JP5075483B2 - Polymer film, method for producing molecular alignment element, and liquid crystal alignment film - Google Patents
Polymer film, method for producing molecular alignment element, and liquid crystal alignment film Download PDFInfo
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本発明は、位相差フィルムや偏光回折素子などの分子配向を制御した光学素子や液晶配向膜の製造に好適である光配向材に関するものである。The present invention relates to an optical alignment material suitable for the production of an optical element or a liquid crystal alignment film in which molecular alignment is controlled, such as a retardation film or a polarization diffraction element.
本発明者は、特開２００２−２０２４０９号、特開２００３−３０７６１８号などに、光照射または光照射と加熱冷却により複屈折を誘起する側鎖型液晶高分子に光照射するまたは光照射と加熱冷却する操作を含む工程によって作製される位相差フィルムおよびその製造法や、特開２００２−９０７５０号には光照射により液晶配向能を付与させた液晶配向膜およびその製造法を提案してきた。 The present inventor disclosed in Japanese Patent Application Laid-Open No. 2002-202409, Japanese Patent Application Laid-Open No. 2003-307618, etc., light irradiation or light irradiation and heating to a side chain liquid crystal polymer that induces birefringence by light irradiation and heating and cooling. JP-A 2002-90750 has proposed a retardation film produced by a process including an operation of cooling and a production method thereof, and a liquid crystal alignment film provided with a liquid crystal orientation ability by light irradiation and a production method thereof.
これら材料では、基材に塗布して製膜した後、直線偏光性紫外線を照射すると、高分子側鎖の軸選択的な光架橋反応によって異方性を付与できる。更に、このような膜を加熱すると、材料自体が液晶性を有することから未反応側鎖が軸選択的に光架橋した側鎖に沿って配向することから膜全体を分子配向させることができる。このような膜では、分子配向により複屈折性が発現することから位相差フィルムとして利用することができる。また、膜表面に液晶分子を接触させると液晶分子の配向能を発現することから液晶配向膜としても機能する。In these materials, anisotropy can be imparted by an axis-selective photocrosslinking reaction of a polymer side chain when irradiated with linearly polarized ultraviolet light after being applied to a substrate and formed into a film. Further, when such a film is heated, since the material itself has liquid crystallinity, the unreacted side chain is aligned along the side chain that has been photocrosslinked selectively, so that the entire film can be molecularly aligned. Such a film can be used as a retardation film because it exhibits birefringence due to molecular orientation. In addition, when liquid crystal molecules are brought into contact with the film surface, the liquid crystal molecules exhibit alignment ability, so that it functions as a liquid crystal alignment film.
このように光照射と加熱により分子配向するという特性からこれら材料は様々な用途で利用することができる。しかしながら、これら提案の材料では光反応性が充分であるとはいえず、照射時間の長時間化など製造上好ましくなく、この課題を解決するために、特願２００６−１３０８３３号には、光反応性基を有し、かつそれらが少なくとも１つの水素結合部位により、２量体を形成する側鎖（以下、光反応性水素結合側鎖と略す）を含有する光反応性高分子を提案している。この光反応性高分子では、光反応性に優れ光照射工程を短縮により製造上のメリットを実現したが、光反応性高分子の原料が高価であるため、製造コストを抑えることが難しかった。
本発明は、光配向材に光照射と加熱冷却する操作を含む工程によって作製される位相差フィルムや偏光回折素子などの分子の配向を制御した光学素子や液晶配向膜の製造法において、従来技術を用いて工業的に提供するにあたり問題となる上記課題を解決しようとするものである。 The present invention relates to a conventional method for producing an optical element or a liquid crystal alignment film in which molecular orientation is controlled, such as a retardation film or a polarization diffraction element, produced by a process including light irradiation and heating / cooling operations on a photo-alignment material. The present invention intends to solve the above-mentioned problem which becomes a problem in providing industrially using the.
