JPH03109356A - Ester derivative - Google Patents
Ester derivativeInfo
- Publication number
- JPH03109356A JPH03109356A JP22649389A JP22649389A JPH03109356A JP H03109356 A JPH03109356 A JP H03109356A JP 22649389 A JP22649389 A JP 22649389A JP 22649389 A JP22649389 A JP 22649389A JP H03109356 A JPH03109356 A JP H03109356A
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- formula
- ester derivative
- ferroelectric liquid
- 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
- 150000002148 esters Chemical class 0.000 title claims abstract description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
- 229910052799 carbon Inorganic materials 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 abstract description 20
- 239000004973 liquid crystal related substance Substances 0.000 abstract description 16
- 239000005262 ferroelectric liquid crystals (FLCs) Substances 0.000 abstract description 12
- 230000003287 optical effect Effects 0.000 abstract description 5
- 230000001747 exhibiting effect Effects 0.000 abstract description 3
- 239000000463 material Substances 0.000 abstract description 3
- 230000010287 polarization Effects 0.000 abstract description 2
- 230000002269 spontaneous effect Effects 0.000 abstract description 2
- 239000007788 liquid Substances 0.000 abstract 1
- 230000009466 transformation Effects 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- -1 n-octyl Chemical group 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- 239000004990 Smectic liquid crystal Substances 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000004020 conductor Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-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
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- PPQAGRXNKROYIP-UHFFFAOYSA-N 1-methyl-2-phenyl-3-propylindole Chemical compound CN1C2=CC=CC=C2C(CCC)=C1C1=CC=CC=C1 PPQAGRXNKROYIP-UHFFFAOYSA-N 0.000 description 1
- YXBOJGHBKKAPOG-UHFFFAOYSA-N 4-octoxybenzoyl chloride Chemical compound CCCCCCCCOC1=CC=C(C(Cl)=O)C=C1 YXBOJGHBKKAPOG-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 239000004988 Nematic liquid crystal Substances 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000005337 azoxy group Chemical group [N+]([O-])(=N*)* 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- IGARGHRYKHJQSM-UHFFFAOYSA-N cyclohexylbenzene Chemical compound C1CCCCC1C1=CC=CC=C1 IGARGHRYKHJQSM-UHFFFAOYSA-N 0.000 description 1
- WVIIMZNLDWSIRH-UHFFFAOYSA-N cyclohexylcyclohexane Chemical compound C1CCCCC1C1CCCCC1 WVIIMZNLDWSIRH-UHFFFAOYSA-N 0.000 description 1
- NLUNLVTVUDIHFE-UHFFFAOYSA-N cyclooctylcyclooctane Chemical compound C1CCCCCCC1C1CCCCCCC1 NLUNLVTVUDIHFE-UHFFFAOYSA-N 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- 230000005621 ferroelectricity Effects 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003935 n-pentoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000010409 thin film Substances 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］
本発明は新規な光学活性エステル誘導体に関するもので
あり、詳しくは液晶化合物又は液晶組成物の成分として
有用な光学活性エステル誘導体に関するものである。DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to a novel optically active ester derivative, and more particularly to an optically active ester derivative useful as a component of a liquid crystal compound or a liquid crystal composition.
［従来の技術］
液晶化合物が電気光学表示装置に利用されて以来、数多
くの液晶化合物が合成され、ネマチック液晶又はネマチ
ック−コレステリンク液晶が、ねじれネマチックモード
表示素子、コレステリック−ネマチック相転移現象利用
表示素子又はゲスト・ホスト効果利用表示素子等に広く
利用されている。[Prior Art] Since liquid crystal compounds were used in electro-optical display devices, many liquid crystal compounds have been synthesized, including nematic liquid crystals or nematic-cholesterlink liquid crystals, twisted nematic mode display elements, and displays using cholesteric-nematic phase transition phenomena. It is widely used in display elements or display elements using guest-host effects.
しかし、これらの表示素子の応答速度は最高でも数ｍ５
ｅｃのオーダーであり、この点が液晶表示素子の応用範
囲をせばめる一因となっている。However, the response speed of these display elements is several meters at most.
