JP2828508B2 - Liquid crystal composition and liquid crystal display device - Google Patents

Description

Description: TECHNICAL FIELD The present invention relates to a nematic liquid crystal composition and a liquid crystal display device using the liquid crystal composition. More specifically, the present invention relates to a liquid crystal composition for an active matrix liquid crystal display device and a liquid crystal display device using the composition.

2. Description of the Related Art Liquid crystal display devices (LCDs) have lower power consumption, smaller size, and lighter weight than CRTs (CRT displays), so they are twisted nematic (TN) and super twisted nematic (STN). Various LCDs such as a thin film transistor (TFT) method have been put to practical use. Among them, active matrix LCDs (AM-LCDs) such as thin film transistors (TFTs) have advanced in color and high definition.
It is drawing attention as the favorite of flat displays.

Characteristics required for the AM-LCD liquid crystal composition include: 1) a high voltage holding ratio (VHR) in order to maintain a high contrast of the LCD.

2) The nematic liquid crystal phase range is large depending on the use environment.

3) An appropriate refractive index anisotropy (Δn) can be obtained depending on the cell thickness.

4) An appropriate threshold voltage can be obtained according to the drive circuit.

Can be mentioned.

The AM-LCD employs a TN display method in which the orientation of liquid crystal molecules on the upper and lower substrates is twisted by 90 °. In this TN display method, in order to prevent coloring due to interference of the liquid crystal cell when no voltage is applied and to obtain an optimum contrast, the refractive index anisotropy (Δn) and the cell thickness (d) μ
The product Δn · d of m is a certain value (for example, Δn · d = 0.5
μm). Under such restrictions, the Δn of the liquid crystal composition for TFTs currently in practical use is about 0.07 to 0.11 in an element utilizing the vicinity of the first minimum value of the light transmittance, and especially 0.08 to 0.10. Has become.

In recent years, notebook personal computers and the like characterized by being small and lightweight and portable have been developed.
Has expanded its use. LCDs intended for portable use are limited in characteristics by the drive power supply. Since it is necessary to reduce power consumption for long-term use, a liquid crystal composition having a low threshold voltage has been required. Further, in order to further reduce the weight and cost of the driving power supply, a liquid crystal having a small threshold voltage has been required.

In addition, developments for outdoor use have been studied along with portability. In order to be able to withstand outdoor use, it is required to exhibit a nematic phase over a region beyond the temperature range of the use environment. From this point of view, the liquid crystal composition for TFT currently in practical use has a nematic-isotropic phase transition temperature (clearing point: T _N1 ).
Is 60 ° C or higher and the smectic-nematic phase transition temperature (T
_SN ) is -20 ° C or less.

Against this background, Japanese Patent Application Laid-Open No. 2-233626 discloses a trifluoro compound having a relatively large dielectric anisotropy (Δε). For example, Application Example 2 discloses a composition example of a trifluoro compound of 15% by weight and a difluoro compound of 85% by weight.
In addition, they have the drawback that they have poor compatibility, especially at low temperatures, and lack practicality due to the small nematic phase range.

WO 94/03558 discloses a composition example of a trifluoro compound and a difluoro compound. However, the compositions disclosed in Examples 1 and 2 have a low clearing point of 50 ° C. or less, and have a Δn of 0.06 or less, which lacks practicality. Some compositions have the disadvantage of having a high threshold voltage.

As described above, although the liquid crystal composition has been intensively studied for various purposes, it is presently demanding a new improvement.

DISCLOSURE OF THE INVENTION An object of the present invention is to provide a liquid crystal composition having a low threshold voltage, excellent low-temperature compatibility, and a large nematic phase range, while satisfying various characteristics required for the liquid crystal composition for AM-LCD. Is to provide.

The present inventors have examined the physical properties of a novel difluorooxymethane derivative derivable from a phenylbenzoate derivative,
That the direction of the dipole moment due to the polarization of two fluorine atoms effectively contributes to an increase in the dielectric constant in the long axis direction of the compound molecule, and is effective in lowering the threshold voltage in order to develop a large dielectric anisotropy; It was also found that the viscosity was extremely low.

Furthermore, they have found that those in which a fluorine-based substituent is selected as a terminal substituent of these compounds are novel liquid crystal compounds for low voltage useful in AM-LCD, and have eagerly studied compositions using these liquid crystal compounds. As a result of the study, it has been found that when the liquid crystal composition of the present invention is used for an AM-LCD, the above problem can be solved. Hereinafter, the present invention will be described in detail.

The present invention relates to a compound of the formula (I) (Wherein l, m, and n are each 0 or 1; rings A ₁ and A ₂ are each independently a trans-1,4-cyclohexylene group; one or more hydrogen atoms of a 6-membered ring are halogen atoms; 1,4-phenylene group, which may be substituted, trans-1,3-
Represents dioxane-2,5-diyl or pyrimidine 2,5-diyl, and ring A ₃ is a 1,4-phenylene group in which one or more hydrogen atoms of a 6-membered ring may be substituted with a halogen atom;
Represents trans-1,3-dioxane-2,5-diyl or pyrimidine-2,5-diyl, wherein Z ₁ , Z ₂ , and Z ₃ are each independently a covalent bond, —CH ₂ CH ₂ —, —COO— , -CF ₂ O-, -OCF _{2
-, - CH 2 O -,} - OCH 2 -, - CH = CH- or -C≡C-
L ₁ , L ₂ , L ₃ , L ₄ are each independently a hydrogen atom or a halogen atom, and X is a halogen atom, CN, C
F ₃ , OCF ₃ , OCHF ₂ , OCH ₂ F, a linear or branched alkyl group having 1 to 10 carbon atoms, an alkenyl group or an alkoxy group, and R is a linear or branched alkyl group having 1 to 10 carbon atoms Alternatively, one or two or more non-adjacent CH ₂ groups in R may be substituted with an oxygen atom. However, X is not an alkyl group, an alkenyl group or an alkoxy group unless Z ₂ is —CF ₂ O— or —OCF ₂ —. In the compound represented by the formula, 1 is 1, m is 0, n is 0 or 1, ring A ₁ is a trans-1,4-cyclohexylene group,
Ring A ₃ is 1,4-phenylene group, Z ₁ is -CH ₂ CH ₂ - or a covalent bond, covalent bond Z ₂ and Z _3, L ₁ and L ₂ are a hydrogen atom,
L ₃ is Y (Y represents a hydrogen atom or a fluorine atom); L ₄ is a fluorine atom; R is an alkyl group represented by C _n H _{2 + 1} (n represents an integer of 1 to 10); Fluorine atom, CF ₃ or OCF ₃
And a liquid crystal composition containing at least one specific difluorooxymethane derivative.

That is, a first aspect of the present invention includes, as a first component, at least one compound represented by formula (I-1) or (I-2), and as a second component, A liquid crystal composition comprising at least one compound represented by formulas (II-1) to (II-7).

(In the formula, n represents an integer of 1 to 10, Z ₁ represents —CH ₂ CH ₂ — or a single bond, X represents F, OCF ₃ or CF ₃ , and Y represents H or F.) The second aspect of the present invention is that the first part is based on the total weight of the liquid crystal composition.
The liquid crystal composition according to the first aspect, wherein the component is 3 to 40% by weight and the second component is 50 to 97% by weight.

A third aspect of the present invention is a liquid crystal composition further comprising a compound represented by the general formula (III) in addition to the liquid crystal composition according to the first or second aspect.

(In the formula, n represents an integer of 1 to 10.) In the fourth aspect of the present invention, in addition to the liquid crystal composition according to any one of the first to third aspects, the general formula (IV-1) and / or A liquid crystal composition further comprising a compound represented by the general formula (IV-2).

(Wherein, n represents an integer of 1 to 10) In the fifth aspect of the present invention, in addition to the liquid crystal composition according to any one of the first to fourth aspects, general formula (V-1) and / or A liquid crystal composition further comprising a compound represented by Formula (V-2).

(Wherein, n represents an integer of 1 to 10) A sixth aspect of the present invention is a liquid crystal display device using the liquid crystal composition according to any one of the first to fifth aspects.

BEST MODE FOR CARRYING OUT THE INVENTION Hereinafter, compounds constituting each component of the present invention will be described.

In the present invention, the compound represented by the general formula (I-1) or (I-2)
The following compounds are preferred as the compounds represented by

In these formulas, n represents an integer of 1 to 10. In the above formula, the formulas (I-1-1), (I-1-2), (I
-1-5), (I-1-7), (I-1-9), (I-
The compound represented by 1-10), (I-2-4) or (I-2-12) is particularly preferred.

The compound of the general formula (I-1) has a dielectric anisotropy (Δε)
Is approximately in the range of 9 to 16 and is excellent in thermal stability and chemical stability, and thus plays a role particularly in reducing the threshold voltage of the liquid crystal composition for TFT. In addition, the general formula (I-2)
Has the role of lowering the threshold voltage,
Since it is a tetracyclic compound, it plays a role of increasing the clearing point of the liquid crystal composition.

The use amount of the first component of the present invention is preferably 3 to 40% by weight. More preferably, the content is 5 to 35% by weight. If the amount is less than 3% by weight, the effect of low voltage, which is the subject of the present invention, is difficult to obtain. If the amount exceeds 40% by weight, the compatibility of the liquid crystal composition at low temperatures may be poor.

