JPH03287564A - Optically active compound and liquid crystal composition - Google Patents
Optically active compound and liquid crystal compositionInfo
- Publication number
- JPH03287564A JPH03287564A JP2089563A JP8956390A JPH03287564A JP H03287564 A JPH03287564 A JP H03287564A JP 2089563 A JP2089563 A JP 2089563A JP 8956390 A JP8956390 A JP 8956390A JP H03287564 A JPH03287564 A JP H03287564A
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- tables
- formulas
- optically active
- 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.)
- Pending
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 35
- 239000000203 mixture Substances 0.000 title claims abstract description 17
- 239000004973 liquid crystal related substance Substances 0.000 title claims description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 10
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 7
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims 12
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 abstract description 12
- 239000004988 Nematic liquid crystal Substances 0.000 abstract description 8
- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 abstract description 6
- LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 abstract description 4
- -1 diester compound Chemical class 0.000 abstract description 3
- 230000000704 physical effect Effects 0.000 abstract description 3
- UWCWUCKPEYNDNV-LBPRGKRZSA-N 2,6-dimethyl-n-[[(2s)-pyrrolidin-2-yl]methyl]aniline Chemical compound CC1=CC=CC(C)=C1NC[C@H]1NCCC1 UWCWUCKPEYNDNV-LBPRGKRZSA-N 0.000 abstract description 2
- GTCCGKPBSJZVRZ-WHFBIAKZSA-N (2s,4s)-pentane-2,4-diol Chemical compound C[C@H](O)C[C@H](C)O GTCCGKPBSJZVRZ-WHFBIAKZSA-N 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- LPNBBFKOUUSUDB-UHFFFAOYSA-M p-toluate Chemical compound CC1=CC=C(C([O-])=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-M 0.000 abstract 1
- GTCCGKPBSJZVRZ-UHFFFAOYSA-N pentane-2,4-diol Chemical compound CC(O)CC(C)O GTCCGKPBSJZVRZ-UHFFFAOYSA-N 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 5
- 238000012844 infrared spectroscopy analysis Methods 0.000 description 5
- 238000010898 silica gel chromatography Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000012265 solid product Substances 0.000 description 3
- SHSGDXCJYVZFTP-UHFFFAOYSA-N 4-ethoxybenzoic acid Chemical compound CCOC1=CC=C(C(O)=O)C=C1 SHSGDXCJYVZFTP-UHFFFAOYSA-N 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 125000004093 cyano group Chemical group *C#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
- 238000001914 filtration Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 239000012263 liquid product Substances 0.000 description 2
- PWIRSGZYRGXAQV-UHFFFAOYSA-N 4-(2-methylbutyl)aniline Chemical compound CCC(C)CC1=CC=C(N)C=C1 PWIRSGZYRGXAQV-UHFFFAOYSA-N 0.000 description 1
- YNBBQLUKHHSKPW-UHFFFAOYSA-N 4-(4-octoxyphenyl)benzoic acid Chemical compound C1=CC(OCCCCCCCC)=CC=C1C1=CC=C(C(O)=O)C=C1 YNBBQLUKHHSKPW-UHFFFAOYSA-N 0.000 description 1
- VACLULPMEXHBMD-UHFFFAOYSA-N 4-(4-propylcyclohexyl)benzoic acid Chemical compound C1CC(CCC)CCC1C1=CC=C(C(O)=O)C=C1 VACLULPMEXHBMD-UHFFFAOYSA-N 0.000 description 1
- WBUQBWQWNDKJJR-UHFFFAOYSA-N 4-[4-(2-methylbutoxy)phenyl]benzonitrile Chemical group C1=CC(OCC(C)CC)=CC=C1C1=CC=C(C#N)C=C1 WBUQBWQWNDKJJR-UHFFFAOYSA-N 0.000 description 1
- DNJQGRFZQMOYGM-UHFFFAOYSA-N 4-[4-(2-methylbutyl)phenyl]benzonitrile Chemical group C1=CC(CC(C)CC)=CC=C1C1=CC=C(C#N)C=C1 DNJQGRFZQMOYGM-UHFFFAOYSA-N 0.000 description 1
- QCNUKEGGHOLBES-UHFFFAOYSA-N 4-propylcyclohexane-1-carboxylic acid Chemical compound CCCC1CCC(C(O)=O)CC1 QCNUKEGGHOLBES-UHFFFAOYSA-N 0.000 description 1
- 239000004986 Cholesteric liquid crystals (ChLC) Substances 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 239000002262 Schiff base Substances 0.000 description 1
- 150000004753 Schiff bases Chemical class 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000003098 cholesteric effect Effects 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000005262 ferroelectric liquid crystals (FLCs) Substances 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
Landscapes
- Liquid Crystal Substances (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は特定の光学活性化合物に関し、詳しくは、光学
活性な２．４−ベンタンジオールのジエステル化合物お
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 [Field of Industrial Application] The present invention relates to a specific optically active compound, and more particularly to an optically active diester compound of 2,4-bentanediol and a liquid crystal composition containing the compound.
