JPH07101904A - Biphenyl methacrylate derivative and polymer dispersion type liquid crystal display element using the same - Google Patents
Biphenyl methacrylate derivative and polymer dispersion type liquid crystal display element using the sameInfo
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- JPH07101904A JPH07101904A JP24711493A JP24711493A JPH07101904A JP H07101904 A JPH07101904 A JP H07101904A JP 24711493 A JP24711493 A JP 24711493A JP 24711493 A JP24711493 A JP 24711493A JP H07101904 A JPH07101904 A JP H07101904A
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- liquid crystal
- display device
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Abstract
Description
【0001】[0001]
【産業上の利用分野】本発明は新規な有機化合物に関わ
り、さらに電気光学的表示要素として用いられる液晶組
成物を構成するために、その一素材を成すビフェニルメ
タクリレート誘導体及びそれを用いた高分子分散型液晶
表示装置に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a novel organic compound, and further to form a liquid crystal composition used as an electro-optical display element, a biphenyl methacrylate derivative which is one of the materials and a polymer using the same. The present invention relates to a dispersion type liquid crystal display device.
【0002】[0002]
【従来の技術】近年偏光板を用いない明るい表示素子と
して、液晶と高分子を互いに分散させた表示素子が注目
されている。この表示素子の動作原理は液晶と高分子の
屈折率の差を利用しており、電界印加により液晶と高分
子の屈折率が一致した場合には透過状態を示し、電界除
去により屈折率が相違した場合には散乱状態を示すこと
による(特表昭58-501631、これをNCAPと呼ぶ)。
また電界無印加時に透過し電界印加時に散乱する逆のモ
ードの表示素子も開発されている(Mol.Cryst.Liq.Crys
t.,198,357(1991)、これをリバースタイプと呼ぶ)。ま
た、これらのモードについては色素を混合することによ
り、視認性を向上させる方法も提案されている。2. Description of the Related Art In recent years, as a bright display element which does not use a polarizing plate, a display element in which a liquid crystal and a polymer are dispersed is drawing attention. The principle of operation of this display element utilizes the difference in the refractive index between the liquid crystal and the polymer.When the refractive index of the liquid crystal and that of the polymer match when an electric field is applied, a transmissive state is shown, and when the electric field is removed, the refractive index differs. In that case, the scattering state is indicated (Tokukaisho Sho 58-501631, which is called NCAP).
In addition, a display element of the opposite mode has been developed, which transmits when no electric field is applied and scatters when an electric field is applied (Mol.Cryst.Liq.Crys
t., 198, 357 (1991), which is called the reverse type). For these modes, a method of improving visibility by mixing a dye has also been proposed.
【0003】[0003]
【発明が解決しようとする課題】しかしながら、NCA
Pにおいては色素を混合した場合に電界を除去して色素
色を表示するときには光散乱を伴うので白みがかったぼ
やけた表示となる。また、電界を印加して透明状態とし
て背面の白い散乱板の色を表示しようとすると色素の吸
収がわずか生じ、白くなりにくい。せいぜい白い紙の6
0%程度の反射率になってしまう。次にリバースタイプ
においては背景に白い紙を置いたのではコントラストが
とれない。すなわち、電界無印加では色素の吸収が生
じ、電界印加で白く散乱するのであるが、この白く散乱
した場合の白が十分ではない。これは素子の散乱のため
に背景板に光が届きにくくなるためである。また、リバ
ースタイプにおいては素子を作製する際に紫外線を用い
るため液晶の比抵抗が低下してしまう。[Problems to be Solved by the Invention] However, NCA
In P, when a dye is mixed and an electric field is removed and a dye color is displayed, light scattering is accompanied, so that the display becomes whitish and blurry. Further, when an electric field is applied to display the color of the white scattering plate on the back surface in a transparent state, the dye is slightly absorbed and it is difficult for the dye to become white. At best white paper 6
The reflectance is about 0%. Next, in the reverse type, the contrast cannot be obtained by putting a white paper on the background. That is, when no electric field is applied, the dye absorbs and scatters white when an electric field is applied, but the white when scattered white is not sufficient. This is because it is difficult for light to reach the background plate due to scattering of the element. Further, in the reverse type, since ultraviolet rays are used when manufacturing the element, the specific resistance of the liquid crystal is lowered.
【0004】本発明はこのような実状における要請に答
えたものであり、その目的は紫外線を照射しても比抵抗
値が低下することがなく、また他の一種または二種以上
の液晶と混合することにより低電圧で駆動でき、明るく
反射率の優れた表示素子を得るのに適している新規化合
物を提供することである。The present invention has responded to such a demand in the actual situation, and its purpose is to prevent the specific resistance value from being lowered even when it is irradiated with ultraviolet rays, and to mix it with other one or more kinds of liquid crystals. By doing so, it is possible to provide a novel compound which can be driven at a low voltage and which is suitable for obtaining a bright and excellent display element.
【0005】[0005]
【課題を解決するための手段】本発明はThe present invention is
【0006】[0006]
【化11】 [Chemical 11]
【0007】(上式中、Xはフッ素原子または水素原子
である)で表されることを特徴とするビフェニルメタク
リレート誘導体である。(In the above formula, X is a fluorine atom or a hydrogen atom) and is a biphenyl methacrylate derivative.