光反応性水素結合側鎖と、光反応性基を有さず、少なくとも１つの水素結合部位により、２量体を形成する側鎖（以下、非反応性水素結合側鎖と略す）とを含有することを特徴とする高分子フィルムを用いることによって上記課題を解決することができる。 Contains a photoreactive hydrogen-bonded side chain and a side chain that has no photoreactive group and forms a dimer with at least one hydrogen-bonding site (hereinafter abbreviated as a non-reactive hydrogen-bonded side chain) The above-described problems can be solved by using a polymer film characterized by:
本発明により、光配向材に光照射と加熱冷却する操作を含む工程によって作製される位相差フィルムや偏光回折素子などの分子の配向を制御した光学素子や液晶配向膜を製造するのに好適な材料を安価で提供できる。これにより従来技術の問題点を解決することができる。 According to the present invention, it is suitable for producing an optical element or liquid crystal alignment film in which molecular alignment is controlled, such as a retardation film or a polarization diffraction element, which is produced by a process including light irradiation and heating / cooling operations on a photo-alignment material. Materials can be provided at low cost. Thereby, the problems of the prior art can be solved.
以下に、本発明の詳細を説明する。本発明では、光反応性水素結合側鎖と、非反応性水素結合側鎖とを含有することを特徴とする高分子フィルムを用いることによって上記課題を解決することができる。 Details of the present invention will be described below. In this invention, the said subject can be solved by using the polymer film characterized by containing a photoreactive hydrogen bond side chain and a non-reactive hydrogen bond side chain.
光反応性水素結合側鎖は、化学式１で示される構造を有する側鎖が好適に用いられ、側鎖末端に光反応性のカルボキシル基を有する液晶性高分子である。この光反応性高分子は、側鎖末端のカルボキシル基の水素結合による２量化により、従来技術の材料のようなメソゲン基を構造に含まなくとも液晶相を発現する構造を有している。 As the photoreactive hydrogen bond side chain, a side chain having a structure represented by Chemical Formula 1 is preferably used, and a liquid crystalline polymer having a photoreactive carboxyl group at the end of the side chain. This photoreactive polymer has a structure that expresses a liquid crystal phase by dimerization of a carboxyl group at the end of a side chain by hydrogen bonding even if the structure does not contain a mesogenic group as in the prior art material.
また、非反応性水素結合側鎖としては、化学式２で示される構造を有する側鎖が好適に用いられ、この側鎖も側鎖末端にカルボキシル基を有し、側鎖末端のカルボキシル基の水素結合による２量化により液晶相を発現する構造を有する。 Further, as the non-reactive hydrogen bonding side chain, a side chain having a structure represented by Chemical Formula 2 is preferably used. This side chain also has a carboxyl group at the end of the side chain, and the hydrogen of the carboxyl group at the end of the side chain. It has a structure that expresses a liquid crystal phase by dimerization by bonding.
これら２つの側鎖を含有する高分子フィルムは、それら単量体を共重合した光反応性高分子、ないしは各々単独で重合した後、得られた高分子を混合した混合体を塗布（スピンコートないしはキャスト）することにより形成できる。 The polymer film containing these two side chains is coated with a photoreactive polymer obtained by copolymerizing these monomers, or a polymer mixture obtained by polymerizing each of these monomers alone (spin coating). Or cast).
非反応性水素結合側鎖としては、４−ヒドロキシ安息香酸を原料とする化学式３で示されるような単量体ないしはその重合体を好適に用いることができる。このような非反応性水素結合側鎖も、メソゲン基を構造に含まなくとも液晶相を発現する材料であり、メソゲン基をその構造に含まないことから、感光性基の光反応を進行させる波長の光を吸収することがなく光反応性を損なうことが無い。また、液晶性を発現する材料であることから配向性を損なうことも無い。 As the non-reactive hydrogen bond side chain, a monomer or a polymer thereof represented by Chemical Formula 3 using 4-hydroxybenzoic acid as a raw material can be preferably used. Such a non-reactive hydrogen-bonded side chain is also a material that develops a liquid crystal phase even if the mesogenic group is not included in the structure, and since the mesogenic group is not included in the structure, the wavelength at which the photoreaction of the photosensitive group proceeds. It does not absorb the light and does not impair the photoreactivity. In addition, since the material exhibits liquid crystallinity, the orientation is not impaired.
