JPH08143865A - Dichroic coloring matter, liquid crystal composition and liquid crystal element containing the same coloring matter - Google Patents

Dichroic coloring matter, liquid crystal composition and liquid crystal element containing the same coloring matter

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Publication number
JPH08143865A
JPH08143865A JP5002095A JP5002095A JPH08143865A JP H08143865 A JPH08143865 A JP H08143865A JP 5002095 A JP5002095 A JP 5002095A JP 5002095 A JP5002095 A JP 5002095A JP H08143865 A JPH08143865 A JP H08143865A
Authority
JP
Japan
Prior art keywords
liquid crystal
group
coloring matter
formula
crystal composition
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.)
Pending
Application number
JP5002095A
Other languages
Japanese (ja)
Inventor
Masaharu Kaneko
雅晴 金子
Hisayo Ishio
尚代 石尾
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Mitsubishi Chemical Corp
Original Assignee
Mitsubishi Chemical Corp
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Mitsubishi Chemical Corp filed Critical Mitsubishi Chemical Corp
Priority to JP5002095A priority Critical patent/JPH08143865A/en
Publication of JPH08143865A publication Critical patent/JPH08143865A/en
Pending legal-status Critical Current

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Abstract

PURPOSE: To obtain the subject coloring matter, containing a specific perfluoroalkylsulfonyl group, having a yellow to a blue color and further high dichroism and tinting strength and capable of constituting a liquid crystal element excellent in contrast and durability. CONSTITUTION: A coloring matter of formula I [B is H or a nonionic substituent group; X is formula II or III; Z<1> to Z<13> are each H, a halogen, methyl, methoxy or trifluoromethyl; Z<1> and Z<2> , Z<4> and Z<5> , Z<7> and Z<8> or Z<10> and Z<11> may mutually be bound to form an aliphatic ring or a (nitrogen-containing) aromatic ring; (n) is 1-18; (m) is 0-2; (p) is 0 or 1]. For example, anilines of formula IV containing a perfluoroalkylsulfonyl group are preferably used to afford the objective coloring matter according to the well-known diazotization coupling reaction.

Description

【発明の詳細な説明】Detailed Description of the Invention

【0001】[0001]

【産業上の利用分野】本発明は新規な黄色から青色のア
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 to blue azo dichroic dye, a liquid crystal composition containing the same and a liquid crystal device.

【0002】[0002]

【従来の技術】現在、液晶素子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)モードなどの他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 At present, liquid crystal elements include twisted nematic (TN) type display mode and super twisted (ST) type.
Various display modes other than the N) mode 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 properties 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、赤色〜青色系の二
色性色素については、従来、末端にアルキル基、ニトロ
基あるいはシアノ基を有する構造の色素などが知られて
いる。しかしながら従来のニトロ基やシアノ基を有する
色素は耐光性や溶解性に大きな難点があり、またアルキ
ル基を有する色素は黄味の赤色などの浅色の色相になり
やすく、青色などの深色の色相にはなりにくいという難
点を有していた。また、従来の色素は最近のTFT液晶
素子などに用いられているフッ素系液晶に対する溶解性
等の親和性が充分ではないという問題点があった。
On the other hand, the yellow, red to blue dichroic dyes necessary for constructing a black liquid crystal composition, which has a great market need, conventionally have an alkyl group, a nitro group or a cyano group at the terminal. Structural dyes are known. However, conventional dyes having a nitro group or a cyano group have great drawbacks in light resistance and solubility, and a dye having an alkyl group is apt to have a pale hue such as yellowish red and a deep color such as blue. It had a drawback that it was difficult to obtain a hue. Further, the conventional dye has a problem that the affinity such as solubility with respect to the fluorine-based liquid crystal used in the recent TFT liquid crystal element is not sufficient.

【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
少ない二色性色素およびこれを含む液晶組成物および液
晶素子を提供することを目的とする。
SUMMARY OF THE INVENTION It is an object of the present invention to provide a dichroic dye having less of the above problems, a liquid crystal composition containing the same and a liquid crystal device.

