JP2018049048A - 硬化性樹脂組成物、ドライフィルム、プリント配線板、および、プリント配線板の製造方法 - Google Patents
硬化性樹脂組成物、ドライフィルム、プリント配線板、および、プリント配線板の製造方法 Download PDFInfo
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- JP2018049048A JP2018049048A JP2016182780A JP2016182780A JP2018049048A JP 2018049048 A JP2018049048 A JP 2018049048A JP 2016182780 A JP2016182780 A JP 2016182780A JP 2016182780 A JP2016182780 A JP 2016182780A JP 2018049048 A JP2018049048 A JP 2018049048A
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- Prior art keywords
- resin
- group
- carboxyl group
- reaction product
- epoxy resin
- Prior art date
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 74
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 49
- 150000001875 compounds Chemical class 0.000 claims abstract description 46
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 41
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- 239000000203 mixture Substances 0.000 claims abstract description 16
- 125000000466 oxiranyl group Chemical group 0.000 claims abstract description 14
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- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 4
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- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
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Abstract
Description
(A)カルボキシル基含有樹脂が有する、フェノール性水酸基およびアルコール性水酸基を含む化合物に由来する構造が、特に柔軟性に寄与していると考えられる。
(式中、xは、0〜5までの整数であり、ベンゼン環の水素と置換する置換基R1の数を表し、R1は、xが1のとき、炭素数1〜4の飽和または不飽和アルキル基、フェニル基またはシクロヘキシル基の中から選ばれる一つの置換基を表し、xが2以上のとき、前記置換基の中から重複を許してx個選ばれる同一または異なる複数の置換基を表す。yは1〜5の整数であり、ベンゼン環の水素と置換する置換基R2−OHの数を表し、R2は、yが1のとき、炭素数1〜20の直鎖、分岐または環状のアルキレン基または
(ここで、R3はエチレン基、プロピレン基、ヒドロキシプロピレン基または
(n=2または3、z=1または2)である。)の中から選ばれる一つの置換基を表し、yが2以上のとき、前記置換基の中から重複を許してy個選ばれる同一または異なる複数の置換基を表す。)
(式中、R1、R2、xは、上記一般式(1)と同じであり、y1は0〜4の整数を表す。)
(B)カルボキシル基含有樹脂が有する、オキシラン環およびエチレン性不飽和基を有する化合物に由来する構造が、特にガラス転移温度および強度に寄与していると考えられる。
(C)光重合開始剤としては、光重合開始剤や光ラジカル発生剤として公知のものであれば、いずれのものを用いることもできる。
(D)エポキシ樹脂としては、(A)カルボキシル基含有樹脂を合成するための成分として挙げたエポキシ樹脂と同様のものが挙げられる。(D)エポキシ樹脂は、1種を単独で用いてもよく、2種以上を組み合わせて用いてもよい。
本発明の硬化性樹脂組成物は、エチレン性不飽和基を有する化合物を含有することができる。エチレン性不飽和基を有する化合物としては、公知慣用の光硬化性モノマーである光重合性オリゴマー、光重合性ビニルモノマー等を用いることができる。エチレン性不飽和基を有する化合物は、1種を単独で用いてもよく、2種以上を組み合わせて用いてもよい。
