JPS59231059A - 2-(4-substituted phenylazo)phenanthrene derivative - Google Patents
2-(4-substituted phenylazo)phenanthrene derivativeInfo
- Publication number
- JPS59231059A JPS59231059A JP10475983A JP10475983A JPS59231059A JP S59231059 A JPS59231059 A JP S59231059A JP 10475983 A JP10475983 A JP 10475983A JP 10475983 A JP10475983 A JP 10475983A JP S59231059 A JPS59231059 A JP S59231059A
- Authority
- JP
- Japan
- Prior art keywords
- phenanthrene
- compound
- liquid crystal
- formula
- general formula
- Prior art date
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Abstract
Description
【発明の詳細な説明】
この発明は、a1規な2−(4−置換フェニルアゾ)フ
ェナントレン誘導体に係り、特に液晶性を示して液晶表
示素子の原料として有用な液晶性化合物に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a1-order 2-(4-substituted phenylazo)phenanthrene derivatives, and particularly to liquid crystalline compounds that exhibit liquid crystallinity and are useful as raw materials for liquid crystal display elements.
近年、電卓やデジタルウォッチを始めとしζ多くの分野
で液晶表示素子が使用されるよう(−なり、この液晶表
示素子についてはその用途の拡大に伴一つで要求される
緒特性も年々多岐に広が−っている。In recent years, liquid crystal display elements have come to be used in many fields, including calculators and digital watches. It's spreading.
このため、このような液晶表示素子が要求される種々の
特注に応じて組合せ使用される液晶化合物についても、
種々の% +<4:を備えたものの開発が要請されてい
る。For this reason, liquid crystal compounds that are used in combination according to various special orders that require such liquid crystal display elements,
There is a demand for the development of products with various %+<4:.
本発明渚等は、かかる要請に応えるべく種々研究を爪ね
た結芽、下記一般式(II又は[[I)(但し、式中A
はアルキル基又はアンル基である。)で示される新規な
2−(小−置換フェニルアゾ)フェナントレン誘導体を
合成し、また、これら一般式CI)又は〔■〕で示され
る化合物が優れた液晶性を備えでいることを見い出して
本発明に到達したものである。In order to meet such demands, the present inventors, Nagisa, et al.
is an alkyl group or anru group. ) and discovered that the compounds represented by the general formula CI) or [■] have excellent liquid crystallinity, and the present invention has been reached.
一般式[1)又は〔11〕で示される本発明化合物は、
フェナントレン骨格の持つ細長い平板状構造に加えてそ
の2−位に極性の大きいフェニルアゾ基を導入したため
に優れた液晶性を発揮し、また、このうちのいく一つか
のものは現在液晶表示素子として主として使用されてい
るネマチック液晶としての性質を備え、ネマチック液晶
又はイ・マチック液晶組成物の構成成分として特に有用
である。The compound of the present invention represented by general formula [1] or [11] is
In addition to the elongated plate-like structure of the phenanthrene skeleton, a highly polar phenylazo group is introduced at the 2-position, resulting in excellent liquid crystal properties. It has the properties of a commonly used nematic liquid crystal and is particularly useful as a constituent of nematic liquid crystal or imatic liquid crystal compositions.
一般式〔ID又は〔11〕で示される本発明化合物とし
ては、具体的には下記一般式〔■〕〜CISす(但し、
式中nは整数である。)で示される化合物がある。これ
らの化合物において、アルキル基の炭素数(n)に一つ
いては1〜20が好ましく、また、これらのアルキル基
は、直鎖状のものが好ましいが、全体として細長い構造
であれば若干の枝分れがあってもよい。Specifically, the compounds of the present invention represented by the general formula [ID or [11]] include the following general formulas [■] to CIS (however,
In the formula, n is an integer. ) There is a compound shown by In these compounds, the number of carbon atoms (n) in the alkyl group is preferably 1 to 20, and these alkyl groups are preferably linear, but if they have an elongated structure as a whole, some branching is possible. There may be some.
一般式CI’l又は[IDで示される本発明化合物は、
種々の合成経路で合成することができるが、代表例とし
てフェナントレン〔■〕から合成する合成経路の18例
を示せば下記の通りである。The compound of the present invention represented by the general formula CI'l or [ID,
Although it can be synthesized by various synthetic routes, 18 typical synthetic routes for synthesizing from phenanthrene [■] are shown below.
