CN114085606A - Resin composition - Google Patents
Resin composition Download PDFInfo
- Publication number
- CN114085606A CN114085606A CN202110967529.0A CN202110967529A CN114085606A CN 114085606 A CN114085606 A CN 114085606A CN 202110967529 A CN202110967529 A CN 202110967529A CN 114085606 A CN114085606 A CN 114085606A
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- CN
- China
- Prior art keywords
- resin composition
- layer
- resin
- group
- component
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000011342 resin composition Substances 0.000 title claims abstract description 230
- 239000010410 layer Substances 0.000 claims abstract description 275
- 239000003822 epoxy resin Substances 0.000 claims abstract description 136
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 136
- 239000000463 material Substances 0.000 claims abstract description 71
- 238000012360 testing method Methods 0.000 claims abstract description 61
- 239000011229 interlayer Substances 0.000 claims abstract description 20
- 229920005989 resin Polymers 0.000 claims description 131
- 239000011347 resin Substances 0.000 claims description 131
- -1 polysiloxane structure Polymers 0.000 claims description 111
- 239000003795 chemical substances by application Substances 0.000 claims description 79
- 239000000758 substrate Substances 0.000 claims description 69
- 239000004065 semiconductor Substances 0.000 claims description 64
- 238000011156 evaluation Methods 0.000 claims description 39
- 238000007789 sealing Methods 0.000 claims description 25
- 239000005062 Polybutadiene Substances 0.000 claims description 21
- 229920002857 polybutadiene Polymers 0.000 claims description 21
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 16
- 229920006332 epoxy adhesive Polymers 0.000 claims description 16
- 238000010438 heat treatment Methods 0.000 claims description 16
- 239000011256 inorganic filler Substances 0.000 claims description 16
- 229910003475 inorganic filler Inorganic materials 0.000 claims description 16
- 239000007788 liquid Substances 0.000 claims description 13
- 238000007585 pull-off test Methods 0.000 claims description 13
- 230000020169 heat generation Effects 0.000 claims description 11
- 239000004417 polycarbonate Substances 0.000 claims description 10
- 229920000515 polycarbonate Polymers 0.000 claims description 10
- 229920001195 polyisoprene Polymers 0.000 claims description 8
- 229920002367 Polyisobutene Polymers 0.000 claims description 7
- 229920000233 poly(alkylene oxides) Polymers 0.000 claims description 7
- 229920000193 polymethacrylate Polymers 0.000 claims description 7
- 230000009477 glass transition Effects 0.000 claims description 4
- 238000005345 coagulation Methods 0.000 claims description 3
- 230000015271 coagulation Effects 0.000 claims description 3
- 238000000034 method Methods 0.000 abstract description 49
- 239000011810 insulating material Substances 0.000 abstract description 39
- 230000007774 longterm Effects 0.000 abstract description 35
- 238000000926 separation method Methods 0.000 abstract description 11
- 238000001723 curing Methods 0.000 description 96
- 125000004432 carbon atom Chemical group C* 0.000 description 71
- 239000000047 product Substances 0.000 description 69
- 125000001424 substituent group Chemical group 0.000 description 66
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 58
- 239000000243 solution Substances 0.000 description 56
- 125000003118 aryl group Chemical group 0.000 description 53
- 229910052751 metal Inorganic materials 0.000 description 52
- 239000002184 metal Substances 0.000 description 52
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 44
- 239000011888 foil Substances 0.000 description 41
- 239000004020 conductor Substances 0.000 description 37
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 33
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 32
- 239000010408 film Substances 0.000 description 32
- 239000002585 base Substances 0.000 description 30
- 238000003475 lamination Methods 0.000 description 26
- 239000002245 particle Substances 0.000 description 26
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 150000002148 esters Chemical group 0.000 description 24
- 229910052802 copper Inorganic materials 0.000 description 23
- 239000010949 copper Substances 0.000 description 23
- 239000011889 copper foil Substances 0.000 description 23
- 239000004593 Epoxy Substances 0.000 description 22
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 22
- 238000004519 manufacturing process Methods 0.000 description 22
- 239000007787 solid Substances 0.000 description 22
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 21
- 229920003986 novolac Polymers 0.000 description 20
- 239000002966 varnish Substances 0.000 description 20
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 19
- 125000000217 alkyl group Chemical group 0.000 description 19
- 238000005227 gel permeation chromatography Methods 0.000 description 19
- RHBKJVRQCIRZGE-UHFFFAOYSA-N 2,3,3-trimethyl-1,2-dihydroindene Chemical group C1=CC=C2C(C)(C)C(C)CC2=C1 RHBKJVRQCIRZGE-UHFFFAOYSA-N 0.000 description 18
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 17
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 17
- 125000001931 aliphatic group Chemical group 0.000 description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 17
- 238000007788 roughening Methods 0.000 description 17
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical class O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 16
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 16
- 238000005259 measurement Methods 0.000 description 16
- 239000000126 substance Substances 0.000 description 16
- 229920001971 elastomer Polymers 0.000 description 15
- 125000003700 epoxy group Chemical group 0.000 description 14
- 239000005060 rubber Substances 0.000 description 14
- 239000000377 silicon dioxide Substances 0.000 description 14
- 239000003960 organic solvent Substances 0.000 description 13
- 239000006087 Silane Coupling Agent Substances 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 12
- 239000004305 biphenyl Substances 0.000 description 12
- 235000010290 biphenyl Nutrition 0.000 description 12
- 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 12
- 150000001875 compounds Chemical class 0.000 description 12
- 238000009826 distribution Methods 0.000 description 12
- 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 description 12
- 239000011572 manganese Substances 0.000 description 12
- 206010042674 Swelling Diseases 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 125000000524 functional group Chemical group 0.000 description 11
- 230000008961 swelling Effects 0.000 description 11
- 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 10
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 10
- 229910052799 carbon Inorganic materials 0.000 description 10
- 125000001624 naphthyl group Chemical group 0.000 description 10
- 229910052759 nickel Inorganic materials 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- 125000004433 nitrogen atom Chemical group N* 0.000 description 10
- 235000013824 polyphenols Nutrition 0.000 description 10
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 9
- 150000008065 acid anhydrides Chemical class 0.000 description 9
- 125000003545 alkoxy group Chemical group 0.000 description 9
- 125000002947 alkylene group Chemical group 0.000 description 9
- 229910045601 alloy Inorganic materials 0.000 description 9
- 239000000956 alloy Substances 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 9
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 9
- KAKZBPTYRLMSJV-UHFFFAOYSA-N butadiene group Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 9
- 230000008859 change Effects 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000004643 cyanate ester Substances 0.000 description 9
- 125000000623 heterocyclic group Chemical group 0.000 description 9
- 229910052742 iron Inorganic materials 0.000 description 9
- 239000004850 liquid epoxy resins (LERs) Substances 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- 235000012431 wafers Nutrition 0.000 description 9
- 229940126062 Compound A Drugs 0.000 description 8
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 8
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
- 239000000654 additive Substances 0.000 description 8
- 239000000853 adhesive Substances 0.000 description 8
- 230000001070 adhesive effect Effects 0.000 description 8
- 125000000753 cycloalkyl group Chemical group 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 238000009499 grossing Methods 0.000 description 8
- 125000005843 halogen group Chemical group 0.000 description 8
- KBJFYLLAMSZSOG-UHFFFAOYSA-N n-(3-trimethoxysilylpropyl)aniline Chemical compound CO[Si](OC)(OC)CCCNC1=CC=CC=C1 KBJFYLLAMSZSOG-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 239000003381 stabilizer Substances 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 239000007822 coupling agent Substances 0.000 description 7
- 238000002788 crimping Methods 0.000 description 7
- 239000000539 dimer Substances 0.000 description 7
- 239000011521 glass Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 7
- 239000007800 oxidant agent Substances 0.000 description 7
- 238000007747 plating Methods 0.000 description 7
- 229910052719 titanium Inorganic materials 0.000 description 7
- 239000010936 titanium Substances 0.000 description 7
- 150000003923 2,5-pyrrolediones Chemical class 0.000 description 6
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 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
- 125000004104 aryloxy group Chemical group 0.000 description 6
- 229910052804 chromium Inorganic materials 0.000 description 6
- 239000011651 chromium Substances 0.000 description 6
- 229920006026 co-polymeric resin Polymers 0.000 description 6
- 229930003836 cresol Natural products 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 238000010030 laminating Methods 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 230000003472 neutralizing effect Effects 0.000 description 6
- 239000012766 organic filler Substances 0.000 description 6
- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical compound NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 description 6
- 229920001721 polyimide Polymers 0.000 description 6
- 230000001681 protective effect Effects 0.000 description 6
- 229910052710 silicon Inorganic materials 0.000 description 6
- 239000010703 silicon Substances 0.000 description 6
- 229920001187 thermosetting polymer Polymers 0.000 description 6
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 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
- 125000004018 acid anhydride group Chemical group 0.000 description 5
- 125000004414 alkyl thio group Chemical group 0.000 description 5
- 239000002518 antifoaming agent Substances 0.000 description 5
- 125000005110 aryl thio group Chemical group 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 5
- 239000007771 core particle Substances 0.000 description 5
- 239000002270 dispersing agent Substances 0.000 description 5
- 238000005530 etching Methods 0.000 description 5
- 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 5
- 239000000203 mixture Substances 0.000 description 5
- 229910052698 phosphorus Inorganic materials 0.000 description 5
- 229920001296 polysiloxane Polymers 0.000 description 5
- 229920002223 polystyrene Polymers 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000012756 surface treatment agent Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 229910052725 zinc Inorganic materials 0.000 description 5
- 239000011701 zinc Substances 0.000 description 5
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 4
- 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
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 4
- 229910000599 Cr alloy Inorganic materials 0.000 description 4
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 4
- 239000004642 Polyimide 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
- 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 4
- 125000002723 alicyclic group Chemical group 0.000 description 4
- ZFVMWEVVKGLCIJ-UHFFFAOYSA-N bisphenol AF Chemical compound C1=CC(O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(O)C=C1 ZFVMWEVVKGLCIJ-UHFFFAOYSA-N 0.000 description 4
- 125000002837 carbocyclic group Chemical group 0.000 description 4
- VPKDCDLSJZCGKE-UHFFFAOYSA-N carbodiimide group Chemical group N=C=N VPKDCDLSJZCGKE-UHFFFAOYSA-N 0.000 description 4
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 4
- 239000000788 chromium alloy Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 239000011258 core-shell material Substances 0.000 description 4
- 230000006866 deterioration Effects 0.000 description 4
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 4
- 239000003063 flame retardant Substances 0.000 description 4
- 125000005647 linker group Chemical group 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 125000004430 oxygen atom Chemical group O* 0.000 description 4
- 150000002978 peroxides Chemical class 0.000 description 4
- 239000011574 phosphorus Substances 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- 229920000139 polyethylene terephthalate Polymers 0.000 description 4
- 239000005020 polyethylene terephthalate Substances 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 4
- 229910052709 silver Inorganic materials 0.000 description 4
- 239000004332 silver Substances 0.000 description 4
- 238000004381 surface treatment Methods 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- 125000003396 thiol group Chemical group [H]S* 0.000 description 4
- 229910052718 tin Inorganic materials 0.000 description 4
- FPZWZCWUIYYYBU-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl acetate Chemical compound CCOCCOCCOC(C)=O FPZWZCWUIYYYBU-UHFFFAOYSA-N 0.000 description 3
- CQOZJDNCADWEKH-UHFFFAOYSA-N 2-[3,3-bis(2-hydroxyphenyl)propyl]phenol Chemical compound OC1=CC=CC=C1CCC(C=1C(=CC=CC=1)O)C1=CC=CC=C1O CQOZJDNCADWEKH-UHFFFAOYSA-N 0.000 description 3
- LYNVLWLRSACENL-UHFFFAOYSA-N 2-decyl-1h-imidazole Chemical compound CCCCCCCCCCC1=NC=CN1 LYNVLWLRSACENL-UHFFFAOYSA-N 0.000 description 3
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-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
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- 229910000881 Cu alloy Inorganic materials 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
- 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
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 125000004423 acyloxy group Chemical group 0.000 description 3
- 239000005456 alcohol based solvent Substances 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 125000004450 alkenylene group Chemical group 0.000 description 3
- 125000001118 alkylidene group Chemical group 0.000 description 3
- 229920013822 aminosilicone Polymers 0.000 description 3
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 150000001718 carbodiimides Chemical class 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 125000000000 cycloalkoxy group Chemical group 0.000 description 3
- 230000032798 delamination Effects 0.000 description 3
- 150000004985 diamines Chemical class 0.000 description 3
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 238000000434 field desorption mass spectrometry Methods 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
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Images
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- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
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- C09D175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/226—Mixtures of di-epoxy compounds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- 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
- C08G59/4007—Curing agents not provided for by the groups C08G59/42 - C08G59/66
- C08G59/4014—Nitrogen containing compounds
- C08G59/4042—Imines; Imides
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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- C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
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- C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
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- C09D179/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen, with or without oxygen, or carbon only, not provided for in groups C09D161/00 - C09D177/00
- C09D179/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C09D179/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
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- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/60—Additives non-macromolecular
- C09D7/61—Additives non-macromolecular inorganic
- C09D7/62—Additives non-macromolecular inorganic modified by treatment with other compounds
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- C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
- H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
- H01L23/293—Organic, e.g. plastic
- H01L23/295—Organic, e.g. plastic containing a filler
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- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K1/00—Printed circuits
- H05K1/02—Details
- H05K1/03—Use of materials for the substrate
- H05K1/0313—Organic insulating material
- H05K1/0353—Organic insulating material consisting of two or more materials, e.g. two or more polymers, polymer + filler, + reinforcement
- H05K1/0373—Organic insulating material consisting of two or more materials, e.g. two or more polymers, polymer + filler, + reinforcement containing additives, e.g. fillers
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- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K3/00—Apparatus or processes for manufacturing printed circuits
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- 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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Abstract
The object of the present invention is to provide a method for obtaining a product which can inhibitA resin composition for an insulating material which exhibits excellent long-term reliability while being warped. The present invention is a resin composition comprising (A) an epoxy resin and (B) a stress relaxation material, wherein the following results are shown when a cured product layer thereof is subjected to 5 times of student pull test<Criterion for determining peeling mode>In the peeling mode I or the peeling mode III, and the load value at the time of peeling is 180kgf/cm2In the above-mentioned manner,<criterion for determining peeling mode>The mode of separation I is a mode of separation II in which the interface of the copper-clad laminate and the cured product layer is separated from each other (interlayer separation) 3 times or more, a mode of separation III in which the cured product layer is cohesively separated from each other (intralayer separation) 3 times or more, and a mode of separation in which the interface of the cured product layer and the stud pin is separated from each other (interlayer separation) 3 times or more.
Description
Technical Field
The present invention relates to a resin composition. Further, the present invention relates to a resin sheet, a printed wiring board, a semiconductor chip package and a semiconductor device obtained using the resin composition.
Background
In recent years, there has been an increasing demand for small and high-function electronic devices such as smartphones and tablet devices, and accordingly, printed wiring boards and insulating materials for semiconductor packages used in these small electronic devices are also required to have further high functions. As such an insulating material, for example, a resin composition disclosed in patent document 1 is known.
Documents of the prior art
[ patent document ]
[ patent document 1] Japanese patent laid-open No. 2016-010964.
Disclosure of Invention
Problems to be solved by the invention
With the miniaturization of electronic devices, the printed wiring boards and semiconductor packages used therein have been made thinner. As printed wiring boards and semiconductor packages have become thinner, warpage due to thermal history and the like may occur. In order to suppress the warpage, it is considered to blend a stress relaxation material in the insulating material, but in this case, it is found that physical properties such as mechanical strength of the insulating material and adhesion strength to the conductor are reduced with time, and long-term reliability is deteriorated. With the development of electronic devices with higher functions and higher performance, the insulating material is exposed to heat preservation, and the deterioration of long-term reliability tends to become more and more significant.
The present invention addresses the problem of providing a resin composition that can provide an insulating material that exhibits good long-term reliability while suppressing warpage.
Means for solving the problems
The reason why the physical properties of the insulating material containing the stress relaxation material deteriorate with time is presumed to be that the stress relaxation material present in the insulating material is oxidized by oxygen in the air and the molecular chain thereof is cut. In particular, in the vicinity of the interface with a conductor (copper or the like), oxidation reaction is promoted by the catalytic action of the conductor, and this is considered to be a factor of lowering the adhesion strength. In a high-temperature environment, oxidation degradation of the stress relaxation material proceeds more remarkably.
It is difficult to determine whether the long-term reliability of the insulating material is good or bad by initial characteristic evaluation. For example, the mechanical strength of the insulating material and the adhesion strength to the conductor can be evaluated by a general pull test and a peel test, but the value of the initial characteristic in these evaluations does not correspond to the quality of the long-term reliability, and it is difficult to predict the quality of the long-term reliability from the initial characteristic value.
In the method from the viewpoint of the composition of the resin composition constituting the insulating material, since the presence or absence of the influence of each component on the long-term reliability is different, and the degree of influence on the long-term reliability is increased or decreased depending on the combination of the components, it is difficult to specify the object (resin composition) of the insulating material exhibiting good long-term reliability by the kind and content of the component to be blended.
As a result of intensive studies to achieve good long-term reliability for an insulating material containing a stress relaxation material for suppressing warpage, the present inventors have found that an insulating material having good long-term reliability can be achieved while maintaining the effect of suppressing warpage obtained by containing a stress relaxation material if the resin composition shows a specific peeling pattern in the student pull test (a pull test using a rivet-shaped jig) and the load value at the time of peeling is a predetermined value or more. In the student pull test, a Stud pin (rivet-like jig) was fixed to a cured product (insulating material) of a resin composition provided on a substrate (copper), and the Stud pin was pulled in a direction perpendicular to the substrate to measure a peeled state of the insulating material and a load value at the time of peeling. In the student pull test, unlike the ordinary pull test and the peeling test, microscopic adhesion of the stress relaxation component to other components and adhesion to a conductor can be evaluated in combination, and it is estimated that long-term reliability can be evaluated precisely from the initial characteristics (student pull test characteristics). It is considered that the higher the microscopic adhesion (covalent bond, hydrogen bond, intermolecular force, etc.) of the stress relaxation component to other components, the more the oxidation by oxygen in the air can be suppressed.
That is, the present invention includes the following.
[1] A resin composition comprising (A) an epoxy resin and (B) a stress relaxation material,
as follows<Stud pull test conditions>When 5 tests were carried out, the following results were shown<Criterion for determining peeling mode>In the peeling mode I or the peeling mode III, and the load value at the time of peeling is 180kgf/cm2In the above-mentioned manner,
< conditions of the Stud pull test (pulling test using a rivet-shaped jig) >
A layer of the resin composition is provided on the roughened copper-clad laminate at a temperature T1Heating at a temperature of 90 deg.C for 90 minutes to cure the resin composition to obtain an evaluation substrate, fixing a Stud pin (rivet-shaped jig; diameter of bonding surface is 2.7mm) on the cured product layer of the resin composition of the evaluation substrate with an epoxy adhesive, heating at 150 deg.C for 1 hour to bond, pulling the Stud pin at a speed of 2 kgf/sec in a direction perpendicular to the main surface of the evaluation substrate with a Stud pull tester, and observing a load value (kgf/cm) at the time of peeling the cured product layer2) And a peeling mode in which when the temperature of a heat generation peak exhibited by the resin composition when the resin composition is heated from 30 ℃ to 350 ℃ at a temperature rise rate of 5 ℃/min using a differential scanning calorimeter is T (. degree. C.), the temperature T is set to1(DEG C) is a temperature of (T +10) (. degree.C.) or higher,
< criterion for determining peeling mode >
Peeling mode I: the copper-clad laminate has been subjected to interface detachable (interlayer peeling) 3 or more times
Peeling mode II: the solidified layer is broken by coagulation (peeling in the layer) for more than 3 times
Peeling mode III: the cured product layer-stud pin interface was peeled (interlayer peeling) 3 times or more.
