JPH0312484A - Ferroelectric chiral smectic liquid crystal composition and liquid crystal element containing same - Google Patents

Abstract

PURPOSE:To obtain the subject composition, excellent in switching characteristics with AC stabilizing effects and suitable as liquid crystal-optical shutters, etc., by mixing a mixture of specific three kinds of liquid crystal compounds with a liquid crystal compound having a negative dielectric anisotropy. CONSTITUTION:The objective composition containing (A) a compound expressed by formula I [R1 and R2 are 1-18C (substituted) alkyl; X1 and X2 are single bond, -O-, -CO2-, etc.], (B) a compound expressed by formula II [R3 and R4 are (substituted) 1-18C alkyl; X3 and X4 are single bond, -O-, -CO2-, etc.; Z1 is -CO2-, etc.; formulas III and IV are phenylene, formula V, etc.; formula VI is phenylene, etc.], (C) a compound expressed by formula VII [R5 is (substituted) 1-18C alkyl; X5 is single bond, -O-, etc.; Z is single bond, -CO2-, etc.; formula VIII is formula V, etc.; m is 1-12] and (D) a liquid crystal compound having a negative dielectric anisotropy ( epsilon).

Description

[Detailed description of the invention]

[Technical Field] The present invention relates to a liquid crystal composition used in a liquid crystal element used in a liquid crystal display element, a liquid crystal light shutter, etc., and more specifically, a novel liquid crystal composition with improved response characteristics to an electric field and a novel liquid crystal composition comprising the same. It relates to liquid crystal elements. [Background Art] Liquid crystals have conventionally been applied as electro-optical elements in various fields. Most of the liquid crystal elements currently in practical use are, for example, M, 5chadt and W, “Applied Physics Letters” by Helfrich.
Vo, 18, No. 4 (1971, 2, 15), P
, 127-128 “Voltage-8 penden
t 0ptical Activity or
aTwisted Nematic Liquid
T N (t w i s
This uses a type of liquid crystal. These are based on the dielectric alignment effect of liquid crystals, and due to the dielectric anisotropy of liquid crystal molecules, the average molecular axis direction is oriented in a specific direction by an applied electric field. It is said that the limit of the optical response speed of an element is milliseconds, which is too slow for many applications.On the other hand, for applications to large flat disks, simple matrices are recommended due to cost, productivity, etc. In the simple matrix method, an electrode configuration in which scanning electrode groups and signal electrode groups are arranged in a matrix is adopted, and for driving, the scanning electrode groups are sequentially and periodically addressed. A time-division drive method is adopted in which signals are selectively applied, and a predetermined information signal is selectively applied in parallel to a group of signal electrodes in synchronization with an address signal. If a liquid crystal is used, a finite electric field will be applied to the area where the scanning electrode is selected and the signal electrode is not selected, or the area where the scanning electrode is not selected and the signal electrode is selected (so-called "half-selected point"). If the difference between the voltage applied to the selected point and the voltage applied to the half-selected point is large enough (and the voltage threshold required to align the liquid crystal molecules perpendicular to the electric field is set to a voltage value in between, The display element operates normally, but if the number of scanning lines (N) is increased, the entire screen (
The time during which an effective electric field is applied to one selected point (duty ratio) decreases at a rate of 1/N while scanning one frame. For this reason, the effective voltage difference between selected points and non-selected points when repeated scanning is
As the number of scanning lines increases, the size becomes smaller, resulting in unavoidable drawbacks such as a reduction in image contrast and crosstalk. This phenomenon is caused by liquid crystals that do not have bistability (the stable state is when the liquid crystal molecules are aligned horizontally with respect to the electrode surface, and they are aligned vertically only while an electric field is effectively applied). ) is essentially an unavoidable problem that arises when driving using the temporal accumulation effect (that is, repeatedly scanning). In order to improve this point, voltage averaging method, dual-frequency driving method, multiple matrix method, etc. have already been proposed, but all of these methods are insufficient, and it is necessary to increase the screen size and density of display elements. Currently, the number of scanning lines has reached a plateau due to the inability to increase the number of scanning lines sufficiently. In order to improve the drawbacks of conventional liquid crystal elements, the use of bistable liquid crystal elements has been proposed for C1ark and L
proposed by Agerwall (Japanese Unexamined Patent Application Publication No. 1983-1999)
1072119-publication, US Pat. No. 4,367,924, etc.). As the bistable liquid crystal, a ferroelectric liquid crystal having a chiral smectic C phase (SmC*) or H phase (SmH*) is generally used. This ferroelectric liquid crystal has a bistable state consisting of a first optically stable state and a second optically stable state in response to an electric field, and therefore is similar to the optical modulation element used in the above-mentioned TN type liquid crystal. For example, the liquid crystal is oriented in a first optically stable state with respect to one electric field vector, and the liquid crystal is oriented in a second optically stable state with respect to the other electric field vector. Further, this type of liquid crystal has a property (bistability) of taking one of the above two stable states in response to an applied electric field and maintaining that state when no electric field is applied. In addition to the above-mentioned feature of bistability, ferroelectric liquid crystals have the excellent feature of high-speed response. This is because the spontaneous polarization of the ferroelectric liquid crystal and the applied electric field act directly to induce a transition in the orientation state, which is 3 to 4 orders of magnitude faster than the response speed due to the effect of the dielectric anisotropy and the electric field. In this way, ferroelectric liquid crystals potentially have extremely excellent properties, and by utilizing these properties, many of the problems of conventional TN-type devices mentioned above can be overcome, which is quite essential. Improvement can be obtained. In particular, it is expected to be applied to high-speed optical shutters and high-density, large-screen displays. For this reason, extensive research has been conducted on liquid crystal materials with ferroelectric properties, but the ferroelectric liquid crystal materials developed to date have sufficient characteristics for use in liquid crystal devices, including low-temperature operation characteristics and high-speed response. It is hard to say that it is equipped with the following. To increase the response speed, (a) increase the magnitude of spontaneous polarization Ps (b) increase the viscosity η
There is a method of increasing the applied voltage E. However, since the applied voltage is driven by an IC etc., there is an upper limit, and it is desirable to lower it as much as possible. , it is necessary to increase the value of the magnitude of spontaneous polarization, Ps. 9 to obtain element configuration
There tends to be more restrictions. Also, even if the spontaneous polarization is unnecessarily made thicker, the viscosity tends to increase as well, and as a result, the response speed may not be as fast. For example, when the temperature is about 5 to 40°C, the response speed generally changes by about 20 times, which exceeds the limit of adjustment by driving voltage and frequency.As mentioned above, ferroelectric In order to put liquid crystal devices into practical use, a ferroelectric chiral smectic liquid crystal composition that has low viscosity, high-speed response, and low temperature dependence of response speed is required. Typical ferroelectric liquid crystal cell The configuration is I on a glass substrate.
Form an electrode pattern with TO, etc., and then form a short-circuit prevention layer for the upper and lower substrates with SiO2, etc. (approximately 1000 people) on top of that with polyimide (PI; Toshisha 5P510.710, etc.)
A film is formed to a thickness of about 400 layers, and the PI films are rubbed and then faced to each other in a vertically symmetrical orientation, and the spacing between the substrates is maintained at 1 to 3 μm. On the other hand, it is known that ferroelectric liquid crystals aligned under such conditions generally connect the upper and lower substrates in a twisted state and do not exhibit -axial alignment (spray alignment). One of the problems in such cases is that the transmittance of the liquid crystal layer is low. Assuming that the molecular orientation is uniaxial, the amount of transmitted light has an intensity of 1 relative to the intensity of the incident light I0 under crossed Nicol conditions. where Δn is the refractive index anisotropy, d is the cell thickness, λ is the wavelength of the incident light, and θa is the angle between bistable states (tilt angle). When using the above-mentioned cell and taking the streak 1 no orientation, θa is currently 5° to 8°. Control of Δndπ/λ cannot be easily performed in terms of physical properties, so it is desirable to increase θa to increase I, but this is difficult to achieve using static alignment techniques. For such problems, it is known that θa can be expanded by using the torque of the Δε term of the ferroelectric liquid crystal (published by A and T T in 1983. 3 ID, JP-A-61-245142). .61-246722.6
1-246723.61-246724.61-249
024.6l-249025). When Δε of the liquid crystal is negative, the liquid crystal molecules tend to become parallel to the substrate due to the application of an electric field. Taking advantage of this property, i.e.