The compounds of the general formulas (I-1) and (I-2) can be produced as follows. First, the general formula (I)
The method for producing the difluorooxymethane derivative represented by

As shown in the following formula 1, using a benzonitrile derivative represented by the general formula (A) as a raw material for production, in an alcohol solvent such as ethyl alcohol, ethylene glycol or diethylene glycol, a base such as sodium hydroxide or potassium hydroxide; Alternatively, it is hydrolyzed using a mineral acid such as hydrochloric acid or sulfuric acid as a catalyst to lead to a carboxylic acid derivative (B). Next, the carboxylic acid derivative (B) is subjected to a general esterification method by using an ion exchange resin such as a mineral acid such as hydrochloric acid or sulfuric acid, or an organic acid such as amberlite such as p-toluenesulfonic acid as an acid catalyst. Alternatively, an ester derivative represented by the general formula (D) is produced by reacting with a phenol derivative represented by the general formula (C) using N, N'-dicyclohexylcarbodiimide (DCC) as a catalyst. Alternatively, (D) can be produced by reacting (B) with thionyl chloride to form a salt oxide and then reacting (C) in the presence of a base such as pyridine. Next, the ester derivative (D) is prepared using a benzene or toluene solvent and a Lawesson reagent [2,4-bis (4-methoxyphenyl) -1,3-dithia-
2,4-Diphosphetane-2,4-disulfide] (Bull. S
oc.Chim.Belg., 87,223,229,299,525 (1978), Synthesi
s, 941 (1979), Tetrahedron, 35,2433 (1979), Tetrahed
ron Lett., 21, 4061 (1980)) at an arbitrary temperature from room temperature to the boiling point of the solvent to induce a thioester (thione type) derivative (E). Next, the thioester (thione type) derivative (E) is prepared by allowing diethylaminosulfur trifluoride (DAST) (Systhesis, 787 (1973)) to act at any temperature from room temperature to the boiling point of the solvent using dichloromethane and chloroform as solvents. Performs gem-fluorination of the thiocarbonyl group to produce the desired difluorooxymethane derivative.

Alternatively, as shown in Formula 2 below, a Grignard reagent is prepared from a bromobenzene derivative (F), and a dithiocarboxylic acid derivative (G) is produced by the action of carbon disulfide. It is possible to produce a thioester (thione type) derivative (E) by reacting with a phenol derivative (C) after inducing the thiocarboxylic acid chloride, and to produce a difluorooxymethane derivative also by reacting with DAST as described above. it can.

Further, among the compounds represented by the general formula (I), the compound (7) which is an analog of the compound represented by the general formula (I-1) or (I-2) which is the first component of the present invention Can be produced by a method as shown in the following formula 3. First, the alkyl benzoic acid derivative 1 is subjected to a general esterification method, for example, using an organic acid such as p-toluenesulfonic acid such as hydrochloric acid or sulfuric acid, or an ion exchange resin such as Amberlite as an acid catalyst, or N, N'-dicyclohexylcarbodiimide (DCC) is used as a catalyst for esterification with 3,4,5-trifluorophenol to produce 3,4,5-trifluorobenzoate derivative 2. Next, (2) is reacted with a Lawesson reagent under toluene reflux to obtain a thioester (thione type) derivative 3, and then DAST is acted on in dichloromethane to produce (7). 3,4,
A phenol having various substituents is used in place of 5-trifluorophenol, and further represented by the general formulas (1-1) and (I-2) from various known benzoic acid derivatives according to the above-mentioned production operation. Can be produced.

3,4,5-trifluorophenol, which is a synthetic raw material,
It can be prepared starting from 3,4,5-trifluorobromobenzene. That is, as shown in the following formula 4, the method of SOLawesson et al. (J. Am. Chem. Soc., 81, 4230)
(1959)) by reacting t-butyl hydroperoxide with a Grignard reagent prepared from 3,4,5-trifluorobromobenzene according to the method of RLKidwewll et al. (Org. Synth., V, 918 (1973)). , A Grignard reagent prepared from 3,4,5-trifluorobromobenzene is treated with a trialkyl borate to obtain a borate ester derivative, and then oxidized with a hydrogen peroxide solution.

Further, among the compounds represented by the general formula (I-1), for example, the compound (I-1-7) can be produced by a method represented by the following formula 5. First, 4- (trans-4-alkylcyclohexyl) benzonitrile 4 is hydrolyzed in the presence of sodium hydroxide in ethylene glycol or diethylene glycol to obtain a benzoic acid derivative 5.
According to a general esterification method, for example, an ion-exchange resin such as a mineral acid such as hydrochloric acid or sulfuric acid, or an organic acid such as amberlite such as p-toluenesulfonic acid is used as an acid catalyst, or N, N'-dicyclohexylcarbodiimide is used. (DCC)
Is subjected to esterification with 3,4,5-trifluorophenol to produce a 4-trifluorobenzoate derivative 6. Next, 6 reacts with Lawesson's reagent under reflux of toluene to obtain a thioester (thione type) derivative 7 and further acts with DAST in dichloromethane to give (I-1-7)
Can be manufactured. In addition, instead of 3,4,5-trifluorophenol, phenols having various substituents are used, and from various known benzoic acid derivatives, compounds (I-1-1) to (I-1-1) to ( I-1-
3), (I-1-8) to (I-1-9) can be produced.

In addition, as shown in the following formula 6, among the compounds represented by the general formula (I-2), for example, the compound (I-2-4)
Can be manufactured by the following method. That is, 4-iodobenzene is converted into a noble metal catalyst such as palladium chloride,
After coupling with a Grignard reagent prepared from 3,4,5-trifluorobromobenzene to obtain a biphenyl derivative 8, bromine is allowed to act on 8 in the presence of a metal powder such as iron powder to convert the bromobiphenyl derivative 9 To manufacture. Then R.
According to the report of L. Kidwell et al. (Org. Synth., V, 918 (1973)), the Grignard reagent prepared from 9 was reacted with trimethyl borate and then oxidized with hydrogen peroxide in the presence of acetic acid to obtain phenylphenol. Derivative 10 is produced.
Compound (I-2-4) can be produced by treating 10 in the same manner as in the case of (7). further,
In place of 3,4,5-trifluorobromobenzene, phenylphenol derivatives prepared using bromobenzene derivatives having various substituents can be converted to other general formulas (I
Compounds (I-2-1) to (I-2-) represented by c)
3), (I-2-5) to (I-2-6) can be produced.

Further, among the compounds represented by the general formula (I-1) or (I-2), a compound in which Z ₁ is —CH ₂ CH ₂ — is produced by a method as shown in the following formula 7. Can be. Starting material 4- [2- (trans-4-alkylcyclohexyl)
Ethyl] benzoic acid 12 is a known compound, 4- [2-
(Trans-4-alkylcyclohexyl) ethyl] benzonitrile 11 can be produced by hydrolysis in ethylene glycol or diethylene glycol in the presence of sodium hydroxide. This benzoic acid derivative
A phenylbenzoate derivative 13 is produced from 12 and various phenol derivatives by the esterification method described above.
This phenylbenzoate derivative is treated with a Lawesson reagent as described above to form a thioester (thione type) derivative, and further, by the action of DAST, the (I-1-4) to (I-1-4)
-1-6), (I-1-10) to (I-1-12), (I-
2-7) to (I-2-12) can be produced.

Formulas (II-1) to (II-7), (III), (IV-
As disclosed in JP-A-2-233626, the trifluoro compounds of 1) and (IV-2)
Is in the range of about 7 to 12, and is a compound well known as a compound for low-voltage TFTs because of its excellent thermal stability and chemical stability (R. Tarao et al., SID 94 Dige
st, p233).

The compounds of the general formulas (II-1) to (II-7) have a nematic-isotropic transition point (clearing point: T _N1 ) of about 50.
It is in the range of 100100 ° C., and is an optimal compound as a base compound for a composition for a low-voltage TFT.

The use amount of the second component of the present invention is preferably 50 to 97% by weight. More preferably, it is 60 to 95% by weight. If it is less than 50% by weight, the compatibility of the liquid crystal composition at low temperatures may be poor. If it exceeds 97% by weight, it is difficult to obtain the effect of the low voltage of the present invention.

Since the compound of the general formula (III) is a two-ring trofluoro compound, it plays a role particularly in reducing the threshold voltage of the liquid crystal composition. Since it is a bicyclic compound, the use of a large amount thereof may lower the clearing point of the liquid crystal composition. General formula (II
The use amount of the compound (I) is preferably 15% by weight or less. More preferably, the content is 10% by weight or less.

The compounds of the general formulas (IV-1) and (IV-2) are trifluoro compounds having four rings, and thus have a role of particularly increasing the clearing point of the liquid crystal composition. When used, the threshold voltage of the liquid crystal composition may increase, and the low-temperature compatibility may deteriorate. The use amount of the compounds of the general formulas (IV-1) and (IV-2) is preferably 20% by weight or less. More preferably, the content is 10% by weight or less.

The compounds of the general formulas (V-1) and (V-2) have two rings,
It is a tricyclic C1 compound. These mainly serve to reduce the viscosity of the liquid crystal composition. Since Δε is as small as 4 to 5, the threshold voltage of the liquid crystal composition may increase when used in a large amount. The use amount of the compound of the general formula (V) is 30
% By weight or less is preferred. More preferably, it is at most 25% by weight.

In the composition of the present invention, a compound other than the compound represented by the above-mentioned general formula can be mixed and used as long as the object of the invention is not impaired.

The liquid crystal compositions used according to the invention are prepared in a customary manner. Generally, a method of dissolving various components at a high temperature is used. Further, the liquid crystal material of the present invention is improved and optimized according to the intended use by appropriate additives. Such additives are described in the literature. In general, the required twist angle is adjusted by inducing the helical structure of the liquid crystal, and the reverse twist
To prevent this, a chiral dopant or the like is added.

