JP2024038791A - Resin composition, prepreg, copper-clad laminate, and printed wiring board - Google Patents
Resin composition, prepreg, copper-clad laminate, and printed wiring board Download PDFInfo
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- JP2024038791A JP2024038791A JP2022143068A JP2022143068A JP2024038791A JP 2024038791 A JP2024038791 A JP 2024038791A JP 2022143068 A JP2022143068 A JP 2022143068A JP 2022143068 A JP2022143068 A JP 2022143068A JP 2024038791 A JP2024038791 A JP 2024038791A
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- Prior art keywords
- resin composition
- cyclic imide
- formula
- compound
- groups
- Prior art date
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- 239000011342 resin composition Substances 0.000 title claims abstract description 64
- -1 cyclic imide compound Chemical class 0.000 claims abstract description 70
- 239000004593 Epoxy Substances 0.000 claims abstract description 40
- 150000001875 compounds Chemical class 0.000 claims abstract description 40
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims abstract description 37
- 125000003700 epoxy group Chemical group 0.000 claims abstract description 30
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 26
- 125000005462 imide group Chemical group 0.000 claims abstract description 23
- 125000002883 imidazolyl group Chemical group 0.000 claims abstract description 15
- 239000000539 dimer Substances 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 125000000962 organic group Chemical group 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000000732 arylene group Chemical group 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- VILAVOFMIJHSJA-UHFFFAOYSA-N dicarbon monoxide Chemical group [C]=C=O VILAVOFMIJHSJA-UHFFFAOYSA-N 0.000 claims description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract description 20
- 229910052802 copper Inorganic materials 0.000 abstract description 10
- 239000010949 copper Substances 0.000 abstract description 10
- 230000001747 exhibiting effect Effects 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 16
- 229920005989 resin Polymers 0.000 description 16
- 239000011347 resin Substances 0.000 description 16
- 150000002430 hydrocarbons Chemical group 0.000 description 13
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000003063 flame retardant Substances 0.000 description 11
- 239000000463 material Substances 0.000 description 11
- 229920003986 novolac Polymers 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 10
- 239000011889 copper foil Substances 0.000 description 10
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 10
- 239000011256 inorganic filler Substances 0.000 description 10
- 229910003475 inorganic filler Inorganic materials 0.000 description 10
- 150000003505 terpenes Chemical class 0.000 description 10
- 235000007586 terpenes Nutrition 0.000 description 10
- 239000000853 adhesive Substances 0.000 description 9
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 9
- 150000004985 diamines Chemical class 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 230000001070 adhesive effect Effects 0.000 description 8
- 239000011521 glass Substances 0.000 description 8
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 239000003505 polymerization initiator Substances 0.000 description 8
- 229910000859 α-Fe Inorganic materials 0.000 description 8
- XQUPVDVFXZDTLT-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C(C=C1)=CC=C1CC1=CC=C(N2C(C=CC2=O)=O)C=C1 XQUPVDVFXZDTLT-UHFFFAOYSA-N 0.000 description 7
- 239000006087 Silane Coupling Agent Substances 0.000 description 7
- 229910045601 alloy Inorganic materials 0.000 description 7
- 239000000956 alloy Substances 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- 239000000835 fiber Substances 0.000 description 7
- 239000010408 film Substances 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- 238000002156 mixing Methods 0.000 description 7
- 239000012766 organic filler Substances 0.000 description 7
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000003963 antioxidant agent Substances 0.000 description 6
- 239000002245 particle Substances 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 5
- ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 description 5
- 238000005227 gel permeation chromatography Methods 0.000 description 5
- 239000011164 primary particle Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 4
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 4
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 4
- 150000008065 acid anhydrides Chemical class 0.000 description 4
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
- 230000003078 antioxidant effect Effects 0.000 description 4
- 230000005540 biological transmission Effects 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 230000018044 dehydration Effects 0.000 description 4
- 238000006297 dehydration reaction Methods 0.000 description 4
- 239000003822 epoxy resin Substances 0.000 description 4
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000000465 moulding Methods 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 229920000647 polyepoxide Polymers 0.000 description 4
- 239000007870 radical polymerization initiator Substances 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- 239000001632 sodium acetate Substances 0.000 description 4
- 235000017281 sodium acetate Nutrition 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- DPQHRXRAZHNGRU-UHFFFAOYSA-N 2,4,4-trimethylhexane-1,6-diamine Chemical compound NCC(C)CC(C)(C)CCN DPQHRXRAZHNGRU-UHFFFAOYSA-N 0.000 description 3
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 3
- 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 3
- AYKYXWQEBUNJCN-UHFFFAOYSA-N 3-methylfuran-2,5-dione Chemical compound CC1=CC(=O)OC1=O AYKYXWQEBUNJCN-UHFFFAOYSA-N 0.000 description 3
- KMKWGXGSGPYISJ-UHFFFAOYSA-N 4-[4-[2-[4-(4-aminophenoxy)phenyl]propan-2-yl]phenoxy]aniline Chemical compound C=1C=C(OC=2C=CC(N)=CC=2)C=CC=1C(C)(C)C(C=C1)=CC=C1OC1=CC=C(N)C=C1 KMKWGXGSGPYISJ-UHFFFAOYSA-N 0.000 description 3
- MQAHXEQUBNDFGI-UHFFFAOYSA-N 5-[4-[2-[4-[(1,3-dioxo-2-benzofuran-5-yl)oxy]phenyl]propan-2-yl]phenoxy]-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(OC2=CC=C(C=C2)C(C)(C=2C=CC(OC=3C=C4C(=O)OC(=O)C4=CC=3)=CC=2)C)=C1 MQAHXEQUBNDFGI-UHFFFAOYSA-N 0.000 description 3
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 description 3
- DRQWQDPSMJHCCM-UHFFFAOYSA-N 6-[2-(2-methylimidazol-1-yl)ethyl]-1,3,5-triazine-2,4-diamine Chemical compound CC1=NC=CN1CCC1=NC(N)=NC(N)=N1 DRQWQDPSMJHCCM-UHFFFAOYSA-N 0.000 description 3
- 239000004925 Acrylic resin Substances 0.000 description 3
- 229920000178 Acrylic resin Polymers 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-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
- 229920000388 Polyphosphate Polymers 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- BGYHLZZASRKEJE-UHFFFAOYSA-N [3-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]-2,2-bis[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxymethyl]propyl] 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCC(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 BGYHLZZASRKEJE-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 3
- CEDDGDWODCGBFQ-UHFFFAOYSA-N carbamimidoylazanium;hydron;phosphate Chemical compound NC(N)=N.OP(O)(O)=O CEDDGDWODCGBFQ-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 229930003836 cresol Natural products 0.000 description 3
- XOSYHSRXLVMOBA-UHFFFAOYSA-N cyclopenta-1,3-diene;phenol Chemical compound C1C=CC=C1.C1C=CC=C1.OC1=CC=CC=C1 XOSYHSRXLVMOBA-UHFFFAOYSA-N 0.000 description 3
- QFTYSVGGYOXFRQ-UHFFFAOYSA-N dodecane-1,12-diamine Chemical compound NCCCCCCCCCCCCN QFTYSVGGYOXFRQ-UHFFFAOYSA-N 0.000 description 3
- 239000011572 manganese Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- KBJFYLLAMSZSOG-UHFFFAOYSA-N n-(3-trimethoxysilylpropyl)aniline Chemical compound CO[Si](OC)(OC)CCCNC1=CC=CC=C1 KBJFYLLAMSZSOG-UHFFFAOYSA-N 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- 229920003192 poly(bis maleimide) Polymers 0.000 description 3
- 239000001205 polyphosphate Substances 0.000 description 3
- 235000011176 polyphosphates Nutrition 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 3
- GRWFGVWFFZKLTI-IUCAKERBSA-N (-)-α-pinene Chemical compound CC1=CC[C@@H]2C(C)(C)[C@H]1C2 GRWFGVWFFZKLTI-IUCAKERBSA-N 0.000 description 2
- CFQZKFWQLAHGSL-FNTYJUCDSA-N (3e,5e,7e,9e,11e,13e,15e,17e)-18-[(3e,5e,7e,9e,11e,13e,15e,17e)-18-[(3e,5e,7e,9e,11e,13e,15e)-octadeca-3,5,7,9,11,13,15,17-octaenoyl]oxyoctadeca-3,5,7,9,11,13,15,17-octaenoyl]oxyoctadeca-3,5,7,9,11,13,15,17-octaenoic acid Chemical compound OC(=O)C\C=C\C=C\C=C\C=C\C=C\C=C\C=C\C=C\OC(=O)C\C=C\C=C\C=C\C=C\C=C\C=C\C=C\C=C\OC(=O)C\C=C\C=C\C=C\C=C\C=C\C=C\C=C\C=C CFQZKFWQLAHGSL-FNTYJUCDSA-N 0.000 description 2
- NOBYOEQUFMGXBP-UHFFFAOYSA-N (4-tert-butylcyclohexyl) (4-tert-butylcyclohexyl)oxycarbonyloxy carbonate Chemical compound C1CC(C(C)(C)C)CCC1OC(=O)OOC(=O)OC1CCC(C(C)(C)C)CC1 NOBYOEQUFMGXBP-UHFFFAOYSA-N 0.000 description 2
- JSNRRGGBADWTMC-UHFFFAOYSA-N (6E)-7,11-dimethyl-3-methylene-1,6,10-dodecatriene Chemical compound CC(C)=CCCC(C)=CCCC(=C)C=C JSNRRGGBADWTMC-UHFFFAOYSA-N 0.000 description 2
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 2
- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 description 2
- IPJGAEWUPXWFPL-UHFFFAOYSA-N 1-[3-(2,5-dioxopyrrol-1-yl)phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC(N2C(C=CC2=O)=O)=C1 IPJGAEWUPXWFPL-UHFFFAOYSA-N 0.000 description 2
- WFUGQJXVXHBTEM-UHFFFAOYSA-N 2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane Chemical compound CCC(C)(OO)OOC(C)(CC)OO WFUGQJXVXHBTEM-UHFFFAOYSA-N 0.000 description 2
- LYPGJGCIPQYQBW-UHFFFAOYSA-N 2-methyl-2-[[2-methyl-1-oxo-1-(prop-2-enylamino)propan-2-yl]diazenyl]-n-prop-2-enylpropanamide Chemical compound C=CCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCC=C LYPGJGCIPQYQBW-UHFFFAOYSA-N 0.000 description 2
- BKEXHEHRHGZBJO-UHFFFAOYSA-N 2-methyl-2-[[2-methyl-1-oxo-1-(propylamino)propan-2-yl]diazenyl]-n-propylpropanamide Chemical compound CCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCC BKEXHEHRHGZBJO-UHFFFAOYSA-N 0.000 description 2
- JZUHIOJYCPIVLQ-UHFFFAOYSA-N 2-methylpentane-1,5-diamine Chemical compound NCC(C)CCCN JZUHIOJYCPIVLQ-UHFFFAOYSA-N 0.000 description 2
- BIISIZOQPWZPPS-UHFFFAOYSA-N 2-tert-butylperoxypropan-2-ylbenzene Chemical compound CC(C)(C)OOC(C)(C)C1=CC=CC=C1 BIISIZOQPWZPPS-UHFFFAOYSA-N 0.000 description 2
- UIDDPPKZYZTEGS-UHFFFAOYSA-N 3-(2-ethyl-4-methylimidazol-1-yl)propanenitrile Chemical compound CCC1=NC(C)=CN1CCC#N UIDDPPKZYZTEGS-UHFFFAOYSA-N 0.000 description 2
- GPXCORHXFPYJEH-UHFFFAOYSA-N 3-[[3-aminopropyl(dimethyl)silyl]oxy-dimethylsilyl]propan-1-amine Chemical compound NCCC[Si](C)(C)O[Si](C)(C)CCCN GPXCORHXFPYJEH-UHFFFAOYSA-N 0.000 description 2
- ZLPORNPZJNRGCO-UHFFFAOYSA-N 3-methylpyrrole-2,5-dione Chemical compound CC1=CC(=O)NC1=O ZLPORNPZJNRGCO-UHFFFAOYSA-N 0.000 description 2
- WECDUOXQLAIPQW-UHFFFAOYSA-N 4,4'-Methylene bis(2-methylaniline) Chemical compound C1=C(N)C(C)=CC(CC=2C=C(C)C(N)=CC=2)=C1 WECDUOXQLAIPQW-UHFFFAOYSA-N 0.000 description 2
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 2
- NWIVYGKSHSJHEF-UHFFFAOYSA-N 4-[(4-amino-3,5-diethylphenyl)methyl]-2,6-diethylaniline Chemical compound CCC1=C(N)C(CC)=CC(CC=2C=C(CC)C(N)=C(CC)C=2)=C1 NWIVYGKSHSJHEF-UHFFFAOYSA-N 0.000 description 2
- QQGYZOYWNCKGEK-UHFFFAOYSA-N 5-[(1,3-dioxo-2-benzofuran-5-yl)oxy]-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(OC=2C=C3C(=O)OC(C3=CC=2)=O)=C1 QQGYZOYWNCKGEK-UHFFFAOYSA-N 0.000 description 2
- ZRSCAJHLPIPKBU-UHFFFAOYSA-N 5-methyl-2-phenyl-1h-imidazol-4-ol Chemical compound N1C(O)=C(C)N=C1C1=CC=CC=C1 ZRSCAJHLPIPKBU-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 2
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
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- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Chemical compound CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 229930009668 farnesene Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- LCWMKIHBLJLORW-UHFFFAOYSA-N gamma-carene Natural products C1CC(=C)CC2C(C)(C)C21 LCWMKIHBLJLORW-UHFFFAOYSA-N 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910021389 graphene Inorganic materials 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 230000017525 heat dissipation Effects 0.000 description 1
- CAYGQBVSOZLICD-UHFFFAOYSA-N hexabromobenzene Chemical compound BrC1=C(Br)C(Br)=C(Br)C(Br)=C1Br CAYGQBVSOZLICD-UHFFFAOYSA-N 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- LIKBJVNGSGBSGK-UHFFFAOYSA-N iron(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Fe+3].[Fe+3] LIKBJVNGSGBSGK-UHFFFAOYSA-N 0.000 description 1
- SZVJSHCCFOBDDC-UHFFFAOYSA-N iron(II,III) oxide Inorganic materials O=[Fe]O[Fe]O[Fe]=O SZVJSHCCFOBDDC-UHFFFAOYSA-N 0.000 description 1
- 229940119545 isobornyl methacrylate Drugs 0.000 description 1
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 235000001510 limonene Nutrition 0.000 description 1
- 229940087305 limonene Drugs 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- GPRDLRZMTVQCHM-UHFFFAOYSA-L magnesium;dihydroxide;hydrate Chemical compound O.[OH-].[OH-].[Mg+2] GPRDLRZMTVQCHM-UHFFFAOYSA-L 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- YSRVJVDFHZYRPA-UHFFFAOYSA-N melem Chemical compound NC1=NC(N23)=NC(N)=NC2=NC(N)=NC3=N1 YSRVJVDFHZYRPA-UHFFFAOYSA-N 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910001092 metal group alloy Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 1
- 238000010295 mobile communication Methods 0.000 description 1
- 235000019837 monoammonium phosphate Nutrition 0.000 description 1
- 239000006012 monoammonium phosphate Substances 0.000 description 1
