JPS6383191A - Liquid crystal material - Google Patents
Liquid crystal materialInfo
- Publication number
- JPS6383191A JPS6383191A JP22797086A JP22797086A JPS6383191A JP S6383191 A JPS6383191 A JP S6383191A JP 22797086 A JP22797086 A JP 22797086A JP 22797086 A JP22797086 A JP 22797086A JP S6383191 A JPS6383191 A JP S6383191A
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- crystal material
- optically active
- phase
- formula
- 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.)
- Granted
Links
- 239000000463 material Substances 0.000 title claims abstract description 22
- 239000004973 liquid crystal related substance Substances 0.000 title claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 7
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 5
- -1 2-octyl Chemical group 0.000 claims abstract description 4
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 1
- 239000004990 Smectic liquid crystal Substances 0.000 abstract description 13
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract description 7
- 239000013078 crystal Substances 0.000 abstract description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract description 3
- 230000001747 exhibiting effect Effects 0.000 abstract description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- 239000012071 phase Substances 0.000 description 19
- 238000000034 method Methods 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 239000005262 ferroelectric liquid crystals (FLCs) Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 230000007704 transition Effects 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000004988 Nematic liquid crystal Substances 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- QPRQEDXDYOZYLA-YFKPBYRVSA-N (S)-2-methylbutan-1-ol Chemical compound CC[C@H](C)CO QPRQEDXDYOZYLA-YFKPBYRVSA-N 0.000 description 1
- RLRJTIVTCUAJJX-UHFFFAOYSA-N 7-octoxy-9h-fluorene-2-carboxylic acid Chemical compound OC(=O)C1=CC=C2C3=CC=C(OCCCCCCCC)C=C3CC2=C1 RLRJTIVTCUAJJX-UHFFFAOYSA-N 0.000 description 1
- 101100257134 Caenorhabditis elegans sma-4 gene Proteins 0.000 description 1
- 206010011878 Deafness Diseases 0.000 description 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000003446 memory effect Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 125000004950 trifluoroalkyl group Chemical group 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Abstract
Description
【発明の詳細な説明】
［発明の目的コ
（産業上の利用分野）
本発明は、新規な液晶材料に関し、特にキラルスメクテ
ックＣ相を有する強誘電性液晶に適した液晶材料に係る
。DETAILED DESCRIPTION OF THE INVENTION [Objective of the Invention (Field of Industrial Application) The present invention relates to a novel liquid crystal material, and particularly to a liquid crystal material suitable for a ferroelectric liquid crystal having a chiral smectic C phase.
（従来の技術）
液晶は、従来よシ小型クラットパネルディスグレーの本
命として電卓１時計等に広く用いられている。また、最
近では自動車用ディスプレー。(Prior Art) Liquid crystals have been widely used in calculators, watches, etc. as the mainstay of conventional small-sized flat panel displays. Also, recently, automotive displays.
パーソナルコンビ、−夕月デイスプレーとしても用いら
れてきている。更に、小聾液晶テレビのような動画用デ
ィスプレーにも応用され始じめている。It has also been used as a personal combination and evening moon display. Furthermore, it is beginning to be applied to video displays such as small-deaf LCD televisions.
ところで、従来、電卓９時計等に用いられる液晶として
はツイストネマティク液晶が知られている。しかしなが
ら、前記液晶を用いた表示方式では応答速度が不十分で
あることや、クロストークが発生すること等の問題があ
った。このため、かかる表示方式では動画用の大′画面
７’４スプレー等の速い応答速度が要求されるものへの
応用は困離であった。こうした問題を解決する九めにｔ
ｈｌｔｚｆｌｌｍ ｔｒａｎｓｌｓｔｏｒ （ＴＦＴ）
ｆ用い九アクティブマトリックスのような方式も開発
されているが、製造コストが高い等の問題があった。Incidentally, twisted nematic liquid crystals are conventionally known as liquid crystals used in calculators, watches, and the like. However, the display method using the liquid crystal has problems such as insufficient response speed and crosstalk. For this reason, it has been difficult to apply this display method to applications that require a fast response speed, such as a large screen 7'4 screen for moving pictures. The ninth step to solving these problems
hltzfllm translster (TFT)
A method using f-based active matrix has also been developed, but it has problems such as high manufacturing cost.
