Alkyl phenylglyoxylates as radical photoinitiators creating negative photoimages1

(Note: The full text of this document is currently only available in the PDF Version )

Shengkui Hu and Douglas C. Neckers


Abstract

Alkyl phenylglyoxylates are shown to be efficient photoinitiators for acrylate polymerization. Benzoyl and phenyl radicals derived from intermolecular hydrogen abstraction are the initiating species. A negative photoimage system was developed based on this observation. The imaging material consists of a polymeric phenylglyoxylate initiator and to-be-crosslinked diacrylate monomers. The contrast and sensitivity of this system have been measured.


References

  1. Contribution No. 311 from the Center for Photochemical Sciences.
  2. W. S. Deforest, Photoresist: Materials and Process, McGraw-Hill, New York, 1975 Search PubMed.
  3. G. Moad, D. H. Soloman, The Chemistry of Free Radical Polymerization, Elsevier Science Ltd, Amsterdam, 1995 Search PubMed.
  4. (a) S. P. Pappas, UV Curing: Science and Technology, Vol. 2, Technology Marketing Corp., CO, 1985 Search PubMed; (b) N. W. Allen, Photopolymerization and Photoimaging Science and Technology, Elsevier Science Ltd., Amsterdam, 1989 Search PubMed.
  5. (a) S. Hu and D. C. Neckers, J. Org. Chem., 1996, 61, 6407 CrossRef CAS; (b) E. S. Huyser and D. C. Neckers, J. Org. Chem., 1964, 29, 276 CAS; (c) A. Schönberg, N. Latif, R. Moubasher and A. Sina, J. Chem. Soc., 1951, 1364 RSC; (d) M. W. Encinas, E. A. Lissi, A. Zanocco, L. C. Stewart and J. C. Scaiano, Can J. Chem., 1984, 62, 386 CAS; (e) P. A. Leermakers, P. C. Warren and G. F. Vesley, J. Am. Chem. Soc., 1964, 86, 1768 CrossRef CAS; (f) R. J. Tepper and M. C. Pirrung, J. Org. Chem., 1995, 60, 2461 CrossRef CAS.
  6. H. Aoyama, M. Sakamoto, K. Yoshida and Y. Omote, J. Heterocycl. Chem., 1983, 20, 1099 CAS.
  7. W. E. Ford and M. A. J. Rodgers, J. Phys. Chem., 1994, 98, 3822 CrossRef CAS.
  8. A. Torres-Filho and D. C. Neckers, J. Appl. Polym. Sci., 1994, 51, 931 CrossRef CAS.
  9. W. F. Jager, A. A. Volkers and D. C. Neckers, Macromolecules, 1995, 28, 81 53 CrossRef CAS.
  10. R. Popielarz and D. C. Neckers, RadTech '96 North America UV/EB Conference Proc., Nashville, TN, 1996. pp. 271–277 Search PubMed.
  11. R. S. Davidson, J. Photochem. Photobiol. A: Chem., 1993, 69, 263 CrossRef; S. N. Gupta, L. Thijs and D. C. Neckers, J. Polym. Sci., Polym. Chem. Ed., 1981, 19, 855 CrossRef CAS; I. Gupta, S. N. Gupta and D. C. Neckers, J. Polym. Sci., Polym. Chem. Ed., 1982, 20, 147 CrossRef CAS.
  12. S. Hu, A. Mejiritski and D. C. Neckers, Chem. Mater., submitted Search PubMed.
  13. Other definitions for Ds have been reported, see L. F. Thompson; C. G. Willson and M. J. Bowden, Introduction to Microlithography, 2nd edn., ACS Professional Reference Book, American Chemical Society, Washington DC, 1994 Search PubMed.
  14. S. A. McDonald, C. G. Willson and J. M. J. Fréchet, Acc. Chem. Res., 1994, 27, 151 CrossRef CAS.
  15. S. Hu and D. C. Neckers, J. Org. Chem., 1997, 62, 564 CrossRef CAS.
  16. S. Hu and D. C. Neckers, J. Am. Chem. Soc., submitted Search PubMed.
  17. M. Kojima, H. Sakuragi and K. Tokumaru, Bull. Chem. Soc. Jpn., 1985, 58, 521.
  18. D. Rehm and A. Weller, Isr. J. Chem., 1970, 8, 259 CAS.
  19. S. L. Murov, Handbook of Photochemistry, Marcel Dekker, New York, 1973 Search PubMed.
Click here to see how this site uses Cookies. View our privacy policy here.