It is on the order of ec, and this point is one of the reasons for narrowing the range of applications of liquid crystal display elements.
これに対して、強誘電性を示す液晶即ち強誘電性液晶を
用いると、μｓｅｃオーダーの高速で応答が得られると
いうことが最近になって確認された。On the other hand, it has recently been confirmed that when a liquid crystal exhibiting ferroelectric properties, that is, a ferroelectric liquid crystal, is used, a response can be obtained at a high speed on the order of μsec.
従来知られている強誘電性液晶の例としては、１９７５
年にＲ，Ｂ、Ｍｅｙｅｒらにより合成された４−（４’
−ｎ−デシルオキシベンジリデンアミノ）ケイ皮酸−２
−メチルブチルエステル（以下、ｒＤＯＢＡＭＢｃＪと
記す、）が挙げられる。ＤＯＢＡＭＢＣは、そのカイラ
ルスメクチックＣ相において強誘電性を示すことを特徴
としている（、Ｊ、Ｐｈｙｓｉｑｕｅ、３６Ｌ−６９（
１９７５））。An example of a conventionally known ferroelectric liquid crystal is the 1975
4-(4'
-n-decyloxybenzylidene amino)cinnamic acid-2
-Methyl butyl ester (hereinafter referred to as rDOBAMBcJ). DOBAMBC is characterized by exhibiting ferroelectricity in its chiral smectic C phase (J, Physique, 36L-69(
1975)).
そして、１９８０年にＮ、Ａ、Ｃ１ａｒｋらがＤｏ Ｂ
ＡＭＢＣを使用した薄膜セルにおいてμｓｅｃオーダー
の高速応答が得られることを見出して以来（Ａｐｐｌ、
Ｐｈｙｓ、Ｌｅｔｔ。Then, in 1980, N, A, C1ark, etc.
Since discovering that a high-speed response on the μsec order can be obtained in a thin film cell using AMBC (Appl.
Phys, Lett.
１至 ８９ （１９８０））、多くの強誘電性液晶の合
成研究がなされて来た。1 to 89 (1980)), many studies have been conducted on the synthesis of ferroelectric liquid crystals.
［発明が解決しようとする課題］
しかしながら、現在において
■ 室温で液晶状態であるのは勿論のこと、低温から高
温までのできるだけ広い範囲で強誘電性液晶状態を示す
。[Problems to be Solved by the Invention] However, at present, (1) It is not only a liquid crystal state at room temperature, but also a ferroelectric liquid crystal state in the widest possible range from low temperatures to high temperatures.
■ 水分、空気、光、熱等に対して安定である。■ Stable against moisture, air, light, heat, etc.
■ 自発分極が大きく低粘性である。■ Large spontaneous polarization and low viscosity.
■ 応答速度が速い。■ Fast response speed.
■ 駆動電圧が低い。■ Drive voltage is low.
等の要求特性の全てを単一化合物で満たす強誘電性液晶
化合物はなく、何種類かの強誘電性液晶化合物を組み合
せた組成物として強誘電性液晶表示素子に使用すること
によって目的を達しているのが現状である。There is no single ferroelectric liquid crystal compound that satisfies all of these required properties, but the purpose can be achieved by using a composition that combines several types of ferroelectric liquid crystal compounds in ferroelectric liquid crystal display elements. The current situation is that
本発明は上記従来の問題点を解決し、強誘電性液晶表示
素子の材料として好適な、上記■〜■の要求特性を十分
に満たす新規光学活性エステル誘導体を提供することを
目的とする。It is an object of the present invention to solve the above-mentioned conventional problems and to provide a novel optically active ester derivative which is suitable as a material for a ferroelectric liquid crystal display element and sufficiently satisfies the required properties (1) to (4) above.
［課題を解決するための手段］
本発明は、一般式［ＩＩ
・・−［Ｉコ
で表わされる光学活性エステル誘導体を要旨とするもの
である。[Means for Solving the Problems] The gist of the present invention is an optically active ester derivative represented by the general formula [II...-[I].
