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Thiophene derivatives, and lc media containing the same

A technology of liquid crystal media and meaning, applied in the field of thiophene derivatives, can solve problems such as long response time

Active Publication Date: 2011-04-13
MERCK PATENT GMBH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

On the other hand, however, liquid-crystalline media with relatively high birefringence values ​​generally also have relatively high values ​​of rotational viscosity, which in turn lead to longer response times

Method used

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  • Thiophene derivatives, and lc media containing the same
  • Thiophene derivatives, and lc media containing the same
  • Thiophene derivatives, and lc media containing the same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0341] Example 1: 2-(4'-ethyl-3-fluorobiphenyl-4-yl)-5-methylthiophene ("PGT-2-1")

[0342] The compound 2-(4'-ethyl-3-fluorobiphenyl-4-yl)-5-methylthiophene ("PGT-2-1") according to the invention was prepared as follows:

[0343]

[0344] 5.0g (28.2mmol) of 2-bromo-5-methylthiophene, 7.70g (28.3mmol) of 4'-ethyl-3-fluoro-4-biphenylboronic acid, 1.70g (1.47mmol) of A mixture of (triphenylphosphine)palladium(0) and 30ml of 2N sodium carbonate solution was heated to reflux for 3h in 90ml of toluene / ethanol (1:2). After cooling, the organic phase was separated and the aqueous phase was extracted several times with toluene. The combined organic phases were washed with water and saturated sodium chloride solution. The solution was dried over sodium sulfate and concentrated completely. The residue was subjected to column chromatography (SiO 2 , n-heptane:toluene=97:3) and purified. Further purification was performed by recrystallization from ethanol and n-heptane; 2-(4'-...

Embodiment 2

[0351] Example 2: 2-(4'-Propyl-3-fluorobiphenyl-4-yl)thiophene ("PGT-3-H")

[0352] The compound 2-(4'-propyl-3-fluorobiphenyl-4-yl)thiophene ("PGT-3-H") according to the invention was prepared as follows:

[0353]

[0354] 25.3g (0.16mol) of 2-bromothiophene, 40.0g (0.16mol) of 4'-propyl-3-fluoro-4-biphenylboronic acid, 8.5g (7.4mmol) of four (triphenylphosphine) ) Palladium (0) mixture and 170ml of 2N sodium carbonate solution in 420ml of toluene / ethanol (1:2) were heated to reflux for 18h. After cooling, the organic phase was separated and the aqueous phase was extracted several times with toluene. The combined organic phases were washed with water and saturated sodium chloride solution. The solution was dried over sodium sulfate and concentrated completely. The residue was subjected to column chromatography (SiO 2 , n-heptane:toluene=9:1) and purified. Further purification is carried out by recrystallization from ethanol and n-heptane; 2-(4'-propyl-3-fluorobiphen...

Embodiment 3

[0361] Example 3: 2-(4'-ethyl-3-fluorobiphenyl-4-yl)-5-propylthiophene ("PGT-2-3")

[0362] The compound 2-(4'-ethyl-3-fluorobiphenyl-4-yl)-5-propylthiophene ("PGT-2-3") according to the present invention was prepared as follows:

[0363] Synthesis of 5-(4'-ethyl-3-fluorobiphenyl-4-yl)thiophene-2-carbaldehyde

[0364]

[0365] 58.5g (0.31mol) of 5-bromothiophene-2-carbaldehyde, 75.5g (0.31mol) of 4'-ethyl-3-fluoro-4-biphenylboronic acid, 17.0g (14.7mmol) of tetrakis( A mixture of triphenylphosphine)palladium(0) and 375 ml of 2N sodium carbonate solution was heated in 935 ml of toluene / ethanol (1:1.5) at 80° C. for 1 h. After cooling, the precipitated product was first dissolved by adding THF. The organic phase was separated and the aqueous phase was extracted with MTBE. The combined organic phases were washed with saturated sodium chloride solution, and the solution was dried over sodium sulfate. The residue remaining after removal of the solvent is soaked in tolu...

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Abstract

The invention relates to thiophene derivatives, methods and intermediate products for the production thereof, the use thereof for optical, electro-optical, and electronic purposes, in particular in liquid crystal (LC) media and LC displays, and LC media and LC displays containing said thiophene derivatives.

Description

Field of Invention [0001] The present invention relates to thiophene derivatives, processes and intermediates for their preparation, their use for optical, electro-optical and electronic purposes, in particular their use in liquid crystal (FK) media and liquid crystal displays and liquid crystal media and liquid crystal displays comprising it. Background technique [0002] Liquid crystals are mainly used as dielectrics in display devices because the optical properties of such substances can be influenced by an applied voltage. Electro-optical devices based on liquid crystals are very well known to those skilled in the art and can be based on various effects. Examples of such devices are cells with dynamic scattering, DAP (distorted aligned phase) cells, guest / host cells, TN cells with twisted nematic (“twisted nematic”) structures, STN (“super twisted nematic”) cells , SBE ("Super Birefringence Effect") cell and OMI ("Optical Mode Interference") cell. The most common displ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K19/34C09K19/42C07D333/38
CPCC07D333/12C09K2019/0466C07D333/38C09K19/42C09K19/3491C09K2019/0448C09K2323/00C09K2323/03
Inventor A·詹森D·保卢特H·希尔施曼M·恰因塔
Owner MERCK PATENT GMBH