JP2004256640A - Resin composition used for interlaminar adhesive film for printed wiring board - Google Patents
Resin composition used for interlaminar adhesive film for printed wiring board Download PDFInfo
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- JP2004256640A JP2004256640A JP2003048057A JP2003048057A JP2004256640A JP 2004256640 A JP2004256640 A JP 2004256640A JP 2003048057 A JP2003048057 A JP 2003048057A JP 2003048057 A JP2003048057 A JP 2003048057A JP 2004256640 A JP2004256640 A JP 2004256640A
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- resin composition
- polyphenylene ether
- adhesive film
- printed wiring
- Prior art date
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- 239000011342 resin composition Substances 0.000 title claims abstract description 20
- 239000002313 adhesive film Substances 0.000 title claims abstract description 17
- 229920001955 polyphenylene ether Polymers 0.000 claims abstract description 34
- 125000003700 epoxy group Chemical group 0.000 claims abstract description 18
- 125000000524 functional group Chemical group 0.000 claims abstract description 13
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 7
- 125000004018 acid anhydride group Chemical group 0.000 claims abstract description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 6
- 125000003277 amino group Chemical group 0.000 claims abstract description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 5
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 6
- 239000004593 Epoxy Substances 0.000 claims description 5
- 230000016507 interphase Effects 0.000 claims description 5
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 239000004020 conductor Substances 0.000 abstract description 8
- 238000000926 separation method Methods 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 14
- -1 polyethylene Polymers 0.000 description 11
- 229920001577 copolymer Polymers 0.000 description 10
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 8
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 7
- 239000003822 epoxy resin Substances 0.000 description 7
- 239000010408 film Substances 0.000 description 7
- 229920000647 polyepoxide Polymers 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 229920000139 polyethylene terephthalate Polymers 0.000 description 5
- 239000005020 polyethylene terephthalate Substances 0.000 description 5
- QQOMQLYQAXGHSU-UHFFFAOYSA-N 2,3,6-Trimethylphenol Chemical compound CC1=CC=C(C)C(O)=C1C QQOMQLYQAXGHSU-UHFFFAOYSA-N 0.000 description 4
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 239000011889 copper foil Substances 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- GVLZQVREHWQBJN-UHFFFAOYSA-N 3,5-dimethyl-7-oxabicyclo[2.2.1]hepta-1,3,5-triene Chemical compound CC1=C(O2)C(C)=CC2=C1 GVLZQVREHWQBJN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- UWFRVQVNYNPBEF-UHFFFAOYSA-N 1-(2,4-dimethylphenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(C)C=C1C UWFRVQVNYNPBEF-UHFFFAOYSA-N 0.000 description 2