このようなことから、ツイストネマチック液晶を用いた
表示方式に代るものとして、強誘電液晶による表示方式
が注目されている。この方式は、１９７５年にＲ，Ｂ、
Ｍａｙｅｒらによって発表されたもので、従来方式に
比べて応答速度が速いこと、メモリ効果を持つこと等の
特徴を有している。かかる強誘電性液晶は、液晶形態が
キラルスメクテックＣ相をとる。こうした強誘電性液晶
となシ得る液晶材料としては、従来よシ多数のものが知
られている。しかしながら、従来の液晶材料は空気中の
水分や光等に対して不安定であシ、しかもキ２ルスメク
テックＣ相をとる温度範囲が狭く、使用上の制約が大き
いという問題があった。For these reasons, a display system using ferroelectric liquid crystal is attracting attention as an alternative to a display system using twisted nematic liquid crystal. This method was developed in 1975 for R, B,
This method was announced by Mayer et al., and has characteristics such as faster response speed and memory effect compared to conventional methods. Such a ferroelectric liquid crystal has a liquid crystal form of a chiral smectic C phase. A large number of liquid crystal materials that can be used as such ferroelectric liquid crystals are known. However, conventional liquid crystal materials are unstable to moisture in the air, light, etc., and the temperature range in which they exhibit the Kirsmectic C phase is narrow, which poses a problem in that they are severely restricted in use.
（発明が解決しようとする問題点）
本発明は、上記従来の問題点を解決するためになされた
もので、強誘電性液晶に適用する上で必要なキラルスメ
クテックＣ相の温度範囲を拡大でき、かつ熱力学的な安
定性の優れた液晶材料を提供しようとするものである。(Problems to be Solved by the Invention) The present invention has been made to solve the above conventional problems, and expands the temperature range of the chiral smectic C phase necessary for application to ferroelectric liquid crystals. The purpose of the present invention is to provide a liquid crystal material that can be used as a liquid crystal material and has excellent thermodynamic stability.
［発明の構成コ
（問題点を解決するための手段及び作用）本発明は、一
般式
〔但し、式中のＲはアルキル基、Ｒ９は不整合炭素原子
を有する光学活性基を示す〕にて表わされる７−アルコ
キシフルオレン−２−カルボン酸エステルからなる液晶
材料である。[Constitution of the Invention (Means and Effects for Solving Problems)] The present invention is based on the general formula [wherein R is an alkyl group and R9 is an optically active group having a mismatched carbon atom]. This is a liquid crystal material made of 7-alkoxyfluorene-2-carboxylic acid ester shown below.
上記一般式（Ａ）中のＲは、キラルスメクテックＣ相の
温度範囲の拡大の観点から炭素数３〜１８の直鎖アルキ
ル基を選定することが望ましく、よシ好ましいＲは炭素
数４〜１４の直鎖状アルキル基である。R in the above general formula (A) is preferably a straight chain alkyl group having 3 to 18 carbon atoms from the viewpoint of expanding the temperature range of the chiral smectic C phase, and more preferably R is a straight chain alkyl group having 4 to 18 carbon atoms. 14 straight-chain alkyl groups.
上記一般式（Ａ）中のＣとしては、キツルスメクテック
Ｃ相の温度範囲の拡大等の観点から一般式〔但し、式中
のＲ１−Ｒ３はアルキル基、）飄ログン基、シアノ基、
トリフルオルアルキル基、水素原子のいずれかで、Ｒ１
’；Ｒ２１Ｒ２笑Ｒ，、Ｒ３（Ｒ１を満足し、ｎはＯ〜
１５の整数（好ましくは０〜８の整数）を示す〕にて表
わされる不整炭素原子を有するアルキル基を用いること
が望ましい。よシ好ましいＲ＊は、光学活性な２−メチ
ルブチル基、２−オクチル基である。From the viewpoint of expanding the temperature range of the Chyrus Mectec C phase, C in the above general formula (A) may be represented by the following general formulas:
Either a trifluoroalkyl group or a hydrogen atom, R1
';R21R2 lol R,, R3 (satisfies R1, n is O~
It is desirable to use an alkyl group having an asymmetric carbon atom represented by an integer of 15 (preferably an integer of 0 to 8). Very preferable R* is an optically active 2-methylbutyl group or 2-octyl group.