- 229930003658 monoterpene Natural products 0.000 description 1
- 150000002773 monoterpene derivatives Chemical class 0.000 description 1
- 235000002577 monoterpenes Nutrition 0.000 description 1
- WVFLGSMUPMVNTQ-UHFFFAOYSA-N n-(2-hydroxyethyl)-2-[[1-(2-hydroxyethylamino)-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCO WVFLGSMUPMVNTQ-UHFFFAOYSA-N 0.000 description 1
- BUGISVZCMXHOHO-UHFFFAOYSA-N n-[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]-2-[[1-[[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]amino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCC(CO)(CO)NC(=O)C(C)(C)N=NC(C)(C)C(=O)NC(CO)(CO)CO BUGISVZCMXHOHO-UHFFFAOYSA-N 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- SFLRURCEBYIKSS-UHFFFAOYSA-N n-butyl-2-[[1-(butylamino)-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound CCCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCCC SFLRURCEBYIKSS-UHFFFAOYSA-N 0.000 description 1
- WMRNGPYHLQSTDL-UHFFFAOYSA-N n-cyclohexyl-2-[[1-(cyclohexylamino)-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound C1CCCCC1NC(=O)C(C)(C)N=NC(C)(C)C(=O)NC1CCCCC1 WMRNGPYHLQSTDL-UHFFFAOYSA-N 0.000 description 1
- OMTJOYXMCBWCFW-UHFFFAOYSA-N n-ethyl-2-[[1-(ethylamino)-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound CCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCC OMTJOYXMCBWCFW-UHFFFAOYSA-N 0.000 description 1
- MQMVFKNUCLYOFA-UHFFFAOYSA-N n-hexyl-2-[[1-(hexylamino)-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound CCCCCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCCCCC MQMVFKNUCLYOFA-UHFFFAOYSA-N 0.000 description 1
- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical compound C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- NXOSIMQLNWIXPE-UHFFFAOYSA-N octadecyl 2-(3,5-ditert-butyl-4,4-dihydroxycyclohexa-1,5-dien-1-yl)propanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C(C)C1=CC(C(C)(C)C)C(O)(O)C(C(C)(C)C)=C1 NXOSIMQLNWIXPE-UHFFFAOYSA-N 0.000 description 1
- SSDSCDGVMJFTEQ-UHFFFAOYSA-N octadecyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SSDSCDGVMJFTEQ-UHFFFAOYSA-N 0.000 description 1
- SRSFOMHQIATOFV-UHFFFAOYSA-N octanoyl octaneperoxoate Chemical compound CCCCCCCC(=O)OOC(=O)CCCCCCC SRSFOMHQIATOFV-UHFFFAOYSA-N 0.000 description 1
- MSRJTTSHWYDFIU-UHFFFAOYSA-N octyltriethoxysilane Chemical compound CCCCCCCC[Si](OCC)(OCC)OCC MSRJTTSHWYDFIU-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- SIWVEOZUMHYXCS-UHFFFAOYSA-N oxo(oxoyttriooxy)yttrium Chemical compound O=[Y]O[Y]=O SIWVEOZUMHYXCS-UHFFFAOYSA-N 0.000 description 1
- AJCDFVKYMIUXCR-UHFFFAOYSA-N oxobarium;oxo(oxoferriooxy)iron Chemical compound [Ba]=O.O=[Fe]O[Fe]=O.O=[Fe]O[Fe]=O.O=[Fe]O[Fe]=O.O=[Fe]O[Fe]=O.O=[Fe]O[Fe]=O.O=[Fe]O[Fe]=O AJCDFVKYMIUXCR-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000002530 phenolic antioxidant Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- XZTOTRSSGPPNTB-UHFFFAOYSA-N phosphono dihydrogen phosphate;1,3,5-triazine-2,4,6-triamine Chemical compound NC1=NC(N)=NC(N)=N1.OP(O)(=O)OP(O)(O)=O XZTOTRSSGPPNTB-UHFFFAOYSA-N 0.000 description 1
- PTMHPRAIXMAOOB-UHFFFAOYSA-N phosphoramidic acid Chemical compound NP(O)(O)=O PTMHPRAIXMAOOB-UHFFFAOYSA-N 0.000 description 1
- XFZRQAZGUOTJCS-UHFFFAOYSA-N phosphoric acid;1,3,5-triazine-2,4,6-triamine Chemical compound OP(O)(O)=O.NC1=NC(N)=NC(N)=N1 XFZRQAZGUOTJCS-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- BWJUFXUULUEGMA-UHFFFAOYSA-N propan-2-yl propan-2-yloxycarbonyloxy carbonate Chemical compound CC(C)OC(=O)OOC(=O)OC(C)C BWJUFXUULUEGMA-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- GRWFGVWFFZKLTI-UHFFFAOYSA-N rac-alpha-Pinene Natural products CC1=CCC2C(C)(C)C1C2 GRWFGVWFFZKLTI-UHFFFAOYSA-N 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 229930004725 sesquiterpene Natural products 0.000 description 1
- 150000004354 sesquiterpene derivatives Chemical class 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
- 229910000679 solder Inorganic materials 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000003746 surface roughness Effects 0.000 description 1
- MUTNCGKQJGXKEM-UHFFFAOYSA-N tamibarotene Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1NC(=O)C1=CC=C(C(O)=O)C=C1 MUTNCGKQJGXKEM-UHFFFAOYSA-N 0.000 description 1
- OPQYOFWUFGEMRZ-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOC(=O)C(C)(C)C OPQYOFWUFGEMRZ-UHFFFAOYSA-N 0.000 description 1
- NMOALOSNPWTWRH-UHFFFAOYSA-N tert-butyl 7,7-dimethyloctaneperoxoate Chemical compound CC(C)(C)CCCCCC(=O)OOC(C)(C)C NMOALOSNPWTWRH-UHFFFAOYSA-N 0.000 description 1
- SWAXTRYEYUTSAP-UHFFFAOYSA-N tert-butyl ethaneperoxoate Chemical compound CC(=O)OOC(C)(C)C SWAXTRYEYUTSAP-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- MDDUHVRJJAFRAU-YZNNVMRBSA-N tert-butyl-[(1r,3s,5z)-3-[tert-butyl(dimethyl)silyl]oxy-5-(2-diphenylphosphorylethylidene)-4-methylidenecyclohexyl]oxy-dimethylsilane Chemical compound C1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)C(=C)\C1=C/CP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 MDDUHVRJJAFRAU-YZNNVMRBSA-N 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- BJQWBACJIAKDTJ-UHFFFAOYSA-N tetrabutylphosphanium Chemical compound CCCC[P+](CCCC)(CCCC)CCCC BJQWBACJIAKDTJ-UHFFFAOYSA-N 0.000 description 1
- GFZMLBWMGBLIDI-UHFFFAOYSA-M tetrabutylphosphanium;acetate Chemical compound CC([O-])=O.CCCC[P+](CCCC)(CCCC)CCCC GFZMLBWMGBLIDI-UHFFFAOYSA-M 0.000 description 1
- RKHXQBLJXBGEKF-UHFFFAOYSA-M tetrabutylphosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)CCCC RKHXQBLJXBGEKF-UHFFFAOYSA-M 0.000 description 1
- LVEOKSIILWWVEO-UHFFFAOYSA-N tetradecyl 3-(3-oxo-3-tetradecoxypropyl)sulfanylpropanoate Chemical compound CCCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCCC LVEOKSIILWWVEO-UHFFFAOYSA-N 0.000 description 1
- BRKFQVAOMSWFDU-UHFFFAOYSA-M tetraphenylphosphanium;bromide Chemical compound [Br-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 BRKFQVAOMSWFDU-UHFFFAOYSA-M 0.000 description 1
- USFPINLPPFWTJW-UHFFFAOYSA-N tetraphenylphosphonium Chemical compound C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 USFPINLPPFWTJW-UHFFFAOYSA-N 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- MZHULIWXRDLGRR-UHFFFAOYSA-N tridecyl 3-(3-oxo-3-tridecoxypropyl)sulfanylpropanoate Chemical compound CCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCC MZHULIWXRDLGRR-UHFFFAOYSA-N 0.000 description 1
- FRGPKMWIYVTFIQ-UHFFFAOYSA-N triethoxy(3-isocyanatopropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCN=C=O FRGPKMWIYVTFIQ-UHFFFAOYSA-N 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
- NBXZNTLFQLUFES-UHFFFAOYSA-N triethoxy(propyl)silane Chemical compound CCC[Si](OCC)(OCC)OCC NBXZNTLFQLUFES-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- NMEPHPOFYLLFTK-UHFFFAOYSA-N trimethoxy(octyl)silane Chemical compound CCCCCCCC[Si](OC)(OC)OC NMEPHPOFYLLFTK-UHFFFAOYSA-N 0.000 description 1
- RMZAYIKUYWXQPB-UHFFFAOYSA-N trioctylphosphane Chemical compound CCCCCCCCP(CCCCCCCC)CCCCCCCC RMZAYIKUYWXQPB-UHFFFAOYSA-N 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- QQBLOZGVRHAYGT-UHFFFAOYSA-N tris-decyl phosphite Chemical compound CCCCCCCCCCOP(OCCCCCCCCCC)OCCCCCCCCCC QQBLOZGVRHAYGT-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 229940070710 valerate Drugs 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Landscapes
- Reinforced Plastic Materials (AREA)
- Epoxy Resins (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Abstract
Description
本発明は、樹脂組成物等に関する。 The present invention relates to resin compositions and the like.
近年、携帯電話に代表される移動体通信機器、その基地局装置、サーバー、ルーター等のネットワークインフラ機器、大型コンピュータ等の電子機器では、使用する信号の高速化及び大容量化が年々進んでいる。これに伴い、これらの電子機器に搭載されるプリント配線板には20GHz領域といった高周波帯が使用されるため、低誘電率、低誘電正接、低熱膨張率、高耐熱性、低吸水性など、プリント配線板用材料に求められる特性はますます高まっている。 In recent years, the speed and capacity of signals used in mobile communication devices such as mobile phones, their base stations, network infrastructure devices such as servers and routers, and electronic devices such as large computers have been increasing year by year. . Along with this, the printed wiring boards installed in these electronic devices use high frequency bands such as the 20 GHz region, so printed wiring boards with low dielectric constant, low dielectric loss tangent, low coefficient of thermal expansion, high heat resistance, and low water absorption, etc. The characteristics required of materials for wiring boards are increasing more and more.
これらの特性を満たす可能性のある材料としては、変性ポリフェニレンエーテル樹脂、マレイミド樹脂、エポキシ樹脂等が挙げられる(特許文献1~3)。これらの中でもマレイミド樹脂は低誘電率、低誘電正接であり、耐熱性も高いことから高周波対応のプリント配線板用材料として用いられている(特許文献4、5)。 Examples of materials that may satisfy these characteristics include modified polyphenylene ether resins, maleimide resins, and epoxy resins (Patent Documents 1 to 3). Among these, maleimide resin has a low dielectric constant, low dielectric loss tangent, and high heat resistance, so it is used as a material for printed wiring boards compatible with high frequencies (Patent Documents 4 and 5).
しかしながら、マレイミド樹脂は硬化温度が高いことや溶融粘度が高いことに起因して、銅張積層板やプリント配線板用の材料としての特性を十分に満たしていない。さらに使用する周波数帯が高まるにつれて、回路を形成する銅の表面粗さを小さくしなければならず、樹脂と銅とのより高い接着性が求められている。 However, maleimide resins do not have sufficient characteristics as materials for copper-clad laminates and printed wiring boards due to their high curing temperatures and high melt viscosity. Furthermore, as the frequency band used increases, the surface roughness of the copper forming the circuit must be reduced, and higher adhesion between the resin and the copper is required.
従って、本発明は、低誘電率、低誘電正接でありながら、銅との高い接着性を有する硬化物となる樹脂組成物を提供することを目的とする。 Therefore, an object of the present invention is to provide a resin composition that becomes a cured product that has a low dielectric constant and a low dielectric loss tangent and has high adhesion to copper.
本発明者らは上記課題を解決するため鋭意研究した結果、下記樹脂組成物が上記目的を達成できることを見出し、本発明を完成した。
すなわち、本発明は、下記の樹脂組成物等を提供するものである。
As a result of intensive research to solve the above-mentioned problems, the present inventors discovered that the following resin composition can achieve the above-mentioned objects, and completed the present invention.
That is, the present invention provides the following resin composition and the like.
[1]
(a)環状イミド化合物、
(b)エポキシ化合物、及び
(c)イミダゾール化合物
を少なくとも有し、前記環状イミド化合物の環状イミド基数、前記エポキシ化合物のエポキシ基数、及び前記イミダゾール化合物のイミダゾール基数が下記2式をいずれも満たす樹脂組成物。
0.3 ≦ 環状イミド基数/エポキシ基数 ≦ 3.0
2.0 ≦ エポキシ基数/イミダゾール基数 ≦ 20.0
[2]
(a)環状イミド化合物が下記式(1)で表される[1]に記載の樹脂組成物。
[3]
式(1)中のAで示される有機基が下記構造式で示される4価の有機基のいずれかである[2]に記載の樹脂組成物。
[4]
式(1)中のQで示される2価の炭化水素基が下記構造式のいずれかで示される2価の炭化水素基及びダイマー酸骨格由来の2価炭化水素基から選ばれるものである[2]または[3]に記載の樹脂組成物。
[5]
式(1)中のBで示されるアリーレン基が下記構造式のいずれかで示されるアリーレン基である[2]~[4]のいずれか1項に記載の樹脂組成物。
[6]
(a)成分の環状イミド化合物が、式(1)中のmが0である環状イミド化合物である[2]~[5]のいずれか1項に記載の樹脂組成物。
[7]
[1]~[6]のいずれか1項に記載の樹脂組成物を含有してなるプリプレグ。
[8]
[7]に記載のプリプレグを有する銅張積層板。
[9]
[8]に記載の銅張積層板を有するプリント配線板。
[1]
(a) cyclic imide compound,
(b) A resin composition comprising at least an epoxy compound and (c) an imidazole compound, in which the number of cyclic imide groups of the cyclic imide compound, the number of epoxy groups of the epoxy compound, and the number of imidazole groups of the imidazole compound satisfy the following two formulas. thing.
0.3 ≦ Number of cyclic imide groups/Number of epoxy groups ≦ 3.0
2.0 ≦ Number of epoxy groups/Number of imidazole groups ≦ 20.0
[2]
(a) The resin composition according to [1], wherein the cyclic imide compound is represented by the following formula (1).
[3]
The resin composition according to [2], wherein the organic group represented by A in formula (1) is any of the tetravalent organic groups represented by the following structural formula.
[4]
The divalent hydrocarbon group represented by Q in formula (1) is selected from a divalent hydrocarbon group represented by any of the following structural formulas and a divalent hydrocarbon group derived from a dimer acid skeleton [ 2] or the resin composition according to [3].
[5]
The resin composition according to any one of [2] to [4], wherein the arylene group represented by B in formula (1) is an arylene group represented by any of the following structural formulas.
[6]
The resin composition according to any one of [2] to [5], wherein the cyclic imide compound as component (a) is a cyclic imide compound in which m in formula (1) is 0.
[7]
A prepreg containing the resin composition according to any one of [1] to [6].
[8]
A copper-clad laminate having the prepreg according to [7].
[9]
A printed wiring board having the copper-clad laminate according to [8].
本発明の樹脂組成物は、低誘電率、低誘電正接でありながら、銅との高い接着性を有する硬化物となる。したがって、本発明の樹脂組成物は高周波用のプリプレグ、銅張積層板、プリント配線板、フレキシブルプリント配線板の基材フィルム、カバーレイフィルム、カバーレイフィルム用接着剤、放熱用接着剤、電磁波シールド、半導体封止材等の用途に有用である。 The resin composition of the present invention becomes a cured product that has a low dielectric constant and a low dielectric loss tangent, and has high adhesion to copper. Therefore, the resin composition of the present invention is suitable for use in high-frequency prepregs, copper-clad laminates, printed wiring boards, base films for flexible printed wiring boards, coverlay films, adhesives for coverlay films, heat dissipation adhesives, and electromagnetic shielding. It is useful for applications such as semiconductor encapsulation materials.
以下、本発明の樹脂組成物について詳細に説明する。 Hereinafter, the resin composition of the present invention will be explained in detail.
[(a)環状イミド化合物]
(a)成分の環状イミド化合物は、本発明の樹脂組成物の主成分となるものである。本発明の樹脂組成物は、環状イミド化合物を含有し、環状イミド基が反応することによって、銅との高い接着性が発現される。
(a)成分の環状イミド化合物は、好ましくは下記式(1)で表される。
The cyclic imide compound (a) is the main component of the resin composition of the present invention. The resin composition of the present invention contains a cyclic imide compound, and the cyclic imide group reacts to exhibit high adhesion to copper.
The cyclic imide compound as component (a) is preferably represented by the following formula (1).
