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Vinyl cyclohexyl methyl ether liquid crystal compounds and preparation method thereof

A technology of liquid crystal compound and hexyl methyl ether, which is applied in the field of fine chemical industry and material chemistry, can solve the problems of insufficient liquid crystal range and no compound involved, and achieve the effects of lower threshold voltage, large dielectric anisotropy, and lower power consumption

Active Publication Date: 2014-01-29
VALIANT CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] However, this patent does not involve compounds where R2 is fluorine, given the properties and data of the compounds, the range of liquid crystals is not wide enough
[0006] Patent 2 JP2007023071A also involves the preparation of vinyl cyclohexyl methyl ether liquid crystal compounds, but does not involve the compounds protected by this patent

Method used

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  • Vinyl cyclohexyl methyl ether liquid crystal compounds and preparation method thereof
  • Vinyl cyclohexyl methyl ether liquid crystal compounds and preparation method thereof
  • Vinyl cyclohexyl methyl ether liquid crystal compounds and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0082] 2. Preparation of methyl 4-formylcyclohexylcarboxylate

[0083]

[0084] Experimental device: 1 liter three-necked flask, equipped with thermometer, stirring, N 2 Protection, ice bath.

[0085] Operation process: Add 56.8g of the above product and 200mL of THF to a three-necked flask, add 500mL of 5% hydrochloric acid dropwise, and control the temperature to be less than 10°C. After the addition is complete, heat to 30°C and keep it for 4 hours. Add 200mL water, use 200mL CH 2 Cl 2 Extract, wash with water to neutral, add anhydrous Na 2 SO 4 After drying, the solvent was removed with a rotary evaporator to obtain 48.5 g of light yellow liquid, yield: 96.0%, GC purity: 90.2%.

[0086] 3. Preparation of methyl 4-vinylcyclohexylcarboxylate

[0087]

[0088] Experimental device: 2-liter three-necked flask, equipped with thermometer, stirring, liquid sealing, N 2 Protection, drying tube.

[0089] Operation process: add CH to the three-necked bottle 3 PPh 3 Br106.8g and 200mLTHF. Pu...

Embodiment 1

[0102] Example 1: Preparation of VC10PUF

[0103] 1. Preparation of OHPUF

[0104]

[0105] Method a: Experimental device: 500mL three-necked flask, liquid seal, mechanical stirring, 0-100°C thermometer, reflux condenser, drying tube.

[0106] Operation process: Add 27.6g potassium carbonate and 55g water into a three-necked flask under the protection of nitrogen, stir and dissolve completely, add 17.6g 3,4,5-trifluorophenylboronic acid, 17.3g p-iodophenol, 0.224g tetratriphenylphosphine Palladium and 80g toluene were incubated at 70~90℃ for 3h. After the reaction, 200mL of water was added to the system and transferred to a separatory funnel. The organic phase was washed with water to neutrality, and the solvent was removed by a rotary evaporator to obtain 26g of crude product. Toluene and n-hexane were recrystallized once to obtain 19.6 g of product, with a yield of 87.0% and a GC purity of 98.2%.

[0107] Method b: Experimental device: 500mL three-necked flask, liquid seal, mechan...

Embodiment 2

[0119] Example 2: Preparation of VC10UUF

[0120] 1. Preparation of VC10U

[0121]

[0122] Method a: Experimental device: 500mL three-necked flask, liquid seal, mechanical stirring, 0~300℃ thermometer, reflux condenser, drying tube.

[0123] Operation process: Add 50g VCMI, 27.3g 3,5-difluorophenol, 22.4g potassium hydroxide and 200g toluene to a three-necked flask under the protection of nitrogen. The temperature is raised to reflux, and the reaction is kept for 10 hours. After the reaction, it is cooled to room temperature and added to the system. Add 200 mL of water, transfer to a separatory funnel, wash the organic phase with water to neutrality, remove the solvent on the rotary evaporator to obtain 48 g of the product, and recrystallize it twice with toluene and absolute ethanol to obtain 43.7 g of the product, yield 87.0%, GC purity 96.4%.

[0124] Method b: Experimental device: 500mL three-necked flask, liquid seal, mechanical stirring, 0~300℃ thermometer, reflux condenser, ...

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Abstract

The invention relates to vinyl cyclohexyl methyl ether liquid crystal compounds and a preparation method thereof. The compounds have great dielectric anisotropy, so that the compounds are beneficial to increase the dielectric constant of mixed liquid crystals and reduce the threshold voltage, thereby reducing the drive voltage of a liquid crystal panel and reducing the power consumption. Thus, the compounds have excellent use value. The structure of the liquid crystal compounds is shown in the specification. In the structural formula of the compounds, a, b, c, d, e, g, h and i are respectively hydrogen or fluorine; and f is fluorine.

Description

Technical field [0001] The invention relates to a vinyl cyclohexyl methyl ether liquid crystal compound and a preparation method thereof, and belongs to the technical field of fine chemicals and material chemistry. Background technique [0002] In recent years, liquid crystals have become more and more widely used. Vinyl cyclohexyl methyl ether liquid crystal compounds are an important part of liquid crystal compounds. Liquid crystal compounds containing this group have the characteristics of low viscosity, high charge retention, and superior performance. [0003] Patent 1WO2010095493A1 relates to the preparation of vinyl cyclohexyl methyl ether liquid crystal compounds, as follows: [0004] [0005] However, this patent does not involve compounds where R2 is fluorine. Given the properties and data of the compounds, the liquid crystal range is not wide enough. [0006] Patent 2 JP2007023071A also relates to the preparation of vinyl cyclohexyl methyl ether liquid crystal compounds, but...

Claims

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Application Information

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IPC IPC(8): C09K19/30C07C43/225C07C41/30
Inventor 付海超葛立权刘忠文万君玲张帆王斌韩娜
Owner VALIANT CO LTD
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