JP2834349B2 - 1-cyclohexenyl-3,5-difluorobenzene derivative - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a liquid crystal material useful as a liquid crystal material.
The present invention relates to a -cyclohexenyl-3,5-difluorobenzene derivative, a liquid crystal composition containing the derivative, and a liquid crystal display device using the liquid crystal composition.

[0002]

2. Description of the Related Art Liquid crystal display devices are widely used in clocks, calculators, word processors, televisions, and the like. Among these liquid crystal display devices, a TN type (twisted nematic type) liquid crystal display device utilizing the optical anisotropy and dielectric anisotropy of a liquid crystal material is particularly frequently used. Characteristics required for liquid crystal materials currently used in liquid crystal display devices include:
The liquid crystal temperature range is wide, the electro-optical response speed is fast, the viewing angle range is wide, the driving voltage is low, and the film is chemically and optically stable.

[0003]

A single liquid crystal compound satisfying all the above characteristics has not been found yet. For this reason, at present, several types of liquid crystal compounds having various characteristics are mixed, or non-liquid crystal compounds are further mixed to be put to practical use.

The driving voltage of the liquid crystal display device is a threshold voltage V
Depending on the value of _th , the threshold voltage V _th is proportional to the square root of the reciprocal of the dielectric anisotropy Δε of the liquid crystal material. Therefore, when a liquid crystal material having a positive dielectric anisotropy Δ △ is used, the threshold voltage V _th can be suppressed to a low value. Therefore, an object of the present invention is to provide a liquid crystal compound having a positive dielectric anisotropy Δ △.

[0005]

The 1-cyclohexenyl-3,5-difluorobenzene derivative of the present invention is represented by the general formula (I).

[0006]

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(Wherein R ¹ is an alkyl group having 1 to 10 carbon atoms or a trans group having an alkyl group having 1 to 10 carbon atoms)
Represents a 4-alkylcyclohexyl group, and R ² represents a hydrogen atom, a cyano group, a halogen atom, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, -DiPh-R
^{3, -CyEN-R 3, -CyEN} -Cy-R 3, -D
It indicates iPh-Cy-R ³ or -COO-R ^4,, R
³ represents an alkyl group having 1 to 10 carbon atoms, R ⁴ represents a hydrogen atom, -Ph-R ⁵ , or -Cy-R ⁵ , and R ⁵ is a cyano group, a halogen atom, an alkyl group having 1 to 10 carbon atoms. A group or an alkoxy group having 1 to 10 carbon atoms;
Represents a 1,4-substituted phenyl group, DiPh represents a 1,4-substituted dihydrophenyl group, CyEN represents a 1,4-substituted cyclohexenyl group, and Cy represents a 1,4-substituted transcyclohexyl group. )

Further, the liquid crystal composition of the present invention contains the 1-cyclohexenyl-3,5-difluorobenzene derivative.

Further, the liquid crystal display device of the present invention is characterized in that
A liquid crystal composition containing a cyclohexenyl-3,5-difluorobenzene derivative was used.

According to the present invention, 1-cyclohexenyl-3,5-
The method for producing the difluorobenzene derivative will be described.
However, R ¹ , R ² , R ³ , R ⁴ and R ⁵ are the same as those described in the claims.

The production method of the compound (1) of the present invention will be described using Chemical formula 3. The compound (1) is prepared by first reacting 1-bromo-3,5-difluorobenzene (a) with magnesium to produce a Grignard reagent (b), and then reacting the Grignard reagent (b) with a 4-substituted cyclohexanone (c). ), Followed by a dehydration reaction.

[0012]

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The method for producing the compound (2) will be described using Chemical formula 4. First, compound (1) is reacted with n-butyllithium to synthesize compound (d), and then compound (d) is reacted with solid carbonic acid to obtain compound (2).

[0014]

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The compound (3) represented by the chemical formula (5) can be produced via the corresponding benzoyl chloride and benzamide by reacting the compound (2) with thionyl chloride, ammonia and thionyl chloride in this order. .

[0016]

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The production method of the compound (4) will be described using Chemical formula 6. This compound (4) is obtained by adding potassium t to compound (d).
It can be obtained by reacting ert butoxide with an alkyl iodide. (R ⁶ represents an alkyl group having 1 to 10 carbon atoms.)

