JP5741898B2 - 感光性樹脂組成物及びこれを用いた感光性エレメント - Google Patents
感光性樹脂組成物及びこれを用いた感光性エレメント Download PDFInfo
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- JP5741898B2 JP5741898B2 JP2010252732A JP2010252732A JP5741898B2 JP 5741898 B2 JP5741898 B2 JP 5741898B2 JP 2010252732 A JP2010252732 A JP 2010252732A JP 2010252732 A JP2010252732 A JP 2010252732A JP 5741898 B2 JP5741898 B2 JP 5741898B2
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- Materials For Photolithography (AREA)
- Non-Metallic Protective Coatings For Printed Circuits (AREA)
Description
また、本発明は、[2] 前記(f)成分のメラミンの最大粒径が、10μm以下である上記[1]記載の感光性樹脂組成物に関する。
また、本発明は、[3] 前記(b)成分が、ジメチロールトリシクロデカンジアクリレート、ジメチロールトリシクロデカンジメタクリレート、トリシクロデカンジオールジアクリレート及びトリシクロデカンジオールジメタクリレートからなる群から選択される1種以上である上記[1]又は[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(b)成分が、下記一般式(2)又は一般式(3)で示される部分構造を有する上記[1]又は[2]に記載の感光性樹脂組成物に関する。
また、本発明は、[5] 前記一般式(2)又は一般式(3)で示される部分構造を有する化合物が、トリシクロデカン構造を含むジオール化合物と、ジイソシアネート化合物と、分子中に少なくとも1個以上のエチレン性不飽和基と1個のヒドロキシル基を有する化合物と、を反応させて得られるウレタン化合物である上記[4]記載の感光性樹脂組成物に関する。
また、本発明は、[6] 前記ジイソシアネート化合物が、環構造を有するジイソシアネートである上記[4]又は[5]記載の感光性樹脂組成物に関する。
また、本発明は、[7] 前記分子中に少なくとも1個以上のエチレン性不飽和基と1個のヒドロキシル基を有する化合物が、エチレン性不飽和基を分子中に3個有する化合物である上記[5]又は[6]記載の感光性樹脂組成物に関する。
また、本発明は、[8] 前記エチレン性不飽和基を分子中に3個有する化合物が、下記一般式(4)で示される上記[7]記載の感光性樹脂組成物に関する。
本発明の(a)成分であるエチレン性不飽和基とカルボキシル基を有する樹脂としては、特に制限はないが、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水酸基及びエポキシ化合物(a1)中に元来ある水酸基と、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KOHの滴定量(mL)を示し、Wpは測定樹脂溶液質量(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。
上記アルキレン基としては、炭素数2〜20のアルキレン基であることが好ましく、炭素数2〜10のアルキレン基であることがより好ましく、炭素数2〜6のアルキレン基であることがさらに好ましい。
炭素数2〜6のアルキレン基としては、エチレン基、プロピレン基、イソプロピレン基、ブチレン基、ペンチレン基、へキシレン基等が挙げられるが、解像度、耐めっき性の点からエチレン基又はイソプロピレン基であることが好ましく、エチレン基であることが特に好ましい。
上記アリーレン基としては、炭素数は6〜14のアリーレン基であることが好ましく、炭素数6〜10のアリーレン基であることがより好ましい。このようなアリーレン基としては、フェニレン、ナフチレン等が挙げられる。
本発明で用いる(c)光重合開始剤としては、使用する露光機の光波長にあわせたものであれば特に制限はなく、公知のものを利用することができる。具体的には例えば、ベンゾフェノン、N,N’−テトラアルキル−4,4’−ジアミノベンゾフェノン、2−ベンジル−2−ジメチルアミノ−1−(4−モルホリノフェニル)−ブタノン−1、2−メチル−1−[4−(メチルチオ)フェニル]−2−モルホリノ−プロパノン−1、4,4’−ビス(ジメチルアミノ)ベンゾフェノン(ミヒラーケトン)、4,4’−ビス(ジエチルアミノ)ベンゾフェノン、4−メトキシ−4’−ジメチルアミノベンゾフェノン等の芳香族ケトン類、アルキルアントラキノン、フェナントレンキノン等のキノン類、ベンゾイン、アルキルベンゾイン等のベンゾイン化合物、ベンゾインアルキルエーテル、ベンゾインフェニルエーテル等のベンゾインエーテル化合物、ベンジルジメチルケタール等のベンジル誘導体、2−(o−クロロフェニル)−4,5−ジフェニルイミダゾール二量体、2−(o−クロロフェニル)−4,5−ジ(m−メトキシフェニル)イミダゾール二量体、2−(o−フルオロフェニル)−4,5−ジフェニルイミダゾール二量体、2−(o−メトキシフェニル)−4,5−ジフェニルイミダゾール二量体、2