By applying a constant effective electric field even during switching, it is possible to eliminate this twisted arrangement, increase θa, and increase the transmittance (AC stabilization effect). The torque r acting on the FLC molecule regarding state switching
'psSAC stabilizes the FLC molecules (torque rAa) is proportional to the following physical properties: I'ps co PsaE... (2
)r■ ω Δε・ε. -E2... (3) As is clear from equation (3), it can be seen that the sign and absolute value of Δε of FLC play an extremely important role. Vr of four types of FLCs with different values of physical properties regarding Δε
FIG. 4 shows the change in θa with respect to ms. The measurement was performed using a rectangular alternating current of 60 KHz to eliminate the influence of Ps. (I) is Δε knee 5.5, (n) is Δε knee 3.0, (
I[[) is Δε knee 0, (rV) is Δε2 1.0, and as can be seen from the graph, θa increases at extremely low voltages where Δε is large and negative, and therefore contributes to ■. I understand. Comparing the difference in transmittance when using (I) and (m), there was a clear difference between 15% for (I) and 6% for (III) (60 K i -1z
±8v square wave applied). As is known from the above examples, the display characteristics of 5SFLC can be greatly changed by controlling the physical properties of Δε and Ps. In order to make the Δε of the ferroelectric liquid crystal composition negative,
It is most effective to mix materials with a negative Δε and a large absolute value. For example, a compound with a large Δε can be obtained by introducing a halogen or cyano group in the short axis direction of the molecule, or by introducing a heteroatom into the molecular ring skeleton. The dielectric anisotropy of a compound with Δε<0 varies depending on its structure. An example is shown below. ε Ku2 2 ≦ ε ≦ 5 1 ε1 > 10 5 Ku ε <10 *R and R' represent an alkyl group. Thick (classified:) Compounds with ε1≦2 (lΔε1 small), compounds with 2×1ε1≦10 (1Δε1 medium), Δεl>
10 (lΔε 1 large). 1Δ
When ε1 is small, there is almost no effect of increasing 1Δεl. A material with 1Δε greater than 1 is a very effective material for increasing 1Δε. At present, dicyanohydroquinone derivatives are the only 1Δε1 material. However, dicyanohydroquinone derivatives are
Although the effect of increasing ε1 is increased, since the viscosity is high, an increase in the content ratio tends to worsen the switching characteristics. On the other hand, among those with medium 1Δεl, the 1Δε increasing effect is smaller than the 1Δε1 major component, but some have low viscosity to some extent. From the above, it is clear that the switching characteristics are good and the A
In order to obtain a liquid crystal composition having a C stabilizing effect and a liquid crystal element containing the same, it is necessary to select a compound with negative dielectric anisotropy, preferably a compound with 1Δε1〉2, and to adjust the mixing partner and the mixing ratio ( [Problems to be Solved by the Invention] An object of the present invention is to provide a chiral smectic liquid crystal that has a high response speed and reduces the temperature dependence of the response speed so that a ferroelectric liquid crystal element can be put to practical use. It is an object of the present invention to provide a composition and a liquid crystal element using such a liquid crystal composition.Another object of the present invention is to further mix a liquid crystal compound having negative dielectric anisotropy with the liquid crystal composition of the present invention. By AC
The object of the present invention is to provide a liquid crystal element that has a stabilizing effect and greatly improves display characteristics. ,・') (blank below) 7' [Means for solving the problem] The present invention is based on the following - (I) single bond, (where RI+R2 is a linear or branched alkyl group of C1 to Cta) Yes, C, ~C1□ as a substituent
It may have an alkoxy group of Indicates either X, or X2. ) and at least one of the compounds represented by
I) (However, R3+R4 is C1 which may have a substituent
- At least one type of compound represented by a linear or branched alkyl group of Cl1l, and the following - C1-Ct (where R5 may have a substituent)
A ferroelectric chiral characterized by containing a linear or branched alkyl group of S, at least one compound represented by the X5 beam, and at least one liquid crystalline compound having negative dielectric anisotropy. The present invention provides a smectic liquid crystal composition and a liquid crystal element formed by disposing the liquid crystal composition between a pair of electrode substrates. Further, in the present invention, the liquid crystalline compound having negative dielectric anisotropy preferably exhibits Δε<-2, more preferably Δε<-5,
More preferably, the present invention provides a ferroelectric chiral smectic liquid crystal composition which is further contained in the ferroelectric chiral smectic liquid crystal composition using a liquid crystal compound exhibiting Δε<-10, and a liquid crystal element having the same. Further, the present invention provides that the liquid crystalline compound having negative dielectric anisotropy is
A ferroelectric chiral smectic liquid crystal composition further containing the ferroelectric chiral smectic liquid crystal composition using a compound selected from the following - (■-■) to (■-■), and a ferroelectric chiral smectic liquid crystal composition comprising the same. The present invention provides a liquid crystal element. - Killing (■-■) General formula (■-■) (R,. Rt is a linear chain that may have a substituent or [,. Rb is a linear chain that may have a substituent or branched alkyl group, branched alkyl group, e A

[ is −÷ sha single bond, where A. At cannot become a single bond at the same time. ] General slaughter ■−■) A@. When both Abs are single bonds, Xb. Xc is a single bond, and Xa. Xd is both a single bond or both are 10-, or X is -Co- and xd is 100-. Ya. Yb is a cyano group. halogen. Hydrogen, however, Ya. Yb cannot become hydrogen at the same time. ] (A+ is a single bond, -g) - Al is a single bond, + R1, R1 is a straight chain or branched alkyl group that may have a substituent, provided that when A is a single bond, it is a straight chain alkyl group. Z3 is a -〇- or -S- general formula, however, when A is a single bond, X is a single bond, (R1゜Rm is a linear or branched alkyl group that may have a substituent, When is a single bond, Xk is a single bond.] Ak. AI cannot be a single bond at the same time. -CH2CH2- -c=c-] Alkyl group, -OCH2- -CH2CH2-',... Among the compounds represented by the above general formula (1), preferred examples of compounds include compounds represented by the following formulas (1-a) to (I-p). Furthermore, R in the above formulas (1-a) to (I-p)
,, Preferred examples of R2 include (I-i) to (I-v
i). R1 is n alkyl group R2 is n alkyl group -1i) R, is n alkyl group CH3 R2 is 6CH2), CHR, s (optically active or racemic) -vi) CH3 Optically active or racemic) CH3 R2 is ÷CH2 gas CH mo Cl-12), CHR7 (optical active or racemic) -iii) -iv) -v) R1 is n alkyl group CH. R2 is +CH2, CH÷CH2"rt (optically active or racemic) CH3 R1 is (-CH2, CHRs (optically active or racemic) R2 is n alkyl group CH3 R1 is moCH2), CHR. (optically active or racemic) CH3 R2 is ÷ CH2 CHR. (Optically active or racemic) R6+ R? r R11 represents a linear or branched alkyl group. pr q+ S is O to 7, and r is 0 Alternatively, among the compounds represented by the above-mentioned general formula (II), preferred compound examples include the following (n-a) to (II-
q) Compounds represented by the formula can be mentioned. Moreover, as a preferable example of X 3 r x4 in the above-mentioned formulas (na) to (II-q), (II-t) to
(■-viii) can be mentioned. x3 is a single bond X3 is a single bond X3 is 10- X3 is 10- x4 is 10- X4 is a single bond x4 is 10- is a single bond (II -1) (II -1i) (U -1ii) (II-iv) (I[-v) (II -vi) (U -vii) X3 is -CO-X4 10-(■-viii) Furthermore, R3 in the above formulas (II-a) to (II-q)
．． A preferred example of R4 is a linear alkyl group. Moreover, among the compounds represented by the above-mentioned general formula (m), preferred examples of the compounds include the following (m-a). (m-b) A compound represented by the formula can be mentioned. An example of a specific structural formula of the liquid crystalline compound represented by the above-mentioned -Sakatsuki (1) is shown below. ! ■-19 ■-21 ■-44 l-87 CH3 The compound represented by the above-mentioned -Sakatsu (I) is, for example,
1-93170. JP-A-61-24576, JP-A-61
-129170. Japanese Patent Publication No. 61-200972. Tokukai Showa 6
1-200973. Japanese Patent Publication No. 61-215372. Japanese Patent Publication No. 61-291574. East German Patent 95892 (1973
It can be obtained by the synthetic method described in 2010). For example, it can be obtained by the synthetic route shown below. Typical synthesis examples of the compound represented by ゝ・-, 'elm' (R1+R21X3 are as described above)--Sakuhatsu (1) are shown below. Synthesis Example 1 (Synthesis of compound No. 1-71) 1.06 5-methoxyhexanol dissolved in 5 ml of pyridine
g (8.0 mmol) of p-toluenesulfonic acid chloride dissolved in 5 mβ of pyridine.
, 6 mmol) was added dropwise at below 5° C. in ice water. After stirring at room temperature for 6 hours, the reaction mixture was poured with 100 mjl of cold water! injected into. After making the mixture acidic with 6N hydrochloric acid, the mixture was extracted with isopropyl ether. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and then the solvent was distilled off to obtain 5-methoxyhexyl-p-toluenesulfonate. 5-decyl-2-(p
-hydroxyphenyl)pyrimidine 2, Og(6,41
mmo1), add 0.61 g of potassium hydroxide, and add 100
Stirred at ℃ for 40 minutes. To this was added the previously obtained 5-methoxyhexyl-p-toluenesulfonate, and the mixture was heated to 100°C.
The mixture was heated and stirred for 4 hours. After the reaction is complete, pour the reaction mixture into 100ml of cold water! and extracted with benzene. After washing with water, it was dried over anhydrous magnesium sulfate and the solvent was distilled off to obtain a pale yellow oil. After purification by column chromatography (silica gel-ethyl acetate/benzene = 1/9),
Recrystallized from hexane to give 5-decyl-2-[4-(5')
1.35 g of -methoxyhexyloxy)phenyl]pyrimidine (compound No. 2-60) was obtained. Phase transition temperature (℃) Synthesis Example 2 (Synthesis of compound No. 1-78) 2.04 g of 6-pentyloxyheptanol was added to 8 mj of pyridine.
