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Indene derivative used as component of liquid crystal medium, preparation method thereof and application thereof

A reaction and compound technology, applied in the preparation of organic compounds, liquid crystal materials, preparation of halogenated hydrocarbons, etc., can solve problems such as low resistivity and voltage retention

Active Publication Date: 2012-09-12
JIANGSU HECHENG DISPLAY TECHCO +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, many liquid crystal compounds with large negative value have been developed, such as US6348244B, CN102153442, WO9919420. The Δε value of the above-mentioned compounds is very large, but Δn is small, and the resistivity and voltage retention are also very low.

Method used

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  • Indene derivative used as component of liquid crystal medium, preparation method thereof and application thereof
  • Indene derivative used as component of liquid crystal medium, preparation method thereof and application thereof
  • Indene derivative used as component of liquid crystal medium, preparation method thereof and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0068] The synthetic route of preparing compound I-1-1 is in figure 1 Said in, its specific process steps are as follows:

[0069]

[0070] 1) compound of synthetic formula 1

[0071] (Formula 1)

[0072] (Formula 2)

[0073] Add 8g of Mg powder and 0.05g of iodine into a 500mL three-necked flask, and 10mL of tetrahydrofuran (THF), under nitrogen protection. Dissolve 45g of the compound of formula 2 in 200mL of tetrahydrofuran solution, slowly add the tetrahydrofuran solution of the compound of formula 2 to the above reaction system, after the reaction is triggered, continue to drop the remaining tetrahydrofuran solution of the compound of formula 2, and drop , keep the system slightly boiling and reflux for 3h, and cool to room temperature. 40g of chlorotrifluoroethylene was slowly passed into the cooled reaction system, and stirred at room temperature for 12h.

[0074] The reaction was quenched with dilute hydrochloric acid, extracted with ethyl acetate, the orga...

Embodiment 2

[0093] The synthetic route of preparing compound I-2-1 is in Figure 4 Said in, its specific process steps are as follows:

[0094]

[0095] 1) The compound of formula 3 was prepared by steps 1)-2) in Example 1.

[0096]2) compound of synthetic formula 6

[0097] (Formula 6)

[0098] (Formula 7)

[0099] (Formula 8)

[0100] (Formula 9)

[0101] In a 250mL round bottom flask, add 9.3g of the compound of formula 7, 6.4g of the compound of formula 8, 100mL of ethylene glycol dimethyl ether, 35mL of potassium carbonate aqueous solution (2mol L -1 ), 0.5g tetrabutylammonium bromide, 0.4g Pd(PPh 3 ) 4 , nitrogen protection, reflux for 5h. The reaction was quenched with water, extracted with ethyl acetate, the organic phase was dried with anhydrous sodium sulfate, the solvent was spin-dried, petroleum ether was used as the mobile phase for column chromatography, and the eluent was concentrated to obtain 7.6 g of a colorless liquid to obtain a compound of formula 9...

Embodiment 3

[0112] The synthetic route of preparing compound I-3-1 is in Figure 7 Said in, its specific process steps are as follows:

[0113]

[0114] 1) The compound of formula 3 was prepared by using the process steps 1)-2) in Example 1.

[0115] 2) compound of synthetic formula 10

[0116] (Formula 10)

[0117] (Formula 11)

[0118] In a 250mL round bottom flask, add 6g of the compound of formula 11, 8.5g p-phenylbromoiodide, dissolve in 100mL ethylene glycol dimethyl ether, and dissolve in 30mL potassium carbonate aqueous solution (2mol L -1 ), 0.5g tetrabutylammonium bromide, 0.4g Pd(PPh 3 ) 4 , nitrogen protection, reflux reaction for 5h. The reaction was quenched with water, extracted with ethyl acetate, the organic phase was dried with anhydrous sodium sulfate, the solvent was spin-dried, petroleum ether was used as the mobile phase for column chromatography, and the eluent was concentrated to obtain 8.5 g of a white solid to obtain the compound of formula 10.

[0...

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Abstract

The invention provides an indene derivative which can be used as a component of a liquid crystal medium and has a general formula (I), a preparation method thereof and an application thereof. Above compound is a negative liquid crystal compound, has the characteristics of high dielectric property, optical anisotropy and clearing point, and wide nematic phase temperature range, and makes displays using the compound have the advantages of fast response speed and wide working range, and well display in various environments. The invention also provides one or more liquid crystal compositions containing the compound, and liquid crystal elements containing the liquid crystal composition(s).

Description

technical field [0001] The present invention relates to compounds as components of liquid-crystalline media, their preparation and use. Background technique [0002] Liquid crystal materials are substances with a liquid crystal phase between a solid phase and a liquid phase, and are mainly used as dielectrics in displays because the optical properties of such substances can be changed by an applied voltage. Electro-optic devices based on liquid crystals are well known to those skilled in the art, in which various effects may be incorporated. Examples of such devices are liquid crystal cells with dynamic scattering, DAP (distorted alignment phase) liquid crystal cells, guest / host type liquid crystal cells, TN cells with twisted nematic structure, STN (super twisted nematic) liquid crystal cells, SBE ( super birefringence effect) liquid crystal cell and OMI (optical film interference) liquid crystal cell. The most common displays are based on the Schadt-Helfrich effect and h...

Claims

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Application Information

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IPC IPC(8): C07C43/225C07C41/30C07C25/24C07C17/263C09K19/32G02F1/13
Inventor 刘琦龚启明谭玉东陈昭远游石枝
Owner JIANGSU HECHENG DISPLAY TECHCO
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