JPS6059893B2 - Carboxylic acid ester derivative of 4-fluorophenol - Google Patents
Carboxylic acid ester derivative of 4-fluorophenolInfo
- Publication number
- JPS6059893B2 JPS6059893B2 JP753980A JP753980A JPS6059893B2 JP S6059893 B2 JPS6059893 B2 JP S6059893B2 JP 753980 A JP753980 A JP 753980A JP 753980 A JP753980 A JP 753980A JP S6059893 B2 JPS6059893 B2 JP S6059893B2
- Authority
- JP
- Japan
- Prior art keywords
- formulas
- liquid crystal
- tables
- formula
- carboxylic 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
- -1 Carboxylic acid ester derivative of 4-fluorophenol Chemical class 0.000 title claims description 19
- 239000004973 liquid crystal related substance Substances 0.000 claims description 29
- 239000000203 mixture Substances 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 20
- 239000000126 substance Substances 0.000 claims description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000004519 manufacturing process Methods 0.000 description 7
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- RHMPLDJJXGPMEX-UHFFFAOYSA-N 4-fluorophenol Chemical compound OC1=CC=C(F)C=C1 RHMPLDJJXGPMEX-UHFFFAOYSA-N 0.000 description 2
- JMAUQQIVJIRNDQ-UHFFFAOYSA-N 4-heptylcyclohexane-1-carboxylic acid Chemical compound CCCCCCCC1CCC(C(O)=O)CC1 JMAUQQIVJIRNDQ-UHFFFAOYSA-N 0.000 description 2
- POEBGIQSFIJHAX-UHFFFAOYSA-N 4-hexylcyclohexane-1-carboxylic acid Chemical compound CCCCCCC1CCC(C(O)=O)CC1 POEBGIQSFIJHAX-UHFFFAOYSA-N 0.000 description 2
- RVLAXPQGTRTHEV-UHFFFAOYSA-N 4-pentylcyclohexane-1-carboxylic acid Chemical compound CCCCCC1CCC(C(O)=O)CC1 RVLAXPQGTRTHEV-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- 239000004990 Smectic liquid crystal Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 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 1
- PUFNCAACUKXZTR-UHFFFAOYSA-N 4-[2-(4-pentylphenyl)phenyl]benzonitrile Chemical group C1=CC(CCCCC)=CC=C1C1=CC=CC=C1C1=CC=C(C#N)C=C1 PUFNCAACUKXZTR-UHFFFAOYSA-N 0.000 description 1
- JFKUBRAOUZEZSL-UHFFFAOYSA-N 4-butylbenzoic acid Chemical compound CCCCC1=CC=C(C(O)=O)C=C1 JFKUBRAOUZEZSL-UHFFFAOYSA-N 0.000 description 1
- HHPCNRKYVYWYAU-UHFFFAOYSA-N 4-cyano-4'-pentylbiphenyl Chemical group C1=CC(CCCCC)=CC=C1C1=CC=C(C#N)C=C1 HHPCNRKYVYWYAU-UHFFFAOYSA-N 0.000 description 1
- HBQUXMZZODHFMJ-UHFFFAOYSA-N 4-hexoxybenzoic acid Chemical compound CCCCCCOC1=CC=C(C(O)=O)C=C1 HBQUXMZZODHFMJ-UHFFFAOYSA-N 0.000 description 1
- 239000004988 Nematic liquid crystal Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 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
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Description
【発明の詳細な説明】
本発明は液晶組成物の成分として有用な、正の誘電異方
性を有する新規な含フッ素化合物及びそれを含有する液
晶組成物に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel fluorine-containing compound having positive dielectric anisotropy, which is useful as a component of a liquid crystal composition, and a liquid crystal composition containing the same.
液晶を応用した表示素子は時計、電卓などに広く使用さ
れる様になつて来た。Display elements using liquid crystals have come to be widely used in watches, calculators, etc.
