JPH0543876A - Ferroelectric liquid crystal composition containing phenylcyclohexane derivative - Google Patents
Ferroelectric liquid crystal composition containing phenylcyclohexane derivativeInfo
- Publication number
- JPH0543876A JPH0543876A JP3200449A JP20044991A JPH0543876A JP H0543876 A JPH0543876 A JP H0543876A JP 3200449 A JP3200449 A JP 3200449A JP 20044991 A JP20044991 A JP 20044991A JP H0543876 A JPH0543876 A JP H0543876A
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- crystal composition
- phase
- compound
- formula
- 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.)
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Links
- 239000000203 mixture Substances 0.000 title claims abstract description 70
- 239000005262 ferroelectric liquid crystals (FLCs) Substances 0.000 title claims abstract description 28
- IGARGHRYKHJQSM-UHFFFAOYSA-N cyclohexylbenzene Chemical class C1CCCCC1C1=CC=CC=C1 IGARGHRYKHJQSM-UHFFFAOYSA-N 0.000 title 1
- 239000004973 liquid crystal related substance Substances 0.000 claims abstract description 82
- 150000001875 compounds Chemical class 0.000 claims abstract description 73
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 22
- 239000002019 doping agent Substances 0.000 claims abstract description 14
- 239000011159 matrix material Substances 0.000 claims abstract description 14
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 12
- 239000004990 Smectic liquid crystal Substances 0.000 claims abstract description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 26
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 4
- 239000000470 constituent Substances 0.000 claims description 4
- 230000004044 response Effects 0.000 abstract description 22
- 239000013078 crystal Substances 0.000 abstract description 3
- 239000012071 phase Substances 0.000 description 49
- 239000000126 substance Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 230000010287 polarization Effects 0.000 description 7
- 230000002269 spontaneous effect Effects 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 230000001747 exhibiting effect Effects 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- 239000004642 Polyimide Substances 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 229920001721 polyimide Polymers 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- FUQOYBLOENRXNS-UHFFFAOYSA-N 1-octoxy-4-(4-octylcyclohexen-1-yl)benzene Chemical compound C1=CC(OCCCCCCCC)=CC=C1C1=CCC(CCCCCCCC)CC1 FUQOYBLOENRXNS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000004988 Nematic liquid crystal Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000012769 display material Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 238000000819 phase cycle Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000004043 responsiveness Effects 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000006850 spacer group Chemical group 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- HCJHGEFNCWGEQR-UHFFFAOYSA-N 1-(4-octoxyphenyl)-4-octylcyclohexan-1-ol Chemical compound CCCCCCCCC1CCC(CC1)(C2=CC=C(C=C2)OCCCCCCCC)O HCJHGEFNCWGEQR-UHFFFAOYSA-N 0.000 description 1
- UVBFFPZGOOKWNR-UHFFFAOYSA-N 1-bromo-4-octoxybenzene Chemical compound CCCCCCCCOC1=CC=C(Br)C=C1 UVBFFPZGOOKWNR-UHFFFAOYSA-N 0.000 description 1
- WZASLAVKNZVYFL-UHFFFAOYSA-N 1-octoxy-4-(4-octylcyclohexyl)benzene Chemical compound CCCCCCCCC1CCC(CC1)C2=CC=C(C=C2)OCCCCCCCC WZASLAVKNZVYFL-UHFFFAOYSA-N 0.000 description 1
- PKOWPSHVZJGPOJ-UHFFFAOYSA-N 4-octylcyclohexan-1-one Chemical compound CCCCCCCCC1CCC(=O)CC1 PKOWPSHVZJGPOJ-UHFFFAOYSA-N 0.000 description 1
- IMJYZXBAEQPEFK-UHFFFAOYSA-N 4-octylcyclohexene Chemical compound C(CCCCCCC)C1CC=CCC1 IMJYZXBAEQPEFK-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 229920006332 epoxy adhesive Polymers 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 1
- 229910000343 potassium bisulfate Inorganic materials 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- -1 trans-1- (4-octyloxyphenyl) -4-octylcyclohexane Chemical compound 0.000 description 1
Landscapes
- Liquid Crystal Substances (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は電気光学的表示材料とし
て有用な強誘電性液晶組成物に関し、更に詳しくは、従
来の液晶材料と比較して、その応答性に優れ、液晶表示
素子の構成材料として有用な強誘電性液晶組成物を提供
するものである。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a ferroelectric liquid crystal composition useful as an electro-optical display material. A ferroelectric liquid crystal composition useful as a material is provided.
【０００２】[0002]
【従来の技術】現在広く用いられている液晶表示素子
は、主にネマチック液晶を利用したＴＮ（ツイスティッ
ド・ネマチック）型、あるいはＳＴＮ（スーパー・ツイ
スティッド・ネマチック）型と呼ばれるものであり、多
くの利点を有しているものの、その応答性においては、
ＣＲＴ等の発光型の表示方式と比較すると格段に遅いと
いう大きな欠点を有し、その応用に大きな制限があっ
た。その他の液晶表示方式も多方面から検討されている
が、その応答性における改善は余りなされていないのが
実情である。2. Description of the Related Art Liquid crystal display elements that are widely used at present are mainly called TN (Twisted Nematic) type or STN (Super Twisted Nematic) type using nematic liquid crystals. Although it has the advantage of, in its responsiveness,
It has a major drawback that it is much slower than a light emitting display method such as a CRT, and its application is greatly limited. Other liquid crystal display systems have been studied from various fields, but the reality is that the response has not been improved so much.
【０００３】ところが、最近見いだされた強誘電性キラ
ルスメクチック液晶を利用した液晶表示素子において
は、従来のＴＮ型などの液晶表示素子の１００倍以上の
高速応答が可能となった。更に双安定性を有するため、
電源を切っても表示の記憶が得られることが明らかにな
った。このため、大画面高解像度ディスプレイ、薄型テ
レビ、光シャッター、プリンターヘッド等への利用可能
性が大きく、現在、その実用化に向けて活発に開発研究
がなされている。However, the recently discovered liquid crystal display device using the ferroelectric chiral smectic liquid crystal has been capable of 100 times faster response than the conventional TN type liquid crystal display device. Furthermore, because it has bistability,
It became clear that the memory of the display can be obtained even when the power is turned off. Therefore, it is highly applicable to large-screen high-resolution displays, thin-screen TVs, optical shutters, printer heads, etc., and currently, active development and research is being conducted toward its practical application.