【0006】[0006]

【課題を解決するための手段】本発明の目的は、下記一
般式〔I〕
The object of the present invention is to provide a compound represented by the following general formula [I]

【0007】[0007]

【化3】 Embedded image

【0008】(式中、Bは水素原子または非イオン性置
換基を示し、Xは
(In the formula, B represents a hydrogen atom or a nonionic substituent, and X represents

【0009】[0009]

【化4】 [Chemical 4]

【0010】を示し、Z1 〜Z13はそれぞれ水素原子、
ハロゲン原子、メチル基、メトキシ基またはトリフルオ
ロメチル基を示し、また、Z1 とZ2 、Z4 とZ5 、Z
7 とZ 8 、Z10とZ11は互い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く、nは1〜1
8、mは0〜2、pは0または1の数を示す。)で表わ
されるパーフルオロアルキルスルホニル基、含有アゾ系
二色性色素、これを含む液晶組成物および液晶素子によ
り達成される。
Indicating Z1~ Z13Are hydrogen atoms,
Halogen atom, methyl group, methoxy group or trifluoro
A methyl group, and Z1And Z2, ZFourAnd ZFive, Z
7And Z 8, ZTenAnd Z11Are linked to each other by an aliphatic ring, aromatic
A group ring or a nitrogen-containing aromatic ring may be formed, and n is 1 to 1
8, m is 0 to 2, and p is 0 or 1. )
Perfluoroalkylsulfonyl group, containing azo type
A dichroic dye, a liquid crystal composition containing the same, and a liquid crystal device
Achieved.

【0011】本発明に用いるアゾ系二色性色素は下記の
反応式〔II〕
The azo dichroic dye used in the present invention has the following reaction formula [II]

【0012】[0012]

【化5】 Embedded image

【0013】により、合成されるパーフルオロアルキル
スルホニル基を含むアニリン類を用いて、公知のジアゾ
化カップリング反応を適用することにより合成すること
ができる。前示一般式〔I〕におけるBは水素原子また
は非イオン性置換基を示し、非イオン性置換基の具体例
としては、
According to the method described above, the aniline having a perfluoroalkylsulfonyl group to be synthesized can be used to apply a known diazotized coupling reaction. B in the general formula [I] shown above represents a hydrogen atom or a nonionic substituent, and specific examples of the nonionic substituent include

【0014】[0014]

【化6】 [Chemical 6]

【0015】などが挙げられ、R1 及びR2 はそれぞれ
直鎖状又は分岐状のアルキル基を示し、R3 は1つ以上
のハロゲン原子を含むアルキル基を示し、R4 及びR5
はそれぞれ水素原子、ハロゲン原子、メチル基、メトキ
シ基、トリフルオロメチル基、ニトロ基またはアルキル
基を示す。Xは
And the like, R 1 and R 2 each represent a linear or branched alkyl group, R 3 represents an alkyl group containing at least one halogen atom, and R 4 and R 5
Each represents a hydrogen atom, a halogen atom, a methyl group, a methoxy group, a trifluoromethyl group, a nitro group or an alkyl group. X is

【0016】[0016]

【化7】 [Chemical 7]

【0017】を示す。Z1 〜Z13はそれぞれ、水素原
子、塩素原子、フッ素原子、臭素原子などのハロゲン原
子、メチル基、メトキシ基またはトリフルオロメチル基
を示し、また、Z1 とZ2 、Z4 とZ5 、Z7 とZ8
たはZ10とZ11は互い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。
Is shown. Z 1 to Z 13 each represent a hydrogen atom, a chlorine atom, a fluorine atom, a halogen atom such as a bromine atom, a methyl group, a methoxy group or a trifluoromethyl group, and Z 1 and Z 2 , Z 4 and Z 5 , Z 7 and Z 8 or Z 10 and Z 11 are connected 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. May be formed.

【0018】nは1〜18、好ましくは1〜8、mは0
〜2、好ましくは1、pは0または1、好ましくは0の
数を示す。mが2の場合、異なるベンジル基に置換して
いるZ1 同士、Z2 同士またはZ3 同士は互いに異なっ
ていてもよい。
N is 1 to 18, preferably 1 to 8 and m is 0.
˜2, preferably 1, p represents 0 or 1, preferably 0. When m is 2, Z 1 s , Z 2 s, or Z 3 s that are substituted by different benzyl groups may be different from each other.

【0019】本発明の液晶組成物は前示一般式〔I〕で
示される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〜p192,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
たは液晶組成物等の液晶物質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。本発明において
使用される液晶化合物の例としては、次のようなものが
挙げられる。
The liquid crystal composition of the present invention comprises an azo 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 to p192, p715 to p722] and a liquid crystal substance such as a biphenyl-based, phenylcyclohexane-based, phenylpyrimidine-based, cyclohexylcyclohexane-based liquid crystal compound or a liquid crystal composition exhibiting a nematic or smectic phase is mixed by a known method. Can be easily prepared. Examples of the liquid crystal compound used in the present invention are as follows.