〔従来の技術および発明が解決しようとする課題〕液晶
は、種々の電気光学素子として応用され、時計、電卓、
自動車のパネル等の各種の表示に実用化されている。現
在実用化されている液晶表示素子は、ねじれネマチック
液晶やコレステリック液晶の誘電的配列効果を利用した
ものが大部分である。しかし、最近は他の方式の液晶表
示方法の開発も盛んに行われ、ＳＴＮ方式やコレステリ
ック・ネマチック相転移型表示方式等も用いられている
。[Prior art and problems to be solved by the invention] Liquid crystals are applied as various electro-optical elements, such as watches, calculators,
It has been put to practical use in various displays such as automobile panels. Most of the liquid crystal display elements currently in practical use utilize the dielectric alignment effect of twisted nematic liquid crystals and cholesteric liquid crystals. However, recently, other liquid crystal display methods have been actively developed, and STN methods, cholesteric nematic phase transition display methods, and the like are also being used.
これらの液晶表示素子に用いられる液晶組成物は、例え
ば、ｐ−アルコキシベンズアルデヒドと（＋）−ｐ−ア
ミノ−２−メチルブチルベンゼンから作られたシッフ塩
基型液晶のようにネマチック液晶に光学活性直換基を導
入するか、あるいは４−（２−メチルブトキシ）−４゛
−シアノビフェニル等の光学活性化合物を添加すること
によりそれぞれ所望のらせんピッチをもつように調整さ
れる。The liquid crystal compositions used in these liquid crystal display devices include nematic liquid crystals with direct optical activity, such as Schiff base liquid crystals made from p-alkoxybenzaldehyde and (+)-p-amino-2-methylbutylbenzene. The desired helical pitch can be adjusted by introducing a substituent or adding an optically active compound such as 4-(2-methylbutoxy)-4'-cyanobiphenyl.
これらの方法の内、光学活性化合物を添加する方法は、
その添加量を変えることにより、母液晶組成物の特性を
維持したままピッチを任意に変えることが可能であり、
好ましい方法である。Among these methods, the method of adding an optically active compound is
By changing the amount added, it is possible to arbitrarily change the pitch while maintaining the characteristics of the mother liquid crystal composition.
This is the preferred method.
しかしながら、これまで知られていた光学活性化合物は
液晶のねじりピッチが長いため、所望の物性を得るため
には多量の配合を必要としたり、温度変化に伴うピッチ
の変化が大きかったりする欠点があった。However, since the optically active compounds known so far have a long twist pitch in liquid crystal, they have the disadvantage that they require a large amount of compounding in order to obtain the desired physical properties, and the pitch changes greatly due to temperature changes. Ta.
また、特開平１−７５４４９号公報、特開平１−９６１
５３号公報、特開平１−１１３３４７号公報、特開平１
−２１３２４９号公報、特開平１−２４２５４２号公報
、特開平１−２５８６３５号公報等には光学活性な２．
４−ベンタンジオール誘導体が記載されているが、これ
らの公報に記載された化合物はモノエステルモノエーテ
ル化合物またはジエーテル化合物に限られ、しかも、上
記モノエステル化合物は強誘電性液晶化合物であること
が記載されているが、ネマチ・ンク液晶組成物に添加し
た場合に所望のピッチを与える効果を有するかどうかに
ついては全く記載されていない。Also, JP-A-1-75449, JP-A-1-961
No. 53, JP-A-1-113347, JP-A-1
-213249, JP-A-1-242542, JP-A-1-258635, etc. disclose optically active 2.
