Liquid crystal aligning agent, liquid crystal aligning film and liquid crystal display element
A technology of liquid crystal orientation and treatment agent, applied in the directions of instruments, optics, nonlinear optics, etc., can solve the problems of reduced contrast, poor representation, etc.
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[0261] Although an Example is given below and this invention is demonstrated more concretely, it is not limited to them.
[0262] Abbreviations used in Synthesis Examples, Examples, and Comparative Examples are as follows.
[0263] (specific compound)
[0264] S1: Phosphotungstic acid (manufactured by Nippon Shinkoku Co., Ltd.)
[0265] S2: Phosphomolybdic acid (12 molybdenum (IV) phosphoric acid n-hydrate) (manufactured by Kanto Chemical Co., Ltd.)
[0266] (specific side chain type diamine compound)
[0267] A1: 1,3-diamino-4-[4-(trans-4-n-heptylcyclohexyl)phenoxy]benzene
[0268] A2: 1,3-diamino-5-[4-(trans-4-n-heptylcyclohexyl)phenoxymethyl]benzene
[0269] A3: 1,3-diamino-4-{4-[trans-4-(trans-4-n-pentylcyclohexyl)cyclohexyl]phenoxy}benzene
[0270] A4: Diamine compound represented by the following formula [A4]
[0271] A5: 1,3-diamino-4-octadecyloxybenzene
[0272]
[0273]
[0274] (Other diamine compounds)
[0275] B1: p-phenylenediamine
[0276] B2: m-ph...
Synthetic example 1
[0314] Mix C4 (5.51g, 18.4mmol), A5 (0.78g, 2.07mmol) and B1 (2.01g, 18.6mmol) in NMP (17.4g), react at 40°C for 6 hours, add C1 (0.40g, 2.04mmol) and NMP (8.70g), and reacted at 40 degreeC for 6 hours, and obtained the polyamic-acid solution whose resin solid content concentration was 25 mass %.
[0315] After adding NMP to the obtained polyamic-acid solution (30.0g) and diluting to 6 mass %, acetic anhydride (3.90g) and pyridine (2.40g) were added as an imidization catalyst, and it was made to react at 70 degreeC for 4 hours. This reaction solution was poured into methanol (460 ml), and the obtained precipitate was collected by filtration. This deposit was wash|cleaned with methanol, and it dried under reduced pressure at 100 degreeC, and obtained the polyimide powder (1). The imidization rate of this polyimide was 84%, the number average molecular weight was 19,300, and the weight average molecular weight was 52,300.
Synthetic example 2
[0317] C2 (6.55g, 26.2mmol), A3 (4.92g, 11.4mmol), B1 (2.46g, 22.7mmol) and B3 (0.77g, 3.79mmol) were mixed in NEP (33.8g) and reacted at 80°C for 5 After one hour, C1 (2.20g, 11.2mmol) and NEP (16.9g) were added, it was made to react at 40 degreeC for 6 hours, and the polyamic-acid solution (2) whose resin solid content concentration was 25 mass % was obtained. The number average molecular weight of this polyamic acid was 19,500, and the weight average molecular weight was 65,800.
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