式(1)中のAで示される有機基は独立して環状構造を含む4価の有機基であり、特に下記構造式で示される4価の有機基のいずれかであることが好ましい。
式(1)中のQは、独立してヘテロ原子を含んでもよい芳香族基を含まない炭素数6以上の2価の炭化水素基であり、好ましくは下記構造式のいずれかで示される2価の炭化水素基又はダイマー酸骨格由来の2価炭化水素基である。
上記構造式中、R1は互いに独立に水素原子または炭素数1~20の直鎖もしくは分岐鎖のアルキル基を示す。R1は、好ましくは水素原子または炭素数1~10の直鎖もしくは分岐鎖のアルキル基であり、更に好ましくは水素原子または炭素数1~10の直鎖のアルキル基である。
上記構造式中、p1及びp2はそれぞれ5以上の数であり、好ましくはそれぞれ5~12の数であり、より好ましくはそれぞれ6~10の数であり、同じであっても異なっていてもよい。
上記構造式中、p3及びp4はそれぞれ0以上の数であり、好ましくはそれぞれ0~4の数であり、より好ましくはそれぞれ0~3の数であり、同じであっても異なっていてもよい。
上記構造式中、p5及びp6はそれぞれ0以上の数であり、好ましくはそれぞれ0~4の数であり、より好ましくはそれぞれ0~2の数であり、同じであっても異なっていてもよい。
In the above structural formula, R 1 independently represents a hydrogen atom or a straight or branched alkyl group having 1 to 20 carbon atoms. R 1 is preferably a hydrogen atom or a straight chain or branched alkyl group having 1 to 10 carbon atoms, and more preferably a hydrogen atom or a straight chain alkyl group having 1 to 10 carbon atoms.
In the above structural formula, p 1 and p 2 are each a number of 5 or more, preferably each is a number of 5 to 12, more preferably each is a number of 6 to 10, and may be the same or different. Good too.
In the above structural formula, p 3 and p 4 are each a number of 0 or more, preferably each is a number of 0 to 4, more preferably each is a number of 0 to 3, and may be the same or different. Good too.
In the above structural formula, p 5 and p 6 are each a number of 0 or more, preferably each is a number of 0 to 4, more preferably each is a number of 0 to 2, and may be the same or different. Good too.
ダイマー酸骨格由来の2価炭化水素基は、植物系油脂などの天然物を原料とする炭素数18の不飽和脂肪酸の二量化によって生成された、炭素数36のジカルボン酸を主成分とする液状の脂肪酸であるダイマー酸に由来する基である。ダイマー酸は単一の骨格ではなく、複数の構造を有し、何種類かの異性体が存在する。ダイマー酸骨格とは、このようなダイマー酸のカルボキシ基を1級アミノメチル基で置換した構造を有するダイマージアミンから誘導される基をいう。ダイマー酸骨格由来の2価炭化水素基は、水添反応により、該ダイマー酸骨格由来の炭化水素基中の炭素-炭素二重結合が低減した構造を有するものが、硬化物の耐熱性や信頼性の観点からより好ましい。
なお、一般的に、ダイマー酸には、植物系油脂などの天然物を原料とすることに起因して、三量体(トリマー酸)が含まれる場合もあるが、ダイマー酸及びトリマー酸由来の炭化水素基のうちダイマー酸由来の炭化水素基が占める割合が例えば95質量%以上、とダイマー酸由来の炭化水素基の割合が高いがことが、誘電特性に優れ、熱時の粘度が下がりやすく成形性に優れ、吸湿の影響も少なくなる傾向にあることから好ましい。
前記の通り、ダイマー酸骨格は複数の構造を有するため、本明細書では、ダイマー酸骨格由来の2価炭化水素基をその平均構造として-C36H70-と表記する場合がある。
The divalent hydrocarbon group derived from the dimer acid skeleton is a liquid whose main component is dicarboxylic acid with 36 carbon atoms, which is produced by dimerizing unsaturated fatty acids with 18 carbon atoms from natural products such as vegetable oils and fats. This is a group derived from dimer acid, which is a fatty acid. Dimer acids do not have a single skeleton, but have multiple structures, and several types of isomers exist. The dimer acid skeleton refers to a group derived from a dimer diamine having a structure in which the carboxy group of such a dimer acid is substituted with a primary aminomethyl group. The divalent hydrocarbon groups derived from the dimer acid skeleton have a structure in which carbon-carbon double bonds in the hydrocarbon groups derived from the dimer acid skeleton are reduced through a hydrogenation reaction, which improves the heat resistance and reliability of the cured product. More preferable from the viewpoint of sex.
In general, dimer acid may contain trimer (trimer acid) because it is made from natural products such as vegetable oils and fats, but dimer acid and trimer acid-derived The proportion of hydrocarbon groups derived from dimer acid among the hydrocarbon groups is, for example, 95% by mass or more, which means that the proportion of hydrocarbon groups derived from dimer acid is high, and the dielectric properties are excellent and the viscosity when heated is easily reduced. It is preferable because it has excellent moldability and tends to be less affected by moisture absorption.
As described above, since the dimer acid skeleton has a plurality of structures, in this specification, the divalent hydrocarbon group derived from the dimer acid skeleton may be expressed as -C 36 H 70 - as its average structure.
式(1)中のBは独立してヘテロ原子を含んでもよい炭素数6以上のアリーレン基であり、好ましくは下記構造式のいずれかで示されるアリーレン基である。
上記式中、R2は互いに独立に水素原子、ハロゲン原子又は炭素数1~6のアルキル基であり、好ましくは水素原子又はメチル基である。
上記式中、R3は互いに独立に水素原子、ハロゲン原子、メチル基又はトリフルオロメチル基であり、好ましくはメチル基又はトリフルオロメチル基である。
上記式中、Zは酸素原子、硫黄原子又はメチレン基であり、好ましくは酸素原子である。
In the above formula, R 2 is independently a hydrogen atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms, preferably a hydrogen atom or a methyl group.
In the above formula, R 3 is independently a hydrogen atom, a halogen atom, a methyl group or a trifluoromethyl group, preferably a methyl group or a trifluoromethyl group.
In the above formula, Z is an oxygen atom, a sulfur atom or a methylene group, preferably an oxygen atom.
式(1)中、Xは水素原子またはメチル基である。 In formula (1), X is a hydrogen atom or a methyl group.
式(1)中、nは0~200であり、好ましくは1~100であり、更に好ましくは2~50である。
式(1)中、mは0~200であり、好ましくは0~100であり、更に好ましくは0~50である。
In formula (1), n is 0 to 200, preferably 1 to 100, and more preferably 2 to 50.
In formula (1), m is 0 to 200, preferably 0 to 100, and more preferably 0 to 50.
上記式(1)中、m=0の場合、(a)成分の環状イミド化合物は、下記式(2)で表されるものである。
式(1)で表される環状イミド化合物の重量平均分子量(Mw)としては特に制限はないが、好ましくは2,000~1,000,000であり、より好ましくは3,000~100,000であり、更に好ましくは3,500~50,000である。重量平均分子量(Mw)がこの範囲であれば、樹脂組成物としての強度を十分に有し、かつ末端の環状イミド基を効率的に反応させることができる。 The weight average molecular weight (Mw) of the cyclic imide compound represented by formula (1) is not particularly limited, but is preferably 2,000 to 1,000,000, more preferably 3,000 to 100,000. and more preferably 3,500 to 50,000. When the weight average molecular weight (Mw) is within this range, the resin composition has sufficient strength and the terminal cyclic imide group can be reacted efficiently.
本明細書中で言及する重量平均分子量(Mw)とは、下記条件で測定したGPCによるポリスチレンを標準物質とした重量平均分子量を指すこととする。
[GPC測定条件]
展開溶媒:テトラヒドロフラン
流速:0.6mL/min
カラム:TSK Guardcolumn SuperH-L
TSKgel SuperH4000(6.0mmI.D.×15cm×1)
TSKgel SuperH3000(6.0mmI.D.×15cm×1)
TSKgel SuperH2000(6.0mmI.D.×15cm×2)
(いずれも東ソー社製)
カラム温度:40℃
試料注入量:20μL(試料濃度:0.5質量%-テトラヒドロフラン溶液)
検出器:示差屈折率計(RI)
The weight average molecular weight (Mw) referred to herein refers to the weight average molecular weight measured by GPC under the following conditions using polystyrene as a standard material.
[GPC measurement conditions]
Developing solvent: tetrahydrofuran Flow rate: 0.6 mL/min
Column:TSK Guardcolumn SuperHL-L
TSKgel SuperH4000 (6.0mm I.D. x 15cm x 1)
TSKgel SuperH3000 (6.0mm I.D. x 15cm x 1)
TSKgel SuperH2000 (6.0mm I.D. x 15cm x 2)
(Both manufactured by Tosoh Corporation)
Column temperature: 40℃
Sample injection amount: 20 μL (sample concentration: 0.5% by mass-tetrahydrofuran solution)
Detector: Differential refractometer (RI)
(a)成分の環状イミド化合物(例えば、マレイミド化合物、シトラコンイミド化合物等)を製造する方法としては特に制限はなく、例えばアミン化合物を過剰の無水マレイン酸または無水シトラコン酸と反応させて製造してもよいし、酸無水物とジアミンとを反応させてアミン末端化合物を合成した後、該アミン末端化合物を過剰の無水マレイン酸または無水シトラコン酸と反応させて製造してもよい。 There are no particular limitations on the method for producing the cyclic imide compound (e.g., maleimide compound, citraconimide compound, etc.) of component (a). For example, it may be produced by reacting an amine compound with excess maleic anhydride or citraconic anhydride. Alternatively, it may be produced by reacting an acid anhydride with a diamine to synthesize an amine-terminated compound, and then reacting the amine-terminated compound with excess maleic anhydride or citraconic anhydride.
酸無水物としては、例えば、無水ピロメリット酸、無水マレイン酸、無水コハク酸、4,4’-カルボニルジフタル酸無水物、4,4’-ジフタル酸無水物、4,4’-スルホニルジフタル酸無水物、4,4’-オキシジフタル酸無水物、4,4’-(4,4’-イソプロピリデンジフェノキシ)ジフタル酸無水物等が挙げられる。これらの酸無水物は目的、用途等に合わせて1種類を単独で用いてもよいし、2種類以上を併用してもよい。環状イミド化合物の電気特性の観点から、酸無水物は、無水ピロメリット酸、4,4’-オキシジフタル酸無水物、4,4’-(4,4’-イソプロピリデンジフェノキシ)ジフタル酸無水物が好ましい。 Examples of acid anhydrides include pyromellitic anhydride, maleic anhydride, succinic anhydride, 4,4'-carbonyldiphthalic anhydride, 4,4'-diphthalic anhydride, and 4,4'-sulfonyldiphthalic anhydride. Examples include phthalic anhydride, 4,4'-oxydiphthalic anhydride, 4,4'-(4,4'-isopropylidenediphenoxy)diphthalic anhydride, and the like. These acid anhydrides may be used alone or in combination of two or more depending on the purpose, use, etc. From the viewpoint of electrical properties of the cyclic imide compound, acid anhydrides include pyromellitic anhydride, 4,4'-oxydiphthalic anhydride, and 4,4'-(4,4'-isopropylidene diphenoxy) diphthalic anhydride. is preferred.
ジアミンとしては、例えば、2,2-ビス(4-(4-アミノフェノキシ)フェニル)プロパン、4,4’-ジアミノ-3,3’-ジメチルジフェニルメタン、4,4’-ジアミノ-3,3’-ジエチルジフェニルメタン、4,4’-ジアミノジフェニルエーテル、4,4’-ジアミノ-3,3’,5,5’-テトラエチルジフェニルメタン、テトラメチル-1,3-ビス(3-アミノプロピル)ジシロキサン、ビス[4-(4-アミノフェノキシ)フェニル]スルホン、4,4’-ジアミノジフェニルメタン、1,3-ビス(4-アミノフェノキシ)ベンゼン、1,12-ジアミノドデカン、1,10-ジアミノデカン、ダイマージアミン、オクチルジアミン、1,3-ジ(アミノメチル)シクロヘキサン、イソホロンジアミン、2,4,4-トリメチルヘキサン-1,6-ジアミン、2-メチルペンタン-1,5-ジアミン、3(4),8(9)-ビス(アミノメチル)トリシクロ[5.2.1.0(2,6)]デカン等が挙げられる。これらのジアミンは目的、用途等に合わせて、1種類を単独で用いてもよいし、2種類以上を併用してもよい。環状イミド化合物の電気特性の観点から、ジアミンは、2,2-ビス(4-(4-アミノフェノキシ)フェニル)プロパン、4,4’-ジアミノ-3,3’-ジメチルジフェニルメタン、4,4’-ジアミノ-3,3’-ジエチルジフェニルメタン、4,4’-ジアミノジフェニルエーテル、4,4’-ジアミノ-3,3’、5,5’-テトラエチルジフェニルメタン等の芳香族ジアミン;テトラメチル-1,3-ビス(3-アミノプロピル)ジシロキサン、1,12-ジアミノドデカン、1,10-ジアミノデカン、ダイマージアミン、オクチルジアミン、1,3-ジ(アミノメチル)シクロヘキサン、1-アミノ-4-(アミノメチル)シクロヘキサン、1,3-ジアミノアダマンタン、イソホロンジアミン、2,4,4-トリメチルヘキサン-1,6-ジアミン、2-メチルペンタン-1,5-ジアミン等の脂肪族ジアミンが好ましく、ダイマージアミン、イソホロンジアミンが特に好ましい。 Examples of the diamine include 2,2-bis(4-(4-aminophenoxy)phenyl)propane, 4,4'-diamino-3,3'-dimethyldiphenylmethane, 4,4'-diamino-3,3' -diethyldiphenylmethane, 4,4'-diaminodiphenyl ether, 4,4'-diamino-3,3',5,5'-tetraethyldiphenylmethane, tetramethyl-1,3-bis(3-aminopropyl)disiloxane, bis [4-(4-aminophenoxy)phenyl]sulfone, 4,4'-diaminodiphenylmethane, 1,3-bis(4-aminophenoxy)benzene, 1,12-diaminododecane, 1,10-diaminodecane, dimer diamine , octyldiamine, 1,3-di(aminomethyl)cyclohexane, isophoronediamine, 2,4,4-trimethylhexane-1,6-diamine, 2-methylpentane-1,5-diamine, 3(4),8 (9)-Bis(aminomethyl)tricyclo[5.2.1.0(2,6)]decane and the like. These diamines may be used alone or in combination of two or more, depending on the purpose, use, etc. From the viewpoint of electrical properties of cyclic imide compounds, diamines include 2,2-bis(4-(4-aminophenoxy)phenyl)propane, 4,4'-diamino-3,3'-dimethyldiphenylmethane, and 4,4' - Aromatic diamines such as diamino-3,3'-diethyldiphenylmethane, 4,4'-diaminodiphenyl ether, 4,4'-diamino-3,3', 5,5'-tetraethyldiphenylmethane; tetramethyl-1,3 -bis(3-aminopropyl)disiloxane, 1,12-diaminododecane, 1,10-diaminodecane, dimer diamine, octyldiamine, 1,3-di(aminomethyl)cyclohexane, 1-amino-4-(amino Aliphatic diamines such as methyl)cyclohexane, 1,3-diaminoadamantane, isophorone diamine, 2,4,4-trimethylhexane-1,6-diamine, and 2-methylpentane-1,5-diamine are preferred; dimer diamine, Isophoronediamine is particularly preferred.
また、(a)成分の環状イミド化合物は市販品を用いてもよい。市販品としては、BMI-689、BMI-1400、BMI-1500、BMI-2500、BMI-3000、BMI-6100(以上、Designer Molecules Inc.製)、SLK-6895、SLK-3000、SLK-2600、SLK-2700、SLK-6100(以上、信越化学工業(株)製)等を挙げることができる。 Moreover, a commercially available product may be used as the cyclic imide compound of component (a). Commercially available products include BMI-689, BMI-1400, BMI-1500, BMI-2500, BMI-3000, BMI-6100 (manufactured by Designer Molecules Inc.), SLK-6895, SLK-3000, SLK-2600, Examples include SLK-2700 and SLK-6100 (manufactured by Shin-Etsu Chemical Co., Ltd.).