,4−ジ(p−メトキシフェニル)−5−フェニルイミダゾール二量体、2−(2,4−ジメトキシフェニル)−4,5−ジフェニルイミダゾール二量体等の2,4,5−トリアリールイミダゾール二量体、N−フェニルグリシン、N−フェニルグリシン誘導体、9−フェニルアクリジン等のアクリジン誘導体、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)]等のオキシムエステル類、7−ジエチルアミノ−4−メチルクマリン等のクマリン系化合物、2,4−ジエチルチオキサントン等のチオキサントン系化合物、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等のアシルホスフィンオキサイド系化合物などが挙げられ、これらは単独で又は二種類以上を組み合わせて用いることができる。
上記オキシムエステルを有する化合物としては、例えば、(2−(アセチルオキシイミノメチル)チオキサンテン−9−オン)、(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)]、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))が挙げられる。市販品としては、IRGACURE−OXE01、IRGACURE−OXE02(いずれもチバ・スペシャルティ・ケミカルズ社製)等が挙げられる。
具体的にはアセトグアナミン、ベンゾグアナミン、四国化成工業株式会社製;2MZ−A、2E4MZ−A、C11Z−A、2MA−OK等が挙げられる。特に溶剤への溶解性の観点から、ベンゾグアナミンが望ましい。
尚、感光性樹脂組成物は、上記した(a)〜(g)成分に加えて所望の特性に応じて、その他の成分を更に含んでもよい。
本発明の感光性エレメントは、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。
表1〜2に示す各成分を同表に示した配合量(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に示した各成分は、下記のものを使用した。
「EXP−2811」:トリシクロデカン構造を含むエポキシ樹脂(EPICLON HP−200、DIC株式会社製、商品名)を変性したトリシクロデカン構造含有の酸変性エポキシアクリレート(DIC株式会社製、試料名)。
「ZFR−1158」: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)。
「UXE−3024」:ウレタン変性エポキシアクリレート(日本化薬株式会社製、商品名)。
「樹脂(1)」:メタクリル酸、メタクリル酸メチル、アクリル酸ブチルの共重合体で重量平均分子量60000、酸価110mgKOH/g、ZP−18、日立化成工業株式会社製)。
「NKエスペルDCP」:トリシクロデカンジメタノールジメタクリレート(新中村化学工業株式会社製、商品名)。
「UX−5002D−M20」:トリシクロデカン構造含有ウレタンアクリレート(日本化薬株式会社製、商品名)。
「ヒタロイド9082」:ウレタンアクリレート(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(日本化薬株式会社製、商品名)。
「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)。
「DAROCURE−TPO」: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)。
「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−907」:2−メチル−1[4−(メチルチオ)フェニル]−2−モリフォリノプロパン−1−オン(チバ・スペシャルティ・ケミカルズ社製、商品名)。
「NC−3000H」:ビフェニルアラルキル型エポキシ樹脂(日本化薬社製、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)。
「ベンゾグアナミン」:2,4−ジアミノ−6−フェニル−1,3,5−トリアジン(日本触媒株式会社製、商品名)。
「2MA−OK」:2,4−ジアミノ−6−[2’−メチルイミダゾリル−(1’)]−エチル−s−トリアジンイソシアヌル酸付加物(四国化成工業株式会社製、商品名)。
「3MT」:3−メルカプト−1,2,4−トリアゾール(アルドリッチ社製、商品名)。
「メラミン−A」:微分メラミン(日産化学工業社製、商品名)を使用し、以下の方法で最大粒径が5μm以下まで分散した、メラミン分散溶液。
「メラミン−B」:微分メラミン(日産化学工業社製、最大粒径約15μm以下、商品名)。
(b)成分40質量部(固形分)、上記メラミン10質量部、及びメチルエチルケトン50質量部を、スターミルLMZ(アシザワファインテック株式会社製)で、直径0.6mmのジルコニアビーズを用い、周速12m/sにて分散し、最大粒径が5μm以下となった時点で分散を終了し、メラミン分散液を得た。メラミンは上記で調製した分散液を配合することで、感光性樹脂組成物に含有させた。
「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株式会社製、商品名)。
「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。
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、20μmであった。
