JPH0548263B2 - - Google Patents
Info
- Publication number
- JPH0548263B2 JPH0548263B2 JP59281220A JP28122084A JPH0548263B2 JP H0548263 B2 JPH0548263 B2 JP H0548263B2 JP 59281220 A JP59281220 A JP 59281220A JP 28122084 A JP28122084 A JP 28122084A JP H0548263 B2 JPH0548263 B2 JP H0548263B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- substituted
- liquid crystal
- compound
- alkoxy group
- 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.)
- Expired - Fee Related
Links
- 239000004973 liquid crystal related substance Substances 0.000 claims description 25
- 125000003545 alkoxy group Chemical group 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 12
- 125000005605 benzo group Chemical group 0.000 claims description 11
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 8
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 claims description 8
- -1 xanthene compound Chemical class 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 description 21
- 239000000975 dye Substances 0.000 description 13
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000004988 Nematic liquid crystal Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- JZCCFEFSEZPSOG-UHFFFAOYSA-L copper(II) sulfate pentahydrate Chemical compound O.O.O.O.O.[Cu+2].[O-]S([O-])(=O)=O JZCCFEFSEZPSOG-UHFFFAOYSA-L 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- IGARGHRYKHJQSM-UHFFFAOYSA-N cyclohexylbenzene Chemical compound C1CCCCC1C1=CC=CC=C1 IGARGHRYKHJQSM-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 241000720945 Hosta Species 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 230000003098 cholesteric effect Effects 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
Landscapes
- Liquid Crystal (AREA)
- Devices For Indicating Variable Information By Combining Individual Elements (AREA)
Description
〔産業上の利用分野〕
本発明は、新規なベンゾ（チオ）キサンテン系
化合物および該化合物を含有する液晶組成物に関
する。
〔従来の技術〕
従来から液晶に色素化合物を溶解してなる液晶
組成物を、対向する２枚の電極間に介在させ、色
素化合物と液晶とのゲスト・ホスト効果を利用し
てカラー表示を行なうことが知られている。
かかる液晶組成物に使用される色素化合物は、
特に、２色性比が高いこと、液晶に対して高い溶
解性を有すること等の性質を有することが必要で
ある。
本発明者らは、上記性質を有し、黄色〜橙色の
色相を示す色素化合物を提供すべく、ベンゾ（チ
オ）キサンテン系化合物に着目して検討を行なつ
た。
〔発明が解決しようとする問題点〕
ベンゾ（チオ）キサンテン系化合物としては、
従来、種々のものが知られているが、それらはも
つぱらポリエステル繊維等の繊維類用の染料とし
て使用されていた（特公昭44−4660、特公昭45−
33551、特公昭53−5888）。
しかしながら、本発明者らの検討によれば、従
来繊維類用の染料として知られているベンゾ（チ
オ）キサンテン系化合物が必ずしも前述の様な液
晶組成物で使用する色素化合物に要求されるよう
な性質を満足するものではなく、これらが直ちに
液晶組成物の色素化合物として適用できるもので
はないことが分つた。
本発明は、高い２色性比及び液晶に対して良好
な溶解性を示す特定のベンゾ（チオ）キサンテン
系化合物およびこれを含有し、良好なカラー表示
が行なえる液晶組成物を提供することを目的とす
る。
〔問題点を解決するための手段〕
本発明は、一般式〔〕
（式中、Ｘは酸素原子または硫黄原子を示し、Ａ
はアルキレン基を示し、R1は水素原子；アルコ
キシ基で置換されていてもよいアルキル基；アル
コキシ基で置換されていてもよいアルコキシ基を
示し、R2はアルキル基、アルコキシ基、アルキ
ルシクロヘキシル基で置換されていてもよいフエ
ニル基；アルキル基、アルキルシクロヘキシル基
で置換されていてもよいシクロヘキシル基を示
す。）
で表わされるベンゾ（チオ）キサンテン系化合物
及び該化合物を含有する液晶組成物を要旨とす
る。
本発明のベンゾ（チオ）キサンテン系化合物は
前記一般式〔〕で表わされるものである。
式中Ａは―（CH2）o――で表わされるアルキレン基
で、ｎは１〜４が好ましく、ｎ＝２が特に好まし
い。R1は水素原子；炭素数１〜８等のアルコキ
シ基で置換されていてもよい炭素数１〜13等のア
ルキル基；炭素数１〜８等のアルコキシ基で置換
されていてもよい炭素数１〜13等のアルコキシ基
を示す。またR2は炭素数１〜13等のアルキル基
で置換されていてもよいフエニル基；炭素数１〜
８等のアルコキシ基で置換されていてもよいフエ
ニル基；トランス−４−アルキル（例えば炭素数
１〜８のアルキル）シクロヘキシル基で置換され
ていてもよいフエニル基、トランス−４−アルキ
ル（例えば炭素数１〜８のアルキル）シクロヘキ
シル基；トランス−４−アルキル（例えば炭素数
１〜８のアルキル）シクロヘキシル基で置換され
ていてもよいシクロヘキシル基を示す。尚、上記
の炭素数３以上のアルキル基またはアルコキシ基
は直鎖状であつても分岐鎖状であつてもよい。
前記一般式〔〕で示されるベンゾ（チオ）キ
サンテン系化合物は、例えば、特公昭44−4660記
載の次の方法により合成される。
上記一般式〔〕〜〔〕におけるＸ、Ａ、
R1およびR2は前記と同義を示す。
本発明で用いるネマチツク液晶としては、動作
温度範囲でネマチツク状態を示すものであれば、
かなり広い範囲で選択することができる。またこ
のようにネマチツク液晶に後述の旋光性物質を加
えることにより、コレステリツク状態をとらせる
ことができる。ネマチツク液晶の例としては第１
表に示される物質、あるいはこれらの誘導体があ
げられる。