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 2
- NGNBLQAYJAKWKR-UHFFFAOYSA-N 5-methyl-3-phenyl-7-oxabicyclo[2.2.1]hepta-1,3,5-triene Chemical compound O1C=2C(C)=CC1=CC=2C1=CC=CC=C1 NGNBLQAYJAKWKR-UHFFFAOYSA-N 0.000 description 2
- OMIHGPLIXGGMJB-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]hepta-1,3,5-triene Chemical compound C1=CC=C2OC2=C1 OMIHGPLIXGGMJB-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 229920000106 Liquid crystal polymer Polymers 0.000 description 2
- 239000004977 Liquid-crystal polymers (LCPs) Substances 0.000 description 2
- 239000004677 Nylon Substances 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000011229 interlayer Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229920001778 nylon Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229920005992 thermoplastic resin Polymers 0.000 description 2
- 229920001187 thermosetting polymer Polymers 0.000 description 2
- 239000002966 varnish Substances 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- USGYMDAUQBQWFU-UHFFFAOYSA-N 1,2,5,6-diepoxycyclooctane Chemical compound C1CC2OC2CCC2OC12 USGYMDAUQBQWFU-UHFFFAOYSA-N 0.000 description 1
- LFKLPJRVSHJZPL-UHFFFAOYSA-N 1,2:7,8-diepoxyoctane Chemical compound C1OC1CCCCC1CO1 LFKLPJRVSHJZPL-UHFFFAOYSA-N 0.000 description 1
- OUPZKGBUJRBPGC-UHFFFAOYSA-N 1,3,5-tris(oxiran-2-ylmethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound O=C1N(CC2OC2)C(=O)N(CC2OC2)C(=O)N1CC1CO1 OUPZKGBUJRBPGC-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- SYEWHONLFGZGLK-UHFFFAOYSA-N 2-[1,3-bis(oxiran-2-ylmethoxy)propan-2-yloxymethyl]oxirane Chemical compound C1OC1COCC(OCC1OC1)COCC1CO1 SYEWHONLFGZGLK-UHFFFAOYSA-N 0.000 description 1
- HPILSDOMLLYBQF-UHFFFAOYSA-N 2-[1-(oxiran-2-ylmethoxy)butoxymethyl]oxirane Chemical compound C1OC1COC(CCC)OCC1CO1 HPILSDOMLLYBQF-UHFFFAOYSA-N 0.000 description 1
- KUAUJXBLDYVELT-UHFFFAOYSA-N 2-[[2,2-dimethyl-3-(oxiran-2-ylmethoxy)propoxy]methyl]oxirane Chemical compound C1OC1COCC(C)(C)COCC1CO1 KUAUJXBLDYVELT-UHFFFAOYSA-N 0.000 description 1
- UPZFLZYXYGBAPL-UHFFFAOYSA-N 2-ethyl-2-methyl-1,3-dioxolane Chemical compound CCC1(C)OCCO1 UPZFLZYXYGBAPL-UHFFFAOYSA-N 0.000 description 1
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 1
- HDHUBPBUIYXNSS-UHFFFAOYSA-N 2-methyl-6-(2-methylbutyl)phenol Chemical compound CCC(C)CC1=CC=CC(C)=C1O HDHUBPBUIYXNSS-UHFFFAOYSA-N 0.000 description 1
- GRXOKDOOUFYKLX-UHFFFAOYSA-N 3,5-dichloro-7-oxabicyclo[2.2.1]hepta-1(6),2,4-triene Chemical compound ClC1=C(O2)C(Cl)=CC2=C1 GRXOKDOOUFYKLX-UHFFFAOYSA-N 0.000 description 1
- MECNWXGGNCJFQJ-UHFFFAOYSA-N 3-piperidin-1-ylpropane-1,2-diol Chemical compound OCC(O)CN1CCCCC1 MECNWXGGNCJFQJ-UHFFFAOYSA-N 0.000 description 1
- OECTYKWYRCHAKR-UHFFFAOYSA-N 4-vinylcyclohexene dioxide Chemical compound C1OC1C1CC2OC2CC1 OECTYKWYRCHAKR-UHFFFAOYSA-N 0.000 description 1
