JP2018044137A - 樹脂組成物、接着剤、フィルム状接着材、接着シート、多層配線板、樹脂付銅箔、銅張積層板、プリント配線板 - Google Patents
樹脂組成物、接着剤、フィルム状接着材、接着シート、多層配線板、樹脂付銅箔、銅張積層板、プリント配線板 Download PDFInfo
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- JP2018044137A JP2018044137A JP2016189014A JP2016189014A JP2018044137A JP 2018044137 A JP2018044137 A JP 2018044137A JP 2016189014 A JP2016189014 A JP 2016189014A JP 2016189014 A JP2016189014 A JP 2016189014A JP 2018044137 A JP2018044137 A JP 2018044137A
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- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
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- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
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- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical compound NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 description 1
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- 239000005011 phenolic resin Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- NAKOELLGRBLZOF-UHFFFAOYSA-N phenoxybenzene;pyrrole-2,5-dione Chemical compound O=C1NC(=O)C=C1.O=C1NC(=O)C=C1.C=1C=CC=CC=1OC1=CC=CC=C1 NAKOELLGRBLZOF-UHFFFAOYSA-N 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- RPGWZZNNEUHDAQ-UHFFFAOYSA-N phenylphosphine Chemical compound PC1=CC=CC=C1 RPGWZZNNEUHDAQ-UHFFFAOYSA-N 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229920003207 poly(ethylene-2,6-naphthalate) Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920003223 poly(pyromellitimide-1,4-diphenyl ether) Polymers 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
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- 239000011112 polyethylene naphthalate Substances 0.000 description 1
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- 239000004926 polymethyl methacrylate Substances 0.000 description 1
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- 230000002265 prevention Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
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- 229960004889 salicylic acid Drugs 0.000 description 1
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- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