(X) (XI)
すなわち、ンクロヘキサンを溶媒にオートクレーブを使
用して精製したフェナントレン〔■〕を銅クロメート触
媒で還元し、得られた9、10−ジヒドロフェナントレ
ンl〕を木酢酸中発煙硝酸でニトロ化し、得られた2−
ニトロ−9,IO−ジヒドロフェナントレン[IX]を
四塩化炭素中で反応促進剤のベンゼンパーオキサイドを
使用してN−ブロムザクシンイミドにより脱水素し、得
られた2−ニトロフェナントレン(X)を抱水ヒドラジ
ンとノーラジウムカーボンを用いてエタノール中で還元
し、得られた2−アミノフェナントレン〔化とフエノ−
ルとをジアゾカップリングして2−(4−ヒドロキシフ
ェニルアゾ)フェナントレン(X[l)を得、この2−
(4−ヒドロキシフェニルアゾ)フェナントレン(X
l+)にアルキルハライド又はアシルハライドあるいは
酸無水物等を反応させて一般式〔I〕で示される化合物
を合成する。また、一般式C[[]で示される化合物の
合成に一ついては、上記2−二トD−<t、 10−ジ
ヒドロフェナントレン[[X]ヲエタノール中で抱水ヒ
ドラジンとパラジウムカーボンを用いて還元し、得られ
た2−アミノ−9,10−ジヒドロフェナントレン〔X
■〕とフェノールとをジアゾカップリングして2−(4
−ヒドロキシフェニルアゾ)−9,10−ジヒド「1フ
エナントレン〔刈■〕を得、この2−(4−ヒドロキシ
フェニルアゾ)−9,to−ジヒドロフェナントレン[
XIV)にアルキルハライド又はアシルハライドあるい
は酸無水物等を反応させて合成する。なお、この合成経
路において使用される還元剤、ニトロ化試薬、溶媒等に
一ついては、」二記のものに限定されないことは勿論で
ある。(X) The obtained 2-
Nitro-9,IO-dihydrophenanthrene [IX] is dehydrogenated with N-bromsuccinimide in carbon tetrachloride using benzene peroxide as a reaction promoter, and the obtained 2-nitrophenanthrene (X) is The resulting 2-aminophenanthrene was reduced in ethanol using hydrazine hydrate and Noradium carbon.
2-(4-hydroxyphenylazo)phenanthrene (X[l) is obtained by diazo coupling with
(4-hydroxyphenylazo)phenanthrene (X
l+) with an alkyl halide, an acyl halide, an acid anhydride, or the like to synthesize a compound represented by the general formula [I]. In addition, for the synthesis of the compound represented by the general formula C[[], the above 2-di-D-<t, 10-dihydrophenanthrene [[X] is reduced in ethanol using hydrazine hydrate and palladium carbon. and the obtained 2-amino-9,10-dihydrophenanthrene [X
■] and phenol through diazo coupling, 2-(4
-Hydroxyphenylazo)-9,10-dihyde "1phenanthrene [Kari■]" was obtained, and this 2-(4-hydroxyphenylazo)-9,to-dihydrophenanthrene [
It is synthesized by reacting XIV) with an alkyl halide, an acyl halide, an acid anhydride, or the like. It goes without saying that the reducing agent, nitration reagent, solvent, etc. used in this synthetic route are not limited to those listed in "2."
以上のような合成経路で製造される本発明化合物は、そ
れがネマチック液晶としての1住質を示すものに一つい
てはそれを単独であるいは2種以−1−絹み合せた混合
物で液晶表示素子に使用でき、また、そのいずれの化合
物も他のイ・マチック液晶を示す化合物と混合して液晶
表示素子として使用することができる。このように、本
発明化合物と混合して使用し得るネマチック液晶を示す
化合物としては従来公知の種々の液晶化合物があり、例
えは、アゾメチン化合物、エステル化合物又はそのオギ
シカルボン酸誘導体、ビフェニル化合物、スヂルベン化
合物、アゾメチン化合物、本発明化合物以外の他のアゾ
化合物等を挙げることができる。本発明化合物は、比較
的高温領域でイ・マチック液晶を示し、高温用液晶表示
素子あるいはその構成成分として最適である。The compound of the present invention produced by the above-mentioned synthetic route can be used alone or in a mixture of two or more to form a liquid crystal display element, if it exhibits a property as a nematic liquid crystal. Furthermore, any of these compounds can be used as a liquid crystal display element by mixing with other compounds exhibiting i-matic liquid crystal. As described above, there are various conventionally known liquid crystal compounds as compounds exhibiting nematic liquid crystal that can be used in combination with the compound of the present invention, such as azomethine compounds, ester compounds or their oxycarboxylic acid derivatives, biphenyl compounds, and dirubene compounds. , azomethine compounds, and other azo compounds other than the compounds of the present invention. The compound of the present invention exhibits i-matic liquid crystal in a relatively high temperature range, and is optimal as a high temperature liquid crystal display element or a component thereof.
