JPS588023A - 1,2-di-(cyclohexylphenyl)ethane derivative - Google Patents
1,2-di-(cyclohexylphenyl)ethane derivativeInfo
- Publication number
- JPS588023A JPS588023A JP10624781A JP10624781A JPS588023A JP S588023 A JPS588023 A JP S588023A JP 10624781 A JP10624781 A JP 10624781A JP 10624781 A JP10624781 A JP 10624781A JP S588023 A JPS588023 A JP S588023A
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- compound
- nematic
- formula
- 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.)
- Pending
Links
Landscapes
- Liquid Crystal Substances (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (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エタン誘導体
の新規ネマチック液晶化金物に関する。本発１１によっ
て提供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−エカトリ
アル）−４′ゴタ午ルキルシクロへキシルフェニル）−
２−４’−（）ランス（エカトリアル−エカトリアル）
−−−アル式（Ｉ）の化合物は弱い負り誘電異方性をも
つ化合物であり例えば、エム・シャット（Ｍ＠８ｈｓｅ
ｔｔ）等〔ムＰＰＬＩ、ＩＤＰＨＹ８ＩＣ８ＬＥＴＴＥ
Ｒ８１８１２７〜１２８（１９７１））によって提案さ
れた電界効釆蓋セル（フィールド拳エフェクトΦモード
・苓ル）又はジー・エイチ・バイルマイヤー（Ｇ＠ＨＨ
ｅ１１ｍ＊１ｓｒ）等（ＰＲＯＣＩＣＩＤＩＮＧ ＯＦ
ＴＨＥＩ、Ｅ、Ｅ、５６ １１６２〜１１７１ （１
９６８） 〕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・モード・セル）又はジー
・エイチ・バイルミイヤー（Ｇ＊ＨＨｅｉｌｍｅｉｅｒ
）等［”ＡＰＰＬＩＥＤ ＰＨＹ８ＩＣ８ＬＥＴＴＥ
Ｒ８１５，９１（１９６８））あるいはディー・エル・
ホワイト（ＤＬＷｈｉｔ＠）等［ＪＯＵＲＮＡＬ ０Ｆ
ＡＰＰＩ、ＩＥＤ ＰＨＹＳＩＣ８４５，４７１８（１
９７４））ｋよって提案されたゲスト拳ホスト型セルな
どに適用することができる。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to novel nematic liquid crystallized metals of ethane derivatives useful as electro-optic display materials. The novel nematic liquid crystal provided by the present invention 11 is represented by the general formula 1-(trans(equatorial-equatorial)-4'Gotanylcyclohexylphenyl)-
2-4'-() Lance (Ecatorial-Equatorial)
---Al The compound of formula (I) is a compound with weak negative dielectric anisotropy, and for example, M Shutt (M@8hse)
tt) etc. [mu PPLI, IDPHY8IC8LETTE
R818127-128 (1971)) or the field-effect button lid cell (Field fist effect Φ mode・Reiru) proposed by G.H. Beilmeyer (G@HH
e11m*1sr) etc. (PROCICIDING OF
THEI, E, E, 56 1162-1171 (1
968)] or the dynamic scattering mode cell proposed by G*HH Heilmeier.
) etc. [”APPLIED PHY8IC8LETTE
R815, 91 (1968)) or D.L.
White (DLWhit@) etc. [JOURNAL 0F
APPI, IED PHYSIC845,4718(1
The present invention can be applied to a guest-hosted cell proposed by K.974)).
式（ｒ）の化合物はネマチック−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
、然も無色乳白色といった幾多の優れた％性を有してい
る。よって式（Ｉ）の化合物を用いれば長寿命でネマチ
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 compound of formula (r) 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. It also has many excellent properties such as being colorless and milky white. Therefore, by using the compound of formula (I), it is possible to produce a liquid crystal display element with a long life, a wide nematic temperature range, and a high speed response.
本発明によれば、式（Ｉ）の化合物は次の製造方法に従
って製造される。According to the invention, the compound of formula (I) is manufactured according to the following manufacturing method.
第１段階一式（■）の化合物に二硫化炭素あるい１ニト
ロベンゼン中で式（ｍ）の化合物と無水塩化アルミニウ
ムを反応させて式（■）の化合物を製造する。First step: A compound of formula (■) is reacted with a compound of formula (m) and anhydrous aluminum chloride in carbon disulfide or 1 nitrobenzene to produce a compound of formula (■).