【０００４】強誘電性液晶の液晶相は、チルト系のキラ
ルスメクチック相に属するが、その中でも最も低粘性の
キラルスメクチックＣ（以下、ＳＣ*と省略する。）相
が実用上望ましい。既に数多くのＳＣ*相を示す液晶化
合物（以下、ＳＣ*化合物という。）が合成され、検討
されているが、強誘電性液晶表示用光スイッチング素子
として用いるのに十分な性質を有するものは未だ知られ
ていない。よって他の液晶化合物と混合して、ＳＣ*相
を示す液晶組成物（以下、ＳＣ*液晶組成物という。）
として用いられている。The liquid crystal phase of the ferroelectric liquid crystal belongs to the tilt type chiral smectic phase, but among them, the chiral smectic C (hereinafter abbreviated as SC * ) phase having the lowest viscosity is practically desirable. A large number of liquid crystal compounds exhibiting an SC * phase (hereinafter referred to as SC * compounds) have already been synthesized and studied, but none of them have properties sufficient for use as an optical switching element for a ferroelectric liquid crystal display. unknown. Therefore, a liquid crystal composition exhibiting an SC * phase when mixed with another liquid crystal compound (hereinafter referred to as SC * liquid crystal composition).
Is used as.
【０００５】このようなＳＣ*液晶組成物の検討は活発
に行われており、現在では、キラルでないスメクチック
Ｃ（以下、ＳＣと省略する。）相を示す母体液晶に、光
学活性化合物から成るキラルドーパントを添加する方法
が一般的である。これによって高速応答性、良好な配向
性、広い作動温度範囲等の特性を合わせ持つＳＣ*液晶
組成物が得られるようになってきた。Such an SC * liquid crystal composition has been actively studied, and at present, a chiral compound composed of an optically active compound is added to a matrix liquid crystal exhibiting a non-chiral smectic C (hereinafter abbreviated as SC) phase. A method of adding a dopant is common. This has made it possible to obtain SC * liquid crystal compositions having properties such as high-speed response, good orientation, and a wide operating temperature range.
【０００６】[0006]
【発明が解決しようとする課題】しかしながら、前記Ｓ
Ｃ*液晶組成物は、その応答性においてはまだ充分とは
いい難く、更に高速応答が望まれているのが実情であ
る。強誘電性液晶組成物の応答を高速化するには、液晶
組成物の自発分極を大きくするか、粘度を小さくする必
要があることは知られている。しかしながら、このうち
自発分極について、あまり大きくするとメモリー性等に
悪影響を与える傾向にあり、ある程度以上に自発分極を
大きくできないのが実情である。そこで液晶組成物の粘
度を小さくする必要があるが、そのためには前記ＳＣ*
液晶組成物の大部分を占める母体液晶の粘度を小さくす
ることが最も重要である。However, the above-mentioned S
It is difficult to say that the C * liquid crystal composition has sufficient responsiveness, and the fact is that a higher speed response is desired. It is known that in order to accelerate the response of the ferroelectric liquid crystal composition, it is necessary to increase the spontaneous polarization of the liquid crystal composition or reduce the viscosity thereof. However, of these, if the spontaneous polarization is too large, it tends to adversely affect the memory property and the like, and in reality, the spontaneous polarization cannot be increased beyond a certain level. Therefore, it is necessary to reduce the viscosity of the liquid crystal composition .
It is of utmost importance to reduce the viscosity of the base liquid crystal that occupies most of the liquid crystal composition.
【０００７】本発明が解決しようとする課題は、粘性の
小さい化合物を添加することによって得られた低粘性の
母体液晶、及び光学活性化合物から成るキラルドーパン
トを含有し、高速応答性、良好な配向性及び広い作動温
度範囲を有する強誘電性液晶組成物を提供することにあ
る。The problem to be solved by the present invention is to contain a low-viscosity host liquid crystal obtained by adding a compound having a low viscosity, and a chiral dopant composed of an optically active compound, and to provide high-speed response and good alignment. To provide a ferroelectric liquid crystal composition having properties and a wide operating temperature range.
【０００８】[0008]
【課題を解決するための手段】本発明は前記課題を解決
するために、下記の第１の強誘電性液晶組成物を提供す
る。In order to solve the above problems, the present invention provides the following first ferroelectric liquid crystal composition.
【０００９】即ち、一般式（Ｉ）That is, the general formula (I)
【００１０】[0010]
【化３】 [Chemical 3]
【００１１】（式中、Ｒ1及びＲ2は、各々独立的に炭素
原子数６〜１４の直鎖状アルキル基を表わす。）で表わ
される化合物を含有する強誘電性液晶組成物を提供す
る。A ferroelectric liquid crystal composition containing a compound represented by the formula: wherein R 1 and R 2 each independently represent a linear alkyl group having 6 to 14 carbon atoms. .
【００１２】更に、本発明は、下記の第２の強誘電性液
晶組成物を提供する。 即ち、（１）一般式（Ｉ）で表わされる化合物、及び
一般式（ＩＩ）Further, the present invention provides the following second ferroelectric liquid crystal composition. That is, (1) the compound represented by the general formula (I), and the general formula (II)
【００１３】[0013]
【化４】 [Chemical 4]
【００１４】（式中、Ｒ3及びＲ4の一方は炭素原子数４
〜１４のアルコキシル基又はアルケニルオキシ基を表わ
し、他方は炭素原子数４〜１４の直鎖状アルキル基を表
わす。）で表わされる化合物を含有し、スメクチックＣ
（ＳＣ）相を示す母体液晶、及び（２）光学活性化合物
から成るキラルドーパントを含有する強誘電性液晶組成
物を提供する。(In the formula, one of R 3 and R 4 has 4 carbon atoms.
Represents an alkoxyl group or an alkenyloxy group having 14 carbon atoms, and the other represents a linear alkyl group having 4 to 14 carbon atoms. ) Smectic C
Provided is a ferroelectric liquid crystal composition containing a matrix liquid crystal exhibiting a (SC) phase and (2) a chiral dopant composed of an optically active compound.