Further, the liquid crystal composition of the present invention may be added with a dichroic dye such as a merocyanine-based, styryl-based, azo-based, azomethine-based, azoxy-based, quinophthalone-based, anthraquinone-based, or tetrazine-based dye for guest host (GH) mode Can be used as a liquid crystal composition. Alternatively, liquid crystal for polymer dispersed liquid crystal display (PDLCD) represented by NCAP made by microencapsulation of nematic liquid crystal or polymer network liquid crystal display (PNLCD) made of three-dimensional network polymer in liquid crystal. It can also be used as a composition. In addition, it can be used as a liquid crystal composition for a birefringence control (ECB) mode or a dynamic scattering (DS) mode.

Hereinafter, the present invention will be described in detail with reference to examples, but the present invention is not limited to these examples.

First, production examples of the compounds of the general formulas (I-1) and (I-2) as the first component of the liquid crystal composition of the present invention will be described.
Incidentally, Cr in each compound, Preparation of represents crystal, N represents nematic phase, S = smectic phase, the I _SO isotropic liquid,
All units of phase transition temperature are ° C.

(Compound Production Example 1) difluoro- [4- (trans-4-propylcyclohexyl) phenyl]-(3,4,5-trifluorophenyloxy) methane [(I-1) In the formula, R = C ₃ H ₇ , Z ₁ is a covalent bond, X = F, Y = F] Production of 4- (trans-4-propylcyclohexyl) in a 500 ml three-necked flask equipped with a stirrer, thermometer, dropping funnel and nitrogen inlet tube under a nitrogen atmosphere. ) Benzoic acid 15.0g (60.9m
mol), 15.1 g (73.1 mmol) of DCC and 0.3 g (2.2 mmo) of DMAP
l) was dissolved in 250 ml of dichloromethane, and 10.8 g (73. mmol) of 3,4,5-trifluorophenol was added dropwise over 3 minutes while stirring at room temperature. After the addition, the mixture was stirred at room temperature for 10 hours. After adding 100 ml of water to the reaction solution, the insolubles in dichloromethane were separated by filtration, the dichloromethane layer was separated, the aqueous layer was extracted with 200 ml of dichloromethane, and the extracted layer was mixed.
x2), washed successively with 100 ml of a saturated aqueous solution of sodium hydrogencarbonate and water (100 ml x2), dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain 23.8 g of a reaction product. The reaction product was purified by column chromatography using silica gel as a filler and toluene as a developing solvent, and further recrystallized from a heptane-ethanol mixed solvent to obtain 13.2 g of a colorless crystal. This is 3,4,5-trifluoro- [4- (trans-
4-propylcyclohexyl) phenyl] benzoate.

Next, in a 1000 ml eggplant flask equipped with a nitrogen inlet tube and a cooling tube, 3,4,5-trifluoro- [4-
(Trans-4-propylcyclohexyl) phenyl]
Benzoate 13.2g (35.2mmol), Lawson reagent 28.5g
(70.4 mmol) was dissolved in 500 ml of toluene, and heated and refluxed for 60 hours while stirring under a nitrogen stream. After the reaction solution was cooled to room temperature, 200 ml of water was added, the toluene layer was separated, and the aqueous layer was further extracted with 150 ml of toluene. Mix the organic layers,
Water (200ml x2), saturated aqueous sodium hydrogen carbonate solution (100m
l), washed successively with 100 ml of a 10% aqueous sodium bisulfite solution and water (200 ml × 2), dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain 13.8 g of a brown crystalline mixture. The reaction product was purified by column chromatography using silica gel as a filler and heptane as a developing solvent, and then recrystallized from heptane to obtain 4.7 g of yellow needle-like crystals having a transition point of Cr 127.7-128.2 ° C Iso. This is 4- (trans-4-propylcyclohexyl) phenylcarbothioic acid-O-3,4,
5-trifluorophenyl.

1H-NMR (CDCl3; δ ppm) 0.8-2.0 (16H, m), 2.57 (1H,
m), 6.78 (2H, m), 7.29 (2H, d, J = 8.2Hz), and 8.23 (2
H, d, J = 8.2Hz). In a 100 ml eggplant flask equipped with a nitrogen inlet tube, at room temperature
-(Trans-4-propylcyclohexyl) phenylcarbothioic acid-O-3,4,5-trifluorophenyl 4.7 g
(12.1 mmol) was dissolved in 50 ml of dichloromethane, and DAST5.9 g
(36.2 mmol) was added and the mixture was stirred at room temperature for 34 hours. After adding 50 ml of water to the reaction solution and separating the dichloromethane layer, the aqueous layer was further extracted with 50 ml of dichloromethane, and the extracted layers were mixed, and water (50 ml x 2), a saturated aqueous solution of sodium hydrogencarbonate 30 m
After washing with water and water (50 ml × 2) in that order, the extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain 4.3 g of colorless crystals.
The reaction product was purified by column chromatography using silica gel as a filler and heptane as a developing solvent, and then recrystallized from heptane to obtain colorless needle-like crystals (transition point: Cr70.5-71.4 I
so) 1.5 g. This is difluoro- [4- (trans-4-propylcyclohexyl) phenyl]-(3,4,5
-Trifluorophenyloxy) methane. 1H-NM
R (CDCl3; δppm) 0.80-2.10 (16H, m), 2.60 (1H, m),
6.96 (2H, m), 7.32 (2H, d, J = 8.6Hz) and 7.62 (2H, d, J
= 8.6Hz). 19F-NMR (CDCl3; δ ppm) -66.754 (2F, s, -CF20-),
−133.521 (2F, d), −164.754 (1F, t). GC-MS (CI) m / z 251 (100%), 379 (M + 1-HF, 3
4), and 125 (27). According to the above production method, the following compounds can be produced by using 4- (trans-4-alkylcyclohexyl) benzoic acid having a different alkyl chain instead of 4- (trans-4-propylcyclohexyl) benzoic acid.

Difluoro- [4- (trans-4-methylcyclohexyl) phenyl]-(3,4,5-trifluorophenyloxy) methane difluoro- [4- (trans-4-ethylcyclohexyl) phenyl]-(3,4, 5-trifluorophenyloxy) methane difluoro- [4- (trans-4-butylcyclohexyl) phenyl]-(3,4,5-trifluorophenyloxy) methane difluoro- [4- (trans-4-pentylcyclohexyl) Phenyl]-(3,4,5-trifluorophenyloxy) methane Cr62.6-63.0 Iso difluoro- [4- (trans-4-hexylcyclohexyl) phenyl]-(3,4,5-trifluorophenyloxy) Methane difluoro- [4- (trans-4-heptylcyclohexyl) phenyl]-(3,4,5-trifluorophenyl C) Methane difluoro- [4- (trans-4-octylcyclohexyl) phenyl]-(3,4,5-trifluorophenyloxy) methane difluoro- [4- (trans-4-nonylcyclohexyl) phenyl]-(3 , 4,5-Trifluorophenyloxy) methane difluoro- [4- (trans-4-decylcyclohexyl) phenyl]-(3,4,5-trifluorophenyloxy) methane The following compounds can be prepared using various known phenol derivatives in place of, 5-trifluorophenol.

