Liquid crystal aligning agent for photo-alignment, liquid crystal aligning film, liquid crystal display device, polymer, and diamine
A technology of liquid crystal display element and liquid crystal alignment agent, which is applied in liquid crystal materials, optics, nonlinear optics, etc.
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[0460] Hereinafter, the present invention will be described through examples. In addition, the evaluation methods and compounds used in the examples are as follows.
[0461] 1. Weight average molecular weight (Mw)
[0462] The weight average molecular weight of a polyamic acid is calculated|required by the GPC method using 2695 separation modules and 2414 differential refractometers (made by Waters), and it performs polystyrene conversion. The obtained polyamic acid was diluted with the phosphoric acid-dimethylformamide (Dimethylformamide, DMF) mixed solution (phosphoric acid / DMF=0.6 / 100:weight ratio) so that the polyamic acid concentration might become about 2 weight%. HSPgel RT MB-M (manufactured by Waters) was used as a column, and the mixed solution was used as a developing solvent, and the measurement was performed at a column temperature of 50° C. and a flow rate of 0.40 mL / min. As the standard polystyrene, TSK standard polystyrene manufactured by Tosoh Co., Ltd. was u...
Synthetic example 1
[0486] [Synthesis Example 1] Synthesis of Compound (4-1)
[0487]
[0488]Methyl 4-nitrobenzoate (25.0 g, 138.0 mmol), hydrazine monohydrate (35.0 mL) and ethanol (600 mL) were added to a 1000 mL three-necked flask equipped with a reflux tube, a thermometer, and a nitrogen gas introduction tube. Thereafter, the solution was stirred at reflux for 5 hours under nitrogen atmosphere. After adding water (150 mL) to the reaction solution, it was filtered to obtain 4-nitrobenzohydrazide (yield: 18.8 g, yield: 75%).
[0489]
[0490] Add 4-nitrobenzohydrazide (18.8g, 103.8mmol), 4-nitrobenzaldehyde (15.7g, 103.9mmol), trifluoroacetic acid to a 500mL three-necked flask equipped with a reflux tube, a thermometer, and a nitrogen inlet tube (1.02g, 10.4mmol) and ethanol (200mL). The solution was stirred under reflux for 1 hour under a nitrogen atmosphere, cooled and then filtered to obtain the following compound (yield: 32.7 g, yield: 100%).
[0491]
[0492]
[0493] Add the ...
Synthetic example 2
[0495] [Synthesis Example 2] Synthesis of Compound (5-1)
[0496]
[0497] Add methyl 4-bromobenzoate (25.0g, 116.3mmol), 4-nitrophenylboronic acid (21.3g, 127.9mmol), potassium carbonate to a 1000mL three-necked flask equipped with a reflux tube, a thermometer, and a nitrogen inlet tube (32.1g, 232.6mmol), PdCl 2 (dppf)CH 2 Cl 2 (1.90 g, 2.33 mmol), water (200 mL) and 1,4-dioxane (200 mL). Thereafter, the solution was stirred at reflux for 3 hours under nitrogen atmosphere. The reaction solution was poured into saturated sodium bicarbonate water (200 mL), and ethyl acetate (300 mL) was added for extraction. After drying the organic layer with magnesium sulfate, the solvent was distilled off under reduced pressure to obtain a crude product. The crude product was purified by silica gel chromatography to obtain the following compound (yield: 29.6 g, yield: 99%).
[0498]
[0499]
[0500] The compound obtained in the first stage (29.6 g, 115.1 mmol), hydrazine monoh...
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