvent Substances 0.000 description 17
- 239000004642 Polyimide Substances 0.000 description 16
- 239000000523 sample Substances 0.000 description 16
- 235000013824 polyphenols Nutrition 0.000 description 15
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 14
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 14
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 14
- 238000003475 lamination Methods 0.000 description 14
- 238000004519 manufacturing process Methods 0.000 description 14
- 125000001424 substituent group Chemical group 0.000 description 14
- 150000001875 compounds Chemical class 0.000 description 13
- 125000006158 tetracarboxylic acid group Chemical group 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 239000010408 film Substances 0.000 description 12
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 12
- 238000007788 roughening Methods 0.000 description 12
- 239000004593 Epoxy Substances 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
- 230000000694 effects Effects 0.000 description 11
- 125000003700 epoxy group Chemical group 0.000 description 11
- 238000010030 laminating Methods 0.000 description 11
- 239000000377 silicon dioxide Substances 0.000 description 11
- 238000012360 testing method Methods 0.000 description 11
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 10
- 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 10
- 239000000956 alloy Substances 0.000 description 10
- 238000005452 bending Methods 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 229910052802 copper Inorganic materials 0.000 description 10
- 239000010949 copper Substances 0.000 description 10
- 239000004850 liquid epoxy resins (LERs) Substances 0.000 description 10
- 238000005259 measurement Methods 0.000 description 10
- 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 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- 206010042674 Swelling Diseases 0.000 description 9
- 229910045601 alloy Inorganic materials 0.000 description 9
- 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 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 230000001681 protective effect Effects 0.000 description 9
- 230000008961 swelling Effects 0.000 description 9
- 229920000858 Cyclodextrin Polymers 0.000 description 8
- DMBHHRLKUKUOEG-UHFFFAOYSA-N N-phenyl aniline Natural products C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 8
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 8
- 150000004985 diamines Chemical class 0.000 description 8
- 238000005227 gel permeation chromatography Methods 0.000 description 8
- 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 8
- 239000007788 liquid Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 238000007747 plating Methods 0.000 description 8
- 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 7
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 7
- 229930003836 cresol Natural products 0.000 description 7
- 239000004643 cyanate ester Substances 0.000 description 7
- 238000009826 distribution Methods 0.000 description 7
- 239000011888 foil Substances 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- MXPYJVUYLVNEBB-UHFFFAOYSA-N 2-[2-(2-carboxybenzoyl)oxycarbonylbenzoyl]oxycarbonylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)OC(=O)C1=CC=CC=C1C(=O)OC(=O)C1=CC=CC=C1C(O)=O MXPYJVUYLVNEBB-UHFFFAOYSA-N 0.000 description 6
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 6
- 239000004805 Cyclohexane-1,2-dicarboxylic acid Substances 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 150000008065 acid anhydrides Chemical class 0.000 description 6
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 125000001624 naphthyl group Chemical group 0.000 description 6
- 239000002904 solvent 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
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 5
- 229920002121 Hydroxyl-terminated polybutadiene Polymers 0.000 description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 5
- 239000004793 Polystyrene Substances 0.000 description 5
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 5
- 239000002518 antifoaming agent Substances 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 229910052804 chromium Inorganic materials 0.000 description 5
- 239000011651 chromium Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 238000001035 drying 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
- 238000002156 mixing Methods 0.000 description 5
- 229910052759 nickel Inorganic materials 0.000 description 5
- 239000007800 oxidant agent Substances 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 229920003192 poly(bis maleimide) Polymers 0.000 description 5
- 229920002223 polystyrene Polymers 0.000 description 5
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 5
- 229910052719 titanium Inorganic materials 0.000 description 5
- 239000010936 titanium Substances 0.000 description 5
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 5
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 5
- 229910052725 zinc Inorganic materials 0.000 description 5
- 239000011701 zinc 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
- 229930185605 Bisphenol Natural products 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
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 4
- 239000002202 Polyethylene glycol Substances 0.000 description 4
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 4
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 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
- 150000008064 anhydrides Chemical class 0.000 description 4
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 4
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 4
- 239000011889 copper foil Substances 0.000 description 4
- 239000007822 coupling agent Substances 0.000 description 4
- 239000003063 flame retardant Substances 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 238000009499 grossing Methods 0.000 description 4
- 125000005647 linker group Chemical group 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 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
- 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 4
- 230000003472 neutralizing effect Effects 0.000 description 4
- 229910000623 nickel–chromium alloy Inorganic materials 0.000 description 4
- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical compound NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- 239000011574 phosphorus Substances 0.000 description 4
- LGRFSURHDFAFJT-UHFFFAOYSA-N phthalic anhydride Chemical class C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- 229920000139 polyethylene terephthalate Polymers 0.000 description 4
- 239000005020 polyethylene terephthalate Substances 0.000 description 4
- 238000003825 pressing Methods 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 4
- 229910052709 silver Inorganic materials 0.000 description 4
- 239000004332 silver Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 229910052718 tin Inorganic materials 0.000 description 4
- VFXMQOBHRJEVDM-UHFFFAOYSA-N (4-amino-2-phenylphenyl) 4-aminobenzoate Chemical compound C1=CC=CC=C1C1=C(OC(=O)C2=CC=C(N)C=C2)C=CC(=C1)N VFXMQOBHRJEVDM-UHFFFAOYSA-N 0.000 description 3
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 description 3
- FPZWZCWUIYYYBU-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl acetate Chemical compound CCOCCOCCOC(C)=O FPZWZCWUIYYYBU-UHFFFAOYSA-N 0.000 description 3
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 3
- 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 3
- GQSMMSNWAYPBIR-UHFFFAOYSA-N 4-[4-[6-(4-aminophenoxy)-1,3,3-trimethyl-2h-inden-1-yl]phenoxy]aniline Chemical compound C=1C=C2C(C)(C)CC(C)(C=3C=CC(OC=4C=CC(N)=CC=4)=CC=3)C2=CC=1OC1=CC=C(N)C=C1 GQSMMSNWAYPBIR-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
- 229920002799 BoPET Polymers 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-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
- 239000005058 Isophorone diisocyanate Substances 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
- 229920000265 Polyparaphenylene Polymers 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000004018 acid anhydride group Chemical group 0.000 description 3
- 239000005456 alcohol based solvent Substances 0.000 description 3
- 125000002723 alicyclic group Chemical group 0.000 description 3
- 229920000180 alkyd Polymers 0.000 description 3
- RSHYBLDYLNAJJV-UHFFFAOYSA-N anthracene-1,2,3,4-tetracarboxylic acid Chemical compound C1=CC=CC2=CC3=C(C(O)=O)C(C(=O)O)=C(C(O)=O)C(C(O)=O)=C3C=C21 RSHYBLDYLNAJJV-UHFFFAOYSA-N 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
- 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 3
- 239000013039 cover film Substances 0.000 description 3
- 230000007547 defect Effects 0.000 description 3
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 3
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Natural products C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 3
- 239000000806 elastomer Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 3
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- 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
- 229910052726 zirconium Inorganic materials 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
- 150000007934 α,β-unsaturated carboxylic acids Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/38—Layered products comprising a layer of synthetic resin comprising epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/42—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof
- C08G59/4246—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof polymers with carboxylic terminal groups
- C08G59/4269—Macromolecular compounds obtained by reactions other than those involving unsaturated carbon-to-carbon bindings
- C08G59/4276—Polyesters
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/12—Powdering or granulating
- C08J3/126—Polymer particles coated by polymer, e.g. core shell structures
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/18—Manufacture of films or sheets
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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
- C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
- C08K3/013—Fillers, pigments or reinforcing additives
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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
- C08L101/00—Compositions of unspecified macromolecular compounds
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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
- C08L51/00—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
- C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C08L79/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
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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
- C08L9/00—Compositions of homopolymers or copolymers of conjugated diene hydrocarbons
-
- 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
- H05K1/0296—Conductive pattern lay-out details not covered by sub groups H05K1/02 - H05K1/0295
- H05K1/0298—Multilayer circuits
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2363/00—Characterised by the use of epoxy resins; Derivatives of epoxy resins
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08J2463/00—Characterised by the use of epoxy resins; Derivatives of epoxy resins
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- 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
- C08L2205/035—Polymer mixtures characterised by other features containing three or more polymers in a blend containing four or more polymers in a blend
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Materials Engineering (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Crystallography & Structural Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Epoxy Resins (AREA)
- Production Of Multi-Layered Print Wiring Board (AREA)
Abstract
The present invention addresses the problem of providing a resin composition that suppresses tackiness to a low level while maintaining excellent flexibility. The present invention provides a resin composition comprising (A) a thermosetting resin, (B) an inorganic filler, (C) an organic filler, and (D) an adhesive flexibilizing agent, wherein the content of the component (C) is 5% by mass or more, assuming that the nonvolatile component in the resin composition is 100% by mass.
Description
Technical Field
The present invention relates to a resin composition containing a thermosetting resin and an inorganic filler.
Background
In recent years, there has been an increasing demand for thinner and lighter semiconductor components with high mounting density. In order to meet this demand, attention has been paid to the use of a flexible substrate as a base substrate used for semiconductor components. The flexible substrate can be thin and lightweight compared to a rigid substrate. In addition, since the flexible substrate is flexible and deformable, it can be mounted by bending it.
In general, it is necessary to blend a flexibilizing resin component in the insulating material of the flexible substrate, but when the flexibilizing resin component is blended, adhesiveness (adhesiveness) may be increased, and handling property may be poor. In this case, the adhesion can be suppressed by blending an inorganic filler (patent document 1), but when the blending ratio of the inorganic filler is increased, it is difficult to achieve both flexibility and adhesion.
Documents of the prior art
Patent document
Patent document 1: japanese patent laid-open No. 2014-95047.
Disclosure of Invention
Problems to be solved by the invention
Accordingly, an object of the present invention is to provide a resin composition in which tackiness is suppressed to a low level while maintaining excellent flexibility.
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 when (C) an organic filler is added in an amount of 5 mass% or more to a resin composition containing (a) a thermosetting resin, (D) an adhesive flexibilizer, and (B) an inorganic filler, the adhesiveness can be suppressed to a low level while maintaining excellent flexibility, and thus the present invention has been completed.
That is, the present invention includes the following,
[1] a resin composition comprising (A) a thermosetting resin, (B) an inorganic filler, (C) an organic filler, and (D) an adhesive flexibilizing agent,
the content of the component (C) is 5% by mass or more, assuming that the nonvolatile component in the resin composition is 100% by mass;
[2] the resin composition according to the above [1], wherein the content of the component (B) is 50% by mass or less, assuming that the nonvolatile component in the resin composition is 100% by mass;
[3] the resin composition according to the above [1] or [2], wherein the content of the component (C) is 10% by mass or less, assuming that the nonvolatile component in the resin composition is 100% by mass;
[4] the resin composition according to any one of the above [1] to [3], wherein the component (D) is selected from the group consisting of a resin having a polybutadiene structure, a polyrotaxane resin, a polyimide resin, and a maleimide resin having a dimer acid skeleton;
[5] the resin composition according to any one of the above [1] to [4], wherein the content of the component (D) is 1% by mass or more, assuming that the nonvolatile component in the resin composition is 100% by mass;
[6] the resin composition according to any one of the above [1] to [5], wherein (C) the organic filler is core-shell type graft copolymer particles;
[7] the resin composition according to the above [6], wherein the monomer component forming the shell portion of the core-shell type graft copolymer particle is a (meth) acrylate;
[8] the resin composition according to the above [6] or [7], wherein the core particle of the core-shell type graft copolymer particle comprises a thermoplastic elastomer;
[9] the resin composition according to any one of the above [1] to [8], wherein the component (A) is an epoxy resin;
[10] the resin composition according to any one of the above [1] to [9], further comprising (E) a curing agent;
[11] the resin composition according to the above [10], wherein the component (E) comprises an active ester curing agent;
[12] the resin composition according to any one of the above [1] to [11], wherein a solid content ratio in the resin composition is 95% by mass or less;
[13] the resin composition according to any one of the above [1] to [12], which is used for forming an insulating layer of a multilayer flexible substrate;
[14] a cured product of the resin composition according to any one of the above [1] to [13 ];
[15] a resin sheet comprising a support and, provided thereon, a resin composition layer formed of the resin composition according to any one of the above [1] to [13 ];
[16] a multilayer flexible substrate comprising an insulating layer formed by curing the resin composition according to any one of the above [1] to [13 ];
[17] a semiconductor device comprising the multilayer flexible substrate according to [16 ].
ADVANTAGEOUS EFFECTS OF INVENTION
According to the resin composition of the present invention, the tackiness can be suppressed to a low level while maintaining excellent flexibility.
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 embodiments and examples described below, and may be modified and implemented as desired within the scope of the claims and their equivalents.
< resin composition >
The resin composition of the present invention comprises (A) a thermosetting resin, (B) an inorganic filler, (C) an organic filler, and (D) an adhesive flexibilizer. The content of the component (C) is 5% by mass or more, assuming that the nonvolatile content in the resin composition is 100% by mass.
