JPS6322042A - Fluoroalkane derivative - Google Patents

Abstract

NEW MATERIAL:A fluoroalkane derivative expressed by formula I (R is 1-16C alkyl; C* is asymmetric carbon atom; R<1> is 1-16C alkyl or alkoxy; rings A, B and C are phenylene, cyclohexylene or pyrimidinylene; p is 0 or 1; q is 1 or 2 when p is 1; r is 0 or 1; l, m and n are 0 or positive integers satisfying the relation. l+m+n>=1). EXAMPLE:2-Fluorooctyl p-octyloxybiphenylcarboxylate. USE:Useful as one component in liquid crystal compositions, capable of enhancing polarity as well as responsiveness of liquid crystals in an electric field. PREPARATION:As shown in the reaction formulas, optionally active intermediates, e.g. 2-fluoro-1-alkanol, (2-fluoroalkyl) p-hydroxybenzoate, etc., are used to afford the aimed compound expressed by formula I.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel liquid crystal compound and a liquid crystal composition containing the same, and more particularly to a liquid crystal compound that is an optically active fluoroalkane derivative and a liquid crystal composition containing the same. This invention relates to a chiral liquid crystal composition containing.

11 鮮” An example of a conventional liquid crystal element is M-Sha.

) ()1.5chadt) and “Applied Phy Physics Letters” by W. Helfrich (W, H61frich).
sicSLetters”) Volume 18, No. 4 (1
Published on February 15, 1971), pp. 127-128 “
Voltage Dependant e Optical Number Activity - of a Twisted Working Nematic Liquid Crystal °゛ (“Voltage Depe
ndentOptical Activit7 o
f a TwiSted NematicLii
A device using a twisted nematic liquid crystal as shown in "quid crystal" is known.This TN liquid crystal has a high pixel density and a matrix electrode structure that reduces crosstalk during time-division driving. The number of pixels per pixel was limited due to the problem that this occurs.

Furthermore, its use as a display has been 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 some problems that make it difficult to create.

To improve the drawbacks of conventional liquid crystal devices, the use of bistable liquid crystal devices has been proposed.
ark) and Lagerwall [JP-A-56-107216,
[U.S. Pat.
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) Those that utilize the cholesteric-nematic phase transition effect in the liquid crystal state (J. J., Wysoki, A.
Adass and W, Haas; Phrs, Rev
, Lett, 20.1024 (196B)).

2) One that utilizes the White-Tiller type guest-host effect in the liquid crystal state (D, L, White and
G, N, Taylor; J, Appl, Phys.
, , 45.4718 (1974)), etc. Although detailed explanations of individual methods will be omitted, they are important as display elements and modulation elements.

In such a method using the electro-responsive optical effect of liquid crystal, it is said that it is preferable to introduce a polar group in order to improve the responsiveness of the liquid crystal. In particular, it is known that the response speed of ferroelectric liquid crystals is proportional to the spontaneous polarization.
In order to increase speed, it is desired to increase spontaneous polarization. From this point of view, P. Keller et al. showed that it is possible to increase spontaneous polarization and speed up the response speed by directly introducing a chlorine group into an asymmetric carbon (C, R,
Acad.

Sc, Paris, 282 G, 839 (197
[1) ), L, However, the chlorine group introduced into the asymmetric carbon is not only chemically unstable, but also has the disadvantage that the stability of the liquid crystal phase decreases due to the large atomic radius. I'm here.

Improvement is desired.

On the other hand, functional materials required for optical elements characterized by having optical activity are often synthesized via optically active intermediates, but the optically active intermediates used conventionally include 2. - Methyl butanol, secondary octyl alcohol, secondary butyl alcohol, P-(2-methylbutyl)benzoic acid chloride, secondary phenethyl alcohol, amino acid salt conductors, camphor derivatives, cholesterol derivatives, etc. are listed, and optically active intermediates such as Polar groups were rarely introduced into the body. For this reason, the method of increasing spontaneous polarization by directly introducing a polar group into an asymmetric carbon atom has not been used effectively.

Men 1 standing 11 The present invention has been made in view of the above points.

