Multicomponent negative-type photoresist based on Noria analog with 12 ethoxy groups

Polymer Journal

Volumn 43, Issue 4, 2011, Pages 407-413

  Niina, Nobumitsu ^a   Kudo, Hiroto ^a   Maruyama, Ken ^b   Kai, Toshiyuki ^b   Shimokawa, Tsutomu ^b   Oizumi, Hiroaki ^c   Itani, Toshiro ^c   Nishikubo, Tadatomi ^a  

^a KANAGAWA UNIVERSITY   (Japan)

^b JSR CORPORATION   (Japan)

^c SEMICONDUCTOR LEADING EDGE TECHNOLOGIES INC   (Japan)

Author keywords

EB; EUV; negative type; noria; resist

Indexed keywords

EB; EUV; NEGATIVE TYPE; NORIA; RESIST;

AMMONIUM COMPOUNDS; AMORPHOUS FILMS; CONDENSATION REACTIONS; ORGANIC SOLVENTS; PHOTORESISTS;

MECHANICAL PROPERTIES;

EID: 79953711448     PISSN: 00323896     EISSN: 13490540     Source Type: Journal    
DOI: 10.1038/pj.2010.146     Document Type: Article

References (23)

1. Silva, A. D., Sundberg, L. K., Ito, H., Sooriyakumaran, R., Allen, R. D. & Ober, C. K. A fundamental study on dissolution behavior of high-resolution molecular glass photoresists. Chem. Mater. 20, 7292-7300 (2008).
2. Silva, A. D., Lee, J.- K., André , X., Felix, N. M., Cao, H. B., Deng, H. & Ober, C. K. Study of the structureproperties relationship of phenolic molecular glass resists for next generation photolithography. Chem. Mater. 20, 1606-1613 (2008). (Pubitemid 351363090)
3. Hirayama, T., Shiono, D., Onodera, J., Yamaguchi, A. & Fukuda, H. Depth profile and line-edge roughness of partially O-1-ethoxyethylated low molecular weight amorphous polyphenol and poly(p-hydroxystyrene) base resists for electron-beam lithography. Polym. Adv. Technol. 17, 116-121 (2006). (Pubitemid 43380277)
4. Yoshiiwa, M., Kageyama, H., Shirota, Y., Wakaya, F., Gamo, K. & Takai, M. Novel class of low molecular-weight organic resists for nanometer lithography. Appl. Phys. Lett. 69, 2605-2607 (1996). (Pubitemid 126595577)
5. Ochiai, Y., Manako, S., Yamamoto, H., Teshima, T., Fujita, J. & Nomura, E. Highresolution, high-purity calix[n]arene electron beam resist. J. Photopolym. Sci. Technol. 13, 413-417 (2000).
6. Fujita, J., Ohnishi, Y., Manako, S., Ochiai, Y., Nomura, E., Sakamoto, T. & Matui, S. Calixarene electron beam resist for nano-lithography. Jpn. J. App. Phys. 36, 7769-7772 (1997).
7. Fujita, J., Ohnishi, Y., Ochiai, Y. & Matui, S. Ultrahigh resolution of calixarene negative resist in electron beam lithography. Appl. Phys. Lett. 68, 1297-1299 (1996). (Pubitemid 126684162)
8. Ueda, M., Takahashi, D., Nakayama, T. & Haba, O. Three-component negative-type photoresist based on calix[4]resorcinarene, a cross-linker, and a photoacid generator. Chem. Mater. 10, 2230-2234 (1998). (Pubitemid 128473973)
9. Nakayama, T., Haga, K., Haba, O. & Ueda, M. A negative-working alkaline developable photoresist based on calix[4]resorcinarene, a cross-linker, and a photoacid generator. Chem. Lett. 26, 265-266 (1997).
10. Hattori, S., Yamada, A., Saito, S., Asakawa, K., Koshiba, T. & Nakasugi, T. High resolution positive-working molecular resist derived from truxene. J. Photopoly. Sci. Technol. 22, 609-614 (2009).
11. Chang, S. W., Ayothi, R., Bratton, D., Yang, D., Felix, N., Cao, H. B., Deng, H. & Ober, C. K. Sub-50nm feature size using positive tone molecular glass resists for EUV lithography. J. Matter. Chem. 16, 1470-1474 (2006). (Pubitemid 43797597)
12. Tully, D. C., Trimble, A. R. & Frechet, J. M. J. Dendrimers with thermally labile end groups: an alternative approach to chemistry. Adv. Mater. 12, 1118-1122 (2000).
13. Tada, T. & Nakayama, T. Nanolithograhpy using fullerene films. Jpn. J. Appl. Phys. 35, 63-65 (1996).
14. Yoshiiwa, M., Kageyama, H., Wakaya, F., Takai, M., Gamo, K. & Shirota, Y. 1,3,5-Tris [4-(tert-Butoxycarbonylmethoxy)-phenyl]benzene as a novel electron-beam positive resist for nanometer lithography. J. Photopolym. Sci. Tech. 9, 57-58 (1996). (Pubitemid 126814331)
15. Kudo, H., Hayashi, R., Mitani, K., Yokozawa, T., Kasuga, N. C. & Nishikubo, T. Molecular Waterwheel (Noria) from a simple condensation of resorcinol and an alkanedial. Angew. Chem. Int. Ed. 45, 7948-7952 (2006). (Pubitemid 44912748)
16. André , X., Lee, J. K., DeSilva, A., Ober, C. K., Cao, H. B., Deng, H., Kudo, H., Watanabe, D. & Nishikubo, T. Phenolic molecular glasses as resists for next generation lithography. SPIE 6519, 65194B (2007).
17. Kudo, H., Watanabe, D., Nishikubo, T., Maruyama, K., Shimizu, D., Kai, T., Shimokawa, T. & Ober, C. K. A novel Noria (Water-wheel-like cyclic oligomer) derivative as a chemically amplified electron-beam resist material. J. Mater. Chem. 18, 3588-3592 (2008).
18. Nishikubo, T., Kudo, H., Suyama, Y., Oizumi, H. & Itani, T. Novel Noria (water wheel-like cyclic oligomer) derivative as a chemically amplified extreme ultraviolet (EUV)-resist material. J. Photopolym. Sci. Technol. 22, 73-76 (2009).
19. Kudo, H., Suyama, Y., Oizumi, H., Itani, T. & Nishikubo, T. Novel extreme ultraviolet (EUV)-resist material based on noria (water wheel-like cyclic oligomer). J. Mater. Chem. 20, 4445-4450 (2010).
20. Seki, H., Kato, Y., Kudo, H., Oizumi, H., Itani, T. & Nishikubo, T. Negative-type extreme ultraviolet resist materials based on water-wheel-like cyclic oligomer (Noria). Jpn. J. Appl. Phys. 49, 06GF06 (2010).
21. Niina, N., Kudo, H. & Nishikubo, T. Synthesis of noria-like macrocycles containing alkoxy groups based on a dynamic covalent chemistry (DCC) system by the A2+B4 condensation. Chem. Lett. 38, 1198-1199 (2009).
22. Lee, S. M. & Fréchet, J. M. J. Mechanism of the acid-catalyzed cross-linking of poly(4- hydroxystyrene) by polyfunctional benzyl alcohols: a model study. Macromolecules 27, 5160-5166 (1994).
23. Posse, A. J. & Belter, R. K. Vitamin C in organic synthesis: reaction with p-hydroxybenzyl alcohol derivatives. J. Org.Chem. 53, 1535-1540 (1988).