化学式４で示される単量体の原料となる４−ヒドロキシ安息香酸は、化粧品、食品の防腐剤・保存料として広く利用されているパラベン（パラオキシ安息香酸エステル）の合成原料となるため、比較的安価に入手可能な化合物であり、単量体自体の製造コストを抑えるこが可能となる。このような単量体ないしは重合体を光反応性高分子に添加しても光反応性や配向性を損なうことがなく、添加することによって光反応性高分子材料自体の製造コストを低減することが可能になる。 4-Hydroxybenzoic acid, which is a raw material for the monomer represented by Chemical Formula 4, is a synthetic raw material for parabens (paraoxybenzoic acid esters) that are widely used as preservatives and preservatives for cosmetics and foods. It is a compound that can be obtained at a low cost, and the production cost of the monomer itself can be suppressed. Even if such a monomer or polymer is added to the photoreactive polymer, the photoreactivity and orientation are not impaired, and the addition reduces the production cost of the photoreactive polymer material itself. Is possible.
非反応性水素結合側鎖の過剰の添加は、高分子フィルム中で光反応性基の密度が著しく低下すると偏光照射による配向性を損なうため、高分子フィルム自体の異方性の発現を阻害する。この光反応性基を有さず、少なくとも１つの水素結合部位により、２量体を形成する側鎖の添加量は、添加する側鎖の種類にもよるが、光反応性水素結合側鎖に対するモル比にして、〔非反応性水素結合側鎖〕：〔光反応性水素結合側鎖〕＝９９：１より少ないことが好ましく、更には、９：１より少ないことが好ましい。 Excessive addition of non-reactive hydrogen-bonded side chains impairs the orientation of the polymer film itself when the density of photoreactive groups in the polymer film is significantly reduced, impairing the orientation due to polarized light irradiation. . The addition amount of the side chain that does not have this photoreactive group and forms a dimer with at least one hydrogen bonding site depends on the type of the side chain to be added, but with respect to the photoreactive hydrogen bonding side chain. The molar ratio is preferably less than [non-reactive hydrogen bond side chain]: [photoreactive hydrogen bond side chain] = 99: 1, and more preferably less than 9: 1.
また、このような光反応性高分子は、液晶性を損なわない程度に耐熱性を向上させるための架橋剤を添加することや、液晶性を損なうことなく液晶性を示さない単量体を感光性の重合体に共重合してもかまわない。 In addition, such a photoreactive polymer can be added with a crosslinking agent for improving heat resistance to the extent that liquid crystallinity is not impaired, or a monomer that does not exhibit liquid crystallinity without damaging liquid crystallinity. It may be copolymerized with a functional polymer.
本発明の光学素子の実施例において用いた光配向材の原料化合物に関する合成方法を以下に示す。
（単量体１）
ｐ−クマル酸と６−クロロ−１−ヘキサノールを、アルカリ条件下で加熱することにより、４−（６−ヒドロキシヘキシルオキシ）桂皮酸を合成した。この生成物にｐ−トルエンスルホン酸の存在下でメタクリル酸を大過剰加えてエステル化反応させ、化学式３に示される単量体１を合成した。
(Monomer 1)
4- (6-Hydroxyhexyloxy) cinnamic acid was synthesized by heating p-coumaric acid and 6-chloro-1-hexanol under alkaline conditions. A large excess of methacrylic acid was added to this product in the presence of p-toluenesulfonic acid for esterification to synthesize monomer 1 represented by Chemical Formula 3.
（単量体２）
４−ヒドロキシ安息香酸と６−クロロ−１−ヘキサノールを、アルカリ条件下で加熱することにより、４−（６−ヒドロキシヘキシルオキシ）安息香酸を合成した。次いでこの生成物にｐ−トルエンスルホン酸の存在下でメタクリル酸を大過剰加えてエステル化反応させ、化学式４に示される単量体２を合成した。
4- (6-hydroxyhexyloxy) benzoic acid was synthesized by heating 4-hydroxybenzoic acid and 6-chloro-1-hexanol under alkaline conditions. Next, a large excess of methacrylic acid was added to this product in the presence of p-toluenesulfonic acid for esterification to synthesize monomer 2 represented by Chemical Formula 4.