本発明の液晶材となる７−アルコキシフルオレノン−２
−カルボン酸は、以下に説明する合成方法によシ製造さ
れる。7-alkoxyfluorenone-2, which is the liquid crystal material of the present invention
-Carboxylic acids are produced by the synthetic method described below.
上記合成方法において、原料（１）の製造及び（Ｉ）〜
（ＩＩＩ）までの反応は公知の方法である。即ち、原料
（１）は、例えばＯｒｇ−５ｙｎｔｈ−１９３３，１３
＃７４に開示されているように市販のフルオレンから３
段階の反応を経て得られる。また、前記（１）〜（Ｉｔ
）までの反応はＣ，Ｈ，Ｃｏａｋ等によるＪ、 Ｏｒｇ
＊ Ｃｈ＠ｍ、 １９５４＋１９．６２６で発表された
方法、前記（ＩＩ）〜（１）までの反応はＧ、Ｗ、 Ｇ
ｒａｙ等によるＪ、、 １９５７ 、３２２８で発表さ
れ九方法、に夫々従りた。一方、（■）の７−アルコキ
シフルオレン−２−カルボン酸エステルは（ＩＩＩ）を
塩化チオニルによシ酸塩化物とした後、ヒＩＪジン中で
光学活性アルコールを反応させることによシ得られる。In the above synthesis method, the production of raw material (1) and (I) -
The reactions up to (III) are known methods. That is, the raw material (1) is, for example, Org-5ynth-1933,13
3 from commercially available fluorene as disclosed in #74.
Obtained through a step-by-step reaction. In addition, the above (1) to (It
), the reaction up to J, Org by C, H, Coak et al.
*The method published in Ch@m, 1954+19.626, the reactions (II) to (1) above are G, W, G
The nine methods published by Ray et al., J., 1957, 3228, were followed respectively. On the other hand, the 7-alkoxyfluorene-2-carboxylic acid ester of (■) can be obtained by converting (III) into thionyl chloride and reacting it with an optically active alcohol in hydroxide. .
しかして、本発明の液晶材料である一般式にて表わされ
る７−アルコキシフルオレン−２−カルボン酸エステル
はキラルスメクテックＣ相の温度範囲が拡大され、かつ
熱力学的な安定性が優れているため、これらの２種以上
を混合するか、又は他のキラルスメクテックＣ相を示す
化合物と混合することによシ従来に比べて広い温度範囲
でキラルスメクテックＣ相を有する強誘電性液晶を実現
できる。Therefore, the 7-alkoxyfluorene-2-carboxylic acid ester represented by the general formula, which is the liquid crystal material of the present invention, has an expanded temperature range of chiral smectic C phase and excellent thermodynamic stability. Therefore, by mixing two or more of these or with other compounds exhibiting a chiral smectic C phase, it is possible to produce ferroelectric liquid crystals having a chiral smectic C phase over a wider temperature range than before. realizable.
（発明の実施例） 以下、本発明の合成例及び実施例を詳細に説明する。(Example of the invention) Synthesis examples and examples of the present invention will be described in detail below.
合成例１
まず、公知の方法で合成し九７−へブチルオキシ−フル
オレン−２−カルボン酸３８．２１！（０，１ｍｏｌ
）と塩化チオニル６０ｗｔ’ｉ攪拌しながら５時間還流
させ次。つづいて、過剰の塩化チオニルを留去した後、
残留物をｎ−ヘキサンによシ再結晶化して２６．４１ｉ
（収率８０％）の白色結晶（酸塩化物）を得た。Synthesis Example 1 First, 97-hebutyloxy-fluorene-2-carboxylic acid was synthesized by a known method to yield 38.21! (0.1 mol
) and 60 wt'i of thionyl chloride and refluxed for 5 hours with stirring. Subsequently, after distilling off excess thionyl chloride,
The residue was recrystallized from n-hexane to give 26.41i
(yield 80%) white crystals (acid chloride) were obtained.