この液晶表示素子はその液晶表示方式によりＴＮ型（ね
じれネマチツク型）、ＤＳ型（動的散乱型）、ゲスト・
ホスト型、ＤＡＰ型などに分けられ、それぞれの方式に
よつて使用される液晶の特性は異なるがいずれも誘電異
方性の絶対値の大きなものが要求されてきている。それ
は誘電異方性の絶対値の大きな液晶組成物を使用するこ
とによソー般に表示素子の駆動電圧を下けることが出来
、又応答特性をよくすることが出来るからてある。しか
し誘電異方性の絶対値が大きくなくても低電圧で駆動出
来る様な液晶があれば表示素子の消費電力を更に小さく
することが出来、一層好ましいものとなる。本発明者は
この様な特性をもつ化合物を広く探．究した結果ある種
の含フッ素化合物がその様な要件を満たすものであるこ
とを発見し本発明に到達した。This liquid crystal display element is TN type (twisted nematic type), DS type (dynamic scattering type), guest type, etc. depending on its liquid crystal display method.
Liquid crystals are divided into host type, DAP type, etc., and the characteristics of the liquid crystal used for each type are different depending on the type, but in both cases, a large absolute value of dielectric anisotropy is required. This is because by using a liquid crystal composition with a large absolute value of dielectric anisotropy, the driving voltage of the display element can generally be lowered and the response characteristics can be improved. However, if there is a liquid crystal that can be driven at a low voltage even if the absolute value of dielectric anisotropy is not large, the power consumption of the display element can be further reduced, which would be even more preferable. The inventor has extensively searched for compounds with such characteristics. As a result of research, it was discovered that a certain type of fluorine-containing compound satisfies such requirements, and the present invention was achieved.
即ち本発明は一般式
（但し上式に於てｘはき（ 〉１１１１、
のいずれかであり、又、Ｒはいずれも炭素数１〜
１５のアルキル基又はアルコキ・シ基を示す）で表わさ
れる４−フルオロフェノールのカルボン酸エステル誘導
体及びそれを少くとも１種含有する液晶組成物である。That is, the present invention is based on the general formula (however, in the above formula, x is substituted ( 〉1111,
and each R has 1 to 1 carbon atoms.
The present invention provides a carboxylic acid ester derivative of 4-fluorophenol represented by the following formula (15 alkyl group or alkoxy group) and a liquid crystal composition containing at least one thereof.
（１）式の化合物は誘電異方性がΔＥ＝１．５前後と小
さい値であるにもかかわらずしきい電圧は１．４〜２．
０Ｖ程度と低く低電圧駆動が可能で、従つてこの化合物
を使用して消費電力の小さい表示素子をつくることが出
来る。又（１）式の化合物は粘度が小さく、それを構成
成分として使用することにより低粘度の液晶組成物を得
ることが出来、従つて応答速度の速い液晶表示素子を得
ることが出来る。更に表示素子用液晶として必要な熱、
光、湿度、電気などに対する安定性も充分有している。
つぎに本発明の化合物の製造法を示すと、まず対応する
カルボン酸に塩化チオニルを反応させてカルボン酸酸塩
化物を製造し、ついで４−フルオロフェノールとピリジ
ンを作用させると目的物が得られる。これを化学式で示
すと、
（上式中Ｒは前記と同じ）
この様にして得られた化合物はあるものはネマチツク液
晶であり、又あるものはスメクチツク液晶であり、又そ
れ自身では液晶とならないものもある。Although the compound of formula (1) has a small dielectric anisotropy of around ΔE=1.5, its threshold voltage is 1.4-2.
It is possible to drive at a low voltage of about 0 V, so this compound can be used to create a display element with low power consumption. Further, the compound of formula (1) has a low viscosity, and by using it as a constituent component, a liquid crystal composition with a low viscosity can be obtained, and therefore a liquid crystal display element with a high response speed can be obtained. Furthermore, the heat required for liquid crystal display elements,
It also has sufficient stability against light, humidity, electricity, etc.