実施例1〜6、参考例1及び比較例1〜6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、塗膜性、解像性、金めっき耐性、密着性、そりについて評価した。得られた結果を表3〜4に示した。
得られた感光性フィルムの外観を観察し、以下の判定基準により塗膜性を判定した。
「A」:塗膜外観に色ムラやスジ/ハジキが観察されないもの。
「B」:塗膜概観に色ムラやスジ/ハジキが多数観察されるもの。
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、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、圧着圧力0.4MPa、プレス熱板温度80℃、真空引き時間20秒、ラミネートプレス時間30秒、気圧4kPa以下でラミネートを行い、評価用積層体を得た。
「A」:ビア径50μmが解像できているもの。
「B」:ビア径50μmが解像できていないもの。
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、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、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、評価用積層体を得た。
「A」:ソルダーレジスト底部への染み込みが認められないもの。
「B」:ソルダーレジスト底部への染み込みが1〜10μmまでのもの。
「C」:上記以外のもの。
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)の銅表面にCZ処理(CZ−8100、メック株式会社製)を行った。このプリント配線板用基板上に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、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、プレス熱板温度80℃、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、評価用積層体を得た。
「A」:密着強度が2.0MPa以上のもの。
「B」:密着強度が2.0MPa未満のもの。
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)の銅箔をエッチングして、銅を全て除去した0.06mm厚のガラスエポキシ基材(50mm×50mm)の片面上に、上記のようにソルダーレジストの硬化物を形成し(全面を露光して、現像、紫外線照射、加熱処理まで行い形成)、次いで、ソルダーレジストが形成された基板を切り出し、4コーナーのそり高さを定規で測定し、以下の判定基準により評価した。
「A」:4コーナーの反り高さの平均値が、5mm未満のもの。
「B」:4コーナーの反り高さの平均値が、5mm以上、10mm未満のもの。
「C」:4コーナーの反り高さの平均値が、10mm以上のもの。
これに対し、(a)〜(g)成分を規定量用いた本発明の実施例によれば、塗膜性、解像性、Ni/Auめっき耐性、そり、密着性に優れた、プリント配線板、半導体パッケージ基板、フレキシブル配線板に最適なソルダーレジストを形成できる感光性樹脂組成物と感光性エレメントを提供することができる。
Claims (9)
- (a)成分:エチレン性不飽和基とカルボキシル基を有する樹脂と、
(b)成分:エチレン性不飽和基とトリシクロデカン構造とを有する光重合性モノマーと
、
(c)成分:光重合開始剤と、
(d)成分:エポキシ樹脂と、
(e)成分:下記一般式(1)で表されるグアナミン誘導体と、
(f)成分:メラミンと、
(g)成分:ジシアンジアミドと、を含有する感光性樹脂組成物であって、
前記(f)成分のメラミンを(a)成分及び(b)成分の合計を100質量部とした際に、0.1質量部以上、10質量部未満含有する感光性樹脂組成物。
- 前記(f)成分のメラミンの最大粒径が、10μm以下である請求項1記載の感光性樹脂組成物。
- 前記(b)成分が、ジメチロールトリシクロデカンジアクリレート、ジメチロールトリシクロデカンジメタクリレート、トリシクロデカンジオールジアクリレート及びトリシクロデカンジオールジメタクリレートからなる群から選択される1種以上である請求項1又は請求項2に記載の感光性樹脂組成物。
- 前記一般式(2)又は一般式(3)で示される部分構造を有する化合物が、トリシクロデカン構造を含むジオール化合物と、ジイソシアネート化合物と、分子中に少なくとも1個以上のエチレン性不飽和基と1個のヒドロキシル基を有する化合物と、を反応させて得られるウレタン化合物である請求項4記載の感光性樹脂組成物。
- 前記ジイソシアネート化合物が、環構造を有するジイソシアネートである請求項4又は請求項5記載の感光性樹脂組成物。
- 前記分子中に少なくとも1個以上のエチレン性不飽和基と1個のヒドロキシル基を有する化合物が、エチレン性不飽和基を分子中に3個有する化合物である請求項5又は請求項請求項6記載の感光性樹脂組成物。
- 支持体と、該支持体上に形成された請求項1〜8のいずれか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、を備える感光性エレメント。
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