JP5201397B2 - 感光性樹脂組成物及びこれを用いた感光性永久レジスト、感光性フィルム、レジストパターンの形成方法 - Google Patents
感光性樹脂組成物及びこれを用いた感光性永久レジスト、感光性フィルム、レジストパターンの形成方法 Download PDFInfo
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- JP5201397B2 JP5201397B2 JP2008115397A JP2008115397A JP5201397B2 JP 5201397 B2 JP5201397 B2 JP 5201397B2 JP 2008115397 A JP2008115397 A JP 2008115397A JP 2008115397 A JP2008115397 A JP 2008115397A JP 5201397 B2 JP5201397 B2 JP 5201397B2
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- 229940043232 butyl acetate Drugs 0.000 description 1
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- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
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Landscapes
- Materials For Photolithography (AREA)
- Polymerisation Methods In General (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Non-Metallic Protective Coatings For Printed Circuits (AREA)
Description
前記感光性樹脂組成物に活性光線を画像状に照射し露光部を光硬化させ、未露光部を現像により除去してレジストパターンを形成し硬化した感光性永久レジストが上記課題を解決できる。
また、本発明は、[2](a)酸変性ビニル基含有エポキシ樹脂が、ウレタン構造を有する酸変性ビニル基含有エポキシ樹脂である上記[1」に記載の感光性樹脂組成物に関する。
また、本発明は、[3](c−2)オキシムエステル構造を有する化合物が、前記(a)+(b)に対し、0.1〜2重量%含有する上記[1]又は上記[2]に記載の感光性樹脂組成物に関する。
また、本発明は、[4]前記(d)熱硬化剤が、エポキシ化合物、オキセタン化合物、ベンゾオキサジン化合物、オキサゾリン化合物、環状カーボナート化合物のいずれか1以上である上記[1]ないし上記[3]のいずれかに記載の感光性樹脂組成物に関する。熱硬化剤が、熱反応して付加反応で進行するのでアウトガス発生量が少なくなる。
また、本発明は、[5]前記(d)熱硬化剤が、ブロック化されたイソシアネート、又はメラミン誘導体である上記[1]ないし上記[3]のいずれかに記載の感光性樹脂組成物に関する。
また、本発明は、[6]前記(d)熱硬化剤が、ブロック化されたイソシアネート、又はメラミン誘導体であり、樹脂組成物中の熱硬化剤の添加量が、樹脂分100重量部に対し、0.1〜15重量部である上記[5]に記載の感光性樹脂組成物に関する。
また、本発明は、[7]さらに、(e)バインダーポリマーを含有する上記[1]ないし上記[6]のいずれかに記載の感光性樹脂組成物に関する。
また、本発明は、[8]上記[1]ないし上記[7]のいずれかに記載の感光性樹脂組成物に、さらに、(e)バインダーポリマーと相溶しない(f)エラストマを含有する感光性樹脂組成物に関する。
また、本発明は、[9]更に、(g)無機フィラーを含有する上記[1]ないし上記[8]のいずれかに記載の感光性樹脂組成物に関する。
また、本発明は、[10]上記[1]ないし上記[9]のいずれかに記載の感光性樹脂組成物を支持体上に塗布、乾燥して形成した感光性積層体からなる感光性フィルムに関する。
また、本発明は、[11]上記[1]ないし上記[9]のいずれかに記載の感光性樹脂組成物に活性光線を画像状に照射し露光部を光硬化させ、未露光部を現像により除去してレジストパターンを形成し硬化してなる感光性永久レジストに関する。
