JPH06157927A - Dichroic pigment, liquid crystal composition containing the pigment and liquid crystal element - Google Patents
Dichroic pigment, liquid crystal composition containing the pigment and liquid crystal elementInfo
- Publication number
- JPH06157927A JPH06157927A JP31365292A JP31365292A JPH06157927A JP H06157927 A JPH06157927 A JP H06157927A JP 31365292 A JP31365292 A JP 31365292A JP 31365292 A JP31365292 A JP 31365292A JP H06157927 A JPH06157927 A JP H06157927A
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- group
- formula
- compound
- water
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/28—Preparation of azo dyes from other azo compounds by etherification of hydroxyl groups
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Liquid Crystal Substances (AREA)
- Liquid Crystal (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は新規な黄色のアゾ系二色
性色素およびこれを含む液晶組成物ならびにそれを用い
た液晶素子に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a novel yellow azo dichroic dye, a liquid crystal composition containing the same, and a liquid crystal device using the same.
【０００２】[0002]
【従来の技術】現在、液晶表示としてはツイストネマチ
ック（ＴＮ）型表示モード、スーパーツイスト（ＳＴ
Ｎ）モードなどの外に各種の表示モードが提案されてい
る。このうち液晶に色素を溶解して用いるゲストホスト
（ＧＨ）型表示方式が、広い視野角などの特徴のため
に、自動車などの表示パネルとして広く用いられてい
る。2. Description of the Related Art Currently, liquid crystal displays include twisted nematic (TN) display mode and super twisted (ST).
In addition to the N) mode, various display modes have been proposed. Of these, a guest-host (GH) type display method in which a dye is dissolved in liquid crystal is widely used as a display panel for automobiles and the like because of its characteristics such as a wide viewing angle.
【０００３】このＧＨモードに用いられる二色性色素の
特性としては下記の項目 １）二色性 ２）溶解性 ３）耐光性 ４）着色力 が優れていることが要求される。The characteristics of the dichroic dye used in the GH mode are required to be excellent in the following items 1) dichroism 2) solubility 3) light resistance 4) coloring power.
【０００４】他方、市場のニーズが大きいブラックの液
晶組成物を構成する上で必要な黄色系の二色性色素につ
いては、従来、アゾ系色素の外にアントラキノン系色
素、ペリレン系色素などが知られている。しかしながら
アゾ系色素は概して耐光性に問題があり、また耐光性の
良好なアントラキノン系色素は着色力が低く、ペリレン
系色素は二色性が充分では無いなど、上記の特性を兼ね
備えた二色性色素は稀であり、特に高い二色性と高い着
色力および実用レベルの耐光性を併せ持つ色素は少ない
ため、ブラックの液晶組成物を構成する上で大きな制約
となっていた。また、最近のフッ素系液晶に対する溶解
性等の親和性の高い二色性色素は少ないという問題点が
生じていた。On the other hand, as for the yellow dichroic dye necessary for forming a black liquid crystal composition, which has a great demand in the market, conventionally, in addition to azo dyes, anthraquinone dyes and perylene dyes are known. Has been. However, azo dyes generally have problems with light resistance, anthraquinone dyes with good light resistance have low coloring power, and perylene dyes do not have sufficient dichroism. Dyes are rare, and there are few dyes that have particularly high dichroism, high tinting strength, and light resistance at a practical level, which has been a major limitation in constructing a black liquid crystal composition. In addition, there has been a problem that there are few dichroic dyes having high affinity with the recent fluorine-based liquid crystals.
【０００５】[0005]
【発明が解決しようとする課題】本発明は上記の難点の
少ない、実用性にすぐれた黄色の二色性色素およびこれ
を含む液晶組成物並びに該組成物を用いた液晶素子を提
供することを目的とする。DISCLOSURE OF THE INVENTION The present invention provides a yellow dichroic dye having less of the above-mentioned difficulties and excellent practicality, a liquid crystal composition containing the same, and a liquid crystal device using the composition. To aim.
