JPH02108656A - Halogenocyanobenzene derivative compound and liquid crystal composition containing the compound - Google Patents
Halogenocyanobenzene derivative compound and liquid crystal composition containing the compoundInfo
- Publication number
- JPH02108656A JPH02108656A JP63260663A JP26066388A JPH02108656A JP H02108656 A JPH02108656 A JP H02108656A JP 63260663 A JP63260663 A JP 63260663A JP 26066388 A JP26066388 A JP 26066388A JP H02108656 A JPH02108656 A JP H02108656A
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- compound
- formula
- carbon
- halogenocyanobenzene
- 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
- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 34
- 150000001875 compounds Chemical class 0.000 title claims abstract description 26
- 239000000203 mixture Substances 0.000 title claims description 11
- 239000000126 substance Substances 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims abstract description 4
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 239000000463 material Substances 0.000 abstract description 18
- 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 6
- 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 4
- 229910052801 chlorine Inorganic materials 0.000 abstract description 3
- 229910052731 fluorine Inorganic materials 0.000 abstract description 3
- 239000012071 phase Substances 0.000 abstract description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract description 3
- 239000007791 liquid phase Substances 0.000 abstract description 2
- 230000007704 transition Effects 0.000 abstract description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000000758 substrate Substances 0.000 description 5
- 210000002858 crystal cell Anatomy 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- FJAZXDVZZJEDAM-UHFFFAOYSA-N 4-[2-(4-propylphenyl)ethyl]benzoic acid Chemical compound C1=CC(CCC)=CC=C1CCC1=CC=C(C(O)=O)C=C1 FJAZXDVZZJEDAM-UHFFFAOYSA-N 0.000 description 2
- -1 8H) 7.6 9-8.08 (m Chemical group 0.000 description 2
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 229950011008 tetrachloroethylene Drugs 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- BDDVAWDNVWLHDQ-UHFFFAOYSA-N 2-chloro-4-hydroxybenzonitrile Chemical compound OC1=CC=C(C#N)C(Cl)=C1 BDDVAWDNVWLHDQ-UHFFFAOYSA-N 0.000 description 1
- REIVHYDACHXPNH-UHFFFAOYSA-N 2-fluoro-4-hydroxybenzonitrile Chemical compound OC1=CC=C(C#N)C(F)=C1 REIVHYDACHXPNH-UHFFFAOYSA-N 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- WPYMKLBDIGXBTP-VQEHIDDOSA-N benzoic acid Chemical compound OC(=O)C1=CC=C[13CH]=C1 WPYMKLBDIGXBTP-VQEHIDDOSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- NJSUFZNXBBXAAC-UHFFFAOYSA-N ethanol;toluene Chemical compound CCO.CC1=CC=CC=C1 NJSUFZNXBBXAAC-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 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】
［産業上の利用分野］
本発明は液晶電気光学素子に用いられるハロゲノシアノ
ベンゼン誘導体化合物及びそれを含有する液晶組成物に
関するものである。DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to a halogenocyanobenzene derivative compound used in a liquid crystal electro-optical element and a liquid crystal composition containing the same.
［従来の技術］
液晶表示素子は、時計、電卓をはじめ、近年では、測定
器、自動車用計器、複写器、カメラ等１種々の用途に使
用され始めており、広い動作温度範囲、低動作電圧、高
速応答性、化学的安定性等の種々の性能要求がなされて
いる。[Prior Art] Liquid crystal display elements have begun to be used in various applications such as watches and calculators, and in recent years, measuring instruments, automobile instruments, copiers, cameras, etc., and have a wide operating temperature range, low operating voltage, There are various performance requirements such as high-speed response and chemical stability.
しかし、現在のところこれらの特性を単独の材料で全て
満たす材料はな（、複数の液晶、及び、非液晶の材料を
混合して液晶組成物とじてシー
要求性能を満たしている状態である。このため各種特性
の全てではなく、−もしくは二以上の特性に優れた液晶
材料または非液晶材料の材料開発が望まれている。However, at present, there is no material that satisfies all of these characteristics with a single material (although liquid crystal compositions that meet the required performance by mixing multiple liquid crystal and non-liquid crystal materials) are currently available. For this reason, there is a desire to develop liquid crystal materials or non-liquid crystal materials that are excellent in not all but one or more of the various characteristics.
