Film forming composition, resist composition, radiation-sensitive composition, method for producing amorphous film, resist pattern formation method, composition for forming lower layer film for lithography, method for producing lower layer film for lithography, and circuit pattern formation method
Composition and lower layer technology, applied to film forming composition, resist composition, radiation sensitive composition, manufacture of amorphous film, resist pattern formation, lower layer film forming composition for photolithography , In the field of the manufacture of the lower layer film for lithography and the formation of circuit patterns, it can solve the problems of the collapse of the resolution resist pattern and the difficulty in obtaining the resist pattern, etc., and achieve the effect of excellent heat resistance and/or etching resistance and/or optical properties
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[0532] Hereinafter, although an Example and a comparative example are shown, and this embodiment is demonstrated in more detail, this embodiment is not limited to these.
[0533] The analysis and evaluation methods of the polycyclic polyphenol resin in this embodiment are as follows.
[0534] The 1H-NMR measurement was carried out under the following conditions using "Advance 600II spectrometer" manufactured by Bruker Corporation.
[0535] Frequency: 400MHz
[0536] Solvent: d6-DMSO
[0537] Internal standard: TMS
[0538] Measuring temperature: 23°C
[0539]
[0540] The molecular weight of the polycyclic polyphenol resin was measured by LC-MS analysis using Acquity UPLC / MALDI-Synapt HDMS manufactured by Water Corporation.
[0541]
[0542] The polystyrene-equivalent weight average molecular weight (Mw) and number average molecular weight (Mn) were determined by gel permeation chromatography (GPC) analysis, and the degree of dispersion (Mw / Mn) was determined.
[0543...
Synthetic example 1
[0554] (Synthesis Example 1) Synthesis of R-DHN
[0555] 16.8 g (105 mmol) of 2,6-dihydroxynaphthalene (agent manufactured by Kanto Chemical Co., Ltd.) and 10.1 g of copper monobutyl phthalate ( 20 mmol), 30 mL of 1-butanol was added as a solvent, and the reaction solution was stirred at 110° C. for 6 hours to perform a reaction. After cooling, the precipitate was filtered, and the obtained crude product was dissolved in 100 mL of ethyl acetate. Next, 5 mL of hydrochloric acid was added, stirred at room temperature, and then neutralized with sodium bicarbonate. The ethyl acetate solution was concentrated, and 200 mL of methanol was added to precipitate the reaction product. After cooling to room temperature, it was filtered and separated. The obtained solid was dried to obtain 27.3 g of the target resin (R-DHN) having a structure represented by the following formula.
[0556] About the obtained resin, the polystyrene conversion molecular weight was measured by the said meth...
Synthetic example 1-2
[0560] (Synthesis Example 1-2) Synthesis of R-2,7DHN
[0561] 16.8 g (105 mmol) of 2,7-dihydroxynaphthalene (a reagent manufactured by Kanto Chemical Co., Ltd.) and 15.2 g of monobutyl phthalate copper ( 30 mmol), 40 mL of 1-butanol was added as a solvent, and the reaction solution was stirred at 110° C. for 6 hours to perform a reaction. After cooling, the precipitate was filtered, and the obtained crude product was dissolved in 100 mL of ethyl acetate. Next, 5 mL of hydrochloric acid was added, stirred at room temperature, and then neutralized with sodium bicarbonate. The ethyl acetate solution was concentrated, and 200 mL of methanol was added to precipitate the reaction product. After cooling to room temperature, it was filtered and separated. The obtained solid was dried to obtain 24.7 g of the target resin (R-2,7DHN) having a structure represented by the following formula.
[0562] About the obtained resin, the polystyrene conversion molecular weight was measured by t...
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