Difluoro- [4- (trans-4-ethylcyclohexyl) phenyl]-(3,4-difluorophenyloxy) methane difluoro- [4- (trans-4-propylcyclohexyl) phenyl]-(3,4-difluorophenyloxy ) Methane difluoro- [4- (trans-4-pentylcyclohexyl) phenyl]-(3,4-difluorophenyloxy) methane Cr42.9-43.4 N66.2-67.5 Iso difluoro- [4- (trans-4-ethyl Cyclohexyl) phenyl]-(4-trifluoromethylphenyloxy) methane difluoro- [4- (trans-4-propylcyclohexyl) phenyl]-(4-trifluoromethylphenyloxy) methane difluoro- [4- (trans-4 -Butylcyclohexyl) phenyl]-(4-trifluoromethyl Phenyloxy) methane Difluoro- [4- (trans-4-pentylcyclohexyl) phenyl]-(4-trifluoromethylphenyloxy) methane Cr79.6-79.9 Iso Difluoro- [4- (trans-4-ethylcyclohexyl) phenyl ]-(4-Trifluoromethoxyphenyloxy) methane Difluoro- [4- (trans-4-propylcyclohexyl) phenyl]-(4-trifluoromethoxyphenyloxy) methane Cr57.3-58.2 SB70.9-72.0 N83. 1-83.5 Iso Difluoro- [4- (trans-4-butylcyclohexyl) phenyl]-(4-trifluoromethoxyphenyloxy) methane Difluoro- [4- (trans-4-pentylcyclohexyl) phenyl]-(4-tri Fluoromethoxyphenyloxy) methane Cr68.1-68.3 SB80.5 -80.8 N90.2-90.4 Iso difluoro- [4- (trans-4-ethylcyclohexyl) phenyl]-(3-fluoro-4-trifluoromethoxyphenyloxy) methane difluoro- [4- (trans-4-propylcyclohexyl) ) Phenyl]-(3-fluoro-4-trifluoromethoxyphenyloxy) methane difluoro- [4- (trans-4-butylcyclohexyl) phenyl]-(3-fluoro-4-trifluoromethoxyphenyloxy) methane difluoro- [4- (trans-4-pentylcyclohexyl) phenyl]-(3-fluoro-4-trifluoromethoxyphenyloxy) methane Cr35.9-36.3 N61.1-61.3 Iso difluoro- [4- (trans-4-ethyl Cyclohexyl) phenyl]-(3-fluoro-4-trifluoromethyl Lphenyloxy) methane difluoro- [4- (trans-4-propylcyclohexyl) phenyl]-(3-fluoro-4-trifluoromethylphenyloxy) methane difluoro- [4- (trans-4-butylcyclohexyl) phenyl] -(3-fluoro-4-trifluoromethylphenyloxy) methane difluoro- [4- (trans-4-pentylcyclohexyl) phenyl]-(3-fluoro-4-trifluoromethylphenyloxy) methane difluoro- [4- (Trans-4-ethylcyclohexyl) phenyl]-(3,5-difluoro-4-trifluoromethoxyphenyloxy) methane difluoro- [4- (trans-4-propylcyclohexyl) phenyl]-(3,5-difluoro- 4-trifluoromethoxyphenyl Loxy] methane difluoro- [4- (trans-4-butylcyclohexyl) phenyl]-(3,5-difluoro-4-trifluoromethoxyphenyloxy) methane difluoro- [4- (trans-4-pentylcyclohexyl) phenyl] -(3,5-difluoro-4-trifluoromethoxyphenyloxy) methane difluoro- [4- (trans-4-ethylcyclohexyl) phenyl]-(3,5-difluoro-4-trifluoromethylphenyloxy) methane difluoro -[4- (trans-4-propylcyclohexyl) phenyl]-(3,5-difluoro-4-trifluoromethylphenyloxy) methane difluoro- [4- (trans-4-butylcyclohexyl) phenyl]-(3, 5-difluoro-4-trifluoromethylphenylo B) Methane difluoro- [4- (trans-4-pentylcyclohexyl) phenyl]-(3,5-difluoro-4-trifluoromethylphenyloxy) methane Cr56.9-57.5 Iso (Compound Production Example 2) difluoro- ｛ 4- [2- (trans-4-propylcyclohexyl) ethyl] phenyl}-(3,4,5-trifluorophenyloxy) methane (in the formula (I-1), n = 3 and Z ₁ is —CH ₂ CH ₂ , Preparation of X = F, Y = F) 4- [2- (trans-4-propylcyclohexyl) under a nitrogen atmosphere in a 500 ml three-necked flask equipped with a stirrer, thermometer, dropping funnel and nitrogen inlet tube. Ethyl] benzoic acid 15.0 g (54.7 mmol), DCC 13.5 g (65.6 mmol) and DMA
Dissolve 0.25 g (1.9 mmol) of P in 250 ml of dichloromethane, and 9.7 g of 3,4,5-trifluorophenol while stirring at room temperature.
(65.6 mmol) was added dropwise over 3 minutes, and the mixture was stirred at room temperature for 15 hours after the addition. After adding 100 ml of water to the reaction solution, the insolubles in dichloromethane were collected by filtration, the dichloromethane layer was separated, the aqueous layer was extracted with 200 ml of dichloromethane, and the extracted layers were mixed. Water (100 ml x 2), saturated sodium hydrogen carbonate Aqueous solution
The mixture was washed successively with 100 ml and water (100 ml × 2), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain 22.5 g of a reaction product. The reaction product was purified by column chromatography using silica gel as a filler and toluene as a developing solvent, and further recrystallized from a heptane-ethanol mixed solvent to obtain 12.9 g of colorless crystals. This is 3,4,5-trifluorophenyl-
{4- [2- (trans-4-propylcyclohexyl) ethyl] phenyl} benzoate.

Next, 3,4,5-trifluorophenyl- obtained in the above operation in a 100 ml eggplant flask equipped with a nitrogen inlet tube and a cooling tube.
12.9 g of {4- [2- (trans-4-propylcyclohexyl) ethyl] phenyl} benzoate (31.9 mmo
l), 25.8 g (63.9 mmol) of Lawson's reagent in 500 ml of toluene
And heated and refluxed for 65 hours while stirring under a nitrogen stream. After the reaction solution was cooled to room temperature, 200 ml of water was added, the toluene layer was separated, and the aqueous layer was further extracted with 150 ml of toluene. The organic layers were mixed, washed successively with water (200 ml x 2), saturated aqueous sodium hydrogen carbonate solution (100 ml), 10% aqueous sodium hydrogen sulfite solution 100 ml, and water (200 ml x 2), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. Thus, 13.3 g of a brown crystalline mixture was obtained. The reaction product was purified by column chromatography using silica gel as a filler and heptane as a developing solvent, and then recrystallized from heptane to yield yellow needle-like crystals.
4.5 g were obtained. This is 4- [2- (trans-4-propylcyclohexyl) ethyl] phenylcarbothioic acid-O
-3,4,5-trifluorophenyl.

Cr 95.5-97.6 Iso 1H-NMR (CDCl3; δ ppm) 0.7-1.9 (19H, m), 2.70 (2H,
m), 6.80 (2H, m), 7.25 (2H, d, J = 8.3Hz), and 8.21 (2
H, d, J = 8.3Hz). In a 100 ml eggplant flask equipped with a nitrogen inlet tube, at room temperature
4.5 g (10.8 mmol) of-[2- (trans-4-propylcyclohexyl) ethyl] phenylcarbothioic acid-O-3,4,5-trifluorophenyl is dissolved in 50 ml of dichloromethane, and 5.3 g (32.6 mmol) of DAST is dissolved. Was added and stirred at room temperature for 40 hours. After adding 50 ml of water to the reaction solution and separating the dichloromethane layer, the aqueous layer was further extracted with 50 ml of dichloromethane,
The extract layers were mixed, washed successively with water (50 ml × 2), a saturated aqueous sodium hydrogen carbonate solution (30 ml) and water (50 ml × 2), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain 3.9 g of colorless crystals. The reaction product was purified by column chromatography using silica gel as a filler and heptane as a developing solvent, and then recrystallized from heptane to obtain 1.5 g of colorless needle crystals. This is difluoro- {4- [2- (trans-4-
Propylcyclohexyl) ethyl] phenyl}-(3,4,
5-trifluorophenyloxy) methane.

Cr36.8-37.5 (NI23.5-23.7) Iso 1H-NMR (CDCl3; δ ppm) 0.7-2.0 (19H, m), 2.68 (2H,
m), 6.93 (2H, m), 7.27 (2H, d, J = 8.4Hz), and 7.58 (2
H, d, J = 8.4Hz). Using 4- [2- (trans-4-alkylcyclohexyl) ethyl] benzoic acid having a different alkyl chain instead of 4- [2- (trans-4-propylcyclohexyl) ethyl] benzoic acid according to the above production method. The following compounds can be prepared:

Difluoro- {4- [2- (trans-4-methylcyclohexyl) ethyl] phenyl}-(3,4,5-trifluorophenyloxy) methane difluoro- {4- [2- (trans-4-ethylcyclohexyl) Ethyl] phenyl}-(3,4,5-trifluorophenyloxy) methane difluoro- {4- [2- (trans-4-butylcyclohexyl) ethyl] phenyl}-(3,4,5-trifluorophenyloxy ) Methane difluoro- {4- [2- (trans-4-pentylcyclohexyl) ethyl] phenyl}-(3,4,5-trifluorophenyloxy) methane difluoro- {4- [2- (trans-4-hexyl) Cyclohexyl) ethyl] phenyl}-(3,4,5-trifluorophenyloxy) methane difluoro- {4- [2- (trans-4-he Tylcyclohexyl) ethyl] phenyl}-(3,4,5-trifluorophenyloxy) methane difluoro- {4- [2- (trans-4-octylcyclohexyl) ethyl] phenyl}-(3,4,5-tri Fluorophenyloxy) methane difluoro- {4- [2- (trans-4-nonylcyclohexyl) ethyl] phenyl}-(3,4,5-trifluorophenyloxy) methane difluoro- {4- [2- (trans- 4-decylcyclohexyl) ethyl] phenyl}-(3,4,5-trifluorophenyloxy) methane Also, various known phenol derivatives are used in place of 3,4,5-trifluorophenol according to the above-mentioned production method. The following compounds can be prepared.