【0008】また本発明の表示素子は液晶及び高分子を
互いに配向分散した表示素子において、高分子を形成す
る前駆体としてビフェニルメタクリレート誘導体を少な
くとも1成分として用いることによってThe display device of the present invention is a display device in which a liquid crystal and a polymer are oriented and dispersed to each other, and a biphenyl methacrylate derivative is used as at least one component as a precursor for forming the polymer.
【0009】[0009]
【化12】 [Chemical 12]
【0010】(上式中、Xはフッ素原子または水素原子
である)で表される構成要素が少なくとも一部分高分子
に存在することを特徴とする。また液晶及び高分子を互
いに配向分散させた表示素子において、相分離させた液
晶と高分子をシアリングにより配向させてもよい。また
液晶及び高分子を互いに配向分散させた表示素子におい
て、液晶と高分子がゲルネットワーク状に相分離してい
てもよい。また液晶及び高分子を互いに配向分散させた
表示素子において、高分子を形成する前駆体としてビフ
ェニルメタクリレート誘導体を1〜20%含有すること
を特徴とする。また液晶及び高分子を互いに配向分散さ
せた表示素子において、2色性色素を含有することを特
徴とする。また液晶あるいは高分子中の少なくとも一方
にカイラル成分が含有あるいは存在することを特徴とす
る。また液晶及び高分子を互いに配向分散させた表示素
子において、表示素子表面側での配向方向が、主たる光
の入射方向と素子表面の法線を含む平面に対して垂直で
あることを特徴とする。あるいは表示素子表面側での高
分子の配向方向が裏面側での高分子の配向方向と異なる
ことを特徴とする。また液晶及び高分子を互いに配向分
散させた表示素子において、液晶及び高分子分散層を挟
持する2枚の電極の1方が光反射性の電極であることを
特徴とする。The constituent element represented by the formula (wherein X is a fluorine atom or a hydrogen atom) is at least partially present in the polymer. In a display element in which liquid crystal and polymer are aligned and dispersed with each other, the phase-separated liquid crystal and polymer may be aligned by shearing. Further, in the display device in which the liquid crystal and the polymer are aligned and dispersed with each other, the liquid crystal and the polymer may be phase-separated in a gel network. A display device in which a liquid crystal and a polymer are oriented and dispersed with each other is characterized by containing 1 to 20% of a biphenyl methacrylate derivative as a precursor for forming the polymer. A display element in which a liquid crystal and a polymer are aligned and dispersed with each other is characterized by containing a dichroic dye. Further, it is characterized in that at least one of the liquid crystal and the polymer contains or exists a chiral component. Further, in the display element in which the liquid crystal and the polymer are orientation-dispersed with each other, the orientation direction on the display element surface side is perpendicular to a plane including the main light incident direction and the element surface normal. . Alternatively, the orientation direction of the polymer on the front surface side of the display element is different from the orientation direction of the polymer on the back surface side. Further, in the display element in which the liquid crystal and the polymer are oriented and dispersed with each other, one of the two electrodes sandwiching the liquid crystal and the polymer dispersion layer is a light-reflecting electrode.
【0011】次に、本発明のビフェニルメタクリレート
誘導体の製造方法について述べる。Next, a method for producing the biphenyl methacrylate derivative of the present invention will be described.
【0012】[0012]
【表1】 [Table 1]
【0013】ステップ1 化合物(II)とヨウ化メチル
を水酸化カリウムのエタノールで反応させて、化合物
(II)を得る。Step 1 Compound (II) is reacted with methyl iodide with ethanol of potassium hydroxide to obtain Compound (II).
【0014】ステップ2 化合物(III)とマグネシ
ウムでグリニャール試薬を調製し、それをテトラヒドロ
フラン中でほう酸トリイソプロピルと反応させ化合物
(IV)を得る。Step 2 A Grignard reagent is prepared from compound (III) and magnesium and reacted with triisopropyl borate in tetrahydrofuran to obtain compound (IV).
【0015】ステップ3 化合物(IV)と化合物
(V)をカップリング反応させて、化合物(VI)を得
る。Step 3 The compound (IV) and the compound (V) are subjected to a coupling reaction to obtain a compound (VI).
【0016】ステップ4 化合物(VI)を酢酸および
臭化水素酸中で還元して化合物(VII)を得る。Step 4 Compound (VI) is reduced in acetic acid and hydrobromic acid to obtain compound (VII).
【0017】ステップ5 化合物(VII)をクロロホ
ルム及びトリエチルアミンに溶解しそこへメタクリロイ
ルクロライド(VIII)を入れてエステル化して、本
発明の化合物(I)を得る。Step 5 Compound (VII) is dissolved in chloroform and triethylamine, and methacryloyl chloride (VIII) is added thereto to effect esterification to obtain compound (I) of the present invention.
【0018】[0018]
〔実施例1〕(化合物) 3−フルオロ−ビフェニル−4,4’−ジイルジメタク
リレートの製造方法。[Example 1] (Compound) A method for producing 3-fluoro-biphenyl-4,4'-diyldimethacrylate.
