JPWO2014010688A1 - 硬化膜形成組成物、配向材および位相差材 - Google Patents
硬化膜形成組成物、配向材および位相差材 Download PDFInfo
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- QURCVMIEKCOAJU-UHFFFAOYSA-N trans-isoferulic acid Natural products COC1=CC=C(C=CC(O)=O)C=C1O QURCVMIEKCOAJU-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/18—Manufacture of films or sheets
-
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Abstract
Description
そして、観察者がメガネを着用して3D画像を観察するディスプレイの方式の1つとしては、円偏光メガネ方式等が知られている(例えば、特許文献1を参照。)。
(A)光配向性基とヒドロキシ基、カルボキシル基およびアミノ基から選ばれるいずれか1つの置換基とを有する化合物、
(B)ヒドロキシ基、カルボキシル基およびアミノ基から選ばれる1種または2種以上の置換基を有する親水性ポリマー、並びに
(C)N−ヒドロキシメチル化合物またはN−アルコキシメチル(メタ)アクリルアミド化合物を含むモノマーを重合したポリマーを含有することを特徴とする硬化膜形成組成物に関する。
また、本発明の第1の態様において、(B)成分が、ヒドロキシアルキル基を側鎖に有するアクリル重合体であることが好ましい。
本実施の形態の硬化膜形成組成物は、(A)成分である低分子の光配向成分と、(B)成分である親水性ポリマーと、(C)成分であるN−ヒドロキシメチル化合物またはN−アルコキシメチル(メタ)アクリルアミド化合物を含むモノマーを重合したポリマーを含有する。本実施の形態の硬化膜形成組成物は、(A)成分、(B)成分、(C)成分に加えて、さらに、(D)成分として架橋触媒、(E)成分として硬化膜の接着性を向上させる成分をも含有することができる。そして、本発明の効果を損なわない限りにおいて、その他の添加剤を含有することができる。
<(A)成分>
本実施の形態の硬化膜形成組成物に含有される(A)成分は、上述した、低分子の光配向成分である。
尚、本発明において、光配向性基としては光二量化または光異性化する構造部位の官能基を言う。
光配向性基とアミノ基とを有する化合物の具体例としてはメチル−4−アミノけい皮酸、エチル−4−アミノけい皮酸、メチル−3−アミノけい皮酸、エチル−3−アミノけい皮酸等が挙げられる。
(A)成分である低分子の光配向成分は、以上の具体例を挙げることができるが、これらに限定されるものではない。
本実施の形態の硬化膜形成組成物に含有される(B)成分は、親水性のポリマーである。
そして、(B)成分であるポリマーは、ヒドロキシ基、カルボキシル基およびアミノ基から選ばれる1種または2種以上の置換基を有するポリマー(以下、特定重合体とも言う。)とすることができる。
このうち、アクリル重合体としてはアクリル酸エステル、メタクリル酸エステル、スチレン等の不飽和二重結合を有するモノマーを重合して得られる重合体が適用されうる。
カルボキシル基およびフェノール性ヒドロキシ基のうち少なくとも一方を有する構造単位として、好ましい構造単位は下記式[B2]で表される。
上述したフェノール性ヒドロキシ基を有するモノマーとしては、例えば、p−ヒドロキシスチレン、m−ヒドロキシスチレン、o−ヒドロキシスチレンが挙げられる。
他方、b2モノマーとしてフェノール性ヒドロキシ基のみを有するモノマーを用いる場合、b1モノマーが2モル%乃至80モル%、b2モノマーが20モル%乃至98モル%であることが好ましい。b2モノマーが過小の場合は液晶配向性が不充分となり易く、過大の場合は(A)成分との相溶性が低下し易い。