2 and cooled with water, 2.26 g of tosyl chloride dissolved in 5 ml of pyridine was gradually added dropwise (below 500, 7 minutes). Thereafter, the mixture was stirred at room temperature for 5 hours. Pour the reaction mixture into 150ml of ice water! After adjusting the pH to about 3 with 6N aqueous hydrochloric acid solution, the mixture was extracted with ethyl acetate. This was washed with water, dried over anhydrous magnesium sulfate, and the solvent was distilled off to give (6-pentyloxyheptyl) p
-) 2.98 g of luenesulfonate was obtained. 3.12 g of 5-n-decyl-2-(4-hydroxyphenyl)pyrimidine and 0.53 g of potassium hydroxide were dissolved in 14 ml of dimethylformamide, heated and stirred at 100°C for 3 hours, and then (6-pentyloxyheptyl)p −
2.98 g of toluene sulfonate was added, and the mixture was heated and stirred at 100° C. for 5 hours. The reaction mixture was poured into 200 mf of ice water, adjusted to pH approximately 3 with a 6N aqueous hydrochloric acid solution, and then extracted with benzene. This was washed with water, dried over anhydrous magnesium sulfate, and the solvent was distilled off to obtain 4.71 g of a crude product. This was purified by silica gel column chromatography (n-hexane/ethyl acetate = 10/2)
After that, it was further recrystallized from hexane to give 5-n-decyl-2-[4-(6-pentyloxyhebutyloxy)
1.56 g of phenyl]pyrimidine was obtained. I R (cm-') 2924.2B52, 1610, 1586, 1472° 1436.1254, 1168, 1096. 798 Phase transition temperature (℃) 22.7 33.3 39
．． 8.For compounds other than the synthesis side, the following synthetic route A is used. It can be obtained by specific combination of the compound represented by the above-mentioned formula (II). An example of a structural formula is shown below. Synthetic route A, synthetic route B (In the above, R I is as described above) ○ ○ ○ n-C7H+a (Mashoki C4H. A typical synthesis example is shown below. Synthesis Example 1 (Synthesis of Compound No. 2-4) 5-dodecyl-
2-(4'-hydroxyphenyl)pyrimidine 1.0
g (2.94 mmoi) was dissolved in 4 ml of toluene and 4 ml of pyridine. To this, 0.55 g of trans-4-n-propylcyclohexanecarboxylic acid chloride (manufactured by Kanto Kagaku ■) dissolved in 4 m of toluene and ff was added in an ice water bath at 5°C.
It was gradually added dropwise. After the dropwise addition was completed, the mixture was stirred at room temperature for 12 hours, and the reaction mixture was poured into 100 ml of ice water. 6N
After acidifying with hydrochloric acid, extract with benzene, and add water and
It was washed successively with a 5% sulfur/lium hydrogen carbonate aqueous solution and water. After drying with magnesium sulfate, the solvent was distilled off to obtain a cream-colored crude product. After the product was purified by column chromatography, it was further recrystallized from a mixed solvent of ethanol and ethyl acetate to obtain 0.94 g of the white title compound. (Yield 64.8%) Phase transition temperature (°C) Synthesis Example 2 (Synthesis of Compound No. 2-72) (I) Trans-4-n-propylcyclohexanecarboxylic acid chloride log (53,6 mmoj2) was dissolved in ethanol 30
A small amount of triethylamine was added thereto, and the mixture was stirred at room temperature for 10 hours. Pour the reaction mixture into 100 mL of ice water.
After adding 6N hydrochloric acid aqueous solution to make it acidic, the mixture was extracted with isopropyl ether. The organic layer was washed with water repeatedly until the washing liquid became neutral, and then dried with magnesium sulfate. After distilling off the solvent, the residue was purified by silica gel column chromatography to obtain 9.9 g of trans-4-n-propylcyclohexanecarboxylic acid ethyl ester. (I[) Lithium aluminum hydride 0.73g (19
, 1 mmoj was added to 30 ml of dry ether, and the mixture was heated and refluxed for 1 hour. After cooling to about 10°C in an ice water bath, 5 g (25.6 mmol) of trans-4-n-propylcyclohexanecarboxylic acid ethyl ester dissolved in 30 mj' of dry ether was gradually added dropwise. After the dropwise addition was completed, the mixture was stirred at room temperature for 1 hour, and further heated under reflux for 1 hour. This was treated with ethyl acetate and a 6N aqueous hydrochloric acid solution, and then poured into 200 mj7 of ice water. After extraction with isopropyl ether, the organic phase was extracted with water,
It was washed successively with an aqueous sodium hydroxide solution and water, and dried over magnesium sulfate. After distilling off the solvent, it was purified by silica gel column chromatography to obtain trans-4-n-
3.5 g of propylcyclohexylmethanol was obtained. (■) Trans-4-n-propylcyclohexylmethanol 3.4g (22°4mmoi') was added to pyridine 2
It was dissolved at 0mf. 5.3 g of p-toluenesulfonic acid chloride dissolved in 20 ml of pyridine was added dropwise to this while cooling to 5° C. or lower in an ice water bath. After stirring at room temperature for 10 hours, the mixture was poured into 200 rrl of ice water. The mixture was made acidic with a 6N aqueous hydrochloric acid solution, and then extracted with isopropyl ether. The organic phase was washed with water repeatedly until the washing liquid became neutral, and then dried with magnesium sulfate. The solvent was distilled off to obtain trans-4-n-propylcyclohexylmethyl-p-toluenesulfonate. (IV) 5-decyl- in 40 ml of dimethylformamide
2-(4'-hydroxyphenyl)pyrimidine 6.3g
(20.2 mmoj?) was melted. 1.5 g of 85% potassium hydroxide was added to this, and the mixture was stirred at 100°C for 1 hour. To this was added 6.9 g of trans-4-n-propylcyclohexylmethyl-p-toluenesulfone-1, and the mixture was further stirred at 1OOoC for 4 hours. After the reaction was completed, the mixture was poured into 200 mj7 of ice water and extracted with benzene. After washing the organic phase with water, it was dried with magnesium sulfate. After distilling off the solvent, the residue was purified by silica gel column chromatography, and further recrystallized from a mixed solvent of ethanol/ethyl acetate to obtain the above-mentioned Exemplary Compound No. 2-72. IR (cm→): 2920, 2840. 1608. 1584142
8, 1258. 1164. 800 phase transition temperature ('C) Also, when Z is a single bond, for example, a compound represented by the formula (Sm2 is S m A. Smectic phase other than SmC. Unidentified) can be synthesized by the following synthetic route. can do. An example of a specific structural formula of the compound represented by the above-mentioned -salt (m) is shown below. -i8 F F ○ ([[) Compounds represented by the following synthetic routes A and B. It can be obtained with C. Synthetic route A Synthetic route B Synthetic route C (XS:O) Representative synthetic examples of the compound represented by general formula (III) are shown below. Synthesis Example 1 (Synthesis of Compound No. 3-17) p-2-fluorooctyloxyphenol! ,OOg(4,16m
M) in 10 ml of pyridine. ) A solution of 1.30 g (6,00 mM) of trans-4-n-pentylcyclohexanecarboxylic acid chloride dissolved in 5 ml of toluene was added dropwise at 5° C. or lower over 20 to 40 minutes. After the dropwise addition, the mixture was stirred at room temperature overnight to obtain a white precipitate. After the reaction was completed, the reaction product was extracted with benzene, and the benzene layer was further washed with distilled water, and then the benzene layer was dried over magnesium sulfate, and the benzene was distilled off. It was further purified using silica gel column chromatography and recrystallized from ethanol/methanol.
n-pentylcyclohexanecarboxylic acid-p-2-fluorooctyloxyphenyl ester 1.20g (2
, 85mM) was obtained. (Yield 68.6%) NMR data (ppm) 0.83-2.83ppm (34H, m) 4.00
~4.50ppm (2HSq)7,llppm
(4HSs) IR data (cm-') 3456, 2928° 1470, 1248° 854° Phase transition temperature ('C) 1742, 1508° 2852° 1166, 1132° 1200° (here, "a, S 4+ S S, S 6 is S
Shows a phase with a higher degree of order than mC*. ) Synthesis Example 2 (Synthesis of Compound No. 3-29) In a container that was sufficiently purged with nitrogen, (-)-2-fluoroheptazole 0
, 40 g (3.0 mm o 1 ) and 1.00 g (13 mmol) of dry pyridine were added and dried under water cooling for 30 minutes. Add 0.69 g (3.6 mmol) of p-toluenesulfonic acid chloride to the solution, and
Stirring was continued for an hour. After the reaction is complete, add 1N HCA aqueous solution 1
After extraction was performed twice with 10 ml of methylene chloride, the extract was washed once with 10 rrl of distilled water. After appropriately adding anhydrous sodium sulfate to the obtained methylene chloride solution and drying, the solvent was distilled off.
g (2.0 mmol) was obtained. Yield is 66%. The specific rotation and IR data of the product are as follows. Specific optical rotation [Cl]'? +2.59° (C=1
, CHCl3). Specific rotation [α] +9.58″ (c=1, CHCl
3). IR(am-'): 2900, 2850, 1600, 1450.13
50, 1170, 1090. 980.810,
660. 550° 0.43 g (1,5
1 to 0.28 g (1.0 mm, ol) of 5-octyl-2-(4-hydroxyphenyl)pyrimidine
-Butanol 0.2 mA' was added and stirred well. Immediately pour into the solution an alkaline solution prepared in advance by dissolving 0.048 g (1.2 mmol) of sodium hydroxide in 1.0 ml of l-butanol.
The mixture was heated under reflux for an hour and a half. After the reaction was completed, 10 ml of distilled water was added, and extraction was performed once each with 10 ml and 5 ml of benzene, and the extract was dried by appropriately adding anhydrous sodium sulfate. After drying, the solvent was distilled off and the target product (+)-S was purified using a silica gel column (chloroform).
-Octyl-2-[4-(2-fluoroheptyloxy)phenyl]pyrimidine O, 17g (0,43mmo
l) was obtained. The yield was 43%, and the specific rotation and IR were as follows:
The data was obtained. Specific optical rotation [α coF'+0.44' (c = 1
, CHCl). Specific optical rotation [α + 4.19° (c=1, CHCl
3). IR (am”): 2900, 2850.1600, l580°1420
, 1250, 1160.800.720, 650, 5
Examples of specific structural formulas of liquid crystal compounds represented by (■-■) to (■-■) are shown below. however,(
TV) In the formula, the number of carbon atoms in the alkyl group represented by each R is 1.