[Industrial Application Field] The present invention relates to a novel benzo(thio)xanthene compound and a liquid crystal composition containing the compound. [Prior art] Conventionally, a liquid crystal composition made by dissolving a dye compound in liquid crystal is interposed between two opposing electrodes, and color display is performed by utilizing the guest-host effect between the dye compound and the liquid crystal. It is known. The dye compound used in such a liquid crystal composition is
In particular, it is necessary to have properties such as a high dichroic ratio and high solubility in liquid crystals. The present inventors conducted studies focusing on benzo(thio)xanthene compounds in order to provide a dye compound having the above properties and exhibiting a yellow to orange hue. [Problems to be solved by the invention] As benzo(thio)xanthene compounds,
A variety of dyes have been known in the past, but they were primarily used as dyes for fibers such as polyester fibers (Special Publications No. 44-4660, No. 4660, No. 45).
33551, Special Publication Showa 53-5888). However, according to the studies of the present inventors, benzo(thio)xanthene compounds, conventionally known as dyes for textiles, do not necessarily meet the requirements for pigment compounds used in liquid crystal compositions as described above. It was found that these properties were not satisfactory, and that they could not be immediately applied as dye compounds for liquid crystal compositions. The present invention aims to provide a specific benzo(thio)xanthene compound that exhibits a high dichroic ratio and good solubility in liquid crystals, and a liquid crystal composition containing the same that provides good color display. purpose. [Means for solving the problems] The present invention solves the problem by solving the general formula [] (In the formula, X represents an oxygen atom or a sulfur atom, and A
represents an alkylene group, R 1 is a hydrogen atom; an alkyl group which may be substituted with an alkoxy group; an alkoxy group which may be substituted with an alkoxy group, R 2 is an alkyl group, an alkoxy group, an alkylcyclohexyl group phenyl group which may be substituted with; a cyclohexyl group which may be substituted with an alkyl group or an alkylcyclohexyl group. ) A benzo(thio)xanthene compound represented by the following and a liquid crystal composition containing the compound are summarized. The benzo(thio)xanthene compound of the present invention is represented by the general formula []. In the formula, A is an alkylene group represented by --(CH 2 ) o --, and n is preferably 1 to 4, particularly preferably n=2. R 1 is a hydrogen atom; an alkyl group having 1 to 13 carbon atoms which may be substituted with an alkoxy group having 1 to 8 carbon atoms; a carbon number which may be substituted with an alkoxy group having 1 to 8 carbon atoms; Indicates an alkoxy group such as 1 to 13. R 2 is a phenyl group which may be substituted with an alkyl group having 1 to 13 carbon atoms;
Phenyl group optionally substituted with an alkoxy group such as 8; trans-4-alkyl (e.g. alkyl having 1 to 8 carbon atoms); phenyl group optionally substituted with a cyclohexyl group; trans-4-alkyl (e.g. carbon (alkyl having 1 to 8 carbon atoms) cyclohexyl group; trans-4-alkyl (for example, alkyl having 1 to 8 carbon atoms) represents a cyclohexyl group which may be substituted with a cyclohexyl group. In addition, the above-mentioned alkyl group or alkoxy group having 3 or more carbon atoms may be linear or branched. The benzo(thio)xanthene compound represented by the general formula [] is synthesized, for example, by the following method described in Japanese Patent Publication No. 44-4660. X, A, in the above general formulas [] to [],
R 1 and R 2 have the same meanings as above. The nematic liquid crystal used in the present invention may be one that exhibits a nematic state within the operating temperature range.
