Photosensitive ray composition and pattern forming method and method for mfg. semiconductor device
A radiation-sensitive and manufacturing method technology is applied in the manufacturing field of electronic devices and semiconductor devices, which can solve problems such as resolution deterioration, and achieve the effects of improving resolution, large changes in dissolution speed, and improving sensitivity.
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Embodiment 1
[0055] Dissolve 10 g of 2-hydroxy-3,3-dimethyl-γ-lactone and 9 g of pyridine in 200 ml of tetrahydrofuran. A solution obtained by dissolving 7.5 g of chlorinated acrylic acid in 30 ml of tetrahydrofuran was dropped therein at 0°C. After the dropwise addition, the precipitated pyridine hydrochloride was filtered off after further stirring at room temperature for 12 hours. Add 300 ml of ethyl acetate to the filtrate, and wash with 200 ml of water 4 times. After washing with water, the organic layer was dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. Purified by vacuum distillation to obtain a colorless and transparent acrylate monomer (8).
[0056] The above-mentioned acrylate monomer (8) 5g (2.7×10 -2 mol) and 24g of 3-hydroxy-1-adamantyl acrylate monomer (1.1×10 -1 mol) was dissolved in 100 ml of tetrahydrofuran at a molar ratio of 2:8, and bubbled with nitrogen gas for 10 minutes. Next, 1.5 g of dimethyl-2,2'-azobisisobutyrate was...
Embodiment 2
[0065] With respect to 100 parts by weight of the polymer synthesized in Example 1, 1 part by weight of the acid generator triphenylsulfonium triflate (triflate), 0.5 parts by weight of triphenylsulfonium nonaflate (nonaflate), and 0.2 parts by weight of triethanolamine and 10 parts by weight of a low molecular weight compound (7) having a carboxylic acid were dissolved in 1200 parts by weight of 1-methoxy-2-propanol, and filtered through a Teflon filter with a pore size of 0.20 μm to form a resist solution. Also, in order to improve storage stability, 0.5N ammonia solution was added to 100 parts by weight of the resist solution.
[0066] Exposure of this resist film was performed through a conversion phase shift mask using an ArF excimer laser stepper (ISI Microstep, NA=0.60) in the same manner as in Example 1. A post-exposure bake was performed at 120° C. for 60 seconds after exposure. Thereafter, imaging was carried out for 10 seconds with a tetramethylammonium hydroxide a...
Embodiment 3
[0069] The synthesis method of Example 1 was repeated except that the 2-hydroxy-3,3-dimethyl-γ-lactone in Example 1 was replaced with 4-hydroxy-γ-butyrolactone. As a result of analyzing the structure of the obtained polymer by various analytical methods, it was found that it was a copolymer (11) in which the molar percentage of acrylate having a γ-hydroxycarboxylic acid structure was 20%.
[0070] As a result of measuring the polystyrene-equivalent molecular weight of this polymer in tetrahydrofuran by gel permeation chromatography (GPC), the weight average molecular weight was 5,500, and the number average molecular weight was 4,300.
[0071] Next, when using an ArF excimer laser stepper (ISIMrostep, NA=0.60) in the same manner as in Example 1, when forming a fine pattern with a transformation-type phase shift mask, at 40mJ / cm 2 A negative-type 0.10 μm line-and-space pattern is obtained. At this time, swelling of the pattern was not observed, and no residue was observed be...
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