Next, the method for producing the compound of the present invention is shown. First, the corresponding carboxylic acid is reacted with thionyl chloride to produce a carboxylic acid acid chloride, and then 4-fluorophenol and pyridine are reacted to obtain the desired compound. . This is expressed as a chemical formula: (R in the above formula is the same as above) Some of the compounds obtained in this way are nematic liquid crystals, others are smectic liquid crystals, and others do not become liquid crystals by themselves. There are some things.
しかし、いずれにしてもその誘電異方性は小さいので、
このものを他の液晶化合物などと組み合わせて液晶組成
物とした場合、誘電異方性が小さく、かつ駆動電圧の低
い液晶表示素子を得ることが出来る。他の液晶化合物は
表示装置のタイプ、用途などによつて適宜選択すればよ
い。他の液晶化合物との相溶性は非常によいので、その
点での制限は殆んどない。以下に実施例として本発明の
（１）式の化合物の製造例及びそれにより得られたもの
の特性値及びそれを含む液晶組成物の特性値を示して本
発明を更に詳細に説明する。However, in any case, the dielectric anisotropy is small, so
When this compound is combined with other liquid crystal compounds to form a liquid crystal composition, a liquid crystal display element with small dielectric anisotropy and low driving voltage can be obtained. Other liquid crystal compounds may be appropriately selected depending on the type of display device, usage, etc. Since it has very good compatibility with other liquid crystal compounds, there are almost no restrictions in that respect. The present invention will be explained in more detail by showing examples of the production of the compound of formula (1) of the present invention, the characteristic values of the products obtained therefrom, and the characteristic values of liquid crystal compositions containing the same.
実施例１
〔トランスー４一置換シクロヘキサンカルボン酸４′−
フルオロフェニルエステル（■）の製造〕
トランスー４一置換シクロヘキサンカルボン酸０．０３
モルに塩化チオニル１０ｍ１を加え、ウォーターバス上
で６０〜８０℃で４時間加温する。Example 1 [Trans-4 monosubstituted cyclohexanecarboxylic acid 4'-
Production of fluorophenyl ester (■)] Trans-4 monosubstituted cyclohexanecarboxylic acid 0.03
Add 10 ml of thionyl chloride to the mole and heat on a water bath at 60-80°C for 4 hours.
均一になるので更に１時間放置してから減圧にして過剰
の塩化チオニルを完全に留去すると油状物が残る。これ
がトランスー４一置換シクロヘキサンカルボン酸酸塩化
物である。次に４−フルオロフェノール３．３ｆをピリ
ジン１０ｍ１に溶かしたものに先の酸塩化物をはげしく
振りまぜながら加える。Once the mixture becomes homogeneous, it is left to stand for an additional hour, and then the pressure is reduced to completely distill off excess thionyl chloride, leaving an oily substance. This is a trans-4 monosubstituted cyclohexanecarboxylic acid chloride. Next, the above acid chloride is added to a solution of 3.3 f of 4-fluorophenol dissolved in 10 ml of pyridine while stirring vigorously.
この反応液を一晩放置後水１００ｍＬ中にあけトルエン
１００ｍ１で油状物を抽出する。トルエン層を６ＮＨＣ
１で、ついで２ＮＮａ０Ｈで洗浄した後、中性になるま
で水洗する。トルエン層を枦過後トルエンを減圧留去す
る。残つた油状物をエタノールで再結晶すると目的のト
ランスー４一置換シクロヘキサンカルボン酸４−フルオ
ロフェニルエステルが得られる。この様にして得られた
一連のこれ等の化合物の物性値（転移点）及び元素分析
値を第１表に示す。又（１）式でＲがＣ２Ｈ５の化合物
のＭ．Ｐは２９．４〜２９．（代）であつた。After leaving the reaction solution overnight, it was poured into 100 mL of water and the oil was extracted with 100 mL of toluene. 6NHC toluene layer
1, then 2N NaOH, and then water until neutral. After the toluene layer is filtered, the toluene is distilled off under reduced pressure. The remaining oil is recrystallized from ethanol to obtain the desired trans-4-monosubstituted cyclohexanecarboxylic acid 4-fluorophenyl ester. Table 1 shows the physical property values (transition points) and elemental analysis values of a series of these compounds thus obtained. Furthermore, the M. P is 29.4-29. It was (generation).