【００１５】特に、一般式（ＩＩ）において、Ｒ3が炭
素原子数６〜１２の直鎖状アルキル基であり、Ｒ4が炭
素原子数６〜１２の直鎖状アルコキシル基である化合物
を含有する上記の強誘電性液晶組成物が好ましい。In particular, in the general formula (II), R 3 is a straight-chain alkyl group having 6 to 12 carbon atoms, and R 4 is a straight-chain alkoxyl group having 6 to 12 carbon atoms. The above-mentioned ferroelectric liquid crystal composition is preferred.
【００１６】本発明において、一般式（Ｉ）で表わされ
る化合物は、非常に低粘性の化合物であり、母体液晶あ
るいは強誘電性液晶組成物に添加することにより、その
粘度を低下させ、応答性を大きく改善することができ
る。しかも、添加することによって、液晶組成物のＳＣ
*相（あるいはＳＣ相）の温度範囲を大きく低下させる
こともなく、実用性の高い組成物が得られる。In the present invention, the compound represented by the general formula (I) is an extremely low-viscosity compound, and when added to the matrix liquid crystal or the ferroelectric liquid crystal composition, its viscosity is lowered and the response is improved. Can be greatly improved. Moreover, when added, SC of the liquid crystal composition is added.
* A highly practical composition can be obtained without greatly reducing the temperature range of the phase (or SC phase).
【００１７】一般式（Ｉ）で表わされる化合物におい
て、Ｒ1及びＲ2共に炭素原子数１〜５程度の低級アルキ
ル基である場合には、従来のネマチック液晶化合物用と
して既に知られており、４−アルコキシ−１−ブロモベ
ンゼンから調製されたグリニヤール化合物と、４−アル
キルシクロヘキサノンとを反応させ、この反応生成物を
更に脱水し、得られた１−（４−アルコキシフェニル）
−４−アルキルシクロヘキセンを接触還元し、次いでト
ランス体を分離することにより容易に得ることができ
る。In the compound represented by the general formula (I), when both R 1 and R 2 are lower alkyl groups having about 1 to 5 carbon atoms, they are already known for conventional nematic liquid crystal compounds, The Grignard compound prepared from 4-alkoxy-1-bromobenzene was reacted with 4-alkylcyclohexanone, and the reaction product was further dehydrated to obtain 1- (4-alkoxyphenyl).
It can be easily obtained by catalytically reducing -4-alkylcyclohexene and then separating the trans form.
【００１８】しかしながら、このような化合物は強誘電
性液晶組成物に添加しても、ＳＣ*相（あるいはＳＣ
相）の温度範囲を大きく低下させてしまうために、実用
上、強誘電性液晶組成物の構成材料として好ましいもの
ではなかった。However, even if such a compound is added to the ferroelectric liquid crystal composition, the SC * phase (or SC
Since the phase) temperature range is greatly reduced, it is not preferable as a constituent material of the ferroelectric liquid crystal composition in practical use.
【００１９】本発明の一般式（Ｉ）で表わされる化合物
は、Ｒ1及びＲ2が各々独立的に、炭素原子数６〜１４と
いう長鎖のアルキル基であり、上記の優れた性質を示す
ことが可能となった。In the compound represented by the general formula (I) of the present invention, R 1 and R 2 are each independently a long-chain alkyl group having 6 to 14 carbon atoms and exhibit the above-mentioned excellent properties. It has become possible.
【００２０】本発明に係わる一般式（Ｉ）で表わされる
化合物は、Ｒ1及びＲ2が共に炭素原子数１〜５の低級ア
ルキル基である場合と全く同様にして合成することがで
きる。The compound represented by the general formula (I) according to the present invention can be synthesized in exactly the same manner as when R 1 and R 2 are both lower alkyl groups having 1 to 5 carbon atoms.
【００２１】本発明に係わる一般式（Ｉ）で表わされる
化合物の代表的なものの例を第１表に掲げる。Typical examples of the compounds represented by formula (I) according to the present invention are shown in Table 1.
【００２２】[0022]
【表１】 [Table 1]
【００２３】（表中、Ｃｒは結晶相を、ＳＢはスメクチ
ックＢ相を、Ｉは等方性液体相をそれぞれ表わす。）上
記の第１表から、一般式（Ｉ）で表わされる化合物は、
非チルト系のスメクチック相であるＳＢ相を示し、ＳＣ
相を示さないが、この化合物を少量添加しても、液晶組
成物のＳＣ*相（あるいはＳＣ相）の温度範囲をあまり
低下させることはない。(In the table, Cr represents a crystalline phase, SB represents a smectic B phase, and I represents an isotropic liquid phase.) From Table 1 above, the compound represented by the general formula (I) is
The SB phase which is a non-tilt smectic phase is shown, and SC
Although it does not exhibit a phase, the addition of a small amount of this compound does not significantly lower the temperature range of the SC * phase (or SC phase) of the liquid crystal composition.
【００２４】本発明の強誘電性液晶組成物における一般
式（Ｉ）で表わされる化合物の含有量は、２〜３０重量
％の範囲が好ましく、あまり少量ではその効果が少な
く、また多量に用いると、液晶組成物のＳＣ*相の温度
範囲を低くしたり、その相系列に影響を与えたりするの
で、５〜２０重量％の範囲が特に好ましい。The content of the compound represented by the general formula (I) in the ferroelectric liquid crystal composition of the present invention is preferably in the range of 2 to 30% by weight. If the amount is too small, the effect is small and if it is used in a large amount. The range of 5 to 20% by weight is particularly preferable because it lowers the temperature range of the SC * phase of the liquid crystal composition and affects the phase series.
【００２５】また、一般式（ＩＩ）で表わされる化合物
は、ＳＣ相を比較的低い温度域で示し、粘度も比較的小
さいので、母体液晶の構成成分としてよく利用されてい
る公知の化合物であり、本発明の第２の液晶組成物にお
いては、この一般式（ＩＩ）で表わされる化合物を母体
液晶の主成分として含有する。Further, the compound represented by the general formula (II) exhibits a SC phase in a relatively low temperature range and has a relatively low viscosity, and is a known compound which is often used as a constituent component of a host liquid crystal. In the second liquid crystal composition of the present invention, the compound represented by the general formula (II) is contained as the main component of the host liquid crystal.
