JPS632246B2 - - Google Patents
Info
- Publication number
- JPS632246B2 JPS632246B2 JP13033080A JP13033080A JPS632246B2 JP S632246 B2 JPS632246 B2 JP S632246B2 JP 13033080 A JP13033080 A JP 13033080A JP 13033080 A JP13033080 A JP 13033080A JP S632246 B2 JPS632246 B2 JP S632246B2
- Authority
- JP
- Japan
- Prior art keywords
- trans
- liquid crystal
- compound
- cyclohexylmethyl
- acid
- 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.)
- Expired
Links
- 239000004973 liquid crystal related substance Substances 0.000 claims description 25
- 239000000203 mixture Substances 0.000 claims description 14
- -1 cyclohexylmethyl 4- Fluorophenyl ether Chemical compound 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- CDAOWUNZBZEBDA-UHFFFAOYSA-N 1-fluoro-2-(2-fluorophenoxy)benzene Chemical compound FC1=CC=CC=C1OC1=CC=CC=C1F CDAOWUNZBZEBDA-UHFFFAOYSA-N 0.000 claims description 2
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
- 150000001875 compounds Chemical class 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 235000019441 ethanol Nutrition 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- RHMPLDJJXGPMEX-UHFFFAOYSA-N 4-fluorophenol Chemical compound OC1=CC=C(F)C=C1 RHMPLDJJXGPMEX-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 239000004988 Nematic liquid crystal Substances 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- VSSAZBXXNIABDN-UHFFFAOYSA-N cyclohexylmethanol Chemical compound OCC1CCCCC1 VSSAZBXXNIABDN-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- OXPDQFOKSZYEMJ-UHFFFAOYSA-N 2-phenylpyrimidine Chemical compound C1=CC=CC=C1C1=NC=CC=N1 OXPDQFOKSZYEMJ-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- 229910010082 LiAlH Inorganic materials 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000005337 azoxy group Chemical group [N+]([O-])(=N*)* 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- UUWSLBWDFJMSFP-UHFFFAOYSA-N bromomethylcyclohexane Chemical compound BrCC1CCCCC1 UUWSLBWDFJMSFP-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- IGARGHRYKHJQSM-UHFFFAOYSA-N cyclohexylbenzene Chemical compound C1CCCCC1C1=CC=CC=C1 IGARGHRYKHJQSM-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- JJOYCHKVKWDMEA-UHFFFAOYSA-N ethyl cyclohexanecarboxylate Chemical compound CCOC(=O)C1CCCCC1 JJOYCHKVKWDMEA-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- OPYYWWIJPHKUDZ-UHFFFAOYSA-N phenyl cyclohexanecarboxylate Chemical compound C1CCCCC1C(=O)OC1=CC=CC=C1 OPYYWWIJPHKUDZ-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Description
【発明の詳細な説明】
本発明は新規な有機化合物に関し、詳しくは液
晶組成物の一成分として有用な液晶化合物に関す
る。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel organic compound, and more particularly to a liquid crystal compound useful as a component of a liquid crystal composition.
正の誘電異方性を有するネマチツク液晶はねじ
れネマチツクモードの液晶表示素子、ゲスト・ホ
スト効果を利用した表示素子に利用されるのをは
じめ、動的散乱効果を利用したDS型表示素子、
電界制御複屈折効果を利用したDAP型表示素子
等にも利用される。これらに用いられる液晶は室
温を含む低温から高温までの出来だけ広い温度範
囲で液晶状態を示すと共に、水分、空気、光、熱
等に対して安定な物であることが必要である。し
かし単一化合物でこの様な条件を全て満たす様な
ものは現在のところなく、何種類かの液晶化合物
又は非液晶化合物を混合した液晶組成物を使用す
ることによつて一応の目的が達せられている。本
発明は、この様な実用的な性能の優れた安定な液
晶組成物を構成する一成分として有用な液晶化合
物を提供するものである。即ち、本発明の化合物
は一般式
（上式に於てＲは炭素数１〜10のアルキル基を示
す）
で表わされる４−トランス（トランス−4′−アル
キルシクロヘキシル）シクロヘキシルメチル４−
フルオロフエニルエーテル及び、少くともその１
種を含有する液晶組成物である。 Nematic liquid crystals with positive dielectric anisotropy are used in twisted nematic mode liquid crystal display elements, display elements that utilize the guest-host effect, and DS type display elements that utilize the dynamic scattering effect.