[0018]

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The method for producing the compound (5) and the compound (6) will be described using Chemical formula 7. First, sulfuric acid is added to chemical compound (2).
Compound (e) is synthesized by reacting sodium nitride.
The compound (e) is reacted with sulfuric acid or sodium nitrite to form a diazonium salt (f), and further reacted with cuprous chloride or hydrochloric acid to obtain a compound (5). Further, the compound (6) is obtained by hydrolyzing the diazonium salt (f) and then reacting with the alkyl bromide. (R ⁶ represents an alkyl group having 1 to 10 carbon atoms.)

[0020]

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The compound (7) represented by the formula (8) is esterified by reacting the compound (2) with a 4-alkylphenol, 4-cyanophenol, 4-fluorophenol, 4-alkoxyphenol, 4-alkylcyclohexanol or the like. Can be manufactured. (R ⁷
Represents a -Ph-R ⁵ or -Cy-R ^5,. )

[0022]

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Compounds (8), (9), (10), (1)
The production method of 1) is shown in Chemical formula 9. These compounds are ketones (g), (h), (i) corresponding to compound (d),
(J) can be obtained by reacting each, followed by a dehydration reaction.

[0024]

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The compound having a 1,4-substituted dihydrophenyl group represented by DiPh has isomers having different double bond positions. Therefore, when these compounds are produced, a reaction product is obtained as a mixture of isomers, and this mixture can be used for the liquid crystal composition and the liquid crystal display of the present invention. Further, the isomers in the mixture can be separated by liquid chromatography or the like, and only one isomer can be used in the liquid crystal composition or the liquid crystal display device of the present invention.

The 1-cyclohexenyl-3,5- of the present invention
The difluorobenzene derivative can be mixed with many liquid crystal compounds to produce a liquid crystal composition. Further, these liquid crystal compositions can be used for a liquid crystal display device. Examples of the liquid crystal compound that can be mixed with the derivative of the present invention include an ester type, a cyclohexylphenyl type, a biphenyl type, a pyrimidine type, a dioxane type and a tolan type.

[0027]

EXAMPLES The present invention will be specifically described with reference to examples, but the present invention is not limited to these examples.
Note that the dielectric anisotropy Δε in the examples is a value at 20 ° C.

Example 1 An ether solution was prepared by dissolving 30.1 g of 3,5-difluorobromobenzene in 90 ml of anhydrous ether. Next, metal magnesium powder 4.5
This ether solution was added dropwise at 15-20 ° C. while stirring g. Thereafter, the mixture was reacted at room temperature for 1 hour to produce 3,5-difluoromagnesium bromobenzene. While stirring the Grignard reagent, 20 g of 4-propylcyclohexanone was added dropwise at -10 to 0 ° C, and then 1 g at room temperature.
Allowed to react for hours. After the reaction is completed, dilute hydrochloric acid is gradually added dropwise.
Thereafter, extraction was performed with diethyl ether. After the extract was washed with saturated saline, anhydrous sodium sulfate was added to dry the extract. This was filtered and the solvent was distilled off from the filtrate under reduced pressure to give 1
-(1-hydroxy-4-propylcyclohexyl)-
A crude product of 3,5-difluorobenzene was obtained.

This crude product was dissolved in 250 ml of toluene, and 0.5 ml of p-toluenesulfonic acid monohydrate was added to the solution.
g was added. Thereafter, the mixture was refluxed with stirring, and water generated by the reaction was removed by a decanter. This dehydration reaction is 3
After 0 minutes, the reaction mixture was cooled. The toluene layer of the reaction mixture was washed successively with a saturated aqueous solution of sodium hydrogencarbonate and brine, dried over anhydrous sodium sulfate, and the toluene was distilled off under reduced pressure.
25 g of 1- (4-propylcyclohexenyl) -3,5-difluorobenzene which was the described compound (12) was obtained. This compound had a melting point of 2 ° C. and a dielectric anisotropy Δ △ 0.5.