By using such a resin composition, the tackiness can be suppressed to a low level while maintaining excellent flexibility.
The resin composition of the present invention may further contain any component in addition to the thermosetting resin (a), the inorganic filler (B), the organic filler (C), and the adhesive flexibilizer (D). Examples of the optional component include (E) a curing agent, (F) a curing accelerator, (G) other additives, and (H) an organic solvent. The components contained in the resin composition will be described in detail below.
< (A) thermosetting resin
The resin composition of the present invention contains (a) a thermosetting resin. (A) The thermosetting resin does not contain a resin belonging to the component (D). (A) The thermosetting resin may be a known thermosetting resin, and is not particularly limited, and examples thereof include polyester resin, polyurethane resin, polyester-polyurethane resin, butyral resin, acrylic resin, cyanate resin, silicone resin, oxetane resin, melamine resin, and the like, and among them, epoxy resin is preferable.
Examples of the epoxy resin include a bisxylenol 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 type epoxy resin, a 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 glycidyl amine type epoxy resin, a glycidyl ester type epoxy resin, a cresol novolac type epoxy resin, a biphenyl type epoxy resin, a linear aliphatic epoxy resin, 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 trimethylol type epoxy resin, Tetraphenylethane type epoxy resins, and the like. The epoxy resin may be used alone in 1 kind, or in combination of 2 or more kinds.
In the resin composition, the epoxy resin is preferably an epoxy resin having 2 or more epoxy groups in 1 molecule. From the viewpoint of remarkably obtaining the desired effect of the present invention, 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.
The epoxy resin includes an epoxy resin which is liquid at a temperature of 20 ℃ (hereinafter sometimes referred to as "liquid epoxy resin") and an epoxy resin which 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, but preferably a liquid epoxy resin and a solid epoxy resin are contained in combination.
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 glycidyl amine type epoxy resin are preferable.
Specific examples of the liquid epoxy resin include "HP 4032", "HP 4032D" and "HP 4032 SS" (naphthalene type epoxy resin) manufactured by DIC corporation; "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" and "630 LSD" (glycidyl amine type epoxy resins) manufactured by mitsubishi chemical corporation; "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; "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.
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 trisphenol-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 "HP 4032H" (naphthalene type 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.
When a liquid epoxy resin and a solid epoxy resin are used in combination as the epoxy resin, the mass ratio thereof (liquid epoxy resin: solid epoxy resin) is preferably 1:1 to 1:50, more preferably 1:3 to 1:30, and particularly preferably 1:5 to 1: 20. By setting the mass ratio of the liquid epoxy resin to the solid epoxy resin within the above range, the desired effects of the present invention can be remarkably obtained.
The epoxy equivalent of the epoxy resin is preferably 50g/eq to 5,000g/eq, more preferably 50g/eq to 3,000g/eq, even more preferably 80g/eq to 2,000g/eq, and even more preferably 110g/eq to 1,000g/eq. When the content is within the above range, the crosslinking density of the cured product of the resin composition becomes sufficient, and an insulating layer having a small surface roughness can be formed. 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.
The weight average molecular weight (Mw) of the epoxy resin is preferably 100 to 5,000, more preferably 250 to 3,000, and even more preferably 400 to 1,500, from the viewpoint of remarkably obtaining the desired effect of the present invention. The weight average molecular weight of the resin can be measured as a value in terms of polystyrene by Gel Permeation Chromatography (GPC).
(A) The content of the thermosetting resin is not particularly limited, and is preferably 5% by mass or more, more preferably 10% by mass or more, further preferably 15% by mass or more, and particularly preferably 20% by mass or more, assuming that the nonvolatile content in the resin composition is 100% by mass. (A) The upper limit of the content of the thermosetting resin is not particularly limited, and is preferably 50% by mass or less, more preferably 40% by mass or less, further preferably 30% by mass or less, and particularly preferably 25% by mass or less, assuming that the nonvolatile content in the resin composition is 100% by mass.
(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 zirconate, barium zirconate, calcium zirconate, zirconium phosphate, and zirconium phosphate tungstate, and the like, and silica is particularly preferable. 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.
(B) The average particle size of the inorganic filler is not particularly limited, but is preferably 10 μm or less, more preferably 5 μm or less, still more preferably 3 μm or less, still more preferably 2 μm or less, and particularly preferably 1 μm or less, from the viewpoint of obtaining the desired effect of the present invention. From the viewpoint of obtaining the desired effect of the present invention, the lower limit of the average particle size of the inorganic filler is preferably 0.01 μm or more, more preferably 0.05 μm or more, still more preferably 0.1 μm or more, still more preferably 0.2 μm or more, and particularly preferably 0.25 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. The measurement sample may be 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 (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.
Examples of commercially available products of the inorganic filler (B) include "UFP-30" manufactured by the electric chemical industry Co., Ltd; "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 (トクヤマ); "SC 2500 SQ", "SO-C4", "SO-C2" and "SO-C1" manufactured by Yadama corporation; and so on.
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, from the viewpoint of improving moisture resistance and dispersibility. Examples of commercially available surface-treating agents include "KBM 403" (3-glycidoxypropyltrimethoxysilane) available from shin-Etsu chemical Co., Ltd., "KBM 803" (3-mercaptopropyltrimethoxysilane) available from shin-Etsu chemical Co., Ltd., "KBE 903" (3-aminopropyltriethoxysilane) available from shin-Etsu chemical Co., Ltd., "KBM 573" (N-phenyl-3-aminopropyltrimethoxysilane) available from shin-Etsu chemical Co., Ltd., "SZ-31" (hexamethyldisilazane) manufactured by shin-Etsu chemical industries, "KBM 103" (phenyltrimethoxysilane) manufactured by shin-Etsu chemical industries, "KBM-4803" (long-chain epoxy silane coupling agent) manufactured by shin-Etsu chemical industries, and "KBM-7103" (3,3, 3-trifluoropropyltrimethoxysilane) manufactured by shin-Etsu chemical industries.
From the viewpoint of improving the dispersibility of the inorganic filler, it is preferable to control the degree of the surface treatment with the surface treatment agent to be within 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 with the surface treatment agent can be evaluated by the amount of carbon per unit surface area of the inorganic filler. From the viewpoint of improving the dispersibility of the inorganic filler, the carbon amount per unit surface area of the inorganic filler is preferably 0.02mg/m2Above, more preferably 0.1mg/m2Above, more preferably 0.2mg/m2The above. On the other hand, fromFrom the viewpoint of preventing the increase in melt viscosity of the resin composition and melt viscosity in the form of a sheet, it is preferably 1mg/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 (for example, 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 components were 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, "EMIA-320V" manufactured by horiba, Ltd., can be used.
(B) The specific surface area of the inorganic filler is preferably 1m2A value of at least g, more preferably 2m2A 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 gram2The 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, the specific surface area was calculated by a BET multipoint method by adsorbing nitrogen gas on the surface of the sample using a specific surface area measuring apparatus (Macsorb HM-1210, Mountech).
The content of the inorganic filler (B) is preferably 70% by mass or less, more preferably 60% by mass or less, further preferably 50% by mass or less, and particularly preferably 45% by mass or less, from the viewpoint of obtaining a cured product having more excellent flexibility, assuming that the nonvolatile content in the resin composition is 100% by mass. (B) The lower limit of the content of the inorganic filler is not particularly limited, and from the viewpoint of obtaining a cured product having sufficient mechanical strength, the nonvolatile content of the resin composition is preferably 20 mass% or more, more preferably 30 mass% or more, further preferably 35 mass% or more, and particularly preferably 38 mass% or more, when taken as 100 mass%.
(C) organic filler
The resin composition of the present invention contains (C) an organic filler. (C) The organic filler material does not contain a material belonging to the component (D). By including the component (C) in the resin composition, tackiness can be reduced and handling properties can be improved.
(C) The organic filler is present in the resin composition in the form of particles. Examples of the organic filler (C) include rubber particles, polyamide microparticles, and silicone particles, and in the present invention, rubber particles are preferably used from the viewpoint of remarkably obtaining the effects desired by the present invention.
Examples of the rubber component contained in the rubber particles include olefin-based thermoplastic elastomers such as polybutadiene, polyisoprene, polychloroprene, ethylene-vinyl acetate copolymers, styrene-butadiene copolymers, styrene-isoprene copolymers, styrene-isobutylene copolymers, acrylonitrile-butadiene copolymers, isoprene-isobutylene copolymers, isobutylene-butadiene copolymers, ethylene-propylene-diene terpolymers, and ethylene-propylene-butene terpolymers; thermoplastic elastomers such as acrylic thermoplastic elastomers such as polypropylene (meth) acrylate, polybutylene (meth) acrylate, polycyclohexyl (meth) acrylate, and octyl (meth) acrylate are preferably olefinic thermoplastic elastomers, and more preferably styrene-butadiene copolymers. The rubber component may further contain a silicone rubber such as polyorganosiloxane rubber. The glass transition temperature of the rubber component contained in the rubber particles is, for example, 0 ℃ or lower, preferably-10 ℃ or lower, more preferably-20 ℃ or lower, and still more preferably-30 ℃ or lower.
The organic filler (C) is preferably a core-shell type particle in terms of remarkably obtaining the desired effect of the present invention. The core-shell type particles are particulate organic fillers formed of "core particles containing a rubber component as described above" and "1 or more shell portions covering the core particles". Further, the core-shell type particles are preferably core-shell type graft copolymer particles formed of "core particles containing a rubber component as exemplified above" and "shell portions obtained by graft-copolymerizing monomer components copolymerizable with the rubber component contained in the core particles". The core-shell type herein does not necessarily mean only those in which the core particle and the shell are clearly distinguished from each other, and includes those in which the boundary between the core particle and the shell is not clear, and the core particle may not be completely covered with the shell.
The rubber component is preferably contained in the core-shell type graft copolymer particles in an amount of 40 mass% or more, more preferably 50 mass% or more, and still more preferably 60 mass% or more. The upper limit of the content of the rubber component in the core-shell type graft copolymer particles is not particularly limited, and is, for example, 95% by mass or less, preferably 90% by mass, from the viewpoint of sufficiently covering the core particles with the shell portion.
Examples of the monomer component forming the shell portion of the core-shell type graft copolymer particle include (meth) acrylic esters such as methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, cyclohexyl (meth) acrylate, octyl (meth) acrylate, and glycidyl (meth) acrylate; (meth) acrylic acid; n-substituted maleimides such as N-methylmaleimide and N-phenylmaleimide; a maleimide; α, β -unsaturated carboxylic acids such as maleic acid and itaconic acid; aromatic vinyl compounds such as styrene, 4-vinyltoluene and α -methylstyrene; (meth) acrylonitrile, etc., preferably (meth) acrylic acid esters, more preferably methyl (meth) acrylate.
Examples of commercially available core-shell graft copolymer particles include "CHT" manufactured by chemical Industries, Inc.; "B602" manufactured by UMGABS corporation; "PARALOID EXL 2602", "PARALOIDEXL 2603", "PARALOID EXL 2655", "PARALOID EXL 2311", "PARALOID EXL 2313", "PARALOIDEXL 2315", "PARALOID KM 330", "PARALOID KM 336P", "PARALOID KCZ 201" manufactured by Dow chemical Japan; "METABLEN C-223A", "METABLEN E-901", "METABLEN S-2001", "METABLEN NW-450A", "METABLEN SRK-200", manufactured by Mitsubishi rayon, Inc.; "Kane Ace M-511", "Kane Ace M-600", "Kane Ace M-400", "Kane Ace M-580", and "Kane Ace MR-01" manufactured by Kaneka corporation. These can be used alone in 1 kind, also can be combined with more than 2 kinds.
The average particle diameter (average primary particle diameter) of the core-shell type graft copolymer particles is not particularly limited, but is preferably 20nm or more, more preferably 50nm or more, further preferably 80nm or more, particularly preferably 100nm or more, preferably 5,000nm or less, more preferably 2,000nm or less, further preferably 1,000nm or less, and particularly preferably 500nm or less. The average particle diameter (average primary particle diameter) of the core-shell type graft copolymer particles can be measured using a Zeta potential particle size distribution measuring instrument or the like.
The content of the (C) organic filler is 5.0 mass% or more, and is preferably 5.5 mass% or more, more preferably 5.8 mass% or more, even more preferably 6.0 mass% or more, and particularly preferably 6.2 mass% or more, from the viewpoint of suppressing the tackiness as much as possible and further suppressing the amount of the (B) inorganic filler used as much as possible to obtain a cured product having higher flexibility, assuming that the nonvolatile content in the resin composition is 100 mass%. The upper limit of the content of the (C) organic filler is preferably 30 mass% or less, 20 mass% or less, and more preferably 15 mass% or less, from the viewpoint of suppressing the viscosity to a low level as much as possible, and from the viewpoint of reducing void defects and achieving more excellent pattern embeddability, the upper limit is more preferably 10 mass% or less, and particularly preferably 8 mass% or less, when the nonvolatile content in the resin composition is 100 mass%.