実施例２
〔４一置換安息香酸４′−フルオロフェニルエステル＊
（■）の製造〕
実施例１におけるトランスー４一置換シクロヘキサンカ
ルボン酸の代りに４一置換安息香酸０．０３モルを用い
る以外は全く同様にして４一置換安息香酸４′−フルオ
ロフェニルエステルが得られる。Example 2 [4-monosubstituted benzoic acid 4'-fluorophenyl ester*
Production of (■)] A 4-substituted benzoic acid 4'-fluorophenyl ester was obtained in exactly the same manner as in Example 1, except that 0.03 mol of a 4-substituted benzoic acid was used instead of the trans-4-substituted cyclohexanecarboxylic acid. It will be done.
第２表にそれらの化合物の物性値及び元素分析値を第２
表に示す。ル）一安息香酸４″−フルオロフェニルエス
テル（■）の製造〕実施例１におけるトランスー４一置
換シクロヘキサンカルボン酸の代りに４−（トランスー
４―ペンチルシクロヘキシル）一安息香酸０．０３モル
を用いる以外は全く同様にして４−（トランスー４″−
ペンチルシクロヘキシル）一安息香酸４″−フルオロフ
ェニルエステル７．５ｙ（収率６７．９％）が得られる
。Table 2 shows the physical properties and elemental analysis values of those compounds.
Shown in the table. l) Production of monobenzoic acid 4''-fluorophenyl ester (■)] Except for using 0.03 mol of 4-(trans-4-pentylcyclohexyl) monobenzoic acid in place of the trans-4 monosubstituted cyclohexanecarboxylic acid in Example 1. In exactly the same way, 4-(trans-4''-
Pentylcyclohexyl) monobenzoic acid 4''-fluorophenyl ester 7.5y (yield 67.9%) is obtained.
このものもスメクチツク液晶でそのＣ−Ｎ点は９１．０
〜９３．３チＣ，．Ｎ−１点は１５９．（代）であつた
。又、その元素分析値はＣ：７９．９％（理論値７８．
２％）Ｈ：７．８％（理論値７．９％）であつた。尚、
同様にして得られた他のアルキル基を有する（■）式の
化合物の物性を上記の結果も含めて第３表に示す。実施
例４
〔６一置換ナフタリンー２−カルボン酸４″−フルオロ
フェニルエステル（■）の製造〕
実施例１に於けるトランスー４一置換シクロヘキサンカ
ルボン酸の代わりに６一置換ナフタリンー２−カルボン
酸０．０３モルを使用する以外は全く同様にして６一置
換ナフタリンー２−カルボン酸４″−フルオロフェニル
エステルが得られる第４表にそれらの化合物の物性値を
示す。This one is also a smectic liquid crystal and its C-N point is 91.0.
~93.3chiC,. N-1 point is 159. It was (generation). In addition, its elemental analysis value is C: 79.9% (theoretical value 78.
2%) H: 7.8% (theoretical value 7.9%). still,
The physical properties of compounds of formula (■) having other alkyl groups obtained in the same manner are shown in Table 3, including the above results. Example 4 [Production of 6-monosubstituted naphthalene-2-carboxylic acid 4''-fluorophenyl ester (■)] In place of the trans-4-monosubstituted cyclohexanecarboxylic acid in Example 1, 6-monosubstituted naphthalene-2-carboxylic acid 0. 6-monosubstituted naphthalene-2-carboxylic acid 4''-fluorophenyl ester was obtained in exactly the same manner except that 0.3 mol was used. Table 4 shows the physical properties of these compounds.
