JPH0629260B2 - Phenylpyrimidine compound and liquid crystal composition - Google Patents

Description

TECHNICAL FIELD The present invention relates to a novel phenylpyrimidine compound and a liquid crystal composition containing the phenylpyrimidine compound, and more specifically to a phenylpyrimidine compound having an optically active group and the same. Liquid crystal composition.

[Prior Art] Conventionally, as a phenylpyrimidine compound, for example, 5-n-octyloxy-2- [4- (2-ethoxy-propyloxy) phenyl] pyrimidine which is a phenylpyrimidine compound exhibiting ferroelectricity [12th Proceedings of Liquid Crystal Symposium Lecture (issued in October 1986) p. 152-153] is known.

[Object of the Invention] The present inventors have proposed a phenylpyrimidine compound having a wider temperature range showing ferroelectricity than the conventional compounds, or a phenylpyrimidine compound useful as a constituent component of a liquid crystal composition, and the phenylpyrimidine compound. As a result of intensive studies on the liquid crystal composition to be contained, the present invention has been achieved.

[Means for Achieving the Object of the Invention] That is, [In the formula, R is a halogen atom or an alkyl group having 3 to 18 carbon atoms which may be substituted with an alkoxy group, X is -O- or a single bond (direct bond), and Z is F (fluorine atom). ) Is substituted with 1,4-phenylene group, m
Is an integer of 2 to 12, R'is an alkyl group having 1 to 12 carbon atoms which may be substituted with a halogen atom or an alkoxy group, and * indicates optically active. ] The phenyl pyrimidine compound shown by and general formula [In the formula, R is a halogen atom or an alkyl group having 3 to 18 carbon atoms which may be substituted with an alkoxy group, X is -O- or a single bond (direct bond), and Z is F (fluorine atom). ) Is substituted with 1,4-phenylene group,
R'is an alkyl group having 1 to 12 carbon atoms which may be substituted with a halogen atom or an alkoxy group, and * indicates that it is optically active. ] A phenylpyrimidine compound represented by, at least a liquid crystal composition characterized by containing at least one phenylpyrimidine compound represented by the general formula (1) as a blending component and at least a phenylpyrimidine compound represented by the general formula (2) A liquid crystal composition comprising one of them as a compounding component.

In the specification of the present application, the phenylpyrimidine compound having ferroelectricity is not only one that can observe a liquid crystal state such as a chiral smectic C phase, a chiral smectic I phase, and a chiral smectic F phase that exhibit ferroelectricity by itself, but is not alone. Even if the liquid crystal state exhibiting ferroelectricity cannot be observed, it also includes a substance having a chemical structure similar to the former and useful as a constituent component of a liquid crystal composition.