【０００６】[0006]
【課題を解決するための手段】本発明は、前記請求項１
に記載の一般式（１）で表されるパーフルオロアルキル
基含有アゾ系二色性色素及び該色素を含む液晶組成物並
びにこの液晶組成物を少くとも一方が透明な電極付基板
間に挾持した液晶素子を要旨とするものである。The present invention provides the above-mentioned claim 1.
The perfluoroalkyl group-containing azo dichroic dye represented by the general formula (1) described in 1 above, a liquid crystal composition containing the dye, and at least one liquid crystal composition sandwiched between substrates with transparent electrodes. A liquid crystal element is the main point.
【０００７】本発明のアゾ系二色性色素は例えば、公知
のジアゾ化カップリング反応により得られる下記のアゾ
化合物The azo dichroic dye of the present invention is, for example, the following azo compound obtained by a known diazotization coupling reaction.
【０００８】[0008]
【化２】 [Chemical 2]
【０００９】（式中、Ｚ1 〜Ｚ9 及びｍ，ｎは前示一般
式（Ｉ）に於けると同一の意義を有する。）に、式Ｙ−
Ｒ（式中、Ｒは前示一般式（Ｉ）に於けると同一の意義
を有し、Ｙはハロゲン原子を示す。）で示される化合物
を反応させることにより得られる。前示一般式（Ｉ）に
於けるＲとしてはメチル、エチル、プロピル、ブチル、
ヘキシル、オクチルなどの直鎖状または分枝状のＣ1 〜
Ｃ18のアルキル基、エトキシメチル、ブトキシメチル、
エトキシエチル、ブトキシエチルなどのアルコキシアル
キル基、パーフルオロメチル基、パーフルオロエチル
基、シアノエチル基、アセトキシエチル基、アリールカ
ルボニルオキシ基、アルコキシカルボニル基などの非水
溶性置換基で置換されたアルキル基、ベンジル基、フェ
ネチル基、メチル、エチル、プロピル、ブチル、ヘキシ
ル、オクチルなどの直鎖状または分枝状のＣ1 〜Ｃ18の
アルキル基で置換されたベンジル基、エトキシメチル、
ブトキシメチル、エトキシエチル、ブトキシエチルなど
のアルコキシアルキル基で置換されたベンジル基、メト
キシ、エトキシ、プロポキシ、ヘプチルオキシ、オクチ
ルオキシなどのアルコキシ基で置換されたベンジル基、
フッ素原子、塩素原子、臭素原子などのハロゲン原子で
置換されたベンジル基などの非水溶性置換基で置換され
てもよいアラルキル基、シクロヘキシルメチル、４−シ
クロヘキシルシクロヘキシルメチル、４−ブチルシクロ
ヘキシルメチル、４−ヘプチルシクロヘキシルメチル、
４−オクチルシクロヘキシルメチル、４′−ブチル−４
−シクロヘキシルシクロヘキシルメチル、４−ブトキシ
エチルシクロヘキシルメチルなどの非水溶性置換基で置
換されてもよいシクロヘキシルアルキル基が挙げられ
る。(Wherein Z 1 to Z 9 and m and n have the same meaning as in the general formula (I) shown above), and the formula Y-
It is obtained by reacting a compound represented by R (wherein R has the same meaning as in the general formula (I) shown above and Y represents a halogen atom). R in the general formula (I) shown above is methyl, ethyl, propyl, butyl,
Hexyl, octyl and other linear or branched C 1-
C 18 alkyl group, ethoxymethyl, butoxymethyl,
Alkoxyalkyl groups such as ethoxyethyl and butoxyethyl, perfluoromethyl groups, perfluoroethyl groups, cyanoethyl groups, acetoxyethyl groups, arylcarbonyloxy groups, alkyl groups substituted with water-insoluble substituents such as alkoxycarbonyl groups, Benzyl group, phenethyl group, benzyl group substituted with a linear or branched C 1 -C 18 alkyl group such as methyl, ethyl, propyl, butyl, hexyl, octyl, ethoxymethyl,
Benzyl group substituted with an alkoxyalkyl group such as butoxymethyl, ethoxyethyl, butoxyethyl, benzyl group substituted with an alkoxy group such as methoxy, ethoxy, propoxy, heptyloxy, octyloxy,
Aralkyl group which may be substituted with a water-insoluble substituent such as benzyl group substituted with halogen atom such as fluorine atom, chlorine atom and bromine atom, cyclohexylmethyl, 4-cyclohexylcyclohexylmethyl, 4-butylcyclohexylmethyl, 4 -Heptylcyclohexylmethyl,
4-octylcyclohexylmethyl, 4'-butyl-4
Examples thereof include a cyclohexylalkyl group which may be substituted with a water-insoluble substituent such as -cyclohexylcyclohexylmethyl and 4-butoxyethylcyclohexylmethyl.
