JPH02115145A - Liquid crystal compound, liquid crystal composition containing the same, and liquid crystal element - Google Patents

Abstract

(57) [Abstract] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

Detailed Description of the Invention [Field of Industrial Application] The present invention relates to a novel liquid crystal compound, a liquid crystal composition containing the same, and a liquid crystal element using the liquid crystal composition. The present invention relates to a liquid crystal compound, a liquid crystal composition containing the same, and a liquid crystal element using the liquid crystal composition.

[Prior Art] As a conventional liquid crystal element, for example, M-Shut (M,
5chadt) and double knee Helfrich (W, Ha
Applied Physics Letters, Vol. 18, No. 4, by lfrich) (ed PhysicsLat
ters, Vol, 18. No, 4) (
1971, 2, 15) Voltage-dependent optical behavior of r-twisted nematic liquid crystals, pp. 127-128 (-Voltage
Dependant Optical Activit
y of a Twisted Ne5atic Li
QuidCrysta1'') Twisted
A device using nematic liquid crystal is known. In this TN liquid crystal, the number of pixels is limited due to the fact that crosstalk occurs during time-division driving using a matrix electrode structure with high pixel density.

Furthermore, its use as a display was limited due to its slow electric field response and poor viewing angle characteristics.

Furthermore, a display element is known in which a switching element using a thin film transistor is connected to each pixel, and each pixel is switched. However, the process of forming the thin film transistor on the substrate is extremely complicated, and the display element has a large area. There are problems that make it difficult to create.

To improve the drawbacks of conventional liquid crystal devices, the use of bistable liquid crystal devices is proposed by Clark (C1
ark) and Lagerwall (Japanese Unexamined Patent Publication No. 56-107216,
Liquid crystals having bistability generally include a chiral smectic phase (US Pat. No. 4,367,924, etc.);
A ferroelectric liquid crystal having SmC") or H phase (SmH") is used.

This ferroelectric liquid crystal has a very fast response speed due to its spontaneous polarization, and can also develop a bistable state with memory properties.Furthermore, it has excellent viewing angle characteristics, so it has a large capacity. Suitable as screen display material.

Furthermore, since the materials used as ferroelectric liquid crystals have asymmetry, in addition to being used as ferroelectric liquid crystals that take advantage of their chiral smectic phase, they can also be used as optical elements such as the following: .

1) One that utilizes the cholesteric-nematic phase transition effect in the liquid crystal state (J, J, Wysoki, ^.

^dams and W, Haas': Phys, R
ev, Lett,, 20.10242) that utilizes the White-Tiller type guest-host effect in the liquid crystal state (D, LJhlte and G, N, Taylor
:J, ^pp1. Phys, 45.471δ (197
4)), etc. Although detailed explanations of individual methods will be omitted, they are important as display elements and modulation elements.

However, a liquid crystal compound that has both stability of the liquid crystal state over a wide temperature range and high-speed response has not yet been obtained.

[Problems to be Solved by the Invention] An object of the present invention is to provide a novel optically active liquid crystal compound for solving the above-mentioned problems. Another object of the present invention is to provide a liquid crystal composition containing at least one kind of this liquid crystal compound, and a liquid crystal element using the liquid crystal composition.

[Means for Solving the Problem] The present invention has been made to achieve the above-mentioned object, and has the following formula [1] % formula % [11 (However, in the above formula [1], R, , R, are each an alkyl group having 1 to 18 carbon atoms, and one of them is a straight chain, and the other is an optically active group in which a fluorine or trifluoromethyl group is introduced into an asymmetric carbon atom. The present invention relates to a novel optically active liquid crystal compound represented by the following formula: X is a symbol; m and n are each 0.1 or 2. Specifically, either one of R, R, is the following formula [2] (where, X represents a fluorine atom or a trifluoromethyl group, p is an integer of 1 to 18, and q is 0 or 1.
, C1 represents an asymmetric carbon atom).

- The compound represented by formula [1] itself preferably has a liquid crystal phase such as a chiral smectic C phase rather than a smectic C phase, but even if it does not exhibit a liquid crystal phase, it may have a smectic C phase or a chiral smectic C phase.
Any compound may be used as long as it can be mixed with other phase-containing liquid crystal compounds with good compatibility.

Further, the present invention provides at least 1f! of the liquid crystalline compound represented by the above formula [1]. The present invention provides a liquid crystal composition characterized by containing Group J.

Furthermore, the present invention provides a liquid crystal element using a liquid crystal composition containing at least one type of liquid crystal compound represented by the above formula [1].

