JP2014145826A - 紫外線硬化型樹脂組成物 - Google Patents
紫外線硬化型樹脂組成物 Download PDFInfo
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- JP2014145826A JP2014145826A JP2013013042A JP2013013042A JP2014145826A JP 2014145826 A JP2014145826 A JP 2014145826A JP 2013013042 A JP2013013042 A JP 2013013042A JP 2013013042 A JP2013013042 A JP 2013013042A JP 2014145826 A JP2014145826 A JP 2014145826A
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Abstract
【解決手段】光増感剤としてスクアリリウム化合物を用いた紫外線硬化型樹脂組成物及びそれを用いて作製した画像形成材。該紫外線硬化型樹脂組成物は、特に紫外線発光ダイオードに対して優れた感度を有するため、少ない露光でも硬化させることができる。
【選択図】なし
Description
特許文献1には紫外線硬化型樹脂組成物に用いる光増感剤として、チオキサン系化合物、アミン系化合物が開示されているが、該化合物では紫外線に対して、十分な感度が得られない問題があった。
本発明に用いる光増感剤は、一般式(A)又は(B)で表されるスクアリリウム化合物を用いる。
光重合開始剤は、スクアリリウム化合物である光増感剤との共存下で光照射されたときに、光増感剤の光励起エネルギーを受け取って活性ラジカルを発生し、エチレン性不飽和化合物を重合に到らしめるラジカル発生剤であって、例えば、ヘキサアリールビイミダゾール系化合物、チタノセン系化合物、ハロメチル化s−トリアジン誘導体、ハロメチル化1,3,4−オキサジアゾール誘導体、ジアリールヨードニウム塩、有機硼素酸塩、及び有機過酸化物等が挙げられる。紫外線硬化型樹脂組成物としての感度、基板に対する密着性及び保存安定性等の面から、ヘキサアリールビイミダゾール系化合物、チタノセン系化合物が好ましく、ヘキサアリールビイミダゾール系化合物が特に好ましく挙げられる。
上記エチレン性不飽和化合物とは、紫外線硬化型樹脂組成物が紫外線の照射を受けたときに、光重合開始剤を含む光重合開始系の作用により付加重合し、場合により架橋、硬化するようなラジカル重合性のエチレン性不飽和結合を分子内に少なくとも1個有する化合物である。
(1)前記の紫外線硬化型樹脂組成物の各成分を適当な溶剤に溶解或いは分散させた塗布液とする。(2)被加工基板上に直接に塗布し乾燥させる。(3)被加工基板上に紫外線硬化型樹脂組成物を硬化させた硬化物の層が形成される。
更に、画像形成材は、以下の画像形成方法に好適に用いられる。即ち、画像形成材の紫外線硬化型樹脂組成物の層を、例えば波長350〜400nmの紫外線発光ダイオードにより走査露光し、現像処理して画像を現出させる。
<紫外線用硬化樹脂組成物と画像形成材の製造>
ペンタエリスリトールアクリレート100部、ポリビニルピロリドン100部、2−[2−(フラン−2−イル)ビニル]−4,6−ビス(トリクロロメチル)−1,3,5−トリアジン10部、3−(2,3−ジヒドロ−1,5−ジメチル−3−オキソ−2−フェニル−1H−ピラゾール−4−イル)−4−(ジメチルアミノ)−3−シクロブテン−1,2−ジオン(MicroCombiChem社製)(スクアリリウム化合物(1))0.1部をメチルセロソルブ900部に溶解して紫外線硬化樹脂組成物を得た。得られた紫外線硬化樹脂組成物をポリエステルフィルムにスピンコーターを用いて塗布し、乾燥させて、画像形成材(膜厚2μm)を作製した。