Although 4-bentanediol derivatives are described, the compounds described in these publications are limited to monoester monoether compounds or diether compounds, and furthermore, it is stated that the monoester compounds are ferroelectric liquid crystal compounds. However, there is no mention of whether or not it has the effect of imparting a desired pitch when added to a nematic liquid crystal composition.
本発明者等は、液晶表示素子用液晶組成物に所望のらせ
んピッチを与え、しかも、温度変化によるピッチの変化
の少ない光学活性化合物を見出すべく鋭意検討を重ねた
結果、次の一般式で表される新規な光学活性化合物が上
記の目的に使用するのに極めて好適な化合物であること
を見出した。The present inventors have conducted intensive studies to find an optically active compound that provides a desired helical pitch to a liquid crystal composition for liquid crystal display elements and that exhibits less change in pitch due to temperature changes. It has been found that the novel optically active compound described above is an extremely suitable compound for use for the above purpose.
々水素原子、炭素原子数１〜１２のアルキル基ま表され
る基を示し、ｍおよびｎは各々０または１を示し、＊は
不斉炭素原子を示す、）
上記−数式で表される本発明の化合物は、例えば、次の
式で表される化合物を包含する。each represents a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, m and n each represent 0 or 1, and * represents an asymmetric carbon atom) The compounds of the invention include, for example, compounds represented by the following formula.
υ
（式中、Ｒ３、Ｒ２及びＲ５は前記の意味を示す。）こ
れらの化合物において、Ｒ，およびＲ８で表される炭素
原子数１〜１２のアルキル基としては、メチル、エチル
、プロピル、ブチル、ペンチル、ヘキシル、ペプチル、
オクチル、デシル、ドデシル等があげられ、アルコキシ
基としては、上記のアルキル基から誘導されるアルコキ
シ基があげられる。υ (In the formula, R3, R2 and R5 have the above meanings.) In these compounds, the alkyl group having 1 to 12 carbon atoms represented by R and R8 includes methyl, ethyl, propyl, butyl. , pentyl, hexyl, peptyl,
Examples include octyl, decyl, dodecyl, etc., and examples of the alkoxy group include alkoxy groups derived from the above-mentioned alkyl groups.
本発明の化合物は、前記のごとく、ネマチック液晶組成
物に所望のらせんピッチを与えるいわゆるカイラル剤と
して有用であり、ネマチック液晶組成物（母液晶）に０
．１〜３０重量％混合することによって所望のピッチを
あたえることができる。As mentioned above, the compound of the present invention is useful as a so-called chiral agent that gives a desired helical pitch to a nematic liquid crystal composition,
．． A desired pitch can be achieved by mixing 1 to 30% by weight.
このネマチック液晶組成物を構成する液晶化合物として
は、これまで多数の化合物が知られており、本願発明の
光学活性２，４−ベンタンジオールジエステル化合物は
これらの任意の混合物に添加することができ、その種類
によって制限を受けるものではない。Many compounds have been known as liquid crystal compounds constituting this nematic liquid crystal composition, and the optically active 2,4-bentanediol diester compound of the present invention can be added to any mixture of these. It is not limited by its type.
以下に、液晶ａ放物に用いられるネマチック液晶化合物
の代表的な例を示す。Typical examples of nematic liquid crystal compounds used in liquid crystal a paraboloids are shown below.