[2] [1] the resin composition, wherein the content of the component (B) is 1% by mass or more, based on 100% by mass of the total nonvolatile components in the resin composition.
[3] [1] the resin composition according to [1] or [2], wherein the number average molecular weight (Mn) of the component (B) is 1,000 or more.
[4] The resin composition according to any one of [1] to [3], wherein the component (B) is at least 1 selected from the group consisting of a resin having a glass transition temperature (Tg) of 25 ℃ or less and a resin that is liquid at 25 ℃.
[5] The resin composition according to any one of [1] to [4], wherein the component (B) is a resin having 1 or more structures selected from a polybutadiene structure, a polysiloxane structure, a poly (meth) acrylate structure, a polyalkylene oxide structure, a polyisoprene structure, a polyisobutylene structure, and a polycarbonate structure in a molecule.
[6] The resin composition according to any one of [1] to [5], further comprising (C) an inorganic filler.
[7] The resin composition according to any one of [1] to [6], further comprising (D) a curing agent.
[8] The resin composition according to any one of [1] to [7], further comprising (E) a maleimide compound.
[9] The resin composition according to any one of [6] to [8], wherein the content of the component (C) is 40% by mass or more, based on 100% by mass of the total nonvolatile components in the resin composition.
[10] The resin composition according to any one of [1] to [9], which is used for an insulating layer of a printed wiring board.
[11] The resin composition according to any one of [1] to [9], which is used for sealing.
[12] A resin sheet comprising a support and a layer of the resin composition described in any one of [1] to [11] provided on the support.
[13] A printed wiring board comprising an insulating layer, wherein the insulating layer comprises a cured product of the resin composition according to any one of [1] to [10 ].
[14] A semiconductor chip package comprising a sealing layer, wherein the sealing layer comprises a cured product of the resin composition according to any one of [1] to [9] and [11 ].
[15] [14] the semiconductor chip package of Fan-Out type.
[16] A semiconductor device comprising a layer containing a cured product of the resin composition according to any one of [1] to [11 ].
Effects of the invention
According to the present invention, a resin composition which can provide an insulating material exhibiting good long-term reliability while suppressing warpage can be provided.
[ description of the drawings ]
FIG. 1 is a schematic diagram for explaining the student pull test.
FIG. 2 is a schematic view showing a peeling pattern in the student pull test.
Detailed Description
The present invention will be described in detail below based on preferred embodiments thereof. However, the present invention is not limited to the embodiments and examples described below, and may be modified and implemented arbitrarily within the scope not departing from the claims and the equivalent scope thereof.
[ resin composition ]
The resin composition of the present invention is characterized by containing
(A) An epoxy resin, and
(B) a stress-relaxing material, which is a material,
as follows<Stud pull test conditions>When 5 tests were carried out, the following results were shown<Criterion for determining peeling mode>In the peeling mode I or the peeling mode III, and the load value at the time of peeling is 180kgf/cm2The above.
< Stud pull test conditions >
A layer of the resin composition is provided on the roughened copper-clad laminate at a temperature T1The resin composition was cured by heating at (. degree.C.) for 90 minutes to obtain an evaluation substrate. The screw pin (the diameter of the bonding surface was 2.7mm) was fixed to the cured product layer of the resin composition of the evaluation substrate with an epoxy adhesive, and the substrate was heated at 150 ℃ for 1 hour to bond the cured product. The Stud pin was pulled at a speed of 2 kgf/sec in a direction perpendicular to the main surface of the evaluation substrate by a student pull tester, and the load value (kgf/cm) at the time of peeling of the cured product layer was observed2) And a peeling mode in which when the temperature of a heat generation peak exhibited by the resin composition when the resin composition is heated from 30 ℃ to 350 ℃ at a temperature rise rate of 5 ℃/min using a differential scanning calorimeter is T (. degree. C.), the temperature T is set to1(° c) refers to temperatures above (T +10) (° c).
< criterion for determining peeling mode >
Peeling mode I: the copper-clad laminate has been subjected to interface detachable (interlayer peeling) 3 or more times
Peeling mode II: the solidified layer is broken by coagulation (peeling in the layer) for more than 3 times
Peeling mode III: the cured product layer-stud pin interface was peeled (interlayer peeling) 3 times or more.
The student pull test is a pull test using a rivet-shaped jig (Stud pin), and is known as a method for measuring the adhesion strength of a thin film. After a film is bonded to a substrate and set, a stud pin is fixed to an exposed surface of the film. The stud pin has a bonding force of a certain value or more (e.g., 700 kgf/cm)2Above) is fixed to the exposed surface of the film. Further, after the base material was fixed, a vertical pulling load was applied to the stud pin, and the load at the time of breaking ・ and peeling was measured, thereby obtaining information on the adhesion strength between the film and the base material. By changing the type of the substrate, the size of the stud pin (the area ・ diameter of the bonding surface), the speed of the vertical pulling load applied to the stud pin, and the like, the properties represented by the adhesion strength to the substrate can be compositely evaluated with respect to the film to be measured.
The conditions of the student pull test in the present invention will be described with reference to FIG. 1.
Preparation of evaluation substrate
First, a copper-clad laminate subjected to roughening treatment was prepared as the base material 1. The thickness of each of the copper foil and the substrate of the copper-clad laminate is not particularly limited as long as any of the peeling modes I, II, and III described later is exhibited without causing breakage of the substrate itself in the Stud pull test, and a single-sided copper-clad laminate or a double-sided copper-clad laminate may be used. In the case of using a single-sided copper-clad laminate, a layer of the resin composition is provided on the surface of the copper foil. The copper foil of the copper-clad laminate is subjected to a roughening treatment before joining with the resin composition. The conditions for the roughening treatment may be those generally used for the base treatment (roughening treatment) of a copper foil as a copper-clad laminate. In the present invention, the peeling mode in the student pull test and the load at the time of peeling were measured using a substrate obtained by etching both sides of a copper-clad laminate (R-1766 manufactured by Panasonic corporation, "18 μm in thickness of copper foil, 0.8mm in thickness of substrate) with a microetching agent (" CZ8101 "manufactured by メック) so that the copper etching amount reached 2 μm as the substrate 1.
Next, a layer of the resin composition was provided on the copper-clad laminated sheet (i.e., the base material 1) subjected to the roughening treatment. Specifically, a layer of a resin composition is provided on the roughened surface of the copper foil of the copper-clad laminate. The layer of the resin composition can be provided by laminating the resin composition layer on the copper-clad laminate so that the resin composition layer is bonded to the roughened surface of the copper foil of the copper-clad laminate, for example, using a resin sheet described later. The lamination may be carried out by a lamination process, and the conditions of the lamination process may be those described later with respect to the manufacturing method of the printed wiring board. In the present invention, the peeling mode and the load at the time of peeling in the student pull test were measured using a resin sheet including a layer of a resin composition, and an evaluation substrate prepared by performing a lamination process and a smoothing process under the following conditions.
And (3) laminating treatment: after the pressure was reduced for 30 seconds to a pressure of 3hPa or less, the resultant was pressed at 100 ℃ and a pressure of 0.74MPa for 30 seconds.
Smoothing treatment: after the lamination treatment, the laminate was hot-pressed at 100 ℃ and 0.5MPa for 60 seconds under atmospheric pressure.
After the layer of resin composition is provided, at a temperature T1The resin composition was cured by heating at (. degree.C.) for 90 minutes. Thus, an evaluation substrate was obtained in which a cured product layer 2 of a resin composition was provided on the copper-clad laminate (i.e., the base material 1) subjected to the roughening treatment. Here, when the temperature of the exothermic peak of the resin composition at the time of heating from 30 ℃ to 350 ℃ at a temperature rise rate of 5 ℃/min using a differential scanning calorimeter is T (. degree. C.), the temperature T is set to1(° c) is a temperature above (T +10) (° c). When a plurality of heat generation peaks are present, the temperature T is determined with the temperature of the heat generation peak in the highest temperature region as T (. degree. C.)1In degrees centigrade. Temperature T1The upper limit is not particularly limited as long as it is (T +10) (. degree. C.) or more, and it is preferably (T +100) (. degree. C.) or less (but not more than 360 ℃).
The thickness of the cured product layer 2 of the resin composition is not particularly limited. In the present invention using the student pull test, the quality of the long-term reliability can be judged based on the peeling mode and the load value at the time of peeling, regardless of the thickness of the cured product layer 2 of the resin composition. The thickness of the cured product layer 2 of the resin composition may be, for example, 5 μm or more and 10 μm or more, and may be 200 μm or less and 150 μm or less.
The Stud pull test-
The screw pin 11 was fixed to the cured product layer 2 of the resin composition of the obtained evaluation substrate with an epoxy adhesive 10, and was heated at 150 ℃ for 1 hour to bond the resin composition. In the present invention, a stud pin having an adhesive surface with a diameter of 2.7mm is used as the stud pin 11. Thus, the quality of the long-term reliability can be determined based on the peeling mode and the load value at the time of peeling. Further, as the epoxy adhesive 10, an epoxy adhesive having an adhesive force of at least a certain value is required, and the adhesive force is 700kgf/cm2The above epoxy adhesive is suitable. In the present invention, the peel mode of the student pull test and the load at the time of peeling were set so that the adhesive strength of the accessory used as the student pull test machine was 700kgf/cm2The epoxy adhesive test above.
After the Stud pin was fixed, the Stud pin was pulled in a direction perpendicular to the main surface of the evaluation substrate using a Stud pull tester, and the load value (kgf/cm) at the time when the cured product layer was peeled off was observed2) And a peel mode. The speed of the pulling load was 2 kgf/sec. Thus, the quality of the long-term reliability can be determined based on the peeling mode and the load value at the time of peeling.
In the present invention, it was found that the above described student pull test conditions showed that the test was carried out 5 times<Criterion for determining peeling mode>In the peeling mode I or the peeling mode III, and the load value at the time of peeling is 180kgf/cm2The above resin composition can realize an insulating material having good long-term reliability while maintaining the effect of suppressing warpage obtained by blending a stress relaxation material.
The peeling mode is explained with reference to fig. 2. The "peeling mode I" is a case where the interface of the copper clad laminated sheet-cured product layer is separated (interlayer peeling) 3 or more times when the test is performed 5 times under the above described studpull test conditions (left side of fig. 2). The "peeling mode II" is a case where the solidified layer is cohesively broken (intralayer peeling) 3 or more times (in the middle of fig. 2), and the "peeling mode III" is a case where the solidified layer-stud interface is peeled (interlayer peeling) 3 or more times (right side of fig. 2).
The delamination at the interface between the copper-clad laminate and the cured product layer (interlayer delamination) means that, except for the case of delamination at the interface between the copper-clad laminate and the cured product layer, when the surface of the copper foil of the copper-clad laminate has irregularities (and when the interface between the copper-clad laminate and the cured product layer is not a straight line (flat surface)), the center line of the irregularities (when the sum of the areas of the valley portions downward from the center line is S1 and the sum of the areas of the mountain portions upward from the center line is S2, the approximate straight line of S1= S2) is used as the reference position of the "surface of the copper-clad laminate", it was determined that peeling (interlayer peeling) occurred at the interface between the copper clad laminate and the cured product layer when a component originating from the cured product layer did not similarly remain at a position distant from a parallel line 4 μm from the center line on the cured product layer side (upper side in fig. 2). This was observed from the screw pin side of the evaluation substrate after the fracture ・ had been peeled off, and if the copper foil of the copper-clad laminate was observed, it was judged that peeling occurred at the interface between the copper-clad laminate and the cured product layer.
The interfacial separation (interlayer separation) between the cured product layer and the stud pin means that the epoxy adhesive is broken by cohesion (intralayer separation) in addition to the interfacial separation between the cured product layer and the epoxy adhesive. The peeling at the interface between the cured product layer and the epoxy adhesive (interlayer peeling) may be determined in the same manner as the peeling at the interface between the copper clad laminate and the cured product layer.
For example, when the copper clad laminate-cured product layer interface was peeled 4 times and the cured product layer aggregation was broken 1 time in a test performed 5 times, the test was judged as "peeling mode I". When the test was performed 5 times, the interface between the copper clad laminate and the cured product layer was peeled 2 times and the cured product layer was broken by cohesion 3 times, the test was judged as "peeling mode II". When the test was performed 5 times, the copper clad laminate was peeled off 2 times from the interface of the cured product layer and was peeled off 3 times from the interface of the cured product layer and the stud pin, and the test was judged to be "peeling mode III". When the peeling mode could not be determined such that the copper clad laminate was peeled 2 times from the cured material layer interface, the cured material layer was broken by cohesion 1 time, and the cured material layer-stud pin interface was peeled 2 times, the test was conducted again by replacing the epoxy adhesive with a higher adhesive strength so that the cured material layer-stud pin interface did not peel. The peeling mode was determined based on the number of times of peeling at the interface between the copper-clad laminated sheet and the cured material layer and the number of times of cohesive failure of the cured material layer.
The average value of 5 tests was 180kgf/cm for the load value at the time of peeling2In view of realizing an insulating material having more excellent long-term reliability, the average value of 5 tests is preferably 190kgf/cm2Above, more preferably 200kgf/cm2The above.
The composition of the resin composition of the present invention will be described below. Here, the presence or absence of the influence of each component constituting the resin composition on the long-term reliability differs in the degree thereof, and the degree of influence on the long-term reliability is increased or decreased depending on the combination of the components, as described above. Hereinafter, preferred examples of the kind and content of each component may be shown, but the preferred kind and preferred content range vary depending on the combination of the components. As described above<Stud pull test conditions>When the test was conducted 5 times, the test showed peeling mode I or peeling mode III, and the load value at the time of peeling was 180kgf/cm2The types (combinations) and contents of the components constituting the resin composition are not limited to the specific types and ranges shown below.
The resin composition of the present invention contains (A) an epoxy resin and (B) a stress relaxation material.
- (A) epoxy resin-
The resin composition of the present invention contains an epoxy resin as the component (a). Examples of the epoxy resin include a bisphenol type epoxy resin, a dicyclopentadiene type epoxy resin, a triphenol type epoxy resin, a naphthol novolac type (ナフトールノボラック type) epoxy resin, a phenol novolac type (フェノールノボラック 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 (クレゾールノボラック type) epoxy resin, a biphenyl type epoxy resin, a linear aliphatic epoxy resin, an epoxy resin having a butadiene structure, an alicyclic epoxy resin, a heterocyclic epoxy resin, a spiro ring-containing epoxy resin, a cyclohexane type epoxy resin, a cyclohexane dimethanol type epoxy resin, a naphthylene ether (ナフチレンエーテル) type epoxy resin, a naphthalene group-containing epoxy resin, a phenol novolac type epoxy resin, a naphthol type (ナフチレンエーテル), a naphthol type epoxy resin, a naphthol compound, a, Trihydroxymethyl epoxy resin and tetraphenylethane epoxy resin. The bisphenol epoxy resin is an epoxy resin having a bisphenol structure, and examples thereof include bisphenol a epoxy resin, bisphenol F epoxy resin, bisphenol S epoxy resin, and bisphenol AF epoxy resin. The biphenyl type epoxy resin means an epoxy resin having a biphenyl structure, and here, the biphenyl structure may have a substituent such as an alkyl group, an alkoxy group, an aryl group, or the like. Accordingly, a bixylenol type epoxy resin, a biphenyl aralkyl type epoxy resin are also included in the biphenyl type epoxy resin. (A) The component (A) may be used alone in 1 kind, or may be used in combination of 2 or more kinds.
The component (a) is preferably an aromatic epoxy resin. The aromatic epoxy resin is an epoxy resin having an aromatic ring in the molecule. The aromatic ring includes not only a monocyclic structure such as a benzene ring but also a polycyclic aromatic structure such as a naphthalene ring and an aromatic heterocyclic structure.
(A) The component (C) preferably has 2 or more epoxy groups in 1 molecule. The proportion of the epoxy resin having 2 or more epoxy groups in 1 molecule is preferably 50% by mass or more, more preferably 60% by mass or more, and further preferably 70% by mass or more, with the nonvolatile component of the component (a) being 100% by mass.
The epoxy resin includes an epoxy resin that is liquid at a temperature of 20 ℃ (hereinafter referred to as "liquid epoxy resin") and an epoxy resin that is solid at a temperature of 20 ℃ (hereinafter referred to as "solid epoxy resin").
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 such as alicyclic epoxy resin having an ester skeleton, cyclohexane type epoxy resin, cyclohexane dimethanol type epoxy resin, and epoxy resin having a butadiene structure are preferable.
Specific examples of the liquid epoxy resin include "HP-4032", "HP-4032D" and "HP-4032 SS" (naphthalene type epoxy resin) manufactured by DIC; "828 US", "jER 828 EL", "825", "エピコート 828 EL" (bisphenol a type epoxy resin) manufactured by mitsubishi ケミカル; "jER 807" and "1750" (bisphenol F type epoxy resin) manufactured by Mitsubishi ケミカル; "jER 152" (phenol novolac type epoxy resin) manufactured by mitsubishi ケミカル corporation; "630" and "630 LSD" (glycidyl amine type epoxy resins) manufactured by mitsubishi ケミカル 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 ナガセケムテックス Co; "セロキサイト゛ 2021P" (alicyclic epoxy resin having an ester skeleton) manufactured by ダイセル; "PB-3600" (epoxy resin having a butadiene structure) manufactured by ダイセル Co; "ZX 1658" and "ZX 1658 GS" (liquid 1, 4-glycidylcyclohexane-type epoxy resins) manufactured by Nippon iron and Japan chemical Co., Ltd.
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 xylylene phenol type epoxy resin, a naphthalene type 4-functional epoxy resin, a cresol novolak type epoxy resin, a dicyclopentadiene type epoxy resin, a triphenol 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 4-functional epoxy resin) 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 HH", "HP-7200H" and "HP-7200" (dicyclopentadiene type epoxy resin) 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 (triphenol 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 ケミカル & マテリアル; ESN485 (naphthol novolac type epoxy resin) manufactured by Nippon iron ケミカル & マテリアル; "YX 4000H", "YX 4000" and "YL 6121" (biphenyl type epoxy resin) manufactured by Mitsubishi ケミカル; "YX 4000 HK" (bixylenol-type epoxy resin) manufactured by Mitsubishi ケミカル Co., Ltd.; "YX 8800" (anthracene-based epoxy resin) manufactured by Mitsubishi ケミカル; PG-100 and CG-500 manufactured by Osaka ガ ス ケミカル company; "YL 7760" (bisphenol AF type epoxy resin) manufactured by Mitsubishi ケミカル; "YL 7800" (fluorene-based epoxy resin) manufactured by Mitsubishi ケミカル; "jER 1010" (solid bisphenol a epoxy resin) manufactured by mitsubishi ケミカル; "jER 1031S" (tetraphenylethane-type epoxy resin) manufactured by Mitsubishi ケミカル, Inc.
The resin composition of the present invention may contain only a liquid epoxy resin as the component (a), may contain only a solid epoxy resin, or may contain a combination of a liquid epoxy resin and a solid epoxy resin. When the liquid epoxy resin and the solid epoxy resin are used in combination, the amount ratio thereof (liquid epoxy resin: solid epoxy resin) is preferably 1:0.01 to 1:20, more preferably 1:0.05 to 1:10, and particularly preferably 1:0.1 to 1:1 in terms of mass ratio.
(A) The epoxy equivalent of the component is preferably 50g/eq to 5000g/eq, more preferably 50g/eq to 3000g/eq, further preferably 80g/eq to 2000g/eq, and further more preferably 110g/eq to 1000g/eq. The epoxy equivalent is the mass of an epoxy resin containing 1 equivalent of an epoxy group. The epoxy equivalent can be measured according to JIS K7236.
