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Preparation and use of low-temperature low-viscosity liquid crystal compositions

A liquid crystal composition and low-viscosity technology, applied in the direction of liquid crystal materials, chemical instruments and methods, etc., can solve the problems of slow low temperature response speed, large temperature dependence, high viscosity of liquid crystal materials, etc., and achieve the effect of improving low temperature response speed

Inactive Publication Date: 2015-04-29
WUHAN POLYTECHNIC UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
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AI Technical Summary

Problems solved by technology

[0003] The main reason for the phenomenon of animation afterimage, trailing and low-temperature response speed is that the existing liquid crystal material has a high viscosity, especially the low-temperature viscosity and low-temperature response speed have a large temperature dependence. The bottleneck of application development (Angew.Chem.Int.Ed., 2000, 39: 4216-4235; J.Mater.Chem., 2004, 14, 1219-1227)
Because reducing the thickness of the box will affect the yield of LCD production, increasing the operating voltage will increase the energy consumption of the LCD

Method used

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  • Preparation and use of low-temperature low-viscosity liquid crystal compositions
  • Preparation and use of low-temperature low-viscosity liquid crystal compositions
  • Preparation and use of low-temperature low-viscosity liquid crystal compositions

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Synthesis of [(4-propyl)benzene-1-difluoromethyleneoxy]-(4’-pentyl)benzene(3PdFOP5)(Ia-1)

[0047] Synthesis of 4-propylbenzene trifluorosulfonium disulfonium salt (Na):

[0048] Under stirring, 8.4g (78mmol) of 1,3-propanedithiol was added to a suspension of 9.8g (60mmol) of 4-propylbenzoic acid (M) mixed with 30ml of toluene and 30ml of n-heptane, and heated to 50 ℃; under the protection of nitrogen, add trifluoromethanesulfonic acid (11.7g, 78mmol) dropwise for about 30 minutes; then heat the reaction solution to reflux, separate out about 3ml of water, continue to stir, heat to reflux for 0.5h, stop heating and Stir. The reaction solution was cooled to 60°C, and 50 ml of isopropyl ether was slowly added. The suspension was lowered to -50°C and isopropyl ether was separated. Then add 50ml×3 isopropyl ether and wash 3 times. Rotary evaporation of the solvent at room temperature to obtain 18.5 g of 4-propylbenzenetrifluorosulfonium bissulfonium salt (Na) as a brown-red ...

Embodiment 2

[0062] Synthesis of [(4-propyl)phenyl-1-difluoromethyleneoxy]-3’,4’-difluorobenzene (3PdFOP(3F, 4F), Id-1):

[0063] The target compound (Ie-1) was synthesized with the method of Example 1. A colorless and transparent liquid was obtained with a yield of 81%.

[0064] IR (vmax, KBr) cm-1: 2959, 2927, 2855, 1618, 1519, 1465, 1331, 1037, 809, 785;

[0065] 1H NMR (300MHz, CDCl3) δ: 7.31(d, J=6.1Hz, 2H), 7.08-7.21(m, 2H), 7.03(d, J=6.2Hz, 2H), 6.68(t, J=15.4Hz) , 1H), 2.62 (t, J = 18.1 Hz, 2H), 1.43-1.59 (m, 2H), 1.01 (t, J = 9.7 Hz, 3H);

[0066] 19C NMR (75MHz, CDCl3): 156.85, 151.52, 145.12, 142.85, 134.28, 132.52, 129.33, 127.45, 119.25, 112.58, 105.22, 35.78, 31.90, 14.13;

[0067] .19F NMR (330MHz CDCl3): -141.07 (s, 1F), -134.58 (s, 1F), -65.76 (s, 2F). m / z (%): 298 [M+].

Embodiment 3

[0069] Synthesis of [trans(4-propyl)cyclohexyl-1-difluoromethyleneoxy]-(4'-pentyl)benzene (3CdFOP5, Ie-1):

[0070] The target compound (Ij-1) was synthesized by the same method as in Example 1. A colorless and transparent liquid was obtained with a yield of 83%.

[0071] IR (vmax, KBr): 2951, 2938, 2848, 1616, 1516, 1451, 1174, 782 (cm-1);

[0072] 1H NMR (300MHz CDCl3) δ: 7.24 (d, J = 6.0 Hz, 2H), 6.98 (d, J = 6.2 Hz, 2H), 2.62 (t, J = 18.4 Hz, 2H), 2.48-2.56 (m, 1H), 1.76-1.59 (m, 6H), 1.29-1.31 (m, 13H), 0.92 (t, J=9.9 Hz, 6H);

[0073] 19C NMR (75MHz CDCl3): 154.65, 134.21, 130.41, 129.82, 114.22, 42.23, 37.13, 35.75, 31.42, 30.98, 29.32, 26.58, 22.72, 20.52, 14.45, 14.23, 13.73;

[0074] 19F NMR (330MHz CDCl3): -78.64 (s, 2F); m / z (%): 338 [M+].

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Abstract

The invention provides preparation and use of low-temperature low-viscosity liquid crystal compositions. The compositions have relatively low viscosity and relatively small temperature dependency under the condition of low temperature, can meet all low-temperature performances needed by liquid crystal materials, and can be used for manufacturing liquid crystal display devices, improving low-temperature liquid crystal display performance and increasing the response speed of liquid crystal low-temperature display. The liquid crystal compositions are characterized by comprising the compound of formula (I), in the formula, R is alkyl or alkoxyl with 1-12 carbons, X is -R, -F, -Cl, OCF3, CF3, CF2CF3 or OCHF2, Y is -H or -F, A is phenylene or cyclohexylidene, or cyclohexane or an aromatic ring, wherein the cyclohexane or the aromatic ring is substituted by -F or -Cl; and when Y is -H, X is not -R or -F. The compound has low-temperature low viscosity and the relatively small temperature dependency, is used as a liquid crystal component to replace ester liquid crystal components with relative structures, effectively reduces the low-temperature viscosity of the liquid crystal compositions and decreases the dependency of the viscosity on temperature, has excellent low-temperature compatibility with other liquid crystal compounds, and is made into the liquid crystal compositions with the low-temperature low viscosity and quick response.

Description

Invention field [0001] The invention belongs to the field of organic compounds, and specifically relates to the preparation and use of a type of low-temperature and low-viscosity liquid crystal composition. Background technique [0002] Thin film transistor liquid crystal display (TFT-LCD) has become the mainstream of flat panel display development. In 2006, the response speed of TFT-LCD on the market has grown to 5 milliseconds (25°C). However, there are still animation afterimages, smearing, and low-temperature display speed in the video display, which limits its outdoor application. The same problem is in the normal TN (twisted nematic) display mode, HTN (highly twisted nematic) display mode, STN (super twisted nematic) mode, PDLC (polymer dispersed liquid crystal) mode, DS (dynamic scattering) ) Mode, GH (guest-host) mode, ECB (electrically controlled birefringence) mode, DAP mode, and DSTN (reflective bistable) mode are common in liquid crystal displays (LCD), and they can'...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09K19/30C09K19/20C09K19/46
Inventor 张智勇张泽龙邓萌萌戴志群任占冬
Owner WUHAN POLYTECHNIC UNIVERSITY
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