JPS58118543A - Trans-4-(4'-substituted phenyl)cyclohexanecarboxylic acid 2,4-dihalogenophenyl ester - Google Patents

Abstract

NEW MATERIAL:The compound of formulaI(R is 1-10C alkyl or alkoxy; X and Y are F or Cl). EXAMPLE:A liquid crystal compound having a dielectric anisotropy as low as -0.1 and low viscosity, and capable of lowering te threshold voltage and saturation voltage of a liquid crystal composition by adding to the composition. Some of the compounds of formulaIhave N-I point of about 100 deg.C, are applicable to high-temperature liquid crystal composition, and have good compatibility with the other liquid crystal compositions. PROCESS:The compound of formulaIis prepared by reacting trans-4-(4'-substituted phenyl)cyclohexanecarboxylic acid with thionyl chloride, and reacting the resultant acid chloride with 2,4-dihalogenophenol in the presence of pyridine.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel power source crystal compound exhibiting a liquid crystal phase and having low viscosity, and a liquid crystal composition containing the same.

Liquid crystal display elements utilize the optical anisotropy and dielectric anisotropy of liquid crystal materials, but depending on the display format, TN
Type (twisted nematic type), Drill (dynamic scattering type)
There are various types such as , guest-host type, DAP type, etc., and the properties of the liquid crystal materials suitable for each type of use are different. However, it is common that all liquid crystal materials must be stable against moisture, air, heat, light, etc., and they must exhibit a liquid crystal phase over as wide a temperature range as possible, centering on room temperature, and display The optimum dielectric anisotropy value (ΔC
). However, at present, there is no single compound that satisfies these conditions, and the current situation is to use liquid crystal compositions obtained by mixing several types of liquid crystal compounds and non-liquid crystal compounds.

An object of the present invention is to provide a novel liquid crystal compound useful as a component of such a liquid crystal composition, and particularly suitable for adjusting the Δε value.

That is, the present invention provides trans-4-(4'-substituted The present invention is a liquid crystal composition characterized by containing 2,4-dihalogenophenyl (phenyl)cyclohexanecarboxylic acid ester and at least one type thereof.

The compound of the present invention has a small ΔC of -0.1 and a low viscosity, and by adding it to a liquid crystal composition, it is possible to lower the electrical properties of the original liquid crystal composition, that is, the threshold voltage and saturation voltage. .

Some of the compounds of the present invention have an N-I point of around 100°C.
It can also be applied to objects with a temperature of 80°C or higher. In addition, it is well soluble in other liquid crystal compositions such as biphenyl-9-azo-7, Kutsuf paste, and phenylcyclohexane, and has a wide range of applications.

Next, the method for producing the compound of the present invention will be described. First, trans-4-(4'-substituted phenyl)cyclohexanecarboxylic acid corresponding to the target compound is reacted with thionyl chloride to produce trans-c-(4'-substituted phenyl)cyclohexanecarboxylic acid. Hexanecarboxylic acid was added to the 2,4-
The desired compound is obtained by reacting with dihalogenophenol. This is represented by a chemical formula: (In the above formula, R, X, and Y are the same as above.) The manufacturing method and usage examples of the compound of the present invention will be explained in more detail with reference to Examples below.

Example 1 () Production of trans-4-(4'-7'ropylphenyl)cyclohexanecarboxylic acid 2-fluoro-4-chlorophenyl ester) trans-4-(4'-7'ropylphenyl)cyclohexanecarboxylic acid [2 ,4t (0.01 mol) 10 mJ of thionyl chloride is placed in a flask and heated to 50°C.

It becomes uniform in 3 hours. Excess thionyl chloride is distilled off under reduced pressure. The remaining oil is filtered with trans-4-(4'-7'robylphenyl)cyclohexanecarboxylic acid chloride. On the other hand, 2-fluoro-4-chlorophenol 1.5
To a solution of f (0.01 mol) in pyridine, add the acid chloride obtained above, add dry toluene, mix well, and set aside overnight. Pour the reaction solution into water, add 6N hydrochloric acid and 2N hydroxide, and then wash with water until neutral. The toluene layer was dried over anhydrous sodium sulfate, filtered, and toluene was distilled off under reduced pressure. The remaining oil was recrystallized from ethanol to give the desired trans-4-(4'-7'ropylphenyl)cyclohexanecarboxylic acid 2-fluoro-4-chloro at 133.6°C.

Examples 2 to 15 Trans-4-(4'-ft-substituted phenyl)cyclohexanecarboxylic acid having another alkyl group instead of trans-4-(4'-propylphenyl)cyclohexanecarboxylic acid in Example 1 and 2-fluoro-4
- 2.4 mol of trans-4-(4'-substituted phenyl)cyclohexanecarboxylic acid shown in Table 1 was carried out in the same manner using 0.01 mol of other 2,4-dihalogenophenol in place of chlorophenol. -Dihalogenophenyl ester was prepared.

These yields, physical properties, etc. are shown in Table 1 together with the results of Example 1.

Example 16 (Use Example 1) 4-benf-4'-cyanobiphenyl 45
Thi-4-hebutyl-4'-cyanobiphenyl 29
-4-octyloxy-4'-cyanobiphenyl 15
Wound 4-pentyl-4'-cyanoterphenyl 11
The N-4 point of the liquid crystal mixture having a composition as follows: 63.3° C., viscosity: 46 Cp at 20° C., and dielectric anisotropy: +12.4.

This liquid crystal mixture was coated with silicon and sealed in a cell with a thickness of 10 m, which was made by assembling two substrates equipped with rubbed tin oxide transparent electrodes to form a liquid crystal cell at 25°C.
When I measured its characteristics, the threshold voltage was 1.65.
V, and the saturation voltage h was 2.31 J.

To 90 parts of this liquid crystal mixture was added 10 parts of Example 70 of the present invention, Tran-4-(4'-benkelphenyl)cyclohexanecarboxylic acid 2-fluoro-4-chlorophenyl ester.
The liquid crystal mixture with a composition of
0.5, respectively, and the threshold voltage is 1.1537.
The saturation voltage was as low as 2,227.

Example 17 (Use example 2) 4-pentyl-4'-7anobiphenyl 51th 4-hebutyl-4'-cyanobiphenyl 32e
Point F-1 of a liquid crystal mixture with the composition s4-octyloxi7-4'-cyanobiphenyl etch, F'i44,3℃,
The viscosity is 4ocp at 20°C, and the dielectric anisotropy is +12.4. This liquid crystal mixture was coated with silicon and sealed in a cell with a thickness of 10 meters, which was made by assembling 92 substrates equipped with transparent tin oxide electrodes treated with 2 pins to form one liquid crystal cell.
When its characteristics were measured at 5℃, the threshold voltage was 1.65
V, the saturation voltage is 2,31v.9.

The N-1 point of the liquid crystal mixture obtained by adding 10 parts of trans-4-(4'-7'ropylphenyl)cyclohexanecarboxylic acid 2-fluoro-4-chlorophenyl ester according to Example IK of the present invention to 90 parts of this liquid crystal mixture was 53. At 20°C, the dielectric anisotropy was +11.0, but the viscosity was at 20°C.
It was the same as 40Cp.

Claims (2)

[Claims] (1) trans-4-(4'-substituted phenyl) represented by the general formula (in the above formula, R represents an alkyl group or an alkoxy group having 1 to 10 carbon atoms, and ) Cyclohexanecarboxylic acid 2,4-dihalogenophenyl ester. (2) trans-4-(4'-substituted phenyl ) A liquid crystal composition containing at least one type of fuclohexanecarboxylic acid 2,4-dihalokecyphenyl ester.