Difluorobenzene derivative and nematic liquid crystal composition by using the same

A technology of liquid crystal composition and compound, which is applied in the direction of liquid crystal materials, chemical instruments and methods, organic chemistry, etc., can solve the problems of unusable and slow liquid crystal composition for VA, and achieve high voltage retention, excellent reliability, and viscosity low effect

Active Publication Date: 2008-02-20
DIC CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, since this compound has a hydroquinone skeleton, it has been found that it cannot be used for an effective matrix in terms of voltage retention (see Non-Patent Document 1), and it has been slow to develop a low-viscosity liquid crystal composition for VA using this compound.

Method used

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  • Difluorobenzene derivative and nematic liquid crystal composition by using the same
  • Difluorobenzene derivative and nematic liquid crystal composition by using the same
  • Difluorobenzene derivative and nematic liquid crystal composition by using the same

Examples

Experimental program
Comparison scheme
Effect test

manufacture example

[0111] (Method 1)

[0112] Make formula (9)

[0113] [chemical 15]

[0114]

[0115] The diketone compound represented is reacted with an ylide prepared from methoxymethyltriphenylsulfonium chloride to obtain formula (10)

[0116] [chemical 16]

[0117]

[0118] indicated compound. This reaction is often called the wittig reaction. The compound of the obtained formula (10) is hydrolyzed by an acid catalyst, and the compound of the formula (11) is obtained by cis-trans isomerization under alkaline conditions

[0119] [chemical 17]

[0120]

[0121] indicated compound. The resulting compound of formula (11) is reacted with an ylide prepared from methyltriphenylsulfonium bromide to obtain formula (12)

[0122] [chemical 18]

[0123]

[0124] indicated compound. The compound of gained formula (12) is reduced using reducing agents such as sodium borohydride to obtain formula (13)

[0125] [chemical 19]

[0126]

[0127] indicated compound. Gaining formula...

Embodiment 1

[0195] (Example 1) 1-((E)-2-butenyloxy)-2,3-difluoro-4-(trans-4-(trans-4-vinylcyclohexyl)cyclohexyl)methoxy Synthesis of Benzene (1a)

[0196] (1-1) Synthesis of 4-(2-butenyloxy)-2,3-difluorophenol

[0197] [chem 35]

[0198]

[0199] Synthesis of (1-1-1)1-(2-butenyloxy)-2,3-difluorobenzene

[0200] In 77.2g of 2,3-difluorophenol in 2-butanol (600ml) solution, add 122g of anhydrous potassium carbonate, then add 90.0ml of 1-bromo-2-butene (E / Z ratio=92 / 8). After heating to reflux for 4 hours, it was cooled to room temperature, and water was added dropwise to stop the reaction. It was extracted with hexane (3 times), and the collected organic layer was washed successively with 3M hydrochloric acid, water, saturated aqueous sodium bicarbonate solution, and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and vacuum distillation (155-160° C., 50 kPa) obtained 1-(2-butenyloxy)-2,3-difluorobenzene (E / Z ratio=82) in the form of 106 ...

Embodiment 2

[0225] (Example 2) Synthesis of 2,3-difluoro-1-(2-propenyloxy)-4-(trans-4-vinylcyclohexylmethoxy)benzene (2a)

[0226] (2-1) Synthesis of 4-(2-propenyloxy)-2,3-difluorophenol

[0227] [chem 37]

[0228]

[0229] In Example 1, the same operation as (1-1) was performed using 3-bromo-1-propene instead of 1-bromo-2-butene to obtain 4-(2-propenyloxy)-2,3- Difluorophenol

[0230] (2-2) Synthesis of 2,3-difluoro-1-(2-propenyloxy)-4-(trans-4-vinylcyclohexylmethoxy)benzene

[0231] [chem 38]

[0232]

[0233] Synthesis of (2-2-1) methyl 4-methoxymethylenecyclohexanecarboxylate

[0234] Disperse 263.4 g of methoxymethyltriphenylsulfonium chloride in 750 mL of tetrahydrofuran, and add 86.2 g of potassium tert-butoxide within 5 minutes at -9 to -4°C. After stirring at -4 to -11°C for 30 minutes, 100.0 g of methyl 4-oxocyclohexanedicarboxylate was dissolved in 300 mL of THF and added dropwise at -10 to 4°C over 80 minutes. After stirring at 0-4° C. for 60 minutes, 7.0 g of ammo...

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Abstract

This invention provides a nematic liquid crystal composition characterized by comprising 10 to 80% by mass of one or at least two compounds represented by general formula (I) as a first component [Chemical formula 1] and 20 to 70% by mass of one or at least two compounds represented by general formula (II) R<3>-B<1>-Y<1>-(B<2>-Y<2>)p-R<4> as a second component [Chemical formula 2] , the permittivity anisotropy of the nematic liquid crystal composition being negative. The use of this nematic liquid crystal composition can realize a liquid crystal display element that can maintain a high voltage retention even in a high temperature region and can realize high-speed response without reducing the cell gap and is highly reliable.

Description

technical field [0001] The present invention relates to a nematic liquid crystal composition having a negative dielectric constant anisotropy Δε for electro-optical liquid crystal display materials and a liquid crystal display element using the same. Background technique [0002] Liquid crystal display devices can be used in various home appliances represented by clocks and electronic calculators, measuring equipment, automotive panels, word processors, electronic notebooks, printers, computers, televisions, and the like. As liquid crystal display methods, TN (twisted nematic) type, STN (super twisted nematic) type, DS (dynamic light scattering) type, GH (guest-host) type, IPS ( In Plain Switching) type, OCB (Optically Compensated Birefringence) type, ECB (Voltage Controlled Birefringence) type, VA (Vertical Alignment) type, CSH (color super homeotropic) type, or FLC (Ferroelectric Liquid Crystal) and the like. In addition, as the driving method, it is generally from the cu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K19/30C07C43/225C09K19/32C09K19/34C09K19/42G02F1/13
CPCC09K19/3066C09K2019/0407C09K2323/00C09K19/04
Inventor 川上正太郎松本隆楠本哲生齐藤佳孝长岛丰根岸真岩洼昌幸
Owner DIC CORP
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