JPS6013731A - Substituted phenyl ether compound - Google Patents
Substituted phenyl ether compoundInfo
- Publication number
- JPS6013731A JPS6013731A JP11998383A JP11998383A JPS6013731A JP S6013731 A JPS6013731 A JP S6013731A JP 11998383 A JP11998383 A JP 11998383A JP 11998383 A JP11998383 A JP 11998383A JP S6013731 A JPS6013731 A JP S6013731A
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- formula
- compound
- substituted phenyl
- trans
- 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
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Abstract
Description
【発明の詳細な説明】
本発明は置換フェニルエーテル化合物および該化合物を
含有する組成物に関し、液晶混合物の成分として有用な
化合物およびそれを含有する液晶組成物に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to substituted phenyl ether compounds and compositions containing the same, and in particular to compounds useful as components of liquid crystal mixtures and liquid crystal compositions containing the same.
液晶表示素子は液晶材料が持つ光学異方性及び誘電異方
性を利用したものであり、その表示様式によってＴＮ型
（ねじれネマチック型）。Liquid crystal display elements utilize the optical anisotropy and dielectric anisotropy of liquid crystal materials, and their display formats are TN type (twisted nematic type).
ＤＳ壓（動的散乱型）、ゲスト・ホスト型。DS 壓 (dynamic scattering type), guest-host type.
ＤＡＰ型など各種の方式に分けられ、夫々の使用に適す
る液晶材料の性質は異る。いずれの液晶材料も水分、空
気、熱、光等に安定であることが必要である事は共通し
ており、室温を中心として出来るだけ広い温度範囲で液
晶相を示すものがめられている。現在の所、単一化合物
ではこの様な条件を満たす物質はなく、数種の液晶化合
物や非液晶化合物を混合して得られる液晶組成物を使用
している。It is divided into various types such as DAP type, and the properties of liquid crystal materials suitable for each use are different. All liquid crystal materials have in common that they must be stable against moisture, air, heat, light, etc., and materials that exhibit a liquid crystal phase over as wide a temperature range as possible, centered around room temperature, are desired. At present, there is no single compound substance that satisfies these conditions, and liquid crystal compositions obtained by mixing several types of liquid crystal compounds and non-liquid crystal compounds are used.
本発明は一般式
〔上式中Ｒは炭素原子１〜８個を含む直鎖アルキル基を
表し、Ｚ＋ｍはそれぞれ０．１又は２の整数を表わしｔ
十ｍと１であシ、Ｘ、Ｙ、Ｚはそれぞれフッ素、塩素、
臭素またはシアン基金表わす。〕で示される置換フェニ
ルエーテル化合物および該化合物を有する組成物でちゃ
、電子−光学装置におけるその用途に関する。The present invention is based on the general formula [In the above formula, R represents a straight chain alkyl group containing 1 to 8 carbon atoms, Z+m each represents an integer of 0.1 or 2, and t
10m and 1, X, Y, and Z are fluorine and chlorine, respectively.
Represents bromine or cyanide foundation. The present invention relates to substituted phenyl ether compounds represented by the following and compositions containing the compounds, and their use in electro-optical devices.
式（１）においてＸがシアノ基ｆｆｉ、Ｙがフッ素。In formula (1), X is a cyano group ffi, and Y is fluorine.
塩素または臭素原子を表わし、２が水素原子を表わす化
合物は強い正の誘電異方性を有する液晶材料用化合物で
ある。従って、各種ネマチック液晶物質は、この化合物
を少量含有することによシミ界効果型セルに適用が可能
となる。電界効果型セルを低電圧で駆動させることは当
該技術分野における重要課題の一つとされているがその
為には使用するネマチック液晶材料のしきい値電圧を出
来るだけ下ける必要がある。本化合物はこの目的に合致
する極めて有効な液晶材料である。A compound in which a chlorine or bromine atom is represented and 2 is a hydrogen atom is a compound for liquid crystal materials having strong positive dielectric anisotropy. Therefore, various nematic liquid crystal substances can be applied to spot field effect cells by containing a small amount of this compound. Driving a field effect cell at a low voltage is considered to be one of the important issues in this technical field, and for this purpose it is necessary to lower the threshold voltage of the nematic liquid crystal material used as much as possible. The present compound is a highly effective liquid crystal material meeting this purpose.
