JP2009029929A - 重合性液晶化合物及びラジカル光重合開始剤を含有する重合性組成物 - Google Patents
重合性液晶化合物及びラジカル光重合開始剤を含有する重合性組成物 Download PDFInfo
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- JP2009029929A JP2009029929A JP2007195230A JP2007195230A JP2009029929A JP 2009029929 A JP2009029929 A JP 2009029929A JP 2007195230 A JP2007195230 A JP 2007195230A JP 2007195230 A JP2007195230 A JP 2007195230A JP 2009029929 A JP2009029929 A JP 2009029929A
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
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Abstract
【解決手段】重合性基としてハロゲン原子で置換されてもよい(メタ)アクリロイル基を有する重合性液晶化合物と、ラジカル光重合開始剤としてカルバゾール骨格及びアシルオキシムエステルを有する化合物とを含有することを特徴とする重合性組成物。
【選択図】なし
Description
本発明の重合性組成物は、重合性基としてハロゲン原子で置換されてもよい(メタ)アクリロイル基を有する重合性液晶化合物と、ラジカル光重合開始剤としてカルバゾール骨格及びアシルオキシムエステル基とを有する化合物とを含有する。
本発明の重合性組成物を用いて作製される重合膜の耐熱性及び光学特性を確保するために、他の単量体の含有量は、上記重合性液晶化合物と上記ラジカル光重合開始剤との合計量100質量部に対して、50質量部以下が好ましく、特に30質量部以下がより好ましい。
また、炭酸カルシウムの針状結晶などの微粒子は光学異方性を有し、このような微粒子によって重合体の光学異方性を調節できる。上記有機物としては、例えばカーボンナノチューブ、フラーレン、デンドリマー、ポリビニルアルコール、ポリメタクリレート、ポリイミド等が挙げられる。
本発明の重合膜は、例えば、上記重合性組成物を溶媒に溶解した後、支持基板に塗布して、重合性組成物中の液晶分子を配向させた状態で脱溶媒し、次いでエネルギー線を照射して重合することにより得ることができる。
重合性液晶化合物である化合物No.1又はNo.6の1.0gを2−ブタノン4.0gに溶解させ、ラジカル光重合開始剤である化合物No.31、No.37又は比較化合物No.1〜No.3の0.03gを添加、完全に溶解させた後0.45μmフィルターで濾過して、実施例1−1〜1−3及び比較例1−1〜1−3の重合性組成物をそれぞれ得た。これらの溶液を、スピンコーターを使用して、ラビング処理したポリイミド付ガラス基板上に塗工し、100℃に設定したホットプレート上で3分乾燥させた。室温に戻し3分放置後、高圧水銀灯(120W/cm)で20秒照射し硬化させ、実施例1−1〜1−3及び比較例1−1〜1−3の重合膜をそれぞれ得た(膜厚が約1μmになるようにスピンコーターの回転数及び時間を調整した。)。得られた各重合膜を以下の手法により評価した。
得られた重合膜をOPTIPHOT2−POL(ニコン社製)偏光顕微鏡を使用し、表面の光学組織の確認を実施した。配向が一様であり、配向欠陥が確認されないものを○とし、表面が透明であるが、一部配向ムラが確認されるものを△とし、結晶化や配向ムラ等が確認されるものを×とした。
<硬化性>
得られた重合膜の表面硬化性を目視で確認した。均一に硬化しており、タックも残っていないものを○とし、均一に硬化しているが、若干タックが残っているものを△とし、全面にタックが残り、表面がベトついているものを×とした。
<耐熱性>