Difluoro- {4- [2- (trans-4-ethylcyclohexyl) ethyl] phenyl}-(4-trifluoromethylphenyloxy) methane Difluoro- {4- [2- (trans-4-propylcyclohexyl) ethyl] phenyl {-(4-trifluoromethylphenyloxy) methane difluoro- {4- [2- (trans-4-butylcyclohexyl) ethyl] phenyl}-(4-trifluoromethylphenyloxy) methane difluoro- {4- [2 -(Trans-4-pentylcyclohexyl) ethyl] phenyl}-(4-trifluoromethylphenyloxy) methane difluoro- {4- [2- (trans-4-ethylcyclohexyl) ethyl] phenyl}-(4-trifluoro Methoxyphenyloxy) methane difluoro- ｛4 [2- (trans-4-propylcyclohexyl) ethyl] phenyl}-(4-trifluoromethoxyphenyloxy) methane Cr60.2-60.9 N72.6-73.2 Iso difluoro- {4- [2- (trans-4- [Butylcyclohexyl) ethyl] phenyl}-(4-trifluoromethoxyphenyloxy) methane difluoro- {4- [2- (trans-4-pentylcyclohexyl) ethyl] phenyl}-(4-trifluoromethoxyphenyloxy) methane difluoro -{4- [2- (Trans-4-ethylcyclohexyl) ethyl] phenyl}-(3-fluoro-
4-trifluoromethoxyphenyloxy) methane difluoro- {4- [2- (trans-4-propylcyclohexyl) ethyl] phenyl}-(3-fluoro-4-trifluoromethoxyphenyloxy) methane Cr30.8-31.3 N76 .9-77.7 Iso Difluoro- {4- [2- (trans-4-butylcyclohexyl) ethyl] phenyl}-(3-fluoro-
4-trifluoromethoxyphenyloxy) methanedifluoro- {4- [2- (trans-4-pentylcyclohexyl) ethyl] phenyl}-(3-fluoro-4-
Trifluoromethoxyphenyloxy) methane difluoro- {4- [2- (trans-4-ethylcyclohexyl) ethyl] phenyl}-(3-fluoro-
4-trifluoromethylphenyloxy) methane difluoro- {4- [2- (trans-4-propylcyclohexyl) ethyl] phenyl}-(3-fluoro-4-trifluoromethylphenyloxy) methane difluoro- {4- [ 2- (trans-4-butylcyclohexyl) ethyl] phenyl}-(3-fluoro-
4-trifluoromethylphenyloxy) methane difluoro- {4- [2- (trans-4-pentylcyclohexyl) ethyl] phenyl}-(3-fluoro-4-trifluoromethylphenyloxy) methane difluoro- {4- [ 2- (trans-4-ethylcyclohexyl) ethyl] phenyl}-(3,5-difluoro-4-trifluoromethoxyphenyloxy) methane difluoro- {4- [2- (trans-4-propylcyclohexyl) ethyl] phenyl {-(3,5-difluoro-4-trifluoromethoxyphenyloxy) methane difluoro- {4- [2- (trans-4-butylcyclohexyl) ethyl] phenyl}-(3,5-difluoro-4-trifluoro Methoxyphenyloxy) methane difluoro- {4- [2- (trans 4-pentylcyclohexyl) ethyl] phenyl {-(3,5-difluoro-4-trifluoromethoxyphenyloxy) methane difluoro- {4- [2- (trans-4-ethylcyclohexyl) ethyl] phenyl}-(3, 5-difluoro-4-trifluoromethylphenyloxy) methane difluoro- {4- [2- (trans-4-propylcyclohexyl) ethyl] phenyl}-(3,5-difluoro-4-trifluoromethylphenyloxy) methane Difluoro- {4- [2- (trans-4-butylcyclohexyl) ethyl] phenyl}-(3,5-difluoro-4-trifluoromethylphenyloxy) methane difluoro- {4- [2- (trans-4- Pentylcyclohexyl) ethyl {phenyl}-(3,5-difluoro-4-trifluoro) Methylphenyloxy) methane (Compound Production Example 3) Difluoro- (3 ′, 4 ′, 5′-trifluorobiphenyloxy)-[4- (trans-4-propylcyclohexyl) phenyl] methane [(I-2) Where n =
3, Z ₁ is a covalent bond, X = F, Y = F] 1) Production of 4- (3,4,5-trifluorophenyl) phenol 4- (3, 4,5-Trifluorophenyl) phenol was produced by the following operation. That is, 7.9 g (324.2 mmol) of shaved magnesium was added to a 1000 ml three-necked flask equipped with a stirrer, a thermometer, a nitrogen introducing tube, a dropping funnel, and a cooling tube, and 65.2 g (308.8 g) of 3,4,5-trifluorobromobenzene was added. (mmol) in 80 ml of tetrahydrofuran (hereinafter abbreviated as THF) was added dropwise over 50 minutes while maintaining the internal temperature at 50 ° C. After completion of the dropwise addition, the mixture was stirred and aged for 1 hour on a warm bath to maintain the same temperature to prepare a Grignard reagent. Then equipped with a separately prepared stirrer, thermometer, nitrogen inlet tube, dropping funnel and cooling tube 1000
35.0 g of iodobenzene (1
71.6 mmol), 1.64 g (9.3 mmol) of palladium chloride and TH
F300 ml was added, and the Grignard reagent prepared by the above operation was added dropwise over 50 minutes while heating and refluxing. After the addition, the mixture was heated and refluxed for another 3 hours, and then cooled to room temperature.
The reaction was terminated by adding l. The reaction solution was extracted with toluene (300 ml × 2) after filtering and separating insolubles. The extract layer is washed with water (300ml x3) and dried over anhydrous magnesium sulfate.
It was concentrated under reduced pressure to obtain 38.4 g of a dark brown solid. The concentrated residue was purified by chromatography using silica gel as a filler and heptane as a developing solvent, and then recrystallized from a heptane-ethanol mixed solvent to obtain 19.0 g of colorless crystals. This is
3,4,5-trifluorobiphenyl. Next, the obtained biphenyl derivative was subjected to bromination. That is, 19.0 g (91.5 mmol) of 3,4,5-trifluorobiphenyl obtained in the above operation was dissolved in 200 ml of dichloromethane in a 100 ml three-necked flask equipped with a stirrer, a thermometer, a nitrogen inlet tube, and a dropping funnel, and stirred. After cooling to -5 ° C, iron powder 0.26g (4.6mm
ol) and further add 8.8 g (109.8 mmol) of bromine to -5
It was added dropwise over 15 minutes to maintain 0 ° C. After completion of the dropwise addition, the mixture was further stirred for 1 hour while maintaining the same temperature. Water in the reaction solution
After the reaction was completed by adding 200 ml, the mixture was extracted with toluene (250 ml x 2). The extract layer was washed with water (200 ml x 4), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give a brown oily substance 25.1.
g was obtained. The concentrated residue was purified by chromatography using silica gel as a filler and heptane as a developing solvent, and then recrystallized from a mixed solvent of heptane and ethanol to obtain 16.6 g of colorless crystals. This is 4-bromo-3 ', 4', 5'-trifluorobiphenyl.

The bromobiphenyl derivative obtained by the above operation is RLKidwel
With reference to the report of l et al. (Org. Synth., V, 918 (1973)), a phenylphenol derivative was derived by the following procedure. That is, equipped with a stirrer, thermometer, nitrogen introduction tube, dropping funnel
1.5g of shaved magnesium in a 300ml three-necked flask (60.9mmo
l) was added, and a solution of 16.6 g (58.0 mmol) of 4-bromo-3 ', 4', 5'-trifluorobiphenyl dissolved in 30 ml of THF was taken over 25 minutes to maintain the internal temperature at 50 ° C. It was dropped. After completion of the dropwise addition, the mixture was stirred and aged for 1 hour on a warm bath to maintain the same temperature to prepare a Grignard reagent. Next, the reaction solution was cooled to −20 ° C. in a dry ice-acetone refrigerant, and 7.2 g of trimethyl borate was added dropwise, followed by stirring at the same temperature for 30 minutes. At the same temperature, 3.5 g (58.0 mmol) of acetic acid was added, the temperature was raised to 20 ° C., and 7.9 g (69.6 mmol) of 30% aqueous hydrogen peroxide was added dropwise over 10 minutes while keeping the temperature at 25 ° C. After the reaction solution was cooled again to −30 ° C. with a refrigerant, 50 ml of a 20% aqueous solution of sodium thiosulfate was added dropwise over 10 minutes to complete the reaction. The reaction solution was extracted with ethyl acetate (150 ml x 3), and saturated saline (200 ml).
lx2), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain 14.5 g of a brown solid. The concentrated residue was recrystallized from a heptane-toluene mixed solvent to obtain 10.9 g of colorless crystals. This is 4- (3,4,5-trifluorophenyl) phenol.

2) Production of difluoro- (3 ', 4', 5'-trifluorobiphenyloxy)-[4- (trans-4-propylcyclohexyl) phenyl] methane Equipped with a stirrer, thermometer, dropping funnel and nitrogen inlet tube. Under a nitrogen atmosphere in a 500 ml three-necked flask, 15.0 g of 4- (trans-4-propylcyclohexyl) benzoic acid (60.9 m
mol), 15.1 g (73.1 mmol) of DCC and 0.27 g (2.2 mmo) of DMAP
l) was dissolved in 300 ml of dichloromethane, and a solution of 16.4 g (73.1 mmol) of 4- (3,4,5-trifluorophenyl) phenol described above in 80 ml of dichloromethane was stirred for 20 minutes at room temperature. The mixture was added dropwise and stirred at room temperature for 10 hours after the addition. After adding 200 ml of water to the reaction solution, the insolubles in dichloromethane were separated by filtration, the dichloromethane layer was separated, the aqueous layer was extracted with 200 ml of dichloromethane, and the extracted layers were mixed. Water (200 ml x 2), saturated sodium hydrogen carbonate Aqueous solution
The extract was washed with 100 ml and water (200 ml × 2) sequentially, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain 26.9 g of a reaction product. The reaction product was purified by column chromatography using silica gel as a filler and using toluene as a developing solvent, and further recrystallized from a heptane-ethanol mixed solvent to obtain 22.8 g of colorless crystals. This is (3 ', 4', 5'-trifluorobiphenyl) -4- (trans-4-cyclohexyl)
Benzoart.

Next, 22.8 g (50.5 mmol) of (3 ', 4', 5'-trifluorobiphenyl) -4- (trans-4-cyclohexyl) benzoate obtained in the above operation in a 100 ml eggplant flask equipped with a nitrogen inlet tube and a cooling tube. ), Lawson's reagent 40.9 (10
1.1 mmol) was dissolved in 500 ml of toluene, and heated and refluxed for 60 hours while stirring with a nitrogen stream. After the reaction solution was cooled to room temperature, 200 ml of water was added, the toluene layer was separated, and the aqueous layer was further extracted with 200 ml of toluene. Combine the organic layers and add water (200
ml x 2), saturated aqueous sodium hydrogen carbonate solution (100 ml), 10
100ml aqueous sodium bisulfite solution and water (200ml x
After successively washing in 2), drying over anhydrous magnesium sulfate and concentration under reduced pressure gave 23.4 g of a brown crystalline mixture. The reaction product was purified by column chromatography using silica gel as a filler and heptane as a developing solvent, and then recrystallized from heptane to obtain 8.3 g of yellow needle crystals. This is 4- (trans-4-prolcyclohexyl) phenylcarbothioic acid-O-3 ', 4', 5'-trifluorobiphenyl.