（Ｒは炭素原子数１〜１８のアルキル基またはアルコキ
シ基を示し、Ｘは塩素原子、フッ素原子、炭素原子数１
〜１８のアルキル基またはアルコキシ基またはシアノ基
を示し、Ｙは水素原子、塩素原子、フッ素原子またはシ
アノ基を示し、ａは１または２を示し、ｂは０または１
を示し、Ｃは０または１を示す）
液晶混合物（母液晶）は、一般に、これらの化合物を数
種類以上組み合わせることによって調製され、この母液
晶に、本発明の光学活性２．４−ベンタンジオールジエ
ステル化合物を添加することによって所望のピッチを有
する液晶組成物が得られる。(R represents an alkyl group or an alkoxy group having 1 to 18 carbon atoms, and X is a chlorine atom, a fluorine atom, or a carbon atom
~18 alkyl group, alkoxy group, or cyano group, Y represents a hydrogen atom, chlorine atom, fluorine atom, or cyano group, a represents 1 or 2, and b represents 0 or 1
and C represents 0 or 1) A liquid crystal mixture (mother liquid crystal) is generally prepared by combining several or more of these compounds, and the optically active 2,4-bentanediol diester of the present invention is added to this mother liquid crystal. By adding the compound, a liquid crystal composition having a desired pitch can be obtained.
次に、本発明を実施例によってさらに詳細に説明するが
、本発明は以下の実施例によって制限を受けるものでは
ない。尚、各実施例中の構造式に実施例 １
性吸収を有しており、目的物であることを確認し・た。Next, the present invention will be explained in more detail with reference to examples, but the present invention is not limited by the following examples. It was confirmed that the structural formula in each Example had sexual absorption in Example 1, and that it was the desired product.
３０２５ｃｍ−’、２９７５ｃ＋ｎ−’ ２９２５ｃ
ｍ＋１７１ＯＣＲ＋−’ １６１０ｃｍ−’ １２
７０ｃｍ−菫１１０５ｃｍ−’、７４５ｃｍ−’、６８
５ｃｍ−’実施例 ２
４−メチル安息香酸３．２６ｇ、（Ｓ、５）−２，４−
ベンタンジオール１．０４ｇ及びトリフェニルホスフィ
ン６．２９ｇを乾燥ジエチルエーテル３０ｍに溶解し、
アゾジカルボン酸ジイソプロピルエステル４．８５ｇの
ジエチルエーテル溶液を滴下し、室温で３時間攪拌した
後ろ過し、ろ液を脱溶媒した。3025cm-', 2975c+n-' 2925c
m+171OCR+-'1610cm-' 12
70cm-Violet 1105cm-', 745cm-', 68
5cm-'Example 2 3.26g 4-methylbenzoic acid, (S,5)-2,4-
1.04 g of bentanediol and 6.29 g of triphenylphosphine were dissolved in 30 m of dry diethyl ether,
A solution of 4.85 g of azodicarboxylic acid diisopropyl ester in diethyl ether was added dropwise, stirred at room temperature for 3 hours, filtered, and the filtrate was desolvated.
得られた残留物をシリカゲルカラムクロマトグラフィー
を用い、ｎ−ヘキサン／酢酸エチル（３／１）を展開溶
媒として精製し、無色液体の生成物を得た。The obtained residue was purified using silica gel column chromatography using n-hexane/ethyl acetate (3/1) as a developing solvent to obtain a colorless liquid product.
赤外分光分析の結果、得られた生成物は次の特４−エト
キシ安息香酸０．８３ｇ、（Ｒ，Ｒ）−２，４−ベンタ
ンジオール０．２６ｇ及びトリフェニルホスフィン１．
４４ｇを乾燥ジエチルエーテル１０−に溶解し、アゾジ
カルボン酸ジイソプロピルエステル１．１１ｇのジエチ
ルエーテル溶液を滴下し、室温で３時間攪拌した後ろ過
し、ろ液を脱溶媒した。As a result of infrared spectroscopic analysis, the obtained products were as follows: 0.83 g of 4-ethoxybenzoic acid, 0.26 g of (R,R)-2,4-bentanediol, and 1.0 g of triphenylphosphine.
44 g was dissolved in dry diethyl ether 10-, and a diethyl ether solution of 1.11 g of azodicarboxylic acid diisopropyl ester was added dropwise, stirred at room temperature for 3 hours, filtered, and the filtrate was desolvated.
得られた残留物を、ｎ−ヘキサン／酢酸エチル（８５／
１５）を展開溶媒としてシリカゲルカラムクロマトグラ
フィーで精製し、融点１２５℃の白色固体の生成物を得
た。The obtained residue was dissolved in n-hexane/ethyl acetate (85/
15) was purified by silica gel column chromatography using a developing solvent to obtain a white solid product with a melting point of 125°C.
