Liquid crystal-like compound, ferroelectric liquid crystal composition containing the same compound and ferroelectric liquid crystal element

[Detailed Description of the Invention]

[Description of the Prior Art] The ferroelectric liquid crystal display type advocated by Clark Lagerwall in 1980, Spiral pitch i which the strong dielectric liquid crystal (following FLC) itself has in 5SFLC (Surface-3 tabilized-ferroelectric-Liquidcrystal) method. The effect of an up-and-down board interface is used, and it is a solution (it has a chief aim in things.). ■ If an up-and-down board interval (cell thickness) is set below to the film thickness which solves the above-mentioned spiral pitch 10, and it sets up so that a liquid crystal molecule may take those for Arrangement in parallel to ■ and also a substrate interface, the direction of a layer in the smectic phase of FLC will be formed at right angles to a substrate. ■ Don't become empty further (if the direction for Arrangement of the molecule on one substrate is regulated, it can cross all over a cell and can form the direction of a layer uniformly.). If the state for Arrangement formed by the above gradual molecule control is seen macroscopically, in a cell side, a stable FLC molecule major axis direction (n) will be limited by the 2-way. An FLC display tends to apply the point which this 2-way (the average direction of n) can classify with light polarizer to a display element. The fundamental mechanism which switches between 2-ways to the above-mentioned stability uses the ferroelectricity which FLC shows in a smectic C* phase. FLC has a dipole moment (mu) of a molecule in a field parallel to a layer, and in some dipole moments (mu), between the substrates of a cell is continuously connected, though a direction is changed -- average -- the upper board from a lower board -- or intrinsic polarization (Ps) is formed in the reverse direction, and it exists. each of the direction (from the bottom from a top, and the bottom -- the upper) of intrinsic polarization (Ps) -- the above-mentioned molecule length axis (n) -- Either - since I am doing, switching by an electric field is possible. If an electric field is made to impress to an FLC layer from the exterior in detail and all the dipole moments (mu) in a layer will cut a set (Ul) electric field in the direction of an electric field, the state "pass relief for a while (at least lmus~2ms changes with FLC)" -- To fall down (S2) (,) Ul is the degree of order or quantity (it is in an optically uniaxial good state optically (uniform state), and since the dipole of FLC is twisted somewhat S2, axiality is in the state whose direction of intrinsic polarization corresponds although it is inferior to Ul (Twisted state).) of a molecule from S2. If the polarity of an external electric field becomes reverse similarly, the state of calling it U2.S2 exists. Between Ul and 2 states of U2 can be chosen by the polarity of an electric field like St and S2 (bistability). In addition to the feature which has the above bistabilities, a strong dielectric liquid crystal has the outstanding feature of being a high-speed response. It is for the intrinsic polarization and the impression electric field which a strong dielectric liquid crystal has to act directly, and to induce transition of the state for Arrangement, and is [ 3~4 order ] quicker than the speed of response of the conventional TN type element by the operation of dielectric constant anisotropy and an electric field. Thus, the strong dielectric liquid crystal has the extremely outstanding characteristic potentially, and the application to a high-speed optical optical shutter, and high density and a big screen display is expected by using such character. For this reason, although research is widely made about liquid crystal material with ferroelectricity, it is hard to say that the ferroelectric liquid crystal material developed by the present is provided with sufficient characteristic of using for a liquid crystal element including low-temperature operational characteristic, a high-speed response, etc. thick ((b) viscosity eta to carry out -- smallness (it carries out)) in size Ps of (a) intrinsic polarization, in order to make quick speed of response of a ferroelectric liquid crystal element (One) It is quantity (it carries out) about impressed electromotive force E. There is a method. However, since it drives by IC etc., impressed electromotive force has a maximum, and its lower possible one is desirable. Therefore, it is necessary to make viscosity eta small in fact, or to enlarge the value of size Ps of intrinsic polarization. the restrictions to the element composition which the internal electric field of the cell which intrinsic polarization brings about is generally also large in the large ferroelectricity chiral smectic liquid crystal compound of intrinsic polarization, and can take a bistable state -- many (it is in a tendency.) It is [ in vain ] thick in intrinsic polarization (even if it carries out, along with it, viscosity is also in the tendency which becomes large and can consider that speed of response does not become not much quick as a result.). When the category temperature range as an actual display