(D) adhesive flexibilizer
The resin composition of the present invention contains (D) an adhesive flexibilizing agent.
(D) The adhesive flexibilizer is a component having a property of improving the adhesiveness of a cured product, among flexibilizers that impart flexibility to the cured product of a thermosetting resin. As the adhesive flexibilizer (D), a known flexibilizer having a property of improving the adhesiveness of a cured product can be widely used. Examples of the adhesive flexibilizing agent (D) include, but are not limited to, resins having a polybutadiene structure (hereinafter referred to as "polybutadiene resins"), polyrotaxane resins, polyimide resins, and maleimide resins having a dimer acid skeleton.
The polybutadiene structure includes not only a structure obtained by polymerizing butadiene but also a structure obtained by hydrogenating the structure. In addition, only a part of the butadiene structure may be hydrogenated, or all of the butadiene structure may be hydrogenated. In addition, the polybutadiene structure may be contained in the main chain or may be contained in the side chain in the component (D).
Preferred examples of the polybutadiene resin include resins having a hydrogenated polybutadiene skeleton, polybutadiene resins having a hydroxyl group, polybutadiene resins having a phenolic hydroxyl group, polybutadiene resins having a carboxyl group, polybutadiene resins having an acid anhydride group, polybutadiene resins having an epoxy group, polybutadiene resins having an isocyanate group, polybutadiene resins having a urethane group, and polyphenylene ether-polybutadiene resins. Here, the "resin having a hydrogenated polybutadiene skeleton" refers to a resin in which at least a part of the polybutadiene skeleton is hydrogenated, and is not necessarily a resin in which the polybutadiene skeleton is completely hydrogenated. Examples of the resin having a hydrogenated polybutadiene skeleton include epoxy resins having a hydrogenated polybutadiene skeleton. Examples of the polybutadiene resin having a phenolic hydroxyl group include resins having a phenolic hydroxyl group and having a polybutadiene structure.
Specific examples of the polybutadiene resin having a polybutadiene structure in the molecule include "BX 360" and "BX 660" (polyphenylene ether-polybutadiene resin) manufactured by japan chemical corporation, "Ricon 657" (polybutadiene containing epoxy group), and "Ricon 130MA 8", "Ricon 130MA 13", "Ricon 130MA 20", "Ricon 131MA 5", "Ricon 131MA 10", "Ricon 131MA 17", "Ricon 131MA 20", "Ricon 184MA 6" (polybutadiene containing acid anhydride group), and "GQ-1000" (polybutadiene having hydroxyl and carboxyl groups introduced therein), "G-1000", "G-2000", "G-3000" (hydroxyl-terminated polybutadiene), and "GI-1000", "GI-2000", "GI-3000" (hydroxyl-terminated hydrogenated polybutadiene), and "360pb 0" manufactured by cellosolve corporation, "PB 4700" (polybutadiene skeleton epoxy compound), "Epofriend A1005", "Epofriend A1010", "Epofriend A1020" (epoxy compound of block copolymer of styrene and butadiene and styrene), "FCA-061L" (hydrogenated polybutadiene skeleton epoxy compound) manufactured by Nagase ChemteX, and "R-45 EPT" (polybutadiene skeleton epoxy compound).
Further, as a preferred example of the polybutadiene resin, there is also mentioned a linear polyimide butadiene resin (polyimide described in japanese patent laid-open publication No. 2006-37083 and international publication No. 2008/153208) which is prepared from hydroxyl-terminated polybutadiene, a diisocyanate compound, and a polybasic acid or an acid anhydride thereof. The content of the polybutadiene structure in the polyimide butadiene resin is preferably 60 to 95% by mass, and more preferably 75 to 85% by mass. The polyimide butadiene resin can be described in detail in Japanese patent laid-open No. 2006-37083 and International publication No. 2008/153208, which are incorporated herein by reference.
The hydroxyl-terminated polybutadiene as a raw material of the polyimide butadiene resin preferably has a number average molecular weight of 500 to 5,000, more preferably 1,000 to 3,000, from the viewpoint of exhibiting the desired effects of the present invention. From the viewpoint of exhibiting the desired effects of the present invention, the hydroxyl equivalent weight of the hydroxyl-terminated polybutadiene is preferably 250 to 1,250.
Examples of the diisocyanate compound as a raw material of the polyimide butadiene resin include aromatic diisocyanates such as 2, 4-tolylene diisocyanate, 2, 6-tolylene diisocyanate, xylylene diisocyanate (xylylene diisocyanate), and diphenylmethane diisocyanate; aliphatic diisocyanates such as hexamethylene diisocyanate; alicyclic diisocyanates such as isophorone diisocyanate. Among these, aromatic diisocyanates are preferable, and 2, 4-tolylene diisocyanate is more preferable.
Examples of the polybasic acid or anhydride thereof as a raw material of the polyimide butadiene resin include, for example, ethylene glycol bistrimellitic acid, pyromellitic acid, benzophenone tetracarboxylic acid, biphenyl tetracarboxylic acid, naphthalene tetracarboxylic acid, 5- (2, 5-dioxotetrahydrofuryl) -3-methyl-cyclohexene-1, 2-dicarboxylic acid, 3,3 '-4, 4' -diphenylsulfone tetracarboxylic acid and other tetrabasic acids and their anhydrides, trimellitic acid, cyclohexanetricarboxylic acid and other tribasic acids and their anhydrides, and 1,3,3a,4,5,9 b-hexahydro-5- (tetrahydro-2, 5-dioxo-3-furanyl) -naphtho (1,2-C) furan-1, 3-dione.
The polyrotaxane resin is a resin having a structure having: the present invention relates to a probe for detecting a probe for a probe tip, and more particularly to a probe for a probe tip that includes a plurality of cyclic molecules, a linear shaft molecule enclosed (enclosed) so as to pass through (pass through) the cyclic molecules, and a capping group that blocks the end of the shaft molecule so that the cyclic molecules do not fall off (slip off). The number of cyclic molecules (inclusion amount) in the polyrotaxane resin is not particularly limited as long as the number of cyclic molecules is within a range of 2 or more, and for example, when 1 axial molecule is included in a state where a plurality of cyclic molecules are penetrated, an amount (maximum inclusion amount) in which 1 axial molecule is included at the maximum in the cyclic molecules is 100%, it is preferably 10% or more, more preferably 15% or more, further preferably 20% or more, preferably 90% or less, more preferably 85% or less, and further preferably 80% or less. The amount of inclusion may be determined by the length of the axial molecules and the thickness of the cyclic molecules. For example, in the case where the axial molecule is polyethylene glycol and the cyclic molecule is α -cyclodextrin molecule, the maximum inclusion amount is experimentally determined (see Macromolecules 1993, 26, 5698-.
As the axial molecule in the polyrotaxane resin, a linear molecule having a molecular weight of 10,000 or more and a terminal that can be chemically modified with a capping group can be used. The term "linear" means a substantially linear chain, and the axial molecule may have a branch as long as the cyclic molecule through which the axial molecule passes can rotate or move. Examples of the axial molecule include polyvinyl alcohol, polyvinyl pyrrolidone, poly (meth) acrylic acid cellulose-based resins, polyacrylamide, polyethylene oxide, polyethylene glycol, polypropylene glycol, polyvinyl acetal-based resins, polyvinyl methyl ether, polyamine, polyethyleneimine, casein, gelatin, starch, polyolefin, polyester, polyvinyl chloride, polystyrene, copolymers such as acrylonitrile-styrene copolymer, acrylic resins, polycarbonate, polyurethane, polyvinyl butyral, polyisobutylene, polytetrahydrofuran, polyamide, polyimide, polydiene, polysiloxane, polyurea, polysulfide, polyphosphazene, polyketone, polyphenylene, polyhaloolefin, and derivatives thereof. Among these, a polyethylene glycol chain can be preferably used. These may be present in a mixture of 2 or more kinds in the polyrotaxane resin.
The length of the axial molecule is not particularly limited as long as the cyclic molecule can rotate or move. The length of the axial molecule can be expressed using the weight average molecular weight. The weight average molecular weight of the axial molecule is preferably 3,000 or more, more preferably 4,000 or more, further preferably 5,000 or more, preferably 100,000 or less, more preferably 90,000 or less, and further preferably 85,000 or less. The weight average molecular weight of the axial molecules was determined by Gel Permeation Chromatography (GPC) and was calculated as a weight average molecular weight in terms of polystyrene.
The axial molecule typically has the following structure: the functional group of the molecule having a functional group at both ends is reacted with and bonded to a molecule having a capping group. Preferable examples of the functional group include an amide group, a hydroxyl group, a carboxyl group, an acryloyl group, a methacryloyl group, an epoxy group, and a vinyl group.
The cyclic molecule in the polyrotaxane resin is a cyclic molecule capable of including an axial molecule in a penetrating state, and a molecule having at least one reactive group (functional group) is used so as to be capable of reacting with the (E) curing agent. The term "cyclic molecule" means a substantially cyclic molecule, and the term "substantially cyclic" means a molecule that does not have a complete closed ring, and the concept thereof includes: a molecule having a helical structure in which one end of the english letter "C" is not bonded to the other end but overlaps. Examples of the cyclic molecule include cyclodextrins, crown ethers, cryptands (cryptands), macrocyclic amines, calixarenes, and cyclophanes (cyclophanes). Among these, cyclodextrins are preferred. These may be present in a mixture of 2 or more kinds in the polyrotaxane resin.
Examples of the cyclodextrin include α -cyclodextrin, β -cyclodextrin, γ -cyclodextrin, dimethylcyclodextrin, glucosylcyclodextrin, and derivatives or modifications thereof.
The cyclic molecule preferably comprises a reactive group. Examples of the reactive group include a hydroxyl group, a carboxyl group, an acryloyl group, a methacryloyl group, an epoxy group, and a vinyl group, and among them, a hydroxyl group is preferable. By having a reactive group in the cyclic molecule, the cyclic molecules can be crosslinked with each other or the polyrotaxane resin and the thermosetting resin can be crosslinked via the curing agent. In addition, the reactive group of one cyclic molecule may be crosslinked with the reactive group of the other cyclic molecule. The reactive group may be 1 kind alone or 2 or more kinds.
The reactive group may not be directly bonded to the cyclic molecule. For example, when the cyclic molecule is cyclodextrin, a hydroxyl group of cyclodextrin itself is a reactive group, and when the hydroxyl group is added to a hydroxypropyl group, a hydroxyl group of the hydroxypropyl group is also a reactive group. Further, when caprolactone is ring-opening polymerized via a hydroxyl group of a hydroxypropyl group and has a caprolactone chain, the hydroxyl group located at the opposite end of the caprolactone chain to the polyester site is also a reactive group.
Each 1 cyclic molecule may have 1 reactive group of the cyclic molecule, or may have 2 or more reactive groups of the cyclic molecule.
The weight average molecular weight of the cyclic molecule is preferably 5,000 or more, more preferably 6,000 or more, further preferably 7,000 or more, preferably 1,500,000 or less, more preferably 1,400,000 or less, and further preferably 1,350,000 or less. The weight average molecular weight of the cyclic molecule is a weight average molecular weight in terms of polystyrene measured by Gel Permeation Chromatography (GPC).
The blocking group in the polyrotaxane resin is not particularly limited as long as it has a structure having a large volume to the extent that the cyclic molecule does not fall off. Examples of the capping group include a cyclodextrin group, an adamantyl group, a dinitrophenyl group, and a trityl group. Among them, an adamantyl group is preferable. These may be 1 type alone or 2 or more types in the polyrotaxane resin.
The weight average molecular weight of the polyrotaxane resin as a whole is preferably 10,000 or more, more preferably 15,000 or more, further preferably 20,000 or more, preferably 1,500,000 or less, more preferably 1,400,000 or less, and further preferably 1,350,000 or less. The weight average molecular weight of the polyrotaxane resin is a weight average molecular weight in terms of polystyrene measured by Gel Permeation Chromatography (GPC).
The hydroxyl value of the polyrotaxane resin is preferably 45mgKOH/g or more, more preferably 50mgKOH/g or more, further preferably 55mgKOH/g or more, preferably 120mgKOH/g or less, more preferably 115mgKOH/g or less, and further preferably 110mgKOH/g or less. The hydroxyl value can be measured according to JIS K0070.
The polyrotaxane resin may be in a liquid state, but is preferably contained in a particulate state in the resin composition. The particulate polyrotaxane resin is easily dispersed, and the viscosity of the resin composition is easily lowered.
The average particle diameter of the particulate polyrotaxane resin is preferably 100nm or more, more preferably 500nm or more, further preferably 800nm or more, preferably 50,000nm or less, more preferably 40,000nm or less, and further preferably 30,000nm or less. The particulate polyrotaxane resin having such an average particle diameter can be easily dispersed uniformly in the resin composition, and the viscosity of the resin composition can be easily lowered. The average particle diameter can be measured by the same method as the measurement of the average particle diameter in the inorganic filler.
