Liquid crystal alignment agent, liquid crystal alignment film and liquid crystal display element
A technology of liquid crystal alignment agent and carbon number, which is applied in liquid crystal materials, instruments, optics, etc., can solve the problems of substrate reusability (poor reworkability, poor peelability of coating film, etc.), and achieve excellent peelability, Show good quality results
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[0152] Hereafter, although an Example demonstrates this invention more concretely, this invention is not limited to these Examples. The solution viscosity of each polymer solution in the synthesis example and the imidization rate of polyimide were measured by the following method.
[0153] [Solution Viscosity of Polymer Solution]
[0154] The solution viscosity (mPa·s) of the polymer solution was measured at 25° C. using an E-type rotational viscometer for the solutions indicated in the respective synthesis examples.
[0155] [Imidation rate of polyimide]
[0156] A small amount of the obtained polyimide solution was dropped into pure water, and the precipitate generated was recovered and fully dried under reduced pressure at room temperature, then dissolved in deuterated dimethyl sulfoxide, and tetramethylsilane was used as a reference, and the measured at room temperature 1 H-NMR. derived from 1 In H-NMR, the imidation rate was calculated|required from the formula shown...
Synthetic example B-1
[0164] 12.1 g (0.10 mol) of N-methylbenzylamine, 100 mL of methanol, and 9.4 mL (0.12 mol) of epichlorohydrin were mixed, stirred at 80° C. for 6 hours, and reacted. After the reaction was over, remove the solvent from the reaction mixture under reduced pressure, and dissolve the resulting viscous body in 100 mL of tert-butanol, then add 10 mL of an aqueous potassium hydroxide solution with a concentration of 0.013 mol / L, and stir at 80 ° C. 2 hours. Next, 500 mL of ethyl acetate was added to the reaction mixture, the obtained organic layer was washed with water, and concentrated to form a heavy solution. The resulting solution was subjected to column chromatography (filler: silica gel, developing solvent: hexane / ethyl acetate=50 / 1 (volume ratio)), and the solvent was removed from the fraction to obtain 13.9 g (0.08 mol) of the compound (B-1-14) solid.
Synthetic example B-2
[0166] Except in above-mentioned synthesis example B-1, use 16.3g (0.10 mole) N-tert-butylbenzylamine to replace N-methylbenzylamine, and synthesis example B-1 is the same, obtain 15.9g (0.07 mole) compound ( B-1-20) solid.
[0167]
[0168] [Polymerization example of polyamic acid]
[0169] Polymerization example PA-1
[0170] With 98g (0.50 mole) 1,2,3,4-cyclobutanetetracarboxylic dianhydride and 109g (0.50 mole) pyromellitic dianhydride as tetracarboxylic dianhydride, and 198g (1.0 mole) as diamine mol) 4,4'-diaminodiphenylmethane, dissolved in a mixed solvent of 230g N-methyl-2-pyrrolidone and 2,060g γ-butyrolactone, reacted at 40°C for 3 hours, and then added 1,350 g of γ-butyrolactone to obtain a solution containing 10% by weight of polyamic acid (PA-1). The solution viscosity of this solution was 118 mPa·s.
[0171] Polymerization example PA-2
[0172] 196g (1.0 mole) of 1,2,3,4-cyclobutanetetracarboxylic dianhydride as tetracarboxylic dianhydride and 212g (1.0 m...
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