High resolution photoresists for semiconductor production

Journal of Information Recording

Volumn 22, Issue 5-6, 1996, Pages 481-520

  Merrem, H J ^a   Dammel, R ^b   Pawlowski, G ^c  

^a SANOFI   (France)

^b Hoechst Celanese Corporation   (United States)

^c Hoechst Industry Japan Ltd   (Japan)

Author keywords

Chemically amplified resists; Diazonaphthoquinone; Novolak; Photoacid generators; Polyhydroxystyrene; Positive photoresists

Indexed keywords

EID: 0000825772     PISSN: 10256008     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (117)

1. J.C. Langston and G.T. Dao: Solid State Technology (3) 57-64 (1995).
2. G.E. Moore: Proc. SPIE 2438 2 (1995).
3. H. Steppen, G. Buhr and H. Vollman: Angew. chem. 94 471 (1982).
4. J. Kosar, Light-Sensitive Systems; Chemistry and Application of Nonsilver Halide Photographic Processes, Wiley, New York 1965.
5. G.A. Delzenne: Adv. Photochem, 11 (1979).
6. K. Neisius and H. Merrem: J. Electron. Mater, 11 (4) 761-78 (1982).
7. R. Dammel: SPIE Tutorial texts, Vol. TT11, (1993).
8. D. Meyerhofer: IEEE Trans. Electr. Dev. ED-27 921 (1980).
9. J. Dicarlo, O.B. Evans, J. Fedyk, S. Ficner, M. Khasim and R. Dammel, SPIE 2196 (1994).
10. C. Schuster, J. Bendig and K. Neumann, J. prakt. Chem., 336 658-662 (1994).
11. H. Meier and K. Zeller: Angew. Chem. Int. Ed. Engl. 14 32 (1975).
12. J. Bendig and S. Helm: Proc. SPE, Ellenville, N.Y. (1994).
13. L. Wolff, Liebig's Ann. Chem. 325 129 (1902);
14. Liebig's Ann. Chem. 394 23 (1912).
15. G. Schroeter: Berr. Dtsch. Chem. Ges. 42 2346 (1909);
16. G. Schroeter: Berr. Dtsch. Chem. Ges. ibid. 49 2704 (1912).
17. O. Süss: Liebig's Ann. Chem. 556 65-84 (1944).
18. F.A. Vollenbroek, W.P.M. Nijssen, C.M.J. Mutsaers, M.J.H.J. Geomini, M.E. Reuhman and R.R. Visser: Proc. SPE, Ellenville, N.Y. 259-279 (1988).
19. K.-P. Zeller: Chem. Ber. 108 3566 (1975).
20. A.M. Komagorov, R.P. Ponomareva, I.S. Isaev and V.A. Koptyug: Izv. Akad. Nauk. SSSR, Ser. Khim. 4 943-945 (1976).
21. K. Nakamura, S. Udagawa and K. Honda: Chem. Lett. 763 (1963).
22. G.N. Rodianova, Y.G. Tuchin, N.P. Protsenko and R.D. Erlikh: Zh. Vsesoyuznogo Khim. Obsh. 18 355 (1973).
23. J. Pacansky and D. Johnson: J. Electrochem. Soc. 124 862-865 (1977).
24. J. Pacansky and J.R. Lyerla: IBM J. Res. Develop. 23 42-55 (1979).
25. N.P. Hacker and N.J. Turro; Tetrahedron Lett. 23 1771 (1982).
26. A. Reiser: Photoreactive Polymers - The Science and Technology of Resists, J. Wiley and sons, New York, 1989.
27. M.E. Reuhman-Huisken, C.M.J. Mutsaers, F.A. Vollenbroek and J.A.H.M. Moonen: Microelectronic Eng. 9 551 (1989).
28. A. Knop and L.A. Pilato: Phenolic Resins, Springer-Verlag, Berlin 1985.
29. K. Kamide and Y. Miyakawa: Macromol. Chem. 179 359 (1978).
30. A. Furuta, M. Hanabata and Y. Uemura; J. Vac. Sci. Technol. B4 430 (1986).