また、本発明は、[12]感光性永久レジストの硬化膜のガラス転移温度(Tg)が、90℃以上、破断強度50MPa以上、伸び率3%以上、硬化収縮80%以上、表面平坦性5μm以下である上記[11]に記載の感光性永久レジストに関する。
また、本発明は、[13]上記[1]ないし[9]のいずれかに記載の感光性樹脂組成物を基板上に積層する工程と、活性光線を画像状に照射し露光部を光硬化させる工程と、未露光部を現像により除去する工程を含む、レジストパターンの形成方法に関する。
なお、本発明における(メタ)アクリル酸とはアクリル酸及びそれに対応するメタクリル酸を意味し、(メタ)アクリレートとはアクリレート及びそれに対応するメタクリレートを意味し、(メタ)アクリロイル基とはアクリロイル基及びそれに対応するメタクリロイル基を意味し、(メタ)アクリロキシ基とはアクリロキシ基及びそれに対応するメタクリロキシ基を意味する。
本発明の(a)成分である酸変性ビニル基含有エポキシ樹脂は、カルボキシル基及びエチレン性不飽和基を有する感光性プレポリマーを用いることができ、例えば、エポキシ化合物(a1)と不飽和モノカルボン酸(a2)のエステル化物に飽和又は不飽和多塩基酸無水物(a3)を付加した付加反応物等を用いることができる。これらは、次の二段階の反応によって得ることができる。最初の反応(以下、便宜的に「第一の反応」という。)では、エポキシ化合物(a1)と不飽和モノカルボン酸(a2)とが反応する。次の反応(以下、便宜的に「第二の反応」という。)では、第一の反応で生成したエステル化物と、飽和又は不飽和多塩基酸無水物(a3)とが反応する。
A=10×Vf×56.1/(Wp×I)
なお、式中、Aは酸価(mgKOH/g)を示し、Vfは0.1NのKOH水溶液の滴定量(mL)を示し、Wpは測定樹脂溶液重量(g)を示し、Iは測定樹脂溶液の不揮発分の割合(重量%)を示す。
本発明の感光性樹脂組成物に光重合開始剤として含まれる(c−1)アシルフォスフィンオキサイド化合物は、前記樹脂成分(a)+(b)の総量に対し0.1〜10重量%であることが好ましく、0.1〜8重量%であることがより好ましい。
エポキシ化合物としては、例えば、ビスフェノールAジグリシジルエーテル等のビスフェノールA型エポキシ樹脂、ビスフェノールFジグリシジルエーテル等のビスフェノールF型エポキシ樹脂、ビスフェノールSジグリシジルエーテル等のビスフェノールS型エポキシ樹脂、ビフェノールジグリシジルエーテル等のビフェノール型エポキシ樹脂、ビキシレノールジグリシジルエーテル等のビキシレノール型エポキシ樹脂、水添ビスフェノールAグリシジルエーテル等の水添ビスフェノールA型エポキシ樹脂、及び、それらの二塩基酸変性ジグリシジルエーテル型エポキシ樹脂などが挙げられる。これらは単独で又は2種類以上を組み合わせて使用される。これらの化合物としては市販のものを用いることができる。例えば、ビスフェノールAジグリシジルエーテルとしてはエピコート828、エピコート1001及びエピコート1002(いずれもジャパンエポキシレジン株式会社製、商品名)等を挙げることができる。ビスフェノールFジグリシジルエーテルとしてはエピコート807(ジャパンエポキシレジン株式会社製、商品名)等を挙げることができ、ビスフェノールSジグリシジルエーテルとしてはEBPS−200(日本化薬株式会社製、商品名)及びエピクロンEXA−1514(大日本インキ化学工業株式会社製、商品名)等を挙げることができる。また、ビフェノールジグリシジルエーテルとしてはYL−6121(ジャパンエポキシレジン株式会社製、商品名)等を挙げることができ、ビキシレノールジグリシジルエーテルとしてはYX−4000(ジャパンエポキシレジン株式会社製、商品名)等を挙げることができる。さらに、水添ビスフェノールAグリシジルエーテルとしてはST−2004及びST−2007(いずれも東都化成株式会社製、商品名)等を挙げることができ、上述した二塩基酸変性ジグリシジルエーテル型エポキシ樹脂としてはST−5100及びST−5080(いずれも東都化成株式会社製、商品名)等を挙げることができる。
