4,6-difluorodibenzofuran derivatives

A compound and atomic technology, applied in the field of 4,6-difluorodibenzofuran derivatives, can solve problems such as unfinished research and development in the field of liquid crystal materials

Active Publication Date: 2015-09-23
MERCK PATENT GMBH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Research and development in the field of liquid crystal materials is still far from complete

Method used

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  • 4,6-difluorodibenzofuran derivatives
  • 4,6-difluorodibenzofuran derivatives
  • 4,6-difluorodibenzofuran derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0116] Example 1: 3-butoxy-4,6-difluoro-7-propoxydibenzofuran

[0117]

[0118] step 1

[0119]

[0120] Initially 50 g of dibenzofuran was introduced into 1500 ml of THF, and 152 g of 15% BuLi in hexane were added dropwise at -60 to -75°C. The mixture was warmed to room temperature and stirred for an additional 3 hours. The mixture was subsequently recooled to -75°C and a solution of 112.5 g of N-fluorobenzenesulfonimide in 1000 ml of THF was added at -75 to -60°C. After an additional 30 minutes at -70°C, the reaction mixture was allowed to warm to ambient temperature, and the batch was hydrolyzed with water and subjected to extractive workup.

[0121] The crude product (red-brown oil) was purified by chromatography (eluent: n-heptane).

[0122] white crystals.

[0123] step 2

[0124]

[0125] Initially 40 g of 4-fluorodibenzofuran was introduced into 450 ml of THF, and 96 g of 15% BuLi in hexane were added dropwise at -60 to -75°C. The mixture was stirred ...

Embodiment 1 and approach 2

[0166] The following compounds were prepared analogously to Example 1 and Scheme 2:

[0167]

[0168] Unless otherwise specified, R 1 / 2 The groups are linear, ie unbranched. In Table 2 the substance data are given.

[0169] Table 2

[0170]

[0171]

[0172]

[0173] *) trans isomer

Embodiment 1 and approach 3

[0174] The following compounds were prepared analogously to Example 1 and Scheme 3:

[0175]

[0176] Unless otherwise specified, R 1 / 2 The groups are linear, ie unbranched. In Table 3 the substance data are given.

[0177] table 3

[0178]

[0179]

[0180] *) trans isomer

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PUM

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Abstract

4,6-difluorodibenzofuran derivatives of the formula I the preparation thereof, the use thereof as components in liquid-crystalline media and electro-optical display elements which contain the liquid-crystalline media.

Description

technical field [0001] The present invention relates to 4,6-difluorodibenzofuran derivatives, to a process for their preparation, to liquid-crystalline media comprising these derivatives, and to electro-optic displays containing these liquid-crystalline media. The compounds have negative dielectric anisotropy. 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. Additional areas of application are displays 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 the molecules in the liquid crystal has an effect...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/91C09K19/34G02F1/1333
CPCC07D307/91C09K2019/3408C09K19/3405G02F1/1333C09K19/32G02F1/13712
Inventor 沃克尔·雷芬拉瑟马蒂亚斯·布雷默罗克·福特哈拉德·赫施曼马丁·恩格尔
Owner MERCK PATENT GMBH
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