(A) The weight average molecular weight (Mw) of the component (B) is preferably 100 to 5000, more preferably 250 to 3000, and still more preferably 400 to 1500. The Mw of the epoxy resin can be determined by Gel Permeation Chromatography (GPC) using polystyrene as a standard.
The content of the component (a) in the resin composition is preferably 0.1% by mass or more, more preferably 0.3% by mass or more, further preferably 0.5% by mass or more, 1% by mass or more, 1.5% by mass or more, or 2% by mass or more, preferably 40% by mass or less, more preferably 35% by mass or less, 30% by mass or less, 25% by mass or less, or 20% by mass or less, based on 100% by mass of the total of nonvolatile components in the resin composition.
- (B) stress relaxation material-
The resin composition of the present invention contains a stress relaxation material as the component (B). By containing the component (B), an insulating material capable of suppressing warpage can be realized.
The component (B) is preferably a resin having 1 or more structures selected from a polybutadiene structure, a polysiloxane structure, a poly (meth) acrylate structure, a polyalkylene oxide structure, a polyisoprene structure, a polyisobutylene structure, and a polycarbonate structure in a molecule, and more preferably a resin having 1 or 2 or more structures selected from a polybutadiene structure, a poly (meth) acrylate structure, a polyalkylene oxide structure, a polyisoprene structure, a polyisobutylene structure, and a polycarbonate structure. It is noted that "(meth) acrylate" is a term encompassing both methacrylate and acrylate. These structures may be contained in the main chain or in the side chain.
(B) The component (c) is preferably a high molecular weight component in view of realizing an insulating material capable of suppressing warpage. (B) The number average molecular weight (Mn) of the component (a) is preferably 1,000 or more, more preferably 1,500 or more, and further preferably 2,000 or more, 2,500 or more, 3,000 or more, 4,000 or more, or 5,000 or more. The upper limit of Mn is preferably 1,000,000 or less, more preferably 900,000 or less, 800,000 or less, or 700,000 or less. The number average molecular weight (Mn) can be determined as a polystyrene equivalent by a Gel Permeation Chromatography (GPC) method.
(B) The component (c) is preferably 1 or more selected from the group consisting of a resin having a glass transition temperature (Tg) of 25 ℃ or less and a resin that is liquid at 25 ℃ from the viewpoint of realizing an insulating material capable of suppressing warpage. Here, a resin having a plurality of tgs is a "resin having a Tg of 25 ℃ or less" if the lowest Tg is 25 ℃ or less.
The Tg of the resin is preferably 20 ℃ or less, more preferably 15 ℃ or less. The lower limit of Tg is not particularly limited, and may be usually-50 ℃ or higher. The resin that is liquid at 25 ℃ is preferably liquid at 20 ℃ or lower, and more preferably liquid at 15 ℃ or lower.
(B) The component (c) preferably has a functional group capable of reacting with the component (a) and the like, from the viewpoint of reacting with the component (a) and the like to obtain an insulating material having high cohesive force (in-layer adhesion strength). Note that the functional group capable of reacting with the component (a) or the like includes a functional group which appears by heating.
In a preferred embodiment, the functional group capable of reacting with the component (a) or the like is 1 or more functional groups selected from a hydroxyl group, a carboxyl group, an acid anhydride group, a phenolic hydroxyl group, an epoxy group, an isocyanate group and a urethane group. Among these, the functional group is preferably a hydroxyl group, an acid anhydride group, a phenolic hydroxyl group, an epoxy group, an isocyanate group, and a urethane group, and more preferably a hydroxyl group, an acid anhydride group, a phenolic hydroxyl group, and an epoxy group. Among them, when the functional group contains an epoxy group, the number average molecular weight (Mn) is preferably 5,000 or more.
In a preferred embodiment, the component (B) contains a resin having a polybutadiene structure (hereinafter also referred to as "polybutadiene resin"). It is noted that the polybutadiene structure may be partially or fully hydrogenated.
Specific examples of the polybutadiene resin include "Ricon 130MA 8", "Ricon 130MA 13", "Ricon 130MA 20", "Ricon 131MA 5", "Ricon 131MA 10", "Ricon 131MA 17", "Ricon 131MA 20", "Ricon 184MA 6" (acid anhydride group-containing polybutadiene), JP-100 "," JP-200 "(epoxidized polybutadiene), GQ-1000" (hydroxyl group-and carboxyl group-introduced polybutadiene), G-1000 "," G-2000 "," G-3000 "(both-terminal hydroxyl group-containing polybutadiene), GI-1000", "GI-2000", "GI-3000" (both-terminal hydroxyl group-containing polybutadiene), PB3600 "," PB4700 "(polybutadiene skeleton epoxy resin), エポフレンド A1005", "and" PCA "manufactured by クレイバレー, "エポフレンド A1010", "エポフレンド A1020" (epoxide of block copolymer of styrene, butadiene and styrene), "FCA-061L" (hydrogenated polybutadiene skeleton epoxy resin) and "R-45 EPT" (polybutadiene skeleton epoxy resin) manufactured by ナガセケムテックス. Examples of the polybutadiene resin include a linear polymer (polymers described in jp 2006-a-37083 and international publication No. 2008/153208) using hydroxyl-terminated polybutadiene, a diisocyanate compound, and a tetrabasic acid anhydride as raw materials, and butadiene containing a phenolic hydroxyl group. The butadiene structure content of the polymer is preferably 50% by mass or more, and more preferably 60% by mass to 95% by mass. The details of the polymer can be found in Japanese patent application laid-open No. 2006-37083 and International publication No. 2008/153208, which are incorporated herein by reference.
In a preferred embodiment, the component (B) contains a resin having a poly (meth) acrylate structure (hereinafter also referred to as "poly (meth) acrylate resin"). Specific examples of the poly (meth) acrylate resin include テイサンレジン "SG-70L", "SG-708-6", "WS-023", "SG-700 AS", "SG-280 TEA" (carboxyl group-containing acrylate copolymer resin, acid value 5 to 34mgKOH/g, weight average molecular weight 40 to 90 ten thousand, Tg-30 to 5 ℃ C.), "SG-80H", "SG-80H-3", "SG-P3" (epoxy group-containing acrylate copolymer resin, epoxy equivalent 4761 to 14285g/eq, weight average molecular weight 35 to 85 ten thousand, Tg11 to 12 ℃ C.), "SG-600 TEA", "SG-790" (hydroxyl group-containing acrylate copolymer resin, hydroxyl value 20 to 40mgKOH/g, weight average molecular weight 50 to 120 ten thousand, etc.), Tg-37 to-32 ℃ C.), ME-2000, W-116.3 (carboxyl group-containing acrylate copolymer resin), W-197C (hydroxyl group-containing acrylate copolymer resin), KG-25, KG-3000 (epoxy group-containing acrylate copolymer resin) manufactured by Kokai industries, Ltd.
In a preferred embodiment, the component (B) contains a resin having a polycarbonate structure (hereinafter also referred to as "polycarbonate resin"). Specific examples of the polycarbonate resin include "T6002" and "T6001" (polycarbonate diol) manufactured by Asahi Kasei ケミカル ズ Co., Ltd, "C-1090", "C-2090" and "C-3090" (polycarbonate diol) manufactured by クラレ Co., Ltd. Further, linear polyimide using a hydroxyl-terminated polycarbonate, a diisocyanate compound and a tetrabasic acid anhydride as raw materials can be used. The content of the carbonate structure in the polyimide resin is preferably 50 mass% or more, and more preferably 60 to 95 mass%. The details of the polyimide resin can be found in International publication No. 2016/129541, which is incorporated herein by reference.
In a preferred embodiment, the component (B) contains a resin containing a polysiloxane structure (hereinafter also referred to as "polysiloxane resin"). Specific examples of the silicone resin include "SMP-2006", "SMP-2003 PGMEA", "SMP-5005 PGMEA", and linear polyimides produced from an amino-terminated polysiloxane and a tetrabasic acid anhydride (International publication No. 2010/053185, Japanese patent application laid-open Nos. 2002-12667 and 2000-319386), which are manufactured by shin-Etsu シリコーン, for example.
In a preferred embodiment, the component (B) contains a resin containing a polyalkylene structure and a polyalkylene oxide structure (hereinafter referred to as "polyalkylene resin" and "polyalkylene oxide resin", respectively). Specific examples of the polyalkylene resin and the polyalkylene oxide resin include "PTXG-1000" and "PTXG-1800" manufactured by Asahi Kasei せ Ph い Co.
In a preferred embodiment, the component (B) contains a resin having a polyisoprene structure (hereinafter also referred to as "polyisoprene resin"). Specific examples of the polyisoprene resin include "KL-610" and "KL 613" manufactured by クラレ.
In a preferred embodiment, the component (B) contains a resin having a polyisobutylene structure (hereinafter also referred to as "polyisobutylene resin"). Specific examples of the polyisobutylene resin include "SIBSTAR-073T" (styrene-isobutylene-styrene triblock copolymer) and "SIBSTAR-042D" (styrene-isobutylene diblock copolymer) manufactured by カネカ.
In another preferred embodiment, the component (B) contains an organic filler. As the organic filler, an organic filler containing a rubber component is widely used. Examples of the rubber component contained in the organic filler include silicone elastomers such as polydimethylsiloxane; olefinic 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; and thermoplastic elastomers such as acrylic thermoplastic elastomers such as polypropylene (meth) acrylate, polybutylene (meth) acrylate, polycyclohexyl (meth) acrylate, and octyl (meth) acrylate. Further, a silicone rubber such as polyorganosiloxane rubber may be mixed in the rubber component. The Tg 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.
In one embodiment, the organic filler material is a core-shell rubber particle comprising: a core particle containing the above-exemplified rubber component, and a shell portion graft-copolymerized with a monomer component copolymerizable with the rubber component contained in the core particle. Here, the core-shell type is not limited to a particle in which the core particle and the shell are clearly distinguishable from each other, and includes a particle 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.
Specific examples of the organic filler containing a rubber component include "CHT" manufactured by チェイルインダストリーズ; "B602" manufactured by UMGABS corporation; "パラロイド EXL-2602", "パラロイド EXL-2603", "パラロイド EXL-2655", "パラロイド EXL-2311", "パラロイド -EXL 2313", "パラロイド EXL-2315", "パラロイド KM-330", "パラロイド KM-336P", "パラロイド KCZ-201", "メタブレン C-223A", "メタブレン E-901", "メタブレン S-2001", "メタブレン W-450A", "メタブレン SRK-200" manufactured by Mitsubishi レイヨン, and "カネエース M-511", "カネエース M-600", "カネエース M-400", "カネエース M-580" manufactured by カネカ, manufactured by Wuyu chemical industries, Ltd, "カネエース MR-01", "スタフィロイド AC 3355", "スタフィロイド AC 3816", "スタフィロイド AC 3832", "スタフィロイド AC 4030" and "スタフィロイド AC 3364" manufactured by アイカ industries, Inc. These are core-shell type rubber particles.
The content of the component (B) in the resin composition is preferably 0.5% by mass or more, more preferably 1% by mass or more, further preferably 3% by mass or more, and further preferably 4% by mass or more, or 5% by mass or more, based on 100% by mass of the total nonvolatile components in the resin composition, from the viewpoint of realizing an insulating material capable of suppressing warpage. The upper limit of the content is preferably 30% by mass or less, more preferably 25% by mass or less, 20% by mass or less, or 15% by mass or less.
The content of the component (B) in the resin composition is preferably 0.5% by mass or more, more preferably 1% by mass or more, further preferably 3% by mass or more, further preferably 5% by mass or more, 8% by mass or more, 10% by mass or more, 15% by mass or more, 20% by mass or more, 25% by mass or more, or 30% by mass or more, based on 100% by mass of the total resin components in the resin composition. The upper limit of the content is preferably 70% by mass or less, more preferably 60% by mass or less, 55% by mass or less, or 50% by mass or less. In the present invention, the "resin component" refers to a component obtained by removing the inorganic filler (C) described later from the components constituting the resin composition.
The content of the component (B) in the resin composition is preferably 0.1 or more, more preferably 0.2 or more, 0.3 or more, 0.4 or more, 0.5 or more, 0.6 or more, 0.8 or more, or 1 or more in terms of the mass ratio of the component (B) to the total of the component (a) and the curing agent (D) described later, that is, the component (B)/[ (a) component + (D) component ]. The upper limit of the mass ratio is preferably 3 or less, more preferably 2.5 or less, 2 or less, 1.8 or less, 1.6 or less, or 1.5 or less.
As described above, the present inventors have found that if a stress relaxation material is added to an insulating material in order to suppress warpage, physical properties directly related to reliability and the like, such as mechanical strength and adhesion strength to a conductor, of the obtained insulating material decrease with time, and long-term reliability is impaired. According to the above<Stud pull test conditions>The test pieces showed a peeling mode I or a peeling mode III in 5 times of tests, and the load value at the time of peeling was 180kgf/cm2The resin composition of the present invention described above can suppress the deterioration (deterioration) of physical properties with time even when the resin composition contains a certain amount or more of the stress relaxation material as described above. Thus, the resin composition of the present invention can realize an insulating material having good long-term reliability while maintaining the effect of suppressing warpage obtained by blending a stress relaxation material.
The resin composition of the present invention may further contain 1 or more selected from (C) an inorganic filler, (D) a curing agent, (E) a maleimide compound, and (F) a curing accelerator.
- (C) inorganic filling materials-
The resin composition of the present invention may contain an inorganic filler as the component (C). By containing the component (C), an insulating material having excellent thermal characteristics can be realized.
Examples of the material of the component (C) 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. Of these, silica is particularly preferable. Examples of the silica include amorphous silica, fused silica, crystalline silica, synthetic silica, and hollow silica. In addition, as the silica, spherical silica is preferable. (C) The component (A) may be used alone in 1 kind, or may be used in combination of 2 or more kinds.
As commercially available products of the component (C), there are exemplified "UFP-30" manufactured by electrochemical chemical industries, Inc.; "SP 60-05" and "SP 507-05" manufactured by Nippon iron ケミカル & マテリアル, Inc.; "YC 100C", "YA 050C", "YA 050C-MJE", "YA 010C" manufactured by アドマテックス; デンカ entitled "UFP-30"; トクヤマ, "シルフィル NSS-3N", "シルフィル NSS-4N" and "シルフィル NSS-5N"; アドマテックス, "SC 2500 SQ", "SO-C4", "SO-C2", "SO-C1"; デンカ, "DAW-03", "FB-105 FD", and the like.
(C) The average particle diameter of the component (A) is not particularly limited, but is preferably 10 μm or less, more preferably 5 μm or less, further preferably 3 μm or less, 2 μm or less, 1 μm or less, or 0.7 μm or less. The lower limit of the average particle size is not particularly limited, but is preferably 0.01 μm or more, more preferably 0.05 μm or more, and still more preferably 0.07 μm or more, 0.1 μm or more, or 0.2 μm or more. (C) The average particle diameter of the component can be measured by a laser diffraction ・ scattering method based on the Mie scattering theory. Specifically, the particle size distribution of the inorganic filler can be prepared on a volume basis by a laser diffraction scattering particle size distribution measuring apparatus, and the median diameter thereof can be measured as an average particle size. As the measurement sample, a sample obtained by weighing 100mg of the inorganic filler and 10g of methyl ethyl ketone in a glass vial and ultrasonically dispersing them for 10 minutes can be used. The volume-based particle size distribution of the inorganic filler was measured in a flow cell system using a laser diffraction particle size distribution measuring apparatus using blue and red light sources as the light source wavelengths of the measurement sample, and the average particle size was calculated from the obtained particle size distribution as the median diameter. Examples of the laser diffraction type particle size distribution measuring apparatus include "LA-960" manufactured by horiba, Inc.
(C) The specific surface area of the component (A) is not particularly limited, but is preferably 0.1m2A value of at least g, more preferably 0.5m2A total of 1m or more, preferably 1m2More than g, 3m2More than g or 5m2More than g. The upper limit of the specific surface area is not particularly limited, but is preferably 100m2A ratio of 80m or less per gram2A ratio of 60m or less per gram2Less than 50 m/g2Less than or equal to 40 m/g2The ratio of the carbon atoms to the carbon atoms is less than g. (C) The specific surface area of the component was obtained by adsorbing nitrogen gas on the surface of a sample by the BET method using a specific surface area measuring apparatus (Macsorb HM-1210, manufactured by マウンテック Co., Ltd.) and calculating the specific surface area by the BET multipoint method.
(C) The component (C) is preferably surface-treated with an appropriate surface-treating agent. By performing the surface treatment, the moisture resistance and dispersibility of the component (C) can be improved. Examples of the surface treatment agent include silane coupling agents such as vinyl silane coupling agents, epoxy silane coupling agents, styrene silane coupling agents, (meth) acrylic silane coupling agents, amino silane coupling agents, isocyanurate silane coupling agents, ureido silane coupling agents, mercapto silane coupling agents, isocyanate silane coupling agents, and acid anhydride silane coupling agents; alkoxysilane compounds other than silane coupling agents such as methyltrimethoxysilane and phenyltrimethoxysilane; silazane compounds, and the like. The surface treatment agent can be used alone in 1 kind, also can be used in 2 or more kinds combination.
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) available from shin-Etsu chemical Co., Ltd.,.
The degree of the surface treatment with the surface treatment agent is preferably within a predetermined range from the viewpoint of improving the dispersibility of the inorganic filler. Specifically, the inorganic filler is preferably surface-treated with 0.2 to 5 mass% of a surface treating agent per 100 mass%.
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. The carbon content per unit surface area of the inorganic filler is preferably 0.02mg/m from the viewpoint of improving the dispersibility of the inorganic filler2Above, more preferably 0.1mg/m2Above, more preferably 0.2mg/m2The above. On the other hand, from the viewpoint of preventing the melt viscosity of the resin composition and the increase in melt viscosity in the form of a sheet, it is preferably 1.0mg/m2The concentration is more preferably 0.8mg/m or less2The concentration is more preferably 0.5mg/m or less2The following. (C) The amount of carbon per unit surface area of the component (a) can be measured after the inorganic filler after the surface treatment is washed with a solvent such as Methyl Ethyl Ketone (MEK). Specifically, a sufficient amount of MEK as a solvent was added to the inorganic filler surface-treated with the surface treatment agent, and ultrasonic washing was performed at 25 ℃ for 5 minutes. After removing the supernatant liquid and drying the solid component, the amount of carbon per surface area of the inorganic filler can be measured using a carbon analyzer. As the carbon analyzer, "EMIA-320V" manufactured by horiba, Ltd.
When the resin composition of the present invention contains the component (C), the content of the component (C) in the resin composition is preferably 30% by mass or more, more preferably 40% by mass or more, and further preferably 45% by mass or more, 50% by mass or more, 55% by mass or more, 60% by mass or more, or 65% by mass or more, based on 100% by mass of the total nonvolatile components in the resin composition, from the viewpoint of achieving an insulating material having good thermal characteristics such as a low linear thermal expansion coefficient. (C) The upper limit of the content of the component (b) is not particularly limited, but is preferably 85 mass% or less, more preferably 80 mass% or less or 75 mass% or less.
- (D) curing agent-
The resin composition of the present invention may contain a curing agent as the component (D). (D) The component (A) generally has a function of curing the resin composition by reacting with the component (A).
Examples of the component (D) include an active ester-based curing agent, a phenol-based curing agent, a naphthol-based curing agent, an acid anhydride-based curing agent, a cyanate-based curing agent, a carbodiimide-based curing agent, and an amine-based curing agent, and among them, it is preferable to contain an active ester-based curing agent, a phenol-based curing agent, and a naphthol-based curing agent from the viewpoint of easily adjusting the above-described peeling mode and the load value at the time of peeling to be within the range of the appropriate mode ・. (D) The component (A) may be used alone in 1 kind, or may be used in combination of 2 or more kinds.
