JPS63313751A - Ester compound - Google Patents
Ester compoundInfo
- Publication number
- JPS63313751A JPS63313751A JP62149602A JP14960287A JPS63313751A JP S63313751 A JPS63313751 A JP S63313751A JP 62149602 A JP62149602 A JP 62149602A JP 14960287 A JP14960287 A JP 14960287A JP S63313751 A JPS63313751 A JP S63313751A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- formula
- liquid crystal
- formulas
- ester compound
- 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.)
- Granted
Links
- -1 Ester compound Chemical class 0.000 title claims abstract description 32
- 150000001875 compounds Chemical class 0.000 claims abstract description 40
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 230000010287 polarization Effects 0.000 claims description 12
- 230000002269 spontaneous effect Effects 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract description 30
- 239000004973 liquid crystal related substance Substances 0.000 abstract description 15
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract description 8
- 239000005262 ferroelectric liquid crystals (FLCs) Substances 0.000 abstract description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract description 4
- 239000002994 raw material Substances 0.000 abstract description 2
- 239000000463 material Substances 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 10
- 230000000875 corresponding effect Effects 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000010992 reflux Methods 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- QPRQEDXDYOZYLA-YFKPBYRVSA-N (S)-2-methylbutan-1-ol Chemical compound CC[C@H](C)CO QPRQEDXDYOZYLA-YFKPBYRVSA-N 0.000 description 2
- YZWKKMVJZFACSU-UHFFFAOYSA-N 1-bromopentane Chemical compound CCCCCBr YZWKKMVJZFACSU-UHFFFAOYSA-N 0.000 description 2
- QPRQEDXDYOZYLA-UHFFFAOYSA-N 2-methyl-1-butanol Substances CCC(C)CO QPRQEDXDYOZYLA-UHFFFAOYSA-N 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-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
- CVNOWLNNPYYEOH-UHFFFAOYSA-N 4-cyanophenol Chemical compound OC1=CC=C(C#N)C=C1 CVNOWLNNPYYEOH-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000002079 cooperative effect Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Liquid Crystal (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Abstract
Description
【発明の詳細な説明】
「産業上の利用分野」
本発明は、液晶表示素子をなす強誘電性液晶として利用
されるエステル化合物に関するものである。DETAILED DESCRIPTION OF THE INVENTION "Field of Industrial Application" The present invention relates to an ester compound used as a ferroelectric liquid crystal forming a liquid crystal display element.
「従来技術」
第４図は、従来のねじれ配列を誘発する液晶性化合物、
即し強請′市性液晶の典ｊ（１！的な模式＋１１４迅を
示す乙のである。"Prior art" Figure 4 shows a conventional liquid crystalline compound that induces twisted alignment.
Therefore, it is a standard of commercial liquid crystal display (1! typical model + 114 times).
図中符号Ｉは中心骨格部で、その両端には側鎖２．３か
結合している。側鎖２．３の何れが一方（この例では側
鎖２）は、不斉構造を有する光学活性入１ζによって形
成されている。Reference numeral I in the figure is the central skeleton, and side chains 2.3 are bonded to both ends of the central skeleton. One of the side chains 2.3 (in this example, side chain 2) is formed by an optically active chain 1ζ having an asymmetric structure.
「発明か解決しようとする問題点」
製造上および配向性などの表示特性上、強誘電性液晶化
合物のらせんピッチは、長い方が有利である。"Problems to be Solved by the Invention" In terms of manufacturing and display characteristics such as orientation, it is advantageous for the helical pitch of the ferroelectric liquid crystal compound to be longer.
ところか、従来の強誘電性液晶化合物の多くはは、らせ
んピッチが数μｍ以下と小さく、 このため、従来は数
種類の液晶化合物をブレンドして、らせんビッヂの長い
液晶組成物を調合しなければならなかった。However, many of the conventional ferroelectric liquid crystal compounds have a small helical pitch of several micrometers or less, and for this reason, conventionally, several types of liquid crystal compounds had to be blended to prepare a liquid crystal composition with a long helical pitch. did not become.
本発明は上記事情に鑑みてなされたものて、ら什んピッ
チの長い新規な液晶化合物を提供することを目的とする
。The present invention was made in view of the above circumstances, and an object of the present invention is to provide a novel liquid crystal compound having a long pitch.
「問題点を解決するための手段」
本発明のエステル化合物は、下記一般式（１）で表され
ろ化合物である。"Means for Solving the Problems" The ester compound of the present invention is a compound represented by the following general formula (1).