-ts, preferably 4 to 16, more preferably 6 to 12
shows. General formula (■-■) Susususususu lili lili interval C SuC LilyC 1"N 1"N Ririsr SuN SuN SuρN Su-Saburu (■-■) Sushi-Saboku (■-■) General formula (■-■) - Killing (■-■) N N N N N The liquid crystal composition of the present invention contains at least one compound represented by the general formula (1) and the compound represented by the general formula (r At least l$f1 of the compound, and at least one kind of the compound represented by the general formula (1), and another liquid crystal compound 1
It can be obtained by mixing at least one species in an appropriate ratio. A liquid crystal composition for another purpose of the present invention can be obtained by further mixing at least one liquid crystal compound having negative dielectric anisotropy in an appropriate ratio to the above liquid crystal composition. Further, the liquid crystal composition according to the present invention is preferably a ferroelectric liquid crystal composition, particularly a ferroelectric chiral smectic liquid crystal composition. Specific examples of other liquid crystal compounds used in the present invention are listed below. CaH170+CO3+ 0CH2ClIC2115* υ υ In the ferroelectric liquid crystal composition of the present invention, a liquid crystalline compound represented by the general formula (I) of the present invention, a liquid crystalline compound represented by -Kiburi (II), and -Kibari (II) The compounding ratio of each of the liquid crystal compounds represented by and one or more of the other liquid crystal compounds mentioned above or a liquid crystal composition containing them (abbreviated as liquid crystal material) is based on the present invention - per 100 parts by weight of the liquid crystal material. Killing (I), - Killing (II) and - Killing (I [
It is preferable that each of the liquid crystalline compounds represented by [) be 1 to 300 parts by weight, more preferably 2 to 100 parts by weight. Furthermore, when using two or more of the liquid crystalline compounds represented by the general formula (I), -Saburi (n) and -Saburi (m) of the present invention, the blending ratio with the liquid crystal material is as follows:
Per 100 parts by weight of the above-mentioned liquid crystal material, the present invention - I
), 1 to 500 parts by weight, more preferably 2 to 100 parts by weight of any one or a mixture of two or more of the liquid crystal compounds represented by -Sakatsu (U) and -Sakatsu (III).
It is preferable to use parts by weight. In addition, the ratio of each of the liquid crystalline compounds represented by -Kakkatsu (I) to (m) is expressed by the general formula (1) /-Kakkatsu (■) /-Kakkatsu (m) = 1
~300/1~300/1~300, and preferably, General formula (I) /-killing (■) /-killing (m) = 1
~50/l~50/l~50 is desirable. When two or more of each of the liquid crystalline compounds represented by formulas (I) to (■) are used, the respective ratios are -Kiraku(1)/
- Killing (■) / - Killing (■) (2 or more types) (2 or more types) (2 or more types) = 1-500/1-500
/1 to 500, and more preferably general formula (1) /-Sakatsu (■) /-Sakatsu (III)
2 or more types) (2 or more types) (2 or more types) = 1
~50/1~50/1~50 is desirable. In addition, the ratio of the above-mentioned liquid crystal material to the total amount of the liquid crystalline compounds represented by -Kakuburu (I) to (m) is based on 100 parts by weight of the above-mentioned liquid crystal material when each of the liquid crystalline compounds is used one by one. -The total amount of liquid crystalline compounds represented by (I) to (III) is 3 to 900 parts by weight, more preferably 6 to 300 parts by weight.
Parts by weight are desirable. - When using any of the liquid crystal compounds represented by (I) to (m) or two or more of each, the ratio of the above-mentioned liquid crystal material to the total amount of the liquid crystal compound is 100% of the above-mentioned liquid crystal material. It is desirable that the total amount of the liquid crystalline compounds represented by (1) to (m) be 3 to 1500 parts by weight, more preferably 6 to 300 parts by weight. Furthermore, the content of the component with negative dielectric anisotropy in the ferroelectric liquid crystal composition containing the component with negative dielectric anisotropy is 1
~97% by weight. In particular, when using a component with Δε<-2, the content of the component with Δε<-2 is desirably 1 to 70% by weight, preferably 1 to 50% by weight. A liquid crystalline compound represented by general formula (I) and
The total amount of the liquid crystalline compound represented by , the liquid crystalline compound represented by -Kiroku (III), and the component with negative dielectric anisotropy is:
It is contained in the ferroelectric liquid crystal composition of the present invention in an amount of 4 to 100% by weight. The dielectric anisotropy of the liquid crystal compound with negative dielectric anisotropy used in the present invention is preferably lε1-2. FIG. 1 is a schematic cross-sectional view of an example of a liquid crystal element having a ferroelectric liquid crystal layer according to the present invention, for explaining the structure of the ferroelectric liquid crystal element. In FIG. 1, 1 is a ferroelectric liquid crystal layer, 2 is a glass substrate, 3 is a transparent electrode, 4 is an insulating alignment control layer, 5 is a spacer, 6 is a lead wire, 7 is a power source, 8 is a polarizing plate, 9 indicates a light source. The two glass substrates 2 are made of In and 203°Sn, respectively.
O2 or ITO (Indium-Tin Oxi
A transparent electrode made of a thin film such as de) is coated. On top of this, a thin film of a polymer such as polyimide is rubbed with gauze or acetate flocked cloth to form an insulating alignment control layer that aligns the liquid crystals in the rubbing direction. Insulating materials such as silicon nitride, hydrogen-containing silicon carbide, silicon oxide, boron nitride, hydrogen-containing boron nitride, cerium oxide, aluminum oxide, zirconium oxide, titanium oxide, and fluoride An inorganic insulating layer such as magnesium is formed, and then polyvinyl alcohol, polyimide, polyamideimide, polyesterimide, polyvaraxylene, polyester, polycarbonate, polyvinyl acetal, polyvinyl chloride, polyvinyl acetate, polyamide, polystyrene, cellulose resin An insulating orientation control layer may be formed of two layers, using an organic insulating material such as melamine resin, Yulia resin, acrylic fat, or photoresist resin as an orientation control layer (or an insulating orientation control layer of an inorganic material). Alternatively, it may be a single layer of an organic insulating orientation control layer.If this insulating orientation control layer is inorganic, it can be formed by a vapor deposition method, or if it is organic, it can be formed by a solution in which an organic insulating material is dissolved or its precursor. body solution (solvent 0.1-20% by weight, preferably 0.2-10% by weight)
) using a spinner coating method, dip coating method, screen printing method, spray coating method, roll coating method, etc.
It can be cured and formed under predetermined curing conditions (for example, under heating). The thickness of the insulating orientation control layer is usually 30 to 1 μm, preferably 30 to 3000, more preferably 50 to 1 μm.
000 people is suitable. These two glass substrates 2 are kept at an arbitrary distance by a spacer 5. For example, using silica beads or alumina beads with a predetermined diameter as spacers, the glass substrate 2
There is a method in which the material is held between two sheets and the surrounding area is sealed using a sealing material such as an epoxy adhesive. In addition, a polymer film or glass fiber may be used as a spacer. A ferroelectric liquid crystal is sealed between these two glass substrates. The ferroelectric liquid crystal layer in which the ferroelectric liquid crystal is sealed is generally 0.5 to 20 μm, preferably 1 to 5 μm. Further, it is desirable that this ferroelectric liquid crystal has an SmC* phase (chiral smectic C phase) in a wide temperature range including room temperature (particularly on the low temperature side) and has high-speed response. Furthermore, it is desired that the temperature dependence of the response speed be small and that the drive voltage margin be wide. In addition, in order to obtain a monodomain state exhibiting good homogeneous orientation, especially when used as an element, the ferroelectric liquid crystal should be changed from the Toyoyoshi phase to the ch phase (cholesteric phase) - SmA phase (smectic human phase) - 3mC* Phase (chiral smectic C phase)
It is desirable to have the following phase transition series. The transparent electrode 3 is connected to an external power source 7 by a lead wire. Further, a polarizing plate 8 is bonded to the outside of the glass substrate 2. The device shown in FIG. 1 is of a transmission type, so it is equipped with a light source 9. FIG. 2 schematically depicts an example of a cell for explaining the operation of a ferroelectric liquid crystal element. 21a and 21b are In2O3, 5n02 or ITO (Indiu
It is a substrate (glass plate) coated with a transparent electrode made of a thin film such as (m-Tin Oxide), between which a liquid crystal of SmC wood phase or SmH* phase is oriented so that the liquid crystal molecular layer 22 is perpendicular to the glass surface. It is enclosed. A thick line 23 represents a liquid crystal molecule, and this liquid crystal molecule 2
3 has a dipole moment (on P) 24 in the direction perpendicular to its molecule. When a voltage higher than a certain threshold is applied between the electrodes on the substrates 21a and 21b, the helical structure of the liquid crystal molecules 23 is unraveled, and the dipole moments (P) 24 are all directed in the direction of the electric field. The liquid crystal molecules 23 have an elongated shape and exhibit refractive index anisotropy in the long axis direction and the short axis direction.
