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Novel LCD compound p-n-heptyloxy cinnamic acid -2-fluoro-4-hydroxy- benzonitrile ester and its preparation method

A technology of n-heptyloxycinnamic and liquid crystal compounds, which is applied in the field of replacing cinnamate organic liquid crystal compounds and its preparation, can solve the problems of low working voltage and low viscosity, achieve high clearing point, stable chemical properties, and wide range of liquid crystals Effect

Inactive Publication Date: 2006-02-08
QINGDAO UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although there have been many reports on liquid crystal materials, not all of them are suitable for use in display devices, because liquid crystal materials for display must meet a wide operating temperature range, low operating voltage, low viscosity, fast response, high Stability and other requirements

Method used

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  • Novel LCD compound p-n-heptyloxy cinnamic acid -2-fluoro-4-hydroxy- benzonitrile ester and its preparation method
  • Novel LCD compound p-n-heptyloxy cinnamic acid -2-fluoro-4-hydroxy- benzonitrile ester and its preparation method
  • Novel LCD compound p-n-heptyloxy cinnamic acid -2-fluoro-4-hydroxy- benzonitrile ester and its preparation method

Examples

Experimental program
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Effect test

Embodiment 1

[0016] 1) Dissolve 0.01mol of p-hydroxycinnamic acid and 0.02mol of potassium hydroxide in 40ml of 95% (volume fraction) ethanol, then add 0.03mol of n-heptane bromide drop by drop at a speed of about 1ml / min, reflux for 24h, and then Add 14ml of 70% (volume fraction) ethanol solution of 0.02mol potassium hydroxide, and continue to reflux for 2h. Add 100ml of water, 20ml of concentrated hydrochloric acid, heat for 15min, cool and filter, wash with distilled water, dry, and then recrystallize with 95% (volume fraction) ethanol to obtain p-heptyloxycinnamic acid as white flaky crystals. 54%.

[0017] 2) Add 0.01mol of p-heptyloxycinnamic acid and 20ml of anhydrous tetrahydrofuran into a three-necked flask, stir to dissolve completely, then add 0.01mol of DCC (N,N-dicyclohexylcarbodiimide), and wait for After the turbidity phenomenon, 0.01mol2-fluoro-4-hydroxybenzonitrile and a small amount of DMAP[4-(N,N-dimethylamino)pyridine] were dissolved in 20ml of anhydrous tetrahydrofura...

Embodiment 2

[0019] 1) Dissolve 0.02mol of p-hydroxycinnamic acid and 0.05mol of potassium hydroxide in 100ml of 95% (volume fraction) ethanol, then add 0.03mol of n-heptane bromide, and reflux for 48h. Then add 35ml of 70% (volume fraction) ethanol solution of 0.03mol potassium hydroxide, and continue to reflux for 2h. Add 100ml of water and 40ml of concentrated hydrochloric acid, mix well, heat for 20min, cool and filter, wash with distilled water, dry, and recrystallize with 95% (volume fraction) ethanol to obtain p-heptyloxycinnamic acid as white flaky crystals , yield 49%.

[0020] 2) Add 0.015mol of p-heptyloxycinnamic acid and 50ml of anhydrous tetrahydrofuran into a three-necked flask, stir to dissolve completely, then add 0.01mol of DCC (N,N-dicyclohexylcarbodiimide), and wait until After the turbidity, 0.015mol 2-fluoro-4-hydroxybenzonitrile and a small amount of DMAP[4-(N,N-dimethylamino)pyridine] were completely dissolved in 35ml of anhydrous tetrahydrofuran to form a solution...

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Abstract

The invention relates to a fluorocyano-containing cinnamic ester liquid crystal compound and its preparing process, wherein the chemical structure of the compound is p-orthopentyloxy cinnamic acid-2-fluoro-4-hydroxybenzene nitrile ester, The preparation process comprises introducing alkoxy to 4-position of cinnamic acid (3-phenylacrylic acid) through Williamson etherification reaction, then carrying out DCC dehydration condensation, so as to make the substituted cinnamic acid and 2-fluoro-4-hydroxybenzene nitrile condense and produce needed compound. The invention also discloses the use of the compound, which can be used in not only mixed liquid crystal, but also in various LCDs.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a substituted cinnamate organic liquid crystal compound containing a fluorine atom and a cyano group, a preparation method and an application thereof. Background technique [0002] In recent years, liquid crystal compounds and liquid crystal materials have become one of the hot spots in the research of applied chemistry and material chemistry, and have been widely used in electronics, optics, acoustics, bioengineering, chemical industry, etc., and the most extensive and important It is its application in electronic display. With the development of the information industry, the requirements for liquid crystal materials are constantly increasing. Although there have been many reports on liquid crystal materials, not all of them are suitable for use in display devices, because liquid crystal materials for display must meet a wide operating temperature range, low operating...

Claims

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Application Information

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IPC IPC(8): C07C255/50C09K19/16G02F1/13
Inventor 张书圣黄学青李强宋修艳任锐
Owner QINGDAO UNIV OF SCI & TECH
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