COMPOUND HAVING A DIFLUOROCYCLOHEXANE RING, LIQUID CRYSTAL COMPOSITION AND LIQUID CRYSTAL DISPLAY DEVICE

Abstract

A liquid crystal compound represented by

##STR00001##

R.sup.1 and R.sup.2 are independently hydrogen, fluorine, chlorine, alkyl or the like; ring A.sup.1 and ring A.sup.3 are independently 1,4-cyclohexylene, 1,4-phenylene or the like; and A.sup.2 is a divalent group represented by formula (A-1) or formula (A-2)

##STR00002##

Z.sup.1, Z.sup.2, Z.sup.3, Z.sup.4 and Z.sup.5 are independently a single bond, COO or the like; and a to d is 0, 1 or the like.

Claims

1. A compound represented by formula (1): ##STR00323## in formula (1), R.sup.1 and R.sup.2 are independently hydrogen, fluorine, chlorine or alkyl having 1 to 20 carbons, and in the alkyl at least one CH.sub.2 may be replaced by O, at least one CH.sub.2CH.sub.2 may be replaced by CHCH, and in these groups at least one hydrogen may be replaced by fluorine; ring A.sup.1 and ring A.sup.3 are independently 1,4-cyclohexylene, 1,4-phenylene, 1,4-phenylene in which at least one hydrogen has been replaced by fluorine, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyridine-2,5-diyl or pyrimidine-2,5-diyl, A.sup.2 is a divalent group represented by formula (A-1) or formula (A-2), ring A.sup.4 is 1,4-phenylene or tetrahydropyran-2,5-diyl, and ring A.sup.5 is 1,4-cyclohexylene or tetrahydropyran-2,5-diyl; ##STR00324## Z.sup.1, Z.sup.2, Z.sup.3, Z.sup.4 and Z.sup.5 are independently a single bond, COO, OCO, OCH.sub.2, CH.sub.2O, CF.sub.2O, OCF.sub.2, CH.sub.2CH.sub.2, CHCH, CC, CF.sub.2CF.sub.2, CFCF, (CH.sub.2).sub.4, CHCHCH.sub.2CH.sub.2 or CH.sub.2CHCHCH.sub.2; and a and b are independently 0, 1 or 2, when A.sup.2 is formula (A-1), c is 0 or 1, and the sum of a, b and c is 1 or 2, and when A.sup.2 is formula (A-2), d is 0 or 1, and the sum of a, b and d is 1 or 2. where at least one of Z.sup.2 and Z.sup.4 is COO, OCO, OCH.sub.2, CH.sub.2O, CF.sub.2O, OCF.sub.2, CHCH, CC, CF.sub.2CF.sub.2, CFCF, (CH.sub.2).sub.4, CHCHCH.sub.2CH.sub.2 or CH.sub.2CHCHCH.sub.2, when A.sup.2 is formula (A-1), ring A.sup.4 is 1,4-phenylene, a and b is 0, and c is 1; where R.sup.1 and R.sup.2 are independently hydrogen, fluorine, chlorine or alkyl having 1 to 20 carbons, and in the alkyl at least one CH.sub.2 may be replaced by O, and in these groups at least one hydrogen may be replaced by fluorine, Z.sup.5 is a single bond, COO, OCO, OCH.sub.2, CH.sub.2O, CF.sub.2O, OCF.sub.2, CHCH, CC, CF.sub.2CF.sub.2, CFCF, (CH.sub.2).sub.4, CHCHCH.sub.2CH.sub.2 or CH.sub.2CHCHCH.sub.2, when A.sup.2 is formula (A-2), ring A.sup.5 is 1,4-cyclohexylene, a and b is 0, and d is 1; where ring A.sup.3 is 1,4-cyclohexylene, 1,4-phenylene in which at least one hydrogen has been replaced by fluorine, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyridine-2,5-diyl or pyrimidine-2,5-diyl, when A.sup.2 is formula (A-2), a and d is 0, and b is 1; where ring A.sup.1 is 1,4-phenylene, 1,4-phenylene in which at least one hydrogen has been replaced by fluorine, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, pyridine-2,5-diyl or pyrimidine-2,5-diyl, when A.sup.2 is formula (A-2), b and d is 0, and a is 1.

2. The compound according to claim 1, wherein the compound is represented by formula (1-1): ##STR00325## in formula (1-1), R.sup.1 and R.sup.2 are independently hydrogen, fluorine, chlorine or alkyl having 1 to 10 carbons, and in the alkyl at least one CH.sub.2 may be replaced by O, at least one CH.sub.2CH.sub.2 may be replaced by CHCH, and in these groups at least one hydrogen may be replaced by fluorine; ring A.sup.1 and ring A.sup.3 are independently 1,4-cyclohexylene, 1,4-phenylene, 1,4-phenylene in which at least one hydrogen has been replaced by fluorine or tetrahydropyran-2,5-diyl, and ring A.sup.4 is tetrahydropyran-2,5-diyl; Z.sup.1, Z.sup.2, Z.sup.3 and Z.sup.4 are independently a single bond, COO, OCO, OCH.sub.2, CH.sub.2O, CF.sub.2O, OCF.sub.2, CH.sub.2CH.sub.2, CHCH, CC, CF.sub.2CF.sub.2 or CFCF; and a and b are independently 0, 1 or 2, c is 0 or 1, and the sum of a, b and c is 1 or 2.

3. The compound according to claim 1, wherein the compound is represented by formula (1-1-1), formula (1-1-2) or formula (1-1-3): ##STR00326## in formula (1-1-1), formula (1-1-2) and formula (1-1-3), R.sup.1 and R.sup.2 are independently alkyl having 1 to 10 carbons, alkoxy having 1 to 9 carbons, alkenyl having 2 to 10 carbons or alkenyloxy having 2 to 9 carbons; ring A.sup.1 and ring A.sup.3 are independently 1,4-cyclohexylene, 1,4-phenylene, 1,4-phenylene in which at least one hydrogen has been replaced by fluorine or tetrahydropyran-2,5-diyl, and ring A.sup.4 is tetrahydropyran-2,5-diyl; and Z.sup.1, Z.sup.2, Z.sup.3 and Z.sup.4 are independently a single bond, COO, OCO, OCH.sub.2, CH.sub.2O, CF.sub.2O, OCF.sub.2, CH.sub.2CH.sub.2 or CHCH.

4. The compound according to claim 1, wherein the compound is represented by any one of formula (1-1-1a) to formula (1-1-1g), formula (1-1-2a) to formula (1-1-2g), formula (1-1-3a) and formula (1-1-3b): ##STR00327## ##STR00328## in formula (1-1-1a) to formula (1-1-1g), formula (1-1-2a) to formula (1-1-2g), formula (1-1-3a) and formula (1-1-3b), R.sup.1 and R.sup.2 are independently alkyl having 1 to 10 carbons, alkoxy having 1 to 9 carbons, alkenyl having 2 to 10 carbons or alkenyloxy having 2 to 9 carbons.

5. The compound according to claim 4, wherein in formula (1-1-1a), formula (1-1-2b) and formula (1-1-2g), R.sup.1 and R.sup.2 are independently alkyl having 1 to 5 carbons or alkoxy having 1 to 4 carbons.