Ｒｈｏ−◎−Ｃ−Ｏ−◎−０Ｒ２−（Ｉ）（（Ｉ）式中
Ｒ１１Ｒ２は、互いに異なる不斉構造を持つアルキル基
またはその誘導体を示す）このエステル化合物は、第１
図に示すように、中心骨格部１の両側に互いに異なる不
斉構造をｂつ光学活性基が側鎖５．６として結合したも
のである。Rho-◎-C-O-◎-0R2-(I) (In the formula (I), R11R2 represents an alkyl group or a derivative thereof having a mutually different asymmetric structure) This ester compound
As shown in the figure, b optically active groups having different asymmetric structures are bonded to both sides of the central skeleton 1 as side chains 5.6.
この構造のエステル化合物は、互いに異なる不斉構造を
有する側鎖５．６の協同作用によって、らせんピッチが
長い強誘電性液晶となる。The ester compound having this structure becomes a ferroelectric liquid crystal with a long helical pitch due to the cooperative action of the side chains 5 and 6 having mutually different asymmetric structures.
本発明のエステル化合物は、 （１）式中のＲ１、Ｒ７
が、 （ＩＩ）式および（ＩＩＩ）式の液晶性化合物に
おいて、同じ向きの自発分極と異なる方向のらせんのね
じれを誘起するものであることが望ましい。The ester compound of the present invention is as follows: R1 and R7 in the formula (1)
However, in the liquid crystal compounds of formulas (II) and (III), it is desirable that the compounds induce spontaneous polarization in the same direction and helical twisting in different directions.
ＲＯ−◎−Ｃ−Ｏ−◎−ＯＲ−（ｎ）
ＲＯ−■−Ｃ−Ｏ−◎−０Ｒ２・・−・（Ｉ［［）（（
■）式、（■）式中Ｒは、不斉構造を持たないアルキル
基を示す）
すなわち、側鎖５．６を形成する光学活性基は、その基
が誘起する液晶化合物のらせんのねじれの方向および自
発分極の向きの関係によって、第１表に示すように（イ
）〜（ニ）の４種類に分類できることか知られている（
Ｊ、Ｗ、Ｇｏｏｄｂｙ ５ｔａｌ、 Ｊ、Ａｍ。RO-◎-C-O-◎-OR-(n) RO-■-C-O-◎-0R2...-(I[[)((
(■) Formula, (■) In the formula, R represents an alkyl group that does not have an asymmetric structure) In other words, the optically active group forming the side chain 5.6 causes the helical twist of the liquid crystal compound that the group induces. It is known that it can be classified into four types (a) to (d) as shown in Table 1, depending on the relationship between the direction and the direction of spontaneous polarization (
J, W, Goodby 5tal, J, Am.
Ｃｈｅｍ、Ｓｏｃ、、 １０ｇ、４７２９ （’８６）
）。Chem, Soc, 10g, 4729 ('86)
).
そ５して、本発明のエステル化合物では、（１）式中の
Ｒ１，ｎ ｖに、 第１表中（イ）と（ロ）に分類され
る光学活性基から１つづつを選んで、あるいは（ハ）と
（ニ）に分類される光学活性基から１つづつを選んで用
いることが望ましい。5. Then, in the ester compound of the present invention, R1 and nv in formula (1) are selected from one optically active group classified as (a) and (b) in Table 1, Alternatively, it is preferable to select and use one optically active group classified into (c) and (d).
以下余白
＝４−
第１表
本発明のエステル化合物を構成するＩ’（、、ｒ（、と
して、より具体的には、
Ｒ，が Ｃ１Ｈ２Ｌ＋ｌ・ＣＨ（ＣＨ２）ｎ −−＝（
Ｎ）さＲ３
（１ｆｍ、 ２≦Ｑ、ｊ≦８）であり、 か−Ｊ Ｒ、
、Ｒ９中に存在する不斉炭素の絶対配置か同一であるも
のを挙げることができる。The following margin = 4- Table 1 I'(,,r(,) constituting the ester compound of the present invention, more specifically, R, is C1H2L+l・CH(CH2)n --=(
N) SaR3 (1fm, 2≦Q, j≦8), and ka-J R,
, those in which the absolute configuration of the asymmetric carbon atoms present in R9 are the same can be mentioned.
