JPH0539287A - シクロヘキサンカルボニトリル誘導体 - Google Patents

シクロヘキサンカルボニトリル誘導体

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Publication number
JPH0539287A
JPH0539287A JP3339895A JP33989591A JPH0539287A JP H0539287 A JPH0539287 A JP H0539287A JP 3339895 A JP3339895 A JP 3339895A JP 33989591 A JP33989591 A JP 33989591A JP H0539287 A JPH0539287 A JP H0539287A
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Japan
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trans
formula
compounds
alkyl
compound
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JP3339895A
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JPH0662603B2 (ja
Inventor
Martin Petrzilka
マルテイン・ペトルツイルカ
Martin Schadt
マルテイン・シヤツト
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F Hoffmann La Roche AG
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F Hoffmann La Roche AG
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Publication of JPH0539287A publication Critical patent/JPH0539287A/ja
Publication of JPH0662603B2 publication Critical patent/JPH0662603B2/ja
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  • Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
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Abstract

(57)【要約】 （修正有） 【構成】 下記式 〔式中、Ｒ1は直鎖状のＣ1〜Ｃ12−アルキルを表わす〕
の化合物、及び該化合物を含む液晶混合物。 【効果】 本化合物は、誘電率の大きな正の異方性、小
さな光学的異方性、低粘度、低閾値電位及び短い応答時
間、改善された中間相挙動等を兼備しており、電子−光
学的表示装置における液晶性誘電体として適している。