【0019】ステップ1 フラスコ中に水酸化カリウ
ム 20.6g をエタノール 500ml に溶かした溶液を入れ、
さらに4−ブロモ−2−フルオロ−フェノール 50g と
ヨウ化メチル 32ml を入れ5時間還流する。反応後エタ
ノールを留去し、残留物に水を100ml 加えてクロロホル
ムで抽出する。抽出液を水で洗浄しクロロホルムを留去
した後メタノールで再結晶して4−ブロモ−2−フルオ
ロ−メトキシベンゼン35.2gを得た。Step 1 A solution of 20.6 g of potassium hydroxide in 500 ml of ethanol was placed in a flask,
Further, 50 g of 4-bromo-2-fluoro-phenol and 32 ml of methyl iodide are added and the mixture is refluxed for 5 hours. After the reaction, ethanol is distilled off, 100 ml of water is added to the residue, and the mixture is extracted with chloroform. The extract was washed with water, chloroform was distilled off, and the residue was recrystallized from methanol to obtain 4-bromo-2-fluoro-methoxybenzene (35.2 g).
【0020】ステップ2 窒素置換したフラスコ中に
マグネシウム 5.0g を入れ、マグネチックスターラーで
攪拌しながら4−ブロモ−2−フルオロ−メトキシベン
ゼン 35.2g をテトラヒドロフラン 150ml に溶かした溶
液をゆっくり滴下する。滴下後、15時間攪拌を続けグリ
ニャール試薬を調製した。新たに用意したフラスコを窒
素置換し、その中へテトラヒドロフラン 50ml にほう酸
トリメチル 39ml を溶かした溶液を入れ、そこへグリニ
ャール試薬を滴下し10時間攪拌する。反応液に20%塩酸
水溶液 150ml を入れてしばらく攪拌した後、目的物を
クロロホルムで抽出して水で3回洗浄しクロロホルムを
留去する。残留物をメタノールと水で再結晶して3−フ
ルオロ−4−メトキシフェニルほう酸 17.5g を得た。Step 2 Magnesium (5.0 g) was placed in a flask purged with nitrogen, and a solution of 4-bromo-2-fluoro-methoxybenzene (35.2 g) in tetrahydrofuran (150 ml) was slowly added dropwise while stirring with a magnetic stirrer. After the dropping, stirring was continued for 15 hours to prepare a Grignard reagent. The flask prepared is replaced with nitrogen, and a solution of trimethyl borate (39 ml) in tetrahydrofuran (50 ml) is placed therein. The Grignard reagent is added dropwise thereto and stirred for 10 hours. Add 150 ml of 20% aqueous hydrochloric acid to the reaction mixture and stir for a while, then extract the target product with chloroform, wash with water three times, and distill off the chloroform. The residue was recrystallized from methanol and water to obtain 17.5 g of 3-fluoro-4-methoxyphenylboric acid.
【0021】ステップ3 窒素置換したフラスコ中に
2M炭酸ナトリウム水溶液 60ml とベンゼン 80ml を入
れ、さらにp−ブロモアニソール 4.4g 及びテトラキス
トリフェニルホスフィンパラジウム 0.24g を入れる。
そこへエタノール 60ml に3−フルオロ−4−メトキシ
フェニルほう酸 4.0g を溶かした物を滴下し、3時間還
流する。反応液冷却後、クロロホルムで抽出し水で洗浄
した後、クロロホルムを留去する。残留物をアセトンと
メタノールで再結晶して、3−フルオロ−4,4’−ジ
メトキシビフェニル 4.6g を得た。Step 3 60 ml of a 2M sodium carbonate aqueous solution and 80 ml of benzene were placed in a flask purged with nitrogen, and 4.4 g of p-bromoanisole and 0.24 g of tetrakistriphenylphosphine palladium were placed.
A solution prepared by dissolving 4.0 g of 3-fluoro-4-methoxyphenylboric acid in 60 ml of ethanol was added dropwise thereto, and the mixture was refluxed for 3 hours. After cooling the reaction solution, extraction with chloroform and washing with water are performed, and then chloroform is distilled off. The residue was recrystallized from acetone and methanol to obtain 3-fluoro-4,4'-dimethoxybiphenyl (4.6 g).
【0022】ステップ4 なす型フラスコに3−フル
オロ−4,4’−ジメトキシビフェニル 4.6g ,臭化水
素酸 10ml,酢酸 50ml を入れ 20時間還流する。反応液
を室温まで冷却した後、濾過して水洗する。残留物をア
セトンとメタノールの混合溶媒中で再結晶して、3−フ
ルオロ−4,4’−ジヒドロキシビフェニル 2.8g を得
た。Step 4 In a eggplant-shaped flask, 4.6 g of 3-fluoro-4,4'-dimethoxybiphenyl, 10 ml of hydrobromic acid and 50 ml of acetic acid are placed and refluxed for 20 hours. The reaction solution is cooled to room temperature, filtered and washed with water. The residue was recrystallized in a mixed solvent of acetone and methanol to obtain 2.8 g of 3-fluoro-4,4'-dihydroxybiphenyl.
