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Liquid crystal compound containing fluoropyrimidine and application thereof

A technology of liquid crystal compounds and pyrimidines, which is applied in the direction of liquid crystal materials, organic chemistry, chemical instruments and methods, etc., can solve the problems of low driving voltage refractive index dielectric anisotropy, high viscosity, low threshold voltage, etc., and achieve large optical Anisotropy, good compatibility, and improved properties

Inactive Publication Date: 2010-05-26
SHIJIAZHUANG CHENGZHI YONGHUA DISPLAY MATERIALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Liquid crystal display products require that the liquid crystal materials used have a wide temperature range of nematic phase, low driving voltage, suitable refractive index and high dielectric anisotropy, as well as excellent chemical and optical stability, while the existing single Liquid crystal materials cannot meet the above requirements at the same time, so the usual practice is to use several liquid crystal materials with different properties to achieve the desired purpose
Pyrimidine liquid crystals usually have a high dielectric constant (ε / / >ε⊥), a relatively low threshold voltage, a large optical anisotropy Δn, and a high clearing point; but its disadvantage is that it has a high viscosity

Method used

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  • Liquid crystal compound containing fluoropyrimidine and application thereof
  • Liquid crystal compound containing fluoropyrimidine and application thereof
  • Liquid crystal compound containing fluoropyrimidine and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Example 1 Synthesis of 2-[4-(5-propylpyrimidine 2-)-2-fluorophenyl]-5-propylpyrimidine

[0038] When R and Z are respectively propyl and X are hydrogen, the compound represented by formula I is 2-[4-(5-propylpyrimidine 2-)-2-fluorophenyl]-5-propyl-pyrimidine, Its synthesis process is carried out according to the following sequence of steps:

[0039] a1. Compound 1-2: Synthesis of valerenamine

[0040] Add 200g of potassium carbonate and 180ml of morpholine into a 500ml three-necked bottle, install a stirrer, a thermometer, and a constant pressure dropping funnel, cool the outside of the bottle to below 5°C, and start adding 86g of n-butyraldehyde (compound 1-1) dropwise for about 30 minutes The dropwise addition is completed; keep at 0-10°C for 8 hours, suction filter the reaction solution, rinse the funnel several times with 1000ml petroleum ether (90-105°C) to concentrate the filtrate, and collect the colorless liquid at 76-86°C / 20mmHg by distillation under reduced pre...

Embodiment 2

[0057] Example 2 Synthesis of 2-[4-(5-propylpyrimidine 2-)-2-fluorophenyl]-5-propylpyrimidine

[0058] In the formula II, R is a propyl group, and when X is a hydrogen group, the compound is 2-[4-(5-propylpyrimidine 2-)-2-fluorophenyl]-5-propyl-pyrimidine, and its synthetic method is as follows The steps are performed in sequence:

[0059] a 2. Compound 2-2: Synthesis of 1-dimethylamino-3-dimethylimino-2-fluoropropene perchlorate

[0060] In a 250ml three-neck flask equipped with a stirring and reflux condenser, 20g of fluoroacetic acid (compound 2-1) and 100g of thionyl chloride were added; the reaction was refluxed for 6h under heating. Evaporate excess solvent to obtain fluoroacetyl chloride (standby); add 200ml N, N-dimethylformamide in another 500ml three-necked flask equipped with stirring and reflux condenser, and add phosphorus oxychloride 60ml and After the addition of the spare fluoroacetyl chloride, react at 20-30°C for 5 hours, pour the reaction solution into 700...

Embodiment 3

[0069] Example 3 Synthesis of 2-[4-(5-propylpyrimidine-2-)-2-fluorophenyl]-5-trifluoromethyl-pyrimidine

[0070] When R is a propyl group and X is a hydrogen group, the compound shown in formula III is 2-[4-(5-propylpyrimidine 2-)-2-fluorophenyl]-5-trifluoromethyl-pyrimidine, and its synthesis The method proceeds in the following order of steps:

[0071] a3. Compound 3-1: Synthesis of 2-[4-(5-bromopyrimidine-2-)-3-fluorophenyl]-5-propyl-pyrimidine

[0072] Add 2-fluoro-4-(5-propylpyrimidin-2-yl) benzamidine hydrochloride (compound 1-6) 29.5g successively in a 500ml three-necked flask equipped with mechanical stirring, reflux condenser and thermometer , bromomalondialdehyde 15g, methanol 200mL and sodium methoxide 8g, heat to reflux for 8h, cool, filter, then use 150ml toluene, 300ml petroleum ether hot melt product overheated silica gel chromatography column, use 80ml toluene and 160ml petroleum ether mixed solution Wash the column, combine the organic phases and concentrate...

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Abstract

The invention discloses a liquid crystal compound containing fluoropyrimidine and application thereof. The compound has the following structure, wherein R is C1-C8 alkyl or alkenyl, or fluorine-containing C1-C8 alkyl or alkenyl; X is a hydrogen group or a fluorine group; Z is one of the C1-C8 alkyl, the fluorine group, difluoromethyl, trifluoromethyl, trifluoromethoxy, difluoromethoxy or pentafluoroethyl. The compound has higher optical refractive index anisotropy (delta n), lower threshold voltage, wide liquid crystal phase temperature range, good optical, thermal, electric and chemical stabilities, and good compatibility with other compounds, can be used for improving the characteristics of a liquid crystal mixture, can be widely applied to mixed liquid crystal materials of TN, HTN, STN and TFT, and can be further applied to liquid crystal displays.

Description

technical field [0001] The invention belongs to the category of compounds, and specifically relates to a fluorine-containing pyrimidine liquid crystal compound and its use in any display mode of TN, HTN, STN or TFT for preparing mixed liquid crystal materials and further applying the mixed liquid crystal materials to liquid crystals in the display. Background technique [0002] In 1888, when F. Reinitzer measured the melting point of organic compounds, he found that some compounds experienced an opaque turbid state after melting. This turbid liquid interphase has a phenomenon similar to that of crystals, and is called liquid crystal. In the 1970s, due to the development of large-scale integrated circuits and liquid crystal materials, breakthroughs were made in the application of liquid crystals in display. By combining the electro-optical effect of twisted nematic liquid crystals with integrated circuits, they were made into display devices. , Realizing the industrializatio...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/26C09K19/34
Inventor 任惜寒梁晓唐洪田秋峰尹环韩耀华孟劲松刘文菊
Owner SHIJIAZHUANG CHENGZHI YONGHUA DISPLAY MATERIALS CO LTD
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