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Compound, composition, liquid crystal composition, and high-frequency phase shifter

A compound and independent technology, applied in liquid crystal materials, chemical instruments and methods, organic chemistry, etc., can solve the problems of low compatibility, insufficient phase modulation characteristics, low dielectric constant anisotropy, etc., and achieve compatibility The effect of high and large dielectric constant anisotropy and large refractive index anisotropy

Pending Publication Date: 2021-06-18
DIC CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, when these compounds are added to a liquid crystal composition for antenna use, they have low compatibility, and there is a problem of precipitation during long-term storage (Non-Patent Document 1, Patent Document 1)
In addition, compounds having a thienothiophene structure and a thioisocyano group have also been reported, but these compounds have low dielectric constant anisotropy in the high-frequency region and insufficient phase modulation characteristics

Method used

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  • Compound, composition, liquid crystal composition, and high-frequency phase shifter
  • Compound, composition, liquid crystal composition, and high-frequency phase shifter
  • Compound, composition, liquid crystal composition, and high-frequency phase shifter

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0322] (Example 1) Production of a compound represented by formula (I-1)

[0323] [chem 63]

[0324]

[0325] [chem 64]

[0326]

[0327] 7.0 g of the compound represented by the formula (I-1-1) and 70 mL of dichloromethane were added to the reaction container. 9.3 g of N-bromosuccinimide was added little by little while cooling with ice, and stirred at room temperature for 5 hours. The reaction liquid was poured into water, and a liquid separation process was performed. The organic layer was washed with brine, and purified by column chromatography (silica gel, dichloromethane / hexane) to obtain 8.8 g of a compound represented by the formula (I-1-2).

[0328] Under nitrogen atmosphere, in reaction container, add the compound represented by 8.8g formula (I-1-2), 8.3g potassium carbonate, the compound represented by 8.6g formula (I-1-3), 88mL toluene, 44mL ethanol, 44 mL of water, 0.3 g of [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane adduc...

Embodiment 2

[0338] (Example 2) Production of a compound represented by formula (I-2)

[0339] [chem 65]

[0340]

[0341]7.0 g of the compound represented by the formula (I-2-1) and 70 mL of dichloromethane were added to the reaction vessel. 7.9 g of N-iodosuccinimide was added little by little while cooling with ice, and stirred at room temperature for 5 hours. The reaction liquid was poured into water, and a liquid separation process was performed. The organic layer was washed with saline, and purified by column chromatography (silica gel, dichloromethane / hexane) to obtain 8.8 g of a compound represented by the formula (I-2-2).

[0342] Under a nitrogen atmosphere, add 8.8g of the compound represented by the formula (I-2-2), 0.2g of copper iodide (I), 0.2g of 2-dicyclohexylphosphino-2',4',6 '-triisopropylbiphenyl [XPhos], 0.2 g palladium(II) acetate, 88 mL diisopropylamine, 176 mL N,N-dimethylformamide. A solution obtained by dissolving 5.4 g of the compound represented by the fo...

Embodiment 3

[0348] (Example 3) Production of the compound represented by formula (I-3)

[0349] [chem 66]

[0350]

[0351] [chem 67]

[0352]

[0353] Under nitrogen atmosphere, 7.0 g of the compound represented by the formula (I-3-1), 4.3 g of pyridine, and 70 mL of dichloromethane were added to the reaction vessel. 11.3 g of trifluoromethanesulfonic anhydride was added dropwise while cooling with ice, and stirred at room temperature for 4 hours. The reaction solution was poured into a 5% aqueous solution of sodium bicarbonate for liquid separation. The organic layer was washed sequentially with 5% hydrochloric acid, water and brine, and then purified by column chromatography (silica gel, dichloromethane / hexane) to obtain 10.6 g of a compound represented by the formula (I-3-2).

[0354] Under nitrogen atmosphere, add the compound represented by 10.6g formula (I-3-2), 9.6g potassium acetate, 10.0g bis(pinacolate) diboron, 106mL dimethyl sulfoxide, 0.4g [1,1'-bis(diphenylphosphi...

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Abstract

The invention provides a compound, a composition, a liquid crystal composition and a high-frequency phase shifter. The present invention addresses the problem of providing the compound which has a large refractive index anisotropy [Delta] n, has high compatibility with a liquid crystal composition, and exhibits a large dielectric anisotropy in a high-frequency region; the liquid crystal composition which contains the compound; and an element which uses the liquid crystal composition. The present invention provides the compound represented by general formula (I), the liquid crystal composition containing the compound, and the element using the liquid crystal composition. The compound of the present invention has high refractive index anisotropy [Delta] n, has high compatibility in a liquid crystal composition, and shows high dielectric constant anisotropy in a high-frequency region. Therefore, the material is useful as a material for elements such as a high-frequency phase shifter, a phased-array antenna, an image recognition device, a distance measurement device, a liquid crystal display element, a liquid crystal lens or a birefringent lens for stereoscopic image display.

Description

technical field [0001] The present invention relates to a compound, a liquid crystal composition containing the compound, and an element using the liquid crystal composition. Background technique [0002] Liquid crystal compositions are used in display applications such as mobile terminals such as smartphones and tablet devices, TVs, and screen displays. As a new application of the liquid crystal composition, antennas for transmitting and receiving radio waves between mobile bodies such as vehicles and communication satellites are attracting attention. [0003] Traditionally, parabolic antennas have been used for satellite communications, but when used for moving objects, the parabolic antenna must always be directed toward the satellite, requiring a large movable part. However, since the antenna using the liquid crystal composition can change the signal transmission and reception direction of radio waves by the operation of the liquid crystal, it is not necessary to move t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/04C09K19/34C09K19/44
CPCC07D495/04C09K19/3491C09K19/44C09K2219/11C09K2019/0444H01P3/16H01P1/182
Inventor 堀口雅弘林正直
Owner DIC CORP
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