Therefore, it is easily understood that, for example, if crossed Nicol polarizers are placed above and below a glass surface, a liquid crystal optical modulation element whose optical characteristics change depending on the polarity of applied voltage can be obtained. The liquid crystal cell preferably used in the optical modulation element of the present invention can have a sufficiently thin thickness (for example, 10 μm or less). As the liquid crystal layer becomes thinner, the helical structure of the liquid crystal molecules unravels even when no electric field is applied, as shown in Figure 3, and the dipole moment Pa or Pb is directed upward (34a) or downward (34b). ). In such a cell, an electric field Ea or Eb of different polarity above a certain threshold value is applied as shown in FIG.
is applied by the voltage applying means 31a and 31b, the dipole moment changes direction to upward direction 34a or downward direction 34b corresponding to the electric field vector of electric field Ea or Eb,
Accordingly, the liquid crystal molecules are aligned in either the first stable state 33a or the second stable state 33b. As mentioned above, there are two advantages to using such ferroelectricity as an optical modulation element. The first is that the response speed is extremely fast, and the second is that the alignment of liquid crystal molecules has bistability. To further explain the second point with reference to FIG. 3, for example, when the electric field Ea is applied, the liquid crystal molecules are oriented in a first stable state 33a, and this state remains stable even when the electric field is turned off. Furthermore, when an electric field Eb in the opposite direction is applied, the liquid crystal molecules are oriented to the second stable state 33b and change their orientation, but they remain in this state even after the electric field is turned off. Also, the electric field E
As long as a or Eb does not exceed a certain threshold, the respective previous orientations are maintained. EXAMPLES The present invention will be explained in more detail with reference to Examples below, but the present invention is not limited to these Examples. Example 1 The following exemplified compounds were mixed in 1 part by weight to prepare liquid crystal composition 1.
-A was created. Exemplary compound No. Structural formula exemplary compound N
o. Structural formula Furthermore, this liquid crystal composition 1. -A was mixed with the following exemplified compounds in the weight parts shown below to prepare liquid crystal composition 1-B. Exemplary compound No., Structural formula
Weight 1 part -A Next, device characteristics etc. were observed using a cell prepared using this liquid crystal composition 1-B according to the following procedure. Two glass plates with a thickness of 1 mm and 1 mm were prepared, an ITO film was formed on each glass plate to form a voltage application electrode, and SiO□ was further vapor-deposited thereon to form an insulating layer. On this substrate, a polyimide resin precursor [Toshi ■ 5P-71
0] 1.0% dimethylacetamide solution at 25 rotations.
Coating was performed for 15 seconds using a spinner at 00 rpm. After the film was formed, a heating condensation firing process was performed at 300° C. for 60 minutes. The thickness of the coating film at this time was about 200. This fired coating was rubbed with acetate flocked cloth, then washed with isopropyl alcohol solution, and silica beads with an average particle size of 1.5 μm were sprinkled on one glass plate. so that they are parallel to each other, and apply adhesive sealant [Rixon Bond (
Glass plates were bonded together using a Chisso (Japanese Society) cooperator and dried by heating at 100° C. for 60 minutes to create a cell. The cell thickness of this cell was measured using a Bereck phase plate and was approximately 1
．． It was 5 μm. A ferroelectric liquid crystal element was prepared by injecting the liquid crystal composition 1-B described above in an isotropic liquid state into this cell and slowly cooling it from the isokyoshi phase to 25°C at a rate of 20°C/h. Using this ferroelectric liquid crystal element, peak-to-peak voltage Vpp=
The response speed (hereinafter referred to as optical response speed) was measured by applying a voltage of 25 V to detect the optical response under crossed Nicols (transmitted light amount change 0 to 90%). The results are shown below. Optical response speed 10°C 25°C 40°C 741 μs
ec 263 μsec 109 μsec
c Also, the contrast during this drive at 25°C is 1
3, a clear switching action was observed, and the bistability was also good when the voltage application was stopped. Comparative Example 1 Liquid crystal composition used in Example 1! -In place of B, Exemplary Compound No. 2-10.2-70.3-5 for 1-A without mixing Exemplary Compound No. 1-8, I-136
Liquid crystal composition 1 in which only 6 was mixed in the same weight part as in Example 1
Exemplified compound No. f -8, for 1-A without mixing -C1 and Exemplified compound No. 2-10.2-70
Liquid crystal composition 1-D in which only 1-136°3-56 was mixed in the same weight part as in Example 1, and further exemplified compound No. 3-
Exemplary compound No. 1 for 1-A without mixing 56
-8.1-136.2-10.2-70 only in Example 1
A liquid crystal composition 1-E was prepared by mixing the same parts by weight. These liquid crystal compositions! -C, 1-D, 1-E and 1-A
A ferroelectric liquid crystal element was prepared in the same manner as in Example 1, except that 100% was used, and the optical response speed was measured in the same manner as in Example 1. The results are shown below. Optical response Speed 10℃ 25℃ 40℃ 1-A 1260 μsec 374 μs
ec 137μsec1-C871μsec
282 μsec 113 μ5ec1-D
852 μsec 265 μsec
104 μsec1-E 1070 μsec
321μsec 129μsec Example 1
As is clear from Comparative Example 1, the ferroelectric liquid crystal element containing the liquid crystal composition of the present invention has improved operating characteristics and high-speed response at low temperatures, and also has reduced temperature dependence of response speed. ing. Example 2 Liquid crystal composition 1-A used in Example 1 was mixed with the following exemplified compounds in the weight parts shown below to obtain liquid crystal composition 2-B. Exemplary compound no. Structural formula
Part by Weight - A The optical response speed was measured in the same manner as in Example 1, except that this liquid crystal composition was used, and the switching state, etc. was observed. The uniform alignment within this device was good. , a monodomain state was obtained.The results are shown below: Optical response speed: 10°C 25°C 40°C 783 μs
ec 256μsec 105μSeC Also, the contrast I during this drive at 25°C is 12
A clear switching action was observed, and the bistability was also good when the voltage application was stopped. Comparative Example 2 In place of liquid crystal composition 2-B used in Example 2, Exemplary Compound No. 1-9. 1-A without mixing 1-58
Liquid crystal composition 2-C1 was prepared by mixing only Exemplified Compound No. 2-161.3-11 in the same weight parts as in Example 1, and 1-A was prepared without mixing Exemplified Compound No. 2-161. Exemplified compound no. Liquid crystal composition 2-D in which only 1-9.1-58.3-11 was mixed in the same parts by weight as in Example 1
1-A without further mixing exemplified compound No. 3-11
Exemplary compound No. 1-9. 1-58.2-
Liquid crystal composition 2-E was prepared by mixing only 161 in the same weight parts as in Example 1. These liquid crystal compositions 2-C, 2-D, 2-E and 1-A
Ferroelectric liquid crystal elements were prepared in the same manner as in Example 1, except that ferroelectric liquid crystal elements were used, and the optical response speeds were measured in the same manner as in Example 1. The results are shown below. Optical response speed 10'0 25℃ 40℃1-A
1260 μsec 374 μsec 13
7 μ5ec2-0 910 p sec 2
85 μsec 116 μ5ec2-D
888 μsec 272 μsec 101
μsec2-E 1025 μsec 3
11 μsec 125 μsec As is clear from Example 2 and Comparative Example 2, the ferroelectric liquid crystal element containing the liquid crystal composition according to the present invention has improved operating characteristics and high-speed response at low temperatures, and also has a lower response speed. The temperature dependence of is also reduced. Example 3 Liquid crystal composition 1-A used in Example 1 was mixed with the following exemplified compounds in the weight parts shown below to obtain liquid crystal composition 3-B. Exemplary compound No., Structural formula
Part by Weight - A The optical response speed was measured in the same manner as in Example 1, except that this liquid crystal composition was used, and the switching state, etc. was observed. The uniform alignment within this device was good. , a monodomain state was obtained.The results are shown below: Optical response speed: 10°C 25°C 40°C 833 μs
ec 285 μsec 117 μsec
c Also, the contrast during this drive at 25°C is 1
2, a clear switching action was observed, and the bistability was also good when the voltage application was stopped. Comparative Example 3 In place of liquid crystal composition 3-B used in Example 3, exemplified compound No. 1-7! , 1 without mixing 1-142
Exemplary compound No. for -A, 2-78.3-95.
Liquid crystal composition 3-01, in which only 3-17 was mixed in the same parts by weight as in Example 1, and exemplified compound No. 2-78. 2
Exemplary compound No. 1 for 1-A without mixing -95
-71゜1-142.3-17 only mixed in the same weight parts as in Example 1, liquid crystal composition 3-Dl, and exemplified compound N
o. Exemplary compound No. 3-17 for l-A without mixing,
1-71. Liquid crystal composition 3-E was prepared by mixing only 1-142, 2-78, and 2-95 in the same parts by weight as in Example 1. These liquid crystal compositions 3-C, 3-D, 3-E and!
Ferroelectric liquid crystal devices were prepared in the same manner as in Example 1, except that -A was used, and the optical response speed was measured in the same manner as in Example 1. The results are shown below. Optical response speed 10℃ 25℃ 40℃ 1-A 1260 μsec 388 μs
ec 137 μ5ec3-Cl005 p se
c 342 μsec 1267. i5e
c3-D 925 μsec 283 μs
ec 111 μsec3-E 1130
μsec 345 μsec 131 μsec
c As is clear from Example 3 and Comparative Example 3, the ferroelectric liquid crystal element containing the liquid crystal composition according to the present invention has improved operating characteristics and high-speed response at low temperatures, and also has improved temperature dependence of response speed. Sexuality has also been reduced. Example 4 Liquid crystal composition 1-A used in Example 1 was mixed with the following exemplified compounds in the weight parts shown below to obtain liquid crystal composition 4-B. Exemplary compound No., Structural formula
Part by weight Exemplary Compound No. Structural formula: The optical response speed was measured in the same manner as in Example 1, except that this liquid crystal composition was used, and the switching state and the like were observed. The uniform orientation within this device was good, and a monodomain state was obtained. The results are shown below. Optical response speed 10℃ 25℃ 40℃792p
sec 283 μsec 109 μ
sec Furthermore, the contrast during this driving at 25° C. was 12, a clear switching operation was observed, and the bistability was also good when the voltage application was stopped. Comparative Example 4 In place of the liquid crystal composition 4-H used in Example 4, 1-A was used without mixing exemplified compound No. 1-68.1-107.