6. The compound according to claim 1, wherein the compound is represented by formula (1-2): ##STR00329## in formula (1-2), R.sup.1 and R.sup.2 are independently hydrogen, fluorine, chlorine or alkyl having 1 to 10 carbons, and in the alkyl at least one CH.sub.2 may be replaced by O, and in these groups at least one hydrogen may be replaced by fluorine; ring A.sup.1 is 1,4-phenylene, 2-fluoro-1,4-phenylene or tetrahydropyran-2,5-diyl, ring A.sup.3 is 1,4-cyclohexylene, 2-fluoro-1,4-phenylene, 2,3-difluoro-1,4-phenylene or tetrahydropyran-2,5-diyl, and ring A.sup.5 is 1,4-cyclohexylene or tetrahydropyran-2,5-diyl; Z.sup.1, Z.sup.2, Z.sup.3 and Z.sup.5 are independently a single bond, COO, OCO, OCH.sub.2, CH.sub.2O, CF.sub.2O, OCF.sub.2, CHCH, CC, CF.sub.2CF.sub.2 or CFCF; and a and b are independently 0, 1 or 2, d is 0 or 1, and the sum of a, b and d is 1 or 2.

7. The compound according to claim 1, wherein the compound is represented by formula (1-2-1), formula (1-2-2) or formula (1-2-3): ##STR00330## in formula (1-2-1), formula (1-2-2) and formula (1-2-3), R.sup.1 and R.sup.2 are independently alkyl having 1 to 10 carbons, alkoxy having 1 to 9 carbons; ring A.sup.1 is 1,4-phenylene, 2-fluoro-1,4-phenylene or tetrahydropyran-2,5-diyl, ring A.sup.3 is 1,4-cyclohexylene, 2-fluoro-1,4-phenylene, 2,3-difluoro-1,4-phenylene or tetrahydropyran-2,5-diyl, and ring A.sup.5 is 1,4-cyclohexylene or tetrahydropyran-2,5-diyl; and Z.sup.2 and Z.sup.5 are independently a single bond, COO, OCO, OCH.sub.2, CH.sub.2O, CF.sub.2O, OCF.sub.2 or CHCH.

8. The compound according to claim 1, wherein the compound is represented by any one of formula (1-2-1a) to formula (1-2-1e), formula (1-2-2a) to formula (1-2-2f) and formula (1-2-3a) to formula (1-1-3c): ##STR00331## ##STR00332## in formula (1-2-1a) to formula (1-2-1e), formula (1-2-2a) to formula (1-2-2f) and formula (1-2-3a) to formula (1-1-3c), R.sup.1 and R.sup.2 are independently alkyl having 1 to 10 carbons, alkoxy having 1 to 9 carbons; and Z.sup.2 and Z.sup.5 are independently a single bond or CH.sub.2O.

9. The compound according to claim 8, wherein in formula (1-2-3a), R.sup.1 and R.sup.2 are independently alkyl having 1 to 5 carbons or alkoxy having 1 to 4 carbons.

10. A liquid crystal composition including at least one compound according to claim 1.

11. The liquid crystal composition according to claim 10, further including at least one compound selected from the group of compounds represented by formulas (2) to (4): ##STR00333## in formulas (2) to (4), R.sup.11 and R.sup.12 are independently alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in the alkyl and alkenyl at least one CH.sub.2 may be replaced by O, and in these groups at least one hydrogen may be replaced by fluorine; ring B.sup.1, ring B.sup.2, ring B.sup.3 and ring B.sup.4 are independently 1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene, 2,5-difluoro-1,4-phenylene or pyrimidine-2,5-diyl; and Z.sup.11, Z.sup.12 and Z.sup.13 are independently a single bond, COO, CH.sub.2CH.sub.2, CHCH or CC.

12. The liquid crystal composition according to claim 11, further including at least one compound selected from the group of compounds represented by formulas (5) to (11): ##STR00334## in formulas (5) to (11), R.sup.13, R.sup.14 and R.sup.15 are independently alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in the alkyl and alkenyl at least one CH.sub.2 may be replaced by O, and in these groups at least one hydrogen may be replaced by fluorine, and R.sup.15 may be hydrogen or fluorine; ring C.sup.1, ring C.sup.2, ring C.sup.3 and ring C.sup.4 are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, 1,4-phenylene in which at least one hydrogen has been replaced by fluorine, tetrahydropyran-2,5-diyl or decahydronaphthalene-2,6-diyl; ring C.sup.5 and ring C.sup.6 are independently 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, tetrahydropyran-2,5-diyl or decahydronaphthalene-2,6-diyl; Z.sup.14, Z.sup.15, Z.sup.16 and Z.sup.17 are independently a single bond, COO, CH.sub.2O, OCF.sub.2, CH.sub.2CH.sub.2 or OCF.sub.2CH.sub.2CH.sub.2; L.sup.11 and L.sup.12 are independently fluorine or chlorine; S.sup.11 is hydrogen or methyl; X is CHF or CF.sub.2; and j, k, m, n, p, q, r and s are independently 0 or 1, the sum of k, m, n and p is 1 or 2, the sum of q, r and s is 0, 1, 2 or 3, and t is 1, 2 or 3.

13. The liquid crystal composition according to claim 11, further including at least one compound selected from the group of compounds represented by formulas (12) to (14): ##STR00335## in formulas (12) to (14), R.sup.16 is alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in the alkyl and alkenyl at least one CH.sub.2 may be replaced by O, and in these groups at least one hydrogen may be replaced by fluorine; X.sup.11 is fluorine, chlorine, CF.sub.3, CHF.sub.2, CH.sub.2F, OCF.sub.3, OCHF.sub.2, OCF.sub.2CHF.sub.2 or OCF.sub.2CHFCF.sub.3; ring D.sup.1, ring D.sup.2 and ring D.sup.3 are independently 1,4-cyclohexylene, 1,4-phenylene, 1,4-phenylene in which at least one hydrogen has been replaced by fluorine, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl or pyrimidine-2,5-diyl; Z.sup.18, Z.sup.19 and Z.sup.20 are independently a single bond, COO, CH.sub.2O, CF.sub.2O, OCF.sub.2, CH.sub.2CH.sub.2, CHCH, CC or (CH.sub.2).sub.4; and L.sup.13 and L.sup.14 are independently hydrogen or fluorine.

14. The liquid crystal composition according to claim 11, further including at least one compound selected from the group of compounds represented by formula (15): ##STR00336## in formula (15), R.sup.17 is alkyl having 1 to 10 carbons or alkenyl having 2 to 10 carbons, and in the alkyl and alkenyl at least one CH.sub.2 may be replaced by O, and in these groups at least one hydrogen may be replaced by fluorine; X.sup.12 is CN or CCCN; ring E.sup.1 is 1,4-cyclohexylene, 1,4-phenylene, 1,4-phenylene in which at least one hydrogen has been replaced by fluorine, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl or pyrimidine-2,5-diyl; Z.sup.21 is a single bond, COO, CH.sub.2O, CF.sub.2O, OCF.sub.2, CH.sub.2CH.sub.2 or CC; L.sup.15 and L.sup.16 are independently hydrogen or fluorine; and i is 1, 2, 3 or 4.

15. A liquid crystal display device containing the liquid crystal composition according to claim 10.

Description

EXAMPLES

1. Examples of Compound (1)

[0146] The invention will be explained in more detail by way of Examples. Examples are typical cases, and thus the invention is not limited by Examples. Compound (1) was prepared according to the procedures described below. Compounds prepared herein were identified by methods such as NMR analysis. The physical properties of compounds or compositions and the characteristics of devices were measured by the methods described below.