You can choose from a fairly wide range. Furthermore, by adding an optically active substance, which will be described later, to the nematic liquid crystal, it can be made to assume a cholesteric state. The first example of a nematic liquid crystal is
Examples include the substances shown in the table or their derivatives.
【表】【table】
【表】【table】
本発明のベンゾ（チオ）キサンテン系化合物
は、液晶に対し良好な溶解性を示し、得られる液
晶組成物の２色性比が高いので、鮮明なカラー表
示が可能である。
〔実施例〕
以下、実施例により本発明を説明するが、本発
明はかかる実施例により限定されるものではな
い。
なお、以下に２色性比を示すオーダー・パラメ
ータについて説明すれば、色素化合物のオーダ
ー・パラメーターＳは実験的には次式から求めら
れる。
Ｓ＝Ａ−Ａ⊥／2A⊥＋Ａ
ここでＡおよびＡ⊥は、それぞれ液晶の配向
方向に対して平行および垂直に偏光した光に対す
る色素の吸光度である。
オーダー・パラメーターＳは具体的にはゲス
ト・ホスト型液晶素子の表示コントラストを示す
値であり、この値が理論上１に近づく程、白ぬけ
部分の残色度が減少し、明るくコントラストの大
きい鮮明な表示が可能となる。
実施例 １
(イ) 下記構造式
で示される化合物1.05ｇを酢酸50ml濃塩酸１ml
に溶解し、水15mlを加えて０℃に冷却する。こ
の溶液に亜硝酸ナトリウム0.24ｇの水溶液を添
加し、０〜５℃で４時間撹拌する。硫酸銅５水
塩2.14ｇを水20mlに溶解し、95℃〜100℃に加
熱する。この溶液に上記の水溶液を１時間かけ
て添加し、この反応混合物を95〜100℃で２時
間撹拌する。析出した結晶をろ過、乾燥し、シ
リカゲル（和光純薬工業株式会社製造；Ｃ−
200商品名）を担体とし、そしてクロロホルム
を分離溶媒とするカラムクロマトグラフイーに
て不純物を分離精製し、下記構造式
で示される化合物190mgを得た。本化合物は318
℃の分解点を示した。
得られた化合物を前述のフエニルシクロヘキ
サン系混合液晶ZLI−1132に添加し、70℃以上
に加熱して液晶が等方性液体になつた状態でよ
くかきまぜた後、放置冷却する工程を繰返し行
ない化合物（色素）を溶解した。
このように調製した上記液晶組成物を、透明
電極を有し、液晶と接する面をポリアミド系樹
脂を塗布硬化後ラビングしてホモジニアス配向
処理を施した上下２枚のガラス基板からなる基
板間ギヤツプ10μｍの素子に封入した。上記配
向処理を施した素子内では電圧無添加のとき上
記液晶は、ホモジアニス配向状態をとり、色素
分子もホスト液晶に従つて同様の配向をとるも
のであつた。
このようにして作製したゲスト・ホスト素子
の吸収スペクトルの測定を、液晶分子の配向方
向に対して平行に偏光した光及び垂直に偏光し
た光の各々を用いて行ない、これら各偏光に対
する色素の最大吸収波長を求めた。色素の吸光
度を求めるにあたつては、ホスタ液晶およびガ
ラス基板による吸収と、素子の反射損失に関し
て補正を行なつた。
また、各偏光に対するＡ及びＡ⊥を用い、
前述の式
Ｓ＝Ａ−Ａ⊥／2A⊥＋Ａ
からオーダー・パラメーターＳの値を算出し
た。
以上の結果を下記第２表（No.１）に示した。
(ロ) 下記構造式
で示される化合物1.23ｇを酢酸60ml濃塩酸１ml
に溶解し水20mlを加えて０℃に冷却する。この
溶液に亜硝酸ナトリウム0.27ｇの水溶液を添加
し、０〜５℃で４時間撹拌する。硫酸銅５水塩
2.45ｇを水20mlに溶解し、95℃〜100℃に加熱
する。この溶液に上記の水溶液を１時間かけて
添加し、この反応混合物を95〜100℃で２時間
撹拌する。析出した結晶をろ過、乾燥し、シリ
カゲル（和光純薬工業株式会社製造；Ｃ−200
商品名）を担体とし、そしてクロロホルムを分
離溶媒とするカラムクロマトグラフイーにて不
純物を精製し、下記構造式
で示される化合物270mgを得た。本化合物は313
℃の分解点を示した。
本化合物を上述の(イ)で得られた化合物と同様
にして前述のフエニルシクロヘキサン系混合液
晶ZLI−1132に溶解して最大吸収波長及びオー
ダー・パラメーターＳを算出し、下記第２表No.
