JPH01135745A - Novel liquid crystal compound and liquid crystal composition - Google Patents

Abstract

NEW MATERIAL:A compound expressed by formula I (R1 and R2 are straight- chain or branched 1-18C alkyl, optically active alkyl halide, alkoxyalkyl, cyano or isothiocyanate; a, b and c are 0, 1 or 2; a+b+c is >=2; A is single bond, -O-, -COO-, -O-COO- or -OCO-; B and D are single bond, -COO-, -OCO-, -N=CH-, -CH=CH-, etc.; X, Y and Z are 1,4-phenylene, 1,4-trans-cyclohexyl, 2,5-pyrimidine, 2,5-pyridine or 2,5-pyrazine). EXAMPLE:2-(4'-Decyloxyphenyl)-5-hexyloxymethylenecarbonyloxypyrimidine. USE:A liquid crystal compound. PREPARATION:An alcohol derivative expressed by formula II is condensed with an alkoxyacetic acid expressed by formula III using a condensing agent, such as N,N'-dicyclohexylcarbodiimide, to afford the aimed compound expressed by formula I.

Description

DETAILED DESCRIPTION OF THE INVENTION Field of Industrial Application The present invention relates to a novel liquid crystal compound and a liquid crystal composition containing the liquid crystal compound.

Further, in this specification, the term "liquid crystal compound" refers to a compound that is useful as a component of a liquid crystal composition even if it is not detected to exhibit a liquid crystal phase by itself.

Conventional technology The currently widely used display systems for liquid crystal display devices are the twisted nematic type (TN type) and the dynamic scattering type (DS type).
This is a display using a nematic liquid crystal cell as the main component. One of the disadvantages of conventional nematic liquid crystal cells is the fact that the response speed is slow, and a response speed of only a few m5ec can be obtained at most. This is one of the factors that limits the range of applications for nematic (alpha) crystal cells. However, it has recently been found that a faster response can be obtained by using a smectic liquid crystal cell.

It has become clear that some optically active smectic liquid crystals exhibit ferroelectricity, and there are great expectations for their use. The liquid crystal was 1975 R, B,
It is a compound synthesized by Meyer et al. and whose representative example is 4-(4-n-decyloxybenzylideneamino)cinnamic acid-2-methylbutyl ester (hereinafter abbreviated as DOBAMBC), and its chiral smectic In the C phase (hereinafter abbreviated as Sm C aqueous phase),
It is characterized by exhibiting ferroelectricity (J, ph
ys 1que, April 4th, L-(39 (1975)).

In recent years, N, A, CIa + Kawa (et al. (A l:1 p l
, P tiVs, Let L, 2L1
1. 8 9 (1980) ): Therefore, DO
With the discovery of high-speed response on the order of seconds in BAMBC's thin-film cells, ferroelectric liquid crystals are being used not only for displays such as LCD TVs, but also for optical printer heads. It is attracting attention as a material that can be used for optoelectronic related elements such as optical Fourier transform elements and light valves.

Problems to be Solved by the Invention DOB AMB C has low spontaneous polarization and is a ship base, so it has poor physical and chemical stability.

Therefore, various physically and chemically stable compounds have been searched for as ferroelectric liquid crystal materials.

The main focus has been on optimizing practical characteristics such as threshold characteristics and temperature 1 characteristics of these various characteristics.

However, currently known ferroelectric liquid crystals alone cannot exhibit various physical properties at room temperature, such as large spontaneous polarization, low viscosity, long helical pitch, and appropriate tilt angle, which are sufficient to achieve the above-mentioned practical properties. There is no indication over a wide temperature range including,
Therefore, in reality, studies have been conducted to optimize the above properties by mixing several types of substances, such as monomer compounds that have or induce large spontaneous polarization, low-viscosity compounds, and compounds with opposite helical pitches. There is. In addition, in order to obtain a liquid crystal composition that exhibits ferroelectricity in a sufficiently wide temperature range, it is necessary to use a ferroelectric liquid crystal that has a wide temperature range or a smectic C that is not chiral.
It is effective to mix liquid crystals.

