Radiation-sensitive resin composition, resist pattern forming method, and acid diffusion controlling agent
A technology of resin composition and radiation, which is applied in the field of acid diffusion control agent and radiation sensitive resin composition, can solve the problems of insufficient storage stability and achieve PEB shrinkage inhibition and storage stability, small LWR, resolution high rate effect
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[0373]
[0374] This radiation-sensitive resin composition can be prepared by, for example, [A] polymer, [B] acid generator, [C] compound, and if necessary, [D] polymer, [E] solvent, and other optional components. The ratio is mixed, and the obtained mixed solution is preferably prepared by filtering, for example, through a filter with a pore size of about 0.2 μm. The lower limit of the solid content concentration of the radiation-sensitive resin composition is preferably 0.1% by mass, more preferably 0.5 parts by mass, and still more preferably 1% by mass. The upper limit of the solid content concentration is preferably 50% by mass, more preferably 30% by mass, and still more preferably 20% by mass.
[0375] This radiation-sensitive resin composition can be used for positive pattern formation using an alkaline developing solution, and can also be used for negative pattern formation using a developing solution containing an organic solvent. Among them, when used for negativ...
Embodiment
[0395] Hereinafter, the present invention will be specifically described based on examples, but the present invention is not limited to these examples. The measurement methods of various physical property values are shown below.
[0396] [Weight average molecular weight (Mw), number average molecular weight (Mn) and degree of dispersion (Mw / Mn)]
[0397] Mw and Mn of the polymer were measured by gel permeation chromatography (GPC) using Tosoh GPC columns (two "G2000HXL", one "G3000HXL", and one "G4000HXL") under the following conditions. In addition, the degree of dispersion (Mw / Mn) was calculated from the measurement results of Mw and Mn.
[0398] Elution solvent: tetrahydrofuran
[0399] Flow: 1.0mL / min
[0400] Sample concentration: 1.0% by mass
[0401] Sample injection volume: 100μL
[0402] Column temperature: 40°C
[0403] Detector: Differential refractometer
[0404] Standard material: monodisperse polystyrene
[0405] [ 1 H-NMR analysis and 13 C-NMR analys...
Synthetic example 1
[0410] [Synthesis Example 1] (Synthesis of Compound (C-1))
[0411] 2.08g (10mmol) of 9,10-phenanthrenequinone, 2.75g (15mmol) of 3,4,5-trimethoxyaniline, 2.54g (10mmol) of 2-trifluoromethanesulfonyloxybenzaldehyde, and 3.85g of ammonium acetate (50 mmol) and 100 mL of acetic acid were put into a reaction vessel, heated to 110° C. and stirred for 4 hours. Next, acetic acid was removed under reduced pressure, and 50 mL of ethyl acetate and 50 mL of saturated aqueous sodium bicarbonate solution were added for liquid separation. The organic layer was dried over anhydrous sodium sulfate, filtered, and the solvent was distilled off. Purification was carried out by silica gel column chromatography to obtain compound (C-1) (yield 4.43 g, yield 73%).
[0412]
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