Side methyl polybiphenyl liquid crystal compound, liquid crystal composition and application of composition

A technology of methyl polybiphenyls, liquid crystal compounds, applied in liquid crystal materials, chemical instruments and methods, waveguide-type devices, etc., can solve the problems of large microwave dielectric loss, insufficient Δn value, affecting low temperature performance, etc. The effect of reducing dielectric loss, reducing eutectic point and reducing loss

Active Publication Date: 2020-02-07
WUHAN POLYTECHNIC UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] At present, there are main problems in liquid crystal materials for microwave use: ① due to insufficient Δn value and low dielectric constant (Δεr), the amount of phase shift is insufficient; ② due to the absorption and polarization of structural groups in liquid crystal molecules, microwave dielectric The electrical loss is too large; ③The lack of high Δn value and low melting point nematic liquid crystal components affects its low temperature performance and outdoor low temperature work

Method used

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  • Side methyl polybiphenyl liquid crystal compound, liquid crystal composition and application of composition
  • Side methyl polybiphenyl liquid crystal compound, liquid crystal composition and application of composition
  • Side methyl polybiphenyl liquid crystal compound, liquid crystal composition and application of composition

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0062] Synthetic compound (5PP (1) UF), its molecular structure is as follows:

[0063]

[0064] Its synthetic route is as follows:

[0065]

[0066] Its synthesis steps are as follows:

[0067] (1) Add 14.14g (0.132mol) of 2-methylaniline, 33.6g (0.135mol) of iodine, 16.6g (0.166mol) of Anhydrous calcium carbonate and 200ml distilled water, after reacting at room temperature for 1 hour, raise the temperature to 68°C and react for 1 hour; TLC tracking monitoring, stop stirring and heating after the reaction is complete, filter with suction, wash the filter cake with CH2Cl2, and wash the filtrate with CH2Cl2 and Extracted with water until neutral, dried over anhydrous sodium sulfate, filtered with suction, and evaporated the organic solvent to obtain 32g of a purple-black crude product, which was recrystallized with 50% absolute ethanol and 50% water to obtain 27.49g of a white solid a(4- Iodo-2-methylaniline), melting point: 86°C-89°C, yield 89.3%.

[0068] (2) Add 45...

Embodiment 2

[0074] Synthetic compound 5PP (1) GF, its molecular structure is as follows:

[0075]

[0076] The specific synthetic route and method are the same as in Example 1, except that the reactant 3,4,5-trifluorophenylboronic acid in the synthetic step (4) is changed into equimolar 3,4-difluorophenylboronic acid (1.57g, 0.01 mol) can be; the specific dosage is 2-methyl-4'-pentyl biphenyl bromide is added 3.17g (0.01mol), 3,4-difluorophenylboronic acid is added 1.58g (0.01mol), tetrakis (triphenyl Phosphine) palladium was added to 0.12g (1×10 -4 mol), potassium carbonate was added to 5.53g (0.04mol); 1.1g of white solid product 1,2-difluoro-2'-methyl-4"-pentyl terphenyl (5PP(1)GF) was finally obtained; melting point: 33°C-34°C, the reaction yield is 81.4%, and the total synthesis yield is 28.76%. IR(KBr, νmax / cm -1 ): 3445.72, 2927.14, 2858.47, 2359.15, 1608.31, 1488.86, 1414.40, 1309.00, 1266.97, 1221.77, 1182.97, 1115.31, 817.66, 772.97cm -1 ; 1 H-NMR (400MHz, CDCl 3 )δ(ppm)...

Embodiment 3

[0078] Synthetic compound 5PPI (1) UF, its molecular structure is as follows:

[0079]

[0080] The specific synthetic route and method are the same as in Example 1, except that the raw material 2-methylaniline of the synthetic step (1) is changed into equimolar 3-methylaniline (14.14g, 0.132mol); The target product 5PPI (1) UF) of color transparent liquid, reaction yield 84.2%, total synthesis yield is 20.25%. Melting point: -40°C. IR(KBr,νmax / cm -1 ): 3025.74, 2928.34, 2860.95, 1613.68, 1528.95, 1445.87, 1370.18, 1251.51, 1045.07, 824.58, 749.33, 698.99, 572.87cm -1 ; 1 H NMR (400MHz, CDCl 3 )δ(ppm):7.59–7.21(m,9H),2.91–2.77(m,2H),2.52(s,2H),1.86(dd,J=10.1,4.6Hz,2H),1.54(dd,J =25.2,21.6Hz,5H),1.12(t,J=6.7Hz,3H); 13 C NMR (100MHz, CDCl 3 )δ(ppm):142.34,142.08,141.98,139.37,138.04,137.32,136.40,135.47,130.75,128.81,128.49,127.14,125.85,124.26,111.02,110.86,77.16,76.85,35.86,31.83,22.77,20.60, 14.17; 19 F NMR (376MHz, CDCl 3 )δ (ppm): -133.97, -134.03, -162.60, -16...

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Abstract

The invention discloses a side methyl polybiphenyl liquid crystal compound, a liquid crystal composition and an application of the composition. A structure of the liquid crystal compound is represented by a formula I shown in the specification, wherein n is an integer of 1 to 7; X1 to X4 are each independently selected from a H atom, a F atom or a Cl atom; k is 0 or 1; Y is NCS, a F atom or an R group; and R is one selected from the group consisting of a straight-chain alkyl group containing 1-6 carbon atoms, an alkenyl-contained straight-chain alkyl group containing 1-6 carbon atoms, and a straight-chain alkyl group containing 1-6 carbon atoms, wherein the a H atom on the alkyl chain of the straight-chain alkyl group is replaced by 1-2 fluorine atoms or one methyl. The compound provided by the invention and other materials are mixed to prepare the liquid crystal composition material with a <delta>n value of greater than 0.35, the microwave phase modulation amount is improved, and themicrowave wave frequency insertion loss amount is reduced.

Description

technical field [0001] The invention belongs to the technical field of liquid crystal materials for microwave devices, and more specifically relates to a pendant methyl polybiphenyl liquid crystal compound, a liquid crystal composition and applications thereof. Background technique [0002] Microwave phase shifter is a key device in the field of microwave K-band (millimeter wave, 0.3-40GHz) communication technology. It has a wide range of applications in many aviation, military and civil fields such as radar systems, satellite antennas, communication systems, and electronic countermeasure systems. . However, with the rapid development of modern communication technology, the phenomenon of communication frequency congestion has become increasingly prominent, requiring communication devices to have higher frequency adjustment, wider frequency band and multi-functionality; traditional ferrite or diode phase shifter radiation unit antenna Due to problems such as large volume, sm...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K19/12H01P1/18H01Q3/30
CPCC09K19/12C09K2019/123C09K2019/124C09K2019/188H01P1/18H01Q3/30
Inventor 张智勇刘曼曼刘豪浩李诗妍瞿毅关金涛乔俊飞陈红梅张海燕汪相如赵怿哲高时汉胡俊祥扈映茹
Owner WUHAN POLYTECHNIC UNIVERSITY
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