Description

【発明の詳細な説明】
【０００１】本発明は一般式
【０００２】
【化３】
【０００３】式中、Ｒ1は直鎖状のＣ1〜Ｃ12−アルキル
を表わす、のトランス−４−（トランス−５−アルキル
−ｍ−ジオキサン−２−イル）シクロヘキサンカルボニ
トリル、並びに上記式Ｉの化合物の製造、これらの化合
物を含む液晶混合物及び電子−光学目的のためのその用
途に関する。
【０００４】式Ｉの化合物は同時に、誘電率の大きな正
の異方性、小さな光学的異方性、低粘度（特に混合物と
して用いた場合）、低閾値電位及び短い応答時間並びに
改善された中間相挙動（ｍｅｓｏｐｈａｓｅ ｂｅｈａ
ｖｉｏｕｒ）を有している。更に、該化合物は高度の化
学的安定性及びわずかな伝導率のみを有し、無色であ
り、全ての通常の液晶と良好な混和性を有し、そして表
示装置において高度のコントラストを示す。従って、本
発明によって提供される化合物は電子−光学的表示装
置、例えば回転セル及びゲスト／ホストセル、殊に回転
セルにおける液晶性誘電体として極めてよく適する。
【０００５】式Ｉの好ましい化合物はＲ1が直鎖状のＣ3
〜Ｃ8−アルキルを表わすものである。
【０００６】式Ｉの化合物は一般式
【０００７】
【化４】
【０００８】式中、Ｒ1は上記の意味を有する、の化合
物をトランス−４−シアノシクロヘキサンカルボキシア
ルデヒドまたはその適当なアセタールと反応させて製造
することができる。
【０００９】式Ｉの化合物は他の液晶または非液晶性物
質、例えばシッフ塩基、アゾベンゼン類、アゾキシベン
ゼン類、安息香酸フェニル類、シクロヘキサンカルボン
酸フェニルエステル類、シクロヘキサンカルボン酸シク
ロヘキシルエステル類、ビフェニル類、ターフェニル
類、フェニルシクロヘキサン類、桂皮酸誘導体、フェニ
ルピリミジン類、ジフェニルピリミジン類、シクロヘキ
シルフェニルピリミジン類、フェニルジオキサン類、２
−シクロヘキシル−１−フェニルエタン類、１，２−ジ
シクロヘキシルエタン類等の群からの物質との混合物の
形態で用いることができる。かかる物質は当業者にとっ
ては既知のものであり、更にその多くのものは市販品と
して入手することができる。しかしながら、非液晶性成
分を用いる場合、全混合物が十分に大きな中間相範囲を
有するように、追加の液晶化合物の十分な量を用いるこ
とに注意すべきである。勿論、また本発明によって提供
される混合物は同時に１種またはそれ以上の式Ｉの化合
物を含んでいてもよい。
【００１０】１種またはそれ以上の式Ｉの化合物の外
に、本発明によって提供される混合物は随時、好ましく
は次の一般式の化合物の１種またはそれ以上を含有す
る：
【００１１】
【化５】
【００１２】式中、環Ｂ1は１，４−フェニレンまたは
トランス−１，４−シクロヘキシレンを表わし、Ｒ2は
直鎖状のＣ2〜Ｃ7−アルキルを表わし、Ｒ3はシアノま
たは直鎖状のＣ1〜Ｃ6−アルコキシを表わし、Ｒ4はシ
アノまたは直鎖状のＣ1〜Ｃ7−アルキルもしくはＣ1〜
Ｃ7−アルコキシを表わし、そしてＲ5及びＲ6は直鎖状
のＣ1〜Ｃ7−アルキルを表わし；ｐは０または１を表わ
し；Ｒ7はトランス−４−アルキルシクロヘキシル、
４′−アルキル−４−ビフェニリル、ｐ−（トランス−
４−アルキルシクロヘキシル）フェニル、２−（トラン
ス−４−アルキルシクロヘキシル）エチルまたはｐ−
［２−（トランス−４−アルキルシクロヘキシル）エチ
ル］フェニルを表わし、そしてＲ8はトランス−４−ア
ルキルシクロヘキシルを表わすか、Ｒ7はトランス−４
−アルキルシクロヘキシルを表わし、そしてＲ8はｐ−
（トランス−４−アルキルシクロヘキシル）フェニル、
ｐ−［２−（トランス−４−アルキルシクロヘキシル）
エチル］フェニルまたは４′−（トランス−４−アルキ
ルシクロヘキシル）−４−ビフェニリルを表わすか、或
いはＲ7はｐ−アルキルフェニルを表わし、そしてＲ8は
ｐ−［２−（トランス−４−アルキルシクロヘキシル）
エチル］フェニルを表わし、そしてＲ7及びＲ8における
アルキル基は直鎖状のＣ1〜Ｃ7−アルキルであり；記号
Ｚ1及びＺ2の一つは−ＣＯＯ−または−ＯＯＣ−を表わ
し、そして記号Ｚ1、Ｚ2、Ｚ3及びＺ4の残りは一つの共
有結合を表わすか、或いはまたこれらの記号の一つは−
ＣＨ2ＣＨ2−を表わし；式ＸＩＶにおける環Ｂ1及びＢ5
は式
【００１３】
【化６】
【００１４】の基またはトランス−１，４−シクロヘキ
シレンを表わし；環Ｂ2、Ｂ3及びＢ4は式ＸＶの基或い
は、これらが一つの共有結合によってこれらの環の他の
二つの少なくとも一つと結合していない限り、またトラ
ンス−１，４−シクロヘキシレンを表わし；Ｙは水素或
いは、一つの共有結合を介して更に環と結合していない
式ＸＶの環の一つ上のフッ素、塩素またはメチルを表わ
し；Ｒ9及びＲ10は直鎖状のＣ1〜Ｃ7−アルキル或いは
また式ＸＶの環上の直鎖状のＣ1〜Ｃ7−アルコキシを表
わす。
【００１５】式ＩＩＩ〜ＸＩＩＩの化合物は既知のもの
であるか、または既知の化合物の同族体である。
【００１６】式ＸＩＶのエステルは新規なものである
が、しかしこれらのものはそれ自体既知のエステル化法
に従って得ることができる。式ＸＩＶのエステルを製造
する際に必要な出発物質は既知のものであるか、または
既知の化合物の同族体であり、既知の方法に従って製造
することができる。
【００１７】式Ｉの化合物との混合物は、式Ｉの化合物
の１種またはそれ以上の外に、好ましくは式ＩＩＩ〜Ｘ
ＩＶの化合物の１種またはそれ以上を含有する。式Ｉの
化合物の量は有利には約１〜５０重量％、好ましくは約
５〜３０重量％である。
【００１８】更に、本発明によって提供される混合物は
適当な光学的活性化合物（例えば光学的活性ビフェニル
類）及び／または二色性着色物質（例えばアゾ、アゾキ
シまたはアントラキノン着色物質）を含んでいてもよ
い。かかる化合物の量は溶解度、所望の色調（ｐｉｔｃ
ｈ）、色、消光等によって決定される。好ましくは光学
的活性化合物の量は最大約４重量％であり、そして二色
性着色物質の量は最大約１０重量％である。
【００１９】本発明によって提供される液晶混合物の製
造はそれ自体既知の方法において、例えば各成分の混合
物をわずかに透明点以上の温度に加熱し、次に該混合物
を冷却することによって行うことができる。
【００２０】また、誘電体として本発明によって提供さ
れる混合物を含む電子−光学装置の製造はそれ自体既知
の方法において、例えば適当なセルを空にし、そしてこ
の空にしたセル中に該混合物を導入することによって行
うことができる。
【００２１】また、本発明は本明細書に記載した全ての
新規化合物、混合物、製法、用途及び装置に関する。
【００２２】本発明によって提供される化合物の製造を
更に詳細に以下の実施例によって説明する。実施例中、
Ｃは結晶相を表わし、Ｓはスメクティク相を表わし、Ｓ
BはスメクティクＢ相を表わし、Ｎはネマティク相を表
わし、そしてＩはイソトロピック（ｉｓｏｔｒｏｐｉ
ｃ）相を表わす。
【００２３】
【実施例】
実施例１ ベンゼン１００ｍｌ中のトランス−４−シアノシクロヘ
キサンカルボキシアルデヒド２．００ｇ、２−ペンチル
−１，３−プロパンジオール２．１３ｇ及びｐ−トルエ
ンスルホン酸６５ｍｇの混合物を水分離器及び還流冷却
器を備えた丸底フラスコ中にてアルゴン通気し且つ水を
分離しながら３時間還流下で加熱した。次に混合物を炭
酸カリウム３．０ｇで処理し、室温で１６時間撹拌し、
次いで濾過し、濾液を濃縮した。結晶性残渣（４．１
ｇ）を０℃でヘキサンから再結晶し、純度９９．１％に
おいて無色の結晶としてトランス−４−（トランス−５
−ペンチル−ｍ−ジオキサン−２−イル）シクロヘキサ
ンカルボニトリル１．４７ｇ（３８％）を得た。更にヘ
キサンから０℃で再結晶後、純度は９９．９％に増加し
た；融点（Ｃ−Ｎ）４５．６℃、透明点（Ｎ−Ｉ）４
６．７℃。
【００２４】同様の方法で次の化合物を製造した：トラ
ンス−４−（トランス−５−プロピル−ｍ−ジオキサン
−２−イル）シクロヘキサンカルボニトリル；融点（Ｃ
−Ｉ）６３．６℃、透明点（Ｎ−Ｉ）３９．３℃、トラ
ンス−４−（トランス−５−ブチル−ｍ−ジオキサン−
２−イル）シクロヘキサンカルボニトリル；融点（Ｃ−
Ｎ）３３．２℃、透明点３５．６℃、トランス−４−
（トランス−５−ヘプチル−ｍ−ジオキサン−２−イ
ル）シクロヘキサンカルボニトリル；融点（Ｃ−Ｉ）５
６．３℃、透明点（Ｎ−Ｉ）４５．０℃。