【００１０】またＺ1 ，Ｚ2 またはＺ4 、Ｚ5 またはＺ
7 ，Ｚ8 は互に連結してテトラリン環の一部などの脂肪
族環、ナフタリン環の一部などの芳香族環またはキノリ
ン環の一部などの含窒素芳香環を形成してもよい。本発
明の液晶組成物は前示一般式（Ｉ）で示されるジスアゾ
系二色性色素を、〔液晶デバイスハンドブック；日本学
術振興会第１４２委員会編（１９８９）；ｐ１５４〜ｐ
１９２，ｐ７１５〜ｐ７２２〕記載のネマチックあるい
はスメクチック相を示すビフェニル系、フェニルシクロ
ヘキサン系、フェニルピリミジン系、シクロヘキシルシ
クロヘキサン系などの各種の液晶化合物または液晶組成
物に公知の方法で混合することにより容易に調製するこ
とができる。Further, Z 1 , Z 2 or Z 4 , Z 5 or Z
7 and Z 8 may be linked to each other to form an aliphatic ring such as a part of tetralin ring, an aromatic ring such as a part of naphthalene ring, or a nitrogen-containing aromatic ring such as a part of quinoline ring. The liquid crystal composition of the present invention comprises the disazo dichroic dye represented by the general formula (I) shown above [Liquid Crystal Device Handbook; Japan Society for the Promotion of Science, 142nd Committee (1989); p154-p.
192, p715 to p722], and easily prepared by mixing with a known method to various liquid crystal compounds or liquid crystal compositions such as a biphenyl-based, phenylcyclohexane-based, phenylpyrimidine-based, cyclohexylcyclohexane-based, etc. exhibiting a nematic or smectic phase. can do.
【００１１】また本発明の液晶組成物はコレステリルノ
ナノエートなどの、液晶相を示しても示さなくても良い
光学活性化合物を含有してもよく、あるいは紫外線吸収
剤、酸化防止剤などの各種の添加剤を含有しても良い。
このようにして得られた液晶組成物を、少なくとも一方
が透明な電極付基板間に挾持することにより、ゲストホ
スト効果を応用した素子を構成することができる。透明
基板としては通常ガラス板或いはアクリル樹脂、ポリカ
ーボネート樹脂、エポキシ樹脂等の各種合成樹脂板が挙
げられ、その基板上に電極層が形成されるが、透明電極
層としては通常は酸化インジウム、酸化インジウムスズ
（ＩＴＯ）、酸化スズ等の金属酸化物等が使用される。The liquid crystal composition of the present invention may also contain an optically active compound such as cholesteryl nonanoate, which may or may not exhibit a liquid crystal phase, or various kinds of ultraviolet absorbers, antioxidants and the like. You may contain an additive.
By sandwiching the liquid crystal composition thus obtained between the substrates with electrodes, at least one of which is transparent, an element applying the guest-host effect can be constructed. The transparent substrate is usually a glass plate or various synthetic resin plates such as acrylic resin, polycarbonate resin, epoxy resin, etc., and the electrode layer is formed on the substrate, but the transparent electrode layer is usually indium oxide, indium oxide. Metal oxides such as tin (ITO) and tin oxide are used.