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- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
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- KLNPWTHGTVSSEU-UHFFFAOYSA-N undecane-1,11-diamine Chemical compound NCCCCCCCCCCCN KLNPWTHGTVSSEU-UHFFFAOYSA-N 0.000 description 1
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- 229910052725 zinc Inorganic materials 0.000 description 1
- JLYXXMFPNIAWKQ-UHFFFAOYSA-N γ Benzene hexachloride Chemical compound ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 0.000 description 1
Abstract
Description
イ.(a1)成分、(a2)成分及び(a3)成分
ロ.(a1)成分及び(a2’)成分
ハ.(a1)成分、(a2’)成分及び(a3)成分
ニ.(a1’)成分及び(a2)成分
ホ.(a1’)成分、(a2)成分及び(a3)成分
ヘ.(a1’)成分及び(a2’)成分
ト.(a1’)成分、(a2’)成分及び(a3)成分
チ.(a1)成分、(a2)成分及び(a4)成分
リ.(a1’)成分、(a2)成分及び(a4)成分
ヌ.(a1)成分、(a2’)成分及び(a4)成分
撹拌機、分水器、温度計及び窒素ガス導入管を備えた反応容器に、市販の芳香族テトラカルボン酸二無水物(商品名「BTDA−UP」、エボニックジャパン(株)製;3,3’,4,4’−ベンゾフェノンテトラカルボン酸二無水物の含有量が99.9%以上)210.0g、シクロヘキサノン1008.0g、メチルシクロヘキサン201.6gを仕込み、溶液を60℃まで加熱した。次いで、水添ダイマージアミン(商品名「PRIAMINE 1075」、クローダジャパン(株)製)341.7gを滴下した後、140℃で10時間かけてイミド化反応させることにより、軟化点約80℃及び重量平均分子量約35,000のポリイミド樹脂(A1−1)の溶液(不揮発分30.0%)を得た。なお、酸成分/アミン成分のモル比は1.03であった。
製造例1と同様の反応容器に、市販の芳香族テトラカルボン酸二無水物(商品名「BisDA2000」、SABICジャパン合同会社製;4,4’−[プロパン−2,2−ジイルビス(1,4−フェニレンオキシ)]ジフタル酸二無水物の含有量が99.5%以上) 60.0g、シクロヘキサノン165.0g、メチルシクロヘキサン27.5gを仕込み、溶液を60℃まで加熱した。次いで、PRIAMINE 1075 59.3g、を滴下した後、140℃で10時間かけてイミド化反応させることにより、軟化点約90℃及び重量平均分子量約30,000のポリイミド樹脂(A1−2)の溶液(不揮発分31.9%)を得た。なお、酸成分/アミン成分のモル比は1.05であった。
製造例1と同様の反応容器に、市販の芳香族テトラカルボン酸二無水物(商品名「BisDA−1000」、SABICジャパン合同会社製;4,4’−[プロパン−2,2−ジイルビス(1,4−フェニレンオキシ)]ジフタル酸二無水物の含有量が98.0%) 65.0g、シクロヘキサノン266.5g、メチルシクロヘキサン44.4gを仕込み、溶液を60℃まで加熱した。次いで、PRIAMINE 1075 43.7g、及び1,3−ビスアミノメチルシクロヘキサン5.4gを滴下した後、140℃で10時間かけてイミド化反応させることにより、軟化点約100℃及び重量平均分子量約30,000のポリイミド樹脂(A2−1)の溶液(不揮発分29.2%)を得た。なお、酸成分/アミン成分のモル比は1.05であった。
製造例1と同様の反応容器に、市販の芳香族テトラカルボン酸二無水物(商品名「BTDA−PF」、エボニックジャパン(株)製;3,3’,4,4’−ベンゾフェノンテトラカルボン酸二無水物の含有量が98%) 200.0g、シクロヘキサノン960.0g、メチルシクロヘキサン192.0gを仕込み、溶液を60℃まで加熱した。次いで、PRIAMINE 1075 319.2gを滴下した後、140℃で10時間かけてイミド化反応させることにより、軟化点約80℃及び重量平均分子量約25,000のポリイミド樹脂(A2−2)の溶液(不揮発分29.8%)を得た。なお、酸成分/アミン成分のモル比は1.05であった。
