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A liquid crystal compound, a preparation method, a composition containing the compound, and a high-frequency component containing the liquid crystal medium

A technology for liquid crystal compositions and compounds, applied in chemical instruments and methods, liquid crystal materials, etc., can solve problems such as reduction, increase in dielectric tuning rate and dielectric loss, and achieve simple post-processing process, high quality factor, easy effect of operation

Active Publication Date: 2021-07-27
XIAN MODERN CHEM RES INST +1
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Problems solved by technology

In the journal "Proc.ofSPIE, 2013, 8642: 86420S-1-86420S-6", a paper entitled "Liquid Crystals for Microwave Applications" also reported a mixed liquid crystal material phase based on a fluorine-containing phenyl tolantylene liquid crystal compound. Compared with traditional cyano-based liquid crystal materials, its dielectric tuning rate and dielectric loss have increased and decreased to a certain extent, but the overall performance is still at a moderate level and needs to be further improved.

Method used

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  • A liquid crystal compound, a preparation method, a composition containing the compound, and a high-frequency component containing the liquid crystal medium
  • A liquid crystal compound, a preparation method, a composition containing the compound, and a high-frequency component containing the liquid crystal medium
  • A liquid crystal compound, a preparation method, a composition containing the compound, and a high-frequency component containing the liquid crystal medium

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Synthesis of 2-chloro-4'-ethyl-4-((4-propylphenyl)ethynyl)-1,1'-biphenyl:

[0037] The specific structure is as follows:

[0038]

[0039] The preparation process is as follows:

[0040] Step 1: Synthesis of 1-bromo-2-chloro-4-((4-propylphenyl)ethynyl)benzene

[0041]

[0042] Under nitrogen protection, 1-bromo-2-chloro-4-iodobenzene (10 g, 0.0315 mol), bis(triphenylphosphine) palladium dichloride (0.22 g, 1% mol), iodine Cuprous chloride (0.18g, 3%mol), PPh 3 (0.25g, 3%mol), triethylamine 50mL. Propylphenylacetylene (4.54 g, 0.0315 mol) was added dropwise at 10° C. After the drop, the mixture was reacted for 2 h under heat preservation for post-treatment. Filter the reaction solution, add n-heptane to dissolve the filtrate after rotary evaporation, wash with saturated ammonium chloride aqueous solution twice until neutral, dry over anhydrous magnesium sulfate, filter, and perform column chromatography on the filtrate, elute with n-heptane, elute After liquid r...

Embodiment 2

[0055] Synthesis of 2-chloro-4'-propyl-4-((4-propylphenyl)ethynyl)-1,1'-biphenyl

[0056] The specific structure is as follows:

[0057]

[0058] Propylphenylboronic acid is used to replace the ethylphenylboronic acid in the step (2) of Example 1, and the same method as in Example 1 is used to synthesize 2-chloro-4'-propyl-4-((4-propylphenyl )ethynyl)-1,1'-biphenyl.

[0059] Structure Identification: 1 H NMR (δ, CDCl 3 ):0.964-0.993(t,3H),1.003-1.032(t,3H),1.647-1.750(m,4H),2.623-2.690(m,4H),7.197-7.213(d,J=8Hz,2H) ,7.274-7.287(m,2H),7.335-7.351(d,J=8Hz,1H),7.398-7.414(m,2H),7.460-7.492(m,3H),7.657-7.660(d,1H); MS(70eV)m / z(%):372.2(M + ,100),343.1(74),314.1(26),276.1(8),157.1(19),139.1(7).

[0060] The above structural identification data show that the synthesized compound is indeed 2-chloro-4'-propyl-4-((4-propylphenyl)ethynyl)-1,1'-biphenyl.

[0061] Use DSC to test the liquid crystal phase transition temperature of 2-chloro-4'-propyl-4-((4-propylphenyl)ethynyl)-1,...

Embodiment 3

[0063] Synthesis of 4'-butyl-2-chloro-4-((4-propylphenyl)ethynyl)-1,1'-biphenyl

[0064] The specific structure is as follows:

[0065]

[0066] Using butylphenylboronic acid instead of ethylphenylboronic acid in step (2) of Example 1, the same method as in Example 1 was used to synthesize 4'-butyl-2-chloro-4-((4-propylphenyl )ethynyl)-1,1'-biphenyl.

[0067] Structure Identification: 1 H NMR (δ, CDCl 3 ):0.967-1.004(m,6H),1.399-1.473(m,2H),1.650-1.725(m,4H),2.626-2.656(t,2H),2.685-2.716(t,2H),7.200-7.216 (d, J=8Hz, 2H), 7.278-7.294(m, 2H), 7.335-7.351(d, J=8Hz, 1H), 7.398-7.414(m, 2H), 7.461-7.496(m, 3H), 7.660-7.663(d,1H); MS(70eV)m / z(%):386.2(M + ,100),343.1(38),314.0(25),276.1(6),157.1(11),139.1(6).

[0068] The above structural identification data show that the synthesized compound is indeed 4'-butyl-2-chloro-4-((4-propylphenyl)ethynyl)-1,1'-biphenyl.

[0069] Use DSC to test the liquid crystal phase transition temperature of 4'-butyl-2-chloro-4-((4-propylphenyl...

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Abstract

The invention discloses a liquid crystal compound, a preparation method, a composition containing the liquid crystal compound and a high-frequency component containing the liquid crystal medium, so as to solve the problem of low comprehensive performance in the prior art. The structure of the liquid crystal compound is: the liquid crystal composition includes 0% to 50% of 0% to 65% less than or equal to 100% and not zero. The present invention not only has low dielectric loss and high quality factor, but also has a wide The advantages of the temperature range of the nematic phase are applicable to fields such as filters, phase shifters, phased array radars, and 5G communication networks. The invention provides a liquid crystal high-frequency component with wide operating temperature range, low loss and high tuning rate.

Description

technical field [0001] The invention belongs to the technical field of liquid crystal materials, and specifically relates to a liquid crystal compound and its composition and a high-frequency component containing the liquid crystal medium, and is mainly suitable for high-frequency components, filters, adjustable frequency selection surfaces, phase shifters, and phase control Array radar, satellite navigation and 5G communication network and other fields. Background technique [0002] In recent years, liquid crystal materials with low dielectric loss and high dielectric tuning rate have been widely used in liquid crystal microwave device technologies such as filters, adjustable frequency selective surfaces, phase shifters, phased array radars, and 5G communication networks. attention. As the core tuning material of microwave devices, the dielectric tuning rate of liquid crystal materials determines the tuning ability of microwave devices. For liquid crystal materials, the d...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09K19/18C09K19/12C09K19/44
CPCC09K19/12C09K19/18C09K19/44C09K2019/122C09K2019/123C09K2019/181C09K2019/183
Inventor 李娟利李建莫玲超杨晓哲车昭毅安忠维张璐胡明刚陈小川朱红赵伟利刘明星李锐孙海雁于美娜
Owner XIAN MODERN CHEM RES INST
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