Liquid crystal alignment agent containing polyamic acid ester, and liquid crystal alignment film
A technology of liquid crystal aligning agent and polyamic acid ester, which is applied in instruments, optics, nonlinear optics, etc., can solve the problems of improving the characteristics of liquid crystal aligning agent, high residual charge, and high volume resistivity, which can improve reliability, Effects of improved interface properties and improved electrical properties
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[0258] Hereinafter, the present invention will be described in more detail by way of examples, but the present invention is not limited thereto.
[0259] Hereinafter, the abbreviations used in the present Examples and Comparative Examples and the measurement methods of each characteristic are as follows.
[0260] 1,3DMCBDE-Cl: Dimethyl 1,3-bis(chlorocarbonyl)-1,3-dimethylcyclobutane-2,4-dicarboxylate
[0261] DA-1: the above formula (D-25)
[0262] BDA: 1,2,3,4-butanetetracarboxylic dianhydride
[0263] CBDA: 1,2,3,4-cyclobutanetetracarboxylic dianhydride
[0264] NMP:N-methyl-2-pyrrolidone
[0265] γ-BL: γ-Butyrolactone
[0266] BCS: Butyl Cellosolve
[0267] PAE: Polyamic acid ester
[0268] PAA: polyamic acid
[0269] DA-2: the above formula (D-29)
[0270] DA-3: The above formula (D-30)
[0271] DA-4: the above formula (D-28)
[0272] DA-5: the above formula (DA-32)
[0273] DA-6: n=5 of the above formula (DA-35)
[0274] DA-7: The following formula (DA-7)
[...
Synthetic example 1
[0325] The diamine compound (DA-1) was synthesized by a four-step route shown below.
[0326] Step 1: Synthesis of Compound (A5)
[0327] [Chemical 58]
[0328]
[0329] In a 500 mL eggplant-shaped flask, propargylamine (8.81 g, 160 mmol), N,N-dimethylformamide (112 mL), and potassium carbonate (18.5 g, 134 mmol) were sequentially added to make it 0° C. A solution obtained by dissolving tert-butyl bromoacetate (21.9 g, 112 mmol) in N,N-dimethylformamide (80 mL) was added dropwise with stirring for about 1 hour. After the dropwise addition, the reaction solution was brought to room temperature and stirred for 20 hours. Then, solid content was removed by filtration, 1 L of ethyl acetate was added to the filtrate, and the mixture was washed four times with 300 mL of water and once with 300 mL of saturated brine. Then, the organic layer was dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. Finally, the residual oil was distilled under redu...
Synthetic example 2
[0343] A 300mL four-necked flask with a stirring device was placed in a nitrogen atmosphere, DA-1 of 4,4'-diaminodiphenylmethane 4.486g (22.63mmol), 2.147g (5.658mmol) was added, NMP 121.37g, and 5.16 g (65.19 mmol) of pyridine as a base was dissolved by stirring. Next, 8.8384 g (27.16 mmol) of 1,3DM-CBDE-Cl was added while stirring the diamine solution, and the reaction was carried out under water cooling for 4 hours. After 4 hours, 134.86 g of NMP was added to the reaction solution, and the mixture was stirred at room temperature (20° C.) for 15 minutes. The obtained polyamic acid ester solution was added to 1349 g of water with stirring, and the precipitated white precipitate was collected by filtration. Then, it was washed once with 1349 g of water, once with 1349 g of ethanol, and 3 times with 337 g of ethanol. After drying, 11.04 g of white polyamic acid ester resin powder was obtained. The yield was 81.9%. Moreover, the molecular weight of this polyamic acid ester is...
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