[0147] NMR Analysis:

[0148] A model DRX-500 apparatus made by Bruker BioSpin Corporation was used for measurement. In the measurement of .sup.1H-NMR, a sample was dissolved in a deuterated solvent such as CDCl.sub.3, and measured under the conditions of room temperature, 500 MHz and 16 scan accumulation. Tetramethylsilane was used as an internal standard. In the measurement of .sup.19F-NMR, CFCl.sub.3 was used as an internal standard, and 24 scans were accumulated. In the explanation of the nuclear magnetic resonance spectra, the symbols s, d, t, q, quin, sex, m and br stand for a singlet, a doublet, a triplet, a quartet, a quintet, a sextet, a multiplet and line-broadening, respectively.

[0149] Gas Chromatographic Analysis:

[0150] A gas chromatograph Model GC-2010 made by Shimadzu Corporation was used for measurement. The column used was a capillary column DB-1 (length 60 meters, bore 0.25 millimeters, film thickness 0.25 micrometers) made by Agilent Technologies, Inc. The carrier gas was helium (1 mL per minute). The sample injector and the detector (FID) were set to 300 C. A sample was dissolved in acetone to give a 0.1% solution by weight, and 1 microliter of the solution was injected into the sample injector. A recorder used was Model GC Solution System made by Shimadzu Corporation or the like.

[0151] HPLC Analysis:

[0152] Model Prominence (LC-20AD; SPD-20A) made by Shimadzu Corporation was used for measurement. A column YMC-Pack ODS-A (length 150 millimeters, bore 4.6 millimeters, particle size 5 micrometers) made by YMC Co., Ltd. was used. Acetonitrile and water were properly mixed and used as eluent. A detector such as a UV detector, a RI detector or a Corona detector was properly used. The measurement wavelength was 254 nanometers when the UV detector was used. A sample was dissolved in acetonitrile to give a 0.1% by weight solution, and then 1 microliter of the solution was injected into the sample injector. Model C-R7Aplus made by Shimadzu Corporation was used as a recorder.

[0153] Ultraviolet and Visible Spectrophotometric Analysis:

[0154] Model PharmaSpec UV-1700 made by Shimadzu Corporation was used for measurement. Wavelengths in the range of 190 nm to 700 nm were used for the detection. A sample was dissolved in acetonitrile, giving a 0.01 mmol/L solution, which was placed in a quartz cell (optical path length: 1 cm) and measured.

[0155] Sample for Measurement:

[0156] A compound itself was used as a sample when the phase structure and the transition temperature (a clearing point, a melting point, a starting temperature of polymerization or the like) were measured. A mixture of the compound and mother liquid crystals was used as a sample when physical properties such as the maximum temperature of a nematic phase, viscosity, optical anisotropy and dielectric anisotropy were measured.

[0157] Extrapolation Method:

[0158] When a mixture of a compound and mother liquid crystals was used as a sample, measurement was carried out in the following manner. The sample was prepared by mixing 15% by weight of the compound and 85% by weight of the mother liquid crystals. An extrapolated value was calculated from the measured value of the sample, according to the following equation, and the value was reported: [Extrapolated value]=(100[Measured value of sample][% by weight of mother liquid crystals][Measured value of mother liquid crystals])/[% by weight of compound].

[0159] When crystals (or a smectic phase) deposited at 25 C. at this ratio, the ratio of the compound to the mother liquid crystals was changed in the order of (10% by weight:90% by weight), (5% by weight:95% by weight), and (1% by weight:99% by weight). The physical properties of the sample were measured at the ratio in which the crystals (or the smectic phase) did not deposit at 25 C. Incidentally, the ratio of the compound to the mother liquid crystals is (15% by weight:85% by weight), unless otherwise noted.

[0160] When the dielectric anisotropy of the compound was zero or positive, mother liquid crystals (A) described below was used. The ratio of each component was expressed as a percentage by weight.

##STR00080##

[0161] When the dielectric anisotropy of the compound was zero or negative, mother liquid crystals (B) described below was used. The ratio of each component was expressed as a percentage by weight.

##STR00081##

[0162] Mother Liquid Crystals (C):

[0163] Mother liquid crystals (C) are sometimes used in which the component is the following fluorine compounds.

##STR00082##

[0164] Measurement Method:

[0165] The physical properties were measured according to the following methods. Most of them are described in the JEITA standards (JEITA-ED-2521B) which was deliberated and established by Japan Electronics and Information Technology Industries Association (abbreviated to JEITA). A modified method was also used. No TFT was attached to a TN device used for measurement.

(1) Phase Structure: A sample was placed on a hot plate of a melting point apparatus (Hot Stage Model FP-52 made by Mettler Toledo International Inc.) equipped with a polarizing microscope, and the phase conditions and their changes were observed with the polarizing microscope while the sample was heated at the rate of 3 C. per minute, and the type of phase was specified.
(2) Transition Temperature ( C.): A differential scanning calorimeter, a Diamond DSC System made by PerkinElmer Inc. or a X-DSC7000 high sensitivity differential scanning analyzer made by SII NanoTechnology Inc. was used for measurement. A sample was heated and then cooled at the rate of 3 C. per minute, and the starting point of an endothermic peak or an exothermic peak caused by the phase change of the sample was obtained by extrapolation, and thus the transition temperature was determined. The melting point and the starting temperature of polymerization of a compound were also measured with this apparatus. The transition temperature of a compound from solid to a liquid crystal phase such as a smectic phase or a nematic phase is sometimes abbreviated to the minimum temperature of a liquid crystal phase. The transition temperature of a compound from a liquid crystal phase to liquid is sometimes abbreviated to clearing point.

[0166] The symbol C stood for crystals. When two types of crystals can be distinguished, each was expressed as C.sub.1 or C.sub.2. The symbols S and N stood for a smectic phase and a nematic phase, respectively. When phases such as a smectic A phase, a smectic B phase, a smectic C phase and a smectic F can be distinguished, they were expressed as S.sub.A, S.sub.B, S.sub.C and S.sub.F, respectively. The symbol I stood for a liquid (isotropic). Transition temperatures were expressed as, for example, C, 50.0; N, 100.0; Iso, which means that the transition temperature from crystals to a nematic phase was 50.0 C., and the transition temperature from the nematic phase to a liquid was 100.0 C.