以下、実施例に基づいて本発明を具体的に説明する。The present invention will be specifically described below based on Examples.
実施例1
上記合成経路〔■〕→〔νl〕→〔j〕→〔X〕→〔X
〕→CXII)で合成した2=(+−ヒドロキシフェニ
ルアゾ)フェナントレンCXII) 0.5 gを環流
冷却器と攪拌装置を備えた100m1三つロフラスコに
装入し、溶媒としてアセトン50m!を加え、さらに、
粉末状にした水酸化ナトリウム0.16gを加え、4時
間加熱攪拌還流を行−っだ。さらに、オクチルブロマイ
ド07gを20m1のアセトンに溶解させたものを約2
0分間でゆっくりと滴下した。滴下終了後、10時間加
熱攪拌還流を行ない、さらに5〜6mlの水を加え、4
時間加熱攪拌還流を行−った。その後12峙間放置し、
放置後にアセトンをエバポレーターで蒸発乾固させ、粗
製物を得た。粗製物を多量の水酸化ナトリウム水溶液で
良く洗浄して未反応の2−(+−ヒドロキシフェニルア
ゾ)フェナントレンを収り除き、さらに水で洗浄した後
、ij過し減圧乾燥した。Example 1 The above synthetic route [■] → [νl] → [j] → [X] → [X
]→CXII) 0.5 g of 2=(+-hydroxyphenylazo)phenanthrene CXII) synthesized by CXII) was placed in a 100ml three-necked flask equipped with a reflux condenser and a stirring device, and 50ml of acetone was added as a solvent. and further,
0.16 g of powdered sodium hydroxide was added, and the mixture was heated under stirring and refluxed for 4 hours. Furthermore, approximately 2 g of octyl bromide dissolved in 20 ml of acetone was added.
It was slowly added dropwise over a period of 0 minutes. After the dropwise addition, heat, stir, and reflux for 10 hours, add 5 to 6 ml of water, and add 4 ml of water.
The mixture was heated under stirring and refluxed for hours. After that, leave it for 12 minutes,
After standing, acetone was evaporated to dryness using an evaporator to obtain a crude product. The crude product was thoroughly washed with a large amount of aqueous sodium hydroxide solution to remove unreacted 2-(+-hydroxyphenylazo)phenanthrene, further washed with water, filtered through an ij filter, and dried under reduced pressure.
得られた生成物をエタノールで2回再結晶し、アルキル
基の炭素数が8である2−(4−アルコキシフェニルア
ゾ)フェナントレン05g(収率q27%)を得た。こ
の化合物は黄色結晶であり、融点測定、赤外線吸収スペ
クトル及び元素分析によってその構造を確認した。また
、この化合物の液晶性を検討するために、加熱板付偏光
顕微鏡及び熱分析法で相の転移温度を観察した。結果を
第1表に示す。The obtained product was recrystallized twice from ethanol to obtain 05 g (yield q: 27%) of 2-(4-alkoxyphenylazo)phenanthrene whose alkyl group has 8 carbon atoms. This compound is a yellow crystal, and its structure was confirmed by melting point measurement, infrared absorption spectrum, and elemental analysis. In addition, in order to examine the liquid crystallinity of this compound, the phase transition temperature was observed using a polarizing microscope with a heating plate and thermal analysis. The results are shown in Table 1.
また、同様にしてアルキル基の炭素数が異なる化合物を
合成し、相の転移温度を観察した。結果を第1表に示す
。In addition, compounds with different numbers of carbon atoms in the alkyl groups were synthesized in the same manner, and the phase transition temperatures were observed. The results are shown in Table 1.
