Radiation-sensitive resin composition, resist pattern formation method, and acid diffusion control agent
A technology of resin composition and radiation, applied in the field of radiation-sensitive resin composition and acid diffusion control agent, can solve the problems of insufficient storage stability, achieve PEB shrinkage inhibition and storage stability, small LWR, and defect little effect
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[0373]
[0374] The radiation-sensitive resin composition can be prepared by combining [A] polymer, [B] acid generator, [C] compound, and optionally containing [D] polymer, [E] solvent, and other optional components. The mixture is mixed at a ratio of, and the obtained mixed liquid is preferably prepared by filtering 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 even more preferably 1% by mass. The upper limit of the solid content concentration is preferably 50% by mass, more preferably 30% by mass, and even more preferably 20% by mass.
[0375] This radiation-sensitive resin composition can be used for positive pattern formation using an alkaline developer, and can also be used for negative pattern formation using a developer containing an organic solvent. Among them, when used for negative pattern formation usin...
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 properties are shown below.
[0396] [Weight average molecular weight (Mw), number average molecular weight (Mn) and degree of dispersion (Mw / Mn)]
[0397] The Mw and Mn of the polymer were measured by gel permeation chromatography (GPC) using GPC columns manufactured by Tosoh Corporation (2 "G2000HXL", 1 "G3000HXL", and 1 "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 rate: 1.0mL / min
[0400] Sample concentration: 1.0% by mass
[0401] Sample injection volume: 100μL
[0402] Column temperature: 40℃
[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] Combine 9,10-phenanthrenequinone 2.08g (10mmol), 3,4,5-trimethoxyaniline 2.75g (15mmol), 2-trifluoromethanesulfonyloxybenzaldehyde 2.54g (10mmol), ammonium acetate 3.85g (50mmol) and 100mL of acetic acid were put into the 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 sodium bicarbonate aqueous solution were added for liquid separation. The organic layer was dried with anhydrous sodium sulfate, filtered, and the solvent was distilled off. Purification was performed by silica gel column chromatography to obtain compound (C-1) (yield 4.43 g, yield 73%).
[0412]
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