製造例1と同様の反応容器に、BTDA−PF 190.0g、シクロヘキサノン277.5g、メチルシクロヘキサン182.4gを仕込み、溶液を60℃まで加熱した。次いで、PRIAMINE 1075 277.5g、及び市販のポリジメチルシロキサン(商品名「KF−8010」、信越化学工業(株)製。)23.8gを滴下した後、140℃で10時間かけてイミド化反応させることにより、軟化点約70℃及び重量平均分子量約15,000のポリイミド樹脂(A2−3)の溶液(不揮発分29.8%)を得た。なお、酸成分/アミン成分のモル比は1.09であった。
製造例1と同様の反応容器に、BTDA−UP 190.0g、シクロヘキサノン912.0g、メチルシクロヘキサン182.4gを仕込み、溶液を60℃まで加熱した。次いで、KF−8010 476.0gを滴下した後、140℃で10時間かけてイミド化反応させることにより、軟化点約20℃及び重量平均分子量約35,000のポリイミド樹脂(A2−4)の溶液(不揮発分36.7%)を得た。なお、酸成分/アミン成分のモル比は1.09であった。
製造例1と同様の反応容器に、BTDA−UP 200.0g、シクロヘキサノン960.0g、メチルシクロヘキサン192.0gを仕込み、溶液を60℃まで加熱した。次いで、市販の非水添ダイマージアミン(商品名「PRIAMINE 1074」、クローダジャパン(株)製) 319.2gを滴下した後、140℃で10時間かけてイミド化反応させることにより、軟化点約70℃及び重量平均分子量約25,000のポリイミド(A2−5)の溶液(不揮発分29.8%)を得た。なお、酸成分/アミン成分のモル比は1.05であった。
製造例1と同様の反応容器に、BisDA−1000 200.0g、シクロヘキサノン700.0g、メチルシクロヘキサン175.0gを仕込み、溶液を60℃まで加熱した。次いで、市販の水添ダイマージアミン(商品名「PRIAMINE 1075」、クローダジャパン(株)製) 190.5gを滴下した後、140℃で10時間かけてイミド化反応させることにより、軟化点約80℃及び重量平均分子量約35,000のポリイミド(A2−6)の溶液(不揮発分29.9%)を得た。なお、酸成分/アミン成分のモル比は1.09であった。
製造例及び比較製造例のポリイミド溶液をそれぞれ、ナフロンPTFEテープTOMBO No.9001(ニチアス(株))上に塗工し、室温で12時間乾燥させた後、200℃で1時間硬化させることによって、膜厚50μmの硬化物シートを得た。次いで、該硬化物シートについて、JIS C2565に準じ、10GHzにおける比誘電率(Dk)及び誘電正接(Df)を、市販の誘電率測定装置(空洞共振器タイプ、エーイーティー製)を用いて測定した。結果を表1に示す。
(A1−1)成分の溶液100.00g、(B)成分としてテトラグリシジルキシレンジアミン(商品名「Tetrad−X」、三菱ガス化学(株)製)1.67g及び水酸基含有ポリフェニレンエーテル(商品名「SA90」SABIC(株)製)1.67g、(C)成分としてトルエンを7.87g、並びに(D)成分として市販のアミノ基含有シランカップリング剤(商品名「KBM603」、信越化学工業(株)製;N−2−(アミノエチル)−3−アミノプロピルトリメトキシシラン) 0.07gを混合し、不揮発分30.0%の樹脂組成物(接着剤)を得た。
(A1−2)成分の溶液100.00g、Tetrad−X 1.78g及びSA90 1.78g、トルエン14.78g、並びにKBM603 0.07gを混合し、不揮発分30.0%の樹脂組成物(接着剤)を得た。
(A1−1)成分の溶液100.00g及び(A2−3)成分の溶液25.17g、Tetrad−X 2.09g及びSA90 2.09g、トルエン9.59g、並びにKBM603 0.08gを混合し、不揮発分30.0%の樹脂組成物(接着剤)を得た。
(A1−1)成分の溶液100.00g及び(A2−3)成分の溶液25.17g、Tetrad−X 3.32g及びSA90 3.32g、トルエン15.32g、並びにKBM603 0.09gを混合し、不揮発分30.0%の樹脂組成物(接着剤)を得た。
(A1−2)成分の溶液100.00g及び(A2−3)成分の溶液26.76g、Tetrad−X 2.21g及びSA90 2.21g、トルエン16.58g、並びにKBM603 0.08gを混合し、不揮発分30.0%の樹脂組成物(接着剤)を得た。
(A1−1)成分の溶液30.00g、(A2−1)成分の溶液30.82g及び(A2−3)成分の溶液15.10g、市販の多官能系エポキシ樹脂(商品名「jER630」、三菱化学(株)製;N,N−ジグリシジル−4−グリシジルオキシアニリン)1.20g及びフェノールノボラック樹脂(商品名「T759」、荒川化学工業(株)製)1.30g、トルエン3.81g、メチルエチルケトン1.30g並びにKBM603 0.05gを混合し、不揮発分30.0%の樹脂組成物(接着剤)を得た。