considers it for example, as a 5~40 degreeC grade, generally there is change of speed of response about 20 times, and the present condition is over the limit of regulation by drive voltage and frequency. As stated above, in order to put a ferroelectric liquid crystal element in practical use, viscosity has a high-speed response low, and the small ferroelectricity chiral smectic liquid crystal constituent of the temperature dependence of speed of response is required. The composition of a typical strong dielectric liquid crystal cell forms an electrode pattern by ITO etc. on a glass substrate, it is formation (about 1000 persons) about the short prevention layer of an up-and-down board at 5i02 grade on it -- forming PK (carrying out east shrine:5P510.710. ...) film by the film thickness like 400lambda on it Each other is made to face so that it may become for Arrangement symmetrical with the upper and lower sides of what carried out rubbing processing of the PI film top with hair transplantation cloths, such as acetate, and it constitutes, and keeps the substrate interval at 1~3 micrometers. FLC arranged under such conditions on the other hand is connected where Guyrefuter n is generally twisted in between substrates, and it is known that those optically uniaxial for Arrangement are not shown by a smectic C phase (the above-mentioned Sl, S2). In such a case, it is that the transmissivity of a liquid crystal layer is low to one of the problems. if light polarizer is set as Klos Nicole, and optical sorting between two stable state Sl and S2 is performed by inserting the above-mentioned cell between them and coincides Sl, either of S2, and the average part secondary shaft of Sl with the absorption axis of light polarizer -- penetration light -- remarkable -- low ("black" can be expressed.) Next, it is Sl when a molecule position is switched to S2 state. In 82, if the angle between 82 is set to 2thetaa, when only 2thetaa shifts from a polarization axis, a molecule position produces penetration light and can express "white." A transmitted light amount will obtain the intensity of I to the intensity of incidence light IO under Klos Nicole, if it assumes optically uniaxial [ of molecular orientation ]. Here, as for deltan, cell thickness and lambda of the refractive-index anisotropy of FLC and d are the wavelengths of incidence light. When the above cells are used, it is known experimentally that thetaa will be 5degree~86 and a I got it. case will not depend those for rye stayed Arrangement on material so much. Since control of the paragraph of deltand pi/lambda cannot be easily performed in physical properties, he would like to enlarge thetaa and to enlarge ■, but depending on a static technique for Arrangement, all cannot be attained easily well. It is known by using the torque of deltaepsilon paragraph of FLC to such a problem that thetaa can be extended (1983. AT & T announces by SID). Canon JP,61-245142.61,A-246722.61-246723.61-246724.61-249024.6l.-249025. The electric field of an effective value fixed in addition to the time of switching is impressed, By generating of charge polarization, the stable state of the molecule in the inside of an electric field is related with Sl and the torque r'ps s A C Stabilize effect committed in the FLC molecule about switching in the state (the AC Stabilize effect) of using changing from S2, and it is Work (torque FA) to an FLC molecule. What's -- each -- it is proportional to the following physical properties. r'ps clPs-E ........ (2) r'Ag 00 and delta epsilon-epsilon. - E2 ..... It turns out that it is indicated also by (3) and (3) type that the role whose numerals and absolute value of deltaepsilon of FLC are very important is clear. Change of thetaa to V r m s of four sorts of FLC with the value from which the physical properties about deltaepsilon differ was shown in Drawing 1. Measurement was performed by 60-kHz rectangle exchange, in order to remove the influence by Ps. (I) deltaepsilon Knee 5.5, (If) -- deltaepsilon Knee 3.0 and (II[) -- deltaepsilon Knee O and (IV) -- deltaepsilon2 -- it is 1.0 -- qualitative -- deltaepsilon -- (I) -- < -- (It) -- < -- (m) -- < -- it was (rv). It turns out that thetaa becomes large by the low voltage, so that it may understand and deltaepsilon is negatively large, even if it sees a glove, therefore it contributes to ■. When the difference of the transmissivity at the time of using this (I) and (I[[) was compared, while it was 15%, by (■), it is 6% and there was a clear difference (1). ° which controls the physical properties of delta epsilon and Ps (eta) to be known also for the above example -- thick [ in the display properties of 5SFLC ] (it is changeable.) by things However, the improvement in display properties according [ deltaepsilon ] to the above-mentioned AC Stabilize effect since it is almost close to 0 can hardly expect many of Is being used ferroelectric liquid crystal constituents for the present condition. [Objects of the Invention] Solve the above-mentioned problem so that the object of the present invention can use a ferroelectric liquid crystal element, i.e., a new liquid crystal compound is used in the first place. Providing the liquid crystal element