- ZFIVKAOQEXOYFY-UHFFFAOYSA-N Diepoxybutane Chemical compound C1OC1C1OC1 ZFIVKAOQEXOYFY-UHFFFAOYSA-N 0.000 description 1
- JHWNWJKBPDFINM-UHFFFAOYSA-N Laurolactam Chemical compound O=C1CCCCCCCCCCCN1 JHWNWJKBPDFINM-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 229920000299 Nylon 12 Polymers 0.000 description 1
- 229920001007 Nylon 4 Polymers 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229930182556 Polyacetal Natural products 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004962 Polyamide-imide Substances 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 239000004695 Polyether sulfone Substances 0.000 description 1
- 239000004697 Polyetherimide Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 239000004734 Polyphenylene sulfide Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 229920001328 Polyvinylidene chloride Polymers 0.000 description 1
- 108010009736 Protein Hydrolysates Proteins 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 229920001893 acrylonitrile styrene Polymers 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000007772 electroless plating Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 125000005843 halogen group Chemical group 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
- 239000012760 heat stabilizer Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- 125000005462 imide group Chemical group 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 239000011810 insulating material Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- JAYXSROKFZAHRQ-UHFFFAOYSA-N n,n-bis(oxiran-2-ylmethyl)aniline Chemical compound C1OC1CN(C=1C=CC=CC=1)CC1CO1 JAYXSROKFZAHRQ-UHFFFAOYSA-N 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- MMCOUVMKNAHQOY-UHFFFAOYSA-L oxido carbonate Chemical compound [O-]OC([O-])=O MMCOUVMKNAHQOY-UHFFFAOYSA-L 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920001643 poly(ether ketone) Polymers 0.000 description 1
- 229920003207 poly(ethylene-2,6-naphthalate) Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002627 poly(phosphazenes) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920002312 polyamide-imide Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920001083 polybutene Polymers 0.000 description 1
- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920001601 polyetherimide Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000011112 polyethylene naphthalate Substances 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920000069 polyphenylene sulfide Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 229920001289 polyvinyl ether Polymers 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- SCUZVMOVTVSBLE-UHFFFAOYSA-N prop-2-enenitrile;styrene Chemical compound C=CC#N.C=CC1=CC=CC=C1 SCUZVMOVTVSBLE-UHFFFAOYSA-N 0.000 description 1
- 238000011403 purification operation Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000000807 solvent casting Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 238000003856 thermoforming Methods 0.000 description 1