【0020】[0020]

【化8】 Embedded image

【0021】(式中、V及びWは、それぞれアルキル
基、アルコキシ基、アルコキシアルキル基、アルキルフ
ェニル基、アルコキシアルキルフェニル基、アルコキシ
フェニル基、アルキルシクロヘキシル基、アルコキシア
ルキルシクロヘキシル基、アルキルシクロヘキシルフェ
ニル基、シアノフェニル基、シアノ基、ハロゲン原子、
フルオロメチル基、フルオロメトキシ基、アルキルフェ
ニルアルキル基、アルコキシアルキルフェニルアルキル
基、アルキルシクロヘキシルアルキル基、アルコキシア
ルコキシシクロヘキシルアルキル基、アルコキシフェニ
ルアルキル基またはアルキルシクロヘキシルフェニルア
ルキル基を表し、これらのアルキル鎖およびアルコキシ
鎖中に、光学活性中心を有してもよい。Yは水素原子、
ハロゲン原子またはシアノ基を表し、また、VおよびW
中のフェニル基またはフェノキシ基は、シアノ基、フッ
素原子、塩素原子等のハロゲン原子でさらに置換されて
いてもよい。また、上記各構造式中のフェニル基は、1
個から4個のフッ素原子、塩素原子等のハロゲン原子、
シアノ基でさらに置換されていてもよい。)
(In the formula, V and W are each an alkyl group, an alkoxy group, an alkoxyalkyl group, an alkylphenyl group, an alkoxyalkylphenyl group, an alkoxyphenyl group, an alkylcyclohexyl group, an alkoxyalkylcyclohexyl group, an alkylcyclohexylphenyl group, Cyanophenyl group, cyano group, halogen atom,
Represents a fluoromethyl group, a fluoromethoxy group, an alkylphenylalkyl group, an alkoxyalkylphenylalkyl group, an alkylcyclohexylalkyl group, an alkoxyalkoxycyclohexylalkyl group, an alkoxyphenylalkyl group or an alkylcyclohexylphenylalkyl group, and these alkyl chains and alkoxy chains It may have an optically active center therein. Y is a hydrogen atom,
Represents a halogen atom or a cyano group, and V and W
The phenyl group or phenoxy group therein may be further substituted with a halogen atom such as a cyano group, a fluorine atom or a chlorine atom. The phenyl group in each of the above structural formulas is 1
From 4 to 4 halogen atoms such as fluorine and chlorine,
It may be further substituted with a cyano group. )

【0022】また本発明の液晶組成物はコレステリルナ
ノエートなどの、液晶相を示しても示さなくても良い光
学活性化合物や、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挟
持することにより、ゲストホスト効果を応用した素子
〔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,SID
85Digest,68(1985)等〕などを構成す
ることができる。
The liquid crystal composition of the present invention contains an optically active compound such as cholesteryl nanoate, which may or may not exhibit a liquid crystal phase, and various additives such as an ultraviolet absorber and an antioxidant. Is also good. An element applying the guest-host effect by sandwiching the liquid crystal composition thus obtained between substrates with at least one of which is transparent [Shouichi Matsumoto, Ichino Tsunoda “Latest Liquid Crystal Technology” Industrial Research Meeting,
34 (1983): J. L. Fergason, SID
85 Digest, 68 (1985), etc.] and the like.

【0023】具体的な表示素子の一例として、図1及び
図2に示す。図1は電圧無印加時、図2は印加時の状態
を示し、各図中、1は観察者、2は透明基板、3は平行
配向処理が施された透明電極、4及び5は本発明の液晶
組成物であり、4は誘電異方性が正のネマチック液晶分
子、5は二色性色素分子を示し、9は入射光、8は偏光
板であり、7はその偏光方向、6は入射偏光を表わす。
この素子においては電圧無印加時には液晶及び二色性色
素の分子長軸が基板と平行であるため、素子は呈色状態
となる。一方、印加時には長軸方向が基板に垂直な状態
となるため無色状態となるものである。
An example of a concrete display device is shown in FIGS. 1 shows the state when no voltage is applied, and FIG. 2 shows the state when no voltage is applied. In each figure, 1 is an observer, 2 is a transparent substrate, 3 is a transparent electrode subjected to parallel alignment treatment, and 4 and 5 are the present invention Liquid crystal composition, 4 is a nematic liquid crystal molecule having a positive dielectric anisotropy, 5 is a dichroic dye molecule, 9 is incident light, 8 is a polarizing plate, 7 is its polarization direction, and 6 is Represents incident polarization.
In this element, when no voltage is applied, the molecular long axes of the liquid crystal and the dichroic dye are parallel to the substrate, so that the element is in a colored state. On the other hand, at the time of application, the long axis direction is perpendicular to the substrate, so that it is in a colorless state.