Polyrotaxane resins can be synthesized by the methods described in, for example, International publication No. 01/83566, Japanese patent application laid-open No. 2005-154675, and Japanese patent application laid-open No. 4482633.
Commercially available polyrotaxane resins can be used. Commercially available products include, for example, "SH 2400B-007", "SH 1310P" and "SERM Super Polymer A1000" manufactured by Advanced Softmaterials. These can be used alone in 1 kind, also can be combined with more than 2 kinds.
The polyimide resin is a resin having an imide bond in a repeating unit. The polyimide resin may generally include a resin obtained by imidization of a diamine compound with tetracarboxylic anhydride. The polyimide resin may also include a modified polyimide resin such as a siloxane-modified polyimide resin.
The polyimide resin may include, for example, a structure represented by formula (1).
[ chemical formula 1]
[ in the formula, X1Represents a tetravalent group obtained by removing 2-CO-O-CO-groups from tetracarboxylic dianhydride, X2Represents the removal of 2-NH groups from a diamine compound2And n represents an integer of 2 or more]。
The diamine compound used for producing the polyimide resin is not particularly limited, and examples thereof include aliphatic diamine compounds and aromatic diamine compounds.
Examples of the aliphatic diamine compound include linear aliphatic diamine compounds such as 1, 2-ethylenediamine, 1, 2-diaminopropane, 1, 3-diaminopropane, 1, 4-diaminobutane, 1, 6-hexamethylenediamine, 1, 5-diaminopentane, and 1, 10-diaminodecane; branched aliphatic diamine compounds such as 1, 2-diamino-2-methylpropane, 2, 3-diamino-2, 3-butane and 2-methyl-1, 5-diaminopentane; alicyclic diamine compounds such as 1, 3-bis (aminomethyl) cyclohexane, 1, 4-diaminocyclohexane, and 4, 4' -methylenebis (cyclohexylamine); dimer acid type diamines (hereinafter also referred to as "dimer diamines"), and the like.
The dimer acid type diamine refers to dimer acid having two terminal carboxylic acid groups (-COOH) substituted by aminomethyl (-CH)2-NH2) Or amino (-NH)2) And a diamine compound obtained by substitution. Dimer acid is a known compound obtained by dimerizing an unsaturated fatty acid (preferably, an unsaturated fatty acid having 11 to 22 carbon atoms, and particularly preferably, an unsaturated fatty acid having 18 carbon atoms), and its industrial production process is generally standardized in the industry. The dimer acid is easily obtained, in particular, from a dimer acid containing 36 carbon atoms, which is obtained by dimerizing an unsaturated fatty acid having 18 carbon atoms such as oleic acid or linoleic acid, which is inexpensive and easily available, as a main component. Further, the dimer acid may contain a monomer acid, a trimer acid, other polymerized fatty acid, and the like in an arbitrary amount depending on the production method, the degree of purification, and the like. In addition, although a double bond remains after the polymerization reaction of the unsaturated fatty acid, in the present specification, a hydride which is further hydrogenated to reduce the degree of unsaturation is also included in the dimer acid. To pairCommercially available dimer-type diamines are available, and examples thereof include PRIAMINE1073, PRIAMINE1074, and PRIAMINE1075 manufactured by Croda Japan, VERSAMINE 551, and VERSAMINE 552 manufactured by Cognis Japan.
Examples of the aromatic diamine compound include a phenylenediamine compound, a naphthalenediamine compound, and a diphenylamine compound.
The phenylenediamine compound is a compound formed of a benzene ring having 2 amino groups, and the benzene ring may optionally have 1 to 3 substituents. The substituent herein is not particularly limited. Specific examples of the phenylenediamine compound include 1, 4-phenylenediamine, 1, 2-phenylenediamine, 1, 3-phenylenediamine, 2, 4-diaminotoluene, 2, 6-diaminotoluene, 3, 5-diaminobiphenyl, 2,4,5, 6-tetrafluoro-1, 3-phenylenediamine and the like.
The naphthalene diamine compound is a compound formed of a naphthalene ring having 2 amino groups, and the naphthalene ring may optionally have 1 to 3 substituents. The substituent herein is not particularly limited. Specific examples of the naphthalenediamine compound include 1, 5-diaminonaphthalene, 1, 8-diaminonaphthalene, 2, 6-diaminonaphthalene, and 2, 3-diaminonaphthalene.
The diphenylamine compound is a compound having 2 aniline structures in a molecule, and 2 benzene rings in each of the 2 aniline structures may optionally have 1 to 3 substituents. The substituent herein is not particularly limited. The 2 aniline structures in the diphenylamine compound may be bonded directly and/or via 1 or 2 divalent linking groups having 1 to 100 (preferably 1 to 50, more preferably 1 to 20) skeleton atoms selected from a carbon atom, an oxygen atom, a sulfur atom and a nitrogen atom. The diphenylamine compound also contains a compound in which 2 aniline structures are combined at two positions.
Specific examples of the "divalent linking group" in the diphenylamine compound include-NHCO-, -CONH-, -OCO-, -COO-, -CH2-、-CH2CH2-、-CH2CH2CH2-、-CH2CH2CH2CH2-、-CH2CH2CH2CH2CH2-、-CH(CH3)-、-C(CH3)2-、-C(CF3)2-、-CH=CH-、-O-、-S-、-CO-、-SO2-、-NH-、-Ph-、-Ph-Ph-、-C(CH3)2-Ph-C(CH3)2-、-O-Ph-O-、-O-Ph-Ph-O-、-O-Ph-SO2-Ph-O-、-O-Ph-C(CH3)2-Ph-O-、-C(CH3)2-Ph-C(CH3)2-、
[ chemical formula 2]
(in the formula, a represents a binding site).
"Ph" represents 1, 4-phenylene, 1, 3-phenylene or 1, 2-phenylene.
Specific examples of the diphenylamine compound include 4,4 '-diamino-2, 2' -bis (trifluoromethyl) -1,1 '-biphenyl, 3, 4' -diaminodiphenyl ether, 4 '-diaminodiphenyl ether, 3' -diaminodiphenyl sulfone, 4 '-diaminodiphenyl sulfide, 4-aminophenyl 4-aminobenzoate, 1, 3-bis (3-aminophenoxy) benzene, 1, 3-bis (4-aminophenoxy) benzene, 1, 4-bis (4-aminophenoxy) benzene, 2-bis (4-aminophenyl) propane, 4' - (hexafluoroisopropylidene) diphenylamine, 2-bis [4- (4-aminophenoxy) phenyl ] propane, 2, 2-bis [4- (4-aminophenoxy) phenyl ] hexafluoropropane, α -bis [4- (4-aminophenoxy) phenyl ] -1, 3-diisopropylbenzene, α -bis [4- (4-aminophenoxy) phenyl ] -1, 4-diisopropylbenzene, 4 '- (9-fluorenylidene)) diphenylamine, 2-bis (3-methyl-4-aminophenyl) propane, 2-bis (3-methyl-4-aminophenyl) benzene, 4' -diamino-3, 3 '-dimethyl-1, 1' -biphenyl, 4 '-diamino-2, 2' -dimethyl-1, 1 '-biphenyl, 9' -bis (3-methyl-4-aminophenyl) fluorene, 5- (4-aminophenoxy) -3- [4- (4-aminophenoxy) phenyl ] -1,1, 3-trimethylindane, 4-aminobenzoic acid 5-amino-1, 1 '-biphenyl-2-yl ester, etc., preferably 5- (4-aminophenoxy) -3- [4- (4-aminophenoxy) phenyl ] -1,1, 3-trimethylindane, and 4-aminobenzoic acid 5-amino-1, 1' -biphenyl-2-yl ester.
As the diamine compound, commercially available diamine compounds can be used, and diamine compounds synthesized by a known method can also be used. The diamine compound may be used alone in 1 kind, or may be used in combination in 2 or more kinds.
The tetracarboxylic anhydride used for the preparation of the polyimide resin is not particularly limited, and examples thereof include aromatic tetracarboxylic dianhydride and aliphatic tetracarboxylic dianhydride.
Examples of the aromatic tetracarboxylic acid dianhydride include pyromellitic acid dianhydride, naphthalene tetracarboxylic acid dianhydride, anthracene tetracarboxylic acid dianhydride, and diphthalic dianhydride (diphthalic dianhydride), and diphthalic dianhydride is preferable.
The pyromellitic dianhydride is a dianhydride of benzene having 4 carboxyl groups, and the benzene ring herein may optionally have 1 to 3 substituents. Here, the substituent is not particularly limited. Specific examples of the pyromellitic dianhydride include pyromellitic dianhydride and 1,2,3, 4-pyromellitic dianhydride.
The naphthalene tetracarboxylic dianhydride is a dianhydride of naphthalene having 4 carboxyl groups, and the naphthalene ring herein may optionally have 1 to 3 substituents. Here, the substituent is not particularly limited. Specific examples of the naphthalene tetracarboxylic dianhydride include 1,4,5, 8-naphthalene tetracarboxylic dianhydride, and 2,3,6, 7-naphthalene tetracarboxylic dianhydride.
The anthracenetetracarboxylic dianhydride is an anthracene dianhydride having 4 carboxyl groups, and the anthracene ring herein may optionally have 1 to 3 substituents. Here, the substituent is not particularly limited. Specific examples of the anthracenetetracarboxylic dianhydride include 2,3,6, 7-anthracenetetracarboxylic dianhydride and the like.
The bisphthalic dianhydride is a compound containing 2 phthalic anhydrides in the molecule, and 2 benzene rings of 2 phthalic anhydrides may optionally have 1 to 3 substituents. Here, the substituent is not particularly limited. The 2 phthalic anhydrides in the diphthalic dianhydride may be bonded directly or via a divalent linking group having 1 to 100 (preferably 1 to 50, more preferably 1 to 20) backbone atoms selected from a carbon atom, an oxygen atom, a sulfur atom and a nitrogen atom.
Specific examples of the divalent linking group include-CH2-、-CH2CH2-、-CH2CH2CH2-、-CH2CH2CH2CH2-、-CH2CH2CH2CH2CH2-、-CH(CH3)-、-C(CH3)2-、-O-、-CO-、-SO2-、-Ph-、-O-Ph-O-、-O-Ph-SO2-Ph-O-、-O-Ph-C(CH3)2-Ph-O-, etc.
Specific examples of the bisphthalic dianhydride include 3,3 ', 4, 4' -benzophenone tetracarboxylic dianhydride, 3,3 ', 4, 4' -diphenyl ether tetracarboxylic dianhydride, 3,3 ', 4, 4' -diphenylsulfone tetracarboxylic dianhydride, 3,3 ', 4, 4' -biphenyl tetracarboxylic dianhydride, 2 ', 3, 3' -biphenyl tetracarboxylic dianhydride, 2,3,3 ', 4' -benzophenone tetracarboxylic dianhydride, 2,3,3 ', 4' -diphenyl ether tetracarboxylic dianhydride, 2,3,3 ', 4' -diphenylsulfone tetracarboxylic dianhydride, 2 '-bis (3, 4-dicarboxyphenoxyphenyl) sulfone dianhydride, methylene-4, 4' -bisphthalic dianhydride, and, 1, 1-ethynylene (ethylidene) -4,4 '-biphthalic dianhydride, 2-propylene (propylidene) -4, 4' -biphthalic dianhydride, 1, 2-ethylene-4, 4 '-biphthalic dianhydride, 1, 3-trimethylene-4, 4' -biphthalic dianhydride, 1, 4-tetramethylene-4, 4 '-biphthalic dianhydride, 1, 5-pentamethylene-4, 4' -biphthalic dianhydride, 1, 3-bis (3, 4-dicarboxyphenyl) benzene dianhydride, 1, 4-bis (3, 4-dicarboxyphenyl) benzene dianhydride, 1, 3-bis (3, 4-dicarboxyphenoxy) benzene dianhydride, 1, 4-bis (3, 4-dicarboxyphenoxy) benzene dianhydride, 2-bis (2, 3-dicarboxyphenyl) propane dianhydride, 2-bis (3, 4-dicarboxyphenyl) propane dianhydride, 4 '- (4, 4' -isopropylidenediphenoxy) diphthalic dianhydride, and the like.
Specific examples of the aliphatic tetracarboxylic acid dianhydride include 1,2,3, 4-cyclobutanetetracarboxylic acid dianhydride, cyclopentanetetracarboxylic acid dianhydride, cyclohexane-1, 2,3, 4-tetracarboxylic acid dianhydride, cyclohexane-1, 2,4, 5-tetracarboxylic acid dianhydride, 3 ', 4, 4' -dicyclohexyltetracarboxylic acid dianhydride, carbonyl-4, 4 '-bis (cyclohexane-1, 2-dicarboxylic acid) dianhydride, methylene-4, 4' -bis (cyclohexane-1, 2-dicarboxylic acid) dianhydride, 1, 2-ethylene-4, 4 '-bis (cyclohexane-1, 2-dicarboxylic acid) dianhydride, oxy-4, 4' -bis (cyclohexane-1, 2-dicarboxylic acid) dianhydride, thio-4, 4 '-bis (cyclohexane-1, 2-dicarboxylic acid) dianhydride, sulfonyl-4, 4' -bis (cyclohexane-1, 2-dicarboxylic acid) dianhydride, and the like.