以下に本発明の詳細な説明する。The present invention will be explained in detail below.
本発明のエステル話導体は、前記一般式［１］で表わさ
れ、［１１式中、Ｒ１及びＲ２で表わされるアルキル基
としては、炭素数２〜！８の直鎖又は分岐鎖状のアルキ
ル基が挙げられ、好ましくはｎ−プロピル、ｎ−ブチル
、５ｅｃ−ブチル、１ｓｏ−ブチル、ｎ−ペンチル、ｎ
−ヘキシル、ｎ−へブチル、ｎ−オクチル、ｎ−ノニル
、ｎ−デシル、ｎ−ウンデシル、ｎ−ドデシル等の炭素
数３〜１２のアルキル基が挙げられる。The ester conductor of the present invention is represented by the above-mentioned general formula [1], [In the formula (11), the alkyl group represented by R1 and R2 has 2 or more carbon atoms! 8 straight-chain or branched alkyl groups, preferably n-propyl, n-butyl, 5ec-butyl, 1so-butyl, n-pentyl, n-
Examples include alkyl groups having 3 to 12 carbon atoms such as -hexyl, n-hebutyl, n-octyl, n-nonyl, n-decyl, n-undecyl, and n-dodecyl.
また Ｒ１で表わされるアルコキシ基としては、炭素数
２〜１８の直鎖又は分岐鎖状のアルコキシ基が挙げられ
、好ましくはｎ−プロポキシ、ｎ−ブトキシ、５ｅｃ−
ブトキシ、１ｓｏ−ブトキシ、ｎ−ペンチルオキシ、ｎ
−へキシルオキシ、ｎ−へブチルオキシ、ｎ−オクチル
オキシ、ｎ−ノニルオキシ、ｎ−デシルオキシ、ｎ−ウ
ンデシルオキシ、ｎ−ドデシルオキシ等の炭素数３〜１
２のアルコキシ基が挙げられる。Further, the alkoxy group represented by R1 includes linear or branched alkoxy groups having 2 to 18 carbon atoms, preferably n-propoxy, n-butoxy, 5ec-
Butoxy, 1so-butoxy, n-pentyloxy, n
-C3 to 1 such as hexyloxy, n-hebutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, n-undecyloxy, n-dodecyloxy, etc.
2 alkoxy groups are mentioned.
本発明のエステル話導体は、例えば次の反応手順に従）
て合成することができる。The ester conductor of the present invention can be prepared, for example, according to the following reaction procedure)
It can be synthesized by
［ＩＩ ］
［ＩＩＩコ
［Ｖ］
［■コ
Ｒ’ ＋ｃｏ ｏ ＋ｃｏ Ｏ）ｌ
［ＶＴ］
Ｒ１＋Ｃ００＋Ｃ０ＣＲ・・・ＣＤ］
［■］
［■］
［ＩＶ］
（なお、一般式［■！］〜［■］中のＲ１及びＲ２は前
記一般式［Ｉ］におけると同意義を示す。）上記反応中
、［Ａ］、［Ｃ］及び［Ｅ］の反応は、例えば、ピリジ
ン中或いはジオキサン、テトラヒドロフラン等のエーテ
ル系溶媒又はベンゼン、トルエン等の芳香族炭化水素系
溶媒中において、ピリジン、キノリン、トリエチルアミ
ン、トリエチレンジアミン等のアミン系脱酸剤又は炭酸
ナトリウム、炭酸カリウム、重炭酸ナトリウム等の無機
系脱酸剤の存在下で、１０〜１５０℃の温度で反応させ
ることにより、実施することができる。[II] [III Co[V] [■CoR' +co o +co O)l [VT] R1+C00+C0CR...CD] [■] [■] [IV] (In addition, the general formula [■!] ~ [■ ], R1 and R2 have the same meanings as in the above general formula [I].) In the above reaction, the reactions of [A], [C] and [E] are carried out, for example, in pyridine or in dioxane, tetrahydrofuran, etc. In ether solvents or aromatic hydrocarbon solvents such as benzene and toluene, amine deoxidizers such as pyridine, quinoline, triethylamine, and triethylenediamine, or inorganic deoxidizers such as sodium carbonate, potassium carbonate, and sodium bicarbonate. It can be carried out by reacting in the presence of at a temperature of 10 to 150°C.