【0023】ステップ5 窒素置換したフラスコ中に
クロロホルム 40ml ,3−フルオロ−4,4’−ヒドロ
キシビフェニル 2.8g ,トリエチルアミン 6.1ml を入
れ溶解させる。そこへ蒸留精製したメタクリロイルクロ
ライド 3.9ml をゆっくり滴下し、3時間攪拌反応を続け
る。反応液を dil.HCl aq. ,飽和 NaHCO3 aq. ,水で洗
浄した後、重合防止のためメタノールを入れてクロロホ
ルムとメタノールを留去する。留去中結晶が現れてきた
ら取り出し、メタノールを入れて再結晶する。さらに生
成物をクロロホルムを展開溶媒とするシリカゲルカラム
で精製して、本発明の化合物3−フルオロ−ビフェニル
−4,4’−ジイルジメタクリレート 2.3g を得た。Step 5 Chloroform (40 ml), 3-fluoro-4,4'-hydroxybiphenyl (2.8 g) and triethylamine (6.1 ml) were placed and dissolved in a nitrogen-purged flask. 3.9 ml of distilled and purified methacryloyl chloride was slowly added dropwise thereto, and the reaction was continued for 3 hours with stirring. After washing the reaction solution with dil.HCl aq., Saturated NaHCO 3 aq., And water, add methanol to prevent polymerization, and distill off chloroform and methanol. If crystals appear during distillation, take them out and recrystallize them by adding methanol. Further, the product was purified by a silica gel column using chloroform as a developing solvent to obtain 2.3 g of the compound of the present invention, 3-fluoro-biphenyl-4,4'-diyldimethacrylate.
【0024】[0024]
【化13】 [Chemical 13]
【0025】融点は105.6℃であった。この化合物の赤
外吸収スペクトルを図1に示す。The melting point was 105.6 ° C. The infrared absorption spectrum of this compound is shown in FIG.
【0026】同様にして以下の化合物を得た。In the same manner, the following compound was obtained.
【0027】3,3’−ジフルオロ−ビフェニル−4,
4’−ジイルジメタクリレート3,3'-difluoro-biphenyl-4,
4'-diyl dimethacrylate
【0028】[0028]
【化14】 [Chemical 14]
【0029】融点は141.2℃であった。この化合物の赤
外吸収スペクトルを図2に示す。The melting point was 141.2 ° C. The infrared absorption spectrum of this compound is shown in FIG.
【0030】〔実施例2〕(表示素子) 図3に示すようにガラス基板1及び2の上に透明電極膜
(例えばITO膜)からなる電極3を形成し、この上に
ポリイミド等よりなる配向膜を塗布する。次にラビング
して配向制御層4を形成し、さらにガラス基板1及び2
をシール剤5を介して対向配置し、ガラス基板間に以下
に示す組成物をそれぞれ注入し、TN型の液晶表示セル
を作成した。Example 2 (Display Element) As shown in FIG. 3, an electrode 3 made of a transparent electrode film (for example, an ITO film) is formed on glass substrates 1 and 2, and an alignment made of polyimide or the like is formed thereon. Apply the film. Next, rubbing is performed to form the orientation control layer 4, and the glass substrates 1 and 2 are further formed.
Were opposed to each other with a sealant 5 in between, and the following compositions were injected between the glass substrates to prepare a TN type liquid crystal display cell.
【0031】本実施例では、液晶としてTL202とMJ91261
(ともにメルク社製)、カイラル成分としてS-1011(メ
ルク社製)、2色性色素としてS-344(三井東圧染料社
製)、高分子前駆体として本発明の3−フルオロ−ビフ
ェニル−4,4’−ジイルジメタクリレート及び3,
3’−ジフルオロ−ビフェニル−4,4’−ジイルジメ
タクリレートを用いた。In this embodiment, TL202 and MJ91261 are used as the liquid crystal.
(Both manufactured by Merck), S-1011 (manufactured by Merck) as a chiral component, S-344 (manufactured by Mitsui Toatsu Dyes) as a dichroic dye, and 3-fluoro-biphenyl- of the present invention as a polymer precursor. 4,4'-diyl dimethacrylate and 3,
3'-difluoro-biphenyl-4,4'-diyldimethacrylate was used.
【0032】測定した組成物は、TL202とMJ91261の8:2
の混合物を90.9%、S-1011を0.5%、S-344を3.6%を混
合したものをベースとした。このベース液晶に高分子前
駆体としてビフェニル−4−イルメタクリレートと本発
明の3−フルオロ−ビフェニル−4,4’−ジイルジメ
タクリレートの2:1の混合物を5%混合した組成物[1]
と、ビフェニル−4−イルメタクリレートと本発明の
3,3’−ジフルオロ−ビフェニル−4,4’−ジイル
ジメタクリレートの2:1の混合物を5%混合した組成物
[2],また比較例としてビフェニル−4−イルメタク
リレートとビフェニル−4,4’−ジイルジメタクリレ
ートの2:1の混合物を5%混合した組成物[比較−1]の
計3種類について測定を行った。液晶組成物は先に説明
した空パネルに封入して、紫外線照射して高分子前駆体
を光重合して液晶と高分子を相分離させた。なお、測定
はセル温度20゜C ,セルギャップ 5μm で行った。The composition measured is TL202 and MJ91261 8: 2.
