Pattern forming method and bilayer film
a technology of bilayer film and pattern forming method, which is applied in the direction of photosensitive materials, instruments, photomechanical equipment, etc., can solve the problems of cracks and peels in resist film, resolution cannot be increased, and the accuracy of the excimer laser using these resins cannot be high,
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synthesis example 1-1
Preparation of Under Layer Film Polymer
[0237] A separable flask equipped with a thermometer was charged with 100 parts of acenaphthylene, 78 parts of toluene, 52 parts of dioxane, and 3 parts of azobisisobutyronitrile under nitrogen atmosphere. The mixture was stirred for 5 hours at 70° C. Next, 5.2 parts of p-toluenesulfonic acid monohydrate and 40 parts of paraformaldehyde were added. After heating to 120° C., the mixture was stirred for 6 hours. The reaction solution was charged into a large amount of isopropanol. The resulting precipitate was collected by filtration and dried at 40° C. under reduced pressure to obtain a polymer.
[0238] Mw of the polymer was found to be 22,000 and 1H-NMR analysis confirmed that the polymer has the structural unit of the following formula (26).
synthesis example 1-2
Preparation of Under Layer Film Polymer
[0239] A separable flask equipped with a thermometer was charged with 6 parts of acenaphthylene, 5 parts of 4-hydroxymethylstyrene, 48 parts of n-butylacetate, and 4 parts of azobisisobutyronitrile under nitrogen atmosphere. The mixture was stirred for 7 hours at 75° C.
[0240] The reaction solution was diluted with 100 parts of n-butyl acetate and charged into a large amount of a water / methanol mixture (weight ratio=½). The resulting precipitate was collected by filtration and the solvent was evaporated to obtain a polymer with an Mw of 1,200.
synthesis example 2
Synthesis of Silane Compound
[0241] A three-necked flask equipped with a stirrer, a reflux condenser, and a thermometer was charged with 76.0 g of triethoxysilane and 100 g of 8-t-butoxycarbonyltetracyclo[4.4.0.12,5.17,10]dodeca-3-ene. The mixture was stirred at room temperature and 5.0 ml of a 0.2 mol chloroplatinic acid (H2PtCl6) solution in i-propyl alcohol was added to initiate the reaction. The reaction was continued for 75 hours at 150° C. while refluxing. The reaction mixture was allowed to cool to room temperature, diluted with n-hexane, and filtered through celite by suction. The solvent was removed from the filtrate by evaporation under vacuum to obtain a crude product. The residue was purified by silica gel column chromatography to obtain 53 g of a reaction product as a n-hexane fraction. As shown by the following results of 1H-NMR spectrum (chemical shift σ) and IR spectrum measurement, this reaction product was identified to be the compound shown by the following formul...
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