[0030]

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Example 2 Instead of 20 g of 4-propylcyclohexanone, 4-pentylcyclohexanone 2
Except that 3.4 g is used, the same method as in Example 1 is used.
28 g of 1- (4-pentylcyclohexenyl) -3,5-difluorobenzene, which is the compound (13) described in 1, was obtained. This compound had a melting point of 5 ° C. and a Δε of 0.8. The infrared absorption spectrum of this compound (13) is shown in FIG.
Shown in

[0032]

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Example 3 A compound represented by the formula (12) was prepared in the same manner as in Example 1 except that 31.6 g of 4- (trans-4-propylcyclohexyl) -cyclohexanone was used instead of 20 g of 4-propylcyclohexanone. 1
36 g of 1- (4- (trans-4-propylcyclohexyl) -cyclohexenyl) -3,5-difluorobenzene which was 4) was obtained. This compound is a nematic liquid crystal with C
-N point 73 ° C, NI point 88 ° C, Δε 1.3.

[0034]

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Example 4 A compound represented by the formula (13) was prepared in the same manner as in Example 1, except that 35.0 g of 4- (trans-4-pentylcyclohexyl) -cyclohexanone was used instead of 20 g of 4-propylcyclohexanone. 1
5), 38 g of 1- (4- (trans-4-pentylcyclohexyl) -cyclohexenyl) -3,5-difluorobenzene was obtained. This compound is a nematic liquid crystal with C
The N point was 62 ° C, the NI point was 95 ° C, and Δε1.5.

[0036]

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Example 5 1- (4) obtained in Example 1
9.46 g of (-propylcyclohexenyl) -3,5-difluorobenzene was dissolved in 40 ml of anhydrous tetrahydrofuran and cooled to -70 ° C. To this solution, 27 ml of a hexane solution of n-butyl lithium (1.5 mol / l) was added dropwise, and after completion of the addition, the mixture was further reacted at -50 ° C. for 5 hours.
(4-Propylcyclohexenyl) -3,5-difluoro-4-lithiumbenzene was produced. This product is
After cooling to 70 ° C., 2 g of solid carbonic acid was added, and the temperature was raised to room temperature with stirring to cause a reaction. After completion of the reaction, dilute hydrochloric acid was gradually added dropwise, followed by extraction with diethyl ether. After the extract was washed with saturated saline, anhydrous sodium sulfate was added to dry the extract. Next, this extract was filtered, and the solvent was distilled off from the filtrate under reduced pressure. The obtained reaction product was recrystallized from a mixed solvent of ethyl acetate and toluene to give 4- (4-propylcyclohexenyl) which is the compound (16) described in Chemical Formula 14.
9.1 g of -2,6-difluorobenzoic acid was obtained. This compound had a melting point of 75 ° C. and a Δε of 1.8.

[0038]

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Example 6 1- (4- (trans-4-propylcyclohexyl) -cyclohexenyl) -3 instead of 9.46 g of 1- (4-propylcyclohexenyl) -3,5-difluorobenzene 4- (4- (trans-4-propylcyclohexyl) -cyclohexenyl)-which is compound (17) described in Chemical formula 15 in the same manner as in Example 5 except that 12.8 g of 5,5-difluorobenzene is used. 12.0 g of 2,6-difluorobenzoic acid was obtained. This compound had a melting point of 72 ° C. and Δ △ 1.5.

[0040]

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Example 7 4- (4) obtained in Example 5
2.8 g of (-propylcyclohexenyl) -2,6-difluorobenzoic acid was dissolved in 20 ml of thionyl chloride and refluxed for 2 hours with stirring. Thereafter, thionyl chloride was distilled off under reduced pressure, aqueous ammonia was added, and the mixture was stirred at 10 ° C for 30 minutes. After completion of the reaction, the precipitated crystals were filtered and recrystallized from a mixed solvent of ethyl acetate and ethanol to obtain 4- (4-propylcyclohexenyl) -2,6-difluorobenzoic amide. This was dissolved in 15 ml of thionyl chloride and refluxed for 2 hours with stirring. Thereafter, thionyl chloride was distilled off under reduced pressure.
Recrystallization from a mixed solvent of ethyl acetate and ethanol
1 g of 4- (4-propylcyclohexenyl) -2,6-diflorocyanobenzene which is the compound (18) according to 6.
I got This compound had a melting point of 59 ° C. and Δε27.9.

[0042]

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Example 8 4- (4-Pentylcyclohexenyl) -2,6-instead of 2.8 g of 4- (4-propylcyclohexenyl) -2,6-difluorobenzoic acid
Compound (19) described in Chemical Formula 17 was prepared in the same manner as in Example 7 except that 3.0 g of difluorobenzoic acid was used.
1.5 g of (4-pentylcyclohexenyl) -2,6-diflorocyanobenzene were obtained. This compound has a melting point of 50.
° C and Δε23.4.