As the active ester-based curing agent, a compound having 1 or more active ester groups in 1 molecule can be used. Among them, as the active ester curing agent, preferred are compounds having 2 or more ester groups having high reactivity in 1 molecule, such as phenol esters, thiophenol esters, N-hydroxylamine esters, and esters of heterocyclic hydroxy compounds. The active ester-based curing agent is preferably obtained by a condensation reaction of a carboxylic acid compound and/or a thiocarboxylic acid compound with a hydroxyl compound and/or a thiol compound. In particular, from the viewpoint of improving heat resistance, an active ester-based curing agent obtained from a carboxylic acid compound and a hydroxyl compound is preferable, and an active ester-based curing agent obtained from a carboxylic acid compound and a phenol compound and/or a naphthol compound is more preferable.
Examples of the carboxylic acid compound include benzoic acid, acetic acid, succinic acid, maleic acid, itaconic acid, phthalic acid, isophthalic acid, terephthalic acid, and pyromellitic acid.
Examples of the phenol compound or naphthol compound include hydroquinone, resorcinol, bisphenol a, bisphenol F, bisphenol S, phenolphthalin, methylated bisphenol a, methylated bisphenol F, methylated bisphenol S, phenol, o-cresol, m-cresol, p-cresol, catechol, α -naphthol, β -naphthol, 1, 5-dihydroxynaphthalene, 1, 6-dihydroxynaphthalene, 2, 6-dihydroxynaphthalene, dihydroxybenzophenone, trihydroxybenzophenone, tetrahydroxybenzophenone, phloroglucinol, benzenetriol, dicyclopentadiene type diphenol compound, phenol novolak and the like. Here, the "dicyclopentadiene type diphenol compound" refers to a diphenol compound obtained by condensing dicyclopentadiene 1 molecules with phenol 2 molecules.
Preferred specific examples of the active ester-based curing agent include an active ester-based curing agent containing a dicyclopentadiene type diphenol structure, an active ester-based curing agent containing a naphthalene structure, an active ester-based curing agent containing an acetylate of phenol novolak, and an active ester-based curing agent containing a benzoylate of phenol novolak. Among them, active ester-based curing agents having a naphthalene structure and active ester-based curing agents having a dicyclopentadiene type diphenol structure are more preferable. The "dicyclopentadiene type diphenol structure" means a 2-valent structural unit formed from phenylene-dicyclopentyl (ジシクロペンチレン) -phenylene.
As commercially available products of active ester compounds, examples of the active ester compounds having a dicyclopentadiene type diphenol structure include "EXB 9451", "EXB 9460S", "EXB-8000L-65M", "EXB-8000L-65 TM", "HPC-8000-65T", "HPC-8000H-65 TM", and DIC (manufactured by DIC); examples of the active ester compound having a naphthalene structure include "EXB-8100L-65T", "EXB-8150-60T", "EXB-8150-62T", "EXB-9416-70 BK", "HPC-8150-60T" and "HPC-8150-62T" (manufactured by DIC); examples of the phosphorus-containing active ester compound include "EXB 9401" (manufactured by DIC corporation), active ester compounds as acetylates of phenol novolacs, such as "DC 808" (manufactured by mitsubishi ケミカル), active ester compounds as benzoylates of phenol novolacs, such as "yllh 1026", "yllh 1030", "yllh 1048" (manufactured by mitsubishi ケミカル), active ester compounds containing styryl and naphthalene structures, such as "PC 1300-02-65 MA" (manufactured by エア; ウォーター).
As the phenol-based curing agent and the naphthol-based curing agent, curing agents having a novolac structure are preferable from the viewpoint of heat resistance and water resistance. In addition, from the viewpoint of adhesion to the conductor layer, a nitrogen-containing phenol curing agent and a nitrogen-containing naphthol curing agent are preferable, and a triazine skeleton-containing phenol curing agent and a triazine skeleton-containing naphthol curing agent are more preferable.
Specific examples of the phenol-based curing agent and the naphthol-based curing agent include "MEH-7700", "MEH-7810", "MEH-7851", "MEH-8000H" manufactured by Minghu Kagaku K.K.; "NHN", "CBN" and "GPH" manufactured by Nippon chemical Co., Ltd.; "SN-170", "SN-180", "SN-190", "SN-475", "SN-485", "SN-495V", "SN-375", "SN-395", manufactured by Nissan ケミカル & マテリアル; "TD-2090", "TD-2090-60M", "LA-7052", "LA-7054", "LA-1356", "LA-3018-50P", "EXB-9500", "HPC-9500", "KA-1160", "KA-1163", "KA-1165", manufactured by DIC; GDP-6115L, GDP-6115H, ELPC75, etc., manufactured by Rongche chemical Co.
Examples of the acid anhydride curing agent include a curing agent having 1 or more acid anhydride groups in the 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, diphenyl ether 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), styrene ・ maleic acid resin obtained by copolymerizing styrene with maleic acid, and other polymer-type acid anhydrides. As a commercially available product of the acid anhydride-based curing agent, "MH-700", manufactured by Nissian chemical and physical Co., Ltd.
Examples of the cyanate ester curing agent include 2-functional cyanate ester resins such as bisphenol a dicyanate, polyphenol cyanate ester, oligo (3-methylene-1, 5-phenylene cyanate ester), 4 '-methylenebis (2, 6-dimethylphenylcyanate), 4' -ethylidene diphenyl dicyanate, hexafluorobisphenol a dicyanate, 2-bis (4-cyanato) phenylpropane, 1-bis (4-cyanatophenylmethane), bis (4-cyanato-3, 5-dimethylphenyl) methane, 1, 3-bis (4-cyanatophenyl-1- (methylethylidene)) benzene, bis (4-cyanatophenyl) sulfide, and bis (4-cyanatophenyl) ether; polyfunctional cyanate ester resins derived from phenol novolak, cresol novolak and the like; prepolymers in which a part of these cyanate ester resins is triazinated, and the like. Specific examples of the cyanate ester-based curing agent include "PT 30" and "PT 60" (phenol novolac-type polyfunctional cyanate ester resin), "ULL-950S" (polyfunctional cyanate ester resin), "BA 230" and "BA 230S 75" (prepolymer in which a part or all of bisphenol a dicyanate ester is triazinized to form a trimer), which are manufactured by ロンザジャパン co.
Specific examples of the carbodiimide-based curing agent include カルボジライト (registered trademark) V-03 (carbodiimide group equivalent: 216g/eq.), V-05 (carbodiimide group equivalent: 262g/eq.), and V-07 (carbodiimide group equivalent: 200g/eq.), manufactured by Nisshinbo ケミカル; v-09 (carbodiimide equivalent: 200 g/eq.); スタバクゾール (registered trademark) P (carbodiimide group equivalent: 302g/eq.) manufactured by ラインケミー Co.
The amine-based curing agent includes a curing agent having 1 or more amino groups in the molecule, and examples thereof include aliphatic amines, polyether amines, alicyclic amines, aromatic amines, and the like, and among them, aromatic amines are preferable from the viewpoint of exerting the desired effect of the present invention. The amine-based curing agent is preferably a primary amine or a secondary amine, and more preferably a primary amine. Specific examples of the amine-based curing agent include 4,4 '-methylenebis (2, 6-dimethylaniline), diphenyldiaminosulfone, 4' -diaminodiphenylmethane, 4 '-diaminodiphenylsulfone, 3' -diaminodiphenylsulfone, m-phenylenediamine, m-xylylenediamine, diethyltoluenediamine, 4 '-diaminodiphenyl ether, 3' -dimethyl-4, 4 '-diaminobiphenyl, 2' -dimethyl-4, 4 '-diaminobiphenyl, 3' -dihydroxybenzidine, 2-bis (3-amino-4-hydroxyphenyl) propane, 3-dimethyl-5, 5-diethyl-4, 4-diphenylmethanediamine, and, 2, 2-bis (4-aminophenyl) propane, 2-bis (4- (4-aminophenoxy) phenyl) propane, 1, 3-bis (3-aminophenoxy) benzene, 1, 3-bis (4-aminophenoxy) benzene, 1, 4-bis (4-aminophenoxy) benzene, 4' -bis (4-aminophenoxy) biphenyl, bis (4- (4-aminophenoxy) phenyl) sulfone, bis (4- (3-aminophenoxy) phenyl) sulfone and the like. As the amine-based curing agent, commercially available ones can be used, and examples thereof include "KAYABOND C-200S", "KAYABOND C-100", "カヤハード A-A", "カヤハード A-B", "カヤハード A-S" manufactured by Nippon Chemicals, and "エピキュア W" manufactured by Mitsubishi ケミカル.
(A) The amount ratio of the component (D) to the component (D) is preferably in the range of 1:0.01 to 1:10, more preferably 1:0.05 to 1:5, and further preferably 1:0.1 to 1:3 in terms of the ratio of [ total number of epoxy groups of epoxy resin ]/[ total number of reactive groups of curing agent ]. The reactive group of the curing agent is an active hydroxyl group or the like, and varies depending on the kind of the curing agent. The total number of epoxy groups of the epoxy resin is a value obtained by summing all the epoxy resins by dividing the mass of the solid content of each epoxy resin by the epoxy equivalent weight, and the total number of reactive groups of the curing agent is a value obtained by summing all the curing agents by dividing the mass of the solid content of each curing agent by the equivalent weight of the reactive groups.
- (E) Maleimide Compounds-
The resin composition of the present invention may contain a maleimide compound as the component (E). By containing the component (E), it was confirmed that the above-mentioned peeling mode and the load value at the time of peeling can be more easily adjusted to the appropriate range of the mode ・.
Component (E) is preferably selected from
(E1) A maleimide compound containing an aliphatic group having 5 or more carbon atoms directly bonded to the nitrogen atom of the maleimide,
(E2) A maleimide compound having a trimethylindan skeleton, and
(E3) maleimide compounds having an aromatic ring directly bonded to the nitrogen atom of the maleimide
1 or more of them.
The term "directly" as used herein means that there is no other group between the nitrogen atom of the maleimide and the aliphatic group having 5 or more carbon atoms in the component (E1), and that there is no other group between the nitrogen atom of the maleimide and the aromatic ring in the component (E3).
(E) The component (C) is preferably a maleimide group (2, 5-dihydro-2, 5-dioxo-1H-pyrrol-1-yl group) having 2 or more maleimide groups in 1 molecule, regardless of whether it is the component (E1), the component (E2) or the component (E3).
Hereinafter, the component (E1), the component (E2), and the component (E3) are described as preferred examples of the component (E), and the term "substituent" means a halogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkyloxy group, an alkylthio group, an aryl group, an aryloxy group, an arylalkyl group, an arylalkoxy group, an arylthio group, a 1-valent heterocyclic group, an alkylidene group, an amino group, a silyl group, an acyl group, an acyloxy group, a carboxyl group, a sulfo group, a cyano group, a nitro group, a hydroxyl group, a mercapto group, and an oxo group unless otherwise specified. Examples of the halogen atom used as a substituent include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom. The alkyl group used as a substituent may be either linear or branched. The number of carbon atoms of the alkyl group is preferably 1 to 20, more preferably 1 to 14, further preferably 1 to 12, further preferably 1 to 6, and particularly preferably 1 to 3. Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an n-butyl group, and a tert-butyl group. The cycloalkyl group used as a substituent preferably has 3 to 20 carbon atoms, more preferably 3 to 12 carbon atoms, and further preferably 3 to 6 carbon atoms. Examples of the cycloalkyl group include cyclopentyl, cyclohexyl, and cycloheptyl. The alkoxy group as a substituent may be linear or branched. The alkoxy group preferably has 1 to 20 carbon atoms, more preferably 1 to 12 carbon atoms, and further preferably 1 to 6 carbon atoms. Examples of the alkoxy group include methoxy, ethoxy, propoxy, and butoxy. The number of carbon atoms of the cycloalkyloxy group as a substituent is preferably 3 to 20, more preferably 3 to 12, and still more preferablyThe selection is 3-6. Examples of the cycloalkyloxy group include a cyclopropyloxy group, a cyclobutyloxy group, a cyclopentyloxy group and a cyclohexyloxy group. The alkylthio group used as a substituent preferably has 1 to 20 carbon atoms, more preferably 1 to 14 carbon atoms, still more preferably 1 to 12 carbon atoms, yet more preferably 1 to 6 carbon atoms, and particularly preferably 1 to 3 carbon atoms. The aryl group used as a substituent is a group obtained by removing 1 hydrogen atom from an aromatic hydrocarbon. The number of carbon atoms of the aryl group used as a substituent is preferably 6 to 24, more preferably 6 to 18, further preferably 6 to 14, and further more preferably 6 to 10. Examples of the aryl group include a phenyl group, a naphthyl group and an anthracenyl group. The number of carbon atoms of the aryloxy group used as a substituent is preferably 6 to 24, more preferably 6 to 18, further preferably 6 to 14, and further more preferably 6 to 10. As the aryloxy group used as a substituent, for example, a phenoxy group, a 1-naphthoxy group and a 2-naphthoxy group are cited. The number of carbon atoms of the arylalkyl group used as the substituent is preferably 7 to 25, more preferably 7 to 19, further preferably 7 to 15, and further more preferably 7 to 11. Examples of the arylalkyl group include phenyl-C1~C12Alkyl, naphthyl-C1~C12Alkyl and anthracenyl-C1~C12An alkyl group. The arylalkoxy group used as the substituent has preferably 7 to 25 carbon atoms, more preferably 7 to 19 carbon atoms, still more preferably 7 to 15 carbon atoms, and still more preferably 7 to 11 carbon atoms. Examples of the arylalkoxy group include phenyl-C1~C12Alkoxy and naphthyl-C1~C12An alkoxy group. The number of carbon atoms of the arylthio group used as a substituent is preferably 6 to 24, more preferably 6 to 18, further preferably 6 to 14, and further more preferably 6 to 10. The 1-valent heterocyclic group used as a substituent means a group obtained by removing 1 hydrogen atom from the heterocycle of the heterocyclic compound. The number of carbon atoms of the 1-valent heterocyclic group is preferably 3 to 21, more preferably 3 to 15, and further preferably 3 to 9. The 1-valent heterocyclic group also includes a 1-valent aromatic heterocyclic group (heteroaryl group). Examples of the heterocyclic ring having a valence of 1 include thienyl, pyrrolyl, furyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, pyrrolidinyl, piperidyl, quinolyl and isoquinolyl. Alkylidene as a substituent means a radical obtained by removing 2 hydrogen atoms from the same carbon atom of an alkaneTo a group of (a). The number of carbon atoms of the alkylidene group is preferably 1 to 20, more preferably 1 to 14, further preferably 1 to 12, further more preferably 1 to 6, and particularly preferably 1 to 3. The acyl group used as a substituent means a group represented by the formula-C (= O) -R (wherein R represents an alkyl group or an aryl group). The alkyl group represented by R may be linear or branched. Examples of the aryl group represented by R include a phenyl group, a naphthyl group and an anthracenyl group. The number of carbon atoms of the acyl group is preferably 2 to 20, more preferably 2 to 13, and further preferably 2 to 7. The acyloxy group used as a substituent means a group represented by the formula-O-C (= O) -R (wherein R is an alkyl group or an aryl group). The alkyl group represented by R may be linear or branched. Examples of the aryl group represented by R include a phenyl group, a naphthyl group and an anthracenyl group, and the carbon number of the acyloxy group is preferably 2 to 20, more preferably 2 to 13, and still more preferably 2 to 7. The above-mentioned substituent may further have a substituent (hereinafter, sometimes referred to as "secondary substituent"). The secondary substituent is not particularly limited, and the same substituents as those described above can be used.
< ingredient (E1) >
(E1) The component (B) is a maleimide compound containing an aliphatic group having 5 or more carbon atoms directly bonded to the nitrogen atom of the maleimide compound. The maleimide compound can be obtained by, for example, imidizing a component containing an aliphatic amine compound (e.g., a dimer diamine compound (ダイマージアミン compound)), maleic anhydride, and, if necessary, tetracarboxylic dianhydride.
In one embodiment, the component (E1) contains a compound represented by the following formula (E1-1).
[ solution 1]
In the formula (E1-1),
A1represents an aliphatic group having 5 or more carbon atoms which may have a substituent,
L1represents a single bond or a 2-valent linking group,
nB1 represents an integer of 0 to 20. A. the1In the case of plural, they may be the same or different, L1When there are plural, they may be the same or different.
A1The aliphatic group represented by (a) has 5 or more carbon atoms, preferably 10 or more, 15 or more, or 20 or more. The upper limit of the number of carbon atoms is not particularly limited, and may be, for example, 100 or less, 80 or less, 60 or less, or 50 or less. Note that the number of carbon atoms does not include the number of carbon atoms of the substituent.
In one embodiment, A1Is a 2-valent group represented by the following formula (E1-2).
[ solution 2]
In the formula (E1-2),
A11represents a single bond, an alkylene group or an alkenylene group (preferably an alkylene group or an alkenylene group),
ring Z1Represents a non-aromatic ring which may have a group selected from an alkyl group and an alkenyl group (preferably a cycloalkane ring or cycloalkene ring which may have a group selected from an alkyl group and an alkenyl group),
nB11 represents an integer of 0 to 3 (preferably 0 or 1, more preferably 1),
denotes the bonding site. A. the11Ring Z1Each independently may have a substituent. A. the11In the case of plural, they may be the same or different, ring Z1When there are a plurality of them, they may be the same or different.
As L1The 2-valent linking group represented by (a) includes a 2-valent organic group (preferably an organic group containing a 2-valent ring (for example, an aromatic ring or a non-aromatic ring)) containing at least 2 (for example, 2 to 3000, 2 to 1000, 2 to 100, 2 to 50) skeleton atoms selected from a carbon atom, an oxygen atom, a nitrogen atom and a sulfur atom, and among them, a 2-valent group represented by the following formula (E1-3) is preferred.
[ solution 3]
In the formula (E1-3),
A12represents a single bond or a 2-valent group containing 1 or more (e.g., 1 to 3000, 1 to 1000, 1 to 100, 1 to 50) skeleton atoms selected from carbon atoms, oxygen atoms, nitrogen atoms and sulfur atoms,
RB1and RB2Each independently represents a substituent group, and each independently represents,
nB12 represents a number 0 or 1,
nB13 and nB14 each independently represent an integer of 0 to 3 (preferably 0 or 1),
denotes the bonding site. RB1When there are plural, they may be the same or different, and R isB2When there are plural, they may be the same or different.
When nB12 is 0, the 2-valent group represented by the formula (E1-3) represents a 2-valent group having a structure represented by the following formula (E1-4). In the formula, RB1nB13 and x as illustrated by formula (E1-3).
[ solution 4]
In the embodiment wherein nB12 in the formula (E1-3) is 1, A is12As the 2-valent group, a 2-valent group represented by the following formula (E1-5) is preferable.
[ solution 5]
In the formula (E1-5),
Y1represents a single bond, alkylene, alkenylene, -O-, -CO-, -S-, -SO-, -SO2-, -CONH-, -NHCO-, -COO-or-OCO-,
ring Z2Represents a non-aromatic ring which may have a substituent or an aromatic ring which may have a substituent,
nB15 represents an integer of 0 to 5 (preferably 0 to 3),
denotes the bonding site. Y is1Ring Z2Each independently may have a substituent. Y is1In the case of plural, they may be the same or different, ring Z2When there are plural, they may be the same or different.
As A12Specific examples of the 2-valent group are not particularly limited, and may include-CH2-、-CH(CH3)-、-CH(CH2CH3)-、-C(CH3)2-、-C(CH3)(CH2CH3)-、-C(CH2CH3)2-, -O-, -CO-, -S-, -SO-and-SO2-, and a 2-valent organic group represented below.