That is, the present invention provides a liquid crystal compound that increases polarity by directly introducing a stable fluorine group with a large dipole moment into an asymmetric carbon atom, and improves the electric field responsiveness of a liquid crystal, and a liquid crystal compound containing at least one type thereof. The purpose is to provide a liquid crystal composition.

In the present invention, it is easy to change the length of the alkyl group, and this allows H, Arnold, Z, Ph7s, C
Hew,.

228.148 (1984), a liquid crystal compound capable of controlling the type and temperature range of a liquid crystal phase developed in a liquid crystal state, and a liquid crystal composition containing at least one compound thereof as a compounded component. The purpose is to

The present invention has been made to achieve the above-mentioned object, and has the general formula CI) [where R represents an alkyl group having 1 to 16 carbon atoms]
” indicates an asymmetric carbon atom, and R1 is a furkyl group or an alkoxy group having 1 to 16 carbon atoms, (), Φ, -@
- indicates phenylene ts<sha), cyclohexylene group (-@-), and pyrimidinylene group (4), respectively.

p is 0 or q, and when p=1, q is 1 or 2. r is 0 or l. Also, j, m, n are
It is O or a positive integer that satisfies the relationship j+m+n≧1. ] An optically active fluoroalkane conductor represented by the following is provided.

The present invention also provides a liquid crystal composition containing at least one of the above optically active fluoroalkane conductors as a compounding component.

The optically active fluoroalkane derivative represented by the above general formula (I) is preferably 2-2 as shown in the specification of Japanese Patent Application No. 60-232886 or Japanese Patent Application No. 61-40793.
Luoro 1-flukanol, p-hydroxybenzoic acid (2-fluoroalkyl) ester, p-hydroxybiphenylcarboxylic acid (2-fluoroalkyl) ester, hydroquinone (2-fluoroalkyl) ether, 4-(4-(2-fluoroalkyl) ester, Synthesized from optically active intermediates such as alkyl)oxyphenyl]phenol.

For example, a liquid crystalline compound represented by general formula (I) can be obtained from these optically active intermediates by the following synthetic route.

(R, R1, (), Φ, sha, P, q, r, l, m, n are as defined above.) Examples of the fluoroalkane derivatives thus obtained are shown in Table 1 below. show.

In the table and the following description, the symbols in the description of phase transition temperature indicate the following phases, respectively.

Crystal: crystalline phase, SmA: smectic A
phase.

5IC! : Chiral smectic C phase.

N: Nematic phase, Ch: Cholesteric, Riphase, Is
o: Tokichi phase, Sm3: SsA, Sac
Smectic phase other than ``(unidentified).

Further, the liquid crystal composition of the great invention contains at least one fluoroalkane derivative represented by the general formula (I) as a compounding component. ) When combined with a ferroelectric liquid crystal as shown in ), spontaneous polarization increases and response speed can be improved.

In such cases, the fluoroalkane derivative of the present invention represented by general formula (1) should be used in a proportion of 0.1 to 99% by weight, particularly 1 to 90% by weight of the resulting liquid crystal composition. is preferred.

(1) OBAMBC) -
Chlorprovir cinnamemate) (HOBACPC)-Methylbutyl-α-cyanocinnamate (DOBAMBC)
C) CH.

-COOCH2CHC2Ha 4.4'-azoxycinnamic acid-bis(2-
methylbutyl) ester octyloxybiphenyl-4
-Carpoxylates, such as those shown by the following formulas 1) to 5), can be blended with smectic liquid crystals that are not chiral per se to obtain compositions that can be used as strongly electrostatic liquid crystals.

In this case, the fluoroalkane derivative of the present invention represented by general formula (I) is preferably used in an amount of 0.1 to 99% by weight, particularly 1 to 90% by weight of the resulting liquid crystal composition.

Such a composition can obtain large spontaneous polarization depending on the content of the fluoroalkane derivative of the present invention.

4.47-zosyloxyazoxybenzene Cryst,
77'OSac 120'CN 123. "O
Lgo.

Cryst, 120'CSa+c189'OSaA
21B'OIsa.

2-(4''-octyloxyphenyl)-5-nonylpyrimidine Cryst, 33'OSac 60''O
SaA 75”C! Iso.

4'-Pentyloxyphenyl-4-octylleoxybenzoate Cryst, 58"C Sagi E14'C:
S@A 8G"CN 85'CIgo.