- 229920006259 thermoplastic polyimide Polymers 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 229920006163 vinyl copolymer Polymers 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
- Polyethers (AREA)
- Production Of Multi-Layered Print Wiring Board (AREA)
- Manufacturing Of Printed Wiring (AREA)
Abstract
Description
【０００１】
【発明の属する技術分野】
本発明は、パターン回路が形成された導体層と樹脂絶縁層を交互に積み上げたビルトアッププリント配線板において、樹脂絶縁層を簡易的に所望の厚みで形成するのに有用な接着フィルムに用いられるポリフェニレンエーテル樹脂組成物に関するものである。
【０００２】
【従来の技術】
ポリフェニレンエーテルは高耐熱特性と低誘電特性を兼ね備え、プリント配線板の相間絶縁材料として有用であることが記載されている。（例えば、特許文献１参照。）
しかし、ポリフェニレンエーテルをプリント配線板用接着フィルムに用いた場合、フィルムと導体回路層との密着性が低いため、導体回路層とフィルムが剥れ易いという欠点が指摘されていた。
【０００３】
【特許文献１】
特公平６−１７４５６号公報（第３頁）
【０００４】
【発明が解決しようとする課題】
本発明は、導体回路層との密着性が高く、導体回路層との剥離が抑えられ、かつ誘電特性と耐熱特性に優れたプリント配線板用層間接着フィルムを与える、ポリフェニレンエーテル樹脂組成物を提供することを目的とする。
【０００５】
【課題を解決するための手段】
本発明者は、プリント配線板用相間接着フィルムに用いるポリフェニレンエーテル樹脂組成物について鋭意検討を進めた結果、エポキシ基、酸無水基、カルボキシル基、アミノ基、水酸基、シアノ基、イソシアネート基の官能基群（Ａ）の中から選ばれる、少なくとも１種類の官能基を有する官能化ポリフェニレンエーテル（Ｂ）、を含む樹脂組成物のフィルムは導体回路層との接着性が高く、フィルムと導体回路層との剥れが抑えられたプリント配線板を与えることを見出し本発明に至った。
【０００６】
即ち本発明は、
エポキシ基、酸無水基、カルボキシル基、アミノ基、水酸基、シアノ基、イソシアネート基の官能基群（Ａ）の中から選ばれる、少なくとも１種類の官能基を有する官能化ポリフェニレンエーテル（Ｂ）、を含むことを特徴とするプリント配線板用層間接着フィルム（Ｃ）に用いられる樹脂組成物である。
【０００７】
【発明の実施の形態】
以下、本発明を詳細に説明する。
本発明の官能化ポリフェニレンエーテル（Ｂ）とは下記（式１）の主鎖構造を持つ重合体または共重合体で、なおかつ官能基を有するものである。
【０００８】
【化１】
［Ｒ１、Ｒ２、Ｒ３、Ｒ４は各々独立して、水素原子、アルキル基またはハロゲン原子を表す。］
具体的には、ポリ（２，６−ジメチル−１，４−フェニレンエーテル）、ポリ（２−メチルー６−フェニルー１，４−フェニレンエーテル）、ポリ（２−メチル−６−フェニルー１，４−フェニレンエーテル）、ポリ（２，６−ジクロロ−１，４−フェニレンエーテル）等である。
【００１０】
本発明の共重合体の具体例としては、２，６−ジメチルフェノールと他のフェノール類（例えば２，３，６−トリメチルフェノールや２−メチル−６−メチルブチルフェノール）との共重合体のようなポリフェニレンエーテル共重合体が挙げられる。
中でもポリ（２，６−ジメチル−１，４−フェニレンエーテル）、２，６−ジメチルフェノールと２，３，６−トリメチルフェノールとの共重合体が好ましく使用でき、最も好ましくはポリ（２，６−ジメチル−１，４−フェニレンエーテル）である。
【００１１】
本発明の官能化ポリフェニレンエーテル（Ｂ）が有する官能基とは、エポキシ基、酸無水基、カルボキシル基、アミノ基、水酸基、シアノ基、イソシアネート基の官能基群（Ａ）の中から選ばれる少なくとも１種類の官能基であり、中でもエポキシ基、酸無水基、カルボキシル基が密着フィルムと導体回路の密着性を向上させる観点から好ましく、エポキシ基が最も好ましい。
本発明の官能化ポリフェニレンエーテル（Ｂ）の数平均分子量は３０，０００未満であり、好ましくは１０，０００未満、特に好ましくは５，０００未満である。分子量が低いほど溶剤への溶解性が向上し、溶剤キャストによる製膜時に製膜性が向上する。
【００１２】
本発明の官能化ポリフェニレンエーテル（Ｂ）の製造方法は特に限定されるものではないが、その一例として、分子内に少なくとも２個のエポキシ基を有するエポキシ化合物（Ｄ）とポリフェニレンエーテルを反応させる方法が挙げられる。
エポキシ化合物（Ｄ）の具体例としては、１，３−ブタジエンジエポキシド、１，２，５，６−ジエポキシシクロオクタン、１，２，７，８−ジエポキシオクタン、ビニルシクロヘキセンジオキサイド、ジグリシジルエーテル、エポキシ樹脂と総称される化合物の一群が具体例として挙げられる。エポキシ樹脂の具体例としては、ブタンジオールジグリシジルエーテル、ネオペンチルグリコールジグリシジルエーテル、トリメチロールプロパントリグリシジルエーテル、グリセリントリグリシジルエーテル、トリグリシジルイソシアヌレート、１，３−ジグリシジルヒダントレイン、ビスフェノールＡ型エポキシ樹脂、エチレングリコールジグリシジルエーテル、ジグリシジルアニリン等が挙げられ、中でもビスフェノールＡ型エポキシ樹脂、または、エチレングリコールジグリシジルエーテルが好ましく用いられる。
【００１３】
別の一例として、特開２０００−１９１７６９号公報では、固体状態のポリフェニレンエーテルと分子内に少なくとも１個の炭素−炭素二重結合または三重結合及び、カルボキシル基、酸化アシル基、イミノ基、イミド基、水酸基およびグリシジル基からなる群から選ばれる少なくとも１個の官能基を有する官能化化合物を反応させて得られる官能化ポリフェニレンエーテルの製造方法が開示されている。
【００１４】
本発明のプリント配線板用相間接着フィルム（Ｃ）は樹脂組成物を熱成形するほか、支持体に樹脂組成物を溶解した樹脂溶液を塗布した後、乾燥させて得ることができる。支持体としてはポリエステル、ポリエチレン、ポリカーボネート、等が挙げられるが、中でもポリエチレンテレフタレートが好ましい。樹脂組成物を溶解する溶剤としては例えば、トルエン、キシレン、アセトン、メチルエチルケトンが挙げられるが、本発明の樹脂組成物が均一に溶解するものであれば特に限定されない。
