JPS6033421B2 - liquid crystal compound - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel liquid crystalline compound exhibiting a nematic layer.

Some organic compounds form a liquid crystal phase, which is an intermediate phase between a crystalline solid and a disordered liquid phase.

Within the liquid crystal phase, molecules are arranged in a wide range of regular arrangements, and the liquid crystal layer can be classified into the following three types depending on the way the molecules are arranged. {1' Smectic layer ■ Nematic layer {3' Cholesteric layer A smectic layer is a type in which a wide range of ordered arrangements are substantially thin layers, and a nematic layer is a type in which the molecular arrangement is substantially linear, meaning that the molecules are This type is arranged parallel to the direction of the long wisteria.

The cholesteric layer is often included as a subclass of the nematic layer, and is very similar to the nematic layer, having a regular arrangement of small spiral regions in addition to the linear arrangement of the nematic intermediate layer. recent years,
In particular, it is well known that it is used as a display element in liquid crystal exhibiting a nematic layer, and is used in the display parts of wristwatches, calculators, and the like.

When liquid crystal is used as a display material in this way, in most cases several types of liquid crystal substances are mixed and used as a liquid crystal composition. As is generally known, the usable liquid crystal temperature range, responsiveness, etc. of the liquid crystal composition can be improved by appropriately selecting the liquid crystal material to be prepared empirically.
An object of the present invention is to provide a nematic liquid crystal compound that can be used as a material for a liquid crystal composition as described above.

The compounds of the present invention have the general formula (However, R represents a straight mirror alkyl group having 1 to 8 carbon atoms.

) and are 2-{4-(trans-4-n-alkylcyclohexylcarbonyloxy)-12-chlorobenzoyloxy}indanes. According to the following example,
The method for producing the compound provided by the present invention will be explained in detail. Example 1 Synthesized according to the following reaction.

(In the formula, R represents a straight mirror alkyl group having 1 to 8 carbon atoms.

) Stepl: 2-chloro-4-hydroxybenzoic acid 1
6. Dissolve 4 ml in 800 ml of toluene, and add 2 ml to this solution.
13.4 hours of hydroxyindane, 0.3 hours of sulfuric acid, and 0.3 hours of acid were added, and the mixture was refluxed for 30 hours. Subsequently, toluene was distilled off, and the remaining crude 2-(4-hydroxy-2-chlorobenzoyloxy)indane was recrystallized from methanol. The infrared absorption diagram of the compound is shown in FIG. Step 2: Trans-4-n-bentylcyclohexylcarboxylic acid chloride was synthesized by a conventional method from the reaction of commercially available trans-4-n-bentylcyclohexylcarboxylic acid and thionyl chloride.

bp 85-88℃/〇, 5 ribs Hgs p3:stepl
2-(4-Hydroxy-2-chlorobenzoyloxy)indan obtained in step 1 was dissolved in pyridine, and 0.62% of trans-4-bentylcyclohexylcarboxylic acid chloride obtained in step 2 was added to this. The mixture was added and left at room temperature.

After 16 hours, the reaction mixture was poured into cold concentrated hydrochloric acid, and the precipitated crystals were filtered out and then recrystallized from hexane.

mp 75q0 Cp 94.90 The infrared absorption diagram of the compound is shown in FIG.

In this way, the related 2-{4-1 (transformer 14-n
-bentylcyclohexylcarbonyloxy)-2-chlorobenzoyloxy}indane was obtained. Example 2,
3 In the same manner as in Example 1, the 2-(4-hydroxy-2
-chlorobenzoyloxy)indane, as shown in Table 1.

No. A few acid chlorides were synthesized and esterified as shown in Table 2. No. A few liquid crystalline compounds were synthesized. Table 1 Table 2 Note that No. 2 in Table 2 related to the present invention. The infrared absorption diagrams of the liquid crystalline compounds 2' and 3' are shown in Figures 3 and 4.

The ester compound provided by the present invention exhibits a nematic liquid crystal phase in the temperature range shown in Table 2. these are,
Applied, Phtanics, Utter, Vo12
Fu No. As a liquid crystal material for dual-frequency drive liquid crystal displays reported in 4,1F Aug Female TL974, etc., and as a material for liquid crystal compositions used in various liquid crystal displays when mixed with existing liquid crystal compounds. Can be used.

BRIEF DESCRIPTION OF THE DRAWINGS Figures 1 to 4 show infrared absorption diagrams of the following compounds, respectively.

Figure 1: 2-(4-hydroxy-2-chlorobenzoyloxy) indane, Figure 2: 2-{4-(trans-41-bentyloxy)-2-chlorobenzoyloxy }Indan, Figure 3...
...2-{4-trans-4-n-propylcyclohexylcarbonyloxy)-2-chlorobenzoyloxy}
Indan, Fig. 4...2-{4-(trans-4-n-
butylcyclohexylcarponyloxy)-2-chlorobenzoyloxy}indane.

figure [ Bran figure N Shigeru figure of ship figure size the gunwale

Claims (1)

[Claims] 1. A liquid crystal compound whose general formula is represented by the following formula. ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (However, R represents a straight chain alkyl group having 1 to 8 carbon atoms.)