Composition for forming silicon-containing resist underlayer film removable by wet process
A technology of resist lower layer and composition, applied in the direction of coating, photoengraving process of pattern surface, photosensitive material for opto-mechanical equipment, etc., can solve problems such as substrate damage
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[0186] (Synthesis of 4-(trimethoxysilyl)benzyl acetate)
[0187]
[0188] 30.0 g of sodium acetate and 150.0 g of N-methylpyrrolidone (hereinafter also referred to as NMP) were added to a 300 mL three-necked flask equipped with an electromagnetic stirrer, and heated to 130° C. in an oil bath. There, 90.25 g of (p-chloromethyl)phenyltrimethoxysilane was added dropwise, followed by heating and stirring for 4 hours. The obtained solution was returned to room temperature, transferred to a separatory funnel, 300 g of toluene and 90 g of water were added, and the organic layer was washed. After washing was repeated three times, magnesium sulfate was added to the organic layer, dried, filtered, and the solvent was evaporated to obtain a crude product. Then, purification was carried out by distillation under reduced pressure to obtain 60 g of 4-(trimethoxysilyl)benzyl acetate as the target substance.
[0189] 1 H-NMR (500MHz, DMSO-d 6 ): 2.08ppm (s, 3H), 3.54ppm (s, 9H), 5.10pp...
Synthetic example 1
[0191] In a 500mL four-necked flask equipped with a stirrer, a reflux condenser, a dropping funnel and a thermometer, 75g of water was added, and 50g of 4-methoxybenzyltrimethoxysilane was added dropwise at a reaction temperature of 20°C (in all silanes, 100mol%) of toluene 75g solution. After completion of the dropwise addition, the reaction was carried out at the same temperature for 2 hours, and liquid separation was carried out after standing still to recover the oil layer. Next, washing was performed with a 5% aqueous sodium bicarbonate solution. Next, this toluene solution was transferred to a 500 mL four-necked flask equipped with a stirrer, a distillation tower, a cooler, and a thermometer, put into an oil bath, and heated slowly to distill off toluene. After toluene was distilled off, the temperature was further increased, and aging was carried out at 200° C. for 2 hours. Then, it was transferred to a 300mL four-necked flask equipped with a stirrer, a reflux condens...
Synthetic example 2
[0193] In a 500mL four-necked flask equipped with a stirrer, a reflux condenser, a dropping funnel and a thermometer, 74g of water was added, and 36.3g of 4-methoxybenzyltrimethoxysilane (in all silanes) was added dropwise at a reaction temperature of 20°C. 70 mol%) and 12.7 g of phenyltrimethoxysilane (30 mol% in all silanes) in 74 g of toluene. After completion of the dropwise addition, the reaction was carried out at the same temperature for 2 hours, and liquid separation was carried out after standing still to recover the oil layer. Next, washing was performed with a 5% aqueous sodium bicarbonate solution. Next, this toluene solution was transferred to a 500 mL four-necked flask equipped with a stirrer, a distillation tower, a cooler, and a thermometer, and placed in an oil bath, and heated slowly to distill off toluene. After toluene was distilled off, the temperature was further increased, and aging was carried out at 200° C. for 2 hours. Then, it was transferred to a ...
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