(B)成分の特定重合体の好ましい一例であるヒドロキシアルキル基を側鎖に有するアクリル重合体としては、例えば、ヒドロキシエチルアクリレート、ヒドロキシエチルメタクリレート、ヒドロキシプロピルアクリレート、ヒドロキシプロピルメタクリレート、ヒドロキシブチルアクリレート、ヒドロキシブチルメタクリレート、ヒドロキシペンチルアクリレート及びヒドロキシペンチルメタクリレート等のヒドロキシアルキルエステルモノマーを重合したもの、または、当該ヒドロキシアルキルエステルモノマーと、上記b1モノマー、上記b2モノマー、及び、これらのモノマー以外のモノマー、例えばヒドロキシ基およびカルボキシ基のいずれも有さないモノマーからなる群から選ばれる1種または2種以上のモノマーとを共重合したものが挙げられる。
(B)成分のメラミンホルムアルデヒド樹脂は、保存安定性の観点からメラミンとホルムアルデヒドの重縮合の際に生成したメチロール基がアルキル化されていることが好ましい。
本実施の形態の硬化膜形成組成物に含有される(C)成分は、N−ヒドロキシメチル化合物またはN−アルコキシメチル(メタ)アクリルアミド化合物を含むモノマーを重合したポリマーである。
本実施の形態の硬化膜形成組成物は、(A)成分、(B)成分、(C)成分に加えて、さらに、(D)成分として架橋触媒を含有することができる。
(D)成分である架橋触媒としては、例えば、酸または熱酸発生剤とすることができる。この(D)成分は、本実施の形態の硬化膜形成組成物の熱硬化反応を促進させることにおいて有効である。
本実施の形態の硬化膜形成組成物は、主として溶剤に溶解した溶液状態で用いられる。その際に使用する溶剤は、(A)成分、(B)成分および(C)成分、必要に応じて(D)成分、および/または、後述するその他添加剤を溶解できればよく、その種類および構造などは特に限定されるものでない。
さらに、本実施の形態の硬化膜形成組成物は、本発明の効果を損なわない限りにおいて、必要に応じて、増感剤、シランカップリング剤、界面活性剤、レオロジー調整剤、顔料、染料、保存安定剤、消泡剤、酸化防止剤等を含有することができる。
本実施の形態の硬化膜形成組成物は、(A)成分である低分子の光配向成分と、(B)成分である、(A)成分の光配向性成分より親水性であるポリマーと、(C)成分であるN−ヒドロキシメチル化合物またはN−アルコキシメチル(メタ)アクリルアミド化合物を含むモノマーを重合したポリマーとを含有する。そして、本発明の効果を損なわない限りにおいて、その他の添加剤を含有することができる。
[1]:(A)成分と(B)成分の配合比が質量比で5:95乃至60:40であり、(A)成分と(B)成分との合計量の100質量部に基づいて、10質量部乃至150質量部の(C)成分を含有する硬化膜形成組成物。
本実施の形態の硬化膜形成組成物における固形分の割合は、各成分が均一に溶剤に溶解している限り、特に限定されるものではないが、1質量%乃至80質量%であり、好ましくは3質量%乃至60質量%であり、より好ましくは5質量%乃至40質量%である。ここで、固形分とは、硬化膜形成組成物の全成分から溶剤を除いたものをいう。
本実施の形態の硬化膜形成組成物の溶液を基板(例えば、シリコン/二酸化シリコン被覆基板、シリコンナイトライド基板、金属、例えば、アルミニウム、モリブデン、クロムなどが被覆された基板、ガラス基板、石英基板、ITO基板等)やフィルム(例えば、トリアセチルセルロース(TAC)フィルム、シクロオレフィンポリマーフィルム、ポリエチレンテレフタレートフィルム、アクリルフィルム等の樹脂フィルム)等の上に、バーコート、回転塗布、流し塗布、ロール塗布、スリット塗布、スリットに続いた回転塗布、インクジェット塗布、印刷などによって塗布して塗膜を形成し、その後、ホットプレートまたはオーブン等で加熱乾燥することにより、硬化膜を形成することができる。
そのため、本実施の形態の硬化膜形成組成物は、各種位相差材(位相差フィルム)や液晶表示素子等の製造に好適に用いることができる。
以下の実施例で用いる略記号の意味は、次のとおりである。
<光配向性基およびヒドロキシ基を有する化合物>
CIN1:4−ヒドロキシヘキシルオキシけい皮酸メチルエステル