Therefore, as the 11 materials used in the ferroelectric liquid crystal composition, 1. Optically active compounds that have or induce large spontaneous polarization; 2. 3. Compounds that are considered to have low viscosity due to their skeleton, or compounds that do not impair their liquid crystallinity even when mixed with compounds that are considered to have low viscosity due to their skeleton; 3. A liquid crystal compound exhibiting ferroelectricity over a wide temperature range; 4. The helical pitch is infinitely long and the mixture m can be freely set in the overall mixture design:
+I! Iii? It is considered necessary to study a large number of optically active compounds and other compounds that can be used to optimize their physical properties.

Means for Solving the Problems In order to solve the above-mentioned problems, the present inventors searched for various liquid crystal materials and arrived at the present invention.

As shown in the examples, the present invention has 1. Even if it is combined with a yC Gakkatsu f11 compound that has or induces large spontaneous polarization, a compound J5 that is considered to have a low viscosity due to its 2° skeleton, or a compound that is considered to have a low viscosity due to its skeleton, the liquid crystal will not change. 3. Compounds that do not have t'R properties. jα crystal compound exhibiting ferroelectricity over a wide temperature range; 4. This makes it possible to provide a group of compounds having properties such as optically active compounds with infinitely long helical pitches and the amount of which can be freely adjusted in the overall formulation design. .

That is, the present invention provides - Formula (1) % Formula % (1) (However, in the above formula, R1 and R2 are a linear or branched alkyl group having 1 to 18 carbon atoms, an optically active halogenated alkyl group, It represents an alkoxyalkyl group, a cyano group or an isothiocyanate group, a, b, and c are 0.1 or 2, and a+b+c is 2 or more, and A is a single bond,
-o-, -coo-, -o-coo-, or -0C
O-, B and D are single bonds, -COO-, -0CO
-, -N=CI+-1-CIl=N-1-CI+2-O
-1-O-CI+2- or -CIl=CI+-, x, y, z are 1,4-phenylene groups, or halogen, cyano group, nitro group, or methyl group in the benzene ring.
1,4-phenylene group, 1゜4-transcyclohexyl group, 2,5-pyrimidine group, 2,5-pyridine group or 2,5-pyrazine group, which is substituted with The present invention relates to a compound and a liquid crystal composition containing the same.

In general, liquid crystal compounds have a rod-like structure consisting of a core portion such as a benzene ring and a chain portion such as an alkyl chain.

Among them, it is well known that those whose alkyl chain has more than a certain number of carbon atoms tend to disperse the smectic phase.

In general, it is well known that compounds having the same skeleton exhibit a similar phase series even if the number of carbon atoms in the alkyl chain differs slightly. In the above-mentioned formula (1), a compound in which R1 is an alkyl group having 6 to 14 carbon atoms is particularly useful as a ferroelectric liquid crystal material because it easily takes a Cursmectic C phase. Further, compounds that do not become ferroelectric iαα crystal materials by themselves can also be used as compounded materials for ferroelectric lα crystals, or liquid crystal materials in general.

For example, the following 1. ．．
2. ．． 3. ．． 4. This is a compound as shown in

-175711, Patent application 1986-023510, Patent application 1973
9-023!51 L Japanese Patent Application 1987-074748, Japanese Patent Application 1987-189232, Japanese Patent Application 1986-22920, Japanese Patent Application 1987-87034, Japanese Patent Application 1986-117053, Japanese Patent Application 1986-144136, 1986-162654, patent application 1982-162656, patent application 1982-250335,
Compound disclosed in Japanese Patent Application No. 60-291179.