In a 100 ml eggplant flask equipped with a nitrogen inlet tube, at room temperature
8.3 g (17.7 mmol) of-(trans-4-propylcyclohexyl) phenylcarbothioic acid-O-3 ', 4', 5'-trifluorobiphenyl is dissolved in 80 ml of dichloromethane,
8.5 g (53.0 mmol) of DAST was added, and the mixture was stirred at room temperature for 40 hours. After adding 50 ml of water to the reaction solution and separating the dichloromethane layer, the aqueous layer was further extracted with 50 ml of dichloromethane, and the extracted layers were mixed, and sequentially extracted with water (50 ml x 2), a saturated aqueous sodium hydrogen carbonate solution 30 ml and water (50 ml x 2). After washing, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give brown crystals 8.1 g.
I got The reaction product was purified by column chromatography using silica gel as a filler and heptane as a developing solvent.
Recrystallization from heptane gave 1.9 g of colorless needle crystals. This is difluoro- (3 ', 4', 5'-trifluorobiphenyloxy)-[4- (trans-4-propylcyclohexyl) phenyl] methane.

According to the above production method, the following compounds can be produced by using 4- (trans-4-alkylcyclohexyl) benzoic acid having a different alkyl chain instead of 4- (trans-4-propylcyclohexyl) benzoic acid.

Difluoro- (3 ', 4', 5'-trifluorobiphenyloxy)-[4- (trans-4-methylcyclohexyl) phenyl] methane difluoro- (3 ', 4', 5'-trifluorobiphenyloxy)- [4- (trans-4-ethylcyclohexyl) phenyl] methane difluoro- (3 ', 4', 5'-trifluorobiphenyloxy)-[4- (trans-4-butylcyclohexyl) phenyl] methane difluoro- (3 ', 4', 5'-Trifluorobiphenyloxy)-[4- (trans-4-pentylcyclohexyl) phenyl] methane Cr73.8-74.4 N163.4-164.0 Iso Difluoro- (3 ', 4', 5 ' -Trifluorobiphenyloxy)-[4- (trans-4-hexylcyclohexyl) phenyl] methane difluoro- (3 ', 4', 5'-trifluorobiph Nyloxy)-[4- (trans-4-heptylcyclohexyl) phenyl] methane difluoro- (3 ', 4', 5'-trifluorobiphenyloxy)-[4- (trans-4-octylcyclohexyl) phenyl] methane difluoro -(3 ', 4', 5'-trifluorobiphenyloxy)-[4- (trans-4-nonylcyclohexyl) phenyl] methane difluoro- (3 ', 4', 5'-trifluorobiphenyloxy)-[ 4- (trans-4-decylcyclohexyl) phenyl] methane (Compound Production Example 4) Various known benzoic acid derivatives and various known phenol derivatives including the compounds whose production examples are described in detail in the above compound production examples Optionally selected, according to the above-mentioned production method, 4- (trans-4-propylcyclohexyl) benzoic acid or ', 4', the following compounds by using in place of 5'-fluoro-biphenol can be produced.

Difluoro- (4'-trifluoromethoxybiphenyloxy)-[4- (trans-4-ethylcyclohexyl) phenyl] methane difluoro- (4'-trifluoromethoxybiphenyloxy)-[4- (trans-4-propylcyclohexyl) ) Phenyl) methane difluoro- (4'-trifluoromethoxybiphenyloxy)-[4- (trans-4-butylcyclohexyl) phenyl] methane difluoro- (4'-trifluoromethoxybiphenyloxy)-[4- (trans- 4-pentylcyclohexyl) phenyl] methane difluoro- (4'-trifluoromethylbiphenyloxy)-[4- (trans-4-ethylcyclohexyl) phenyl] methane difluoro- (4'-trifluoromethylbiphenyloxy)-[ -(Trans-4-propylcyclohexyl) phenyl] methane difluoro- (4'-trifluoromethylbiphenyloxy)-[4- (trans-4-butylcyclohexyl) phenyl] methane difluoro- (4'-trifluoromethylbiphenyloxy )-[4- (trans-4-pentylcyclohexyl) phenyl] methane difluoro- (3'-fluoro-4'-trifluoromethoxybiphenyloxy)-[4- (trans-4-
Ethylcyclohexyl) phenyl] methane difluoro- (3'-fluoro-4'-trifluoromethoxybiphenyloxy)-[4- (trans-4-
Propylcyclohexyl) phenyl] methane difluoro- (3'-fluoro-4'-trifluoromethoxybiphenyloxy)-[4- (trans-4-
Butylcyclohexyl) phenyl] methane difluoro- (3'-fluoro-4'-trifluoromethoxybiphenyloxy)-[4- (trans-4-
Pentylcyclohexyl) phenyl] methane difluoro- (3'-fluoro-4'-trifluoromethylbiphenyloxy)-[4- (trans-4-ethylcyclohexyl) phenyl] methane difluoro- (3'-fluoro-4'-tri Fluoromethylbiphenyloxy)-[4- (trans-4-propylcyclohexyl) phenyl] methane difluoro- (3'-fluoro-4'-trifluoromethylbiphenyloxy)-[4- (trans-4-butylcyclohexyl) phenyl Methane difluoro- (3'-fluoro-4'-trifluoromethylbiphenyloxy)-[4- (trans-4-pentylcyclohexyl) phenyl] methane difluoro- (3 ', 5'-difluoro-4'-trifluoro Methoxybiphenyloxy)-[ 4- (trans-4-ethylcyclohexyl) phenyl] methane difluoro- (3 ', 5'-difluoro-4'-trifluoromethoxybiphenyloxy)-[4- (trans-4-propylcyclohexyl) phenyl] methane difluoro- (3 ', 5'-difluoro-4'-trifluoromethoxybiphenyloxy)-[4- (trans-4-butylcyclohexyl) phenyl] methane difluoro- (3', 5'-difluoro-4'-trifluoromethoxy Biphenyloxy)-[4- (trans-4-pentylcyclohexyl) phenyl] methane difluoro- (3 ', 5'-difluoro-4'-trifluoromethylbiphenyloxy)-[4- (trans-
4-ethylcyclohexyl) phenyl] methane difluoro- (3 ', 5'-difluoro-4'-trifluoromethylbiphenyloxy)-[4- (trans-
4-propylcyclohexyl) phenyl] methane difluoro- (3 ', 5'-difluoro-4'-trifluoromethylbiphenyloxy)-[4- (trans-
4-butylcyclohexyl) phenyl] methane difluoro- (3 ', 5'-difluoro-4'-trifluoromethylbiphenyloxy)-[4- (trans-
4-pentylcyclohexyl) phenyl] methane difluoro- (3 ', 4', 5'-trifluorobiphenyloxy)-[2-fluoro-4- (trans-4-ethylcyclohexyl) phenyl] methane difluoro- (3 ', 4 ', 5'-trifluorobiphenyloxy)-[2-fluoro-4- (trans-4-propylcyclohexyl) phenyl] methane difluoro- (3', 4 ', 5'-trifluorobiphenyloxy)-[2 -Fluoro-4- (trans-4-butylcyclohexyl) phenyl] methane difluoro- (3 ', 4', 5'-trifluorobiphenyloxy)-[2-fluoro-4- (trans-4-pentylcyclohexyl) phenyl ] Methane difluoro- (3 ', 4', 5'-trifluorobiphenyloxy)-{4- [2- (trans-4 -Ethylcyclohexyl) ethyl] phenyl} methane difluoro- (3 ', 4', 5'-trifluorobiphenyloxy)-{4- [2- (trans-4-propylcyclohexyl) ethyl] phenyl} methane difluoro- (3 ', 4', 5'-Trifluorobiphenyloxy)-{4- [2- (trans-4-butylcyclohexyl) ethyl] phenyl} methane difluoro- (3 ', 4', 5'-trifluorobiphenyloxy) -{4- [2- (trans-4-pentylcyclohexyl) ethyl] phenyl} methane difluoro- (4'-trifluoromethoxybiphenyloxy)-{4- [2- (trans-4-ethylcyclohexyl) ethyl] phenyl {Methane difluoro- (4'-trifluoromethoxybiphenyloxy)-{4- [2- ( [S-4-propylcyclohexyl) ethyl] phenyl} methane difluoro- (4'-trifluoromethoxybiphenyloxy)-{4- [2- (trans-4-butylcyclohexyl) ethyl] phenyl} methane difluoro- (4'- Trifluoromethoxybiphenyloxy)-{4- [2- (trans-4-pentylcyclohexyl) ethyl] phenyl} methane difluoro- (4'-trifluoromethylbiphenyloxy)-{4- [2- (trans-4- Ethylcyclohexyl) ethyl] phenyl} methane difluoro- (4'-trifluoromethylbiphenyloxy)-{4- [2- (trans-4-propylcyclohexyl) ethyl] phenyl} methane difluoro- (4'-trifluoromethylbiphenyl Oxy)-{4- [2- Trans-4-butylcyclohexyl) ethyl] phenyl} methane difluoro- (4'-trifluoromethylbiphenyloxy)-{4- [2- (trans-4-pentylcyclohexyl) ethyl] phenyl} methane difluoro- (3 ', 5'-difluoro-4'-trifluoromethylbiphenyloxy)-{4- [2- (trans-4-ethylcyclohexyl) ethyl] phenyl}
Methane difluoro- (3 ', 5'-difluoro-4'-trifluoromethylbiphenyloxy)-{4- [2- (trans-4-propylcyclohexyl) ethyl] phenyl} methane Cr101.8-102.1 N134.4- 135.0 Iso difluoro- (3 ', 5'-difluoro-4'-trifluoromethylbiphenyloxy)-{4- [2- (trans-4-butylcyclohexyl) ethyl] phenyl}
Methane difluoro- (3 ', 5'-difluoro-4'-trifluoromethylbiphenyloxy)-{4- [2- (trans-4-pentylcyclohexyl) ethyl] phenyl} methane Next, the liquid crystal composition of the present invention Examples and Comparative Examples are shown below. The composition ratios of Comparative Examples and Examples are all shown by weight%. The compounds used in Examples and Comparative Examples are represented by symbols based on the definitions shown in Table 1.