画像形成材を50×60mmの大きさに切り出したサンプルを、回折分光照射装置を用い、キセノンランプ(ウシオ電機社製「UI−501C」)を光源として300〜500nmの波長域で分光した光を横軸方向に露光波長が直線的に、縦軸方向に露光強度が対数的に変化するように設定して10秒間照射して露光し、次いで25℃の0.7質量%炭酸ナトリウム水溶液を現像液として0.15MPaとなるように吹き付け、最小現像時間の1.5倍の時間でスプレー現像することにより、各露光波長の感度に応じた画像が得られ、その画像高さから画像形成可能な露光エネルギーを算出し、横軸に波長、縦軸にその露光エネルギーの逆数をプロットすることにより得られる分光感度曲線における極大ピークを読みとった。露光感度の極大ピーク(nm)の波長を表1に示す。
紫外線硬化樹脂組成物を用いて作製した硬化物層を、中心波長370nm、レーザー出力5mWの紫外線発光ダイオードを用いて、像面照度2mW、ビームスポット径2μmで、ビーム走査間隔及び走査速度を変えながら操作露光し、次いで、30℃の1質量%炭酸ナトリウム水溶液を現像液として0.15MPaとなるように吹き付け、最小現像時間の2倍の時間でスプレー現像することによりネガ画像を現出させた。得られた画像について20μmの線幅が再現するのに要する露光量を求め露光感度とした。露光感度の測定結果を表1に示す。
実施例1に記載の3−(2,3−ジヒドロ−1,5−ジメチル−3−オキソ−2−フェニル−1H−ピラゾール−4−イル)−4−(ジメチルアミノ)−3−シクロブテン−1,2−ジオン(MicroCombiChem社製)(スクアリリウム化合物(1))を、3−(2,3−ジヒドロ−1,5−ジメチル−3−オキソ−2−フェニル−1H−ピラゾール−4−イル)−4−(1−ピペリジニル)−3−シクロブテン−1,2−ジオン(MicroCombiChem社製)(スクアリリウム化合物(2))に代えた以外は、実施例1と同様にして画像形成材を製造し、分光感度の極大ピークと露光感度を測定した。
実施例1に記載の3−(2,3−ジヒドロ−1,5−ジメチル−3−オキソ−2−フェニル−1H−ピラゾール−4−イル)−4−(ジメチルアミノ)−3−シクロブテン−1,2−ジオン(MicroCombiChem社製)(スクアリリウム化合物(1))を、3−(2,3−ジヒドロ−1,5−ジメチル−3−オキソ−2−フェニル−1H−ピラゾール−4−イル)−4−フェニル−3−シクロブテン−1,2−ジオン(MicroCombiChem社製)(スクアリリウム化合物(9))に代えた以外は、実施例1と同様にして画像形成材を製造し、分光感度の極大ピークと露光感度を測定した。
実施例1に記載の3−(2,3−ジヒドロ−1,5−ジメチル−3−オキソ−2−フェニル−1H−ピラゾール−4−イル)−4−(ジメチルアミノ)−3−シクロブテン−1,2−ジオン(MicroCombiChem社製)(スクアリリウム化合物(1))を、3−(2,3−ジヒドロ−1,5−ジエチル−3−オキソ−2−フェニル−1H−ピラゾール−4−イル)−4−フェニル−3−シクロブテン−1,2−ジオン(MicroCombiChem社製)(スクアリリウム化合物(10))に代えた以外は、実施例1と同様にして画像形成材を製造し、分光感度の極大ピークと露光感度を測定した。
Claims (5)
- 一般式(A)又は(B)で表されるスクアリリウム化合物からなる光増感剤が、350nm〜400nmに露光感度の極大ピークを有することを特徴とする請求項1に記載の紫外線硬化型樹脂組成物。
- 請求項1又は2に記載の紫外線硬化型樹脂組成物を、波長350nm〜400nmのレーザー光によって光硬化させることを特徴とする硬化物。
- 仮支持フィルム上に、請求項1又は2に記載の紫外線硬化型樹脂組成物の層を形成させ、350nm〜400nmのレーザー光によって光硬化させて得られる硬化物層を有することを特徴とする画像形成材料。
- 被加工基板上に請求項4に記載の画像形成材料が、硬化物層側で積層されてなることを特徴とする画像形成材。
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