実施例５
〔６一置換−１●２●３●４−テトラヒドロナフタリン
ー２−カルボン酸４″−フルオロフェニルエステル（■
）の製造〕
実施例１におけるトランスー４一置換シクロヘキサンカ
ルボン酸の代りに６置換−１・２・３・４−テトラヒド
ロナフタリンー２−カルボン酸０．０３モルを使用する
外は全く同様にして６一置換−１●２●３●４−テトラ
ヒドロナフタリンー２−カルボン酸４′−フルオロフェ
ニルエステルが得られる。Example 5 [6-monosubstituted-1●2●3●4-tetrahydronaphthalene-2-carboxylic acid 4″-fluorophenyl ester (■
) Production of 6 in exactly the same manner as in Example 1 except that 0.03 mol of 6-substituted-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid was used instead of trans-4 monosubstituted cyclohexanecarboxylic acid. Monosubstituted-1●2●3●4-tetrahydronaphthalene-2-carboxylic acid 4'-fluorophenyl ester is obtained.
（■）式でＲがＣ５Ｈｌｌの場合、収量５．５ｙ（収率
５３．９％）融点７７．０〜７＆（代）、ＲがＣ，Ｈｌ
５のものは収量６．１ｆ１（収率５５．３％）、融点５
＆６〜５９．７℃であつた。実施例６（応用例１）トラ
ンスー４−ペンチルシクロヘキサンカルボン酸４’−フ
ルオロフェニルエステル１部トランスー４−ヘキシルシ
クロヘキサンカルボン酸４’−フルオロフェニルエステ
ル１部トランスー４−ヘプチルシクロヘキサンカルボン
酸４’−フルオロフェニルエステル３部なる組成の液晶
組成物のＮ−１点は２９．４℃であり、ΔＥは＋１．４
である。In the formula (■), when R is C5Hll, the yield is 5.5y (yield 53.9%), the melting point is 77.0~7&(substitute), and R is C, Hll.
5 has a yield of 6.1f1 (yield 55.3%) and a melting point of 5.
&6-59.7°C. Example 6 (Application Example 1) Trans-4-pentylcyclohexanecarboxylic acid 4'-fluorophenyl ester 1 part trans-4-hexylcyclohexanecarboxylic acid 4'-fluorophenyl ester 1 part trans-4-heptylcyclohexanecarboxylic acid 4'-fluorophenyl ester The N-1 point of the liquid crystal composition with a composition of 3 parts of ester is 29.4°C, and ΔE is +1.4
It is.
この組成物を、酸化ケイ素でコートし、ラピング処理し
た酸化スズ透明電極を組合せて作つた厚さＩＯＰ７ＴＬ
厚のセルを用いて２５℃で特性を測つたところしきい電
圧は１．８Ｖ）飽和電圧は２．６Ｖであつた。実施例７
（応用例２）
トランスー４−ペンチルシクロヘキサンカルボン酸４’
−フルオロフェニルエステル１部トランスー４−ヘキシ
ルシクロヘキサンカルボン酸４’−フルオロフェニルエ
ステル１部トランスー４−ヘプチルシクロヘキサンカル
ボン酸４’−フルオロフェニルエステル４部なる組成の
液晶組成物のＮ−Ｉ点は３０．０℃でありΔＥは＋１．
５１であつた。Thickness IOP7TL made by combining this composition with a tin oxide transparent electrode coated with silicon oxide and subjected to wrapping treatment.
When the characteristics were measured at 25°C using a thick cell, the threshold voltage was 1.8V) and the saturation voltage was 2.6V. Example 7
(Application example 2) Trans-4-pentylcyclohexanecarboxylic acid 4'
- Fluorophenyl ester 1 part trans-4-hexylcyclohexanecarboxylic acid 4'-fluorophenyl ester 1 part trans-4-heptylcyclohexanecarboxylic acid 4'-fluorophenyl ester 4 parts The N-I point is 30. 0°C and ΔE is +1.
It was 51.
