Polymerizable compound, and liquid crystal composition and liquid crystal display device using same
A compound, alkyl halide technology, used in liquid crystal materials, organic chemistry, nonlinear optics, etc., can solve problems such as high cost, and achieve uniform vertical orientation, stable tilt angle, and excellent preservation.
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Embodiment 1
[0276] 20 g of 3-fluoro-4-nonylphenylboronic acid, 10.6 g of bromophenol, 17 g of potassium carbonate, 200 mg of tetrakis-triphenylphosphine palladium, and 150 ml of ethanol were charged into a reaction vessel including a stirring device, a cooler, and a thermometer. The reaction was carried out at 90° C. for 5 hours. After the reaction was completed, it was cooled, 300 ml of ethyl acetate was added, the organic layer was washed with water and saturated brine, the solvent was distilled off, and recrystallized with toluene to obtain 18 g of the compound represented by (1).
[0277] [Chemical 61]
[0278]
[0279] Next, 18 g of compound (1) and 200 ml of dichloromethane were added to a reaction vessel including a stirring device, a dropping funnel, and a thermometer, and a dichloromethane solution of 27 g of bromine was slowly added dropwise at room temperature. After completion of the dropwise addition, it was further reacted at room temperature for 2 hours. After completi...
Embodiment 2
[0295] 30 g of 3-fluoro-4'-heptyl-[1,1'-biphenyl]-4-yl)boronic acid, 4-bromo-2-( 20 g of 3-hydroxypropyl)phenol, 18 g of potassium carbonate, 200 mg of tetrakis-triphenylphosphine palladium, and 200 ml of ethanol were reacted at 90° C. for 5 hours. After the reaction was completed, it was cooled, 300 ml of ethyl acetate and 100 ml of tetrahydrofuran were added, the organic layer was washed with water and saturated brine, the solvent was distilled off, and recrystallized with toluene to obtain 32 g of the compound represented by (5).
[0296] [chem 66]
[0297]
[0298] Next, 32 g of compound (5), 1.5 g of diisopropylamine, and 150 ml of dichloromethane were placed in a reaction vessel including a stirring device, a dropping funnel, and a thermometer, and cooled to 10°C. 30 ml of an acetonitrile solution of 13.5 g of N-bromosuccinimide was slowly added dropwise. After the dropwise addition, 10% sodium bisulfite was added after the reaction, the organic layer was washed wit...
Embodiment 3
[0318] 10 g of the compound (P-1-23) of Example 2 and 100 ml of dichloromethane were added to a reaction vessel including a stirring device, a dropping funnel, and a thermometer, and cooled to below 10°C. Then, 2 g of ethyl chloroformate was slowly added dropwise. After completion of the dropwise addition, the mixture was stirred for 30 minutes. Then, 2 g of triethylamine was added dropwise. After the reaction, the organic layer was washed with water and saturated brine, and the solvent was distilled off. Then, purification was performed with a silica gel column to obtain 9 g of the target compound represented by compound (P-1-24).
[0319] [chem 72]
[0320]
[0321] Melting point 75°C
[0322] 1 H-NMR (solvent: deuterated chloroform): δ: 0.83-0.88(m,6H), 1.27(s,8H), 1.63-1.69(m,4H), 1.91(m,2H), 1.97(s,6H ),2.63(t,4H),3.80(s,2H),3.89(d,4H),4.11-4.20(m,2H),5.60(s,1H),6.14(m,3H),7.02(m, 1H),7.28(d,2H),7.38(s,1H),7.61-7.64(m,3H),7.65(d,1H),7.94(m,1H)
[0323] 13 C-NM...
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