Effect of polymer structure on dissolution-rate characteristics in carboxylated alicyclic polymers for 193-nm lithography

We characterize the effect of structure on the dissolution rate and adhesion of poly(carboxy-tricyclodecylmethyl methacrylate) which is the base polymer for ArF excimer laser lithography. The adhesion of the polymer decreases with an increase in the protection ratio, and 60% tert-butyl protection causes stripping and collapse of the pattern in 2.38% tetramethylammonium hydroxide (TMAH) developer. We synthesize novel protection groups: menthyl derivatives and a hydroxy-tricyclodecyl (meth)acrylate [TCD(M)AOH] unit, and confirm their improved adhesion and dissolution inhibiting effects in the 2.38% TMAH developer. We obtain a 0.35 micrometer pattern using a resist based on a terpolymer containing TCDAOH and the standard developer.

[1]  Hiroshi Yanazawa.  Adhesion model and experimental verification for polymer—SiO2 system , 1984 .

[2]  Takeshi Ohfuji,et al.  Novel alkaline-soluble alicyclic polymer poly(TCDMACOOH) for ArF chemically amplified positive resists , 1996, Advanced Lithography.

[3]  Naomi Shida,et al.  NOVEL ArF EXCIMER LASER RESISTS BASED ON MENTHYL METHACRYLATE TERPOLYMER , 1996 .

[4]  Richard A. Di Pietro,et al.  193-nm single-layer positive resists: building etch resistance into a high-resolution imaging system , 1995, Advanced Lithography.

[5]  Katsumi Maeda,et al.  Positive chemically amplified resist for ArF excimer laser lithography composed of a novel transparent photoacid generator and an alicyclic terpolymer , 1995, Advanced Lithography.

[6]  Naomichi Abe,et al.  Evaluation of chemically amplified resist based on adamantyl methacrylate for 193-nm lithography , 1995, Advanced Lithography.

[7]  Ei Yano,et al.  Impact of 2-Methyl-2-Adamantyl Group Used for 193-nm Single-layer Resist , 1996 .

[8]  F. Fowkes.  ATTRACTIVE FORCES AT INTERFACES , 1964 .

[9]  Katsumi Maeda,et al.  Dissolution behavior of alicyclic polymers designed for ArF excimer laser lithography , 1996, Advanced Lithography.

[10]  R. D. Allen,et al.  RESOLUTION AND ETCH RESISTANCE OF A FAMILY OF 193nm POSITIVE RESISTS , 1995 .

[11]  G. Drescher,et al.  Surface tension, adhesion and wetting of materials for photolithographic process , 1996 .

[12]  Naomichi Abe,et al.  Alicyclic polymer for ArF and KrF excimer resist based on chemical amplification , 1992, Advanced Lithography.

[13]  Jun-ichi Yano,et al.  Transparent photoacid generator (ALS) for ArF excimer laser lithography and chemically amplified resist , 1994, Advanced Lithography.