Liquid crystal aligning agent, liquid crystal alignment layer, liquid crystal display device and polyorganosilioxane compound
A polyorganosiloxane, liquid crystal aligning agent technology, applied in liquid crystal materials, chemical instruments and methods, instruments and other directions, can solve the problem of poor image sticking characteristics, can not fully meet the voltage retention rate, pretilt angle change with time, stability of printing and other problems, to achieve the effect of excellent afterimage characteristics and good stability over time.
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[0348] Hereinafter, although this invention is demonstrated in detail based on an Example, this invention is not limitedly interpreted by description of this Example.
[0349] In addition, the synthesis of raw material compounds and polymers in the synthesis routes shown in the following synthesis examples was repeated as necessary to ensure the required amounts of raw material compounds and polymers used in the following examples. The epoxy equivalent is measured according to the "hydrochloric acid-methyl ethyl ketone method" of JIS C2105.
[0350] The solution viscosity (mPa·s) was measured at 25° C. using an E-type rotational viscometer for a solution in which the polymer concentration of the polymer solution was adjusted to 10% by mass in each synthesis example.
[0351]
Synthetic example 1
[0353] In the reaction vessel with stirrer, thermometer, dropping funnel and reflux condenser, add 100.0g of 2-(3,4-epoxycyclohexyl) ethyl trimethoxysilane, 500g methyl isobutyl ketone and 10.0 g of triethylamine and mixed at room temperature. Next, 100 g of deionized water was dropped from the dropping funnel over 30 minutes, mixed under reflux, and reacted at 80° C. for 6 hours. After the reaction, the organic layer was taken out, washed with 0.2% by mass of ammonium nitrate aqueous solution until the washed water was neutral, and then the solvent and water were distilled off under reduced pressure to obtain a viscous transparent liquid having epoxy groups. organosiloxane.
[0354] The polyorganosiloxane with epoxy group is carried out 1 As a result of H-NMR analysis, an epoxy group-based peak with the same theoretical intensity was obtained around chemical shift (δ) = 3.2 ppm, thereby confirming that there was no side reaction in which epoxy groups were generated during t...
Synthetic example 2
[0358] The cinnamic acid derivative (A-1) was synthesized according to the following synthetic route.
[0359]
[0360] In a 1L eggplant-shaped flask, add 91.3g of methyl 4-hydroxybenzoate, 182.4g of potassium carbonate and 320mL of NMP, and stir at room temperature for 1 hour, then add 157.1g of 1-iodo-4,4, 4-Trifluorobutane, stirred at 100°C for 5 hours. After the reaction was completed, reprecipitation was performed with water. Next, 48 g of sodium hydroxide and 400 mL of water were added to the precipitate, and the mixture was refluxed for 3 hours to perform a hydrolysis reaction. After completion of the reaction, it was neutralized with hydrochloric acid, and the resulting precipitate was recrystallized with ethanol to obtain 110 g of white crystals of compound (A-1-1).
[0361] 12.41 g of compound (A-1-1) was weighed in a reaction vessel, and 100 mL of thionyl chloride and 77 μL of N,N-dimethylformamide were added thereto, and stirred at 80° C. for 1 hour. Next, th...
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