（重合体１）
単量体１を１，４−ジオキサン中に溶解し、反応開始剤としてＡＩＢＮ（アゾビスイソブチロニトリル）を添加して重合することにより重合体１を得た。この重合体１は１３５℃から１８７℃の温度範囲で液晶相を示した。また、可視光域に全く吸収を示さなかった。(Polymer 1)
Monomer 1 was dissolved in 1,4-dioxane, and polymer was obtained by adding AIBN (azobisisobutyronitrile) as a reaction initiator for polymerization. The polymer 1 exhibited a liquid crystal phase in the temperature range of 135 ° C. to 187 ° C. In addition, no absorption was observed in the visible light region.
（重合体２）
単量体２を１，４−ジオキサン中に溶解し、中に溶解し、反応開始剤としてＡＩＢＮを添加して重合することにより感光性の重合体２を得た。この重合体２も液晶相を示した。(Polymer 2)
Monomer 2 was dissolved in 1,4-dioxane, dissolved therein, and AIBN was added as a reaction initiator for polymerization to obtain photosensitive polymer 2. This polymer 2 also exhibited a liquid crystal phase.
（重合体３）
単量体１と単量体２をモル比８：２で１，４−ジオキサン中に溶解し、反応開始剤としてＡＩＢＮを添加して重合することにより感光性の重合体３を得た。この重合体３も液晶相を示した。(Polymer 3)
Monomer 1 and monomer 2 were dissolved in 1,4-dioxane at a molar ratio of 8: 2, and AIBN was added as a reaction initiator for polymerization to obtain photosensitive polymer 3. This polymer 3 also showed a liquid crystal phase.
（重合体４）
単量体１と単量体２をモル比６：４で１，４−ジオキサン中に溶解し、反応開始剤としてＡＩＢＮを添加して重合することにより感光性の重合体４を得た。この重合体４も液晶相を示した。(Polymer 4)
Monomer 1 and monomer 2 were dissolved in 1,4-dioxane at a molar ratio of 6: 4, and AIBN was added as a reaction initiator for polymerization to obtain photosensitive polymer 4. This polymer 4 also exhibited a liquid crystal phase.
（重合体５）
単量体１と単量体２をモル比３：７で１，４−ジオキサン中に溶解し、反応開始剤としてＡＩＢＮを添加して重合することにより感光性の重合体５を得た。この重合体５も液晶相を示した。(Polymer 5)
Monomer 1 and monomer 2 were dissolved in 1,4-dioxane at a molar ratio of 3: 7, and AIBN was added as a reaction initiator for polymerization to obtain photosensitive polymer 5. This polymer 5 also exhibited a liquid crystal phase.
（重合体６）
単量体１と単量体２をモル比２：８で１，４−ジオキサン中に溶解し、反応開始剤としてＡＩＢＮを添加して重合することにより感光性の重合体６を得た。この重合体６も液晶相を示した。(Polymer 6)
Monomer 1 and monomer 2 were dissolved in 1,4-dioxane at a molar ratio of 2: 8, and AIBN was added as a reaction initiator for polymerization to obtain photosensitive polymer 6. This polymer 6 also exhibited a liquid crystal phase.
