Design of photoresists with reduced environmental impact. 1. Water-soluble resists based on photo-cross-linking of poly(vinyl alcohol)

Chemistry of Materials

Volumn 11, Issue 3, 1999, Pages 719-725

  Havard, Jennifer M ^a   Shim, Sang Yeon ^a   Fréchet, Jean M J ^a   Lin, Qinghuang ^b   Medeiros, David R ^b   Grant Willson, C ^b   Byers, Jeffrey D ^c  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b The University of Texas at Austin   (United States)

^c SEMATECH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001235395     PISSN: 08974756     EISSN: None     Source Type: Journal    
DOI: 10.1021/cm980603y     Document Type: Article

References (56)

1. Havard, J. M.; Fréchet, J. M. J.; Pasini, D.; Mar, B.; Yamada, S.; Medeiros, D.; Willson, C. G. Proc. SPIE 1997, 3049, 437.
2. (a) Lin, Q.; Simpson, L.; Steinhäusler, T.; Wilder, M.; Willson, C. G.; Havard, J.; Fréchet, J. M. J. Proc. SPIE 1996, 2725, 308.
3. (b) Lin, Q.; Steinhäusler, T.; Simpson, L.; Wilder, M.; Medeiros, D. R.; Willson, C. G.; Havard, J.; Fréchet, J. M. J. Chem. Mater. 1997, 9, 1725.
4. (a) Aoki, H.; Tokuda, T.; Nagasaki, Y.; Kato, M. J. Polym. Sci., Polym. Chem. 1997, A35, 2827.
5. (b) Aoki, H.; Tokuda, T.; Nagasaki, Y.; Kato, M. Macromol. Rapid Commun. 1997, 18, 31.
6. Mirle S. K.; Berrier A. L. U.S. Patent 5,143,819, 1992.
7. Shirai, M.; Katsuta, N.; Tsunooka, M.; Tanaka, M. Makromol. Chem., Macromol. Chem. Phys. 1989, 190 (9), 2099.
8. (a) Borden, D. G.; Williams, J. L. R. Makromol. Chem. 1977, 178, 3035.
9. (b) Barker, I. C.; Allen, N. S.; Edge, M.; Sperry, J. A.; Batten, R. J. J. Chem. Soc., Faraday Trans. 1994, 90 (24), 3677.
10. (c) Ichimura, K.; Watanabe, S. J. Polym. Sci., Polym. Lett. Ed. 1980, 18, 613.
11. (d) Ichimura, K. J. Polym. Sci. Polym. Chem. 1982, 20, 1411.
12. (a) Angelopoulos, M.; Patel, N.; Shaw, J. M.; Labianca, N. C.; Rishton, S. A. J. Vac. Sci. Technol. B 1993, 11 (6), 2794.
13. (b) Shimomura, K.; Otagaki, T.; Tamagawa, Y.; Kobayashi, M.; Aoki, H.; Sano, Y.; Terakawa, S. Proc. SPIE 1994, 2195, 823.
14. (c) Dauth, J.; Nuyken, O.; Strohriegl, P.; Voit, B. Makromol. Chem. Macromol. Chem. Phys. 1992, 193 (3), 723.
15. (d) Matusche, P.; Nuyken, O.; Voit, B.; Van Damme, M.; Vermeersch, J.; De Winter, W.; Alaerts, L. Reactive Polym. 1995, 24, 271.
16. (e) Matusche, P.; Nuyken, O.; Voit, B.; Van Damme, M. J. M. S.s Pure Appl. Chem. 1997, A34 (1), 201.
17. (a) Taylor, L. D.; Kolesinski, H. S.; Edwards, B. J. Polym. Sci. C Polym. Lett. 1988, 26, 177.
18. Taylor L. D.; Haubs M. K. U.S. Patent 4,617,253, 1986.
19. (a) MacDonald, S. A.; Willson, C. G.; Fréchet, J. M. J. Acc. Chem. Res. 1994, 27, 151.
20. (b) Fréchet, J. M. J.; Ito, H.; Willson, C. G. Proc. Microcircuit Eng. 1982, 260.
21. (c) C. Willson, C. G.; Ito, H.; Fréchet, J. M. J.; Houlihan, F. Proceedings of IUPAC 28th Symposium on Macromolecules; Amherst, 1982, 448.
22. (d) Fréchet, J. M. J.; Eichler, E.; Ito, H.; Willson, C. G. Polymer 1983, 24, 995.