[0044]

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Example 9 4- (4- (Trans-4-pentylcyclohexyl) -cyclohexenyl) -2 instead of 2.8 g of 4- (4-propylcyclohexenyl) -2,6-difluorobenzoic acid In the same manner as in Example 7, except that 3.9 g of 2,6-difluorobenzoic acid was used.
4- (4- (trans-) which is compound (20) according to 8.
4-pentylcyclohexyl) -cyclohexenyl)-
1.2 g of 2,6-diflorocyanobenzene were obtained. This compound was a nematic liquid crystal and had a CN point of 119 ° C., an NI point of 143 ° C., and Δε12.5.

[0046]

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(Example 10) 4-
2.8 g of (4-propylcyclohexenyl) -2,6-difluorobenzoic acid and 1.19 g of 4-cyanophenol were dissolved in 20 ml of methylene chloride, and 2.47 g of N, N′-dicyclohexylcarbodiimide was added thereto. Stir at room temperature for 3 hours. After completion of the reaction, the precipitated crystals were filtered and the mother liquor was purified by a silica gel column, and methylene chloride was distilled off under reduced pressure to give 4- (4-propylcyclohexenyl) -2, a compound (21) according to Chemical formula 19. 3.0 g of 2,4-difluorobenzoic acid- (4-cyanophenyl) were obtained. This compound is a nematic liquid crystal with a CN point of 110 ° C.
The NI point was 178 ° C. and Δε 16.4.

[0048]

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Example 11 4-cyanophenol
Except that 1.12 g of 4-fluorophenol is used in place of 19 g, compound (22) described in Chemical formula 20 is 4- (4-propylcyclohexenyl) -2,6-difluorobenzoate in the same manner as in Example 10. 2.8 g of acid- (4-fluorophenyl) were obtained. This compound is a nematic liquid crystal with C
-N point 53 ° C, NI point 90 ° C, Δε12.1.

[0050]

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Example 12 4-cyanophenol
Except that 1.36 g of 4-propylphenol is used instead of 19 g, compound (23) described in Chemical formula 21 is 4- (4-propylcyclohexenyl) -2,6-difluorobenzoic acid in the same manner as in Example 10. 3.1 g of acid- (4-propylphenyl) were obtained. This compound was a nematic liquid crystal and had a CN point of 50 ° C., an NI point of 87 ° C., and Δε1.7.

[0052]

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Example 13 4- (4- (Trans-4-propylcyclohexyl) -cyclohexenyl) -2 instead of 2.8 g of 4- (4-propylcyclohexenyl) -2,6-difluorobenzoic acid 4- (4- (trans-4-propylcyclohexyl) -cyclohexenyl)-which is the compound (24) described in Chemical formula 22 in the same manner as in Example 10 except that 3.6 g of 2,6-difluorobenzoic acid is used. 4.0 g of 2,6-difluorobenzoic acid- (4-cyanophenyl) was obtained. This compound is a nematic liquid crystal with C
-N point 134 ° C, NI point 320 ° C, Δε 8.5.

[0054]

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(Example 14) 1- obtained in Example 1
4.72 g of (4-propylcyclohexenyl) -3,5-difluorobenzene was added to 20 ml of anhydrous tetrahydrofuran.
And cooled to -70 ° C. Thereafter, 13 ml of a hexane solution (1.5 mol / l) of n-butyllithium was added dropwise. After the completion of the dropwise addition, the mixture was further reacted at -50 ° C for 5 hours.
-(4-Propylcyclohexenyl) -3,5-difluoro-4-lithiumbenzene was produced. The product was cooled to -70 ° C and 4-pentylcyclohexanone.
3 g was added dropwise, and after completion of the addition, the temperature was raised to room temperature with stirring to cause a reaction. After completion of the reaction, dilute hydrochloric acid was gradually added dropwise, followed by extraction with diethyl ether. After the extract was washed with saturated saline, anhydrous sodium sulfate was added and dried.
This was filtered and the solvent was distilled off from the filtrate under reduced pressure to give 1- (4-propylcyclohexenyl) -4- (1-hydroxy-4
-Pentylcyclohexyl) -3,5-difluorobenzene was obtained. This crude product is mixed with 50 ml of toluene
After adding 0.1 g of p-toluenesulfonic acid monohydrate to this solution, the mixture was refluxed while stirring, and water generated by the reaction was removed by a decanter. After performing the dehydration reaction for 30 minutes, the reaction mixture was cooled. The toluene layer of the reaction mixture was washed successively with a saturated aqueous solution of sodium hydrogen carbonate and saturated saline, dried over anhydrous sodium sulfate, and the toluene was distilled off under reduced pressure. The obtained reaction product is passed through a silica gel column, and recrystallized with a mixed solvent of ethyl acetate and ethanol to obtain 1- (4-propylcyclohexenyl) -4- (4-pentylcyclo) which is compound (25) described in 23. Hexenyl) -3,5-difluorobenzene 3.2 g was obtained. This compound is a nematic liquid crystal and has C—N
Point 43 ° C, NI point 107 ° C, Δε2.7.