Here, the symbols indicate the following phases, respectively.

Crystal: Crystal phase, 5 prayers: Smectic physiognomy.

5IIB: smectic B phase, 5IIc: smectic C phase, N: nematic phase, Igo: isokichi phase The present invention will be explained in more detail with reference to Examples below.

p-octyloxybiphenylcarboxylic acid 2-fluorooctyl ester represented by the above formula was produced by the following reaction steps.

C@, Htt Om COOH11 co=shi≦≧−L”shi−2, C@Hl? OmCOC1 i.e. p-octyloxybiphenylcarboxylic acid 0.74g (2,3
After heating and refluxing mmo I) with 5 ml of thionyl chloride for 2 hours and 30 minutes, unreacted thionyl chloride was distilled off to obtain the corresponding acid chloride.

Next, 0.50 g (4.5 mmol) of triethylenediamine
) was dissolved in 5 ml of dry benzene, potassium hydroxide was added, and the mixture was dried for about 30 minutes. This solution was mixed with (-)2-
Fluoro-1-octanol 0.40 g (2.7 m
mol) and shaken and stirred. This solution was added dropwise to the above acid chloride under stirring, and after completion the solution was added at 50°C.
The mixture was stirred for 2 hours.

After the reaction was completed, IN hydrochloric acid and water were added and the mixture was extracted with benzene.

Furthermore, IN sodium carbonate aqueous solution was added to this benzene layer for benzene extraction.

Anhydrous sodium sulfate was added to this benzene solution and dried overnight.

Distill the benzene and convert it into benzene:hexane=1:1
The mixture was separated by silica gel column chromatography as eluent to obtain 0.53 g of p-octyloxybiphenyldicarboxylic acid 2-fluorooctyl ester.
(yield 50%). The following specific rotation and IR (infrared absorption) data were obtained for the product.

(C=2@).

IR (cm-'): 2900.1715.1605.1300.1200.
1120, 830. 770°2.5 and 13 In Example 1, in place of p'-octyloxybiphenylcarboxylic acid and 2-fluoro-1-octanol, the groups R1, zoX, 4), (), shown in Table 1 above were used, respectively.
! , m, carboxylic acid giving n, and 2 giving group R
Fluoroalkane visiting conductors of the present invention as shown in Table 1 above were obtained in the same manner as in Example 1 except that -fluoro-1-alkanol was used.

The specific optical rotation and phase transition temperature characteristic data of the product are summarized with those of Example 1 in Table 1 above.

Production of 5-octyl-2-[4-(2-fluoroheptyloxy)phenyl]pyrimidine.
g (3.0 mmo) and dry pyridine 1.0 Og (
13 mmol) and stirred for 30 minutes under water cooling. Add 0.69 g of P-toluenesulfonic acid chloride (
After the reaction was completed, 110 ml of INHC was added and extracted twice with 10 ml of methylene chloride, and the extract was washed once with 10 ml of distilled water. Anhydrous sodium sulfate was suitably added to the obtained methylene chloride solution for drying, and then the solvent was distilled off to obtain 0.59 g (2.0 mmol) of 2-fluoroheptyl p-toluenesulfonic acid ester.

Yield is 66%. The specific rotation and IR data of the product are as follows.

Specific optical rotation [α]2:” + 2, 59° (c; 1, C
HCI3).

Specific optical rotation [α] 21°' + 9.58° 4J, f- (cm 1.CHC13) - IR (cm →): 2900.2850.1, 600.1450° 1350
．． 1170, 1090, 98o.

810, 660, 55o.

0°43 g of (+)-2-fluoroheptyl P-)luenesulfonic acid ester obtained as above (1,
5 mmol) and 0.28 g of 5-octyl-2-(4-hydroxyphenyl)pyrimidine (1,0 mmol 1
) was added with 0.2 ml of 1-butanol and stirred well. Add 1.0 ml of l-butanol to the solution in advance. Immediately pour in an alkaline solution prepared by dissolving 0.048 g (1.2 mmo 1) of sodium hydroxide in oml.
After the reaction was heated and refluxed for an hour and a half, 10 ml of distilled water was added and extracted once with 10 ml and 5 ml of benzene, respectively, and anhydrous sodium sulfate was appropriately added to the extract to dry it. After drying, the solvent was distilled off and the target product (+)- was collected using a silica gel column (chloroform).
0.17 g (0.43 mm
I got a reward.

