JPS5810529A - 1,4-di-(cyclohexylethyl)biphenyl derivative - Google Patents
1,4-di-(cyclohexylethyl)biphenyl derivativeInfo
- Publication number
- JPS5810529A JPS5810529A JP10624981A JP10624981A JPS5810529A JP S5810529 A JPS5810529 A JP S5810529A JP 10624981 A JP10624981 A JP 10624981A JP 10624981 A JP10624981 A JP 10624981A JP S5810529 A JPS5810529 A JP S5810529A
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- Prior art keywords
- formula
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- compound shown
- liquid crystal
- equatorial
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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】
本発明は電気光学的表示材料として有用なジエチルビフ
ェニル−導体の新規ネマチック液晶化合物に関する。本
発明によって−される新規ネマチック液晶は一般式
で表わされる１−（トランス（エカトリアルーエカトリ
ア／’）−４’−ｎ−アルキルシクロヘキシルエチルｊ
−４−（トランス（エカトリアル−エカトリアル）−４
’−ｎ−アルキルシクロヘキシルエチル）ビフェニルで
ある。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to novel nematic liquid crystal compounds of diethylbiphenyl-conductors useful as electro-optic display materials. The novel nematic liquid crystal according to the present invention is 1-(trans(ecatria-ecatria/')-4'-n-alkylcyclohexylethyl j
-4-(Trans(Equatorial-Equatorial)-4
'-n-alkylcyclohexylethyl)biphenyl.
式（Ｉ）０化合書は弱い負の誘電異方性をもつ化合物で
あり例えば、エム嗜シャット（Ｍ１１８ｈａｏｔｔ）等
〔ムＰＰＬＩＩＤＰＨＹＳＩＣ８ＬＥＴＴＥＲ８１８１
２７〜１２８（１９７１））によって提案された電界効
果型セル（フィールド・エフェクト・モード・セル）又
はジー−エイチーバイルマイヤー（Ｇ１１ＨＨ＠ｉ１ｍ
＊ｉ＠ｒ）等（ＰＲＯ（ＪＥＤＩＮＧＯＦＴＨＥｌ、Ｅ
、Ｅ、１．長１１６２〜１１７１（１９５８プ〕によっ
て提案された動的光散型セル（ダイナミック・スキャツ
タリング・峰−ド・セル）又はジー嗜エイチ・バイルマ
イヤー（Ｇ＠ｍＨ＊ｉ１ｍ＠ｉｅｒ）等〔ムＰＰＬＩＩ
ＤＰＨＹ［Ｃ３Ｌｌ？Ｔｍ１ｌｌｊ、９１（１９６８）
）あるいはディーｅエル・ホワイト（ＤＬＷｈｉｔ・）
等（ＪＯＵＲＮＡＩ、ＯＦムＰＰＬＩＩＤＰＩｆｆ８Ｉ
０１ｉ土δ４７１８（１９７４））によって提案された
ゲスト・ホスト瀝セルなどに適用することができる。The compound of formula (I)0 is a compound with weak negative dielectric anisotropy, and for example, M118haott etc.
27-128 (1971)) or the field-effect mode cell proposed by G-H Beilmeier (G11HH@i1m).
*i@r) etc. (PRO(JEDINGOFTHel, E
,E,1. The dynamic scattering cell proposed by Cho 1162-1171 (1958) or G. Beilmeier (G@mH*i1m@ier), etc. PPLII
DPHY[C3Ll? Tm1llj, 91 (1968)
) or DLWhit.
etc. (JOURNAI, OFMUPPLIIDPIff8I
The present invention can be applied to the guest-host cell proposed by 01i Sat.delta.4718 (1974)).