【００１２】透明電極層の液晶に接する表面は必要に応
じ配向処理されるが、配向処理方法としては、例えばオ
クタデシルジメチル〔３−（トリメトキシシリル）プロ
ピル〕アンモニウムクロライド、ヘキサデシルトリメチ
ルアンモニウムブロマイド等を塗布して垂直配向にする
方法、ポリイミドを塗布して平行配向にする方法、綿
布、脱脂面等でラビングして平行配向にする方法、Ｓｉ
Ｏを斜めの角度から蒸着して平行配向にする方法等が適
宜用いられる。The surface of the transparent electrode layer which is in contact with the liquid crystal is subjected to an alignment treatment as required. As the alignment treatment method, for example, octadecyldimethyl [3- (trimethoxysilyl) propyl] ammonium chloride, hexadecyltrimethylammonium bromide or the like is used. A method of applying a vertical orientation by coating, a method of applying a polyimide for parallel orientation, a method of rubbing with a cotton cloth, a degreased surface or the like to obtain a parallel orientation, Si
A method of vapor-depositing O from an oblique angle to obtain parallel alignment is appropriately used.
【００１３】基体は互に配向処理層面が対向するように
してスペーサー等を介して一体化し、１〜５０μ好まし
くは１〜１５μの素子間隔の素子を構成し、この素子間
隔の中に液晶を封入する。〔松本正一、角田市良“液晶
の最新技術”工業調査会，３４（１９８３）；Ｊ．Ｌ．
Ｆｅｒｇａｓｏｎ，ＳＩＤ８５Ｄｉｇｅｓｔ，６８（１
９８５）等参照〕。The substrates are integrated with each other with spacers or the like so that the surfaces of the alignment treatment layers face each other to form elements having element intervals of 1 to 50 μ, preferably 1 to 15 μ, and liquid crystal is enclosed in the element intervals. To do. [Shouichi Matsumoto, Ryo Kakuda “Latest Technology of Liquid Crystals” Industrial Research Committee, 34 (1983); L.
Fergason, SID85Digest, 68 (1
985) etc.].
【００１４】[0014]
【発明の効果】本発明の黄色色素は高い二色性と高い着
色力および良好な耐光性をもつ二色性色素であるので、
液晶にこれを含ませた液晶組成物を使用することによ
り、コントラストおよび耐久性に優れた表示素子などの
液晶素子を構成することができる。The yellow dye of the present invention is a dichroic dye having high dichroism, high tinting strength and good light resistance.
By using the liquid crystal composition containing the liquid crystal, it is possible to form a liquid crystal element such as a display element having excellent contrast and durability.
【００１５】[0015]
【実施例】次に、本発明を実施例により具体的に説明す
るが、本発明はこれら実施例により限定されるものでは
ない。 実施例１ 下記構造式で示されるパーフルオロアルキル基含有アミ
ノアゾ化合物EXAMPLES Next, the present invention will be specifically described with reference to examples, but the present invention is not limited to these examples. Example 1 Aminoazo compound containing a perfluoroalkyl group represented by the following structural formula
【００１６】[0016]
【化３】 [Chemical 3]
【００１７】６．１ｇを酢酸２０ｍｌ、プロピオン酸１
０ｍｌ、リン酸１ｍｌに溶解して０〜５℃に冷却し、こ
れに０〜５℃に冷却した４３％ニトロシル硫酸３．２ｇ
を攪拌下に加えた。同温度で２時間攪拌した後、スルフ
ァミン酸０．２ｇを加えてジアゾ液を調製する。6.1 g of acetic acid 20 ml, propionic acid 1
3.2 ml of 43% nitrosylsulfate dissolved in 0 ml and phosphoric acid 1 ml and cooled to 0 to 5 ° C.
Was added with stirring. After stirring for 2 hours at the same temperature, 0.2 g of sulfamic acid is added to prepare a diazo solution.
