JPS60197637A - Beta-(4-substituted phenyl)propionic acid phenyl ester derivative - Google Patents

Abstract

NEW MATERIAL:A beta-(4-substituted phenyl)propionic acid phenyl ester derivative shown by the formula I (R<1> and R<2> are 1-15C alkyl or alkoxy; R<2> is group shown by the formula II or formula III). EXAMPLE:beta-(4-Butyloxyphenyl)propionic acid-4'-propyl-4-biphenylyl ester. USE:A component of liquid crystal composition. Having improved stability to water, heat, light, etc. PREPARATION:For example, a 4-substituted cinnamic ester derivative is reduced in the presence of palladium-active carbon as a catalyst, to give a compound shown by the formula I .

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel compound and a liquid crystal composition containing the compound.

Display elements using liquid crystals are widely used in watches, calculators, etc. These liquid crystal display elements utilize the optical anisotropy and dielectric anisotropy of liquid crystal substances, and the liquid crystal phases include a nematic liquid crystal phase, a smectic liquid crystal phase, and a cholesteric liquid crystal phase. is the most widely put into practical use. These include TN type (twisted nematic W), D8m (dynamic scattering type), guest-host W, DAP type, etc., and the properties required of the liquid crystal compound used for each type are different. It is desirable that the liquid crystal compounds used in these display elements exhibit a liquid crystal phase over as wide a natural temperature range as possible, and at present there is no single compound that satisfies such conditions; several types of liquid crystal compounds are currently available. Alternatively, it is used practically by mixing a non-liquid crystal compound.

These compounds are desired to be stable against moisture, light, heat, air, etc., and to have low threshold voltages and saturation voltages for driving liquid crystal display elements.

The compound according to the present invention is useful as a component of a liquid crystal composition. A β-(4-substituted phenyl)propionic acid phenyl ester derivative and a liquid crystal composition comprising the compound.

Although it does not exhibit a liquid crystal phase, it can be added to a liquid crystal composition to extend the liquid crystal temperature range to a low temperature range. In the general formula representing the compound of the present invention, R2 is Rg) or -0-0-
The compound has a liquid crystal clearing point of 100° C. or higher, and can be added to a liquid crystal composition to widen the liquid crystal temperature range to a high temperature range and a low temperature range. All compounds of the present invention have good stability against moisture, heat, light, etc.

Next, a method for producing the compound of the present invention will be described.

β-(4-fi! substituted phenyl)propionic acid chloride and 4-substituted phenol or 4-(trans-4-[
(substituted cyclohexyl)phenol or 4-substituted-4'-
The desired ester derivative of β-(4-substituted phenyl)propionic acid can be produced by reacting hydroxybiphenyl in the presence of pyridine.

The manufacturing method is shown below using the chemical formula.

(R1, Ha and R2 in the formula are the same as above.)
or 4-substituted cinnamate derivatives with palladium-
The target β-(4-R-substituted phenyl)furopionate derivative can be produced by reduction using activated carbon as a catalyst.

The manufacturing method is shown below using the chemical formula.

(R1, Ha and R2 in the formula are the same as above.)
The compounds of the present invention will be explained in more detail in the following examples.

In each example, the crystalline phase is abbreviated as 8m for the C1 smectic phase, 8m for the transparent phase, ``P'' for the melting point, and N for the nematic phase.

Example 1 β-(4-butyloxyphenyl)propionic acid-4'
-Production of propyl-4-biphenylyl ester 4-k: )"Roxy4'-7'ropylbiphenyl 2.5F (0,012 mol) was added to viridiy 10tnl
After stirring well, 2.49 (0.01 mol) of β-(4-butyloxyphenyl)propionic acid chloride was added. This reaction solution was left overnight, poured into 100 ml of water, and an oily substance was extracted with 100 ml of toluene. The toluene layer was washed with 6N-HCI, then with 2N-NaOH, and then with water until it became neutral, filtered, and the toluene was distilled off under reduced pressure. The remaining crystals were recrystallized from ethanol to obtain -2,3t (55th) of β-(4-butyloxyphenyl)propionic acid-4/-propyl-4-biphenylyl ester. C-N point: 123.6-125.4°C, N-I point: 125. ．． The temperature was 6°C.

Examples 2 to 12 The desired compounds were produced by performing the same operation as in Example 1. The results are shown in Table 1 together with the results of Example 1.

The nematic liquid crystal temperature range of the liquid crystal composition with the following usage example is θ℃
~44°C. β-(4-Hentyloxyphenyl)furopionic acid-4-()? prepared in Example 6, which is one of the compounds of the present invention, is added to 9 parts by weight of the composition. The nematic liquid crystal temperature range of the composition consisting of 1 weight and 11 parts of 4-pentylcyclohexyl) phenyl ester is 15°C to 49°C.
℃ and was able to expand the nematic liquid crystal temperature range to high and low temperatures.

that's all

Claims (2)

[Claims] (1) A β-(4-substituted phenyl)propionic acid phenyl ester n-conductor represented by the general formula (in the formula, R1 and R3 each represent 1 to 15 carbon atoms). (2) β-(4-substituted phenyl)propionic acid phenyl ester n represented by the general formula (in the formula, R1 and Ha each represent an alkyl group or an alkoxy group having 1 to 15 carbon atoms, and R2 represents t) A liquid crystal composition containing a conductor.