第２段階−第」段階で製造された式（■）の化合物にジ
エチレングリコールある一寸トリエチレングリコール中
でヒト □ラジンと水酸イヒカリウムを反応させて
式（Ｉ）の化合物を製造する。Step 2 - The compound of formula (■) prepared in step 2 is reacted with diethylene glycol. The compound of formula (I) is prepared by reacting human □radin with potassium hydroxide in triethylene glycol.
斯くして製造された式（Ｉ）の化合物の転移温度を第１
表に掲げる。The transition temperature of the compound of formula (I) thus prepared is
Listed in the table.
第１表
Ｒ１ｇ、 転移温度（℃）ｎ−Ｃ３Ｈ７−
Ｔｌ−０３Ｈ？−１７５（Ｃ−ｅＮ） ２２２（Ｎ：
工） ｆ’７３（ＳＲＮ）ｎ−Ｃ６Ｈ１３−ｎ−Ｃ５Ｈ
１２−判り≠１白７５（Ｃ−４８）２１４（８；：Ｉ）
表中、Ｃは結晶、Ｓはスメクチック相、Ｎはネマチック
相、■は等方性液体相を夫々表わす。Table 1 R1g, Transition temperature (°C) n-C3H7-
Tl-03H? -175(C-eN) 222(N:
Engineering) f'73 (SRN) n-C6H13-n-C5H
12-obvious≠1white75(C-48)214(8;:I) In the table, C represents a crystal, S represents a smectic phase, N represents a nematic phase, and ■ represents an isotropic liquid phase.
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、紋化合物の２種以上の混合
物の形態或は該化合物の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。式（Ｉ）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Ｎｐ型液晶という）及び／又はＮ
ｐ型液晶の同族体である非ネマチック液晶化合物（以下
Ｎｐ型液晶同族体といつ）、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Ｎｍ’ｌｌ液晶の同族体である非ネマチ
ック液晶化合物（以下Ｍａｉｌ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) may be used in the form of a mixture of two or more types of black-and-white compounds, or in the form of a mixture of one or more of these compounds and other nematic liquid crystal compounds and It can be used in the form of a mixture with/or a non-nematic liquid crystal compound, but preferably, a mixture of two or more compounds of formula (I) is used as a matrix liquid crystal, and this matrix liquid crystal is combined with other nematic liquid crystal compounds and/or It is recommended to use a mixed form of 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 formula (I) include nematic liquid crystal compounds with large positive dielectric constant anisotropy (hereinafter referred to as Np-type liquid crystal); and/or N
Non-nematic liquid crystal compounds that are homologs of p-type liquid crystals (hereinafter referred to as Np-type liquid crystal homologs), nematic liquid crystal compounds having negative or small positive dielectric constant anisotropy (hereinafter referred to as Nn-type liquid crystals), and/or Nm' Included are non-nematic liquid crystal compounds (hereinafter referred to as Mail liquid crystal homologs) that are homologues of the 11 liquid crystal, 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Ｎｐ１ｉ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 type liquid crystals and Np1i liquid crystal homologues are listed below.
Ｒ擾ヴしｏｆｉｃｗ
次に１式（Ｉ）の化合物と混合して使用することのでき
るＮ＋ａＪｌｌ液晶及びＮｎｆｊｌ！液晶同族体の好ま
しい具体例を列記する。Next, N+aJll liquid crystal and Nnfjl! which can be used in combination with the compound of formula (I). Preferred specific examples of liquid crystal homologs are listed below.
式（Ｉ）の化合物の２種以上の混合物の形態或は式（Ｉ
）の化合物の１種又は２種以上と前記したＮｕ型液晶及
び／又はその同族体との混合物の形態でＤＳＭセル用液
晶として使用できる。In the form of a mixture of two or more compounds of formula (I) or in the form of a mixture of two or more compounds of formula (I)
) can be used as a liquid crystal for a DSM cell in the form of a mixture of one or more of the above compounds and the above-mentioned Nu-type liquid crystal and/or its homolog.
また、式（Ｉ）の化合物の１１１又は２種以上と前記し
たＮｐ型液晶及び／又はその同族体と前記したＮ＋ａｉ
Ｊｌｌｌｔ晶及び／又はその同族体との混合物の形態で
ＦＫＭセル用液晶として使用で會る。Further, 111 or two or more of the compounds of formula (I), the above-mentioned Np type liquid crystal and/or its homolog, and the above-mentioned N+ai
It is used as a liquid crystal for FKM cells in the form of a mixture with Jllt crystal and/or its congeners.