本発明の硬化性樹脂組成物は、熱硬化触媒を含有することができる。熱硬化触媒としては、例えば、イミダゾール、2−メチルイミダゾール、2−エチルイミダゾール、2−エチル−4−メチルイミダゾール、2−フェニルイミダゾール、4−フェニルイミダゾール、1−シアノエチル−2−フェニルイミダゾール、1−(2−シアノエチル)−2−エチル−4−メチルイミダゾール等のイミダゾール誘導体;ジシアンジアミド、ベンジルジメチルアミン、4−(ジメチルアミノ)−N,N−ジメチルベンジルアミン、4−メトキシ−N,N−ジメチルベンジルアミン、4−メチル−N,N−ジメチルベンジルアミン等のアミン化合物、アジピン酸ジヒドラジド、セバシン酸ジヒドラジド等のヒドラジン化合物;トリフェニルホスフィン等のリン化合物等が挙げられる。また、グアナミン、アセトグアナミン、ベンゾグアナミン、メラミン、2,4−ジアミノ−6−メタクリロイルオキシエチル−S−トリアジン、2−ビニル−2,4−ジアミノ−S−トリアジン、2−ビニル−4,6−ジアミノ−S−トリアジン・イソシアヌル酸付加物、2,4−ジアミノ−6−メタクリロイルオキシエチル−S−トリアジン・イソシアヌル酸付加物等のS−トリアジン誘導体を用いることもでき、好ましくはこれら密着性付与剤としても機能する化合物を熱硬化触媒と併用する。熱硬化触媒は、1種を単独で用いてもよく、2種以上を組み合わせて用いてもよい。
本発明の硬化性樹脂組成物は、無機フィラーを含有することができる。無機フィラーとしては、例えば、硫酸バリウム、チタン酸バリウム、酸化ケイ素粉、微粉状酸化ケイ素、シリカ、タルク、ハイドロタルサイト、ノイブルグ珪土、クレー、炭酸マグネシウム、炭酸カルシウム、酸化アルミニウム、水酸化アルミニウム、雲母粉等の公知慣用のフィラーが使用できる。これらの中でも、硫酸バリウムおよびシリカが好ましい。無機フィラーは、1種を単独で用いてもよく、2種以上を組み合わせて用いてもよい。
本発明の硬化性樹脂組成物は、着色剤を含有することができる。着色剤としては、赤、青、緑、黄、黒、白等の公知の着色剤を使用することができ、顔料、染料、色素のいずれでもよい。但し、環境負荷低減並びに人体への影響の観点からハロゲンを含有しないことが好ましい。着色剤は、1種を単独で用いてもよく、2種以上を組み合わせて用いてもよい。
本発明の硬化性樹脂組成物には、カルボキシル基含有樹脂の合成、組成物の調製、基材やキャリアフィルムに塗布する際の粘度調整等の目的で、有機溶剤を含有させることができる。有機溶剤としては、メチルエチルケトン、シクロヘキサノン等のケトン類;トルエン、キシレン、テトラメチルベンゼン等の芳香族炭化水素類;エタノール、メタノール、プロパノール、イソプロパノール、シクロヘキサノール、エチレングリコール、プロピレングリコール等のアルコール類:シクロヘキサン、メチルシクロヘキサン等の脂環式炭化水素類;セロソルブ、メチルセロソルブ、ブチルセロソルブ、カルビトール、メチルカルビトール、ブチルカルビトール、プロピレングリコールモノメチルエーテル、プロピレングリコールモノエチルエーテル、ジプロピレングリコールモノメチルエーテル、ジプロピレングリコールジエチルエーテル、ジエチレングリコールモノメチルエーテルアセテート、トリエチレングリコールモノエチルエーテル、トリプロピレングリコールモノメチルエーテル等のグリコールエーテル類;酢酸エチル、酢酸ブチル、乳酸ブチル、セロソルブアセテート、ブチルセロソルブアセテート、カルビトールアセテート、ブチルカルビトールアセテート、プロピレングリコールモノメチルエーテルアセテート、ジプロピレングリコールモノメチルエーテルアセテート、炭酸プロピレン等のエステル類;オクタン、デカン等の脂肪族炭化水素類;石油エーテル、石油ナフサ、水添石油ナフサ、ソルベントナフサ等の石油系溶剤など、公知慣用の有機溶剤が使用できる。これらの有機溶剤は、1種を単独で用いてもよく、2種以上を組み合わせて用いてもよい。
本発明の硬化性樹脂組成物には、電子材料の分野において公知慣用の他の添加剤を配合してもよい。他の添加剤としては、熱重合禁止剤、紫外線吸収剤、シランカップリング剤、可塑剤、難燃剤、帯電防止剤、老化防止剤、抗菌・防黴剤、消泡剤、レベリング剤、増粘剤、密着性付与剤、チキソ性付与剤、光開始助剤、増感剤、光塩基発生剤、熱可塑性樹脂、有機フィラー、離型剤、表面処理剤、分散剤、分散助剤、表面改質剤、安定剤、蛍光体等が挙げられる。
(合成例1:カルボキシル基含有樹脂A−1の合成)
クレゾールノボラック型エポキシ樹脂のECON−104S(日本化薬社製、エポキシ当量=220)220部(1当量)を撹拌機及び還流冷却器の付いた四つ口フラスコに入れ、カルビトールアセテート218部を加え、加熱溶解した。次に、重合禁止剤としてメチルハイドロキノン0.46部と、反応触媒としてトリフェニルホスフィン1.38部を加えた。この混合物を95〜105℃に加熱し、アクリル酸50.4部(0.7当量)、p−ヒドロキシフェネチルアルコール41.5部(0.3当量)を徐々に滴下し、16時間反応させた。この反応生成物(水酸基:1.3当量)を、80〜90℃まで冷却し、テトラヒドロフタル酸無水物91.2部(0.6当量)を加え、8時間反応させ、冷却後、取り出した。このようにして得られた感光性カルボキシル基含有樹脂の溶液は、不揮発分65質量%、固形物の酸価83mgKOH/gであった。以下、この溶液を(A)カルボキシル基含有樹脂A−1とする。
