Sulfonium Salts of Alicyclic Group Functionalized Semifluorinated Alkyl Ether Sulfonates As Photoacid Generators

作者: Yi Yi , Ramakrishnan Ayothi , Yueh Wang , Mingqi Li , George Barclay

DOI: 10.1021/CM901366R

关键词: Thermal stabilitySulfonateOrganic chemistryPolymer chemistryX-ray photoelectron spectroscopySolubilityPolymerSulfoniumFluorideChemistryAlicyclic compound

摘要: We describe new sulfonium salts incorporating semifluorinated sulfonate anions and their successful application as photoacid generators (PAGs) intended to solve the environmental problems caused by perfluorooctyl (PFOS). By utilizing simple unique chemistries based on 5-iodooctafluoro-3-oxapentanesulfonyl fluoride, a series of alicyclic-group functionalized octafluoro-3-oxapentane-sulfonate were prepared in high purity yield. Triphenylsulfonium (TPS) norbornyl γ-butyrolactone groups octafluoro-3-oxapentanesulfonates extensively studied. They have excellent thermal stability good solubility various polar solvents. Their optical properties thoroughly investigated. Angle resolved X-ray photoelectron spectroscopy (XPS) analysis confirmed that TPS are uniformly distributed polymer films, whereas PFOS is heavily segregated film surface. Lithographic performance together with ...

参考文章(34)
Maharshi M. Chauhan, Paul F. Nealey, Outgassing of photoresists in extreme ultraviolet lithography Journal of Vacuum Science & Technology B. ,vol. 18, pp. 3402- 3407 ,(2000) , 10.1116/1.1321754
Pawel J. Serafinowski, Peter B. Garland, Novel photoacid generators for photodirected oligonucleotide synthesis. Journal of the American Chemical Society. ,vol. 125, pp. 962- 965 ,(2003) , 10.1021/JA017635Y
Dhaval A Doshi, Nicola K Huesing, Mengcheng Lu, Hongyou Fan, Yunfeng Lu, Kelly Simmons-Potter, BG Potter Jr, Alan J Hurd, C Jeffrey Brinker, Optically defined multifunctional patterning of photosensitive thin-film silica mesophases. Science. ,vol. 290, pp. 107- 111 ,(2000) , 10.1126/SCIENCE.290.5489.107
Taku Hirayama, Daiju Shiono, Junichi Onodera, Atsuko Yamaguchi, Hiroshi Fukuda, Depth profile and line-edge roughness of partiallyO-1-ethoxyethylated low molecular weight amorphous polyphenol and poly(p-hydroxystyrene) base resists for electron-beam lithography Polymers for Advanced Technologies. ,vol. 17, pp. 116- 121 ,(2006) , 10.1002/PAT.670
Taku Hirayama, Daiju Shiono, Shogo Matsumaru, Toshiyuki Ogata, Hideo Hada, Junichi Onodera, Tadashi Arai, Toshio Sakamizu, Atsuko Yamaguchi, Hiroshi Shiraishi, Hiroshi Fukuda, Mitsuru Ueda, Depth Profile and Line-Edge Roughness of Low-Molecular-Weight Amorphous Electron Beam Resists Japanese Journal of Applied Physics. ,vol. 44, pp. 5484- 5488 ,(2005) , 10.1143/JJAP.44.5484
G. G. Barclay, D. R. Medeiros, R. F. Sinta, Thermal Stability of Sulfonate Ester Photoacid Generators in Phenolic Matrixes Chemistry of Materials. ,vol. 7, pp. 1315- 1324 ,(1995) , 10.1021/CM00055A007
Ramakrishnan Ayothi, Yi, Heidi B. Cao, Wang Yueh, Steve Putna, Christopher K. Ober, Arylonium photoacid generators containing environmentally compatible aryloxyperfluoroalkanesulfonate groups Chemistry of Materials. ,vol. 19, pp. 1434- 1444 ,(2007) , 10.1021/CM062802K
Hiroshi ITO, Greg BREYTA, Don HOFER, R. SOORIYAKUMARAN, Karen PETRILLO, David SEEGER, ENVIRONMENTALLY STABLE CHEMICAL AMPLIFICATION POSITIVE RESIST: PRINCIPLE, CHEMISTRY, CONTAMINATION RESISTANCE, AND LITHOGRAPHIC FEASIBILITY Journal of Photopolymer Science and Technology. ,vol. 7, pp. 433- 447 ,(1994) , 10.2494/PHOTOPOLYMER.7.433