【００２６】一般式（ＩＩ）で表わされる化合物のう
ち、例えば、以下のような化合物が好ましい。 （ａ）Ｒ3が炭素原子数４〜１４の直鎖状アルキル基で
あり、Ｒ4が炭素原子数４〜１４の直鎖状アルコキシル
基である一般式（ＩＩａ）の化合物。 （ｂ）Ｒ3が炭素原子数４〜１４の直鎖状アルキル基で
あり、Ｒ4が炭素原子数４〜１４の分岐状アルコキシル
基である一般式（ＩＩｂ）の化合物。 （ｃ）Ｒ3が炭素原子数４〜１４の直鎖状アルキル基で
あり、Ｒ4が炭素原子数４〜１４の直鎖状アルケニルオ
キシ基である一般式（ＩＩｃ）の化合物。 （ｄ）Ｒ3が炭素原子数４〜１４の直鎖状アルコキシル
基であり、Ｒ4が炭素原子数４〜１４の直鎖状アルキル
基である一般式（ＩＩｄ）の化合物。 （ｅ）Ｒ3が炭素原子数４〜１４の分岐状アルコキシル
基であり、Ｒ4が炭素原子数４〜１４の直鎖状アルキル
基である一般式（ＩＩｅ）の化合物。 （ｆ）Ｒ3が炭素原子数４〜１４の直鎖状アルケニルオ
キシ基であり、Ｒ4が炭素原子数４〜１４の直鎖状アル
キル基である一般式（ＩＩｆ）の化合物。Of the compounds represented by the general formula (II), the following compounds are preferable. (A) A compound of the general formula (IIa), wherein R 3 is a linear alkyl group having 4 to 14 carbon atoms and R 4 is a linear alkoxyl group having 4 to 14 carbon atoms. (B) A compound of the general formula (IIb) in which R 3 is a linear alkyl group having 4 to 14 carbon atoms and R 4 is a branched alkoxyl group having 4 to 14 carbon atoms. (C) A compound of the general formula (IIc), wherein R 3 is a linear alkyl group having 4 to 14 carbon atoms and R 4 is a linear alkenyloxy group having 4 to 14 carbon atoms. (D) A compound of the general formula (IId) in which R 3 is a linear alkoxy group having 4 to 14 carbon atoms and R 4 is a linear alkyl group having 4 to 14 carbon atoms. (E) A compound of the general formula (IIe), wherein R 3 is a branched alkoxyl group having 4 to 14 carbon atoms, and R 4 is a linear alkyl group having 4 to 14 carbon atoms. (F) A compound of the general formula (IIf), wherein R 3 is a linear alkenyloxy group having 4 to 14 carbon atoms and R 4 is a linear alkyl group having 4 to 14 carbon atoms.
【００２７】一般式（ＩＩａ）、（ＩＩｂ）及び（ＩＩ
ｃ）の化合物の例を、第２表及び第３表に示す。The general formulas (IIa), (IIb) and (II)
Examples of compounds of c) are shown in Tables 2 and 3.
【００２８】[0028]
【表２】 [Table 2]
【００２９】[0029]
【表３】 [Table 3]
【００３０】また、一般式（ＩＩｄ）、（ＩＩｅ）及び
（ＩＩｆ）の化合物の例を、第４表に示す。Table 4 shows examples of the compounds represented by the general formulas (IId), (IIe) and (IIf).
【００３１】[0031]
【表４】 [Table 4]
【００３２】本発明の強誘電性液晶組成物においては、
これらの化合物のうち、一般式（ＩＩａ）で表わされる
化合物を含有することが特に好ましい。本発明の第２の
液晶組成物における一般式（ＩＩ）で表わされる化合物
の含有量は、１０〜８０重量％の範囲が好ましく、３０
〜６０重量％の範囲が特に好ましい。In the ferroelectric liquid crystal composition of the present invention,
Among these compounds, it is particularly preferable to contain the compound represented by the general formula (IIa). The content of the compound represented by the general formula (II) in the second liquid crystal composition of the present invention is preferably in the range of 10 to 80% by weight, 30
A range of ˜60% by weight is particularly preferred.
【００３３】また、一般式（ＩＩ）で表わされる化合物
として、上記の一般式（ＩＩａ）の化合物を、一般式
（ＩＩ）で表わされる化合物の全量に対して５０〜１０
０重量％用いることが好ましい。As the compound represented by the general formula (II), the compound represented by the general formula (IIa) is added in an amount of 50 to 10 relative to the total amount of the compound represented by the general formula (II).
It is preferable to use 0% by weight.
【００３４】本発明の液晶組成物においては、母体液晶
の構成材料として、一般式（Ｉ）あるいは一般式（Ｉ
Ｉ）で表わされる化合物以外にも、例えば、以下のよう
な化合物を用いることができる。In the liquid crystal composition of the present invention, the general formula (I) or the general formula (I
In addition to the compound represented by I), for example, the following compounds can be used.
【００３５】室温に近い温度範囲でＳＣ相を示す化合物
として、下記の一般式（ＩＩＩａ）、（ＩＩＩｂ）、
（ＩＩＩｃ）あるいは（ＩＩＩｄ）As compounds showing the SC phase in a temperature range close to room temperature, the following general formulas (IIIa), (IIIb),
(IIIc) or (IIId)
【００３６】[0036]
【化５】 [Chemical 5]
【００３７】（式中、Ｒa及びＲbは、各々独立的にアル
キル基又はアルコキシル基を表わすが、少なくとも一方
はアルコキシル基を表わす。）で表わされる化合物等を
挙げることができる。(In the formula, R a and R b each independently represent an alkyl group or an alkoxyl group, but at least one of them represents an alkoxyl group).
【００３８】また、高温域までＳＣ相を示す化合物とし
ては、下記の一般式（ＩＶａ）、（ＩＶｂ）、（ＩＶ
ｃ）、（ＩＶｄ）あるいは（ＩＶｅ）Further, as the compound exhibiting the SC phase up to a high temperature range, the following general formulas (IVa), (IVb), (IV
c), (IVd) or (IVe)
【００３９】[0039]
【化６】 [Chemical 6]
【００４０】（式中、Ｒc及びＲdは、各々独立的にアル
キル基又はアルコキシル基を表わすが、少なくとも一方
はアルキル基を表わし、ｍ及びｎは、各々独立的に０又
は１を表わす。）で表わされる化合物等を挙げることが
できる。(In the formula, R c and R d each independently represent an alkyl group or an alkoxyl group, at least one of which represents an alkyl group, and m and n each independently represent 0 or 1. ) And the like.