得られた重合膜について、OPTIPHOT2−POL(ニコン社製)偏光顕微鏡を用いてセナルモン法に基づく複屈折測定法に従い、室温25℃で波長546nmにおけるリターデーションを測定した。更にその重合膜を150℃オーブンで30分放置後、室温に冷却し上記方法に準じてリターデーションを測定し、下記式にて変化率を算出した。(変化率が小さい程熱による光学物性変化が小さく、耐熱性が高いと言える。)
(リターデーション変化率/%)=100−(リターデーション(耐熱試験後)/リターデーション(耐熱試験前)×100)
これに対し、本発明の重合性組成物は、均一に硬化し、配向性が一様であり、耐熱試験後のリターデーション変化も小さく、硬化性、配向性及び耐熱性に優れることが確認できた。特に化合物No.1を用いたものは耐熱性に優れることが確認できた。
重合性液晶化合物である化合物No.1の0.94gと光学活性化合物である化合物No.52の0.06gとを2−ブタノン2.0gに溶解させ、ラジカル光重合開始剤である化合物No.31又は比較化合物No.1若しくはNo.2の0.03gを添加、完全に溶解させた後0.45μmフィルターで濾過して、実施例2−1及び比較例2−1〜2−2の重合性組成物を調製した。この溶液を、スピンコーターを使用して、ラビング処理したポリイミド付ガラス基板上に塗工し、100℃に設定したホットプレート上で3分乾燥させた。室温に戻し3分放置後、高圧水銀灯(120W/cm)で20秒照射し硬化させ、実施例2−1及び比較例2−1〜2−2の重合膜を得た。(膜厚が約4μmになるようにスピンコーターの回転数及び時間を調整した。)得られた重合膜を以下の手法により評価した。
得られた重合膜をOPTIPHOT2−POL(ニコン社製)偏光顕微鏡を使用し、表面の光学組織の確認を実施した。選択反射が一様に確認され、配向欠陥が確認されないものを○とし、選択反射が確認できるが、オイリーストリーク欠陥が確認されるものを△とし、結晶化や配向ムラ等が確認されるものを×とした。
<硬化性>
得られた重合膜の表面硬化性を目視で確認した。均一に硬化しており、タックも残っていないものを○とし、均一に硬化しているが、若干タックが残っているものを△とし、全面にタックが残り、表面がベトついているものを×とした。
<選択反射>
5°正反射付属装置を取り付けた分光光度計(U−3010形:日立ハイテクノロジーズ社製)を使用し、25℃、波長800〜400nmの範囲で、得られた重合膜の反射率測定を実施し、選択反射中心波長(λ)を測定した。
これに対し、本発明の重合性組成物は、均一に硬化し、選択反射が一様に確認され、硬化性及び配向性に優れることが確認できた。
Claims (13)
- 重合性基としてハロゲン原子で置換されてもよい(メタ)アクリロイル基を有する重合性液晶化合物と、ラジカル光重合開始剤としてカルバゾール骨格及びアシルオキシムエステル基を有する化合物とを含有することを特徴とする重合性組成物。
- 上記重合性液晶化合物が、下記一般式(I)で表される二官能(メタ)アクリレート化合物である請求項1に記載の重合性組成物。
- 上記一般式(I)又は(II)において、Eがすべて水素原子である請求項2又は3に記載の重合性組成物。
- 上記一般式(II)において、環A1及び環A3がベンゼン環又はナフタレン環である請求項2〜4のいずれかに記載の重合性組成物。
- 上記一般式(II)において、環A1及び環A3の少なくとも一つがナフタレン環である請求項2〜5のいずれかに記載の重合性組成物。
- 上記ラジカル光重合開始剤が、下記一般式(III)で表される化合物である請求項1〜6のいずれかに記載の重合性組成物。
- 光学活性化合物を含有し、コレステリック相を発現する請求項1〜9のいずれかに記載の重合性組成物。
- 30℃以下で液晶相を示す請求項1〜10のいずれかに記載の重合性組成物。
- 請求項1〜11のいずれかに記載の重合性組成物が液晶相を示す状態で、光重合させることにより作製された重合膜。
- 請求項12に記載の重合膜を使用してなるディスプレイ用光学フィルム。
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