90.9%, S-1011 0.5%, S-344 3.6% as a mixture. A composition in which 5% of a 2: 1 mixture of biphenyl-4-ylmethacrylate and 3-fluoro-biphenyl-4,4'-diyldimethacrylate of the present invention as a polymer precursor is mixed with this base liquid crystal [5].
And 5% of a 2: 1 mixture of biphenyl-4-yl methacrylate and 3,3′-difluoro-biphenyl-4,4′-diyl dimethacrylate of the present invention [2] as a comparative example. The measurement was carried out on a total of three kinds of compositions [Comparison-1] in which 5% of a 2: 1 mixture of biphenyl-4-ylmethacrylate and biphenyl-4,4'-diyldimethacrylate was mixed. The liquid crystal composition was enclosed in the empty panel described above, and was irradiated with ultraviolet rays to photopolymerize the polymer precursor to phase-separate the liquid crystal and the polymer. The measurement was performed at a cell temperature of 20 ° C and a cell gap of 5 µm.
【0033】こうして作製した表示素子を図4に示した
ような光学系に配置して、1KHzの短形波で波高値を変化
させた信号を印加したところ、図5,図6,図7に示し
たような電気光学特性があらわれた。図5,6はそれぞ
れ本発明の化合物を混合した液晶組成物[1],[2]
を用いて測定した電気光学特性で、図7は従来の高分子
前駆体を混合した液晶組成物[比較−1]の電気光学特
性である。横軸は電圧を縦軸は反射率を示し、反射率10
0%とは素子の替わりに白色上質紙を配置した場合の明
るさを示している。ところで素子の反射率は、パネルへ
の入射角度を一定にしても光の入射方向により反射率の
値が変わるという回転視角依存性があることがすでに調
べられわかっている。したがって測定条件を合わせるた
めに、ここで示した反射率は最も反射率が大きくなる入
射角度でパネルを固定したときの値を用いた。The display element thus produced was arranged in an optical system as shown in FIG. 4, and a signal having a peak value changed by a 1 KHz square wave was applied. The electro-optical characteristics shown are exhibited. 5 and 6 show liquid crystal compositions [1] and [2] in which the compound of the present invention is mixed.
FIG. 7 shows electro-optical characteristics of a liquid crystal composition [Comparative-1] in which a conventional polymer precursor is mixed. The horizontal axis shows the voltage and the vertical axis shows the reflectance.
0% indicates the brightness when white fine paper is placed instead of the element. By the way, it has been already investigated and found that the reflectance of the element has a rotational viewing angle dependency that the reflectance value changes depending on the incident direction of light even when the incident angle to the panel is constant. Therefore, in order to match the measurement conditions, the reflectance shown here is the value when the panel is fixed at the incident angle at which the reflectance is maximized.
【0034】[0034]
【表2】 [Table 2]
【0035】以上の結果から、本発明の液晶組成物を用
いることにより従来の表示素子より駆動電圧が1Vある
いはそれ以上低く、最大反射率が15%以上大きな液晶
表示素子を得ることができた。また、本発明の化合物を
高分子前駆体として含んだ液晶組成物の表示素子として
の比抵抗は1.6×1011Ωcmであり、操作上問題のない充
分大きな値を維持することができた。From the above results, by using the liquid crystal composition of the present invention, it was possible to obtain a liquid crystal display device having a driving voltage lower than that of the conventional display device by 1 V or more and a maximum reflectance of 15% or more. Further, the specific resistance of the liquid crystal composition containing the compound of the present invention as a polymer precursor as a display element was 1.6 × 10 11 Ωcm, and it was possible to maintain a sufficiently large value without any operational problem.
【0036】さらに、上記の実施例においてはTN型の
液晶表示セルを用いたが、MIM素子,TFT素子など
を用いた場合にも同様な効果が得られた。Further, although the TN type liquid crystal display cell is used in the above-mentioned embodiment, the same effect can be obtained when the MIM element, the TFT element or the like is used.
【0037】ここで、液晶の混合比率は上記の例に限ら
ないが、あまりMJ91261を増やすと比抵抗が落ちるため
好ましくない。またTL202が多すぎると駆動電圧が高く
なり、また散乱度も低下して好ましくない。この液晶組
成物に他の液晶を任意の割合で混ぜても表示素子として
機能する。Here, the mixing ratio of the liquid crystal is not limited to the above example, but it is not preferable to increase MJ91261 too much because the specific resistance decreases. On the other hand, if the amount of TL202 is too large, the driving voltage will be high and the degree of scattering will be low, which is not preferable. Even if this liquid crystal composition is mixed with another liquid crystal at an arbitrary ratio, it functions as a display element.
【0038】カイラル成分はここに示した物に限らず用
いることができる。カイラル成分としては高分子前駆体
にカイラル中心を持つ物も利用できる。また混合比率に
ついてもここに示した量に限らない、ただしあまり多く
入れるとヒステリシスが大きくなる傾向がある。The chiral component can be used without being limited to those shown here. As the chiral component, a polymer precursor having a chiral center can also be used. Also, the mixing ratio is not limited to the amount shown here, but if too much is added, the hysteresis tends to increase.
