Diamine
An amide bond, independent technology, used in instruments, organic chemistry, liquid crystal materials, etc., can solve the problems of small anisotropy of polymer films, generation of afterimages, insufficient liquid crystal orientation, etc., and achieve excellent liquid crystal orientation. The effect of high stability, high reliability and high irradiation sensitivity
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[0184] Although an Example is given below and this invention is demonstrated in more detail, this invention is not limited to these. The abbreviations of the compounds used are as follows.
[0185] NMP: N-methyl-2-pyrrolidone, BCS: Butyl cellosolve
[0186]
[0187] [Synthesis of DA-1 (4'-(2-(4-aminophenoxy)ethoxy)-[1,1'-biphenyl]-4-amine)]
[0188] Step 1: Synthesis of 4-nitro-4'-(2-(4-nitrophenoxy)ethoxy)-1,1'-biphenyl (DA-1-1)
[0189]
[0190] 4-Hydroxy-4'-nitrobiphenyl (10.0g, 46.5mmol) was dissolved in DMF (40.0g), potassium carbonate (17.2g, 69.7mmol) was added, and β-bromo-4- DMF solution (40.0 g) of nitrophenetole (17.2 g, 69.7 mmol).
[0191] It stirred at 80 degreeC for 2 hours as it was, and the disappearance of the raw material was confirmed by high-performance liquid chromatography (hereinafter, abbreviated as HPLC). Then, the reaction liquid was allowed to cool to room temperature, and water (500.0 g) was added to filter out the precipitate, and the fi...
Synthetic example 1
[0219] Weigh 1.44g (4.50mmol) of DA-1 and 0.49g (4.53mmol) of DA-2 into a 50mL four-neck flask with a stirring device and a nitrogen gas introduction tube, add 25.38g of NMP, and carry out the process while feeding nitrogen gas. Stir to dissolve. While stirring this diamine solution, 1.92 g (8.56 mmol) of 1,3-dimethyl-1,2,3,4-cyclobutanetetracarboxylic dianhydride was added so that the solid content concentration became 12% by mass. 2.82 g of NMP was added in such a way that it was stirred at room temperature for 24 hours to obtain a polyamic acid solution (A). The viscosity of the polyamic acid solution at a temperature of 25° C. was 1680 mPa·s. In addition, the molecular weight of this polyamic acid was Mn=14700, Mw=35000.
Synthetic example 2
[0221] Weigh 2.24g (7.00mmol) of DA-1 into a 50mL four-neck flask equipped with a stirring device and a nitrogen gas introduction tube, add 24.64g of NMP, and stir while feeding nitrogen gas to dissolve it. While stirring this diamine solution, 1.49 g (6.65 mmol) of 1,3-dimethyl-1,2,3,4-cyclobutanetetracarboxylic dianhydride was added so that the solid content concentration became 12% by mass. 2.73 g of NMP was added in such a manner that it was stirred at room temperature for 24 hours to obtain a polyamic acid solution (B). The viscosity of the polyamic acid solution at a temperature of 25° C. was 2650 mPa·s. In addition, the molecular weight of this polyamic acid was Mn=21300, Mw=52300.
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