JPH02218646A - Liquid crystal ester compound - Google Patents
Liquid crystal ester compoundInfo
- Publication number
- JPH02218646A JPH02218646A JP1037830A JP3783089A JPH02218646A JP H02218646 A JPH02218646 A JP H02218646A JP 1037830 A JP1037830 A JP 1037830A JP 3783089 A JP3783089 A JP 3783089A JP H02218646 A JPH02218646 A JP H02218646A
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- formula
- compound
- formulas
- tables
- 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
- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 37
- -1 ester compound Chemical class 0.000 title claims abstract description 11
- 239000000203 mixture Substances 0.000 claims abstract description 14
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 2
- 239000000126 substance Substances 0.000 claims description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract description 19
- 150000002148 esters Chemical class 0.000 abstract description 4
- 235000010290 biphenyl Nutrition 0.000 abstract description 3
- IGARGHRYKHJQSM-UHFFFAOYSA-N cyclohexylbenzene Chemical class C1CCCCC1C1=CC=CC=C1 IGARGHRYKHJQSM-UHFFFAOYSA-N 0.000 abstract description 3
- 238000000034 method Methods 0.000 abstract description 3
- 239000000463 material Substances 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 abstract description 2
- 238000003512 Claisen condensation reaction Methods 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 150000004074 biphenyls Chemical class 0.000 abstract 1
- 239000002994 raw material Substances 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000004988 Nematic liquid crystal Substances 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 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 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- YZWKKMVJZFACSU-UHFFFAOYSA-N 1-bromopentane Chemical compound CCCCCBr YZWKKMVJZFACSU-UHFFFAOYSA-N 0.000 description 1
- MDURQPNBPHBIFN-UHFFFAOYSA-N 2-pentoxyphenol Chemical compound CCCCCOC1=CC=CC=C1O MDURQPNBPHBIFN-UHFFFAOYSA-N 0.000 description 1
- FURZYCFZFBYJBT-UHFFFAOYSA-N 4-(4-pentylcyclohexyl)benzonitrile Chemical compound C1CC(CCCCC)CCC1C1=CC=C(C#N)C=C1 FURZYCFZFBYJBT-UHFFFAOYSA-N 0.000 description 1
- XXUSEPRYHRDKFV-UHFFFAOYSA-N 4-(4-propylcyclohexyl)benzonitrile Chemical compound C1CC(CCC)CCC1C1=CC=C(C#N)C=C1 XXUSEPRYHRDKFV-UHFFFAOYSA-N 0.000 description 1
- JCLFHZLOKITRCE-UHFFFAOYSA-N 4-pentoxyphenol Chemical compound CCCCCOC1=CC=C(O)C=C1 JCLFHZLOKITRCE-UHFFFAOYSA-N 0.000 description 1
- NNJMFJSKMRYHSR-UHFFFAOYSA-N 4-phenylbenzoic acid Chemical class C1=CC(C(=O)O)=CC=C1C1=CC=CC=C1 NNJMFJSKMRYHSR-UHFFFAOYSA-N 0.000 description 1
- 239000004986 Cholesteric liquid crystals (ChLC) Substances 0.000 description 1
- 238000005821 Claisen rearrangement reaction Methods 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000004990 Smectic liquid crystal Substances 0.000 description 1
- 150000001347 alkyl bromides Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 210000002858 crystal cell Anatomy 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
- Liquid Crystal (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、新規な液晶エステル化合物および該化合物を
含有する液晶組成物に関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to a novel liquid crystal ester compound and a liquid crystal composition containing the compound.