【0039】2色性色素については、ここに示した物に
限らず用いることができるが、できれば紫外線領域で吸
収の少ない物が好ましい。もちろん2色比が高ければさ
らに好ましい。色素の色については用途に応じて任意に
選ぶことができる。色素の含有量についてはここに示し
た量に限らないが、あまり多いと色素が結晶化したり表
示が暗くなる。The dichroic dye can be used without being limited to the ones shown here, but if possible, a dye that absorbs little in the ultraviolet region is preferable. Of course, it is more preferable if the two-color ratio is high. The color of the dye can be arbitrarily selected according to the application. The content of the dye is not limited to the amount shown here, but if it is too large, the dye crystallizes or the display becomes dark.
【0040】重合開始剤についてはここでは用いなかっ
たが、光増感剤も含めて用いることができる。ただし、
比抵抗が低下しやすいため注意して用いる。Although the polymerization initiator was not used here, a photosensitizer can also be used. However,
Use with caution because the specific resistance tends to decrease.
【0041】用いる高分子の前駆体は単独で用いてもよ
く、フェニル基の一部をアルキル基,ハロゲン基,シア
ノ基などの置換基で置き換えることもできる。さらに、
他の光重合性の高分子前駆体を混合して用いることもで
きる。特に二官能あるいは多官能の高分子前駆体を混合
すると高分子含有量を減らしても表示状態の焼き付きな
どの現象は生じにくくなる。高分子前駆体の含有量につ
いてはここに示した量でなくてもよいが、あまり少ない
と散乱度が弱くなり、あまり多いと駆動電圧が高くな
る。The polymer precursor to be used may be used alone, or part of the phenyl group may be replaced with a substituent such as an alkyl group, a halogen group or a cyano group. further,
Other photopolymerizable polymer precursors may be mixed and used. In particular, when a bifunctional or polyfunctional polymer precursor is mixed, even if the polymer content is reduced, a phenomenon such as image sticking in the display state hardly occurs. The content of the polymer precursor may not be the amount shown here, but if it is too small, the scattering degree becomes weak, and if it is too large, the driving voltage becomes high.
【0042】重合条件は、ここでは300nm以長の紫外線
を用いたが、これより短い光を用いても重合できる。た
だし、比抵抗が低下しやすいので重合には注意を要す
る。光強度については3mW/cm2としたが、これに限らな
い。光強度が弱ければ重合時間を長くし、光強度が強け
れば重合時間を短くする。ただしあまり光強度が強いと
比抵抗が低下しやすい。光重合時にわずか加熱(20〜50
℃程度)すると重合しやすい。As the polymerization conditions, ultraviolet rays having a length of 300 nm or more were used here, but the polymerization can be performed by using light shorter than this. However, the specific resistance is likely to decrease, so care must be taken in polymerization. The light intensity was set to 3 mW / cm 2 , but it is not limited to this. If the light intensity is weak, the polymerization time is lengthened, and if the light intensity is strong, the polymerization time is shortened. However, if the light intensity is too high, the specific resistance tends to decrease. Slight heating during photopolymerization (20-50
Polymerization is easy when (° C.).
【0043】反射性電極についてはアルミニウム、銀、
ニッケル、クロムなど光を反射する電極であれば用いる
ことができる。また電極を透明なものとし、素子の裏側
に反射性背景板を用いても良い。For the reflective electrode, aluminum, silver,
Any electrode that reflects light, such as nickel or chromium, can be used. Alternatively, the electrodes may be transparent and a reflective background plate may be used on the back side of the device.
【0044】配向処理については、液晶が配向するよう
な処理であればどのような方法であっても構わない。Any method may be used for the alignment treatment as long as it is a treatment for aligning the liquid crystal.
【0045】[0045]
【発明の効果】以上述べたように本発明の化合物あるい
はそれを用いた表示素子は、従来の化合物及び組成物を
用いた表示素子より駆動電圧が低く、反射率が大きい反
射型表示素子を作製することが可能となった。また、本
発明の化合物は従来のあらゆる液晶組成物と混ぜた場合
に相溶性が良好であった。本発明の化合物を用いれば、
大容量ディスプレイなどの明るい省電力マンマシンイン
ターフェイスを容易に、そして安価に作製することがで
きる。As described above, the compound of the present invention or the display device using the same produces a reflective display device having a lower driving voltage and a higher reflectance than the display device using the conventional compounds and compositions. It became possible to do. Further, the compound of the present invention had good compatibility when mixed with any conventional liquid crystal composition. With the compounds of the present invention,
A bright power-saving man-machine interface such as a large-capacity display can be easily and inexpensively manufactured.
【図1】本発明の実施例1で得られた3−フルオロ−ビ
フェニル−4,4’−ジイルジメタクリレートの赤外吸
収スペクトル図。FIG. 1 is an infrared absorption spectrum diagram of 3-fluoro-biphenyl-4,4′-diyldimethacrylate obtained in Example 1 of the present invention.
【図2】本発明の実施例1で得られた3,3’−ジフル
オロ−ビフェニル−4,4’−ジイルジメタクリレート
の赤外吸収スペクトル図。FIG. 2 is an infrared absorption spectrum diagram of 3,3′-difluoro-biphenyl-4,4′-diyldimethacrylate obtained in Example 1 of the present invention.