式（Ｉ）の化金物はネマチック−等方性液体の転移温度
が高く粘度が低いことを特色とするものであり、更に化
学的に非常に安定であって水分、光等によって分解せず
、然も無色乳白色と−った幾多の優れた特性を有してい
る。よって式（１）ｆ）化合物を用いれば長寿命でネ！
チック温度範囲の広い高速応答の液晶表示素子を制作す
ることができる。The metal compound of formula (I) is characterized by a high nematic-isotropic liquid transition temperature and low viscosity, and is also chemically very stable and does not decompose due to moisture, light, etc. However, it has many excellent properties including being colorless and milky white. Therefore, if the compound of formula (1) f) is used, it will have a long life!
It is possible to produce liquid crystal display elements with a wide temperature range and high-speed response.
本発＠によれば、式■）の化合物は次の製造方法に従つ
て製造される。According to the present invention, the compound of formula (1) is produced according to the following production method.
第１段階□二硫化炭素あるいはニトロベンゼン中でビフ
ェニルに式（６）の化合物と無水塩化アル建ニウムを反
応させて式−の化合物を製造する。1st step □ Biphenyl is reacted with a compound of formula (6) and anhydrous aluminum chloride in carbon disulfide or nitrobenzene to produce a compound of formula -.
第２段階□第１段階で製造された弐−の化合物にジエチ
レングリコールあるいはトリエチレングリコール中でヒ
ドラジンと水酸化カリウムを反応させて弐■の化合物を
製造する。2nd step □ Compound 2 produced in step 1 is reacted with hydrazine and potassium hydroxide in diethylene glycol or triethylene glycol to produce compound 2.
第３段階□第２段階で製造された式■の化合物に二硫化
炭素あるいはニトロベンゼン中で弐餌の化合物と無水塩
化アル１＝クムを反応させて弐Ｍの化合物を製造する。3rd step □ The compound of formula (1) produced in the second step is reacted with a bait compound and anhydrous aluminum chloride in carbon disulfide or nitrobenzene to produce a compound of 2M.
第４段階□ＩＫ５段階で展進された弐Ｍの化合物にジエ
チレングリコールあるいはトリエチレングリコール中で
ヒドラジンと水酸化カリウムを反応させて式（Ｉ）の化
合物を製造する。4th step □ The compound of formula (I) is produced by reacting the compound of 2M developed in step IK5 with hydrazine and potassium hydroxide in diethylene glycol or triethylene glycol.
斯くして製造された蝉■り化合物の転移温度を第１表に
掲げる。Table 1 lists the transition temperatures of the cicada compounds thus produced.
第１表
Ｒ，Ｒ，転移温度（”Ｃ）
ｒｒ−Ｃ＠Ｈ，−ｎ−Ｃ＊Ｈｙ４０（Ｃ−＋８）２０９
（ＥＥり２２３（Ｎｔ：±■）表中、Ｃは結晶、Ｓはス
メクチック相、Ｎはネｉチック相、■は等方性液体を夫
々表わす。Table 1 R, R, transition temperature (''C) rr-C@H, -n-C*Hy40(C-+8)209
(EE Ri 223 (Nt: ±■) In the table, C represents a crystal, S represents a smectic phase, N represents a natic phase, and ■ represents an isotropic liquid.