Below, a typical manufacturing process of the liquid crystal compound represented by the above-mentioned formula [1] will be illustrated.

However, in the above formula, R1, R2, X, A, Q, m, and n are as defined above.

Examples of compounds that can be produced as described above are listed below.

The liquid crystal composition of the present invention contains at least one liquid crystal compound represented by formula [1] above as a compounding component. When combined with a ferroelectric liquid crystal represented by the following formulas (1) to (13), spontaneous polarization increases and response speed can be improved.

In such a case, the liquid crystal compound represented by the formula [1] of the present invention may be added to the resulting liquid crystal composition in an amount of 0.1 to
It is preferable to use it in a proportion of 99% by weight, particularly 1 to 90% by weight.

Crystal thin - Goshi C', mko S engineering A + - - Isotropic phase υ' C00CHzCHCt Hs 4.4'-7 Zoxycinnamitsukuashi 7]! -Bis(2
-Methylbutyl) ester 91.5"C crystal □ SmC" - 93+C □ SmA Compounds may be used as well.

Moreover, by blending the liquid crystalline compound represented by the general formula [1] of the present invention with a smectic liquid crystal that is not chiral itself, as shown by the following formulas (19) to (23), strong telephone A liquid crystal composition that can be used as a liquid crystal is obtained.

In this case, - the liquid crystalline compound represented by the formula [1] is added in an amount of 0.1 to 99% by weight, particularly 1 to 90% by weight of the resulting liquid crystal composition.
[It is preferable to use i amount%.

Such a liquid crystal composition can obtain large spontaneous polarization depending on the content of the liquid crystal compound of the present invention.

4.4'-decyloxyazoxybenzene Crrst,
7 colors! S<120"ON+23.'l
:: Igo.

4'-Pentyloxyphenyl-4-octyloxybenzoate Cryst, 58°C Sw!
2 64℃ SmA 66℃
N 85°C Iso.

−1−−ri −1−−−contest −11step −1÷Here, the symbols indicate the following aspects, respectively.

Crystal: Crystalline phase; Shea: Smectic A phase.

S-: smectic B phase, SdC: smectic C phase, N: nematic phase, Iso: isokichi phase.

Cryst - Hiroshi Yutaka 189T h^-J l5o-
2-(4'-octyloxyphenyl)-5-nonylpyrimidine Cryst, 33"CSsC60"C35
IIA 75” CIso.

In addition to the compounds of formulas (]9) to (23) above, compounds represented by the following structural formulas can be suitably used for the same purpose.

Furthermore, by using a liquid crystal composition containing at least one liquid crystal compound represented by the formula [1] of the present invention, liquid crystal elements such as confabulatory liquid crystal elements and twisted nematic liquid crystal elements can be manufactured. can be obtained.

[Example code] Hereinafter, the present invention will be explained in more detail with reference to Examples.

Ten J1 starvation 4-dodecyloxy-3-fluorobenzoic acid 4”-(2
-Production of fluorooctyloxy)phenyl ester 4-dodecyloxy-3-fluorobenzoic acid 4''-(2-fluorooctyloxy)phenyl ester was produced according to the following steps.

Step 1) Production of (+)-4-(2-fluorooctyloxy)phenol.

(-), -2-fluorooctatotool 2.66 g (18
msol) and 4.25 g of dry pyridine (54!1110
1) were placed together in a container with a nitrogen atmosphere and stirred. Cool this container with ice and add 3.75 g of p-toluenesulfonyl chloride.
(20 + smol) was added in two portions and stirred for 3 hours. After the reaction was completed, it was neutralized with 2N hydrochloric acid, and methylene chloride 1
The aqueous layer was extracted twice with 51 liters of methylene chloride. Water was added to this methylene chloride layer, and the mixture was extracted with methylene chloride in the same manner as before. Anhydrous sodium sulfate was added to this methylene chloride solution and dried overnight.

Methylene chloride was distilled off to obtain 5.11 g of (+)-p-toluenesulfonic acid 2-fluorooctyl ester (yield 94%). Add to this 3.74g of hydroquinone (34m
mol) and 5 ml of 1-butanol were added and stirred. Add 12o2g (25mwol) of sodium hydroxide to it.
- Slowly add a solution dissolved in butanol 131, dropwise and react at 130°C for 7 hours.After the reaction is complete, add water 40
Ill was added and extracted with ether. Anhydrous sodium sulfate was added to this ether solution and dried overnight. The solvent was distilled off, and the residue was separated by silica gel chromatography using methylene chloride to obtain 227 g (yield: 56%) of purified -4-(2-fluorooctyloxy)phenol.