その特性を応用例１と同様にして測定したところ２５℃
に於いてしきい電圧は１．４４Ｖ）飽和電圧は２．１２
Ｖであり、又３Ｖ）３２Ｈｚでの立上り時間１４０Ｗ１
，ＳｅＣ）立下り時間は１６０ｍｓｅＣであつた。又１
５℃におけるしきい電圧は１．９１Ｖ）飽和電圧は２．
７４Ｖであつた。実施例８（応用例３）
４−ペンチルー４’−シアノビフェニル４５％４−ペブ
チルー４’−シアノビ（混合物Ａ）フェニル２９％４−
オクチルオキシー４’−シアノビフェニル１５％４−ペ
ンチルー４″−シアノターフエニル１１％なる組成の液
晶混合物Ａ（７）Ｎ−Ｉ点は６３．冗、ΔＥは１２．収
２０℃での粘度は６ｐである。When its characteristics were measured in the same manner as in Application Example 1, the temperature was 25°C.
The threshold voltage is 1.44V) The saturation voltage is 2.12
V, also 3V) rise time 140W1 at 32Hz
, SeC) fall time was 160 msecC. Again 1
Threshold voltage at 5°C is 1.91V) Saturation voltage is 2.
It was 74V. Example 8 (Application example 3) 4-pentyl-4'-cyanobiphenyl 45% 4-pebutyl-4'-cyanobi (mixture A) phenyl 29% 4-
Liquid crystal mixture A (7) with a composition of octyloxy-4'-cyanobiphenyl 15% and 4-pentyl-4''-cyanoterphenyl 11%.N-I point is 63.0%, ΔE is 12.0%, viscosity at 20°C is 6p. It is.
これを応用例１と同じ条件で測定したところ２５℃での
しきい電圧は１．６５Ｖ）飽和電圧は２．３１Ｖであつ
た。この液晶混合物Ａ８Ｏｍに本発明の４−ブチル安息
香酸４’−フルオロフェニルエステル２園を加えた液晶
組成物はＮ−Ｉ点が４４℃でΔξは１１．６’Ｃと低下
したにも抱らず、しきい電圧値は１．３１Ｖ）飽和電圧
は１．９１Ｖと動作電圧は低くなり、又２０℃に於ける
粘度も５０Ｃｐと低くなつた。実施例９（応用例４）
応用例３に於ける液晶混合物Ａ８園に４−ヘキシルオキ
シ安息香酸４’−フルオロフェニルエステル２（２）を
加えた液晶混合物はＮ−Ｉ点が４８．６℃、Δｔは１１
．７、２０℃の粘度は４５Ｃｐである。When this was measured under the same conditions as Application Example 1, the threshold voltage at 25°C was 1.65V) and the saturation voltage was 2.31V. A liquid crystal composition in which two 4-butylbenzoic acid 4'-fluorophenyl esters of the present invention were added to this liquid crystal mixture A8Om had an N-I point of 44°C and a Δξ of 11.6'C. First, the threshold voltage value was 1.31V) The saturation voltage was 1.91V, which was a low operating voltage, and the viscosity at 20°C was also low, 50Cp. Example 9 (Application Example 4) The liquid crystal mixture obtained by adding 4-hexyloxybenzoic acid 4'-fluorophenyl ester 2 (2) to the liquid crystal mixture A8 in Application Example 3 has an N-I point of 48.6°C. , Δt is 11
．． 7. The viscosity at 20°C is 45 Cp.
これを応用例３と同じ条件で測定するとしきい電圧は１
．４５Ｖ）飽和電圧２．０２Ｖと混合Ａより低い値にな
つていた。実施例１０（応用例５）
応用例３に於ける液晶混合物Ａ９園に４−（トランスー
４’−ペンチルシクロヘキシル）一安息香酸４″−フル
オロフェニルエステルｍ部を加えた液晶組成物のＮ−Ｉ
点は７０．２℃とより、ΔＥは１２．１、２昨での粘度
は６０Ｃｐであつた。When this is measured under the same conditions as Application Example 3, the threshold voltage is 1
．． 45V) The saturation voltage was 2.02V, which was lower than that of Mixture A. Example 10 (Application Example 5) N-I of a liquid crystal composition obtained by adding m parts of 4-(trans-4'-pentylcyclohexyl)monobenzoic acid 4''-fluorophenyl ester to the liquid crystal mixture A9 in Application Example 3.
The point was 70.2°C, ΔE was 12.1, and the viscosity at 2 days ago was 60Cp.