Data on the properties of the liquid crystal composition include a clearing point (T _N1 ), a smectic-nematic phase transition point (T _SN ), a viscosity at 20 ° C. (η ₂₀ ), a refractive index anisotropy at 25 ° C. (Δn),
It was expressed by dielectric anisotropy (Δε) at 25 ° C. and threshold voltage (V _th ) at 20 ° C.

The voltage holding ratio was measured by the area method (Tatsuo Shimazaki et al., TFT-LCD
Voltage holding characteristics I, p.78, Proceedings of the 14th LCD Discussion Meeting (1
Frame period 60H based on the method described in 988)
z, voltage 5.0 volts, ON time 60 μsec, liquid crystal layer thickness 7.0
The test was performed at 25 ° C. using a liquid crystal cell in which a polyimide-based alignment film was rubbed on a glass substrate on which an ITO pattern having a μ and an electrode area of 1 cm ² was deposited. The _TSN point was 0 ° C and -10
The liquid crystal phase was determined after standing for 30 days in a freezer at -20 ° C, -20 ° C and -30 ° C.

Comparative Example 1 The following composition disclosed in Application Example 2 of JP-A-2-233626 was prepared.

 3-HHB-FFF 15.0% 2-HHB-FF 28.4% 3-HHB-FF 28.3% 5-HHB-FF 28.3% The physical properties of this liquid crystal composition are shown below.

T _N1 = 110.7 ° C. T _SN <0 ° C. η ₂₀ = 25.0 mPa · s Δn = 0.077 V _th = 2.32 (V) VHR = 98.8% This liquid crystal composition has a large threshold voltage and a low-temperature compatibility. Not good (T _SN is high).

Comparative Example 2 The following composition disclosed in Example 1 of WO94 / 03558 was prepared.

 7-HB-FFF 10.0% 2-HHB-FFF 25.0% 3-HHB-FFF 35.0% 5-HHB-FFF 18.0% 7-HB-FF 12.0% The physical properties of this liquid crystal composition are shown below.

T _N1 = 42.9 ° C. T _SN <0 ° C. η ₂₀ = 22.2 mPa · s Δn = 0.059 V _th = 1.07 (V) VHR = 98.7% This liquid crystal composition has a small threshold voltage but a small clearing point. Also, the low-temperature compatibility is not good. Further, Δn is small and lacks practicality.

Comparative Example 3 The following composition disclosed in Example 2 of WO94 / 03558 was prepared.

 2-HHB-FFF 26.0% 3-HHB-FFF 26.0% 5-HHB-FFF 26.0% 7-HB-FF 12.0% 5-H2B-FF 10.0% The physical properties of this liquid crystal composition are shown below.

T _N1 = 46.0 ° C. T _SN <0 ° C. η ₂₀ = 21.6 mPa · s Δn = 0.58 V _th = 1.17 V VHR = 98.5% This liquid crystal composition has a small threshold voltage, a small clearing point, and a low temperature. Poor compatibility. Further, Δn is small and lacks practicality.

Comparative Example 4 The following composition disclosed in Example 4 of WO94 / 03558 was prepared.

 2-HHB-FFF 10.0% 3-HHB-FFF 10.0% 5-HHB-FFF 10.0% 5-H2B-FF 10.0% 5-HEB-F 7.5% 7-HEB-F 7.5% 2-HHB-FF 11.7% 3 -HHB-FF 11.7% 5-HHB-FF 11.6% 3-HHB-F 5.0% 5-HHEB-F 2.5% 7-HHEB-F 2.5% The physical properties of this liquid crystal composition are shown below.

T _N1 = 71.3 ° C. T _SN <−20 ° C. η ₂₀ = 19.2 mPa · s Δn = 0.070 V _th = 1.77 V VHR = 98.2% This liquid crystal composition has a threshold voltage for a clearing point of about 70 ° C. Is big. Further, Δn is slightly small.

Example 1 3-HBCF2OB (F, F) -F 5.0% 3-H2HB (F, F) -F 7.0% 5-H2HB (F, F) -F 11.0% 3-HHB (F, F) -F 10.0 % 4-HHB (F, F) -F 6.0% 3-HH2B (F, F) -F 12.0% 5-HH2B (F, F) -F 8.0% 3-HBB (F, F) -F 14.0% 5 -HBB (F, F) -F 14.0% 3-HHEB (F, F) -F 9.0% 5-HHEB (F, F) -F 4.0% The physical properties of this liquid crystal composition are shown below.

T _N1 = 77.2 ° C. T _SN <−30 ° C. η ₂₀ = 27.4 mPa · s Δn = 0.089 Δε = 9.5 V _th = 1.54 V VHR = 98.5% This liquid crystal composition has excellent low-temperature compatibility and a large nematic phase range. , Its threshold voltage is small, and it is practical.

Example 2 5-HBCF2OB (F) -OCF3 5.0% 3-HBCF2OB (F, F) -F 2.0% 5-HBCF2OB (F, F) -F 6.0% 3-H2BCF2OBB (F, F) -CF3 2.0% 7 -HB- (F, F) -F 5.0% 3-HHB (F, F) -F 7.0% 3-HH2B (F, F) -F 6.0% 3-HBB (F, F) -F 10.0% 5- HBB (F, F) -F 15.0% 3-H2BB (F, F) -F 4.0% 5-H2BB (F, F) -F 4.0% 3-HBEB (F, F) -F 3.0% 4-HBEB ( F, F) -F 3.0% 5-HBEB (F, F) -F 3.0% 3-HHEB (F, F) -F 15.0% 4-HHEB (F, F) -F 5.0% 5-HHEB (F, F F) -F 5.0% The physical properties of this liquid crystal composition are shown below.

T _N1 = 66.3 ° C. T _SN <−10 ° C. η ₂₀ = 31.1 mPa · s Δn = 0.094 Δε = 11.3 V _th = 1.26 V VHR = 98.6% This liquid crystal composition has excellent low-temperature compatibility and a large nematic phase range. , Its threshold voltage is small, and it is practical.

Example 3 5-HBCF2OB (F) -F 5.0% 5-HBCF2OB (F) -OCF3 8.0% 3-HBCF2OB (F, F) -F 7.0% 3-HBB (F, F) -F 12.0% 5-HBB (F, F) -F 12.0% 3-HHB (F, F) -F 4.0% 3-H2BB (F, F) -F 8.0% 4-H2BB (F, F) -F 8.0% 5-H2BB (F , F) -F 8.0% 3-HBEB (F, F) -F 4.0% 3-HHEB (F, F) -F 12.0% 4-HHEB (F, F) -F 4.0% 5-HHEB (F, F ) -F 4.0% 3-HH2BB (F, F) -F 4.0% The physical properties of this liquid crystal composition are shown below.

T _N1 = 72.6 ° C. T _SN <−30 ° C. η ₂₀ = 30.5 mPa · s Δn = 0.106 Δε = 10.5 V _th = 1.44 V VHR = 98.7% This liquid crystal composition has excellent low-temperature compatibility and a large nematic phase range. , Its threshold voltage is small, and it is practical.

Example 4 3-HBCF2OB (F, F) -F 5.0% 5-HBCF2OB (F, F) -F 5.0% 5-HBCF2OB (F, F) -CF3 5.0% 3-HBB (F, F) -F 18.0 % 5-HBB (F, F) -F 18.0% 5-H2BB (F, F) -F 10.0% 3-HBEB (F, F) -F 4.0% 3-HHEB (F, F) -F 10.0% 3 -HB-CL 6.0% 2-HHB-CL 4.0% 4-HHB-CL 10.0% 5-HHB-CL 5.0% The physical properties of this liquid crystal composition are shown below.

T _N1 = 77.4 ° C. T _SN <−20 ° C. η ₂₀ = 25.6 mPa · s Δn = 0.111 Δε = 9.7 V _th = 1.58 V VHR = 98.5% This liquid crystal composition has excellent low-temperature compatibility and a large nematic phase range. , Its threshold voltage is small, and it is practical.

Example 5 5-HBCF2OB (F, F) -F 10.0% 5-HBCF2OB (F) -OCF3 10.0% 7-HB- (F, F) -F 8.0% 3-HHB (F, F) -F 8.0% 4-HHB (F, F) -F 4.0% 3-H2HB (F, F) -F 10.0% 4-H2HB (F, F) -F 10.0% 3-HH2B (F, F) -F 10.0% 5- HH2B (F, F) -F 8.0% 3-HBB (F, F) -F 8.0% 5-HBB (F, F) -F 8.0% 3-HHBB (F, F) -F 3.0% 3-HH2BB ( F, F) -F 3.0% The physical properties of this liquid crystal composition are shown below.

T _N1 = 65.2 ° C. T _SN <−30 ° C. η ₂₀ = 25.8 mPa · s Δn = 0.084 Δε = 8.5 V _th = 1.51 V VHR = 98.6% This liquid crystal composition has excellent low-temperature compatibility and a large nematic phase range. , Its threshold voltage is small, and it is practical.