【００４１】斯くして、本発明の液晶組成物が得られる
が、本発明におけるＳＣ*液晶組成物の特徴はその応答
が非常に高速であることにある。後述の実施例に示した
ように、一般式（ＩＩａ）で表わされる化合物８０重量
％、及び一般式（ＩＶａ）で表わされる化合物２０重量
％から成る母体液晶（Ｈ−ａ）を調製した。Thus, the liquid crystal composition of the present invention can be obtained. The characteristic feature of the SC * liquid crystal composition of the present invention is that the response is very fast. As shown in Examples described later, a base liquid crystal (Ha) was prepared, which was composed of 80% by weight of the compound represented by the general formula (IIa) and 20% by weight of the compound represented by the general formula (IVa).
【００４２】尚、母体液晶（Ｈ−ａ）は、The matrix liquid crystal (Ha) is
【００４３】[0043]
【化７】 [Chemical 7]
【００４４】から成るものである。この母体液晶（Ｈ−
ａ）８０重量％及び式（Ｐ）It consists of This host liquid crystal (H-
a) 80% by weight and formula (P)
【００４５】[0045]
【化８】 [Chemical 8]
【００４６】（式中、Ｐｒはｎ−プロピル基を表わ
す。）から成るキラルドーパント２０重量％から成るＳ
Ｃ*液晶組成物（Ｍ−ａ）は、６７℃以下でＳＣ*相を示
し、その２５℃における応答は４７μ秒であった。(Wherein Pr represents an n-propyl group) S consisting of 20% by weight of a chiral dopant.
The C * liquid crystal composition (Ma) showed an SC * phase at 67 ° C. or lower, and its response at 25 ° C. was 47 μsec.
【００４７】次に、母体液晶（Ｈ−ａ）８５重量％及び
第１表中のＮｏ．１の化合物１５重量％から成る母体液
晶（Ｈ−１）を調製した。この母体液晶（Ｈ−１）８０
重量％及び上記の式（Ｐ）のキラルドーパント２０重量
％から成るＳＣ*液晶組成物（Ｍ−１）では、その応答
速度は２５℃で３５μ秒と、ＳＣ*液晶組成物（Ｍ−
ａ）に比べてかなり高速であった。Next, 85% by weight of the base liquid crystal (Ha) and No. 1 in Table 1 were used. A host liquid crystal (H-1) consisting of 15% by weight of the compound of 1 was prepared. This host liquid crystal (H-1) 80
In the SC * liquid crystal composition (M-1) composed of 20% by weight of the chiral dopant of the above formula (P), the response speed is 35 μsec at 25 ° C. and the SC * liquid crystal composition (M-
It was considerably faster than a).
【００４８】このことから、本発明の液晶組成物が非常
に低粘性であることが理解できる。またＳＣ*相の上限
温度は５５．５℃とあまり低下していないことも理解で
きる。 従って、本発明の強誘電性液晶組成物は、実際
の表示用材料としてデバイス作成上、非常に好適であ
る。From this, it can be understood that the liquid crystal composition of the present invention has a very low viscosity. Also, it can be understood that the upper limit temperature of the SC * phase is 55.5 ° C., which is not so low. Therefore, the ferroelectric liquid crystal composition of the present invention is very suitable as an actual display material for producing a device.
【００４９】次に、母体液晶（Ｈ−ａ）９０重量％及び
一般式（Ｉ）と同様の骨格を有し、両末端のアルキル鎖
が短い化合物である式（Ｂ）Next, the formula (B), which is a compound having 90% by weight of the base liquid crystal (Ha) and a skeleton similar to that of the general formula (I), and having short alkyl chains at both ends.
【００５０】[0050]
【化９】 [Chemical 9]
【００５１】の化合物１０重量％から成る母体液晶（Ｈ
−ｂ）を調製した。この母体液晶（Ｈ−ｂ）８４重量％
及び前記の式（Ｐ）のキラルドーパント１６重量％から
成るＳＣ*液晶組成物（Ｍ−ｂ）は、４８．５℃以下で
ＳＣ*相を示し、その２５℃における応答速度は６７μ
秒であった。A matrix liquid crystal (H
-B) was prepared. 84% by weight of this host liquid crystal (Hb)
And a SC * liquid crystal composition (Mb) consisting of 16% by weight of the chiral dopant of the above formula (P) exhibits a SC * phase at 48.5 ° C. or lower, and its response speed at 25 ° C. is 67 μ.
It was seconds.
【００５２】一方、母体液晶（Ｈ−ａ）８４重量％及び
式（Ｐ）のキラルドーパント１６重量％から成るＳＣ*
液晶組成物（Ｍ−ｃ）は、ＳＣ*相の上限温度は６７．
５℃であり、その２５℃における応答速度は４５μ秒で
あった。On the other hand, SC * comprising 84% by weight of the base liquid crystal (Ha) and 16% by weight of the chiral dopant of the formula (P) .
In the liquid crystal composition (M-c), the maximum temperature of the SC * phase is 67.
The temperature was 5 ° C., and the response speed at 25 ° C. was 45 μsec.
【００５３】このことから、式（Ｂ）の化合物を母体液
晶中にわずか１０重量％含有する液晶組成物は、ＳＣ*
相の上限温度が１９度も低下し、応答速度もかなり遅く
なっていることが理解できる。From this, a liquid crystal composition containing the compound of formula (B) in the host liquid crystal in an amount of only 10% by weight is SC *.
It can be understood that the upper limit temperature of the phase is lowered by 19 degrees and the response speed is considerably slowed.
【００５４】このことから、式（Ｂ）の化合物のように
アルキル鎖の短い化合物を含有する液晶組成物では、好
ましい効果を得ることはできないことが明らかである。
また、本発明は上記の強誘電性液晶組成物を構成要素と
する液晶表示素子も提供する。この場合、本発明のＳＣ
*液晶組成物を、２枚の透明ガラス電極間に１〜２０μ
ｍ程度の薄膜として封入することにより、表示用セルと
して使用できる。 良好なコントラストを得るためには
均一に配向したモノドメインとする必要があり、このた
め多くの方法が試みられているが、液晶材料が高温側か
らＩ相−Ｎ*（キラルネマチック）相−ＳＡ相−ＳＣ
*相、又はＩ相−ＳＡ相−ＳＣ*相の相系列を示し、Ｎ*
相及びＳＣ*相における螺旋ピッチを大きくすることが
必要である。From this, it is clear that the liquid crystal composition containing a compound having a short alkyl chain such as the compound of the formula (B) cannot obtain a preferable effect.