(a)成分の環状イミド基の当量としては、0.001~0.5mol/100gが好ましく、0.003~0.4mol/100gがより好ましく、0.01~0.3mol/100gが更に好ましく、0.02~0.2mol/100gが更により好ましい。この範囲であれば、樹脂組成物の硬化物が低比誘電率、低誘電正接、高接着となるため好ましい。 The equivalent weight of the cyclic imide group in component (a) is preferably 0.001 to 0.5 mol/100g, more preferably 0.003 to 0.4 mol/100g, and even more preferably 0.01 to 0.3 mol/100g. , 0.02 to 0.2 mol/100g is even more preferred. This range is preferable because the cured product of the resin composition has a low dielectric constant, low dielectric loss tangent, and high adhesion.
(a)成分の配合量は、後述するエポキシ化合物のエポキシ基数との比率が下記式を満たす必要がある。
0.3 ≦ 環状イミド基数/エポキシ基数 ≦ 3.0
好ましくは下記式を満たす。
0.5 ≦ 環状イミド基数/エポキシ基数 ≦ 2.5
更に好ましくは下記式を満たす。
0.7 ≦ 環状イミド基数/エポキシ基数 ≦ 2.0
Regarding the blending amount of component (a), the ratio of the number of epoxy groups in the epoxy compound described below must satisfy the following formula.
0.3 ≦ Number of cyclic imide groups/Number of epoxy groups ≦ 3.0
Preferably, the following formula is satisfied.
0.5 ≦ Number of cyclic imide groups/Number of epoxy groups ≦ 2.5
More preferably, the following formula is satisfied.
0.7 ≦ Number of cyclic imide groups/Number of epoxy groups ≦ 2.0
環状イミド基数/エポキシ基数の比率が0.3より小さいと、比誘電率、誘電正接の値が高くなってしまう。また、イミダゾール化合物を触媒とした場合、環状イミド基はエポキシ基がないと反応しない、または反応温度が高くなってしまう。したがって、環状イミド基数/エポキシ基数の比率が3.0より大きいと環状イミド基が反応せずに残ってしまい、銅との接着力が低くなってしまう。 If the ratio of the number of cyclic imide groups/the number of epoxy groups is smaller than 0.3, the values of the relative dielectric constant and the dielectric loss tangent will become high. Furthermore, when an imidazole compound is used as a catalyst, the cyclic imide group will not react without the epoxy group, or the reaction temperature will become high. Therefore, if the ratio of the number of cyclic imide groups/the number of epoxy groups is larger than 3.0, the cyclic imide groups will remain unreacted and the adhesive strength with copper will become low.
[(b)エポキシ化合物]
(b)成分のエポキシ化合物は(a)成分の環状イミド化合物と共重合し、本発明の樹脂組成物の主成分となるものである。エポキシ基が環状イミド基と共重合することによって、環状イミド基の硬化が早くなり、接着性をより高めることができる。
[(b) Epoxy compound]
The epoxy compound (b) is copolymerized with the cyclic imide compound (a) and becomes the main component of the resin composition of the present invention. By copolymerizing the epoxy group with the cyclic imide group, the cyclic imide group can be cured more quickly and the adhesiveness can be further improved.
(b)成分のエポキシ化合物としては、特に限定されないが、例えば、ビスフェノールA型エポキシ化合物、ビスフェノールF型エポキシ化合物、3,3’,5,5’-テトラメチル-4,4’-ビフェノール型エポキシ化合物、4,4’-メチレンビス(N,N-ジグリシジアニリン)や4-グリシジロキシ(N,N-ジグリシジアニリン)等の液状多官能型エポキシ化合物、4,4’-ビフェノール型エポキシ化合物等のビフェノール型エポキシ化合物、ビフェノールノボラック型エポキシ化合物、ビフェニルアラルキル型エポキシ化合物、フェノールノボラック型エポキシ化合物、クレゾールノボラック型エポキシ化合物、ビスフェノールAノボラック型エポキシ化合物、ナフタレンジオール型エポキシ化合物、トリスフェニロールメタン型エポキシ化合物、テトラキスフェニロールエタン型エポキシ化合物、フェノールジシクロペンタジエンノボラック型エポキシ化合物、並びにフェノールジシクロペンタジエンノボラック型エポキシ化合物の芳香環を水素化したエポキシ化合物等が挙げられる。これらの中でも、液状多官能型エポキシ化合物、ビフェノールノボラック型エポキシ化合物、フェノールノボラック型エポキシ化合物、クレゾールノボラック型エポキシ化合物、ビスフェノールAノボラック型エポキシ化合物、ビフェニルアラルキル型エポキシ化合物、フェノールジシクロペンタジエンノボラック型エポキシ化合物が好ましい。エポキシ化合物は1種類を単独で用いてもよいし、2種類以上を併用してもよい。また必要に応じて、上記以外のエポキシ化合物を目的に応じて一定量併用することができる。 The epoxy compound of component (b) is not particularly limited, but for example, bisphenol A type epoxy compound, bisphenol F type epoxy compound, 3,3',5,5'-tetramethyl-4,4'-biphenol type epoxy compounds, liquid polyfunctional epoxy compounds such as 4,4'-methylenebis (N,N-diglycidianiline) and 4-glycidyloxy (N,N-diglycidianiline), 4,4'-biphenol type epoxy compounds, etc. Biphenol type epoxy compound, biphenol novolac type epoxy compound, biphenylaralkyl type epoxy compound, phenol novolak type epoxy compound, cresol novolac type epoxy compound, bisphenol A novolac type epoxy compound, naphthalene diol type epoxy compound, trisphenylormethane type epoxy compound, Examples include a tetrakisphenyloethane type epoxy compound, a phenol dicyclopentadiene novolac type epoxy compound, and an epoxy compound obtained by hydrogenating the aromatic ring of a phenol dicyclopentadiene novolac type epoxy compound. Among these, liquid polyfunctional epoxy compounds, biphenol novolac type epoxy compounds, phenol novolak type epoxy compounds, cresol novolak type epoxy compounds, bisphenol A novolak type epoxy compounds, biphenylaralkyl type epoxy compounds, phenol dicyclopentadiene novolac type epoxy compounds is preferred. One type of epoxy compound may be used alone, or two or more types may be used in combination. Furthermore, if necessary, epoxy compounds other than those mentioned above can be used in combination in a certain amount depending on the purpose.
(b)成分の配合量は、前述した環状イミド基との比率を満たし、更に後述するイミダゾール基数との比率が下記式を満たす必要がある。
2.0 ≦ エポキシ基数/イミダゾール基数 ≦ 20.0
好ましくは下記式を満たす。
4.0 ≦ エポキシ基数/イミダゾール基数 ≦ 17.0
更に好ましくは下記式を満たす。
6.0 ≦ エポキシ基数/イミダゾール基数 ≦ 15.0
The blending amount of component (b) must satisfy the ratio with the cyclic imide group described above, and the ratio with the number of imidazole groups described below must satisfy the following formula.
2.0 ≦ Number of epoxy groups/Number of imidazole groups ≦ 20.0
Preferably, the following formula is satisfied.
4.0 ≦ Number of epoxy groups/Number of imidazole groups ≦ 17.0
More preferably, the following formula is satisfied.
6.0 ≦ Number of epoxy groups/Number of imidazole groups ≦ 15.0
エポキシ基数/イミダゾール基数の比率が2.0より小さいと、イミダゾール基がすぐにエポキシ基を開環していまい、通常の硬化条件では環状イミド基が反応せずに残ってしまい、銅との接着力が低くなってしまう。また、エポキシ基数/イミダゾール基数の比率が20.0より大きいと樹脂組成物全体の硬化反応が遅くなってしまう。したがって、通常の硬化条件ではエポキシ基と環状イミド基が反応せずに残ってしまい、銅との接着力が低くなってしまう。 If the ratio of the number of epoxy groups/the number of imidazole groups is less than 2.0, the imidazole group will open the epoxy group immediately, and the cyclic imide group will remain unreacted under normal curing conditions, resulting in poor adhesion with copper. The power becomes low. Moreover, if the ratio of the number of epoxy groups/the number of imidazole groups is larger than 20.0, the curing reaction of the entire resin composition will be delayed. Therefore, under normal curing conditions, the epoxy group and the cyclic imide group remain unreacted, resulting in low adhesive strength with copper.
[(c)イミダゾール化合物]
(c)成分のイミダゾール化合物は、本発明の樹脂組成物の硬化触媒となるものである。
(c)成分のイミダゾール化合物としては、樹脂の硬化触媒として用いられるもの、例えば、2-メチルイミダゾール、2-エチルイミダゾール、2-フェニルイミダゾール、2-エチル-4-メチルイミダゾール、2-ウンデシルイミダゾール、1-シアノエチル-2-エチル-4-メチルイミダゾール、2,4-ジアミノ-6-[2-(2-メチル-1-イミダゾリル)エチル]-1,3,5-トリアジン、2-フェニル-4-ヒドロキシ-5-メチルイミダゾール等が挙げられる。また、(c)成分のイミダゾール化合物として、C11Z、2PZ、2P4MZ、2MZ-CN、C11Z-A、2MA-OK、2PHZ、2P4MHZ(以上、四国化成工業(株)製)等を用いてもよい。これらの中でも、2-エチル-4-メチルイミダゾール、1-シアノエチル-2-エチル-4-メチルイミダゾール、2,4-ジアミノ-6-[2-(2-メチル-1-イミダゾリル)エチル]-1,3,5-トリアジン、2PHZ、2P4MHZが好ましい。イミダゾール化合物は1種類を単独で用いてもよいし、2種類以上を併用してもよい。また必要に応じて、上記以外のイミダゾール化合物を目的に応じて一定量併用することができる。
(c)成分の配合量は、前述したエポキシ基数との比率を満たす必要がある。
[(c) Imidazole compound]
The imidazole compound (c) serves as a curing catalyst for the resin composition of the present invention.
The imidazole compound of component (c) is one used as a curing catalyst for resins, such as 2-methylimidazole, 2-ethylimidazole, 2-phenylimidazole, 2-ethyl-4-methylimidazole, 2-undecylimidazole. , 1-cyanoethyl-2-ethyl-4-methylimidazole, 2,4-diamino-6-[2-(2-methyl-1-imidazolyl)ethyl]-1,3,5-triazine, 2-phenyl-4 -hydroxy-5-methylimidazole and the like. Furthermore, as the imidazole compound of component (c), C11Z, 2PZ, 2P4MZ, 2MZ-CN, C11Z-A, 2MA-OK, 2PHZ, 2P4MHZ (all manufactured by Shikoku Kasei Kogyo Co., Ltd.), etc. may be used. Among these, 2-ethyl-4-methylimidazole, 1-cyanoethyl-2-ethyl-4-methylimidazole, 2,4-diamino-6-[2-(2-methyl-1-imidazolyl)ethyl]-1 , 3,5-triazine, 2PHZ, and 2P4MHZ are preferred. One type of imidazole compound may be used alone, or two or more types may be used in combination. Further, if necessary, imidazole compounds other than those mentioned above can be used in combination in a certain amount depending on the purpose.
The blending amount of component (c) needs to satisfy the ratio with the number of epoxy groups mentioned above.
本発明の樹脂組成物中、(a)~(c)成分は50~100質量%であることが好ましく、70~95質量%であることがより好ましい。 In the resin composition of the present invention, the content of components (a) to (c) is preferably 50 to 100% by mass, more preferably 70 to 95% by mass.
[その他の成分]
[重合開始剤]
本発明の樹脂組成物は(c)成分のイミダゾール化合物で硬化させた後、より完全に硬化させるためにその他の重合開始剤を含有してもよい。重合開始剤としては、特に制限はないが、例えば熱ラジカル重合開始剤、熱アニオン重合開始剤等が挙げられる。
[Other ingredients]
[Polymerization initiator]
After the resin composition of the present invention is cured with the imidazole compound as component (c), it may contain other polymerization initiators in order to more completely cure it. The polymerization initiator is not particularly limited, and examples thereof include thermal radical polymerization initiators, thermal anionic polymerization initiators, and the like.
