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A kind of binaphthyl diol chiral compound and its preparation method and application

A chiral compound, binaphthol technology, applied in the field of liquid crystals, can solve problems such as low HTP value, poor solubility, easy crystal precipitation, etc., and achieve the effect of reducing negative effects

Active Publication Date: 2020-06-26
BEIJING BAYI SPACE LCD MATERIALS TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Existing chiral compounds usually have a low HTP value, so a high amount of doping is required to meet the helical pitch requirements; in addition, the existing chiral compounds have poor solubility in liquid crystal mixtures, and crystals are easy to precipitate in low temperature environments, making it impossible to use In addition, existing chiral compounds still have the problems of high synthesis difficulty and high cost

Method used

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  • A kind of binaphthyl diol chiral compound and its preparation method and application
  • A kind of binaphthyl diol chiral compound and its preparation method and application
  • A kind of binaphthyl diol chiral compound and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] The structural formula of embodiment 1 chiral compound is:

[0050]

[0051] The synthetic route for preparing compound BYLC-01 is as follows:

[0052]

[0053] Specific steps are as follows:

[0054] (1) Synthesis of compound BYLC-01-1:

[0055] Add 44.8g of potassium tert-butoxide and 300ml of N,N-dimethylformamide into the reaction flask, control the temperature below 50°C, add 64g of diethyl malonate dropwise, and stir naturally for 1 hour. Control the temperature at 50°C to 60°C, add 69.6g of 4-n-propylcyclohexylmethyl chloride dropwise, and react at 60°C for 3 hours after dropping. The reaction was quenched with 300ml of 2M hydrochloric acid aqueous solution, followed by conventional post-treatment, and high vacuum and reduced pressure distillation to obtain 73.9g of a colorless transparent liquid (compound BYLC-01-1), GC: 96.7%, yield 62%;

[0056] (2) Synthesis of compound BYLC-01-2:

[0057]Under the protection of nitrogen, add 200ml tetrahydrofuran a...

Embodiment 2

[0064] According to the technical scheme of Example 1, the following chiral compounds can be synthesized by simply replacing the corresponding raw materials without changing any substantive operations. The HTP value of each compound was detected by the same method as in Example 1, and the results showed that the HTP value was substantially the same as in Example 1.

[0065]

[0066]

Embodiment 3

[0068] The structural formula of a chiral compound is:

[0069]

[0070] The synthetic route for preparing compound BYLC-03 is as follows:

[0071]

[0072] Specific steps are as follows:

[0073] (1) Synthesis of compound BYLC-03-1:

[0074] Add 44.8g of potassium tert-butoxide and 300ml of N,N-dimethylformamide into the reaction flask, control the temperature below 50°C, add 64g of diethyl malonate dropwise, and stir naturally for 1 hour. Control the temperature at 50°C to 60°C, add 82.4g of 3,4-difluorobenzyl bromide dropwise, and react at 60°C for 3 hours after dropping. Quench the reaction with 300ml of 2M hydrochloric acid aqueous solution, perform conventional post-treatment, and distill under high vacuum to obtain 75.5g of a colorless transparent liquid (compound BYLC-03-1), GC: 94.1%, yield 66%;

[0075] (2) Synthesis of compound BYLC-03-2:

[0076] Under the protection of nitrogen, add 300ml tetrahydrofuran and 9.6g lithium aluminum tetrahydrogen to the rea...

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Abstract

The invention belongs to the technical field of liquid crystal, and particularly relates to a binaphthol chiral compound and a preparation method and application thereof. The structure of the chiral compound is shown in the description, the chiral compound has an extremely high HTP value, and in a liquid crystal composition, liquid crystal composition small in pitch and high in helical distortioncan be obtained simply by adding at the amount being 5% or below; on the condition that the pitches are the same, due to the fact that the number of added chiral compounds is reduced, negative influence of the chiral compounds on liquid crystal phase behaviors and photoelectric performance parameters of the liquid crystal composition is greatly lowered.

Description

technical field [0001] The invention belongs to the field of liquid crystals, and in particular relates to a binaphthyl diol chiral compound and a preparation method and application thereof. Background technique [0002] The application of liquid crystal materials as environmental materials in the fields of information display materials and organic optoelectronic materials has great research value and bright application prospects. Liquid crystal materials have many advantages as new display materials, such as extremely low power consumption and low driving voltage. At the same time, compared with other materials, it also has the advantages of small size, light weight, long life, large amount of displayed information, and no electromagnetic radiation, which can almost meet the requirements of various information displays. [0003] For many applications, liquid crystal mixtures with twisted phases are required, and these liquid crystal mixtures can be used to prepare displays...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D321/00C09K19/58G02F1/1333
CPCC07D321/00C09K19/588G02F1/1333
Inventor 田会强谭小玉储士红高立龙姜天孟陈海光苏学辉
Owner BEIJING BAYI SPACE LCD MATERIALS TECH
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