本発明のプリント配線板用相間接着フィルム（Ｃ）の上に、スパッタリング法、蒸着法、無電解メッキ法等により金属薄膜を形成する。金属薄膜としては銅が好ましい。この金属薄膜にアディティブ法、サブトラクティブ法等により、回路パターンを形成する。
【００１５】
本発明の樹脂組成物には他の熱可塑性樹脂、あるいは熱硬化性樹脂を一種または二種以上配合することも可能である。熱可塑性樹脂としてはポリエチレン、ポリプロピレン、ポリブテン、エチレン・プロピレン共重合体、ポリ（４−メチル−ペンテン）等のポリオレフィン類およびその誘導体、ナイロン４、ナイロン６、ナイロン６・６、ナイロン６・１０、ナイロン１２などのポリアミド類およびその誘導体、ポリエチレンテレフタレート、ポリブチレンテレフタレート、ポリエチレンナフタレート、ポリエチレンテレフタレート・ポリエチレングリコールブロック共重合体などのポリエステル類およびその誘導体、変性ポリフェニレンエーテル、ポリカーボネート、ポリアセタール、ポリスルフォン、ポリ塩化ビニ
ルおよびその共重合体、ポリ塩化ビニリデンおよびその共重合体、ポリメチルメタクリレート類、アクリル酸（またはメタクリル酸）エステル共重合体類、ポリスチレン類、アクリロニトリルスチレン共重合体類、アクリロニトリルスチレンブタジエン系共重合体等のポリスチレン類およびその共重合体類、ポリ酢酸ビニル類、ポリビニルホルマール、ポリビニルアセタール、ポリビニルブチラール類、エチレン酢酸ビニル共重合体およびその加水分解物類、ポリビニルアルコール類、スチレンブタジエンブロック共重合体類、ポリブタジエン、ポリイソプレン等のゴム類、ポリメトキシエチレン、ポリエトキシエチレン等のポリビニルエーテル類、ポリアクリルアマイド、ポリホスファーゼン類、ポリエーテルスルホン、ポリエーテルケトン、ポリエーテルイミド、ポリフェニレンサルファイド、ポリアミドイミド、熱可塑性ポリイミド、芳香族ポリエステル等の液晶ポリマー、側鎖に液晶成分を含有する側鎖型液晶ポリマー等が挙げられる。熱硬化性樹脂としてはエポキシ樹脂、フェノール樹脂、ポリイミド前駆体等が挙げられる。
【００１６】
本発明の硬化性樹脂組成物には目的に応じ、適当な添加剤を添加しても良い．添加剤としては、難燃剤、熱安定剤、酸化防止剤、ＵＶ吸収剤、界面活性剤、滑剤、無機充填剤、有機充填剤、ポリマー添加剤、ジアルキルパーオキサイド、パーオキシ、パーオキシカーボネート、ヒドロパーオキサイド、パーオキシケタール等が挙げられる。
【００１７】
【発明の実施の形態】
次に実施例により本発明を更に詳細に説明するが、本発明はこれらの例によってなんら限定されるべきではない。
＜評価方法＞
１．反応直後のエポキシ基を有するポリフェニレンエーテルの精製
まず、反応後のエポキシ基を有するポリフェニレンエーテル粉末に残存する未反応の多官能エポキシ化合物を除去するために、反応生成物２ｇを２０ｍｌのトルエンに溶解し後、大過剰のメタノールを加えてポリマーを沈殿させた。沈殿したポリマーをろ過して分離した後、１５０℃、０．１ｍｍＨｇの条件で１時間、減圧乾燥させた。
２．エポキシ基を有するポリフェニレンエーテルのプロトンＮＭＲ測定
１の精製操作によって得られた官能化ポリフェニレンエーテルを重クロロホルムに溶解し２７０ＭＨｚＮＭＲにて測定を行った。ピークのケミカルシフトはテトラメチルシランのピーク（０．００ｐｐｍ）を基準として決定した。ポリフェニレンエーテル１分子当たりのエポキシ基の数はポリフェニレンエーテルの芳香環３，５位プロトンに起因するピーク（６．４７ｐｐｍ）とエポキシ基に起因するピークの面積比から求めた。
【００１８】
【実施例１】
数平均分子量２，１００の粉体状ポリフェニレンエーテル２．０ＫｇとビスフェノールＡ型エポキシ樹脂（旭化成エポキシ（株）製ＡＥＲ２５０）６００ｇ、トリ−ｎ−ブチルアミン１００ｇを良く混合した後オートクレーブに密閉し、１５０℃、２時間、加熱した。反応生成物を上記、１．エポキシ基を有するポリフェニレンエーテルの精製に記載の方法に従って処理し、ＧＰＣ及びプロトンＮＭＲ測定を行った。反応後ポリマーのＧＰＣ曲線の形状は原料ポリフェニレンエーテルのＧＰＣ曲線の形状と良く一致し、架橋反応が起きていないことが確認された。エポキシ化ポリフェニレンエーテルのプロトンＮＭＲ測定を行い、２．７３〜２．７５ｐｐｍ、２．８７〜２．９１ｐｐｍ、および３．３４ｐｐｍのピークはエポキシ基のプロトンに起因する。これらのピーク面積とフェニレンエーテルユニットの３，５位プロトンのピーク面積比から計算した結果、反応後ポリマーは１分子当たり平均１．２個のエポキシ基を有することが判った。
【００１９】
【実施例２】
ビスフェノールＡ型エポキシ樹脂（旭化成エポキシ（株）製ＡＥＲ２５０）１００重量部、実施例１で得られたエポキシ化ポリフェニレンエーテル５０重量部、ジシアンジアミド３部、２−メチルイミダゾール１部をメチルエチルケトンに溶解させワニスを作成した。このワニスをポリエチレンテレフタレート（ＰＥＴ）支持体の上にローラーコーターで塗布、乾燥させ、接着フィルムを得た。このフィルム上に０．５μｍの銅箔層を形成し銅箔層付き接着フィルムを得た。この銅箔層付き接着フィルムを厚さ１８μｍのガラスエポキシ両面銅張積層板の両面にラミネートし、１８０℃、３０分加熱し、両面に銅箔層付き接着フィルムが形成された銅張り積層板（１）を作成した。この積層板（１）をＪＩＳＣ６４８１に基づき銅密着強度を測定した結果、１．５Ｋｇ／ｃｍ２であった。
【００２０】
【比較例１】
数平均分子量２，１００のポリフェニレンエーテルを用いた他は実施例２と同様に行った。銅密着強度は０．６Ｋｇ／ｃｍ２であった。
【００２１】
【発明の効果】
本発明はビルトアッププリント配線板において、樹脂絶縁層を簡易に形成可能な密着フィルムに用いられるポリフェニレンエーテル樹脂組成物に関するものである。[0001]
TECHNICAL FIELD OF THE INVENTION
INDUSTRIAL APPLICABILITY The present invention is used for an adhesive film useful for simply forming a resin insulating layer with a desired thickness in a built-up printed wiring board in which conductor layers and resin insulating layers on which pattern circuits are formed are alternately stacked. The present invention relates to a polyphenylene ether resin composition.