（実施例１）
重合体３を１，４−ジオキサンに溶解し溶液を調整した。この溶液をカバーガラス基板上にスピンコーターを用いて約１．７μｍの厚みとなるよう塗布した。この基板を室温で乾燥させ、続いて、この基板に高圧水銀灯からの紫外光を、グランテーラープリズムを介して直線偏光性として照射した。照射後、１３５℃まで加熱後徐冷することによって配向を誘起した。最後に、高圧水銀灯からの紫外光を、グランテーラープリズムを介さず照射して配向を固定し複屈折性を有する基板を作製した。このようにして作製した基板は異方性を発現し、面内位相差は、１３０．０ｎｍであった。
また、このようにして作製した基板を２枚用意し、１２μｍのポリイミドスペーサーを挟持しこれら基板を対向させて配置し、基板間に低分子液晶ＺＬ１４７９２（メルク社）を注入してパラレル型液晶セルを作製した。このように作製した液晶セルを偏光顕微鏡で観察すると低分子液晶が配向していることが確認された。Example 1
Polymer 3 was dissolved in 1,4-dioxane to prepare a solution. This solution was applied on a cover glass substrate to a thickness of about 1.7 μm using a spin coater. The substrate was dried at room temperature, and then the substrate was irradiated with ultraviolet light from a high-pressure mercury lamp as linearly polarized light through a Grand Taylor prism. After irradiation, orientation was induced by heating to 135 ° C. and then slowly cooling. Finally, ultraviolet light from a high-pressure mercury lamp was irradiated without passing through the Grand Taylor prism to fix the orientation and produce a birefringent substrate. The substrate thus produced exhibited anisotropy and the in-plane retardation was 130.0 nm.
In addition, two substrates prepared in this way are prepared, 12 μm polyimide spacers are sandwiched and these substrates are placed facing each other, and a low-molecular liquid crystal ZL14792 (Merck) is injected between the substrates. Was made. When the liquid crystal cell thus prepared was observed with a polarizing microscope, it was confirmed that the low-molecular liquid crystals were aligned.
（実施例２）
重合体４を１，４−ジオキサンに溶解し溶液を調整した。この溶液をカバーガラス基板上にスピンコーターを用いて約１．６μｍの厚みとなるよう塗布した。この基板を室温で乾燥させ、続いて、この基板に高圧水銀灯からの紫外光を、グランテーラープリズムを介して直線偏光性として照射した。照射後、１３５℃まで加熱後徐冷することによって配向を誘起した。最後に、高圧水銀灯からの紫外光を、グランテーラープリズムを介さず照射して配向を固定し複屈折性を有する基板を作製した。このようにして作製した基板は異方性を発現し、面内位相差は、１１２．３ｎｍであった。
また、このようにして作製した基板を２枚用意し、１２μｍのポリイミドスペーサーを挟持しこれら基板を対向させて配置し、基板間に低分子液晶ＺＬ１４７９２（メルク社）を注入してパラレル型液晶セルを作製した。このように作製した液晶セルを偏光顕微鏡で観察すると低分子液晶が配向していることが確認された。(Example 2)
Polymer 4 was dissolved in 1,4-dioxane to prepare a solution. This solution was applied on a cover glass substrate to a thickness of about 1.6 μm using a spin coater. The substrate was dried at room temperature, and then the substrate was irradiated with ultraviolet light from a high-pressure mercury lamp as linearly polarized light through a Grand Taylor prism. After irradiation, orientation was induced by heating to 135 ° C. and then slowly cooling. Finally, ultraviolet light from a high-pressure mercury lamp was irradiated without passing through the Grand Taylor prism to fix the orientation and produce a birefringent substrate. The substrate thus produced developed anisotropy and the in-plane retardation was 112.3 nm.
In addition, two substrates prepared in this way are prepared, 12 μm polyimide spacers are sandwiched and these substrates are placed facing each other, and a low-molecular liquid crystal ZL14792 (Merck) is injected between the substrates. Was made. When the liquid crystal cell thus prepared was observed with a polarizing microscope, it was confirmed that the low-molecular liquid crystals were aligned.