［発明の解決しようとする課題］
液晶を用いた表示素子分野において用いられる液晶化合
物に要求される種々の特性の中でも、動作温度範囲を狭
めることなく、低電圧で駆動でき、さらに他の液晶材料
または非液晶材料との相溶性に優れ、化学的にも安定な
材料を提供することは重要な課題である。[Problem to be solved by the invention] Among the various properties required of liquid crystal compounds used in the field of display elements using liquid crystals, it is desirable to be able to drive at low voltage without narrowing the operating temperature range, and to be able to use other liquid crystal materials. Alternatively, it is an important issue to provide a chemically stable material that has excellent compatibility with non-liquid crystal materials.
［課題を解決するための手段］
本発明は、前述の問題点を解決すべく新規な材料を提供
するものであり、一般式
（式中Ｒは炭素数１〜１０の直鎖アルキル基（この基中
の炭素−炭素結合の間またはこの基とフェニレン環との
間の炭素−炭素結合の間に酸素原子が挿入されていても
よい）を示し、Ｘは塩素原子またはフッ素原子を示す）
で表されるハロゲノシアノベンゼン誘導体化合物及びそ
の少なくとも１種を組成物中に含有することを特徴とす
る液晶組成物を提供するものである。[Means for Solving the Problems] The present invention provides a novel material in order to solve the above-mentioned problems. (X represents a chlorine atom or a fluorine atom)
The present invention provides a liquid crystal composition containing a halogenocyanobenzene derivative compound represented by the following formula and at least one thereof.
本発明の一般式（Ｉ）の化合物は、非常に大きな正の誘
電異方性（△ε）を有しており、比較的高温において、
ネマチック相から等方性液体相への転移温度を有してい
る。また、他の液晶材料または非液晶材料との相溶性に
優れ、化学的にも安定な材料であり、液晶組成物として
、動作温度範囲を狭めることなく、駆動電圧を下げるの
に適した材料である。The compound of general formula (I) of the present invention has a very large positive dielectric anisotropy (Δε), and at a relatively high temperature,
It has a transition temperature from a nematic phase to an isotropic liquid phase. In addition, it is a chemically stable material that has excellent compatibility with other liquid crystal materials or non-liquid crystal materials, and is suitable for lowering the driving voltage without narrowing the operating temperature range as a liquid crystal composition. be.
本発明の一般式（Ｉ）の化合物は、他の液晶材料、非液
晶材料に少なくとも１種を混合することにより、液晶組
成物として使用される。The compound of general formula (I) of the present invention is used as a liquid crystal composition by mixing at least one of the compounds with other liquid crystal materials and non-liquid crystal materials.
本発明の化合物として混合させる物質としては、例えば
以下のようなものがある。Examples of substances to be mixed as the compound of the present invention include the following.
以下の式でのＲ，Ｒ’は、本発明でのＲとは異なり、ア
ルキル基、アルコキシ基、ハロゲン原子、シアノ基等の
基を表す。Unlike R in the present invention, R and R' in the following formula represent groups such as an alkyl group, an alkoxy group, a halogen atom, and a cyano group.
なお、これらの化合物は単なる例示にすぎな（、水素原
子のハロゲン原子、シアノ基、メチル基等への置換、シ
クロヘキサン環、ベンゼン環の他の六員環、五員環等へ
の置換、環の間の結合基の変更等積々の材料が選択使用
される。These compounds are merely examples (substitution of a hydrogen atom with a halogen atom, a cyano group, a methyl group, etc., substitution of a cyclohexane ring, a benzene ring with another six-membered ring, a five-membered ring, etc.), Many materials can be selected and used, such as changing the bonding group between them.
本発明の組成物は、液晶セルに注入されて用いられる。The composition of the present invention is used by being injected into a liquid crystal cell.
上づツ
代表的な液晶セルとしては、ツイストネマチック（ＴＮ
）液晶素子があり、ガラス、プラスチック等の透明基板
内面にＩｎｔＯｓ−ＳｎＯ□等の透明電極を所望のパタ
ーン状に形成して、必要に応じて、ＳｉＯ□、ポリイミ
ド等のオーバーコートをし、水平配向層を形成した基板
を相対向せしめ周辺をシールし、液晶を注入し、注入口
を封止したものであり、この両外面に偏光板を積層して
使用される。又、この外、最近注目されている高ツイス
ト角のスーパーツイストネマチック（ＳＴＮ）型、相転
移型、ゲストホスト型、動的散乱型又はそれらを組み合
せて用いられても良いし、電気的にでな（熱による書き
込みをするタイプのものに用いてもよい。Twisted nematic (TN) is a typical liquid crystal cell.