using the liquid crystal constituent which is excellent in the response characteristic, and the liquid crystal constituent, and by using a new liquid crystal compound for the second, the AC Stabilize effect is given and it is in providing the liquid crystal element using the liquid crystal constituent greatly raised in display properties, and the liquid crystal constituent. [Summary of the Invention] It is made in order to achieve the above-mentioned object, and the present invention is following general formula (I). inside of [above-mentioned general formula, A and Is a single bond, /8, /, and A 2 Ha #X, or an apricot -- is shown, X shows hydrogen, halogen, or a cyano group, and Y shows oxygen or sulfur. The Alkyl machine of the straight chain shape of carbon number 1~18, or the letter of branching with which R and R2 may have a substitution machine, An alkoxy group, an alkylcarbonyloxy machine, an alkyloxy carbonyl group, or alkyloxy carbonyloxy group is shown, and the substitution machine in this case shows chlorine, bromine, a cyano group, an alkoxy group, or an alkyloxy carbonyl group. It is shown. ] The ferroelectric liquid crystal constituent which comes out and contains the liquid crystallinity compound and it which are expressed as acid content for at least one-kind Arrangement is provided. The present invention also provides the ferroelectric liquid crystal element which uses such a liquid crystal constituent. These artificers introduce a hetero atom into a ring frame, and give unique pi electronic structure, It is a ferroelectric liquid crystal compound about the liquid crystallinity compound denoted by general formula (I) which increased the dielectric constant of the direction of a molecule short axis, The ferroelectric liquid crystal element using the ferroelectric liquid crystal constituent obtained by mixing to a ferroelectric liquid crystal constituent etc. and the liquid crystal constituent is excellent in the response characteristic, and also the AC Stabilize effect is given, and it finds out that display properties with the good result are acquired. [Detailed description of the invention] It is compounded in the third step of the liquid crystallinity compound shown by general formula (I) of the present invention. (A) General formula (1) B= CH2 In the of case The third step It is compoundable also by the fourth step, however the following method. The first step The fifth step In the case of B=-OCH2- The third step The fourth step B The thing of CO- is compounded in the following courses. (B) General formula B is -CH2. The thing of O is compounded in the following courses. The fifth step (C) General formula General formula It comes out and the example of a liquid crystallinity compound expressed is shown. A 23 * C6H13 The. Eaves 0CH2 A house CII HI7 B-6 * B 11 * B-1 * 2 * B-3 * B-5 * 17 * B-20 * B-22 * B-23 * B-32 * B-34 * B-35 * B-28 * B-29 * B-36 * B-38 * B-48 * B-44 * B-46 * 47 * The liquid crystal constituent of the present invention contains the liquid crystallinity compound denoted by the above-mentioned general formula (1) as an at least one-kind combination ingredient. In order that the liquid crystal constituent of the present invention may adjust the intrinsic polarization, the spiral pitch, a phase sequence, its temperature range, the response characteristic, a Tilt angle, dielectric constant anisotropy, etc. other than a liquid crystallinity compound which are denoted by the above-mentioned general formula (1), The compound chosen from the compound shown in each group which carries out the following is contained as a composition ingredient. In this case, it is desirable to use the liquid crystallinity compound shown by general formula (I) at 0.5~60% of the weight preferably of the liquid crystal constituent which can be obtained, and 5~40 % of the weight. A group: Optically active compound 8 group which produces a spiral by adding to the nematic phase which is not chiral; the smectic phase which is not chiral -- and (Up) It was The liquid crystal compound which has a nematic phase ■ 05H, 1-CgammagO" - CI2H28■C, Hta-@o-oc 6H, 3 ■ C6H13 mother @oc5H11 U ■ Cl5Hu m?, O+QC 5H. C5HuO<\FiascoCe1H13 -N ■ c5H, o (peak) -N C3HI7 ■ CsH+t (C\FiascoQC7H) -N U And in the above-mentioned example of a compound, the ferroelectric liquid crystal constituent which has a liquid crystallinity compound denoted by general formula (I) of the invention in this application and a compound of the system which has phenyl pyrimidine also especially in B group can form a good liquid crystal constituent. The present invention is explained still in detail using an example below. However, the present invention is not limited by the example of the present invention, and the example. Example 1 2-n-Decyl- 5-C4 - Composition (illustration compound A-3) of (transformer 47-n-pentyl cyclohexyl carbonyloxy)-phenyl]-1, 3, and 4-oxadiazole 2-n-Decyl- 5-[4-hydroxyphenyl]-1, 3, 1.5g of 4-oxadiazole (4,97X 10-" Mol) and 2.5 m of dry pyridine are 17 and dry toluene 2, 5 Into the mixed solution of m4, dry toluene 2 of 1.08 g (4, 97X10-" Mol) of transformer 4-n-pentyl cyclohexane carbonyl chloride and 5 mA' solution were dropped in 20 minutes below by 5 degreeC. It