JP5311725B2 - 重合性組成物 - Google Patents
重合性組成物 Download PDFInfo
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- JP5311725B2 JP5311725B2 JP2006189772A JP2006189772A JP5311725B2 JP 5311725 B2 JP5311725 B2 JP 5311725B2 JP 2006189772 A JP2006189772 A JP 2006189772A JP 2006189772 A JP2006189772 A JP 2006189772A JP 5311725 B2 JP5311725 B2 JP 5311725B2
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- 0 CCC(C)(C*(C)(C)OC(C=C)=*)Oc(cc1)ccc1C(Oc(cc1)cc(CC)c1OC(c1ccc(cc(cc2)OC(C=C)=O)c2c1)=O)=O Chemical compound CCC(C)(C*(C)(C)OC(C=C)=*)Oc(cc1)ccc1C(Oc(cc1)cc(CC)c1OC(c1ccc(cc(cc2)OC(C=C)=O)c2c1)=O)=O 0.000 description 8
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- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
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- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
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- C09K19/2007—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers the chain containing -COO- or -OCO- groups
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- C09K19/322—Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
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- C09K2019/0448—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group the end chain group being a polymerizable end group, e.g. -Sp-P or acrylate
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- C09K2323/00—Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition
Description
上記比率が、20/80より小さいと、重合して得られる重合膜の耐熱性や耐溶剤性が不足する場合があり、上記比率が、95/5より大きいと重合性組成物の配向制御が困難となるからである。
また、上記二官能(メタ)アクリレート化合物及び上記単官能(メタ)アクリレート化合物の含有量の和は、本発明の重合性組成物(但し、溶剤を除く)中、少なくとも50質量%以上であることが好ましく、70質量%以上であることが特に好ましい。
また、本発明の重合性組成物は、少なくとも室温付近、具体的には30℃以下で液晶相を示すことが好ましく、特に25℃以下で液晶相を示すことがより好ましい。
ただし、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付与するために、他の単量体の含有量は、上記二官能(メタ)アクリレート化合物及び上記単官能(メタ)アクリレート化合物の合計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。
界面活性剤の好ましい使用割合は、界面活性剤の種類、組成物の成分比などに依存するが、重合性組成物に対して、100ppmから5質量%の範囲であることが好ましく、特に0.05から1質量%の範囲が好ましい。
まず、下記の手順(〔1〕重合性組成物の調製、〔2〕支持基板の製作、〔3〕支持基板への塗布)に従い本発明の重合性組成物から重合膜を作製した。
表1に記載の組成物1.0gを溶剤(シクロヘキサノン/2−ブタノン=1/1(質量%))4gに添加して溶解した後、ラジカル重合開始剤(N−1919;株式会社ADEKA製)0.03gを加えて完全に溶解した後に、0.1μmフィルターでろ過処理を実施して溶液を調整した。
中性洗剤で洗浄後、純水で洗い流し乾燥したガラス板にポリビニルアルコール5%水溶液を、スピンコーターで均一に塗工し、100℃で3分間乾燥させた。乾燥後、ガラス基板に指示されたポリビニルアルコールの表面をレーヨン布で一定方向に擦り、塗布用支持基板を製作した。
〔1〕で調製した溶液を〔2〕で製作した支持基板上にスピンコーターで均一に塗工し、ホットプレートを用いて100℃で3分間乾燥後、室温下で3分間冷却し、高圧水銀灯(120W/cm)で20秒間照射して硬化して重合膜を得た。
上記の方法で得られた重合膜について、下記の試験を実施し、これらの結果について表1に併せて示す。
(1)リターデーション(R)
上記の方法で得られた重合膜に対して、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(R)を測定した。
得られた重合膜に対して、触針式表面形状測定器(Dektak6M;(株)アルバック製)を用いて室温25℃で膜厚(d)を測定した。
重合性組成物の光学(屈折率)異方性(Δn)と該組成物を重合して得られる重合膜の光学(屈折率)異方性(Δn)は下記の方法によって測定した。
重合性組成物の光学(屈折率)異方性(Δn)については、室温25℃の環境下で波長589nmにおける光学(屈折率)異方性(Δn)が0.0979であるエステル系ネマチック液晶に対して、重合性組成物を10質量%添加した組成物の物性から外挿して、重合性組成物の光学(屈折率)異方性(Δn)を算出した。一方、重合膜の光学(屈折率)異方性(Δn)については、下記の関係式において上記のリターデーション(R)及び膜厚(d)を代入して、重合膜の光学(屈折率)異方性(Δn)を算出した。
光学(屈折率)異方性(Δn)=リターデーション(R)/膜厚(d)
重合膜の均質性について偏光顕微鏡を用いて評価した。試料を、クロスニコル下で重合膜を設置したステージを回転させることによって、重合膜の配向状態を観察し、膜の均質性について評価した。重合膜の配向が均一に得られていれば○、配向が得られても不均一であれば△、重合膜に結晶等が発生して配向が全く得られていなければ×とした。