) There is a liquid crystal element, in which transparent electrodes such as IntOs-SnO□ are formed in a desired pattern on the inner surface of a transparent substrate such as glass or plastic, and if necessary, an overcoat of SiO□, polyimide, etc. is applied, and horizontal The substrates on which alignment layers are formed are placed facing each other, the periphery is sealed, liquid crystal is injected, and the injection port is sealed, and polarizing plates are laminated on both outer surfaces. In addition, a super twisted nematic (STN) type with a high twist angle, which has recently been attracting attention, a phase change type, a guest host type, a dynamic scattering type, or a combination thereof may be used. (It may be used for a type of writing using heat.)
さらにセルの構造としては透明基板と透明電極の間に、
５ｉ０２． Ａｌ□０８等のアンダーコート層を設けた
り、反射性電極を用いたり、複層電極を用いたり、カラ
ー偏光板を用いたり、カラーフィルターを用いたり、半
導体基板を用いたり、複層素子としたりする等積々の応
用が可能であり、時計、電卓、計測器、自動車用計器、
′ゲーム、コンピュータ一端末機等積々の用途に使用可
能である。Furthermore, as for the structure of the cell, between the transparent substrate and the transparent electrode,
5i02. Providing an undercoat layer such as Al□08, using a reflective electrode, using a multilayer electrode, using a color polarizing plate, using a color filter, using a semiconductor substrate, or using a multilayer element. It can be used in many applications such as watches, calculators, measuring instruments, automobile instruments, etc.
'It can be used for many purposes such as games, computer terminals, etc.
本発明の一般式（Ｉ）の化合物は例えば、次のような方
法に従って製造される。The compound of general formula (I) of the present invention can be produced, for example, according to the following method.
（式中Ｒ，Ｘは夫々式（Ｉ）におけるＲ、Ｘと同じ意味
を持つ。）
即ち、式（ＩＩ）の化合物を塩化チオニルと反応させ酸
塩化物（Ｉ）とする。この（Ｉ）をピリジンの存在下、
式（ＩＶ ）の化合物と反応させ、式（１）の化合物が
得られる。なお、この製造法は単なる例示に過ぎなく、
種々の製造方法が使用できる。(In the formula, R and X have the same meanings as R and X in formula (I), respectively.) That is, the compound of formula (II) is reacted with thionyl chloride to form acid chloride (I). This (I) in the presence of pyridine,
Reaction with a compound of formula (IV) yields a compound of formula (1). Please note that this manufacturing method is merely an example.
Various manufacturing methods can be used.
［実施例］
以下実施例により、本発明の化合物の製造法、及び、本
発明の化合物を用いた液晶組成物により、本発明を更に
詳しく説明する。[Example] The present invention will be explained in more detail in the following Examples using a method for producing the compound of the present invention and a liquid crystal composition using the compound of the present invention.
実施例１
４− （２−（４−ｎ−プロピルフェニル）エチル］安
息香酸６．７１ｇ （０，０２５ｍｏｌ）をテトラクロ
ロエチレン５０ｍ１に溶解し、これに塩化チオニル４．
５ｇを加え４時間加熱還流した。冷却した後、過剰の塩
化チオニルとテトラクロロエチレンを留去し、酸塩化物
７．１８ｇを得た。Example 1 6.71 g (0,025 mol) of 4-(2-(4-n-propylphenyl)ethyl)benzoic acid was dissolved in 50 ml of tetrachloroethylene, and 4.0 ml of thionyl chloride was dissolved therein.
5 g was added and heated under reflux for 4 hours. After cooling, excess thionyl chloride and tetrachloroethylene were distilled off to obtain 7.18 g of acid chloride.
