Adhesive sheet and semiconductor device and process for producing the same
A thin-film, adhesive technology, used in semiconductor/solid-state device manufacturing, semiconductor devices, adhesive types, etc., to solve problems such as reduced adhesion and low adhesion
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[0323] Hereinafter, the present invention will be described in more detail using examples. The present invention is not limited by these examples. In addition, the evaluation of the adhesive sheet can be performed according to the method described in the evaluation method column described later, unless otherwise specified in each Example.
Synthetic example 1
[0324] (Synthesis Example 1) [Synthesis of Photobase Generating Agent]
[0325] 30 g of 2-nitrobenzyl alcohol was dissolved in 300 g of tetrahydrofuran by stirring using a magnetic stirrer at room temperature. To this solution, a premixed solution consisting of 24.5 g of 4,4'-diphenylmethane diisocyanate and 100 g of tetrahydrofuran was added dropwise over 30 minutes, and stirred at room temperature for 1 hour. Thereafter, a Liebig cooling tube was attached, and reaction was performed for 2 hours while heating to 60° C. in an oil bath. After the reaction, it was cooled to room temperature, and the reaction solution was concentrated to half using a rotary evaporator.
[0326] Once the obtained concentrate was added to 1000 parts by weight of n-hexane, a white precipitate was obtained. The precipitate was suction-filtered and dried overnight at 60° C. under vacuum to obtain the target product 2-nitrobenzylcarbamate derivative (PB-1). Yield was 49.5 g (91% yield).
Synthetic example 2
[0327] (Synthesis Example 2) [Synthesis of Photobase Generating Agent]
[0328]Add methyl p-nitrobenzoate (2.00g, 11mmol), N,N-dimethylhydrazine (0.66g, 11mmol), phenyl glycidyl ether (1.66, 11mmol) in tert-butanol (15.0g) , after stirring at 50°C for 10 hours, and then stirring at room temperature (25°C) for 48 hours, a white precipitate was formed. The white precipitate was filtered, washed twice with ethyl acetate, and dried with a vacuum dryer to obtain an amine imide compound (PB-2). The yield was 3.67 g, the yield was 85%, and the melting point was 146-147°C.
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