（実施例３）
重合体５を１，４−ジオキサンに溶解し溶液を調整した。この溶液をカバーガラス基板上にスピンコーターを用いて約１．７μｍの厚みとなるよう塗布した。この基板を室温で乾燥させ、続いて、この基板に高圧水銀灯からの紫外光を、グランテーラープリズムを介して直線偏光性として照射した。照射後、１３５℃まで加熱後徐冷することによって配向を誘起した。最後に、高圧水銀灯からの紫外光を、グランテーラープリズムを介さず照射して配向を固定し複屈折性を有する基板を作製した。このようにして作製した基板は異方性を発現し、面内位相差は、１４１．９ｎｍであった。
また、このようにして作製した基板を２枚用意し、１２μｍのポリイミドスペーサーを挟持しこれら基板を対向させて配置し、基板間に低分子液晶ＺＬ１４７９２（メルク社）を注入してパラレル型液晶セルを作製した。このように作製した液晶セルを偏光顕微鏡で観察すると低分子液晶が配向していることが確認された。(Example 3)
Polymer 5 was dissolved in 1,4-dioxane to prepare a solution. This solution was applied on a cover glass substrate to a thickness of about 1.7 μm using a spin coater. The substrate was dried at room temperature, and then the substrate was irradiated with ultraviolet light from a high-pressure mercury lamp as linearly polarized light through a Grand Taylor prism. After irradiation, orientation was induced by heating to 135 ° C. and then slowly cooling. Finally, ultraviolet light from a high-pressure mercury lamp was irradiated without passing through the Grand Taylor prism to fix the orientation and produce a birefringent substrate. The substrate thus produced developed anisotropy and the in-plane retardation was 141.9 nm.
In addition, two substrates prepared in this way are prepared, 12 μm polyimide spacers are sandwiched and these substrates are placed facing each other, and a low-molecular liquid crystal ZL14792 (Merck) is injected between the substrates. Was made. When the liquid crystal cell thus prepared was observed with a polarizing microscope, it was confirmed that the low-molecular liquid crystals were aligned.
（実施例４）
重合体６を１，４−ジオキサンに溶解し溶液を調整した。この溶液をカバーガラス基板上にスピンコーターを用いて約１．１μｍの厚みとなるよう塗布した。この基板を室温で乾燥させ、続いて、この基板に高圧水銀灯からの紫外光を、グランテーラープリズムを介して直線偏光性として照射した。照射後、１３５℃まで加熱後徐冷することによって配向を誘起した。最後に、高圧水銀灯からの紫外光を、グランテーラープリズムを介さず照射して配向を固定し複屈折性を有する基板を作製した。このようにして作製した基板は異方性を発現し、面内位相差は、８７．１ｎｍであった。
また、このようにして作製した基板を２枚用意し、１２μｍのポリイミドスペーサーを挟持しこれら基板を対向させて配置し、基板間に低分子液晶ＺＬ１４７９２（メルク社）を注入してパラレル型液晶セルを作製した。このように作製した液晶セルを偏光顕微鏡で観察すると低分子液晶が配向していることが確認された。Example 4
The polymer 6 was dissolved in 1,4-dioxane to prepare a solution. This solution was applied on a cover glass substrate to a thickness of about 1.1 μm using a spin coater. The substrate was dried at room temperature, and then the substrate was irradiated with ultraviolet light from a high-pressure mercury lamp as linearly polarized light through a Grand Taylor prism. After irradiation, orientation was induced by heating to 135 ° C. and then slowly cooling. Finally, ultraviolet light from a high-pressure mercury lamp was irradiated without passing through the Grand Taylor prism to fix the orientation and produce a birefringent substrate. The substrate thus produced developed anisotropy, and the in-plane retardation was 87.1 nm.
In addition, two substrates prepared in this way are prepared, 12 μm polyimide spacers are sandwiched and these substrates are placed facing each other, and a low-molecular liquid crystal ZL14792 (Merck) is injected between the substrates. Was made. When the liquid crystal cell thus prepared was observed with a polarizing microscope, it was confirmed that the low-molecular liquid crystals were aligned.
