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Fluorinated dibenzofuran and dibenzothiophene derivative

A compound and phenylene technology, applied in the field of electro-optic display elements, can solve problems such as unfinished development in the field of liquid crystal materials, and achieve the effect of good width

Active Publication Date: 2016-10-26
MERCK PATENT GMBH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Development in the field of liquid crystal materials is still far from complete

Method used

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  • Fluorinated dibenzofuran and dibenzothiophene derivative
  • Fluorinated dibenzofuran and dibenzothiophene derivative
  • Fluorinated dibenzofuran and dibenzothiophene derivative

Examples

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specific Embodiment approach

[0111] The present invention is explained in more detail below with reference to Examples, but it is not intended to be limited thereto. Those skilled in the art will be able to glean from the examples operational details not given in detail in the general description, generalize them based on general expertise and apply them to specific problems.

[0112] In addition to the usual and well-known abbreviations, the following abbreviations are used:

[0113] C: liquid crystal phase; N: nematic phase; Sm: smectic phase; I: isotropic phase. The numbers between these symbols show the transition temperature of the substances involved.

[0114] Temperature data are in °C unless otherwise stated.

[0115] By generally known methods, as described inter alia in the handbook "Merck Liquid Crystals- - Methods in Physical Properties of Liquid Crystals - Description of the Measurement Methods", 1998, Merck KGaA, Darmstadt for the determination of physical, physicochemical or electro-opt...

Embodiment 1

[0128] Example 1: 4,6-Difluoro-3-trifluoromethoxy-7-pentyloxydibenzofuran

[0129] 1.1: 1,2-Difluoro-3-pentyloxybenzene

[0130]

[0131] 19.0 g (146 mmol) of 2,3-difluorophenol and 20.1 ml (163 mmol) of 1-bromopentane were dissolved in ethyl methyl ketone, 22.4 g of potassium carbonate were added, and the mixture was heated at boiling overnight . A solid then separates out and the solvent is removed. The amyl 2,3-difluorophenyl ether obtained was used without further purification in the subsequent step.

[0132] 1.2: 2,3-Difluoro-4-pentyloxyphenylborane acid

[0133]

[0134] 108 ml of a 15% solution of n-butyllithium in n-hexane (172 mmol) were added to a solution of 31.2 g of the crude product (10) from step 1 in 225 ml of THF at -70°C. After 1 hour at this temperature, 20 ml (176 mmol) of trimethylborate dissolved in 25 ml of THF were added. After an additional hour, the batch was warmed to 0° C., water was added, and the mixture was adjusted to pH 1 using 2...

Embodiment 25

[0165] Example 25 : Butoxy-4,6-difluoro-7-trifluoromethoxydibenzothiophene

[0166] 25.1 :3,2',3'-Trifluoro-4'-butyloxy-4-trifluoromethoxybiphenyl-2-ol

[0167]

[0168] Phenol 22 was prepared analogously to compound 14 by Suzuki coupling of compound 13 and commercially available 4-butoxy-2,3-difluorophenylborane acid.

[0169] 25.2 :3,2',3'-Trifluoro-4'-butyloxy-4-trifluoromethoxybiphenyl-2-yl trifluoromethanesulfonate

[0170]

[0171] Add triethylamine (5.0ml) and DMAP (60mg) dropwise to 3,2',3'-trifluoro-4'-butyloxy-4-trifluoromethoxybiphenyl-2-ol (9.7g) in a solution in dichloromethane (70ml). Trifluoromethanesulfonic anhydride (5.0 ml) was then added dropwise at 5°C, and the reaction mixture was stirred at room temperature for 20 hours. The mixture was filtered through silica gel, washed with dichloromethane, dried (Na 2 SO 4 ) and evaporated under vacuum. 3,2',3'-Trifluoro-4'-butyloxy-4-trifluoromethoxybiphenyl-2-yl triflate 9 was isolated as a residue a...

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Abstract

The invention relates to a dibenzofuran and dibenzothiophene derivative with a general formula I (shown in the description), wherein X1, X2, W, Y, R, A, Z and m are defined in claims. The invention relates to a manufacturing method, the application of a component serving a liquid crystal medium, and an electro-optic display element comprising the liquid crystal medium.

Description

technical field [0001] The present invention relates to fluorinated dibenzofuran and dibenzothiophene derivatives, a process for their preparation, liquid crystal (LC) media comprising these derivatives, and electro-optic display elements containing these liquid crystal media. Background technique [0002] Liquid crystals have been widely used since commercially available liquid crystal compounds were first discovered about 30 years ago. Known fields of application of conventional mixtures are in particular displays for watches and pocket calculators, and large display panels used in railway stations, airports and stadiums. Further fields of application are monitors for laptop and desktop computers, navigation systems and video applications. Especially for the last-mentioned applications, the response time and contrast of the image are highly required. [0003] The spatial arrangement of molecules in liquid crystals has direction-dependent effects on many of its properties...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/91C07D333/76C09K19/34G02F1/1333
CPCC07D307/91C07D333/76C09K19/3405C09K19/3491C09K2019/3408G02F1/1333C09K19/3402C09K19/42
Inventor 拉斯·利曹康斯坦泽·布洛克沃克尔·雷芬拉瑟真边笃孝
Owner MERCK PATENT GMBH
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