(A1−1)成分の溶液30.00g、(A2−1)成分の溶液30.82g及び(A2−3)成分の溶液15.10g、jER630 0.57g及びT759 0.62g、トルエン1.33g、メチルエチルケトン0.62g並びにKBM603 0.05gを混合し、不揮発分30.0%の樹脂組成物(接着剤)を得た。
(A1−1)成分の溶液100.00g、Tetrad−X 1.67g、トルエン3.90gを混合し、不揮発分30.0%の樹脂組成物(接着剤)を得た。
(A1−1)成分の溶液30.00g、(A2−1)成分の溶液30.82g及び(A2−6)成分の溶液15.05g、jER630 0.57g及びT759 0.62g、トルエン1.37g、メチルエチルケトン0.62g並びにKBM603 0.05gを混合し、不揮発分30.0%の樹脂組成物(接着剤)を得た。
(A1−1)成分の溶液30.00g、(A2−1)成分の溶液30.82g及び(A2−6)成分の溶液15.05g、jER630 3.30g及びBis−A型シアネートエステル(商品名「CYTESTER TA」、三菱ガス化学(株)製)2.34g、トルエン8.96g、メチルエチルケトン3.51g並びにKBM603 0.05gを混合し、不揮発分30.0%の樹脂組成物(接着剤)を得た。
(A1−1)成分の溶液30.00g、(A2−1)成分の溶液30.82g及び(A2−6)成分の溶液15.05g、jER630 0.70g及びCYTESTER TA 0.49g、トルエン1.39g、メチルエチルケトン0.74g並びにKBM603 0.05gを混合し、不揮発分30.0%の樹脂組成物(接着剤)を得た。
(A1−1)成分の溶液100.00g及び(A2−3)成分の溶液25.17g、Tetrad−X 0.58g及びSA90 0.58g、トルエン2.54g、並びにKBM603 0.08gを混合し、不揮発分30.0%の樹脂組成物(接着剤)を得た。
(A2−2)成分の溶液100.00g、Tetrad−X 1.65g及びSA90 1.65g、トルエン7.05g、並びにKBM603 0.07gを混合し、不揮発分30.0%の樹脂組成物(接着剤)を得た。
(A2−3)成分の溶液100.00g、Tetrad−X 1.65g及びSA90 1.65g、トルエン7.05g、並びにKBM603 0.07gを混合し、不揮発分30.0%の樹脂組成物(接着剤)を得た。
(A1−1)成分の溶液20.00g及び(A2−3)成分80.54g、Tetrad−X 1.67g及びSA90 1.67g、トルエン7.47g、並びにKBM603 0.07gを混合し、不揮発分30.0%の樹脂組成物(接着剤)を得た。
(A1−1)成分の溶液100.00g及び(A2−3)成分25.17g、Tetrad−X 6.26g及びSA90 6.26g、トルエン29.00g、並びにKBM603 0.09gを混合し、不揮発分30.0%の樹脂組成物(接着剤)を得た。
(A1−1)成分の溶液100.00g及び(A2−3)成分25.17g、Tetrad−X 0.19g及びSA90 0.19g、トルエン0.71g、並びにKBM603 0.08gを混合し、不揮発分30.0%の樹脂組成物(接着剤)を得た。
(A2−4)成分の溶液100.00g、Tetrad−X 2.04g及びSA90 2.04g、トルエン32.04g、並びにKBM603 0.08gを混合し、不揮発分30.0%の樹脂組成物(接着剤)を得た。
(A2−5)成分の溶液100.00g、Tetrad−X 1.66g及びSA90 1.66g、トルエン7.26g、並びにKBM603 0.07gを混合し、不揮発分30.0%の樹脂組成物(接着剤)を得た。
実施例1の接着剤を、支持シート(商品名「カプトン100EN」、東レ・デユポン(株)製;膜厚25μm;熱膨張係数;15ppm/℃)に、乾燥後の厚みが10μmとなるようギャップコーターにて塗布した後、180℃で3分間乾燥させることによって接着シートを得た。他の実施例及び比較例の接着剤についても同様にして接着シートを得た。
実施例及び比較例の接着剤をそれぞれ、フッ素樹脂PFA平皿(直径75mm, (株)相互理化学硝子製作所製)に約7g注ぎ、30℃×10時間、70℃×10時間、100℃×6時間、120℃×6時間、150℃×6時間、180℃×12時間の条件で硬化させることによって、膜厚約300µmの硬化物シートを得た。次いで、該硬化物シートについて、JIS C2565に準じ、10GHzにおける比誘電率(Dk)及び誘電正接(Df)を、市販の誘電率測定装置(空洞共振器タイプ、エーイーティー製)を用いて測定した。
実施例及び比較例の各積層体について、JIS C−6481(フレキシブルプリント配線板用銅張積層板試験方法)に準じ、引き剥がし強さ(N/cm)を測定した。