電卓、腕時計その他の機器の表示素子材料として用いる
場合、式（Ｉ）の化合物は、該化合物の２種以上の混合
物の形ｌＩ＊は該化合物の１種又は２種以上と他のネマ
チック液晶化合物及び／又は非ネマチック液晶化合物と
の混合物の形態で用いることができるが、好ましくは、
式（Ｉ）の化合物の２種以上の混合物を母体液晶とし、
この母体液晶に他のネマチック液晶化合物及び／又は非
ネマチック液晶化合物を混合した形態で用いることが推
奨される。カー）の化合物と混合して使用することので
きる他のネマチック液晶化合物及び／又は非ネマチック
液晶化合物には、大きい正の誘電率異方性をもつネマチ
ック液晶化合物（以下ＮｐＩＪ液晶という）及び／又は
Ｎｐ型液晶の同族体である非ネマチック液晶化合物（以
下Ｎｐ型液晶同族体という）、負又は小さい正の誘電率
異方性をもつネマチック液晶化合物（以下Ｎｎ型液晶と
いう）及び／又はＮｎｆＪ液晶の同族体である非ネマチ
ック液晶化合物（以下ＮＩｌ型液晶同族体という）、更
にそれらの混合物が含まれる。When used as a display element material for calculators, wristwatches, and other devices, the compound of formula (I) is a mixture of two or more of the compounds, i.e., one or more of the compounds and another nematic liquid crystal compound. and/or in the form of a mixture with a non-nematic liquid crystal compound, but preferably,
A mixture of two or more compounds of formula (I) is used as a host liquid crystal,
It is recommended to use this base liquid crystal in a mixed form with other nematic liquid crystal compounds and/or non-nematic liquid crystal compounds. Other nematic liquid crystal compounds and/or non-nematic liquid crystal compounds that can be used in combination with the compound of (Carr) include nematic liquid crystal compounds with large positive dielectric constant anisotropy (hereinafter referred to as NpIJ liquid crystals) and/or Non-nematic liquid crystal compounds that are homologs of Np-type liquid crystals (hereinafter referred to as Np-type liquid crystal homologues), nematic liquid crystal compounds having negative or small positive dielectric constant anisotropy (hereinafter referred to as Nn-type liquid crystals), and/or NnfJ liquid crystals. It includes non-nematic liquid crystal compounds that are homologs (hereinafter referred to as NIl-type liquid crystal homologs), as well as mixtures thereof.
式（Ｉ）の化合物と混合して使用することのできるＮｐ
型液晶及びＮｐ型液晶同族体の好ましい具体例を次に列
記する。Np which can be used in mixture with the compound of formula (I)
Preferred specific examples of the Np-type liquid crystal and Np-type liquid crystal homolog are listed below.
？
Ｒ＋Ｃ−０−Ｃ）−ＮＯ２
？
Ｒ（γｃ−ｓ−ＣΣＣＮ
Ｒ（γ（ＸＣＮ
次に、式（Ｉ）の化合物と混合して使用することのでき
るＮｎ型液晶及びＮｎ型液晶同族体の好ましい具体例を
列記する。? R+C-0-C)-NO2? R(γc-s-CΣCN R(γ(XCN) Next, preferred specific examples of Nn-type liquid crystals and Nn-type liquid crystal homologs that can be used in combination with the compound of formula (I) are listed.
式（Ｉ）の化合物の２種以上の混合物の形ＩＩ＊は式（
Ｉ）の化合物の１種又は２種以上と前記したＮｎＷ液晶
及び／又はその同族体との混合物の形態でＤＡＭセル用
液晶として使用できる。Form II* of a mixture of two or more compounds of formula (I) has the formula (
It can be used as a liquid crystal for a DAM cell in the form of a mixture of one or more of the compounds of I) and the above-mentioned NnW liquid crystal and/or its homolog.
また、式（夏）の化合物の１種スは２種以上と前記した
Ｎｐ型液晶及び／又はその−襄体と前記したＮｎ型液晶
及び／又はその同族体との混合物の形態でＦＥＭセル用
液晶として使用できる。Further, one of the compounds of the formula (summer) can be used for FEM cells in the form of a mixture of two or more types, the above-mentioned Np-type liquid crystal and/or its homologue, and the above-mentioned Nn-type liquid crystal and/or its homolog. Can be used as a liquid crystal.
・次に本発明を実施例をもって具体的に説明する。-Next, the present invention will be specifically explained using examples.