[ solution 6]
(E1) The weight average molecular weight (Mw) of the component (B) is not particularly limited, but is preferably 150 to 50000, more preferably 300 to 20000, and more specifically, in the formula (E1-1), nB1 is an integer of 1 or more, preferably 500 to 50000, more preferably 1000 to 20000, and nB1 is 0, preferably 150 to 5000, more preferably 300 to 1000. (E1) The Mw of the component (A) can be measured in terms of polystyrene by Gel Permeation Chromatography (GPC).
In addition, for the component (E1), the equivalent weight of the functional group of the maleimide group is preferably 50 to 20000g/eq, more preferably 100 to 20000g/eq, and more particularly, in the mode that nB1 in the formula (E1-1) is an integer of 1 or more, preferably 300g/eq to 20000g/eq, more preferably 500g/eq to 10000g/eq, and nB1 is 0, preferably 50g/eq to 2000g/eq, more preferably 100g/eq to 1000g/eq, further preferably 200g/eq to 600g/eq, and particularly preferably 300g/eq to 400g/eq.
In the insulating material containing the component (B), the component (E1) preferably contains a maleimide compound having any one of the structure represented by the following formula (E1-6), the structure represented by the following formula (E1-7) and the structure represented by the following formula (E1-8), from the viewpoint of making it easier to adjust the above-described peeling mode and load value at the time of peeling to an appropriate range of the form ・.
[ solution 7]
In the formula (E1-6), A11And ring Z1As described above, A11-Ring Z1-A11The number of carbon atoms per 1 block of (2) is preferably 20 to 100 (more preferably 30 to 60 or 30 to 50), and particularly preferably a so-called dimer acid skeleton (C36 skeleton; C36 alkylene skeleton derived from dimer diamine). nB16 represents an integer of 1 to 10.
[ solution 8]
In the formula (E1-7), A11、Y1Ring Z1Ring Z2And nB15 As described above, A11-Ring Z1-A11The number of carbon atoms per 1 block of (2) is preferably 20 to 100 (more preferably 30 to 60 or 30 to 50), and particularly preferably a so-called dimer acid skeleton (C36 skeleton; C36 alkylene skeleton derived from dimer diamine). In addition, the block formed by nB15+ 1Y 1 and nB15 ring Z2 corresponds to the 2-valent radical A previously explained12Among them, a 2-valent group containing an oxygen atom is preferable. nB17 represents an integer of 1 to 10.
[ solution 9]
In the formula (E1-8), A11And ring Z1As previously explained, A11-Ring Z1-A11The number of carbon atoms per 1 block of (2) is preferably 20 to 100 (more preferably 30 to 60 or 30 to 50), and particularly preferably a so-called dimer acid skeleton (C36 skeleton; C36 alkylene skeleton derived from dimer diamine). nB11 represents an integer of 0 to 10.
Examples of commercially available maleimide compounds having a structure represented by formula (E1-6) include "BMI-3000J" and "BMI-5000" manufactured by デザイナーモレキュールズ (デジグナーモレキュールズ). Examples of commercially available maleimide compounds having a structure represented by formula (E1-7) include "BMI-1400", "BMI-1500" and "BMI-1700" manufactured by デザイナーモレキュールズ. Examples of commercially available maleimide compounds having a structure represented by formula (E1-8) include "BMI-689" manufactured by デザイナーモレキュールズ.
< ingredient (E2) >
(E2) The component (B) is a maleimide compound containing a trimethylindane skeleton. The trimethylindan skeleton is represented by the following formula (E2-1).
[ solution 10]
The benzene ring in the trimethylindane skeleton may have a substituent. When the benzene ring in the trimethylindane skeleton has a substituent, the number of the substituent may be 1 or 2 or more. The upper limit of the number of substituents contained in the benzene ring in the trimethylindane skeleton is usually 3 or less. When the number of the substituents is 2 or more, they may be the same or different from each other. Among them, the benzene ring in the trimethylindane skeleton preferably has no substituent.
(E2) The number of trimethylindan skeletons contained in 1 molecule of component (a) may be 1, or 2 or more. The upper limit may be, for example, 10 or less, 8 or less, 7 or less, or 6 or less.
(E2) Component (c) preferably contains an aromatic ring skeleton in addition to the aforementioned trimethylindan skeleton. The aromatic ring skeleton may be either a carbocyclic skeleton or a heterocyclic skeleton, and is more preferably a carbocyclic skeleton. The number of carbon atoms in the constituent ring of the aromatic ring skeleton is preferably 3 to 20, more preferably 4 to 16, 5 to 14, or 6 to 10. Examples of the aromatic ring skeleton include a benzene ring skeleton, a naphthalene ring skeleton, and an anthracene ring skeleton. (E2) The number of aromatic ring skeletons contained in 1 molecule of component (a) is preferably 1 or more, more preferably 2 or more, preferably 6 or less, more preferably 4 or less, and further preferably 3 or less. (E2) When the component (a) contains 2 or more aromatic ring skeletons in addition to the trimethylindane skeleton, these aromatic ring skeletons may be the same as or different from each other.
The aromatic ring skeleton may have a substituent. When the aromatic ring skeleton has a substituent, the number of the substituent may be 1 or 2 or more. The upper limit of the number of substituents contained in the aromatic ring skeleton is usually 4 or less. When the number of substituents is 2 or more, they may be the same as or different from each other.
(E2) Component (C) preferably contains a 2-valent aliphatic hydrocarbon group in addition to the trimethylindane skeleton. In particular, when the component (E2) contains an aromatic ring skeleton in addition to the benzene ring in the trimethylindane skeleton, the component (E2) preferably contains a 2-valent aliphatic hydrocarbon group. In this case, the 2-valent aliphatic hydrocarbon group preferably links the benzene ring in the trimethylindan skeleton to the aromatic ring skeleton. Further, it is preferable that the aromatic ring skeletons are connected to each other by a 2-valent aliphatic hydrocarbon group.
The number of carbon atoms of the aliphatic hydrocarbon group having a valence of 2 is preferably 1 or more, preferably 12 or less, more preferably 8 or less, and further preferably 5 or less. The aliphatic hydrocarbon group having a valence of 2 may be either a saturated hydrocarbon group having a valence of 2 or an unsaturated hydrocarbon group having a valence of 2, preferably a saturated hydrocarbon group having a valence of 2, and more preferably an alkylene group. Examples of the aliphatic hydrocarbon group having a valence of 2 include linear alkylene groups such as methylene, ethylene, trimethylene, tetramethylene, pentamethylene, and hexamethylene; ethylidene (-CH (CH)3) -) propylidene (-CH (CH)2CH3) -) isopropylidene (-COOR-), C (-CH (CH)3)2-) ethylmethylmethylene (-C (CH)3)(CH2CH3) -) diethyl methylene (-C (CH)2CH3)2-) branched alkylene groups and the like. (E2) When the component (A) contains 2 or more aliphatic hydrocarbon groups having a valence of 2 in addition to the trimethylindane skeleton, these aliphatic hydrocarbon groups having a valence of 2 may be the sameAnd may be different from each other.
In the insulating material containing the component (B), the component (E2) preferably contains a structure represented by the following formula (E2-2) in view of easier adjustment of the above-described peeling mode and load value at the time of peeling to an appropriate range of the form ・. The whole component (E2) may have a structure represented by the formula (E2-2), or a part of the component (E2) may have a structure represented by the formula (E2-2).
[ solution 11]
In the formula (E2-2),
Ara1represents a 2-valent aromatic ring group which may have a substituent,
Ra1and Ra2Each independently represents a substituent group, and each independently represents,
Ra3represents an aliphatic hydrocarbon group having a valence of 2,
na1which represents a positive integer number of times,
na2each independently represents an integer of 0 to 4,
na3each independently represents an integer of 0 to 3. Ra1When there are plural, they may be the same or different, and R isa2When there are plural, they may be the same or different, and plural R' sa3May be the same or different from each other.
Ara1Represents a 2-valent aromatic ring group which may have a substituent. The number of carbon atoms of the 2-valent aromatic ring group is preferably 6 or more, and preferably 20 or less, more preferably 16 or less, 14 or less, or 10 or less. Examples of the 2-valent aromatic ring group include a phenylene group and a naphthylene group. The substituents that the 2-valent aromatic ring group may have include the aforementioned substituents, and among them, preferred are an alkyl group having 1 to 10 carbon atoms, an alkyloxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, an arylthio group having 6 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a halogen atom, a hydroxyl group, and a mercapto group. The hydrogen atoms of the substituents may beOne step is replaced by a halogen atom. When the 2-valent aromatic ring group has a substituent, the number of the substituent is preferably 1 to 4. When the number of substituents included in the 2-valent aromatic ring group is 2 or more, these 2 or more substituents may be the same or different. Wherein Ar isa1Preferred is a 2-valent aromatic ring group which may have a substituent.
Ra1Represents a substituent. As Ra1The substituent(s) include the above-mentioned substituents, and among them, preferred are an alkyl group having 1 to 10 carbon atoms, an alkyloxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, an arylthio group having 6 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a halogen atom, a nitro group, a hydroxyl group and a mercapto group. The hydrogen atom of each substituent may be further replaced by a halogen atom.
Wherein R isa1Preferably 1 or more groups selected from the group consisting of an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms and an aryl group having 6 to 10 carbon atoms, and more preferably an alkyl group having 1 to 4 carbon atoms.
Ra2Represents a substituent. As Ra2The substituent(s) include the aforementioned substituents, and among them, preferred are an alkyl group having 1 to 10 carbon atoms, an alkyloxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, an arylthio group having 6 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a halogen atom, a hydroxyl group and a mercapto group. The hydrogen atom of each substituent may be further replaced by a halogen atom.
Wherein R isa2More preferably 1 or more groups selected from the group consisting of C1-4 alkyl groups, C3-6 cycloalkyl groups, and C6-10 aryl groups.
Ra3Represents a 2-valent aliphatic hydrocarbon group. Preferred aliphatic hydrocarbon groups having a valence of 2 are as defined above.
na1Representing a positive integer. n isa1Preferably 1 or more, preferably 10 or less, and more preferably 8 or less.
na2Each independently represents 0 to 4An integer number. n isa2Preferably 2 or 3, more preferably 2. A plurality of na2May be different from each other, preferably the same. n isa2In the case of 2 or more, a plurality of Ra1May be the same or different from each other.
na3Represents an integer of 0 to 3. n isa3In the case of a plurality of the compounds, they may be different from each other, and preferably the same. n isa3Preferably 0.
In the insulating material containing the component (B), the component (E2) preferably further contains a structure represented by the following formula (E2-3) from the viewpoint of easier adjustment of the above-described peeling mode and the load value at the time of peeling to a preferable range of the embodiment ・. The whole component (E2) may have a structure represented by the formula (E2-3), or a part of the component (E2) may have a structure represented by the formula (E2-3).
[ solution 12]
In the formula (E2-3), Ra1、Ra2、na1、na2And na3The following is illustrated by the formula (E2-2).
(E2) The component (C) may further have a structure represented by the following formula (E2-4).
[ solution 13]
In the formula (E2-4), Ra1、Ra2、na2And na3The following is illustrated by the formula (E2-2). In addition, nc1The number of the repeating units is an integer of 1 to 20. Denotes a bonding site.
For example, in the formula (E2-2), n represents a group of (E2)a23 or less, and 2 or more of ortho-and para-positions of the maleimide group-bonded benzene ring to which maleimide groups are bonded are not bonded with Ra1In the case of (2), the structure represented by the above formula (E2-4) may be incorporated in the structure represented by the formula (E2-2).
In addition, for example, in the formula (E2-3) for the component (E2), na23 or less, and 2 or more of ortho-and para-positions of the maleimide group-bonded benzene ring to which maleimide groups are bonded are not bonded with Ra1In the case of (2), the structure represented by the above formula (E2-4) may be incorporated in the structure represented by the formula (E2-3).
(E2) The method for producing the component is not particularly limited, and the component can be produced, for example, by the method described in the invention Association public bulletin technique No. 2020-. According to the production method described in the disclosure of the patent publication of the present Association, Japanese patent application No. 2020 and Japanese patent application No. 500211, a maleimide compound having a distribution in the number of repeating units of the trimethylindane skeleton can be obtained. The maleimide compound obtained by this method has a structure represented by the following formula (E2-5). Therefore, the component (E) may contain a maleimide compound having a structure represented by the formula (E2-5).
[ solution 14]
In the formula (E2-5), R1、R2、n2And n3Are respectively reacted with R in the formula (E2-2)a1、Ra2、na2And na3The same applies to the preferred species and ranges. n is1The average number of repeating units is 0.95 to 10.0.
In the formula (E2-5), n1Represents the average number of repeating units, and is in the range of 0.95 to 10.0. According to the production method described in the patent publication of the invention Association, Japanese patent publication No. 2020-500211, a group of maleimide compounds containing a structure represented by the formula (E2-5) can be obtained. Represented by the average number n of repeating units in the formula (E2-5)1It is understood that the maleimide compound having a structure represented by the formula (E2-5) thus obtained may contain a maleimide compound having a repeating unit number of 0 of trimethylindan skeleton. Therefore, the maleimide compound having a structure represented by the formula (E2-5) can be purified to remove the maleimide compound having a repeating unit number of 0 of trimethylindane skeleton to obtain the component (E2), and the resin composition can contain only the maleimide compoundThe maleimide compound having a repeating unit number of 0 of the trimethylindane skeleton is preferably not removed from the obtained (E2) component, and the resin composition contains a maleimide compound having a structure represented by formula (E2-5).
In the formula (E2-5), the average number of repeating units n1Preferably 0.95 or more, more preferably 0.98 or more, further preferably 1.0 or more, particularly preferably 1.1 or more, preferably 10.0 or less, more preferably 8.0 or less, further preferably 7.0 or less, and particularly preferably 6.0 or less. Average number of repeating units n1In the case of this range, the effect of the present invention can be obtained remarkably.
Among these, in the insulating material containing the component (B), from the viewpoint of easier adjustment of the above-described peeling mode and load value at the time of peeling to a preferable mode and range, specific examples of the structure of the component (E2) include the following:
[ solution 15]
The maleimide compound having a structure represented by the formula (E2-5) may further have a structure represented by the above formula (E2-4). For example, with respect to the maleimide compound having a structure represented by the formula (E2-5), n in the formula (E2-5)2Is 3 or less, and 2 or more of ortho-and para-positions of the maleimide group bonding position of the benzene ring to which the maleimide group is bonded are not bonded with R1In the case of (2), the structure represented by the formula (E2-4) may be incorporated in the structure represented by the formula (E2-5).
The molecular weight distribution Mw/Mn, which is calculated by Gel Permeation Chromatography (GPC) measurement and contains the maleimide compound having a structure represented by the formula (E2-5), is preferably in a specific range. Specifically, the molecular weight distribution Mw/Mn of the maleimide compound having a structure represented by the formula (E2-5) is preferably 1.0 to 4.0, more preferably 1.1 to 3.8, still more preferably 1.2 to 3.6, and particularly preferably 1.3 to 3.4.
The equivalent of the maleimide group functional group in the component (E2) is preferably 50 g/eq.or more, more preferably 100 g/eq.or more, still more preferably 200 g/eq.or more, preferably 2000 g/eq.or less, still more preferably 1000 g/eq.or less, and still more preferably 800 g/eq.or less.
< ingredient (E3) >
(E3) The component (A) is a maleimide compound having an aromatic ring directly bonded to the nitrogen atom of the maleimide compound. The maleimide compound can be obtained, for example, by subjecting a component containing an aromatic amine compound (such as an aromatic diamine compound) and maleic anhydride to imidization.
In one embodiment, the component (E3) contains a compound represented by the following formula (E3-1).
[ solution 16]
In the formula (E3-1),
ring Ar1Represents an aromatic ring which may have a substituent,
L2represents a single bond or a 2-valent linking group,
nB2 represents an integer of 1 to 100. Multiple rings Ar1Which may be the same or different from each other, L2When there are plural, they may be the same or different from each other.
As ring Ar1The aromatic ring represented by (a) may be either a carbocyclic ring or a heterocyclic ring, and is more preferably a carbocyclic ring. Ring Ar1The aromatic ring has preferably 3 to 20 carbon atoms, more preferably 5 to 14 or 6 to 10 carbon atoms. The number of carbon atoms does not include the number of carbon atoms of the substituent.
As L2The linking group having a valence of 2 represented by (A) is not particularly limited as long as it is a 2-valent group containing 1 or more (for example, 1 to 3000, 1 to 1000, 1 to 100, 1 to 50) skeleton atoms selected from a carbon atom, an oxygen atom, a nitrogen atom and a sulfur atom, and examples thereof include A in the formula (E1-3)12The 2-valent radical described.
Among these, in the insulating material containing the component (B), the above-mentioned peeling mode and the load value at the time of peeling can be more easily adjusted to an appropriate form and rangeFrom the viewpoint of (1), ring Ar1Preferably an optionally substituted aromatic carbocyclic ring having 6 to 10 carbon atoms (more preferably an optionally substituted benzene ring), and L is preferably2(L2In case of plural, at least 1L2) Is a 2-valent group having a biphenyl skeleton. Accordingly, in one embodiment, the component (E3) has a biphenyl skeleton.
In the component (E3), the nitrogen atom of maleimide is directly bonded to the aromatic ring. Bonding position of maleimide to aromatic ring, L bonded to aromatic ring2For reference, any position may be used. For example, in the case where the aromatic ring is a benzene ring, L at the bonding position of maleimide to the benzene ring is bonded to the benzene ring2The compound may be any of ortho-, meta-and para-positions, and the bond to the para-position is preferable from the viewpoint of further enjoying the effects of the present invention.
In a preferred embodiment, the component (E3) contains a compound represented by the following formula (E3-2).
[ solution 17]
In the formula (E3-2),
RB3、RB4、RB5and RB6Each independently represents a substituent group, and each independently represents,
nB21 represents an integer of 1 to 100,
nB22 and nB23 each independently represent an integer of 1 to 10,
nB24 and nB25 each independently represent an integer of 0 to 3,
nB26 and nB27 each independently represent an integer of 0 to 4. RB3In the case of plural, they may be the same or different from each other, as for RB4、RB5And RB6The same applies.
nB21 is preferably 1 to 50, more preferably 1 to 20, and further preferably 1 to 5.
Each of nB22 and nB23 is independently preferably 1 to 6, more preferably 1 to 3, and further preferably 1 or 2.
Each of nB24 and nB25 is independently an integer of preferably 0 to 2, more preferably 0 or 1. When nB24 and nB25 are 1 or more, R is preferablyB3And RB4The substituents represented are each independently an alkyl group or an aryl group.
Each of nB26 and nB27 is independently an integer of preferably 0 to 2, more preferably 0 or 1. When nB26 and nB27 are 1 or more, R is preferablyB5And RB6The substituents represented are each independently an alkyl group or an aryl group.
Among them, nB26 and nB27 are preferably 0. Therefore, in a preferred embodiment, the component (E3) contains a compound represented by the following formula (E3-3).
[ solution 17]
In the formula (E3-3), RB3、RB4nB21, nB22, nB23, nB24 and nB25 are illustrated by the formula (E3-2) below.
(E3) When the molecular weight of the component (a) has a molecular weight distribution, the weight average molecular weight (Mw) is 500 or more, preferably 550 or more. The upper limit of the Mw is not particularly limited, but is preferably 5000 or less, and more preferably 2500 or less. (E3) The Mw of the component (A) can be measured as a polystyrene equivalent by a Gel Permeation Chromatography (GPC) method.
In addition, for the component (E3), the functional group equivalent of the maleimide group is preferably 50g/eq to 2000g/eq, more preferably 100g/eq to 1000g/eq, further preferably 150g/eq to 500g/eq, and particularly preferably 200g/eq to 300g/eq.
In the insulating material containing the component (B), the component (E3) preferably contains a maleimide compound having a structure represented by the following formula (E3-4) from the viewpoint of making it easier to adjust the above-described peeling mode and load value at the time of peeling to an appropriate form and range.
