Lateral difluoromethylene ether bridge double-terminal alkylcyclohexylbiphenyl derivatives and preparation method and application thereof

A technology of alkyl ring and hexyl, which is applied in the field of side difluoromethylene ether bridge double-terminal alkyl cyclohexyl biphenyl derivatives and its preparation and application, which can solve the problem of large conjugated system and optical anisotropy Big, limited, etc.

Active Publication Date: 2019-07-12
TSINGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the three benzene rings in the structure of the terphenyl liquid crystal compound, the conjugated system of the liquid crystal molecule is larger, which in turn leads to a larger optical anisotropy (Δn) of the liquid crystal molecule, which makes it restricted in application. certain restrictions

Method used

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  • Lateral difluoromethylene ether bridge double-terminal alkylcyclohexylbiphenyl derivatives and preparation method and application thereof
  • Lateral difluoromethylene ether bridge double-terminal alkylcyclohexylbiphenyl derivatives and preparation method and application thereof
  • Lateral difluoromethylene ether bridge double-terminal alkylcyclohexylbiphenyl derivatives and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0163] The preparation of embodiment 1,1-methoxy group-4-(4-pentylcyclohexyl) benzene

[0164] 250mL three-necked bottle, equipped with mechanical stirring, thermometer, reflux condenser, put 4.92g (20.0mmol) 4-(4-pentylcyclohexyl) phenol, 2.84g (20.0mmol) CH 3 I, 2.76g (20.0mmol) K 2 CO 3 , 70mL of acetone, reflux (temperature is 56 ℃) for 6 hours, stop the reaction. The solid was removed by filtration, and the solvent was evaporated by a rotary evaporator, and the obtained crude product was purified by silica gel column chromatography, and the eluent was petroleum ether. The eluent was evaporated to remove the solvent with a rotary evaporator to obtain 4.80 g of a crude solid product. The crude product was recrystallized from petroleum ether to obtain 3.50 g of white crystals (GC purity 99%), with a yield of 65%.

[0165] Structural Confirmation Data:

[0166] IR(KBr)ν max / cm -1 :3035, 3001, 2954, 2916, 2846, 1614, 1514, 1248, 1036;

[0167] 1 HNMR (300MHz) δ: 7.12...

Embodiment 2

[0179] The preparation of embodiment 2,1-methoxy-2-bromo-4-(4-pentylcyclohexyl)benzene

[0180] 2L three-necked flask, equipped with a mechanical stirrer and a thermometer, put in 36.00g (138.0mmol) 1-methoxy-4-(4-pentylcyclohexyl)benzene, 1000mL acetonitrile, 10°C, and stir until all solids in the reaction solution are dissolved , added 24.60g (138.0mmol) NBS in batches, and reacted for another 7 hours after the addition was completed. The solvent was evaporated by a rotary evaporator, and the obtained crude product was purified by silica gel column chromatography, and the eluent was petroleum ether. The eluent was evaporated to remove the solvent with a rotary evaporator to obtain 53.00 g of crude product. The crude product was recrystallized from petroleum ether to obtain 42.00 g of white crystals (GC purity 96%), with a yield of 89%.

[0181] Structural Confirmation Data:

[0182] IR(KBr)ν max / cm -1 : 3032, 3007, 2953, 2918, 2848, 1257, 1055;

[0183] 1 HNMR (300MHz)...

Embodiment 3

[0196] The preparation of embodiment 3,1-methoxy-2-cyano-4-(4-pentylcyclohexyl)benzene

[0197] 250mL three-necked flask, equipped with mechanical stirring, thermometer, reflux condenser, put 2.78g (8.2mmol) 1-methoxy-2-bromo-4-(4-pentylcyclohexyl)benzene, 1.80g (20.0mmol) CuCN, 70mL N-methylpyrrolidone, reflux (at 203°C) for 6 hours, cool down to 60°C, add 2.00g FeCl 3 , 0.5mL HCl, 20mL water, stirred for 1 hour. The reaction solution was cooled to room temperature, extracted with chloroform (30 mL×3), and the organic phase was washed with water until neutral. After removing the solvent with a rotary evaporator, 2.50 g of crude product was obtained. The obtained crude product was purified by silica gel column chromatography, and the eluent was a mixed solvent of ethyl acetate and petroleum ether with a volume ratio of 1:10. The eluent was evaporated to remove the solvent with a rotary evaporator to obtain 2.00 g of crude product. The crude product was recrystallized with ...

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Abstract

The invention discloses double-alkyl-terminated cyclohexylbiphenyl derivative with lateral difluoromethylene ether bridge bonds and a preparation method and application thereof; a structural formula of the compound is as shown in formula I that is shown in the description; in the formula I, both R and R' are C1-C10 linear or branched alkyl; difluoromethylene ether group is introduced to cyclohexylbiphenyl ring structure; under electronegative accumulative action of C-F bonds in the group and the group being in lateral position of the molecular long axis, these molecules have great dielectric constant (epsilon T) perpendicular to the molecular axis and negative dielectric anisotropy (Delta<epsilon><0); due to the introduction of the difluoromethylene ether group, conjugation of the biphenyl structure is broken, great anisotropy (Delta<epsilon><0) is imparted; this compound has low melting point and improved solubility and is a high-performance liquid crystal display material.

Description

technical field [0001] The invention relates to a lateral difluoromethylene ether bridge double-terminal alkyl cyclohexyl biphenyl derivative and a preparation method and application thereof, belonging to the field of liquid crystal display materials. Background technique [0002] With the rapid development of the liquid crystal display technology, the liquid crystal display shows stronger and stronger market competitiveness, but the liquid crystal display technology also faces many problems to be solved urgently. For a period of time, how to expand the viewing angle of liquid crystal displays has been one of the main problems plaguing designers. In response to this, various display modes have been designed to try to increase the viewing angle of liquid crystal displays, such as In-Plane-Switching Thin Solid Film (IPS-TFT) mode and Vertical Alignment Thin Film Transistor (Vertical Alignment Thin Film Transistor) mode. Solid Film, referred to as VA-TFT) mode development, bot...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/80C09K19/34G02F1/1333
CPCC07D311/80C09K19/3402C09K2019/3425G02F1/1333
Inventor 唐洪梁晓李楠
Owner TSINGHUA UNIV
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