中でも、０≦ｎ、ｍ≦８であるような基が特に好適に用
いられる。Among these, groups satisfying 0≦n and m≦8 are particularly preferably used.
「製造方法廖
次に、本発明のエステル化合物の製造方法の一例を説明
する。``Manufacturing method'' Next, an example of the manufacturing method of the ester compound of the present invention will be explained.
本発明のエステル化合物は、下記中間体（Ｂ）をトルエ
ンに溶解し、ピリジン存在下で下記中間体（Ａ）を作用
させろことによって製造できる。The ester compound of the present invention can be produced by dissolving the following intermediate (B) in toluene and reacting the following intermediate (A) in the presence of pyridine.
Ｒ−◎−Ｃα 川・（Ａ） ＨＯ−◎−０Ｒ２−・・・（Ｂ） また、中間体（Ａ）は、次のような工程で製造できる。R-◎-Cα River (A) HO-◎-0R2-...(B) Moreover, the intermediate (A) can be manufactured by the following steps.
以下余白
５ アルコ−Ｌ＋シルエステルＲ，ＯＴｓ −−−
−（Ａ−２）さらに、中間体（Ｂ）は、次のような工程
で製造できる。Below margin 5 Alco-L + Silester R, OTs ---
-(A-2) Furthermore, the intermediate (B) can be produced by the following steps.
「実施例」
次に、実施例に沿って本発明のエステル化合物を更に詳
しく説明する。"Example" Next, the ester compound of the present invention will be described in more detail with reference to Examples.
（実施例Ｉ） （Ｖｌ）式で表されろ本発明の液晶化合物を作成した。(Example I) A liquid crystal compound of the present invention represented by the formula (Vl) was prepared.
なお、以下の式に添えた（Ｓ）および（Ｒ）の記号は、
その側鎖の部分を絶対配置Ｓ型あるいはＲ型の原料アル
コールによって合成したことを示す。In addition, the symbols (S) and (R) added to the following formula are:
This indicates that the side chain portion was synthesized using a raw material alcohol with an absolute configuration of S type or R type.
この化合物（Ｖｌ）は次のように製造した。This compound (Vl) was produced as follows.
まず、（Ｃ）式に示す市販の光学活性アミルアルコール
（絶対配置Ｓ型）を当量の塩化トシルと、２．５倍当量
のピリジン存在下で反応させた。First, a commercially available optically active amyl alcohol (absolute configuration S type) shown by formula (C) was reacted with an equivalent amount of tosyl chloride in the presence of 2.5 times equivalent amount of pyridine.
ＣＨ３
Ｃ２Ｈ５ＣＨ（ＣＨ２）４０Ｈ・・・・（Ｃ）反応は室
温以下で行い、約８時間を要した。得られた溶液から、
トルエン抽出の後、６Ｎ−ＨＯθ、２Ｎ−ＮａＯＨ１水
を順次用いて洗浄し、次いで無水硫酸マグネシウムを用
いて乾燥した後、トルエンを溜去し、前記（Ａ−２）式
に相当するトシルエステルを得た。収率は約９０％であ
った。CH3C2H5CH(CH2)40H...(C) The reaction was carried out below room temperature and required about 8 hours. From the resulting solution,
After toluene extraction, the tosyl ester corresponding to the formula (A-2) was washed by washing with 6N-HOθ and 2N-NaOH1 water in sequence, and then drying with anhydrous magnesium sulfate, and distilling off the toluene. Obtained. The yield was about 90%.
次に、この得られたトシルエステルを、当量のＰ〜シア
ノフェノールとＩ １倍当量の苛性ソーダが存在するエ
タノール中に添加した。これを、還流温度にて十分攪拌
しなから、約２４時間反応さＵ°八。ついで、得られた
反応液を室温にもどし、エタノールを溜去した後、トル
エン抽出した。次に、これを６ Ｎ −ＨＣＱ、 ２
Ｎ−Ｎａ０ Ｈ，水の順次用いて洗浄し、無水硫酸マ
グネ７ウムで乾燥させた。その後、トルエンを溜去し、
エタノールから再結晶して、前記（Ａ −４）式に相当
するシアノ化合物を得た。収率は８５％であった。The obtained tosyl ester was then added to ethanol in the presence of equivalents of P-cyanophenol and 1 equivalent of caustic soda. This was stirred thoroughly at reflux temperature and reacted for about 24 hours. Then, the resulting reaction solution was returned to room temperature, ethanol was distilled off, and then extracted with toluene. Next, this is 6N-HCQ, 2
It was washed successively with N-Na0H and water, and dried over anhydrous magnesium sulfate. After that, toluene was distilled off,
Recrystallization from ethanol gave a cyano compound corresponding to the formula (A-4). The yield was 85%.