第1表
1−・・
[J
2
ト
−5
[−6
8
9
し2
L!−4
−Iμ
実施例2
実施例1と同様に、100m1三つロフラスコに攪拌装
置、還流器、および滴下ロートをとり一つけ、三一つ目
フラスコに2−(4−ヒドロキンフェニルアゾ)フェナ
ントレン05g、水酸化ナトリウム02g、溶媒として
アセトン50m1を加え、還流温度において、2〜3時
間加熱攪拌を行−っだ。ナトリウム塩とし、室温に冷却
した後、アセトン10m7!によ−って希釈したC3H
1□C0(J 1.Ogを滴下ロートより、05〜1時
間で滴下し、その後1時間攪拌を行−っだ。Table 1 1--[J 2 To-5 [-6 8 9 Shi2 L! -4 -Iμ Example 2 In the same manner as in Example 1, a 100 ml three-necked flask was equipped with a stirrer, a reflux device, and a dropping funnel, and a third flask was filled with 2-(4-hydroquinphenylazo)phenanthrene. 05 g of sodium hydroxide, 02 g of sodium hydroxide, and 50 ml of acetone as a solvent were added, and the mixture was heated and stirred at reflux temperature for 2 to 3 hours. After making the sodium salt and cooling to room temperature, 10 m7 of acetone! C3H diluted with
1□C0 (J 1.0g) was added dropwise from the dropping funnel over a period of 0.5 to 1 hour, followed by stirring for 1 hour.
次に反応物を熱水中に投じ、〕2時間以上だ一つだ後に
、吸引j−f過を行ない、l−1過物をトルエンに溶か
し、共沸蒸留により、水分を除き、室温で活性アルミナ
のカラムクロマトにより未反応物などを除き、エタノー
ルから2〜4回再結晶を行い、アルキル基の炭素数が8
である2−(4−アルコキシフェニルアゾ)フェナント
レン0.82g (収率43.7%)を得た。この化合
物は黄色結晶であり、融点測定、赤外線吸収スペクトル
及び元素分析によ一つてその構造を確認した。また、こ
の化合物の液晶性を検討するために、加熱板付偏光顕微
鏡及び熱分析法で相の転移温度を観察した。結果を第2
表に示す。Next, the reactant was poured into hot water, and after standing for more than 2 hours, it was subjected to suction filtration, the 1-1 filtrate was dissolved in toluene, water was removed by azeotropic distillation, and the mixture was heated at room temperature. Unreacted substances were removed by activated alumina column chromatography, recrystallized from ethanol 2 to 4 times, and the number of carbon atoms in the alkyl group was reduced to 8.
0.82 g (yield: 43.7%) of 2-(4-alkoxyphenylazo)phenanthrene was obtained. This compound is a yellow crystal, and its structure was confirmed by melting point measurement, infrared absorption spectrum, and elemental analysis. In addition, in order to examine the liquid crystallinity of this compound, the phase transition temperature was observed using a polarizing microscope with a heating plate and thermal analysis. Second result
Shown in the table.
また、同様にしてアルキル基の炭素数が異なる化合物を
合成し、相の転移湿度を観察した。結果を第2表に示す
。In addition, compounds with different numbers of carbon atoms in the alkyl groups were synthesized in the same manner, and the phase transition humidity was observed. The results are shown in Table 2.
第2表
(注) Meは液晶相に転移する湿度実施例3
上記合成経路(Vll:] −+ [、Vl[l −+
CIX:l →[X1ll] −+[:XJV) テ
合成した2−(4−ヒドロキンフェニルアゾ)−9、1
0−シヒf’07.:r−jン) L/ン[:XIV:
] 0.5 gを環流冷却器と攪拌装置を備えた100
mA三つロフラスコに装入し、溶媒としてシクロヘキサ
ン80m!を加え、さらに無水炭酸カリウム1.88g
を加えた後、オクチルブロマイド0.7gを20m1の
シクロへギザノンに溶解させたものを加熱攪拌還流しな
がら約20分間でゆっくり滴下した。滴下終了後、さら
に約3時間加熱攪拌還流を行った。e過した後シクロヘ
キサノンを蒸発乾固させ粗製物を得た。Table 2 (Note) Humidity at which Me transitions to liquid crystal phase Example 3 The above synthesis route (Vll:] −+ [, Vl[l −+
CIX:l → [X1ll] −+[:XJV) Te synthesized 2-(4-hydroquinphenylazo)-9,1
0-shihi f'07. :r-jn) L/n[:XIV:
] 0.5 g in a 100 ml bottle equipped with a reflux condenser and a stirring device.
mA in a three-necked flask, and use 80 mA of cyclohexane as the solvent! and then 1.88g of anhydrous potassium carbonate.