As the tetracarboxylic acid dianhydride, commercially available tetracarboxylic acid dianhydrides can be used, and tetracarboxylic acid dianhydrides synthesized by a known method or a method based on the known method can also be used. The tetracarboxylic dianhydride may be used alone in 1 kind, or in combination of 2 or more kinds.
The content of the structure derived from an aromatic tetracarboxylic dianhydride is preferably 10 mol% or more, more preferably 30 mol% or more, even more preferably 50 mol% or more, even more preferably 70 mol% or more, even more preferably 90 mol% or more, and particularly preferably 100 mol% based on the entire structure derived from a tetracarboxylic dianhydride constituting the polyimide resin.
The polyimide resin preferably has a weight average molecular weight of 1,000 to 100,000.
The maleimide resin having a dimer acid skeleton is, for example, a bismaleimide compound having a hydrocarbon skeleton derived from a dimer acid. The maleimide resin having a dimer acid skeleton is, for example, a bismaleimide compound obtained by imidizing at least dimer acid-based diamine and maleic anhydride, and further includes a bismaleimide compound obtained by imidizing dimer acid-based diamine, tetracarboxylic dianhydride and maleic anhydride.
The maleimide resin having a dimer acid skeleton is, for example, a bismaleimide compound represented by the following formula (2).
[ chemical formula 3]
[ in the formula, Y1And Y3Each independently represents the removal of 2-NH groups from dimer acid-based diamines2And the resulting divalent radical, Y2Represents a tetravalent group obtained by removing 2-CO-O-CO-groups from tetracarboxylic dianhydride, and m represents 0 or 1]。
Specific examples of the maleimide resin having a dimer acid skeleton include "BMI 689", "BMI 1500", "BMI 1700", and "BMI 3000" manufactured by DESIGNER MOLECULES co. These can be used alone in 1 kind, also can be combined with more than 2 kinds.
(D) The content of the adhesive flexibilizing agent is not particularly limited, and is preferably 1 mass% or more, more preferably 5 mass% or more, further preferably 10 mass% or more, and particularly preferably 15 mass% or more, when the nonvolatile content in the resin composition is 100 mass%, from the viewpoint of obtaining a cured product having more excellent flexibility. (D) The upper limit of the content of the adhesive flexibilizing agent is not particularly limited, and is preferably 50% by mass or less, more preferably 40% by mass or less, further preferably 30% by mass or less, and particularly preferably 25% by mass or less, assuming that the nonvolatile component in the resin composition is 100% by mass.
(E) curing agent
The resin composition of the present invention may contain (E) a curing agent as an optional component. (E) The curing agent has a function of curing the thermosetting resin (a).
The curing agent (E) is not particularly limited, and when the thermosetting resin (a) is an epoxy resin, examples thereof include phenol curing agents, naphthol curing agents, acid anhydride curing agents, active ester curing agents, benzoxazine curing agents, cyanate curing agents, and carbodiimide curing agents, and phenol curing agents, naphthol curing agents, and active ester curing agents are preferable. (E) The curing agent preferably comprises an active ester curing agent. The curing agent may be used alone in 1 kind, or in combination of 2 or more kinds.
As the phenol curing agent and the naphthol curing agent, a phenol curing agent having a novolac structure or a naphthol curing agent having a novolac 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 Minghu chemical Co., Ltd, "NHN", "CBN", "GPH" manufactured by Nippon chemical Co., Ltd, "SN-170", "SN-180", "SN-190", "SN-475", "SN-485", "SN-495", "SN-375", "SN-395", and "LA-7052", "LA-7054", "LA-3018-50P", "LA-1356", "TD 2090" and "TD-2090-60M" manufactured by DIC.
Examples of the acid anhydride-based curing agent include a curing agent having 1 or more acid anhydride groups in 1 molecule. Specific examples of the acid anhydride 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-furyl) -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. As commercially available products of the acid anhydride-based curing agent, "HNA-100" and "MH-700" manufactured by Nissan chemical and chemical Co., Ltd.
The active ester curing agent is not particularly limited, and in general, 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 hydroxyl compounds, can be preferably used. The active ester curing agent is preferably an active ester curing agent 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 curing agent obtained from a carboxylic acid compound and a hydroxyl compound is preferable, and an active ester 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 novolak and the like. Here, the "dicyclopentadiene type diphenol compound" refers to a diphenol compound obtained by condensing 2 molecules of phenol on 1 molecule of dicyclopentadiene.
Specifically, 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 phenol novolac, and an active ester compound containing a benzoyl compound of phenol novolac are preferable, and among them, an active ester compound containing a naphthalene structure and 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.
As the commercially available products of the active ester curing agent, there may be mentioned "EXB 9451", "EXB 9460S", "HPC-8000H", "HPC-8000-65T", "HPC-8000H-65 TM", "EXB-8000L-65M", "EXB-8000L-65 TM" (manufactured by DIC) which are active ester compounds having a dicyclopentadiene type diphenol structure; "EXB 9416-70 BK" and "EXB 8150-65T" (manufactured by DIC) as active ester compounds having a naphthalene structure; "DC 808" (manufactured by mitsubishi chemical corporation) which is an active ester compound containing an acetylate of phenol novolac; "YLH 1026" (manufactured by mitsubishi chemical corporation) which is an active ester compound including a benzoyl compound of phenol novolac; "DC 808" (manufactured by Mitsubishi chemical corporation) as an active ester curing agent which is an acetylate of phenol novolak; "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 curing agents that are benzoylates of phenol novolac; 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 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) phenylpropane, 1-bis (4-cyanate phenylmethane), bis (4-cyanate-3, 5-dimethylphenyl) methane, 1, 3-bis (4-cyanate-phenyl-1- (methylethylidene)) benzene, bis (4-cyanate-phenyl) sulfide, and bis (4-cyanate-phenyl) ether, and polyfunctional cyanate ester resins derived from phenol novolac, cresol novolac, and the like, Prepolymers obtained by partially triazinating these cyanate ester resins, and the like. 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.
Specific examples of the carbodiimide-based curing agent include "V-03" and "V-07" manufactured by Nisshinbo chemical Co.
When the resin composition contains the (E) curing agent, the ratio of the amount of the (a) thermosetting resin to the amount of the (E) curing agent is expressed as [ total number of reactive groups of thermosetting resin ]: the ratio of [ total number of reactive groups of the curing agent ] is preferably in the range of 1:0.2 to 1:2, more preferably 1:0.3 to 1:1.5, and further preferably 1:0.4 to 1: 1.2. The reactive group of the curing agent means an active hydroxyl group, an active ester group, and the like, and varies depending on the type of the curing agent. The reactive group of the thermosetting resin means an epoxy group and the like, and varies depending on the kind of the thermosetting resin.
When the resin composition contains the curing agent (E), the content thereof is not particularly limited, and when the nonvolatile content in the resin composition is 100% by mass, the content is preferably 0.1% by mass or more, more preferably 1% by mass or more, further preferably 3% by mass or more, and particularly preferably 4% by mass or more. (E) The upper limit of the content of the curing agent is not particularly limited, and is preferably 30% by mass or less, more preferably 20% by mass or less, further preferably 15% by mass or less, and particularly preferably 10% by mass or less, assuming that the nonvolatile content in the resin composition is 100% by mass.
(F) curing Accelerator
The resin composition of the present invention may contain (F) a curing accelerator as an optional component. (F) The curing accelerator has a function of accelerating the curing speed of the thermosetting resin (a).
The curing accelerator (F) is not particularly limited, and when the thermosetting resin (a) is an epoxy resin, examples thereof include a phosphorus-based curing accelerator, an amine-based curing accelerator, an imidazole-based curing accelerator, a guanidine-based curing accelerator, and a metal-based curing accelerator. Among them, preferred are phosphorus-based curing accelerators, amine-based curing accelerators, imidazole-based curing accelerators and metal-based curing accelerators, and more preferred are amine-based curing accelerators. The curing accelerator may be used alone in 1 kind, or in combination of 2 or more kinds.
Examples of the phosphorus-based curing accelerator include triphenylphosphine, a phosphonium borate compound, tetraphenylphosphonium tetraphenylborate, n-butylphosphonium tetraphenylborate, tetrabutylphosphonium decanoate, (4-methylphenyl) triphenylphosphonium thiocyanate, tetraphenylphosphonium thiocyanate, butyltriphenylphosphonium thiocyanate and the like.
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, with 4-dimethylaminopyridine being preferred.
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, 2-heptadecylimidazole, 1, 2-dimethylimidazole, 2-ethylimidazole, 1-cyanoethyl-2-methylimidazole, 1-cyanoethyl-2-phenylimidazole, 2-cyanoethyl-2, 1-cyanoethyl-2-undecylimidazolium trimellitate, 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, and mixtures thereof, Imidazole compounds such as 2-phenylimidazole isocyanuric acid adduct, 2-phenyl-4, 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.
As the imidazole-based curing accelerator, commercially available products can be used, and examples thereof include "P200-H50" manufactured by Mitsubishi chemical corporation.
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-octadecylbiguanide, 1-dimethylbiguanide, 1-diethylbiguanide, 1-cyclohexylbiguanide, 1-allylbiguanide, 1-phenylbiguanide, 1- (o-tolyl) biguanide and the like.
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.
When the resin composition contains the (F) curing accelerator, the content thereof is not particularly limited, and when the nonvolatile content in the resin composition is 100 mass%, the content is preferably 0.001 mass% or more, more preferably 0.01 mass% or more, further preferably 0.05 mass% or more, and particularly preferably 0.1 mass% or more. (F) The upper limit of the content of the curing accelerator is not particularly limited, and is preferably 2% by mass or less, more preferably 1% by mass or less, further preferably 0.5% by mass or less, and particularly preferably 0.3% by mass or less, assuming that the nonvolatile content in the resin composition is 100% by mass.
< (G) other additives
The resin composition of the present invention may further contain an optional additive as a nonvolatile component. Examples of such additives include thermoplastic resins such as phenoxy resins, polyvinyl acetal resins, polyolefin resins, polysulfone resins, polyethersulfone resins, polyphenylene ether resins, polycarbonate resins, polyetheretherketone resins, and polyester resins; 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 siloxane; thickeners such as 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 silane coupling agents, 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; flame retardants such as phosphorus flame retardants (e.g., phosphate ester compounds, phosphazene compounds, phosphonic 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. The content of the (G) other additives may be appropriately set by those skilled in the art.
(H) 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 (H), any known organic solvent can be suitably used as long as it can dissolve at least a part of the nonvolatile components, and the kind thereof is not particularly limited. Examples of the organic solvent (H) 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. 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.
The content of the organic solvent (H) may be set so that the mass ratio of the nonvolatile component to the total mass of the resin composition, that is, the solid content ratio is preferably 30 mass% or more, more preferably 35 mass% or more, still more preferably 40 mass% or more, and particularly preferably 45 mass% or more, from the viewpoint of efficiently drying the resin composition. The upper limit of the solid content ratio is not particularly limited, and may be preferably 100% by mass or less, more preferably 95% by mass or less, further preferably 92% by mass or less, and particularly preferably 90% by mass or less, from the viewpoint of handling properties of the resin composition.
< method for producing resin composition >
The resin composition of the present invention can be produced, for example, by: the thermosetting resin (a), the inorganic filler (B), the organic filler (C), the adhesive flexibilizer (D), the curing agent (E) used as needed, (F) the curing accelerator (F) used as needed, (G) the other additives (G) used as needed, and the organic solvent (H) used as needed are added to an arbitrary reaction vessel in an arbitrary order and/or partially or entirely simultaneously, and mixed. 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 throughout. In addition, the components may be stirred or shaken during the mixing process. In addition, when or after the addition and mixing, the resin composition may be stirred and uniformly dispersed by using a stirring device such as a mixer.
< Property of resin composition >
The resin composition of the present invention contains not only (a) a thermosetting resin, (D) an adhesive flexibilizing agent, and (B) an inorganic filler, but also (C) an organic filler in an amount of 5 mass% or more, and therefore, can suppress the tackiness to a low level while maintaining excellent flexibility.
The resin composition of the present invention has sufficient flexibility because of the inclusion of the adhesive flexibilizer (D), and therefore, for example, the number of folding endurance tests performed on a layered cured product of a resin composition having a thickness of 40 μm, a width of 15mm, and a length of 110mm under the conditions of a load of 2.5N, a bending angle of 90 degrees, a bending speed of 175 times/minute, and a bending radius of 1.0mm according to JIS C-5016 may be preferably 3,000 or more, more preferably 5,000 or more, further preferably 7,000 or more, and particularly preferably 8,000 or more.