得られた酸塩化物をトルエン８０ｍ１に溶解し、４−シ
アノ−３−フロロフェノール３．４３ｇ（０，０２５１
１Ｉｏｌ） 、及びピリジン２．４ｇを加え３時間加熱
還流した。冷却した後、５％希塩酸にて洗浄、水洗し、
さらに３％水酸化ナトリウム水溶液にて洗浄、水洗した
。これを乾燥した後、トルエンを留去し、カラムクロマ
トグラフィー及び、エタノール−トルエン混合溶媒によ
る再結晶にて精製し、目的とする下記化合物５．９６ｇ
（０，Ｏ１５４ｍｏｌ）を得た。収率６１．５％、融点
（Ｃ−Ｎ）７８．２℃、透明点（Ｎ −Ｉ ） １２１
．１ ”Ｃ’Ｈ−ＮＭＲ（ＣＤＣ１，溶媒、ＴＭＳ内部
標準）スペクトルの帰属は以下の通りであった。The obtained acid chloride was dissolved in 80 ml of toluene, and 3.43 g (0,0251
1 Iol) and 2.4 g of pyridine were added, and the mixture was heated under reflux for 3 hours. After cooling, wash with 5% diluted hydrochloric acid and water.
Further, it was washed with a 3% aqueous sodium hydroxide solution and with water. After drying this, toluene was distilled off and purified by column chromatography and recrystallization with an ethanol-toluene mixed solvent to obtain 5.96 g of the target compound below.
(0.0154 mol) was obtained. Yield 61.5%, melting point (C-N) 78.2°C, clearing point (N-I) 121
．． 1''C'H-NMR (CDC1, solvent, TMS internal standard) spectrum assignments were as follows.
δ（ｐｐｍ）
０．９４ （ｔ、 −ＣＨ５，３Ｈ）１．５６
（ｍ、 −ＣＨｚＣＨｓ、 ２Ｈ）２．５６
（ｔ、 −ＣＨ，ＣＨ，Ｃ）１．、２Ｈ）７．０８
−７．３３ （ｍ、ａｒｏｍａｔｉｃ、８Ｈ）７．６
９−８．０８ （ｍ、 ａｒｏｍａｔｉｃ、 ３
８）また、この化合物のＩＲスペクトル（ＫＢｒ錠）を
第１図に示す。δ (ppm) 0.94 (t, -CH5,3H) 1.56
(m, -CHzCHs, 2H)2.56
(t, -CH,CH,C)1. , 2H) 7.08
-7.33 (m, aromatic, 8H) 7.6
9-8.08 (m, aromatic, 3
8) Also, the IR spectrum of this compound (KBr tablet) is shown in FIG.
同様にして、４− ［２−（４−ｎ−プロピルフェニル
）エチル］安息香酸に代え、対応する４−［２−（４−
ｎ−アルキルフェニル）エチル１安息香酸、４− ［２
−（４−ｎ−アルコキシフェニル）エチル］安息香酸等
を用い、
また、
４−シアノ−３−
フロロフェノ−
ルに代え、
対応する４−シアノ−３−
クロロフェノ
ールを用いることにより、
以下に示すような化
合物が合成できる。Similarly, instead of 4-[2-(4-n-propylphenyl)ethyl]benzoic acid, the corresponding 4-[2-(4-
n-alkylphenyl)ethyl 1benzoic acid, 4-[2
-(4-n-alkoxyphenyl)ethyl]benzoic acid, etc., and by using the corresponding 4-cyano-3-chlorophenol in place of 4-cyano-3-fluorophenol, as shown below. Compounds can be synthesized.
融点
（Ｃ−Ｎ）
８７．４
℃、
透明点
（Ｎ−Ｉ）
１０５．１℃
融点
（Ｃ−Ｎ）
７７．３
℃、
透明点
（Ｎ−Ｉ）
１０４．５℃
融点
（（ニーＮ）
８１．７
℃、
透明点
（Ｎ−Ｉ）
１１４．１”ｃ
ｎ（：ｔＨｔｓ（Ｓ殖函０←か
板上に酸化ケイ素のコート層を形成し、ラビング処理し
た基板間に挟持するようにして基板間隙８μｍの液晶セ
ルを作成した。Melting point (C-N) 87.4°C, Clearing point (N-I) 105.1°C Melting point (C-N) 77.3°C, Clearing point (N-I) 104.5°C Melting point ((N-I) 81.7 °C, clearing point (N-I) 114.1"c n A liquid crystal cell with a substrate gap of 8 μm was fabricated.
この液晶セルの２５℃におけるしきい値電圧を測定した
ところ、２．３８Ｖであった。The threshold voltage of this liquid crystal cell at 25° C. was measured and found to be 2.38V.