熱ラジカル重合開始剤としては、例えば、メチルエチルケトンパーオキサイド、メチルシクロヘキサノンパーオキサイド、メチルアセトアセテートパーオキサイド、アセチルアセトンパーオキサイド、1,1-ビス(t-ブチルパーオキシ)3,3,5-トリメチルシクロヘキサン、1,1-ビス(t-ヘキシルパーオキシ)シクロヘキサン、1,1-ビス(t-ヘキシルパーオキシ)3,3,5-トリメチルシクロヘキサン、1,1-ビス(t-ブチルパーオキシ)シクロヘキサン、2,2-ビス(4,4-ジ-t-ブチルパーオキシシクロヘキシル)プロパン、1,1-ビス(t-ブチルパーオキシ)シクロドデカン、n-ブチル-4,4-ビス(t-ブチルパーオキシ)バレレート、2,2-ビス(t-ブチルパーオキシ)ブタン、1,1-ビス(t-ブチルパーオキシ)-2-メチルシクロヘキサン、t-ブチルハイドロパーオキサイド、p-メンタンハイドロパーオキサイド、1,1,3,3-テトラメチルブチルハイドロパーオキサイド、t-ヘキシルハイドロパーオキサイド、ジクミルパーオキサイド、2,5-ジメチル-2,5-ビス(t-ブチルパーオキシ)ヘキサン、α、α’-ビス(t-ブチルパーオキシ)ジイソプロピルベンゼン、t-ブチルクミルパーオキサイド、ジ-t-ブチルパーオキサイド、2,5-ジメチル-2,5-ビス(t-ブチルパーオキシ)ヘキシン-3、イソブチリルパーオキサイド、3,5,5-トリメチルヘキサノイルパーオキサイド、オクタノイルパーオキサイド、ラウロイルパーオキサイド、桂皮酸パーオキサイド、m-トルオイルパーオキサイド、ベンゾイルパーオキサイド、ジイソプロピルパーオキシジカーボネート、ビス(4-t-ブチルシクロヘキシル)パーオキシジカーボネート、ジ-3-メトキシブチルパーオキシジカーボネート、ジ-2-エチルヘキシルパーオキシジカーボネート、ジ-sec-ブチルパーオキシジカーボネート、ジ(3-メチル-3-メトキシブチル)パーオキシジカーボネート、ジ(4-t-ブチルシクロヘキシル)パーオキシジカーボネート、α、α’-ビス(ネオデカノイルパーオキシ)ジイソプロピルベンゼン、クミルパーオキシネオデカノエート、1,1,3,3-テトラメチルブチルパーオキシネオデカノエート、1-シクロヘキシル-1-メチルエチルパーオキシネオデカノエート、t-ヘキシルパーオキシネオデカノエート、t-ブチルパーオキシネオデカノエート、t-ヘキシルパーオキシピバレート、t-ブチルパーオキシピバレート、2,5-ジメチル-2,5-ビス(2-エチルヘキサノイルパーオキシ)ヘキサン、1,1,3,3-テトラメチルブチルパーオキシ-2-エチルへキサノエート、1-シクロヘキシル-1-メチルエチルパーオキシ-2-エチルヘキサノエート、t-ヘキシルパーオキシ-2-エチルヘキサノエート、t-ブチルパーオキシ-2-エチルヘキサノエート、t-ブチルパーオキシイソブチレート、t-ブチルパーオキシマレイックアシッド、t-ブチルパーオキシラウレート、t-ブチルパーオキシ-3,5,5-トリメチルヘキサノエート、t-ブチルパーオキシイソプロピルモノカーボネート、t-ブチルパーオキシ-2-エチルヘキシルモノカーボネート、2,5-ジメチル-2,5-ビス(ベンゾイルパーオキシ)ヘキサン、t-ブチルパーオキシアセテート、t-ヘキシルパーオキシベンゾエート、t-ブチルパーオキシ-m-トルオイルベンゾエート、t-ブチルパーオキシベンゾエート、ビス(t-ブチルパーオキシ)イソフタレート、t-ブチルパーオキシアリルモノカーボネート、3,3’,4,4’-テトラ(t-ブチルパーオキシカルボニル)ベンゾフェノン等の有機過酸化物;2,2’-アゾビス(N-ブチル-2-メチルプロピオンアミド)、2,2’-アゾビス(N-シクロヘキシル-2-メチルプロピオンアミド)、2,2’-アゾビス[N-(2-メチルプロピル)-2-メチルプロピオンアミド]、2,2’-アゾビス[N-(2-メチルエチル)-2-メチルプロピオンアミド]、2,2’-アゾビス(N-ヘキシル-2-メチルプロピオンアミド)、2,2’-アゾビス(N-プロピル-2-メチルプロピオンアミド)、2,2’-アゾビス(N-エチル-2-メチルプロピオンアミド)、2,2’-アゾビス[2-メチル-N-(2-ヒドロキシエチル)プロピオンアミド]、2,2’-アゾビス[N-(2-プロペニル)-2-メチルプロピオンアミド]、2,2’-アゾビス{2-メチル-N-[1,1-ビス(ヒドロキシメチル)-2-ヒドロキシエチル]プロピオンアミド}、2,2’-アゾビス[N-(2-プロペニル)-2-メチルプロピオンアミド]、ジメチル-1,1’-アゾビス(1-シクロヘキサンカルボキシレート)等のアゾ化合物が挙げられる。 Examples of the thermal radical polymerization initiator include methyl ethyl ketone peroxide, methyl cyclohexanone peroxide, methyl acetoacetate peroxide, acetylacetone peroxide, 1,1-bis(t-butylperoxy)3,3,5-trimethylcyclohexane, 1,1-bis(t-hexylperoxy)cyclohexane, 1,1-bis(t-hexylperoxy)3,3,5-trimethylcyclohexane, 1,1-bis(t-butylperoxy)cyclohexane, 2 , 2-bis(4,4-di-t-butylperoxycyclohexyl)propane, 1,1-bis(t-butylperoxy)cyclododecane, n-butyl-4,4-bis(t-butylperoxy) ) valerate, 2,2-bis(t-butylperoxy)butane, 1,1-bis(t-butylperoxy)-2-methylcyclohexane, t-butyl hydroperoxide, p-menthane hydroperoxide, 1 , 1,3,3-tetramethylbutyl hydroperoxide, t-hexyl hydroperoxide, dicumyl peroxide, 2,5-dimethyl-2,5-bis(t-butylperoxy)hexane, α, α' -Bis(t-butylperoxy)diisopropylbenzene, t-butylcumyl peroxide, di-t-butylperoxide, 2,5-dimethyl-2,5-bis(t-butylperoxy)hexine-3, iso Butyryl peroxide, 3,5,5-trimethylhexanoyl peroxide, octanoyl peroxide, lauroyl peroxide, cinnamic acid peroxide, m-toluoyl peroxide, benzoyl peroxide, diisopropyl peroxydicarbonate, bis(4 -t-butylcyclohexyl) peroxydicarbonate, di-3-methoxybutylperoxydicarbonate, di-2-ethylhexyl peroxydicarbonate, di-sec-butylperoxydicarbonate, di(3-methyl-3- methoxybutyl) peroxydicarbonate, di(4-t-butylcyclohexyl)peroxydicarbonate, α,α'-bis(neodecanoylperoxy)diisopropylbenzene, cumyl peroxyneodecanoate, 1,1, 3,3-Tetramethylbutylperoxyneodecanoate, 1-cyclohexyl-1-methylethylperoxyneodecanoate, t-hexylperoxyneodecanoate, t-butylperoxyneodecanoate, t -Hexylperoxypivalate, t-butylperoxypivalate, 2,5-dimethyl-2,5-bis(2-ethylhexanoylperoxy)hexane, 1,1,3,3-tetramethylbutylperoxy -2-ethylhexanoate, 1-cyclohexyl-1-methylethylperoxy-2-ethylhexanoate, t-hexylperoxy-2-ethylhexanoate, t-butylperoxy-2-ethylhexanoate , t-butylperoxyisobutyrate, t-butylperoxymaleic acid, t-butylperoxylaurate, t-butylperoxy-3,5,5-trimethylhexanoate, t-butylperoxyisopropyl Monocarbonate, t-butylperoxy-2-ethylhexyl monocarbonate, 2,5-dimethyl-2,5-bis(benzoylperoxy)hexane, t-butylperoxyacetate, t-hexylperoxybenzoate, t-butyl Peroxy-m-toluoylbenzoate, t-butylperoxybenzoate, bis(t-butylperoxy)isophthalate, t-butylperoxyallyl monocarbonate, 3,3',4,4'-tetra(t- Organic peroxides such as butylperoxycarbonyl) benzophenone; 2,2'-azobis(N-butyl-2-methylpropionamide), 2,2'-azobis(N-cyclohexyl-2-methylpropionamide), 2 , 2'-azobis[N-(2-methylpropyl)-2-methylpropionamide], 2,2'-azobis[N-(2-methylethyl)-2-methylpropionamide], 2,2'- Azobis(N-hexyl-2-methylpropionamide), 2,2'-azobis(N-propyl-2-methylpropionamide), 2,2'-azobis(N-ethyl-2-methylpropionamide), 2 , 2'-azobis[2-methyl-N-(2-hydroxyethyl)propionamide], 2,2'-azobis[N-(2-propenyl)-2-methylpropionamide], 2,2'-azobis {2-methyl-N-[1,1-bis(hydroxymethyl)-2-hydroxyethyl]propionamide}, 2,2'-azobis[N-(2-propenyl)-2-methylpropionamide], dimethyl Examples include azo compounds such as -1,1'-azobis(1-cyclohexanecarboxylate).
熱アニオン重合開始剤としては、トリエチルアミン、トリエチレンジアミン、2-(ジメチルアミノメチル)フェノール、1,8-ジアザ-ビシクロ[5.4.0]ウンデセン-7、トリス(ジメチルアミノメチル)フェノール、ベンジルジメチルアミン等のアミン化合物;トリフェニルホスフィン、トリブチルホスフィン、トリオクチルホスフィン、テトラブチルホスホニウムヘキサフルオロホスファート、テトラブチルホスホニウムテトラフェニルボラート、テトラブチルホスホニウムアセテート、テトラフェニルホスホニウムテトラフェニルボラート、テトラフェニルホスホニウムブロミド、テトラブチルホスホニウムブロミド、テトラブチルホスホニウムラウレート、テトラフェニルホスホニウムハイドロジェンフタレート、ビス(テトラフェニルホスホニウム)ジハイドロジェンピロメリテート、ビス(テトラブチルホスホニウム)ジハイドロジェンピロメリテート等の有機リン化合物が挙げられる。 Examples of thermal anionic polymerization initiators include triethylamine, triethylenediamine, 2-(dimethylaminomethyl)phenol, 1,8-diaza-bicyclo[5.4.0]undecene-7, tris(dimethylaminomethyl)phenol, and benzyldimethyl. Amine compounds such as amines; triphenylphosphine, tributylphosphine, trioctylphosphine, tetrabutylphosphonium hexafluorophosphate, tetrabutylphosphonium tetraphenylborate, tetrabutylphosphonium acetate, tetraphenylphosphonium tetraphenylborate, tetraphenylphosphonium bromide , tetrabutylphosphonium bromide, tetrabutylphosphonium laurate, tetraphenylphosphonium hydrogen phthalate, bis(tetraphenylphosphonium) dihydrogenpyromellitate, bis(tetrabutylphosphonium)dihydrogenpyromellitate, etc. Can be mentioned.
これらの中でも、熱ラジカル重合開始剤が好ましく、中でも、メチルエチルケトンパーオキサイド、ジクミルパーオキサイド、t-ブチルクミルパーオキサイド、ジ-t-ブチルパーオキサイド、ラウロイルパーオキサイド、桂皮酸パーオキサイドが特に好ましい。
これら重合開始剤は1種類を単独で使用してもよいし、2種類以上を併用してもよい。熱ラジカル重合開始剤や熱アニオン重合開始剤の配合量は特に限定されないが、本発明の組成物中の(a)成分100質量部に対して0.01~10質量部であることが好ましく、0.1~5質量部であることがより好ましく、0.3~3質量部であることが更に好ましい。この範囲であれば、樹脂組成物の物性に悪影響を与えることなく、十分に硬化させることができる。
Among these, thermal radical polymerization initiators are preferred, and among them, methyl ethyl ketone peroxide, dicumyl peroxide, t-butylcumyl peroxide, di-t-butyl peroxide, lauroyl peroxide, and cinnamic acid peroxide are particularly preferred.
These polymerization initiators may be used alone or in combination of two or more. The amount of the thermal radical polymerization initiator and the thermal anionic polymerization initiator is not particularly limited, but it is preferably 0.01 to 10 parts by weight based on 100 parts by weight of component (a) in the composition of the present invention. It is more preferably 0.1 to 5 parts by weight, and even more preferably 0.3 to 3 parts by weight. Within this range, sufficient curing can be achieved without adversely affecting the physical properties of the resin composition.
[無機充填剤]
本発明の樹脂組成物は、さらに無機充填剤を含有してもよい。
無機充填剤としては、特に制限はないが、例えばシリカ、二酸化チタン、酸化イットリウム、酸化アルミニウム、酸化マグネシウム、酸化亜鉛、酸化ベリリウム等の金属酸化物;窒化ホウ素、窒化アルミニウム、窒化ケイ素等の金属窒化物;炭化ケイ素、ダイヤモンド、グラフェン等の炭素含有粒子;シリカバルーン(中空シリカ)、カーボンバルーン、アルミナバルーン、アルミノシリケートバルーン等の中空粒子;金、銀、銅、パラジウム、アルミニウム、ニッケル、鉄、コバルト、チタン、マンガン、亜鉛、タングステン、白金、鉛、錫等の金属単体;半田、鋼、ステンレス鋼等の合金;ステンレス、Fe-Cr-Al-Si合金、Fe-Si-Al合金、Fe-Ni合金、Fe-Cu-Si合金、Fe-Si合金、Fe-Si―B(-Cu-Nb)合金、Fe-Si-Cr-Ni合金、Fe-Si-Cr合金、Fe-Si-Al-Ni-Cr合金等の磁性金属合金;ヘマタイト(Fe2O3)、マグネタイト(Fe3O4)、Mn-Zn系フェライト、Ni-Zn系フェライト、Mg-Mn系フェライト、Zr-Mn系フェライト、Ti-Mn系フェライト、Mn-Zn-Cu系フェライト、バリウムフェライト、ストロンチウムフェライト等のフェライト類が挙げられる。これらは1種単独で使用してもよいし、2種以上を併用してもよい。
[Inorganic filler]
The resin composition of the present invention may further contain an inorganic filler.
Inorganic fillers are not particularly limited, but include metal oxides such as silica, titanium dioxide, yttrium oxide, aluminum oxide, magnesium oxide, zinc oxide, and beryllium oxide; metal nitrides such as boron nitride, aluminum nitride, and silicon nitride. Carbon-containing particles such as silicon carbide, diamond, and graphene; Hollow particles such as silica balloons (hollow silica), carbon balloons, alumina balloons, and aluminosilicate balloons; gold, silver, copper, palladium, aluminum, nickel, iron, cobalt , titanium, manganese, zinc, tungsten, platinum, lead, tin, etc.; alloys such as solder, steel, stainless steel; stainless steel, Fe-Cr-Al-Si alloy, Fe-Si-Al alloy, Fe-Ni Alloy, Fe-Cu-Si alloy, Fe-Si alloy, Fe-Si-B (-Cu-Nb) alloy, Fe-Si-Cr-Ni alloy, Fe-Si-Cr alloy, Fe-Si-Al-Ni -Magnetic metal alloys such as Cr alloy; hematite (Fe 2 O 3 ), magnetite (Fe 3 O 4 ), Mn-Zn ferrite, Ni-Zn ferrite, Mg-Mn ferrite, Zr-Mn ferrite, Ti Examples include ferrites such as -Mn ferrite, Mn-Zn-Cu ferrite, barium ferrite, and strontium ferrite. These may be used alone or in combination of two or more.
金属酸化物、金属窒化物、炭素含有粒子を加えることによって樹脂組成物の硬化物の線膨張係数を下げ、熱伝導率を上げることができ、中空粒子を加えることによって樹脂組成物の硬化物の比誘電率、誘電正接、密度等を下げることができ、金属、合金を加えることによって樹脂組成物の硬化物の電気伝導率、熱伝導率等を上げることができ、フェライト類を加えることによって樹脂組成物の硬化物に電磁波吸収能を付与することができる。 By adding metal oxides, metal nitrides, and carbon-containing particles, the coefficient of linear expansion of the cured resin composition can be lowered and the thermal conductivity can be increased. It is possible to lower the relative dielectric constant, dielectric loss tangent, density, etc., it is possible to increase the electrical conductivity, thermal conductivity, etc. of the cured resin composition by adding metals and alloys, and it is possible to increase the electrical conductivity, thermal conductivity, etc. of the cured product of the resin composition. Electromagnetic wave absorption ability can be imparted to the cured product of the composition.
前記無機充填剤の形状としては、特に制限はなく、例えば球状、鱗片状、フレーク状、針状、棒状、楕円状等が挙げられ、中でも球状、鱗片状、フレーク状、楕円状、棒状が好ましく、球状、鱗片状、フレーク状、楕円状が更に好ましい。 The shape of the inorganic filler is not particularly limited, and examples thereof include spherical, scale-like, flake-like, needle-like, rod-like, and elliptical shapes, among which spherical, scale-like, flake-like, elliptical, and rod-like shapes are preferred. , spherical, scaly, flaky, and elliptical shapes are more preferable.
前記無機充填剤の一次粒径としては特に制限はないが、レーザー回折式粒度分布測定装置で測定されたメジアン径として0.05~500μmが好ましく、0.1~300μmがより好ましく、1~100μmが更に好ましい。この範囲内であれば、樹脂組成物中に前記無機充填剤を均一に分散させることが容易であり、経時で該無機充填剤が沈降、分離、偏在してしまうこともないため好ましい。 The primary particle size of the inorganic filler is not particularly limited, but the median diameter measured with a laser diffraction particle size distribution analyzer is preferably 0.05 to 500 μm, more preferably 0.1 to 300 μm, and 1 to 100 μm. is even more preferable. Within this range, it is easy to uniformly disperse the inorganic filler in the resin composition, and the inorganic filler does not settle, separate, or become unevenly distributed over time, which is preferable.
前記無機充填剤の配合量としては特に制限はないが、本発明の組成物中の(a)成分100質量部に対して5~3,000質量部であることが好ましく、10~2,500質量部であることがより好ましく、50~2,000質量部であることが更に好ましい。この範囲であれば樹脂組成物の強度を保持したまま、無機充填剤の機能を十分に発揮することができる。 The amount of the inorganic filler to be blended is not particularly limited, but it is preferably 5 to 3,000 parts by mass, and 10 to 2,500 parts by mass based on 100 parts by mass of component (a) in the composition of the present invention. It is more preferably 50 to 2,000 parts by weight, and even more preferably 50 to 2,000 parts by weight. Within this range, the function of the inorganic filler can be fully exhibited while maintaining the strength of the resin composition.
[有機充填剤]
本発明の樹脂組成物は、さらに有機充填剤を含有してもよい。
有機充填剤としては、特に制限はないが、例えばアクリル-ブタジエン共重合体、スチレン-ブタジエン共重合体、アクリロニトリル-スチレン-ブタジエン共重合体、アクリルブロック共重合体のような熱可塑性樹脂粒子、炭素繊維、セルロース繊維、シリコーンパウダー、アクリルパウダー、ポリテトラフルオロエチレン粉、ポリエチレン粉、ポリプロピレン粉などが挙げられる。これらは1種単独で使用してもよいし、2種以上を併用してもよい。
[Organic filler]
The resin composition of the present invention may further contain an organic filler.
The organic filler is not particularly limited, but includes thermoplastic resin particles such as acrylic-butadiene copolymer, styrene-butadiene copolymer, acrylonitrile-styrene-butadiene copolymer, acrylic block copolymer, and carbon. Examples include fiber, cellulose fiber, silicone powder, acrylic powder, polytetrafluoroethylene powder, polyethylene powder, polypropylene powder, and the like. These may be used alone or in combination of two or more.