For the resin composition of the present invention, for example, the minimum melt viscosity of the resin composition measured under the conditions of an initial temperature of 60 ℃ to 200 ℃, a temperature rise rate of 5 ℃/minute, a vibration frequency of 1Hz, and a deformation of 1 deg. may be preferably 40,000 poise or less, preferably 30,000 poise or less, preferably 20,000 poise or less, preferably 10,000 poise or less.
Since the resin composition of the present invention contains (C) an organic filler, for example, a Probe tack tester (Probe tack tester) is used for a layered resin composition, and the Probe diameter is 5mm and the load is 1kgf/cm2The adhesive force measured under the conditions of a contact speed of 0.5 mm/sec, a stretching speed of 0.5 mm/sec, a holding time of 10 sec and a temperature of 80 ℃ may be preferably 2.0N or less, more preferably 1.8N or less, still more preferably 1.7N or less, and particularly preferably 1.6N or less.
In addition, the resin composition of the present invention has a feature that, particularly when the content of the (C) organic filler is 10 mass% or less, void defects can be suppressed and pattern embeddability is more excellent.
< resin sheet >
The resin sheet of the present invention comprises a support and a resin composition layer formed of the resin composition of the present invention provided on the support.
The thickness of the resin composition layer is preferably 200 μm or less, more preferably 150 μm or less, still more preferably 100 μm or less, and particularly preferably 70 μm or less. The lower limit of the thickness of the resin composition layer is not particularly limited, and may be usually 1 μm or more, 1.5 μm or more, 2 μm or more, or the like.
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 abbreviated as "PET") and polyethylene naphthalate (hereinafter, sometimes abbreviated as "PEN"), acrylic polymers such as polycarbonate (hereinafter, sometimes abbreviated as "PC") and polymethyl methacrylate (PMMA), cyclic polyolefins, triacetyl cellulose (TAC), polyether sulfide (PES), polyether ketone, and polyimide. 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, and a 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 matting treatment, corona treatment, or antistatic treatment.
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 with a release layer include 1 or more release agents selected from alkyd resins, polyolefin resins, polyurethane resins, and silicone resins. As the support having a release layer, commercially available products can be used, and examples thereof include a PET film having a release layer containing an alkyd resin-based release agent as a main component, "SK-1", "AL-5" and "AL-7" manufactured by Linekuki, a "Lumiror T60" manufactured by Toray, a "Purex" manufactured by Ditika, a "Unipel" manufactured by Unitika, and the like.
The thickness of the support is not particularly limited, but 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.
In one embodiment, the resin sheet may further include other layers as necessary. Examples of the other layer include a protective film provided on a surface of the resin composition layer not bonded to the support (i.e., a surface opposite to the support) and selected for the support. The thickness of the protective film is not particularly limited, and is, for example, 1 μm to 40 μm. By laminating the protective film, it is possible to suppress adhesion of dust or the like to the surface of the resin composition layer or generation of damage on the surface of the resin composition layer.
The resin sheet can be produced by: the resin composition is directly applied to the support using a die coater or the like, or a resin varnish prepared by dissolving the resin composition in an organic solvent is applied to the support and dried to form a resin composition layer.
Examples of the organic solvent that can be used when applying the coating composition to the support include the same organic solvents as those listed in the description of the organic solvent (H). The organic solvent may be used alone in 1 kind, or may be used in combination of 2 or more kinds.
The drying can be carried out by a known method such as heating or blowing hot air. The drying conditions are not particularly limited, and drying is performed so that the content of the organic solvent in the resin composition layer is 10 mass% or less, preferably 5 mass% or less. Although the boiling point of the organic solvent in the resin composition or the resin varnish varies, for example, when a resin composition or a resin varnish containing 30 to 60 mass% of the organic solvent is used, the resin composition layer can be formed by drying at 50 to 150 ℃ for 3 to 10 minutes.
The resin sheet may be wound into a roll and stored. When the resin sheet has a protective film, the protective film can be peeled off and used.
< laminated sheet >
The laminated sheet is produced by laminating and curing a plurality of resin composition layers. The laminated sheet includes a plurality of insulating layers as a cured product of the resin composition layer. In general, the number of resin composition layers stacked for manufacturing the laminated sheet corresponds to the number of insulating layers included in the laminated sheet. The specific number of insulating layers per 1-layer laminated sheet is usually 2 or more, preferably 3 or more, particularly preferably 5 or more, preferably 20 or less, more preferably 15 or less, particularly preferably 10 or less.
The laminated sheet is a sheet used by being bent (folded in half) so that one surface thereof faces each other. The minimum bend radius of the laminated sheet in bending is not particularly limited, but is preferably 0.1mm or more, more preferably 0.2mm or more, further preferably 0.3mm or more, preferably 5mm or less, more preferably 4mm or less, and particularly preferably 3mm or less.
Holes may be formed in each of the insulating layers included in the laminated sheet. The holes may function as through holes or through holes in the multilayer flexible substrate.
The laminated sheet may further include any element in addition to the insulating layer. For example, the laminated sheet may include a conductor layer as an arbitrary element. The conductor layer may be formed partially on the surface of the insulating layer or between the insulating layers. The conductor layer generally functions as a wiring in a multilayer flexible substrate.
The conductor material used in the conductor layer is not particularly limited. In a preferred embodiment, the conductor layer contains 1 or more metals selected from the group consisting of gold, platinum, palladium, silver, copper, aluminum, cobalt, chromium, zinc, nickel, titanium, tungsten, iron, tin, and indium. The conductor material may be a single metal or an alloy. Examples of the alloy include alloys of 2 or more metals selected from the above-mentioned group (for example, nickel-chromium alloy, copper-nickel alloy, and copper-titanium alloy). Among them, chromium, nickel, titanium, aluminum, zinc, gold, palladium, silver, or copper as a single metal is preferable from the viewpoints of versatility of forming a conductor layer, cost, ease of patterning, and the like; and alloys such as nickel-chromium alloy, copper-nickel alloy, and copper-titanium alloy. Among them, a single metal of chromium, nickel, titanium, aluminum, zinc, gold, palladium, silver, or copper is more preferable; and nickel-chromium alloys, more preferably copper.
The conductor layer may have a single-layer structure, or may have a multilayer structure including 2 or more single metal layers or alloy layers made of different metals or alloys. When the conductor layer has a multilayer structure, the layer in contact with the insulating layer is preferably a single metal layer of chromium, zinc, or titanium, or an alloy layer of a nickel-chromium alloy.
The conductor layer may be patterned to function as a wiring.
The thickness of the conductor layer depends on the design of the multilayer flexible substrate, 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 thickness of the laminated sheet is preferably 100 μm or more, more preferably 150 μm or more, particularly preferably 200 μm or more, preferably 2,000 μm or less, more preferably 1,000 μm or less, and particularly preferably 500 μm or less.
< method for producing laminated sheet >
The laminated sheet can be produced by a production method including the steps of: (a) a step of preparing a resin sheet; and (b) a step of laminating and curing a plurality of resin composition layers using the resin sheet. The order of lamination and curing of the resin composition layer is arbitrary as long as a desired laminated sheet can be obtained. For example, after the plurality of resin composition layers are all stacked, the stacked plurality of resin composition layers may be collectively cured. In addition, for example, the curing of the laminated resin composition layer may be performed each time another resin composition layer is laminated on a certain resin composition layer.
Hereinafter, a preferred embodiment of the step (b) will be described. In the embodiments described below, for the sake of distinction, the resin composition layers are indicated by symbols as "first resin composition layer" and "second resin composition layer", and further, on the insulating layer obtained by curing these resin composition layers, the same symbols as those for the resin composition layers are indicated by "first insulating layer" and "second insulating layer".
In a preferred embodiment, the step (b) includes the steps of:
(II) a step of curing the first resin composition layer to form a first insulating layer,
(VI) a step of laminating a second resin composition layer on the first insulating layer,
(VII) a step of curing the second resin composition layer to form a second insulating layer. The step (b) may further include any of the following steps as necessary:
(I) a step of laminating a first resin composition layer on a sheet-like support base material,
(III) a step of forming a hole in the first insulating layer,
(IV) a step of roughening the first insulating layer,
(V) forming a conductor layer on the first insulating layer;
hereinafter, each step will be explained.
The step (I) is a step of laminating a first resin composition layer on a sheet-like support base material before the step (II). The sheet-like support substrate is a peelable member, and for example, a plate-like, sheet-like or film-like member can be used.
The lamination of the sheet-like support substrate with the first resin composition layer may be performed using a vacuum lamination method. In the vacuum lamination method, the heating and pressure bonding temperature is preferably 60 to 160 ℃, more preferably 80 to 140 ℃, the heating and pressure bonding pressure is preferably 0.098 to 1.77MPa, more preferably 0.29 to 1.47MPa, and the heating and pressure bonding time is preferably 20 to 400 seconds, more preferably 30 to 300 seconds. The lamination is preferably performed under a reduced pressure of 26.7hPa or less.
The lamination can be carried out by means of a commercially available vacuum laminator. Examples of commercially available vacuum laminators include a vacuum pressure laminator manufactured by Nikko-Materials, vacuum applicators (vacuums applicators) manufactured by Nikko-Materials, and a batch vacuum pressure laminator.
In the case of using a resin sheet, the lamination of the sheet-like support base material and the first resin composition layer can be performed, for example, by pressing the resin sheet from the support side and heat-pressure bonding the first resin composition layer of the resin sheet to the sheet-like support base material. Examples of the member for heat-pressure bonding the resin sheet to the sheet-like support base material (hereinafter, also referred to as "heat-pressure bonding member" as appropriate) include a heated metal plate (SUS end plate or the like) and a metal roll (SUS roll). It is preferable that the thermocompression bonding member is not directly pressed against the resin sheet, but pressed via an elastic material such as a heat-resistant rubber so that the first resin composition layer sufficiently follows the surface irregularities of the sheet-like support base material.
After the lamination, the smoothing treatment of the first resin composition layer may be performed by pressing under normal pressure (atmospheric pressure), for example, with a heat crimping member. For example, in the case of using a resin sheet, the first resin composition layer of the resin sheet can be smoothed by pressing the resin sheet with the heat and 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 smoothing treatment can be performed using a commercially available laminator. The lamination and smoothing processes can be performed continuously using a commercially available vacuum laminator as described above.
The step (II) is a step of curing the first resin composition layer to form a first insulating layer. The conditions for heat curing of the first resin composition layer are not particularly limited, and the conditions employed in forming the insulating layer of the printed wiring board can be arbitrarily applied.
In general, specific heat curing conditions vary depending on the kind of the resin composition. For example, the curing temperature is preferably 120 to 240 ℃, more preferably 150 to 220 ℃, and still more preferably 170 to 210 ℃. The curing time is preferably 5 to 120 minutes, more preferably 10 to 110 minutes, and still more preferably 20 to 100 minutes.
The first resin composition layer may be preheated at a temperature lower than the curing temperature before the first resin composition layer is thermally cured. For example, the first resin composition layer may be preheated at a temperature of 50 ℃ or higher and lower than 120 ℃ (preferably 60 ℃ or higher and 115 ℃ or lower, more preferably 70 ℃ or higher and 110 ℃ or lower) for 5 minutes or longer (preferably 5 minutes to 150 minutes, more preferably 15 minutes to 120 minutes, and further preferably 15 minutes to 100 minutes) before the first resin composition layer is thermally cured.
The step (III) is a step of forming a hole in the first insulating layer. In the step (III), a via hole, a through hole, or the like can be formed in the first insulating layer. The opening may be performed using, for example, a drill, a laser, plasma, etc., according to the composition of the resin composition. The size and shape of the hole may be appropriately set according to the design of the multilayer flexible substrate.
The step (IV) is a step of performing roughening treatment on the first insulating layer. In general, in this step (IV), the removal of the scum is also performed. Therefore, the roughening treatment may be referred to as desmear treatment. Examples of the roughening treatment include a method in which swelling treatment with a swelling liquid, roughening treatment with an oxidizing agent, and neutralization treatment with a neutralizing liquid are sequentially performed.
The swelling liquid is not particularly limited, and examples thereof include alkaline aqueous solutions such as an aqueous sodium hydroxide solution and an aqueous potassium hydroxide solution. Examples of commercially available Swelling liquids include "spinning Dip securigranthP" and "spinning Dip securigranth SBU" manufactured by ATOTECH JAPAN. The swelling treatment with the swelling solution can be performed, for example, by immersing the cured product in the swelling solution at 30 to 90 ℃ for 1 to 20 minutes. From the viewpoint of suppressing swelling of the resin of the insulating layer to an appropriate level, the insulating layer is preferably immersed in a swelling solution at 40 to 80 ℃ for 5 to 15 minutes.