Claims (2)

    【特許請求の範囲】
  1. 【請求項１】 式 【化１】 式中、Ｒ1は直鎖状のＣ1〜Ｃ12−アルキルを表わす、の
    化合物。
  2. 【請求項２】 少なくとも２種の化合物からなり、その
    うちの少なくとも１種が式 【化２】 式中、Ｒ1は直鎖状のＣ1〜Ｃ12−アルキルを表わす、の
    化合物であることを特徴とする液晶混合物。
JP3339895A 1983-03-16 1991-11-28 シクロヘキサンカルボニトリル誘導体 Expired - Lifetime JPH0662603B2 (ja)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
CH143683 1983-03-16
CH153983 1983-03-22
CH226/84-4 1984-01-19
CH1539/83-1 1984-01-19
CH1436/83-2 1984-01-19
CH22684 1984-01-19

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JPH0662603B2 JPH0662603B2 (ja) 1994-08-17

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2008502754A (ja) * 2004-06-18 2008-01-31 メルク　パテント　ゲゼルシャフト　ミット　ベシュレンクテル　ハフトング 液晶媒体
JP4932705B2 (ja) * 2004-06-18 2012-05-16 メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング 液晶媒体

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US5013478A (en) 1991-05-07
HK3189A (en) 1989-01-20
EP0122389A2 (de) 1984-10-24
JPH0662603B2 (ja) 1994-08-17
EP0122389A3 (en) 1985-10-02
EP0122389B1 (de) 1987-08-05
SG67988G (en) 1989-05-26
DE3465192D1 (en) 1987-09-10
US4676604A (en) 1987-06-30

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