短鎖ジオールとしてはエチレングリコール、プロピレングリコール、1,4−ブタンジオール、ビスフェノールA等が例示でき、短鎖ジオールの数平均分子量は、48〜500であることが好ましい。上記ウレタン系エラストマは、商業的にはPANDEX T−2185、T−2983N(以上、大日本インキ化学工業株式会社製)等として入手可能である。ポリエステル系エラストマは、ジカルボン酸又はその誘導体とジオール化合物又はその誘導体とを重縮合して得られるエラストマである。ジカルボン酸としては、テレフタル酸、イソフタル酸、ナフタレンジカルボン酸及びこれらの芳香環がメチル基、エチル基、フェニル基等で置換された芳香族ジカルボン酸;アジピン酸、セバシン酸、ドデカンジカルボン酸等の炭素数2〜20の脂肪族ジカルボン酸;シクロヘキサンジカルボン酸などの脂環式ジカルボン酸などが例示でき、これらの化合物の1種又は2種以上を用いることができる。
本発明の感光性フィルムは、支持体と、該支持体上に形成された本発明の感光性樹脂組成物からなる感光性樹脂組成物層とを備えるものである。感光性樹脂組成物層上には、該感光性樹脂組成物層を被覆する保護フィルムを更に備えていてもよい。
更に直接描画方式のダイレクトレーザ露光を用いても良い。其々のレーザ光源、露光方式に対応する成分(c)光重合開始剤を用いることにより優れたパターンを形成することが可能となる。
本発明の感光性永久レジストの硬化膜のガラス転移温度(Tg)は、90℃以上であることが好ましく、また、破断強度が50MPa以上、伸び率が3%以上、硬化収縮が、80%以上、表面平坦性5μm以下であると好ましい。
表1に示した各成分を同表に示す配合量(重量部)で混合することにより、感光性樹脂組成物溶液を得た。表1及び表2に示した各成分は、下記のものを使用した。
「UXE−3024」:ポリウレタン化合物(日本化薬株式会社製、重量平均分子量:10000、酸価:60mgKOH/g)。
「ZFR−1158」:酸変性ビスフェノールF型エポキシアクリレート(日本化薬株式会社製、商品名、重量平均分子量:10000、酸価:60mgKOH/g)。
「ZAR−2003H」:酸変性ビスフェノールA型エポキシアクリレート(日本化薬株式会社製、商品名、重量平均分子量:13000、酸価:82mgKOH/g)。
「FA−321M」:2,2−ビス(4−(メタクリロキシペンタエトキシ)フェニル)プロパン(日立化成工業株式会社製、商品名)。
「KAYARAD−DPHA」:ジペンタエリスリトールヘキサアクリレート(日本化薬株式会社製、商品名)。
「IRGACURE−819」:ビス(2,4,6−トリメチルベンゾイル)−フェニルホスフィンオキサイド(チバ・スペシャルティ・ケミカルズ社製、商品名)。
<(c−2)成分(光重合開始剤)>
「IRGACURE−OXE02」:エタノン,1−[9−エチル−6−(2−メチルベンゾイル)−9H−カルバゾール−3−イル]−,1−(O−アセチルオキシム)(チバ・スペシャルティ・ケミカルズ社製、商品名)。
<その他(c)成分>
「N−1717」:1,7−ビス(9−アクリジニル)ヘプタン(アデカ株式会社製、商品名)。
「9−PA」:9−フェニルアクリジン(新日鐵化学株式会社製、商品名)。
「IRGACURE−369」:2−ベンジル−2−ジメチルアミノ−1−(4−モルフォリノフェニル)−ブタノン−1(チバ・スペシャルティ・ケミカルズ社製、商品名)。
「KAYACURE−DETX」:2,4−ジエチルチオキサントン(日本化薬株式会社製、商品名)。
「BL−3175」:ブロック型イソシアネート(住友バイエルウレタン株式会社製、商品名)。
「サイメル300」:メチロール化メラミン(三井東圧サイメル株式会社製、商品名)。
「樹脂(1)」:メタクリル酸/メタクリル酸メチル/アクリル酸ブチル(配合割合17/53/30(重量比))を共重合させて得られた、重量平均分子量60000、酸価70mgKOH/gのアクリル樹脂。
「バリエースB−30」:硫酸バリウム「バリエースB−30」(堺化学工業株式会社製、商品名)を使用し、以下の方法で調製した硫酸バリウム分散液。
「エスペル1108」:ポリエステル系エラストマ(日立化成工業株式会社製、商品名)。
グリーン顔料:「F767グリーン」(東洋インキ株式会社製、商品名)
ジシアンジアミド:「エピキュアDICY7」(ジャパンエポキシレジン社製、商品名)
次いで、上記で得られた感光性樹脂組成物溶液を、支持体である16μm厚のポリエチレンテレフタレートフィルム(G2−16、帝人株式会社製、商品名)上に均一に塗布することにより感光性樹脂組成物層を形成し、それを、熱風対流式乾燥機を用いて100℃で約10分間乾燥した。感光性樹脂組成物層の乾燥後の膜厚は、25μmであった。
実施例1〜9及び比較例1〜5の感光性フィルムをそれぞれ用いて以下の各試験を行い、各感光性エレメントを用いた場合の、表面平坦性、はんだ耐熱性、及びめっき耐性について評価した。得られた結果を表2に示した。