赤外分光分析の結果、得られた生成物は次の特性吸収を
有しており、目的物であることを確認した。As a result of infrared spectroscopic analysis, the obtained product had the following characteristic absorption, and was confirmed to be the desired product.
２９７８ｃ＋ｗ−’ １７０７ｃｍ−’
１６０９ｃｍ−’１２７４Ｃ＠−’ １２５８ＣＩＩ
−’ １１７０ＣＩ＋−’１１５９ｃｍ−’
１１１４ｃｍ−’ １０９４ｃｍ−’１０４０ｃ
ｍ−’、７６４ｃｍ−’
実施例 ３
溶解し、アゾジカルボン酸ジイソプロピルエステル３．
０３ｇのジエチルエーテル溶液を滴下し、室温で３時間
攪拌した後ろ遇し、ろ液を脱溶媒した。2978c+w-'1707cm-'
1609cm-'1274C@-' 1258CII
-'1170CI+-'1159cm-'
1114cm-'1094cm-'1040c
m-', 764 cm-' Example 3 Dissolve azodicarboxylic acid diisopropyl ester 3.
0.3 g of diethyl ether solution was added dropwise to the mixture, stirred at room temperature for 3 hours, and then the filtrate was desolvated.
得られた残留物をシリカゲルカラムクロマトグラフィー
を用い、ｎ−ヘキサン／酢酸エチル（９５１５）を展開
溶媒として精製し、無色液体の生成物を得た。The obtained residue was purified using silica gel column chromatography using n-hexane/ethyl acetate (9515) as a developing solvent to obtain a colorless liquid product.
赤外分光分析の結果、得られた生成物は次の特性吸収を
有しており、目的物であることを確認した。As a result of infrared spectroscopic analysis, the obtained product had the following characteristic absorption, and was confirmed to be the desired product.
２９３０ｃｍ−’、２８６０ｃｍ−’ １７３０
ｃｍ−’１４５０ｃｍ−’ １３８０ｃｍ−’ １
３１５ｃｍ−’１２６０ｃｍ−’ １１８０ｃｍ−’
１１４０ｃｍ−’実施例 ４
トランス−４−ｎ−プロピルシクロヘキサンカルボン酸
０．８５ｇ、（Ｒ，Ｒ）−２，４−ベンタンジオール０
．２６ｇ及びトリフェニルホスフィン３．９３ｇを乾燥
ジエチルエーテル１０ａｄ！に４− （４−ｎ−プロピ
ルシクロヘキシル）安息香酸１．４８ｇ、（Ｒ，Ｒ）−
２，４−ベンタンジオール０．２６ｇ及びトリフェニル
ホスフィン１．５７ｇを乾燥ジエチルエーテル１５ａ１
に溶解し、アゾジカルボン酸ジイソプロピルエステル１
゜２１ｇのジエチルエーテル溶液を滴下し、室温で３時
間攪拌した後ろ過し、ろ液を脱溶媒した。2930cm-', 2860cm-' 1730
cm-'1450cm-'1380cm-' 1
315cm-'1260cm-'1180cm-'
1140cm-'Example 4 Trans-4-n-propylcyclohexanecarboxylic acid 0.85g, (R,R)-2,4-bentanediol 0
．． 26 g and triphenylphosphine 3.93 g of dry diethyl ether 10 ad! to 1.48 g of 4-(4-n-propylcyclohexyl)benzoic acid, (R,R)-
0.26 g of 2,4-bentanediol and 1.57 g of triphenylphosphine were dissolved in dry diethyl ether 15a1.
Dissolved in azodicarboxylic acid diisopropyl ester 1
21 g of diethyl ether solution was added dropwise, stirred at room temperature for 3 hours, filtered, and the filtrate was desolvented.
得られた残留物をシリカゲルカラムクロマトグラフィー
を用い、ｎ−ヘキサン／酢酸エチル（３／１）を展開溶
媒として精製し、融点１３４．１°Ｃの白色固体の生成
物を得た。The obtained residue was purified using silica gel column chromatography using n-hexane/ethyl acetate (3/1) as a developing solvent to obtain a white solid product with a melting point of 134.1°C.