次いで、上記酸塩化物２０Ｉ！（０，０６ｍｏｌ）の８
０ｍピリジン溶液に（−）−２−メチル−１−ブタノー
ル４．８１１ （０，０６５ｍｏｌ ）の１０−ピリジ
ン溶液を１０分間かけて滴下した後、攪拌しなから油浴
を用いて９０℃で４時間加熱した。つづいて、室＠まで
冷却した後、得られたピリジン溶液ｔ−ｓｏ。Then, the above acid chloride 20I! (0.06 mol) of 8
A solution of 4.811 (0,065 mol) of (-)-2-methyl-1-butanol in 10-pyridine was added dropwise to the 0mM pyridine solution over a period of 10 minutes. heated for an hour. Subsequently, after cooling to room temperature, the obtained pyridine solution t-so.
−のイオン交換水中に注ぎ、生成された沈澱物をろ取し
た。ひきつづき、この沈澱物をエタノールによシ２回再
結晶化して白色結晶１９．５ｊｌ（収率８５％）を得た
〇
得られた白色結晶ｆ：！アセトンで溶解し、ＮＭＲで分
析したところ、図面に示す罵スペクトルが得られた。更
に、白色結晶の元素分析を行なったところ、Ｃニア９．
４．Ｈ：８．３，０：１２．２（計算値ｃ ： ７９．
１９． Ｈ： ８．６ ａ 、 ｏ ： １２．１８）
であった。これら図示した間スペクトル及び元素分キシ
フルオレンー２−カル？ン！−２−１ｆｌＶｆチルエス
テルであることが確認された。- was poured into ion-exchanged water, and the resulting precipitate was collected by filtration. Subsequently, this precipitate was recrystallized twice from ethanol to obtain 19.5 jl of white crystals (yield 85%) 〇 Obtained white crystals f:! When dissolved in acetone and analyzed by NMR, the spectrum shown in the drawing was obtained. Furthermore, elemental analysis of the white crystal revealed that it was C near 9.
4. H: 8.3, 0: 12.2 (calculated value c: 79.
19. H: 8.6 a, o: 12.18)
Met. The spectrum and elemental content between these diagrams: xyfluorene-2-cal? hmm! -2-1flVf thyl ester was confirmed.
合成例２〜５
７−オクチルオキシ−フルオレン−２−カルボン酸、７
−ノニルオキシ−フルオレン−２−カルゴン酸、７−デ
シルオキシ−フルオレン−２−カル？ン酸、７−ｆ）ン
デシルオキシーフルオレンー２−カルゴン酸を夫々０．
１ ｍｏｌ用意し、これらを合成例１と同様な反応を行
なうことによシ光学活性な７−オクチルオキシ７レオレ
ンー２−カルボン酸−２−メチルブチルエステル、７−
ノニルオキシフルオレン−２−カルゼン酸−２−メチル
ブチルエステル、７−デシルオキシフルオレン−２−カ
ルゴン酸−２−メチルブチルエステル及び７−ウンデシ
ルオキシフルオレン−２−カルゴン酸−２−メチルブチ
ルエステルを得た。これらの化合物は、罵スペクトル分
析及び元素分析によシ前記構造であることを確認した。Synthesis Examples 2 to 5 7-octyloxy-fluorene-2-carboxylic acid, 7
-nonyloxy-fluorene-2-cargonic acid, 7-decyloxy-fluorene-2-cargonic acid? 7-f)endecyloxy-fluorene-2-cargonic acid, respectively.
By preparing 1 mol of these and performing the same reaction as in Synthesis Example 1, optically active 7-octyloxy7leolelene-2-carboxylic acid-2-methylbutyl ester, 7-
nonyloxyfluorene-2-cargonic acid-2-methylbutyl ester, 7-decyloxyfluorene-2-cargonic acid-2-methylbutyl ester, and 7-undecyloxyfluorene-2-cargonic acid-2-methylbutyl ester. Obtained. These compounds were confirmed to have the above structure by spectroscopic analysis and elemental analysis.
