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Binaphthalene diol chiral compound and its preparation method and application

A technology of compounds and groups, applied in chemical instruments and methods, organic chemistry, nonlinear optics, etc., can solve problems such as low HTP value of chiral additives

Active Publication Date: 2015-09-16
SHIJIAZHUANG CHENGZHI YONGHUA DISPLAY MATERIALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

If the HTP value of the chiral additive is low, a high amount of addition is required to adjust to the required smaller pitch p, and a high amount of addition will increase the dielectric anisotropy (△ε) and optical anisotropy ( △n), clearing point (Cp), viscosity (γ 1 ), drive voltage, response time and other electro-optical properties have more negative effects

Method used

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  • Binaphthalene diol chiral compound and its preparation method and application
  • Binaphthalene diol chiral compound and its preparation method and application
  • Binaphthalene diol chiral compound and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0086]

[0087] step 1

[0088]

[0089] Add 149g (1mol) cyclopentane bromide and 314.4g (1.2mol) triphenylphosphine to a 1L three-neck flask, heat to 120°C under nitrogen protection, react for 10 hours under stirring, cool down to 100°C, add 400ml of toluene under stirring , the reaction solution was made into a slurry, cooled to room temperature, filtered, and rinsed with toluene to obtain 267g of white crystal bromocyclopentane triphenylphosphine salt with a yield of 65%. DSC:

[0090] step 2

[0091]

[0092] Add 267g (0.65mol) of white crystal bromocyclopentane triphenylphosphine salt into a 2L three-necked flask, add 800ml of tetrahydrofuran, cool down to -5°C, replace the air with nitrogen, and add 73g (0.65mol) of tert-butyl in batches Potassium alkoxide turns yellow. Half an hour later, add 85.8g (0.55mol) monoethylene glycol acetal 1,4-cyclohexanedione solution in 150ml tetrahydrofuran dropwise, and then react at room temperature for 4 hours.

[0093] Pou...

Embodiment 2

[0137]

[0138] As in Steps 6 and 7 of Example 1, the raw material was replaced with 4-propylcyclohexyl alcohol to prepare diethyl 2-(4-propylcyclohexyl)malonate.

[0139] step 1

[0140]

[0141] 85.2 g (0.3 mol) of cis+trans-diethyl 2-(4-propylcyclohexyl)malonate and 63.6 g (0.6 mol) of sodium carbonate were stirred together in 300 ml of ethanol and 100 ml of water overnight.

[0142] Add 300ml of water, dilute hydrochloric acid to adjust the pH to strong acidity, extract with 100ml×2 toluene, wash twice with water, evaporate the solvent under reduced pressure, and recrystallize from toluene to obtain trans-2-(4-propylcyclohexyl)malonic acid as a white solid 21.3g, yield 31%.

[0143] step 2

[0144]

[0145] 5.1g (0.018mol) binaphthyldiol is dissolved in 50ml methylene chloride, then add DCC9.1g (0.044mol), DMAP0.3g, add 4.56g (0.02mol) trans-2-(4 -Propylcyclohexyl) malonic acid, after adding one hour, remove the low-temperature tank, and stir and react at room te...

Embodiment 3

[0154]

[0155] Add 0.127g (0.0055mol) of sodium metal to 100ml of absolute ethanol. After the sodium block disappears, add 2.39g (0.005mol) of the product (2-a) of Example 2. After half an hour, add 0.85g (0.006mol) Iodomethane, reacted at room temperature for 8 hours.

[0156] Add 300ml of water and 50ml of toluene, separate the organic layer, extract the aqueous phase with 50ml of toluene once more, wash the organic phase with water, evaporate the solvent under reduced pressure, and recrystallize with a mixed solvent of ethanol and toluene to obtain 1.88g of white crystals, with a yield of 76%.

[0157] DSC: 150°C

[0158] HPLC: 99.67%

[0159] HTP: 99

[0160] The raw materials of different substituents are used, prepared according to the above method, and the compound shown in the following formula I is obtained. The HTP value and response time comparison test results of the following compounds are as in Example 1. The resulting product has no substantial difference,...

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Abstract

The invention discloses a 1,1'-binaphthalene-2,2'-diol chiral compound, a preparation method and application thereof. The 1,1'-binaphthalene-2,2'-diol chiral compound is shown as a formula I and has a high HTP (High Thread Pitch) value, it means that a liquid crystal mixture with high-spiral warping, namely fine pitch, can be prepared by only adding a small quantity of the chiral compound shown as the formula I in a liquid crystal mixture. The addition of small quantity of the chiral compound shown as the formula hardly causes adverse effects on parameters of dielectric anisotropy (Delta epsilon), optical anisotropy (Delta n), a clearing point (Cp) and a viscosity (Gamma 1) of the liquid crystal mixture; and compared with the existing chiral compound, the 1,1'-binaphthalene-2,2'-diol chiral compound has the effect of reducing response time including rise time (Tau on) and fall time (Tau off).

Description

technical field [0001] The invention relates to a binaphthyl diol chiral compound, a preparation method and application thereof. Background technique [0002] Liquid crystals have a variety of phase states, such as smectic phase in lamellar arrangement, nematic phase, and cholesteric phase in helical structure. Among them, nematic liquid crystals can be further classified according to the relative orientation of molecules, and smectic phase is the most common Arrangement, molecules are arranged layer by layer. Another common phase is the cholesteric phase, or chiral nematic phase, in which the orientation of the molecules in each layer is slightly twisted from that of the adjacent layer, resulting in a helical twisted structure in its natural state. When a voltage is applied to this liquid crystal, it will be twisted at a corresponding angle in the direction of the applied voltage. Therefore, it can be used to control the passage of light. [0003] Chiral compounds can be...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D321/00C09K19/34C08F22/14C09K19/38G02F1/1333
Inventor 员国良华瑞茂王奎王健吕文海侯泽峰
Owner SHIJIAZHUANG CHENGZHI YONGHUA DISPLAY MATERIALS CO LTD
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