Chlorobenzene derivative, optically isotropic liquid crystal medium, and optical element

A liquid crystal compound and compound technology, which is applied in optics, liquid crystal materials, nonlinear optics, etc., can solve problems such as unrecognizable compound properties, reduced operating voltage, and high voltage

Inactive Publication Date: 2012-03-21
JNC CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0015] Although there is a report (Patent Document 13) that chlorobenzene derivatives similar to the compound of the present case have large dielectric constant anisotropy and large refractive index anisotropy, there is no chlorobenzene derivative that can be thought of in the present invention. There is no description of the compound, and there is no description that can think of the excellent characteristics of the compound of this case
Moreover, in the optically isotropic polymer / liquid crystal composite materials disclosed in Patent Document 1 to Patent Document 3 and Non-Patent Document 1 to Non-Patent Document 3, the voltage required for device operation is high
In Patent Document 4 to Patent Document 9, although the optically isotropic liquid crystal composition and the polymer / liquid crystal composite material that can lower the operating voltage compared with the above are disclosed, there is nothing about the chlorine-containing Description of Optically Isotropic Liquid Crystal Composition of Benzene Moiety Compound and Polymer / Liquid Crystal Composite Material

Method used

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  • Chlorobenzene derivative, optically isotropic liquid crystal medium, and optical element
  • Chlorobenzene derivative, optically isotropic liquid crystal medium, and optical element
  • Chlorobenzene derivative, optically isotropic liquid crystal medium, and optical element

Examples

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example

[0322] The resulting compound is obtained by 1 The nuclear magnetic resonance spectrum obtained in the H-NMR analysis, the gas chromatogram obtained in the gas chromatography (gas chromatography, GC) analysis, etc. are identified, and therefore the analysis method will be described first.

[0323] 1 H-NMR analysis: DRX-500 (manufactured by Bruker BioSpin Co., Ltd.) was used as a measurement device. Dissolve the samples prepared in Examples etc. in CDCl 3 In the deuterated solvent in which the sample is soluble, the measurement is carried out at room temperature, 500 MHz, and the cumulative number of times is 24. In addition, in the description of the obtained nuclear magnetic resonance spectrum, s represents a singlet, d represents a doublet, t represents a triplet, q represents a quartet, and m represents a multiplet. Also, tetramethylsilane (TMS) was used as a zero point standard substance for the chemical shift δ value.

[0324] GC analysis: A GC-14B gas chromatograph m...

example 1

[0352] Synthesis of compound (S1-11)

[0353] Compound (S1-11) is in formula (1-4-3), R 1 for C 4 h 9 , L 1 is hydrogen, L 2 , L 4 and L 5 Both are fluorine, X 1 for-CF 3 compound of. (same as compound (1-4-3-a))

[0354]

[0355] The synthesis process is shown in the figure below.

[0356]

[0357] where r.t. is room temperature.

[0358] Synthesis of compound (S1-2)

[0359] Under a nitrogen atmosphere, prepare a Grignard reagent from 11.3 g of dry magnesium and 75.0 g of 1-bromo-3-chloro-5-fluorobenzene (S1-1) using 220 ml of tetrahydrofuran (hereinafter referred to as THF), and cool it to -70°C. A solution of 52.0 g of trimethyl borate in 200 ml of THF was added dropwise there, and after stirring at this temperature for 3 hours, it was heated to room temperature over 1 hour and stirred for 12 hours. 2N-hydrochloric acid was added dropwise to the reaction solution and stirred for 1 hour, the product was extracted with eth...

example 2

[0383] Synthesis of compound (S2-1)

[0384] Compound (S2-1) is in formula (1-4-3), R 1 for C 5 h 11 , L 1 is hydrogen, L 2 , L 4 and L 5 Both are fluorine, X 1 for-CF 3 compound of.

[0385]

[0386] Synthesis of compound (S2-1)

[0387] The synthesis of (S2-1) was carried out according to the synthesis method of (S1-11) in Example 1. The phase transition temperature of the obtained compound (S2-1) is shown below.

[0388] Phase transition temperature (°C): K 91.4 (N 34.4)I.

[0389] 1 The chemical shift δ (ppm) of the H-NMR analysis is shown below, and the obtained compound was identified as (S2-1). In addition, the determination solvent is CDCl 3 . Chemical shift δ(ppm): 7.53(m, 1H), 7.37~7.33(m, 2H), 7.12~7.07(m, 3H), 7.04~7.01(m, 3H), 2.66(t, 2H), 1.69~ 1.63(m, 2H), 1.41~1.31(m, 4H), 0.92(t, 3H).

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PUM

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Abstract

Disclosed are a compound which has a large refractive index anisotropy, a large dielectric constant anisotropy, and a low melting point; and a liquid crystal medium which has a wide liquid crystal phase temperature range, a large refractive index anisotropy, a large dielectric constant anisotropy, and an optically isotropic liquid crystal phase. Specifically disclosed are a liquid crystal compound which has a chlorobenzene ring, and a liquid crystal medium which contains the liquid crystal compound and a chiral agent and exhibits an optically isotropic liquid crystal phase.

Description

technical field [0001] The present invention relates to liquid crystal compounds and liquid crystal media that can be used as materials for optical elements. Specifically, the present invention relates to a compound having a large dielectric constant anisotropy (permittivity anisotropy), a refractive index anisotropy (refractive index anisotropy), and a low melting point; and a compound with a wide liquid crystal phase temperature range , Liquid crystal media with large dielectric constant anisotropy and refractive index anisotropy. In addition, the present invention also relates to an optical element using the liquid crystal medium. Specifically, the present invention relates to an optical element that can be used in a wide temperature range, can be driven at low voltage, and can obtain high-speed electro-optical response. Background technique [0002] Liquid crystal display elements using liquid crystal compositions are widely used in displays such as clocks, calculators...

Claims

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Application Information

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IPC IPC(8): C07C43/225C09K19/12C09K19/14C09K19/16C09K19/18C09K19/20C09K19/30C09K19/34C09K19/38C09K19/54G02F1/13
CPCC09K19/20C09K2019/0466C09K19/588C09K2019/0411C09K2323/00
Inventor 长谷场康宏国信隆史
Owner JNC CO LTD
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