Step 2) Production of 4-dodecyloxy-3-fluorobenzoic acid, i'(2-fluorooctyloxy)phenyl ester.

4-dodecyloxy-3-fluorobenzoic acid 0.36g
(1.1 mmol) and thionyl chloride 21 were reacted under heating under reflux for 2 hours, and then excess thionyl chloride was distilled off to obtain an acid chloride. On the other hand, 0.26 g (1.1 mmol) of 4-(2-fluorooctyloxy)phenol
), Torie f L/ :/ Cyanine 0. 25
g (2.2 mmol) was dissolved in dry benzene 2-1, and a solution of the previously obtained acid chloride in dry benzene 21 was added dropwise. After stirring at 50°C for 2 hours, 661g of 60% sodium hydride was added, and
The mixture was heated to reflux for an hour.

After the reaction was completed, the mixture was poured into ice water, made acidic with hydrochloric acid, and then extracted with diethyl ether. The obtained ether layer was washed with saturated brine and then dried over anhydrous magnesium sulfate. The solvent was distilled off, and the resulting crude product was subjected to silica gel column chromatography (mobile phase: hexane/dichloromethane = 1
71). The target product, 4-dodecyloxy-
The yield of 3-fluorobenzoic acid 4”-(2-fluorooctyloxy)phenyl ester was 0.49 g, obtained by OCR
C13) JC11 Production of 4'-octyloxyphenyl 3-fluoro-4-(2-fluorodecyloxy)benzoate.

According to the following steps, 3-fluoro-4-(2-fluorodecyloxy)benzoic acid 4'-octyloxyphenyl ester was obtained.

Step 1) Production of 3-fluoro-4-hydroxybenzoic acid methyl ester.

3-fluoro-4-hydroxybenzoic acid 0.79 g (5
miol) and methanol 0. 48g (15m mo
1 to 2 drops of concentrated sulfuric acid were added to a solution of 1) dissolved in 1.5 ml of dichloromethane, heated under reflux for 30 hours, poured into water, and extracted with methylene chloride. The obtained organic layer was dried over anhydrous sodium sulfate, and after distilling off the solvent, it was purified by silica gel column chromatography (mobile phase: dichloromethane). As a result, the target product, 3-fluoro-4
-Hydroxybenzoic acid was obtained in an amount of 0.72 g (yield: 85%).

Step 2) Production of 3-fluoro-4-(2-fluorodecyloxy)benzoic acid methyl ester.

In the same operation as Step 1 of Example 1, (-)-2-
495 μg of 2-fluorodecyl (+)-p-toluenesulfonate obtained by using (-)-2-fluorodecanol instead of fluorooctatool and 255 mg of methyl 3-fluoro-4-hydroxybenzoate. was dissolved in 1.51 dimethylformamide, 70 mg of sodium hydride (60%) was added, and the mixture was reacted at 130°C for 2 hours, then further stirred at room temperature for 10 hours. Next, the reaction solution was poured into water. The mixture was acidified with hydrochloric acid and extracted with dichloromethane.

The obtained organic layer was washed, dried over anhydrous sodium sulfate, and the solvent was distilled off to obtain 0.7 g of a crude product. This was purified by silica gel column chromatography (mobile phase: ethyl acetate/hexane = 1/2), and
10 mg of the target product was obtained (yield 53%).

Step 3) Production of 3-fluoro-4-(2-fluorodecyloxy)benzoic acid.

3-Fluoro-4-(2-fluorodecyloxy)
Methanol solution of 410 mg of benzoic acid methyl ester (
Add methanol 251) and react at 60 to 70°C for 4 hours. After the reaction, water was added and methanol was distilled off.
The mixture was made acidic with 6N hydrochloric acid. The precipitated carboxylic acid was collected, dried over diline pentoxide overnight, and 320+I1g of 3-
Fluoro-4-(2-fluorodecyloxy)benzoic acid was obtained (yield 81%).

m, p, 102.4-io2.9°C Step 4) Production of 3-fluoro-4-(2-fluorodecyloxy)benzoic acid 4'-octyloxyphenyl ester.

