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Ortho ester derivative, liquid crystal composition, and liquid crystal display element

一种液晶组成物、群组的技术，应用在液晶性化合物,液晶性化合物及液晶组成物领域，能够解决液晶显示元件驱动电压降低、电压保持率低、介电常数各向异性不大等问题

Active Publication Date: 2013-12-11
JNC CORP +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the compound (a) has a small dielectric constant anisotropy and cannot be used for purposes such as reducing the driving voltage of a liquid crystal display element.
Moreover, the compound (b) has a cyano group, so the voltage retention rate is low, and the dipoles of the cyano group and the 2,6,7-trioxabicyclo[2.2.2]octane ring face in the opposite direction, so the dielectric constant Anisotropy is not great

Method used

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  • Ortho ester derivative, liquid crystal composition, and liquid crystal display element
  • Ortho ester derivative, liquid crystal composition, and liquid crystal display element
  • Ortho ester derivative, liquid crystal composition, and liquid crystal display element

Examples

Experimental program
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example

[0194] Hereinafter, the present invention will be described in more detail by examples, but the present invention is not limited by these examples. In addition, "%" means "wt%" unless otherwise specified.

[0195] The resulting compound is obtained by 1 The nuclear magnetic resonance spectrum obtained by the H-NMR analysis, the gas chromatogram obtained by the gas chromatography (GC) analysis, and the like are used for identification, so the analysis method will be described first.

[0196] 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 16. 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 ...

example 1

[0223] Synthesis of 4-propyl-1-(4-(3,4,5-trifluorophenyl)cyclohexyl)-2,6,7-trioxabicyclo[2.2.2]octane (No.21)

[0224]

[0225] Step 1

[0226] Add 4.8g (120mmol) of fully dry powdered sodium hydroxide, 100ml of acetonitrile and 9.9g (330mmol) of paraformaldehyde into the reactor under nitrogen atmosphere, and add 8.4g of valeraldehyde dropwise for 20 minutes while stirring at room temperature (97mmol). After the dropwise addition was completed, the temperature was 60°C. Then, the temperature was raised to 80° C. and stirred for 30 minutes. After cooling to room temperature, the insoluble matter was separated by filtration, and the solvent was distilled off under reduced pressure. The obtained residue was purified by a fractionation operation using a column chromatography (the column chromatography used ethyl acetate as a developing solvent and silica gel as a filler), and dried to obtain 2-(Hydroxymethyl)-2-propylpropane-1,3-diol 6.6 g.

[0227] Step 2

[0228] Add 2...

example 2

[0241] Synthesis of 4-ethyl-1-(4-(3,4,5-trifluorophenyl)cyclohexyl)-2,6,7-trioxabicyclo[2.2.2]octane (No.20)

[0242]

[0243] Using 3-ethyl-3-hydroxymethyl propylene oxide instead of 3-propyl-3-hydroxymethyl propylene oxide, it was synthesized in the same manner as in the third and fourth steps of Example 1, thereby synthesizing 4 -Ethyl-1-(4-(3,4,5-trifluorophenyl)cyclohexyl)-2,6,7-trioxabicyclo[2.2.2]octane.

[0244] 1 The chemical shift δ (ppm) of the H-NMR analysis is as follows, and the obtained compound can be identified as 4-ethyl-1-(4-(3,4,5-trifluorophenyl)cyclohexyl)-2,6 , 7-trioxabicyclo[2.2.2]octane. In addition, the determination solvent is CDCl 3 .

[0245] Chemical shift δ(ppm); 6.79(m, 2H), 3.91(s, 6H), 2.39(m, 1H), 1.98(m, 2H), 1.90(m, 2H), 1.60(m, 1H), 1.3 -1.1(m, 6H), 0.83(t, 3H).

[0246] The transition temperature of the obtained compound (No. 20) is shown below.

[0247] Transition temperature: C 168.5 I

[0248]Physical properties of compound...

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Abstract

Provided is a liquid crystal compound, which has large dielectric anisotropy, a high voltage retention rate and good stability in the presence of light and heat, becomes a nematic phase within a broad temperature range, has the appropriate optical anisotropy, and has excellent compatibility with other liquid crystal compounds, particularly a liquid crystal compound having large dielectric anisotropy. The compound is represented by formula (1) (1) where, for instance, R1 is a C1-20 alkyl, rings A1, A2, A3, A4, A5 and A6 are, independently, 1,4-cyclohexylene or 1,4-phenylene; Z1, Z2, Z3, Z4, Z5, Z6 and Z7 are, independently, single bonds, -(CH2)2-, -COO-, -OCO-, -CF2O-, -OCF2-, or -CH=CH-; X1 is a fluorine, -CF3, or -OCF3; and Y1 and Y2 are, independently, hydrogen or fluorine.

Description

technical field [0001] The invention relates to a novel liquid crystal compound and liquid crystal composition, in particular to a liquid crystal compound having a 2,6,7-trioxabicyclo[2.2.2]octane ring and having a large dielectric constant anisotropy and high A liquid crystal compound with a voltage holding rate of 100%, a liquid crystal composition containing the liquid crystal compound, and a liquid crystal display element containing the liquid crystal composition. Background technique [0002] Display elements using liquid crystal compounds (in the present invention, the term liquid crystal compound is used as a generic term for compounds having a liquid crystal phase and compounds that do not have a liquid crystal phase but can be used as constituent components of liquid crystal compositions) are widely used. In the displays of clocks, calculators, word processors, etc. These display elements utilize optical anisotropy, dielectric anisotropy, and the like of liquid cry...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/08C09K19/12C09K19/14C09K19/16C09K19/18C09K19/20C09K19/30C09K19/34C09K19/54G02F1/13
CPCC07D493/08C09K19/3402C09K2019/3425C09K2019/3427G02F1/137G02F1/13706G02F1/13712C09K19/06C09K19/34G02F1/13
Inventor 益川解文
Owner JNC CORP
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