In the general formulas (1) and (2), as the alkyl group having 3 to 18 carbon atoms which may be substituted with a halogen atom or an alkoxy group for R, a linear alkyl group (propyl group, butyl group, pentyl group, Hexyl group, heptyl group, octyl group, nonyl group, decyl group, undecyl group, dodecyl group,
Tridecyl group, tetradecyl group, pentadecyl group, hexadecyl group, octadecyl group, etc.), branched alkyl group (1-methylpropyl group, 1-methylbutyl group, 1-methylhexyl group, 1-methylheptyl group, 2-methylbutyl group, 2 -Methylpentyl group, 2-methylhexyl group, 2-methylheptyl group, 2-methyloctyl group, 3
-Methylpentyl group, 4-methylpentyl group, 4-methylhexyl group, 5-methylheptyl group, 6-methyloctyl group, 7-methylnonyl group, 8-methyldecyl group, 9
-Methyldecyl group, etc.), an alkyl group having a substituent [for example, an alkyl group substituted with Cl (chlorine atom) (2
-Chloropropyl group, 2-chlorobutyl group, 2-chloropentyl group, 2-chlorohexyl group, 2-chloroheptyl group, 2-chlorooctyl group, 1-chloro-2-methylpropyl group, 1-chloro-2- Methylbutyl group, 1-chloro-3-methylbutyl group, etc.), F (fluorine atom) -substituted alkyl group (2-fluoropropyl group, 2-
Fluorobutyl group, 2-fluoropentyl group, 2-fluorohexyl group, 2-fluoroheptyl group, 2-fluorooctyl group, 1-fluoro-2-methylpropyl group,
1-fluoro-2-methylbutyl group, 1-fluoro-3
-Methylbutyl group, etc.), alkyl group substituted with an alkyloxy group (2-methoxypropyl group, 2-ethoxypropyl group, 2-propyloxypropyl group, 3-methoxybutyl group, 3-ethoxybutyl group, 3-propyl Oxybutyl group, 4-methoxypentyl group, 4-ethoxypentyl group, 4-propyloxypentyl group, 3-methoxypropyl group, 3-ethoxypropyl group, 3-propyloxypropyl group, 3-hexyloxypropyl group,
4-methyloxybutyl group, 4-propyloxybutyl group, 4-hexyloxybutyl group, etc.], an optically active alkyl group (optically active 2-methylbutyl group, optically active 2-methylpentyl group, optically active 2- Methylhexyl group, optically active 2-methylheptyl group, optically active 2-methyloctyl group, optically active 3-methylpentyl group, optically active 4-methylhexyl group, optically active 5-methylheptyl group, optically active 6-methyloctyl group Group, an optically active 1-methylpropyl group, an optically active 1-methylbutyl group, an optically active 1-methylheptyl group, an optically active 1-methyloctyl group) and an optically active alkyl group having a substituent [for example, Cl (chlorine Atom-substituted optically active alkyl group (optically active 2-chloropropyl group, optically active 2-chlorobutyl group, light Active 2-chloropentyl group, optically active 2-chlorohexyl group, optically active 2-chloroheptyl group, optically active 2-chlorooctyl group, optically active 1-chloro-2-methylpropyl group, optically active 1-chloro-2 −
Methylbutyl group, optically active 1-chloro-3-methylbutyl group, etc.), optically active alkyl group substituted with F (fluorine atom) (optically active 2-fluoropropyl group, optically active 2-fluorobutyl group, optical activity 2) -Fluoropentyl group, optically active 2-fluorohexyl group, optically active 2-
Fluoroheptyl group, optically active 2-fluorooctyl group, optically active 1-fluoro-2-methylpropyl group, optically active 1-fluoro-2-methylbutyl group, optically active 1
-Fluoro-3-methylbutyl group) and an alkyloxy group-substituted optically active alkyl group (optically active 2-methoxypropyl group, optically active 2-ethoxypropyl group, optically active 2-propyloxypropyl group, optically active 3-methoxybutyl group, optically active 3-ethoxybutyl group, optically active 3-propyloxybutyl group, optically active 4
-Methoxypentyl group, optically active 4-ethoxypentyl group, optically active 4-propyloxypentyl group, optically active 4- (2-methylbutyloxy) butyl group, etc.)]
Is mentioned. Of these, preferably 6 to 18 carbon atoms
Is a straight-chain alkyl group.

Examples of the 1,4-phenylene group substituted with F (fluorine atom) of Z include, for example, And so on.