液晶を利用した表示素子は時計、電卓等に広く使用され
ている。これらの液晶表示素子は液晶物質の光学異方性
および誘電異方性を利用したものである。液晶相にはネ
マチック液晶相、スメクチック液晶相、コレステリック
液晶相があシ、そのうちネマチック液晶を利用したもの
が最も広く実用化されている。それらには液晶表示に応
用されている電気光学効果に対応し、ＴＮ（ねじれネマ
チック）型、ＤＳ（動的散乱）型、ゲスト・ホスト型、
ＤＡＰ型等の表示素子がｔｊシ、それぞれに使用される
液晶物質は自然界のなるべく広い温度範囲で液晶相を示
すものが望ましい。Display elements using liquid crystals are widely used in watches, calculators, etc. These liquid crystal display elements utilize optical anisotropy and dielectric anisotropy of liquid crystal substances. The liquid crystal phase includes a nematic liquid crystal phase, a smectic liquid crystal phase, and a cholesteric liquid crystal phase, and among these, those using nematic liquid crystal are most widely put into practical use. They correspond to the electro-optical effect applied to liquid crystal displays, and include TN (twisted nematic) type, DS (dynamic scattering) type, guest-host type,
It is desirable that the liquid crystal material used in display elements such as DAP type display a liquid crystal phase over as wide a natural temperature range as possible.
現在のところ単一の液晶物質でそのような条件をみたす
物質はなく、数種の液晶物質またはさらに非液晶物質を
混合して実用に供している。これらの物質は水分、光、
熱、空気等に対しても安定であることを要求されている
。At present, there is no single liquid crystal substance that satisfies these conditions, and several types of liquid crystal substances or even non-liquid crystal substances are mixed and put into practical use. These substances include water, light,
It is also required to be stable against heat, air, etc.
近年表示素子の多桁駆動表示が望まれているが、従来の
ＴＮ型方式では表示品位が劣るため、新たに一連のスー
パー・ツイスト・ネマチック型表示素子（ＳＴＮと略す
）がＭ、シャット（５ｃｈａｄｔ ）らによシ提案され
（Ａｐｐｌ。Ｐｈｙｓ、 Ｌｅｔｔ、 、 ５０．２３
６（１９８７） ） 、多桁駆動表示でも品位が優れた
ものである。In recent years, multi-digit drive display of display elements has been desired, but since the display quality of the conventional TN type display element is inferior, a new series of super twisted nematic type display elements (abbreviated as STN) has been developed. ) et al. (Appl. Phys, Lett, 50.23
6 (1987)), the quality is excellent even in multi-digit drive display.
この方式に望まれる液晶の性質はに＠／Ｋｌが大きく、
ｘＶ’Ｋｓは小さく、Δ＠／／ε上は小さい値が望まれ
ている（ Ｍ、 ５ａｈａｄｔ他、５ｏｃｉｅｔｙ ｆ
ｏｒ ＩｎｆｏｒｍａｔｉｏｎＤｉｓｐｌａｙ Ｉｎｔ
ｓ＋ｒｎａｔｉｏｎａｌ Ｓｙｍｐｏｓｉｕｍ Ｄｉｇ
ｅｓｔ ｏｆ ＴｅｃｈｎｉｃａｌＰａｐａｒｓ Ｍｏ
１． Ｘ ’４ Ｎｅｗ ０ｒｌｅａｎｓ、 Ｌｏｕｉ
ｓｉａａａ、Ｍａｙ １２−１４Ｆ（１９８７） ３７
２−３７５）。The properties of the liquid crystal desired for this method are that @/Kl is large;
xV'Ks is small, and Δ@//ε is desired to have a small value (M, 5ahadt et al., 5ociety f
or Information Display Int
s+national Symposium Dig
est of TechnicalPaparsMo
1. X '4 New 0rleans, Loui
siaaa, May 12-14F (1987) 37
2-375).
本発明の目的は上述のＳＴＮ型表不表示素子用するに好
適な、Ｋ、／Ｋｌが大きく、相溶性に優れている化合物
およびそれを含有する液晶組成物を提供することである
。An object of the present invention is to provide a compound having large K, /Kl and excellent compatibility, suitable for use in the above-mentioned STN type non-display element, and a liquid crystal composition containing the same.