300 mg of 3-fluoro-4-(2-fluorodecyloxy)benzoic acid was dissolved in 2 ml of thionyl chloride, heated under reflux for 2 hours, and after the reaction was completed, excess thionyl chloride was distilled off to obtain an acid chloride. On the other hand, triethylenediamine 22018 and 4-octyloxyphenol were dissolved in 2 ml of dry benzene, and while stirring on a water bath, a solution of the previously obtained acid chloride dissolved in 3+al of dry benzene was added dropwise. Ta. After that, the reaction was carried out at 50°C for 2 hours, cooled on ice again, 60mg of 60% sodium hydride was added, and an additional 1 hour was added.
The mixture was heated under reflux for an hour. After the reaction was completed, the reaction solution was poured into water and extracted with diethyl ether. The obtained ether layer was washed with brine, dried over anhydrous sodium sulfate, and the solvent was distilled off to obtain a crude product. This was purified by silica gel column chromatography (mobile phase: benzene) to obtain 400 mg of 3-fluoro-4=(2-fluorodecyloxy)benzoic acid 4'octyloxyphenyl ester (yield: 80%). .

and λriyu 4-dodecyloxy-3-fluorobenzoic acid 4'-(3
-1-Lifluoromethylheptanoyloxy)-4-biphenyl ester production.

According to the following steps, 4-dodecyloxy-3-fluorobenzene, fl14'-(3-)lifluoromethylheptanoyloxy)-4''-biphenyl ester was produced.

Step 1) Production of 4-(3-1-lifluoromethylheptanoyloxy)-4'-biphenol.

(+) -3-Trifluoromethylhebutanoic acid 2.1g
and 6 Ill of thionyl chloride were mixed, and after heating for 2 hours, excess thionyl chloride was distilled off to obtain the acid chloride. In a separate container, 4.6 g of biphenol, 4 oml of pyridine, I
A mixed solution of Z-dried benzene IQmt was prepared, and a solution of the previously obtained acid chloride dissolved in dry benzene 51 was added dropwise. After reacting at 50°C for 2 hours and further at 90°C for 2 hours, the mixture was poured into ice water and extracted with diethyl ether 1501. The obtained ether layer was washed with brine and dried over anhydrous sodium sulfate. After distilling off the solvent, the obtained crude product was recrystallized from hexane to obtain 2.0 g of the target product (
yield 52%).

Step 2) 4-dodecyloxy-3-fluorobenzoic acid 4'-(3-trifluoromethylheptanoyloxy)
-4“-Production of biphenyl ester.

4-Dodecyloxy-3-fluorobenzoic acid 32411
After dissolving 1 g in 1 ml of thionyl chloride and heating under reflux for 2 hours, excess thionyl chloride was distilled off to obtain an acid chloride. On the other hand, the previously obtained acid chloride was dissolved in 1 ml of benzene in a solution of 4-(3-1-lifluoromethylheptanoyloxy)-4'-biphenol 366B and 224 mg of triethylenediamine dissolved in 2 ml of dry benzene. Add the solution dropwise, react at 50 ° C. for 2 hours, cool with water, add 60 mg of 60% sodium hydride, and heat under reflux for another 2 hours. After the reaction is completed, the reaction solution is poured into water, The mixture was acidified with hydrochloric acid and extracted with diethyl ether. The obtained ether layer was washed with brine, dried over anhydrous sodium sulfate, the solvent was distilled off, and 0.5
．． A crude product of Og was obtained. This was subjected to silica gel column chromatography (mobile phase: methylene chloride/hexane = 1
71) and further recrystallized using a hexane-ethanol mixed solvent to obtain 200+*g of the desired product (yield 30%).

The phase transition temperatures of the compounds shown in Examples 1 to 3 are shown below.

(+14) A liquid crystal composition A containing the liquid crystal compound shown in Example 2 as a compounding component was prepared.As a comparative example, the cyclic group of the skeleton was substituted with fluorine instead of the liquid crystal compound shown in Example 2. A liquid crystal composition B containing a liquid crystal compound that had not been prepared was prepared.

The phase transition temperature and spontaneous polarization values of liquid crystal compositions A and B are shown below.

Cryst, : crystal, Iso, : isotropic liquid, S^
: Smectic A phase, S, unidentified smectic phase.

[Liquid Crystal Composition A] [Liquid Crystal Composition B Phase Inversion X3 Temperature (°C) Phase Inversion ■3 Temperature (1) Represents a smectic phase. (Unidentified) Spontaneous polarization (nC/am2) Next, two glass plates with a thickness of 0.7 mm were prepared, an ITO film was formed on each glass plate, and a voltage was applied. 5102 was vapor-deposited to form a recording layer. Silane coupling agent on a glass plate [Shin-Etsu Chemical Co., Ltd.]
KBM-602] 0.2% isopropyl alcohol solution was applied for 15 seconds using a spinner with a rotational speed of 200 Orp, p, m to perform surface treatment. After that, a heat drying treatment was performed at 120° C. for 20 minutes.