agitated at after-dropping room temperature for 27 hours. Reaction solution is poured into ice water 50m1 after the end of a reaction, and they are 6N and H (pH 1 was used by J'.). The solvent (benzene) was distilled off and the rough product was obtained, after extracting, washing in cold water and drying with benzene. Silica gel [ this ] chromatography refining using a n-hexane/ethyl acetate =5/l mixed solvent is performed, It re-crystallizes by ethanol and is 1.92-g 2-n-Decyl- 5-[4-() lance 4'-n-pentyl cyclohexyl carbonyloxy-phenyl ]. -1, 3, and 4-oxadiazole was obtained. (80.1% of yield) 73.6degreeC 120.3 degreeC fruit" 1 Argument 234 2-n-Decyl- 5-[4-hydroxyphenyl ] used in Example 1 Using -1, 3, and 4-oxadiazole, the reactional phase hand was changed and the dielectric was compounded in the similar way. Brancho 1" Reactional phase hand Transformer 4-n-propyl cyclohexane carbonyl chloride 2-n-Decyl- 5-[4-() lance 4'-n-propyl cyclohexyl carbonyloxy-phenyl]-1, 3 *4-oxadiazole (illustration compound A-2) output reactional phase hand Output p-n-Decyl benzoic acid chloride 2-n-Decyl- 5[(4(4'-n-Decyl benzoyloxy)-phenyl] -1, 3, 4-oxadiazole (illustration compound A-12) reactional phase hand) Output 3-full Oro- 4-n-octyloxy benzoic acid chloride 2-n-Decyl- 5-[phenyl [ 4 -(3-full Oro- 4'-n-octyloxy benzoyloxy)- ]]-1, 3 *4-oxadiazole (illustration compound) A-15) Phase transition 123.9 degreeC 126.5 " C 113-degreeC 124.7degreeC Cusp11Specialj 2-n-octyl 5-[4-hydroxy Phenylco- 1,3,4-oxadiazole and transformer 4-n-propyl cyclohexane carbonyl chloride are used, It was made to react by the same method as Example 1, and 2-n-octyl 5-[lance 4'-n-propyl cyclohexyl carbonyloxy-4-0 Phenyl] 1.3.4-oxadiazole was obtained. (85% of yield) 66.9 degrees C 110 or 2 degreeC fruit JL animal J 2-n-Decyl- 5-[4 - () Lance 4'-4n= propyl cyclohexyl methylene Oxy-phenyl]1 and composition (illustration compound A-22) of 3.4-oxadiazole 2-n-Decyl- 5-[4-hydroxyphenyl]-1, 3, 1.5g of 4-oxadiazole (4 and 97X 10-" Mol) were dissolved in the Dimethylform amide of 1 20 m. Potassium hydrate 0.75g was added to this 85%, and it agitated by 100 degreeC for 1 hour. 1.54 g (4, 97X10-" Mol) of transformer 4-n-propyl cyclohexyl methyl =p-Ruen sulfonate was added to this, and also it agitated by 100 degreeC for 4 hours. This was poured into ice water 200mf after the end of a reaction, the solvent was distilled off and the rough product was obtained, after having Benzendé-extracted, washing and drying. Silica gel column chromatography refining was performed, and also this was re-crystallized by ethanol, and 0.94-g 2-n-Decyl- 5-[phenyl [ 4 -(transformer 4'-n-propyl cyclohexyl methylene Oxy)- ]]-1, 3, and 4-talent Xazadiazole was obtained. (43.2% of yield) 42.6degreeC 98.4degreeC Real"L carp 1 A-2 was mixed at a rate of 4= 1 among the examples of a liquid crystallinity compound denoted by the general formula (1) of (9) and the above-mentioned present invention among the examples (A group) of the above-mentioned ferroelectric liquid crystal compound, and liquid crystal constituent A was obtained. It pinched among a pair of electrode substrates which performed rubbing processing to polyimide covering which covers an electrode for the above-mentioned ferroelectric liquid crystal compound (9) and liquid crystal constituent A, respectively (2 micrometers of cell thickness), and produced the liquid crystal element. Using these liquid crystal elements, the optical response under crossed nicols was detected by electric field impression of peaked peak voltage 20V, and speed of response was measured. A result is shown below. 40degreeC 25degreeC Ferroelectric liquid crystal compound (9) 400micro5610microsecond liquid crystal constituent A 280 mus The thing more than 420 mus showed that the response characteristic improved by mixing the liquid crystallinity compound [example A-2] of the present invention to ferroelectric liquid crystal compound [example (9) Co. Real"L animal J (38) was mixed with (1) at a rate of 4= 1 among the examples (A group) of the above-mentioned ferroelectric liquid crystal compound, and liquid crystal constituent B was obtained. Next, inside A-23 of the example of a liquid crystallinity compound denoted by the general formula (1) of the above-mentioned liquid crystal constituent B and the above-mentioned present invention was mixed at a rate of 9= 1, and liquid crystal constituent C was obtained. The liquid crystal element was produced like the case of Example 6 using the above-mentioned liquid crystal constituent B and liquid crystal constituent C, respectively. and also it set impressed electromotive force to 30V using these liquid crystal elements -- Example 6 -- all (speed of response was measured in the similar way.) A result is shown below. 