2. A group of compounds having a smectic C phase, such as the following.

Alkoxybiphenylcarboxylic acid alkyl ester, alkylcarbonyloxybiphenylcarboxylic acid alkyl ester, alkoxybenzoic acid alkoxyphenyl ester, alkoxybenzoic acid alkyloxycarbonylphenyl ester, alkoxybenzoic acid alkoxyalkoxyphenyl ester, alkoxybenzoic acid alkoxybiphenyl ester, alkoxybiphenyl carbon Acid alkoxyphenyl ester, alkylbenzoic acid alkoxybiphenyl ester, alkylbiphenylcarboxylic acid alkoxyphenyl ester, alkoxybenzoic acid alkylbiphenyl ester, alkoxybiphenylcarboxylic acid alkylphenyl ester, alkylcarbonyloxybenzoic acid alkoxybiphenyl ester, alkylcarbonyloxybiphenylcarboxylic acid Alkoxyphenyl ester, alkoxybenzoic acid alkylcarbonyloxybiphenyl ester, alkylbiphenylcarboxylic acid alkylcarbonyloxyphenyl ester,
5-alkyl-2-(4'-alkoxyphenyl)pyrimidine, 5-alkoxy-2-(4'-alkoxyphenyl)pyrimidine, 5-alkyl-2-(4'-alkylcarbonyloxyphenyl)pyrimidine, 5-alkoxy -2-(4'-alkylcarbonyloxyphenyl)pyrimidine, 5-furkyl-2-(4'-alkyloxycarbonylphenyl)pyrimidine, 5-alkoxy-2-(4'-alkyloxycarbonylphenyl)pyrimidine, 5- Furkyl-2-lukoxy-2-(4'-
alkoxyphenyl) pyrazine, 5-alkyl-2-(
4'-alkylcarbonyloxyphenyl)pyrazine, 5-alkoxy-2-(4'-alkylcarbonyloxyphenyl)pyrazine, 5-argyl-2-(4'
-alkyloxycarbonylphenyl)pyrazine, 5-
Alkoxy-2-(4'-alkyloxycarbonylphenyl)pyrazine, 3-(4'-alkylphenyl)
-6-alkoxypyridazine, 3-(4'-alkoxyphenyl)-6-alkoxypyridazine, 3-(4'
-alkoxyphenyl)-6-alkylpyridazine, 5
- (4'-alkoxyphenyl) -2-(4''-alkoxyphenyl)pyrimidine, 5- (4'-alkoxyphenyl)-2-(4''-alkoxyphenyl)
Pyrimidine, 5-(4'-alkylphenyl)-2-
(4"-alkylcarbonyloxyphenyl>pyrimidine, 5-(4'-alkoxyphenyl)-2-(4"
-alkylcarbonyloxyphenyl)pyrimidine, 5
-(4'-alkylphenyl')-2-(4''-alkyloxycarbonylphenyl)pyrimidine, 5- (4
'-alkoxyphenyl)-2-(4''-alkyloxycarbonylphenyl)pyrimidine, 5-(4'-alkoxyphenyl)-2-(4''-alkoxyphenylcarbonyloxy)pyrimidine, 5-(4'-alkylphenyl) )-2-(4''-alkoxyphenylcarbonyloxy)pyrimidine, 5-(4'-alkoxyphenyl)-2-(4''-furkylphenylcar;1tenyloxy)pyrimidine, 5-(4'-alkylphenyl')
)-2-(4”-furkylphenylcarbonyloxy)
Pyrimidine, 5-(4'-alkylphenyl)-2
-(4''-alkoxyphenyl)-1,2,4-1 riazine, 5-(4'-alkoxyphenyl) -2-(
4"-alkoxyphenyl)-1,2,4-)riazine, 5-(4'-alkylphenyl')-2-(4"-
alkylcarbonyloxyphenyl)-1,2,4-triazine, 5-(4'-alkoxyphenyl) -2-
(4”-alkylcarbonyloxyphenyl)-1,2
゜4-triazine, 5- (4'-alkylphenyl)
-2-(4”-furkyloxycarbonylphenyl)-
1,2,4-) riazine, 5-(4'-alkoxyphenyl)-2-(4''-alkyloxycarbonylphenyl)-1,2,4-) riazine, etc. A compound having a smectic C phase in which one or more hydrogen atoms contained in an alkyl moiety or skeleton are replaced with a halogen, a cyano group, a nitro group, a trifluoromethyl group, an alkoxy group, an alkyl J&, etc.

4.2. Or 3. One or more hydrogen atoms in the alkyl moiety of the alkyl group, alkoxy group, alkylcarbonyloxy group, alkyloxycarbonyl group of the compound groups listed in A group of compounds in which an asymmetric carbon is introduced by substitution with a smectic compound, and which are made into ferroelectric liquid crystals exhibiting a chiral smectic C phase either alone or by mixing with a smectic compound.

The compound represented by general formula (1) is synthesized as follows.

The compound represented by the general formula (1) has the modified general formula (A)
An alcohol derivative represented by the following and an alkoxyacetic acid represented by the following general formula (i) are N.

Condensation using a condensing agent such as N'-dicyclohexylcarbodiimide, or reaction with an alkoxyacetic acid chloride derived from a compound represented by the formula (-) in the presence of a tertiary amine such as pyridine. Just let it happen.