The yield was 43%, and the specific rotation and IR were as follows:
The data was obtained.

(c = 1. CHCIs) - (c = 1.
CHCIm)-IR(cm-') U2900, 2B50. 1600, 1580°14
20.1250.1160. 800.720
, 650. 550°424.25.26 and 27 in real jll13, 2-fluoroheptator, 5
-octyl-2-(4-hydroxyphenyl)pyrimidine, 2- giving the group R shown in Table 1 above, respectively.
Fluoro-1-flukanol and groups R', -(), -
Fluoroalkane derivatives of the present invention as shown in Table 1 above were obtained in the same manner as in Example 3, except that 4-substituted phenol conductors giving $, (), l, m, and n were used.

By the reaction steps shown in the following (1), (2), and (3), p'-octyloxybiphenylcarboxylic acid-p of the above formula
″-(2-fluorooctyloxycarbonyl)phenyl ester was produced.

(1) Production of p-acetyloxybenzoic acid 2-fluorooctyl ester 0.68 g (3,7
mm01) with 7 ml thionyl chloride for 2 hours 30
After heating under reflux for several minutes, unreacted thionyl chloride was distilled off.
Acid chloride was obtained.

Next, 0.83 g (7.4 mmol) of triethylenediamine
) was dissolved in 5 ml of dry benzene, potassium hydroxide was added, and the mixture was dried for about 30 minutes. This solution (-)
2-Fluoro-1-year-old tanol 0.86g (4,5
The mixture was placed in a container containing mmo 1) and shaken and stirred. This solution was added dropwise to the above acid chloride under stirring, and after 5 minutes
The mixture was stirred at 0°C for 2 hours.

After the reaction is complete, add 8 ml of IN hydrochloric acid to 1. Added 30ml of water.

This solution was extracted with benzene, and the aqueous layer was further extracted with benzene.
Extracted twice with ml. Add 15 ml of IN sodium carbonate aqueous solution to this benzene layer, extract benzene in the same manner as before, and extract 8 ml of benzene from the aqueous layer! Extracted twice. Anhydrous sodium sulfate was added to this benzene layer and it was dried overnight.

Benzene was distilled off to obtain a crude product. Benzene this:
The mixture was separated by silica gel chromatography using 1:1 hexane to obtain 0.80 g (yield 69%) of p-7 cetyloxybenzoic acid (2-fluorooctyl) ester.

Zen).

IR (cm-”): 2850~2950.1760.1720°1600.
1265.1190° (2) Production of p-hydroxybenzoic S2-fluorodooctyl ester 0.750 g (2,5
mmol) was dissolved in 1.5 ml of ether. A solution of 0.27 g (2.5 mmol) of benzylamine dissolved in 1.5 ml of ether was added thereto, and the mixture was left at room temperature overnight.

After that, the ether was distilled off and p-hydroxybenzoic acid (
A mixture of 2-fluorooctyl) ester (4) and N-7 cetylbenzylamine (5) was obtained. This was separated by silica gel column chromatography using a mixture of ethyl acetate and methylene chloride = 1:9 to obtain 0.53 g of purified product A (yield: 78%). The specific rotation and IR data of the product are as follows.

Specific optical rotation [α] 2Z + 12.6° (C = 2, Ben ρ Zen).

IR (cm-”): 3390.2850~2940.1675°1605.
1590.1265゜(3)p'-octyloxybiphenylcarboxylic acid-p
Production of ``-(2-fluorooctyloxycarbonyl)phenyl ester P'-octyloxybiphenylcarboxylic acid 0゜65g
After heating and refluxing (2 mmol) with 4 ml of thionyl chloride for 2 hours and 30 minutes, unreacted thionyl chloride was distilled off to obtain an acid chloride.

Next, 0.44 g (4 mmol) of triethylenediamine
was dissolved in 5 ml of dry benzene, potassium hydroxide was added, and the mixture was dried for about 30 minutes.