[ solution 18]
In the formula (E3-4), nB21 is as defined above.
Examples of commercially available maleimide compounds having a structure represented by formula (E3-4) include "MIR-3000-70 MT" manufactured by Nippon chemical Co., Ltd. As the component (E3) and the compound represented by the formula (E3-1), "BMI-4000" manufactured by Dahe Kabushiki Kaisha, and "BMI-80" manufactured by ケイアイ Kabushiki Kaisha may be used.
When the resin composition of the present invention contains the component (E), the content of the component (E) in the resin composition is preferably 0.5% by mass or more, more preferably 1% by mass or more, 2% by mass or more, 3% by mass or more, or 5% by mass or more, based on 100% by mass of the total of nonvolatile components in the resin composition, from the viewpoint of making it easier to adjust the above-described peeling mode and load value at the time of peeling to an appropriate form and range even when the content of the component (B) is relatively high. (E) The upper limit of the content of the component (b) is not particularly limited, but is preferably 30% by mass or less, more preferably 25% by mass or less, 20% by mass or less, or 15% by mass or less.
The blending amount ratio of the component (E) to the component (B), that is, the mass ratio of the component (E)/the component (B) is preferably 0.1 or more, more preferably 0.15 or more, 0.2 or more, 0.25 or more, 0.3 or more, 0.35 or more, or 0.4 or more, in terms of nonvolatile components, from the viewpoint of making it easier to adjust the above-described peeling mode and load value at the time of peeling to an appropriate form and range even when the content of the component (B) is relatively high. The upper limit of the mass ratio is not particularly limited, and may be, for example, 10 or less, 8 or less, 6 or less, 5 or less, or the like.
- (F) curing accelerators-
The resin composition of the present invention may contain a curing accelerator as the component (F).
Examples of the component (F) include phosphorus-based curing accelerators, amine-based curing accelerators, imidazole-based curing accelerators, guanidine-based curing accelerators, metal-based curing accelerators, peroxide-based curing accelerators, and the like. (F) The component (A) may be used alone in 1 kind, or may be used 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 caprate, (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, benzyldimethylamine, 2,4, 6-tris (dimethylaminomethyl) phenol, and 1, 8-diazabicyclo (5,4,0) -undecene.
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-methylimidazole, 2-decylimidazole, 2-ethylimidazole, 2-decylimidazole, 2-methylimidazole, 2-decylimidazole, 2-iodonium, 2-methylimidazole, and the like, 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.
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.
Examples of the peroxide curing accelerator include peroxides such as t-butylcumyl peroxide, t-butyl peroxyacetate, α' -di (t-butylperoxy) diisopropylbenzene, t-butyl peroxylaurate, t-butyl peroxy2-ethylhexanoate, t-butyl peroxyneodecanoate, and t-butyl peroxybenzoate. Examples of commercially available peroxide-based curing accelerators include "Perbutyl C", "Perbutyl a", "Perbutyl P", "Perbutyl L", "Perbutyl O", "Perbutyl ND", "Perbutyl Z", "Perhexyl D", "Percumyl P" and "Percumyl D" manufactured by nippon oil co.
When the resin composition of the present invention contains the component (F), the content of the component (F) in the resin composition is preferably 0.001 mass% or more, more preferably 0.005 mass% or more, further preferably 0.01 mass% or more, preferably 1 mass% or less, more preferably 0.8 mass% or less, 0.6 mass% or less, or 0.4 mass% or less, based on 100 mass% of the total nonvolatile components in the resin composition.
Other ingredients-
The resin composition of the present invention may further contain optional additives. Examples of such additives include organic metal compounds such as organic copper compounds, organic zinc compounds, and organic cobalt compounds; thermoplastic resins such as phenoxy resins, polyvinyl acetal resins, polysulfone resins, polyethersulfone resins, polyphenylene ether resins, polyetheretherketone resins, and polyester resins; colorants such as phthalocyanine blue, phthalocyanine green, iodine green, diazo yellow, crystal violet, titanium oxide, and carbon black; polymerization inhibitors of hydroquinone, catechol, pyrogallol, phenothiazine, and the like; leveling agents such as silicone leveling agents and acrylic polymer leveling agents; thickeners such as bentonite 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; an adhesion-imparting agent such as a triazole-based adhesion-imparting agent, a tetrazole-based adhesion-imparting agent, or a triazine-based adhesion-imparting agent; antioxidants such as hindered phenol antioxidants and hindered amine antioxidants; fluorescent whitening agents such as stilbene derivatives; surfactants such as fluorine-based surfactants and silicone-based surfactants; flame retardants such as phosphorus flame retardants (e.g., phosphate ester compounds, phosphazene compounds, phosphinic acid compounds, and red phosphorus), nitrogen flame retardants (e.g., melamine sulfate), halogen flame retardants, and inorganic flame retardants (e.g., antimony trioxide); a phosphate-based dispersing agent, a polyoxyalkylene-based dispersing agent, an acetylene-based dispersing agent, an anionic dispersing agent, a cationic dispersing agent, and the like; and stabilizers such as borate stabilizers, titanate stabilizers, aluminate stabilizers, zirconate stabilizers, isocyanate stabilizers, carboxylic acid stabilizers, and carboxylic acid anhydride stabilizers. These additives may be used alone in 1 kind, or in combination of 2 or more kinds. The respective contents can be arbitrarily set by those skilled in the art.
The resin composition of the present invention may contain an optional organic solvent as a volatile component in addition to the nonvolatile component. As the organic solvent, a known organic solvent can be suitably used, and the kind thereof is not particularly limited. Examples of the organic solvent include ketone solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone; ester-based 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, diethylene glycol ethyl ether acetate, γ -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; and aromatic hydrocarbon solvents such as benzene, toluene, xylene, ethylbenzene, and trimethylbenzene. The organic solvent may be used alone in 1 kind, or 2 or more kinds may be used in combination.
The resin composition of the present invention can be produced, for example, by adding and mixing the component (a), the component (B), or, if necessary, the component (C), the component (D), the component (E), the component (F), other additives, and an organic solvent in an arbitrary preparation vessel in an arbitrary order and/or in a part or all at once. In addition, the temperature may be appropriately set during the addition and mixing of the components, and heating and/or cooling may be performed for a short time or all the time. In addition, during or after the addition and mixing, the resin composition may be uniformly dispersed by stirring or shaking using a stirring device such as a mixer or a shaking device. Further, defoaming can be performed under low pressure conditions such as vacuum while stirring or shaking.
The resin composition of the present invention can be suitably used as a resin composition for forming an insulating material. Specifically, the resin composition is suitably used as a resin composition for forming an insulating layer of a printed wiring board (resin composition for an insulating layer of a printed wiring board), and more suitably used as a resin composition for forming an interlayer insulating layer of a printed wiring board (resin composition for an interlayer insulating layer of a printed wiring board). The resin composition of the present invention can provide an insulating layer having excellent component embedment properties, and therefore, is suitable for use in the case where a printed wiring board is a component-embedded circuit board. The resin composition of the present invention is also applicable as a resin composition for forming an insulating layer on which a conductor layer (including a redistribution layer) is provided (resin composition for forming an insulating layer for a conductor layer). The resin composition of the present invention is suitably used as a resin composition (a resin composition for sealing) for sealing electronic devices such as organic EL devices and semiconductors, and particularly, as a resin composition (a resin composition for sealing semiconductors) for sealing semiconductors, preferably a resin composition (a resin composition for sealing semiconductor chips) for sealing semiconductor chips. The resin composition of the present invention can be widely used in applications requiring a resin composition, such as a resin sheet, a sheet-like laminate material such as a prepreg, a solder resist, an underfill material, a die-bonding material, a hole-filling resin, and a component-embedding resin.
[ resin sheet ]
The resin composition of the present invention can be applied in the form of varnish, and is generally industrially suitable for use in the form of a sheet-like laminate containing the resin composition.
As the sheet-like laminate, a resin sheet and a prepreg described below are preferable.
In one embodiment, the resin sheet includes a support and a layer of a resin composition provided on the support (hereinafter simply referred to as "resin composition layer"), and the resin composition layer is characterized by being formed of the resin composition of the present invention.
The thickness of the resin composition layer is suitably determined depending on the purpose, and may be suitably determined depending on the purpose. The insulating material obtained using the resin composition of the present invention exhibits excellent effects of suppressing warpage without being affected by the thickness and also having good long-term reliability. For example, the thickness of the resin composition layer is preferably 200 μm or less, more preferably 150 μm or less, 120 μm or less, 100 μm or less, 80 μm or less, 60 μm or less, or 50 μm or less, from the viewpoint of thinning of a printed wiring board or a semiconductor package and providing a cured product which can suppress warpage even if the resin composition is a film. The lower limit of the thickness of the resin composition layer is not particularly limited, and may be usually 5 μm or more and 10 μm or more.
Examples of the support include a film made of a plastic material, a metal foil, and a release paper, and preferably a film made of a plastic material and a metal foil.
When a film made of a plastic material is used as the support, examples of the plastic material include polyesters such as polyethylene terephthalate (PET) and polyethylene naphthalate (PEN), acrylic, cyclic polyolefins such as Polycarbonate (PC) and polymethyl methacrylate (PMMA), 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 support may be subjected to matte treatment, corona treatment, or antistatic treatment on the surface bonded to the resin composition layer. In addition, as the support, a support with a release layer having a release layer on a surface 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 with a release layer, commercially available ones can be used, and examples thereof include PET films having a release layer comprising an alkyd resin-based release agent as a main component, that is, "SK-1", "AL-5" and "AL-7" manufactured by LINTEC, and "ルミラー T60" manufactured by Toray, and "ピューレックス" manufactured by imperial, and "ユニピール" manufactured by ユニチカ.
The thickness of the support is not particularly limited, but is preferably in the range of 5 μm to 75 μm, and more preferably in the range of 10 μm to 60 μm. When the support with a release layer is used, the thickness of the entire support with a release layer is preferably within the above range.
As the support, a metal foil with a support base, in which a releasable support base is bonded to a thin metal foil, may be used. In one embodiment, a metal foil with a supporting substrate includes a supporting substrate, a release layer disposed on the supporting substrate, and a metal foil disposed on the release layer. When a metal foil with a supporting base material is used as the support, the resin composition layer is provided on the metal foil.
In the metal foil with a supporting base, the material of the supporting base is not particularly limited, and examples thereof include copper foil, aluminum foil, stainless steel foil, titanium foil, and copper alloy foil. When a copper foil is used as the supporting base material, the copper foil may be an electrolytic copper foil or a rolled copper foil. The release layer is not particularly limited if the metal foil can be released from the supporting substrate, and examples thereof include an alloy layer of an element selected from Cr, Ni, Co, Fe, Mo, Ti, W, and P; organic coatings, and the like.
Among the metal foils with a supporting base material, copper foil and copper alloy foil are preferable as the material of the metal foil.
In the metal foil with a supporting base material, the thickness of the supporting base material is not particularly limited, but is preferably in the range of 10 μm to 150 μm, and more preferably in the range of 10 μm to 100 μm. The thickness of the metal foil may be, for example, in the range of 0.1 to 10 μm.
In one embodiment, the resin sheet may further contain an optional layer as necessary. Examples of the optional 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). The thickness of the protective film is not particularly limited, and is, for example, 1 μm to 40 μm. By laminating the protective film, adhesion and damage of dirt and the like on the surface of the resin composition layer can be suppressed.
The resin sheet can be produced, for example, by preparing a resin varnish in which a liquid resin composition is dissolved in an organic solvent as it is or by coating the resin varnish on a support with a die coater or the like and then drying the coating to form a resin composition layer.
The organic solvent may be the same as the organic solvent described as a component of the resin composition. The organic solvent may be used alone in 1 kind, or 2 or more kinds may be used in combination.
The drying may be carried out by a known method such as heating or blowing hot air. The drying conditions are not particularly limited, and the 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. The boiling point of the organic solvent in the resin composition or the resin varnish varies, but when the resin composition or the resin varnish containing 30 to 60 mass% of the organic solvent is used, for example, the resin composition layer can be formed by drying at 50 to 150 ℃ for 3 to 10 minutes.
The resin sheet can be stored in a roll form. When the resin sheet has a protective film, the protective film can be peeled off and used.
In one embodiment, a prepreg is formed by impregnating a sheet-like fibrous base material with the resin composition of the present invention.
The sheet-like fibrous base material used in the prepreg is not particularly limited, and a base material commonly used as a base material for the prepreg, such as a glass cloth, an aramid nonwoven fabric, or a liquid crystal polymer nonwoven fabric, can be used. The thickness of the sheet-like fibrous base material is preferably 50 μm or less, more preferably 40 μm or less, still more preferably 30 μm or less, and particularly preferably 20 μm or less, from the viewpoint of thinning of the printed wiring board. The lower limit of the thickness of the sheet-like fibrous base material is not particularly limited. Usually 10 μm or more.
The prepreg can be produced by a known method such as a hot melt method or a solvent method.
The thickness of the prepreg may be in the same range as the resin composition layer in the resin sheet.
The sheet-like laminate material of the present invention is suitable for forming an insulating layer of a printed wiring board (for an insulating layer of a printed wiring board), and is more suitable for forming an interlayer insulating layer of a printed wiring board (for an interlayer insulating layer of a printed wiring board). The sheet-like laminate of the present invention is also suitable as a resin composition (for sealing) for sealing electronic devices such as organic EL devices and semiconductors, particularly suitable as a resin composition (for sealing semiconductors) for sealing semiconductors, and preferably suitable as a resin composition (for sealing semiconductor chips) for sealing semiconductor chips.
[ printed Wiring Board ]
The printed wiring board of the present invention comprises an insulating layer comprising a cured product of the resin composition of the present invention.
The printed wiring board can be produced, for example, by a method including the steps (I) and (II) described below using the above-described resin sheet.
(I) A step of laminating a resin sheet on the inner layer substrate and bonding the resin composition layer of the resin sheet to the inner layer substrate,
(II) a step of curing (e.g., thermosetting) the resin composition layer to form an insulating layer
The "inner layer substrate" used in the step (I) is a member to be a substrate of a printed wiring board, and examples thereof include a glass epoxy substrate, a metal substrate, a polyester substrate, a polyimide substrate, a BT resin substrate, a thermosetting polyphenylene ether substrate, and the like. The substrate may have a conductive layer on one surface or both surfaces thereof, and the conductive layer may be patterned. An inner layer substrate having a conductor layer (circuit) formed on one or both surfaces of a substrate is sometimes referred to as an "inner layer circuit substrate". In addition, in the case of manufacturing a printed wiring board, an intermediate product in which an insulating layer and/or a conductor layer should be further formed is also included in the "inner layer substrate" according to the present invention. When the printed wiring board is a component-embedded circuit board, an inner layer substrate with embedded components may be used.
The lamination of the inner layer substrate and the resin sheet can be performed, for example, by heat-crimping the resin sheet to the inner layer substrate from the support side. Examples of the member for heat-pressure bonding the resin sheet to the inner layer substrate (hereinafter also referred to as "heat-pressure bonded member") include a heated metal plate (such as an SUS mirror plate) and a metal roll (SUS roll). The heat-pressure bonding member may be directly pressure-bonded to the resin sheet, or may be pressed through an elastic material such as heat-resistant rubber so that the resin sheet sufficiently follows the surface irregularities of the inner layer substrate.
The lamination of the inner substrate and the resin sheet may be performed by a vacuum lamination method. In the vacuum lamination method, the heating and crimping temperature is preferably 60-160 ℃, more preferably 80-140 ℃, the heating and crimping pressure is preferably 0.098-1.77 MPa, more preferably 0.29-1.47 MPa, and the heating and crimping time is preferably 20-400 seconds, more preferably 30-300 seconds. The lamination can be 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 vacuum pressure laminators manufactured by Nikko-Materials, and batch vacuum pressure laminators.
After the lamination, the smoothing treatment of the laminated resin sheets may be performed by pressing, for example, the heat and pressure bonding member from the support body side under normal pressure (atmospheric pressure). The pressing conditions for the smoothing treatment may be the same as the conditions for the thermocompression bonding of the laminate. The smoothing treatment may be performed by a commercially available laminator. The lamination and smoothing treatment can be continuously performed using the above-mentioned commercially available vacuum laminator.
The support may be removed between step (I) and step (II) or after step (II). When a metal foil is used as the support, the conductor layer can be formed using the metal foil without peeling the support. In addition, when a metal foil with a supporting base is used as the support, the supporting base (and the release layer) can be peeled off. Also, the conductor layer may be formed using a metal foil.
In the step (II), the resin composition layer is cured (for example, thermally cured) to form an insulating layer including a cured product of the resin composition. The curing conditions for the resin composition layer are not particularly limited, and the conditions generally employed in forming the insulating layer of a printed wiring board can be used.
For example, the heat curing conditions of the resin composition layer vary depending on the kind of the resin composition, and in one embodiment, the curing temperature is preferably 120 ℃ to 250 ℃, more preferably 150 ℃ to 240 ℃, and still more preferably 180 ℃ to 230 ℃. The curing time is preferably 5 to 240 minutes, more preferably 10 to 150 minutes, and still more preferably 15 to 120 minutes. In the case of determining the temperature for thermosetting, it is preferable to confirm the heat generation peak of the target resin composition by using a differential scanning calorimeter and determine the temperature for thermosetting based on the temperature of the heat generation peak, from the viewpoint of sufficiently curing the resin composition layer to achieve a desired degree of curing (and hence a desired cohesive force (in-layer adhesive strength)). For example, when the temperature of the heat generation peak exhibited by the subject resin composition is T (. degree.C.) when the resin composition is heated from 30 ℃ to 350 ℃ at a temperature rise rate of 5 ℃/min, the temperature for heat curing is preferably at least (T +10) (. degree.C.). When there are a plurality of heat generation peaks, the temperature of the heat generation peak in the highest temperature range may be defined as T (° c) and the temperature of the heat curing may be determined.
Before the resin composition layer is thermally cured, the resin composition layer may be preheated at a temperature lower than the curing temperature. For example, before the resin composition layer is thermally cured, the resin composition layer may be preheated at a temperature of 50 ℃ to 120 ℃, preferably 60 ℃ to 115 ℃, more preferably 70 ℃ to 110 ℃ for 5 minutes or more, preferably 5 minutes to 150 minutes, more preferably 15 minutes to 120 minutes, and further preferably 15 minutes to 100 minutes.
In the production of the printed wiring board, (III) a step of forming holes in the insulating layer, (IV) a step of roughening the insulating layer, and (V) a step of forming a conductor layer may be further performed. These steps (III) to (V) can be carried out according to various methods known to those skilled in the art used in the manufacture of printed wiring boards. When the support is removed after step (II), the support may be removed between step (II) and step (III), between step (III) and step (IV), or between step (IV) and step (V). If necessary, the insulating layers and the conductor layers in steps (I) to (V) may be repeatedly formed to form a multilayer wiring board.
In another embodiment, the printed wiring board of the present invention can be manufactured using the prepreg described above. The manufacturing method is basically the same as the case of using the resin sheet.
Step (III) is a step of opening a hole in the insulating layer, whereby a hole such as a via hole (ビアホール), a via hole (スルーホール), or the like can be formed in the insulating layer. Step (III) may be performed using, for example, a drill, a laser, plasma, or the like, depending on the composition of the resin composition used for forming the insulating layer, or the like. The size and shape of the holes may be determined as appropriate depending on the design of the printed wiring board.
The step (IV) is a step of subjecting the insulating layer to roughening treatment. Typically, in this step (IV), the removal of the smear is also performed. The flow and conditions of the roughening treatment are not particularly limited, and known flows and conditions generally used for forming an insulating layer of a printed wiring board can be used. For example, the insulating layer may be subjected to a roughening treatment by sequentially performing a swelling treatment with a swelling liquid, a roughening treatment with an oxidizing agent, and a neutralizing treatment with a neutralizing liquid.
