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Spiro[3,5]nonane derivatives and their preparation methods and applications

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

Active Publication Date: 2016-03-16
BEIJING CHENGZHI YONGHUA DISPLAY TECHNOLOGY 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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  • Spiro[3,5]nonane derivatives and their preparation methods and applications
  • Spiro[3,5]nonane derivatives and their preparation methods and applications
  • Spiro[3,5]nonane derivatives and their preparation methods and applications

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0136] Compound of Example 1 Synthesis of (I-14) (Method 1)

[0137]

[0138] Step 1 (I-14-a) synthesis

[0139] Add 400ml tetrahydrofuran (solvent) and 101g (0.25mol) methyl iodide phosphonium salt (reactant) into a 1L three-necked flask, stir and cool down to 0°C, add 28g (0.25mol) potassium tert-butoxide (reactant) in batches, and complete the addition Stir for 1 hour, add dropwise a solution of 42g (0.2mol) 3,5-difluorophencyclohexanone (reactant) and 100ml tetrahydrofuran, stir for 1 hour after dropping, add 300ml water, stir for 10 minutes, separate the liquids, and steam Solvent, add 300ml of petroleum ether column chromatography, evaporate to dryness to obtain product 37.4g yield 90%, gas chromatography purity 97%;

[0140] Synthesis of Step 2 (I-14-b)

[0141] Add 300ml ether (solvent), 62.4g (0.3mol) (I-14-a) (reactant), 31.4g (0.483mol) zinc (catalyst) and 1.5g copper (II) acetate monohydrate to a 1L three-necked flask (catalyst), followed by dropwise additi...

Embodiment 2

[0159] Embodiment 2, Synthesis of (method 1)

[0160]

[0161] Step 1 (I-15-a) synthesis

[0162] Add 400ml tetrahydrofuran (solvent) and 101g (0.25mol) methyl iodide phosphonium salt (reactant) into a 1L three-necked flask, stir and cool down to 0°C, add 28g (0.25mol) potassium tert-butoxide (reactant) in batches, and complete the addition Stir for 1 hour, add dropwise a solution of 34.8g (0.2mol) phenylcyclohexanone (reactant) and 100ml tetrahydrofuran, stir for 1 hour after dropping, add 300ml of water, stir for 10 minutes, separate liquids, evaporate the solvent, add 500ml Petroleum ether column chromatography, evaporated to dryness to obtain product 31g, yield 90%, gas chromatography purity 97%

[0163] Synthesis of Step 2 (I-15-b)

[0164] Add 400ml ether (solvent), 51.6g (0.3mol) (I-15-a) (reactant), 31.4g (0.483mol) zinc (catalyst) and 1.5g copper (II) acetate monohydrate to a 1L three-necked flask (catalyst), followed by dropwise addition of 60 g (0.33 mol) of...

Embodiment 3

[0187] Embodiment 3, Synthesis of (method 2)

[0188]

[0189] Synthesis of Step 1 (I-16-a)

[0190] Add 0.1mol (Ⅰ-15-d) (reactant) obtained in the step to the reaction bottle, 120ml tetrahydrofuran (solvent), install and seal and stir, replace the air with nitrogen, cool to -70°C, add dropwise 0.1mol concentration to 2.5M butyllithium (reactant), 20 minutes after the addition, dry carbon dioxide gas (reactant), to saturation, reacted at this temperature for 2 hours, pour this reaction solution into 20ml concentrated hydrochloric acid (adjust pH Value) and 100ml water in a beaker for hydrolysis, liquid separation, 50ml ethyl acetate (solvent) to extract the water phase once, combine the organic phase, wash with saturated saline until neutral, dry with anhydrous sodium sulfate (desiccant), concentrate to remove the solvent , to obtain a light yellow solid, which was recrystallized once with 2 times of toluene and 1 times of ethyl acetate (solvent) to obtain white crystals...

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Abstract

The invention discloses a spiro [3,5] nonane derivative, and a preparation method and application thereof. The structural general formula of the compound is as shown in a formula I (refer to the Specification). The compound has a stable structure, wide liquid crystal state temperature range, high low-temperature intersolubility and large dielectric anisotropy delta epsilon, can realize low threshold voltage and low rotary viscosity gamma 1 when being used by an optical device, can improve the performance of a liquid crystal composite material and a display and has important significance in realizing quick response of the display. A liquid crystal composition containing the compound can be applied to preparation of a liquid crystal display with low driving voltage, wide temperature range and high response speed. The formula I is shown in specifications.

Description

technical field [0001] The invention belongs to the field of synthesis and application of liquid crystal compounds, and relates to a spiro[3,5]nonane derivative and a preparation method and application thereof. 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 terms of achieving fast response and reducing driving voltage to reduce 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 disp...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C43/225C07C41/16C07C41/01C09K19/44C09K19/46G02F1/1333
CPCC07C41/01C07C41/16C07C43/225C07C2601/14C07C2602/50C09K19/32C09K19/44C09K19/46G02F1/1333
Inventor 韩耀华夏治国华瑞茂赵利峰张建立王奎
Owner BEIJING CHENGZHI YONGHUA DISPLAY TECHNOLOGY CO LTD
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