The oxidizing agent is not particularly limited, and examples thereof include an alkaline permanganate solution obtained by dissolving permanganate in an aqueous sodium hydroxide solution or an aqueous potassium hydroxide solution. The concentration of permanganate in the alkaline permanganate solution is preferably 5 to 10 mass%. Examples of commercially available oxidizing agents include alkaline permanganic acid solutions such as "Concentrate Compact P", "Concentrate Compact CP" and "Dosing Solution securigrant P" manufactured by ATOTECH JAPAN. The roughening treatment with an oxidizing agent may be performed by immersing the cured body in an oxidizing agent solution heated to 60 to 80 ℃ for 10 to 30 minutes.
In addition, as the neutralizing solution, an acidic aqueous solution can be used. Examples of commercially available products include "Reduction Solution securigant P" manufactured by ato ech JAPAN. The treatment with the neutralizing solution can be performed by immersing the cured product in the neutralizing solution at 30 to 80 ℃ for 5 to 30 minutes. From the viewpoint of handling and the like, the cured product is preferably immersed in a neutralization solution at 40 to 70 ℃ for 5 to 20 minutes.
The arithmetic average roughness (Ra) of the surface of the first insulating layer after the roughening treatment is preferably 400nm or less, more preferably 300nm or less, and further preferably 200nm or less. The lower limit is not particularly limited, and may be 30nm or more, 40nm or more, or 50nm or more.
The step (V) is a step of forming a conductor layer on the first insulating layer as necessary. Examples of the method for forming the conductor layer include plating, sputtering, and vapor deposition, and among them, plating is preferred. A preferable example is a method of forming a conductor layer having a desired wiring pattern by plating on the surface of the first insulating layer by an appropriate method such as a semi-additive method or a full-additive method. Among them, the semi-addition method is preferable from the viewpoint of ease of production.
An example of forming a conductor layer by a semi-additive method is shown below. First, a plating seed layer is formed on the surface of the first 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 corresponding to a desired wiring pattern. On the exposed plating seed layer, a metal layer is formed by electrolytic plating, and then the mask pattern is removed. Then, the unnecessary plating seed layer is removed by etching or the like, and a conductor layer having a desired wiring pattern can be formed.
In the step (II), the first insulating layer is obtained, and the step (III), the step (IV), and the step (V) are performed as necessary, followed by the step (VI). Step (VI) is a step of laminating a second resin composition layer on the first insulating layer. The lamination of the first insulating layer and the second resin composition layer can be performed by the same method as the lamination of the sheet-like support base material and the first resin composition layer in the step (I).
However, in the case where the first resin composition layer is formed using a resin sheet, the support of the resin sheet is removed before the step (VI). The removal of the support may be performed between the steps (I) and (II), between the steps (II) and (III), between the steps (III) and (IV), or between the steps (IV) and (V).
After the step (VI), the step (VII) is performed. Step (VII) is a step of curing the second resin composition layer to form a second insulating layer. The curing of the second resin composition layer can be performed by the same method as the curing of the first resin composition layer in the step (II). This makes it possible to obtain a multilayer sheet including a plurality of insulating layers, such as a first insulating layer and a second insulating layer.
In the method according to the above embodiment, (VIII) the step of forming a hole in the second insulating layer, (IX) the step of roughening the second insulating layer, and (X) the step of forming a conductor layer on the second insulating layer may be performed as necessary. The opening of the second insulating layer in the step (VIII) can be performed by the same method as the opening of the first insulating layer in the step (III). In addition, the roughening treatment of the second insulating layer in the step (IX) can be performed by the same method as the roughening treatment of the first insulating layer in the step (IV). Further, the formation of the conductor layer on the second insulating layer in the step (X) can be performed by the same method as the formation of the conductor layer on the first insulating layer in the step (V).
In the above-described embodiment, the embodiment in which the laminated sheet is produced by laminating and curing 2 resin composition layers such as the first resin composition layer and the second resin composition layer was described, but the laminated sheet may be produced by laminating and curing 3 or more resin composition layers. For example, in the method according to the embodiment described above, the lamination and curing of the resin composition layer by the steps (VI) to (VII), and if necessary, the drilling of the insulating layer, the roughening treatment of the insulating layer, and the formation of the conductor layer on the insulating layer by the steps (VIII) to (X) may be repeatedly performed to manufacture the laminated sheet. This can provide a laminated sheet including 3 or more insulating layers.
The method according to the above embodiment may further include any process other than the above process. For example, when the step (I) is performed, a step of removing the sheet-like support base material may be performed.
< multilayer Flexible substrate >
The multilayer flexible substrate includes a laminated sheet. The multilayer flexible substrate may include only the laminated sheet, or may include not only the laminated sheet but also any member. Examples of the optional member include an electronic component and a cover film.
The multilayer flexible substrate can be manufactured by a manufacturing method including a method of manufacturing the laminated sheet described above. Accordingly, the multilayer flexible substrate can be manufactured by a manufacturing method including the steps of: (a) a step of preparing a resin sheet, and (b) a step of laminating and curing a plurality of resin composition layers using the resin sheet.
The method for manufacturing a multilayer flexible substrate may include not only the above-described steps but also any other steps. For example, a method for manufacturing a multilayer flexible substrate provided with an electronic component may include a step of bonding the electronic component to the laminated sheet. As for the bonding condition between the laminated sheet and the electronic component, any condition can be adopted in which the terminal electrode of the electronic component and the conductor layer provided on the laminated sheet as a wiring can be conductor-connected. For example, the method for manufacturing a multilayer flexible substrate provided with a cover film may include a step of laminating a laminated sheet and the cover film.
The multilayer flexible substrate described above can be generally used by bending a laminated sheet included in the multilayer flexible substrate so that one surface faces each other. For example, the multilayer flexible substrate is housed in a case of a semiconductor device in a state of being bent and reduced in size. Further, for example, in a semiconductor device having a flexible movable portion, a multilayer flexible substrate is provided in the movable portion.
< semiconductor device >
The semiconductor device includes the multilayer flexible substrate. The semiconductor device includes, for example, a multilayer flexible substrate and a semiconductor chip mounted on the multilayer flexible substrate. In many semiconductor devices, a multilayer flexible substrate is folded so that one surface of a laminated sheet included in the multilayer flexible substrate faces each other, and is stored in a case of the semiconductor device.
Examples of the semiconductor device include various semiconductor devices which can be used in, for example, electric products (for example, computers, mobile phones, digital cameras, televisions, and the like) and vehicles (for example, motorcycles, automobiles, electric trains, ships, aircrafts, and the like).
The semiconductor device can be manufactured by a manufacturing method including, for example, the steps of: the method includes a step of preparing a multilayer flexible substrate, a step of bending the multilayer flexible substrate so that one surface of the laminated sheet faces each other, and a step of housing the bent multilayer flexible substrate in a case.
Examples
The present invention will be specifically described below with reference to examples. However, the present invention is not limited to the following examples. In the following description, "part" and "%" representing amounts represent "part by mass" and "% by mass", respectively, unless otherwise explicitly stated. Unless otherwise explicitly stated, the operations described below are performed in an environment at normal temperature and normal pressure.
< Synthesis example 1: synthesis of polybutadiene resin containing phenolic hydroxyl group
69G of bifunctional hydroxyl-terminated polybutadiene ("G-3000" manufactured by Nippon Caoda corporation, number average molecular weight =3000, hydroxyl equivalent =1800G/eq.), 40G of an aromatic hydrocarbon-based mixed solvent ("Izode 150" manufactured by Takekushi chemical corporation), and 0.005G of dibutyltin laurate were put into a reaction vessel and mixed to be uniformly dissolved. After the mixture was homogenized, the temperature was raised to 60 ℃, 8g of isophorone diisocyanate (IPDI manufactured by Evonik Degussa Japan, isocyanate group equivalent =113g/eq.) was added with stirring, and the reaction was carried out for about 3 hours.
Then, 23g of cresol novolak resin ("KA-1160" manufactured by DIC corporation and hydroxyl equivalent =117g/eq.) and 60g of diethylene glycol monoethyl ether acetate (manufactured by cellosolve corporation) were added to the reaction product, and the temperature was raised to 150 ℃ while stirring, and the reaction was carried out for about 10 hours. By FT-IR pair 2250cm-1The disappearance of the NCO peak of (2) was confirmed. When disappearance of NCO peak was confirmed, the reaction was regarded as the end point of the reaction, and the reaction product was cooled to room temperature. Then, the reaction mixture was filtered through a 100-mesh filter cloth to obtain an elastomer having a butadiene structure and a phenolic hydroxyl group (phenolic hydroxyl group-containing polybutadiene resin: 50% by mass of nonvolatile matter). The number average molecular weight of the elastomer was 5900 and the glass transition temperature was-7 ℃.
< Synthesis example 2: synthesis of polyimide resin 1
Into a 500ml separable flask equipped with a nitrogen introduction tube and a stirring device, 9.13g (30 mmol) of 5-amino-1, 1 ' -biphenyl-2-yl 4-aminobenzoate, 15.61g (30 mmol) of 4,4 ' - (4,4 ' -isopropylidenediphenoxy) bisphthalic dianhydride, 94.64g of N-methyl-2-pyrrolidone, 0.47g (6 mmol) of pyridine, and 10g of toluene were charged, and imidization was performed for 4 hours while removing toluene halfway out of the system under a nitrogen atmosphere at 180 ℃ to obtain a polyimide solution (nonvolatile content: 20 mass%) containing polyimide resin 1. In the polyimide solution, no precipitation of the synthesized polyimide resin 1 was observed.
< Synthesis example 3: synthesis of polyimide resin 2
65.0g of aromatic tetracarboxylic dianhydride (BisDA-1000 manufactured by SABIC JAPAN; 4,4 '- (4, 4' -isopropylidenediphenoxy) diphthalic dianhydride), 266.5g of cyclohexanone, and 44.4g of methylcyclohexane were charged into a reaction vessel equipped with a stirrer, a water separator, a thermometer, and a nitrogen gas inlet tube, and the solution was heated to 60 ℃. Next, 43.7g of dimer diamine ("PRIAMINE 1075" manufactured by Croda Japan) and 5.4g of 1, 3-bis (aminomethyl) cyclohexane were added dropwise thereto, and then imidization was carried out at 140 ℃ for 1 hour. Thus, a polyimide solution (nonvolatile content: 30% by mass) containing the polyimide resin 2 was obtained. In addition, the weight average molecular weight of the polyimide resin 2 was 25,000.
< Synthesis example 4: synthesis of polyimide resin 3
A500 mL separable flask equipped with a quantitative moisture receiver connected to a reflux condenser, a nitrogen inlet tube, and a stirrer was prepared. To the flask were added 20.3g of 4, 4' -oxydiphthalic anhydride (ODPA), 200g of gamma-butyrolactone, 20g of toluene, and 29.6g of 5- (4-aminophenoxy) -3- [4- (4-aminophenoxy) phenyl ] -1,1, 3-trimethylindane, and the mixture was stirred at 45 ℃ for 2 hours under a nitrogen stream to effect a reaction. Then, the reaction solution was heated to about 160 ℃ and the condensation water was azeotropically removed together with toluene under a nitrogen stream. The results of "a predetermined amount of water was stored in the quantitative water receiver" and "no outflow of water was observed" were confirmed. After confirmation, the reaction solution was further heated and stirred at 200 ℃ for 1 hour. Then, the mixture was cooled to obtain a polyimide solution (nonvolatile content: 20 mass%) containing the polyimide resin 3. The obtained polyimide resin 3 has a repeating unit represented by the following formula (X1) and a repeating unit represented by the following formula (X2). In addition, the weight average molecular weight of the foregoing polyimide resin 3 was 12,000.
[ chemical formula 4]
[ chemical formula 5]
< example 1 >
5 parts of bicresol-type epoxy resin ("YX 4000 HK" manufactured by Mitsubishi chemical corporation, having an epoxy equivalent of about 185g/eq.) and naphthalene were added while stirringA mixed solvent of 5 parts of a bisphenol AF-type epoxy resin ("YL 7760" manufactured by Mitsubishi chemical corporation and having an epoxy equivalent of about 238g/eq.) 2 parts of a cyclohexane-type epoxy resin ("ZX 1658 GS" manufactured by Mitsubishi chemical corporation and having an epoxy equivalent of about 135g/eq.) 40 parts of the phenolic hydroxyl group-containing polybutadiene resin (having a nonvolatile content of 50 mass%) obtained in Synthesis example 1 and 10 parts of cyclohexanone was dissolved by heating. After cooling to room temperature, 4 parts of a curing agent of cresol novolak type having a triazine skeleton (a 2-methoxypropanol solution having a hydroxyl equivalent of about 151 and a nonvolatile content of 50% manufactured by DIC Co., Ltd.), 6 parts of an active ester curing agent (an MEK solution having an active group equivalent of about 220 and a nonvolatile content of 65% manufactured by DIC Co., Ltd.), and 6 parts of spherical silica (an MEK solution having an average particle diameter of 0.5 μ M and a specific surface area of 11.2M, SC2500SQ manufactured by Yadu Mar Co., Ltd.) (having a hydroxyl equivalent of about 151, and a nonvolatile content of about 65% by mass) were mixed2The resin composition was prepared by uniformly dispersing 100 parts of silica 40 parts of surface-treated silica with 1 part of N-phenyl-3-aminopropyltrimethoxysilane ("KBM 573", manufactured by shin-Etsu chemical Co., Ltd.), 6 parts of core-shell type graft copolymer rubber particles ("EXL 2655", manufactured by Takara chemical Co., Ltd.), and 0.2 part of amine curing accelerator (4-Dimethylaminopyridine (DMAP)) in a high-speed rotary mixer, and then filtering the resulting dispersion with a drum filter ("SHP 020", manufactured by ROKITECHNO Co., Ltd.).