(3) Compatibility of Compounds: Samples were prepared by mixing a compound with mother liquid crystals so that the ratio of the compound became 20% by weight, 15% by weight, 10% by weight, 5% by weight, 3% by weight or 1% by weight. The samples were placed in glass vials, and kept in a freezer at a temperature of 10 C. and -20 C. for a certain period of time. They were observed to determine whether or not the nematic phase was maintained or whether or not crystals (or a smectic phase) were deposited. The conditions that the nematic phase was maintained were used as a measure of the compatibility. The ratio of the compound or the temperature in the freezer may be changed, as requested.
(4) Maximum Temperature of a Nematic Phase (T.sub.NI or NI; C.): A sample was placed on a hot plate in a melting point apparatus equipped with a polarizing microscope and was heated at the rate of 1 C. per minute. The temperature was measured when part of the sample began to change from a nematic phase to an isotropic liquid. The symbol T.sub.NI means that the sample was a mixture of compound (1) and mother liquid crystals. This value was calculated using the extrapolation method described above. The symbol NI means that the sample was a mixture of a compound (1) and compounds selected from compounds (2) to (15). The maximum temperature of a nematic phase is sometimes abbreviated to maximum temperature.
(5) Minimum Temperature of a Nematic Phase (T.sub.C; C.): A sample having a nematic phase was placed in a glass vials and kept in freezers at temperatures of 0 C., 10 C., 20 C., 30 C. and -40 C. for 10 days, and then the liquid crystal phases were observed. For example, when the sample maintained the nematic phase at 20 C. and changed to crystals or a smectic phase at 30 C., T.sub.C was expressed as <20 C. A lower limit of the temperature range of a nematic phase is sometimes abbreviated to minimum temperature.
(6) Viscosity (bulk viscosity; q; measured at 20 C.; mPa.Math.s): An E-type viscometer made by Tokyo Keiki Inc. was used for measurement.
(7) Optical Anisotropy (Refractive Index Anisotropy; n; measured at 25 C.): Measurement was carried out using an Abbe refractometer with a polarizing plate attached to the ocular, using light at a wavelength of 589 nanometers. The surface of the main prism was rubbed in one direction, and then a sample was placed on the main prism. The refractive index (n) was measured when the direction of the polarized light was parallel to that of the rubbing. The refractive index (n) was measured when the direction of polarized light was perpendicular to that of the rubbing. The value of the optical anisotropy (n) was calculated from the equation: n=nn.
(8) Specific Resistance (; measured at 25 C.; cm): A sample of 1.0 mL was poured into a vessel equipped with electrodes. A DC voltage (10 V) was applied to the vessel, and the DC current was measured after 10 seconds. The specific resistance was calculated from the following equation: (specific resistance)=[(voltage)(electric capacity of vessel)]/[(DC current)(dielectric constant in vacuum)].
(9) Voltage Holding Ratio (VHR-1; measured at 25 C.; %): A TN device used for measurement had a polyimide-alignment film, and the distance between the two glass substrates (cell gap) was 5 micrometers. A sample was poured into the device, and then the device was sealed with a UV-curable adhesive. A pulse voltage (60 microseconds at 5 V) was applied to the device and the device was charged. A decreasing voltage was measured for 16.7 milliseconds with a high-speed voltmeter, and area A between a voltage curve and a horizontal axis in a unit cycle was obtained. Area B was an area without the decrease. The voltage holding ratio was a percentage of area A to area B.
(10) Voltage Holding Ratio (VHR-2; measured at 80 C.; %): The voltage holding ratio was measured by the method described above, except that it was measured at 80 C. instead of 25 C. The resulting value was represented by the symbol VHR-2.
(11) Flicker Rate (measured at 25 C.; %): A multimedia display tester 3298F made by Yokogawa Electric Corporation was used for measurement. The light source was LED. A sample was poured into an FFS device having a normally black mode, in which the distance between the two glass substrates (cell gap) was 3.5 micrometers and the rubbing direction was antiparallel. This device was sealed with a UV-curable adhesive. A voltage was applied to the device and a voltage was measured when the amount of light passed through the device reached a maximum. The sensor was brought close to the device while this voltage was applied to the device, and the flicker rate displayed was recorded.
(12) Viscosity (Rotational Viscosity; 1; measured at 25 C.; mPa.Math.s): The measurement was carried out according to the method described in M. Imai, et al., Molecular Crystals and Liquid Crystals, Vol. 259, p. 37 (1995). A sample was poured into a VA device in which the distance between the two glass substrates (cell gap) was 20 micrometers. A voltage was applied to the device and increased from 39 V to 50 V in increments of 1 V. After a period of 0.2 seconds with no voltage, a voltage was applied repeatedly under the conditions of only one rectangular wave (rectangular pulse; 0.2 seconds) and no voltage (2 seconds). The peak current and the peak time of the transient current generated by the applied voltage were measured. The value of rotational viscosity was obtained from these measured values and equation (8) on page 40 of the paper presented by M. Imai, et al. The value of the dielectric anisotropy necessary for the present calculation was obtained by the method that will be described below, under the heading Dielectric anisotropy.
(13) Dielectric Anisotropy (; measured at 25 C.): The value of dielectric anisotropy was calculated from the equation: =. Dielectric constants ( and ) were measured as follows.
1) Measurement of a dielectric constant (): A solution of octadecyltriethoxysilane (0.16 mL) in ethanol (20 mL) was applied to thoroughly cleaned glass substrates. The glass substrates were rotated with a spinner, and then heated at 150 C. for one hour. A sample was poured into a VA device in which the distance between the two glass substrates (cell gap) was 4 micrometers, and then this device was sealed with a UV-curable adhesive. Sine waves (0.5 V, 1 kHz) were applied to this device, and the dielectric constant () in the major axis direction of liquid crystal molecules was measured after 2 seconds.
2) Measurement of a dielectric constant (): A polyimide solution was applied to thoroughly cleaned glass substrates. The glass substrates were calcined, and then the resulting alignment film was subjected to rubbing. A sample was poured into a TN device in which the distance between the two glass substrates (cell gap) was 9 micrometers and the twist angle was 80 degrees. Sine waves (0.5 V, 1 kHz) were applied to this device, and the dielectric constant () in the minor axis direction of liquid crystal molecules was measured after 2 seconds.
(14) Elastic Constants (K.sub.11 and K.sub.33; measured at 25 C.; pN): An elastic constant measurement system Model EC-1 made by Toyo Corporation was used for measurement. A sample was poured into a homeotropic device in which the distance between the two glass substrates (cell gap) was 20 micrometers. An electric charge of 20 V to 0 V was applied to this device, and electrostatic capacity and applied voltage were measured. The values of the electrostatic capacity (C) and the applied voltage (V) were fitted to equation (2.98) and equation (2.101) on page 75 of the Ekisho Debaisu Handobukku (Liquid Crystal Device Handbook, in English; The Nikkan Kogyo Shimbun, Ltd., Japan), and the value of the elastic constant was obtained from equation (2.100).
(15) Threshold Voltage (Vth; measured at 25 C.; V): The measurement was carried out with an LCD evaluation system Model LCD-5100 made by Otsuka Electronics Co., Ltd. The light source was a halogen lamp. A sample was poured into a VA device having a normally black mode, in which the distance between the two glass substrates (cell gap) was 4 micrometers and the rubbing direction was antiparallel, and then this device was sealed with a UV-curable adhesive. The voltage to be applied to this device (60 Hz, rectangular waves) was stepwise increased in 0.02 V increments from 0 V up to 20 V. The device was simultaneously irradiated with light in the perpendicular direction, and the amount of light passing through the device was measured. A voltage-transmittance curve was prepared, in which the maximum amount of light corresponded to 100% transmittance and the minimum amount of light corresponded to 0% transmittance. The threshold voltage was voltage at 10% transmittance.
(16) Response Time (; measured at 25 C.; millisecond): The measurement was carried out with an LCD evaluation system Model LCD-5100 made by Otsuka Electronics Co., Ltd. The light source was a halogen lamp. The low-pass filter was set at 5 kHz. A sample was poured into a PVA device having a normally black mode, in which the distance between the two glass substrates (cell gap) was 3.2 micrometers, and the rubbing direction was antiparallel. This device was sealed with a UV-curable adhesive. A voltage that was a little more than the threshold voltage was applied to this device for 1 minute, and then the device was irradiated with ultraviolet light of 23.5 mW/cm.sup.2 for 8 minutes while a voltage of 5.6 V was applied. Rectangular waves (60 Hz, 10 V, 0.5 seconds) were applied to this device. The device was simultaneously irradiated with light in the perpendicular direction, and the amount of light passing through the device was measured. The transmittance was regarded as 100% when the amount of light reached a maximum. The transmittance was regarded as 0% when the amount of light reached a minimum. The response time was expressed as the period of time required for the change from 90% to 10% transmittance (fall time: millisecond).