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
硫化炭素１００ｄ中に無水塩化アル１ニウム１＆Ｏ１（
α１２０ｍｏｌ）を加え室温で攪拌しなからトランス−
４−ｎ−プロピルシクロヘキシルフェニル酢酸クロライ
ド２７、９ Ｎ （α１００ｍｏｌ）を滴下した。これ
を０℃に冷却し、攪拌しながらトランス−４−ｍ−プロ
ピル−１−フェニルシクロヘキサン２０．２Ｉ！（０，
１００ｍｏｌ）を滴下し、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。In an example, anhydrous aluminum chloride 1&O1 (
Add α120 mol) and stir at room temperature, then trans-
4-n-propylcyclohexylphenylacetic acid chloride 27.9 N (α100 mol) was added dropwise. This was cooled to 0° C. and, with stirring, 20.2 I of trans-4-m-propyl-1-phenylcyclohexane! (0,
After dropping 100 mol) and reacting at 0°C for 5 hours,
The mixture was brought to room temperature and reacted for 2 hours.
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−−ヘキサン−エタノー
ルで再結晶精製し、下記化合物３α６１Ｃα０６８９ｍ
１）を得た。After the reaction, carbon disulfide was distilled off, and the mixture was added to ice water and stirred at 60°C for 1 hour. After cooling, extract with ether,
Washing with water, drying, distilling off ether, recrystallizing with hexane-ethanol, and obtaining the following compound 3α61Cα0689m.
1) was obtained.
この化合物にトリエチレングリコール１００ｍ１．ヒド
ラジンハイドレイド５．５０１ （［Ｌｌ １０ｍｏｌ
）、水酸カリウム１１４Ｎ（α２０４！ＩＩ・ｌ）を加
え、攪拌しながら温度を徐々に上げ、１８０℃で３時間
反応させた。冷却後、水１５０ｄを加えｎ−ヘキサンで
抽出しへ水で洗浄後、無水硫酸ナトリウムで乾燥した後
ｎ−ヘキナンを留去し、鳳−ヘキサン−エタノールで再
結晶精製し、下記化合物２５．２Ｊ’（α０５８６ｍ＠
ｌ）を得た。Add 100 ml of triethylene glycol to this compound. Hydrazine hydrate 5.501 ([Ll 10mol
) and potassium hydroxide 114N (α204!II·l) were added, the temperature was gradually raised while stirring, and the reaction was carried out at 180° C. for 3 hours. After cooling, 150 d of water was added, extracted with n-hexane, washed with water, dried over anhydrous sodium sulfate, n-hexane was distilled off, recrystallized with hexane-ethanol and purified to obtain 25.2 J of the following compound. '(α0586m@
l) was obtained.
収率５８．６％ 転移温度 １７５℃（Ｃ−ｅＮ
）２２２℃（Ｎ、：Ｉ）
１７３℃（８：Ｎ）
実施例２
実施例１と同様の要領で下記化合物を得た。Yield 58.6% Transition temperature 175°C (C-eN
) 222°C (N,:I) 173°C (8:N) Example 2 The following compound was obtained in the same manner as in Example 1.
収率 ５２．７％ 転移温度 ７３℃（Ｃ−＋
８ ）２１４℃（Ｓ、：Ｉ）Yield: 52.7% Transition temperature: 73°C (C-+
8) 214℃ (S, :I)
Claims (1)
キル基を表わす。〕 で表わされる化合物・[Claims] General formula [wherein R1 and R2 each represent a linear alkyl group having 1 to 7 carbon atoms. ] The compound represented by
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10624781A JPS588023A (en) | 1981-07-09 | 1981-07-09 | 1,2-di-(cyclohexylphenyl)ethane derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10624781A JPS588023A (en) | 1981-07-09 | 1981-07-09 | 1,2-di-(cyclohexylphenyl)ethane derivative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS588023A true JPS588023A (en) | 1983-01-18 |
Family
ID=14428772
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10624781A Pending JPS588023A (en) | 1981-07-09 | 1981-07-09 | 1,2-di-(cyclohexylphenyl)ethane derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS588023A (en) |
Cited By (10)
| 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 |
| US4472592A (en) * | 1982-07-09 | 1984-09-18 | Dainippon Ink And Chemicals, Inc. | Nematic liquid crystalline compounds |
| US4526704A (en) * | 1982-07-28 | 1985-07-02 | Hoffmann-La Roche Inc. | Multiring liquid crystal esters |
| JPS60204731A (en) * | 1984-03-29 | 1985-10-16 | Dainippon Ink & Chem Inc | Novel tolan nematic liquid crystal compound |
| US4583826A (en) * | 1981-10-14 | 1986-04-22 | Hoffmann-La Roche Inc. | Phenylethanes |
| US4606845A (en) * | 1983-05-14 | 1986-08-19 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Bicyclohexylethanes |