【００１８】他方、フェノール１．１ｇを水１００ｍｌ
に溶解させ酢酸ナトリウムを加えてpH８に調整したカッ
プラー液を準備し、これを０〜５℃に冷却して攪拌下に
pHをアンモニア水により８〜１０に保ちながら上記ジア
ゾ液を徐々に加え、同温度で２時間反応させた。反応
後、塩酸を加えてpH６とし析出物を濾過、水洗、乾燥し
て得られた下記構造式On the other hand, 1.1 g of phenol is added to 100 ml of water.
A coupler solution prepared by dissolving in water and adjusting the pH to 8 by adding sodium acetate was prepared, cooled to 0 to 5 ° C, and stirred.
The above diazo solution was gradually added while keeping the pH at 8 to 10 with aqueous ammonia, and the reaction was carried out at the same temperature for 2 hours. After the reaction, hydrochloric acid was added to adjust the pH to 6, and the precipitate was filtered, washed with water, and dried to obtain the following structural formula.
【００１９】[0019]
【化４】 [Chemical 4]
【００２０】のジスアゾ色素の粗結晶を得た。ジスアゾ
色素２．００ｇをＮ−メチルピロリドン１１ｍｌに溶解
し、これに４−ブチルオキシベンジルクロライド１．０
８ｇ，炭酸ナトリウム０．８ｇを加えて７０℃で３時間
反応させた後、室温に冷却しメタノールで希釈して析出
物を濾過、水洗、乾燥して得られた粗結晶をカラムクロ
マトにより精製し、クロロホルム、メタノール混合溶液
から析出させて、下記構造式Crude crystals of the disazo dye of were obtained. Disazo dye 2.00 g was dissolved in N-methylpyrrolidone 11 ml, and 4-butyloxybenzyl chloride 1.0
After adding 8 g and sodium carbonate 0.8 g and reacting at 70 ° C. for 3 hours, the mixture was cooled to room temperature, diluted with methanol, and the precipitate was filtered, washed with water and dried to obtain crude crystals, which were purified by column chromatography. , The following structural formula
【００２１】[0021]
【化５】 [Chemical 5]
【００２２】で示されるジスアゾ化合物を得た。このジ
スアゾ化合物を商品名ＺＬＩ−１５６５（Ｅ．ＭＥＲＣ
Ｋ社製）として市販されているフェニルシクロヘキサン
系液晶混合物に１ｗｔ％の濃度で溶解させ黄色のゲスト
ホスト液晶組成物を調製した。これをポリイミド系樹脂
を塗布、硬化、ラビング処理した透明電極付きガラス基
板を対向させ、液晶が平行配向となるように構成したギ
ャップ９μのセルに封入した。A disazo compound represented by the following formula was obtained. This disazo compound is traded under the trade name ZLI-1565 (E.MERC
A yellow guest-host liquid crystal composition was prepared by dissolving it at a concentration of 1 wt% in a phenylcyclohexane liquid crystal mixture marketed by K. Co., Ltd.). This was coated with a polyimide resin, cured, and rubbed to face a glass substrate with a transparent electrode, and the glass substrate was sealed in a cell having a gap of 9 μm configured so that liquid crystals were aligned in parallel.
【００２３】この黄色に着色したセルの配向方向に平行
な直線偏光に対する吸光度（Ａ//）および配向方向に垂
直な直線偏光に対する吸光度（Ａ⊥）を測定し、その吸
収ピーク（λmax ：４６３ｎｍ）におけるオーダーパラ
メーター（Ｓ）を下記の式 Ｓ＝（Ａ//−Ａ⊥）／（Ａ//＋２Ａ⊥） から求めた結果、Ｓ＝０．７７であった。The absorbance (A //) of linearly polarized light parallel to the orientation direction of this yellow-colored cell and the absorbance (A⊥) of linearly polarized light perpendicular to the orientation direction were measured, and the absorption peak (λ max : 463 nm) was measured. ), The order parameter (S) was calculated from the following formula S = (A // − A⊥) / (A // + 2A⊥), and as a result, S = 0.77.
【００２４】また、４−ブチルオキシベンジルクロライ
ドの代りに４−ペンチルオキシベンジルクロライドを使
用し、他は同様にして下記構造式Further, 4-pentyloxybenzyl chloride was used in place of 4-butyloxybenzyl chloride, and the other components were the same as in the following structural formula.
