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Liquid crystal compound containing 5-cyclobutyl-1,3-dioxy cyclohexane structure, preparation method and applications thereof

A compound and liquid crystal technology, applied in chemical instruments and methods, organic chemistry, liquid crystal materials, etc., can solve the problems of lowering the clearing point of liquid crystals, restricting the space for increasing the response speed of liquid crystal mixtures, etc.

Inactive Publication Date: 2016-04-13
SHIJIAZHUANG CHENGZHI YONGHUA DISPLAY MATERIALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But-CF 2 The introduction of O-group will greatly reduce the clearing point of liquid crystal
When formulating the liquid crystal mixture, it is necessary to add a high-definition bright spot compound with a higher viscosity to balance the -CF 2 The decrease of the clearing point caused by the O-group restricts the space for improving the response speed of the liquid crystal mixture

Method used

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  • Liquid crystal compound containing 5-cyclobutyl-1,3-dioxy cyclohexane structure, preparation method and applications thereof
  • Liquid crystal compound containing 5-cyclobutyl-1,3-dioxy cyclohexane structure, preparation method and applications thereof
  • Liquid crystal compound containing 5-cyclobutyl-1,3-dioxy cyclohexane structure, preparation method and applications thereof

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Experimental program
Comparison scheme
Effect test

preparation example Construction

[0088] The general preparation method of the compound represented by formula I provided by the present invention is shown in Synthetic Scheme 1.

[0089] Wherein, the preparation method of the compound represented by formula II is shown in the synthetic route 2,3.

[0090] The principle, operation process, conventional post-treatment, silica gel column, recrystallization and purification of such methods are well known to those skilled in the art. According to the following introduction, the synthesis process can be completely realized and the target product can be obtained.

[0091] The reaction process generally monitors the progress of the reaction by TLC. The post-treatment after the reaction is generally washed with water, extracted, combined with organic phases, dried, evaporated under reduced pressure to remove solvent, and recrystallization, column chromatography. Those skilled in the art can follow The following description implements the present invention.

[0092] R...

Embodiment 1

[0124] Embodiment 1, compound shown in preparation formula I1 (route 3)

[0125]

[0126] step 1

[0127]

[0128] Add 17.7g (0.77mol) sodium silk in batches to 450ml of absolute ethanol, stir until the sodium completely disappears, heat to reflux, add 112g (0.7mol) diethyl malonate dropwise, reflux for 1 hour and cool to 60°C, drop Add 104g (0.77mol) cyclobutyl bromide, reflux for 4 hours after dripping, pour into an equivalent amount of sherwood oil and water, stir and let stand, separate liquids, wash with water, dry under reduced pressure over anhydrous sodium sulfate, and collect the compound (1 -a) 105g, yield 70%.

[0129] step 2

[0130]

[0131] 40.5g (0.75mol) of potassium borohydride and 31.9g (0.75mol) of anhydrous lithium chloride were added to 500ml of tetrahydrofuran, heated to reflux under nitrogen protection, heating was stopped, and 53.5g (0.25mol) of compound (1-a) was added dropwise. After dropping, heat and reflux for 12 hours, pour the reaction ...

Embodiment 2

[0159] Embodiment 2, compound shown in preparation formula I2 (route 2)

[0160]

[0161] step 1

[0162]

[0163] Using p-bromobenzaldehyde and ethylene glycol as raw materials, refer to Step 9 of Example 1 to obtain product (2-a).

[0164] step 2

[0165]

[0166] Dissolve (2-a) 50.8g (0.222mol) and 39g (0.244mol) of 3,5-difluorophenylboronic acid obtained in step 1 in a mixed solution of 600ml of toluene, 300ml of ethanol and 300ml of water, and add 27g (0.256mol) Sodium carbonate, heated and stirred under nitrogen protection, added 2g tetrakistriphenylphosphine palladium during reflux, stopped the reaction in 7 hours, separated liquids, extracted the water layer with toluene, combined the toluene layers, spin-dried the solution, petroleum ether column chromatography, spin-dried After drying the solvent, it was recrystallized with petroleum ether to obtain 50 g of product (2-b) with a yield of 86%.

[0167] Step 3 is obtained with reference to step 5 of Example ...

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Abstract

The present invention discloses a liquid crystal compound containing 5-cyclobutyl-1,3-dioxy cyclohexyl and a difluoromethyleneoxy linking group, a preparation method and applications thereof, wherein the compound is represented by a formula I. According to the present invention, in the molecular structure of the compound represented by the formula I, the liquid crystal compound containing the 5-cyclobutyl-1,3-dioxy cyclohexyl terminal group and the difluoromethyleneoxy linking group (-CF2O-) has characteristics of high dielectric anisotropy, extremely rapid response speed and high clearing point so as to provide important significance for blending of the liquid crystal mixture. The formula I is defined in the specification.

Description

technical field [0001] The invention belongs to the field of liquid crystal compounds and applications, and relates to a liquid crystal compound containing 5-cyclobutyl-1,3-dioxcyclohexyl and a difluoromethyleneoxy linking group, a preparation method and application thereof. Background technique [0002] At present, the application range of liquid crystal compounds is expanding more and more widely, and it can be applied to various types of displays, electro-optic devices, sensors, and the like. There are various types of liquid crystal compounds used in the above-mentioned display fields, among which nematic liquid crystals are most widely used. Nematic liquid crystals have been used in passive TN, STN matrix displays and systems with TFT active matrix. [0003] For the application field of thin film transistor technology (TFT-LCD), although the market has been huge in recent years and the technology has gradually matured, people's requirements for display technology are a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D319/12C09K19/34C09K19/42C09K19/44G02F1/1333
Inventor 李明张兴员国良吕文海赵磊王瑾华瑞茂
Owner SHIJIAZHUANG CHENGZHI YONGHUA DISPLAY MATERIALS CO LTD
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