The present invention also provides a liquid crystal display device containing the above ferroelectric liquid crystal composition as a constituent element. In this case, the SC of the present invention
* Liquid crystal composition between 1 and 20μ between two transparent glass electrodes
By enclosing it as a thin film of about m, it can be used as a display cell. In order to obtain good contrast, it is necessary to form uniformly aligned monodomains, and many methods have been attempted for this reason. However, liquid crystal materials have an I phase-N * (chiral nematic) phase-SA from the high temperature side. Phase-SC
* Phase or I phase-SA phase-SC * phase phase series, N *
It is necessary to increase the spiral pitch in the phase and SC * phase.
【００５５】一般的に、液晶組成物の螺旋ピッチの大き
さは、使用するキラルドーパントに依存し、相系列は使
用する全ての化合物に依存するが、一般式（Ｉ）で表わ
される化合物は、特定の液晶相を消失させたり、あるい
は拡大させる傾向はほとんどないので、本発明の強誘電
性液晶組成物においては、所望の相系列を得ることは容
易である。Generally, the size of the helical pitch of the liquid crystal composition depends on the chiral dopant used, and the phase sequence depends on all the compounds used, but the compound represented by the general formula (I) is Since there is almost no tendency to eliminate or expand a specific liquid crystal phase, it is easy to obtain a desired phase sequence in the ferroelectric liquid crystal composition of the present invention.
【００５６】[0056]
【実施例】以下に実施例をあげて本発明を具体的に説明
するが、本発明の主旨及び適用範囲はこれらの実施例に
よって制限されるものではない。EXAMPLES The present invention will be specifically described below with reference to examples, but the gist and the scope of application of the present invention are not limited to these examples.
【００５７】本実施例において、相転移温度の測定は温
度調節ステージを備えた偏光顕微鏡及び示差走査熱量計
（ＤＳＣ）を併用して行った。また、組成物中における
「％」はすべて『重量％』を表わす。 （合成例１） １−（４−オクチルオキシフェニル）−
４−オクチルシクロヘキセンの合成 ４−オクチルシクロヘキサノン９．６７ｇをテトラヒド
ロフラン（ＴＨＦ）４０ｍｌに溶解した。これに４−オ
クチルオキシ−１−ブロモベンゼン１３．１ｇ及び金属
マグネシウム１．２３ｇから調製したグリニヤール化合
物の１００ｍｌＴＨＦ溶液を５℃で加え、３時間反応さ
せた。この混合物に１Ｎ塩酸を加え、エーテルで抽出
し、抽出液を水、次いで飽和食塩水で洗滌した後、有機
層を無水硫酸ナトリウムで脱水した。この有機層の溶媒
を減圧下で溜去して、１−（４−オクチルオキシフェニ
ル）−４−オクチルシクロヘキサン−１−オールの粗製
物１６．０ｇを得た。この粗製物の全量をトルエン８０
ｍｌに溶解し、硫酸水素カリウム２．０ｇを加え、３時
間加熱還流した。放冷した後、飽和炭酸水素ナトリウム
水溶液、水、次いで飽和食塩水で洗滌し、無水硫酸ナト
リウムで脱水した。溶媒を溜去して得られた粗製物をカ
ラムクロマトグラフィー（シリカゲル、ヘキサン／酢酸
エチル＝１０／１）を用いて精製して、１−（４−オク
チルオキシフェニル）−４−オクチルシクロヘキセンの
結晶１３．３ｇを得た。 （合成例２） トランス−１−（４−オクチルオキシフ
ェニル）−４−オクチルシクロヘキサン（第１表中のＮ
ｏ．１の化合物）の合成 実施例１で得られた１−（４−オクチルオキシフェニ
ル）−４−オクチルシクロヘキセン１．０ｇを酢酸エチ
ル２５ｍｌに溶解した。これにパラジウムカーボン１０
０ｍｇを加え、常圧下、室温で１２時間水素添加を行っ
た。反応終了後、反応混合物から触媒を濾別し、濾液を
減圧濃縮し、得られた粗製物をカラムクロマトグラフィ
ー（シリカゲル、ヘキサン／酢酸エチル＝２０／１）を
用いて分離精製した。この精製物を更にエタノールから
再結晶させて、シス体を完全に除き、トランス−１−
（４−オクチルオキシフェニル）−４−オクチルシクロ
ヘキサンの結晶７０ｍｇを得た。In this example, the phase transition temperature was measured by using a polarizing microscope equipped with a temperature adjusting stage and a differential scanning calorimeter (DSC). Further, all "%" in the composition represent "% by weight". (Synthesis example 1) 1- (4-octyloxyphenyl)-
Synthesis of 4-octylcyclohexene 9.67 g of 4-octylcyclohexanone was dissolved in 40 ml of tetrahydrofuran (THF). A 100 ml THF solution of a Grignard compound prepared from 13.1 g of 4-octyloxy-1-bromobenzene and 1.23 g of metallic magnesium was added thereto at 5 ° C. and reacted for 3 hours. 1N Hydrochloric acid was added to this mixture, and the mixture was extracted with ether. The extract was washed with water and then with saturated saline, and the organic layer was dried over anhydrous sodium sulfate. The solvent of this organic layer was distilled off under reduced pressure to obtain 16.0 g of a crude product of 1- (4-octyloxyphenyl) -4-octylcyclohexan-1-ol. The total amount of this crude product is toluene 80
It was dissolved in ml, 2.0 g of potassium hydrogen sulfate was added, and the mixture was heated under reflux for 3 hours. After allowing to cool, it was washed with a saturated aqueous solution of sodium hydrogen carbonate, water, and then saturated saline, and dehydrated with anhydrous sodium sulfate. The crude product obtained by distilling off the solvent was purified by column chromatography (silica gel, hexane / ethyl acetate = 10/1) to give 1- (4-octyloxyphenyl) -4-octylcyclohexene as crystals. 13.3 g was obtained. Synthesis Example 2 trans-1- (4-octyloxyphenyl) -4-octylcyclohexane (N in Table 1
o. Compound of 1) 1.0 g of 1- (4-octyloxyphenyl) -4-octylcyclohexene obtained in Example 1 was dissolved in 25 ml of ethyl acetate. Palladium carbon 10
0 mg was added, and hydrogenation was carried out under normal pressure at room temperature for 12 hours. After completion of the reaction, the catalyst was filtered off from the reaction mixture, the filtrate was concentrated under reduced pressure, and the obtained crude product was separated and purified by column chromatography (silica gel, hexane / ethyl acetate = 20/1). The purified product was further recrystallized from ethanol to completely remove the cis form, and trans-1-
70 mg of crystals of (4-octyloxyphenyl) -4-octylcyclohexane were obtained.