The swelling solution used for the roughening treatment is not particularly limited, and examples thereof include an alkali solution and a surfactant solution, and the alkali solution is preferably an alkali solution, and more preferably a sodium hydroxide solution and a potassium hydroxide solution. Examples of commercially available Swelling liquids include "Swelling Dip securigranth P (スウェリング seed ディップ seed セキュリガンス P)" and "Swelling Dip securigranth SBU (スウェリング seed ディップ seed セキュリガンス SBU)" manufactured by Atotech Japan. The swelling treatment with the swelling solution is not particularly limited, and may be performed by, for example, immersing the insulating layer 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 minutes to 15 minutes.
The oxidizing agent used in the roughening treatment is not particularly limited, and examples thereof include an alkaline permanganic acid solution obtained by dissolving potassium permanganate or sodium permanganate in an aqueous solution of sodium hydroxide. The roughening treatment with an oxidizing agent such as an alkaline permanganic acid solution is preferably performed by immersing the insulating layer in an oxidizing agent solution heated to 60 to 100 ℃ for 10 to 30 minutes. In addition, 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 "コンセントレート seed コンパクト CP" and "ドージングソリューション seed セキュリガンス P" manufactured by Atotech Japan.
The neutralizing solution used for the roughening treatment is preferably an acidic aqueous solution, and examples of commercially available products include "Reduction solution securiganthP (リダクションソリューション seed セキュリガント P)" manufactured by Atotech Japan.
The treatment with the neutralizing solution can be performed by immersing the treated surface subjected to the roughening treatment with the oxidizing agent in the neutralizing solution at 30 to 80 ℃ for 5 to 30 minutes. From the viewpoint of workability, the method is preferably a method of immersing the object subjected to the roughening treatment with the oxidizing agent in a neutralizing solution at 40 ℃ to 70 ℃ for 5 minutes to 20 minutes.
Step (V) is a step of forming a conductor layer, which is formed on the insulating layer. The conductor material used for the conductor layer is not particularly limited. In a suitable embodiment, the conductor layer comprises 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 layer may be a single metal layer or an alloy layer, and examples of the alloy layer include layers formed of an alloy of 2 or more metals selected from the above group (e.g., a nickel ・ chromium alloy, a copper ・ nickel alloy, and a copper ・ titanium alloy). Among them, from the viewpoints of versatility of conductor layer formation, cost, easiness of pattern formation, and the like, a single metal layer of chromium, nickel, titanium, aluminum, zinc, gold, palladium, silver, or copper, or an alloy layer of nickel ・ chromium alloy, copper ・ nickel alloy, or copper ・ titanium alloy is preferable, a single metal layer of chromium, nickel, titanium, aluminum, zinc, gold, palladium, silver, or copper, or an alloy layer of nickel ・ chromium alloy is more preferable, and a single metal layer of copper is even more preferable.
The conductor layer may have a single-layer structure, or may have a multilayer structure in which 2 or more single metal layers or alloy layers made of different metals or alloys are stacked. 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 nickel ・ chromium alloy.
The thickness of the conductor layer varies depending on the design of the desired printed wiring board, and is generally 3 μm to 35 μm, preferably 5 μm to 30 μm.
In one embodiment, the conductor layer is preferably formed by plating. For example, a conductor layer having a desired wiring pattern can be formed by plating on the surface of the insulating layer by a conventionally known technique such as a semi-additive method or a full-additive method. From the viewpoint of ease of production, the formation by a semi-addition method is preferable. 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 insulating layer by electroless plating. Next, a mask pattern for exposing a part of the plating seed layer is formed on the formed plating seed layer in accordance with a desired wiring pattern. After a metal layer is formed on the exposed plating seed layer by electrolytic plating, the mask pattern is removed. Thereafter, the unnecessary plating seed layer is removed by etching or the like, whereby a conductor layer having a desired wiring pattern can be formed.
In other embodiments, the conductor layer may be formed using a metal foil. In the case where a metal foil is used to form the conductor layer, it is appropriate that step (V) be carried out between step (I) and step (II). For example, after step (I), the support is removed, and a metal foil is laminated on the surface of the exposed resin composition layer. The lamination of the resin composition layer and the metal foil may be performed by a vacuum lamination method. The conditions for lamination may be the same as those described for step (I). Next, step (II) is performed to form an insulating layer. Then, a conductor layer having a desired wiring pattern can be formed by a conventionally known technique such as a subtractive method or a modified semi-additive method using a metal foil on an insulating layer.
The metal foil can be produced by a known method such as an electrolytic method or a rolling method. As commercially available products of metal foil, for example, HLP foil, JXUT-III foil, 3EC-III foil, TP-III foil, etc. available from JX Nikki Stone Metal Co., Ltd.
Alternatively, when a metal foil or a metal foil with a supporting base material is used as the support of the resin sheet, the conductor layer may be formed using the metal foil as described above.
[ semiconductor Package ]
The semiconductor package of the present invention includes a sealing layer containing a cured product of the resin composition of the present invention. The semiconductor package of the present invention may further contain an insulating layer (redistribution layer-forming layer) for forming a redistribution layer, the insulating layer containing a cured product of the resin composition of the present invention, as described above.
The semiconductor package can be produced by a method including the following steps (1) to (6) using the resin composition and the resin sheet of the present invention, for example. The resin composition and the resin sheet of the present invention may be used to form the sealing layer in step (3) or the redistribution layer in step (5). An example of forming the sealing layer and the redistribution layer using the resin composition and the resin sheet will be described below, and techniques for forming the sealing layer and the redistribution layer of the semiconductor package are known.
(1) A step of laminating a pre-fixing film on a substrate,
(2) A step of pre-fixing the semiconductor chip on the pre-fixing film,
(3) A step of forming a sealing layer on the semiconductor chip,
(4) A step of peeling the base material and the pre-fixing film from the semiconductor chip,
(5) A step of forming a rewiring formation layer as an insulating layer on a surface of the semiconductor chip from which the base material and the pre-fixing film are peeled, and
(6) a step of forming a rewiring layer as a conductor layer on the rewiring-forming layer
Step (1)
The material used for the base material is not particularly limited. As the substrate, silicon wafers; a glass wafer; a glass substrate; metal substrates such as copper, titanium, stainless steel, and cold-rolled steel Sheet (SPCC); a substrate (for example, FR-4 substrate) in which epoxy resin or the like is impregnated into glass fibers and thermosetting is performed; a substrate containing bismaleimide triazine resin (BT resin), and the like.
The material of the pre-fixing film is not particularly limited if the semiconductor chip can be pre-fixed while being peelable from the semiconductor chip in the step (4). The pre-fixed film may be a commercially available one. Examples of commercially available products include リヴァアルファ manufactured by Nindon electric engineering Co.
Step (2)
The semiconductor chip may be pre-fixed by using a known device such as a flip chip bonder (flip chip bonder) or a die bonder (die bonder). The arrangement and the number of semiconductor chips can be set as appropriate depending on the shape and size of the pre-fixing film, the number of production processes of the target semiconductor package, and the like, and for example, the pre-fixing can be performed in a matrix form in which the semiconductor chips are arranged in a plurality of rows and a plurality of columns.
Step (3)
The resin composition layer of the resin sheet of the present invention is laminated on a semiconductor chip, or the resin sheet of the present invention is coated on a semiconductor chip and heat-cured to form a sealing layer.
For example, the lamination of the semiconductor chip and the resin sheet may be performed by heat-crimping the resin sheet to the semiconductor chip from the support side after removing the protective film of the resin sheet. Examples of a member for heat-crimping a resin sheet to a semiconductor chip (hereinafter also referred to as "heat-crimping member") include a heated metal plate (such as an SUS mirror plate) and a metal roll (SUS roll). It is preferable that the thermocompression bonding member is pressed through an elastic material such as heat-resistant rubber so that the resin sheet sufficiently follows the surface irregularities of the semiconductor chip, instead of directly bonding the thermocompression bonding member to the resin sheet. The lamination of the semiconductor chip and the resin sheet may be performed by a vacuum lamination method, and the lamination conditions are the same as those described for the method for manufacturing the printed wiring board, and the preferable ranges are also the same.
After lamination, the resin composition is thermally cured to form a sealant layer. The conditions for the thermal curing are the same as those described for the method for producing a printed wiring board.
The support of the resin sheet may be peeled off after the resin sheet is laminated on the semiconductor chip and thermally cured, or may be peeled off before the resin sheet is laminated on the semiconductor chip.
When the sealing layer is formed by applying the resin composition of the present invention, the coating conditions are the same as the application conditions for forming the resin composition layer described with respect to the resin sheet of the present invention, and the preferable ranges are also the same.
Step (4)
The method of peeling the substrate and the pre-fixing film may be appropriately changed depending on the material of the pre-fixing film, and examples thereof include a method of peeling the pre-fixing film by heating and foaming (or expanding) the pre-fixing film, and a method of peeling the pre-fixing film by irradiating the substrate side with ultraviolet rays to decrease the adhesive force of the pre-fixing film.
In the method of heating the pre-fixing film to foam (or expand) the film for peeling, the heating condition is usually 100 to 250 ℃ for 1 to 90 seconds or 5 to 15 minutes. In the method of peeling the pre-fixing film by irradiating the substrate side with ultraviolet light to reduce the adhesive force of the pre-fixing film, the irradiation amount of the ultraviolet light is usually 10mJ/cm2~1000mJ/cm2。
Step (5)
The material for forming the redistribution layer (insulating layer) is not particularly limited if it has insulating properties when forming the redistribution layer (insulating layer), and a photosensitive resin or a thermosetting resin is preferable from the viewpoint of ease of manufacturing the semiconductor chip package. The redistribution layer-forming layer can be formed using the resin composition and the resin sheet of the present invention.
After the redistribution line formation layer is formed, a via hole may be formed in the redistribution line formation layer in order to connect the semiconductor chip and a conductor layer to be described later, and the via hole may be formed by a known method depending on the material of the redistribution line formation layer.
Step (6)
The formation of the conductor layer on the rewiring-forming layer can be carried out in the same manner as in the step (V) described with respect to the method of manufacturing a printed wiring board. Note that, the steps (5) and (6) may be repeated, and the conductor layer (redistribution layer) and the redistribution layer forming layer (insulating layer) may be alternately laminated (laminated).
In the case of manufacturing a semiconductor package, (7) a step of forming a solder resist layer on a conductor layer (redistribution layer), (8) a step of forming bumps, and (9) a step of dicing a plurality of semiconductor chip packages into individual semiconductor chip packages and dicing the individual semiconductor chip packages may be further performed. These steps may be performed according to various methods known to those skilled in the art employed in the manufacture of semiconductor packages.
By forming the sealing layer using the resin composition and the resin sheet of the present invention, which can provide an insulating material having excellent long-term reliability while suppressing warpage, a semiconductor package having excellent long-term reliability while suppressing warpage can be realized regardless of whether the semiconductor package is a Fan-In (Fan-In) type package or a Fan-Out (Fan-Out) type package. In one embodiment, the semiconductor package of the present invention is a Fan-Out (Fan-Out) type package. The resin composition and the resin sheet of the present invention are applicable to both fan-out type board level packages (FOPLPs) and fan-out type wafer level packages (FOWLPs). In one embodiment, the semiconductor package of the present invention is a fan-out panel-level package (FOPLP). In another embodiment, the semiconductor package of the present invention is a fan-out wafer level package (FOWLP).
[ semiconductor device ]
The semiconductor device of the present invention comprises a layer containing a cured product of the resin composition layer of the present invention. The semiconductor device of the present invention can be manufactured using the printed wiring board or the semiconductor package of the present invention.
Examples of the semiconductor device include various semiconductor devices used in electric products (for example, computers, mobile phones, digital cameras, televisions, and the like) and vehicles (for example, motorcycles, automobiles, trains, ships, aircrafts, and the like).
[ examples ]
The present invention will be specifically described below with reference to examples. The present invention is not limited to these examples. In the following, the terms "part(s)" and "%" representing the amount are "part(s) by mass" and "% by mass", respectively, unless otherwise explicitly indicated. Further, the temperature conditions and pressure conditions in the case where no particular designation is made are room temperature (25 ℃) and atmospheric pressure (1 atm).
First, the evaluation methods of the measurement methods ・ will be described.
< Stud pull test >
1. Preparation of evaluation substrate
(1) Base treatment of copper foil
A glass cloth substrate epoxy resin double-sided copper-clad laminate having a copper foil on the surface thereof (thickness of copper foil 18 μm, thickness of substrate 0.8mm, "R-1766" manufactured by Panasonic Co.) was prepared. Both surfaces were roughened by etching with a microetching solution (CZ 8101, メック) so that the copper etching amount was 2 μm. The thus-obtained copper-clad laminate is referred to as a "roughened copper-clad laminate".
(2) Lamination of resin sheets
The resin sheets prepared in examples and comparative examples were laminated on one surface of the roughened copper-clad laminate using a batch type vacuum press laminator (2-stage laminator "CVP 700" manufactured by Nikko-Materials) so that the resin composition layer was bonded to the roughened copper-clad laminate. The lamination was carried out by reducing the pressure to 3hPa or less for 30 seconds and then pressing the laminate at 100 ℃ and 0.74MPa for 30 seconds. After the lamination treatment, the resin sheet was thermally pressed at 100 ℃ and 0.5MPa for 60 seconds at atmospheric pressure to be smoothed. After the smoothing treatment, the resultant was put into an oven at 200 ℃ and heated for 90 minutes to cure the resin composition layer. Thus, an "evaluation substrate a" was obtained in which a cured product layer of the resin composition was provided on the roughened copper-clad laminate. For each resin composition, 5 evaluation substrates a were prepared.
Stud pull test
(1) Test conditions
The peel mode and the load value (kgf/cm) at the time of peeling were evaluated by using a student pull tester (ROMULUS, manufactured by the company of the Quad Group Inc.) according to the following procedures2)。
That is, aluminum stud pins (diameter of the bonding surface 2.7 mm. phi.; P/N901106) having an epoxy adhesive fixed thereto were heated in an oven at 150 ℃ for 1 hour to bond the stud pins to the cured product layer of the resin composition of the evaluation substrate A. Then, the Stud pin was pulled at a speed of 2 kgf/sec in a direction perpendicular to the main surface of the evaluation substrate by the above-mentioned student pull tester, and the load value (kgf/cm) at the time of peeling of the cured product layer was measured2) The peeling pattern was observed with an optical microscope. Tests were performed on 5 evaluation substrates a prepared for each resin composition (N = 5).
(2) Determination of peeling mode
As a result of the 5-time test, the case where the interface between the copper clad laminated sheet and the cured product layer was peeled (interlayer peeling) 3 times or more was determined as "peeling mode I", the case where the cured product layer was broken by cohesion (intralayer peeling) 3 times or more was determined as "peeling mode II", and the case where the interface between the cured product layer and the stud pin was peeled (interlayer peeling) 3 times or more was determined as "peeling mode III". The cases of "peeling mode I" and "peeling mode III" indicate that the cohesive force (in-layer adhesion strength) of the cured product layer is higher than the interface adhesion strength of the cured product layer-copper foil or the interface adhesion strength of the cured product layer-Stud pin (epoxy adhesive), and is larger than the Stud pull measurement value (load value at the time of peeling). In contrast, the case of "peel mode II" indicates that the cohesive strength of the cured product layer is lower than the interfacial adhesion strength of the cured product layer-copper foil or the cured product layer-stud pin (epoxy adhesive).
< evaluation of warpage >
The resin sheets prepared in examples and comparative examples were laminated on the entire surface of a 12-inch silicon wafer (thickness 775 μm) by using a batch type vacuum press laminator (2-stage laminator "CVP 700" manufactured by Nikko-Materials corporation) so that the resin composition layer was bonded to the silicon wafer. The support was peeled off by further laminating a resin sheet on the exposed surface of the resin composition layer in the same manner. Thus, 2 resin composition layers (total thickness: 100 μm) were formed on one surface of a 12-inch silicon wafer. Note that the lamination (lamination processing and smoothing processing) was performed under the same conditions as in the above 1. (2).
The obtained laminate was heated in an oven at 180 ℃ for 90 minutes to cure the resin composition layer, thereby forming an insulating layer. The end of the obtained silicon wafer with an insulating layer was pressed against a horizontal table, and the distance between the end of the wafer on the opposite side of the pressed portion and the table was measured as the amount of warpage. Then, warpage was evaluated by the following criteria.
Evaluation criteria for warpage:
o, warpage of 0mm to 2mm (2000 μm)
A warp amount of more than 2mm
< evaluation of Long-term reliability >
1. Production of cured product for evaluation
A part of the resin sheets produced in examples and comparative examples was cut out, and heated at 200 ℃ for 90 minutes to cure the resin composition layer. The support was then peeled off to obtain a cured product A for evaluation.
2. Evaluation of Long term reliability
Evaluation of Long-term reliability the evaluation was carried out by subjecting the cured product A to an HTS test, measuring the breaking point strength before and after the HTS (high Thermal storage) test, and calculating the change rate (%) of the breaking point strength.
(1) HTS assay
The cured product A for evaluation was subjected to HTS test. In the HTS test, the cured product A for evaluation was held at 150 ℃ for 1000 hours. Thus, a cured product A' for evaluation after HTS test was obtained.
(2) Determination of Break Point Strength before and after HTS testing
The cured product A for evaluation was cut into a 1-shaped sample viewed in a dumbbell shape in plan view, thereby obtaining 5 test pieces B. Similarly, the cured product A 'for evaluation was cut into No. 1 dumbbell-shaped pieces viewed from above, thereby obtaining 5 test pieces B'. For each test piece B, B', a tensile test was carried out using a tensile tester "RTC-1250A" manufactured by オリエンテック company under the measurement conditions of 23 ℃ and a test speed of 5mm/min, and the tensile breaking point strength (also simply referred to as "breaking point strength") was determined from the stress-strain curve. The measurement was carried out in accordance with JIS K7127: 1999. The average of the breaking point strengths of 5 test pieces B was defined as the tensile breaking point strength σ 0 before the HTS test. The average of the breaking point strengths of 5 test pieces B' was defined as the tensile breaking point strength σ 1 after the HTS test. Then, the change rate (%) of the tensile breaking point strength before and after the HTS test was calculated based on the following formula.
Rate of change (%) = { (σ 1- σ 0)/σ 0} × 100
The long-term reliability was evaluated based on the calculated change rate (%) according to the following criteria.
Evaluation criteria for long-term reliability:
case where the absolute value of the change rate (%) is less than 10% (small change rate, excellent long-term reliability)
X-case where the absolute value of the change rate (%) is 10% or more (large change rate, poor long-term reliability)
The test piece B' of comparative example 1, which was evaluated to have poor long-term reliability, was observed to confirm the deterioration due to oxidation. In addition, with respect to each of the resin compositions prepared in examples and comparative examples, evaluation was also performed on resin sheets in which the thickness of the resin composition layer was changed to 25 μm, 100 μm, and the like, and it was confirmed that the peel mode and the measured strength in the Stud pull test were not changed, and the same tendency was exhibited in the long-term reliability.
< Synthesis example 1> (Synthesis of stress relaxation Material A)
To a reaction vessel, 69G of 2-functional 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 ("イプゾール 150" manufactured by Bright petrochemicals), and 0.005G of dibutyltin laurate were added, mixed and dissolved uniformly. The temperature of the resulting solution was raised to 60 ℃ and 8g of isophorone diisocyanate (IPDI, manufactured by エボニックデグサジャパン Co., Ltd.; isocyanate group equivalent: 113g/eq.) was added while stirring, and the reaction was carried out for about 3 hours. Thus, a1 st reaction solution was obtained.