Furthermore, a 32% dimethylacetamide solution containing a polyimide resin precursor (Toshiku Co., Ltd.) sp-51 was applied onto the surface-treated glass plate with the ITO film using a spinner with a rotational speed of 200 Or, p, m for 15 seconds. After formation III, for 60 minutes,
A heating condensation firing treatment was performed at 300°C. The thickness of the coating film at this time was about 700. After firing, the film is rubbed with acetate flocked cloth, and then
After cleaning with isopropyl alcohol solution and scattering alumina beads with an average particle size of 2 μm on one glass plate, the rubbing axes of each plate were made parallel to each other, and an adhesive sealant [Rixon Bond (Chisso Corporation)] was applied. ] The glass plates were glued together and dried by heating at 100° C. for 60 minutes to create a cell. The cell thickness of this cell was measured using a Berek phase plate and was found to be approximately 2 μm.

Here, the ferroelectric liquid crystal elements A and B prepared earlier were each in an isotropic phase, in a uniformly mixed liquid state, and then slowly cooled at 0.5°C/h from the 0 isotropic phase that was vacuum injected into the fabricated cell. By doing this, a ferroelectric liquid crystal device was created.

Using this ferroelectric liquid crystal element, the optical response under crossed Nicols (transmitted light amount change 0 to 90%) is detected by applying a voltage of 30 V peak to peak voltage, and the response time (
Hereinafter referred to as optical response time) was measured. The results are shown below.

Optical Response Time (μ5ec) By adding the liquid crystalline compound shown in Example 2 in this manner, a liquid crystal composition having a wide range of SmC'' phases and excellent responsiveness was obtained.

The following compounds were mixed in 111 at the following composition ratio to obtain liquid crystal composition C.

C+ 2H250-1,=3→Giant〒=Giant->“<Se〒=
=Giant E=::-Oc ♂H, A12*tk Next, the above composition C and the compound of Example 3 were mixed at a ratio of 955 to obtain a liquid crystal composition. Liquid crystal elements were prepared using liquid crystal composition C1 and liquid crystal composition R under exactly the same conditions as in Example 4, and the response times were measured under exactly the same conditions except that the peak-to-peak voltage was 20V. The response time measurement results at 25°C are shown below.

Liquid crystal composition C 310 μsec Liquid crystal composition 0 265 μsec From the above results, the compound of the present invention, 4-dodecyloxy-3-fluorobenzoic acid 4'-(3
-Trifluoromethylheptanoyloxy)-4"-biphenyl ester was found to improve the response characteristics.

``1 cold'' - ITO (Indium Tln 0) as a transparent electrode
xide)lli was formed on the glass substrate by spinner coating using a polyimide resin precursor [SP, -5101 manufactured by Toshishiku Co., Ltd.], and then baked at 300° C. for 60 minutes to obtain a polyimide film. Next, this film was subjected to an orientation treatment by rubbing, and cells were prepared so that the rubbing axes were perpendicular to each other (cell spacing: 8 μm).

A nematic liquid crystal composition [Rixon GR-63
: Biphenyl liquid crystal mixture manufactured by Chisso Corporation] was injected,
When a TN (twisted nematic) type cell was observed using a polarizing microscope, it was found that a reverse domain (striped pattern) was formed.

When a TN cell was observed in the same manner as above using a liquid crystal mixture obtained by adding the liquid crystal compound of Example 2 of the present invention (lfflfTc part) to the Rixon GR-63 (99 parts by weight), reverse domain was observed. There was no visible nematic phase, indicating a well-uniform nematic phase. This indicates that the liquid crystalline compound of the present invention is effective in preventing reverse domains.

Liquid crystal composition E was obtained by mixing the following compounds in the following composition ratio.

Parts by weight For comparison with the above liquid crystal composition E, a liquid crystal composition F was prepared as follows.

Weight part Conducted using liquid crystal composition E and liquid crystal composition F Weight part A liquid crystal element was created under exactly the same conditions as Example 4, and the Example The response time was measured under exactly the same conditions as in Example 5.

Measurement results The results are shown below.

Also, Spontaneous polarization was measured using this liquid crystal element.