Exemplary compound No. 2-55.2-116.2
-130°3-30. Liquid crystal composition 4-01 prepared by mixing only 3-14 in the same 1 part weight as in Example 1 and Exemplary Compound N
1 without mixing 002-55.2-116.2-130
Exemplary compound No. 1-68 for -A. 1-10
7.3-30゜Liquid crystal composition 4-Dl in which only 3-14 was mixed in the same parts by weight as in Example 1, and exemplified compound No. 3
Exemplary compound No. 1-68.1-107.2-55.2-11 for l-A without mixing -30°3-14
Liquid crystal composition 4-E was prepared by mixing only 6.2-130 in the same weight parts as in Example 1. These liquid crystal compositions 4-C, 4-D, 4-E and 1-
Ferroelectric liquid crystal elements were prepared in the same manner as in Example 1, except that A was used, and the optical response speed was measured in the same manner as in Example 1. The results are shown below. Optical response speed 10℃ 25℃40℃ 1-A I260 μsec 388 (,
t sec 137 μ5ec4-C9711t
see 327μSeC124715eC4-D
865 μsec 311 μsec
107 μsec4-E 1050 μsec
341 μsec 1231 t sec As is clear from Example 4 and Comparative Example 4, the ferroelectric liquid crystal element containing the liquid crystal composition of the present invention has improved operating characteristics and high-speed response at low temperatures, and also has a lower response speed. The temperature dependence of is also reduced. Example 5 The following exemplified compounds were mixed in the following ffflfl portion to prepare liquid crystal composition 5-A. Exemplary compound no. C8゜H210+COO+OCs H17 Weight part Cs Hl? +Coo+QCto H21C8°H2,
o+coo+oc 6 H13C1゜H,, +coo+
ocs HI7 Exemplary Compound No. Structural formula: With respect to this liquid crystal composition 5-A, the exemplified compounds shown below were mixed in the weight parts shown below to prepare crystal composition 5-B. Exemplary compound no. Weight part'-)\-A Except for using this liquid crystal composition, the optical response speed was measured in the same manner as in Example 1, and the switching state etc. were observed. The uniform orientation within this device was good, and a monodomain state was obtained. The results are shown below. Optical response speed 10℃ 25℃ 40℃516 μs
ec 203 It sec 87 μs
ec Furthermore, the contrast during this driving at 25° C. was 13, a clear switching operation was observed, and the bistability was also good when the voltage application was stopped. Comparative Example 5 In place of liquid crystal composition 5-B used in Example 5, Exemplary Compound No. 1-8. 5-A without mixing 1-136
Exemplary compound No. 2-10.2-70.3-
Liquid crystal composition 5-01 in which only 56 was mixed in the same parts by weight as in Example 1, and exemplified compounds No. 2-No. 2-70
Exemplary compound No. 1-8 for 5-A without mixing
．． Liquid crystal composition 5-Dl in which only 1-136°3-56 was mixed in the same weight part as in Example 1, and exemplified compound No. 3
Exemplary compound No. for 5-A without mixing -56,
A liquid crystal composition 5-E was prepared by mixing only 1-8°1-136.2-10.2-70 in the same weight parts as in the example. These liquid crystal compositions 5-C, 5-D, 5-E and 5
Ferroelectric liquid crystal devices were prepared in the same manner as in Example 1, except that -A was used, and the optical response speed was measured in the same manner as in Example 1. The results are shown below. Optical response speed 10°C 25°C 40°C3-A
762 μsec 246 psec 98
μ5ee5-C606 μsec 217 μsec
c 91 μ5ec5-D 581 μse
c 210 μsec 84 μsec5-E
693 μsec 233 μsec
94 μsec As is clear from Example 5 and Comparative Example 5, the ferroelectric liquid crystal element containing the liquid crystal composition according to the present invention has improved operating characteristics and high-speed response at low temperatures,
Furthermore, the temperature dependence of response speed is also reduced. Example 6 The following exemplified compounds were mixed with the liquid crystal composition 5-A used in Example 5 in the weight parts shown below to obtain a liquid crystal composition 6-B. Exemplary compound No., Structural formula
Part by Weight - A A ferroelectric liquid crystal element was prepared in the same manner as in Example 1, except that this liquid crystal composition was used, and the optical response speed was measured in the same manner as in Example 1. etc. were observed. The uniform alignment within this liquid crystal element was good, and a monodomain state was obtained. The measurement results are shown below. Optical response speed 10℃ 25℃ 40℃488 μs
ec 182 μsec 81 μsec
c Also, the contrast during this drive at 25°C is 1
3, a clear switching action was observed, and the bistability was also good when the voltage application was stopped. Comparative Example 6 In place of the liquid crystal composition 6-B used in Example 6, Exemplary Compound No. 1-96. 5- without mixing l-139
Exemplary compound No. 2-65 for A. 2-145
Liquid crystal composition 6- in which the same weight parts as in Example 1 were mixed with
01 and Exemplary Compound No. 2-65. Exemplary compound No. 1-96 for 5-A without mixing 2-145
．． Liquid crystal composition 6-Dl prepared by mixing only 1-139°3-40 in the same 1 part weight as in Example 1, and exemplified compound No. 3
Exemplary compound No. for 5-A without mixing -40,
A liquid crystal composition 6-E was prepared by mixing only 2-65°2-145.3-40 in the same weight parts as in Example 1. These liquid crystal compositions 6-C, 6-D, 6-E and 5-A
Ferroelectric liquid crystal elements were prepared in the same manner as in Example 1, except that ferroelectric liquid crystal elements were used, and the optical response speeds were measured in the same manner as in Example 1. The results are shown below. Optical response speed lOoC25℃ 40'C 3-A 762 μsec 246 μsec
c 98 μ5ec6-C567μsec 2
08 μsec 84 μ5ec6-D 5
43 μsec 200 μsec 80 μsec
5ec6-E 672 μsec, 22
6 μsec 96 μsec Example 6 and Comparative Example 6
As is clearer, the ferroelectric liquid crystal element containing the liquid crystal composition according to the present invention has improved operating characteristics and high-speed response at low temperatures, and also has reduced temperature dependence of the response speed. Example 7 Liquid crystal composition 5-A used in Example 5 was mixed with the following exemplified compounds in the following weight parts to obtain liquid crystal composition 7-B. Exemplary compound No., Structural formula
Part by weight Exemplary compound No. Structure
A ferroelectric liquid crystal element was prepared in the same manner as in Example 1, except that this liquid crystal composition was used, and the optical response speed was measured in the same manner as in Example 1 and the switching state etc. The uniform alignment within this liquid crystal element was good, and a monodomain state was obtained.The measurement results are shown below.Optical response speed: 10°C 25°C 40°C 492 μs
ec 183 μsec 77 μsec
Also, the contrast during this drive at 25°C is 12
A clear switching action was observed, and the bistability was also good when the voltage application was stopped. Comparative Example 7 In place of liquid crystal composition 7-B used in Example 7, Exemplary Compound No. 1-48. 5- without mixing l-100
Exemplary compound No. 2-12.2-18.3 for A
Liquid crystal composition 7-C1 in which only -4°3-26 was mixed in the same parts by weight as in Example 1 and Exemplary Compound No. 2-12.
Exemplary compound N for 5-A without mixing 2-18
o. Liquid crystal composition 7-D in which only 1-48.1-100.3-4.3-26 was mixed in the same weight part as in Example 1, and exemplified compound No. 3-4.3-26 was not mixed. Exemplary compound No. 1-48.1-100.2- for 5-A
Liquid crystal composition 7-E was prepared by mixing only 12°2-18 in the same weight parts as in Example 1. These liquid crystal compositions 7-C, 7-D, 7-E and 5-A
Ferroelectric liquid crystal elements were prepared in the same manner as in Example 1, except that ferroelectric liquid crystal elements were used, and the optical response speeds were measured in the same manner as in Example 1. The results are shown below. Optical response speed 10℃ 25℃40℃ 5-A 762 μsec 246 μsec
c 98 μ5ec7-0 547 μsec
200 μsec 82 μ5ec7-D
5261t sec 198 μsec
75 μsec7-E 633 μsec
227 μsec 92 μsec Example 7 and Comparative Example 7
As is clearer, the ferroelectric liquid crystal element containing the liquid crystal composition according to the present invention has improved operating characteristics and high-speed response at low temperatures, and also has reduced temperature dependence of the response speed. Example 8 The following exemplified compounds were mixed in the following parts by weight to prepare liquid crystal composition 8.