Synthetic Example 1

Preparation of Compound (No. 139)

[0167] ##STR00083##

First Step:

[0168] Compound (e-1) (made by Organoscience Co., Ltd.) (10.5 g, 27.7 mmol) and ethanedithiol (5.3 g, 56.3 mmol) were added to toluene (50 ml) under an atmosphere of nitrogen. Boron trifluoride-acetic acid complex (5.3 g, 28.1 mmol) was added dropwise at 30 C., and the mixture was stirred overnight at room temperature. An aqueous solution (10%; 45 g) of sodium hydroxide was added to adjust the pH to 12. The mixture was extracted with toluene (50 ml), the extract was washed with brine, and dried over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure to give compound (e-2) (10.8 g, 23.8 mmol).

Second Step:

[0169] Compound (e-2) (10.8 g, 23.8 mmol) and dichloromethane (140 ml) were placed in a reaction vessel under an atmosphere of nitrogen, and cooled to 15 C. (Diethylamino) sulfur trifluoride (DAST) (77.0 g, 477.7 mmol) was added dropwise in the temperature range of 15 C. to 10 C. After the addition, the reaction mixture was returned to 25 C., and stirred for 48 hours. The reaction mixture was added dropwise to an aqueous solution of sodium carbonate to which ice was added, and the resulting precipitates were filtered. The organic layer of the filtrate was washed successively with an aqueous solution (10%) of sodium hydroxide, dilute hydrochloric acid, a saturated aqueous solution of sodium hydrogencarbonate and brine, and dried over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (heptane). Recrystallization from Solmix A-11 gave compound (No. 139) (2.7 g, 6.7 mmol). Solmix (registered trademark) A-11 was a mixture of ethanol (85.5%), methanol (13.4%) and isopropanol (1.1%), and was available from Japan Alcohol Trading Co., Ltd.

[0170] .sup.1H-NMR ( ppm; CDCl.sub.3): 6.83 (m, 1H), 6.66 (m, 1H), 4.08 (q, 2H), 2.73 (m, 1H), 2.10 (m, 1H), 1.99-1.75 (m, 7H), 1.53-1.19 (m, 16H), 0.89 (t, 3H).

[0171] The physical properties of compound (No. 139) were as follows. Transition temperature: C, 78.6; N, 162.1; I. T.sub.NI=128.3 C.; =62.7 mPa.Math.s: n=0.114; =3.7.

Synthetic Example 2

Preparation of Compound (No. 140)

[0172] ##STR00084##

[0173] In Synthetic example 1, a similar reaction using compound (e-3) (made by Organoscience Co., Ltd.) (9.7 g, 27.8 mmol) instead of compound (e-1) gave compound (No. 140) (4.5 g, 12.1 mmol).

[0174] .sup.1H-NMR ( ppm; CDCl.sub.3): 6.84 (m, 2H), 2.78 (m, 1H), 2.25 (s, 3H), 2.11 (m, 1H), 1.99-1.76 (m, 7H), 1.58-1.20 (m, 13H), 0.89 (t, 3H).

[0175] The physical properties of compound (No. 140) were as follows. Transition temperature: C, 94.2; N, 120.0; I. T.sub.NI=95.0 C.; =45.0 mPa.Math.s: n=0.100; =1.8.

Comparative Example 1

Comparison of Physical Properties

[0176] Compound (C-1) was prepared as a comparative compound. This was because this compound was described in Example 24 of DE 3906058 A1, and was similar to the compound of the invention.

##STR00085##

[0177] .sup.1H-NMR ( ppm; CDCl.sub.3): 6.85-6.81 (m, 1H), 6.68-6.64 (m, 1H), 4.08 (q, 2H), 2.85-2.69 (m, 1H), 1.88-1.71 (m, 8H), 1.44-0.96 (m, 16H), 0.89-0.82 (m, 5H).

[0178] The physical properties of comparative compound (C-1) were as follows. Transition temperature: C, 66.9; S.sub.B; 79.9; N, 185.1; I. T.sub.NI=159.9 C.; =41.0 mPa.Math.s: n=0.112; =5.32.

Compatibility of Compounds

[0179] The compatibility of compound (No. 139) obtained in Synthetic example 1 and comparative compound (C-1) was measured and the results were summarized in Table 2. The compatibility of compounds was measured according to the method described above. A sample was dissolved in mother liquid crystals (B), and kept at 10 C. for 30 days. Compound (No. 139) maintained a nematic phase at 15%, however, comparative compound (C-1) deposited its solids. This compound maintained a nematic phase when the concentration was 3%. It was found from these results that compound (No. 139) was superior in terms of the compatibility.

TABLE-US-00002 TABLE 2 Physical properties of compound (No. 139) and comparative compound (C-1) Compound (No. 139) Comparative compound (C-1) Structure [00086] [00087] Compatibility of the 15% (10 C.) 3% (10 C.) compound

Comparative Example 2

Comparison of Physical Properties

[0180] Compound (C-2) was prepared as a comparative compound. This was because this compound was compound (CCP-31FF) described in Example 7 of JP H08-048978 (1996), and was similar to the compound of the invention.

##STR00088##

[0181] .sup.1H-NMR ( ppm; CDCl.sub.3): 6.86-6.81 (m, 2H), 2.80-2.74 (m, 1H), 2.25 (d, 3H), 1.88-1.82 (m, 4H), 1.77-1.71 (m, 4H), 1.46-1.39 (m, 2H), 1.34-1.26 (m, 2H), 1.20-0.93 (m, 9H), 0.87-0.82 (m, 5H).

[0182] The physical properties of comparative compound (C-2) were as follows. Transition temperature: C, 67.1; N, 146.4; I. T.sub.NI=123.0 C.; =27.4 mPa.Math.s: n=0.107; =2.9.

[0183] The compatibility of compound (No. 140) obtained in Synthetic example 2 and comparative compound (C-2) was measured in the same manner as Comparative example 1, and the results were summarized in Table 3. It was found from Table 3 that compound (No. 140) was superior in terms of the compatibility.

TABLE-US-00003 TABLE 3 Physical properties of compound (No. 140) and comparative compound (C-2) Compound (No. 140) Comparative compound (C-2) Structure [00089] [00090] Compatibility of the 10% (10 C.) 3% (10 C.) compound

[0184] Compound (1) is prepared according to 2. Preparation of compound (1) and Synthetic examples, these of which were described above. Examples of this type of compounds include compounds (No. 1) to (No. 216) described below.