［Ｂ］の反応は、例えば、エチルエーテル、イソプロピ
ルエーテル、テトラヒドロフラン等のエーテル系溶媒中
、ブチルアミン等のアルキルアミンの存在下で５〜８０
℃の温度で反応させることにより実施することができる
。The reaction [B] is carried out, for example, in an ether solvent such as ethyl ether, isopropyl ether, or tetrahydrofuran in the presence of an alkylamine such as butylamine at a reaction rate of 5 to 80%.
It can be carried out by reacting at a temperature of °C.
ＣＤ］の反応は、例えば、塩化チオニル、塩化オキサリ
ル、五塩化リン等の塩素化剤を使用して５〜１００℃の
温度で反応させることにより実施することができる。CD] can be carried out, for example, by using a chlorinating agent such as thionyl chloride, oxalyl chloride, phosphorus pentachloride, etc. at a temperature of 5 to 100°C.
本発明のエステル話導体の具体例としては、例えば前記
一般式［Ｉ］中のＲＩ 、 Ｒ２が以下の第１表に示す
ものを挙げることができる。Specific examples of the ester conductor of the present invention include those in which RI and R2 in the general formula [I] are shown in Table 1 below.
第 １ 表 （その１）
第 １ 表 （その２）
第 １ 表 （その３）
このような本発明のエステル誘導体は、単独であっても
、それらの混合物であっても液晶化合物として用いるこ
とができる。Table 1 (Part 1) Table 1 (Part 2) Table 1 (Part 3) Such ester derivatives of the present invention can be used as a liquid crystal compound either alone or as a mixture thereof. can.
また、本発明のエステル誘導体は、適当な公知の液晶化
合物と組み合せて使用することもでき、本発明のエステ
ル誘導体を混合使用することにより高温部の液晶温度範
囲の広い液晶組成物を得ることができる。かかる公知の
液晶化合物としては、エステル系、ジエステル系、アゾ
キシ系、アゾ系、シッフ系、ピリミジン系、ビフェニル
系、フェニルシクロヘキサン系、シクロへキシルシクロ
ヘキサン系、ビシクロオクタン系、ジオキサン系、或い
は、ベンゼン環、シクロヘキサン環より成る多環化合物
系等が挙げられる。Furthermore, the ester derivative of the present invention can be used in combination with an appropriate known liquid crystal compound, and by mixing and using the ester derivative of the present invention, a liquid crystal composition with a wide liquid crystal temperature range in the high temperature region can be obtained. can. Such known liquid crystal compounds include ester type, diester type, azoxy type, azo type, Schiff type, pyrimidine type, biphenyl type, phenylcyclohexane type, cyclohexylcyclohexane type, bicyclooctane type, dioxane type, or benzene ring type. , a polycyclic compound system consisting of a cyclohexane ring, and the like.
更に、本発明のエステル誘導体により液晶組成物を形成
する場合、公知の二色性色素、光安定化剤或いは減粘剤
等の添加剤を併用することもできる。Furthermore, when a liquid crystal composition is formed using the ester derivative of the present invention, known additives such as dichroic dyes, light stabilizers, or viscosity reducers may also be used.
［作用］
前記一般式［Ｉ］で表わされるエステル誘導体によれば
、強屈電性液晶の要求特性を十分に満足する化合物が提
供される。[Function] The ester derivative represented by the general formula [I] provides a compound that fully satisfies the required characteristics of a ferroelectric liquid crystal.
［実施例］
次に、実施例を挙げて本発明をより具体的に説明するが
、本発明は、その要旨を超えない限り、以下の実施例に
限定されるものではない。[Examples] Next, the present invention will be described in more detail with reference to Examples, but the present invention is not limited to the following Examples unless it exceeds the gist thereof.