-A was created. Exemplary Compound No., Structural Formula % Formula % Structure Formula Weight Parts Furthermore, the following exemplary compounds were mixed with the liquid crystal composition 8-A in the weight parts shown below to form a liquid crystal composition 8-B. It was created. Exemplary compound No., Structural formula
Part by Weight - A A ferroelectric liquid crystal element was prepared in the same manner as in Example 1, except that this liquid crystal composition was used, and the optical response speed was measured in the same manner as in Example 1. The uniform alignment within this liquid crystal element was good, and a monodomain state was obtained.The measurement results are shown below.Optical response speed: 10°C, 25°C, 40°C, 821 μsec, 287 μsec, 1
The contrast during this driving at 25° C. was 18 μsec, and a clear switching operation was observed, and the bistability was also good when the voltage application was stopped. Comparative Example 8 In place of liquid crystal composition 8-B used in Example 8, Exemplary Compound No. 1-8. Exemplary compound No. 2-! for 8-A without mixing 1-136! 0.2-70.3-56
Liquid crystal composition 8- in which 1 part of the same weight as in Example 1 was mixed with
Exemplary compound No. 1-8,l for 8-A without mixing C1 and exemplified compound No. 2-10.2-70
Liquid crystal composition 8-D in which only -136°3-56 was mixed in the same parts by weight as in Example 1, and also exemplified compound No. 3-5
Exemplary compound No. 1- for 8-A without mixing 6
Liquid crystal composition 8-E was prepared by mixing only 8°1-136.2-10.2-70 in the same weight parts as in Example 1. Ferroelectric liquid crystal elements were prepared in the same manner as in Example 1, except that these liquid crystal compositions 8-C, 8-D, 8'-E, and 8-A were used. The optical response speed was measured in the same manner. The results are shown below. Optical response speed 10°C 25°0 40°C3-A
l360 μsec 430 μsec 1
47 μ5ec8-0 922 μsec 3
05 μsec 115 μ5ec8-D
901 μsec 291 μsec 109
p 5ea8-E 1136 μsec 3
53) t sec 133 μsec As is clear from Example 8 and Comparative Example 8, the ferroelectric liquid crystal element containing the liquid crystal composition according to the present invention has improved operating characteristics and high-speed response at low temperatures, and The temperature dependence of response speed is also reduced. Example 9 The following exemplified compounds were mixed with the liquid crystal composition 8-A used in Example 8 in the weight parts shown below to obtain a liquid crystal composition 9-B. Exemplary compound No., Structural formula
Part by Weight - A A ferroelectric liquid crystal element was prepared in the same manner as in Example 1, except that this liquid crystal composition was used, and the optical response speed was measured in the same manner as in Example 1. etc. were observed. The uniform alignment within this liquid crystal element was good, and a monodomain state was obtained. The measurement results are shown below.゛Optical response speed 10℃ 25℃ 40'0811μ
sec 265 μsec 106 μ
sec Furthermore, the contrast during this driving at 25° C. was 13, a clear switching operation was observed, and the bistability was also good when the voltage application was stopped. Comparative Example 9 In place of liquid crystal composition 9-B used in Example 9, exemplified compounds No. 1-9. ! Exemplary compound No. 2-161 for 8-A without mixing -68. Liquid crystal composition 9-C1 in which only 3-11 was mixed in the same weight part as in Example 1 and exemplified compound No. 1-9. 1-58.3-1
．． Liquid crystal composition 9-Dl in which only 1 was mixed in the same weight part as in Example 1, and 8-A without further mixing exemplified compound No. 3-11, exemplified compound No. 1-9, 1-58,
Liquid crystal composition 9-E was prepared by mixing only 2-161 in the same weight parts as in Example 1. These liquid crystal compositions 9-C, 9-D, 9-E and 8-A
A ferroelectric liquid crystal element was prepared in the same manner as in Example 1, except that 100% was used, and the optical response speed was measured in the same manner as in Example 1. The results are shown below. Optical response Speed 10℃ 25℃ 40℃ 8-A 1360 μsec 430 μs
ec 147 μ5ec9-0 932 μs
ec 318 μsec 119 μ5ec9
-D 890 μsec 285 μsec
103 μ5ec9-E 1170 μs
ec 360 μsec 137 μsec As is clear from Example 9 and Comparative Example 9, the ferroelectric liquid crystal element containing the liquid crystal composition of the present invention has improved operating characteristics and high-speed response at low temperatures, and The temperature dependence of the speed is also reduced. Example IO Liquid crystal composition 8-A used in Example 8 was mixed with 1 part of the exemplified compound shown below to obtain liquid crystal composition 10-B. Exemplary compound No., Structural formula
Part by Weight - A A ferroelectric liquid crystal element was prepared in the same manner as in Example 1, except that this liquid crystal composition was used, and the optical response speed was measured in the same manner as in Example 1. etc. were observed. The uniform alignment within this liquid crystal element was good, and a monodomain state was obtained. The measurement results are shown below. Optical response speed 10°0 25℃ 40℃1360μ
sec 430. czsec 147μ
sec Furthermore, the contrast during this driving at 25° C. was 13, a clear switching operation was observed, and the bistability was also good when the voltage application was stopped. Comparative Example 10 In place of the liquid crystal composition 10-B used in Example 10, Exemplary Compound No. 1-96. 8 without mixing 1-139
-A, exemplified compound No. 2-65. 2-145
Liquid crystal composition 10 in which the same weight parts as in Example 1 were mixed with
-C, and Exemplary Compound No. 2-65. 2-145
Exemplary compound No. 1-96 for 8-A without mixing
Liquid crystal composition to-D in which only ゜1-139.3-40 was mixed in the same weight part as in Example 1, and further exemplified compound No.
Exemplary compound No. 8-A without mixing 3-40,
! A liquid crystal composition 10-E was prepared by mixing only -96, 1-139, 2-65, and 2-145 in the same parts by weight as in Example 1. These liquid crystal compositions 10-C, 10-D, 10-E
Ferroelectric liquid crystal elements were prepared in the same manner as in Example 1, except that 10-A and 10-A were used, and the optical response speed was measured in the same manner as in Example 1.The results are shown below. Optical response speed 10℃ 25℃ 40℃ 8-A 1360 μsec 430
p sec 147 μ5ec10-0
723 μsec 290 μsec
1241t 5ec10-0 709 μs
ec 260 μsec! 12μ
5ec10-E 1060 μsec
375 μsec 140 μsec Example 1
As is clear from Comparative Example 10 and Comparative Example 10, the ferroelectric liquid crystal element containing the liquid crystal composition of the present invention has improved operating characteristics and high-speed response at low temperatures, and also has reduced temperature dependence of response speed. has been done. Examples 11 to 18 In place of the exemplified compounds and liquid crystal compositions used in the examples, the exemplified compounds and liquid crystal compositions shown in Table 1 were used in respective parts by weight to produce 1l-B-18-B liquid crystal. A composition was obtained. A ferroelectric liquid crystal element was prepared in the same manner as in Example 1, except that these elements were used, and the optical response speed was measured in the same manner as in Example 1, and the switching state and the like were observed. The uniform alignment within this liquid crystal element was good, and a monodomain state was obtained. The measurement results are shown in Table 1. Example 19 Liquid crystal composition 19-B used in Example 1 was mixed with the following exemplified compounds in the weight parts shown below to obtain liquid crystal composition 19-B. Exemplary compound Na Structural formula Part by weight A ferroelectric liquid crystal device was prepared in the same manner as in Example 1, except that this liquid crystal composition was used, and the optical response speed was measured in the same manner as in Example 1. .Optical response speed 10℃ 25℃ 40℃878 μs
ec 302 μsec 122 μsec Further, using the above liquid crystal element, the tilt angle was measured under crossed Nicols at 25° C. and found to be 7.56. Next, the tilt angle was measured while applying a ±8v square wave at a frequency of 60 KHz, and found to be 13.8°. When the transmittance was measured at this time, it was 14%. At the same time, the contrast ratio was measured and found to be 51:1. Comparative Example 19 In place of Liquid Crystal Composition 1-H, Liquid Crystal Composition 19-C was prepared by adding the aforementioned Nα4-10 compound to Liquid Crystal Composition 1-A in the same ratio as in Example 19. These 19-C and 1-A,! Ferroelectric liquid crystal elements were prepared using the liquid crystal compositions of -B in the same manner as in Example 1, and the optical response speeds were measured in the same manner as in Example 1. Furthermore, the tilt angle was measured in exactly the same manner as in Example 19. The results are shown below. Optical response speed 10℃ 25℃ 40℃! -A 1260μsec 374μsec
137. czsecl-B 741μsec 26
3μsec 109μ5ec19-Cl602μsec
c 468μsec 158μsec tilt angle (
25°C) Initial tilt angle During AC stabilization (without electric field) (When applying 60KHz, ±8v square wave) 1-8 8° 8.2° 1-B
7.6° 8.0°19-C7,7°
14° As is clear from Example 19 and Comparative Example 19, by mixing a liquid crystal compound with negative dielectric anisotropy into the liquid crystal composition of the present invention, not only the response characteristics were improved, but also the AC It has been found that when used in a display method using a stabilizing effect, display characteristics are significantly improved. Example 20 The following exemplified compounds were mixed with the liquid crystal composition 1-B used in Example 1 in the parts by weight shown below to obtain a liquid crystal composition 20-B. Exemplified Compound Nα Structural Formula −1 part Exemplified Compound Nα Structural Formula A ferroelectric liquid crystal element was prepared in the same manner as in Example 1 except that this liquid crystal composition was used. The optical response speed was measured. Optical response speed 10℃ 25℃ 40℃875μse
c 305 μsec 125 μsec Further, using the above liquid crystal element, the tilt angle was measured under crossed Nicols at 25° C. and found to be 8.5°. Next, the tilt angle was measured while applying a square wave of ±8 V at a frequency of 60 KHz, and found to be 13.6°. When the transmittance was measured at this time, it was 14%. At the same time, the contrast ratio was measured and found to be 45:. Comparative Example 20 Instead of liquid crystal composition 1-B, liquid crystal composition 1-A was added with the above (
DNa4-90.4-12.4-112.4-70.4
-107°4-111. A liquid crystal composition 20-C containing the compound No. 4-166 in the same ratio as in Example 20 was prepared. These 20-C and! Ferroelectric liquid crystal elements were prepared using the liquid crystal compositions -A and 1-H in the same manner as in Example 1, and the optical response speeds were measured in the same manner as in Example 1. Furthermore, the tilt angle was measured in the same manner as in Example 20. The results are shown below. Optical response speed 10°C 2.59C 40°C!-A I260μsec 374μsec 1
37μsec! -B 74! μsec 263
μsec 109 μ5ec20-CI470 μs
ec 476 μsec 164 μsec Tilt angle (25℃) Initial tilt angle At AC stabilization (no electric field) (When applying 60KHz, ±8V square wave) 1-Ag3 8.2゜1-87.6
° 8.0020-0 8,7°
14° As is clear from Example 20 and Comparative Example 20, by mixing a liquid crystal compound with negative dielectric anisotropy into the liquid crystal composition according to the present invention, not only the response characteristics were improved, but also the AC It has been found that when used in a display method using a stabilizing effect, display characteristics are significantly improved. As is clear from Examples 11 to 20, the ferroelectric liquid crystal elements containing the liquid crystal compositions 11-B to 20-B according to the present invention have improved operating characteristics and high response speed at low temperatures, and have improved response speed. Temperature dependence is reduced. Further, as is clear from Examples 19 and 20, when the liquid crystal composition according to the present invention is used in a display method based on the AC stabilization effect, the display characteristics are significantly improved. Example 21 The liquid crystal composition used in Example 1 and Comparative Example 1 was
A ferroelectric liquid crystal element was created in the same manner as in Example 1, except that the alignment control layer was created only with polyimide resin, and the optical response speed was measured in the same manner as in Example 1. . The results are shown below. Optical response speed 10°C 25°0 40°C1-8 720
μsec 253 μsec 98 μsec
c1-A 1240μsec 365μsec
132μ5ec1-CB55 μsec 2
70 μsec 105 μsec1-D 8
45 μsec 258 μsec 102
μ5ec1-E 1020μsec 315μ
sec, 122 μsec As is clear from Example 21, even when the element configuration is changed, the element containing the ferroelectric liquid crystal element according to the present invention can be operated at low temperature in the same manner as in Example 1 than the element containing other liquid crystal compositions. The characteristics have been improved, and the temperature dependence of the response speed has also been reduced. [Effects of the Invention] The device containing the ferroelectric liquid crystal composition of the present invention has good switching characteristics and improved operating characteristics.