12μm厚の銅箔を0.06mm厚のガラスエポキシ基材に積層した100×100mm角のプリント配線板用基板(E−679、日立化成工業株式会社社製、商品名)に、半径0.1及び0.2mmのスルーホールを1mm間隔にて作製し、これを平坦性評価基板とした。この基板の銅表面を砥粒ブラシで研磨し、水洗後、乾燥した。このプリント配線板用基板両面に連続プレス式真空ラミネータ(MVLP−500、株式会社名機製作所製、商品名)を用いて、プレス熱板温度70℃、真空引き時間20秒、ラミネートプレス時間30秒、気圧4kPa以下、圧着圧力0.4MPaの条件の下、前記感光性フィルムのポリエチレンフィルムを剥離して積層し、評価用積層体を得た。
12μm厚の銅箔をガラスエポキシ基材に積層したプリント配線板用基板(E−679、日立化成工業株式会社製、商品名)の銅表面を砥粒ブラシで研磨し、水洗後、乾燥した。このプリント配線板用基板上に連プレス式真空ラミネータ(MVLP−500、株式会社名機製作所製、商品名)を用いて、プレス熱板温度70℃、真空引き時間20秒、ラミネートプレス時間30秒、気圧4kPa以下、圧着圧力0.4MPaの条件の下、前記感光性フィルムのポリエチレンフィルムを剥離して積層し、評価用積層体を得た。
上記はんだ耐熱性の評価と同様にして得られた評価基板に対し、無電解ニッケルめっき(上村工業株式会社製、商品名ニムデンNPR−4)を施し(15分間処理)、更に無電解金めっき(上村工業株式会社製、商品名ゴブライトTAM−54)を施した(10分間処理)。
Claims (13)
- (a)酸変性ビニル基含有エポキシ樹脂、(b)分子中に少なくとも1個以上のエチレン性不飽和基を有する光重合性モノマ、(c−1)下記一般式(I)で表されるアシルフォスフィンオキシド化合物、(c−2)オキシムエステル構造を有する化合物及び(d)熱硬化剤を含有し、(c−1)の添加量が前記(a)+(b)に対し、0.1〜10重量%であり、(d)熱硬化剤の添加量が前記(a)+(b)に対し、0.1〜20重量%である感光性樹脂組成物。
- (a)酸変性ビニル基含有エポキシ樹脂が、ウレタン構造を有する酸変性ビニル基含有エポキシ樹脂である請求項1に記載の感光性樹脂組成物。
- (c−2)オキシムエステル構造を有する化合物が、前記(a)+(b)に対し、0.1〜2重量%含有する、請求項1又は請求項2に記載の感光性樹脂組成物。
- 前記(d)熱硬化剤がエポキシ化合物、オキセタン化合物、ベンゾオキサジン化合物、オキサゾリン化合物、環状カーボナート化合物のいずれか1以上である請求項1ないし請求項3のいずれかに記載の感光性樹脂組成物。
- 前記(d)熱硬化剤が、ブロック化されたイソシアネート、又はメラミン誘導体である請求項1ないし請求項3のいずれかに記載の感光性樹脂組成物。
- 前記(d)熱硬化剤が、ブロック化されたイソシアネート、又はメラミン誘導体であり、樹脂組成物中の熱硬化剤の添加量が、樹脂分100重量部に対し、0.1〜15重量部である請求項5に記載の感光性樹脂組成物。
- さらに、(e)バインダーポリマーを含有する請求項1ないし請求項6のいずれかに記載の感光性樹脂組成物。
- 請求項1ないし請求項7のいずれかに記載の感光性樹脂組成物に、さらに、(e)バインダーポリマーと相溶しない(f)エラストマを含有する感光性樹脂組成物。
- 更に、(g)無機フィラーを含有する請求項1ないし請求項8のいずれかに記載の感光性樹脂組成物。
- 請求項1ないし請求項9のいずれかに記載の感光性樹脂組成物を支持体上に塗布、乾燥して形成した感光性積層体からなる感光性フィルム。
- 請求項1ないし請求項9のいずれかに記載の感光性樹脂組成物に活性光線を画像状に照射し露光部を光硬化させ、未露光部を現像により除去してレジストパターンを形成し硬化してなる感光性永久レジスト。
- 感光性永久レジストの硬化膜のガラス転移温度(Tg)が、90℃以上、破断強度50MPa以上、伸び率3%以上、硬化収縮80%以上、表面平坦性5μm以下である請求項11に記載の感光性永久レジスト。
- 請求項1ないし請求項9のいずれかに記載の感光性樹脂組成物を基板上に積層する工程と、活性光線を画像状に照射し露光部を光硬化させる工程と、未露光部を現像により除去する工程を含む、レジストパターンの形成方法。
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