Hostname: page-component-78c5997874-ndw9j Total loading time: 0 Render date: 2024-11-06T09:12:52.371Z Has data issue: false hasContentIssue false

Influence of material and process parameters in the dry-development of positive-tone, polyaldehyde photoresist

Published online by Cambridge University Press:  10 September 2020

Anthony Engler
Affiliation:
School of Chemical and Biomolecular Engineering, Georgia Institute of Technology, Atlanta, Georgia30332-0100, USA
Cassidy Tobin
Affiliation:
School of Chemical and Biomolecular Engineering, Georgia Institute of Technology, Atlanta, Georgia30332-0100, USA
Chi Kin Lo
Affiliation:
School of Chemical and Biomolecular Engineering, Georgia Institute of Technology, Atlanta, Georgia30332-0100, USA
Paul A. Kohl*
Affiliation:
School of Chemical and Biomolecular Engineering, Georgia Institute of Technology, Atlanta, Georgia30332-0100, USA
*
a)Address all correspondence to this author. e-mail: [email protected]
Get access

Abstract

Poly(phthalaldehyde) (pPHA) and copolymers with aliphatic aldehydes were investigated as dry-develop, positive-tone photoresist. Exposure of the films loaded with a photoacid generator to 248 nm radiation creates an acid that depolymerizes the polymer into volatile monomers, allowing the development of features by vaporization rather than solution-based processes. By controlling the acid content, the vaporization rate of the reaction products, and the degree of liquid formation of the decomposed polymer, control of spatial resolution and the quality of polyaldehyde dry-develop photoresist was achieved. Heat, vacuum, and forced convection were evaluated as development techniques in determining the resist sensitivity, contrast, and resolution. Forced convection of heated nitrogen was the most controllable development method for pPHA films. Five-micron lines and spaces were printed. Poly(aldehyde) copolymer resins had slightly lower spatial resolution but were able to be developed faster due to higher vapor pressure of the depolymerized monomers. Cold photo-exposures and development were used to prevent detrimental liquid formation of the decomposed copolymers. In addition to exploring new dry-development methods that have not been tested before, these findings offer insights into designing better material systems and optimizing processes for dry-develop photoresists.

Type
Article
Copyright
Copyright © The Author(s), 2020, published on behalf of Materials Research Society by Cambridge University Press

Access options

Get access to the full version of this content by using one of the access options below. (Log in options will check for institutional or personal access. Content may require purchase if you do not have access.)