次に、表2に記載の組成物1.0gを溶媒(メチルエチルケトン)4gに添加して溶解した後、ラジカル重合開始剤(N−1919;株式会社ADEKA製)0.0025gを加え、完全に溶解させた後に0.1μmフィルターでろ過処理を実施して溶液を調製し、上記製造例1で製作した支持基板上にスピンコーターで調整した溶液を均一に塗工し、ホットプレートを用いて100℃で3分間乾燥後、室温下で1分間冷却し、高圧水銀灯(120W/cm)で20秒間照射して硬化させることによって重合膜を得た。得られた重合膜について選択反射と膜の均質性の評価を実施した。これらの結果について表2に併せて示す。
Claims (10)
- 下記一般式(1)で表される二官能(メタ)アクリレート化合物及び下記一般式(2)で表される単官能(メタ)アクリレート化合物を含有する重合性組成物。
- 上記一般式(1)中の環A1、A2及びA3において、少なくとも一つはナフタレン環である請求項1〜3の何れか1項に記載の重合性組成物。
- 上記一般式(1)で表される二官能(メタ)アクリレート化合物に対する上記一般式(2)で表される単官能(メタ)アクリレート化合物の比率(質量比)が、20/80〜95/5の範囲内である請求項1〜4の何れか1項に記載の重合性組成物。
- 30℃以下で液晶相を示す請求項1〜5の何れか1項に記載の重合性組成物。
- さらに、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1〜6の何れか1項に記載の重合性組成物。
- さらに、ラジカル重合開始剤及び界面活性剤を含有する請求項7記載の重合性組成物。
- 請求項1〜8の何れか1項に記載の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9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。
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2006189772A JP5311725B2 (ja) | 2006-07-10 | 2006-07-10 | 重合性組成物 |
US12/307,828 US7981320B2 (en) | 2006-07-10 | 2007-03-14 | Polymerizable composition |
CN2007800260810A CN101490117B (zh) | 2006-07-10 | 2007-03-14 | 聚合性组合物 |
KR1020097000268A KR101313044B1 (ko) | 2006-07-10 | 2007-03-14 | 중합성 조성물 |
PCT/JP2007/055075 WO2008007479A1 (fr) | 2006-07-10 | 2007-03-14 | Composition polymérisable |
EP07738545A EP2039707B1 (en) | 2006-07-10 | 2007-03-14 | Polymerizable composition |
TW096109826A TWI408148B (zh) | 2006-07-10 | 2007-03-22 | Polymerizable composition |
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JP2006189772A JP5311725B2 (ja) | 2006-07-10 | 2006-07-10 | 重合性組成物 |
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JP2008019290A JP2008019290A (ja) | 2008-01-31 |
JP5311725B2 true JP5311725B2 (ja) | 2013-10-09 |
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JP2006189772A Active JP5311725B2 (ja) | 2006-07-10 | 2006-07-10 | 重合性組成物 |
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US (1) | US7981320B2 (ja) |
EP (1) | EP2039707B1 (ja) |
JP (1) | JP5311725B2 (ja) |
KR (1) | KR101313044B1 (ja) |
CN (1) | CN101490117B (ja) |
TW (1) | TWI408148B (ja) |
WO (1) | WO2008007479A1 (ja) |
Families Citing this family (20)
Publication number | Priority date | Publication date | Assignee | Title |
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JP5219583B2 (ja) * | 2008-03-31 | 2013-06-26 | 住友化学株式会社 | 組成物、光学フィルムとその製造方法、光学部材及び表示装置 |
JP5219594B2 (ja) * | 2008-04-08 | 2013-06-26 | 住友化学株式会社 | 組成物、光学フィルム及びフラットパネル表示装置 |
JP5454084B2 (ja) * | 2008-12-16 | 2014-03-26 | Jnc株式会社 | 重合性液晶組成物およびホメオトロピック配向液晶フィルム |
JP2012058266A (ja) * | 2009-01-09 | 2012-03-22 | Sharp Corp | 液晶表示装置及び液晶層形成用組成物 |
US20120133882A1 (en) * | 2009-08-10 | 2012-05-31 | Jx Nippon Oil & Energy Corporation | Liquid crystal film and optical element produced using same |
DE102011105930A1 (de) * | 2010-07-21 | 2012-01-26 | Merck Patent Gmbh | Polymerisierbare Mischungen und ihre Verwendung in Flüssigkristallanzeigen |
JP2015510529A (ja) * | 2012-01-17 | 2015-04-09 | エルジー・ケム・リミテッド | 液晶組成物 |
CN102540545A (zh) * | 2012-02-24 | 2012-07-04 | 刘景利 | 聚合物分散液晶开关效应处理各波段射线的方法 |
