Compounds including indene and difluoroethylene bridge bond, preparation method thereof and application thereof

A compound and reaction technology, applied in the compound containing indene ring and difluoroethylene bridge and its preparation and application field, can solve the problems of unsatisfactory liquid crystal materials, performance not suitable for market development, etc., and achieve large optical anisotropy , The synthesis route is simple and easy, and the effect of wide temperature range of nematic phase

Active Publication Date: 2012-08-08
JIANGSU HECHENG DISPLAY TECHCO +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In recent years, people have begun to pay attention to some liquid crystal materials with large optical anisotropy (Δn), low rotational viscosity (γ), and high-definition bright spots (Cp), and have also synthesized some liquid crystal materials that partially meet the above requirements (such as the applicant Submitted Chinese patent application: 201010288759.6), however, its performance does not meet the needs of market development, and still cannot satisfy users of liquid crystal materials

Method used

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  • Compounds including indene and difluoroethylene bridge bond, preparation method thereof and application thereof
  • Compounds including indene and difluoroethylene bridge bond, preparation method thereof and application thereof
  • Compounds including indene and difluoroethylene bridge bond, preparation method thereof and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] The synthetic route of the prepared compound I-3-1 is in figure 1 Said in, its specific process steps are as follows:

[0057]

[0058] 1) Synthesis of lithium diisopropylamide (LDA)

[0059] Add 115mL of diisopropylamine and 100mL of tetrahydrofuran (THF) into a 1000mL three-necked flask, under nitrogen protection, and add 320mL of n-butyllithium (n-BuLi, 2.4mol / L) dropwise under temperature control at 0°C to -20°C. Stir at ~-20°C for 1 hour to prepare LDA.

[0060] 2) Synthesis of trifluorovinyl zinc chloride

[0061]

[0062] Add 53g of anhydrous zinc chloride and 100mL THF to a 1000mL three-necked flask, protect it with nitrogen, cool down to -70°C, inject 54g of 1,1,1,2-tetrafluoroethane gas, and control the temperature from -50°C to -70°C Slowly inject LDA under the liquid surface through the needle tube, and stir for 2 hours after the addition, to obtain trifluorovinyl zinc chloride.

[0063] 3) compound of synthetic formula 6

[0064] (Formula 6)

...

Embodiment 2

[0083] The synthetic route of the prepared compound I-3-2 is in image 3 Said in, its specific process steps are as follows:

[0084]

[0085] 1) Prepare the compound of formula 9 with steps 1) to 5) in Example 1.

[0086] 2) compound of synthetic formula 10

[0087] Formula 10

[0088] Take a dry 50ml single-necked bottle, add a magnetic stirrer, connect a condenser, add 1.75g ​​of 3,5-difluoro-4-(2,2,2-trifluoroethaneoxy)bromobenzene, 5ml of 2mol / L potassium carbonate Aqueous solution, 0.5g tetrabutylammonium bromide, 15ml ethylene glycol dimethyl ether (DME), stirring, 1.6g compound of formula 9, 0.01g tetrakis (triphenylphosphine) palladium, nitrogen protection, reflux at 80°C for 3h .

[0089] The reaction solution was poured into 50 mL of water, extracted with ethyl acetate, the organic layers were combined, washed with water, and the solvent was evaporated under reduced pressure. Silica gel column chromatography with petroleum ether as eluent. Beat with absol...

Embodiment 3

[0097]The synthetic route of the prepared compound I-5-1 is in Figure 5 Said in, its specific process steps are as follows:

[0098]

[0099] 1) Prepare the compound of formula 6 with steps 1) to 3) in Example 1.

[0100] 2) compound of synthetic formula 11

[0101] Formula 11

[0102] Add 2.9g of 3.5-difluorobromobenzene and 50ml of tetrahydrofuran to a 100ml three-necked flask, protect with nitrogen, cool down to -78°C, slowly add 7.5ml of 2.4mol / L n-butyllithium dropwise, and react for 2 hours at a temperature controlled below -70°C , to prepare m-fluorophenyllithium reagent.

[0103] Dissolve the obtained compound of formula 6 (14 g) in 20 mL of tetrahydrofuran, control the temperature below -70°C, drop it into the m-fluorophenyllithium reagent prepared above, and react overnight at room temperature.

[0104] After the reaction was complete, the reaction was quenched with dilute glacial hydrochloric acid water, extracted with ethyl acetate, washed with water, dri...

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PUM

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Abstract

The invention provides compounds including an indene and a difluoroethylene bridge bond and having a general formula (I), a preparation method thereof and an application thereof. The compounds have large optical anisotropies (delta n), low rotary viscosities (gamma) and wide nematic phase temperature ranges, so the response speed of liquid crystal devices using the compounds can be accelerated, and the working range of the liquid crystal devices can be enlarged, thereby the liquid crystal devices can maintain good display in various environments. The invention also provides one or more liquid crystal compositions of the compounds, and liquid crystal elements including the 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 crystals are primarily used as dielectrics in displays because the optical properties of such substances can be changed by applying an electrical 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 have a twisted nematic structure. Furthermore, there are also liquid crystal cells ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C43/247C07C41/30C07C41/24C07C41/16C07C22/08C07C25/24C07C17/269C09K19/32G02F1/13
Inventor 刘琦谭玉东闵国庆龚启明胡全陈昭远游石枝
Owner JIANGSU HECHENG DISPLAY TECHCO
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