[0056]

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Example 15 1- (4- (Trans-4-propylcyclohexyl) -cyclohexenyl) -3 instead of 4.72 g of 1- (4-propylcyclohexenyl) -3,5-difluorobenzene 1- (4- (trans-4-propylcyclohexyl) -cyclohexenyl)-which is the compound (26) described in Chemical formula 24 in the same manner as in Example 14 except that 6.36 g of 5,5-difluorobenzene is used. 4- (4-pentylcyclohexenyl) -3,
6.0 g of 5-difluorobenzene were obtained. This compound is a nematic liquid crystal having a CN point of 91 ° C., an NI point of 209 ° C.,
ε 4.8.

[0058]

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(Example 16) 1- Obtained in Example 4
3.4 g of (4- (trans-4-pentylcyclohexyl) -cyclohexenyl) -3,5-difluorobenzene
Was dissolved in 40 ml of anhydrous tetrahydrofuran,
And cooled. Thereafter, 6.7 ml of a hexane solution of n-butyllithium (1.5 mol / l) was added dropwise, and after completion of the addition, the mixture was further reacted at -50 ° C for 5 hours to obtain 1- (4- (trans-4-pentylcyclohexyl) -cyclohexenyl. )
-3,5-Difluoro-4-lithium benzene was produced. While cooling this product to −70 ° C. and stirring, a solution of 1.1 g of potassium tert-butoxide in 20 ml of anhydrous tetrahydrofuran is added dropwise over 1 hour. After completion of the dropwise addition, the mixture is stirred at the same temperature for 10 minutes, and then a solution of 1.71 g of iodoethane in 5 ml of anhydrous tetrahydrofuran is added dropwise with stirring. After completion of the dropping, the temperature is raised to room temperature with stirring to cause a reaction. After completion of the reaction, dilute hydrochloric acid was gradually added dropwise, followed by extraction with diethyl ether. The extract was washed successively with a saturated aqueous solution of sodium hydrogen sulfite, a saturated aqueous solution of sodium hydrogen carbonate, and saturated saline, and then dried by adding anhydrous sodium sulfate. This was filtered, and the solvent was distilled off from the filtrate under reduced pressure.
3.5 g of-(trans-4-pentylcyclohexyl) -cyclohexenyl) -3,5-difluoro-4-ethylbenzene were obtained. This compound is a nematic liquid crystal and has C—N
Point 43 ° C, NI point 105 ° C, Δε0.5.

[0060]

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Example 17 A compound (28) represented by Chemical Formula 26 was prepared in the same manner as in Example 14 except that 3.2 g of 4-pentylcyclohexenone was used instead of 3.3 g of 4-pentylcyclohexanone. 2.8 g of-(4-propylcyclohexenyl) -4- (4-pentyldihydrophenyl) -3,5-difluorobenzene was obtained. This compound is a nematic liquid crystal having a C—N point of 10 ° C. and an N−I point of 6.
5 ° C. and Δε0.6.

[0062]

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(Example 18) Chemical formula 27 is described in the same manner as in Example 14 except that 4.9 g of 4- (trans-4-pentylcyclohexyl) -cyclohexenone is used instead of 3.3 g of 4-pentylcyclohexanone. 1- (4-propylcyclohexenyl) which is the compound (29) of
3.5 g of -4- (4- (trans-4-pentylcyclohexyl) -dihydrophenyl) -3,5-difluorobenzene was obtained. This compound is a nematic liquid crystal and has C—N
Point 59 ° C, NI point 232 ° C, Δε0.4.