次に、水／エタノール−１／１（体積比）の混合溶媒に
ｌＯ倍当世の苛性ソーダを溶解し、この溶液に、得られ
た前記シアノ化合物を当量溶解し、約３日間還流した。Next, 10 times the amount of caustic soda was dissolved in a mixed solvent of water/ethanol-1/1 (volume ratio), and an equivalent amount of the obtained cyano compound was dissolved in this solution, followed by refluxing for about 3 days.
アンモニアガスの発生が終了してから、反応液を室温に
戻しこれを大量の冷水中に注ぎ、塩酸で酸性にしたとこ
ろ、大量の結晶が析出した。これを１戸数し、エタノー
ルから再結晶して、前記（Ａ−５）式に相当ずろカルボ
ン酸化合物を得た。収率は約８０％であった。次に、こ
のものに４倍当量の塩化チオニルを加え、４時間の加熱
還流を行い、余分な５ＯＣＱを溜去して、前記中間体（
Ａ）に相当する化合物（Ｄ）を得た。After the generation of ammonia gas was completed, the reaction solution was returned to room temperature, poured into a large amount of cold water, and made acidic with hydrochloric acid, resulting in the precipitation of a large amount of crystals. This was separated into several units and recrystallized from ethanol to obtain a carboxylic acid compound corresponding to the formula (A-5). The yield was about 80%. Next, 4 times the equivalent of thionyl chloride was added to this, heated under reflux for 4 hours, excess 5OCQ was distilled off, and the intermediate (
A compound (D) corresponding to A) was obtained.
１ｌ−
（Ｓ−４°−５−メチルへキンルオキシ安息香酸クロリ
ド）
一方、絶対配置Ｓ型の市販光学活性アミルアルコール（
Ｅ）を、当量の三臭化リン（Ｐ Ｂ ｒ３）で処理して
アミルブロマイドを合成し、このアミルブロマイドから
グリニヤール試薬を調整し、これにオキセタンを作用さ
せて前記（Ｂ−１）式に相当する化合物を得た。1l- (S-4°-5-Methylhekynyloxybenzoic acid chloride) On the other hand, commercially available optically active amyl alcohol with absolute configuration S type (
E) is treated with an equivalent amount of phosphorus tribromide (P B r3) to synthesize amyl bromide, prepare a Grignard reagent from this amyl bromide, and react with oxetane to obtain the formula (B-1) above. The corresponding compound was obtained.
次に、前記化合物（Ｄ）の場合と同様の操作で、１ｉｉ
ｊ記（Ｂ−２）式に相当するトシルエステルを調整した
。次に、このトシルエステルを１．１倍当量の苛性ソー
ダと当量のハイドロキノンが添加されたエタノール溶液
中に加熱攪拌しながら添加した。Next, in the same manner as in the case of compound (D), 1ii
A tosyl ester corresponding to formula (B-2) was prepared. Next, this tosyl ester was added to an ethanol solution containing 1.1 equivalents of caustic soda and an equivalent amount of hydroquinone while stirring while heating.
その後、還流下で約２日間反応させ、次いてエタノール
を溜去した後、酸性下でトルエン抽出し、この抽出物を
水洗して、前記中間体（Ｂ）に相当する化合物（Ｐ）を
得た。Thereafter, the reaction was carried out for about 2 days under reflux, and then ethanol was distilled off, followed by extraction with toluene under acidic conditions, and this extract was washed with water to obtain compound (P) corresponding to the intermediate (B). Ta.