Examples of the alkyl group having 1 to 12 carbon atoms which may be substituted with a halogen atom or an alkoxy group of R ′ include a linear alkyl group (methyl group, ethyl group, propyl group, butyl group,
Pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, undecyl group, dodecyl group, etc.),
Branched alkyl group (isopropyl group, 1-methylpropyl group, 1-methylbutyl group, 1-methylhexyl group, 1-
Methylheptyl group, 2-methylbutyl group, 2-methylpentyl group, 2-methylhexyl group, 2-methylheptyl group, 2-methyloctyl group, 3-methylpentyl group, 4
-Methylpentyl group, 4-methylhexyl group, 5-methylheptyl group, 6-methyloctyl group, 7-methylnonyl group, 8-methyldecyl group, 9-methyldecyl group, etc.), an alkyl group having a substituent [eg Cl ( Alkyl group substituted with chlorine atom (2-chloropropyl group,
2-chlorobutyl group, 2-chloropentyl group, 2-chlorohexyl group, 2-chloroheptyl group, 2-chlorooctyl group, 1-chloro-2-methylpropyl group, 1-chloro-2-methylbutyl group, 1- Chloro-3-methylbutyl group, etc.), alkyl group substituted with F (fluorine atom) (2-fluoropropyl group, 2-fluorobutyl group, 2
-Fluoropentyl group, 2-fluorohexyl group, 2-
Fluoroheptyl group, 2-fluorooctyl group, 1-fluoro-2-methylpropyl group, 1-fluoro-2-methylbutyl group, 1-fluoro-3-methylbutyl group, etc.), alkyl group substituted with an alkyloxy group ( 2-
Methoxypropyl group, 2-ethoxypropyl group, 2-propyloxypropyl group, 3-methoxybutyl group, 3-
Ethoxybutyl group, 3-propyloxybutyl group, 4-
Methoxypentyl group, 4-ethoxypentyl group, 4-propyloxypentyl group, 3-methoxypropyl group, 3
-Ethoxypropyl group, 3-propyloxypropyl group, 3-hexyloxypropyl group, 4-methyloxybutyl group, 4-propyloxybutyl group, 4-hexyloxybutyl group, etc.)], an optically active alkyl group ( Optically active 2-methylbutyl group, optically active 2-methylpentyl group, optically active 2-methylhexyl group, optically active 2
-Methylheptyl group, optically active 2-methyloctyl group,
Optically active 3-methylpentyl group, optically active 4-methylhexyl group, optically active 5-methylheptyl group, optically active 6
-Methyloctyl group, optically active 1-methylpropyl group,
An optically active 1-methylbutyl group, an optically active 1-methylheptyl group, an optically active 1-methyloctyl group, etc.) and an optically active alkyl group having a substituent [for example, an optically active alkyl substituted with Cl (chlorine atom)] Group (optically active 2-chloropropyl group, optically active 2-chlorobutyl group,
Optically active 2-chloropentyl group, optically active 2-chlorohexyl group, optically active 2-chloroheptyl group, optically active 2
-Chlorooctyl group, optically active 1-chloro-2-methylpropyl group, optically active 1-chloro-2-methylbutyl group, optically active 1-chloro-3-methylbutyl group, etc.),
Optically active alkyl group substituted with F (fluorine atom) (optically active 2-fluoropropyl group, optically active 2-fluorobutyl group, optically active 2-fluoropentyl group, optically active 2-fluorohexyl group, optically active 2 -Fluoroheptyl group, optically active 2-fluorooctyl group, optically active 1-fluoro-2-methylpropyl group, optically active 1-fluoro-2-methylbutyl group, optically active 1-fluoro-
3-methylbutyl group etc.) and an optically active alkyl group substituted with an alkyloxy group (optically active 2-methoxypropyl group, optically active 2-ethoxypropyl group, optically active 2-propyloxypropyl group, optically active 3-methoxy Butyl group, optically active 3-ethoxybutyl group, optically active 3-propyloxybutyl group, optically active 4-methoxypentyl group, optically active 4-ethoxypentyl group, optically active 4-propyloxypentyl group, optically active 4- ( 2-methylbutyloxy) butyl group etc.)]. Of these, an alkyl group having 1 to 9 carbon atoms is preferable.

In the general formula (1), m is preferably an integer of 2-4. When m is 0, the temperature range showing ferroelectricity is narrow, and when it exceeds 4, the raw optically active alcohol is difficult to obtain.

Specific examples of the phenylpyrimidine compound represented by the general formula (1) include compounds having groups and numbers shown in Table 1. Further, specific examples of the phenylpyrimidine compound represented by the general formula (2) include compounds having a group shown in Table-2.

The compound represented by the general formula (1) may be used alone, but it is preferably used as a mixture of two or more kinds with the compound represented by the other general formula (1) and / or other components. Further, the compound represented by the general formula (2) may be used alone, but it is preferably used as a mixture of two or more kinds with the compound represented by the other general formula (2) and / or other components. .

