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Liquid crystal compound containing tetrahydro-thiopyran group and preparation method thereof, and liquid crystal composition

A technology of thiotetrahydropyranyl and liquid crystal compounds, applied in chemical instruments and methods, liquid crystal materials, etc., to achieve the effects of good compatibility, wide nematic phase temperature range, and faster response time

Active Publication Date: 2014-02-05
BEIJING CHENGZHI YONGHUA DISPLAY TECHNOLOGY CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, so far, no single liquid crystal compound has been found that can meet the above performance requirements. It is necessary to combine multiple liquid crystal compounds into a liquid crystal composition to meet the performance requirements of liquid crystal display materials.

Method used

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  • Liquid crystal compound containing tetrahydro-thiopyran group and preparation method thereof, and liquid crystal composition
  • Liquid crystal compound containing tetrahydro-thiopyran group and preparation method thereof, and liquid crystal composition
  • Liquid crystal compound containing tetrahydro-thiopyran group and preparation method thereof, and liquid crystal composition

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0151] Preparation of compound I-a:

[0152] Its synthetic route is:

[0153]

[0154]

[0155] Its concrete preparation steps are as follows:

[0156] 1.1 Preparation of intermediate Ⅰ-a-1:

[0157] Add 9.5g (0.11mol) n-valeraldehyde, 9.5g (0.11mol) methyl acrylate, 16g (0.11mol) trimethylsilyldiethylamine, 1g p-hydroxyanisole and 130ml acetonitrile (solvent) to a 250ml reaction bottle , heated to reflux under the protection of nitrogen, and refluxed for 24 hours; after the reaction, the temperature was lowered, and the solvent was evaporated; then 22ml of glacial acetic acid and 44ml of water were added to the reaction bottle, the temperature was raised again, and the reaction was refluxed for 2h; after the reaction was completed, it was cooled to room temperature, and 100ml of Methyl tert-butyl ether and 100ml water, extract and separate; the aqueous layer is extracted with 50ml×2 methyl tert-butyl ether (that is, each time with 50ml methyl tert-butyl ether, a tot...

Embodiment 2

[0188] Preparation of compound I-b:

[0189] The preparation of compound I-b is carried out using the intermediate I-a-4 prepared in Example 1 as a starting material, and its synthetic route is:

[0190]

[0191] Its concrete preparation steps are as follows:

[0192] 2.1 Preparation of intermediate Ⅰ-a-4:

[0193] Intermediate I-a-4 was prepared according to the preparation method of step 1.1 to step 1.4 in Example 1.

[0194] 2.2 Reactant I-b-1 Preparation of:

[0195] The synthesis was carried out according to the method in the literature Peer.Kirsch et al., Angew.Chem.Int.Ed., 2001.40.1480.

[0196] 2.3 Preparation of compound Ⅰ-b

[0197] Add 29.2g (0.11mol) intermediate I-a-4, 38.9g (0.1mol) reactant I-b-1, 0.3g tetrakistriphenylphosphine palladium, 15g sodium carbonate, 100ml toluene, 100ml Water and 100ml of ethanol were heated to reflux under stirring, and refluxed for 4 hours; after the reaction, the temperature was lowered, and 100ml of water was added f...

Embodiment 3

[0211] Preparation of compound I-c:

[0212] The preparation of compound I-c is carried out using the intermediate I-a-2 prepared in Example 1 as a starting material, and its synthetic route is:

[0213]

[0214] Its concrete preparation steps are as follows:

[0215] 3.1 Preparation of intermediate Ⅰ-a-2:

[0216] Intermediate I-a-2 was prepared according to the preparation method of step 1.1 to step 1.2 in Example 1.

[0217] 3.2 Preparation of intermediate Ⅰ-c-1:

[0218] Add 17.5g (0.1mol) 3-fluorobromobenzene and 250ml tetrahydrofuran into the reaction bottle, stir to dissolve and cool down to -60°C ~ -50°C, and drop 40ml of 2.5M under the condition that the system temperature is not higher than -50°C (0.1mol) of butyllithium; then continue to dropwise add 15.8g (0.1mol) of intermediate Ⅰ-a-2 in tetrahydrofuran (15.8g of intermediate Ⅰ-a-2 dissolved in 50ml of tetrahydrofuran), and stir the reaction for 30min after dropping ;Naturally raise the temperature to -20...

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Abstract

The invention discloses a liquid crystal compound containing a tetrahydro-thiopyran group and a preparation method thereof and a liquid crystal composition. The liquid crystal compound is represented by a general formula I. The liquid crystal composition comprises no more than 40% but more than 0 of the compound as represented by the general formula I, 4 to 50% of a compound as represented by a general formula II, 5 to 50% of a compound as represented by a general formula III and 3 to 45% of a compound as represented by a general formula IV. The liquid crystal compound provided by the invention has low rotary viscosity gamma 1, great dielectric anisotropy, a wide nematic phase temperature range, good intermiscibility, light stability and thermal stability and is fairly applicable as a liquid crystal monomer; the liquid crystal composition containing the liquid crystal compound has a great liquid crystalline phase temperature range, appropriate optical anisotropy, small rotary viscosity and low starting voltage and is especially applicable to liquid crystal display elements of a TN mode, a VA mode, an IPS mode and a PDLC mode.

Description

technical field [0001] The invention relates to a liquid crystal compound containing a thiotetrahydropyranyl group, a preparation method thereof and a liquid crystal composition containing the liquid crystal compound, belonging to the field of liquid crystal compounds and applications. Background technique [0002] In recent years, liquid crystal displays have replaced traditional cathode ray tube displays and become mainstream products in the field of information display today, widely used in various displays such as instruments, computers, and televisions. According to different liquid crystal display methods, liquid crystal display elements can be divided into twisted nematic (TN) mode, super twisted nematic (STN) mode, in-plane (IPS) mode, vertical alignment (VA) mode and other modes. [0003] Thin Film Transistor Liquid Crystal Display (TFT-LCD) is one of the most promising display technologies in the 21st century and is widely used in notebook computers, LCD TVs and ot...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K19/34C09K19/44C09K19/46
Inventor 张建立邵哲韩耀华史正魏景景华瑞茂
Owner BEIJING CHENGZHI YONGHUA DISPLAY TECHNOLOGY CO LTD
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