【0024】[0024]

【発明の効果】本発明の高い二色性と高い着色力をもつ
二色性色素およびこれを含む液晶組成物により、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 dichroic dye having high dichroism and high coloring power of the present invention and the liquid crystal composition containing the same can form a liquid crystal element such as a display element excellent in contrast and durability. .

【0025】[0025]

【実施例】以下に実施例により本発明をさらに具体的に
説明する。本発明はその要旨を越えない限り、以下の実
施例に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エチルスルホニル基
を含有するモノアゾ化合物
EXAMPLES The present invention will be described in more detail with reference to the following examples. The present invention is not limited to the following examples unless it exceeds the gist. Example 1 Monoazo compound containing perfluoroethylsulfonyl group represented by the following structural formula

【0026】[0026]

【化9】 [Chemical 9]

【0027】0.43g(1.0mmol)を酢酸8m
l、プロピオン酸5mlに溶解し、0〜5℃に冷却し、
43%ニトロシル硫酸0.44gを攪拌下に加え、この
温度で1時間反応させてジアゾ液を調製した。他方、下
記のカップラー
0.43 g (1.0 mmol) of acetic acid 8 m
1, dissolved in 5 ml of propionic acid, cooled to 0-5 ° C.,
0.44 g of 43% nitrosylsulfuric acid was added with stirring and reacted at this temperature for 1 hour to prepare a diazo solution. On the other hand, the following coupler

【0028】[0028]

【化10】 [Chemical 10]

【0029】0.50gをメタノール50mlに溶解し
て0〜5℃に冷却し、攪拌下にジアゾ液を徐々に加え、
アンモニア水を加えてpHを4に調製した後、同温度で
2時間反応させた。反応後、析出物を濾取し、カラムク
ロマトにより精製して下記構造式の色素0.22gを得
た。
0.50 g was dissolved in 50 ml of methanol, cooled to 0-5 ° C., and diazo solution was gradually added with stirring,
Ammonia water was added to adjust the pH to 4, and the mixture was reacted at the same temperature for 2 hours. After the reaction, the precipitate was collected by filtration and purified by column chromatography to obtain 0.22 g of the dye having the following structural formula.

【0030】[0030]

【化11】 [Chemical 11]

【0031】このアゾ色素を商品名ZLI−1565
(E.MERCK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0.2wt%の濃度で溶
解させ青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。
This azo dye is called as ZLI-1565 under the trade name.
A blue guest-host liquid crystal composition was prepared by dissolving it in a phenylcyclohexane-based liquid crystal mixture marketed as (E. MERCK) at a concentration of 0.2 wt%. A glass substrate with a transparent electrode, which was coated with a polyimide resin, cured and rubbed, faced, and was sealed in a cell having a gap of 9 μm so that the liquid crystal was aligned in parallel.

【0032】この青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 :602nm)におけるオーダーパラ
メーター(S)を下記の式
The absorbance for linearly polarized light parallel to the alignment direction (A // ) and the absorbance for linearly polarized light perpendicular to the alignment direction (A⊥) of this blue-colored cell were measured, and the absorption peak (λ max : 602 nm) was measured. ) The order parameter (S) in

【0033】[0033]

【数1】S=(A//−A⊥)/(A//−2A⊥) から求めた結果、S=0.75であった。[Formula 1] As a result of obtaining from S = (A // −A⊥) / (A // −2A⊥), S = 0.75.

【0034】上記のZLI−1565の代わりに商品名
ZLI−4792(E.MERCK社製)として市販さ
れているフッ系液晶混合物を用いて、同様にしてオーダ
パラメータを求めた結果、S=0.77(λmax :59
4nm)であった。
In the same manner as described above, an order parameter was determined using a fluorine-based liquid crystal mixture marketed under the trade name ZLI-4792 (manufactured by E. MERCK) instead of the above ZLI-1565. As a result, S = 0. 77 (λ max : 59
4 nm).