CIN2:3−メトキシ−4−ヒドロキシヘキシルオキシけい皮酸メチルエステル
MAA:メタクリル酸
MMA:メタクリル酸メチル
HEMA:2−ヒドロキシエチルメタクリレート
AIBN:α、α’−アゾビスイソブチロニトリル
PCTO:ポリカプロラクトントリオール(分子量500)
HPCEL:ヒドロキシプロピルセルロース
PHEM:ポリヒドロキシエチルメタクリレート(25重量%PM溶液)
PEPO:ポリエステルポリオール(アジピン酸/ジエチレングリコール共重合体)(分子量4,800)
PCDO:ポリカーボネートジオール(Mw:500)
HMM:ヘキサメトキシメチルメラミン
BMAA:N−ブトキシメチルアクリルアミド
PTSA:p−トルエンスルホン酸一水和物
PM:プロピレングリコールモノメチルエーテル
MAA 2.5g、MMA 9.2g、HEMA 5.0g、重合触媒としてAIBN 0.2gをPM 50.7gに溶解し、70℃にて20時間反応させることによりアクリル共重合体溶液(固形分濃度25質量%)(P1)を得た。得られたアクリル共重合体のMnは19,600、Mwは45,200であった。
BMAA 25.0g、重合触媒としてAIBN 1.04gをPM 48.4gに溶解し、85℃にて20時間反応させることによりアクリル共重合体溶液(固形分濃度35質量%)(P2)を得た。得られたアクリル共重合体のMnは4,800、Mwは3,100であった。
BMAA 25.0g、重合触媒としてAIBN 0.52gをPM 47.4gに溶解し、70℃にて20時間反応させることによりアクリル共重合体溶液(固形分濃度35質量%)(P3)を得た。得られたアクリル共重合体のMnは10,500、Mwは17,370であった。
実施例および比較例の各硬化膜形成組成物をTACフィルム上にスピンコータを用いて2000rpmで30秒間回転塗布した後、温度110℃で120秒間、熱循環式オーブン中で加熱乾燥を行い、硬化膜を形成した。この硬化膜に313nmの直線偏光を垂直に照射し、配向材を形成した。基板上の配向材の上に、メルク株式会社製の水平配向用重合性液晶溶液RMS03−013Cを、スピンコータを用いて塗布し、次いで、60℃で60秒間ホットプレート上においてプリベークを行い、膜厚1.0μmの塗膜を形成した。この基板上の塗膜を1000mJ/cm2で露光し、位相差材を作製した。作製した基板上の位相差材を一対の偏光板で挟み込み、位相差材における位相差特性の発現状況を観察し、配向材が液晶配向性を示すのに必要な偏光UVの露光量を配向感度とした。
実施例および比較例の各硬化膜形成組成物を10cm角のTACフィルム上にスピンコータを用いて2000rpmで30秒間回転塗布した後、温度110℃で120秒間、熱循環式オーブン中で加熱乾燥を行い、硬化膜を形成した。この硬化膜に313nmの直線偏光を20mJ/cm2垂直に照射し、配向材を形成した。基板上の配向材の上に、メルク株式会社製の水平配向用重合性液晶溶液RMS03−013Cを、スピンコータを用いて塗布し、次いで、60℃で60秒間ホットプレート上においてプリベークを行い、膜厚1.0μmの塗膜を形成した。この基板上の塗膜を1000mJ/cm2で露光し、位相差材を作製した。作製した基板上の位相差材を一対の偏光板で挟み込み、光漏れのない面積が90%以上のものを○、90%に満たないものを×とした。
実施例および比較例の各硬化膜形成組成物をTACフィルム上にスピンコータを用いて2000rpmで30秒間回転塗布した後、温度110℃で120秒間、熱循環式オーブン中で加熱乾燥を行い硬化膜を形成した。この硬化膜に100μmのラインアンドスペースマスクを介し313nmの直線偏光を30mJ/cm2垂直に照射した。マスクを取り外し、基板を90度回転させた後、313nmの直線偏光を15mJ/cm2垂直に照射し、液晶の配向制御方向が90度異なる2種類の液晶配向領域が形成された配向材を得た。この基板上の配向材の上に、メルク株式会社製の水平配向用重合性液晶溶液RMS03−013Cを、スピンコータを用いて塗布し、次いで、60℃で60秒間ホットプレート上においてプリベークを行い、膜厚1.0μmの塗膜を形成した。この基板上の塗膜を1000mJ/cm2で露光し、パターン化位相差材を作製した。作製した基板上のパターン化位相差材を、偏光顕微鏡を用いて観察し、配向欠陥なく位相差パターンが形成されているものを○、配向欠陥が見られるものを×として評価した。
