Fluorine-containing alicyclic dianhydride compound, preparation method thereof and application thereof
A compound and polymer technology, applied in chemical instruments and methods, organic chemistry, semiconductor/solid-state device manufacturing, etc., can solve the problems of high cost and expensive PI alignment agent, and achieve the effect of low residual DC voltage
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Embodiment 1、3
[0050] Example 1, 3,4-carboxy-1,2,3,4-tetrahydro-6-fluoro-1-naphthalene dioic anhydride (FTDA) synthesis
[0051] Add 43.75g (0.446mol) maleic anhydride, 108.9g (0.892mol) 4-fluorostyrene, 0.1g (0.446mmol) 2 , 5-Di-tert-butylhydroquinone, heated to 120°C under the catalysis of nitric oxide gas, and maintained constant temperature for 6h, and a large amount of orange solid was precipitated. Add 60 mL of acetonitrile, raise the temperature to reflux for 0.5 h, and the reaction system dissolves into a clear liquid. Add 60 mL of toluene and cool. A large number of crystals precipitated, filtered and washed three times with toluene. After washing with petroleum ether three times, loose white crystals were obtained, and vacuum-dried at 80° C. for 24 hours to obtain 54.9 g of white crystals, with a yield of 77.3%.
[0052] The structure of this compound is shown in formula I-1, wherein R 1 =-H:
[0053] (Formula I-1)
[0054] The detection data are as follows (the proton nucl...
Embodiment 2、3
[0062] Embodiment 2, 3,4-carboxy-1,2,3,4-tetrahydro-6-fluoro-1-naphthalene dioic anhydride (FTDA) synthesis
[0063] Add 43.75g (0.446mol) maleic anhydride, 83.30g (0.682mol) 4-fluorostyrene, 0.1g (0.446mmol) 2 , 5-Di-tert-butylhydroquinone, heated to 120°C under the catalysis of nitric oxide gas, and maintained constant temperature for 6h, and a large amount of orange solid was precipitated. Add 60 mL of acetonitrile, raise the temperature to reflux for 0.5 h, and the reaction system dissolves into a clear liquid. Add 60 mL of toluene and cool. A large number of crystals precipitated, filtered and washed three times with toluene. After washing with petroleum ether three times, loose white crystals were obtained, and vacuum-dried at 80° C. for 24 hours to obtain 54.6 g of white crystals, with a yield of 77%.
[0064] The structure of this compound is shown in formula I-1, wherein R 1 =-H:
[0065] (Formula I-1)
[0066] Detection data is consistent with embodiment 1. ...
Embodiment 3
[0067] Embodiment 3, prepare polyimide (FTDA-MDA) by FTDA and 4,4'-diaminodiphenylmethane (MDA)
[0068] In a 100mL three-necked flask equipped with a nitrogen inlet and equipped with a thermometer, water separator, condenser and mechanical stirring, 1.9826g (10mmol) of MDA and 10g of m-cresol were added. After stirring at room temperature to make it dissolve completely, add 3.1825g (10mmol) of FTDA prepared in Example 1 and 10g of m-cresol, and adjust the solid content to 15% (mass percentage) with m-cresol. g isoquinoline and 30 g toluene, heat up to reflux, separate water for 4 hours, then release toluene from the water separator and continue to heat up, raise the temperature to 180°C for 6 hours, stop the reaction, and lower the temperature. After cooling down to room temperature, the resulting yellow viscous solution resin solution was poured into a large amount of ethanol to obtain a white filamentous PI resin (4.95 g), which is the polyimide shown in formula IV provided...
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