これに対して、本発明の実施例１の化合物を１０ｗｔ％
添加した混合液晶は、透明点（Ｎ−Ｉ）は８８．２℃と
上昇し、しきい値電圧は２．０９Ｖと低下することがで
きた。In contrast, 10 wt% of the compound of Example 1 of the present invention
In the added mixed liquid crystal, the clearing point (N-I) increased to 88.2° C., and the threshold voltage decreased to 2.09V.
［発明の効果］
以上の如（、本発明は新規な化合物である、一般式
メルク社製液晶組成物ＺＬＩ−１５６５の透明点（Ｎ−
Ｉ）は８５．９℃であり、これをＩＴＯ電極基（式中Ｒ
は炭素数１〜１０の直鎖アルキル基（この基中の炭素−
炭素結合の間またはこの基とフェニレン環との間の炭素
−炭素結合の間に酸素原子が挿入されていてもよい）を
示し、Ｘは塩素原子またはフッ素原子を示す）で表され
るハロゲノシアノベンゼン誘導体化合物を提供すること
により、液晶素子としての動作温度範囲を狭めることな
く、低動作電圧で駆動でき、かつ、化学的にも安定な液
晶組成物を構成させつる効果を生ずる優れたものである
。[Effects of the Invention] As described above, the present invention improves the clearing point (N-
I) is 85.9°C, which is connected to the ITO electrode group (in the formula R
is a straight-chain alkyl group having 1 to 10 carbon atoms (carbon-
(oxygen atoms may be inserted between carbon bonds or carbon-carbon bonds between this group and the phenylene ring), and X represents a chlorine atom or a fluorine atom) By providing a benzene derivative compound, we can create a chemically stable liquid crystal composition that can be driven at a low operating voltage without narrowing the operating temperature range of the liquid crystal element, and is excellent in producing a vine effect. be.
第１図は、本発明の実施例１の化合物のＩＲスペクトル
図である。FIG. 1 is an IR spectrum diagram of the compound of Example 1 of the present invention.
Claims (2)
の炭素−炭素結合の間またはこの基とフェニレン環との
間の炭素−炭素結合の間に酸素原子が挿入されていても
よい）を示し、Ｘは塩素原子またはフッ素原子を示す）
で表されるハロゲノシアノベンゼン誘導体化合物。(1) General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (I) (In the formula, R is a straight-chain alkyl group having 1 to 10 carbon atoms (between the carbon-carbon bond in this group or between this group and the phenylene ring) An oxygen atom may be inserted between the carbon-carbon bonds between
A halogenocyanobenzene derivative compound represented by
の炭素−炭素結合の間またはこの基とフェニレン環との
間の炭素−炭素結合の間に酸素原子が挿入されていても
よい）を示し、Ｘは塩素原子またはフッ素原子を示す）
で表されるハロゲノシアノベンゼン誘導体化合物の少な
くも１種を組成物中に含有することを特徴とする液晶組
成物。(2) General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (I) (In the formula, R is a straight-chain alkyl group having 1 to 10 carbon atoms (between the carbon-carbon bond in this group or between this group and the phenylene ring) An oxygen atom may be inserted between the carbon-carbon bonds between
A liquid crystal composition comprising at least one halogenocyanobenzene derivative compound represented by:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63260663A JP2684197B2 (en) | 1988-10-18 | 1988-10-18 | Halogenocyanobenzene derivative compound and liquid crystal composition containing the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63260663A JP2684197B2 (en) | 1988-10-18 | 1988-10-18 | Halogenocyanobenzene derivative compound and liquid crystal composition containing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02108656A true JPH02108656A (en) | 1990-04-20 |
| JP2684197B2 JP2684197B2 (en) | 1997-12-03 |
Family
ID=17351039
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63260663A Expired - Fee Related JP2684197B2 (en) | 1988-10-18 | 1988-10-18 | Halogenocyanobenzene derivative compound and liquid crystal composition containing the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2684197B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1993024442A1 (en) * | 1992-05-29 | 1993-12-09 | Yamanouchi Pharmaceutical Co., Ltd. | Medicine containing benzoic acid derivative and novel benzoic acid derivative |
-
1988
- 1988-10-18 JP JP63260663A patent/JP2684197B2/en not_active Expired - Fee Related
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1993024442A1 (en) * | 1992-05-29 | 1993-12-09 | Yamanouchi Pharmaceutical Co., Ltd. | Medicine containing benzoic acid derivative and novel benzoic acid derivative |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2684197B2 (en) | 1997-12-03 |
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