Then, 23g of cresol novolak resin ("KA-1160" manufactured by DIC corporation and having a hydroxyl equivalent of 117g/eq.) and 60g of diethylene glycol ethyl ether acetate (manufactured by ダイセル corporation) were added to the first reaction solution 1, and the temperature was raised to 150 ℃ while stirring, and a reaction was carried out for about 10 hours. Thus, a2 nd reaction solution was obtained. Tong (Chinese character of 'tong')FT-IR passage confirmation of 2250cm-1Disappearance of NCO peak (b). The disappearance of NCO peak was confirmed as the end point of the reaction, and the reaction solution No. 2 was cooled to room temperature. Then, the 2 nd reaction solution was filtered through a100 mesh filter cloth. Thus, as the filtrate, a solution (nonvolatile content 50 mass%) containing the stress relaxation material a having a reactive functional group (phenolic hydroxyl group-containing polybutadiene resin) as a nonvolatile component was obtained. The number average molecular weight of the stress relaxation material A was 5,900, and the glass transition temperature was-7 ℃.
< Synthesis example 2> (Synthesis of Maleimide Compound A)
An MEK solution (nonvolatile content: 70 mass%) of the maleimide compound A was prepared in accordance with the method described in Synthesis example 1 of the public bulletin technique No. 2020-500211 of the Association of the invention. The maleimide compound A has a structure represented by the following formula.
[ solution 19]
Determination of Maleimide Compound A1The FD-MS spectrum of (a), peaks of M + =560, 718, and 876 were confirmed. These peaks correspond to n, respectively1In the case of 0, 1 and 2. In addition, the maleimide compound A was analyzed by GPC1The number n of repeating units in the indane skeleton part is determined based on the number average molecular weight1A value of (1), then n1=1.47, molecular weight distribution (Mw/Mn) = 1.81. Further, maleimide compound A1Average number of repeating units n in 100 area% of the total amount of (A)1The content ratio of the maleimide compound of 0 was 26.5 area%.
The FD-MS spectrum of the maleimide compound A was measured by the following measurement apparatus and measurement conditions.
(FD-MS Spectrum measuring apparatus and measuring conditions)
A measuring device: JMS-T100GC AccuTOF
Measurement conditions
Measurement range: m/z =4.00~2000.00
Rate of change: 51.2mA/min
Final current value: 45mA
Anode voltage: -10kV
Recording interval: 0.07sec
GPC of the maleimide compound A was measured by the following measurement apparatus and measurement conditions.
A measuring device: HLC-8320 GPC, manufactured by Tosoh corporation "
Column: "HXL-L" manufactured by Tosoh corporation, "TSK-GEL G2000 HXL" manufactured by Tosoh corporation, "TSK-GEL G3000 HXL" manufactured by Tosoh corporation, and "TSK-GEL G4000 HXL" manufactured by Tosoh corporation "
A detector: RI (differential refractometer)
Data processing: "GPC word station EcoSEC-workbench" manufactured by Tosoh corporation "
The measurement conditions were as follows: column temperature 40 deg.C
Elution solvent tetrahydrofuran
Flow rate 1.0 ml/min
The standard is as follows: monodisperse polystyrene of known molecular weight was used according to the aforementioned measurement guidelines "GPC word station EcoSEC-WorkStation".
Sample preparation: the resulting tetrahydrofuran solution containing 1.0 mass% of maleimide compound in terms of nonvolatile components was filtered through a microfilter (50. mu.l).
The molecular weight distribution (weight average molecular weight (Mw)/number average molecular weight (Mn)) of the maleimide compound A, and the average number of repeating units "n" relating to the indane skeleton in the maleimide compound1"means calculated from a GPC chart obtained by the GPC measurement. In addition, the average number of repeating units "n1"means calculated based on the number average molecular weight (Mn). In particular, for n10 to 4, the theoretical molecular weight and the actual molecular weight in GPC are plotted on a scattergram, and an approximate straight line is drawn. Then, the number average molecular weight (Mn) is obtained from the point indicated by the actually measured value Mn (1) on the straight line, and the average repeating unit "n" is calculated1". Further, based on the results of GPC measurement, the maleimide compound A was calculated1Average number of repeating units n in 100 area% of the total amount of (A)1Content of maleimide Compound 0Ratio (area%). For details, reference may be made to the invention association public technical publication No. 2020-.
[ example 1]
(1) Preparation of resin composition
3 parts of bisphenol A type epoxy resin ("828 EL" manufactured by Mitsubishi ケミカル, epoxy equivalent 189g/eq.), 1 part of naphthylene ether type epoxy resin ("HP 6000" manufactured by DIC, epoxy equivalent 250g/eq.), 2 parts of glycidylamine type epoxy resin ("630" manufactured by Mitsubishi ケミカル, epoxy equivalent 95g/eq.), 20 parts of a stress relaxation material A, and spherical silica ("SO-C2" manufactured by アドマテックス, average particle size 0.5 μm, specific surface area 5.8 m) surface-treated with an aminosilicone type coupling agent ("KBM 573" manufactured by shin-Etsu chemical Co., Ltd265 parts/g), 4 parts of a maleimide compound (manufactured by デザイナーモレキュールズ, BMI-689), 2 parts of a phenol curing agent (manufactured by DIC, "KA-1160", phenolic hydroxyl equivalent: 117g/eq), 0.05 part of a curing accelerator (manufactured by Siguo chemical industries, "1B 2 PZ", 1-benzyl-2-phenylimidazole), and 15 parts of methyl ethyl ketone were mixed and uniformly dispersed in a high-speed rotary mixer to prepare a varnish of a resin composition.
(2) Production of resin sheet
As a support, a PET film having a release layer (manufactured by LINTEC, "AL 5", 38 μm thick) was prepared. The prepared varnish was uniformly applied to the release layer of the support so that the thickness of the dried resin composition layer was 50 μm. Then, the varnish was dried at 80 ℃ to 120 ℃ (average 100 ℃) for 4 minutes to prepare a resin sheet containing a support and a resin composition layer provided on the support.
[ example 2]
(1) Preparation of resin composition
4 parts of bisphenol A type epoxy resin ("828 EL" manufactured by Mitsubishi ケミカル, epoxy equivalent 189g/eq.), 1 part of naphthylene ether type epoxy resin ("HP 6000" manufactured by DIC, epoxy equivalent 250g/eq.), 4 parts of glycidylamine type epoxy resin ("630" manufactured by Mitsubishi ケミカル, epoxy equivalent 95g/eq.), 12 parts of a stress relaxation material A, and an aminosilane coupling agent (CROSS CHEMICAL CO., LTD.) were added"KBM 573", manufactured by ASHI corporation ") of surface-treated spherical silica (" SO-C2 ", manufactured by アドマテックス Co., Ltd., average particle diameter of 0.5 μm and specific surface area of 5.8m260 parts/g), 1 part of a maleimide compound (manufactured by デザイナーモレキュールズ, BMI-689), 1 part of a phenol curing agent (manufactured by DIC, KA-1160; phenolic hydroxyl equivalent: 117g/eq), 6.2 parts of an active ester curing agent (manufactured by DIC, HPC-8000-65T; active group equivalent: 223g/eq, 65 mass% solids in toluene solution), 0.05 part of a curing accelerator (4-Dimethylaminopyridine (DMAP)), and 15 parts of methyl ethyl ketone were mixed and uniformly dispersed in a high-speed rotary mixer to prepare a varnish of a resin composition.
(2) Production of resin sheet
Using the varnish thus obtained, a resin sheet was produced in the same manner as in example 1.
[ example 3]
(1) Preparation of resin composition
4 parts of naphthalene type epoxy resin ("HP-4032" manufactured by DIC corporation, epoxy equivalent 144g/eq.), 2 parts of glycidylamine type epoxy resin ("630" manufactured by Mitsubishi ケミカル, epoxy equivalent 95g/eq.), 20 parts of stress relaxation material A, 1 part of epoxidized polybutadiene resin ("JP-100" manufactured by Nippon Cauda corporation, acrylic rubber particles ("EXL 2655" manufactured by Wu Yu chemical industry Co.), 1 part of spherical silica surface-treated with an aminosilane-based coupling agent ("KBM 573" manufactured by shin-Etsu chemical industry Co., デンカ, "UFP-30" manufactured by UFP-30, average particle size 0.3 μm, specific surface area 30.7m245 parts/g), 2 parts of a maleimide compound (manufactured by デザイナーモレキュールズ, BMI-689), 2 parts of a phenol curing agent (manufactured by DIC, "KA-1160", phenolic hydroxyl equivalent: 117g/eq), 3.1 parts of an active ester curing agent (manufactured by DIC, "HPC-8000-65T", active group equivalent 223g/eq, 65 mass% solids in toluene solution), 0.05 part of a curing accelerator (manufactured by Sikka chemical industry, "1B 2 PZ"), and 15 parts of methyl ethyl ketone were mixed and uniformly dispersed in a high-speed rotary mixer to prepare a varnish of a resin composition.
(2) Production of resin sheet
Using the varnish thus obtained, a resin sheet was produced in the same manner as in example 1.
[ example 4]
(1) Preparation of resin composition
3 parts of bisphenol A type epoxy resin ("828 EL" manufactured by Mitsubishi ケミカル Co., Ltd., epoxy equivalent of 189g/eq.), 2 parts of naphthalene type epoxy resin ("HP-4032" manufactured by DIC Co., Ltd., epoxy equivalent of 144g/eq.), 2 parts of naphthylene ether type epoxy resin ("HP 6000" manufactured by DIC Co., Ltd., epoxy equivalent of 250g/eq.), 2 parts of naphthol type epoxy resin ("ESN 475V" manufactured by Nippon iron ケミカル & マテリアル Co., Ltd., epoxy equivalent of 330g/eq.), 1 part of phenoxy resin ("YX 7200" manufactured by Mitsubishi ケミカル Co., Ltd.), 0.5 part of epoxidized polybutadiene resin ("JP-100" manufactured by Nippon Cauda corporation), 2 parts of acrylic rubber particles ("EXL 2655" manufactured by Wuyu chemical Co., Ltd., and spherical silica surface-treated with aminosilicone-based coupling agent ("KBM 573" manufactured by Kuntze chemical industry Co., Ltd.) (SO-C46 2 "manufactured by Wookuyu chemical industry Co., Ltd."), Average particle diameter of 0.5 μm and specific surface area of 5.8m2(g) 80 parts, 3 parts of a maleimide compound (manufactured by デザイナーモレキュールズ, BMI-689), 15.4 parts of an active ester-based curing agent (manufactured by DIC, "HPC-8000-65T", active base equivalent 223g/eq, 65 mass% solids in toluene solution), 0.2 parts of a curing accelerator (manufactured by four chemical industries, 1B2 PZ), 0.01 parts of a curing accelerator (DMAP), and 15 parts of methyl ethyl ketone were mixed and uniformly dispersed in a high-speed rotary mixer to prepare a varnish of a resin composition.
(2) Production of resin sheet
Using the varnish thus obtained, a resin sheet was produced in the same manner as in example 1.
[ example 5]
A resin varnish was prepared and a resin sheet was produced in the same manner as in example 1, except that 4 parts of the maleimide compound a prepared in synthetic example 2 was used in place of 4 parts of the maleimide compound (manufactured by デザイナーモレキュールズ, "BMI-689").
Comparative example 1
Except for (i) the point that the amount of the stress relaxation material A was changed from 10 parts to 18 parts and (ii) the point that an aminosilicone-based coupling agent (manufactured by shin-Etsu chemical industries Co., Ltd.) was used "KBM 573'), surface-treated spherical silica ("SO-C2" manufactured by アドマテックス Co., Ltd.), and having an average particle diameter of 0.5 μm and a specific surface area of 5.8m2A resin varnish was prepared in the same manner as in example 1 except that the compounding amount of (i)/g) was changed from 65 parts to 95 parts, and (iii) 1.6 parts of an active ester-based curing agent ("HPC-8000-65T", available from DIC corporation, active group equivalent of 223g/eq, and a toluene solution having a solid content of 65 mass%) was further compounded, to prepare a resin sheet.
Comparative example 2
Except for (i) a point not containing the stress relaxation material A and (ii) a spherical silica (SO-C2, manufactured by アドマテックス, average particle diameter 0.5 μm, specific surface area 5.8 m) surface-treated with an aminosilane-based coupling agent (KBM 573, manufactured by shin-Etsu chemical Co., Ltd.)2(ii)/g) was changed from 65 parts to 45 parts, and (iii) 9.2 parts of an active ester-based curing agent (a toluene solution having a solid content of 65 mass% and an equivalent weight of 223g/eq, manufactured by DIC) was added in place of 2 parts of a phenol-based curing agent (a toluene solution having a solid content of 65 mass%, manufactured by DIC) to prepare a resin varnish and prepare a resin sheet in the same manner as in example 1.
Comparative example 3
(1) Preparation of resin composition
3 parts of naphthalene-type epoxy resin ("HP-4032" manufactured by DIC Co., Ltd., epoxy equivalent 144g/eq.), 1 part of naphthol-type epoxy resin ("ESN 475V" manufactured by Nippon iron ケミカル & マテリアル Co., epoxy equivalent 330g/eq.), 0.5 part of phenoxy resin ("YX 7200" manufactured by Mitsubishi ケミカル Co., Ltd.), 10 parts of core-shell type rubber particles ("MR-01" manufactured by カネカ Co., Ltd.), and spherical silica (SO-C2 "manufactured by アドマテックス Co., Ltd., average particle diameter 0.5 μm, specific surface area 5.8 m) surface-treated with an aminosilicone-type coupling agent (" KBM573 "manufactured by shin-Etsu chemical Co., Ltd.)265 parts/g), 1 part of phenol curing agent (KA-1160, phenolic hydroxyl equivalent: 117g/eq, manufactured by DIC Co., Ltd.), 9.2 parts of active ester curing agent (toluene solution with 65 mass% solid content, manufactured by DIC Co., Ltd. "HPC-8000-65T", active group equivalent 223 g/eq), 0.4 part of curing accelerator (1B 2PZ, manufactured by Sikko chemical industries Co., Ltd.), and 0.4 part of curing accelerator0.01 part of the (DMAP) component and 15 parts of methyl ethyl ketone were mixed and uniformly dispersed in a high-speed rotary mixer to prepare a varnish of the resin composition.
(2) Production of resin sheet
Using the varnish thus obtained, a resin sheet was produced in the same manner as in example 1.
Comparative example 4
A varnish of a resin composition was prepared and a resin sheet was produced in the same manner as in example 4, except that 5 parts of a benzoxazine compound (P-d type benzoxazine compound manufactured by four kingdoms chemical industry) was further added.
The resin compositions prepared in examples 1 to 5 and comparative examples 1 to 4 exhibited a heat generation peak in a range of 120 to 190 ℃ when the temperature was raised from 30 ℃ to 350 ℃ at a temperature raising rate of 5 ℃/min using a differential scanning calorimeter.
The results of examples 1 to 5 and comparative examples 1 to 4 are shown in Table 1.
[ Table 1]
[ description of the drawings ]
1 base material (roughened copper-clad laminate)
2 a cured product layer of the resin composition
10 epoxy adhesive
11 stud pin.
Claims (16)
1. A resin composition comprising (A) an epoxy resin and (B) a stress relaxation material,
as follows<Stud pull test conditions>When 5 tests were carried out, the following results were shown<Criterion for determining peeling mode>In the peeling mode I or the peeling mode III, and the load value at the time of peeling is 180kgf/cm2In the above-mentioned manner,
< conditions of the Stud pull test (pulling test using a rivet-shaped jig) >
A layer of the resin composition is provided on the roughened copper-clad laminate at a temperature T1Heating at a temperature of 90 deg.C for 90 minutes to cure the resin composition to obtain an evaluation substrate, fixing a Stud pin (rivet-shaped jig; diameter of bonding surface is 2.7mm) on the cured product layer of the resin composition of the evaluation substrate with an epoxy adhesive, heating at 150 deg.C for 1 hour to bond, pulling the Stud pin at a speed of 2 kgf/sec in a direction perpendicular to the main surface of the evaluation substrate with a Stud pull tester, and observing a load value (kgf/cm) at the time of peeling the cured product layer2) And a peeling mode in which when the temperature of a heat generation peak exhibited by the resin composition when the resin composition is heated from 30 ℃ to 350 ℃ at a temperature rise rate of 5 ℃/min using a differential scanning calorimeter is T (. degree. C.), the temperature T is set to1(DEG C) is a temperature of (T +10) (. degree.C.) or higher,
< criterion for determining peeling mode >
Peeling mode I: the copper-clad laminate has been subjected to interface detachable (interlayer peeling) 3 or more times
Peeling mode II: the solidified layer is broken by coagulation (peeling in the layer) for more than 3 times
Peeling mode III: the cured product layer-stud pin interface was peeled (interlayer peeling) 3 times or more.
2. The resin composition according to claim 1, wherein the content of the component (B) is 1% by mass or more based on 100% by mass of the total nonvolatile components in the resin composition.
3. The resin composition according to claim 1, wherein the number average molecular weight (Mn) of the component (B) is 1,000 or more.
4. The resin composition according to claim 1, wherein the component (B) is at least 1 selected from the group consisting of a resin having a glass transition temperature (Tg) of 25 ℃ or lower and a resin that is liquid at 25 ℃.
5. The resin composition according to claim 1, wherein the component (B) is a resin having 1 or more structures selected from a polybutadiene structure, a polysiloxane structure, a poly (meth) acrylate structure, a polyalkylene oxide structure, a polyisoprene structure, a polyisobutylene structure, and a polycarbonate structure in a molecule.
6. The resin composition according to claim 1, further comprising (C) an inorganic filler.
7. The resin composition according to claim 1, further comprising (D) a curing agent.
8. The resin composition according to claim 1, further comprising (E) a maleimide compound.
9. The resin composition according to claim 6, wherein the content of the component (C) is 40% by mass or more based on 100% by mass of the total nonvolatile components in the resin composition.
10. The resin composition according to claim 1, which is used for an insulating layer of a printed wiring board.
11. The resin composition according to claim 1, which is used for sealing.
12. A resin sheet comprising a support and a layer of the resin composition according to any one of claims 1 to 11 provided on the support.
13. A printed wiring board comprising an insulating layer, the insulating layer comprising a cured product of the resin composition according to any one of claims 1 to 10.
14. A semiconductor chip package comprising a sealing layer comprising a cured product of the resin composition according to any one of claims 1 to 9 and 11.
15. The semiconductor chip package of claim 14, which is a Fan-Out (Fan-Out) type package.
16. A semiconductor device comprising a layer comprising a cured product of the resin composition according to any one of claims 1 to 11.
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JP2020141247A JP7409262B2 (en) | 2020-08-24 | 2020-08-24 | resin composition |
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CN117384443A (en) * | 2023-12-12 | 2024-01-12 | 上海睿聚环保科技有限公司 | Flame-retardant regenerated plastic and preparation method thereof |
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JP2016010964A (en) | 2014-06-03 | 2016-01-21 | 三菱瓦斯化学株式会社 | Resin sheet and printed wiring board |
KR20170023719A (en) | 2015-08-24 | 2017-03-06 | 신에쓰 가가꾸 고교 가부시끼가이샤 | Heat-curable resin composition |
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CN105504677A (en) * | 2014-10-08 | 2016-04-20 | 太阳油墨制造株式会社 | Dry film, cured product and printed wiring board |
CN107556740A (en) * | 2016-07-01 | 2018-01-09 | 味之素株式会社 | Resin combination |
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CN117384443B (en) * | 2023-12-12 | 2024-03-01 | 上海睿聚环保科技有限公司 | Flame-retardant regenerated plastic and preparation method thereof |
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KR20220025677A (en) | 2022-03-03 |
JP7409262B2 (en) | 2024-01-09 |
TW202219166A (en) | 2022-05-16 |
JP2022036840A (en) | 2022-03-08 |
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