【図3】本発明の実施例2における表示素子の断面を示
す図。FIG. 3 is a diagram showing a cross section of a display element in Example 2 of the present invention.
【図4】本発明の実施例2における表示素子の電気光学
特性を測定した際の光学系を示す図。FIG. 4 is a diagram showing an optical system when measuring electro-optical characteristics of a display element in Example 2 of the present invention.
【図5】本発明の実施例2における表示素子[1]の電
気光学特性を示す図。FIG. 5 is a diagram showing electro-optical characteristics of the display element [1] in Example 2 of the present invention.
【図6】本発明の実施例2における表示素子[2]の電
気光学特性を示す図。FIG. 6 is a diagram showing electro-optical characteristics of the display element [2] in Example 2 of the present invention.
【図7】本発明の実施例2における表示素子[比較−
1]の電気光学特性を示す図。FIG. 7 shows a display device in Example 2 of the present invention [comparison-
1] is a diagram showing electro-optical characteristics of [1].
1,2 ガラス基板 3 電極 4 配向制御層 5 シール剤 6 色素 7 液晶 8 高分子 (9 反射電極を用いない場合には反射性背景板) 10 表示素子 11 光源 12 結像用レンズ 13 光電子増倍管 1, 2 Glass substrate 3 Electrode 4 Alignment control layer 5 Sealant 6 Dye 7 Liquid crystal 8 Polymer (9 Reflective background plate when not using reflective electrode) 10 Display element 11 Light source 12 Imaging lens 13 Photoelectron multiplication tube
Claims (10)
されることを特徴とするビフェニルメタクリレート誘導
体。Claims: (Wherein X is a fluorine atom or a hydrogen atom), a biphenyl methacrylate derivative.
表示素子において、高分子を形成する前駆体としてビフ
ェニルメタクリレート誘導体を少なくとも1成分として
用いることによって、 【化2】 (上式中、Xはフッソ原子または水素原子である)で表
される構成要素が少なくとも一部分高分子に存在するこ
とを特徴とするビフェニルメタクリレート誘導体を用い
た高分子分散型液晶表示素子。2. In a display device in which a liquid crystal and a polymer are aligned and dispersed with each other, by using a biphenyl methacrylate derivative as at least one component as a precursor for forming the polymer, A polymer-dispersed liquid crystal display device using a biphenyl methacrylate derivative, wherein a constituent element represented by the formula (X is a fluorine atom or a hydrogen atom) is present in at least a part of the polymer.
表示素子において、相分離させた液晶と高分子をシアリ
ングにより配向させる方法をとり、高分子を形成する前
駆体としてビフェニルメタクリレート誘導体を少なくと
も1成分として用いることによって、 【化3】 (上式中、Xはフッ素原子または水素原子である)で表
される構成要素が少なくとも一部分高分子に存在するこ
とを特徴とする請求項2に記載のビフェニルメタクリレ
ート誘導体を用いた高分子分散型液晶表示素子。3. In a display device in which a liquid crystal and a polymer are aligned and dispersed with each other, a method of aligning the phase-separated liquid crystal and the polymer by shearing is used, and at least one biphenyl methacrylate derivative is used as a precursor for forming the polymer. By using it as a component, The polymer-dispersed type using a biphenyl methacrylate derivative according to claim 2, wherein the constituent element represented by the formula (wherein X is a fluorine atom or a hydrogen atom) is present at least partially in the polymer. Liquid crystal display device.
表示素子において、液晶と高分子がゲルネットワーク状
に相分離しており、高分子を形成する前駆体としてビフ
ェニルメタクリレート誘導体を少なくとも1成分として
用いることによって、 【化4】 (上式中、Xはフッ素原子または水素原子である)で表
される構成要素が少なくとも一部分高分子に存在するこ
とを特徴とする請求項2に記載のビフェニルメタクリレ
ート誘導体を用いた高分子分散型液晶表示素子。4. A display device in which a liquid crystal and a polymer are aligned and dispersed with each other, wherein the liquid crystal and the polymer are phase-separated into a gel network, and a biphenyl methacrylate derivative is used as at least one component as a precursor for forming the polymer. By using, The polymer-dispersed type using a biphenyl methacrylate derivative according to claim 2, wherein the constituent element represented by the formula (wherein X is a fluorine atom or a hydrogen atom) is present at least partially in the polymer. Liquid crystal display device.
表示素子において、高分子を形成する前駆体として 【化5】 (上式中、Xはフッ素原子または水素原子である)で表
されるビフェニルメタクリレート誘導体を1〜20%含
有することを特徴とするビフェニルメタクリレート誘導
体を用いた請求項2に記載の高分子分散型液晶表示素
子。5. In a display device in which a liquid crystal and a polymer are orientation-dispersed with each other, as a precursor for forming the polymer: The polymer dispersion type according to claim 2, wherein the biphenyl methacrylate derivative represented by the formula (wherein X is a fluorine atom or a hydrogen atom) is contained in an amount of 1 to 20%. Liquid crystal display device.