（実施例５）
重合体１と重合体２を重量比１：１で１，４−ジオキサンに溶解し溶液を調整した。この溶液をカバーガラス基板上にスピンコーターを用いて約１．７μｍの厚みとなるよう塗布した。この基板を室温で乾燥させ、続いて、この基板に高圧水銀灯からの紫外光を、グランテーラープリズムを介して直線偏光性として照射した。照射後、１３５℃まで加熱後徐冷することによって配向を誘起した。最後に、高圧水銀灯からの紫外光を、グランテーラープリズムを介さず照射して配向を固定し複屈折性を有する基板を作製した。このようにして作製した基板は異方性を発現し、面内位相差は、１０３．４ｎｍであった。
また、このようにして作製した基板を２枚用意し、１２μｍのポリイミドスペーサーを挟持しこれら基板を対向させて配置し、基板間に低分子液晶ＺＬ１４７９２（メルク社）を注入してパラレル型液晶セルを作製した。このように作製した液晶セルを偏光顕微鏡で観察すると低分子液晶が配向していることが確認された。(Example 5)
Polymer 1 and polymer 2 were dissolved in 1,4-dioxane at a weight ratio of 1: 1 to prepare a solution. This solution was applied on a cover glass substrate to a thickness of about 1.7 μm using a spin coater. The substrate was dried at room temperature, and then the substrate was irradiated with ultraviolet light from a high-pressure mercury lamp as linearly polarized light through a Grand Taylor prism. After irradiation, orientation was induced by heating to 135 ° C. and then slowly cooling. Finally, ultraviolet light from a high-pressure mercury lamp was irradiated without passing through the Grand Taylor prism to fix the orientation and produce a birefringent substrate. The substrate thus produced exhibited anisotropy and the in-plane retardation was 103.4 nm.
In addition, two substrates prepared in this way are prepared, 12 μm polyimide spacers are sandwiched and these substrates are placed facing each other, and a low-molecular liquid crystal ZL14792 (Merck) is injected between the substrates. Was made. When the liquid crystal cell thus prepared was observed with a polarizing microscope, it was confirmed that the low-molecular liquid crystals were aligned.
（実施例６）
重合体１と重合体２を重量比１：９で１，４−ジオキサンに溶解し溶液を調整した。この溶液をカバーガラス基板上にスピンコーターを用いて約１．８μｍの厚みとなるよう塗布した。この基板を室温で乾燥させ、続いて、この基板に高圧水銀灯からの紫外光を、グランテーラープリズムを介して直線偏光性として照射した。照射後、１３５℃まで加熱後徐冷した。この基板でも異方性の発現が確認された。(Example 6)
Polymer 1 and polymer 2 were dissolved in 1,4-dioxane at a weight ratio of 1: 9 to prepare a solution. This solution was applied on a cover glass substrate to a thickness of about 1.8 μm using a spin coater. The substrate was dried at room temperature, and then the substrate was irradiated with ultraviolet light from a high-pressure mercury lamp as linearly polarized light through a Grand Taylor prism. After irradiation, it was heated to 135 ° C. and then cooled slowly. Anisotropy was also confirmed on this substrate.
実施例１〜実施例６から、光反応性水素結合側鎖に、非反応性水素結合側鎖を、共重合ないしは各々単独で重合した後、得られた高分子を混合して添加しても配向性が損なわれること無く異方性を発現することが確認された。このことから、光配向材に光照射と加熱冷却する操作を含む工程によって作製される位相差フィルムや偏光回折素子などの分子の配向を制御した光学素子や液晶配向膜の製造法において、光反応性水素結合側鎖に、原料コストが安価な非反応性水素結合側鎖を添加することが可能であることが立証され、従来課題を解決した光学素子、液晶配向膜およびその製造法が得られることが確認された。 From Example 1 to Example 6, a non-reactive hydrogen bond side chain may be copolymerized or polymerized independently to the photoreactive hydrogen bond side chain, and then the resulting polymer may be mixed and added. It was confirmed that anisotropy was developed without impairing the orientation. Therefore, in the method of manufacturing an optical element or a liquid crystal alignment film in which the alignment of molecules such as a retardation film and a polarization diffraction element produced by a process including an operation of light irradiation and heating / cooling is performed on a photo-alignment material, It is proved that it is possible to add a non-reactive hydrogen bond side chain with a low raw material cost to the reactive hydrogen bond side chain, and an optical element, a liquid crystal alignment film, and a method for producing the same that have solved the conventional problems are obtained. It was confirmed.
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