実施例および比較例の各硬化膜形成組成物を石英基板上にスピンコータを用いて2000rpmで30秒間回塗布した後、温度110℃で120秒間ホットプレート上において加熱乾燥ベークを行い膜厚300nmの硬化膜を形成した。膜厚はFILMETRICS社製 F20を用いて測定した。この硬化膜を紫外線可視分光光度計((株)島津製作所製SHIMADZU UV−2550型番)を用いて波長400nmの光に対する透過率を測定した。
以上の評価を行った結果を、次の表2に示す。
Claims (15)
- (A)光配向性基とヒドロキシ基、カルボキシル基およびアミノ基から選ばれるいずれか1つの置換基とを有する化合物、
(B)ヒドロキシ基、カルボキシル基およびアミノ基から選ばれる1種または2種以上の置換基を有する親水性ポリマー、並びに
(C)N−ヒドロキシメチル化合物またはN−アルコキシメチル(メタ)アクリルアミド化合物を含むモノマーを重合したポリマーを含有することを特徴とする硬化膜形成組成物。 - (A)成分の光配向性基が光二量化または光異性化する構造の官能基であることを特徴とする請求項1に記載の硬化膜形成組成物。
- (A)成分の光配向性基がシンナモイル基であることを特徴とする請求項1または請求項2に記載の硬化膜形成組成物。
- (A)成分の光配向性基がアゾベンゼン構造の基であることを特徴とする請求項1または請求項2に記載の硬化膜形成組成物。
- (A)成分が2個以上のヒドロキシ基を有することを特徴とする請求項1乃至請求項4のいずれか1項に記載の硬化膜形成組成物。
- (B)成分が、ポリエーテルポリオール、ポリエステルポリオール、ポリカーボネートポリオールおよびポリカプロラクトンポリオールよりなる群から選ばれた少なくとも1種のポリマーであることを特徴とする請求項1乃至請求項5のいずれか1項に記載の硬化膜形成組成物。
- (B)成分がセルロースまたはその誘導体であることを特徴とする請求項1乃至請求項5のいずれか1項に記載の硬化膜形成組成物。
- (B)成分が、ポリエチレングリコールエステル基および炭素原子数2乃至5のヒドロキシアルキルエステル基のうちの少なくとも一方と、カルボキシル基およびフェノール性ヒドロキシ基のうちの少なくとも一方とを有するアクリル重合体であることを特徴とする請求項1乃至請求項5のいずれか1項に記載の硬化膜形成組成物。
- (B)成分が、ヒドロキシアルキル基を側鎖に有するアクリル重合体であることを特徴とする請求項1乃至請求項5のいずれか1項に記載の硬化膜形成組成物。
- (D)成分として架橋触媒をさらに含有することを特徴とする請求項1乃至請求項9のいずれか1項に記載の硬化膜形成組成物。
- (A)成分と(B)成分の比率が質量比で5:95乃至60:40であることを特徴とする請求項1乃至請求項10のいずれか1項に記載の硬化膜形成組成物。
- (A)成分と(B)成分合計量の100質量部に基づいて、10質量部乃至150質量部の(C)成分を含有することを特徴とする請求項1乃至請求項11のいずれか1項に記載の硬化膜形成組成物。
- (A)成分の化合物と(B)成分のポリマーとの合計量の100質量部に対して0.01質量部乃至10質量部の(D)成分を含有する請求項9乃至請求項12のいずれか1項に記載の硬化膜形成組成物。
- 請求項1乃至請求項13のいずれか1項に記載の硬化膜形成組成物を用いて得られることを特徴とする配向材。
- 請求項1乃至請求項13のいずれか1項に記載の硬化膜形成組成物から得られる硬化膜を使用して形成されることを特徴とする位相差材。
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US9598547B2 (en) | 2017-03-21 |
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