式（Ｉ）において電子１．ｍ＝ＱでＸがフッ素原子、Ｙ
及び２が水素原子でるる化合物は非液晶物を加えた液晶
組成物の粘度を低下させる効果は著しい。In formula (I), electron 1. m=Q, X is a fluorine atom, Y
A compound in which 2 is a hydrogen atom has a remarkable effect of lowering the viscosity of a liquid crystal composition to which a non-liquid crystal substance is added.
本発明の化合物は安定なもので液晶材料に於て使用する
のに非常に有利である本発明の化合物は相溶性にすぐれ
ており、他の液晶化合物例エバ、シクロヘキサンカルボ
ン酸フェニルエステル系、安息香酸フェニルエステル系
、フェニルメタジオキサン系、シクロヘキサンカルボン
酸シクロヘキシルエステル系、シッフ塩基系。The compound of the present invention is stable and very advantageous for use in liquid crystal materials.The compound of the present invention has excellent compatibility and can be used with other liquid crystal compounds such as EVA, cyclohexane carboxylic acid phenyl ester, benzoate, etc. Acid phenyl ester type, phenylmetadioxane type, cyclohexanecarboxylic acid cyclohexyl ester type, Schiff base type.
アゾキシ系等の他のネマチック液晶及び液晶組合物と混
合させる事にょシ、その液晶組成物の特性を改善する事
ができる。By mixing it with other nematic liquid crystals and liquid crystal combinations such as azoxy type, the properties of the liquid crystal composition can be improved.
この様に秀れた特徴を有する本発明の化合物は次に示す
反応によって製造することができる。The compound of the present invention having such excellent characteristics can be produced by the following reaction.
（１）
（式中Ｒ，ｔ、ｍ＋ ｘｌ ｙ、Ｚは前述と同じである
。）
即ち上記ハロゲン化物（４）とフェノール誘導体の）を
アルコール溶媒中にて水酸化ナトリウム等のアルカリ金
属の水酸化物存在下にて反応させる。反応は常圧及び室
温から反応混合物の還流温度範凹の温度で行なうことが
できる。反応生成物に溶剤抽出、水洗、乾燥、再結晶等
の一連の精製処理を施すことによって目的とする式（Ｉ
）の化合物を単離することができる。(1) (In the formula, R, t, m+ React in the presence of an oxide. The reaction can be carried out at normal pressure and at temperatures ranging from room temperature to the reflux temperature of the reaction mixture. The desired formula (I
) can be isolated.
以下実施例により本発明の化合物（１）の製造方法及び
応用例を詳細に説明する。The manufacturing method and application examples of the compound (1) of the present invention will be explained in detail with reference to Examples below.
