JP5417716B2 - 感光性樹脂組成物、並びにこれを用いた感光性フィルム、レジストパターンの形成方法及び永久レジスト - Google Patents
感光性樹脂組成物、並びにこれを用いた感光性フィルム、レジストパターンの形成方法及び永久レジスト Download PDFInfo
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- JP5417716B2 JP5417716B2 JP2008039067A JP2008039067A JP5417716B2 JP 5417716 B2 JP5417716 B2 JP 5417716B2 JP 2008039067 A JP2008039067 A JP 2008039067A JP 2008039067 A JP2008039067 A JP 2008039067A JP 5417716 B2 JP5417716 B2 JP 5417716B2
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- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- NIUZJTWSUGSWJI-UHFFFAOYSA-M triethyl(methyl)azanium;chloride Chemical compound [Cl-].CC[N+](C)(CC)CC NIUZJTWSUGSWJI-UHFFFAOYSA-M 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 238000007039 two-step reaction Methods 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 229920006163 vinyl copolymer Polymers 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 238000004804 winding Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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Description
本発明の(a)成分である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としては、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。
ここで、一般式(3)中、R7はエポキシアクリレートの残基、R8はジイソシアネートの残基、R9は炭素数1〜5のアルキル基、R10は水素原子又はメチル基を示す。なお、残基とは、原料成分から結合に供された官能基を除いた部分の構造をいう。また、式中に複数ある基は、それぞれ同一でも異なってもいてもよい。また、上記ポリウレタン化合物が有する末端の水酸基は、飽和若しくは不飽和多塩基酸無水物で処理されていてもよい。
A=10×Vf×56.1/(Wp×I)
なお、式中、Aは酸価(mgKOH/g)を示し、Vfはフェノールフタレインの滴定量(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(質量%)を示す。
式(1)中、R1、R2及びR3はそれぞれ独立に、炭素数1〜20のアルキル基又はアリール基を示し、式(2)中、R4、R5及びR6はそれぞれ独立に、炭素数1〜20のアルキル基又はアリール基を示す。式(1)中、R1、R2、R3は、炭素数1〜20のアルキル基の場合、炭素数5〜10のアルキル基がより好ましい。また、式(2)中、R4、R5、R6は、炭素数1〜20のアルキル基の場合、炭素数5〜10のアルキル基がより好ましい。
まず、表1及び表2に示す各成分を同表に示す配合量(質量部)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に示す各成分は、下記のものを使用した。
「UXE−3024」:ポリウレタン化合物(日本化薬社製、サンプル名、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(日本化薬社製、商品名)。
[(c−1)成分]
「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)。
「DAROCUR−TPO」:2,4,6−トリメチルベンゾイル−ジフェニル−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]
「N−1717」:1,7−ビス(9−アクリジニル)ヘプタン(アデカ社製、商品名)。
「9−PA」:9−フェニルアクリジン(新日鐵化学社製、商品名)。
[(c−3)成分]
「IRGACURE−OXE01」:1,2−オクタンジオン,1−[4−(フェニルチオ)−,2−(O−ベンゾイルオキシム)](チバ・スペシャルティ・ケミカルズ社製、商品名)。
「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)。
「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)。
「IRGACURE−907」:2−メチル−1−[4−(メチルチオ)フェニル]−2−モルフォリノプロパン−1−オン(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)製、商品名)。
「EAB」:4,4’−ビス(ジエチルアミノ)ベンゾフェノン(保土ヶ谷化学工業社製、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(三井東圧サイメル社製、商品名)。
「YX4000H」:ビフェニル型エポキシ樹脂(ジャパンエポキシレジン社製、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(質量比))を共重合させて得られた、重量平均分子量60000、酸価70mgKOH/gのアクリル樹脂である。
「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。
フタロシアニンブルー:「F784ブルー」(東洋インキ 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1〜14及び比較例1〜10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、感度、レジスト形状、表面硬度、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3及び4に示す。