35degreeC 25degreeC Liquid crystal constituent B685microsecond From the thing beyond 1275microsecond liquid crystal constituent C450micro5680microsecond, by mixing liquid crystallinity compound A'-23 of the present invention to liquid crystal constituent B showed that the response characteristic improved. Cuspm A-12 was mixed by the following ratio among [ A-3 ] the liquid crystallinity compounds expressed in the general formula (1) of the present invention as zero among the examples (B group) of liquid crystal constituent B used in Example 7, and the smectic liquid crystal compound which is not chiral [ above-mentioned ], and liquid crystal Composition was obtained. Liquid crystal Composition Liquid crystal constituent B : (the liquid crystal element was produced on the completely same conditions as Example 7 using the 1:A-3:A-12= 14:4:1:1 above-mentioned liquid crystal Composition, and speed of response was measured on the completely same conditions.) A result is shown below. 35degreeC 25degreeC Liquid crystal constituent B (example 7) 685 microseconds It is with liquid crystallinity compound A-3 of the present invention, and A-12 from the thing beyond 1275microsecond liquid crystal constituent D470micro5620microsecond to liquid crystal constituent B, By mixing combining smectic liquid crystal compound 0 which is not chiral as for others showed that the response characteristic improved. L Cusp"" Tow deltaepsilon mixed inside A-22 of the example of a liquid crystallinity compound denoted by general formula (I) of liquid crystal C31014 by Chisso Corp. [deltaepsilonand0.4] (a sin wave, 1oOKHz), and the present invention which is almost O at a rate of 92:8, and obtained liquid crystal constituent E. Liquid crystal layer thickness was 1.5 micrometers using the above-mentioned C5IO14 and liquid crystal constituent E, and also it produced the liquid crystal element by the completely same method as Example 6, respectively. When the Tilt angle was measured under crossed nicols in 25 degreeC using the above-mentioned liquid crystal element, 7 * liquid crystal constituent E was 7.2 degrees C31014. Next, when microscope observation was performed and the Tilt angle was measured, impressing the rectangle wave of ±8v on the frequency of 60 kHz, 8.8 degrees and liquid crystal constituent E became 11.4 degrees C31014. When transmissivity was measured at this time, C31014 was 7.8% and the liquid crystal constituent was 11%. When the contrast ratio was measured, as for C51014, 8:11 liquid-crystal constituent E is 30. : It was 1. It turned out that the above things can improve display properties according [ the liquid crystal element obtained by mixing liquid crystallinity compound A-22 expressed with general formula (I) of the present invention to C51014 which is almost O ] to the AC Stabilize effect in deltaepsilon. Supportm 1.2g of synthetic (illustration compound B-20) 2-n-Decyl- 5-[4-hydroxy Phenylco 1.3.4-thiadiazole of 2-n-Decyl- 5-[4-() lance 4'-n-propyl cyclohexyl carbonyloxy-phenyl]-1, 3, and 4-thiadiazole (3 and 77X 10= Mol) dry pyridine 2.5 m l and dry toluene 2, 5 Into the mixed solution of m 47, the dry toluene 2.5mj? solution of 0.71 g (3, 77X10-" Mol) of transformer 4-n-propyl cyclohexane carbonyl chloride was dropped in 15 minutes below by 5 degreeC. It agitated at after-dropping room temperature for 19 hours. Reaction solution was poured into after [ the end of a reaction ] ice water 50mjl!, and it was made pH 1 by 6N and HCI!. The solvent (benzene) was distilled off and the rough product was obtained, after extracting, washing and drying with benzene. Silica gel [ this ] chromatography refining using n-hexane/ethyl acetate =3/1 mixed solvent is performed, It re-crystallizes by ethanol and is 1.15-g 2-n-Decyl- 5-[4(transformer 4'-n-propyl cyclohexyl carbonyloxy)-phenyl ]. -1, 3, and 4-thiadiazole was obtained. (64.9% of yield) Phase-transition-temperature (degreeC) IR (cm-') 2925, 2850. 1740. 1600. 1510. 1470*1450, 1205. 1165. In Synthetic (Illustration Compound B-34) Example 11 of 1130. 980. 862 Fruit"1 Sail" Lambda2-N-Decyl- 5-[Phenyl [ 4 -(Transformer 4-N Pentyl Cyclohexyl Carbonyloxy)- ]]-1, 3, and 4-Thiadiazole, Instead of transformer 4-n-propyl cyclohexane carbonyl chloride, transformer 4-n-pentyl cyclohexane power report nil chloride is used, 2-n-Decyl- 5-[4-() lance 4-n-pentyl cyclohexyl carbonyloxy phenyl ] -1, 3, and 4-thiadiazole was obtained. yield: 60 or 2% Phase transition temperature (degreeC) IR(cm-') Two B60,2825,1750,1600, 1508,1470*1450, and 1205. 1162. 1135. 980. 860 Cusp"1 animal""2-n-Decyl- 5-[4-(transformer 4-n-propyl cyclohexyl methylene Oxy) phenyl]-1, 3, Composition (illustration compound B-3) of 4-thiadiazole 2-n-Decyl- 5-[4-hydroxyphenyl]-1, 3, and 4-Oxacyi / l/ 1.0g (3, 28x 10-" Mol) were dissolved in the Dimethylform amide of 20 m l. Potassium hydrate 0.5g was added to this 85%, and it agitated by 100 degreeC for 1 hour. 1.02 g (3, 28X10-" Mol) of transformer 4-n-propyl cyclohexyl methyl p-Ruen sulfonate was added to this, and also it agitated by 100 degreeC for 4 hours. The solvent was distilled off and the rough product was obtained, after pouring this into ice water 200 m j7 after the end of a reaction and extracting, washing and drying with benzene. Silica gel chromatography refining was performed, and also this was re-crystallized by ethanol, and 0.8 g of 2-n-Decyl- 5~[phenyl [ 4 -(transformer 4'-n-propyl cyclohexyl methylene Oxy)- ]]-1, 3, and 4-thiadiazole was obtained. (53.3% of yield) Phase-transition-temperature (degreeC) IR (cm-') 2945.2860. 