実施例に
硫化Ｒ素５Ｑａｌ中に無水塩化アルミニウム１６．０．
ｐ（Ｑ、１２０ｍｏｌ）４加え室温で攪拌しながらトラ
ンス−４−ｎ−プロピルシクロヘキシル酢酸クロライド
２０．５１１（０，１００ｍｏｌ）を滴下した。これを
０″ｔｌＪｃ冷却し、攪拌しながらビフェニルを二硫化
ｆｌ５０ｉｕに溶解させた溶液を滴下し０℃で５時間反
応させた後、室温にもどして２時間反応させた。反応後
、二硫化炭素を留去した後、これを氷水中に加え６０℃
で１時間攪拌した。冷却後エーテルで抽出し、水洗、乾
燥し、エーテル留去後エタノールで再結晶精製し、下記
化合物２６．６．＠（０，０８３１ｍｏｌ）を得た。In an example, anhydrous aluminum chloride 16.0.
p(Q, 120 mol) 4 was added, and 20.511 (0,100 mol) of trans-4-n-propylcyclohexyl acetic acid chloride was added dropwise while stirring at room temperature. This was cooled to 0"tlJc, and a solution of biphenyl dissolved in fl50iu of disulfide was added dropwise with stirring, and reacted at 0°C for 5 hours, then returned to room temperature and reacted for 2 hours. After the reaction, carbon disulfide was added. After distilling off, it was added to ice water at 60°C.
The mixture was stirred for 1 hour. After cooling, it was extracted with ether, washed with water, dried, and after distilling off the ether, it was recrystallized and purified with ethanol to obtain the following compound 26.6. @(0,0831 mol) was obtained.
この化合物にトリエチレングリコール８５縦、ヒドラジ
ンハイドレイド６．６５．！ｉ’（ＣＬ１３３ｍｏｌ）
、水酸化カリウム１５８．ｐ（０，２４６ｍｏｌ）を加
え、攪拌しながら温度を除々に上げ１８０℃で６時間反
応させた。冷却後、水２００＋１１７’＆加えエーテル
で抽出した。水で洗浄後、無水硫酸す）ＩＪウムで乾燥
した後エーテルを留去し、ｎ−ヘキサン−エタノールで
再結晶精製し、下記化合安’２４１，９（０，０７５５
ｍｏｌ）を得た。This compound contains triethylene glycol 85% and hydrazine hydrate 6.65%. ! i' (CL133mol)
, potassium hydroxide 158. p (0,246 mol) was added, and the temperature was gradually raised while stirring, and the reaction was carried out at 180° C. for 6 hours. After cooling, the mixture was extracted with 200+117' water and ether. After washing with water and drying with anhydrous sulfuric acid (IJ), the ether was distilled off, and recrystallization was carried out with n-hexane-ethanol.
mol) was obtained.
二憾化炭１４Ｑａｊ中に無水塩化アルミニウム１２．１
．＠（０，９０７ｍｏｌ）を加え室温で攪拌しながらト
ランス−４−ｎ−プロピルシクロヘキシル酢酸クロライ
ド１５．３．Ｆ（ｃＬ０７５５ｍｏｌ）を滴下した。こ
れを０℃に冷却し、攪拌しなから上記化合物２５１．９
（０，０７５５ｍｏ１．）を二硫化炭素４０−に溶解さ
せた溶液を膚下し、０℃で５時間反応させた後室温にも
として２時間反応させた。反応俊二硫化縦素を留去した
後、これを氷水中に加え６０”Ｃで１時間攪拌した。冷
却後エーテルで抽出し、水洗、乾燥し、エーテル留去後
ｎ−ヘキサンーエタノールで再結晶精製し、下記化合物
２８．８＃（Ｑ、０６１０ｍｏｌ）ｔ’得た。Anhydrous aluminum chloride 12.1 in carbon dioxide 14Qaj
．． (0,907 mol) was added and while stirring at room temperature, trans-4-n-propylcyclohexyl acetic acid chloride 15.3. F (cL0755 mol) was added dropwise. This was cooled to 0°C, and without stirring, the above compound 251.9 was added.
