Retrospective of work at Bell Laboratories on the effect of fluorine substitution on the properties of photoacid generators

Journal of Fluorine Chemistry

Volumn 122, Issue 1, 2003, Pages 47-55

  Houlihan, Frank M ^a   Nalamasu, O ^a   Reichmanis, E ^a  

^a LUCENT TECHNOLOGIES   (United States)

Author keywords

2 Nitrobenzyl; Chemically amplified resists; PAG; Photoacid generator

Indexed keywords

ACID; FLUORINE; NITROBENZENE DERIVATIVE;

CHEMICAL STRUCTURE; CONTROLLED STUDY; MOLECULE; PHOTOCHEMISTRY; QUANTUM YIELD; RETROSPECTIVE STUDY; REVIEW; SENSITIVITY ANALYSIS; SUBSTITUTION REACTION; THERMOSTABILITY;

EID: 0037633557     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-1139(03)00079-4     Document Type: Article

References (35)

1. J.T. Welch, Transformations of fluorinated compounds, in: B. Baasner, Aya Il'Chenko (Eds.), Methods of Organic Chemistry, fourth ed., vol. E10, Part 2, Houben Weyl, 2000, pp. 293-305.
2. D.R. Lide, CRC Handbook of Chemistry and Physics, 80th ed., 2000-2001, pp. 9-74.
3. Yagupolskii L.M. J. Fluorine Chem. 36 1987 1-28
4. W.M. Lamanna, C.R. Kessel, P.M. Savu, Y. Cheburkov, S. Brinduse, T. Kestner, G. Lillquist, M. Parent, K.S. Moorhouse, Y. Zhang, G. Birznieks, T. Kruger, M. Pallazzotto, in: T. Fedynyshyn (Ed.), Proceedings of the Society Photo-Optical Instruments Engineering, Advances in Resist Technology and Processing, vol. 4690, 2002.
5. A. Reiser, Photoreactive Polymers the Science and Technology of Resists, Wiley, New York, 1989, pp. 102-178/252-293.
6. Reichmanis E.Houlihan F.M.Nalamasu O.Neenan T.X. Chem. Mater. 3 1991 397
7. Willson C.G. Frechet J.M.J. Tessier T. Houlihan F.M. J. Electrochem. Soc. 1331 1986 181
8. H. Ito, in: Proceedings of the KTI Microelectronics Seminar, 1988, p. 81.
9. Lamola A.Szmanda C.R.Thackeray J.W. Solid State Technol. 348 1991 53
10. Houlihan F.M. Shugard A. Gooden R. Reichmanis E. Macromolecules 21 1988 2001
11. G.L. Li-Bassi, J. Rad. Cur. (1987) 18.
12. G.L. Berner, Radcure Europe, Basel, Switzerland, 1985, p. 446.
13. Yamaoka Y.Omote T.Adachi H.Kikuchi H.Watanabe Y.Shirosaki T. J. Photopolym. Sci. Technol. 3 3 1990 275
14. Shirai M.Tsunooka M. J. Photopolym. Sci. Technol. 3 3 1990 301
15. Schlegel L.Ueno T.Shiraishi H.Hayashi N.Iwayanagi T. Chem. Mater. 2 3 1990 300
16. Dossel K.F.Huber H.L.Oertel H. Microelectr. Eng. 5 1986 97
17. Menschig A. Forchel A. Dammel R. Lingnau J. Scheunemann U. Theis J. Pongratz S. Microelectr. Eng. 9 1989 571
18. Neenan T.X. Houlihan F.M. Reichmanis E. Kometani J.M. Bachman B.J. Thompson L.F. Macromolecules 23 1990 145
19. F.M. Houlihan, T.X. Neenan, E. Reichmanis, US Patent 5,200,544 (1993)
20. Neenan T.X. Houlihan F.H. Reichmanis E. Kometani J.M. Chin T. J. Photopolym. Sci. Technol. 43 1991 341
21. Houlihan F.M. Chin E. Nalamasu O. Kometani J.M. Neenan T.X. Pangborn A.J. J. Photopolym. Sci. Technol. 64 1993 515
22. Houlihan F.M. Chin E. Nalamasu O. Kometani J.M. Neenan T.X. Pangborn A.J. Proc. Soc. Photo-Opt. Instrum. Eng. 2195 1994 137
23. F.M. Houlihan, E. Chin, O. Nalamasu, J.M. Kometani, in: Proceedings of the ACS Symposium Series 537, American Chemical Society, Washington, DC, 1992, p. 25
24. J.M. Kometani, F.M. Houlihan, S.A. Heffner, E. Chin, O. Nalamasu, Microelectronics technology, in: E. Reichmanis, S.A. MacDonald, I. Iwayanagi (Eds.), Proceedings of the ACS Symposium Series 614 on Polymers for Advanced Imaging and Packaging, American Chemical Society, Washington, DC, 1995, p. 207.
25. F.M. Houlihan, J.M. Kometani, E. Chin, R. Harley, O. Nalamasu, in: ACS Symposium Series 614, American Chemical Society, Washington, DC, 1995, p. 84.
26. F.M. Houlihan, et al., Processes Using Photosensitive Materials Including a Nitro Benzyl Ester Photoacid Generator, US Patent 6,159,665 (2000).
27. F.M. Houlihan, I.L. Rushkin, H.S. Hutton, A.G. Timko, E. Reichmanis, O. Nalamasu, A.H. Gabor, A.N. Medina, S. Malik, N. Neisser, R.R. Kunz, D.K. Downs, in: Proceedings of the Microlithography Symposium Interface'99, 1999, p. 133.
28. Houlihan F.M.Rushkin I.L.Hutton H.S.Timko A.G.Reichmanis E.Nalamasu O.Gabor A.H. Medina A.N. Malik S. Neisser N. Kunz R.R. Downs D.K. J. Photopolym. Sci. Technol. 12 1999 525
29. J.F. King, Acidity, in: S. Patain, Z. Rappoport (Eds.), The Chemistry of Sulphonic Acids, Esters and Their Derivatives, Wiley, New York, 1991, p. 197.
30. N. Furukawa, H. Fujihara, Acidity hydrogen bonding and metal complexation of sulfonic acids and derivatives, in: S. Patain, Z. Rappoport (Eds.), The Chemistry of Sulphonic Acids, Esters and Their Derivatives, Wiley, New York, 1991, p. 249.
31. W.-Y. Huang, Q.-Y. Chen, Perfluoroakanesulfonic acids and their derivatives, in: S. Patain, Z. Rappoport (Eds.), The Chemistry of Sulphonic Acids, Esters and Their Derivatives, Wiley, New York, 1991, p. 903.
32. Nalamasu O. Reichmanis E. Cheng M. Pol V. Kometani J.M. Houlihan F.M. Neenan T.X. Bohrer M.P. Mixon D.A.Thompson L.F. Proc. Soc. Photo-Opt. Instrum. Eng. 1466 1991 13
33. MacDonald S.A.Clecak N.J.Wendt H.R.Willson C.G.Snyder C.D.Knors C.J.Peyoe N. Maltabes J. Morrow J. McGuire A.E. Holmes S.J. Proc. Soc. Photo-Opt. Instrum. Eng. 1466 1991 2
34. Ito H.England W.P.Clecak N.J.Breyta G.Lee H.Yoon D.Y.Sooriyakumaran R.Hinsberg W.D. Proc. Soc. Photo-Opt. Instrum. Eng. 1925 1993 65
35. D. Coates, Liquid crystals applications and uses, in: B. Bahadur (Ed.), World Scientific, New Jersey, 1990, p. 69.