赤外分光分析の結果、得られた生成物は次の特性吸収を
有しており、目的物であることを確認した。As a result of infrared spectroscopic analysis, the obtained product had the following characteristic absorption, and was confirmed to be the desired product.
２９５０ｃ＊−’、 ２９２０ｃｍ−盲、 ２８５
０ｃｍ−’１７００ｃｍ−’ １６００ｃ＋＋＋−’
１２７０ｃｍ−’１１１０ｃｍ−’、７６０ｃｍ−
’、 ６８５ｃｍ−’実施例 ５
Ｓ Ｓ −２４−ペン フジイルビス４−ｎ−オク
トキシフェニル ベンゾニー生金底
４− （４−ｎ−オクトキシフェニル）安息香酸０．９
８ｇ、（Ｒ，Ｒ）−２，４−ベンタンジオール０．１６
ｇ及びトリフェニルホスフィン０゜４３ｇを乾燥ジエチ
ルエーテル１０Ｍ１に溶解し、アゾジカルボン酸ジイソ
プロピルエステル０．３３ｇのジエチルエーテル溶液を
滴下し、室温で３時間攪拌した。2950c*-', 2920cm-blind, 285
0cm-'1700cm-'1600c+++-'
1270cm-'1110cm-', 760cm-
', 685cm-'Example 5 S S -24-pen Fujiylbis4-n-octoxyphenyl Benzony raw metal bottom 4-(4-n-octoxyphenyl)benzoic acid 0.9
8g, (R,R)-2,4-bentanediol 0.16
g and triphenylphosphine (0.43 g) were dissolved in 10M1 of dry diethyl ether, and a solution of 0.33 g of azodicarboxylic acid diisopropyl ester in diethyl ether was added dropwise, followed by stirring at room temperature for 3 hours.
大量のｎ−へキサンを加えて生成した沈澱をろ過して集
め、メタノールを加えた。メタノール不溶物をろ過して
集め、ｎ−ヘキサン／酢酸エチル（７／３）を展開溶媒
としてシリカゲルカラムクロマトグラフィーで精製し、
融点１２２．５°Ｃの白色固体の生成物を得た。A large amount of n-hexane was added, a precipitate formed was collected by filtration, and methanol was added. Methanol insoluble matter was collected by filtration and purified by silica gel column chromatography using n-hexane/ethyl acetate (7/3) as a developing solvent.
A white solid product with a melting point of 122.5°C was obtained.
赤外分光分析の結果、得られた生成物は次の特性吸収を
有しており、目的物であることをｎＵ２した。As a result of infrared spectroscopic analysis, the obtained product had the following characteristic absorption, and was determined to be the desired product.
２９５２ｃｍ−’、２９２８ｃ＋ｓ−’、２８５２ｃｍ
−’１７０８ｃｓ＋−’ １６０４ｃｍ−’
１２９６ｃ＋＋−’１１９７ｃｍ−’ １０８８ｃ
ｍ−’、 ８２９ｃｍ−’７６５ｃｍ−’
実施例 ６
母液晶組成物として、代表的なネマチック液晶であるメ
ルク社製ＺＬＩ−１５６５を用い、これに本発明の化合
物または４−シアノ−４’ −（２−メチルブチル）ビ
フェニル（比較例化合物）を２重量％混合し、カッのク
サビ形セルを用い、３０°Ｃでのピッチ（μｍ）を測定
した。2952cm-', 2928c+s-', 2852cm
-'1708cs+-'1604cm-'
1296c++-'1197cm-' 1088c
m-', 829cm-'765cm-' Example 6 ZLI-1565 manufactured by Merck & Co., which is a typical nematic liquid crystal, was used as the mother liquid crystal composition, and the compound of the present invention or 4-cyano-4'-( 2-methylbutyl)biphenyl (comparative example compound) was mixed in an amount of 2% by weight, and the pitch (μm) at 30°C was measured using a wedge-shaped cell.
その結果を下の表−１に示す。The results are shown in Table 1 below.