【００２５】[0025]
【化６】 [Chemical 6]
【００２６】で示されるジスアゾ化合物を得た。これを
上記と同様にしてオーダーパラメーターを測定した結
果、Ｓ＝０．７９（λmax ：４６３ｎｍ）であった。ま
た、４−ブチルオキシベンジルクロライドの代りに４−
ヘプチルオキシベンジルクロライドを使用し、他は同様
にして下記構造式A disazo compound represented by the following formula was obtained. As a result of measuring the order parameter in the same manner as above, S = 0.79 (λ max : 463 nm) was obtained. In addition, 4-butyloxybenzyl chloride is replaced by 4-
Heptyloxybenzyl chloride was used, but otherwise the same as the following structural formula.
【００２７】[0027]
【化７】 [Chemical 7]
【００２８】で示されるジスアゾ化合物を得た。これを
上記と同様にしてオーダーパラメーターを測定した結
果、Ｓ＝０．７９（λmax ：４６３ｎｍ）であった。A disazo compound represented by the following formula was obtained. As a result of measuring the order parameter in the same manner as above, S = 0.79 (λ max : 463 nm) was obtained.
【００２９】実施例２ 下記構造式で示されるパーフルオロアルキル基含有アミ
ノアゾ系化合物Example 2 Perfluoroalkyl group-containing aminoazo compound represented by the following structural formula
【００３０】[0030]
【化８】 [Chemical 8]
【００３１】１１．３ｇを酢酸５０ｍｌ、３５％塩酸
５．３ｍｌ、水１００ｍｌに溶解させ、０〜５℃に冷却
して亜硝酸ナトリウム１．４５ｇを加え、同温度で２時
間反応させ、スルファミン酸０．１０ｇを加えてジアゾ
液を調製した。他方、１−ナフトール２．９ｇをメタノ
ール６０ｍｌに溶解させ５％苛性ソーダ水溶液を加えて
pH９のカップラー液を調製し、これを０〜５℃に冷却し
て攪拌下にジアゾ液とアンモニア水を交互に加えてpHを
８〜１０に保ちながら上記ジアゾ液をカップラー液に加
えた後、同温度で２時間反応させた。反応後、塩酸を加
えてpH６とし析出物を濾過、水洗、乾燥して下記構造式11.3 g was dissolved in 50 ml of acetic acid, 5.3 ml of 35% hydrochloric acid and 100 ml of water, cooled to 0 to 5 ° C., 1.45 g of sodium nitrite was added, and the mixture was reacted at the same temperature for 2 hours to give sulfamic acid. A diazo solution was prepared by adding 0.10 g. On the other hand, 2.9 g of 1-naphthol was dissolved in 60 ml of methanol, and a 5% aqueous sodium hydroxide solution was added.
After preparing a coupler solution having a pH of 9 and cooling it to 0 to 5 ° C., the diazo solution and ammonia water were alternately added with stirring to add the above diazo solution to the coupler solution while keeping the pH at 8 to 10. The reaction was carried out at the same temperature for 2 hours. After the reaction, hydrochloric acid was added to adjust the pH to 6, and the precipitate was filtered, washed with water and dried to obtain the following structural formula.
【００３２】[0032]
【化９】 [Chemical 9]
【００３３】のジスアゾ色素の粗結晶を得た。ジスアゾ
色素２．１６ｇをＮ−メチルピロリドン１５ｍｌに溶解
し、これに４−ペンチルオキシベンジルクロライド２．
５３ｇ，炭酸ナトリウム０．９９ｇを加えて８０℃で７
時間反応させた後、室温に冷却しメタノールで希釈して
析出物を濾過、水洗、乾燥して得られた粗結晶をカラム
クロマトにより精製し、クロロホルム、メタノール混合
溶液から析出させて、下記構造式Crude crystals of the disazo dye of were obtained. 2.16 g of disazo dye was dissolved in 15 ml of N-methylpyrrolidone, and 4-pentyloxybenzyl chloride 2.