[0064]

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(Example 19) Chemical formulas 28, 29, 30,
Compound (12) 1 of the present invention was added to 90 parts by weight of a liquid crystal composition obtained by mixing the compounds described in Chemical formulas 31, 32, 33 and 34.
The liquid crystal composition was prepared by adding 0 parts by weight. Table 1 shows the characteristics of the liquid crystal composition. The threshold voltage V _{th in the} table is a value when this liquid crystal composition is mounted on a TN type liquid crystal display device having a cell thickness of 9 μm.

Here, chemical formulas 28, 29, 30, 30, 31
The characteristics of the liquid crystal composition composed of only the compounds described in Chemical formulas 32, 33 and 34 were as follows: NI point: 63 ° C., Δn: 0.107, viscosity: 37.2 cps, V _th: 1.49 V.

[0067]

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[0068]

[Table 1]

(Examples 20 to 32) In the same manner as in Example 19, 90 parts by weight of a liquid crystal composition obtained by mixing the compounds described in Chemical formulas 28, 29, 30, 31, 32, 33 and 34 was added.
Compounds (13), (14), (15) and (1) of the present invention
8), (19), (20), (21), (22), (2)
3), (24), (25), (26), and (27) were each added in an amount of 10 parts by weight to prepare a liquid crystal composition. Tables 1, 2, and 3 show the characteristics of the liquid crystal composition.

[0070]

[Table 2]

[0071]

[Table 3]

[0072]

According to the present invention, 1-cyclohexenyl-3,5
The difluorobenzene derivative has a positive dielectric anisotropy Δε. Therefore, a liquid crystal composition containing the compound of the present invention has excellent characteristics as a liquid crystal material, and a liquid crystal display device using the liquid crystal composition has good display characteristics. Further, the derivative of the present invention has a high mutual solubility with various compounds, and can be used in combination with many liquid crystal materials as a constituent material of a liquid crystal composition, and is useful for improving characteristics of the liquid crystal composition.

[Brief description of the drawings]

FIG. 1 is a diagram showing an infrared absorption spectrum of a compound of the present invention.

────────────────────────────────────────────────── ─── Continued on the front page (51) Int.Cl. ⁶ Identification code FI C07C 255/55 C07C 255/55 C09K 19/30 C09K 19/30 19/42 19/42 G02F 1/13 500 G02F 1/13 500 (58) Field surveyed (Int.Cl. ⁶ , DB name) C07C 25/18 C07C 69/76 C07C 69/773 C07C 255/46 C07C 255/50 C07C 255/55 C09K 19/30 C09K 19/42 G02F 1 / 13 CA (STN)

Claims (3)

(57) [Claims] 1. A 1-cyclohexenyl-3,5-difluorobenzene derivative represented by the general formula (I). Embedded image (Where R ¹ represents an alkyl group having 1 to 10 carbon atoms or a trans-4-alkylcyclohexyl group having an alkyl group having 1 to 10 carbon atoms, and R ² represents a hydrogen atom, a cyano group, a halogen atom, a carbon atom 1-10 alkyl group, an alkoxy group having 1 to 10 carbon atoms, -DiPh-R ^3, -C
^{yEN-R 3, -CyEN-Cy} -R 3, -DiPh-
Indicates cy-R ³ or -COO-R ^4,, R ³ represents an alkyl group having 1 to 10 carbon atoms, R ⁴ is a hydrogen atom, -P
h-R ^5, or indicates -Cy-R ^5, R ⁵ represents a cyano group, a halogen atom, an alkyl group having 1 to 10 carbon atoms or an alkoxy group having 1 to 10 carbon atoms,, Ph is 1,4
A substituted phenyl group, DiPh is a 1,4-substituted dihydrophenyl group, CyEN is a 1,4-substituted cyclohexenyl group, Cy
Represents a 1,4-substituted transcyclohexyl group. ) 2. The 1-cyclohexenyl- according to claim 1,
A liquid crystal composition containing a 3,5-difluorobenzene derivative. 3. The 1-cyclohexenyl- according to claim 2,
A liquid crystal display device using a liquid crystal composition containing a 3,5-difluorobenzene derivative.