After that, 0.7 g of octyl bromide dissolved in 20 ml of cyclohegizanone was slowly added dropwise over about 20 minutes while heating, stirring, and refluxing. After the dropwise addition was completed, the mixture was heated and stirred under reflux for about 3 hours. After filtration, cyclohexanone was evaporated to dryness to obtain a crude product.
粗製物を多電の水酸化す)リウムで良く洗浄し、未反応
の2−(キーヒドロキシフェニルアゾ)−9,10−ジ
ヒドロフェナントレンを取り除き、さらに水で洗浄した
後、j−i過して生成物を得た。The crude product was thoroughly washed with polyhydric sodium hydroxide to remove unreacted 2-(keyhydroxyphenylazo)-9,10-dihydrophenanthrene, further washed with water, and then filtered through ji. The product was obtained.
得られた生成物をエタノールで再結晶し、アルキル基の
炭素数が8である2−(4−アルコキシフェニルアゾ)
−9,10−ジヒドロフェナントレン0.49g (
収率71.84% )を得た。この化合物は黄色結晶
であり、融点測定、赤外線吸収スペクトル及び元素分析
によってその構造を確認した。また、この化合物の液晶
性を検討するため(二、加熱板付偏光顕微鏡及び熱分析
法で相の転移温度を観。The obtained product was recrystallized from ethanol to obtain 2-(4-alkoxyphenylazo) in which the alkyl group has 8 carbon atoms.
-9,10-dihydrophenanthrene 0.49g (
A yield of 71.84% was obtained. This compound is a yellow crystal, and its structure was confirmed by melting point measurement, infrared absorption spectrum, and elemental analysis. In addition, to examine the liquid crystallinity of this compound (2. Observe the phase transition temperature using a polarizing microscope with a heating plate and thermal analysis.
察した。結果を第3表(二示す。I guessed it. The results are shown in Table 3.
また、同様にしてアルキル基の炭素数が異なる化合物を
合成し、相の転移温度を観察した。結果を第3表に示す
。In addition, compounds with different numbers of carbon atoms in the alkyl groups were synthesized in the same manner, and the phase transition temperatures were observed. The results are shown in Table 3.
第3表
手続補正書
昭和「3年7月22日
特許庁長官 若 杉 和 夫 殿
】、事件の表示
昭和58年特rl願第104759号
2 発明の名称
2−(手−置換フェニルアゾ)
フェナントレン誘導体
3 補正をする者
事件との関係 特許出願人
住所 東京都世Fil谷区世H」谷1丁目4番15号名
称 永 井 芳 男 (外1名)Φ代理
人〒104電話03(543)1675住所 東京都中
央区銀座7丁目]4番2号 在庁ビル8階氏名 (82
73)弁理千成 瀬勝 夫 (外1名)6 補正によ
り増加する発明の数
7 補正の対象
明細書の「発明の詳細な説明」の欄
8 補正の内容
明細書の第5頁及び第6頁について別紙のを補干する。Table 3 Procedural Amendments Showa ``July 22, 3rd year, Mr. Kazuo Wakasugi, Commissioner of the Patent Office'', Indication of the case 1982 Patent application No. 104759 2 Title of the invention 2-(Hand-substituted phenylazo) Phenanthrene derivative 3 Relationship with the case of the person making the amendment Patent Applicant Address: 1-4-15, Seh'ya, Sefilya-ku, Tokyo Name: Yoshio Nagai (1 other person) Φ Agent: 104 Phone: 03 (543) 1675 Address: 7-chome, Ginza, Chuo-ku, Tokyo] 4-2, 8th floor, Office Building Name (82
73) Patent attorney Chinari Sekatsuo (1 other person) 6 Number of inventions increased by amendment 7 “Detailed explanation of the invention” column 8 of the specification to be amended Pages 5 and 6 of the description of the contents of the amendment Please add the attached sheet regarding the page.
