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1-alkoxy-2, 3-difluoro-4-(2-(4-(trans-4-alkyl cyclohexyl) phenyl) acetenyl) benzene and preparation method thereof

A technology of alkoxybenzene and alkoxy, which is applied in the field of benzyne-based negative liquid crystal materials, can solve the problems of poor chemical stability and photochemical stability, weak negative dielectric anisotropy, and high viscosity of liquid crystal materials. Good stability and photochemical stability, enhanced negative dielectric anisotropy, and moderate negative dielectric anisotropy

Inactive Publication Date: 2012-08-15
BENGBU CHINA SYNCHEM TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The melting point of traditional liquid crystal materials is high, resulting in high viscosity of liquid crystal materials, and the response speed will be reduced; and the negative dielectric anisotropy is weak, and the chemical stability and photochemical stability are poor.
In traditional preparation methods, triphenylphosphine palladium chloride or palladium chloride is usually used as a catalyst, which is expensive and difficult to recycle, resulting in increased production costs

Method used

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  • 1-alkoxy-2, 3-difluoro-4-(2-(4-(trans-4-alkyl cyclohexyl) phenyl) acetenyl) benzene and preparation method thereof
  • 1-alkoxy-2, 3-difluoro-4-(2-(4-(trans-4-alkyl cyclohexyl) phenyl) acetenyl) benzene and preparation method thereof
  • 1-alkoxy-2, 3-difluoro-4-(2-(4-(trans-4-alkyl cyclohexyl) phenyl) acetenyl) benzene and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Under the protection of nitrogen, 0.1725mol, 46.06gg (1.0eq) of 4-(4-ethylcyclohexyl)bromobenzene, 0.1725mol, 28.98g (1.0eq) 2,3-difluoro-4-methyl Oxyphenyl acetylene, 4.0g palladium-carbon, 0.1725mol, 0.328g (0.01eq) cuprous iodide, 0.00345mol, 0.904g triphenylphosphine, 0.1725mol, 18.3g sodium carbonate, 200ml, 1.9mol toluene into the reaction flask In the medium, start stirring, heat up to 50°C to keep the temperature for the reaction, and control the gas phase. After the reaction of the raw materials is completed, the palladium-carbon is removed by suction filtration, the reaction solution is frozen until the product precipitates, and the 1-methoxy-2,3-bis is obtained after suction filtration Crude fluoro-4-[2-[4-(trans-4-ethylcyclohexyl)phenyl]ethynyl]benzene. To the above crude 1-methoxy-2,3-difluoro-4-[2-[4-(trans-4-ethylcyclohexyl)phenyl]ethynyl]benzene was added 5 times equivalent of ethanol and 5% equivalent of activated carbon is heated and refluxed for re...

Embodiment 2

[0024] Under the protection of nitrogen, 0.1725mol, 48.47g (1.0eq) of 4-(4-propylcyclohexyl) bromobenzene, 0.19mol, 34.5g (1.1eq) 2,3-difluoro-4-ethane Oxyphenyl acetylene, 4.0g palladium on carbon, 0.1725mol, 0.328g (0.01eq) cuprous iodide, 0.00345mol, 0.904g triphenylphosphine, 0.1725mol, 18.3g sodium carbonate, 200ml, 1.4mol triethylamine In the reaction flask, turn on the stirring, heat up to 60°C to keep the reaction warm, and control the gas phase. After the reaction of the raw materials is completed, the palladium carbon is removed by suction filtration. The reaction solution is frozen until the product precipitates. After suction filtration, 1-ethoxy-2,3 is obtained. -Crude difluoro-4-[2-[4-(trans-4-propylcyclohexyl)phenyl]ethynyl]benzene. To the crude 1-ethoxy-2,3-difluoro-4-[2-[4-(trans-4-propylcyclohexyl)phenyl]ethynyl]benzene was added 5 times equivalent of petroleum ether and 5% equivalent of activated carbon is heated and refluxed to recrystallize. The activat...

Embodiment 3

[0026] Under the protection of nitrogen, 0.1725mol, 54.34g (1.0eq) of 4-(4-pentylcyclohexyl) bromobenzene, 0.207mol, 46.37g (1.2eq) 2,3-difluoro-4-pentane Oxyphenyl acetylene, 4.0g palladium-carbon, 0.1725mol, 0.328g (0.01eq) cuprous iodide, 0.00345mol, 0.904g triphenylphosphine, 0.1725mol, 18.3g sodium carbonate, 200ml, 1.9mol toluene into the reaction flask In the medium, turn on the stirring, heat up to 80°C to keep the reaction, and control the gas phase. After the raw material reaction is completed, the palladium-carbon is removed by suction filtration, the reaction solution is frozen until the product precipitates, and the 1-pentyloxy-2,3-bis is obtained after suction filtration Crude fluoro-4-[2-[4-(trans-4-pentylcyclohexyl)phenyl]ethynyl]benzene. Add 5 times equivalent of petroleum ether to the above crude 1-pentoxy-2,3-difluoro-4-[2-[4-(trans-4-pentylcyclohexyl)phenyl]ethynyl]benzene And 5% equivalent of activated carbon heated and refluxed for recrystallization, suct...

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Abstract

The invention discloses a benzyne negative liquid crystal material 1-alkoxy-2, 3-difluoro-4-(2-(4-(trans-4-alkyl cyclohexyl) phenyl) acetenyl) benzene and a preparation method of the 1-alkoxy-2, 3-difluoro-4-(2-(4-(trans-4-alkyl cyclohexyl) phenyl) acetenyl) benzene. The 1-alkoxy-2, 3-difluoro-4-(2-(4-(trans-4-alkyl cyclohexyl) phenyl) acetenyl) benzene has the structural formula as shown in the specification, wherein R in the formula is linear chain alkyl with 2-5 carbon atoms, and R' is linear chain alkyl with 2-5 carbon numbers; coupling reaction is carried out between 2, 3-difluoro-4-alkoxy phenylacetylene and 4-(4-alkyl cyclohexyl) bromobenzene, and a reaction product is purified to obtain a product with the content of more than 98%; the delta n of liquid crystal molecules can be increased by introducing acetylenic bonds, and due to the introduction of fluorine atoms with maximum electronegativity and shorter semidiameter, the physical property of the liquid crystal molecules can be improved, the negative dielectric anisotropy can be greatly increased, and the thermal stability and the viscosity of matrix liquid crystals are basically invariable; and the benzyne negative liquid crystal material provided by the invention has the advantages of being low in melting point, proper in negative dielectric anisotropy, and good chemical stability and photochemical stability.

Description

Technical field [0001] The present invention relates to a negative liquid crystal material of benzyne type, especially 1-alkoxy-2,3-difluoro-4-[2-[4-(trans-4-alkylcyclohexyl)phenyl] Ethynyl]benzene and its preparation method. Background technique [0002] In recent years, as liquid crystal displays have been widely used in the field of information display, people's research interest in liquid crystal materials has been stimulated. Optical anisotropy (Δn) is an important property of liquid crystal materials. With people's pursuit of the performance of liquid crystal display such as wide viewing angle and fast response, optical anisotropy (Δn) liquid crystal materials have attracted much attention. At the same time, the low temperature performance of liquid crystal materials is also the focus of the industry. The high melting point of traditional liquid crystal materials results in high viscosity of the liquid crystal materials and lower response speed; and the negative dielectri...

Claims

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Application Information

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IPC IPC(8): C07C43/225C07C41/30C09K19/30
Inventor 杨青刘兴华赵士民徐剑霄汪平刘洪强
Owner BENGBU CHINA SYNCHEM TECH CO LTD
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