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、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、感光性フィルムの保護フィルムを剥離して積層し、評価用積層体を得た。
上記感度の評価と同様にして得られた評価用積層体を室温で1時間以上放置した後、直径80μmの開口パターンを有するデジタルデータを、オルボテック社製Paragon9000型露光機を使用して21段ステップタブレットの残存ステップ段数が8.0となるエネルギー量で、評価用積層体の支持体上から直接描画露光した。
上記レジスト形状の評価と同様にして得た永久マスクレジストパターン表面の鉛筆硬度を、JIS K5600−5−4に準拠して測定し、レジスト表面におけるきずの有無を目視で観察した。測定には硬さ4Hの鉛筆(三菱鉛筆社製)を用いた。表面硬度の評価は、4Hでレジスト表面にきずが生じないもの、すなわち鉛筆硬度が4H以上であるものを「○」とし、4Hでレジスト表面にきずが生じたもの、すなわち鉛筆硬度が3H以下であるものを「×」とした。
上記感度の評価と同様にして得られた評価用積層体を室温で1時間以上放置した後、2mm角の開口パターンを有するデジタルデータを、オルボテック株式会社製Paragon9000型露光機を使用して21段ステップタブレットの残存ステップ段数が8.0となるエネルギー量で、評価用積層体の支持体上から直接描画露光した。
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)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)製、商品名ゴブライトTAM−54)を施した(10分間処理)。
Claims (11)
- (a)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、(b)分子中に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ー、(c)光重合開始剤、及び
ジシアンジアミドを含有する感光性樹脂組成物であって、
前記(c)光重合開始剤が、(c−1)アシルホスフィンオキサイド系化合物と、(c−2)アクリジン環を有する化合物と、を含有する、又は、(c−1)アシルホスフィンオキサイド系化合物と、(c−2)アクリジン環を有する化合物と、(c−3)オキシムエステルを有する化合物と、を含有し、
前記アクリジン環を有する化合物は、9−フェニルアクリジン、9−ピリジルアクリジン、9−ピラジニルアクリジン、9−モノペンチルアミノアクリジン、1,2−ビス(9−アクリジニル)エタン、1,3−ビス(9−アクリジニル)プロパン、1,4−ビス(9−アクリジニル)ブタン、1,5−ビス(9−アクリジニル)ペンタン、1,6−ビス(9−アクリジニル)ヘキサン、1,7−ビス(9−アクリジニル)ヘプタン、1,8−ビス(9−アクリジニル)オクタン、1,9−ビス(9−アクリジニル)ノナン、1,10−ビス(9−アクリジニル)デカン、1,11−ビス(9−アクリジニル)ウンデカン、1,12−ビス(9−アクリジニル)ドデカン、1,3−ビス(9−アクリジニル)−2−オキサプロパン、1,3−ビス(9−アクリジニル)−2−チアプロパン、及び1,5−ビス(9−アクリジニル)−3−チアペンタンからなる群より選択される1種以上であることを特徴とする感光性樹脂組成物。 - 前記感光性樹脂組成物中における、前記(c−1)アシルホスフィンオキサイド系化合物の合計含有量と、前記(c−2)アクリジン環を有する化合物及び前記(c−3)オキシムエステルを有する化合物の合計含有量と、の比[(c−1)]:[(c−2)+(c−3)]が、質量比で1:0.01〜0.5であることを特徴とする請求項1又は2に記載の感光性樹脂組成物。
- 前記(a)感光性プレポリマーが、分子内に2つ以上の水酸基及びエチレン性不飽和基を有するエポキシアクリレート化合物と、ジイソシアネート化合物と、カルボキシル基を有するジオール化合物と、を反応させて得られるポリウレタン化合物、を含むことを特徴とする請求項1〜3のいずれか一項に記載の感光性樹脂組成物。
- (d)熱硬化剤を更に含有することを特徴とする請求項1〜4のいずれか一項に記載の感光性樹脂組成物。
- 前記(d)熱硬化剤が、ブロック型イソシアネートを含むことを特徴とする請求項5に記載の感光性樹脂組成物。
- (e)バインダーポリマーを更に含有することを特徴とする請求項1〜6のいずれか一項に記載の感光性樹脂組成物。
- 前記(e)バインダーポリマーが、重量平均分子量が50000〜100000であるアクリル樹脂を含むことを特徴とする請求項7に記載の感光性樹脂組成物。
- 支持体と、該支持体上に設けられ、請求項1〜8のいずれか一項に記載の感光性樹脂組成物からなる感光性樹脂組成物層と、を備えることを特徴とする感光性フィルム。
- 回路形成用基板上に請求項1〜8のいずれか一項に記載の感光性樹脂組成物からなる感光性樹脂組成物層を設け、当該感光性樹脂組成物層に直接描画方式によりレーザ光線を画像状に照射して露光部を光硬化させ、未露光部を現像により除去することを特徴とするレジストパターンの形成方法。
- 回路形成用基板上に請求項1〜8のいずれか一項に記載の感光性樹脂組成物からなる感光性樹脂組成物層を設け、当該感光性樹脂組成物層に活性光線を画像状に照射して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する工程を経て形成されることを特徴とする永久レジスト。
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JP4790460B2 (ja) * | 2006-03-24 | 2011-10-12 | 富士フイルム株式会社 | 感光性組成物、感光性フィルム、感光性積層体、永久パターン形成方法、及びプリント基板 |
JP4827088B2 (ja) * | 2006-04-13 | 2011-11-30 | 太陽ホールディングス株式会社 | アルカリ現像型ソルダーレジスト及びその硬化物並びにそれを用いて得られるプリント配線板 |
JP5098411B2 (ja) * | 2006-04-19 | 2012-12-12 | 日立化成工業株式会社 | 感光性樹脂組成物、並びにこれを用いた感光性フィルム及び感光性永久レジスト |
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