即ち、本発明は一般式
（上式中、Ｒ１、Ｈ！はそれぞれ直鎖または枝分れした
炭素数１〜１５のアルキル基またはアルコキシラフ塩基
系、ビフェニル系、フェニルシクロヘキサン系、複素環
系等の液晶化合物をあげることができる。That is, the present invention relates to the general formula (in the above formula, R1 and H! are each a linear or branched alkyl group having 1 to 15 carbon atoms, an alkoxylough base system, a biphenyl system, a phenylcyclohexane system, a heterocyclic system, etc.) Liquid crystal compounds can be mentioned.
本発明の化合物は、次式の反応によって示されるように
製造できる。The compounds of the present invention can be prepared as shown by the reaction of the following formula.
であることを示す）
で表わされる液晶エステル化合物および該化合物の少く
とも１種を含有することを特徴とする液晶組成物である
。A liquid crystal composition characterized by containing a liquid crystal ester compound represented by the following formula and at least one of the compounds.
本発明の液晶組成物の成分にできる本発明の化合物以外
の他の成分としては、例えばエステル系、（上式中 １
１ 、 ＲＭ、（シは前記に同じである）すなわち、４
−アリルオキシビフェニリル−４′−カルボン酸エチル
エステルをＮ、Ｎ−ジエチルアニリン溶媒中、クライゼ
ン転移反応を行って、３−アリル−４−ヒドロキシビフ
ェニリル−４′−カルボン酸エチルエステルとし、つい
で臭化アルキルと無水炭酸ナトリウムとアセトン中で反
応を行って、３−アリル−４−アルコキシビフェニリル
−４′−カルボン酸エチルエステルとした。これを水酸
化カリウムを用いて加水分解して、カルボン酸とし、こ
のカルボン酸と塩化チオニルと反応して酸クロリドとし
、これをピリジン存在下フェノール類またはアルコール
類と反応して目的の液晶エステル化合物を製造した。Other components other than the compound of the present invention that can be used as a component of the liquid crystal composition of the present invention include, for example, esters, (in the above formula 1
1, RM, (S is the same as above), i.e. 4
-Allyloxybiphenylyl-4'-carboxylic acid ethyl ester was subjected to Claisen rearrangement reaction in N,N-diethylaniline solvent to form 3-allyl-4-hydroxybiphenylyl-4'-carboxylic acid ethyl ester, and then The alkyl bromide and anhydrous sodium carbonate were reacted in acetone to give 3-allyl-4-alkoxybiphenylyl-4'-carboxylic acid ethyl ester. This is hydrolyzed using potassium hydroxide to form a carboxylic acid, this carboxylic acid is reacted with thionyl chloride to form an acid chloride, and this is reacted with phenols or alcohols in the presence of pyridine to form the desired liquid crystal ester compound. was manufactured.
本発明の化合物は他の多くの液晶化合物、すなわちエス
テル系、シップ塩基系、ビフェニル系、フェニルシクロ
ヘキサン系、複素環系等の液晶化合物との相溶性がよく
、本発明の液晶エステル化合物を液晶組成物に少量添加
することによってぞ゛のＮ−Ｉ点を上昇せしめることが
できる。The compound of the present invention has good compatibility with many other liquid crystal compounds, such as ester-based, ship base-based, biphenyl-based, phenylcyclohexane-based, and heterocyclic-based liquid crystal compounds. By adding a small amount to a substance, the N-I point of the substance can be raised.
その上本発明の化合物を液晶組成物に加えるとＫＶＫ□
の値を大きくすることができるのでＳＴＮ型表示素子用
の液晶組成物に好適な化合物である。Moreover, when the compound of the present invention is added to a liquid crystal composition, KVK□
It is a compound suitable for liquid crystal compositions for STN type display elements because it can increase the value of .
以下に述べる実施例によシ本発明の化合物につきさらに
詳細に説明する。The compounds of the present invention will be explained in more detail in the following examples.