表−１
実施例 ６
ピッチの温度依存性をみるために、実施例５と同様の液
晶組成物を用い、３０℃及び６０℃でのピッチを測定し
、その比率（Ｐｉ。／Ｐ３°）を求めた。Table 1 Example 6 In order to examine the temperature dependence of pitch, the same liquid crystal composition as in Example 5 was used, the pitch was measured at 30°C and 60°C, and the ratio (Pi./P3°) was calculated. I asked for it.
その結果を下の表−２に示す。The results are shown in Table 2 below.
表−２
〔発明の奏する効果〕
表−１の結果から、本発明の化合物が、液晶組成物に所
望のピッチを与えるカイラル化合物として極めて有用で
あることが明らかである。また、本発明の化合物は、従
来用いられていた代表的なカイラル化合物である４−シ
アノ−４°−（２メチルブチル）ビフェニルよりも短い
ピッチを与えるので、所望のピッチを得るために必要な
添加量が少ないことも明らかである。Table 2 [Effects of the Invention] From the results in Table 1, it is clear that the compound of the present invention is extremely useful as a chiral compound that provides a desired pitch to a liquid crystal composition. In addition, the compound of the present invention provides a shorter pitch than 4-cyano-4°-(2-methylbutyl)biphenyl, which is a typical chiral compound conventionally used, so additions necessary to obtain the desired pitch are required. It is also clear that the amount is small.
さらに、表−２の結果から、本発明の化合物を添加した
場合は、ピッチの温度依存性が小さく、広い温度範囲で
所期の物性を保持しえることも明らかである。Furthermore, from the results in Table 2, it is clear that when the compound of the present invention is added, the temperature dependence of the pitch is small and the desired physical properties can be maintained over a wide temperature range.
Claims (2)
化学式、表等があります▼、▲数式、化学式、表等があ
ります▼および▲数式、化学式、表等があります▼は各
々▲数式、化学式、表等があります▼または▲数式、化
学式、表等があります▼を示し、Ｒ＿１およびＲ＿３は
各々水素原子、炭素原子数１〜１２のアルキル基または
アルコキシ基を示し、Ｒ＿２は式▲数式、化学式、表等
があります▼で表される基を示し、ｍおよびｎは各々０
または１を示し、＊は不斉炭素原子を示す。）(1) An optically active compound represented by the following general formula. ▲There are mathematical formulas, chemical formulas, tables, etc.▼
There are chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ and ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ are respectively ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, R_1 and R_3 each represent a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, or an alkoxy group, R_2 represents a group represented by the formula ▲There are mathematical formulas, chemical formulas, tables, etc.▼, and m and n are each 0
or 1, * indicates an asymmetric carbon atom. )
も一種を含有する液晶組成物。 ▲数式、化学式、表等があります▼ （式中、▲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▼および▲数式、化学式、表等があります▼は各
々▲数式、化学式、表等があります▼または▲数式、化
学式、表等があります▼を示し、Ｒ＿１およびＲ＿３は
各々水素原子、炭素原子数１〜１２のアルキル基または
アルコキシ基を示し、Ｒ＿２は式▲数式、化学式、表等
があります▼で表される基を示し、ｍおよびｎは各々０
または１を示し、＊は不斉炭素原子を示す。）(2) A liquid crystal composition containing at least one optically active compound represented by the following general formula. ▲There are mathematical formulas, chemical formulas, tables, etc.▼
There are chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ and ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ are respectively ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, R_1 and R_3 each represent a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, or an alkoxy group, R_2 represents a group represented by the formula ▲There are mathematical formulas, chemical formulas, tables, etc.▼, and m and n are each 0
or 1, * indicates an asymmetric carbon atom. )
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2089563A JPH03287564A (en) | 1990-04-04 | 1990-04-04 | Optically active compound and liquid crystal composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2089563A JPH03287564A (en) | 1990-04-04 | 1990-04-04 | Optically active compound and liquid crystal composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH03287564A true JPH03287564A (en) | 1991-12-18 |
Family
ID=13974285
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2089563A Pending JPH03287564A (en) | 1990-04-04 | 1990-04-04 | Optically active compound and liquid crystal composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH03287564A (en) |
-
1990
- 1990-04-04 JP JP2089563A patent/JPH03287564A/en active Pending
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