Add 53g and 0.99g of sodium carbonate and add at 80 ℃ for 7
After reacting for a time, cooled to room temperature, diluted with methanol, filtered the precipitate, washed with water, and dried to obtain a crude crystal, which was purified by column chromatography and precipitated from a mixed solution of chloroform and methanol.
【００３４】[0034]
【化１０】 [Chemical 10]
【００３５】で示されるジスアゾ化合物を得た。これを
実施例１と同様にしてオーダーパラメーターを測定した
結果、Ｓ＝０．７９（λmax ：４５５ｎｍ）であった。
４−ペンチルオキシベンジルクロライドの代りに４−ヘ
プチルオキシベンジルクロライドを使用し、他は同様に
して下記構造式A disazo compound represented by the following formula was obtained. When the order parameter was measured in the same manner as in Example 1, S = 0.79 (λ max : 455 nm) was obtained.
4-heptyloxybenzyl chloride was used in place of 4-pentyloxybenzyl chloride, and otherwise the same as in the following structural formula.
【００３６】[0036]
【化１１】 [Chemical 11]
【００３７】で示されるジスアゾ化合物を得た。これを
上記と同様にしてオーダーパラメーターを測定した結
果、Ｓ＝０．８０（λmax ：４５５ｎｍ）であった。A disazo compound represented by the following formula was obtained. As a result of measuring the order parameter in the same manner as above, S = 0.80 (λ max : 455 nm) was obtained.
【００３８】実施例３ 上記の実施例に準じた方法により得られたジスアゾ化合
物のフェニルシクロヘキサン系液晶混合物：商品名ＺＬ
Ｉ−１５６５（Ｅ．ＭＥＲＣＫ社製）中におけるオーダ
ーパラメーター（Ｓ）と色相を表−１に示す。Example 3 Phenylcyclohexane type liquid crystal mixture of disazo compound obtained by the method according to the above example: trade name ZL
Table 1 shows the order parameter (S) and hue in I-1565 (manufactured by E. MERCK).
【００３９】[0039]
【表１】 [Table 1]
【００４０】[0040]
【表２】 [Table 2]
【００４１】[0041]
【表３】 [Table 3]
【００４２】[0042]
【表４】 [Table 4]
【００４３】[0043]
【表５】 [Table 5]
【００４４】[0044]
【表６】 [Table 6]
【００４５】[0045]
【表７】 [Table 7]
【００４６】[0046]
【表８】 [Table 8]
【図１】第１図は本発明の液晶素子の電圧無印加状態の
略示的な断面図である。FIG. 1 is a schematic cross-sectional view of a liquid crystal element of the present invention when no voltage is applied.
【図２】第２図は本発明の液晶素子の電圧印加状態の略
示的な断面図を示す。FIG. 2 is a schematic sectional view of a liquid crystal element of the present invention in a voltage applied state.
１ 観察者 ２ 透明基板 ３ 平行配向処理が施された透明電極、 ４ 誘電異方性が正のネマチック液晶分子 ５ 二色性色素分子 ６ 入射偏光 ７ 入射偏光の偏光方向 ８ 偏光板 ９ 入射光 1 observer 2 transparent substrate 3 transparent electrode subjected to parallel alignment treatment, 4 nematic liquid crystal molecule with positive dielectric anisotropy 5 dichroic dye molecule 6 incident polarized light 7 polarization direction of incident polarized light 8 polarizing plate 9 incident light
Claims (3)
ル基、非水溶性置換基で置換されてもよいアラルキル
基、またはアルキル基、アルコキシアルキル基で置換さ
れてもよいシクロヘキシルアルキル基を示し、ｍは３〜
１８、ｎは０、１、２の整数を示し、Ｚ1 〜Ｚ9 は水素
原子、ハロゲン原子、メチル基、メトキシ基を示し、Ｚ
1 ，Ｚ2 またはＺ4 、Ｚ5 またはＺ7 ，Ｚ8 は互に連結
して脂肪族環、芳香族環または含窒素芳香環を形成して
もよい。）で表されるパーフルオロアルキル基含有アゾ
系色素。1. A compound represented by the general formula (1): (In the formula, R represents an alkyl group which may be substituted with a water-insoluble substituent, an aralkyl group which may be substituted with a water-insoluble substituent, or an alkyl group, a cyclohexylalkyl group which may be substituted with an alkoxyalkyl group. And m is 3 to
18, n represents an integer of 0, 1, 2 and Z 1 to Z 9 represent a hydrogen atom, a halogen atom, a methyl group or a methoxy group, Z
1 , Z 2 or Z 4 , Z 5 or Z 7 , Z 8 may be linked to each other to form an aliphatic ring, an aromatic ring or a nitrogen-containing aromatic ring. ) Perfluoroalkyl group-containing azo dye represented by
るパーフルオロアルキル基含有アゾ系色素及び液晶物質
を含む液晶組成物。2. A liquid crystal composition comprising a perfluoroalkyl group-containing azo dye represented by the general formula (1) according to claim 1 and a liquid crystal substance.