実施例１
３−アリル−４−ペンチルオキシビフェニリル−４′−
カルボン酸４−ペンチルオキシフェニルエステルの製造
（式ＩでＲ”＝Ｃ，ｌ（１，０−−■−一（＝とＲ咄Ｃ
，Ｈ□缶の場合）
４−アリルビフェニル−４７−カルボン酸エチルエステ
ル１７１１ｔＮＮ−ジエチルアニリン１００ゴに溶かし
、８時間窒素雰囲気下、煮沸還流した。Example 1 3-allyl-4-pentyloxybiphenylyl-4'-
Preparation of carboxylic acid 4-pentyloxyphenyl ester (Formula I, R''=C,l(1,0--■-1(= and R-C
, H□ can) 4-allylbiphenyl-47-carboxylic acid ethyl ester was dissolved in 1711tNN-diethylaniline (100g) and boiled and refluxed under nitrogen atmosphere for 8 hours.
放冷後、反応液を３Ｎ塩９５００−に加えよく撹拌した
。析出した沈澱物を濾過し、よく水洗を行った後乾燥し
た。この固体を全量アセトンＩＪ。After cooling, the reaction solution was added to 3N salt 9500- and stirred well. The deposited precipitate was filtered, thoroughly washed with water, and then dried. Add all of this solid to acetone IJ.
無水炭酸ナトリウムと共に激しく撹拌しながら、臭化ペ
ンチル２０ｇを加え、さらＩＣ２４時間煮沸還流した。While stirring vigorously with anhydrous sodium carbonate, 20 g of pentyl bromide was added, and the mixture was further boiled and refluxed for 24 hours.
熱いうちに沈澱物を戸別し、アセトンを留去した。残っ
た固型物をトルエン３００ゴに溶解し、２Ｎ水酸化ナト
リウムで洗滌後、水で中性になるまで洗った。トルエン
層を無水硫酸ナトリウム乾燥後、トルエンを減圧にて留
去し、残った油状物をエタノール５００ゴに溶かした。The precipitate was separated from house to house while it was still hot, and the acetone was distilled off. The remaining solid matter was dissolved in 300 g of toluene, washed with 2N sodium hydroxide, and then washed with water until neutral. After drying the toluene layer over anhydrous sodium sulfate, the toluene was distilled off under reduced pressure, and the remaining oil was dissolved in 500 g of ethanol.
別の反応器に水２００ｍ１に水酸化カリウム３０ｇを溶
かしたものを入れ、常温にて激しく撹拌しながらさきに
つくっておいたエタノール溶液を１０分で加えた。５時
間煮沸還流後冷却し、この反応液を６Ｎ塩酸７ＱＱｍ／
に加えると沈澱物が析出した。A solution of 30 g of potassium hydroxide in 200 ml of water was placed in another reactor, and the previously prepared ethanol solution was added over 10 minutes while stirring vigorously at room temperature. After boiling and refluxing for 5 hours, the reaction solution was cooled and diluted with 6N hydrochloric acid 7QQm/
When added to the solution, a precipitate was deposited.
ｐ過後水でよく洗い、乾燥した。このものが３−アリル
−４−ペンチルオキシビフェニル−４′−カルボン酸で
ある。After filtration, it was thoroughly washed with water and dried. This is 3-allyl-4-pentyloxybiphenyl-4'-carboxylic acid.
このようにして製造した３−アリル−４−ペンチルオキ
シビフェニル−４７−カルボン酸６．４ｇと大過剰の塩
化チオニルをマントルヒーター上で４時間加熱還流した
。ついで水流ポンプを用いて減圧にし、過剰の塩化チオ
ニルを留去すると結晶物が析出した。これが酸塩化物で
ある。別のフラスコに４−ペンチルオキシフェノール３
．６１ｉ’ｌ’！Ｊジン２Ｑｖｔｌに溶解し、これに、
先に製造した酸クロリドを加え、更にトルエン２００ｒ
！１１を加え激しく撹拌した。6.4 g of 3-allyl-4-pentyloxybiphenyl-47-carboxylic acid produced in this manner and a large excess of thionyl chloride were heated under reflux on a mantle heater for 4 hours. Then, the pressure was reduced using a water jet pump, and excess thionyl chloride was distilled off to precipitate crystals. This is an acid chloride. 4-pentyloxyphenol 3 in another flask
．． 61i'l'! Dissolved in Jgin 2Qvtl and added to it,
Add the acid chloride prepared earlier and add 200 r of toluene.
