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Multifluoro substituted diphenyl acetylene derivative, composition containing multifluoro substituted diphenyl acetylene derivatire, its preparation method and use

A technology of diphenylacetylene and derivatives, applied in the field of compounds, can solve problems such as limited compatibility, and achieve the effects of good miscibility, wide nematic phase temperature range, and simple and feasible synthesis route

Inactive Publication Date: 2007-02-14
SHIJIAZHUANG CHENGZHI YONGHUA DISPLAY MATERIALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0022] Although the above-mentioned liquid crystal compound Δn is large and the temperature range of the nematic phase is very wide, its compatibility with other liquid crystal compounds is still limited, especially at low temperatures.

Method used

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  • Multifluoro substituted diphenyl acetylene derivative, composition containing multifluoro substituted diphenyl acetylene derivatire, its preparation method and use
  • Multifluoro substituted diphenyl acetylene derivative, composition containing multifluoro substituted diphenyl acetylene derivatire, its preparation method and use
  • Multifluoro substituted diphenyl acetylene derivative, composition containing multifluoro substituted diphenyl acetylene derivatire, its preparation method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] This example is the preparation of 2,3-difluoro-4-(4``-butylphenyl)-2`-fluoro-4`-methyltolanyne (I-1)

[0057]

[0058] Step 1-1: Synthesis of 4`-butyl-2,3-difluorobiphenyl: Add 25.5g (0.12mol) 4-butylbromobenzene, 2,3-difluorophenylboronic acid 15.8 g (0.1mol), 21.2g (0.2mol) of sodium carbonate, 100ml of toluene, 80ml of ethanol, 60ml of water, 0.5g of Pd[0], exhaust the air with nitrogen, heat and reflux for 7 hours, cool down, and pour it into a 1L separatory funnel , separated to remove the water layer, extracted twice with 25ml toluene, combined the organic layers, washed with water until neutral, evaporated toluene to dryness, collected 17.5g of 134~136°C / 3mmHg fraction under reduced pressure, and the gas chromatography purity of the product was ≥99%, and the yield was 71 %.

[0059] Step 1-2: Synthesis of 4`-butyl-2,3-difluorobiphenyl iodide: add 29.6g (0.12mol) 4`-butyl-2,3-difluorobiphenyl into a three-necked flask, Cool 200mlTHF to -80°C, start to drop 0...

Embodiment 2

[0070] This example is the preparation of 2,3-difluoro-4-(4``-butylphenyl)-3`-fluoro-4`-methyltolanyne (I-2)

[0071]

[0072] Preparation Process Example 1, the difference is that the raw material 3-fluoro-4-bromotoluene in step 2-1 is replaced by 2-fluoro-4-bromotoluene to prepare 3-fluoro-4-methylphenylacetylene, Then it was coupled with the product 4'-butyl-2,3-difluoroiodobiphenyl in step 1-2, and purified by recrystallization to obtain the target compound (I-2), with a total yield of 34%.

[0073] The experimental results are as follows:

[0074] (1) Compound phase texture: C56.85°C S m 59.19°C N133.29°C I.

[0075] molecular formula

Characteristic ions (M / Z + ) and abundance (%)

C 25 h 21 f 3

378(M + 、58.97)、335(100)、319(11.38)、167(6.06)

[0076] (3) Elemental analysis:

[0077] Theoretical calculation value: C (79.35%), H (5.59%);

[0078] Experimental values: C (79.33%), H (5.60%).

Embodiment 3

[0080] This embodiment is the preparation (I-3) of 2,3-difluoro-4-(4``-butylphenyl)-2`-fluoro-4`-propyl tolueneacetylene:

[0081]

[0082] The preparation process is the same as in Example 1, except that the raw material 3-fluoro-4-bromotoluene in step 2-1 is changed to 3-fluoro-4-bromopropylbenzene.

[0083] The experimental results are as follows:

[0084] (1) Compound phase texture: C46.57℃ N158.03℃I

[0085] molecular formula

Characteristic ions (M / Z + ) and abundance (%)

C 27 h 25 f 3

406(M + 、100)、377(20.75)、363(88.37)、334(52.12)、167(11.79)

[0086] (3) Elemental analysis:

[0087] Theoretical calculation value: C (79.78%), H (6.20%);

[0088] Experimental values: C (79.77%), H (6.18%).

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Abstract

The present invention relates to one kind of polyfluoro substituted diphenyl acetylene derivative and its composition, preparation process and use as the liquid crystal material for display. The polyfluoro substituted diphenyl acetylene derivative has the general expression as shown, great optical anisotropy, relatively low viscosity, relatively wide nematic phase temperature range, excellent low temperature compatibility, facile material, and simple and feasible synthetic path, and is suitable for use as displaying liquid crystal material with improved response speed and driving voltage. The liquid crystal composition has excellent performance, including greatly improved response speed and low temperature compatibility, and may be used in liquid crystal display of TN mode, STN mode, TFT mode, etc.

Description

technical field [0001] The invention relates to a polyfluorinated tolan derivative, a composition containing the polyfluorinated tolan derivative, a preparation method thereof and its use as a liquid crystal material for display, belonging to the field of compounds. Background technique [0002] Liquid crystal materials develop rapidly along with the development of liquid crystal displays, among which nematic phase materials for display are the fastest growing type of liquid crystal materials with the largest market share. Nematic liquid crystal displays include TN (twisted nematic) mode, STN (super twisted nematic) mode, TFT (thin film transistor) mode and other liquid crystal displays. Has been widely used in watches, electronic calculators, PDAs, mobile phones, information terminals and portable computers, TV-LCD and other displays. Especially in the 21st century, with the rapid development of information technology, there are higher requirements for response speed and i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C25/24C07C43/247C09K19/18G02F1/13
Inventor 刘鑫勤李邵辉员国良尹子言李强
Owner SHIJIAZHUANG CHENGZHI YONGHUA DISPLAY MATERIALS CO LTD
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