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Dioxane derivatives as well as preparation method and application thereof

A kind of technology of alkyl and compound, applied in the field of dioxane derivatives and preparation thereof

Inactive Publication Date: 2014-04-02
SHIJIAZHUANG CHENGZHI YONGHUA DISPLAY MATERIALS 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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  • Dioxane derivatives as well as preparation method and application thereof
  • Dioxane derivatives as well as preparation method and application thereof
  • Dioxane derivatives as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0110] Embodiment 1, Synthesis of (method 1)

[0111]

[0112] Step 1: Synthesis of I-17-a

[0113] Add 68g (1mol) sodium ethoxide and 1L absolute ethanol to the reaction flask, add 132g (1mol) dimethyl malonate under stirring and heat to reflux for 1 hour, 149g (1mol) cyclopentyl bromide (reactant) is added dropwise to the reaction flask In the bottle, reflux and stir for 2 hours, add 1L of water, 1L of n-heptane, process according to the conventional method, combine the organic phase and spin dry the solvent, and distill under reduced pressure to obtain 160g of the product, with a yield of 80%.

[0114] Step 2: Synthesis of I-17-b

[0115] Add 38g of lithium aluminum hydride and 1L of tetrahydrofuran to a 2L three-necked flask, add 160g (0.8mol) of I-17-a (reactant) dropwise under stirring, heat and stir under reflux for 8 hours, cool down to 0°C, and drop in 105g of potassium sodium tartrate The solution prepared with 300g of water was left to stand for 10 minutes, a...

Embodiment 2

[0139] Embodiment 2, compound Synthesis of (method 2)

[0140]

[0141] Add 30.4g (0.11mol) (I-17-d) (reactant) to the reaction flask, 38.9g (0.1mol) (Reactant) (synthesized according to Peer.Kirsch et al., Angew.Chem.Int.Ed.2001.40.1480.), tetrakis (triphenylphosphine) palladium 0.3g (catalyst), sodium carbonate 15g (catalyst), toluene 100ml (solvent), 100ml water, 100ml ethanol (solvent), heated to reflux for 4 hours, added 100ml water, separated, the organic phase was evaporated to dryness, and recrystallized by column chromatography to obtain 37.8g of the product with a yield of 70%.

[0142] The structural confirmation data of this product are as follows:

[0143] GC: 99.9%;

[0144] MS: m / s%540 (M + 1.2) 393 (100) 267 (82.3) 239 (57.8)

[0145] 1H-NMR: δ (ppm)

[0146] 1.35(m,2H)1.56(m,8H)3.64(m,2H)3.88(m,2H)5.98(s,1H)6.89(m,2H)7.22(d,2H)7.40(m,4H)

[0147] As can be seen from the above, the product has a correct structure and is a compound shown in formula I...

Embodiment 3

[0154] Embodiment 3, Synthesis of (Method 3)

[0155]

[0156] Step 1: Synthesis of I-19-a

[0157] In a 500ml three-necked flask, add 0.1mol I-17-b and 12.4g (0.1mol) of 3-fluorobenzaldehyde (reactant) in a solution of 250ml toluene (solvent), then add 2g p-toluenesulfonic acid, The mixture was stirred and refluxed for 3 hours, cooled naturally to 20°C, added 50ml of water, separated, the organic phase was washed with 4×50ml of water, and the solvent was evaporated to dryness to obtain I-19-a

[0158] Step 2: Synthesis of I-19-b

[0159] Add 40ml of 2.5M (0.1mol) butyllithium (reactant) dropwise to 25g (0.1mol) of I-19-a (reactant) 11.2g (0.1mol) potassium tert-butoxide ( Reactant) in a solution of 250ml tetrahydrofuran (solvent), then dropwise add a solution of 13.5g (0.13mol) trimethyl borate (reactant) in 50ml tetrahydrofuran (solvent), stir the mixture at -60°C for 30 minutes, and heat up naturally At -20°C, add 50ml of water and 10ml of concentrated hydrochloric ...

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Abstract

The invention discloses a liquid crystal compound containing dioxane derivatives. The compound has a general structural formula as shown in a formula I, is more stable in structure, wide in liquid crystal state temperature range, better in low-temperature intersolubility and larger in dielectric anisotropy delta epsilon, can achieve lower threshold voltage and low rotary viscosity gamma 1 during the use of an optical device and improve the performance of a liquid crystal composition and a display, and has great significance to quick response of the display. The liquid crystal composition containing the compound can be applied to preparation of the liquid crystal display with low drive voltage, wide temperature range and high response speed.

Description

technical field [0001] The invention belongs to the field of synthesis and application of liquid crystal compounds, and relates to a dioxane derivative and a preparation method and application thereof. Background technique [0002] Liquid crystal displays using liquid crystal compositions are widely used in displays such as instruments, computers, and televisions. For the field of liquid crystal display technology, although the market has been very huge in recent years, the technology has gradually matured. With the rapid development of modern display technology, liquid crystal displays have experienced Twisted Nematic (TN) type and Super Twisted Nematic (STN) type. , thin film transistor liquid crystal display (TFT-LCD) has become the mainstream of flat panel display development. High-quality TFT-LCD requires high contrast, high definition, high-speed response, high brightness and wide viewing angle. In addition, low power consumption is also required. Therefore, liquid ...

Claims

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Application Information

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IPC IPC(8): C07D319/06C09K19/34C09K19/44G02F1/1333
CPCC07D319/06C09K19/3402C09K19/44C09K2019/3422G02F1/1333
Inventor 赵利峰韩耀华田秋峰赵磊段雅杰史正华瑞茂
Owner SHIJIAZHUANG CHENGZHI YONGHUA DISPLAY MATERIALS CO LTD
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