The compound of general formula (1) can be synthesized, for example, through the following steps. [Wherein R, X, Z, m and R ′ are general formulas
It is the same as in (1). ] [In the formula, Ts represents a p-toluenesulfonyl group. Further, instead of the Ts-O- group, other leaving groups such as methyloxy group and Bγ (bromine atom) can be used. ] That is, the compound represented by the general formula (3) and the compound represented by the general formula (4), ethanol, dimethylformamide,
In a solvent such as dimethylsulfoxide, toluene, xylene, dioxane, for example, alkali metal hydroxide (sodium hydroxide, potassium hydroxide etc.), alkali metal (sodium, potassium etc.) or alkali metal hydride (sodium hydride etc.) The compound of general formula (1), which is the target compound, is obtained by condensation using the compound.

The compound of the general formula (4), which is the starting material for the above synthesis, can be easily obtained by the reaction of an optically active alcohol synthesized by the method described in Japanese Patent Application No. 62-141919 and p-toluenesulfonic acid chloride. You can

The compound of general formula (2) can be synthesized, for example, through the following steps. [In the following formula, R, X, Z and R'are represented by the general formula (2)
Is the same as ] [In the formula, Ts represents a p-toluenesulfonyl group. Further, instead of the Ts-O- group, other leaving groups such as methyloxy group and Bγ (bromine atom) can be used. ] That is, the compound represented by the general formula (3) and the compound represented by the general formula (5), ethanol, dimethylformamide,
In a solvent such as dimethylsulfoxide, toluene, xylene, dioxane, for example, alkali metal hydroxide (sodium hydroxide, potassium hydroxide etc.), alkali metal (sodium, potassium etc.) or alkali metal hydride (sodium hydride etc.) The compound of general formula (1), which is the target compound, is obtained by condensation using the compound. The compound of the general formula (5), which is the starting material for the above synthesis, is disclosed in Japanese Patent Application No.
It can be easily obtained by reacting an optically active alcohol synthesized by the method described in 2-141920 with p-toluenesulfonic acid chloride.

The liquid crystal composition of the present invention contains at least one compound represented by the general formula (1) or (2) as a blending component. The liquid crystal composition includes a chiral smectic liquid crystal other than the compound of the general formula (1) or (2) of the present invention, for example, JP-A-62-135.
Compound of the general formula (1) described in JP-A-449-2, JP-A-62-228043
Of formula (1), 4-n-alkyloxy-4′-biphenylcarboxylic acid-p ′-(2-methylbutoxycarbonyl) phenyl ester, 4-n-alkyloxy-4′-biphenyl Carboxylic acid-2-methylbutyl ester, p-alkyloxybenzylidene-
p'-amino-2-chloro-propyl cinnamate, p
Ferroelectric liquid crystal such as -alkyloxybenzylidene-p'-amino-2-methylbutylcinnamate and / or 4- (p-alkyloxybiphenyl-p'-oxycarbonyl) -4 '-(2-methylbutyloxy It may contain a conventional chiral smectic liquid crystal such as carbonyl) -cyclohexane and pn-alkyloxybenzylidene-p '-(2-methylbutyloxycarbonyl) aniline. Further, it may contain a dichroic dye such as an anthraquinone dye or an azo dye.

The formulation examples of the liquid crystal composition are as follows.

(I) Compound of the general formula (1) or (2): 1 to 100% by weight
(Preferably 1 to 80% by weight) (II) Other chiral smectic liquid crystal: 0 to 99% by weight
(Preferably 5 to 95% by weight) (III) Dichroic dye: 0 to 5% by weight The liquid crystal composition of the present invention has a chiral smectic phase (hereinafter,
S ^* phase as abbreviated) are those exhibiting, S ^* the upper limit of the temperature range indicating the phase (i.e. a temperature which varies from S ^* phase to smectic A phase or chiral nematic phase or isotropic liquid phase) is usually 30 to 80 ℃, and its lower limit (ie S
^{* The} temperature at which a phase changes to a solid or a higher order smectic phase) is usually -10 to 40 ° C, and ferroelectricity is exhibited in this range. A liquid crystal exhibiting ferroelectricity causes an optical switching phenomenon when a voltage is applied, and a display element having a fast response can be manufactured by utilizing this phenomenon (for example, JP-A-56-107216).
JP-A-59-118744, NA Clarke (N.
A. Clark), ST Ragawall (S.
T. Lagerwall); Applied Physics Letter
er) 36 , 899 (1980), etc.].