1608.1580.1520.14B0*1460, 1320.1260.1180.1125.1040*985, 858 Real"1 animal "A 2-(l-methylpropyl ")-5 - (4 -(transformer 4-n-pentyl cyclohexyl carbonyloxy)- phenyl) Synthetic (illustration compound B-51) 1-methylpropyl 5-[4-hydroxyphenyl of -1, 3, and 4-thiadiazole -1, 3, and 0.3 g (1, 28X 10-" Mol) of 4-thiadiazole, Transformer 4-n-pentyl cyclohexyl carboxylic acid 0.26g It is 0.27 g (1, 31X 10-" Mol) of Xylcarbobo diimide to Dicyclo (1, 31X 10" Mol), Methylene chloride 15mI! was added to 0.03 g of 4-(1-pyrrolidinyl) pyridine, and it agitated at room temperature for 20 hours. Reaction solution was filtered after the end of a reaction, and also the methylene chloride washed. The solvent was distilled off and the rough product was obtained, after drying Filtrate and Wash liquid. This is re-crystallized twice by ethanol and it is 2-(1-methylpropyl)-5 [ 0.24-g ]. -(4-() lance 4-n-pentyl cyclohexyl carbonyloxy)- Phenyl]-1 *3.4-thiadiazole was obtained. (45.2% of yield) (degreeC) phase transition temperature B-7 was mixed at a rate of 4:1 among the examples of a liquid crystallinity compound denoted by general formula (I) of (9) and the above-mentioned present invention among examples (A group), and liquid crystal constituent F was obtained. It pinched among a pair of electrode substrates which performed rubbing processing to polyimide covering which covers an electrode for the above-mentioned ferroelectric liquid crystal compound (9) and liquid crystal constituent F, respectively, and produced the liquid crystal element like Example 7. Using these liquid crystal elements, the optical response under crossed nicols was detected by electric field impression of peaked peak voltage 20V, and speed of response was measured. A result is shown below. 40degreeC 25degreeC Ferroelectric liquid crystal compound (9) 400micro5610microsecond liquid crystal constituent F 320micro the thing for 5435 or more microseconds showed that the response characteristic improved by mixing the liquid crystallinity compound [example B-7] of the present invention to a ferroelectric liquid crystal compound [example (9)]. SupportW (38) was mixed with (1) at a rate of 4= 1 among the above-mentioned examples (A group), and liquid crystal constituent B was obtained. Next, inside B-2 of the example of a liquid crystallinity compound denoted by general formula (I) of the above-mentioned liquid crystal constituent B and the above-mentioned present invention was mixed at a rate of 9= 1, and liquid crystal constituent G was obtained. The liquid crystal element was produced like the case of Example 15 using the above-mentioned liquid crystal constituent B and liquid crystal constituent G, respectively. Impressed electromotive force was set to 30V using these liquid crystal elements, and also speed of response was measured by the completely same method as Example 15. A result is shown below. 35degreeC 25degreeC Liquid crystal constituent B 685 B s 1275 mus liquid crystal composition Acid 510 microseconds From the thing for 820 microseconds or more, by mixing liquid crystallinity compound B-2 of the present invention to liquid crystal constituent B showed that the response characteristic improved. Real]

L carp "1 B-34 was mixed by the following ratio among [ B-3 ] the liquid crystallinity compounds expressed in the general formula (1) of the present invention as zero among liquid crystal constituent B used in Example 16, and the above-mentioned example (B group), and liquid crystal constituent H was obtained. Liquid crystal constituent H all the (producing a liquid crystal element on the same conditions -- all (speed of response was measured on the same conditions.)) 1: B -3: B-34= 14 : 4: -- using the l above-mentioned liquid crystal constituent H -- Example 15 -- liquid crystal constituents B : A result is shown below. 35degreeC 25degreeC Liquid crystal constituent B (example 16) 685 p s 1275 p s liquid crystal constituent H520microsecond 670 From the thing more than p s, by mixing combining liquid crystallinity compound B-3 of the present invention, B-34, and other liquid crystal compounds 0 to liquid crystal constituent B showed that the response characteristic improved. Back Application j mouth" deltaepsilon mixed inside B-20 of the example of a liquid crystallinity compound denoted by the general formula (1) of liquid crystal C31014 by Chisso Corp. [deltaew-0, 4 (sin wave, 100 kHz)] which is almost O, and the present invention at a rate of 9:1, and obtained liquid crystal constituent I. and also liquid crystal layer thickness was 1.5 micrometers using above C51014 and liquid crystal constituent ■ -- Example 15 -- all (the liquid crystal element was produced in the similar way, respectively.) When the Tilt angle was measured under crossed nicols in 25 degreeC using the above-mentioned liquid crystal element, 7 * liquid crystal constituent ■ was 8.2' C51014. Next, when microscope observation was performed and the Tilt angle was measured, impressing the rectangle wave of ±8v on the frequency of 60 kHz, 8.8 degrees and liquid crystal constituent I became 14.2 degrees C51014. When transmissivity was measured at this time, C81014 was 7.8% and the liquid crystal constituent was 13%. When the contrast ratio was measured, 8:11 liquid-crystal constituent I was 40:1 C31014. It turned out that the above things can improve display properties according [ the liquid crystal element obtained by mixing liquid crystallinity compound B-20 expressed with the general formula (1) of the present invention to C31014 which is almost 0 ] to the AC Stabilize effect in deltaepsilon. Large"L eel "j (8) among the examples (A group) of the optically active compound which produces a spiral by adding to the nematic phase which is not chiral [ above-mentioned ], (13), (17), (18), (20) (33), ■, ■, ■, ■, and ■ were mixed by the following ratio among the liquid crystal compounds (B group) which have a smectic phase which is not chiral again, and (or) the Manet Chick phase for (34), (36), and (38), and liquid crystal constituent J was obtained. Liquid crystal constituent J (8): (13) : (17) : (18) : (20) : (33) : (34) : (36) : (38) :■2■:■:■:■=10:9:10 : lO:5:6:3:5:5:5:6:6: It is the Above-mentioned Constituent J to 12:8th Order, A-2, A-6*A-17, A-23, A-26, B-3, B-21, and B-33 were mixed by the following ratio among the examples of a liquid crystal compound denoted by general formula (I) of the above-mentioned present invention, and liquid crystal constituent K was obtained. To a liquid crystal constituent Liquid crystal constituent J : A-2 : A-6 : A-17 : A-23:A-26 : B-3 : B-21 : The liquid crystal element was created completely like Example 7 using the B-33=80:3:2:3:3:2:2:2:3 above-mentioned liquid crystal constituent J and liquid crystal constituent K. and also it made impressed electromotive force into peak to peak 35V using this liquid crystal element -- all (speed of response was measured on the same conditions.) A result is shown below. 10degreeC 25degreeC 40degreeC Liquid crystal constituent J 980 p see 3581t sec 135 p sec liquid crystal constituent Acid 900 p see 362 musec To 137 musec order, The place which measured the Tilt angle on the completely same conditions as Example 7 using these liquid crystal elements (60 kHz.) ±8v rectangle wave liquid crystal constituent J turned into 8.3' and a liquid crystal constituent to 13.8'. When the temperature dependence of reaction velocity had been improved by mixing the liquid crystal compound of the present invention from the above thing to liquid crystal constituent J and also it used for the method of presentation by the AC Stabilize effect, it turned out that display properties are improved. One gloss" Sen A-10, A-20, A-25, A-31*A-32, B-2, B-17, B-34, B-41, and B-43 were mixed by the following ratio to liquid crystal constituent J used in Example 19 among the examples of a liquid crystal compound denoted by general formula (I) of the above-mentioned present invention, and liquid crystal Composition was obtained. Liquid crystal Composition Liquid crystal constituent J : A-10, A-20, A-25 : A-31:A-32 : B-2 : B-17 : B-34 : B-41 : A liquid crystal element is created completely like Example 19 using the B-43=80:2:2:2:1:1:3:2:5: 1:1 above-mentioned liquid crystal Composition, Speed of response and a Tilt angle were completely measured on the same conditions. A result is shown below. Speed of response 10degreeC 25degreeC40'C 945microsec 370 musec From the thing more than 139 musec Tilt angle 14.3 *, the liquid crystal compound of the present invention is mixed to liquid crystal constituent J, When the temperature dependence of speed of response had been improved and also it used for the method of presentation by the AC Stabilize effect, it turned out that display properties are improved. Real"1 example "■2 (14) among the above-mentioned examples (A group), (21) (39), (107), (110), ■ among [ ■ ] (B groups), ■. ■ A [phase] and 0 were mixed by the following ratio and liquid crystal constituent M was obtained. Liquid crystal constituent M (14) + (21) : (39) : (107) : (110) :■:■:■:■: [phase] :@l=8 : 2 : 9 : 5 : 3 : 15 : 10 : 10 : 15 : 3 : To the 20th order, Inside B-6 of the example of a liquid crystallinity compound denoted by the above-mentioned liquid crystal constituent M and the above-mentioned general formula (I) was mixed by the following ratio, and a liquid crystal group and Acid N were obtained. Liquid crystal constituent N Liquid crystal constituent M : B-6=93 : The liquid crystal element was produced like Example 7 using the 7 above-mentioned liquid crystal constituent M and liquid crystal constituent N, respectively. using the above-mentioned liquid crystal element -- Example 7 -- all (when the Tilt angle was measured on the same conditions (60 kHz, ±8v rectangle wave), as for liquid crystal constituent M, 8.6 degrees and liquid crystal constituent N became 12.8 degrees.) From the above thing. It turned out that display properties according [ the liquid crystal element using liquid crystal constituent N obtained by mixing liquid crystallinity compound B-6 expressed with general formula (I) of the present invention by liquid crystal constituent M ] to the AC Stabilize effect are improved. SupportL" deafness Inside B-19 of the example of a liquid crystallinity compound denoted by liquid crystal constituent M of Example 21 and the above-mentioned general formula (I) was mixed by the ratio of 9:l, and liquid crystal constituent O was obtained. producing a liquid crystal element by the same method as Example 7 using the above-mentioned liquid crystal constituent O -- the completely same conditions as Example 7 -- a Tilt angle -- having measured (60 kHz, ±8v rectangle wave) -- time -- 14.2 degrees -- having become . 