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Liquid crystalline compound having 2,6-difluorophenyl ether structure and liquid crystal composition thereof

一种化合物、-CH2-的技术，应用在有机化学、液晶材料、有机化学方法等方向，能够解决粘度高、T→i降低等问题，达到低粘度、高混合性的效果

Active Publication Date: 2016-02-03
DIC CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, molecules with linking groups are generally not only highly viscous, but also exist so that T →i Significantly reduce the disadvantage of such

Method used

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  • Liquid crystalline compound having 2,6-difluorophenyl ether structure and liquid crystal composition thereof
  • Liquid crystalline compound having 2,6-difluorophenyl ether structure and liquid crystal composition thereof
  • Liquid crystalline compound having 2,6-difluorophenyl ether structure and liquid crystal composition thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0292] (Example 1) trans-2-(3,4,5-trifluorophenyl)-5-[(2,6-difluoro-4-propylphenyloxy)methyl]-1,3 -two Production of alkane(1-1)

[0293][chem 47]

[0294]

[0295] (1-1) Under a nitrogen atmosphere, 3,4,5-trifluorobenzaldehyde (7.5 g), 2-hydroxymethyl-1,3-propanediol (5.0 g) and p-toluenesulfonic acid monohydrate ( 0.5 g) was suspended in toluene (30 mL), refluxed, and stirred for 3 hours while distilling off generated water. After standing to cool, saturated aqueous sodium bicarbonate solution (15 mL) was added for liquid separation, the organic layer was washed with saturated aqueous sodium bicarbonate solution and saturated brine, and dried by adding anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure to obtain crude 5-hydroxymethyl-2-(3,4,5-trifluorophenyl)-1,3-bis Alkane (11.3 g).

[0296] (1-2) Under a nitrogen atmosphere, the 5-hydroxymethyl-2-(3,4,5-trifluorophenyl)-1,3-bis Alkane (11.3 g), 2,6-difluoro-4-propylphenol (...

Embodiment 2

[0300] (Example 2) trans-2-[4-(3,4,5-trifluorophenyl)phenyl]-5-[(2,6-difluoro-4-propylphenyloxy)methyl base]-1,3-di Manufacturing of alkanes

[0301] [chem 48]

[0302]

[0303] (2-1) Under a nitrogen atmosphere, mix 4-bromobenzaldehyde (20.0g), tetrakis(triphenylphosphine)palladium(0) (2.5g), THF (100mL) and 2mol% potassium carbonate aqueous solution (110mL) Mix and heat to 60°C. A solution in which 3,4,5-trifluorophenylboronic acid (20.9 g) was dissolved in THF (60 mL) was slowly added under heating, and stirred at 60° C. for 15 hours. After standing to cool, the insoluble matter was filtered, toluene (30 mL) was added for liquid separation, the organic layer was washed twice with saturated brine (100 mL), and dried with anhydrous sodium sulfate. After distilling off the solvent under reduced pressure, it purified by silica gel column chromatography and recrystallized from a mixed solvent of toluene and hexane to obtain 4-(3,4,5-trifluorophenyl)benzaldehyde (24.6 g)....

Embodiment 3

[0308] (Example 3) trans-2-[4-(3,4,5-trifluorophenyl)-3-fluorophenyl]-5-[(2,6-difluoro-4-propylphenyl Oxy)methyl]-1,3-bis Manufacturing of alkanes

[0309] [chem 49]

[0310]

[0311] (3-1) Under a nitrogen atmosphere, 3-fluorobenzaldehyde (6.0 g), 2-hydroxymethyl-1,3-propanediol (5.0 g) and p-toluenesulfonic acid monohydrate (0.5 g) were suspended in Toluene (30 mL) was refluxed, and stirred for 3 hours while distilling off generated water. After standing to cool, saturated aqueous sodium bicarbonate solution (15 mL) was added for liquid separation, the organic layer was washed with saturated aqueous sodium bicarbonate solution and saturated brine, and dried by adding anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure to obtain crude 5-hydroxymethyl-2-(3-fluorophenyl)-1,3-di Alkane (10.1 g).

[0312] (3-2) Under a nitrogen atmosphere, the 5-hydroxymethyl-2-(3-fluorophenyl)-1,3-bis obtained from (3-1) Alkane (10.1g), triphenylp...

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Abstract

The present invention pertains to compounds having a 2,6-difluorophenyl ether structure useful as an organic electronic material, or a medical or agricultural chemical, and particularly as a material for liquid crystal display elements; and to an effective manufacturing method for the compounds. Provided are a compound represented by general formula (1), as well as a liquid crystal composition containing the compound, and a liquid crystal display element employing the liquid crystal composition. Through the use of a compound represented by general formula (1) as a component of a liquid crystal composition, there can be obtained liquid crystal compositions exhibiting low viscosity, and exhibiting the liquid crystal phase over a wide temperature range. The compounds are therefore extremely useful as constituent components of liquid crystal compositions for use in liquid crystal display elements of which fast response is required.

Description

technical field [0001] The present invention relates to a compound having a 2,6-difluorophenyl ether structure useful as an organic electronic material, a medicine / agricultural chemical, and particularly a material for a liquid crystal display element, and an effective production method thereof. Background technique [0002] From clocks and calculators, liquid crystal display components have developed into various measurement equipment, automotive panels, word processors, electronic notepads, printers, computers, televisions, clocks, advertising display boards, etc. Typical liquid crystal display methods include TN (Twisted Nematic) type, STN (Super Twisted Nematic) type, vertical alignment type using TFT (Thin Film Transistor), and IPS (In-Plane Switching) type. The liquid crystal compositions used in these liquid crystal display elements are required to be stable to external factors such as moisture, air, heat, light, and in addition, to exhibit a liquid crystal phase (nem...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D319/06C09K19/34C07B61/00
CPCC07D319/06C09K19/0403C09K19/3402C09K2019/3422
Inventor 东条健太楠本哲生
Owner DIC CORP
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