R+-A-(X)a-B-(Y)b-D-(Z)c-O
ll (A) R20C112COO1+
The compound represented by (i) - formula (i) is
Alcohol and halogenoacetic acid with sodium hydride, 9
The reaction may be carried out using a base such as thorium agutoxide, and suitable solvents include N,N-dimethylformamide, diethyl ether, and tetrahydrofuran.

Moreover, the compound represented by formula (i) can also be synthesized using hydroxyacetic acid and an alkyl halide.

Among the groups represented by R1 or R2 in the above-mentioned formula (2), optically active groups are easily derived from, for example, the following optically active alcohols and optically active carboxylic acids.

2-methylbutanol, 3-methylpentanol, 4-
Methylhexanol, 2-butanol, 2-pentanol, 2-hexanol, 2-heptatool, 3-hexanol, 2-octatool, 1-phenylethanol,
p-(2-methylbutyl)phenol, p-(2-methylbutoxy)phenol, linalool, nerolidol,
Sobrerol, carbomenthol, menthol, isomenthol, borneol, isoborneol, carveol, cholesterol, 2-halo 2-phenylethanol, 2-phenyl-3-halo l-propatol, 3
-Fe=2-halo 1-propatol, l-phenyl-2-halo 1-propanol, 3-halo 2-methyl-1-propatol, 1.1.1-) dihalo-2-propatol, 2 -halo 1-butanol, 3-halo,
l-7tanol, 2,3-dihalo-1-butanol, 2
゜4-dihalo-1-butanol, 3,4-dihalo-1-
Butanol, 1,1.1-trihalo-2-butanol,
4.4.4-) rimlow 3-halo l-butanol, 2
．． 3.4-) Rehalo l-butanol, 3.3.4,
4.4-pentahalo 2-butanol, 2-to〇-3-
Methyl-1-butanol, 2-halo 3,3-dimethyl-1-butanol, 2-halo l-pentanol, 3-
Halo 1-pentanol, 4-Hero 1-pentanol, 2.4-dihalo-1-pentanol, 2.5-dihalo-1-pentanol, 1,1.1-)rimuro 2-pentanol, 1. ．． 1,1.2.2-Pentahalo 3-pentanol, 2-he〇-3-methyl-1-pentanonyl, 2-halo 4-methyl-1-pentanol, 2-halo 3-monohalomethyl XXX4-methyl-1 -pentanol, 2-halo 1-hexanol, 3-halo 1-hexanol, 4-halo 1-hexanol, 5-halo 1-hexanol, 2,5-dihalo-1-J\xanol, 2,6-cyhalo 1-hexanol, 1,1.1-
Trihalo 2-hexanol, 2,5.6-) Limulow 1-hexanol, 2-halo l-heptatool, 1.
1.1-) Dihalo-2-heptatool, 2-halo1-
octatool, 1,4.1-trihalo 2-octatool, 2-halo 2-phenylethanoic acid, 3-halo 2
-Methylpropanoic acid, 2-phenyl-3-herobutanoic acid, 3-phenyl-2-methylpropanoic acid, 2-phenyl-3-herobropanic acid, 2-halobutanoic acid, 3-octabutanoic acid, 2 .3-dihalobutanoic acid, 2゜4-dihalobutanoic acid, 3,4-dihalobutanoic acid, 4.4.4-)lihalo-3-octabutanoic acid, 2゜3.4-)dihalobutanoic acid, 2-halo 3-methylbutane acid, 2-halo 3.3-
Dimethylbutanoic acid, 2-halopentanoic acid, 3-halopentanoic acid, 4-halopentanoic acid, 2,4-dihalopentanoic acid, 2,5-dihalopentanoic acid, 2-halo-3-methylpentanoic acid, 2-halo-4-methylpentane acid, 2-halo 3-monohalomethyl-4-methylpentanoic acid, 2-
Halohexanoic acid, 3-halohexanoic acid, 4-halohexanoic acid, 5-halohexanoic acid, 2.5-dihalohexanoic acid, 2.6-dihalohexanoic acid, 2,5.6-)dihalohexanoic acid, 2-halohexanoic acid, 2-to 〇Octanoic acid,
2-phenylpropanoic acid, 2-phenylbutanoic acid, 3-
Phenyl-2-methylpropanoic acid, 2-methylbutanoic acid, 2.3-dimethylbutanoic acid, 2.3.3-trimethylbutanoic acid, 2-methylpentanoic acid, 3-methylpentanoic acid, 2.3-dimethylpentanoic acid , 2.4-dimethylpentanoic acid, 2.3.3゜4-tetramethylpentanoic acid,
2-Methylhexanoic acid, 3-methylhexanoic acid, 4-methylhexanoic acid, 2,5-dimethylhexanoic acid, 2-methylhebutanoic acid, 2-methyloctanoic acid, 2-trihalomethylpentanoic acid, 2-trihexanoic acid lomethylhexanoic acid, 2
-Trihalomethylhebutanoic acid, etc.