31. M. Hanabata, A. Furuta und Y. Uemrua: Proc SPIE 771 85 (1987)
32. Proc. SPIE 631 76 (1986).
33. M. Hanabata, Y. Uetani and A. Furata: Proc. SPIE 920 349 (1988).
34. A. Furuta and M. Hanabata; J. Photopolym. Sci. Technol. 2 383 (1989).
35. M. Hanabata and A. Furuta: Proc, SPIE 1262 476 (1990).
36. M.K. Templeton. C.R. Szmanda and A. Zampini: Proc. SPIE 771 136 (1987).
37. C.D. Gutsche, Calixarenes, Monographs in Supramolecular Chemistry I, Roy. Soc. Chem., Cambridge, UK, 1989.
38. R.A. Arcus: Proc. SPIE 631 124 (198 ).
39. C.M. Garza, C.R. Szmanda and R.L. Fischer: Jr. Proc. SPIE 920 321 (1988).
40. G.R. Sprengling: J. Am. Chem. Soc. 76 1190 (1954).
41. V. Böhmer, E. Schade, C. Antes, J. Pachta, W. Vogt and H. Kämmerer: Macromol. Chem. 184 2361 (1983).
42. P.J. Paniez, D.C. Demattei and M.J.M. Abadie: Proc. Microcircuit Eng. 1991.
43. J,-P. Huang, T.K. Kwei and A. Reiser: Macromolecules 22 4106 (1989).
44. T.F. Yeh, H.Y. Shi and A. Reiser: Macromolecules 25 5345 (1992).
45. H.Y. Shih, T.F. Yeh, A. Reiser, R.R. Dammel, H.J. Merrem and G. Pawlowski: Macromolecules 27 3330 (1994).
46. T.F. Yeh, A. Reiser, R.R. Dammel, G. Pawlowski and H. Röschert: Macromol. 26 3862 (1993).
47. H.Y. Shih and A. Reiser: Macromol. 28 5595 (1995).
48. H.Y. Shih, T.F. Yeh J.P. Huang and A. Reiser: to be published
49. M. Koshiba, M. Murata, M. Matsui and Y. Harita: Proc. SPIE 920 364 (1988).
50. K. Honda, B.T. Beauchemin, Jr., R.J. Hurditch, A.J. Blakeney, Y. Kawabe and T. Kobuko: Proc. SPIE 1262 493 (1990).
51. A. Blakeney, L. Ferreira and N. Reynolds: Proc. SPIE 2438 312 (1995).
52. K. Honda, B.T. Beauchemin, Jr. E.A. Fitzgerald, A.T. Jeffries, III, S.P. Tadros, A.J. Blakeney, R.J. Hurditch, S. Tan and S. Sakaguchi: Proc. SPIE 2438 141 (1991)
53. P. Trefonas and B.K. Daniels: Proc. SPIE 771 194 (1987).
54. P. Trefonas and C. Mack: Proc. SPIE 1466 117 (1991).
55. C.R. Szmanda, A. Zampini, D.C. Madoux and C.L. McCants: Proc. SPIE 1086 363 (1989).
56. K. Uenishi, Y. Kawabe, T. Kobuko, S. Slater and A. Blakeney: Proc. SPIE 1466 102 (1991).
57. S. Kishimura, A. Yamacuchi, Y. Yamada and H. Nagata: Polym. Eng. Sci. 32 (20) 1550 (1992).
58. M. Hanabata, Y. Uetani and A. Furata: Proc. SPIE 920 349 (1988).
59. U.S.patent 5 143, 814
60. K. Jain, C.G. Willson and B.J. Lin: IEEE Electron Device Lett, EDL-3 53 (1982).
61. K.J. Orvek, S.R. Palmer, C.M. Garza and G.E. Fuller: Proc. SPIE 631 83 (1986)
62. J. Electrochem. Soc. 141 (11) 3141 (1994).
63. R. Hayase, Y. Onishi, H. Niki, N. Oyasato and S. Hayase, J. Electrochem. Soc. 141 (11), 3141 (1994).
64. W.M. Moreau, Semiconductor Lithography, "Principles, Practices and Materials", Plenum. N.Y. 372 (1988).
65. M. Hatzakis, J. Electrochem, Soc. 116 1033 (1969).
66. J.N. Helbert, C.Y. Chen, C.U. Pittman Jr. and G.L. Hagnauer, Macromolecules 11 1104 (1978).