Mix the following compounds in the following composition ratio, liquid crystal composition I got a G.

For comparison with the above liquid crystal composition G, an example liquid crystal composition H was prepared using liquid crystal composition G and liquid crystal composition H as described below.

A liquid crystal element was created under exactly the same conditions as Example 4, and the Example The response time was measured under exactly the same conditions as in No. 5.

Measurement result Weight part The results are shown below.

Also, Spontaneous polarization was measured using this liquid crystal element.

Mix the following compounds in the following composition ratio, liquid crystal composition I got K.

Parts by Weight For comparison with the above liquid crystal composition, a liquid crystal composition was prepared as follows.

Implemented using a liquid crystal composition and a liquid crystal composition. A liquid crystal element was created under exactly the same conditions as Example 4, and the Example The response time was measured under exactly the same conditions as in No. 5.

Measurement result The results are shown below.

Also, Spontaneous polarization was measured using this liquid crystal element.

Mix the following compounds in the following composition ratio, liquid crystal compound I got item M.

For comparison with the liquid crystal composition M above, a liquid crystal composition N was prepared as follows.

Liquid crystal elements were prepared using Liquid Crystal Composition M and Liquid Crystal Composition N under exactly the same conditions as in Example 4, and the response times were measured under exactly the same conditions as in Example 5. The measurement results are shown below.

Furthermore, spontaneous polarization was measured using this liquid crystal element.

Further, the contrast at 25° C. during driving was 18, a clear switching operation was observed, and the bistability was also good when the voltage application was stopped.

From the above results, it was found that the liquid crystal composition containing the liquid crystal compound of the present invention has large spontaneous polarization and improved response characteristics.

Example 11 Exactly the same procedure was carried out except that a 2% aqueous solution of polyvinyl alcohol resin [PυA-117 manufactured by Kurari Co., Ltd.] was used in place of the 1.5% dimethylacetamide solution of the polyimide resin precursor used in Example 10. A strongly electrostatic liquid crystal element was prepared using the method, and the optical response speed was measured using the same method as in Example 7.

The results are shown below.

25℃ 35℃ 45℃ 102 μsec 82 u see 68
The contrast during this driving at 25° C. was 19 μsec.

1〓1 (1 m 1 u S used in Example 10) All except that the orientation control layer was created only with polyimide resin without using 0. Example 10
A strong-conductivity liquid crystal element was prepared in the same manner as in Example 10.
The optical response speed was measured in the same manner. The results are shown below.

25℃ 35℃ 45℃ 98 p sec 79 μsec 65 μ
As is clear from sec Example 11.12, even when the device configuration is changed, the device containing the strong electroconductive liquid crystal composition according to the present invention has greatly improved low temperature operating characteristics as in Example 10. In addition, the temperature dependence of the response speed is reduced.

[Effects of the Invention] According to the present invention, a liquid crystal compound having good electric field responsiveness was obtained. Furthermore, it was confirmed that the liquid crystal composition and liquid crystal element containing the liquid crystal compound not only improve the response speed but also are effective in preventing reverse domains.

Claims (1)

[Claims] 1. The following general formula [1] ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [1] (However, in the above general formula [1], R_1 and R_2 each have 1 to 18 carbon atoms. is an alkyl group, one of which is linear, and the other is an optically active group in which fluorine or trifluoromethyl group is introduced into an asymmetric carbon atom; X is -CH_2O-, ▲ formula, There are chemical formulas, tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ or -CH_2-, and Y is ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ or ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼;Z There are ▲mathematical formulas, chemical formulas, tables, etc.▼, ▲mathematical formulas, chemical formulas,
Choose from ▼, -OCH_2-; A is ▲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.▼ Yes; m and n are 0, 1, or 2, respectively, and satisfy the condition of m+n=1 or 2; Q has ▲mathematical formula, chemical formula, table, etc.▼, ▲
An optically active liquid crystalline compound represented by a mathematical formula, a chemical formula, a table, etc. (selected from ▼, ▲ a mathematical formula, a chemical formula, a table, etc.). 2. In general formula [1], one of R_1 and R_2 is the following general formula [2] ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [2] (However, X represents a fluorine atom or a trifluoromethyl group, p is an integer from 1 to 16, q is 0 or 1
, C^* represents an asymmetric carbon atom)
The liquid crystalline compound described above. 3. A liquid crystal composition containing at least one component of the liquid crystal compound according to claim 1 or 2. 4. A liquid crystal element using the liquid crystal composition according to claim 3.