Novel design of carbon-rich polymers for 193 nm microlithography: Adamantane-containing cyclopolymers

Advanced Materials

Volumn 12, Issue 5, 2000, Pages 347-351

  Pasini, Dario ^a   Low, Eric ^a   Fréchet, Jean M J ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ESTERS; ETCHING; LITHOGRAPHY; POLYMERIZATION; SYNTHESIS (CHEMICAL);

CYCLOPOLYMERS; ETCH RESISTANCE; IMAGEABLE POLYMERIC MATERIALS;

PLASTIC FILMS;

EID: 0033906855     PISSN: 09359648     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-4095(200003)12:5<347::AID-ADMA347>3.0.CO;2-D     Document Type: Article

References (34)

1. The National Technology Roadmap for Semiconductors, Semiconductor Industry Association (SIA), San Jose, CA 1997.
2. a) J. M. J. Fréchet, E. Eichler, H. Ito, C. G. Willson, Polymer 1983, 24, 995.
3. b) H. Ito, C. G. Willson, J. M. J. Fréchet, U.S. Patent 4491 628, 1985.
4. c) C. G. Willson, H. Ito, J. M. J. Fréchet, T. G. Tessier, F. M. Houlihan, J. Electrochem. Soc. 1986, 133, 181.
5. S. A. MacDonald, C. G. Willson, J. M. J. Fréchet, Acc. Chem. Res. 1994, 27, 151.
6. H. Gokan, S. Esho, Y. Ohnishi, J. Electrochem. Soc. 1983, 130, 143.
7. a) R. R. Kunz, R. D. Allen, W. D. Hinsberg, G. M. Wallraff, Proc. SPIE-Int. Soc. Opt. Eng. 1993, 1925, 167.
8. b) R. D. Allen, G. M. Wallraff, W. D. Hinsberg, W. E. Conley, R. R. Kunz, J. Photopolym. Sci. Technol. 1993, 6, 575.
9. c) R. R. Kunz, S. C. Palmateer, A. R. Forte, R. D. Allen, G. M. Wallraff, R. A. DiPietro, D. C. Hofer, Proc. SPIE-Int. Soc. Opt. Eng. 1996, 2724, 365.
10. a) U. Okoroanyanwu, T. Shimokawa, J. Byers, C. G. Willson, Chem. Mater. 1998, 10, 3319.
11. b) U. Okoroanyanwu, J. Byers, T. Shimokawa, C. G. Willson, Chem. Mater. 1998, 10, 3328.
12. a) E. Reichmanis, O. Nalamasu, F. M. Houlihan, Acc. Chem. Res. 1999, 32, 659.
13. b) F. M. Houlihan, T. I. Wallow, O. Nalamasu, E. Reichmanis. Macromolecules 1997, 30, 6517.
14. c) S.-J. Choi, Y. Kang, D.-W. Jung, C.-G. Park, J.-T. Moon, Proc. SPIE-Int. Soc. Opt. Eng. 1997, 3049, 104.
15. a) Q. J. Niu, J. M. J. Fréchet, Angew. Chem. Int. Ed. 1998, 37, 667.
16. b) D. Pasini, Q. J. Niu, R. P. Meagley, D. C. Tully, A. R. Trimble, J. M. J. Fréchet, J. Photopolym. Sci. Technol. 1999, 12, 405.
17. a) C. S. Marvel, R. D. West, J. Am. Chem. Soc. 1957, 79, 5771.
18. b) G. B. Butler, Acc. Chem. Res. 1982, 15, 370.
19. c) G. B. Butler, in Encyclopedia of Polymer Science and Engineering (Ed: J. I. Kroschwitz), Wiley, New York 1986, Vol. 4, pp. 543-598.
20. d) L. J. Mathias, Trends Polym. Sci. 1996, 10, 330.
21. e) R. P. Meagley, D. Pasini, L. Y. Park, J. M. J. Fréchet, Chem. Commun. 1999, 1587.
22. f) D. Pasini, E. Low, R. P. Meagley, J. M. J. Fréchet, C. G. Willson, J. D. Byers, Proc. SPIE-Int. Soc. Opt. Eng. 1999, 3678, 94.
23. a) L. J. Mathias, R. M. Warren, S. Huang, Macromolecules 1991, 24, 2036.
24. b) T. Tsuda, L. J. Mathias, Macromolecules 1993, 26, 6359.
25. The choice of five-membered ring repeating structural units in the representation of the polymers shown in Scheme 3 is based on the following considerations: a) NMR studies have shown that similar cyclopolymers (e.g., poly[ethyl α-(allyloxy)methyl]-acrylate) exclusively possess five-membered ring repeating units; see: R. D. Thompson, W. L. Jarrett, L. J. Mathias, Macromolecules 1992, 25, 6455, and ref. 9d. b) Malonate esters containing an allylic and an α-methacrylic substituent undergo free-radical cyclization reactions to afford cyclopentane systems. See: C.-P. Chuang, Tetrahedron 1991, 47, 5425.