しかして、合成例１〜５によシ得た化合物の融点及び各
相転移温度を調べた。その結果を下記表に示す。Therefore, the melting points and phase transition temperatures of the compounds obtained in Synthesis Examples 1 to 5 were investigated. The results are shown in the table below.
上表において、Ｃは結晶相、ＳｍＣ＊はキラルスメクテ
ックＣ相、ＳｍＡはスメクチックＡ相、Ｉは等方性液体
相、を夫々示す。また、（）はモノトロピック相転移温
度を示す。In the above table, C indicates a crystalline phase, SmC* indicates a chiral smectic C phase, SmA indicates a smectic A phase, and I indicates an isotropic liquid phase. Further, () indicates the monotropic phase transition temperature.
実施例１
前記合成方法によシ得た光学活性な７−へグチルオキシ
フルオレン−２−カルビン酸−２−メチルブチルエステ
ル及び７−オクチルオキシフルオレン−２−カルボン酸
−２−メチルブチルエステル’ｉｌ ： １の割合で混
合して混合物を調製した。Example 1 Optically active 7-hegyloxyfluorene-2-carbic acid-2-methylbutyl ester and 7-octyloxyfluorene-2-carboxylic acid-2-methylbutyl ester obtained by the above synthesis method : A mixture was prepared by mixing at a ratio of 1:1.
得られた混合物の各相転移温度を測定したところ、Ｃ−
４８ｍＣ” ３５．５℃、 ＳｍＣ” →ＳｍＡ ４
２℃、 ＳｍＡ→Ｉ７０．５℃であった。この結果から
、前記化合物の混合に二Ｆ） ＳｍＣ“の安定化が図ら
れた液晶組成物が得られることがわかった。When the phase transition temperature of the obtained mixture was measured, it was found that C-
48mC" 35.5℃, SmC" →SmA 4
2°C, SmA→I70.5°C. From this result, it was found that a liquid crystal composition in which 2F) SmC" was stabilized by mixing the above-mentioned compounds could be obtained.
実施例２
前記方法によシ合成した光学活性な７−へグチルオキシ
フルオレン−２−カルボン酸−メチルブチルエステル、
７−オクチルオキシフルオレン−２−カルメン酸−２−
メチルブチルエステル、γ−デシルオキシフレオレンー
２−カルがン酸−２−メチルブチルエステＡ／を当モル
混合して混合物をｉ！ｌｉ製した。Example 2 Optically active 7-hegyloxyfluorene-2-carboxylic acid-methylbutyl ester synthesized by the above method,
7-octyloxyfluorene-2-carmenic acid-2-
Methyl butyl ester and γ-decyloxyfluorene-2-calanoic acid-2-methylbutyl ester A/ are mixed in equimolar amounts to form a mixture i! Made from li.
得られた混合物の各相転移温度を測定したところ、Ｃ−
ｅ ＳｍＣ” ２７．５℃、 ＳｍＣ”→ＳｍＡ４４
℃。When the phase transition temperature of the obtained mixture was measured, it was found that C-
e SmC” 27.5℃, SmC”→SmA44
℃.
ＳｍＡ→Ｉ ７５℃であっ九。この結果から、前記各
化合物の混合によシ実施例１と同様、ＳｍＣ”の安定化
が図られた液晶組成物が得られることがわかった。SmA→I at 75°C. From this result, it was found that, as in Example 1, a liquid crystal composition in which SmC'' was stabilized could be obtained by mixing the above-mentioned compounds.
［発明の効果コ
以上詳述した如く、本発明によればキラルスメクテック
Ｃ相の温度範囲が拡大され、かつ熱力学的な安定性が優
れた一般式（Ａ）に示す化合物からなる液晶材料を得る
ことができ、ひいてはこれら液晶材料の混合又は他のキ
２ルスメクテックＣ相を示す液晶材料との混合によシ広
い温度範囲で安定的にキラルスメクテックＣ相を有する
強訴電性液晶を実現できる等顕著な効果を有する。[Effects of the Invention] As detailed above, according to the present invention, the temperature range of the chiral smectic C phase is expanded, and a liquid crystal material comprising the compound represented by the general formula (A), which has excellent thermodynamic stability, is produced. By mixing these liquid crystal materials or with other liquid crystal materials exhibiting a chiral smectic C phase, it is possible to obtain a highly electrostatic liquid crystal having a chiral smectic C phase stably over a wide temperature range. It has remarkable effects such as being able to be realized.