2リットル容のセパラブルフラスコに、エチルカルビトールアセテート411.4g、o−クレゾールノボラック型エポキシ樹脂[日本化薬社製、EOCN−103S、エポキシ当量215、軟化点83℃]430g及びアクリル酸144g(2モル)を仕込んだ。撹拌しつつ120℃まで加熱し、120℃を保ったまま10時間反応を続けた。いったん反応生成物を室温まで冷却し、無水コハク酸190g(1.9モル)を加え、80℃に加熱して4時間反応した。ふたたび、この反応生成物を室温まで冷却した。この反応生成物の溶液としての酸価は91mgKOH/gであり、樹脂としての酸価は140mgKOH/gであった。この反応生成物にグリシジルメタクリレート85.2g(0.6モル)及びプロピレングリコールメチルエーテルアセテート45.9gを加え、撹拌しつつ110℃まで加熱し、110℃を保ったまま6時間反応を続けた。この反応生成物を室温まで冷却したところ、粘調な溶液が得られた。このようにして得られた感光性カルボキシル基含有樹脂の溶液の不揮発分は65質量%であり、溶液として56mgKOH/gの酸価を示した。この溶液を(B)カルボキシル基含有樹脂B−1とする。
下記の表1中に示す配合に従い、各成分を配合、攪拌して、3本ロールにて分散させて、それぞれ硬化性樹脂組成物を調製した。なお、表1中の配合量は、質量部を示す。
硬化性樹脂組成物を銅箔上に全面塗布し、80℃30分で乾燥し、マイラーフィルム上600mJ/cm2で高圧水銀灯により光照射し、30℃の1wt%炭酸ナトリウム水溶液で現像し、1000mJ/cm2で高圧水銀灯により光照射し、150℃60分で熱硬化させて硬化膜を得た。得られた硬化膜を銅箔上より剥離した。
硬化膜のガラス転移点を下記条件下で動的粘弾性測定(DMA)より求めた。
測定温度:−30〜300℃
昇温速度:5℃/分
硬化性樹脂組成物を銅箔上に全面塗布し、80℃30分で乾燥し、マイラーフィルム上600mJ/cm2で露光し、30℃の1wt%炭酸ナトリウム水溶液で現像し、1000mJ/cm2で高圧水銀灯により光照射し、150℃60分で熱硬化させて得た硬化膜を銅箔上より剥離した。
硬化膜を幅約5mm、長さ約80mmの試験片に切断し、引っ張り試験機(島津製作所社製、オートグラフAGS−100N)を用いて、破断点での強度と破断点伸び率を測定した。測定条件は、サンプル幅約10mm、支点間距離約40mm、引っ張り速度は1.0mm/分とし、破断点での引っ張り弾性率を破断点強度とし、破断点までの伸び率を破断点伸び率とした。
上記ガラス転移温度の測定と同様にして、銅上に、100μmの開口を有する硬化性樹脂組成物の硬化物パターンを形成し、SEM(走査型電子顕微鏡)により観察した。得られた開口形状を確認し、以下の基準にて評価した。
○:硬化物の開口部壁面に凹凸が生じることなく、良好に開口できる。
△:硬化物に開口を形成することは可能であるが、開口部壁面に凹凸が生じる。
×:開口できなかった。
*2:合成例2で合成したカルボキシル基含有樹脂B−1(固形分0.65質量%)
*3:日本化薬社製EPPN−201
*4:三菱化学社製jER YX−4000
*5:日本化薬社製KAYARAD DPHA
*6:信越シリコーン社製
*7:BASFジャパン社製イルガキュアTPO(2,4,6−トリメチルベンゾイル−ジフェニル−フォスフィンオキサイド)
*8:堺化学社製
*9:有機溶剤
Claims (6)
- (A)エポキシ樹脂とフェノール性水酸基およびアルコール性水酸基を含む化合物と不飽和カルボン酸との反応生成物(A1)と、多塩基酸無水物との反応生成物である感光性カルボキシル基含有樹脂、
(B)エポキシ樹脂と不飽和カルボン酸との反応生成物(B1)と多塩基酸無水物との反応生成物(B2)と、オキシラン環およびエチレン性不飽和基を有する化合物との反応生成物である感光性カルボキシル基含有樹脂、
(C)光重合開始剤、および、
(D)エポキシ樹脂を含むことを特徴とする硬化性樹脂組成物。 - 前記(A)カルボキシル基含有樹脂と前記(B)カルボキシル基含有樹脂との配合比(質量比)が、3:7〜7:3であることを特徴とする請求項1に記載の硬化性樹脂組成物。
- 請求項1または2に記載の硬化性樹脂組成物を、フィルム上に塗布、乾燥して得られる樹脂層を有することを特徴とするドライフィルム。
- 請求項1または2に記載の硬化性樹脂組成物、または、請求項3に記載のドライフィルムの樹脂層を硬化して得られることを特徴とする硬化物。
- 請求項4に記載の硬化物を備えることを特徴とするプリント配線板。
- 基材上に、請求項1または2に記載の硬化性樹脂組成物を塗布、乾燥して、または、請求項3に記載のドライフィルムの樹脂層をラミネートして、基材上に樹脂層を形成する工程、
基材上の前記樹脂層に選択的に光照射して光硬化させる光硬化工程、
光硬化工程後に現像により未照射部分を除去しパターン層を得る現像工程、
パターン層に光照射する光照射工程、および、
前記光照射されたパターン層を加熱する工程、を含むことを特徴とするプリント配線板の製造方法。
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JP2019178307A (ja) * | 2018-03-30 | 2019-10-17 | 太陽インキ製造株式会社 | 硬化性樹脂組成物、ドライフィルム、硬化物、および、電子部品 |
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