26. The choice of five-membered ring repeating structural units in the representation of the polymers shown in Scheme 3 is based on the following considerations: a) NMR studies have shown that similar cyclopolymers (e.g., poly[ethyl α-(allyloxy)methyl]-acrylate) exclusively possess five-membered ring repeating units; see: R. D. Thompson, W. L. Jarrett, L. J. Mathias, Macromolecules 1992, 25, 6455, and ref. 9d. b) Malonate esters containing an allylic and an α-methacrylic substituent undergo free-radical cyclization reactions to afford cyclopentane systems. See: C.-P. Chuang, Tetrahedron 1991, 47, 5425.
27. S. Bizilj, D. P. Kelly, A. K. Serelis, D. H. Solomon, K. E. White, Aust. J. Chem. 1985, 38, 1657.
28. F. Jahanzad, M. Kazemi, S. Sajjadi, F. Taromi, Polymer 1993, 34, 3542.
29. Triphenyl sulfonium nonafluorobutane sulfonate was used in all resist formulations.
30. Monomers 4 and 5 contain two different types of tertiary esters, both of which could be chemically deprotected in the presence of strong acids. However, whereas tert-butyl esters form a carbocation that eliminates a proton to yield isobutene [3], adamantane forms a relatively stable carbocation at the bridgehead tertiary carbon that can accept anions from the reaction mixture but cannot lose a proton to form an olefin. See: a) S. M. Iossifidou, C. C. Froussios, Synthesis 1996, 1355. b) W. L. Haas, E. V. Krumkalns, K. Gerzon, J. Am. Chem. Soc. 1966, 88, 1988. c) Y. Okada, S. Iguchi, J. Chem. Soc. Perkin Trans. 1 1988, 2129. d) P. von R. Schleyer, R. D. Nicholas, J. Am. Chem. Soc. 1961, 83, 2700.
31. Monomers 4 and 5 contain two different types of tertiary esters, both of which could be chemically deprotected in the presence of strong acids. However, whereas tert-butyl esters form a carbocation that eliminates a proton to yield isobutene [3], adamantane forms a relatively stable carbocation at the bridgehead tertiary carbon that can accept anions from the reaction mixture but cannot lose a proton to form an olefin. See: a) S. M. Iossifidou, C. C. Froussios, Synthesis 1996, 1355. b) W. L. Haas, E. V. Krumkalns, K. Gerzon, J. Am. Chem. Soc. 1966, 88, 1988. c) Y. Okada, S. Iguchi, J. Chem. Soc. Perkin Trans. 1 1988, 2129. d) P. von R. Schleyer, R. D. Nicholas, J. Am. Chem. Soc. 1961, 83, 2700.
32. Monomers 4 and 5 contain two different types of tertiary esters, both of which could be chemically deprotected in the presence of strong acids. However, whereas tert-butyl esters form a carbocation that eliminates a proton to yield isobutene [3], adamantane forms a relatively stable carbocation at the bridgehead tertiary carbon that can accept anions from the reaction mixture but cannot lose a proton to form an olefin. See: a) S. M. Iossifidou, C. C. Froussios, Synthesis 1996, 1355. b) W. L. Haas, E. V. Krumkalns, K. Gerzon, J. Am. Chem. Soc. 1966, 88, 1988. c) Y. Okada, S. Iguchi, J. Chem. Soc. Perkin Trans. 1 1988, 2129. d) P. von R. Schleyer, R. D. Nicholas, J. Am. Chem. Soc. 1961, 83, 2700.
33. Monomers 4 and 5 contain two different types of tertiary esters, both of which could be chemically deprotected in the presence of strong acids. However, whereas tert-butyl esters form a carbocation that eliminates a proton to yield isobutene [3], adamantane forms a relatively stable carbocation at the bridgehead tertiary carbon that can accept anions from the reaction mixture but cannot lose a proton to form an olefin. See: a) S. M. Iossifidou, C. C. Froussios, Synthesis 1996, 1355. b) W. L. Haas, E. V. Krumkalns, K. Gerzon, J. Am. Chem. Soc. 1966, 88, 1988. c) Y. Okada, S. Iguchi, J. Chem. Soc. Perkin Trans. 1 1988, 2129. d) P. von R. Schleyer, R. D. Nicholas, J. Am. Chem. Soc. 1961, 83, 2700.
34. J. M. J. Fréchel, D. Pasini, E. Low, R. Meagley, J. Niu, Polym. Mater. Sci. Eng. 1999, 80, 487.