実施例１ 一般式［１１においてＲ’ ＝ＯＣａ Ｈ＋ｙ（ｎ）。Example 1 In the general formula [11, R'=OCaH+y(n).
Ｒ” ｅｃ６１（＋５（ｎ）で表わされる化合物（第１
表動、２４の化合物）の合成
（ｉ） （ｎ））Ｉ＋ｙＣａＯＶじｗ ｃ ｏ ｏ
＋ｃ ｏ ＯＨの合成４−ｎ−オクチルオキシ安息香酸
５．０ｇを塩化チオニル５０ｍｆ及び四塩化炭素５０ｍ
Ｊ２に溶解し、ＤＭＦ （ジメチルホルムアミド）を触
媒量加えた。４時間加熱還流した後、減圧下、溶媒を留
去して４−オクチルオキシ安息香酸塩化物を得た。R”ec61(+5(n) compound (first
Synthesis of 24 compounds) (i) (n)) I+yCaOVjiw c o o
Synthesis of +c o OH 5.0 g of 4-n-octyloxybenzoic acid was mixed with 50 mf of thionyl chloride and 50 mf of carbon tetrachloride.
It was dissolved in J2 and a catalytic amount of DMF (dimethylformamide) was added. After heating under reflux for 4 hours, the solvent was distilled off under reduced pressure to obtain 4-octyloxybenzoic acid chloride.
この塩化物全量をトルエン２５ｍ１に溶解した溶液を、
ｐ−ヒドロキシ安息香酸２．７６ｇをトルエン２５ｍｊ
ｌ及びピリジン５０ｍｊ！に溶解した溶液中に滴下した
。５０〜６０℃にて１１時間攪拌した後、溶媒を留去し
た。得られた残漬をエタノールから再結晶することによ
り、目的の下記式％式％
で表わされる化合物１．０３ｇを得た。A solution in which the entire amount of chloride was dissolved in 25 ml of toluene,
2.76 g of p-hydroxybenzoic acid and 25 mj of toluene
l and 50 mj of pyridine! was added dropwise into the solution. After stirring at 50 to 60°C for 11 hours, the solvent was distilled off. By recrystallizing the obtained residue from ethanol, 1.03 g of the desired compound represented by the following formula % was obtained.
の合成
（ｉ）で得られた化合物３２２ｍｇを塩化チオニル５ｍ
ｌと四塩化炭素５ｍｊ２に溶解し、触媒量のＤＭＦを加
えた。３時間加熱還流した後、減圧下、溶媒を留去して
塩化物を得た。322 mg of the compound obtained in synthesis (i) was mixed with 5 m of thionyl chloride.
1 and carbon tetrachloride were dissolved in 5 mj2 of carbon tetrachloride, and a catalytic amount of DMF was added. After heating under reflux for 3 hours, the solvent was distilled off under reduced pressure to obtain a chloride.
この塩化物全量をトルエン５ｍｊ！に溶解し、ｐ−ヒド
ロキシ安息香酸（１−トリフルオロメチルへブチル）エ
ステル（［α］：’＋４ａ、４ｓ。The total amount of this chloride is 5mj of toluene! Dissolved in p-hydroxybenzoic acid (1-trifluoromethylhebutyl) ester ([α]:'+4a, 4s.
（ｃｌ、３１．クロロホルム））をトルエン５ｍ２及び
ピリジン５ｍｉに溶解した溶液の中に滴下した。室温に
て１０時間攪拌した後、反応液を１０重量％塩酸４０ｍ
ｊｌ中に性別し、クロロホルム１００ｍｆＬにて抽出し
た。有機層を１０１ｉ量％塩酸、飽和炭酸水素ナトリウ
ム水溶液、飽和塩化ナトリウム水溶液にて順次洗浄した
後、無水硫酸ナトリウムにて乾燥した。溶媒を留去後、
シリカゲルカラムクロマトグラフィーにより精製して目
的の下記式
％式％
）
（）
また、このエステル誘導体は以下のような相転穆を示し
た。(cl, 31.chloroform)) was added dropwise into a solution of 5 m2 of toluene and 5 mi of pyridine. After stirring at room temperature for 10 hours, the reaction solution was diluted with 40 ml of 10% by weight hydrochloric acid.
