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Isothiocyano fluorine-containing quaterphenyl liquid crystal compound and its preparation method, liquid crystal composition and application

A technology for liquid crystal compositions and liquid crystal compounds, applied in chemical instruments and methods, liquid crystal materials, etc., can solve the problems that microwave liquid crystal materials cannot meet, affect the low temperature performance of liquid crystal materials, and the dielectric loss of liquid crystal materials is large, etc. Optical anisotropy, low melting point, effect of reducing dielectric loss

Active Publication Date: 2021-09-17
WUHAN POLYTECHNIC UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In the process of a large number of existing researches, it is found that the current liquid crystal materials for microwave use mainly have the following problems in practical applications: first, the optical anisotropy Δn value is too small, less than 0.22, resulting in insufficient phase shift; second, due to The wave-absorbing and polarizable effects of structural groups in liquid crystal molecules lead to large dielectric loss of liquid crystal materials; finally, the lack of liquid crystal solvents and nematic liquid crystal components with high Δn values ​​and low melting points affects the properties of liquid crystal materials. low temperature performance
The above problems make microwave liquid crystal materials unable to meet the requirements of microwave devices. Therefore, it is urgent to develop a new type of nematic liquid crystal compound and its mixture liquid crystal material with high stability, Δn≥0.35, low melting point, high dielectric loss and low consumption.

Method used

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  • Isothiocyano fluorine-containing quaterphenyl liquid crystal compound and its preparation method, liquid crystal composition and application
  • Isothiocyano fluorine-containing quaterphenyl liquid crystal compound and its preparation method, liquid crystal composition and application
  • Isothiocyano fluorine-containing quaterphenyl liquid crystal compound and its preparation method, liquid crystal composition and application

Examples

Experimental program
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Effect test

preparation example Construction

[0056] figure 1 The schematic flow chart of an embodiment of the preparation method of the isothiocyano fluorine-containing quaternyl liquid crystal compound provided by the present invention includes the following steps:

[0057] Step S10: under nitrogen protection, the first reactant, the second reactant, palladium catalyst, K 2 CO 3 , ethanol, toluene and water were subjected to a Suzuki coupling reaction under heating and stirring conditions, and then separated, washed, dried and purified to obtain the first intermediate;

[0058] The first reactant is a compound having the structure shown in the following structural formula (II), and the second reactant is a compound having the structure shown in the following structural formula (III):

[0059]

[0060] Wherein, X in structural formula (II) and (III) 5 and x 6 each independently selected from H atom, F atom, Cl atom or -CH 3 .

[0061] In this step, separation, washing and purification can be carried out accordin...

Embodiment 1

[0099] Example 1 Synthesis of isothiocyanate fluorine-containing quaterphenyl liquid crystal compound 5PGPUS, the structural formula is:

[0100]

[0101] The preparation process is:

[0102](1) Add 20.1g (0.1mol) p-bromophenylboronic acid (the first reactant), 25.5g (0.1mol) of 2, 6-difluoro-4-iodoaniline (the second reactant), 55.2g (0.4mol) of potassium carbonate, then add 150ml of absolute ethanol, 100ml of toluene and 30ml of deionized water; nitrogen replacement 4 times, added under nitrogen protection 0.116g tetrakistriphenylphosphine palladium (0.1% mol ratio), heating, control system temperature 70°C-75°C; stir for 5-6h. TLC tracking and monitoring, after the reaction is complete, stop stirring and heating; the reaction solution is naturally cooled to room temperature, after the reaction solution is filtered by suction, and finally filter out the insoluble matter; the filtrate is extracted three times with 150ml of dichloromethane, and the organic Layer to neutra...

Embodiment 2

[0109] Example 2 Synthesis of isothiocyanate fluorine-containing quaterphenyl liquid crystal compound 4PGPUS, the structural formula is:

[0110]

[0111] The steps are the same as in Example 1, except that the 3-fluoro-4'-pentylbiphenylboronic acid in step (2) is replaced with 3-fluoro-4'-butylbiphenylboronic acid, step (3) The temperature was cooled to 5°C in an ice-water bath, the temperature was naturally raised to 20°C, and then reacted for 0.5h, heated to 50°C and stirred under reflux for 0.5h. Its molecular structure is identified as follows:

[0112] 1 H NMR (400MHz, CDCl 3 )δ7.72(d, J=7.6Hz, 2H), 7.68–7.42(m, 3H), 7.42–7.18(m, 8H), 2.72(t, J=7.7Hz, 2H), 1.84–1.65(m , 2H), 1.56–1.36 (m, 2H), 1.02 (t, J=7.3Hz, 3H).

[0113] 13 C NMR (101MHz, CDCl 3 )δ161.35,158.88,156.99,145.04,142.89, 142.81,140.48,136.88,136.23,130.66,129.68,128.15,126.88,125.74,122.89, 114.37,110.29,109.70,77.41,35.38,33.63,22.48,14.04。

[0114] 19 F NMR (376MHz, CDCl 3 )δ-116.88,-117.50....

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Abstract

The invention discloses an isothiocyano fluorine-containing quaterphenyl liquid crystal compound, a preparation method thereof, a liquid crystal composition and an application thereof. The structure of the isothiocyano fluorine-containing quaterphenyl liquid crystal compound simultaneously has a quaterphenyl structure, Alkyl substituents, F atoms and groups such as -NCS, the quaterphenyl structure makes the liquid crystal compound have the advantages of large optical anisotropy, and the alkyl substituent can reduce the melting point of the liquid crystal compound, so that the liquid crystal compound has a relative The advantage of lower melting point, F atoms can increase the dielectric constant of liquid crystal compounds, and the ‑NCS group prolongs the length of the quaterphenyl π‑electron conjugated system, which can increase the optical anisotropy of liquid crystal compounds, making this type of liquid crystal When the compound is applied to liquid crystal materials with high dielectric anisotropy, due to the comprehensive effect of these groups, it is beneficial to reduce the dielectric loss of liquid crystal microwave devices, improve the phase modulation ability and improve the quality factor of liquid crystal materials.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to an isothiocyano fluorine-containing quaterphenyl liquid crystal compound, a preparation method thereof, a liquid crystal composition and an application thereof. Background technique [0002] At present, liquid crystals have been widely used in the display field. With the development of science and technology, the application range of liquid crystals has gradually increased. The research on liquid crystals for microwave devices began at the end of the 20th century and developed rapidly at the beginning of this century, especially in recent years. It has received widespread attention from all over the world and has developed rapidly. Research has found that it can be used in important fields such as tuneable filters, reconfigurable antennas, adjustable frequency selectors, and adjustable phase shifters. However, there are basic problems to be solved urgently in many aspec...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09K19/12C09K19/42
CPCC09K19/12C09K19/42C09K2019/125
Inventor 关金涛李诗妍洪磊刘豪浩王聪张智勇乔俊飞陈红梅蔡雄辉丁佩佩汪相如余承勇赵怿哲高时汉胡俊祥
Owner WUHAN POLYTECHNIC UNIVERSITY