It is also used in DAP-type display elements that utilize the electric field-controlled birefringence effect. The liquid crystal used in these devices must exhibit a liquid crystal state over as wide a temperature range as possible from low temperatures to high temperatures, including room temperature, and must be stable against moisture, air, light, heat, and the like. However, there is currently no single compound that satisfies all of these conditions, and the objective has been achieved to some extent by using a liquid crystal composition that is a mixture of several types of liquid crystal compounds or non-liquid crystal compounds. ing. The present invention provides a liquid crystal compound useful as a component constituting such a stable liquid crystal composition with excellent practical performance. That is, the compound of the present invention has the general formula (In the above formula, R represents an alkyl group having 1 to 10 carbon atoms) 4-trans(trans-4'-alkylcyclohexyl)cyclohexylmethyl 4-
Fluorophenyl ether and at least one of them
A liquid crystal composition containing seeds.
本発明の化合物は広いネマチツク温度範囲を有
するが融点が高いため、この化合物単独では表示
素子用として実用的に使用できないが、他の液晶
化合物との相溶性にすぐれ、又透明点が高いため
他のＰ型（誘電異方性が正の物）又はＮ型（誘電
異方性が負のもの）の液晶物質、例えばビフエニ
ル系液晶、エステル系液晶、アゾキシ系液晶、シ
クロヘキサンカルボン酸フエニルエステル系液
晶、フエニルシクロヘキサン系液晶、フエニルピ
リミジン系液晶、フエニルメタジオキサン系液晶
などの１種又は数種のものと混合することにより
透明点を上昇させることができ、又低粘度である
ため本化合物を加えることにより応答速度は早く
なり、温度依存性の少ないすぐれた液晶組成物を
得るのに有用である。更に本発明の化合物は誘電
異方性△εは正であるがかなり小さく、それにも
かかわらず動作電圧を低くする使用を有し、又動
作電圧の温度依存性も小さいため動的駆動用液晶
を構成する成分としても有用である。 The compound of the present invention has a wide nematic temperature range but has a high melting point, so it cannot be used practically as a display element alone, but it has excellent compatibility with other liquid crystal compounds and has a high clearing point, so it can be used in other applications. P-type (positive dielectric anisotropy) or N-type (negative dielectric anisotropy) liquid crystal materials, such as biphenyl liquid crystal, ester liquid crystal, azoxy liquid crystal, cyclohexanecarboxylic acid phenyl ester type The clearing point can be raised by mixing it with one or more of liquid crystals, phenylcyclohexane liquid crystals, phenylpyrimidine liquid crystals, phenylmethadioxane liquid crystals, etc. Addition of the compound increases the response speed and is useful for obtaining an excellent liquid crystal composition with less temperature dependence. Furthermore, the compound of the present invention has a positive dielectric anisotropy △ε, but it is quite small, and despite this, it can be used to lower the operating voltage, and the temperature dependence of the operating voltage is also small, so it is suitable for dynamic driving liquid crystals. It is also useful as a constituent component.
本発明の化合物は次の様な工程により製造する
ことが出来る。 The compound of the present invention can be produced by the following steps.
即ち、まず４−トランス（トランス−4′−アル
キルシクロヘキシル）シクロヘキサンカルボン酸
にハロゲン化剤を反応させてその酸塩化物とし、
それにエタノールを反応させてそのエチルエステ
ルを得る。この場合カルボン酸とエタノールを鉱
酸等を触媒として直接エステル化することにより
得ることも可能である。次いでテトラヒドロフラ
ンの如き溶媒中で水素化アルミニウム、リチウム
（LiAlH4）を低温で反応させて環元し４−トラン
ス（トランス−4′−アルキルシクロヘキシル）シ
クロヘキシルメチルアルコールとし、これに硫酸
酸性下で臭化水素酸を反応させるとその臭化物が
得られる。これをＰ−フルオロフエノールとアル
コール中でアルカリ存在下に反応させることによ
り目的とする（）式の化合物、即ち４−トラン
ス（トランス−4′−アルキルシクロヘキシル）シ
クロヘキシルメチル４−フルオロフエニルエーテ
ルが得られる。 That is, first, 4-trans(trans-4'-alkylcyclohexyl)cyclohexanecarboxylic acid is reacted with a halogenating agent to form its acid chloride,
It is reacted with ethanol to obtain its ethyl ester. In this case, it is also possible to directly esterify carboxylic acid and ethanol using a mineral acid or the like as a catalyst. Next, aluminum hydride and lithium (LiAlH 4 ) are reacted at low temperature in a solvent such as tetrahydrofuran to obtain 4-trans(trans-4'-alkylcyclohexyl)cyclohexylmethyl alcohol, which is then bromated under acidic sulfuric acid. When hydrogen acid is reacted, its bromide is obtained. By reacting this with P-fluorophenol in alcohol in the presence of an alkali, the target compound of formula (), namely 4-trans(trans-4'-alkylcyclohexyl)cyclohexylmethyl 4-fluorophenyl ether, is obtained. It will be done.
尚、原料として使用した４−トランス（トラン
ス−4′−アルキルシクロヘキシル）シクロヘキサ
ンカルボン酸は４−アルキルジフエニル−4′−カ
ルボン酸を酢酸を溶媒とし、Pt触媒にて150℃、
50気圧で水添反応を行なつて得られるものを再結
晶により精製して使用した。 The 4-trans(trans-4'-alkylcyclohexyl)cyclohexanecarboxylic acid used as a raw material was prepared by heating 4-alkyldiphenyl-4'-carboxylic acid in acetic acid as a solvent at 150°C over a Pt catalyst.
The product obtained by carrying out the hydrogenation reaction at 50 atm was purified by recrystallization and used.
以下、実施例により本発明の化合物の製造法及
びその使用例について更に詳細に説明する。 Hereinafter, the method for producing the compound of the present invention and examples of its use will be explained in more detail with reference to Examples.
実施例 １
〔４−トランス（トランス−4′−ペンチルシク
ロヘキシル）シクロヘキシルメチル４−フルオ
ロフエニルエーテルの製造〕
４−トランス（トランス−4′−ペンチルシクロ
ヘキシル）シクロヘキサンカルボン酸30.0ｇ
（0.107モル）と塩化チオニル23.8ｇ（0.2モル）を
加熱還流下で１時間反応させ、過剰の塩化チオニ
ルを減圧にて留去して29.8ｇ（0.1モル）の酸塩
化物を得る。これに23ｇ（0.5モル）のエチルア
ルコールを除々に加え、混合物を約60℃で２時間
加熱撹拌する。反応後、冷極してから50mlのｎ−
ヘキサンで抽出し、抽出液を20％塩酸、次いで10
％NaOH水溶液で洗浄し、更に水で中性になる
まで洗浄してからｎ−ヘキサンを留去して29.3ｇ
（0.095モル）の４−トランス（トランス−4′−ペ
ンチルシクロヘキシル）シクロヘキサンカルボン
酸エチルエステルを得る。これをよく乾燥したテ
トラハイドロフラン60mlに溶解し、それを水素化
アルミニウムリチウム2.1ｇ（0.056モル）を乾燥
したテトラハイドロフラン50mlに懸濁させ激しく
撹拌しているところへ滴下する。滴下終了後、還
流下に２時間加熱し、冷却後、過剰の水素化アル
ミニウムリチウムを分解するために注意深く水20
mlを加え、次いでこの混合物を20％硫酸100mlに
除々に加えて無機物が全部溶解するまで撹拌す
る。それを100mlのテトラハイドロフランで抽出
し、水洗し、無水硫酸マグネシウムを用いて乾燥
後テトラハイドロフランを留去し、残留物を25ml
のｎ−ヘキサンで再結晶して21.8ｇ（0.08モル）
の４−トランス（トランス−4′−ペンチルシクロ
ヘキシル）シクロヘキシルメチルアルコールを得
た。このものの融点は128℃であつた。Example 1 [Production of 4-trans(trans-4'-pentylcyclohexyl)cyclohexylmethyl 4-fluorophenyl ether] 30.0 g of 4-trans(trans-4'-pentylcyclohexyl)cyclohexanecarboxylic acid
(0.107 mol) and 23.8 g (0.2 mol) of thionyl chloride are reacted under heating under reflux for 1 hour, and excess thionyl chloride is distilled off under reduced pressure to obtain 29.8 g (0.1 mol) of the acid chloride. 23 g (0.5 mol) of ethyl alcohol is gradually added to this, and the mixture is heated and stirred at about 60° C. for 2 hours. After the reaction, 50ml of n-
Extracted with hexane, extracted with 20% hydrochloric acid, then 10%
% NaOH aqueous solution, further washed with water until neutral, and n-hexane was distilled off to give 29.3g.
(0.095 mol) of 4-trans(trans-4'-pentylcyclohexyl)cyclohexanecarboxylic acid ethyl ester is obtained. This was dissolved in 60 ml of well-dried tetrahydrofuran, and the solution was added dropwise to a suspension of 2.1 g (0.056 mol) of lithium aluminum hydride in 50 ml of dry tetrahydrofuran, which was being vigorously stirred. After the addition is complete, heat under reflux for 2 hours, and after cooling, carefully add 20 ml of water to decompose the excess lithium aluminum hydride.
ml and then gradually add this mixture to 100 ml of 20% sulfuric acid and stir until all the inorganic matter is dissolved. It was extracted with 100ml of tetrahydrofuran, washed with water, dried over anhydrous magnesium sulfate, and the tetrahydrofuran was distilled off, leaving a residue of 25ml.
Recrystallized with n-hexane to give 21.8g (0.08mol)
4-trans(trans-4'-pentylcyclohexyl)cyclohexylmethyl alcohol was obtained. The melting point of this product was 128°C.
次に濃硫酸9.2ｇに臭化水素酸（47％）28.8ｇ
を除々に加えて得られる液中に先のアルコールを
全量加え約100℃で４時間加熱撹拌した。放冷後
トルエン20mlを加えて抽出し、抽出液を10％炭酸
ナトリウム水溶液で、次いで水で洗浄した後、ト
ルエンを留去し、残留物をエタノール40mlで再結
晶して14.8ｇ（0.045モル）の４−トランス（ト
ランス−4′−ペンチルシクロヘキシル）シクロヘ
キシルメチルブロミドを得た。この物の融点は45
℃であつた。一方、４−フルオロフエノール5.16
ｇ（0.046モル）を50mlのエチルアルコールに溶
解し、これに更に1.84ｇの水酸化ナトリウムを５
mlの水に溶解したものを加え、これを加熱還流し
ておき、そこへ先に得られたブロミドの全量
（14.8ｇ）を50mlのエチルアルコール溶解したも
のを滴下して行く。滴下後、加熱還流下で４時間
反応させ、反応終了後放冷し、トルエン50mlを加
えて抽出し、それをまず10％水酸化ナトリウム水
溶液で、次いで水で洗浄後、無水硫酸マグネシウ
ムを用いて乾燥し、更にトルエンを留去して、残
留物をエチルアルコールを用いて２回再結晶して
目的物である４−トランス（トランス−4′−ペン
チルシクロヘキシル）シクロヘキシルメチル４−
フルオロフエニルエーテル11.1ｇ（0.03モル）を
得た。このものはネマチツク液晶物質で、融点
（Ｃ−Ｎ点）は66.5℃、透明点（Ｎ−Ｉ点）は
134.8℃であつた。又このものの元素分析値は下
記の通りで理論値とよく一致した。 Next, add 28.8 g of hydrobromic acid (47%) to 9.2 g of concentrated sulfuric acid.
The entire amount of alcohol was added to the liquid obtained by gradually adding the alcohol, and the mixture was heated and stirred at about 100°C for 4 hours. After cooling, 20 ml of toluene was added for extraction, and the extract was washed with a 10% aqueous sodium carbonate solution and then with water, the toluene was distilled off, and the residue was recrystallized with 40 ml of ethanol to yield 14.8 g (0.045 mol). 4-trans(trans-4'-pentylcyclohexyl)cyclohexylmethyl bromide was obtained. The melting point of this thing is 45
It was warm at ℃. On the other hand, 4-fluorophenol 5.16
g (0.046 mol) in 50 ml of ethyl alcohol, and further added 1.84 g of sodium hydroxide to 50 ml of ethyl alcohol.
ml of water is added, this is heated to reflux, and the entire amount of bromide obtained earlier (14.8 g) dissolved in 50 ml of ethyl alcohol is added dropwise. After the dropwise addition, the reaction was heated under reflux for 4 hours, and after the reaction was completed, the mixture was allowed to cool, and 50 ml of toluene was added to extract it, which was first washed with a 10% aqueous sodium hydroxide solution and then with water, and then washed with anhydrous magnesium sulfate. After drying, the toluene was further distilled off, and the residue was recrystallized twice using ethyl alcohol to obtain the target product, 4-trans(trans-4'-pentylcyclohexyl)cyclohexylmethyl 4-
11.1 g (0.03 mol) of fluorophenyl ether was obtained. This material is a nematic liquid crystal material, with a melting point (C-N point) of 66.5℃ and a clearing point (N-I point) of
The temperature was 134.8℃. The elemental analysis values of this product were as shown below, and agreed well with the theoretical values.
分析値(%) 理論値(%)（C23H33OFとして）
Ｃ 86.3 86.0
Ｈ 6.9 7.22
実施例 ２、３
出発原料としてアルキル基の異なつたものを使
用する以外は実施例１と全く同様にして４−トラ
ンス（トランス−4′−プロピルシクロヘキシル）
シクロヘキシルメチル４−フルオロフエニルエー
テル（実施例２）及び４−トランス（トランス−
４−ヘプチルシクロヘキシル）シクロヘキシルメ
チル４−フルオロフエニルエーテルを得た。前者
のＣ−Ｎ点は92.0℃、Ｎ−Ｉ点は132.3℃であり、
後者のＣ−Ｎ点は74.5℃Ｎ−Ｉ点は129.0℃であ
つた。 Analytical value (%) Theoretical value (%) (as C 23 H 33 OF) C 86.3 86.0 H 6.9 7.22 Examples 2 and 3 Completely the same as Example 1 except that starting materials with different alkyl groups were used. 4-trans(trans-4'-propylcyclohexyl)
Cyclohexylmethyl 4-fluorophenyl ether (Example 2) and 4-trans (trans-
4-heptylcyclohexyl)cyclohexylmethyl 4-fluorophenyl ether was obtained. The former C-N point is 92.0℃, the N-I point is 132.3℃,
The latter C-N point was 74.5°C and N-I point was 129.0°C.
実施例４（使用例１）
本発明の（）式の化合物15部を含む上記処方
の液晶組成物のＮ−Ｉ点は62.3℃で、（）式の
化合物15部を除いたもののＮ−Ｉ点53.5℃より上
昇し、又粘度は（）式の化合物15部を加えたこ
とにより27cpから25cpに低下した。この液晶組
成物をセル厚10μｍのねじれネマチツク型セルに
封入してその動作特性を測定したところ、しきい
電圧は1.70V、飽和電圧は2.30Vであつた。又△
εは9.9であつた。Example 4 (Usage example 1) The N-I point of the liquid crystal composition with the above formulation containing 15 parts of the compound of formula () of the present invention is 62.3°C, which is higher than the N-I point of 53.5°C when 15 parts of the compound of formula () is excluded. The viscosity decreased from 27 cp to 25 cp by adding 15 parts of the compound of formula (). When this liquid crystal composition was sealed in a twisted nematic cell with a cell thickness of 10 μm and its operating characteristics were measured, the threshold voltage was 1.70V and the saturation voltage was 2.30V. Also△
ε was 9.9.
Claims (1)
を示す） で表わされる４−トランス（トランス−4′−アル
キルシクロヘキシル）シクロヘキシルメチル４−
フルオロフエニルエーテル。 ２ 一般式 （但し上式に於てＲは炭素数１〜10のアルキル基
を示す） で表わされる４−トランス（トランス−4′−アル
キルシクロヘキシル）シクロヘキシルメチル４−
フルオロフエニルエーテルを少くとも１種類含有
することを特徴とする液晶組成物。[Claims] 1. General formula (However, in the above formula, R represents an alkyl group having 1 to 10 carbon atoms.) 4-trans(trans-4'-alkylcyclohexyl)cyclohexylmethyl 4-
Fluorophenyl ether. 2 General formula (However, in the above formula, R represents an alkyl group having 1 to 10 carbon atoms.) 4-trans(trans-4'-alkylcyclohexyl)cyclohexylmethyl 4-
A liquid crystal composition containing at least one type of fluorophenyl ether.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13033080A JPS5754137A (en) | 1980-09-19 | 1980-09-19 | 4-trans(trans-4'-alkylcyclohexyl)cyclohexylmethyl4- fluorophenyl ether |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13033080A JPS5754137A (en) | 1980-09-19 | 1980-09-19 | 4-trans(trans-4'-alkylcyclohexyl)cyclohexylmethyl4- fluorophenyl ether |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5754137A JPS5754137A (en) | 1982-03-31 |
| JPS632246B2 true JPS632246B2 (en) | 1988-01-18 |
Family
ID=15031774
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP13033080A Granted JPS5754137A (en) | 1980-09-19 | 1980-09-19 | 4-trans(trans-4'-alkylcyclohexyl)cyclohexylmethyl4- fluorophenyl ether |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5754137A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6437938U (en) * | 1987-08-27 | 1989-03-07 |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3040632A1 (en) * | 1980-10-29 | 1982-05-27 | Merck Patent Gmbh, 6100 Darmstadt | CYCLOHEXYLPHENYL DERIVATIVES, THESE DIELECTRICS AND ELECTROOPTIC DISPLAY ELEMENT |
| DE3206269A1 (en) * | 1982-02-20 | 1983-09-01 | Merck Patent Gmbh, 6100 Darmstadt | BICYCLOHEXYL DERIVATIVES |
| DE3374415D1 (en) * | 1982-03-26 | 1987-12-17 | Chisso Corp | Liquid-crystalline compounds |
| EP0107759B1 (en) * | 1982-08-26 | 1992-12-16 | MERCK PATENT GmbH | Cyclohexane derivatives and their use as components for liquid crystals |
| JPS5993482U (en) * | 1982-12-08 | 1984-06-25 | 株式会社ソフィア | pachinko machine |
| DE3317597A1 (en) * | 1983-05-14 | 1984-11-15 | Merck Patent Gmbh, 6100 Darmstadt | BICYCLOHEXYLETHANE |
| DE3332691A1 (en) * | 1983-09-10 | 1985-03-28 | Merck Patent Gmbh, 6100 Darmstadt | ANISOTROPE COMPOUNDS AND LIQUID CRYSTAL MIXTURES |
| US5252252A (en) * | 1983-09-10 | 1993-10-12 | Merck Patent Gesellschaft Mit Beschraenkter Haftung | Anisotropic compounds and liquid crystal mixtures |
| DE3332692A1 (en) * | 1983-09-10 | 1985-03-28 | Merck Patent Gmbh, 6100 Darmstadt | ANISOTROPE COMPOUNDS AND LIQUID CRYSTAL MIXTURES |
| CH660003A5 (en) * | 1984-04-16 | 1987-03-13 | Merck Patent Gmbh | ANISOTROPE COMPOUNDS AND FK MIXTURES WITH THESE. |
| US4931209A (en) * | 1986-09-25 | 1990-06-05 | Crystaloid Electronics, Inc. | Liquid crystalline materials and method of making |
-
1980
- 1980-09-19 JP JP13033080A patent/JPS5754137A/en active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6437938U (en) * | 1987-08-27 | 1989-03-07 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5754137A (en) | 1982-03-31 |
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