実施例１
４−）ランス（トランス−４′−ペンチルシクロヘキシ
ル）シクロヘキシルメチル−３−クロｏ−４−シアンフ
ェニルエーテルの製造（（Ｉ）式においてＲ−Ｃ３Ｈ１
１＋ １−２ ｔ ｍ −０＋Ｘ＝ＣＮ、Ｙ＝Ｃ１，Ｚ
＝Ｈである化合物）８−クロロ−４−シアノフェノール
１．５４Ｆ（０，０１モル）を１ｏｃｃのエチルアルコ
ールに溶解し、これに更に０．８４ＩＣ０，０１５モル
）の水酸化カリウムを２ｃｃの水に溶解したものを加え
、これを加熱還流しておき、そこへ４−トランス（トラ
ンス−４′−ペンチルシクロヘキシル）シクロヘキシル
メチルプロミ）’ ３．８１（０，０１モル）を１０ｃ
ｃのエチルアルコールに溶解した溶液を加えた。この後
還流させつつ４時間反応させた。反応終了後、室温にま
で放冷し析出した結晶をトルエン１０ｃｃを加え抽出し
た。トルエン抽出液を１０％水酸化ナトリウム溶液で、
次いで水で洗浄後無水硫酸ナトリウムを用いて乾燥後、
トルエンを留去した。残った固型物をｌθ医の酢酸エチ
ルを用いて再結晶して目的物２．’１８９を得た。Example 1 4-) Production of lance (trans-4'-pentylcyclohexyl)cyclohexylmethyl-3-chloro o-4-cyanphenyl ether (R-C3H1 in formula (I)
1+ 1-2 t m -0+X=CN, Y=C1,Z
=H compound) 8-chloro-4-cyanophenol 1.54F (0.01 mol) was dissolved in 1 occ of ethyl alcohol, and to this, 0.84 IC (0.015 mol) of potassium hydroxide was dissolved in 2 cc of water. 4-trans(trans-4'-pentylcyclohexyl)cyclohexylmethylpromi)' 3.81 (0.01 mol) was added to the mixture and heated to reflux, and 10 c of 4-trans(trans-4'-pentylcyclohexyl)cyclohexylmethylpromi)'
A solution of c in ethyl alcohol was added. Thereafter, the mixture was reacted for 4 hours under reflux. After the reaction was completed, the mixture was allowed to cool to room temperature, and the precipitated crystals were extracted by adding 10 cc of toluene. Toluene extract with 10% sodium hydroxide solution,
Next, after washing with water and drying using anhydrous sodium sulfate,
Toluene was distilled off. The remaining solid substance was recrystallized using lθ ethyl acetate to obtain the desired product 2. '189 was obtained.
この物はネマチック液晶物質で、融点（以下Ｃ−Ｎ点と
略記する。、）は９７．５℃、透明点（以下Ｎ−Ｉ点と
略記する。）は１１１．７℃であった。又ξのものの元
Ｉ分析値は次の通シで理ｈＩＩｌ値とよく一致した。This material was a nematic liquid crystal material, and had a melting point (hereinafter abbreviated as CN point) of 97.5°C and a clearing point (hereinafter abbreviated as NI point) of 111.7°C. Moreover, the element I analysis value of ξ was in good agreement with the theoretical hIIl value in the following passage.
分＋ｉ値（■１Ｐ外） 回Ω丘直（重量％）（ＣｎＨａ
ａＯ目・ＣＡとして）Ｃ７５，１７４，’Ｉ
Ｈ８，７９，０
実施例１に準じた方法にて製造した化合物の物性全第１
表に示す。min + i value (■1P outside) times Ω hill straight (weight%) (CnHa
a0 order/CA) C75,174,'I H8,79,0 All physical properties of the compound produced by the method according to Example 1
Shown in the table.
表中で結晶−透明点をＣ−Ｉ点、認定異方性を△εと略
記する。表中でＮ−Ｉ点の〔〕はモノドロピンクを表わ
す。In the table, the crystal-clearing point is abbreviated as C-I point, and the certified anisotropy is abbreviated as Δε. In the table, the mark [ ] at the point NI represents monochrome pink.
△ε＝ε／−ε土、但しε／は分子の長軸方向の誘電率
でε±は分子の長袖と垂直方向の誘電率を衣わす。△ε
は次の組成のネマチック液晶組成物（Ｑに混合して外挿
によ請求めた値である。Δε=ε/−ε soil, where ε/ is the dielectric constant in the direction of the long axis of the molecule, and ε± is the dielectric constant in the direction perpendicular to the long axis of the molecule. △ε
is the value obtained by extrapolation after mixing with a nematic liquid crystal composition (Q) having the following composition.