Example 6 3-H2BCF2OB (F, F) -F 2.0% 3-HBCF2OB (F, F) -F 4.0% 5-HBCF2OB (F, F) -CF3 4.0% 3-HHB (F, F) -F 10.0 % 3-HBB (F, F) -F 15.0% 5-HBB (F, F) -F 15.0% 3-H2BB (F, F) -F 10.0% 5-H2BB (F, F) -F 10.0% 3 -HB-CL 10.0% 5-HB-CL 3.0% 7-HB (F, F) -F 3.0% 4-HHB-CL 5.0% 5-HHB-CL 6.0% 3-HH2BB (F, F) -F 3.0 % Physical properties of the liquid crystal composition are shown below.

T _N1 = 58.4 ° C. T _SN <−30 ° C. η ₂₀ = 23.0 mPa · s Δn = 0.102 Δε = 7.7 V _th = 1.50 V VHR = 98.6% This liquid crystal composition has excellent low-temperature compatibility and a large nematic phase range. , Its threshold voltage is small, and it is practical.

Example 7 3-HBCF2OB (F, F) -F 5.0% 5-HBCF2OB (F, F) -F 10.0% 5-HBCF2OB (F) -OCF3 10.0% 3-H2BCF2OBB (F, F) -CF3 5.0% 3 -HHB (F, F) -F 6.0% 4-HHB (F, F) -F 4.0% 3-H2HB (F, F) -F 6.0% 4-H2HB (F, F) -F 5.0% 5-H2HB (F, F) -F 5.0% 3-HBB (F, F) -F 14.0% 5-HBB (F, F) -F 14.0% 3-HH2B (F, F) -F 10.0% 5-HH2B (F , F) -F 6.0% The physical properties of this liquid crystal composition are shown below.

T _N1 = 65.0 ° C. T _SN <−10 ° C. η ₂₀ = 27.9 mPa · s Δn = 0.094 Δε = 9.8 V _th = 1.47 V VHR = 98.7% This liquid crystal composition has excellent low-temperature compatibility and a large nematic phase range. , Its threshold voltage is small, and it is practical.

Example 8 3-H2BCF2OBB (F, F) -CF3 10.0% 3-H2HB (F, F) -F 10.0% 4-H2HB (F, F) -F 10.0% 5-H2HB (F, F) -F 10.0 % 3-HHB (F, F) -F 8.0% 3-HH2B (F, F) -F 7.0% 5-HH2B (F, F) -F 7.0% 3-HBB (F, F) -F 12.0% 5 -HBB (F, F) -F 11.0% 2-HHB (F) -F 1.6% 3-HHB (F) -F 1.7% 5-HHB (F) -F 1.7% 2-HBB (F) -F 1.3 % 3-HBB (F) -F 1.3% 5-HBB (F) -F 2.4% 3-HB (F) VB-2 5.0% The physical properties of this liquid crystal composition are shown below.

T _N1 = 91.0 ° C. T _SN <−30 ° C. η ₂₀ = 33.9 mPa · s Δn = 0.106 Δε = 9.2 V _th = 1.75 V VHR = 98.7% This liquid crystal composition has excellent low-temperature compatibility and a large nematic phase range. Also, the threshold voltage is small for a transparent point of about 90 ° C. Also, Δn is moderately large, and is practical.

Example 9 3-HBCF2OB (F, F) -F 5.0% 5-HBCF2OB (F, F) -F 10.0% 7-HB (F, F) -F 4.0% 3-HBB (F, F) -F 12.0 % 5-HBB (F, F) -F 12.0% 3-HHB (F, F) -F 4.0% 3-H2BB (F, F) -F 9.0% 4-H2BB (F, F) -F 9.0% 5 -H2BB (F, F) -F 9.0% 3-HBEB (F, F) -F 3.0% 3-HHEB (F, F) -F 12.0% 4-HHEB (F, F) -F 4.0% 5-HHEB (F, F) -F 4.0% 2-HHHB (F, F) -F 3.0% The physical properties of this liquid crystal composition are shown below.

T _N1 = 60.6 ° C. T _SN <−20 ° C. η ₂₀ = 29.3 mPa · s Δn = 0.098 Δε = 11.1 V _th = 1.31 V VHR = 98.6% This liquid crystal composition has excellent low-temperature compatibility and a large nematic phase range. , Its threshold voltage is small, and it is practical.

Example 10 3-HBCF2OB (F, F) -F 5.0% 5-HBCF2OB (F, F) -F 10.0% 7-HB (F, F) -F 4.0% 3-HBB (F, F) -F 12.0 % 5-HBB (F, F) -F 12.0% 3-HHB (F, F) -F 4.0% 3-H2BB (F, F) -F 9.0% 4-H2BB (F, F) -F 13.0% 5 -H2BB (F, F) -F 9.0% 2-HBEB (F, F) -F 3.0% 2-HH2B (F, F) -F 12.0% 3-HH2BB (F, F) -F 4.0% 2-HHHB (F, F) -F 3.0% The physical properties of this liquid crystal composition are shown below.

T _N1 = 54.9 ° C. T _SN <−30 ° C. η ₂₀ = 31.0 mPa · s Δn = 0.122 Δε = 9.3 V _th = 1.29 V VHR = 98.5% This liquid crystal composition has excellent low-temperature compatibility and a large nematic phase range. , Its threshold voltage is small, and it is practical.

Further examples of the composition according to the present invention are described below.

Example 11 3-HBCF2OB (F) -F 10.0% 5-HBCF2OBB (F, F) -F 10.0% 7-HB (F, F) -F 5.0% 3-HHB (F, F) -F 5.0% 3 -H2HB (F, F) -F 5.0% 3-HBB (F, F) -F 15.0% 5-HBB (F, F) -F 11.0% 3-H2BB (F, F) -F 5.0% 4-H2BB (F, F) -F 5.0% 5-H2BB (F, F) -F 5.0% 4-HBEB (F, F) -F 3.0% 5-HBEB (F, F) -F 3.0% 3-HHEB (F , F) -F 8.0% 4-HHEB (F, F) -F 5.0% 5-HHEB (F, F) -F 5.0% Example 12 3-H2BCF2OB (F) -OCF3 10.0% 3-H2BCF2OB (F, F F) -F 7.0% 3-H2HB (F, F) -F 8.0% 5-H2HB (F, F) -F 7.0% 3-HHB (F, F) -F 10.0% 4-HHB (F, F) -F 4.0% 3-HH2B (F, F) -F 10.0% 5-HH2B (F, F) -F 5.0% 3-HBB (F, F) -F 15.0% 5-HBB (F, F) -F 10.0% 3-HHEB (F, F) -F 8.0% 5-HHEB (F, F) -F 2.0% 3-HHBB (F, F) -F 2.0% 3-HH2BB (F, F) -F 2.0% Example 13 3-H2BCF2OB (F) -OCF3 10.0% 5-HBCF2OBB (F, F) -F 3.0% 3-H2HB (F, F) -F 12.0% 5-H2HB (F, F) -F 11.0% 3 -HHB (F, F) -F 10.0% 4-HHB (F, F) -F 6.0% 3-HH2B (F, F) -F 12.0% 5-HH2B (F, F) -F 8.0% 3-HBB (F, F) -F 14.0% 5-HBB (F, F) -F 14.0% Table 2 shows the characteristics of the liquid crystal compositions of the above comparative examples and examples. As is clear from Table 2, the present invention provides an AM-LCD
While satisfying various characteristics required for liquid crystal compositions for
In particular, the threshold voltage is small, and the low-temperature compatibility is excellent,
A liquid crystal composition having a large nematic phase range can be provided.

INDUSTRIAL APPLICABILITY The liquid crystal composition of the present invention is useful as a low voltage liquid crystal material in various modes such as an active matrix mode and an STN mode.

──────────────────────────────────────────────────続 き Continuation of the front page (72) Inventor Etsuo Nakagawa 8890 Goi, Ichihara-shi, Chiba (72) Inventor Shinichi Sawada 316-1 168, Nishihiro, Ichihara-shi, Chiba 11 (56) References JP-A-5-95 112778 (JP, A) JP-A-2-289529 (JP, A) JP-A-2-233626 (JP, A) (58) Fields investigated (Int. Cl. ⁶ , DB name) C09K 19/42-19 / 46 G02F 1/13 CA (STN) CAOLD (STN) REGISTRY (STN)

Claims (6)

(57) [Claims] (1) The first component contains at least one compound represented by the general formula (I-1) or (I-2), and the second component has a general formula (II-1) A liquid crystal composition comprising at least one compound represented by any one of the above (II-7). (In the formula, n represents an integer of 1 to 10, Z ₁ represents —CH ₂ CH ₂ — or a single bond, X represents F, OCF ₃ or CF ₃ , and Y represents H or F.) 2. The liquid crystal composition according to claim 1, wherein
A liquid crystal composition characterized in that the first component is 3 to 40% by weight and the second component is 50 to 97% by weight based on the total weight thereof. 3. A liquid crystal composition further comprising a compound represented by the general formula (III) in addition to the liquid crystal composition according to claim 1. (Where n represents an integer of 1 to 10) 4. The composition according to claim 1, further comprising a compound represented by formula (IV-1) and / or formula (IV-2) in addition to the liquid crystal composition according to claim 1. A liquid crystal composition characterized by the following. (Where n represents an integer of 1 to 10) 5. The liquid crystal composition according to claim 1, further comprising a compound represented by formula (V-1) and / or formula (V-2). A liquid crystal composition characterized by the following. (Where n represents an integer of 1 to 10) 6. A liquid crystal display device using the liquid crystal composition according to any one of claims (1) to (5).