The liquid crystal composition of the present invention is sealed in a liquid crystal cell having a cell interval of 0.5 to 10 μm, preferably 0.5 to 3 μm in vacuum, and an optical switching element (display element) is provided by installing polarizers on both sides.
Can be used as

The above liquid crystal cell was provided with a transparent electrode, and the surface was subjected to orientation treatment.
It can be manufactured by laminating two glass substrates with a spacer interposed therebetween. Examples of the spacer include alumina beads, glass fiber, and polyimide film. As the alignment treatment method, a normal alignment treatment, for example, a polyimide film, a rubbing treatment, or a Si
O Diagonal vapor deposition can be applied.

[Examples] Hereinafter, the present invention will be further described with reference to Examples, but the present invention is not limited thereto.

In the following examples,% indicates% by weight.

In the following description, the phase transition temperature slightly varies depending on the measuring method and the purity.

Reference Example 1 Optically active 5-n-octyloxy-2- [4
Preparation of-(4-ethoxy-pentoxy) phenyl] pyrimidine In 8 ml of ethanol, 0.33 g of KOH and the known substance 5
1.40 g of -n-octyloxy-2- (4-hydroxyphenyl) pyrimidine was added and uniformly dissolved, and then optically active p-
Toluenesulfonic acid-4-ethoxy-pentyl ester
After 1.33 g was added and the mixture was reacted under reflux for 5 hours, ethanol was distilled off under reduced pressure, followed by extraction with toluene. After washing with water, diluted KOH aqueous solution and water, toluene was distilled off under reduced pressure to obtain a target product (crude product). The hexane-soluble part was treated with a silica gel column, and then recrystallized twice with ethanol to obtain optically active 5-n-octyloxy-2- [4- (4-ethoxy-pentoxy) which is the phenylpyrimidine compound of the present invention. Phenyl]
1.02 g of pyrimidine was obtained.

The structure of the compound was confirmed by NMR (nuclear magnetic resonance analysis), MS (mass spectrometry) and IR (infrared absorption spectrum analysis). IR spectrum and H-NM of the above compound
The R spectra are shown in FIGS. 1 and 2, respectively.

Example 1 Optically active 5-n-octyloxy-2- [4
Preparation of-(4-Ethoxy-pentoxy) -3-fluorophenyl] pyrimidine (Compound No. 2 in Table 1) In 14 ml of ethanol, 0.46 g of KOH and 5 are known substances.
After 2.21 g of -n-octyloxy-2- (4-hydroxy-3-fluorophenyl) pyrimidine was added and uniformly dissolved,
1.35 g of optically active 1-bromo-4-ethoxypentane was added, and the mixture was stirred at room temperature for 5 hours. After ethanol was distilled off under reduced pressure, it was extracted with ether, washed with water, diluted HCL aqueous solution, and washed with water,
The ether was distilled off to obtain the desired product (crude product). The hexane-soluble part was treated with a silica gel column, and then recrystallized twice with ethanol to obtain optically active 5-n-octyloxy-2- [4- (4
1.30 g of -ethoxy-pentoxy) -3-fluorophenyl] pyrimidine were obtained.

The IR, H-NMR and ¹⁹ F-NMR spectra of this compound are shown in FIG. 1, FIG. 2 and FIG. 3, respectively.

Example 2 Optical activity 5-n-nonyloxy-2- [4-
Preparation of (4-ethoxy-pentoxy) -3-fluorophenyl] pyrimidine (Compound of Table 1, No. 3) In 14 ml of ethanol, 0.44 g of KOH and 5 are known substances.
After 2.23 g of -n-octyloxy-2- (4-hydroxy-3-fluorophenyl) pyrimidine was added and uniformly dissolved,
1.31 g of optically active 1-bromo-4-ethoxypentane was added, and the mixture was stirred at room temperature for 5 hours. The same post-treatment and purification as in Example 8 were carried out to give 1.25 g of optically active 5-n-nonyloxy-2- [4- (4-ethoxy-pentoxy) -3-fluorophenyl] pyrimidine which is a phenylpyrimidine compound of the present invention. Got

The IR, H-NMR and ¹⁹ F-NMR spectra of this compound are shown in FIGS. 4, 5 and 6, respectively.

