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3,7-disubstituted trans-dicyclo[3,3,0] octane compound and its prepn and use

A compound and disubstitution technology, applied in chemical instruments and methods, organic chemistry, instruments, etc., to achieve good low-temperature miscibility, moderate birefringence, and low power consumption

Inactive Publication Date: 2004-11-24
石家庄永生华清液晶有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, no single liquid crystal compound has been used alone in display devices

Method used

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  • 3,7-disubstituted trans-dicyclo[3,3,0] octane compound and its prepn and use
  • 3,7-disubstituted trans-dicyclo[3,3,0] octane compound and its prepn and use
  • 3,7-disubstituted trans-dicyclo[3,3,0] octane compound and its prepn and use

Examples

Experimental program
Comparison scheme
Effect test

Example Embodiment

Example 1

This example relates to the synthesis of intermediate 7,7-ethylenedioxy-3-trans bicyclo[3.3.0]octanone. 1) Synthesis of trans-bicyclo[3.3.0]octane 3,7-dione

Add 5.3 g of NaOH and 95 ml of anhydrous methanol to a 250 ml Erlenmeyer flask, stir until the NaOH is completely dissolved, and filter to obtain a NaOH / anhydrous methanol solution. Add 22.5 g of dimethyl acetone dicarboxylate, N 2 Under protection, add NaOH / anhydrous methanol solution with stirring, a white solid precipitates out, heat to reflux until the solid dissolves. Add 9.4 ml of 40% glyoxal aqueous solution dropwise, add in 25 minutes, and a solid precipitates out, then heat to reflux for 10 minutes, cool to room temperature, filter to obtain a yellow solid, and wash twice with 50 ml of cold methanol respectively.

Add 21 ml of 37% hydrochloric acid and 60 ml of water solution and yellow solid into a 250 ml three-necked flask, heat reflux for 3 hours, cool, and extract three times...

Example Embodiment

Example 2

3-pentyl-7-(4′-propylphenyl)ethyl-trans bicyclo[3.3.0]octane

The reaction process is as follows:

Add 3 g of magnesium shavings and 20 ml of anhydrous tetrahydrofuran to a 250 ml three-necked flask, and add 22 g of 3,5-difluorobromobenzene (99.7%) and 40 ml of anhydrous tetrahydrofuran to a 100 ml dropping funnel. Add 5 ml of the solution dropwise to initiate the reaction. The tetrahydrofuran solution was slowly added dropwise to maintain a slight reflux. After dripping, heat to reflux for 1 hour until the magnesium chips almost disappeared. A solution of 18 g of 7,7-ethanedioxy-3-trans bicyclo[3.3.0]octanone and 40 ml of tetrahydrofuran was added dropwise, and the solution was refluxed for 2 hours. Cool down to about 0°C. Add 24 ml of 6M hydrochloric acid dropwise, control the temperature below 30°C, and hydrolyze for half an hour. Pour into water, a large amount of sediment will separate out, filter, and discard the filtrate. Put 2 grams of...

Example Embodiment

Example 3

3-pentyl-7-(4′-propylphenyl)ethyl-trans bicyclo[3.3.0]octane

Add 20 grams of 3,3-ethylenedioxy-7-(3',4'-difluorophenyl)-trans-bicyclo[3.3.0]octane obtained in Example 2 to a 500-ml single-mouth bottle, 600 One milliliter of 88% formic acid, 200 milliliters of toluene, stir at room temperature for 12 hours, separate the layers, wash the toluene layer until it is neutral, and anhydrous Na 2 SO 4 Dry for 4 hours, filter and evaporate the solvent to obtain 16.15 g of 3-oxo-7-(3',4'-difluorophenyl)-trans-bicyclo[3.3.0]octane, melting point 44℃, gas purity 99.7 %.

The compound (b-n) obtained in Example 3 was hydrolyzed by referring to the same method as above to obtain the following compound:

3-oxo-7-(3′,5′-difluorophenyl)-trans bicyclo[3.3.0]octane

3-pentyl-7-(4′-propylphenyl)ethyl-trans bicyclo[3.3.0]octane

3-pentyl-7-(4′-propylphenyl)ethyl-trans bicyclo[3.3.0]octane

3-pentyl-7-(4′-propylphenyl)ethyl-trans bicyclo[3.3.0]octane

3-pent...

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Abstract

The present invention provides one novel kind of 3, 7-disubstituted trans-dicyclo[3, 3, 0] octane compound and its preparation process and the application in liquid crystal composition. The compound has stable structure, stable property, excellent low temperature intersolubility, relatively low viscosity and short response time. It may be used in liquid crystal composition and the liquid crystal composition has low power consumption, low viscosity and short response time. It has excellent application foreground in TN, STN, HTN, TFT, FMLCD whole wavelength cholest LCD display.

Description

Technical field: The present invention relates to a novel 3,7-disubstituted trans-bicyclo[3.3.0]octane compound, its preparation method and the application of the compound in liquid crystal composition and liquid crystal display. Background technique: Liquid crystal materials develop rapidly along with the development of liquid crystal displays (LCDs), among which nematic liquid crystal materials for display are the fastest growing liquid crystal materials with the largest market share. As a liquid crystal material for display, it has also been greatly developed, and a large number of liquid crystal compounds have appeared. From biphenyl nitriles, esters, oxygen-containing heterocyclic benzenes, and pyrimidine ring liquid crystal compounds to cyclohexyl (bi) benzenes, diphenylacetylenes, ethyl bridges, olefinic end group liquid crystals and various Fluorine-containing aromatic ring liquid crystal compounds, Japan recently synthesized structurally stable difluoride vinyl li...

Claims

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Application Information

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IPC IPC(8): C07C25/18C07C25/24C07C43/235C07C49/443C07C49/517C07C49/67C07C49/687C07C49/753C07D317/72
Inventor 康杰姜天孟田秋峰
Owner 石家庄永生华清液晶有限公司
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