A solution of (0,0755 mo1.) dissolved in 40-carbon disulfide was poured onto the skin, reacted at 0°C for 5 hours, and then brought to room temperature and reacted for 2 hours. After distilling off the reacted hydrogen disulfide, it was added to ice water and stirred at 60"C for 1 hour. After cooling, it was extracted with ether, washed with water, dried, and after distilling off the ether, it was recrystallized with n-hexane-ethanol. The product was purified to obtain the following compound 28.8# (Q, 0610 mol) t'.
この化合物にトリエチレングリコール５０Ｍ１、ヒドラ
ジシバイドレイド５．７９．９（０，０７５６ｍｏｌ）
、水酸化カリウム７８７ｇ（０，１４０ｍｏｌ）ｔ’加
え、攪拌しながら温度を除々に上げ１８０℃で６時間反
応させた。冷却後、水１５Ｑｄ７加えエーテルで抽出し
た。水で洗浄後、無水硫酸ナトリウムで乾燥した後エー
テルを留去し、ｎ−ヘキサン−エタノールで再結晶精製
し、下記化合物２４．ｉ（α０５３１ｍｏｌ）を得た。This compound contains triethylene glycol 50M1, hydrazibide 5.79.9 (0,0756 mol)
, 787 g (0,140 mol) of potassium hydroxide were added, and the temperature was gradually raised while stirring, and the reaction was carried out at 180° C. for 6 hours. After cooling, 15Qd7 of water was added and extracted with ether. After washing with water and drying over anhydrous sodium sulfate, the ether was distilled off and recrystallized from n-hexane-ethanol to obtain the following compound 24. i (α0531 mol) was obtained.
収率５５．１％転移温度４０℃（Ｃ１０）２０９℃（８
＃Ｎ）
２２３℃（Ｎ２Ｎ）Yield 55.1% Transition temperature 40℃ (C10) 209℃ (8
#N) 223℃ (N2N)
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10624981A JPS5933566B2 (en) | 1981-07-09 | 1981-07-09 | 1,4-di-(cyclohexylethyl)biphenyl derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10624981A JPS5933566B2 (en) | 1981-07-09 | 1981-07-09 | 1,4-di-(cyclohexylethyl)biphenyl derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5810529A true JPS5810529A (en) | 1983-01-21 |
| JPS5933566B2 JPS5933566B2 (en) | 1984-08-16 |
Family
ID=14428823
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10624981A Expired JPS5933566B2 (en) | 1981-07-09 | 1981-07-09 | 1,4-di-(cyclohexylethyl)biphenyl derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5933566B2 (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5872528A (en) * | 1981-10-14 | 1983-04-30 | エフ・ホフマン―ラ ロシユ アーゲー | Phenylethanes |
| US4439015A (en) * | 1981-01-30 | 1984-03-27 | Hoffmann-La Roche Inc. | Disubstituted ethanes |
| US4583826A (en) * | 1981-10-14 | 1986-04-22 | Hoffmann-La Roche Inc. | Phenylethanes |
| US4613208A (en) * | 1982-11-29 | 1986-09-23 | Hoffmann-La Roche Inc. | Coloring substance-containing liquid crystal mixtures |
-
1981
- 1981-07-09 JP JP10624981A patent/JPS5933566B2/en not_active Expired
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4439015A (en) * | 1981-01-30 | 1984-03-27 | Hoffmann-La Roche Inc. | Disubstituted ethanes |
| JPS5872528A (en) * | 1981-10-14 | 1983-04-30 | エフ・ホフマン―ラ ロシユ アーゲー | Phenylethanes |
| US4583826A (en) * | 1981-10-14 | 1986-04-22 | Hoffmann-La Roche Inc. | Phenylethanes |
| JPH0329050B2 (en) * | 1981-10-14 | 1991-04-23 | Efu Hofuman Ra Roshu Ag | |
| US4613208A (en) * | 1982-11-29 | 1986-09-23 | Hoffmann-La Roche Inc. | Coloring substance-containing liquid crystal mixtures |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5933566B2 (en) | 1984-08-16 |
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