Fluorine-containing biphenyl acetylene liquid crystal compound and preparation method thereof

A liquid crystal compound and phenylacetylene technology, which is applied in the fields of liquid crystal optical devices, liquid crystal displays, and fluorine-containing biphenylacetylene liquid crystal compounds, can solve the problems of difficulty in forming a eutectic liquid crystal mixture, high melting point, and inability to meet application requirements in low temperature performance. , to achieve the effect of high birefringence, low melting point and large dielectric anisotropy

Active Publication Date: 2014-10-08
XIAN MODERN CHEM RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0018] Although the melting point of the liquid crystal compound is significantly lower than that of the monofluorine-substituted liquid crystal material, its melting point is still higher.
Since the usual fluorine-containing alkyne liquid crystal has a relatively high melting point, it is difficult to form a liquid crystal mixture with a eutectic point, and the low-temperature performance cannot meet the application requirements

Method used

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  • Fluorine-containing biphenyl acetylene liquid crystal compound and preparation method thereof
  • Fluorine-containing biphenyl acetylene liquid crystal compound and preparation method thereof
  • Fluorine-containing biphenyl acetylene liquid crystal compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0063] Preparation of 2,3',4',5'-tetrafluoro-4-((4-propylphenyl)ethynyl)biphenyl:

[0064] The specific structural formula is as follows:

[0065]

[0066] The preparation process is as follows:

[0067] (1) 30.1g (0.1mol) 3-fluoro-4-bromoiodobenzene, 100ml THF (not dried), 0.7g (0.001mol) bis(triphenylphosphine) palladium chloride, 0.57g (0.003mol) iodine Cuprous sulfide and 20.2g (0.2mol) of triethylamine were sequentially added to a 500ml three-necked flask, the air was replaced by high-purity nitrogen, and the temperature was lowered to 5°C. Dissolve 14.4g of 4-propylphenylacetylene in 100ml of THF, add dropwise to the reaction flask, and complete the drop within 1hr. After dripping, the temperature was naturally raised to room temperature and reacted for 5 hours. The by-product salt was removed by filtration, the filtrate was evaporated to dryness, and the obtained oily product was dissolved through a silica gel column with n-heptane. The resulting solution was concentrated ...

Embodiment 2～ Embodiment 6

[0079] Use 4-ethylphenylacetylene, 4-butylphenylacetylene, 4-pentylphenylacetylene, 4-hexylphenylacetylene, 4-heptylphenylacetylene to replace 4-propylphenylacetylene in Example 1, respectively, the same The method synthesizes:

[0080] 2,3',4',5'-tetrafluoro-4-((4-ethylphenyl)ethynyl)biphenyl;

[0081] 2,3',4',5'-tetrafluoro-4-((4-butylphenyl)ethynyl)biphenyl;

[0082] 2,3',4',5'-tetrafluoro-4-((4-pentylphenyl)ethynyl)biphenyl;

[0083] 2,3',4',5'-tetrafluoro-4-((4-hexylphenyl)ethynyl)biphenyl;

[0084] 2,3',4',5'-tetrafluoro-4-((4-heptylphenyl)ethynyl)biphenyl.

Embodiment 7

[0086] The preparation of 2,3',4'-trifluoro-4-((4-propylphenyl)ethynyl)biphenyl, the specific structural formula is as follows:

[0087]

[0088] Using 3,4-difluorophenylboronic acid instead of 3,4,5-trifluorophenylboronic acid in Example 1, 2,3',4'-trifluoro-4-(( 4-propylphenyl)ethynyl)biphenyl, the yield is 64%.

[0089] The liquid crystal phase transition temperature of 2,3',4'-trifluoro-4-((4-propylphenyl)ethynyl)biphenyl was tested by DSC at a temperature of 5℃ / min. The result is: C59.5N118 .4I.

[0090] Dissolve it in the basic formula at a mass ratio of 15% to test its refractive index, and extrapolate to obtain the birefringence Δn=0.3173, Δε=13.10, γ at 25°C and 589nm 1 = 109.8mPa·s. The compound has the advantages of high birefringence, large dielectric anisotropy, and low rotational viscosity.

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Abstract

The invention discloses a fluorine-containing biphenyl acetylene liquid crystal compound and a preparation method thereof. The structural general formula of the compound is shown as (1) in the specification, wherein R is straight-chain alkane with the number of carbons being 1-9, X1, X2, X3 and X4 are H or F, and at least one of X3 and X4 is F. The fluorine-containing biphenyl acetylene liquid crystal compound has the advantages of being high in birefringence, low in melting point and viscosity, and large in dielectric anisotropy, and is suitable for the application fields of liquid crystal display, laser communication and the like.

Description

Technical field [0001] The invention belongs to the technical field of liquid crystal materials, and specifically relates to a fluorine-containing biphenyl acetylene liquid crystal compound, which is mainly used for liquid crystal displays, liquid crystal optical devices and the like. Background technique [0002] Liquid crystal displays are classified according to the display mode, including twisted nematic (TN), super twisted nematic (STN), dynamic scattering mode (DSP), thin film transistor drive mode (TFT), etc. TFT liquid crystal display can realize full color, high resolution, wide viewing angle, fast response, etc., and has been widely used. The liquid crystal materials used in liquid crystal displays generally have a nematic phase within the operating environment temperature range from -20°C to +70°C. At the same time, they must have a high degree of chemical stability, low viscosity, and birefringence suitable for the application. Liquid crystal physical properties such...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K19/18C09K19/44C07C25/24C07C17/263
Inventor 安忠维李建李娟利杨晓哲车昭毅胡明刚武斌杨志莫玲超
Owner XIAN MODERN CHEM RES INST
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