【0035】実施例2 実施例1に準じた方法により得られたアゾ化合物のフェ
ニルシクロヘキサン系液晶混合物:商品名ZLI−15
65(E.MERCK社製)中におけるオーダーパラー
メーター(S)と色相を表−1に示す。表中、
Example 2 Phenylcyclohexane type liquid crystal mixture of azo compound obtained by the method according to Example 1: Trade name ZLI-15
Table 1 shows the order parameter (S) and hue in 65 (manufactured by E. MERCK). In the table,

【0036】[0036]

【化12】 [Chemical 12]

【0037】はトランス体を示す。Represents a trans form.

【0038】[0038]

【表1】 [Table 1]

【0039】[0039]

【表2】 [Table 2]

【0040】[0040]

【表3】 [Table 3]

【0041】[0041]

【表4】 [Table 4]

【0042】[0042]

【表5】 [Table 5]

【図面の簡単な説明】[Brief description of drawings]

【図1】本発明に係る液晶素子の電圧無印加状態の略示
的な断面図を表わす。
FIG. 1 is a schematic cross-sectional view of a liquid crystal element according to the present invention in a state in which no voltage is applied.

【図2】本発明に係る液晶素子の電圧印加状態の略示的
な断面図を表わす。
FIG. 2 shows a schematic cross-sectional view of a voltage applied state of a liquid crystal element according to the present invention.

【符号の説明】[Explanation of symbols]

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 polarization 7 Polarization direction of incident polarization 8 Polarizing light 9 Incident light

Claims (3)

【特許請求の範囲】[Claims] 【請求項1】 一般式〔I〕 【化1】 (式中、Bは水素原子または非イオン性置換基を示し、
Xは 【化2】 を示し、Z1 〜Z13はそれぞれ水素原子、ハロゲン原
子、メチル基、メトキシ基またはトリフルオロメチル基
を示し、また、Z1 とZ2 、Z4 とZ5 、Z7 とZ 8
10とZ11は互い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く、nは1〜18、mは0
〜2、pは0または1の数を示す。)で表わされること
を特徴とするパーフルオロアルキルスルホニル基を含有
するアゾ系二色性色素。
1. A compound represented by the general formula [I]:(In the formula, B represents a hydrogen atom or a nonionic substituent,
X is, Z1~ Z13Are hydrogen atom and halogen atom respectively
Child, methyl group, methoxy group or trifluoromethyl group
, And also Z1And Z2, ZFourAnd ZFive, Z7And Z 8,
ZTenAnd Z11Are linked to each other by an aliphatic ring, an aromatic ring or
A nitrogen-containing aromatic ring may be formed, n is 1 to 18 and m is 0.
˜2, p is a number of 0 or 1. )
Containing a perfluoroalkylsulfonyl group characterized by
Azo-based dichroic dye.
【請求項2】 液晶物質と請求項1に記載のパーフルオ
ロアルキルスルホニル基を含有するアゾ系二色性色素を
含むことを特徴とする液晶組成物。
2. A liquid crystal composition comprising a liquid crystal substance and the azo-based dichroic dye having a perfluoroalkylsulfonyl group according to claim 1.
【請求項3】 請求項2に記載の液晶組成物を用いたこ
とを特徴とする液晶素子。
3. A liquid crystal device using the liquid crystal composition according to claim 2.
JP5002095A 1994-09-21 1995-03-09 Dichroic coloring matter, liquid crystal composition and liquid crystal element containing the same coloring matter Pending JPH08143865A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP5002095A JPH08143865A (en) 1994-09-21 1995-03-09 Dichroic coloring matter, liquid crystal composition and liquid crystal element containing the same coloring matter

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
JP6-227082 1994-09-21
JP22708294 1994-09-21
JP5002095A JPH08143865A (en) 1994-09-21 1995-03-09 Dichroic coloring matter, liquid crystal composition and liquid crystal element containing the same coloring matter

Publications (1)

Publication Number Publication Date
JPH08143865A true JPH08143865A (en) 1996-06-04

Family

ID=26390465

Family Applications (1)

Application Number Title Priority Date Filing Date
JP5002095A Pending JPH08143865A (en) 1994-09-21 1995-03-09 Dichroic coloring matter, liquid crystal composition and liquid crystal element containing the same coloring matter

Country Status (1)

Country Link
JP (1) JPH08143865A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2008133421A (en) * 2006-05-30 2008-06-12 Mitsubishi Chemicals Corp Azo dye for anisotropic dye film

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2008133421A (en) * 2006-05-30 2008-06-12 Mitsubishi Chemicals Corp Azo dye for anisotropic dye film

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