３に示した。
上記と同様な操作により下記第２表に示す化
合物を製造し、上記と同様な操作により単離し
た化合物の最大吸収波長及びオーダー・パラメ
ーター(S)を測定し、あわせて第２表にその結果
を示した。（但し、
The benzo(thio)xanthene compound of the present invention exhibits good solubility in liquid crystal, and the obtained liquid crystal composition has a high dichroic ratio, so that clear color display is possible. [Examples] The present invention will be explained below with reference to Examples, but the present invention is not limited to these Examples. The order parameter indicating the dichroic ratio will be explained below.The order parameter S of the dye compound can be experimentally determined from the following equation. S=A-A⊥/2A⊥+A where A and A⊥ are the absorbances of the dye for light polarized parallel and perpendicular to the alignment direction of the liquid crystal, respectively. Specifically, the order parameter S is a value that indicates the display contrast of a guest-host type liquid crystal element.Theoretically, as this value approaches 1, the degree of residual color in white areas will decrease, resulting in brighter, clearer images with greater contrast. It is possible to display Example 1 (a) The following structural formula Add 1.05g of the compound shown to 50ml of acetic acid and 1ml of concentrated hydrochloric acid.
Add 15 ml of water and cool to 0°C. An aqueous solution of 0.24 g of sodium nitrite is added to this solution, and the mixture is stirred at 0 to 5°C for 4 hours. 2.14 g of copper sulfate pentahydrate is dissolved in 20 ml of water and heated to 95°C to 100°C. The above aqueous solution is added to this solution over a period of 1 hour, and the reaction mixture is stirred at 95-100°C for 2 hours. The precipitated crystals were filtered and dried, and silica gel (manufactured by Wako Pure Chemical Industries, Ltd.; C-
200 (trade name) as a carrier and chloroform as a separation solvent, impurities were separated and purified, and the following structural formula was obtained. 190 mg of the compound shown was obtained. This compound is 318
The decomposition point in °C is shown. The obtained compound was added to the above-mentioned phenylcyclohexane mixed liquid crystal ZLI-1132, heated to 70℃ or higher to turn the liquid crystal into an isotropic liquid, stirred well, and then left to cool.The process was repeated. The compound (dye) was dissolved. The above-mentioned liquid crystal composition prepared in this manner was applied to two glass substrates, each having a transparent electrode and a polyamide resin applied to the surface in contact with the liquid crystal, cured, and subjected to homogeneous alignment treatment by rubbing, with a gap of 10 μm between the substrates. encapsulated in the element. In the element subjected to the above alignment treatment, the liquid crystal was in a homodianis alignment state when no voltage was applied, and the dye molecules were also aligned in the same manner according to the host liquid crystal. The absorption spectrum of the guest-host device thus prepared was measured using light polarized parallel to and perpendicular to the alignment direction of the liquid crystal molecules. The absorption wavelength was determined. When determining the absorbance of the dye, corrections were made for absorption by the hosta liquid crystal and glass substrate and reflection loss of the element. Also, using A and A⊥ for each polarized light,
The value of the order parameter S was calculated from the above equation S=A-A⊥/2A⊥+A. The above results are shown in Table 2 (No. 1) below. (b) The following structural formula Add 1.23g of the compound shown to 60ml of acetic acid and 1ml of concentrated hydrochloric acid.