This solution was mixed with 0.53 g of p-7 cetyloxybenzoic acid (2-fluorooctyl) ester obtained in (2) above (
The mixture was placed in a container containing 2 mmO1) and shaken and stirred. This solution was added dropwise to the above acid chloride under stirring and finished at t & 50°C.
The mixture was stirred for 2 hours.

After the reaction was completed, IN hydrochloric acid and water were added and extracted with benzene, followed by addition of IN aqueous sodium carbonate solution and extracted with benzene. Anhydrous sodium sulfate was added to this benzene solution and the mixture was dried and smoked overnight.

Benzene was distilled off, and the product was further separated by silica gel column chromatography using benzene as an eluent to obtain 0.58 g of P-octyloxybiphenylcarboxylic acid-p″-(2-fluorooctyloxycarbonyl)phenyl ester. (yield 50%). The specific rotation and IR data of the product are as follows.

Specific optical rotation [α] +8.7° (C=2, benzene).

IR (cm-'): 2950-2850, 1740, 1730.1610,
1295, 1285, l 120.1080,
830, 760゜6.12゛ and 16 In Example 7, providing P, q, r instead of P-7 setoxybenzoic acid, 2-fluoro-1-octatool and p'-octyloxybiphenylcarboxylic acid. Carboxylic acid, 2-fluoro-1-7 lucanol giving the group R and carboxylic acid giving the group R'', ()-14, 1.m, n, were used in the same manner as in Example 7, Fluoroalkane derivatives of the present invention as shown in the above-mentioned coating 1 were obtained.

The specific rotation and phase transition temperature characteristic data of the product are summarized with those of Example 7 and are shown in the coating 1 above.

Practical Example-L The p- of the above formula is obtained by the reaction steps shown in (1) and (2) below.
Octyloxybenzoic acid-p-(2-fluorodecyloxy)phenyl ester was produced.

(1) p-hydroquinone mono(2-fluorodecyl)
Manufacture of ether.

Clear i.e. 2-fluorodecanol (6) 3, 15g
(18 mmol) and 4.25 g (54 mmol) of dry pyridine.
mmol) were placed together in a container with a nitrogen atmosphere and stirred.

Cool the container with ice and add P-toluenesulfonyl chloride 3
．． 75 g (20 mmol 1) was added in two portions and stirred for 3 hours. After the reaction was completed, it was neutralized with 2N hydrochloric acid and diluted with methylene chloride lom! The aqueous layer was further extracted twice with 5 ml 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, and 5.60 g of 2-fluorodecyl p-toluenesulfonic acid ester (7) (yield 94%) was obtained.
) was obtained. Its specific optical rotation and IR data are as follows.

Specific optical rotation [αf2-0 +4.2° (C=2, methylene chloride).

IR (cm□I): 2850-2900.1600.1350.1170.
1100. 660. 550°5 of 7 obtained above.
60g (17mmol).

Hydroquinone 3.74g (34mmol)l -
5 ml of butanol was added and stirred. A solution of 1.02 g (25 mmol) of sodium hydroxide dissolved in 13 ml of 1-butanol was slowly added thereto, and after 1 drop,
After the reaction was completed at 0.degree. C. for 7 hours, 40 ml of water 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 2.57 g (yield: 56%) of purified p-hydroquinone mono(2-fluorodecyl) ether (8). The specific rotation and IR data of the product are as follows.

Specific optical rotation [α]o” + t, ao (c=2.methylene chloride).

IR (cm'): 3600-3200.2900.1680.1590.
1280.1160. 700° (2) P-octyloxybenzoic acid-p'-(2-fluorodecyloxy)
Production of phenyl esters.

sp-octyloxybenzoic acid 0.93g (3°7mmo
After heating and refluxing 1) with 8 ml of thionyl chloride for 2 hours, unreacted thionyl chloride was distilled off to obtain an acid chloride.

Separately, 0.81 g of triethylenediamine (7°4 mmo
1) was dissolved in 5 ml of dry benzene, potassium hydroxide was added, and the mixture was dried for about 30 minutes. Add this solution to (1) above.
P-hydroquinone mono(2-fluorodecyl)ether obtained in 1. og (3.7 mmol 1) and shaken and stirred. This solution was added dropwise to the above acid chloride at a rate of 1 to 2 times, and then heated at 50° C. for 2 hours.

