Achiral side methylalkyl quaterphenyl liquid crystal compound and preparation method, liquid crystal composition and microwave communication device

A technology of methyl alkyl quaterphenyls and liquid crystal compounds, which is applied in the field of organic synthesis, can solve the problems that microwave liquid crystal materials cannot meet, affect the low-temperature performance of liquid crystal materials, and have large dielectric loss of liquid crystal materials, etc., and achieve increased optical efficiency. Great sum of anisotropy and optical anisotropy, effect of reducing dielectric loss

Active Publication Date: 2020-02-04
WUHAN POLYTECHNIC UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] 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 propose a new type of nematic liquid crystal compound with high stability, Δn≥0.35, low melting point, high dielectric loss and low consumption.

Method used

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  • Achiral side methylalkyl quaterphenyl liquid crystal compound and preparation method, liquid crystal composition and microwave communication device
  • Achiral side methylalkyl quaterphenyl liquid crystal compound and preparation method, liquid crystal composition and microwave communication device
  • Achiral side methylalkyl quaterphenyl liquid crystal compound and preparation method, liquid crystal composition and microwave communication device

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preparation example Construction

[0062] figure 1 A schematic flow diagram of an embodiment of the preparation method of the achiral pendant methyl alkyl quaterphenyl liquid crystal compound (I-1) provided by the present invention, at this time, Y is an F atom, comprising the following steps:

[0063] Step S10: under the protection of nitrogen, dissolve bromobenzene in tetrahydrofuran, then add it to the mixture of magnesium powder, tetrahydrofuran and iodine, and react fully to obtain a Grignard reagent, which is added to copper chloride, In the mixture of DL-1-iodo-2-methylbutane and tetrahydrofuran, reflux reaction, then add dilute hydrochloric acid, stir, and then separate, wash and purify to obtain the first intermediate;

[0064] In this step, separation, washing and purification can be carried out according to conventional methods in the field of organic synthesis. For example, separation can be carried out by extraction and layering, washing with water until the product is neutral, and recrystallizatio...

Embodiment 1

[0123] Example 1 Synthesis of achiral pendant methyl alkyl quaterphenyl liquid crystal compound 4 (1) PGPUS, the structural formula is:

[0124]

[0125] The preparation process is:

[0126] (1) In a 500mL three-necked flask equipped with magnetic stirring, add 7g (0.285mol) of magnesium chips, 10mL of anhydrous tetrahydrofuran and 1-2 iodine simple substances, and then dissolve 43.6g (0.28mol) of iodine in 100mL of anhydrous tetrahydrofuran ) bromobenzene solution was added to the 250ml constant pressure dropping funnel. Under nitrogen protection, add a little bromobenzene dropwise from the constant pressure dropping funnel into the three-necked flask, and heat slightly. After the reaction was initiated, the heating was stopped. Stir slowly, and at the same time, drop bromobenzene into the three-necked flask at a constant speed to make the reflux stable. After dripping, raise the temperature and reflux for about 30 minutes until the magnesium is almost completely reacte...

Embodiment 2

[0136] Example 2 Synthesis of achiral pendant methyl alkyl quaterphenyl liquid crystal compound 4 (1) PWPUS, the structural formula is:

[0137]

[0138] The steps are the same as in Example 1, except that the m-fluorophenylboronic acid in step (3) is replaced with m-chlorophenylboronic acid; the temperature is raised to 110°C in step (2), and cooled to -75°C in step (4). ℃, rise to 20 ℃ after stirring for 2h, the molar ratio of the third intermediate, n-butyllithium, trimethyl borate and hydrochloric acid is 1:1.2:1.4, the fourth intermediate, the third reactant in step (5) 、K 2 CO 3 The molar ratio with the palladium catalyst is 1:2:5:0.001, the molar ratio of the fifth intermediate, calcium carbonate and carbon dichlorosulfide in step (6) is 1:2:2, the ice bath is cooled to 5 ° C, and then Naturally, the temperature was raised to 25°C, and finally to 50°C.

[0139] Detection by hydrogen-nuclear magnetic resonance spectrum and fluorine-nuclear magnetic resonance spectr...

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Abstract

The invention discloses an achiral side methylalkyl quaterphenyl liquid crystal compound and a preparation method thereof, a liquid crystal composition and a microwave communication device. The achiral side methylalkyl quaterphenyl liquid crystal compound has a structure shown by a structural formula (I). The compound (I) has quaterphenyl and branched chain methylalkyl structural units, because the branched chain methylalkyl group has an achiral conformation, the molecular flexibility of the quaterphenyl liquid crystal compound is increased, and thereby the achiral side methylalkyl quaterphenyl liquid crystal compound (I) has a stable structure, and has the advantages of relatively low melting point, large optical anisotropy, wide temperature nematic phase, and the like. The quaterphenyl liquid crystal compound is applied in high dielectric anisotropic liquid crystal materials, the reduction of the dielectric loss of a liquid crystal microwave device is facilitated, the microwave phasemodulation capability is increased, and the quality factor of the liquid crystal materials is improved.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to an achiral side methyl alkyl quaterphenyl liquid crystal compound, a preparation method thereof, a liquid crystal composition and a microwave communication device. 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 as...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K19/12C09K19/44C07C331/28C07C25/18C07F3/02C07C1/32C07C15/14C07C17/12C07F5/02C07C209/68C07C211/52C07C17/263H01Q15/00H01P1/18H01P1/20
CPCC09K19/12C09K19/44C07C331/28C07C25/18C07F3/02C07C1/326C07C17/12C07F5/025C07C209/68C07C17/263H01Q15/002H01P1/18H01P1/20C07C15/14C07C211/52
Inventor 张智勇卢金应李诗妍黄舒豪刘豪浩关金涛乔俊飞陈红梅张海燕丁佩佩汪相如余承勇赵怿哲高时汉胡俊祥
Owner WUHAN POLYTECHNIC UNIVERSITY
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