Add 20 ml of water and cool to 0°C. An aqueous solution of 0.27 g of sodium nitrite is added to this solution, and the mixture is stirred at 0 to 5°C for 4 hours. copper sulfate pentahydrate
Dissolve 2.45g in 20ml of water and heat to 95°C to 100°C. The above aqueous solution is added to this solution over a period of 1 hour, and the reaction mixture is stirred at 95-100°C for 2 hours. The precipitated crystals were filtered and dried, and silica gel (manufactured by Wako Pure Chemical Industries, Ltd.; C-200
The impurities were purified by column chromatography using (trade name) as a carrier and chloroform as a separation solvent, and the following structural formula was obtained. 270 mg of the compound shown was obtained. This compound is 313
The decomposition point in °C is shown. This compound was dissolved in the above-mentioned phenylcyclohexane mixed liquid crystal ZLI-1132 in the same manner as the compound obtained in (a) above, and the maximum absorption wavelength and order parameter S were calculated, and the results are shown in Table 2 below, No.
Shown in 3. The compounds shown in Table 2 below were produced by the same operations as above, and the maximum absorption wavelength and order parameter (S) of the isolated compounds were measured by the same operations as above, and the results are also shown in Table 2. showed that. (however,
【式】はトランス −シクロヘキシルを示す。）[Formula] is transformer - indicates cyclohexyl. )
【表】【table】
【表】【table】
Claims (1)
はアルキレン基を示し、R1は水素原子；アルコ
キシ基で置換されていてもよいアルキル基；アル
コキシ基で置換されていてもよいアルコキシ基を
示し、R2はアルキル基、アルコキシ基、アルキ
ルシクロヘキシル基で置換されていてもよいフエ
ニル基；アルキル基、アルキルシクロヘキシル基
で置換されていてもよいシクロヘキシル基を示
す。） で表わされるベンゾ（チオ）キサンテン系化合
物。 ２ 一般式〔〕 （式中、Ｘは酸素原子または硫黄原子を示し、Ａ
はアルキレン基を示し、R1は水素原子；アルコ
キシ基で置換されていてもよいアルキル基；アル
コキシ基で置換されていてもよいアルコキシ基を
示し、R2はアルキル基、アルコキシ基、アルキ
ルシクロヘキシル基で置換されていてもよいフエ
ニル基；アルキル基、アルキルシクロヘキシル基
で置換されていてもよいシクロヘキシル基を示
す。） で表わされるベンゾ（チオ）キサンテン系化合物
を含有する液晶組成物。[Claims] 1. General formula [] (In the formula, X represents an oxygen atom or a sulfur atom, and A
represents an alkylene group, R 1 is a hydrogen atom; an alkyl group which may be substituted with an alkoxy group; an alkoxy group which may be substituted with an alkoxy group, R 2 is an alkyl group, an alkoxy group, an alkylcyclohexyl group phenyl group which may be substituted with; a cyclohexyl group which may be substituted with an alkyl group or an alkylcyclohexyl group. ) A benzo(thio)xanthene compound represented by 2 General formula [] (In the formula, X represents an oxygen atom or a sulfur atom, and A
represents an alkylene group, R 1 is a hydrogen atom; an alkyl group which may be substituted with an alkoxy group; an alkoxy group which may be substituted with an alkoxy group, R 2 is an alkyl group, an alkoxy group, an alkylcyclohexyl group phenyl group which may be substituted with; a cyclohexyl group which may be substituted with an alkyl group or an alkylcyclohexyl group. ) A liquid crystal composition containing a benzo(thio)xanthene compound represented by:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59281220A JPS61155465A (en) | 1984-12-27 | 1984-12-27 | Benzo(thio)xanthene compound and liquid crystal compound containing same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59281220A JPS61155465A (en) | 1984-12-27 | 1984-12-27 | Benzo(thio)xanthene compound and liquid crystal compound containing same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61155465A JPS61155465A (en) | 1986-07-15 |
| JPH0548263B2 true JPH0548263B2 (en) | 1993-07-21 |
Family
ID=17636037
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59281220A Granted JPS61155465A (en) | 1984-12-27 | 1984-12-27 | Benzo(thio)xanthene compound and liquid crystal compound containing same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61155465A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0553167U (en) * | 1991-12-17 | 1993-07-13 | 株式会社電研社 | Coaxial cable connector |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102005037115A1 (en) * | 2005-08-03 | 2007-02-08 | Basf Ag | polychromophores |
-
1984
- 1984-12-27 JP JP59281220A patent/JPS61155465A/en active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0553167U (en) * | 1991-12-17 | 1993-07-13 | 株式会社電研社 | Coaxial cable connector |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61155465A (en) | 1986-07-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |