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Liquid crystal compound containing acetal ring and preparation method thereof

A liquid crystal compound and compound technology, applied in chemical instruments and methods, liquid crystal materials, organic chemistry, etc., can solve the problem that liquid crystal monomers cannot meet the needs of liquid crystal display, etc., to improve the light response speed, broaden the application range, and clear the point. high effect

Active Publication Date: 2016-10-26
XIAN CAIJING OPTO ELECTRICAL SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] In short, researchers have been working hard to explore the relationship between liquid crystal molecular structure and performance, expecting to obtain liquid crystal monomers with different properties, and striving to further meet the development of modern liquid crystal display technology, but the research and development of liquid crystal monomers is still not enough. Meet the needs of liquid crystal display

Method used

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  • Liquid crystal compound containing acetal ring and preparation method thereof
  • Liquid crystal compound containing acetal ring and preparation method thereof
  • Liquid crystal compound containing acetal ring and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Under nitrogen protection at a flow rate of 0.6mL / min, 2.55g of 2-methyl-4-(4-trans-(4-n-propylcyclohexyl)ethylphenyl)-3-butyn-2-ol , 0.25g tetra-n-butylammonium bromide, 5.23g potassium hydroxide, 16mL toluene and 4mL distilled water are added in the three-necked flask that thermometer, magnetic stirring bar, condenser tube are housed, and the three-necked flask is placed in the oil bath, and Raise the temperature to 60°C and react for 40 minutes. After the solid is completely dissolved, add 2.00g of 4-bromophenylpropionaldehyde acetal and 0.27g of tetrakis(triphenyl)phosphine palladium, raise the temperature to 80°C, and stir the reaction at constant temperature for 12 hours to end the reaction , the reaction solution was cooled to room temperature, and filtered with diatomaceous earth, the filtrate was extracted with ethyl acetate, and the organic phase obtained after liquid separation was washed to neutrality, then dried with anhydrous magnesium sulfate and concentra...

Embodiment 2

[0043] In Example 1, the 4-bromophenylpropionaldehyde acetal used was replaced with an equimolar 3-fluoro-4-bromophenylpropionaldehyde acetal, and the other steps were the same as in Example 1 to obtain white crystals—containing acetal The liquid crystal compound of ring, its yield is 50%, and chemical name is 1-{4-[2-(4-n-propylcyclohexyl) ethyl] phenyl}-2-[2-fluoro-4-(propane Aldehyde (ethylene glycol acetal) phenyl] acetylene, the specific chemical reaction equation is as follows:

[0044]

[0045] The structural characterization data of the resulting white crystals are as follows:

[0046] 13 C-NMR (CDCl 3 as solvent, internal standard is TMS, 75MHz, ppm): 164.2, 160.9, 144.6, 144.0, 133.2, 131.6, 128.4, 124.1, 120.2, 115.3, 109.6, 103.5, 94.2, 82.2, 65.0, 39.8, 39.1, 37.5, 37.5 , 35.0, 33.3, 33.3, 33.3, 29.9, 20.1, 14.5. Spectrum such as Figure 4 shown.

[0047] 1 H-NMR (CDCl 3 As a solvent, the internal standard is TMS, 300MHz, ppm): 7.40 (dd, J = 18.0, 7.8Hz...

Embodiment 3

[0052] In Example 1, the 2-methyl-4-(4-trans-(4-n-propylcyclohexyl)ethylphenyl)-3-butyn-2-alcohol was used with equimolar 2-methyl Base-4-(4-trans-(4-n-ethylcyclohexyl)ethylphenyl)-3-butyn-2-alcohol was replaced, and other steps were the same as in Example 1 to obtain white crystals—containing acetal The liquid crystal compound of ring, its yield is 45%, and chemical name is 1-{4-[2-(4-n-ethylcyclohexyl) ethyl] phenyl}-2-[4-(propionaldehyde ethylene glycol Acetal) phenyl] acetylene, the specific chemical reaction equation is as follows:

[0053]

[0054] The NMR structure confirmation data showed that the obtained white crystal was the target product, and its optical anisotropy and dielectric anisotropy properties were not substantially different from those of the liquid crystal compound obtained in Example 1.

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Abstract

The invention discloses a liquid crystal compound containing acetal. A structural formula of the compound is as shown in the specification, wherein R is C2-C5 linear alkyl, m is 0 or 1, and cyclohexyl is trans-cyclohexyl. The liquid crystal compound is obtained by enabling substituted aryl alkynol and substituted benzenepropanal acetal to generate sonogashira coupling reaction, and the synthesis method is simple, relatively low in cost, and suitable for industrial production. The liquid crystal compound disclosed by the invention has positive dielectric anisotropy and a certain nematic phase liquid crystal region, a relatively high clearing point and proper optical anisotropy, is excellent in solubility with other liquid crystal compounds, and can be applied to an IPS display mode and a TN display mode.

Description

technical field [0001] The invention belongs to the technical field of liquid crystal compounds, and in particular relates to a novel liquid crystal compound containing an acetal ring and a preparation method thereof. Background technique [0002] Since the development of liquid crystal display, it is still impossible to find a liquid crystal monomer to meet the many requirements of liquid crystal materials for display. It is still necessary to mix various liquid crystal compounds in appropriate proportions in order to obtain the best match of various special parameters to meet various requirements. Different display requirements. Therefore, liquid crystal materials for display have grown along with the development of liquid crystal displays, and a large number of liquid crystal compounds have appeared. From azo, azo oxide, benzylidene, biphenylene cyanide, esters, oxygen-containing heterocyclic rings, pyrimidine ring liquid crystal compounds to cyclohexyl (bi)benzenes, tol...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09K19/34C07D317/12C07D317/16
Inventor 安忠维陈然陈新兵陈沛
Owner XIAN CAIJING OPTO ELECTRICAL SCI & TECH
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