Diamine compound, and polyimide precursor and polyimide film using same
A technology of amine compounds and divalent organic groups, applied in chemical instruments and methods, organic chemistry, coatings, etc., can solve the problems of glass substrate weight, difficult continuous process, etc., and achieve the effect of improving thermal and mechanical properties
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[0150] Hereinafter, embodiments of the present invention will be described in detail so that those skilled in the art can easily carry out the present invention. However, this invention may be embodied in many different forms and should not be construed as limited to the embodiments set forth herein.
Synthetic example 1
[0151] Preparation of Compound 1
[0152]
[0153] Preparation of Compound 1-3
[0154] Compound 1-1 (108.0 g, 0.65 mol) and compound 1-2 (73.0 g, 0.32 mol) were dissolved in THF (500 mL) and potassium carbonate (135.2 g, 0.97 mol) was dissolved in water under nitrogen atmosphere (250 mL), then heated to 100 °C. To the reaction mixture was added tetrakistriphenylphosphine palladium (11.29 g) under reflux and stirred for 12 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, and then ethyl acetate (250 mL) was added to separate the organic layer. The separated organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed by vacuum distillation apparatus (BUCHI Rotavapor R-300) to obtain compound 1-3 (60.3 g, yield 69%).
[0155] Preparation of Compound 1-5
[0156] Compound 1-3 (20.0 g, 74.3 mmol) and Compound 1-4 (4.0 g, 37.1 mmol) were added to propionic acid (500 mL) under reflux, and stirred for 12 ho...
Synthetic example 2
[0160] Preparation of Compound 2
[0161]
[0162] Preparation of compound 2-2
[0163] Compound 1-3 (20.0 g, 74.3 mmol) and Compound 2-1 (9.07 g, 37.1 mmol) were added to propionic acid (500 mL) under reflux, and stirred for 12 hours. After the reaction was complete, the reaction mixture was cooled to room temperature, and ethanol (500 mL) was added to disperse the resulting solid. After the reaction mixture was filtered, the obtained solid was washed with water and ethanol (1:1, volume ratio) to obtain compound 2-2 (24.9 g, yield 90%).
[0164] Preparation of compound 2
[0165] Compound 2-2 (24.9 g, 33.3 mmol) was dissolved in THF (200 mL), and a Pd / C catalyst was added, followed by heating to 60°C. The reaction mixture was stirred for 4 hours with continuous injection of hydrogen. After the reaction was completed, the reaction mixture was cooled to room temperature and filtered to obtain a solid. The obtained solid was recrystallized from ethanol (200 mL) to obtai...
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