一方が透明な電極付基板間に挾持した液晶素子。3. A liquid crystal device in which the liquid crystal composition according to claim 2 is sandwiched between substrates with electrodes, at least one of which is transparent.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP31365292A JPH06157927A (en) | 1992-11-24 | 1992-11-24 | Dichroic pigment, liquid crystal composition containing the pigment and liquid crystal element |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP31365292A JPH06157927A (en) | 1992-11-24 | 1992-11-24 | Dichroic pigment, liquid crystal composition containing the pigment and liquid crystal element |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH06157927A true JPH06157927A (en) | 1994-06-07 |
Family
ID=18043889
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP31365292A Pending JPH06157927A (en) | 1992-11-24 | 1992-11-24 | Dichroic pigment, liquid crystal composition containing the pigment and liquid crystal element |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH06157927A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002296417A (en) * | 2001-03-30 | 2002-10-09 | Nippon Kayaku Co Ltd | Dye-based polarizing film |
| WO2018164252A1 (en) * | 2017-03-09 | 2018-09-13 | 富士フイルム株式会社 | Composition, dichroic material, light-absorbing anisotropic film, laminate, and image display device |
| WO2019221267A1 (en) * | 2018-05-18 | 2019-11-21 | Ｊｘｔｇエネルギー株式会社 | Liquid crystalline compound, ionic conductor, electrolytic film, and secondary battery |
-
1992
- 1992-11-24 JP JP31365292A patent/JPH06157927A/en active Pending
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002296417A (en) * | 2001-03-30 | 2002-10-09 | Nippon Kayaku Co Ltd | Dye-based polarizing film |
| WO2018164252A1 (en) * | 2017-03-09 | 2018-09-13 | 富士フイルム株式会社 | Composition, dichroic material, light-absorbing anisotropic film, laminate, and image display device |
| KR20190108634A (en) * | 2017-03-09 | 2019-09-24 | 후지필름 가부시키가이샤 | Compositions, Dichroic Materials, Light Absorption Anisotropic Films, Laminates, and Image Display Devices |
| CN110461951A (en) * | 2017-03-09 | 2019-11-15 | 富士胶片株式会社 | Composition, dichroic substance, extinction anisotropic membrane, laminated body and image display device |
| JPWO2018164252A1 (en) * | 2017-03-09 | 2020-04-23 | 富士フイルム株式会社 | Composition, dichroic material, light-absorption anisotropic film, laminate and image display device |
| JP2022008941A (en) * | 2017-03-09 | 2022-01-14 | 富士フイルム株式会社 | Composition, dichroic substance, light absorption anisotropic film, laminate, and image display device |
| CN110461951B (en) * | 2017-03-09 | 2022-04-08 | 富士胶片株式会社 | Composition, dichroic material, light-absorbing anisotropic film, laminate, and image display device |
| WO2019221267A1 (en) * | 2018-05-18 | 2019-11-21 | Ｊｘｔｇエネルギー株式会社 | Liquid crystalline compound, ionic conductor, electrolytic film, and secondary battery |
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