(但し、式中nは整数である。)で示される化合物があ
る。これらの化合物において、アルキル基の炭素数fn
lについては1〜20が好ましく、また、これらのアル
キル基は、直鎖状のものが好ましいが、全体として細長
い構造であれば若干の枝分れがあってもよい。(However, in the formula, n is an integer.) There is a compound represented by the following formula. In these compounds, the number of carbon atoms in the alkyl group fn
l is preferably 1 to 20, and these alkyl groups are preferably linear, but may have some branching as long as they have an elongated structure as a whole.
一般式〔1〕又は〔11〕で示される本発明化合物は、
徨々の合成経路で合成することができるが、代表例とし
てフェナントレンIJII)から合成する合成経路の1
例を示せば下記の通りである。The compound of the present invention represented by general formula [1] or [11] is
It can be synthesized by various synthetic routes, but a typical example is one of the synthetic routes synthesized from phenanthrene IJII).
An example is as follows.
Claims (5)
示される2−(4−置換フェニルアゾ)フェナントレン
誘導体。(1) A 2-(4-substituted phenylazo)phenanthrene derivative represented by the following general formula [■] or [II] (wherein, the person in the formula is an alkyl group or anru group).
2(4−F=アルコキンフェニルアゾ)フェナントレン
である特許請求の範囲第1項記載の2−(4−置換フェ
ニルアゾ)フェナントレン誘導体。(2) The compound represented by the general formula [I] is 2(4-F=alcoquinphenylazo)phenanthrene represented by the following general formula (where n is an integer from 0 to 2o). A 2-(4-substituted phenylazo)phenanthrene derivative according to claim 1.
〕 (但し、式中nは1〜20の整数である。)で示される
2−(4−アルコキシフェニルアゾ)フェナントレンで
ある特許請求の範囲第1項記載の2−(4−置換フェニ
ルアゾ)フェナントレン誘導体。(3) The compound represented by the general formula [I] has the following general formula [■
2-(4-substituted phenylazo)phenanthrene according to claim 1, which is 2-(4-alkoxyphenylazo)phenanthrene represented by the formula (where n is an integer of 1 to 20) derivative.
V〕 (但し、式中r、は]〜20の整数である。)で示され
る2−(48−アルコキシフェニルアゾ)−9,10−
ジヒドロフェナントレンである特許請求の範囲第1項記
載の2−(4−置換フェニルアゾ)フェナントレン誘導
体。(4) The compound represented by the general formula [rt+] has the following general formula [
2-(48-alkoxyphenylazo)-9,10- represented by V] (wherein r is an integer from ] to 20)
The 2-(4-substituted phenylazo)phenanthrene derivative according to claim 1, which is dihydrophenanthrene.
晶性化合物である特許請求の範囲第1項ないし第4項の
いずれかに記載の2−(4−置換フェニル:=’ ソ)
フェナントレン誘導体。(5) 2-(4-substituted phenyl: =' so) according to any one of claims 1 to 4, wherein the compound represented by general formula CI) or [11] is a liquid crystal compound.
Phenanthrene derivative.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP10475983A JPS59231059A (en) | 1983-06-12 | 1983-06-12 | 2-(4-substituted phenylazo)phenanthrene derivative |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP10475983A JPS59231059A (en) | 1983-06-12 | 1983-06-12 | 2-(4-substituted phenylazo)phenanthrene derivative |
Publications (1)
Publication Number | Publication Date |
---|---|
JPS59231059A true JPS59231059A (en) | 1984-12-25 |
Family
ID=14389413
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP10475983A Pending JPS59231059A (en) | 1983-06-12 | 1983-06-12 | 2-(4-substituted phenylazo)phenanthrene derivative |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS59231059A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN108238973A (en) * | 2016-12-23 | 2018-07-03 | 北京大学深圳研究生院 | A kind of liquid crystal semi-conducting material and its preparation method and application |
-
1983
- 1983-06-12 JP JP10475983A patent/JPS59231059A/en active Pending
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN108238973A (en) * | 2016-12-23 | 2018-07-03 | 北京大学深圳研究生院 | A kind of liquid crystal semi-conducting material and its preparation method and application |
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