実施例及び比較例の各積層体について、硬化後、288℃のはんだ浴に銅箔側を下にして30秒浮かべ、外観変化の有無を確認した。変化無しを○、発泡や膨れがある場合を×とした。
実施例1の接着剤を、離型フィルム(商品名「WH52−P25CM(白)」、サンエー化研(株)製)に、乾燥後の厚みが約25µmとなるようギャップコーターにて塗工後、150℃で5分間乾燥させることによってボンディングシートを得た。他の実施例及び比較例の接着剤についても同様にしてボンディングシートを得た。
実施例1に係る銅張積層板の両面の銅箔に、ライン/スペース=0.2/0.2(mm)のレジストパターンを形成したものを、濃度40%の塩化第二鉄水溶液に浸漬することによってエッチングし、銅回路を形成した。このようにして、プリント配線板が得られた。
得られたプリント配線板をコア材とし、その両面に、実施例1に係る樹脂付銅箔を重ね、圧力4.5MPa、200℃及び30分間の条件で圧着させたものの外層の未処理銅箔に、ライン/スペース=0.2/0.2(mm)のレジストパターンを形成した。次いで、得られた基板を濃度40%の塩化第二鉄水溶液への浸漬によってエッチングすることにより、銅回路を形成した。この銅回路が形成された表層の上に、前記接着シートを重ね合わせ、圧力1MPa、180℃及び30分間の条件で加熱プレスすることにより、積層した。このようにして、回路パターン層を4つ備える多層配線板が得られた。
実施例1に係る片面銅張積層板の銅箔に、ライン/スペース=0.2/0.2(mm)のレジストパターンを形成したものを、濃度40%の塩化第二鉄水溶液に浸漬することによってエッチングし、銅回路を形成した。同じものを用意し、銅回路の無い基材側同士に前記ボンディングシートを挟み込み、圧力1MPa、180℃及び30分間の条件で加熱プレスすることにより、積層した。その後、積層体の銅回路が形成された表層の上に、前記接着シートを重ね合わせ、圧力1MPa、180℃及び30分間の条件で加熱プレスすることにより、積層した。このようにして、回路パターン層を4つ備える多層配線板が得られた。
Claims (20)
- 遊離カルボン酸の含有量が1重量%未満の芳香族テトラカルボン酸ニ無水物(a1)及び水添ダイマージアミン(a2)を含み、かつジアミノポリシロキサン(a3)を含まないモノマー群(1)を反応させてなるポリイミド(A1)、を含む樹脂組成物。
- (1)成分における(a1)成分及び(a2)成分のモル比〔(a1)/〔(a2)〕が1〜1.5である、請求項1又は2の樹脂組成物。
- 更に、(A1)成分以外のポリイミド(A2)を含有する、請求項1〜3のいずれかの樹脂組成物。
- (A2)成分が、(a1)成分及び/又は遊離カルボン酸の含有量が1重量%以上の芳香族テトラカルボン酸ニ無水物(a1’)と、(a2)成分及び/又は非水添ダイマージアミン(a2’)とを含むモノマー群(2)を反応させてなるポリイミド樹脂であることを特徴とする、請求項4の樹脂組成物。
- (2)成分が更に(a3)成分を含む、請求項5の樹脂組成物。
- (A1)成分と(A2)成分の固形分重量比〔(A1)/(A2)〕が40/60〜99/1である、請求項4〜6のいずれかの樹脂組成物。
- 更に架橋剤(B)を含有する、請求項1〜7のいずれかの樹脂組成物。
- (B)成分が、ポリエポキシ化合物(B1)及び/又はポリフェニレンエーテル化合物(B2)である、請求項8の樹脂組成物。
- 更に有機溶剤(C)を含有する請求項1〜11のいずれかのポリイミド樹脂組成物。
- 更に一般式:Q−Si(R1)a(OR2)3−a(式中、Qは酸無水物基と反応する官能基を含む基を、R1は水素又は炭素数1〜8の炭化水素基を、R2は炭素数1〜8の炭化水素基を、aは0、1又は2を示す。)で表される反応性アルコキシシリル化合物(D)を含有する、請求項1〜12のいずれかのポリイミド樹脂組成物。
- 請求項1〜13のいずれかの樹脂組成物からなる接着剤。
- 請求項14の接着剤の硬化物からなるフィルム状接着材。
- 請求項14の接着剤の硬化物を接着層とする接着シート。
- 請求項14の接着剤、請求項15のフィルム状接着材及び請求項16の接着シートからなる群より選ばれる少なくとも一種を用いて得られる多層配線板。
- 請求項14の接着剤、請求項15のフィルム状接着材及び請求項16の接着シートからなる群より選ばれる少なくとも一種を用いて得られる樹脂付銅箔。
- 請求項18の樹脂付銅箔を用いて得られる銅張積層板。
- 請求項19の銅張積層板を用いて得られるプリント配線板。
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CN111303424A (zh) * | 2020-04-15 | 2020-06-19 | 江阴骏驰新材料科技有限公司 | 一种透明的高分子材料组合物及其应用 |
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