TABLE-US-00004 No. 1 [00091] 2 [00092] 3 [00093] 4 [00094] 5 [00095] 6 [00096] 7 [00097] 8 [00098] 9 [00099] 10 [00100] 11 [00101] 12 [00102] 13 [00103] 14 [00104] 15 [00105] 16 [00106] 17 [00107] 18 [00108] 19 [00109] 20 [00110] 21 [00111] 22 [00112] 23 [00113] 24 [00114] 25 [00115] 26 [00116] 27 [00117] 28 [00118] 29 [00119] 30 [00120] 31 [00121] 32 [00122] 33 [00123] 34 [00124] 35 [00125] 36 [00126] 37 [00127] 38 [00128] 39 [00129] 40 [00130] 41 [00131] 42 [00132] 43 [00133] 44 [00134] 45 [00135] 46 [00136] 47 [00137] 48 [00138] 49 [00139] 50 [00140] 51 [00141] 52 [00142] 53 [00143] 54 [00144] 55 [00145] 56 [00146] 57 [00147] 58 [00148] 59 [00149] 60 [00150] 61 [00151] 62 [00152] 63 [00153] 64 [00154] 65 [00155] 66 [00156] 67 [00157] 68 [00158] 69 [00159] 70 [00160] 71 [00161] 72 [00162] 73 [00163] 74 [00164] 75 [00165] 76 [00166] 77 [00167] 78 [00168] 79 [00169] 80 [00170] 81 [00171] 82 [00172] 83 [00173] 84 [00174] 85 [00175] 86 [00176] 87 [00177] 88 [00178] 89 [00179] 90 [00180] 91 [00181] 92 [00182] 93 [00183] 94 [00184] 95 [00185] 96 [00186] 97 [00187] 98 [00188] 99 [00189] 100 [00190] 101 [00191] 102 [00192] 103 [00193] 104 [00194] 105 [00195] 106 [00196] 107 [00197] 108 [00198] 109 [00199] 110 [00200] 111 [00201] 112 [00202] 113 [00203] 114 [00204] 115 [00205] 116 [00206] 117 [00207] 118 [00208] 119 [00209] 120 [00210] 121 [00211] 122 [00212] 123 [00213] 124 [00214] 125 [00215] 126 [00216] 127 [00217] 128 [00218] 129 [00219] 130 [00220] 131 [00221] 132 [00222] 133 [00223] 134 [00224] 135 [00225] 136 [00226] 137 [00227] 138 [00228] 139 [00229] C 78.6 N 162.1 I NI = 128.3 C., = 3.7, n = 0.114, = 62.7 mPa .Math. m 140 [00230] C 94.2 N 120.0 I NI = 95.0 C., = 1.8, n = 0.100, = 45.0 mPa .Math. m 141 [00231] 142 [00232] 143 [00233] 144 [00234] 145 [00235] 146 [00236] 147 [00237] 148 [00238] 149 [00239] 150 [00240] 151 [00241] 152 [00242] 153 [00243] 154 [00244] 155 [00245] 156 [00246] 157 [00247] 158 [00248] 159 [00249] 160 [00250] 161 [00251] 162 [00252] 163 [00253] 164 [00254] 165 [00255] 166 [00256] 167 [00257] 168 [00258] 169 [00259] 170 [00260] 171 [00261] 172 [00262] 173 [00263] 174 [00264] 175 [00265] 176 [00266] 177 [00267] 178 [00268] 179 [00269] 180 [00270] 181 [00271] 182 [00272] 183 [00273] 184 [00274] 185 [00275] 186 [00276] 187 [00277] 188 [00278] 189 [00279] 190 [00280] 191 [00281] 192 [00282] 193 [00283] 194 [00284] 195 [00285] 196 [00286] 197 [00287] 198 [00288] 199 [00289] 200 [00290] 201 [00291] 202 [00292] 203 [00293] 204 [00294] 205 [00295] 206 [00296] 207 [00297] 208 [00298] 209 [00299] 210 [00300] 211 [00301] 212 [00302] 213 [00303] 214 [00304] 215 [00305] 216 [00306]

2. Examples of the Compositions

[0185] The invention will be explained in more detail by way of examples. The invention is not limited by the examples, since they are typical examples. For example, the invention includes a mixture of the composition in Use example 1 and the composition in Use example 2, in addition to the composition in Use example. The invention also includes a mixture prepared by mixing at least two of the compositions in Use examples. The compounds described in Use Examples were expressed in terms of symbols based on the definition in Table 4 described below. In Table 4, the configuration of 1,4-cyclohexylene is trans. A parenthesized number next to a symbolized compound in Use Example represents the chemical formula to which the compound belongs. The symbol () means a liquid crystal compound that is different from compounds (1) to (15). The ratio (percentage) of a liquid crystal compound means the percentages by weight (% by weight) based on the weight of the liquid crystal composition excluding additives. Last, the physical property-values of the composition are summarized. Physical properties were measured according to the method described above, and the measured value was reported as it was (without extrapolation).

TABLE-US-00005 TABLE 4 Method of Description of Compounds using Symbols R(A1)Zr. . .Zn(An)R 1) Left-terminal Group R Symbol FC.sub.nH.sub.2n Fn C.sub.nH.sub.2n+1 n C.sub.nH.sub.2n+1O nO C.sub.mH.sub.2m+1OC.sub.nH.sub.2n mOn CH.sub.2CH V C.sub.nH.sub.2n+1CHCH nV CH.sub.2CHC.sub.nH.sub.2n Vn C.sub.mH.sub.2m+1CHCHC.sub.nH.sub.2n mVn CF.sub.2CH VFF CF.sub.2CHC.sub.nH.sub.2n VFFn 2) Right-terminal Group R Symbol C.sub.nH.sub.2n+1 n OC.sub.nH.sub.2n+1 On COOCH.sub.3 EMe CHCH.sub.2 V CHCHC.sub.nH.sub.2n+1 Vn C.sub.nH.sub.2nCHCH.sub.2 nV C.sub.mH.sub.2mCHCHC.sub.nH.sub.2n+1 mVn CHCF.sub.2 VFF F F Cl CL OCF.sub.3 OCF3 OCF.sub.2H OCF2H CF.sub.3 CF3 OCF.sub.2CFCFCF.sub.3 OCF2FVFCF3 CN C 3) Bonding Group Z.sub.n Symbol C.sub.nH.sub.2n n COO E CHCH V CH.sub.2O 1O OCH.sub.2 O1 CF.sub.2O X CC T 4) Ring Structure A.sub.n Symbol [00307] H [00308] B [00309] B(F) [00310] B(2F) [00311] B(F,F) [00312] B(2F,5F) [00313] B(2F,3F) [00314] G [00315] dh [00316] Dh [00317] Cro(7F,8F) [00318] B(2F,3CL) [00319] H(3F2) [00320] H(2F2) 5) Examples of Description Example 1. 3H(3F2)HB(2F,3F)1 [00321] Example 2. 3HBB(F,F)F [00322]

Use Example 1

[0186]

TABLE-US-00006 3-H(3F2)HB(2F,3F)-1 (No. 140) 5% 2-HB-C (15-1) 5% 3-HB-C (15-1) 12% 3-HB-O2 (2-5) 15% 2-BTB-1 (2-10) 3% 3-HHB-F (13-1) 4% 3-HHB-1 (3-1) 8% 3-HHB-O1 (3-1) 5% 3-HHB-3 (3-1) 14% 3-HHEB-F (13-10) 2% 5-HHEB-F (13-10) 2% 2-HHB(F)-F (13-11) 7% 3-HHB(F)-F (13-11) 6% 5-HHB(F)-F (13-11) 7% 3-HHB(F,F)-F (13-12) 5%

[0187] NI=94.7 C.; =16.6 mPa.Math.s: n=0.098; =4.3.