前記有機充填剤の形状としては、特に制限はなく、例えば球状、繊維状、フレーク状、針状、棒状、楕円状等が挙げられ、中でも球状、繊維状、フレーク状、楕円状、棒状が好ましく、球状、繊維状、フレーク状、楕円状が更に好ましい。 The shape of the organic filler is not particularly limited, and examples thereof include spherical, fibrous, flake, needle, rod, and elliptical shapes, among which spherical, fibrous, flake, elliptical, and rod shapes are preferred. , spherical, fibrous, flaky, and elliptical shapes are more preferable.
前記有機充填剤の一次粒径としては特に制限はないが、レーザー回折式粒度分布測定装置で測定されたメジアン径として0.05~500μmが好ましく、0.1~300μmがより好ましく、1~100μmが更に好ましい。この範囲内であれば、樹脂組成物中に前記有機粒子を均一に分散させることが容易であり、経時で該有機粒子が沈降、分離、偏在してしまうこともないため好ましい。 The primary particle size of the organic filler is not particularly limited, but the median diameter measured with a laser diffraction particle size distribution analyzer is preferably 0.05 to 500 μm, more preferably 0.1 to 300 μm, and 1 to 100 μm. is even more preferable. Within this range, it is easy to uniformly disperse the organic particles in the resin composition, and the organic particles do not settle, separate, or become unevenly distributed over time, which is preferable.
前記有機充填剤の配合量としては特に制限はないが、本発明の組成物中の(a)成分100質量部に対して1~400質量部であることが好ましく、5~200質量部であることがより好ましく、10~100質量部であることが更に好ましい。この範囲であれば樹脂組成物の強度を上げることが可能となる。 The amount of the organic filler to be blended is not particularly limited, but it is preferably 1 to 400 parts by weight, and 5 to 200 parts by weight, based on 100 parts by weight of component (a) in the composition of the present invention. The amount is more preferably 10 to 100 parts by mass. Within this range, it is possible to increase the strength of the resin composition.
[接着性付与剤]
本発明の樹脂組成物は、接着性あるいは粘着性(感圧接着性)を付与するため、必要に応じて接着性付与剤を含有してもよい。接着性付与剤としては、例えば、アクリル樹脂、ウレタン樹脂、フェノール樹脂、テルペン樹脂、シランカップリング剤等が挙げられる。中でも接着性を付与するにはアクリル樹脂、シランカップリング剤が好ましく、粘着性(感圧接着性)を付与するにはテルペン樹脂が好ましい。
[Adhesive agent]
The resin composition of the present invention may contain an adhesion-imparting agent as necessary in order to impart adhesiveness or tackiness (pressure-sensitive adhesiveness). Examples of the adhesion imparting agent include acrylic resin, urethane resin, phenol resin, terpene resin, and silane coupling agent. Among these, acrylic resins and silane coupling agents are preferred for imparting adhesive properties, and terpene resins are preferred for imparting tackiness (pressure-sensitive adhesiveness).
アクリル樹脂としては、特に制限はないが、例えばラウリルアクリレート、ステアリルアクリレート、イソステアリルアクリレート、フェノキシエチルアクリレート、フェノキシジエチレングリコールアクリレート、テトラヒドロフルフリルアクリレート、イソボルニルアクリレート、2-アクリロイロキシエチルフタル酸、2-アクリロイルオキシエチルアシッドホスフェート、ポリエチレングリコールジアクリレート、ジメチロールトリシクロデカンジアクリレート、トリメチロルプロパントリアクリレート、ジペンタエリスリトールヘキサアクリレート、ジオキサングリコールジアクリレート、9,9-ビス[4-(2-ヒドロキシエトキシ)フェニル]フルオレンジアクリレート、ラウリルメタクリレート、フェノキシエチルメタクリレート、フェノキシジエチレングリコールメタクリレート、テトラヒドロフルフリルメタクリレート、イソボルニルメタクリレート、2-メタクリロイロキシエチルフタル酸、2-メタクリロイルオキシエチルアシッドホスフェート、ポリエチレングリコールジメタクリレート、ジメチロールトリシクロデカンジメタクリレート等が挙げられる。 The acrylic resin is not particularly limited, but includes, for example, lauryl acrylate, stearyl acrylate, isostearyl acrylate, phenoxyethyl acrylate, phenoxydiethylene glycol acrylate, tetrahydrofurfuryl acrylate, isobornyl acrylate, 2-acryloyloxyethyl phthalic acid, - Acryloyloxyethyl acid phosphate, polyethylene glycol diacrylate, dimethylol tricyclodecane diacrylate, trimethylolpropane triacrylate, dipentaerythritol hexaacrylate, dioxane glycol diacrylate, 9,9-bis[4-(2-hydroxyethoxy) ) phenyl] fluorene diacrylate, lauryl methacrylate, phenoxyethyl methacrylate, phenoxydiethylene glycol methacrylate, tetrahydrofurfuryl methacrylate, isobornyl methacrylate, 2-methacryloyloxyethyl phthalic acid, 2-methacryloyloxyethyl acid phosphate, polyethylene glycol dimethacrylate, Examples include dimethylol tricyclodecane dimethacrylate.
テルペン樹脂としては、特に制限はないが、例えば、α-ピネン、β-ピネン、ジペンテン、及びリモネン等のモノテルペン類、セドレン、ファルネセン等のセスキテルペン類、アビエチン酸等のジテルペン類のようなテルペン類の単独重合体や、スチレン、α-メチルスチレン等の芳香族ビニル化合物と前記テルペン類との共重合体である芳香族変性テルペン樹脂、フェノール、クレゾール、ヒドロキノン、ナフトール、ビスフェノールA等のフェノール類と前記テルペン類との共重合体であるテルペンフェノール樹脂等が挙げられる。また、これらのテルペン樹脂を水素添加した水素添加テルペン樹脂等も使用可能である。 Terpene resins are not particularly limited, but include, for example, monoterpenes such as α-pinene, β-pinene, dipentene, and limonene, sesquiterpenes such as cedrene and farnesene, and terpenes such as diterpenes such as abietic acid. homopolymers of the above, aromatic modified terpene resins which are copolymers of aromatic vinyl compounds such as styrene and α-methylstyrene and the above terpenes, phenols such as phenol, cresol, hydroquinone, naphthol, and bisphenol A. Examples include terpene phenol resins which are copolymers of and the above-mentioned terpenes. Further, hydrogenated terpene resins obtained by hydrogenating these terpene resins can also be used.
シランカップリング剤としては、特に制限はないが、例えば、n-プロピルトリメトキシシラン、n-プロピルトリエトキシシラン、n-オクチルトリメトキシシラン、n-オクチルトリエトキシシラン、フェニルトリメトキシシラン、フェニルトリエトキシシラン、メチルトリメトキシシラン、メチルトリエトキシシラン、2-[メトキシ(ポリエチレンオキシ)プロピル]-トリメトキシシラン、メトキシトリ(エチレンオキシ)プロピルトリメトキシシラン、3-グリシドキシプロピルトリメトキシシラン、3-アミノプロピルトリメトキシシラン、N-フェニル-3-アミノプロピルトリメトキシシラン、3-メルカプトプロピルトリメトキシシラン、3-(メタクリロイルオキシ)プロピルトリメトキシシラン、3-イソシアナトプロピルトリエトキシシラン、3-イソシアナトプロピルトリメトキシシラン等のシランカップリング剤等が挙げられる。 The silane coupling agent is not particularly limited, but examples include n-propyltrimethoxysilane, n-propyltriethoxysilane, n-octyltrimethoxysilane, n-octyltriethoxysilane, phenyltrimethoxysilane, and phenyltrimethoxysilane. Ethoxysilane, methyltrimethoxysilane, methyltriethoxysilane, 2-[methoxy(polyethyleneoxy)propyl]-trimethoxysilane, methoxytri(ethyleneoxy)propyltrimethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3- Aminopropyltrimethoxysilane, N-phenyl-3-aminopropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, 3-(methacryloyloxy)propyltrimethoxysilane, 3-isocyanatopropyltriethoxysilane, 3-isocyanato Examples include silane coupling agents such as propyltrimethoxysilane.
前記接着性付与剤の配合量としては特に制限はないが、(a)成分100質量部に対して0.1~20質量部が好ましく、0.5~10質量部がより好ましく、1~5質量部が更に好ましい。この範囲であれば、樹脂組成物の機械物性を変えることなく、該樹脂組成物の接着力あるいは粘着力をより向上させることができる。 There is no particular restriction on the amount of the adhesion imparting agent, but it is preferably 0.1 to 20 parts by weight, more preferably 0.5 to 10 parts by weight, and more preferably 1 to 5 parts by weight based on 100 parts by weight of component (a). Parts by mass are more preferred. Within this range, the adhesive force or adhesive force of the resin composition can be further improved without changing the mechanical properties of the resin composition.
[酸化防止剤]
酸化防止剤としては、特に制限はないが、例えば、n-オクタデシル-3-(3,5-ジ-t-ブチル-4-ヒドロキシフェニル)プロピオネート、n-オクタデシル-3-(3,5-ジ-t-ブチル-4-ヒドロキシフェニル)アセテート、ネオドデシル-3-(3,5-ジ-t-ブチル-4-ヒドロキシフェニル)プロピオネート、ドデシル-β-(3,5-ジ-t-ブチル-4-ヒドロキシフェニル)プロピオネート、エチル-α-(4-ヒドロキシ-3,5-ジ-t-ブチルフェニル)イソブチレート、オクタデシル-α-(4-ヒドロキシ-3,5-ジ-t-ブチルフェニル)イソブチレート、オクタデシル-α-(4-ヒドロキシ-3,5-ジ-t-ブチル-4-ヒドロキシフェニル)プロピオネート、2-(n-オクチルチオ)エチル-3,5-ジ-t-ブチル-4-ヒドロキシフェニルアセテート、2-(n-オクタデシルチオ)エチル-3,5-ジ-t-ブチル-4-ヒドロキシフェニルアセテート、2-(n-オクタデシルチオ)エチル-3-(3,5-ジ-t-ブチル-4-ヒドロキシフェニル)プロピオネート、2-(2-ステアロイルオキシエチルチオ)エチル-7-(3-メチル-5-t-ブチル-4-ヒドロキシフェニル)ヘプタノエート、2-ヒドロキシエチル-7-(3-メチル-5-t-ブチル-4-ヒドロキシフェニル)プロピオネート、ペンタエリスリトールテトラキス[3-(3,5-ジ-t-ブチル-4-ヒドロキシフェニル)プロピオネート]等のフェノール系酸化防止剤;ジラウリル-3,3’-チオジプロピオネート、ジミリスチル-3,3’-チオジプロピオネート、ジステアリル-3,3’-チオジプロピオネート、ジトリデシル-3,3’-チオジプロピオネート、ペンタエリスリチルテトラキス(3-ラウリルチオプロピオネート)等の硫黄系酸化防止剤;トリデシルホスファイト、トリフェニルホスファイト、トリス(2,4-ジ-t-ブチルフェニル)ホスファイト、2-エチルヘキシルジフェニルホスファイト、ジフェニルトリデシルホスファイト、2,2-メチレンビス(4,6-ジ-t-ブチルフェニル)オクチルホスファイト、ジステアリルペンタエリスリトールジホスファイト、ビス(2,6-ジ-t-ブチル-4-メチルフェニル)ペンタエリスリトールジホスファイト、2-[[2,4,8,10-テトラキス(1,1-ジメチルエチル)ジベンゾ[d,f][1,3,2]ジオキサホスフェピン-6-イル]オキシ]-N,N-ビス[2-[[2,4,8,10-テトラキス(1,1-ジメチルエチル)ジベンゾ[d,f][1,3,2]ジオキサホスフェピン-6-イル]オキシ]-エチル]エタナミン等のリン系酸化防止剤が挙げられる。
[Antioxidant]
There are no particular limitations on the antioxidant, but for example, n-octadecyl-3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate, n-octadecyl-3-(3,5-di -t-butyl-4-hydroxyphenyl) acetate, neododecyl-3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate, dodecyl-β-(3,5-di-t-butyl-4 -hydroxyphenyl) propionate, ethyl-α-(4-hydroxy-3,5-di-t-butylphenyl) isobutyrate, octadecyl-α-(4-hydroxy-3,5-di-t-butylphenyl) isobutyrate, Octadecyl-α-(4-hydroxy-3,5-di-t-butyl-4-hydroxyphenyl)propionate, 2-(n-octylthio)ethyl-3,5-di-t-butyl-4-hydroxyphenylacetate , 2-(n-octadecylthio)ethyl-3,5-di-t-butyl-4-hydroxyphenylacetate, 2-(n-octadecylthio)ethyl-3-(3,5-di-t-butyl- 4-hydroxyphenyl)propionate, 2-(2-stearoyloxyethylthio)ethyl-7-(3-methyl-5-t-butyl-4-hydroxyphenyl)heptanoate, 2-hydroxyethyl-7-(3-methyl Phenolic antioxidants such as -5-t-butyl-4-hydroxyphenyl) propionate, pentaerythritol tetrakis [3-(3,5-di-t-butyl-4-hydroxyphenyl) propionate]; dilauryl-3, 3'-thiodipropionate, dimyristyl-3,3'-thiodipropionate, distearyl-3,3'-thiodipropionate, ditridecyl-3,3'-thiodipropionate, pentaerythrityltetrakis ( Sulfur-based antioxidants such as tridecyl phosphite, triphenyl phosphite, tris(2,4-di-t-butylphenyl) phosphite, 2-ethylhexyldiphenyl phosphite, diphenyl Tridecyl phosphite, 2,2-methylenebis(4,6-di-t-butylphenyl)octyl phosphite, distearylpentaerythritol diphosphite, bis(2,6-di-t-butyl-4-methylphenyl) ) Pentaerythritol diphosphite, 2-[[2,4,8,10-tetrakis(1,1-dimethylethyl)dibenzo[d,f][1,3,2]dioxaphosphepin-6-yl ]oxy]-N,N-bis[2-[[2,4,8,10-tetrakis(1,1-dimethylethyl)dibenzo[d,f][1,3,2]dioxaphosphepine- Examples include phosphorous antioxidants such as 6-yl]oxy]-ethyl]ethanamine.
前記酸化防止剤の配合量としては特に制限はないが、(a)成分100質量部に対して0.00001~5質量部が好ましく、0.0001~4質量部がより好ましく、0.001~3質量部が更に好ましい。この範囲内であれば、樹脂組成物の機械物性を変えることなく、該樹脂組成物の酸化を防止できる。 The amount of the antioxidant to be blended is not particularly limited, but is preferably 0.00001 to 5 parts by weight, more preferably 0.0001 to 4 parts by weight, and 0.001 to 4 parts by weight per 100 parts by weight of component (a). 3 parts by mass is more preferred. Within this range, oxidation of the resin composition can be prevented without changing the mechanical properties of the resin composition.
[難燃剤]
本発明の樹脂組成物は、難燃性を付与するため、必要に応じて難燃剤を含有してよい。難燃剤としては、特に制限はないが、例えば、リン系難燃剤、金属水和物、ハロゲン系難燃剤、グアニジン系難燃剤等が挙げられる。リン系難燃剤としては、例えば、赤リン、リン酸一アンモニウム、リン酸二アンモニウム、リン酸三アンモニウム、ポリリン酸アンモニウム等のリン酸アンモニウム、リン酸グアニジン、リン酸アミド等の無機系含窒素リン化合物、リン酸、ホスフィンオキシド、トリフェニルホスフェート、トリクレジルホスフェート、トリキシレニルホスフェート、クレジルジフェニルホスフェート、クレジルジ-2,6-キシレニルホスフェート、レゾルシノールビス(ジフェニルホスフェート)、1,3-フェニレンビス(ジ-2,6-キシレニルホスフェート)、ビスフェノールA-ビス(ジフェニルホスフェート)、1,3-フェニレンビス(ジフェニルホスフェート)、フェニルホスホン酸ジビニル、フェニルホスホン酸ジアリル、フェニルホスホン酸ビス(1-ブテニル)、ジフェニルホスフィン酸フェニル、ジフェニルホスフィン酸メチル、ビス(2-アリルフェノキシ)ホスファゼン、ジクレジルホスファゼン等のホスファゼン化合物、リン酸メラミン、ピロリン酸メラミン、ポリリン酸メラミン、ポリリン酸メラム、ポリリン酸メレム、9,10-ジヒドロ-9-オキサ-10-ホスファフェナントレン-10-オキシド、10-(2,5-ジヒドロキシフェニル)-9,10-ジヒドロ-9-オキサ-10-ホスファフェナントレン-10-オキシド等が挙げられる。金属水和物としては、例えば、水酸化アルミニウム水和物、水酸化マグネシウム水和物等が挙げられる。ハロゲン系難燃剤としては、例えば、ヘキサブロモベンゼン、ペンタブロモトルエン、エチレンビス(ペンタブロモフェニル)、エチレンビステトラブロモフタルイミド、1,2-ジブロモ-4-(1,2-ジブロモエチル)シクロヘキサン、テトラブロモシクロオクタン、ヘキサブロモシクロドデカン、ビス(トリブロモフェノキシ)エタン、臭素化ポリフェニレンエーテル、臭素化ポリスチレン、2,4,6-トリス(トリブロモフェノキシ)-1,3,5-トリアジン等が挙げられる。グアニジン系難燃剤としては、スルファミン酸グアニジン、リン酸グアニジン等が挙げられる。
[Flame retardants]
The resin composition of the present invention may contain a flame retardant, if necessary, in order to impart flame retardancy. The flame retardant is not particularly limited, and examples thereof include phosphorus-based flame retardants, metal hydrates, halogen-based flame retardants, guanidine-based flame retardants, and the like. Examples of phosphorus-based flame retardants include red phosphorus, ammonium phosphates such as monoammonium phosphate, diammonium phosphate, triammonium phosphate, and ammonium polyphosphate, and inorganic nitrogen-containing phosphorus such as guanidine phosphate and phosphoric acid amide. Compound, phosphoric acid, phosphine oxide, triphenyl phosphate, tricresyl phosphate, tricylenyl phosphate, cresyl diphenyl phosphate, cresyl di-2,6-xylenyl phosphate, resorcinol bis(diphenyl phosphate), 1,3-phenylene Bis(di-2,6-xylenyl phosphate), bisphenol A-bis(diphenyl phosphate), 1,3-phenylene bis(diphenyl phosphate), divinyl phenylphosphonate, diallyl phenylphosphonate, bis(1) phenylphosphonate -butenyl), phenyl diphenylphosphinate, methyl diphenylphosphinate, bis(2-allylphenoxy)phosphazene, dicresylphosphazene and other phosphazene compounds, melamine phosphate, melamine pyrophosphate, melamine polyphosphate, melam polyphosphate, melem polyphosphate , 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide, 10-(2,5-dihydroxyphenyl)-9,10-dihydro-9-oxa-10-phosphaphenanthrene-10- Examples include oxides. Examples of metal hydrates include aluminum hydroxide hydrate, magnesium hydroxide hydrate, and the like. Examples of halogen flame retardants include hexabromobenzene, pentabromotoluene, ethylenebis(pentabromophenyl), ethylenebistetrabromophthalimide, 1,2-dibromo-4-(1,2-dibromoethyl)cyclohexane, and tetrabromobenzene. Bromocyclooctane, hexabromocyclododecane, bis(tribromophenoxy)ethane, brominated polyphenylene ether, brominated polystyrene, 2,4,6-tris(tribromophenoxy)-1,3,5-triazine, etc. . Examples of the guanidine flame retardant include guanidine sulfamate and guanidine phosphate.
前記難燃剤の配合量としては特に制限はないが、(a)成分100質量部に対して0.01~5質量部が好ましく、0.05~4質量部がより好ましく、0.1~3質量部が更に好ましい。この範囲内であれば、樹脂組成物の機械物性を変えることなく、該樹脂組成物に難燃性を付与できる。 The amount of the flame retardant to be blended is not particularly limited, but is preferably 0.01 to 5 parts by weight, more preferably 0.05 to 4 parts by weight, and more preferably 0.1 to 3 parts by weight based on 100 parts by weight of component (a). Parts by mass are more preferred. Within this range, flame retardancy can be imparted to the resin composition without changing the mechanical properties of the resin composition.
[製造方法]
本発明の樹脂組成物の製造方法は、(a)~(c)成分並びに必要に応じて加えられるその他の添加剤を、例えば、プラネタリーミキサー(井上製作所(株)製)や、攪拌機THINKY CONDITIONING MIXER(シンキー(株)製)を使用して混合する方法が挙げられ、好ましくは更に有機溶剤(例えば、シクロペンタノン、シクロペンタノン、シクロヘキサノン、メシチレン、アニソール、ジブチルエーテル、ジフェニルエーテル、1,4-ジオキサン、N,N-ジメチルホルムアミド、N,N-ジメチルアセトアミド、ジメチルスルホキシド、N-メチルピロリドン等)を添加して混合する方法が挙げられる。有機溶剤を添加することによって樹脂組成物の粘度を下げ、より均一に混合することができる。前記有機溶剤は混合後に減圧留去することで樹脂組成物が得られるが、プリプレグなどとして用いる場合は留去せずにそのまま用いたり、所望する濃度に調整して用いたりしてもよい。
[Production method]
In the method for producing the resin composition of the present invention, components (a) to (c) and other additives added as necessary are mixed using a planetary mixer (manufactured by Inoue Seisakusho Co., Ltd.) or a stirrer THINKY CONDITIONING. A method of mixing using MIXER (manufactured by Shinky Co., Ltd.) is mentioned, and preferably an organic solvent (for example, cyclopentanone, cyclopentanone, cyclohexanone, mesitylene, anisole, dibutyl ether, diphenyl ether, 1,4- Examples include a method of adding and mixing dioxane, N,N-dimethylformamide, N,N-dimethylacetamide, dimethylsulfoxide, N-methylpyrrolidone, etc.). By adding an organic solvent, the viscosity of the resin composition can be lowered and more uniform mixing can be achieved. A resin composition can be obtained by distilling off the organic solvent under reduced pressure after mixing, but when used as a prepreg or the like, it may be used as it is without being distilled off, or it may be adjusted to a desired concentration before use.
[プリプレグ]
本発明の樹脂組成物は、上記した有機溶剤に溶解させ、繊維基材に含浸させて加熱乾燥させることでプリプレグとしても使用できる。
前記繊維基材としては、積層板に使用されている公知のものを使用できる。例えばEガラス、Sガラス、Tガラス、NEガラス、Qガラス(石英ガラス)等の無機繊維;ポリエチレン、ポリエステル、ポリアミド、ポリテトラフルオロエチレン等の有機繊維などが挙げられる。これらは1種類を単独で使用してもよいし、2種以上を併用してもよい。これらの中でも誘電特性の観点から、無機繊維が好ましく、Tガラス、NEガラス、Qガラスがより好ましい。
繊維基材の厚さとしては特に制限はないが、5~500μmが好ましく、10~100μmがより好ましく、20~80μmが更に好ましい。この範囲であれば、柔軟性に優れ、低反り、高強度のプリプレグが得られる。
これらの繊維基材は、誘電特性の向上、樹脂への親和性を向上させるために、加熱又はシランカップリング剤等で表面処理してもよい。
プリプレグ中における樹脂組成物の含有量は特に制限はないが、20~90体積%が好ましく、30~80体積%がより好ましく、40~70体積%が更に好ましい。この範囲であれば、誘電特性、低反りを維持したまま、導体への接着強度を高めることができる。
本発明のプリプレグの厚さは特に制限はないが、10~500μmが好ましく、25~300μmがより好ましく、40~200μmが更に好ましい。この範囲であれば、銅張積層板を良好に作製することができる。
本発明のプリプレグは、あらかじめ加熱によって半硬化(B-stage化)させてもよい。B-stage化の方法としては特に制限はないが、例えば、本発明の樹脂組成物を溶剤に溶解させ、繊維基材に含浸させて乾燥させた後、80~200℃の温度で1~30分間、加熱することでB-stage化ができる。
[Prepreg]
The resin composition of the present invention can also be used as a prepreg by dissolving it in the above-mentioned organic solvent, impregnating it into a fiber base material, and drying it by heating.
As the fiber base material, known materials used in laminates can be used. Examples include inorganic fibers such as E glass, S glass, T glass, NE glass, and Q glass (quartz glass); organic fibers such as polyethylene, polyester, polyamide, and polytetrafluoroethylene. These may be used alone or in combination of two or more. Among these, from the viewpoint of dielectric properties, inorganic fibers are preferred, and T glass, NE glass, and Q glass are more preferred.
The thickness of the fiber base material is not particularly limited, but is preferably 5 to 500 μm, more preferably 10 to 100 μm, and even more preferably 20 to 80 μm. Within this range, a prepreg with excellent flexibility, low warpage, and high strength can be obtained.
These fiber base materials may be surface-treated by heating or with a silane coupling agent or the like in order to improve dielectric properties and affinity for resins.
The content of the resin composition in the prepreg is not particularly limited, but is preferably 20 to 90% by volume, more preferably 30 to 80% by volume, and even more preferably 40 to 70% by volume. Within this range, the adhesive strength to the conductor can be increased while maintaining dielectric properties and low warpage.
The thickness of the prepreg of the present invention is not particularly limited, but is preferably 10 to 500 μm, more preferably 25 to 300 μm, and even more preferably 40 to 200 μm. Within this range, a copper-clad laminate can be produced satisfactorily.
The prepreg of the present invention may be semi-cured (B-staged) by heating in advance. There are no particular limitations on the method for forming the B-stage, but for example, the resin composition of the present invention is dissolved in a solvent, impregnated into a fiber base material, dried, and then heated at a temperature of 80 to 200°C for 1 to 30 minutes. B-stage can be achieved by heating for a few minutes.
[銅張積層板]
本発明のプリプレグは銅箔を重ねてプレスして加熱硬化させ、銅張積層板として使用してもよい。
銅張積層板の製造方法としては、特に制限はないが、例えば前記プリプレグを1~20枚、好ましくは2~10枚用い、その片面又は両面に銅箔を配置してプレスして加熱硬化することにより製造することができる。
銅箔の厚みとしては特に制限はないが、3~70μmが好ましく、10~50μmがより好ましく、15~40μmが更に好ましい。この範囲であれば、高信頼性を保持した、多層の銅張積層板を成形することができる。
銅張積層板の成形条件は、特に制限はないが、例えば、多段プレス、多段真空プレス、連続成形、オートクレーブ成形機等を使用し、温度100~400℃、圧力1~100MPa、加熱時間0.1~4時間の範囲で成形することができる。また、本発明のプリプレグ、銅箔、内層用配線板を組合せて成形し、銅張積層板を成形することもできる。
[Copper-clad laminate]
The prepreg of the present invention may be used as a copper-clad laminate by stacking copper foils, pressing them, heating and curing them.
There are no particular restrictions on the method for producing a copper-clad laminate, but for example, 1 to 20 sheets, preferably 2 to 10 sheets of the prepreg are used, copper foil is placed on one or both sides of the prepreg, and the sheet is pressed and cured by heating. It can be manufactured by
The thickness of the copper foil is not particularly limited, but is preferably 3 to 70 μm, more preferably 10 to 50 μm, and even more preferably 15 to 40 μm. Within this range, it is possible to form a multilayer copper-clad laminate that maintains high reliability.
There are no particular restrictions on the molding conditions for the copper-clad laminate, but for example, a multistage press, multistage vacuum press, continuous molding, autoclave molding machine, etc. are used, the temperature is 100 to 400°C, the pressure is 1 to 100 MPa, and the heating time is 0. Molding can be carried out within a range of 1 to 4 hours. Furthermore, a copper-clad laminate can be formed by combining the prepreg of the present invention, copper foil, and wiring board for inner layer.
[プリント配線板]
本発明の銅張積層板は回路加工し、プリント配線板として使用してもよい。
回路加工の方法としては、特に制限はないが、例えば穴開け加工、金属めっき加工、金属箔のエッチング等による回路形成加工が挙げられる。
また、本発明の樹脂組成物やプリプレグと銅箔を順次積層するビルドアップ法でプリント配線板を製造してもよい。
[Printed wiring board]
The copper-clad laminate of the present invention may be processed into a circuit and used as a printed wiring board.
There are no particular limitations on the method of circuit processing, but examples include circuit forming processing such as hole drilling, metal plating, and etching of metal foil.
Alternatively, a printed wiring board may be manufactured by a build-up method in which the resin composition or prepreg of the present invention and copper foil are sequentially laminated.
以下、実施例及び比較例を示し、本発明をより詳細に説明するが、本発明は下記の実施例に制限されるものではない。 EXAMPLES Hereinafter, the present invention will be explained in more detail by showing examples and comparative examples, but the present invention is not limited to the following examples.
下記実施例に示した分子量はポリスチレンを標準物質としたゲルパーミエーションクロマトグラフィー(GPC)によって測定した重量平均分子量(Mw)である。以下に測定条件を示す。
[GPC測定条件]
展開溶媒:テトラヒドロフラン
流速:0.6mL/min
カラム:TSK Guardcolumn SuperH-L
TSKgel SuperH4000(6.0mmI.D.×15cm×1)
TSKgel SuperH3000(6.0mmI.D.×15cm×1)
TSKgel SuperH2000(6.0mmI.D.×15cm×2)
(いずれも東ソー社製)
カラム温度:40℃
試料注入量:20μL(試料濃度:0.5質量%-テトラヒドロフラン溶液)
検出器:示差屈折率計(RI)
The molecular weights shown in the following examples are weight average molecular weights (Mw) measured by gel permeation chromatography (GPC) using polystyrene as a standard material. The measurement conditions are shown below.
[GPC measurement conditions]
Developing solvent: tetrahydrofuran Flow rate: 0.6 mL/min
Column:TSK Guardcolumn SuperHL-L
TSKgel SuperH4000 (6.0mm I.D. x 15cm x 1)
TSKgel SuperH3000 (6.0mm I.D. x 15cm x 1)
TSKgel SuperH2000 (6.0mm I.D. x 15cm x 2)
(Both manufactured by Tosoh Corporation)
Column temperature: 40℃
Sample injection amount: 20 μL (sample concentration: 0.5% by mass-tetrahydrofuran solution)
Detector: Differential refractometer (RI)
(a)環状イミド化合物
(a-1)マレイミド化合物
N-メチルピロリドン196gに、1,12-ジアミノドデカン200g(1.0mol)及びピロメリット酸無水物207g(0.95mol)を添加し、25℃で3時間撹拌し、その後、さらに150℃で3時間撹拌した。得られた溶液に、無水マレイン酸196g(2.0mol)、酢酸ナトリウム82g(1.0mol)及び無水酢酸204g(2.0mol)を加え、80℃で1時間撹拌した。その後、トルエン500gを加え、更に水洗、脱水後、溶剤を減圧留去し、下記式で示されるビスマレイミド(a-1)を得た。(重量平均分子量3,500、マレイミド当量0.057mol/100g)
(a-2)マレイミド化合物
N-メチルピロリドン361gに、2,4,4-トリメチルヘキサン-1,6-ジアミン158g(1.0mol)及びピロメリット酸無水物214g(0.99mol)を添加し、25℃で3時間撹拌し、その後、さらに150℃で10時間撹拌した。得られた溶液に、無水マレイン酸196g(2.0mol)、酢酸ナトリウム82g(1.0mol)及び無水酢酸204g(2.0mol)を加え、80℃で1時間撹拌した。その後、トルエン1,000gを加え、更に水洗、脱水後、溶剤を減圧留去し、下記式で示されるビスマレイミド(a-2)を得た。(重量平均分子量9,500、マレイミド当量0.021mol/100g)
(a-3)マレイミド化合物
N-メチルピロリドン263gに、イソホロンジアミン170g(1.0mol)及び4,4’-(4,4’-イソプロピリデンジフェノキシ)ジフタル酸無水物499g(0.96mol)を添加し、25℃で3時間撹拌し、その後、さらに150℃で5時間撹拌した。得られた溶液に、無水マレイン酸196g(2.0mol)、酢酸ナトリウム82g(1.0mol)及び無水酢酸204g(2.0mol)を加え、80℃で1時間撹拌した。その後、トルエン500gを加え、更に水洗、脱水後、溶剤を減圧留去し、下記式で示されるビスマレイミド(a-3)を得た。(重量平均分子量20,000、マレイミド当量0.010mol/100g)
(a-4)シトラコンイミド化合物
N-メチルピロリドン263gに、ダイマージアミン523g(1.0mol)及びピロメリット酸無水物211g(0.97mol)を添加し、25℃で3時間撹拌し、その後、さらに150℃で5時間撹拌した。得られた溶液に、無水シトラコン酸226g(2.0mol)、酢酸ナトリウム82g(1.0mol)及び無水酢酸204g(2.0mol)を加え、80℃で1時間撹拌した。その後、トルエン500gを加え、更に水洗、脱水後、溶剤を減圧留去し、下記式で示されるシトラコンイミド(a-4)を得た。(重量平均分子量10,000、マレイミド当量0.020mol/100g)
(a-5)マレイミド化合物
下記式で示されるマレイミド化合物(BMI-2500、Designer Molecules Inc.製)(重量平均分子量3,500、マレイミド当量0.057mol/100g)
(a-6)マレイミド化合物
下記式で示されるマレイミド化合物(BMI-3000、Designer Molecules Inc.製)(重量平均分子量10,000、マレイミド当量0.020mol/100g)
(a-7)マレイミド化合物
アニソール500gに、2,2-ビス(4-(4-アミノフェノキシ)フェニル)プロパン431g(1.05mol)及び4,4’-(4,4’-イソプロピリデンジフェノキシ)ジフタル酸無水物520g(1.0mol)を添加し、室温で5時間撹拌し、更に120℃で3時間撹拌した。得られた溶液に無水マレイン酸19g(0.2mol)を加え、150℃で1時間撹拌した。その後、溶剤、未反応の無水マレイン酸を減圧留去し、下記式で示される(a-7)マレイミドを得た。(重量平均分子量45,000、マレイミド当量0.0044mol/100g)
(b)エポキシ化合物
(b-1)ビフェニルアラルキル型エポキシ樹脂(商品名:「NC-3000」(日本化薬(株)製、エポキシ当量0.30mol/100g))
(b-2)ビスフェノールA型エポキシ樹脂(商品名:「jER-828EL」(三菱ケミカル(株)製、エポキシ当量0.59mol/100g))
(b-3)液状多官能型エポキシ樹脂(商品名:「jER-630」(三菱ケミカル(株)製、エポキシ当量1.1mol/100g))
(b) Epoxy compound (b-1): Biphenyl aralkyl type epoxy resin (product name: "NC-3000" (manufactured by Nippon Kayaku Co., Ltd., epoxy equivalent: 0.30 mol/100 g))
(b-2) Bisphenol A type epoxy resin (product name: "jER-828EL" (manufactured by Mitsubishi Chemical Corporation, epoxy equivalent: 0.59 mol/100 g))
(b-3) Liquid multifunctional epoxy resin (product name: "jER-630" (manufactured by Mitsubishi Chemical Corporation, epoxy equivalent: 1.1 mol/100 g))
(c)イミダゾール化合物
(c-1)2-エチル-4-メチルイミダゾール(イミダゾール当量0.91mol/100g)
(c-2)2,4-ジアミノ-6-[2-(2-メチル-1-イミダゾリル)エチル]-1,3,5-トリアジン(イミダゾール当量0.46mol/100g)
(c-3)2-フェニル-4-ヒドロキシ-5-メチルイミダゾール(イミダゾール当量0.54mol/100g)
(c) Imidazole compound (c-1) 2-ethyl-4-methylimidazole (imidazole equivalent: 0.91 mol/100 g)
(c-2) 2,4-diamino-6-[2-(2-methyl-1-imidazolyl)ethyl]-1,3,5-triazine (imidazole equivalent 0.46 mol/100 g)
(c-3) 2-phenyl-4-hydroxy-5-methylimidazole (imidazole equivalent: 0.54 mol/100 g)
(d)重合開始剤
(d-1)ジクミルパーオキサイド
(d) Polymerization initiator (d-1) Dicumyl peroxide
(e)無機充填剤
(e-1)シリカ「SFP-130MC」(一次粒径のメジアン径0.6μm)(デンカ(株)製)
(e-2)アルミナ「AO-41R」(一次粒径のメジアン径6μm)(アドマテックス(株)製)
(e) Inorganic filler (e-1) Silica “SFP-130MC” (median primary particle size 0.6 μm) (manufactured by Denka Co., Ltd.)
(e-2) Alumina "AO-41R" (median primary particle size 6 μm) (manufactured by Admatex Co., Ltd.)
(f)有機充填剤
(f-1)シリコーンパウダー「KMP-600」(一次粒径のメジアン径5μm)(信越化学工業(株)製)
(f) Organic filler (f-1) Silicone powder "KMP-600" (median primary particle size 5 μm) (manufactured by Shin-Etsu Chemical Co., Ltd.)
(g)接着性付与剤
(g-1)シランカップリング剤(3-グリシドキシプロピルトリメトキシシラン、商品名「KBM-403」、信越化学工業(株)製)
(g-2)シランカップリング剤(N-フェニル-3-アミノプロピルトリメトキシシラン、商品名「KBM-573」、信越化学工業(株)製)
(g) Adhesive agent (g-1) Silane coupling agent (3-glycidoxypropyltrimethoxysilane, trade name "KBM-403", manufactured by Shin-Etsu Chemical Co., Ltd.)
(g-2) Silane coupling agent (N-phenyl-3-aminopropyltrimethoxysilane, trade name "KBM-573", manufactured by Shin-Etsu Chemical Co., Ltd.)
(h)酸化防止剤
(h-1)ペンタエリスリトールテトラキス[3-(3,5-ジ-tert-ブチル-4-ヒドロキシフェニル)プロピオネート](商品名「アデカスタブAO-60」、(株)ADEKA製)
(h) Antioxidant (h-1) Pentaerythritol tetrakis [3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate] (Product name: ADEKA STAB AO-60, manufactured by ADEKA Co., Ltd.) )
(i)難燃剤
(i-1)リン酸グアニジン(商品名「アピノン-303」、(株)三和ケミカル製)
(i) Flame retardant (i-1) Guanidine phosphate (trade name "Apinon-303", manufactured by Sanwa Chemical Co., Ltd.)
[樹脂組成物の調製方法]
実施例1~17及び比較例1~7について、表1~3に示す配合(質量部)に追加して、各成分の合計100質量部に対してシクロペンタノンを100質量部加えて混合し、プラネタリーミキサー(井上製作所(株)製)を使用して80℃で30分混練し、その後25℃まで冷却した。得られた溶液をフラスコに移し、溶剤を減圧留去して樹脂組成物を調製した。
[Method for preparing resin composition]
For Examples 1 to 17 and Comparative Examples 1 to 7, in addition to the formulations (parts by mass) shown in Tables 1 to 3, 100 parts by mass of cyclopentanone was added and mixed with respect to a total of 100 parts by mass of each component. The mixture was kneaded at 80°C for 30 minutes using a planetary mixer (manufactured by Inoue Seisakusho Co., Ltd.), and then cooled to 25°C. The obtained solution was transferred to a flask, and the solvent was distilled off under reduced pressure to prepare a resin composition.
[比誘電率及び誘電正接]
30mm×40mm×100μm厚の金型枠に、調製した樹脂組成物を挟み、180℃で1時間プレスキュアして、試験サンプルを作製した。作製した試験サンプルにネットワーク・アナライザ(キーサイト社製 E5063-2D5)とストリップライン(キーコム株式会社製)を接続して、周波数10GHzにおける比誘電率及び誘電正接を測定した。結果を表1~3に記載した。
[Relative permittivity and dielectric loss tangent]
The prepared resin composition was sandwiched between mold frames of 30 mm x 40 mm x 100 μm thick, and press cured at 180° C. for 1 hour to prepare a test sample. A network analyzer (manufactured by Keysight Corporation, E5063-2D5) and a strip line (manufactured by Keycom Corporation) were connected to the prepared test sample, and the dielectric constant and dielectric loss tangent at a frequency of 10 GHz were measured. The results are listed in Tables 1 to 3.
[ピール強度]
上記の方法で調製した樹脂組成物を厚さ25μmになるようにフィルム状に塗工し樹脂フィルムを作製し、SUS板、該樹脂フィルム、厚さ18μmの銅箔(商品名:TQ-M4-VSP、(株)三井金属製)の順に重ねてプレスし、180℃で1時間加熱して硬化させた。プリント配線板用銅張積層板試験の規格JIS-C-6481:1996に準拠し、テンシロンテスター(東洋精機製作所社製、商品名;ストログラフVE-1D)を用いて、10mm幅で90°方向に50mm/minの速度で、樹脂フィルムから銅箔を剥離するときの力(ピール強度)を求めた。結果を表1~3に記載した。
[Peel strength]
A resin film was prepared by coating the resin composition prepared by the above method into a film with a thickness of 25 μm, and a SUS plate, the resin film, and a copper foil with a thickness of 18 μm (product name: TQ-M4- VSP (manufactured by Mitsui Kinzoku Co., Ltd.) were stacked in this order and pressed, and heated at 180° C. for 1 hour to harden. In accordance with JIS-C-6481:1996, the standard for testing copper-clad laminates for printed wiring boards, using a Tensilon tester (manufactured by Toyo Seiki Seisakusho Co., Ltd., product name: Strograph VE-1D), the test was performed in a 90° direction with a width of 10 mm. The force (peel strength) when peeling the copper foil from the resin film at a speed of 50 mm/min was determined. The results are listed in Tables 1 to 3.
実施例1~17では、硬化物は低比誘電率及び低誘電正接であり、高いピール強度を有していた。
比較例1、2、6では、組成物中にエポキシ基を含有する成分がない、または環状イミド基数/エポキシ基数の値が大きく、硬化が不十分なため、ピール強度が低く、また、比誘電率及び誘電正接も高くなった。
比較例3では、環状イミド基数/エポキシ基数の値が小さいため、比誘電率及び誘電正接が高くなった。
比較例4では、エポキシ基数/イミダゾール基数の値が小さいため、ピール強度が低くなった。
比較例5、7では、エポキシ基数/イミダゾール基数の値が大きいため、ピール強度が低くなった。
In Examples 1 to 17, the cured products had a low dielectric constant and a low dielectric loss tangent, and had high peel strength.
In Comparative Examples 1, 2, and 6, there was no component containing an epoxy group in the composition, or the value of the number of cyclic imide groups/the number of epoxy groups was large, resulting in insufficient curing, resulting in low peel strength and poor dielectric strength. The coefficient and dielectric loss tangent were also increased.
In Comparative Example 3, the relative dielectric constant and dielectric loss tangent were high because the value of the number of cyclic imide groups/the number of epoxy groups was small.
In Comparative Example 4, the peel strength was low because the value of the number of epoxy groups/the number of imidazole groups was small.
In Comparative Examples 5 and 7, the peel strength was low because the value of the number of epoxy groups/the number of imidazole groups was large.
[プリプレグの製造方法]
実施例18~21、比較例8、9では、実施例1~4、比較例3、4で調製した各樹脂組成物1,000gとシクロペンタノン1,000gを混合し、石英ガラスクロスSQX2116AC(厚さ90μm、信越化学工業(株)製)に含浸させ、120℃で5分加熱してシクロペンタノンを揮発させ、プリプレグを製造した。樹脂組成物の含有量(質量%)、プリプレグの厚さを表4に記載した。
[Prepreg manufacturing method]
In Examples 18 to 21 and Comparative Examples 8 and 9, 1,000 g of each resin composition prepared in Examples 1 to 4 and Comparative Examples 3 and 4 and 1,000 g of cyclopentanone were mixed, and quartz glass cloth SQX2116AC ( A prepreg having a thickness of 90 μm (manufactured by Shin-Etsu Chemical Co., Ltd.) was impregnated and heated at 120° C. for 5 minutes to volatilize cyclopentanone. The content (mass%) of the resin composition and the thickness of the prepreg are listed in Table 4.
[銅張積層板の製造方法]
上記で得られたプリプレグ10枚と厚さ18μmの銅箔(商品名:TQ-M4-VSP、(株)三井金属製)9枚を交互に重ね、更に上下最表面に銅箔を重ね、3MPaでプレスし、180℃で1時間加熱して両面銅張積層板を製造した。
[Method for manufacturing copper-clad laminates]
10 sheets of the prepreg obtained above and 9 sheets of 18 μm thick copper foil (product name: TQ-M4-VSP, manufactured by Mitsui Kinzoku Co., Ltd.) were stacked alternately, and further copper foil was stacked on the top and bottom outermost surfaces. and heated at 180° C. for 1 hour to produce a double-sided copper-clad laminate.
[プリント配線板の製造方法]
上記で得られた両面銅張積層板の両側の表面に、厚さ30μmのドライレジストフィルム(NIT430E、(株)ニッコー・マテリアルズ製)を80℃、60秒で真空ラミネートして張り合わせた。その後回路パターンが形成されたマスクを接触させ、上下からUVを照度500mWで10秒照射した。その後、10%炭酸水素ナトリウム水溶液に40℃で10分含浸させて現像した。その後、エッチング液(H-1000A、(株)サンハヤト製)に40℃で10分含浸させてエッチングした。その後、10%水酸化ナトリウム水溶液に40℃で20分含浸させて洗浄することで、両面に回路が形成されたプリント配線板を製造した。
[Manufacturing method of printed wiring board]
Dry resist films (NIT430E, manufactured by Nikko Materials Co., Ltd.) having a thickness of 30 μm were vacuum laminated and pasted together at 80° C. for 60 seconds on both surfaces of the double-sided copper-clad laminate obtained above. Thereafter, a mask on which a circuit pattern was formed was brought into contact with the mask, and UV was irradiated from above and below at an illuminance of 500 mW for 10 seconds. Thereafter, the film was developed by being immersed in a 10% aqueous sodium hydrogen carbonate solution at 40°C for 10 minutes. Thereafter, it was etched by being impregnated with an etching solution (H-1000A, manufactured by Sanhayato Co., Ltd.) at 40° C. for 10 minutes. Thereafter, a printed wiring board with circuits formed on both sides was manufactured by impregnating and cleaning it in a 10% aqueous sodium hydroxide solution at 40° C. for 20 minutes.
[伝送損失]
ネットワークネットワークアナライザアナライザ(キーサイトテクノロジー社製、品番E5071C)を用い、導体長さを400mm、銅箔厚さを18μm、ライン幅を0.12mm、絶縁層の厚さを0.20mmとし、特性インピーダンスが50Ωになるように調整して、40GHzにおける伝送損失を測定した。結果を表4に記載した。
[Transmission loss]
Using a network analyzer (manufactured by Keysight Technologies, product number E5071C), the conductor length was 400 mm, the copper foil thickness was 18 μm, the line width was 0.12 mm, the insulating layer thickness was 0.20 mm, and the characteristic impedance was was adjusted to 50Ω, and the transmission loss at 40GHz was measured. The results are listed in Table 4.
実施例18~21では、いずれも伝送損失が低い値となった。
比較例8、9では、比較例3、4で示したとおり比誘電率、誘電正接が高いので、伝送損失が高い値となった。
In Examples 18 to 21, the transmission losses were all low.
In Comparative Examples 8 and 9, as shown in Comparative Examples 3 and 4, the relative permittivity and dielectric loss tangent were high, so the transmission loss was a high value.
Claims (9)
(b)エポキシ化合物、及び
(c)イミダゾール化合物
を含有し、前記環状イミド化合物の環状イミド基数、前記エポキシ化合物のエポキシ基数、及び前記イミダゾール化合物のイミダゾール基数が下記2式をいずれも満たす樹脂組成物。
0.3 ≦ 環状イミド基数/エポキシ基数 ≦ 3.0
2.0 ≦ エポキシ基数/イミダゾール基数 ≦ 20.0
(a) cyclic imide compound,
(b) A resin composition containing an epoxy compound and (c) an imidazole compound, in which the number of cyclic imide groups of the cyclic imide compound, the number of epoxy groups of the epoxy compound, and the number of imidazole groups of the imidazole compound satisfy the following two formulas. .
0.3 ≦ Number of cyclic imide groups/Number of epoxy groups ≦ 3.0
2.0 ≦ Number of epoxy groups/Number of imidazole groups ≦ 20.0
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