次に、トルエン中、２倍当量のピリジン存在下で、中間
体（Ｂ）に相当する化合物（Ｆ）を当量溶解し、次いで
これに徐々に中間体（Ａ）に相当する化合物（Ｄ）を添
加し、還流攪拌を約８時間行った後、反応液を室温に戻
した。次いてこの反応液を、トルエン抽出に供し、続い
て６Ｎ−ＨＣｌ２．２Ｎ−ＮａＯＨ１水を順次用いて洗
浄した。 このものを、無水硫酸マグネシウムで乾燥し
た後、トルエンを溜去し、次いでエタノールから再結晶
した。得られた結晶をｎ−ヘキサン／クロロホルム＝９
／１の混合溶媒と、シリカゲルカラムを用いたカラムク
ロマトグラフィーによって精製し、次いて、エタノール
で３回再結晶を行い、前記エステル化合物（Ｖｌ）を得
た。このものは純白であった。Next, an equivalent amount of compound (F) corresponding to intermediate (B) was dissolved in toluene in the presence of two equivalents of pyridine, and then compound (D) corresponding to intermediate (A) was gradually added thereto. After addition and stirring under reflux for about 8 hours, the reaction solution was returned to room temperature. Next, this reaction solution was subjected to toluene extraction, and then washed with 6N-HCl2.2N-NaOH1 water in sequence. This product was dried over anhydrous magnesium sulfate, toluene was distilled off, and then recrystallized from ethanol. The obtained crystals were mixed with n-hexane/chloroform = 9
The product was purified by column chromatography using a silica gel column and a mixed solvent of 1/1, and then recrystallized three times with ethanol to obtain the ester compound (Vl). This one was pure white.
以上の操作によって製造されたエステル化合物（■）と
、−Ｆ記（ｃ ）（１−１）（Ｊ ）式で表される従来
の液晶化合物（比較例１〜３）の相転位温度、らせんピ
、ソチおよび自発分極を調べた。The phase transition temperature, helical The P, Sochi and spontaneous polarizations were investigated.
（Ｒ）（Ｓ）
（Ｓ）
第２表
注／ ピッチ：Ｓｃ＊上限温度よりも１０℃下の温度
で測定（以下の実施例において同様）。(R) (S) (S) Table 2 Note/ Pitch: Sc* Measured at a temperature 10°C lower than the upper limit temperature (same in the following examples).
自発分極、最大値（以下の実施例において同様）。Spontaneous polarization, maximum value (same in the following examples).
以」−の結果から、実施例１のエステル化合物（Ｖｌ）
は従来のものに比較してらせんピッチが長いことか判明
した。From the results below, the ester compound (Vl) of Example 1
It was found that the helical pitch was longer than that of the conventional one.
これは、化合物（Ｖｌ）においては、一方の側鎖がマイ
ナス方向の自発分極と右巻きのらせんのねじれを誘起す
るものであり、他方の側鎖がマイナス方向の自発分極を
左巻きのらせんのねじれを誘起するものであるためと考
えられる。This is because in compound (Vl), one side chain induces negative spontaneous polarization and right-handed helical twist, and the other side chain induces negative spontaneous polarization and left-handed helical twist. This is thought to be because it induces
これに対して、比較例１の化合物（Ｇ）は、らせんのピ
ッチが短く、また自発分極も小であった。On the other hand, the compound (G) of Comparative Example 1 had a short helical pitch and a small spontaneous polarization.
これは、化合物（Ｇ）の左側の側鎖が、左回りのらせん
のねじれとプラス方向の自発分極を誘起する光学活性基
からなり、右側の側鎖が左回りのらせんのねしれとマイ
ナス方向の自発分極を誘起ずろ光学活性基からなるため
と思われる。This is because the left side chain of compound (G) consists of an optically active group that induces counterclockwise helical twist and positive spontaneous polarization, and the right side chain induces counterclockwise helical twist and negative direction. This is thought to be because it consists of an optically active group that induces spontaneous polarization.
−１５＝
続いて、この実施例Ｉの化合物（Ｖｌ）を質量分析法と
赤外線吸収スペクトルで調べた。結果を第２図および第
３図に示す。第３図において、各ピークの波数は第３表
の通りである。-15= Subsequently, the compound (Vl) of Example I was examined by mass spectrometry and infrared absorption spectroscopy. The results are shown in FIGS. 2 and 3. In FIG. 3, the wave numbers of each peak are as shown in Table 3.
これらの結果から、この化合物（Ｖｌ）は、上記（Ｖｌ
）式の構造のものであることを確認できた。From these results, this compound (Vl) is the same as the above (Vl
) was confirmed to have the structure of the formula.
第３表 （実施例２〜４） 化合物（■）、（■）、（ＩＸ）を合成した。Table 3 (Examples 2 to 4) Compounds (■), (■), and (IX) were synthesized.