1 order" deafness B-40 was mixed by the following ratio among [ B-22*B-37 ] the examples of a liquid crystallinity compound denoted by liquid crystal constituent M of Example 21, and the above-mentioned general formula (I), and liquid crystal constituent P was obtained. Liquid crystal constituent P A liquid crystal element is produced by the same method as Example 7 using the liquid crystal constituent M2 above-mentioned liquid crystal constituent P, and they are the completely same conditions (60 kHz.) as Example 7. : B-22 : B-37 : B-40=90 : 6 : 2 : It became 13.7 * when the Tilt angle was measured by the ±8v rectangle wave. Mercy difference" day" ■, ■, 0 *o, o, o, and o were mixed by the following ratio among the above-mentioned examples (A group) (30), (40), (106), and among [ ■ ] the above-mentioned liquid crystal compounds (B group), and liquid crystal constituent Q was obtained. Liquid crystal constituent Q (30) : (40) : (106) :■, ■, ■, 0.■, 0.0.0= 3:4:3 Near: 12:9:15: B-15, B-21, B-23, and B-33 were mixed by the following ratio among [ B3 ] the examples of a liquid crystallinity compound denoted by the general formula (1) of 12:18:8:9, next the above-mentioned liquid crystal constituent Q and the above-mentioned present invention, and liquid crystal constituent R was obtained. Liquid crystal constituent R Liquid crystal constituent Q : B-3 : B-15 : B-21 : B-23 : The liquid crystal element was produced like the case of Example 7 using the B-33=90:2:2:2:3:1 above-mentioned liquid crystal constituent Q and liquid crystal constituent R, respectively. Speed of response was measured on the completely same conditions as Example 7 using these liquid crystal elements. A result is shown below. 35degreeC 25degreeC 15degreeC Place which measured the Tilt angle on the completely same conditions as Example 7 using Q 290 microseconds of liquid crystal constituent liquid crystal constituent R110micro5170micro5305microseconds, next these liquid crystal elements 93 microseconds (60 kHz.) 160 microseconds As for the ±8v rectangle wave and liquid crystal constituent Q, 8.2 degrees and liquid crystal constituent R became 13.4 degrees. When the temperature dependence of the response characteristic had been improved and liquid crystal constituent R which mixed the liquid crystal compound of the present invention to liquid crystal constituent Q was further used for the method of presentation by the AC Stabilize effect from the above thing, it turned out that display properties are improved sharply. 1 Wound" Jing Among the examples (A group) (6) of the above-mentioned optically active compound, (8), (26), (31), (33), (34), (39), (50) (92), They are [ (116) and ] a [phase] and a [phase] among liquid crystal compounds (B group) [a phase]. ■ ■ was mixed by the following ratio and liquid crystal constituent S was obtained. Liquid crystal constituent 5 (6) : (8) + (26) : (31) : (33) : (34) : (39) : (50) : (92) : (116) : [Phase]:[phase]: [phase] :@:■ = 5:6:4:8:3 Near: -- 20:10:2:5:32 -- B-31 and B-36 were mixed by the following ratio among [ B-5*B-17 ] the examples of a liquid crystallinity compound denoted by general formula (I) of 4:3:14:6, next the above-mentioned liquid crystal constituent S and the above-mentioned present invention, and liquid crystal constituent T was obtained. Liquid crystal constituent T Liquid crystal constituent S : Using the 5:17:31:36=85:3:2:4:6 above-mentioned liquid crystal constituent S and liquid crystal constituent T, cell thickness was 1.3 micrometers, and also it produced the liquid crystal element like Example 7. Impressed electromotive force was made into peaked peak 40V using these liquid crystal elements, and also speed of response was measured on the same conditions. A result is shown below. 35degreeC 25degreeCI5"C Place which measured the Tilt angle on the completely same conditions as Example 7 using S 70micro of liquid crystal constituent 5150micro5285microseconds, next these liquid crystal elements 751t s (60 kHz.) 175 mus 330 mus liquid crystal composition Acid As for the ±8■ rectangle wave and liquid crystal constituent S, 14 or 6 degrees and liquid crystal constituent T became 15.9 degrees. When speed of response and its temperature dependence had been improved from the above thing by mixing the liquid crystal compound of the present invention to liquid crystal constituent S and it used for the method of presentation by the AC Stabilize effect further, it turned out that display properties are improved. [Effect of the Invention] Re from the above example, or To -- like, the liquid crystal constituent and liquid crystal element using the liquid crystallinity compound denoted by general formula (I) of the present invention had the good response characteristic, and when using for the method of presentation by the AC Stabilize effect, it turned out that display properties are improved sharply.

[Brief Description of the Drawings]

Drawing 1 shows change of thetaa to V r m s of FLC from which the value of deltaepsilon differs.