第 １ 表
応用例１（使用例１）
前述の液晶組成物（ｑのネマチック液晶温度範囲は−５
〜７１．９℃である。この液晶組成物をセル厚１０μｍ
のＴＮセルに封入したものの動作しきい電圧は１．８４
Ｖ、飽和電圧は２．４３Ｖであった。又粘度は２０°Ｃ
で２８ｃｐであった。上記の液晶組成物９０重量部に本
発明の化合物の１つである実施例１に示す４−トランス
（トランス−４′−ペンチルシクロヘキシル）シクロヘ
キシルメトキシ−３−クロロ−４−シアノフェニルエス
テルｔｏ重ｉ部を加えたネマチック液晶温度範囲は一８
〜７８℃に広がシ、これを１０μｐｉｔのセル厚のＴ
Ｎセルに封入したものの動作しきい電圧は１．５６Ｖ、
飽和電圧は２．ｌＯＶと低下し、粘度は２０°Ｃで８８
．５ｃｐで粘度をそれほど増加させることなく本化合物
を使用した液晶組成物の駆動電圧を低下させ、液晶温度
範囲を広げる効果は著しい。Table 1 Application example 1 (Usage example 1) The above-mentioned liquid crystal composition (the nematic liquid crystal temperature range of q is -5
~71.9°C. This liquid crystal composition has a cell thickness of 10 μm.
The operating threshold voltage of the TN cell sealed in is 1.84.
V, the saturation voltage was 2.43V. Also, the viscosity is 20°C
It was 28 cp. 4-trans(trans-4'-pentylcyclohexyl)cyclohexylmethoxy-3-chloro-4-cyanophenyl ester shown in Example 1, which is one of the compounds of the present invention, is added to 90 parts by weight of the above liquid crystal composition. The nematic liquid crystal temperature range including
Spread at ~78°C, and transfer this to a T with a cell thickness of 10μpit.
The operating threshold voltage of the sealed N cell is 1.56V,
The saturation voltage is 2. 1OV and the viscosity is 88 at 20°C.
．． At 5 cp, the effect of lowering the driving voltage of a liquid crystal composition using this compound without significantly increasing the viscosity and widening the liquid crystal temperature range is remarkable.
応用例２（使用例２）
応用例１と同じ液晶組成物９０重量部に本発明の化合物
の１つである実施例３に示す４−（）ランス−４１−エ
チルシクロヘキシルメトキシ〕フルオロベンゼン１０！
ｉ部を加えたネマチック液晶温度範囲は一１Ｏ〜５７℃
になり低温側の温度領域は改善されこれを前述の如＜１
０１１ｍのセル厚のＴＮセルに封入したものの動作しき
い電圧は１．４５Ｖ、飽和電圧は２．０８ Ｖと低下し
又粘度は２０°Ｃで２２、５ ＣＰと大幅に改善された
。Application Example 2 (Use Example 2) 4-() lance-41-ethylcyclohexylmethoxy]fluorobenzene shown in Example 3, which is one of the compounds of the present invention, was added to 90 parts by weight of the same liquid crystal composition as in Application Example 1.
Nematic liquid crystal temperature range with i part added is -10 to 57℃
As a result, the temperature range on the low temperature side is improved, and this can be reduced to <1 as described above.
When sealed in a TN cell with a cell thickness of 0.011 m, the operating threshold voltage decreased to 1.45 V, the saturation voltage decreased to 2.08 V, and the viscosity was significantly improved to 22.5 CP at 20°C.