(However, in the above chemical formula, halo represents fluorine, chlorine, bromine, or iodine.) Some of the above optically active alcohols are asymmetric reduction of the corresponding ketone by a chiral metal catalyst, a microorganism, or an enzyme, and an amino acid. It can be obtained by reductive deamination etc. of easily obtained. Others can be derived from optically active amino acids and optically active oxyacids, such as those naturally occurring or obtained by resolution.

Furthermore, some of the above-mentioned optically active carboxylic acids can be obtained by oxidation of the corresponding alcohol and reductive deamination of the amino acid. Others can be derived from optically active amino acids and optically active oxyacids, such as those naturally occurring or obtained by resolution.

Alanine, valine, leucine, isoleucine, phenylalanine, serine, threonine, allothreonine, homoserine, alloisoleucine, tert-0 nonsine, γ-
Methylleucine, 2-7minobutyric acid, norvaline, norleucine, ornithine, lysine, hydroxylysine, phenylglycine, trifluoroalanine, aspartic acid, glutamic acid, lactic acid, mandelic acid, trobic acid, 3-hydroxybutyric acid, malic acid, tartaric acid, Isopropyl malate etc.

Effects of the Invention Some of the compounds of the present invention become ferroelectric liquid crystals when used alone. Further, among the compounds of the present invention, substances that do not form ferroelectric liquid crystals by themselves can also be used as constituent materials for ferroelectric liquid crystal compositions.

Among the compounds of the present invention, optically active compounds can be used for purposes such as white tiller color display, cholesteric nematic phase change display, prevention of reverse domain generation in TN type cells, pitch:A adjustment in STNTN type cells, etc. It can also be used by adding it to Nemanac liquid crystal.

Furthermore, among the compounds of the present invention, compounds that form smectic liquid crystals can also be used for memory type display elements such as thermal writing laser writing.

Effects of the Invention The compound of the present invention can be used as a constituent material of a liquid crystal composition. Furthermore, some of the compounds of the present invention can be used as constituent materials of ferroelectric liquid crystal compositions. According to the present invention, it is possible to provide a useful material for a compound, which has a considerably long helical pitch and whose amount can be freely adjusted.

EXAMPLES The compounds of the present invention will be explained in more detail with reference to Examples below, but the present invention is not limited to these Examples.

Hereinafter, C, SX, Sc, Sc-tree, N-tree, ■ phase are respectively crystalline phase, chiral smectic phase that cannot be clearly identified, smectic C phase, and chiral smectic C phase.
Purification of the compounds of the present invention exhibiting phase, chiral nematic phase, isotropic phase was carried out by silica gel chromatography and recrystallization from alcohol or hexane. The phase transition point measurement Ill shown below may be influenced to some extent by the purity of the material.

Example 1 Synthesis of 1'l-hexyloxyacetic acid 11-hexanol 5.40g (52,91 former nol
), add 30 ml of DMF, add 4.44 g (0.11 mol) of 60% hydrogen IL sodium under water cooling, and add 30 ml of DMF.
Stir for a minute. Add 5 g of chloroacetic acid to this suspended solution.
A solution of (52.9 mmol) dissolved in 20 ml of DMF was added, stirred at room temperature for 2 hours, and then heated to 80°C.

After stirring in this state for 48 hours, it was cooled with water and diluted with 50% diluted hydrochloric acid.
ml and extracted three times with 100 ml of ether. Ether layer IQ 1llE Dry with magnesium hydroxide sulfate, concentrate, and distill under reduced pressure to obtain target compound 1.1
5g was obtained.

b, 9.140℃15mmHg Synthesis of 2-(4'-decyloxyphenyl)-5-hexyloxymethylenecarbonyloxypyrimidine Combine n-hexyloxyacetic acid and 2-(4'-decyloxyphenyl)-6-hydroxypyrimidine. The target compound was obtained by condensation using a conventional method.