Use Example 2

[0188]

TABLE-US-00007 3-H(3F2)HB(2F,3F)-O2 (No. 139) 4% 3-HB-CL (12-2) 13% 3-HH-4 (2-1) 10% 3-HB-O2 (2-5) 7% 3-HHB(F,F)-F (13-3) 3% 3-HBB(F,F)-F (13-24) 29% 5-HBB(F,F)-F (13-24) 24% 5-HBB(F)B-2 (4-5) 5% 5-HBB(F)B-3 (4-5) 5%

[0189] NI=73.4 C.; =21.5 mPa.Math.s: n=0.118; =5.3.

Use Example 3

[0190]

TABLE-US-00008 3-HH(2F2)B(2F,3F)-O2 (No. 1) 6% 7-HB(F,F)-F (12-4) 3% 3-HB-O2 (2-5) 7% 2-HHB(F)-F (13-2) 10% 3-HHB(F)-F (13-2) 10% 5-HHB(F)-F (13-2) 10% 2-HBB(F)-F (13-23) 9% 3-HBB(F)-F (13-23) 9% 5-HBB(F)-F (13-23) 10% 2-HBB-F (13-22) 4% 3-HBB-F (13-22) 4% 5-HBB-F (13-22) 3% 3-HBB(F,F)-F (13-24) 5% 5-HBB(F,F)-F (13-24) 10%

Use Example 4

[0191]

TABLE-US-00009 3-H(3F2)HB(2F,3F)-1 (No. 140) 3% 5-HB-CL (12-2) 16% 3-HH-4 (2-1) 12% 3-HH-5 (2-1) 4% 3-HHB-F (13-1) 4% 3-HHB-CL (13-1) 3% 4-HHB-CL (13-1) 4% 3-HHB(F)-F (13-2) 10% 4-HHB(F)-F (13-2) 9% 5-HHB(F)-F (13-2) 9% 7-HHB(F)-F (13-2) 8% 5-HBB(F)-F (13-23) 4% 3-HHBB(F,F)-F (14-6) 2% 4-HHBB(F,F)-F (14-6) 3% 5-HHBB(F,F)-F (14-6) 3% 3-HH2BB(F,F)-F (14-15) 3% 4-HH2BB(F,F)-F (14-15) 3%

[0192] NI=110.2 C.; =18.9 mPa.Math.s: n=0.088; =3.7.

Use Example 5

[0193]

TABLE-US-00010 3-H(3F2)HB(2F,3F)O2 (No. 139) 5% 3-HHB(F,F)F (13-3) 9% 3-H2HB(F,F)F (13-15) 7% 4-H2HB(F,F)F (13-15) 8% 5-H2HB(F,F)F (13-15) 7% 3-HBB(F,F)F (13-24) 21% 5-HBB(F,F)F (13-24) 20% 3-H2BB(F,F)F (13-27) 8% 5-HHBB(F,F)F (14-6) 3% 5-HHEBBF (14-17) 2% 3-HH2BB(F,F)F (14-15) 3% 1O1HBBH-4 (4-1) 3% 1O1HBBH-5 (4-1) 4%

[0194] NI=99.2 C.; =36.2 mPa.Math.s: n=0.116; =8.6.

[0195] The helical pitch was 63.8 m, when compound (Op-5) was added to the preceding composition in the ratio of 0.25% by weight.

Use Example 6

[0196]

TABLE-US-00011 3-HH(2F2)B(2F,3F)O2 (No. 1) 5% 5-HBF (12-2) 12% 6-HBF (12-2) 9% 7-HBF (12-2) 7% 2-HHBOCF3 (13-1) 5% 3-HHBOCF3 (13-1) 6% 4-HHBOCF3 (13-1) 7% 5-HHBOCF3 (13-1) 5% 3-HH2BOCF3 (13-4) 3% 5-HH2BOCF3 (13-4) 4% 3-HHB(F,F)OCF2H (13-3) 4% 3-HHB(F,F)OCF3 (13-3) 4% 3-HH2B(F)F (13-5) 3% 3-HBB(F)F (13-23) 10% 5-HBB(F)F (13-23) 10% 5-HBBH-3 (4-1) 3% 3-HB(F)BH-3 (4-2) 3%

Use Example 7

[0197]

TABLE-US-00012 3-H(3F2)HB(2F,3F)-1 (No. 140) 4% 5-HBCL (12-2) 11% 3-HH-4 (2-1) 8% 3-HHB-1 (3-1) 5% 3-HHB(F,F)F (13-3) 8% 3-HBB(F,F)F (13-24) 19% 5-HBB(F,F)F (13-24) 14% 3-HHEB(F,F)F (13-12) 8% 4-HHEB(F,F)F (13-12) 4% 5-HHEB(F,F)F (13-12) 3% 2-HBEB(F,F)F (13-39) 3% 3-HBEB(F,F)F (13-39) 5% 5-HBEB(F,F)F (13-39) 3% 3-HHBB(F,F)F (14-6) 5%
NI=80.0 C.; =22.2 mPa.Math.s: n=0.102; =8.2.

Use Example 8

[0198]

TABLE-US-00013 3-H(3F2)HB(2F,3F)O2 (No. 139) 5% 3-HBCL (12-2) 6% 5-HBCL (12-2) 4% 3-HHBOCF3 (13-1) 5% 3-H2HBOCF3 (13-13) 5% 5-H4HBOCF3 (13-19) 15% VHHB(F)F (13-2) 3% 3-HHB(F)F (13-2) 4% 5-HHB(F)F (13-2) 5% 3-H4HB(F,F)CF3 (13-21) 8% 5-H4HB(F,F)CF3 (13-21) 10% 5-H2HB(F,F)F (13-15) 5% 5-H4HB(F,F)F (13-21) 7% 2-H2BB(F)F (13-26) 5% 3-H2BB(F)F (13-26) 8% 3-HBEB(F,F)F (13-39) 5%

[0199] NI=65.2 C.; =24.0 mPa.Math.s: n=0.092; =7.9.

Use Example 9

[0200]

TABLE-US-00014 3-HH(2F2)B(2F,3F)O2 (No. 1) 5% 5-HBCL (12-2) 16% 7-HB(F,F)F (12-4) 3% 3-HH-4 (2-1) 9% 3-HH-5 (2-1) 5% 3-HBO2 (2-5) 14% 3-HHB-1 (3-1) 8% 3-HHBO1 (3-1) 4% 2-HHB(F)F (13-2) 6% 3-HHB(F)F (13-2) 7% 5-HHB(F)F (13-2) 6% 3-HHB(F,F)F (13-3) 6% 3-H2HB(F,F)F (13-15) 6% 4-H2HB(F,F)F (13-15) 5%

[0201] Use example 10

TABLE-US-00015 3-H(3F2)HB(2F,3F)-1 (No. 140) 5% 5-HBCL (12-2) 3% 7-HB(F)F (12-3) 7% 3-HH-4 (2-1) 9% 3-HH-5 (2-1) 10% 3-HBO2 (2-5) 13% 3-HHEBF (13-10) 8% 5-HHEBF (13-10) 8% 3-HHEB(F,F)F (13-12) 8% 4-HHEB(F,F)F (13-12) 3% 3-GHB(F,F)F (13-109) 5% 4-GHB(F,F)F (13-109) 6% 5-GHB(F,F)F (13-109) 5% 2-HHB(F,F)F (13-3) 5% 3-HHB(F,F)F (13-3) 5%

[0202] NI=71.6 C.; =18.3 mPa.Math.s: n=0.069; =5.2.

