Actinic-ray- or radiation-sensitive resin composition and method of forming pattern using the composition
A technology of resin composition and actinic ray, which is applied in the photoplate-making process of patterned surface, photosensitive material for optomechanical equipment, optics, etc., can solve the problem of unstable resist composition and achieve pattern shape Effects of improved and line edge roughness and high stability
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Embodiment 1
[0751] Synthesis Example 1 (Synthesis of Monomer (Compound (4)))
[0752] [Compound (1)]
[0753] Compound (1) shown below was synthesized by the method described in International Publication No. 07 / 037213 (single volume).
[0754] [Compound (2)]
[0755] Water in an amount of 150.00 g was added to 35.00 g of Compound (1), and 27.30 g of NaOH was further added to the mixture. The resulting mixture was stirred while heating at reflux for 9 hours. Subsequently, hydrochloric acid was added to acidify the mixture. Thereafter, extraction with ethyl acetate was performed. The organic phase was collected and concentrated to obtain 36.90 g of compound (2) (yield 93%).
[0756] 1 H-NMR (400MHz, in (CD 3 ) 2 CO): σ(ppm)=1.56-1.59(1H), 1.68-1.72(1H), 2.13-2.15(1H), 2.13-2.47(2H), 3.49-3.51(1H), 3.68(1H), 4.45 -4.46(1H)
[0757] [Compound (3)]
[0758] 200ml of CHCl 3 To 20.00 g of compound (2), 50.90 g of 1,1,1,3,3,3-hexafluoroisopropanol and 30.00 g of 4-dimethylaminopyridin...
Embodiment 2
[0764] Synthesis Example 2: Synthesis of Hydrophobic Resin (C-7)
[0765] Monomers corresponding to the repeating units shown below were charged at a molar ratio of 90 / 10 and dissolved in PGMEA to obtain 450 g of a solution with a solid content of 15% by mass. Thereafter, 1 mol % of a polymerization initiator V-60 manufactured by Wako Pure Chemical Industries, Ltd. was added to the solution. The resulting mixture was dropped into 50 g of PGMEA heated at 100° C. in a nitrogen atmosphere over a period of 6 hours. After the dropwise addition was completed, the reaction liquid was stirred for two hours. After the reaction was completed, the reaction liquid was cooled to room temperature and crystallized in 5 liters of methanol. The white powder thus precipitated was collected by filtration. Thus, the desired resin (C-7) was recovered.
[0766] The polymer composition ratio measured by NMR was 90 / 10. As determined by GPC measurement, its weight average molecular weight based o...
Embodiment 1 to 35 and comparative example 1 and 2
[0770]
[0771] Dissolution of the components in the solvent as shown in Table 3 below was performed so as to obtain a solution with a solid content of 5% by mass. The solution was passed through a polyethylene filter with a pore size of 0.1 μm to obtain a positive resist composition. The positive resist composition thus obtained was evaluated by the following method, and the evaluation results are shown in Table 4.
[0772]
[0773] An organic antireflection film ARC29A (manufactured by Nissan Chemical Industries, Ltd.) was coated on a silicon wafer and baked at 205° C. for 60 seconds, thereby forming an antireflection film with a thickness of 98 nm. Each of the prepared positive resist compositions was coated thereon and baked at 130° C. for 60 seconds, thereby forming a 120 nm-thick resist film. The resulting wafer was exposed by an ArF excimer laser liquid-immersion scanner (manufactured by ASML, XT1700i, NA 1.20) through a 6% dot mask of 65 nm 1:1 line and space patt...
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