Example 2 Synthesis of n-butyloxyacetic acid 2.56 g (0.11 utt) of sodium metal was added to 35 g (0.47 mol) of n-butanol and heated to 40°C under argon to prepare sodium butoxide. . After cooling with water, 5 g of chloroacetic acid (52.9 mmo
1) was added, heated to 60°C, stirred for 48 hours, and excess butanol was distilled off. After adding 30 ml of dilute hydrochloric acid to the residue and extracting three times with 40 ml of ether, the ether layer was dried over anhydrous magnesium sulfate, concentrated, and then distilled under reduced pressure to obtain 1.19 g of the target compound.

b, p, 155℃/21mmHg Synthesis of 2-(4'-butyloxymethylenecarbonyloxyphenyl)-5-octylpyrimidine (c) 11-Butyloxyacetic acid and 2-(4'-hydroxyphenyl)-5-octyl The target compound was obtained by condensing pyrimidine (U) in a conventional manner.

Example 3 Synthesis of 2-methylbutyloxyacetic acid By reacting 2-methylbutanol and chloroacetic acid in the same manner as in Example 1, the desired compound No. 1 was obtained. b
, 9.180℃/12mmHgp, Synthesis of p'-nonylcarbonyloxybiphenyl-2-methylbutyloxyacetic ester 2-methylbutyloxyacetic acid, p, p'
The target compound was obtained by condensing -nonylcarbonyloxybiphenol in a conventional manner.

Example 4 Synthesis of 2-(p-(p'-(2''-methylbutyloxymethylenecarbonyloxy)phenyl)carbonyloxy)phenyl-5-octylpyrimidine (2-methylbutyloxymethylenecarbonyloxybenzoic acid) The target compound (e) was obtained by condensing 2-(4'-hydroxyphenyl)-5-octylpyrimidine in a conventional manner.

Example 5 Table 1 summarizes the phase transition points of the compounds shown in Examples 1 to 4 and the compounds synthesized in the same manner.゛Among the compounds of the present invention, the compound having an optically active 2-methylbutyl group as an asymmetric source has a pitch of 10μ in the chiral nematic phase.
mn or more, and the pitch in the chiral smectic C phase is as long as 5 μm or more, making it a compound suitable for use as a ferroelectric liquid crystal material in the sense that the blending amount can be freely determined without damaging the alignment. .

Example 6 A ferroelectric liquid crystal compound (O) was obtained by blending the compounds of the present invention as follows.

2-(4'-decyloxyphenyl)-5-hexyloxymethylenecarbonyloxypyrimidine)
13wt% 2-(p-(p'-(2''-methylbutyloxymethylenecarbonyloxy)phenyl)carbonyloxy)phenyl-5-octylpyrimidine) (30
wt% 2-(p-octyloxyphenyl)-5-(p'-(
2”-methylbutyloxymethylenecarbonyloxy)
Phenyl)carbonyloxypyrimidine 27wt% Blend (O) was a blend that exhibited a chiral smectic C phase from 65°C to 124°C and a chiral nematic phase from 144°C.

Example 7 A ferroelectric liquid crystal compound was obtained by blending the compound of the present invention and a compound exhibiting a smectic C phase in the following manner.

Blend (O) 34wt% p-alkoxybenzoic acid p'-alkoxyphenyl ester 13wt% 2-(p-alkoxyphenyl)-5-alkylpyrimidine 19wt% 2-(p-alkoxyphenyl)-5-alkoxypyrimidine 23wt% 2-(p-alkoxyphenyl)-5-alkylcarbonyloxypyrimidine 9 wt% p-(p'-alkoxyphenyl)benzoic acid alkyl ester 2 wt% The formulation was heated from room temperature to 82°C t. The formulation exhibited a chiral nematic phase up to 104°C.

EXAMPLE A ferroelectric liquid crystal compound was obtained by blending the compound of the Japanese invention, a compound exhibiting a smectic C phase, and a compound exhibiting a chiral smectic C phase as follows.