< example 2 >
A resin composition was prepared in the same manner as in example 1 except that 100 parts (nonvolatile content 20 mass%) of the polyimide solution obtained in synthesis example 2 was used instead of 40 parts (nonvolatile content 50 mass%) of the phenolic hydroxyl group-containing polybutadiene resin obtained in synthesis example 1.
< example 3 >
A resin composition was prepared in the same manner as in example 1 except that 66.7 parts (30 mass% nonvolatile content) of the polyimide solution obtained in synthesis example 3 was used instead of 40 parts (50 mass% nonvolatile content) of the phenolic hydroxyl group-containing polybutadiene resin obtained in synthesis example 1.
< example 4 >
A resin composition was prepared in the same manner as in example 1 except that 100 parts (nonvolatile content 20 mass%) of the polyimide solution obtained in synthesis example 4 was used instead of 40 parts (nonvolatile content 50 mass%) of the phenolic hydroxyl group-containing polybutadiene resin obtained in synthesis example 1.
< example 5 >
A resin composition was prepared in the same manner as in example 1 except that 40 parts of a resin having a polybutadiene structure (BX 360, a block copolymer of polyphenylene ether and polybutadiene, 50 mass% nonvolatile toluene solution, manufactured by japan chemicals) was used instead of 40 parts of the polybutadiene resin having a phenolic hydroxyl group (50 mass% nonvolatile), which was obtained in synthesis example 1.
< example 6 >
A resin composition was prepared in the same manner as in example 1, except that 20 parts of bismaleimide resin ("BMI 689" from DM) was used instead of 40 parts of the phenolic hydroxyl group-containing polybutadiene resin (nonvolatile content: 50 mass%) obtained in synthesis example 1.
< example 7 >
A resin composition was prepared in the same manner as in example 1, except that 50 parts of a 40% methyl ethyl ketone solution of polyrotaxane resin ("SH 1310P", manufactured by Advanced software materials, in which the axial molecule includes a polyethylene glycol chain and the cyclic molecule includes a cyclodextrin) was used instead of 40 parts of the phenolic hydroxyl group-containing polybutadiene resin (50% by mass of nonvolatile content) obtained in synthesis example 1.
< example 8 >
A resin composition was prepared in the same manner as in example 1 except that the amount of the core-shell type graft copolymer rubber particles (EXL 2655, manufactured by Takara chemical Co., Ltd.) used in example 1 was changed from 6 parts to 12 parts.
< comparative example 1 >
A resin composition was prepared in the same manner as in example 1 except that the amount of the spherical silica (product of gazette corporation, "SC 2500 SQ", surface-treated material) used in example 1 was changed from 40 parts to 70 parts, and the amount of the core-shell type graft copolymer rubber particles (product of dow chemical japan, "EXL 2655") used was changed from 6 parts to 5 parts.
< comparative example 2 >
A resin composition was prepared in the same manner as in example 1 except that 6 parts of the core-shell type graft copolymer rubber particles (EXL 2655, manufactured by Takara chemical Co., Ltd.) of example 1 were not used.
< comparative example 3 >
A resin composition was prepared in the same manner as in example 1, except that 42 parts of a phenoxy resin ("YX 7553BH 30" manufactured by mitsubishi chemical corporation, 30 mass% in solid content) was used instead of 40 parts of the phenolic hydroxyl group-containing polybutadiene resin (50 mass% in nonvolatile content) obtained in synthesis example 1.
< test example 1: evaluation of flexibility (MIT folding endurance)
The resin compositions of examples and comparative examples were uniformly applied to the release-treated surface of a PET film (38 μm in thickness) treated with an alkyd-based release agent using a die coater so that the thickness of the dried resin composition layer became 40 μm, and dried at 80 to 120 ℃ (average 100 ℃) for 6 minutes to obtain a resin sheet.
The obtained resin sheet was laminated on a polyimide film (UPILEX S, manufactured by yukexing co., ltd.) using a batch vacuum pressure laminator ("MVLP-500"), manufactured by wako corporation. For lamination, the pressure was reduced for 30 seconds to 13hPa or less, and then the laminate was pressure-bonded at 120 ℃ and 0.74MPa for 30 seconds to obtain a resin sheet with a protective film. Then, the PET film was peeled from the resin sheet with the protective film, and the resin composition was cured at 190 ℃ for 90 minutes to peel the polyimide film, thereby obtaining a cured product sample.
The obtained cured product sample was cut into test pieces having a width of 15mm and a length of 110mm, and the number of times of breaking of the cured product was measured according to JIS C-5016 under the measurement conditions of a load of 2.5N, a bending angle of 90 degrees, a bending radius of 1.0mm, and a bending speed of 175 times/minute using an MIT tester (MIT-MIT, manufactured by Toyo Seiki Seisaku-Sho Ltd.). The 5 samples were measured, and the average of the samples ranked first three times from large to small was calculated. The case where the folding endurance was less than 8,000 was evaluated as "x", and the case where the folding endurance was 8,000 or more was evaluated as "O".
< test example 2: evaluation of pattern embeddability and flatness >
< test example 2-1: measurement of minimum melt viscosity >
The lowest melt viscosity of the resin composition layer of the resin sheet obtained in test example 1 was measured using a dynamic viscoelasticity measuring apparatus ("Rheosol-G3000" manufactured by UBM corporation). For 1g of the resin composition sampled from the resin composition layer, the dynamic viscoelasticity modulus was measured using a parallel plate having a diameter of 18mm, at a temperature rising rate of 5 ℃/min from an initial temperature of 60 ℃ to 200 ℃, under measurement conditions of a measurement temperature interval of 2.5 ℃, a vibration frequency of 1Hz, and a deformation of 1 deg.g, and the minimum melt viscosity (poise) was measured.
< test examples 2-2: measurement of adhesion force
The protective film was peeled off from the resin sheet with the protective film obtained in test example 1, and a probe tack TESTER ("TE-6002" manufactured by TESTER INDUSTRIAL Co.) was used for the resin composition layer, and a measurement load of 1kgf/cm was measured with a glass probe having a diameter of 5mm2The adhesive force (N) under the conditions of a contact speed of 0.5 mm/sec, a stretching speed of 0.5 mm/sec, a holding time of 10 seconds and a temperature of 80 ℃ was evaluated as "×" when the adhesive force was more than 1.6N and as "○" when the adhesive force was 1.6N or less.
< test examples 2 to 3: evaluation of pattern embeddability and voids >
As the inner layer circuit board, a glass cloth-based epoxy resin double-sided copper-clad laminate (copper foil 18 μm thick, substrate 0.15mm thick, "HL 832NSF LCA" manufactured by mitsubishi gas chemical corporation, 255 × 340mm in size) having circuit conductors (copper) formed of 1mm square wiring patterns (residual copper ratio 59%) on both sides was prepared. The inner layer circuit board was roughened on both surfaces by a copper surface roughening treatment (copper etching amount: 0.5 μm) using "CZ 8201" manufactured by MEC K.
The resin sheet obtained in test example 1 was laminated on both sides of the inner layer circuit board so that the resin composition layer was in contact with the inner layer circuit board using a batch vacuum press Laminator (2-Stage build sheet Laminator, CVP700, manufactured by Nikko Materials co., ltd.). The lamination was carried out by: the pressure was reduced for 30 seconds to a pressure of 13hPa or less, and the pressure was bonded at 130 ℃ and a pressure of 0.74MPa for 45 seconds. Next, hot pressing was performed at 120 ℃ for 75 seconds under a pressure of 0.5 MPa.
The inner layer circuit board laminated with the resin sheet was put into an oven at 100 ℃ under a temperature condition of 100 ℃ and then thermally cured for 30 minutes, and then was moved into an oven at 180 ℃ under a temperature condition of 180 ℃ and then thermally cured for 30 minutes, thereby forming an insulating layer. This was used as a "substrate for evaluation".
The support was peeled off from the evaluation substrate, and the surface of the insulating layer was observed with a micro optical microscope. Regarding the pattern embeddability, a case where the pattern is sufficiently embedded is evaluated as "o", and a case where the pattern is insufficiently embedded is evaluated as "x". Regarding the voids, the case where no voids were generated was evaluated as "o", and the case where voids were generated was evaluated as "x".
The amounts of nonvolatile components used in 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]
It is found that by using a resin composition comprising (a) a thermosetting resin, (B) an inorganic filler, (C) an organic filler in an amount of 5 mass% or more, and (D) an adhesive flexibilizing agent, the tackiness can be suppressed to a low level while maintaining excellent flexibility. In particular, when the content of the organic filler (C) is 10 mass% or less, it is found that the void defect can be suppressed and the pattern embeddability is excellent.
Claims (17)
1. A resin composition comprising (A) a thermosetting resin, (B) an inorganic filler, (C) an organic filler, and (D) an adhesive flexibilizing agent,
wherein the content of the component (C) is 5% by mass or more, assuming that the nonvolatile content in the resin composition is 100% by mass.
2. The resin composition according to claim 1, wherein the content of the component (B) is 50% by mass or less, assuming that the nonvolatile content in the resin composition is 100% by mass.
3. The resin composition according to claim 1, wherein the content of the component (C) is 10% by mass or less, assuming that the nonvolatile content in the resin composition is 100% by mass.
4. The resin composition according to claim 1, wherein the component (D) is selected from the group consisting of a resin having a polybutadiene structure, a polyrotaxane resin, a polyimide resin, and a maleimide resin having a dimer acid skeleton.
5. The resin composition according to claim 1, wherein the content of the component (D) is 1% by mass or more, assuming that the nonvolatile content in the resin composition is 100% by mass.
6. The resin composition according to claim 1, wherein (C) the organic filler is a core-shell type graft copolymer particle.
7. The resin composition according to claim 6, wherein the monomer component forming the shell portion of the core-shell type graft copolymer particle is a (meth) acrylate.
8. The resin composition according to claim 6, wherein the core particle of the core-shell graft copolymer particle comprises a thermoplastic elastomer.
9. The resin composition according to claim 1, wherein the component (A) is an epoxy resin.
10. The resin composition according to claim 1, further comprising (E) a curing agent.
11. The resin composition according to claim 10, wherein the (E) component comprises an active ester curing agent.
12. The resin composition according to claim 1, wherein a solid content ratio in the resin composition is 95% by mass or less.
13. The resin composition according to claim 1, which is used for forming an insulating layer of a multilayer flexible substrate.
14. A cured product of the resin composition according to any one of claims 1 to 13.
15. A resin sheet, comprising:
support body, and
a resin composition layer formed of the resin composition according to any one of claims 1 to 13 provided on the support.
16. A multilayer flexible substrate comprising an insulating layer formed by curing the resin composition according to any one of claims 1 to 13.
17. A semiconductor device comprising the multilayer flexible substrate according to claim 16.
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JP6904441B1 (en) * | 2020-01-30 | 2021-07-14 | 横浜ゴム株式会社 | Epoxy resin composition for prepreg and prepreg |
CN112409700B (en) * | 2020-11-19 | 2022-12-02 | 江苏金发科技新材料有限公司 | High-performance polypropylene composite material for vehicles and preparation method thereof |
WO2023074429A1 (en) * | 2021-10-25 | 2023-05-04 | パナソニックIpマネジメント株式会社 | Heat-curable resin composition, resin sheet, resin-coated metal foil, metal-clad laminate, and printed wiring board |
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JP6343575B2 (en) * | 2015-02-27 | 2018-06-13 | 株式会社ダイセル | Curable epoxy resin composition |
JP2018012777A (en) * | 2016-07-20 | 2018-01-25 | 日立化成株式会社 | Insulation resin material, resin film for interlayer insulation and production method of the same, composite film and production method of the same, and printed wiring board and production method of the same |
JP2018070668A (en) * | 2016-10-24 | 2018-05-10 | 信越化学工業株式会社 | Liquid epoxy resin composition |
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US20070090299A1 (en) * | 2005-10-20 | 2007-04-26 | Shin-Etsu Chemical Co., Ltd. | Adhesive composition and sheet having an adhesive layer of the composition |
JP2014185330A (en) * | 2013-02-20 | 2014-10-02 | Hitachi Chemical Co Ltd | Resin composition, primer layer for plating process, primer layer for plating process supported by substrate, cured primer layer for plating process, laminate for wiring board, method of producing laminate for wiring board, multilayer wiring board, and method of producing multilayer wiring board |
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CN108727942A (en) * | 2017-04-24 | 2018-11-02 | 味之素株式会社 | Resin combination |
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