表示素子において、液晶中に2色性色素を含有し、高分
子を形成する前駆体としてビフェニルメタクリレート誘
導体を少なくとも1成分として用いることによって、 【化6】 (上式中、Xはフッ素原子または水素原子である)で表
される構成要素が少なくとも一部分高分子に存在するこ
とを特徴とする請求項2に記載のビフェニルメタクリレ
ート誘導体を用いた高分子分散型液晶表示素子。6. A display device in which a liquid crystal and a polymer are oriented and dispersed to each other, wherein the liquid crystal contains a dichroic dye, and a biphenyl methacrylate derivative is used as at least one component as a precursor for forming the polymer. [Chemical 6] The polymer-dispersed type using a biphenyl methacrylate derivative according to claim 2, wherein the constituent element represented by the formula (wherein X is a fluorine atom or a hydrogen atom) is present at least partially in the polymer. Liquid crystal display device.
表示素子において、液晶あるいは高分子中の少なくとも
一方にカイラル成分が含有あるいは存在し、高分子を形
成する前駆体としてビフェニルメタクリレート誘導体を
少なくとも1成分として用いることによって、 【化7】 (上式中、Xはフッ素原子または水素原子である)で表
される構成要素が少なくとも一部分高分子に存在するこ
とを特徴とする請求項2に記載のビフェニルメタクリレ
ート誘導体を用いた高分子分散型液晶表示素子。7. A display device in which a liquid crystal and a polymer are oriented and dispersed to each other, and at least one of the liquid crystal and the polymer contains or exists a chiral component, and at least one biphenyl methacrylate derivative is used as a precursor for forming the polymer. By using it as a component, The polymer-dispersed type using a biphenyl methacrylate derivative according to claim 2, wherein the constituent element represented by the formula (wherein X is a fluorine atom or a hydrogen atom) is present at least partially in the polymer. Liquid crystal display device.
表示素子において、表示素子表面側での配向方向が主た
る光の入射方向と素子表面の法線を含む平面に対して垂
直であり、高分子を形成する前駆体としてビフェニルメ
タクリレート誘導体を少なくとも1成分として用いるこ
とによって、 【化8】 (上式中、Xはフッ素原子または水素原子である)で表
される構成要素が少なくとも一部分高分子に存在するこ
とを特徴とする請求項2に記載のビフェニルメタクリレ
ート誘導体を用いた高分子分散型液晶表示素子。8. In a display device in which a liquid crystal and a polymer are aligned and dispersed with each other, the alignment direction on the display device surface side is perpendicular to a plane including a main light incident direction and a normal line of the device surface, and By using a biphenyl methacrylate derivative as at least one component as a molecule-forming precursor: The polymer-dispersed type using a biphenyl methacrylate derivative according to claim 2, wherein the constituent element represented by the formula (wherein X is a fluorine atom or a hydrogen atom) is present at least partially in the polymer. Liquid crystal display device.
表示素子において、表示素子表面側での配向方向が素子
裏側での高分子の配向方向と異なり、高分子を形成する
前駆体としてビフェニルメタクリレート誘導体を少なく
とも1成分として用いることによって、 【化9】 (上式中、Xはフッ素原子または水素原子である)で表
される構成要素が少なくとも一部分高分子に存在するこ
とを特徴とする請求項2に記載のビフェニルメタクリレ
ート誘導体を用いた高分子分散型液晶表示素子。9. In a display device in which a liquid crystal and a polymer are aligned and dispersed with each other, the orientation direction on the surface side of the display device is different from the orientation direction of the polymer on the back side of the device, and biphenyl methacrylate is used as a precursor for forming the polymer. By using the derivative as at least one component, The polymer-dispersed type using a biphenyl methacrylate derivative according to claim 2, wherein the constituent element represented by the formula (wherein X is a fluorine atom or a hydrogen atom) is present at least partially in the polymer. Liquid crystal display device.
た表示素子において、高分子分散層を挟持する2枚の電
極の一方が光反射性の電極であり、高分子を形成する前
駆体としてビフェニルメタクリレート誘導体を少なくと
も1成分として用いることによって、 【化10】 (上式中、Xはフッ素原子または水素原子である)で表
される構成要素が少なくとも一部分高分子に存在するこ
とを特徴とする請求項2に記載のビフェニルメタクリレ
ート誘導体を用いた高分子分散型液晶表示素子。10. In a display device in which a liquid crystal and a polymer are oriented and dispersed to each other, one of the two electrodes sandwiching the polymer dispersion layer is a light-reflecting electrode, and biphenyl is used as a precursor for forming the polymer. By using a methacrylate derivative as at least one component, The polymer-dispersed type using a biphenyl methacrylate derivative according to claim 2, wherein the constituent element represented by the formula (wherein X is a fluorine atom or a hydrogen atom) is present at least partially in the polymer. Liquid crystal display device.
Priority Applications (1)
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JP24711493A JPH07101904A (en) | 1993-10-01 | 1993-10-01 | Biphenyl methacrylate derivative and polymer dispersion type liquid crystal display element using the same |
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Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP24711493A JPH07101904A (en) | 1993-10-01 | 1993-10-01 | Biphenyl methacrylate derivative and polymer dispersion type liquid crystal display element using the same |
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ID=17158647
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