! 11 was added and stirred vigorously.
一晩放置してから、水５００！ｊにあけ、トルエン１０
０ｄを加えて抽出した。トルエン層を６Ｎ塩酸で、りｈ
で２Ｎ水酸化ナトリウムで洗滌後、中性になるまで水洗
した。トルエン層を無水硫酸ナトリウムで乾燥後、トル
エンを減圧で留去し、残った結晶物を活性アルミナのカ
ラムを用いて、トルエン溶媒でクロマト処理した。溶出
したトルエンを減圧にて留去し、残った結晶物をエタノ
ールで再結晶して目的の３−アリル−４−ペンチルオキ
シビフェニル−４′−カルボン酸４−ペンチルオキシフ
ェニルエステルを製造した。収量は３．３Ｉ（収率３５
％）、結晶−ネマチック液晶転移点（Ｃ−Ｎ点）は７２
．７〜７３．７℃、ネマチック液晶−透明点（Ｎ−Ｉ点
）は１０８．３℃であった。After leaving it overnight, water 500! Add 10 toluene to J.
0d was added and extracted. Rinse the toluene layer with 6N hydrochloric acid.
After washing with 2N sodium hydroxide, the solution was washed with water until neutral. After drying the toluene layer over anhydrous sodium sulfate, the toluene was distilled off under reduced pressure, and the remaining crystalline material was chromatographed with a toluene solvent using an activated alumina column. The eluted toluene was distilled off under reduced pressure, and the remaining crystals were recrystallized with ethanol to produce the desired 3-allyl-4-pentyloxybiphenyl-4'-carboxylic acid 4-pentyloxyphenyl ester. The yield is 3.3I (yield 35
%), crystal-nematic liquid crystal transition point (C-N point) is 72
．． 7 to 73.7°C, and the nematic liquid crystal clearing point (N-I point) was 108.3°C.
実施例２．３
実施例１において、３−アリル−４−ペンチルオキシビ
フェニル−４′−カルボン酸の代シに種々の３−アリル
−４−置換ビフェニル−４′−カルボン酸を、また４−
ペンチルオキシフェノールの代シに種々のフェノール類
またはアルコール類を用いて目的のエステル誘導体を製
造した結果を第１表に実施例１の結果と共に示した。Example 2.3 In Example 1, various 3-allyl-4-substituted biphenyl-4'-carboxylic acids were substituted for 3-allyl-4-pentyloxybiphenyl-4'-carboxylic acid, and 4-
The results of producing the desired ester derivatives using various phenols or alcohols in place of pentyloxyphenol are shown in Table 1 together with the results of Example 1.
実施例４（応用例１）
トランス−４−プロピル−（４−シアノフェニル）シク
ロヘキサン ３０重ｆｉ％トランスー４−ペ
ンチル−（４−シアノフェニル）シクロヘキサン
４０重量％トランス−４−へブチル−（４−シア
ノフェニル）シクロヘキサン ３０１１ｆ１
％なる組成の液晶混合物（Ａ）のＮ−Ｉ点は５２．１℃
、ΔＪは１１．２．２０℃における粘度は２３．４ｅｐ
。Example 4 (Application Example 1) Trans-4-propyl-(4-cyanophenyl)cyclohexane 30% trans-4-pentyl-(4-cyanophenyl)cyclohexane
40% by weight trans-4-hebutyl-(4-cyanophenyl)cyclohexane 3011f1
The N-I point of liquid crystal mixture (A) with a composition of 52.1°C
, ΔJ is 11.2.The viscosity at 20℃ is 23.4ep
.
