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2-methyl-1,3-dioxepane derivative

A technology of alkyl and compound, applied in the field of liquid crystal compound synthesis and application

Inactive Publication Date: 2014-06-25
SHIJIAZHUANG CHENGZHI YONGHUA DISPLAY MATERIALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But so far, no single liquid crystal monomer has been used alone in liquid crystal displays without being combined with other compounds to meet the performance requirements.

Method used

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  • 2-methyl-1,3-dioxepane derivative
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  • 2-methyl-1,3-dioxepane derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0111] Example 1, Synthesis of Compound I-17 (Synthesis Route 1)

[0112]

[0113] step 1:

[0114]

[0115] Add 44.4g (0.24mol) p-bromobenzaldehyde (reactant), 21.6g (0.24mol) (reactant) of 1,4-butanediol, 400ml dry toluene (solvent), 2g p-toluenesulfonic acid to a 1L three-necked flask , heated to reflux for 4 hours, separated the formed water, cooled to room temperature, washed with 100ml of water, and evaporated to dryness to obtain 55.5g of (I-17-a), with a yield of 90% and a purity of 98% by gas chromatography.

[0116] step 2

[0117] Add 25.7g (0.1mol) (I-17-a) (reactant) and 150ml tetrahydrofuran (solvent) into the reaction flask, protect it with nitrogen, cool down to -60°C, add dropwise 0.2mol n-butyllithium (reactant ) of petroleum ether (solvent) solution, the dropwise addition was completed within 1 hour, and the reaction was stirred at -50°C for 30 minutes. Then cool down to -60°C, add dropwise 13g (0.13mol) trimethyl borate (reactant) in 70ml tetrahy...

Embodiment 2

[0130] Example 2, Synthesis of Compound I-18 (Synthesis Route 2)

[0131] step 1

[0132]

[0133] Add 0.1mol (Ⅰ-17-a), 0.12mol m-fluorophenylboronic acid (reactant), 0.13mol sodium carbonate (reactant), 80ml toluene (solvent), 60ml ethanol (solvent), 60ml water (solvent) to the reaction bottle ), under the protection of nitrogen, add 0.4g tetrakis (triphenylphosphine) palladium (catalyst), stir and heat to reflux for 3 hours. Cool down to room temperature, separate the layers, extract the aqueous phase with 50ml of toluene (solvent), and wash the organic phase with water until neutral. Evaporate the solvent to dryness, dissolve the resultant in 100ml of toluene, decolorize it through a silica gel column, elute with toluene (solvent), collect the eluent and evaporate the solvent to dryness, dissolve with 3 times of petroleum ether, freeze and recrystallize at -20°C, and filter with suction. 24.5 g of (I-18-a) were obtained as white crystals. The yield is 90%, and the gas...

Embodiment 3

[0149] Embodiment 3, the synthesis of compound I-19

[0150] step 1

[0151]

[0152] Add 25.7g (0.1mol) (Ⅰ-17-a) (reactant) and 120ml tetrahydrofuran (solvent) to the reaction bottle, install the seal and stir, replace the air with nitrogen, drop the temperature to -70°C, and add 0.1mol Concentration of 2.5M butyllithium (reactant), 20 minutes after the addition, dry carbon dioxide gas (reactant), to saturation, react at this temperature for 2 hours, pour this reaction solution into 20ml concentrated Hydrochloric acid (to adjust the pH value) and 100ml of water in a beaker for hydrolysis, liquid separation, 50ml of ethyl acetate (solvent) to extract the water phase once, combine the organic phase, wash with saturated saline until neutral, dry with anhydrous sodium sulfate (drying agent), Concentrate to remove the solvent to obtain a light yellow solid, which is recrystallized once with 2 times of toluene and 1 times of ethyl acetate (solvent) to obtain 20 g of white cryst...

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Abstract

The invention discloses a 2-methyl-1,3-dioxepane derivative. The structural general formula of the compound is as shown in the formula I. The compound is stable in structure, has a wide liquid crystal state temperature range, good low-temperature intersolubility and large dielectric anisotropy delta epsilon, can be used for realizing a low threshold voltage and low rotary viscosity gamma 1 when being used in an optical device, can be used for improving the performances of a liquid crystal composition material and a display device, and has great significance in quick response of the display device. A liquid crystal composition containing the compound can be applied to preparation of liquid crystal display devices with low driving voltage, wide temperature range and quick response speed. The formula I is as shown in the specification.

Description

technical field [0001] The invention belongs to the field of liquid crystal compound synthesis and application, and relates to a dioxepane derivative. Background technique [0002] Liquid crystal displays using liquid crystal compositions are widely used in displays such as instruments, computers, and televisions. For the field of liquid crystal display technology, although the market has become very large in recent years and the technology has gradually matured, people's requirements for display technology are also constantly improving. , especially in achieving fast response, reducing driving voltage, and reducing power consumption. As one of the important optoelectronic materials of liquid crystal display, liquid crystal material plays an important role in improving the performance of liquid crystal display. [0003] Liquid crystal display elements are divided into the following modes according to the display mode: twisted nematic (TN) mode, super twisted nematic (STN) m...

Claims

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Application Information

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IPC IPC(8): C07D321/06C09K19/44G02F1/1333
CPCC07D321/06C09K19/3402C09K19/44G02F1/1333
Inventor 韩耀华史正尚洪勇殷科张少勃华瑞茂
Owner SHIJIAZHUANG CHENGZHI YONGHUA DISPLAY MATERIALS CO LTD
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