Reference Example 2 Optical activity 5-n-octyloxy-2- [4
Preparation of-(3-ethoxy-butyloxy) phenyl] pyrimidine In 10 ml of ethanol, 0.37 g of KOH and a known substance 5
After 1.61 g of -n-octyloxy-2- (4-hydroxyphenyl) pyrimidine was added and uniformly dissolved, optically active p-
Toluenesulfonic acid-3-ethoxy-butyl ester 1.
46 g was added and the mixture was reacted under reflux for 5 hours. The same post-treatment and purification as in Example 1 were carried out to give an optically active 5-n-octyloxy-2- [4 which is a phenylpyrimidine compound of the present invention.
1.09 g of-(3-ethoxy-butyloxy) phenyl] pyrimidine was obtained.

IR (cm ^-1 ; 1605,1440,1245,785 H-NMR (300MHz, CDCl ₃ ) δ (ppm); 8.40 (s, 2H) 8.25 (d, 2H) 6.95 (d, 2H) 4.10 (m, 2H ) 4.05 (t, 2H) 3.60 (m, 2H) 3.40 (m, 1H) 1.90 (m, 2H) 1.80 (m, 2H) 1.3 (m, 10H) 1.20 (m, 6H) 0.90 (t, 3H) Implementation The characteristics (phase transition temperature) of the compounds shown in Examples 1 and 2 are shown in Table 3.

Compound of Comparative Example 1: [Proceedings of the 12th Liquid Crystal Symposium Lecture (issued in October 1986)
p. 152 to 153] When the SC ^* phase temperature ranges of the compounds of Examples 1 and 2 and the compound of Comparative Example 1 are compared, the compound of Example 1 is 23.3 to 53.9 ° C. The compound of Example 2 is -6.7 to 52 ° C. Comparative Example 1 Compound 34-49 ° C. That is, the compound of Example 1 has almost twice the SC ^* phase temperature range of the compound of Example 1 and the compound of Example 2 has almost four times that of the compound of Comparative Example 1, and thus are very excellent compounds.

Examples 4 and 5 are the compounds of Reference Example 1 or the compounds of Reference Example 2 and known smectic liquid crystal compounds (Compounds A and B below).
The liquid crystal compositions of Reference Examples 3 and 4 were obtained by mixing in the proportions shown in. In the method for preparing the composition, the compounds in Table 4 were weighed in a predetermined weight ratio, and the three compounds were mixed while being heated and dissolved in the sample bottle.

Compound A: optically active p-n-decyloxybenzoic acid-
p ′-(2-methylbutoxycarbonyl) phenyl ester Compound B: Optically active 4′-decyloxy-4- (2-methylbutyloxycarbonyl) tran Polyvinyl alcohol was applied as an alignment treatment agent, and the composition was injected into a cell having a cell thickness of 2 μm provided with a transparent electrode which was rubbed on the surface and subjected to parallel alignment treatment, to prepare an optical switching element. This device was placed between two orthogonal polarizers, a voltage of ± 10 V was applied, and the response time was calculated from the change in transmitted light intensity. At 30 ° C., the composition of Reference Example 3 was about 400 μsec. The composition of Example 4 is about 250 μs
It was ec.

Examples 3 and 4 The compound of Example 1 or the compound of Example 2 and a known smectic liquid crystal compound (compounds A and B similar to Reference Examples 3 and 4) were blended in the proportions shown in Table-5 to prepare the compound of the present invention. A liquid crystal composition was obtained. As for the method for preparing the composition, the compounds in Table 5 were weighed in a predetermined weight ratio, and the three compounds were mixed while being heated and dissolved in the sample bottle. This is a useful liquid crystal composition which exhibits a chiral smectic phase in a wide temperature range including room temperature as shown in Table 5 and is chemically stable.