Claims (1)
▼、▲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▼ のいずれかであり、又、Ｒはいずれも炭素数１〜１５の
アルキル基又はアルコキシ基を示す）で表わされる４−
フルオロフェノールのカルボン酸エステル誘導体。 ２ 一般式（ I ）が ▲数式、化学式、表等があります▼（II）（Ｒは前記と
同じ） である特許請求の範囲第１項記載の化合物。 ３ 一般式（ I ）が ▲数式、化学式、表等があります▼（III）（Ｒは前記
と同じ） である特許請求の範囲第１項記載の化合物。 ４ 一般式 ▲数式、化学式、表等があります▼（ I ）（但し上式
に於てＸ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▼ のいずれかであり、又、Ｒはいずれも炭素数１〜１５の
アルキル基又はアルコキシ基を示す）で表わされる４−
フルオロフェノールのカルボン酸エステル誘導体を少く
とも１成分含むことを特徴とする液晶組成物。[Scope of Patent Claims] 1 General formula▲There are mathematical formulas, chemical formulas, tables, etc.▼ (However, in the above formula, X is▲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. ▼ 4-
Carboxylic acid ester derivative of fluorophenol. 2. The compound according to claim 1, wherein the general formula (I) is ▲a numerical formula, a chemical formula, a table, etc.▼(II) (R is the same as above). 3. The compound according to claim 1, wherein the general formula (I) is ▲A mathematical formula, a chemical formula, a table, etc.▼(III) (R is the same as above). 4 General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (I) (However, in the above formula, There are chemical formulas, tables, etc.▼,▲mathematical formulas, chemical formulas,
There are tables, etc. ▼ ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ 4-
A liquid crystal composition comprising at least one component of a fluorophenol carboxylic acid ester derivative.
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP753980A JPS6059893B2 (en) | 1980-01-25 | 1980-01-25 | Carboxylic acid ester derivative of 4-fluorophenol |
| DE3102017A DE3102017C2 (en) | 1980-01-25 | 1981-01-22 | Halogenated ester derivatives and liquid crystal compositions containing them |
| CH40681A CH645876A5 (en) | 1980-01-25 | 1981-01-22 | HALOGENED ESTER DERIVATIVES WITH POSITIVE ANISOTROPY AND LIQUID CRYSTAL MIXTURES CONTAINING THESE COMPOUNDS. |
| US06/227,942 US4340498A (en) | 1980-01-25 | 1981-01-23 | Halogenated ester derivatives |
| GB8102277A GB2070593B (en) | 1980-01-25 | 1981-01-26 | Halogenated ester derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP753980A JPS6059893B2 (en) | 1980-01-25 | 1980-01-25 | Carboxylic acid ester derivative of 4-fluorophenol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS56104844A JPS56104844A (en) | 1981-08-20 |
| JPS6059893B2 true JPS6059893B2 (en) | 1985-12-27 |
Family
ID=11668587
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP753980A Expired JPS6059893B2 (en) | 1980-01-25 | 1980-01-25 | Carboxylic acid ester derivative of 4-fluorophenol |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6059893B2 (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR920008357Y1 (en) * | 1990-10-11 | 1992-11-20 | 삼성전자 주식회사 | Stereo high frequency modulator |
| JP4560688B2 (en) * | 1999-07-28 | 2010-10-13 | Ｄｉｃ株式会社 | Compound having tetrahydronaphthalene skeleton and liquid crystal composition containing the same |
| JP5641286B2 (en) * | 2010-03-29 | 2014-12-17 | Dic株式会社 | Transparent insulating composition |
| JP5811417B2 (en) * | 2013-10-21 | 2015-11-11 | Dic株式会社 | Transparent insulating composition |
| JP6487281B2 (en) * | 2014-06-23 | 2019-03-20 | 国立大学法人千葉大学 | Liquid crystal composition and liquid crystal display element |
-
1980
- 1980-01-25 JP JP753980A patent/JPS6059893B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS56104844A (en) | 1981-08-20 |
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