Liquid crystal alignment agent, liquid crystal alignment film, liquid crystal display element, polymer and compound
A liquid crystal alignment agent and liquid crystal alignment technology, which are used in the fields of liquid crystal display elements, polymers and compounds, liquid crystal alignment agents, and liquid crystal alignment films, can solve problems such as irradiation, and achieve good printability, good electrical properties, and good printability. Effect
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[0172] Hereinafter, the present invention will be described more specifically by way of examples, but the present invention is not limited by these examples.
[0173] The solution viscosity of each polymer solution in a polymerization example, and the imidation ratio of a polyimide can be measured by the following method.
[0174] [Solution Viscosity of Polymer Solution]
[0175] The solution viscosity (mPa·s) of the polymer solution can be measured at 25° C. using an E-type rotational viscometer on a solution adjusted to a polymer concentration of 10% by weight using a predetermined solvent.
[0176] [Imidation rate of polyimide]
[0177] Put the polyimide solution into pure water, dry the resulting precipitate under reduced pressure at room temperature, dissolve it in deuterated dimethyl sulfoxide, and measure it at room temperature using tetramethylsilane as a standard substance 1 H-NMR. From the obtained 1H-NMR spectrum, the imidation rate [%] was calculated|required fr...
Synthetic example 1
[0183] Diamine (B-1) was synthesized according to the following Scheme 1.
[0184] [chemical 9]
[0185]
[0186] Process 1
[0187] 198mmol (27.9g) of 4-fluoronitrobenzene, 90.0mmol (9.01g) of homopiperazine (homopiperazine), 198mmol (27.4g) of potassium carbonate and 198ml of dimethylacetamide were mixed, and heated at 100°C for 7 It was made to react by stirring for an hour. 300 ml of distilled water was mixed, and the precipitated solid was collected by filtration. It was sufficiently washed with distilled water and tetrahydrofuran, and dried to obtain 84.4 mmol (28.9 g, yield: 93.8%) of the target intermediate (B-1-a) as a yellow powder.
[0188] 84.4 mmol (28.9 g) of the above-mentioned intermediate, 2.89 g Pd / C, 317 ml tetrahydrofuran, 106 ml ethanol, and 28.9 ml hydrazine monohydrate (hydrazine) monohydrate were mixed and stirred while heating at 70° C. for 24 hours. its reaction. After removing Pd / C by filtration, 500 ml of ethyl acetate was added, and extract...
Synthetic example 2
[0190] Diamine (B-2) was synthesized according to the following Scheme 2.
[0191] [chemical 10]
[0192]
[0193] Process 2
[0194] Mix 154mmol (21.7g) of 3-fluoronitrobenzene, 70.0mmol (7.01g) of homopiperazine, 154mmol (21.3g) of potassium carbonate, and 154ml of methylacetamide, and stir while heating at 100°C for 9 hours and make it react. 250 ml of distilled water was mixed, and the precipitated solid was collected by filtration. It was sufficiently washed with distilled water and tetrahydrofuran, and dried to obtain 63.6 mmol (21.8 g, yield: 90.9%) of the target intermediate (B-2-a) as a yellow powder.
[0195] 63.6 mmol (21.8 g) of the above-mentioned intermediate, 2.18 g of Pd / C, 239 ml of tetrahydrofuran, 80 ml of ethanol, and 21.8 ml of hydrazine monohydrate were mixed, and heated and stirred at 70°C for 20 hours to react. After removing Pd / C by filtration, 500 ml of ethyl acetate was added, and extraction and washing were performed five times with 250 ml of...
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