In addition, a liquid crystal element with reduced temperature dependence of response speed can be obtained. Furthermore, by using the ferroelectric liquid crystal composition containing the specific compound of the present invention, it is possible to obtain a liquid crystal element that not only has the above-mentioned characteristics but also has greatly improved display characteristics due to the AC stabilization effect.

[Brief explanation of the drawing]

Figure 1 is a schematic cross-sectional view of an example of a liquid crystal display element using ferroelectric liquid crystal, and Figures 2 and 3 are schematic diagrams of an example of an element cell to explain the operation of a ferroelectric liquid crystal element. FIG. 4 is a diagram showing changes in θa with respect to V r m s of FLCs having different values of Δε. In FIG. 1, l... Ferroelectric liquid crystal layer 2...
......Glass substrate 3...
・・・・・・・・・・・・Transparent electrode 4・・・・・・・
...Insulating orientation control layer 5 ......
・・・・・・Spacer 6 ・・・・・・・・・・・・
・・・・・・Lead wire 7・・・・・・・・・・・・・・・
・・・・・・Power supply 8・・・・・・・・・・・・・・・・・・
・・・Polarizing plate 9・・・・・・・・・・・・・・・・・・
・・Light source No.・・・・・・・・・・・・・・・・Incoming light ■ Transmitted light In Figure 2, 1a 1b 24 ・・・・・・・・・ In Figure 3, 1a 311] 3a 3b 4a 4b a b Substrate Substrate Ferroelectric liquid crystal layer Liquid crystal molecule Dipole moment (P soil) Voltage application means Voltage application means First stable state Second stable state Upward dipole moment Downward dipole moment Upward electric field Downward electric field Z1υ

Claims (6)

[Claims] (1) The following general formula (I) ▲Mathematical formulas, chemical formulas, tables, etc.▼(I) (However, R_1 and R_2 are linear or branched alkyl groups of C_1 to C_1_8, and the substituent is C
It may have an alkoxy group of _1 to C_1_2. X_1 and X_2 are single bonds, -O-, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼,
▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲Mathematical formulas, chemical formulas,
There are tables etc. ▼ Show one of them. ) and at least one compound represented by the following general formula (I
I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (II) (However, R_3 and R_4 are C_1 to C_1_8 linear or branched alkyl groups that may have substituents,
X_3 and X_4 are single bonds, -O-, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼,
Z_1 has ▲mathematical formulas, chemical formulas, tables, etc.▼, ▲mathematical formulas,
Chemical formulas, tables, etc. are available▼, -CH_2O-, -OCH
＿２−, single bond, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲mathematical formulas, chemical formulas,
There are tables, etc. ▼ is ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ , ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ , ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ , ▲ Mathematical formulas, chemical formulas, There are tables, etc.▼, However, there are ▲mathematical formulas, chemical formulas, tables, etc.▼, ▲mathematical formulas,
There are chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ At least one of them is ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ or ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼. ) and the following general formula (III) ▲ Numerical formulas, chemical formulas, tables, etc. ▼ (III) (However, R_5 is C_1 ~ which may have a substituent)
C_1_8 is a linear or branched alkyl group, X_5 is a single bond, -O-, ▲There are mathematical formulas, chemical formulas, tables, etc.▼,
Z_2 is a single bond, ▲ there are mathematical formulas, chemical formulas, tables, etc. ▼,
▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼or ▲There are mathematical formulas, chemical formulas, tables, etc.▼, m is 1 to 12. ) A ferroelectric chiral smectic liquid crystal composition, characterized in that it contains at least one type of compound represented by the following: and at least one type of liquid crystal compound having negative dielectric anisotropy (Δε). (2) The liquid crystal compound with negative dielectric anisotropy is Δε<−2
The ferroelectric chiral smectic liquid crystal composition according to claim 1. (3) The liquid crystal compound with negative dielectric anisotropy is Δε<−5
3. The ferroelectric chiral smectic liquid crystal composition according to claim 2. (4) The liquid crystal compound with negative dielectric anisotropy is Δε<−1
4. The ferroelectric chiral smectic liquid crystal composition according to claim 3, wherein the ferroelectric chiral smectic liquid crystal composition is 0. (5) The liquid crystalline compound having negative dielectric anisotropy is selected from compounds represented by any of the following general formulas (IV-[1]) to (IV-[5]). Claims 1 to 4
The ferroelectric chiral smectic liquid crystal composition described in 1. General formula (IV-[1]) ▲Mathematical formulas, chemical formulas, tables, etc.▼ [R_a, R_b are linear or branched alkyl groups that may have substituents, X_a, X_d are single bonds, -O-, ▲There are mathematical formulas, chemical formulas, tables, etc.▼,▲There are mathematical formulas, chemical formulas, tables, etc.▼X
＿b, X_c are single bonds, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, -CH_2
CH_2-, A_a, A_b are single bonds, ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (trans), ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (
trans, trans), ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (trans), ▲There are mathematical formulas, chemical formulas, tables, etc.▼, If A_a and A_b are both single bonds, X_b and X_c are single bonds, and X_
a, X_d are both single bonds or both -O-, or X_a is ▲There is a mathematical formula, chemical formula, table, etc.▼, and X_d
is ▲There are mathematical formulas, chemical formulas, tables, etc.▼. Y_a and Y_b are a cyano group, halogen, and hydrogen; however, Y_a and Y_b cannot be hydrogen at the same time. ] General formula (
IV-[2]) ▲Mathematical formulas, chemical formulas, tables, etc.▼ [R_e, R_f are linear or branched alkyl groups that may have substituents, X_e, X_h are single bonds, -O- ,▲There are mathematical formulas, chemical formulas, tables, etc.▼,▲There are mathematical formulas, chemical formulas, tables, etc.▼,
X_f, X_g have ▲mathematical formulas, chemical formulas, tables, etc.▼,
▲There are mathematical formulas, chemical formulas, tables, etc.▼, single bond, A_e,
A_f has ▲mathematical formulas, chemical formulas, tables, etc.▼, ▲mathematical formulas,
There are chemical formulas, tables, etc. ▼, single bond, but A_e, A
__f cannot be a single bond at the same time. ] General formula (IV-[3
]) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [A_i is a single bond, ▲There are mathematical formulas, chemical formulas, tables, etc.▼
, A_j is a single bond, ▲ there are mathematical formulas, chemical formulas, tables, etc. ▼,
▲There are mathematical formulas, chemical formulas, tables, etc.▼, R_i, R_j are straight chain or branched alkyl groups that may have substituents, however, when A_j is a single bond, it is a straight chain alkyl group, and Z_3 is -O- Or -S-, X_i, X_k are single bonds, -O-, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼,
▲There are mathematical formulas, chemical formulas, tables, etc.▼, X_j is a single bond,
▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲Mathematical formulas, chemical formulas,
There are tables, etc. ▼, -CH_2O-, -OCH_2-,
However, when A_i is a single bond, X_i is a single bond, and A
When __j is ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, then X_j is not a single bond, and when A_j is a single bond, X_k is a single bond. ] General formula (IV-[4]) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [R_l, R_m are linear or branched alkyl groups that may have substituents, A_l, A_m are single bonds, ▲ There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, but A
_k and A_l cannot be a single bond at the same time. X_l is a single bond, -O-, ▲ there are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ there are mathematical formulas, chemical formulas, tables, etc. ▼, X_m is a single bond, ▲ there are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ mathematical formulas,
Chemical formulas, tables, etc. are available▼, -CH_2O-, -OCH
_2-, -CH_2CH_2-, -C≡C-] General formula (IV-[5]) ▲ Numerical formulas, chemical formulas, tables, etc. are available▼ [R_n, R_o are linear or branched chains that may have substituents The alkyl group, X_n,
X_o, X_p are single bonds, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, -CH_
2O-, -OCH_2-, -CH_2CH_2-, A_n, A_p are single bonds, ▲ there are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ there are mathematical formulas, chemical formulas, tables, etc. ▼, A_o is ▲ mathematical formulas, chemical formulas, tables, etc. There are ▼, ▲mathematical formulas, chemical formulas,
There are tables, etc. ▼, Z_4 is ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ or ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼] (6) A liquid crystal element comprising the ferroelectric chiral smectic liquid crystal composition according to claim 1 disposed between a pair of electrode substrates.