以上that's all
Claims (2)
Ｌ、ｍはそれぞれ０．１または２の整数を表わしＬ＋ｍ
≧１であＪ、Ｘ、Ｙ。 ２はそれぞれフッ素、塩素、臭素、水素またはシアノ基
を表わす。）で示される置換フェニルエーテル化合物。(1) General formula (wherein R represents an alkyl group having 1 to 8 carbon atoms,
L and m each represent an integer of 0.1 or 2, L+m
≧1 and J, X, Y. 2 represents fluorine, chlorine, bromine, hydrogen or cyano group, respectively. ) Substituted phenyl ether compound represented by
、ｌ、ｍはそれぞれ０．ｉｔたは２の整数を表わしＬ
＋ ｍ≧１であり、Ｘ、Ｙ。 ２はそれぞれフッ素、塩素、臭素、水素またはシアノ基
を表わす。）で示される置換フェノールエーテル化合物
を含有することを特徴とする組成物。(2) General formula (in the formula, IC represents an alkyl group having 1 to 8 carbon atoms, l and m each represent an integer of 0.it or 2, and L
+ m≧1, and X, Y. 2 represents fluorine, chlorine, bromine, hydrogen or cyano group, respectively. ) A composition characterized by containing a substituted phenol ether compound represented by:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11998383A JPS6013731A (en) | 1983-07-01 | 1983-07-01 | Substituted phenyl ether compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11998383A JPS6013731A (en) | 1983-07-01 | 1983-07-01 | Substituted phenyl ether compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6013731A true JPS6013731A (en) | 1985-01-24 |
| JPH0460976B2 JPH0460976B2 (en) | 1992-09-29 |
Family
ID=14774999
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11998383A Granted JPS6013731A (en) | 1983-07-01 | 1983-07-01 | Substituted phenyl ether compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6013731A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4668427A (en) * | 1984-09-04 | 1987-05-26 | Chisso Corporation | Liquid crystal compound having methyleneoxy group and composition containing same |
| US4710315A (en) * | 1984-04-16 | 1987-12-01 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Anisotropic compounds and liquid crystal mixtures therewith |
| US4797228A (en) * | 1985-06-10 | 1989-01-10 | Chisso Corporation | Cyclohexane derivative and liquid crystal composition containing same |
| US5230826A (en) * | 1987-11-06 | 1993-07-27 | Hoffmann-La Roche Inc. | Halobenzene liquid crystals |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5780485A (en) * | 1980-11-07 | 1982-05-20 | Daido Steel Co Ltd | Controlling method in treatment for melting industrial waste or the like |
-
1983
- 1983-07-01 JP JP11998383A patent/JPS6013731A/en active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5780485A (en) * | 1980-11-07 | 1982-05-20 | Daido Steel Co Ltd | Controlling method in treatment for melting industrial waste or the like |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4710315A (en) * | 1984-04-16 | 1987-12-01 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Anisotropic compounds and liquid crystal mixtures therewith |
| JPH0764767B2 (en) * | 1984-04-16 | 1995-07-12 | メルク・パテント・ゲゼルシヤフト・ミツト・ベシユレンクテル・ハフツング | Anisotropic compounds and liquid crystal mixtures using them |
| USRE36849E (en) * | 1984-04-16 | 2000-09-05 | Merck Patent Gmbh | Anisotropic compounds and liquid crystal mixtures therewith |
| US4668427A (en) * | 1984-09-04 | 1987-05-26 | Chisso Corporation | Liquid crystal compound having methyleneoxy group and composition containing same |
| US4751019A (en) * | 1984-09-04 | 1988-06-14 | Chisso Corporation | Liquid crystal compound having methyleneoxy group and composition containing same |
| US4797228A (en) * | 1985-06-10 | 1989-01-10 | Chisso Corporation | Cyclohexane derivative and liquid crystal composition containing same |
| US4917819A (en) * | 1985-06-10 | 1990-04-17 | Chisso Corporation | Cyclohexane derivative and liquid crystal composition containing same |
| US5230826A (en) * | 1987-11-06 | 1993-07-27 | Hoffmann-La Roche Inc. | Halobenzene liquid crystals |
| US5302317A (en) * | 1987-11-06 | 1994-04-12 | Hoffmann-La Roche Inc. | Halobenzene liquid crystals |
| US5454974A (en) * | 1987-11-06 | 1995-10-03 | Hoffmann-La Roche Inc. | Halobenzene liquid crystals |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0460976B2 (en) | 1992-09-29 |
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