図面は１合成例１で合成された７−へブチルオキシフル
オレン−２〜カル２ンａ−２−）ｆルプチルエステルの
蘭−スイクトルを示す図である。
出願人代理人 弁理士 鈴 江 武 彦手続補正書
昭和 年６２・４・１４日
特許庁長官 黒 １）明 雄 殿
１、事件の表示
特願昭６１−２２７９７０号
２、発明の名称
液晶材料
３、補正をする者
事件との関係 特許出願人
（３０７）株式会社 東芝
４、代理人
東京都千代田区霞がｒＩＪＪ３丁目７番２号 ＬＩＢＥ
ピル７、補正の内容
明ｍｖａ中第５頁下から２〜３行目にかけて「本発明の
液晶材となる７−アルコキシフルオレノン−２−カルボ
ン酸は」とあるを「本発明の液晶材料となる７−アルコ
キシフルオレン−
エステルは」と訂正する。The drawing shows the orchid-suictor of 7-hebutyloxyfluorene-2-car2-a-2-)f rubutyl ester synthesized in Synthesis Example 1. Applicant's representative Patent attorney Takehiko Suzue Procedural amendment April 14, 1948 Director General of the Patent Office Kuro 1) Akio Yu 1, Indication of case Patent application No. 1983-227970 2, Title of invention Liquid crystal material 3 , Relationship with the case of the person making the amendment Patent applicant (307) Toshiba Corporation 4, agent Kasumi 3-7-2 Chiyoda-ku, Tokyo LIBE
Pill 7, Amendment Contents MVA, page 5, lines 2-3 from the bottom, the phrase "7-alkoxyfluorenone-2-carboxylic acid is the liquid crystal material of the present invention" has been changed to "the liquid crystal material of the present invention is "7-alkoxyfluorene-ester" is corrected.
Claims (4)
を有する光学活性基を示す〕にて表わされる７−アルコ
キシフルオレン−２−カルボン酸エステルからなる液晶
材料。(1) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (A) [However, R in the formula is an alkyl group, and R^* is an optically active group having an asymmetric carbon atom] 7- A liquid crystal material made of alkoxyfluorene-2-carboxylic acid ester.
キル基であることを特徴とする特許請求の範囲第１項記
載の液晶材料。(2) The liquid crystal material according to claim 1, wherein R in the general formula (A) is a linear alkyl group having 3 to 18 carbon atoms.
ブチル基であることを特徴とする特許請求の範囲第１項
記載の液晶材料。(3) The liquid crystal material according to claim 1, wherein R^* in the general formula (A) is an optically active 2-methylbutyl group.
ル基であることを特徴とする特許請求の範囲第１項記載
の液晶材料。(4) The liquid crystal material according to claim 1, wherein R^* in the general formula (A) is an optically active 2-octyl group.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22797086A JPH0739579B2 (en) | 1986-09-29 | 1986-09-29 | Liquid crystal material |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22797086A JPH0739579B2 (en) | 1986-09-29 | 1986-09-29 | Liquid crystal material |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6383191A true JPS6383191A (en) | 1988-04-13 |
| JPH0739579B2 JPH0739579B2 (en) | 1995-05-01 |
Family
ID=16869107
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP22797086A Expired - Lifetime JPH0739579B2 (en) | 1986-09-29 | 1986-09-29 | Liquid crystal material |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0739579B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4976887A (en) * | 1988-01-21 | 1990-12-11 | Kabushiki Kaisha Toshiba | Optically active liquid crystal compound and method of manufacturing the same, liquid crystal composition containing the same and liquid crystal display device |
-
1986
- 1986-09-29 JP JP22797086A patent/JPH0739579B2/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4976887A (en) * | 1988-01-21 | 1990-12-11 | Kabushiki Kaisha Toshiba | Optically active liquid crystal compound and method of manufacturing the same, liquid crystal composition containing the same and liquid crystal display device |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0739579B2 (en) | 1995-05-01 |
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