[0002]
[Prior art]
It is described that polyphenylene ether has both high heat resistance and low dielectric properties, and is useful as an interphase insulating material of a printed wiring board. (For example, refer to Patent Document 1.)
However, when polyphenylene ether is used for an adhesive film for a printed wiring board, a drawback has been pointed out that the conductor circuit layer and the film are easily peeled off due to low adhesion between the film and the conductor circuit layer.
[0003]
[Patent Document 1]
Japanese Patent Publication No. 6-17456 (page 3)
[0004]
[Problems to be solved by the invention]
The present invention provides a polyphenylene ether resin composition having high adhesion to a conductor circuit layer, suppressing peeling from the conductor circuit layer, and providing an interlayer adhesive film for a printed wiring board having excellent dielectric properties and heat resistance properties. The purpose is to do.
[0005]
[Means for Solving the Problems]
The present inventors have conducted intensive studies on the polyphenylene ether resin composition used for the interphase adhesive film for a printed wiring board, and have found that the epoxy group, acid anhydride group, carboxyl group, amino group, hydroxyl group, cyano group, and isocyanate group A film of a resin composition containing a functionalized polyphenylene ether (B) having at least one type of functional group selected from the group (A) has high adhesion to a conductive circuit layer, and the film and the conductive circuit layer The present invention was found to provide a printed wiring board in which peeling of the printed wiring board was suppressed, and reached the present invention.
[0006]
That is, the present invention
Functionalized polyphenylene ether (B) having at least one kind of functional group selected from functional group (A) of epoxy group, acid anhydride group, carboxyl group, amino group, hydroxyl group, cyano group and isocyanate group. It is a resin composition used for an interlayer adhesive film (C) for a printed wiring board, characterized in that:
[0007]
BEST MODE FOR CARRYING OUT THE INVENTION
Hereinafter, the present invention will be described in detail.
The functionalized polyphenylene ether (B) of the present invention is a polymer or copolymer having a main chain structure represented by the following (formula 1) and having a functional group.
[0008]
Embedded image
[R1, R2, R3 and R4 each independently represent a hydrogen atom, an alkyl group or a halogen atom. ]
Specifically, poly (2,6-dimethyl-1,4-phenylene ether), poly (2-methyl-6-phenyl-1,4-phenylene ether), poly (2-methyl-6-phenyl-1,4-phenylene ether) Phenylene ether) and poly (2,6-dichloro-1,4-phenylene ether).
[0010]
Specific examples of the copolymer of the present invention include copolymers of 2,6-dimethylphenol with other phenols (for example, 2,3,6-trimethylphenol and 2-methyl-6-methylbutylphenol). Polyphenylene ether copolymer.
Among them, poly (2,6-dimethyl-1,4-phenylene ether) and a copolymer of 2,6-dimethylphenol and 2,3,6-trimethylphenol can be preferably used, and most preferably, poly (2,6 -Dimethyl-1,4-phenylene ether).
[0011]
The functional group of the functionalized polyphenylene ether (B) of the present invention is at least one selected from the functional group group (A) of an epoxy group, an acid anhydride group, a carboxyl group, an amino group, a hydroxyl group, a cyano group, and an isocyanate group. It is one type of functional group, among which an epoxy group, an acid anhydride group, and a carboxyl group are preferred from the viewpoint of improving the adhesion between the adhesive film and the conductor circuit, and the epoxy group is most preferred.
The number average molecular weight of the functionalized polyphenylene ether (B) of the present invention is less than 30,000, preferably less than 10,000, particularly preferably less than 5,000. The lower the molecular weight is, the more the solubility in a solvent is improved, and the better the film forming property is at the time of film formation by solvent casting.
[0012]
The method for producing the functionalized polyphenylene ether (B) of the present invention is not particularly limited, but as an example, a method of reacting an epoxy compound (D) having at least two epoxy groups in a molecule with polyphenylene ether. Is mentioned.
Specific examples of the epoxy compound (D) include 1,3-butadiene diepoxide, 1,2,5,6-diepoxycyclooctane, 1,2,7,8-diepoxyoctane, vinylcyclohexene dioxide, A specific example is a group of compounds generally referred to as glycidyl ether and epoxy resin. Specific examples of the epoxy resin include butanediol diglycidyl ether, neopentyl glycol diglycidyl ether, trimethylolpropane triglycidyl ether, glycerin triglycidyl ether, triglycidyl isocyanurate, 1,3-diglycidyl hydantolein, and bisphenol A type Epoxy resins, ethylene glycol diglycidyl ether, diglycidyl aniline and the like can be mentioned, and among them, bisphenol A type epoxy resin or ethylene glycol diglycidyl ether is preferably used.
[0013]
As another example, Japanese Patent Application Laid-Open No. 2000-191969 discloses that polyphenylene ether in a solid state, at least one carbon-carbon double bond or triple bond in a molecule, a carboxyl group, an acyl oxide group, an imino group, and an imide group are disclosed. A method for producing a functionalized polyphenylene ether obtained by reacting a functionalized compound having at least one functional group selected from the group consisting of a hydroxyl group and a glycidyl group is disclosed.
[0014]
The interphase adhesive film (C) for a printed wiring board of the present invention can be obtained by thermoforming a resin composition, applying a resin solution in which the resin composition is dissolved on a support, and then drying. Examples of the support include polyester, polyethylene, and polycarbonate. Among them, polyethylene terephthalate is preferable. Examples of the solvent that dissolves the resin composition include toluene, xylene, acetone, and methyl ethyl ketone, but are not particularly limited as long as the resin composition of the present invention can be uniformly dissolved.
A metal thin film is formed on the interphase adhesive film (C) for a printed wiring board of the present invention by a sputtering method, a vapor deposition method, an electroless plating method, or the like. Copper is preferred as the metal thin film. A circuit pattern is formed on the metal thin film by an additive method, a subtractive method, or the like.
[0015]
The resin composition of the present invention may contain one or more other thermoplastic resins or thermosetting resins. Examples of the thermoplastic resin include polyethylene, polypropylene, polybutene, ethylene / propylene copolymer, polyolefins such as poly (4-methyl-pentene) and derivatives thereof, nylon 4, nylon 6, nylon 6.6, nylon 6.6, Polyamides such as nylon 12 and derivatives thereof, polyethylene terephthalate, polybutylene terephthalate, polyethylene naphthalate, polyesters such as polyethylene terephthalate / polyethylene glycol block copolymer and derivatives thereof, modified polyphenylene ether, polycarbonate, polyacetal, polysulfone, poly Vinyl chloride and its copolymer, polyvinylidene chloride and its copolymer, polymethyl methacrylates, acrylic acid (or methacrylic acid) ester Polystyrenes such as copolymers, polystyrenes, acrylonitrile styrene copolymers, acrylonitrile styrene butadiene copolymers and copolymers thereof, polyvinyl acetates, polyvinyl formal, polyvinyl acetal, polyvinyl butyral, ethylene acetic acid Vinyl copolymers and their hydrolysates, polyvinyl alcohols, styrene butadiene block copolymers, rubbers such as polybutadiene, polyisoprene, polyvinyl ethers such as polymethoxyethylene and polyethoxyethylene, polyacrylamide, poly Phosphazenes, polyether sulfone, polyether ketone, polyether imide, polyphenylene sulfide, polyamide imide, thermoplastic polyimide, liquid crystal polymer such as aromatic polyester, Chain side chain type liquid crystal polymer or the like that includes the liquid crystal ingredient in a. Examples of the thermosetting resin include an epoxy resin, a phenol resin, and a polyimide precursor.
[0016]
An appropriate additive may be added to the curable resin composition of the present invention according to the purpose. Additives include flame retardants, heat stabilizers, antioxidants, UV absorbers, surfactants, lubricants, inorganic fillers, organic fillers, polymer additives, dialkyl peroxides, peroxy, peroxycarbonate, hydroper Oxides, peroxyketals and the like can be mentioned.
[0017]
BEST MODE FOR CARRYING OUT THE INVENTION
Next, the present invention will be described in more detail by way of examples, but the present invention should not be limited by these examples.
<Evaluation method>
1. Purification of Polyphenylene Ether Having Epoxy Group Immediately After Reaction First, in order to remove unreacted polyfunctional epoxy compound remaining in the polyphenylene ether powder having an epoxy group after reaction, 2 g of the reaction product was dissolved in 20 ml of toluene. Thereafter, a large excess of methanol was added to precipitate the polymer. After the precipitated polymer was separated by filtration, the polymer was dried under reduced pressure at 150 ° C. and 0.1 mmHg for 1 hour.
2. Proton NMR measurement of polyphenylene ether having an epoxy group The functionalized polyphenylene ether obtained by the purification operation of the first measurement was dissolved in deuterated chloroform and measured by 270 MHz NMR. The peak chemical shift was determined based on the tetramethylsilane peak (0.00 ppm). The number of epoxy groups per molecule of polyphenylene ether was determined from the area ratio of the peak (6.47 ppm) attributed to the proton at the aromatic ring 3,5 position of the polyphenylene ether and the peak attributed to the epoxy group.
[0018]
Embodiment 1
2.0 Kg of powdery polyphenylene ether having a number average molecular weight of 2,100, 600 g of bisphenol A type epoxy resin (AER250 manufactured by Asahi Kasei Epoxy Co., Ltd.), and 100 g of tri-n-butylamine were mixed well, and the mixture was sealed in an autoclave and heated at 150 ° C. Heated for 2 hours. The reaction product was prepared as described in 1. above. Treatment was performed according to the method described in Purification of Polyphenylene Ether Having Epoxy Group, and GPC and proton NMR measurements were performed. After the reaction, the shape of the GPC curve of the polymer was in good agreement with the shape of the GPC curve of the raw material polyphenylene ether, and it was confirmed that no crosslinking reaction had occurred. Proton NMR measurement of the epoxidized polyphenylene ether was performed, and the peaks at 2.73 to 2.75 ppm, 2.87 to 2.91 ppm, and 3.34 ppm were attributed to epoxy group protons. As a result of calculation from these peak areas and the peak area ratio of the protons at the 3,5-positions of the phenylene ether unit, it was found that the polymer after the reaction had an average of 1.2 epoxy groups per molecule.
[0019]
Embodiment 2
100 parts by weight of a bisphenol A type epoxy resin (AER250 manufactured by Asahi Kasei Epoxy Co., Ltd.), 50 parts by weight of the epoxidized polyphenylene ether obtained in Example 1, 3 parts of dicyandiamide, and 1 part of 2-methylimidazole are dissolved in methyl ethyl ketone to prepare a varnish. Created. The varnish was applied on a polyethylene terephthalate (PET) support with a roller coater and dried to obtain an adhesive film. A 0.5 μm copper foil layer was formed on this film to obtain an adhesive film with a copper foil layer. This adhesive film with a copper foil layer is laminated on both sides of a glass epoxy double-sided copper-clad laminate having a thickness of 18 μm, and heated at 180 ° C. for 30 minutes to form a copper-clad laminate having an adhesive film with a copper foil layer on both sides ( 1) was created. As a result of measuring the copper adhesion strength of this laminate (1) based on JIS C6481, it was 1.5 kg / cm 2 .
[0020]
[Comparative Example 1]
Example 2 was repeated except that polyphenylene ether having a number average molecular weight of 2,100 was used. The copper adhesion strength was 0.6 kg / cm 2 .
[0021]
【The invention's effect】
The present invention relates to a polyphenylene ether resin composition used for an adhesive film that can easily form a resin insulating layer in a built-up printed wiring board.
Claims (5)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2003048057A JP2004256640A (en) | 2003-02-25 | 2003-02-25 | Resin composition used for interlaminar adhesive film for printed wiring board |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2003048057A JP2004256640A (en) | 2003-02-25 | 2003-02-25 | Resin composition used for interlaminar adhesive film for printed wiring board |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JP2004256640A true JP2004256640A (en) | 2004-09-16 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003048057A Pending JP2004256640A (en) | 2003-02-25 | 2003-02-25 | Resin composition used for interlaminar adhesive film for printed wiring board |
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| Country | Link |
|---|---|
| JP (1) | JP2004256640A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20150162615A1 (en) * | 2013-12-11 | 2015-06-11 | Robert Bosch Gmbh | Binder Materials for Anode and Cathode Materials of Lithium Cells |
-
2003
- 2003-02-25 JP JP2003048057A patent/JP2004256640A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20150162615A1 (en) * | 2013-12-11 | 2015-06-11 | Robert Bosch Gmbh | Binder Materials for Anode and Cathode Materials of Lithium Cells |
| US10862123B2 (en) * | 2013-12-11 | 2020-12-08 | Robert Bosch Gmbh | Binder materials for anode and cathode materials of lithium cells |
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