JPS60199867A - Alpha-methyl-beta-(4-substituted phenyl)propionic acid cyanophenyl ester derivative - Google Patents

Abstract

NEW MATERIAL:A compound of formula I (R is 1-18C alkyl or alkoxy; n is 1, 2). EXAMPLE:alpha-Methyl-beta-(4-butyloxyphenyl)propionic acid 4'-cyano-4-biphenylyl ester. USE:A liquid crystal composition: it can expand the liquid crystal range to lower temperatures. It has about +10 dielectric anisotropy and shows good stability to moisture, heat and light. PREPARATION:The reaction between alpha-methyl-beta-(4-substituted phenyl)propionic chloride of formula II and 4-cyanophenol (n=1) or 4-hydroxy-4'-cyanobiphenyl in the presence of pyridine gives a compound of formula I .

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to novel compounds of cyanophenyl ester derivatives and liquid crystal compositions containing the compounds.

Display elements using liquid crystals are widely used in watches, calculators, etc. These liquid crystal display elements utilize the optical anisotropy and self-directed anisotropy of liquid crystal materials, and the liquid crystal phases include nematic liquid crystal phase, smectic liquid crystal phase, and cholesteric liquid crystal phase, among which nematic liquid crystal is used. The one that has been put into practical use is the most widely used. These K types are TN type (twisted nematic type), DB type (III-like scattering type), guest type,
There are host type, DAPM, etc., and the properties required of the liquid crystal compound used for each type are different. It is desirable for the liquid crystal compounds used in these display elements to be pure white at as wide a temperature range as possible in the natural world and exhibit 46 liquid phases.Currently, there is no single compound that satisfies such conditions, and several types of liquid crystal compounds are available. Compounds or non-liquid crystal compounds are mixed and put into practical use. These compounds are required to be stable against moisture, light, heat, air, etc., and furthermore, it is desirable that the threshold voltage and saturation voltage for driving the display element be as low as possible.

The compound of the present invention is useful as a component of a liquid crystal composition, and can extend the liquid crystal temperature range of the liquid crystal composition to a low temperature range.

The present invention relates to α-methyl-β-(4-substituted phenyl)furopionic acid represented by the general formula (in the formula, R represents an alkyl group or an alkoxy group having 1 to 15 carbon atoms and represents nt'il or 2). An anophenyl ester conductor, and a liquid crystal composition containing the compound.

A compound of the present invention having a general formula where n == 1 does not exhibit a liquid crystal phase, but by adding it to a liquid crystal composition, the liquid crystal temperature range can be expanded to a low temperature range.

In the general formula representing the compound of the present invention, n-2 is about 50°C
By adding it to a liquid crystal composition, the liquid crystal temperature range can be extended to a low temperature range without significantly changing the liquid crystal clearing point. All of the compounds of the present invention have a dielectric anisotropy of about +10, and have good stability against moisture, heat, light, etc.

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

α-Methyl-β-(4-1 substituted phenyl)propionic acid chloride and 4-cyanphenol or 4-hydroxy-4′-7anobiphenyl are reacted in the presence of pyridine to obtain the desired α-methyl-β- A 7-anophenyl derivative of (4-substituted phenyl)propionic acid can be produced.

The manufacturing method is shown below using the chemical formula.

(R and n in the formula are the same as described above) Compounds of the present invention are shown below in Examples. The snout will be explained in more detail.

In each example, the crystalline phase is abbreviated as C1 transparent phase, the melting point is abbreviated as m, p, and the nematic phase is abbreviated as N.

Example 1 Preparation of α-methyl-β-(4-butyloxyphenyl)propionic acid-4'-cyano-4-biphenylyl ester 4-hydroxy-4-phanobiphenyl 2.3? (0
, 012 mol) in 710 ml of pyridine, shake well, and dissolve α-methyl-β-(4-butyloxyphenyl)propionic acid chloride 2,'7 # ([), 0
1 mol) was added. After leaving this reaction solution overnight, Loom/
of water and extracted the oily substance with 100ml of toluene.

Toluene layer with 5N-HC/21J-IJ with Lye
After washing with aOH, the solution was further washed with water until it became neutral, filtered through a p-filter, and the toluene was distilled off under reduced pressure. The remaining crystals are recrystallized with ethanol to obtain the target product, α-methyl-β.
-(4-butyloxyphenyl)propioyff-4/
-7'7'/-4-biphenylyl ester at 2.6f (
61 buns). m, p of this compound.

V'176J~77.1°C, N-work start 59. Showed o'c.

Examples 2 to 4 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 0℃
~44°C. The α-methyl-β-(4-
butyloxy7phenyl)propio/acid-4'-cyano-
The nematic liquid crystal temperature range of the composition consisting of one electroplated portion of 4-biphenylyl ester was -5°C to 45°C, and the nematic liquid crystal temperature range was expanded to a high temperature range and a low temperature range.

that's all

Claims (2)

[Claims] (1) α-Methyl-β-(4-substituted phenyl) represented by the general formula (in the formula, rc'RVi represents an alkyl group or alkoxy group having 1 to 15 carbon atoms, and nf''i represents 1 or 2) Cyanophenyl ester derivative of propionic acid. (2) α represented by the general formula (in the formula, R represents an alkyl group or an alkoxy group having 1 to 15 carbon atoms, and n represents 1 or 2)
- A liquid crystal composition containing a cyanophenyl ester derivative of methyl-β-(4-substituted phenyl)propionic acid.