67. M.J. Bowden, L.F. Thompson and J.P. Ballantyne, J. Vac. Sci. Technol. 12 (6) 1294 (1975).
68. R.G. Tarascon, E. Reichmanis, F.M. Houlihan, A. Shugard and L.F. Thompson, Polym. Eng. Sci. 1989.
69. J.M. Kometani, M.E. Galvin, S.A. Heffner, F.M. Houlihan, O. Nalamasu, E. Chin and E. Reichmanis, Macromolecules 26 2165 (1993).
70. U. Schaedli, N. Münzel, H. Holzwarth, S.G. Slater and O. Nalamasu, Proc. SPIE, 2195 98, (1994).
71. C. Osuch, K. Brahim, F.R. Hopf, M.J. McFarland, A. Mooring and C.J. Wu, Proc. SPIE 631, 68 (1986).
72. K. Przybilla, H. Röschert, W. Spieß, C. Eckes, S. Chatterjee, D. Khanna, G. Pawlowski and R. Dammel, Proc. SPIE 1466 (1991).
73. K. Przybilla, R. Dammel, H. Röschert, W. Spieß and G. Pawlowski, J. Photogr, Sci. Tech. 4 (3), 421 (1991).
74. J.M. Frechet, E. Eichler, H. Ito and C.G. Willson, Polymer, 24 995 (1983).
75. H. Ito, C.G. Willson, J.M. Frechet, M.J. Farrall and E. Eichler, Macromolecules, 16 510 (1983).
76. B.D. Grant, N.J. Clecak, R.J. Twieg and C.G. Willson, IEEE Trans, Electron, Dev. ED-28 (11), 1300 (1981).
77. G. Schwartzkopf, Proc, SPIE 920 51 (1988).
78. H. Sugiyama, K. Ebata, A. Mizushima and K. Nate, Proc. Spe.Conf. Photopolym Ellenville, N.Y. 51 (1988).
79. G. Pawlowski, R. Dammel, C.R. Lindley, H.J. Merrem, H. Röschert and P. Wilharm, Microelectronic eng. 11 491 (1990).
80. C.G. Willson, R.D. Miller and D.R. McKean, Proc. SPIE 771 2 (1987).
81. E. Reichmanis, C.W. Wilkins Jr. and E.A. Chandross, J. Vac. Sci. Technol. 19 (4) 1338 (1981).
82. F.M. Houlihan, E. Chin, O. Nalamasu, J.M. Kometani, T.X. Neena and A. Pangborn, Proc. SPIE 2195 137 (1994).
83. H. Ito and C.G. Willson, Polym. Eng. Sci. 23 1012 (1983).
84. J.V. Crivello, ACS Symp. Series 242 2 (1984).
85. H. Ito and C.G. Willson, ACS Symp. Series 242 11 (1984).
86. T.W. Greene, Protective Groups in Organic Synthesis, John Wiley & Sons, N.Y. (1981).
87. R. Vicari, D.J. Gordon, R.W. Rupp, R. Dammel, K.F. Dössei, J. Lingnau, J.P. Lockard, M. Aslam, W.B. Ray and K.G. Davenport, EP 307 752 (1989).
88. J.G. Maltabes, S.J. Holmes, J.R. Morrow, R.L. Barr, M. Hakey, G. Reynolds, W. Brunsvold, C.G. Willson, N. Clecak, S. MacDonald and H. Ito, Proc. SPIE 2438 551 (1995).
89. E. Yano, Y. Kuramitsu, K. Watanabe, T. Namiki, K. Nozaki and M. Igarashi, Proc. SPIE 2438 551 (1995).
90. T. Itani, H. Iwasaki, H. Yoshino, M. Fujimoto and K. Kasama, Proc. SPIE 2438, 191 (1995).
91. T. Aoai, T. Yamanaka and T. Kokubo, Proc. SPIE 2195 111 (1994).
92. G. Pawlowski, T. Sauer, R. Dammel, D.J. Gordon, W, Hinsberg, D. McKean, C.R. Lindley, H.J. Merrem, H. Röschert, R. Vicari and C.G. Willson, Proc. SPIE 1262 (1990).
93. M. Padamanaban, Y. Kinoshita, T. Kudo T. Lynch, S. Masuda, Y. Nozaki, H. Okasaki, G. Pawlowski, H. Röschert, W. Spieß, N. Suehiro and H. Wengenroth, Proc. SPIE 2195 61 (1994).