After the reaction was completed, IN hydrochloric acid and water were added and extracted with benzene, followed by addition of IN aqueous sodium carbonate solution and extracted with benzene. Anhydrous sodium sulfate was added to this benzene solution and dried overnight.

Benzene was distilled off, and the product was separated by silica gel chromatography using benzene as a solution to give 1.49 g of p-octyloxybenzoic acid-p'-(2-fluorodecyloxy)phenyl ester (yield: 81%). I got it.

The specific rotation and IR data of the product are as follows.

benzene).

IR(am-1): 2900.1740.1610.1520.1280.
1250. ．． 1210.1170.1130, 76
0. 690° and 31 In Example 11? -2-fluoro- fluorodecanol, P-hydroquinone and P-octyloxybenzoic acid, each with a group R shown in Table 1 above.
1-Flukanol, p-hydroquinone or p, p'-
didroxibif, nil and the group R1, (), (), sha, l.

Fluoroalkane derivatives of the present invention as shown in Table 1 above were obtained in the same manner as in Example 1, except that carboxylic acids giving m and n were used.

The specific rotation and phase transition temperature characteristic data of the product are shown in Table 1 above, along with that of Example 11.

11] Liquid crystalline compound produced in Example 1 (p-octyloxybiphenylcarboxylic acid?-fluorooctyl ester)
A liquid crystal composition containing this as a compounding component was prepared.

The composition and phase transition temperature of the liquid crystal composition are shown below.

This composition had a spontaneous polarization of 8.8 nC/cm'', which was about 20 times higher than that of MORA-8 alone, which was 0.45 nC/cm''.

A liquid crystal element was formed using the liquid crystal compound produced in Example 11. Approximately 1,000 ITO films were placed as electrodes on the highly precisely polished 1O10×20 glass, and approximately 1
Ooo's SiO□ was deposited in a kiln using the ion beam method.

The liquid crystal compound (P-octyloxybenzoic acid-p'-(
2-fluorodecyloxy)phenyl ester) was added dropwise, and the glass substrates were stacked facing each other. When parallel interlocking was performed while holding the substrate at 80°C, horizontally aligned monodomains were obtained.

The film thickness at that time was 1.2 gm, and when driven at 65°C with a driving voltage ±IOV and a pulse width of 200 sec,
Good switching conditions were obtained with a contrast of 18.

Claims (1)

[Claims] 1. The following general formula (I) ▲There are numerical formulas, chemical formulas, tables, etc.▼(I) [Here, R represents an alkyl group having 1 to 16 carbon atoms, and C
^* indicates an asymmetric carbon atom. Also, R^1 is a carbon number of 1 to 1
6 alkyl or alkoxy groups, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼ are respectively phenylene groups (▲Mathematical formulas, etc.) , chemical formulas, tables, etc. ▼)
, cyclohexylene group (▲Mathematical formula, chemical formula, table, etc. available▼), and pyrimidinylene group (▲Mathematical formula, chemical formula, table, etc. available▼). p is 0 or 1, and when p=1, q is 1 or 2. r is 0 or 1. Further, l, m, and n are 0 or positive integers that satisfy the relationship l+m+n≧1. ] A fluoroalkane derivative represented by. 2. General formula (I) below ▲ Numerical formulas, chemical formulas, tables, etc. are available ▼ (I) [Here, R represents an alkyl group having 1 to 16 carbon atoms, and C
^* indicates an asymmetric carbon atom. Also, R^1 is a carbon number of 1 to 1
6 alkyl or alkoxy groups, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲There are mathematical formulas, chemical formulas, tables, etc.▼ are respectively phenylene groups (▲Mathematical formulas, etc.) , chemical formulas, tables, etc. ▼)
, cyclohexylene group (▲Mathematical formula, chemical formula, table, etc. available▼), and pyrimidinylene group (▲Mathematical formula, chemical formula, table, etc. available▼). p is 0 or 1, and when p=1, q is 1 or 2. r is 0 or 1. Further, l, m, and n are 0 or positive integers that satisfy the relationship l+m+n≧1. ] A liquid crystal composition comprising at least one fluoroalkane derivative represented by the following as a compounding component.