CN102732264B (zh) * | 2012-06-04 | 2013-12-25 | 深圳市华星光电技术有限公司 | 一种液晶活性单体及液晶面板 |
TWI567171B (zh) | 2012-06-12 | 2017-01-21 | Lg化學股份有限公司 | 聚合性液晶化合物、包含該化合物之液晶組成物、以及包含該組成物之光學各向異性體 |
WO2013187668A1 (ko) * | 2012-06-12 | 2013-12-19 | 주식회사 엘지화학 | 중합성 액정 화합물, 이를 포함하는 액정 조성물 및 광학 이방체 |
WO2014003416A1 (ko) * | 2012-06-28 | 2014-01-03 | 주식회사 엘지화학 | 중합성 액정 화합물, 이를 포함하는 액정 조성물 및 광학 이방체 |
CN104379699B (zh) * | 2012-06-28 | 2016-08-24 | Lg化学株式会社 | 可聚液晶化合物、包含该化合物的液晶组合物、和光学各向异性体 |
JP6206413B2 (ja) * | 2012-10-19 | 2017-10-04 | 日本ゼオン株式会社 | 重合性化合物、重合性組成物、高分子、及び光学異方体 |
JP5905419B2 (ja) * | 2013-03-13 | 2016-04-20 | 富士フイルム株式会社 | 重合性液晶化合物、液晶組成物、高分子材料とその製造方法、フィルム、偏光板および液晶表示装置 |
KR101682591B1 (ko) | 2013-09-30 | 2016-12-05 | 주식회사 엘지화학 | 중합성 액정 화합물, 이를 포함하는 액정 조성물 및 광학 이방체 |
KR102422667B1 (ko) | 2014-12-26 | 2022-07-18 | 삼성전자주식회사 | 광학 필름용 조성물, 필름 및 표시 장치 |
CN105602578A (zh) * | 2015-12-18 | 2016-05-25 | 石家庄诚志永华显示材料有限公司 | 一种广视角的pdlc组合物 |
US20200050077A1 (en) * | 2018-08-13 | 2020-02-13 | Sharp Kabushiki Kaisha | Optical shutter for camera module and production method thereof |
CN113527143B (zh) * | 2020-04-20 | 2023-06-20 | 杭州光粒科技有限公司 | 书写单体及其制备方法以及光致聚合物组合物及其光栅 |
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JPH083111A (ja) | 1993-12-24 | 1996-01-09 | Dainippon Ink & Chem Inc | 重合性液晶組成物及びこれを用いた光学異方体 |
DE4408171A1 (de) * | 1994-03-11 | 1995-09-14 | Basf Ag | Neue polymerisierbare flüssigkristalline Verbindungen |
JP4010583B2 (ja) | 1996-09-17 | 2007-11-21 | 株式会社Adeka | 単官能重合性化合物及びその重合物からなる液晶性高分子 |
JP3948799B2 (ja) | 1997-10-27 | 2007-07-25 | 株式会社Adeka | 3官能化合物および高分子液晶 |
KR100675996B1 (ko) * | 1999-07-02 | 2007-01-29 | 메르크 파텐트 게엠베하 | 다층 콜레스테릭 필름의 제조 방법 |
KR20050108351A (ko) * | 2003-02-12 | 2005-11-16 | 니폰 가야꾸 가부시끼가이샤 | 수직 배향용 기판 및 수직 배향 액정 위상차 필름의 제조방법 |
JP4788123B2 (ja) * | 2003-09-19 | 2011-10-05 | Jnc株式会社 | 光重合性液晶組成物、その重合体または重合体組成物及び光学異方性膜 |
JP4721721B2 (ja) * | 2004-02-18 | 2011-07-13 | 株式会社Adeka | 重合性化合物及び該化合物を含有する重合性液晶組成物 |
JP2005309255A (ja) * | 2004-04-23 | 2005-11-04 | Asahi Denka Kogyo Kk | 配向性高分子 |
EP1813594B1 (en) * | 2004-11-04 | 2011-05-11 | Adeka Corporation | Polymerizable compound and composition containing the polymerizable compound |
JP4792731B2 (ja) * | 2004-11-12 | 2011-10-12 | Dic株式会社 | 重合性液晶組成物及び当該組成物の硬化物 |
JP5084148B2 (ja) * | 2005-02-25 | 2012-11-28 | Jnc株式会社 | 放熱部材およびその製造方法 |
JP4188932B2 (ja) * | 2005-03-23 | 2008-12-03 | 早川産機株式会社 | 液体冷却装置 |
JP5098223B2 (ja) * | 2005-06-09 | 2012-12-12 | Jnc株式会社 | 重合性液晶組成物およびその重合体 |
JP2007119415A (ja) * | 2005-10-31 | 2007-05-17 | Adeka Corp | 縮合環を有する重合性液晶化合物並びに該重合性液晶化合物の単独重合物及び共重合物 |
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CN101490117A (zh) | 2009-07-22 |
WO2008007479A1 (fr) | 2008-01-17 |
EP2039707B1 (en) | 2011-11-23 |
TW200804434A (en) | 2008-01-16 |
EP2039707A4 (en) | 2009-12-02 |
US20090294730A1 (en) | 2009-12-03 |
US7981320B2 (en) | 2011-07-19 |
JP2008019290A (ja) | 2008-01-31 |
CN101490117B (zh) | 2011-06-15 |
KR101313044B1 (ko) | 2013-09-30 |
EP2039707A1 (en) | 2009-03-25 |
TWI408148B (zh) | 2013-09-11 |
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