94. G.M. Wallraff, W.D. Hinsberg, F. Houle, J. Opitz, D. Hopper and J.M. Hutchinson, Proc. SPIE 2438 182 (1995).
95. G. Pawlowski, R. Dammel, C.R. Lindley, H.J. Merrem, H. Röschert and J. Lingnau, Proc. SPIE 1262 (1990).
96. G. Pawlowski, R. Dammel, K.J. Przybilla, H. Röschert and W. Spieß, J. Phot. Sci. Tech. 4 (3) 389 (1991).
97. C. Mertesdorf, N. Münzel, H. Holzwarth, H.T. Schacht, O. Rohde, R. Schulz, S.G. Slater, D. Frey, O. Nalamasu, A.G. Timko and T.X. Neenan, Proc. SPIE 2438 84 (1995).
98. F.M. Houlihan, E. Reichmanis, L.F. Thompson and R.G. Tarascon, ACS Series 412 39 (1989).
99. H. Ito, W. England, N. Clecak, G. Breyta, H. Lee, D. Yoon, R. Sooriyakumaran and W. Hinsberg, Proc. SPIE 1925 65 (1993).
100. P.J. Paniez, J.P. Chollet, M.J. Pons, Proc. SPIE 1925 614 (1993).
101. P.J. Paniez, C. Rosilio, B. Mouanda and F. Vinet, Proc. SPIE 2195 14 (1994).
102. F. Vinet, N. Buffet, P. Fanton, L. Pain and P.J. Paniez, Proc. SPIE 2438 202 (1995).
103. S.A. MacDonald, N.J. Clecak, H.R. Wendt, C.G. Willson, C.D. Snyder, C.J. Knors, N.B. Deyoe, J.B. Maltabes, J.R. Morrow, A.E. McGuire and S.J. Holmes, Proc. SPIE 1466 2 (1991).
104. O. Nalamasu, E. Reichmanis, M. Cheng, V. Pol, J.M. Kometani, F.M. Houlihan, T.X. Neenan, M.P. Bohrer, D.A. Mixon and L.F. Thompson, Proc. SPIE 1466 13 (1991).
105. M.F. Cronin, T. Adams, T. Fedynyshyn, J. Georger, J.M. Mori and J.W. Thackeray, Proc. SPIE 2195 214 (1994).
106. M. Zuniga, G.-Wallraff, E. Tomacruz, B. Smith, C. Larson, W.D. Hinsberg and A.R. Neureuther, J. Vac. Sci. Technol. B 11 (6), 2862 (1993).
107. M. Zuniga, E. Tomacruz and A.R. Neureuther, Proc. SPIE 2195 320 (1994).
108. H. Ito, G. Breyta, D. Hofer, T. Fischer and B. Prime, Proc. SPIE 2438 53 (1995).
109. P. Jagannathan, W.S. Huang, A.D. Katnani, G.J. Hefferon and R.L. Wood, Proc. SPIE 2195 28 (1994).
110. H. Röschert, C. Eckes, H. Endo, Y. Kinoshita, T. Kudo, S. Masuda, H. Okazaki, G. Pawlowski, Proc. SPIE 1925 14, 106 (1993).
111. K.J. Przybilla, Y. Kinoshita, T. Kudo, S. Masuda, H. Okazaki, M. Padmanaban, G. Pawlowski, H. Röschert, W. Spieß and N. Suehiro, Proc. SPIE 2438 61 (1995).
112. H. Horibe, T. Kumada, S, Kubota and Y. Kimura, Proc. SPIE 2438 61 (1995).
113. Y. Kawai, A.Otaka, A. Tanaka and T. Matuda, Jpn. J. Appl. Phys. 33 7023 (1994).
114. K. Asakawa, T. Ushirogouchi and M. Nakase, Proc. SPIE 2438 563 (1995).
115. E. Yano, Y. Kuramitsu, K. Watanabe, T. Namiki, K. Nozaki and M. Igarashi, Proc. SPIE 2438 551 (1995).
116. R. Schwalm, H. Binder, T. Fischer, D. Funhoff, M. Goethals, A. Grassmann, H. Moritz, P. Paniez, M. Reuhman-Huisken, F. Vinet, H. Dijkstra and A. Krause, Proc. SPIE 2195 2 (1994).
117. K. Nakano, K. Maeda, S. Iwasa, J. Yano and E. Hasegawa, Proc. SPIE 2195 194 (1994).