| US4613208A (en) * | 1982-11-29 | 1986-09-23 | Hoffmann-La Roche Inc. | Coloring substance-containing liquid crystal mixtures |
| US4652089A (en) * | 1983-11-02 | 1987-03-24 | Hoffmann-La Roche Inc. | Liquid crystalline compounds and mixtures |
| US4684478A (en) * | 1985-01-07 | 1987-08-04 | Chisso Corporation | Novel liquid crystal compound for high temperatures |
| DE3926190A1 (en) * | 1988-08-09 | 1990-02-15 | Seiko Epson Corp | New 5-(alkylcyclohexyl)-2-alkyl-cyclohexyl phenyl)-pyrimidine cpds. - useful liq. crystal components e.g. for electro=optical displays |
-
1981
- 1981-07-09 JP JP10624781A patent/JPS588023A/en active Pending
Cited By (12)
| 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 |
| 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 | |
| US4472592A (en) * | 1982-07-09 | 1984-09-18 | Dainippon Ink And Chemicals, Inc. | Nematic liquid crystalline compounds |
| US4526704A (en) * | 1982-07-28 | 1985-07-02 | Hoffmann-La Roche Inc. | Multiring liquid crystal esters |
| US4613208A (en) * | 1982-11-29 | 1986-09-23 | Hoffmann-La Roche Inc. | Coloring substance-containing liquid crystal mixtures |
| US4606845A (en) * | 1983-05-14 | 1986-08-19 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Bicyclohexylethanes |
| US4652089A (en) * | 1983-11-02 | 1987-03-24 | Hoffmann-La Roche Inc. | Liquid crystalline compounds and mixtures |
| JPS60204731A (en) * | 1984-03-29 | 1985-10-16 | Dainippon Ink & Chem Inc | Novel tolan nematic liquid crystal compound |
| JPH041731B2 (en) * | 1984-03-29 | 1992-01-14 | Dainippon Ink & Chemicals | |
| US4684478A (en) * | 1985-01-07 | 1987-08-04 | Chisso Corporation | Novel liquid crystal compound for high temperatures |
| DE3926190A1 (en) * | 1988-08-09 | 1990-02-15 | Seiko Epson Corp | New 5-(alkylcyclohexyl)-2-alkyl-cyclohexyl phenyl)-pyrimidine cpds. - useful liq. crystal components e.g. for electro=optical displays |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4431853A (en) | Dicyclohexylethane derivatives | |
| JPS588023A (en) | 1,2-di-(cyclohexylphenyl)ethane derivative | |
| JPS588022A (en) | 1-cyclohexyl-2-cyclohexylbiphenylethane derivative | |
| JPS6033411B2 (en) | 1-cyclohexyl-2-cyclohexyl phenylethane derivative | |
| JPS5849324A (en) | 1-cyclohexyl-2-(4'-halobiphenyl)ethane derivative | |
| EP0198714B1 (en) | Liquid cristalline compositions containing cyclohexylcyclohexene derivatives, and their use | |
| JPS5935901B2 (en) | 1-Cyclohexyl-2-(4'-halolophenyl)ethane derivative | |
| JPH0247971B2 (en) | ||
| JPS59141527A (en) | Partially reduced naphthalene derivative | |
| JPS59141540A (en) | Tricyclic carboxylic acid ester derivative | |
| JPS60204780A (en) | 4-(trans-5-alkyl-1,3-dioxa-2-yl)benzoic acid derivative | |
| JPS5933566B2 (en) | 1,4-di-(cyclohexylethyl)biphenyl derivative | |
| JP2829436B2 (en) | Cyclobutane derivative | |
| JPS61291536A (en) | Crotyloxybenzene derivative | |
| JPS59110630A (en) | 1-cyclohexyl-2-cyclohexylbiphenylethane derivative | |
| JPS59193848A (en) | Novel nematic liquid crystal compound | |
| JPH0338572A (en) | Pyrimidine derivative | |
| JPS62286943A (en) | 4'-substituted biphenyl crotyl ether derivative | |
| JP2822083B2 (en) | Alkyneoxyphenylbicyclohexanes compounds | |
| JPS59170030A (en) | Liquid crystal compound | |
| JP2636347B2 (en) | Fluoro compound | |
| JPS6287556A (en) | Ester compound | |
| JPH0261471B2 (en) | ||
| JP2819682B2 (en) | Pyrimidine derivative and liquid crystal composition | |
| JPH0142261B2 (en) |