Δｎは０．１１９、Ｋ＠ ／ Ｋ□は１．８２である。Δn is 0.119, and K@/K□ is 1.82.
液晶セルとして、酸化ケイ素をコーティングし、ラビン
グ処理した酸化スズ透明電極を有する基板を対向させて
組立てた、電極間距離が１０μｍのものを用意し、上記
の液晶組成物（Ａ）を封入してｖｔｈを測定したところ
１．５５ Ｖでらった。A liquid crystal cell was prepared in which substrates coated with silicon oxide and having transparent electrodes of rubbed tin oxide were assembled to face each other, and the distance between the electrodes was 10 μm, and the above liquid crystal composition (A) was sealed. When I measured vth, it was 1.55V.
この液晶組成物（Ａ） ９０重量係に本発明実施例２で
製造した３−アリル−４−ペンチルオキシビフェニル−
４７−カルボン酸４−（トランス−４′−プロピルシク
ロヘキシル）フェニルエステル１０重量係を溶解した液
晶組成物のＮ−Ｉ点は６４．５℃、Δεは９．６、Δｎ
は０．１１５、ｖｔｈは１．５９ｖ１粘度は２７．Ｑｃ
ｐであった。Ｋ、／に、は１．９５と大きくなシ、また
Ｎ−Ｉ点を上昇させることができＳＴＮ用として好適で
ある。This liquid crystal composition (A) 90% by weight 3-allyl-4-pentyloxybiphenyl produced in Example 2 of the present invention
The N-I point of the liquid crystal composition in which 47-carboxylic acid 4-(trans-4'-propylcyclohexyl)phenyl ester was dissolved in 10 parts by weight was 64.5°C, Δε was 9.6, and Δn
is 0.115, vth is 1.59, v1 viscosity is 27. Qc
It was p. K, / is as large as 1.95, and the N-I point can be raised, making it suitable for STN applications.
以上that's all
Claims (2)
した炭素数１〜１５のアルキル基またはアルコキシ基を
表わし、 ▲数式、化学式、表等があります▼は▲数式、化学式、
表等があります▼、▲数式、化学式、表等があります▼
、▲数式、化学式、表等があります▼、 ▲数式、化学式、表等があります▼、▲数式、化学式、
表等があります▼、▲数式、化学式、表等があります▼
、 ▲数式、化学式、表等があります▼、▲数式、化学式、
表等があります▼、 ▲数式、化学式、表等があります▼、▲数式、化学式、
表等があります▼、 ▲数式、化学式、表等があります▼、▲数式、化学式、
表等があります▼、 ▲数式、化学式、表等があります▼、▲数式、化学式、
表等があります▼、 ▲数式、化学式、表等があります▼ なる群から選ばれた一つであることを示す）で表わされ
る液晶エステル化合物。(1) General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (In the above formula, R^1 and R^2 each represent a linear or branched alkyl group or alkoxy group having 1 to 15 carbon atoms, ▲There are mathematical formulas, chemical formulas, tables, etc.▼ is ▲mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ Mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
, ▲There are mathematical formulas, chemical formulas, tables, etc.▼,▲Mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ Mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ Mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ Mathematical formulas, chemical formulas,
There are tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼ A liquid crystal ester compound represented by one selected from the group.
化合物を含有することを特徴とする液晶組成物。(2) A liquid crystal composition containing a liquid crystal ester compound represented by the general formula according to claim 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1037830A JPH02218646A (en) | 1989-02-17 | 1989-02-17 | Liquid crystal ester compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1037830A JPH02218646A (en) | 1989-02-17 | 1989-02-17 | Liquid crystal ester compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH02218646A true JPH02218646A (en) | 1990-08-31 |
Family
ID=12508447
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1037830A Pending JPH02218646A (en) | 1989-02-17 | 1989-02-17 | Liquid crystal ester compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH02218646A (en) |
-
1989
- 1989-02-17 JP JP1037830A patent/JPH02218646A/en active Pending
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