The cells were sexed in Jl and extracted with 100 mfL of chloroform. The organic layer was washed successively with 101i% hydrochloric acid, a saturated aqueous sodium bicarbonate solution, and a saturated aqueous sodium chloride solution, and then dried over anhydrous sodium sulfate. After distilling off the solvent,
After purification by silica gel column chromatography, the desired compound was obtained using the following formula (%) (%) () Moreover, this ester derivative showed the following phase inversion.
で表わされる化合物１３７ｍｇを得た。137 mg of the compound represented by was obtained.
このエステル誘導体の分析結果は下記の通りであった。The analysis results of this ester derivative were as follows.
元素分析値（％）
Ｃ：８７．６９
Ｈ： ６．５７
（但し、Ｃｒｙは結晶相、５重は結晶に近いスメクチッ
ク相、Ｓｃ”はスメクチックｃ１相、ｓＡはスメクチッ
クＡ相を、Ｉｓｏは等方性液体を示す、）
実施例２〜６
実施例１と同様な方法により下記第２表に示すエステル
誘導体を合成した。その元素分析値を計算値と共に第２
表に示す。Elemental analysis value (%) C: 87.69 H: 6.57 (However, Cry is a crystalline phase, 5-fold is a smectic phase close to crystal, Sc" is a smectic c1 phase, sA is a smectic A phase, and Iso is an equal phase. Examples 2 to 6 The ester derivatives shown in Table 2 below were synthesized by the same method as in Example 1.The elemental analysis values are shown in Table 2 along with the calculated values.
Shown in the table.
第２表
得られたエステル誘導体は、いずれも良好な光学活性を
示すものであった。The ester derivatives obtained in Table 2 all exhibited good optical activity.
［発明の効果］
本発明で提供されるエステル誘導体は、強誘電性液晶表
示素子材料に要求される前記Φ〜■の特性を満たすもの
であって、液晶テレビ等のデイスプレィ、光プリンター
ヘッド、光フーリエ変換素子、ライトバルブ等に使用す
る強誘電性液晶化合物又は組成物用成分として極めて有
用である。[Effects of the Invention] The ester derivative provided by the present invention satisfies the above-mentioned properties of Φ to ■ required for ferroelectric liquid crystal display element materials, and is suitable for displays such as liquid crystal televisions, optical printer heads, and optical It is extremely useful as a component for ferroelectric liquid crystal compounds or compositions used in Fourier transform elements, light valves, etc.
Claims (1)
数２〜１８のアルコキシ基を示し、 Ｒ＾２は炭素数２〜１８のアルキル基を示し、Ｃ＾■は
不斉炭素原子を示す。］ で表わされる光学活性エステル誘導体。(1) General formula [I] ▲There are mathematical formulas, chemical formulas, tables, etc.▼... [I] [In the formula, R^1 is an alkyl group having 2 to 18 carbon atoms or an alkoxy group having 2 to 18 carbon atoms. , R^2 represents an alkyl group having 2 to 18 carbon atoms, and C^■ represents an asymmetric carbon atom. ] An optically active ester derivative represented by:
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1-139755 | 1989-06-01 | ||
| JP13975589 | 1989-06-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH03109356A true JPH03109356A (en) | 1991-05-09 |
Family
ID=15252634
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP22649389A Pending JPH03109356A (en) | 1989-06-01 | 1989-09-01 | Ester derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH03109356A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6159757A (en) * | 1997-12-16 | 2000-12-12 | Sharp Kabushiki Kaisha | Process for producing a solar battery and a sheet material for protective covering thereof |
-
1989
- 1989-09-01 JP JP22649389A patent/JPH03109356A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6159757A (en) * | 1997-12-16 | 2000-12-12 | Sharp Kabushiki Kaisha | Process for producing a solar battery and a sheet material for protective covering thereof |
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