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Adamantane derivatives and their preparation methods and applications

A kind of compound, straight-chain alkyl technology, applied in the field of adamantane derivatives and their preparation

Active Publication Date: 2015-09-02
BEIJING CHENGZHI YONGHUA DISPLAY TECHNOLOGY CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But so far, no single liquid crystal monomer has been used alone in liquid crystal displays without being combined with other compounds to meet the performance requirements.

Method used

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  • Adamantane derivatives and their preparation methods and applications
  • Adamantane derivatives and their preparation methods and applications
  • Adamantane derivatives and their preparation methods and applications

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0113] Example 1 Synthesis of Compound I-13

[0114]

[0115] Step 1 Synthesis of I-13-a

[0116] Add 29.1g (0.1mol) 4-(1-adamantane)p-bromobenzene (reactant), 80ml of tetrahydrofuran (solvent) into the reaction flask, protect by nitrogen, cool to -60℃, add 0.1mol n-butyl dropwise The petroleum ether (solvent) solution of lithium (reactant) was added dropwise within 1 hour, and the reaction was stirred at -50°C for 30 minutes. Then the temperature was lowered to -60°C, and 13g (0.13mol) of trimethyl borate (reactant) in 70ml of tetrahydrofuran (solvent) solution was added dropwise within 1 hour. After the addition, the reaction was continued with temperature control and stirring for 1 hour, and the temperature was raised to room temperature. Add 0.2mol hydrochloric acid and stir for 1 hour. After washing with water, extract with 50ml of ethyl acetate (solvent) and separate the liquids. Wash the organic phase with water until it is neutral. After evaporating the solvent, 20.5g of c...

Embodiment 2

[0128] Example 2 Synthesis of Compound I-14

[0129]

[0130] Add 28.2g (0.11mol) of I-13-1 (reactant) in Example 1, 48.3g (0.1mol) gP into the reaction flask 3 (Reactant), 0.3g of tetrakistriphenylphosphine palladium (catalyst), 15g of sodium carbonate (catalyst), 100ml of toluene (solvent), 100ml of water, 100ml of ethanol (solvent), heat and reflux for 4 hours, add 100ml of water, divide The organic phase was evaporated to dryness, and the product was obtained by column chromatography and recrystallization. The yield of 43 g was 70%.

[0131] The test results are as follows:

[0132] GC: 99.9%

[0133] MP: 178°C

[0134] CP: 232°C

[0135] MS: 614 (3.5) 467 (100) 346 (16.7) 359 (8.0)

[0136] 1H-NMR: δ(ppm:) 1.72(t,6H), 1.87(m,3H), 1.99(d,6H), 6.89(m,2H), 7.02(d,1H), 7.22(d,2H) , 7.38 (s, 4H) 7.58 (d, 1H), 7.83 (m, 1H)

[0137] It can be seen from the above that the product has a correct structure and belongs to the target product of formula I.

[0138] The liquid crystal performance t...

Embodiment 3

[0150] Example 3. Preparation of liquid crystal composition a

[0151] Mix the compounds according to the following mass percentages to obtain liquid crystal composition a:

[0152]

[0153]

[0154] The performance test results of the liquid crystal composition are as follows:

[0155] Cp=98℃

[0156] △n=0.105

[0157] △ε=7.5

[0158] It can be seen from the above that the liquid crystal composition has a wide temperature range of the liquid crystal phase, low viscosity, suitable refractive index anisotropy and low starting voltage, and has important application value.

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Abstract

The invention discloses an adamantane derivative and a preparation method and application thereof. The structural general formula of the compound is shown in a formula I. The compound shown in the formula I has necessary general physical properties of all compounds, and has light stability and thermal stability, a wide nematic phase and good intermiscibility with other compounds; particularly, the compound has a large dielectric anisotropic (delta [epsilon] is more than 0) characteristic, and has a great significance to development of monomer liquid crystal compounds with high dielectric anisotropy (delta [epsilon]). The liquid crystal composition containing the compound shown in the formula I is wide in temperature range of a liquid crystalline phase and small in viscosity, has proper refractive index anisotropy and low starting voltage, and also has important application value.

Description

Technical field [0001] The invention belongs to the field of synthesis and application of liquid crystal compounds, and relates to an adamantane derivative and a preparation method and application thereof. Background technique [0002] Liquid crystal displays using liquid crystal compositions are widely used in monitors, computers, TVs and other displays. For the field of liquid crystal display technology, although the market has been very huge in recent years and the technology has gradually matured, people’s requirements for display technology are also increasing , Especially in terms of achieving fast response and reducing drive voltage to reduce power consumption. As one of the important optoelectronic materials for liquid crystal displays, liquid crystal materials play an important role in improving the performance of liquid crystal displays. [0003] Liquid crystal display elements are divided into the following modes according to the display mode: twisted nematic (TN) mode,...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C41/30C07C43/225C09K19/44C09K19/32G02F1/1333
Inventor 韩耀华华瑞茂张芳苗夏治国员国良田秋峰张建立王奎
Owner BEIJING CHENGZHI YONGHUA DISPLAY TECHNOLOGY CO LTD
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