Achiral side methyl alkyl terphenyl liquid crystal compound, production method, liquid crystal composition and application

A technology for methyl alkyl terphenyls and liquid crystal compounds, which is applied in the field of achiral side methyl alkyl terphenyl liquid crystal compounds and their preparation, can solve the problem that liquid crystal materials for microwaves cannot meet the requirements, and the low temperature performance of liquid crystal materials is affected. The problem of large dielectric loss of liquid crystal materials can increase the microwave phase modulation capability, increase the optical anisotropy, and reduce the effect of resonance absorption.

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

AI Technical Summary

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 methyl alkyl terphenyl liquid crystal compound, production method, liquid crystal composition and application
  • Achiral side methyl alkyl terphenyl liquid crystal compound, production method, liquid crystal composition and application
  • Achiral side methyl alkyl terphenyl liquid crystal compound, production method, liquid crystal composition and application

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preparation example Construction

[0065] figure 1 A schematic flow diagram of an embodiment of the preparation method of the achiral pendant methyl alkyl terphenyl liquid crystal compound provided by the present invention, including the following steps:

[0066] Step S10: under the protection of nitrogen, dissolve the first reactant 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 the chlorinated In the mixture of copper, 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;

[0067] Wherein, the first reactant in step S10 is a compound having the structure shown in the following structural formula (II):

[0068]

[0069] Wherein, X in structural formula (II) 1 and x 2 each independently selected from H atom, F atom, Cl atom or -CH 3 .

[0070] In this step, separation, washin...

Embodiment 1

[0119] Example 1 Synthesis of achiral pendant methyl alkyl terphenyl liquid crystal compound 4(1) PPUS, the structural formula is:

[0120]

[0121] The preparation process is:

[0122] (1) In a 500mL three-necked flask equipped with magnetic stirring, add 3g (0.124mol) of magnesium chips, 10mL of tetrahydrofuran and 1-2 iodine simple substances, and then dissolve 26.7g (0.115mol) of bromine in 100mL of anhydrous tetrahydrofuran The biphenyl solution was added to a 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 dropping, heat up and reflux for 30 minutes until the magnesium is nearly completely reacted, stop heating, and cool to room tem...

Embodiment 2

[0132] Example 2 Synthesis of achiral pendant methyl alkyl terphenyl liquid crystal compound 4 (1) PPGS, the structural formula is:

[0133]

[0134] The steps are the same as in Example 1, except that the 2,6-difluoro-4-bromoaniline in step (4) is replaced by 2-fluoro-4-bromoaniline; the temperature is raised to 100°C in step (2) , in step (3), cool down to -80°C in a low-temperature tank, heat up to 25°C after stirring for 2 hours, control the reaction temperature at 40°C in step (4), cool down to 5°C in an ice bath in step (5), and then naturally The temperature was raised to 25°C, and then to 50°C to continue the reaction for 50 minutes.

[0135] Detection by hydrogen-nuclear magnetic resonance spectrum and fluorine-nuclear magnetic resonance spectrum proves that the structure of the prepared target compound is consistent with the structure shown in the above structural formula.

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Abstract

The invention discloses an achiral side methyl alkyl terphenyl liquid crystal compound, a production method of the achiral side methyl alkyl terphenyl liquid crystal compound, a liquid crystal composition and application. The achiral side methyl alkyl terphenyl liquid crystal compound is of a molecular structure as shown in a formula (I) as shown in the specification. An achiral conformation branch end group of the compound (I) makes the compound (I) have a wide-temperature nematic phase state, and the branch end group improves the flexibility of a molecule, so that the compound (I) has a lowmelting point and large dielectric and optical anisotropy; due to a stable molecular structure of the compound (I), microwave absorption is little so that dielectric loss of a microwave device can bereduced; the compound (I) and other nematic liquid crystal compounds can be mixed to form a nematic liquid crystal material with large dielectric anisotropy and large optical anisotropy; and by applying the compound (I) into the microwave device, improvement of the phase modulation capability of the liquid crystal microwave device is facilitated, and a quality factor of the liquid crystal materialas a microwave medium is increased.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to an achiral pendant methyl alkyl terphenyl 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 aspects such...

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
CPCC07C1/326C07C17/12C07C17/263C07C25/18C07C209/68C07C331/28C07F3/02C07F5/025C09K19/12C09K19/44H01P1/18H01P1/20H01Q15/002C07C15/14C07C211/52
Inventor 张智勇卢金应胡晨洪磊刘豪浩关金涛乔俊飞陈红梅汪洋汪相如余承勇赵怿哲高时汉胡俊祥
Owner WUHAN POLYTECHNIC UNIVERSITY
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