【００５８】この化合物の相転移温度は第１表に示し
た。 （実施例１） 液晶組成物の調製 一般式（ＩＩａ）で表わされる化合物８０％及び一般式
（ＩＩＩａ）で表わされる化合物２０％から成る、ＳＣ
相を示す母体液晶（Ｈ−ａ）を調製した。The phase transition temperature of this compound is shown in Table 1. (Example 1) Preparation of liquid crystal composition SC comprising 80% of the compound represented by the general formula (IIa) and 20% of the compound represented by the general formula (IIIa).
A matrix liquid crystal (Ha) exhibiting a phase was prepared.
【００５９】母体液晶（Ｈ−ａ）は、The host liquid crystal (Ha) is
【００６０】[0060]
【化１０】 [Chemical 10]
【００６１】から成るものである。次に、この母体液晶
（Ｈ−ａ）８５％及び一般式（Ｉ）で表わされる第１表
中のＮｏ．１の化合物１５％から成る母体液晶（Ｈ−
１）を調製した。It consists of: Next, 85% of the base liquid crystal (Ha) and No. 1 in Table 1 represented by the general formula (I). 1 of the matrix liquid crystal (H-
1) was prepared.
【００６２】この母体液晶（Ｈ−１）８０％及び式
（Ｐ）This matrix liquid crystal (H-1) 80% and the formula (P)
【００６３】[0063]
【化１１】 [Chemical 11]
【００６４】（式中、Ｐｒはｎ−プロピル基を表わ
す。）の光学活性化合物から成るキラルドーパント２０
％から成るＳＣ*液晶組成物（Ｍ−１）を調製した。こ
のＳＣ*液晶組成物は５５．５℃までＳＣ*相を、６８℃
までＳＡ相を、７１℃までＮ*相を、それぞれ示した。 （実施例２） 液晶表示素子の作成 実施例１で得られた液晶組成物（Ｍ−１）を用いて、以
下の手順で液晶表示素子を作成した。(Wherein Pr represents an n-propyl group) a chiral dopant 20 composed of an optically active compound.
% SC * liquid crystal composition (M-1) was prepared. This SC * liquid crystal composition has SC * phase up to 55.5 ° C and 68 ° C
SA phase and N * phase up to 71 ° C., respectively. (Example 2) Preparation of liquid crystal display element The liquid crystal composition (M-1) obtained in Example 1 was used to prepare a liquid crystal display element by the following procedure.
【００６５】まず、ＩＴＯ蒸着ガラス板（ＥＨＣ社製、
電極面積７０mm2）を洗浄、乾燥した。これにポリイミ
ド形成溶液「ＰＩＱ」（日立化成工業社製）をスピナー
塗布機で塗布し、ポリイミド被膜を形成した（基板
Ａ）。First, an ITO vapor-deposited glass plate (manufactured by EHC,
The electrode area 70 mm 2 ) was washed and dried. A polyimide forming solution "PIQ" (manufactured by Hitachi Chemical Co., Ltd.) was applied to this with a spinner coater to form a polyimide coating (substrate A).
【００６６】同様にして、グラスファイバーのスペーサ
ーを混合した、上記のポリイミド形成溶液を用いて、ス
ペーサーを含んだポリイミド被膜を形成した（基板
Ｂ）。 基板Ａ及び基板Ｂをナイロン布でラビング処理を施した
後、一方の基板に熱硬化型エポキシ接着剤を塗布して、
基板Ａ及び基板Ｂをそのラビング方向が互いに平行かつ
逆向きになるように重ね合わせ、８０℃で３時間放置
し、硬化させ、セルを作製した。Similarly, a polyimide coating containing spacers was formed using the above-mentioned polyimide forming solution mixed with glass fiber spacers (substrate B). After rubbing the substrates A and B with a nylon cloth, a thermosetting epoxy adhesive is applied to one of the substrates,
Substrates A and B were stacked so that the rubbing directions were parallel and opposite to each other, and the substrates were left at 80 ° C. for 3 hours to be cured to prepare a cell.
【００６７】こうして作製したセルに、ＳＣ*液晶組成
物（Ｍ−１）を加熱して等方性液体相とした状態で注入
し、次いで、１分間に１℃の割合で徐冷を行い、Ｎ
*相、ＳＡ相、ＳＣ*相を配向させ、液晶表示素子を得
た。このセル厚を測定したところ、２．０μｍであっ
た。SC * liquid crystal composition (M-1) was injected into the cell thus prepared in a state of being heated to form an isotropic liquid phase, and then gradually cooled at a rate of 1 ° C. for 1 minute, N
A liquid crystal display device was obtained by orienting the * phase, the SA phase, and the SC * phase. When the cell thickness was measured, it was 2.0 μm.
【００６８】このセルに電界強度１０Ｖp-p／μｍの矩
形波を印加してその電気光学応答速度を測定したとこ
ろ、２５℃で３５μ秒という高速応答が確認できた。こ
の時の自発分極は１８．５ｎＣ／ｃｍ2であり、チルト
角は２４．２゜であった。コントラストは良好であっ
た。 （比較例１）実施例１において調製した母体液晶（Ｈ−
ａ）８０％及び式（Ｐ）の光学活性化合物から成るキラ
ルドーパント２０％から成るＳＣ*液晶組成物（Ｍ−
ａ）を調製した。このＳＣ*液晶組成物（Ｍ−ａ）は６
７℃までＳＣ*相を、６９．５℃までＳＡ相を、７６℃
までＮ*相をそれぞれ示した。A rectangular wave having an electric field intensity of 10 V pp / μm was applied to this cell and its electro-optical response speed was measured. As a result, a high-speed response of 35 μsec at 25 ° C. was confirmed. At this time, the spontaneous polarization was 18.5 nC / cm 2 and the tilt angle was 24.2 °. The contrast was good. (Comparative Example 1) The matrix liquid crystal (H-
a) SC * liquid crystal composition (M-) comprising 80% and 20% of a chiral dopant consisting of an optically active compound of formula (P).
a) was prepared. This SC * liquid crystal composition (Ma) has 6
SC * phase up to 7 ℃, SA phase up to 69.5 ℃, 76 ℃
Up to N * phase respectively.