23. (e) Willson, C. G.; In Introduction to Microlithography; Thompson, L. F., Willson, C. G., Bowden, M. J., Eds.; American Chemical Society: Washington, DC, 1993; pp 139-258.
24. (f) Reichmanis, E.; Houlihan, F. M.; Nalamasu, O.; Neenan, T. X. Chem. Mater. 1991, 3 (3), 394.
25. (g) Reichmanis, E.; Thompson, L. F. Chem. Rev. 1989, 89, 1273.
26. (a) Crivello, J. V.; Lam, J. H. W. J. Org. Chem. 1978, 43, 3055.
27. (b) Shirai, M.; Tsunooka, M. Prog. Polym. Sci. 1996, 21, 1.
28. (a) Hult, A.; Skolling, O.; Göthe, S.; Mellström, U. In Polymers for High Technology; Bowden, M. J., Turner, S. R., Eds.; ACS Symp. Ser. 346; American Chemical Society: Washington, DC, 1987; p 162.
29. (b) Davidson, K.; Hadley, P. C. High Perform. Polym. 1995, 7, 503.
30. Kim, J.-B.; Jung, M.-H.; Chang, K.-H. Eur. Polym. J. 1997, 33 (8), 1239.
31. (a) Fréchet, J. M. J., Shim, S. Y. U.S. Patent 5,648,196, 1997.
32. (b) Sakamizu, T.; Shiraishi, H.; Ueno, T. In Microelectronics Technology; Reichmanis, E., Ober, C. K., MacDonald, S. A., Iwayanagi, T., Nishikubo, T., Eds.; ACS Symp. Ser. 614; American Chemical Society: Washington, DC, 1995; p 124.
33. (a) Vekselman, A. M.; Darling, G. D. Proc. SPIE 1996, 2724, 296.
34. (b) Darling, G. D.; Vekselman, A. M. Polym. Mater. Sci. Eng. 1997, 77, 422.
35. Pritchard, J. G. Poly (vinyl alcohol): Basic Properties and Uses; Gordon and Breech: New York, 1970.
36. (a) Migitaka, S.; Morishita, H.; Ito, M.; Hayashi, N. J. Photopolym. Sci. Technol. 1993, 6 (1), 83.
37. (b) Larach, S.; McGowan, J. E. RCA Review 1984, 45, 337.
38. Grimm, L.; Hilke, K.-J.; Scharrer, E. J. Electrochem. Soc. 1983, 130(8), 1767.
39. (a) Bauer, D. R.; Dickie, R. A. J. Coatings Technol. 1982, 54 (685), 57.
40. (b) Chu, G.; Jones, F. N. J. Coatings Technol. 1993, 65 (819), 43.
41. (c) Takahashi, S.; Okoshi, N.; Matsumoto, T.; Ikeda, T. J. Appl. Polym. Sci. 1988, 36, 613.
42. (d) Mukhopadhyay, S. K.; Basu, D.; Banerjee, A. J. Appl. Polym. Sci. 1997, 65, 2075.
43. (e) Fukada, T. J. Appl. Polym. Sci. 1995, 58, 1925. (f)
44. (a) Blank, W. J. J. Coatings Technol. 1979, 51 (656), 61.
45. (b) Blank, W. J.; Hensley, W. L. J. Paint Technol. 1974, 46 (593), 46.
46. (a) Meijer, E. W. J. Polym. Sci. Polym. Chem. 1986, A24, 2199.
47. (b) Koral, J. N.; Petropoulos, J. C. J. Paint Technol. 1966, 38 (501), 600.
48. (c) Bauer, D. R.; Dickie, R. A. J. Polym. Sci., Polym. Phys. Ed. 1980, 18, 1997.
49. (d) Bauer, D. R.; Dickie, R. A. J. Polym. Sci., Polym. Phys. Ed. 1980, 18, 2015.
50. (e) Saxon, R.; Lestienne, F. C. J. Appl. Polym. Sci. 1964, 8, 475.
51. (f) Bauer, D. R.; Budde, G. F. J. Appl. Polym. Sci. 1983, 28, 253.
52. Thackeray, J. W.; Orsula, G. W.; Rajaratnam, M. M.; Sinta, R.; Herr, D.; Pavelchek, E. Proc. SPIE 1991, 1466, 39.
53. Gokan, H.; Esho, S.; Ohnishi, Y. J. Electrochem. Soc. 1983, 130, 143.
54. (a) Fahey, J.; Moreau, W.; Welsh, K.; Miura, S.; Eib, N.; Spinillo, G.; Sturtevant, J. Proc. SPIE 1994, 2195, 422.
55. (b) Perera, T. Solid State Technol. 1995, 38 (7), 131.
56. Willson, C. G.; Ito, H.; Fréchet, J. M. J.; Tessier, T. G.; Houlihan, F. M. J. Electrochem. Soc. 1986, 133 (1), 181.