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
Prior art keywords
trans
formula
compounds
alkyl
compound
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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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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
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
7−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
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
1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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JPH0539287A true JPH0539287A (ja) 1993-02-19
JPH0662603B2 JPH0662603B2 (ja) 1994-08-17

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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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