ｊＬ（−）／石（−）
左（−）／ｊｏ＋−）
これらの化合物（■）、（■）、（ＩＸ）の調べたとこ
ろ、化合物（■）、（■）はらせんピッチが５μｍ以上
、自発分極が４０ ｎＣ／ｃｍ’てあった。これら化合
物（■）。jL(-)/Stone(-) Left(-)/jo+-) When we investigated these compounds (■), (■), and (IX), we found that compounds (■) and (■) have a helical pitch of 5 μm or more. , the spontaneous polarization was 40 nC/cm'. These compounds (■).
（■）のＳｃ＊相はモノトロピックであった。The Sc* phase in (■) was monotropic.
他方、化合物（ＩＸ）は、前記実施例１の化合物（ＶＩ
）と略同−のＳｃ＊相を持ち、らせんピッチおよび自発
分極も略同程度の値であった。On the other hand, compound (IX) is the compound (VI
), and the helical pitch and spontaneous polarization were also approximately the same.
「発明の効果」
本発明のエステル化合物は、互いに異なる不斉構造を有
する光学活性基が骨格部の両端に結合されたものなので
、らせんピッチが長い液晶化合物となる。"Effects of the Invention" Since the ester compound of the present invention has optically active groups having mutually different asymmetric structures bonded to both ends of the skeleton, it becomes a liquid crystal compound with a long helical pitch.
従って、本発明のエステル化合物を用いることによって
、液晶表示素子の生産性を向上することができ、また液
晶表示素子の配向性等の表示特性を向上できる。Therefore, by using the ester compound of the present invention, productivity of liquid crystal display elements can be improved, and display characteristics such as orientation of the liquid crystal display element can be improved.
Claims (4)
造を持つアルキル基またはその誘導体を示す）で表され
るエステル化合物。(1) General formula▲There are mathematical formulas, chemical formulas, tables, etc.▼・・・(I) (In the formula (I), R_1 and R_2 represent alkyl groups or derivatives thereof that have different asymmetric structures.) ester compound.
す液晶性化合物において、互いに同じ自発分極の向きと
異なるらせんのねじれ方向を誘起するものであることを
特徴とする特許請求の範囲第１項記載のエステル化合物
。 ▲数式、化学式、表等があります▼・・・（II） ▲数式、化学式、表等があります▼・・・・（III） （（II）式、（III）式中Ｒは、不斉構造を持たないア
ルキル基を示す）(2) A patent claim characterized in that R_1 and R_2 induce the same direction of spontaneous polarization and different helical twist directions in the liquid crystalline compounds represented by formulas (II) and (III). Ester compound according to scope 1. ▲There are mathematical formulas, chemical formulas, tables, etc.▼...(II) ▲There are mathematical formulas, chemical formulas, tables, etc.▼...(III) (R in formulas (II) and (III) is an asymmetric structure (indicates an alkyl group without)
・・（IV） Ｒ＿２が▲数式、化学式、表等があります▼・・・・（
Ｖ） （但し、ｎ≠ｍ、２≦ｌ、ｊ≦８）であり、かつＲ＿１
、Ｒ＿２中に存在する不斉炭素の絶対配置が同一である
ことを特徴とする特許請求の範囲第２項記載のエステル
化合物。(3) R_1 has ▲ mathematical formulas, chemical formulas, tables, etc. ▼...
...(IV) R_2 is ▲There are mathematical formulas, chemical formulas, tables, etc.▼...(
V) (however, n≠m, 2≦l, j≦8), and R_1
The ester compound according to claim 2, wherein the asymmetric carbon atoms present in R_2 have the same absolute configuration.
の範囲第３項記載のエステル化合物。(4) The ester compound according to claim 3, wherein 0≦n and m≦8.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62149602A JPH07116108B2 (en) | 1987-06-16 | 1987-06-16 | Ester compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62149602A JPH07116108B2 (en) | 1987-06-16 | 1987-06-16 | Ester compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63313751A true JPS63313751A (en) | 1988-12-21 |
| JPH07116108B2 JPH07116108B2 (en) | 1995-12-13 |
Family
ID=15478792
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62149602A Expired - Lifetime JPH07116108B2 (en) | 1987-06-16 | 1987-06-16 | Ester compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH07116108B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6442454A (en) * | 1987-08-07 | 1989-02-14 | Dainippon Ink & Chemicals | Novel optically active compound |
-
1987
- 1987-06-16 JP JP62149602A patent/JPH07116108B2/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6442454A (en) * | 1987-08-07 | 1989-02-14 | Dainippon Ink & Chemicals | Novel optically active compound |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH07116108B2 (en) | 1995-12-13 |
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