Blend 77wt% p-octyloxybenzoic rIi p'-(2-methylbutoxy)phenyl ester L5wL%2-chloro-
3-Methylpentanoic acid 1)-(+)'-octyloxyphenyl)phenyl ester 4wt% 2-chloro-3-methylpentanoic acid 1)-(1)'-
The hebutylcarbonyloxyphenyl) phenyl ester 4wt% formulation was a formulation that exhibited a chiral smectic C phase from below freezing to 65°C and a chiral nematic phase up to 82°C.

ITO coated with polyimide using the blend as an alignment film
The mixture was injected into a liquid crystal cell with a cell thickness of 2 microns constructed using glass, and observed under a polarizing microscope while applying an IOV rectangular wave. Good contrast and high-speed response were observed, confirming that the composition of the present invention can be used as a ferroelectric liquid crystal material.

Claims (7)

[Claims] (1) General formula (I) R1-A-(X)a-B-(Y)b-D-(Z)c-O
COCH_2O-R2(I) (However, in the above formula,
R1 and R2 represent a linear or branched alkyl group having 1 to 18 carbon atoms, an optically active halogenated alkyl group, an alkoxyalkyl group, a cyano group or an isothiocyanate group,
a, b, c are 0, 1 or 2, and a+b+c is 2 or more, and A is a single bond, -O-, -COO-, -O-
COO- or -OCO-, B and D are single bonds, -COO-, -OCO-, -N=CH-, -CH=N
-, -CH2-O-, -O-CH2- or -CH=C
H-, and X, Y, and Z are a 1,4-phenylene group, or a 1,4-phenylene group in which the benzene ring is substituted with one or more halogen, cyano group, nitro group, or methyl group, 1 , 4-transcyclohexyl group, 2,5-pyrimidine group, 2,5-pyridine group or 2,5-pyrazine group. ) A new liquid crystal compound represented by (2) General formula (I) R1-A-(X)a-B-(Y)b-D-(Z)c-O
COCH_2O-R2(I) (However, in the above formula,
R1 and R2 represent a linear or branched alkyl group having 1 to 18 carbon atoms, an optically active halogenated alkyl group, an alkoxyalkyl group, a cyano group or an isothiocyanate group,
a, b, c are 0, 1 or 2, and a+b+c is 2 or more, and A is a single bond, -O-, -COO-, -O-
COO- or -OCO-, B and D are single bonds, -COO-, -OCO-, -N=CH-, -CH=N
-, -CH2-O-, -O-CH2- or -CH=C
H-, and X, Y, and Z are a 1,4-phenylene group, or a 1,4-phenylene group in which the benzene ring is substituted with one or more halogen, cyano group, nitro group, or methyl group, 1 , 4-transcyclohexyl group, 2,5-pyrimidine group, 2,5-pyridine group or 2,5-pyrazine group. ) A liquid crystal composition comprising at least one novel liquid crystal compound represented by: (3) A liquid crystal composition comprising at least one novel liquid crystal compound represented by the general formula (I) in claim (1) and at least one non-chiral smectic C liquid crystal. (4) Claims (1), characterized by containing at least one novel liquid crystal compound represented by the general formula (I) and at least one non-chiral smectic C liquid crystal represented by the following formula (II) A liquid crystal composition. R-Ph-Py-R'(II) (R, R' is an alkyl group, alkoxy group, acyloxy group or alkoxycarbonyl group, Ph is a 1,4-phenylene group, Py is a 2,5-pyrimidine group show.) (5) Item (1) of the claims, characterized by containing at least one novel liquid crystal compound represented by the general formula (I) and at least one non-chiral smectic C liquid crystal represented by the following formula (III). A liquid crystal composition. R-Ph-COO-Ph-R'(III) (R and R' represent an alkyl group, an alkoxy group, an acyloxy group, or an alkoxycarbonyl group, and Ph represents a 1,4-phenylene group.) (6) Claims (1), characterized by containing at least one novel liquid crystal compound represented by the general formula (I) and at least one non-chiral smectic C liquid crystal represented by the following formula (IV). A liquid crystal composition. R-Ph-Ph-R'(IV) (R and R' represent an alkyl group, an alkoxy group, an acyloxy group, or an alkoxycarbonyl group, and Ph represents a 1,4-phenylene group.) (7) Among the liquid crystal compositions set forth in claims (4), (5), and (6), a liquid crystal composition in which the helical pitch in the chiral nematic phase and chiral smectic C phase is 2 micrometers or more.