Use Example 11

[0203]

TABLE-US-00016 3-H(3F2)HB(2F,3F)O2 (No. 139) 3% 3-HBO1 (2-5) 12% 3-HH-4 (2-1) 5% 3-HBO2 (2-5) 4% 3-HB(2F,3F)O2 (5-1) 12% 5-HB(2F,3F)O2 (5-1) 12% 2-HHB(2F,3F)-1 (6-1) 12% 3-HHB(2F,3F)-1 (6-1) 10% 3-HHB(2F,3F)O2 (6-1) 11% 5-HHB(2F,3F)O2 (6-1) 12% 3-HHB-1 (3-1) 7%

[0204] NI=84.4 C.; =35.6 mPa.Math.s: n=0.087; =3.3.

Use Example 12

[0205]

TABLE-US-00017 3-HH(2F2)B(2F,3F)O2 (No. 1) 7% 2-HH-5 (2-1) 3% 3-HH-4 (2-1) 15% 3-HH-5 (2-1) 3% 3-HBO2 (2-5) 12% 3-H2B(2F,3F)O2 (5-4) 13% 5-H2B(2F,3F)O2 (5-4) 14% 3-HHB(2F,3CL)O2 (6-1) 5% 2-HBB(2F,3F)O2 (6-7) 3% 3-HBB(2F,3F)O2 (6-7) 8% 5-HBB(2F,3F)O2 (6-7) 8% 3-HHB-1 (3-1) 3% 3-HHB-3 (3-1) 3% 3-HHBO1 (3-1) 3%

Use Example 13

[0206]

TABLE-US-00018 3-H(3F2)HB(2F,3F)-1 (No. 140) 6% 2-HH-3 (2-1) 19% 3-HH-4 (2-1) 9% 1-BB-3 (2-8) 8% 3-HBO2 (2-5) 2% 3-BB(2F,3F)O2 (5-3) 8% 5-BB(2F,3F)O2 (5-3) 6% 2-HH1OB(2F,3F)O2 (6-5) 13% 3-HH1OB(2F,3F)O2 (6-5) 19% 3-HHB-1 (3-1) 5% 3-HHBO1 (3-1) 3% 2-BBB(2F)-5 (3-8) 2%

[0207] NI=76.8 C.; =17.0 mPa.Math.s: n=0.097; =3.1.

Use Example 14

[0208]

TABLE-US-00019 3-H(3F2)HB(2F,3F)O2 (No. 139) 5% 2-HH-3 (2-1) 16% 3-HH-4 (2-1) 5% 7-HB-1 (2-5) 5% 5-HBO2 (2-5) 8% 3-HB(2F,3F)O2 (5-1) 17% 5-HB(2F,3F)O2 (5-1) 16% 4-HHB(2F,3CL)O2 (6-1) 3% 3-HH1OCro(7F,8F)-5 (9-6) 5% 5-HBB(F)B-2 (4-5) 10% 5-HBB(F)B-3 (4-5) 10%

[0209] NI=78.3 C.; =22.3 mPa.Math.s: n=0.103; =2.4.

Use Example 15

[0210]

TABLE-US-00020 3-HH(2F2)B(2F,3F)O2 (No. 1) 4% 1-BB-3 (2-8) 10% 3-HHV (2-1) 29% 3-BB(2F,3F)O2 (5-3) 9% 2-HH1OB(2F,3F)O2 (6-5) 20% 3-HH1OB(2F,3F)O2 (6-5) 14% 3-HHB-1 (3-1) 8% 2-BBB(2F)-5 (3-8) 6%

Use Example 16

[0211]

TABLE-US-00021 3-H(3F2)HB(2F,3F)-1 (No. 140) 7% 2-HH-3 (2-1) 6% 3-HHV1 (2-1) 10% 1V2HH-1 (2-1) 8% 1V2HH-3 (2-1) 7% 3-BB(2F,3F)O2 (5-3) 8% 5-BB(2F,3F)O2 (5-3) 4% 2-HH1OB(2F,3F)O2 (6-5) 8% 3-HH1OB(2F,3F)O2 (6-5) 19% 3-HDhB(2F,3F)O2 (6-3) 7% 3-HHB-1 (3-1) 3% 3-HHB-3 (3-1) 2% 2-BB(2F,3F)B-3 (7-1) 11%

[0212] NI=91.0 C.; =22.4 mPa.Math.s: n=0.110; =3.9.

Use Example 17

[0213]

TABLE-US-00022 3-H(3F2)HB(2F,3F)O2 (No. 139) 5% 1V2BEB(F,F)C (15-15) 6% 3-HBC (15-1) 16% 2-BTB-1 (2-10) 10% 5-HHVFF (2-1) 28% 3-HHB-1 (3-1) 4% VFFHHB-1 (3-1) 8% VFF2HHB-1 (3-1) 10% 3-H2BTB-2 (3-17) 5% 3-H2BTB-3 (3-17) 4% 3-H2BTB-4 (3-17) 4%

[0214] NI=84.5 C.; =14.5 mPa.Math.s: n=0.131; =6.2.

Use Example 18

[0215]

TABLE-US-00023 3-HH(2F2)B(2F,3F)O2 (No. 1) 3% 5-HB(F)B(F,F)XB(F,F)F (14-41) 5% 3-BB(F)B(F,F)XB(F,F)F (14-47) 3% 4-BB(F)B(F,F)XB(F,F)F (14-47) 6% 5-BB(F)B(F,F)XB(F,F)F (14-47) 3% 3-HHV (2-1) 40% 3-HHV1 (2-1) 7% 3-HHEH-5 (3-13) 3% 3-HHB-1 (3-1) 3% VHHB-1 (3-1) 5% V2BB(F)B-1 (3-6) 5% 1V2BBF (2-8) 3% 3-BB(F,F)XB(F,F)F (13-97) 11% 3-HHBB(F,F)F (14-6) 3%

Use Example 19

[0216]

TABLE-US-00024 3-H(3F2)HB(2F,3F)-1 (No. 140) 3% 3-H(3F2)HB(2F,3F)O2 (No. 139) 4% 3-GB(F)B(F,F)XB(F,F)F (14-57) 4% 3-BB(F)B(F,F)XB(F,F)F (14-47) 3% 4-BB(F)B(F,F)XB(F,F)F (14-47) 7% 5-BB(F)B(F,F)XB(F,F)F (14-47) 3% 3-HHV (2-1) 41% 3-HHV1 (2-1) 6% 3-HHEH-5 (3-13) 3% 3-HHB-1 (3-1) 3% VHHB-1 (3-1) 3% V2BB(F)B-1 (3-6) 5% 1V2BBF (2-8) 3% 3-BB(F,F)XB(F,F)F (13-97) 5% 3-GB(F,F)XB(F,F)F (13-113) 4% 3-HHBB(F,F)F (14-6) 3%

[0217] NI=83.1 C.; =14.6 mPa.Math.s: n=0.103; =6.2.

INDUSTRIAL APPLICABILITY

[0218] The liquid crystal compound of the invention has good physical properties. A liquid crystal composition including this compound can be utilized for a liquid crystal display device in personal computers, television sets and so forth.