References

Campbell, S.: Engineering at the Micro and Nanoscale, 4th ed. (Oxford University Press, New York, 2013).Google Scholar
Dick, A.R., Bell, W.K., Luke, B., Maines, E., Mueller, B., Rawlings, B., Kohl, P.A., and Grant Willson, C.: High aspect ratio patterning of photosensitive polyimide with low thermal expansion coefficient and low dielectric constant. J. Micro/Nanolith. MEM. 15, 033503 (2016).CrossRefGoogle Scholar
Mueller, B.K., Schwartz, J.M., Sutlief, A.E., Bell, W.K., Hayes, C.O., Elce, E., Willson, C.G., and Kohl, P.A.: Chemically amplified, positive tone, polynorbornene dielectric for microelectronics packaging. ECS J. Solid State Sci. Technol. 4, N3001 (2015).CrossRefGoogle Scholar
Ito, H. and Willson, C.G.: Chemical amplification in the design of dry developing resist materials. Polym. Eng. Sci. 23, 1012 (1983).CrossRefGoogle Scholar
Willson, C.G., Dammel, R.R., and Reiser, A.: Photoresist materials: a historical perspective. In Proceedings of SPIE 3050, Metrology, Inspection, and Process Control for Microlithography XI, Vol. 3050 (1997).Google Scholar
Fréchet, J.M.J., Tessier, T.G., and Houlihan, F.M.: Approaches to the design of radiation-sensitive polymeric imaging systems with improved sensitivity and resolution. J. Electrochem. Soc. 133, 181 (1986).Google Scholar
Ito, H. and Schwalm, R.: Thermally developable, positive resist systems with high sensitivity. J. Electrochem. Soc. 136, 241 (1989).CrossRefGoogle Scholar
Frechet, J.M.J., Fahey, J., Willson, C.G., Iizawa, T., Igarashi, K., and Nishikubo, T.: Synthesis of polyformals and their use as dry-developing imgaing systems. Proc. ACS Div. Polym. Mater. Sci. Eng. 60, 174 (1989).Google Scholar
Houlihan, F.M., Bouchard, F., Fréchet, J.M.J., and Willson, C.G.: Thermally depolymerizable polycarbonates. 2. Synthesis of novel linear tertiary copolycarbonates by phase-transfer catalysis. Macromolecules 19, 13 (1986).CrossRefGoogle Scholar
Uzunlar, E., Schwartz, J., Phillips, O., and Kohl, P.A.: Decomposable and template polymers: Fundamentals and applications. J. Electron. Packag. Trans. ASME 138, 1 (2016).CrossRefGoogle Scholar
Chen, L., Goh, Y.-K., Lawrie, K., Smith, B., Montgomery, W., Zimmerman, P.A., Blakey, I., and Whittaker, A.K.: Non-chemically amplified resists for 193-nm immersion lithography: influence of absorbance on performance. Adv. Resist Mater. Process. Technol. XXVII 7639, 76390V (2010)CrossRefGoogle Scholar
Lawrie, K.J., Blakey, I., Blinco, J.P., Cheng, H.H., Gronheid, R., Jack, K.S., Pollentier, I., Leeson, M.J., Younkin, T.R., and Whittaker, A.K.: Chain scission resists for extreme ultraviolet lithography based on high performance polysulfone-containing polymers. J. Mater. Chem. 21, 5629 (2011).CrossRefGoogle Scholar
Bowden, M.J. and Thompson, L.F.: Electron irradiation of poly(olefin sulfones). Application to electron beam resists. J. Appl. Polym. Sci. 17, 3211 (1973).CrossRefGoogle Scholar
Reichmanis, E. and Novembre, A.E.: Lithographic resist materials chemistry. Annu. Rev. Mater. Sci. 23, 11 (1993).CrossRefGoogle Scholar
Wang, F. and Diesendruck, C.E.: Polyphthalaldehyde: Synthesis, derivatives, and applications. Macromol. Rapid Commun. 39, 1 (2018).Google ScholarPubMed
Hatada, K., Kitayama, T., Danjo, S., Yuki, H., Aritome, H., Namba, S., Nate, K., and Yokono, H.: Highly sensitive self developing electron-beam resist of aldehyde copolymer. Polym. Bull. 8, 469 (1982).CrossRefGoogle Scholar
Nate, K., Inoue, T., Yokono, H., and Hatada, K.: Highly sensitive self-developing soft X-ray resists of silicon-containing aldehyde copolymers and sensitive novolac-based composite resists containing aldehyde copolymer. J. Appl. Polym. Sci. 35, 913 (1988).CrossRefGoogle Scholar
Paul, P.C., Knoll, A.W., Holzner, F., Despont, M., and Duerig, U.: Rapid turnaround scanning probe nanolithography. Nanotechnology 22, 275306 (2011).CrossRefGoogle ScholarPubMed
de Marneffe, J.-F., Chan, B.T., Spieser, M., Vereecke, G., Naumov, S., Vanhaeren, D., Wolf, H., and Knoll, A.W.: Conversion of a patterned organic resist into a high performance inorganic hard mask for high resolution pattern transfer. ACS Nano 12, 11152 (2018).CrossRefGoogle Scholar
Holzner, F., Paul, P., Despont, M., Cheong, L.L., Hedrick, J., Dürig, U., and Knoll, A.: Thermal probe nanolithography: in-situ inspection, high-speed, high-resolution, 3D. In 29th Eur. Mask Lithogr. Conf., Vol. 888605 (2013).Google Scholar
Schwartz, J.M., Phillips, O., Engler, A., Sutlief, A., Lee, J., and Kohl, P.A.: Stable, high-molecular-weight Poly(phthalaldehyde). J. Polym. Sci. Polym. Chem. 55, 1166 (2017).CrossRefGoogle Scholar
Frechet, J.M.J., Bouchard, F., Eichler, E., Houlihan, F.M., Iizawa, T., Kryczka, B., and Willson, C.G.: Thermally depolymerizable polycarbonates V. acid catalyzed thermolysis of allylic and benzylic polycarbonates: A new route to resist imaging. Polym. J. 19, 31 (1987).CrossRefGoogle Scholar
Engler, A., Phillips, O., Miller, R.C., Tobin, C., and Kohl, P.A.: Cationic copolymerization of o-Phthalaldehyde and functional aliphatic aldehydes. Macromolecules 52, 4020 (2019).Google Scholar