JPS615054A - Phenethyl cyclohexanecarboxylate derivative - Google Patents

Abstract

NEW MATERIAL:A compound expressed by formula I (R represents 1-15C alkyl; X represents CN, 1-15C alkyl or alkoxyl; n is 1 or 2). EXAMPLE:beta-( 4-Ethoxyphenyl )ethyl trans-4-( trans-4-ethylcyclohexyl )cyclohexanecarboxylate. USE:A component of liquid crystal compositions having excellent stability against water, heat, light, etc. PREPARATION:A trans-4-substituted cyclohexanecarboxylic acid chloride expressed by formula II is reacted with a beta-(4-substituted phenyl)ethylalcohol expressed by formula III in the presence of pyridine to obtain a beta-(4-substituted- phenyl)ethyl trans-4-substituted-cyclohexanecarboxylate expressed by formula I. The degree of freedom in choice of components constituting the liquid crystal composition is enlarged by using the compound expressed by formula I as one component thereof.

Description

DETAILED DESCRIPTION OF THE INVENTION [Field of Application] The present invention relates to a novel cyclohexanecarboxylic acid phenethyl ester derivative and a liquid crystal composition containing the compound.

[Background of the invention]

Displays and 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 materials, and the liquid crystal phases include nematic liquid crystal phase, smectic liquid crystal phase, and cholesteric liquid crystal phase. Most widely put into practical use. There are TN type (twisted nematic type), D8 type (dynamic scattering type), guest-host type, DAP type, etc., and the properties required of the liquid crystal compound used for each type are different. However, in any case, it is desirable that the liquid crystal compounds used in these display elements exhibit a liquid crystal phase over as wide a temperature range as possible, and they are also required to be stable against moisture, light, heat, air, etc. ing. However, at present, there is no single compound that satisfies all of these conditions, and the current situation is that a mixture of several types of liquid crystal compounds or liquid crystal-like compounds is used for practical use.

[Purpose of the invention]

An object of the present invention is to provide a novel liquid crystal compound useful as a component of a liquid crystal composition used for the above purposes.

[Structure of the invention]

That is, the present invention is based on the general formula (in the above formula, R represents an alkyl group having 1 to 15 carbon atoms, and
represents CN or an alkyl group or alkoxy group having 1 to 15 carbon atoms, and ru is 1 or 2) A liquid crystal composition containing a Schiff tetrahexanecarboxylic acid phenethyl ester derivative represented by the following and at least one thereof as one component. It is a thing.

〔Effect of the invention〕

All of the compounds of the present invention have excellent stability against moisture, heat, light, etc., and are compatible with other liquid crystal compounds, such as ester-based, chic-based, azoxy-based, hyphenyl-based, and cyclohexane-based liquid crystal compounds. By mixing these compounds or mixtures thereof, liquid crystal compositions suitable for various liquid crystal display devices can be constructed.

Among the compounds of formula (1), those with l = 1 often exhibit a relatively low N-I point around room temperature, as shown in the examples below, and those with l = 2 exhibit a relatively low N-I point of 100°C or higher. relatively high N
- has an I point. In any case, by using the compound of the present invention in -C, the degree of freedom in selecting components when forming a liquid crystal composition is expanded.

[Production method of compound]

Next, the method for producing the compound of the present invention is shown. The desired trans- -4-substituted cyclohexanecarboxylic acid β-(4-substituted phenyl)ethyl ester is obtained.

This can be expressed as a formula (in the above formula, R, L, and X are the same as above). [Examples] The compounds of the present invention will be explained in more detail with reference to Examples below. In each example, the melting point is abbreviated as m, Po, the crystalline phase as C, the nematic phase as N1, and the transparent phase as I.

Example 1 [trans-4-()trans-4-ethylcyclohexyl)cyclohexanecarboxylic acid β-(4-ethoxyphenyl)ethyl ester (R” C2Hs in formula (I),
Production of β-(
4-ethoxyphenyl)ethyl alcohol 1.7 S'
(0,01-T-ru) was dissolved in 710 ml of viridi,
While stirring well, 2.6 t (0.01 mol) of trans-4-(trans-4-ethylcyclohexyl)cyclohexanecarboxylic acid chloride was added. This reaction solution was left overnight, poured into 100 d of water, and an oily substance was extracted with 100 d of toluene.

The toluene layer was washed with 6N-HCI, then with 2N-NaOH, further washed with water until neutral, and then filtered.
Toluene was distilled off under reduced pressure. The remaining crystals were recrystallized with ethanol to obtain the target product, trans-4-()trans-4-ethylcyclohexyl)cyclohexanecarboxylic acid β-(4-ethoxyphenyl)ethyl ester (tsr (yield: 39cm)). Ta. The C-N point of this is 83
．． The temperature was 9-85.5°C, and the N-I point was 107.5°C.

Examples 2 and 3 The following operation was carried out in accordance with Example 1 to produce the following compound of Formula I1.

trans-4-()trans-4-butylcyclohexyl)cyclohexanecarboxylic acid β-(4-ethoxyphenyl)ethyl ester (Example C-N points 112.7-11
3.3°C, N-I point 130.1°C.

trans-4-heptylcyclohexanecarphonic acid β-
(4-Ethoxyphenyl)ethyl ester (Example 3) m, P, 42.9-43.4°C, N-I point 21.5
℃.

Example 4 (Usage Example 1) Trans-4-propyl-(4-cyanophenyl)cyclohexay 25.5% (weight,
(same below) trans-4-pentyl-(4-cyanophenyl)cyclohexane 34. o-thitrans-4-heptyl-(4-cyanophenyl)cyclohexane 25.5% trans-
4-()Lance-4-ethylcyclohexyl)cyclohexanecarboxylic acid β-(4-ethoxyphenyl)ethyl ester (from Example 1) The nematic temperature range of the 15.0-inch liquid crystal mixture was -5 to 58°C. B. It is sufficiently practical as a nematic liquid crystal composition for display devices.

Example 5 (Use Example 2) Trans-4-propyl-(4'-cyanophenyl)cyclohexane 20% Trans-4-pentyl-(4'-cyanophenyl)cyclohexane 31 Thitrans-4-hebutyl-(4'-cyanophenyl) ) cyclohexane 21 thitrans-4-benthyl(4“-cyanobiphenyl)
Cyclohexane 13 H) U, 7-4-heptylcyclohexanecarboxylic acid β
-(4-ethoxyphenyl)ethyl ester (Example 3)
The nematic temperature range of the 15% liquid crystal mixture is 0 to 62°C, and it is sufficiently usable as a nematic liquid crystal composition for display devices.

that's all

Claims (2)

[Claims] (1) General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (In the above formula, R is an alkyl group having 1 to 15 carbon atoms, and X is C
A cyclohexanecarboxylic acid phenethyl ester derivative represented by N or an alkyl group or alkoxy group having 1 to 15 carbon atoms, and n is 1 or 2. (2) General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (In the above formula, R is an alkyl group having 1 to 15 carbon atoms, and X is C
Consisting of two or more components characterized by containing at least one component of a cyclohexanecarboxylic acid phenethyl ester derivative represented by N or an alkyl group or alkoxy group having 1 to 15 carbon atoms, where n is 1 or 2 liquid crystal composition.