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Thioether-derivatives of dibenzothiophens and dibenzofurans

A compound and an independent technology, applied in the field of thioether derivatives of dibenzothiophene and dibenzofuran, can solve the problems of image quality degradation and achieve easy preparation, rich mixed components, and good nematic phase width Effect

Active Publication Date: 2020-02-21
MERCK PATENT GMBH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

If the display is tilted relative to the viewing direction, the image quality will degrade dramatically in some cases

Method used

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  • Thioether-derivatives of dibenzothiophens and dibenzofurans
  • Thioether-derivatives of dibenzothiophens and dibenzofurans
  • Thioether-derivatives of dibenzothiophens and dibenzofurans

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0126] step 1

[0127]

[0128] 0.058 mol of 2-bromo-6-fluorophenol was dissolved in 100 ml of THF and mixed with 40 ml of water and 0.09 mol of potassium carbonate. After heating to boiling point temperature, add 0.3mmol tris(dibenzylideneacetone)dipalladium(0) and 0.9mmol A (bis(1-adamantyl)-n-butylphosphine), and 0.062mol (4-ethoxy-2,3-difluorophenyl) dimethoxyborane was added dropwise within half an hour to dissolve in Solution in 100ml THF. The mixture was boiled at reflux for a further 16 hours, then admixed with water and MTB and worked up by extraction. The crude product 4'-ethoxy-3,2',3'-trifluorobiphenyl-2-ol was purified by chromatography (eluent: chlorobutane). White crystals were obtained.

[0129] step 2

[0130]

[0131] 0.022 mol of 4'-ethoxy-3,2',3'-trifluorobiphenyl-2-ol, 0.036 mol of triethylamine and 0.6 mmol of DMAP were dissolved in 50 ml of dichloromethane. To this solution was added dropwise 0.03 mol of trifluoromethanesulfonic anhydride...

Embodiment 2

[0144]

[0145] 9.9 g (30 mmol) of phenol 1 (prepared analogously to Example 1) were dissolved in 90 ml of DCM and mixed with 8 ml of triethylamine and 150 mg of DMAP. At 5°C, 8 ml (48 mmol) of trifluoromethanesulfonic anhydride were added. The batch was then stirred for 1 hour without cooling. The reaction solution was placed onto silica gel and product 2 was eluted with DCM. Yield: 90%.

[0146] Under protective gas, mix 13.9g (30mmol) triflate 2 with 70ml toluene, 4.5ml (73mmol) ethanethiol, 10.5g (76mmol) potassium carbonate, 1.6g (3.1mmol) bis(2-bis Phenylphosphinophenyl)ether and 1.4 g (1.5 mmol) of tris(dibenzylideneacetone)dipalladium(0) were mixed and heated to a boil overnight. Pass the cooled batch through Filter, concentrate and place onto silica gel. Product 3 was eluted with n-heptane.

[0147] Melting point: 73°C.

[0148] Phase: C73N(26)I (see also table).

[0149] The following dibenzothiophene compounds were prepared analogously to Example 1:

[...

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Abstract

The invention relates to 4,6-dihalogen-dibenzothiophene and 4,6-dihalogen-dibenzofuran-3-thioether derivatives of formula (I), in which W, X, R1, R2, A1, Z1 and n are defined as cited in claim 1, to their production, their use as components in liquid crystal media and to electrooptic display elements containing the liquid crystal media according to the invention.

Description

technical field [0001] The invention relates to 4,6-dihalodibenzothiophene and 4,6-dihalodibenzofuran-3-sulfide derivatives, to processes for their preparation, to liquid-crystalline media comprising these derivatives, and It relates to electro-optical display elements containing these liquid-crystalline media. The compounds have negative dielectric anisotropy. Background technique [0002] Since the discovery of the first commercially available liquid crystal compounds about 30 years ago, liquid crystals have found a wide range of applications. Known fields of application of the conventional mixtures are in particular displays for watches and pocket calculators, and large display panels such as are used in railway stations, airports and sports arenas. Further fields of application are displays for portable and desktop computers, navigation systems and video applications. Especially for the last-mentioned applications, high demands are placed on the response time and the ...

Claims

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Application Information

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IPC IPC(8): C07D333/76C07D307/91C09K19/34
CPCC07D333/76C07D307/91C09K19/34C09K19/3491C09K2019/3408
Inventor L·列特扎A·戈茨H·赫施曼M·恩格尔
Owner MERCK PATENT GMBH
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