【００６９】実施例４と全く同様にして測定した電気光
学応答速度は、２５℃において４７μ秒であり、実施例
４と比較してかなり遅くなった。また、このときの自発
分極は２１．７ｎＣ／ｃｍ2であり、チルト角は２７．
６゜であった。 （比較例２）母体液晶（Ｈ−ａ）８４％及び式（Ｐ）の
光学活性化合物から成るキラルドーパント１６％から成
るＳＣ*液晶組成物（Ｍ−ｃ）は、６７．５℃以下でＳ
Ｃ*相を示し、その２５℃における応答は４５μ秒であ
った。またこのときの自発分極は１４．４ｎＣ／ｃｍ2
であり、チルト角は３０．６゜であった。The electro-optical response speed measured in exactly the same manner as in Example 4 was 47 μsec at 25 ° C., which was considerably slower than that in Example 4. The spontaneous polarization at this time was 21.7 nC / cm 2 , and the tilt angle was 27.
It was 6 °. (Comparative Example 2) An SC * liquid crystal composition (Mc) comprising 84% of a matrix liquid crystal (Ha) and 16% of a chiral dopant composed of an optically active compound of the formula (P) has an S content of 67.5 ° C or lower.
The C * phase was exhibited, and the response at 25 ° C. was 45 μsec. The spontaneous polarization at this time is 14.4 nC / cm 2.
And the tilt angle was 30.6 °.
【００７０】これに対し、母体液晶（Ｈ−ａ）９０％及
び式（Ｂ）On the other hand, the base liquid crystal (Ha) 90% and the formula (B)
【００７１】[0071]
【化１２】 [Chemical 12]
【００７２】の化合物１０％から成る母体液晶（Ｈ−
ｂ）を調製した。この母体液晶（Ｈ−ｂ）８４％及び式
（Ｐ）の光学活性化合物から成るキラルドーパント１６
％から成るＳＣ*液晶組成物（Ｍ−ｂ）を調製した。A matrix liquid crystal (H-
b) was prepared. Chiral dopant 16 composed of 84% of the base liquid crystal (Hb) and the optically active compound of the formula (P).
% SC * liquid crystal composition (Mb) was prepared.
【００７３】このＳＣ*液晶組成物（Ｍ−ｂ）のＳＣ*相
の上限温度は４８．５℃とかなり低くなった。また、応
答速度は６７μ秒とかなり遅くなった。このときの自発
分極は９．８ｎＣ／ｃｍ2であり、チルト角は２０．４
゜であり、本発明のＳＣ*液晶組成物と比較して小さく
なった。The maximum temperature of the SC * phase of this SC * liquid crystal composition (Mb) was 48.5 ° C., which was considerably low. The response speed was 67 μsec, which was considerably low. At this time, the spontaneous polarization was 9.8 nC / cm 2 , and the tilt angle was 20.4.
Was smaller than the SC * liquid crystal composition of the present invention.
【００７４】[0074]
【発明の効果】本発明の一般式（Ｉ）で表わされる化合
物を含有する強誘電性液晶組成物は、低粘性であるので
４０μ秒以下という高速応答が可能であり、広いＳＣ*
相の温度範囲を得ることも容易である。従って、表示用
光スイッチング素子の材料として極めて有用である。The ferroelectric liquid crystal composition containing the compound represented by the general formula (I) of the present invention has a low viscosity, so that a high speed response of 40 μsec or less is possible and a wide SC *
It is also easy to obtain the temperature range of the phases. Therefore, it is extremely useful as a material for the optical switching element for display.
Claims (4)
４の直鎖状アルキル基を表わす。）で表わされる化合物
を含有する強誘電性液晶組成物。1. A compound represented by the general formula (I): (In the formula, R 1 and R 2 each independently have 6 to 1 carbon atoms.
4 represents a linear alkyl group. ) A ferroelectric liquid crystal composition containing a compound represented by:
コキシル基又はアルケニルオキシ基を表わし、他方は炭
素原子数４〜１４の直鎖状アルキル基を表わす。）で表
わされる化合物を含有し、スメクチックＣ（ＳＣ）相を
示す母体液晶及び （２）光学活性化合物から成るキラルドーパント を含有することを特徴とする請求項１記載の強誘電性液
晶組成物。2. (1) General formula (II): (In the formula, one of R 3 and R 4 represents an alkoxyl group or an alkenyloxy group having 4 to 14 carbon atoms, and the other represents a linear alkyl group having 4 to 14 carbon atoms). 2. The ferroelectric liquid crystal composition according to claim 1, further comprising: a matrix liquid crystal containing a liquid crystal and showing a smectic C (SC) phase, and (2) a chiral dopant composed of an optically active compound.
子数６〜１２の直鎖状のアルキル基であり、Ｒ4が炭素
原子数６〜１２の直鎖状アルコキシル基である化合物を
含有する請求項２記載の強誘電性液晶組成物。3. A compound represented by the formula (II), wherein R 3 is a linear alkyl group having 6 to 12 carbon atoms and R 4 is a linear alkoxy group having 6 to 12 carbon atoms. The ferroelectric liquid crystal composition according to claim 2, which contains.
組成物を構成要素とする液晶表示素子。4. A liquid crystal display device comprising the ferroelectric liquid crystal composition according to claim 1, 2 or 3 as a constituent element.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3200449A JPH0543876A (en) | 1991-08-09 | 1991-08-09 | Ferroelectric liquid crystal composition containing phenylcyclohexane derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3200449A JPH0543876A (en) | 1991-08-09 | 1991-08-09 | Ferroelectric liquid crystal composition containing phenylcyclohexane derivative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0543876A true JPH0543876A (en) | 1993-02-23 |
Family
ID=16424492
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3200449A Pending JPH0543876A (en) | 1991-08-09 | 1991-08-09 | Ferroelectric liquid crystal composition containing phenylcyclohexane derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0543876A (en) |
-
1991
- 1991-08-09 JP JP3200449A patent/JPH0543876A/en active Pending
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