Polyvinyl alcohol was applied as an alignment treatment agent, and the composition was injected into a cell having a cell thickness of 2 μm provided with a transparent electrode which was rubbed on the surface and subjected to parallel alignment treatment, to prepare an optical switching element. This element was placed between two orthogonal polarizers, a voltage of 10 V was applied, and the response time was calculated from the change in transmitted light intensity.
About 380 μsec for the composition of Example 4 and about 270 μsec for the composition of Example 4.
Met.

[Effects of the Invention] The present invention provides a novel phenylpyrimidine compound and a liquid crystal composition, and these phenylpyrimidine compound and liquid crystal composition exhibit the following remarkable effects.

(1) A chiral smectic phase exhibiting ferroelectricity is obtained at around room temperature, and its temperature range is wide, and it is an epoch-making material in obtaining a practical ferroelectric liquid crystal.

(2) A chiral smectic phase exhibiting ferroelectricity is obtained at around room temperature and its temperature range is wide, and it is useful as a constituent component of a practical ferroelectric liquid crystal composition.

(3) Good stability against light, heat and moisture.

(4) Response is as fast as or higher than that of a conventional liquid crystal composition exhibiting ferroelectricity.

[Brief description of drawings]

1, 2 and 3 show IR, H-NMR and ¹⁹ F-NMR spectra of the compound of Example 1, respectively, and FIGS. 4, 5 and 6 show Example 2 respectively.
Shows the IR, H-NMR and ¹⁹ F-NMR spectra of the compound of.

 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Hiroshi Kishi 1 1-11, Hitotsubinohonmachi, Higashiyama-ku, Kyoto City, Kyoto Prefecture Sanyo Chemical Industry Co., Ltd. No. 1 Sanyo Chemical Industry Co., Ltd. (72) Inventor, Kuniyoshi Yoshio No. 1 Hitotsubashi Honmachi, Higashiyama-ku, Kyoto City, Kyoto Prefecture No. 1 Sanyo Chemical Industry Co., Ltd.

Claims (4)

[Claims] 1. A general formula [In the formula, R is a halogen atom or an alkyl group having 3 to 18 carbon atoms which may be substituted with an alkoxy group, X is -O- or a single bond (direct bond), and Z is F (fluorine atom). ) Is substituted with 1,4-phenylene group, m
Is an integer of 2 to 12, R'is an alkyl group having 1 to 12 carbon atoms which may be substituted with a halogen atom or an alkoxy group, and * indicates optically active. ] The phenyl pyrimidine compound shown by these. 2. General formula [In the formula, R is a halogen atom or an alkyl group having 3 to 18 carbon atoms which may be substituted with an alkoxy group, X is -O- or a single bond (direct bond), and Z is F (fluorine atom). ) Is substituted with 1,4-phenylene group,
R'is an alkyl group having 1 to 12 carbon atoms which may be substituted with a halogen atom or an alkoxy group, and * indicates that it is optically active. ] The phenyl pyrimidine compound shown by these. 3. General formula [In the formula, R is a halogen atom or an alkyl group having 3 to 18 carbon atoms which may be substituted with an alkoxy group, X is -O- or a single bond (direct bond), and Z is F (fluorine atom). ) Is substituted with 1,4-phenylene group, m
Is an integer of 2 to 12, R'is an alkyl group having 1 to 12 carbon atoms which may be substituted with a halogen atom or an alkoxy group, and * indicates optically active. ] The liquid crystal composition containing at least 1 sort (s) of the phenyl pyrimidine compound shown by these as a compounding component. 4. A general formula [In the formula, R is a halogen atom or an alkyl group having 3 to 18 carbon atoms which may be substituted with an alkoxy group, X is -O- or a single bond (direct bond), and Z is F (fluorine atom). ) Is substituted with 1,4-phenylene group,
R'is an alkyl group having 1 to 12 carbon atoms which may be substituted with a halogen atom or an alkoxy group, and * indicates that it is optically active. ] The liquid crystal composition containing at least 1 sort (s) of the phenyl pyrimidine compound shown by these as a compounding component.