Molecular Structure of Advanced Photoresists

doi:10.7517/j.issn.1674-0475.2011.06.417

Abstract

Abstract: This article reviews the development of lithography technology and photoresists as well as their molecular structure for 193 nm and extreme ultravioletlithography (EUVL,the next generation lithography).Especially,we describe the recent research and development of EUV photoresists in detail for the purpose of being conducive to the domestic research on advanced photoresists.

Key words: photoresists, EUV lithography, 193 nm lithography, chemically amplified photoresists, molecular glass

CLC Number:

O64
TN305

XU Jian, CHEN Li, TIAN Kai-jun, HU Rui, LI Sha-yu, WANG Shuang-qing, YANG Guo-qiang. Molecular Structure of Advanced Photoresists[J]. Imaging Science and Photochemistry, 2011, 29(6): 417-429.

References

[1] 郑金红.光刻胶的发展及应用[J].精细与专用化学品,2006,14(16):24-30.Zheng J H.Development trends and market of photoresist[J].Fine and Specialty Chemicals,2006,14(16):24-30.
[2] Pfeiffer F,Felix N M,Neuber C,Ober C K,Schmidt H-W.Physical vapor deposition of molecular glass photoresists:a new route to chemically amplified patterning[J].Adv.Funct.Mater.,2007,17:2336-2342.
[3] Moore G E.Cramming more components onto integrated circuits[J].Electron,1965,38:114-117.
[4] Wagner C,Hamed N.EUV lithography:lithography gets extreme[J].Nature Photonics,2010,4:24-26.
[5] Tallents G,Wagenaars E,Pert G.Lithography at EUV wavelengths[J].Nature Photonics,2010,4:809-811.
[6] 郑金红.我国光刻胶的市场现状及发展趋势[J].精细与专用化学品,2008,17(9):28-31.Zheng J H.Matket status quo and development trends of photoresist in China[J].Fine and Specialty Chemicals,2008,17(9):28-31.
[7] Totzeck M,Ulrich W,Gohnermeier A,Kaiser W.Pushing deep ultraviolet lithography to its limits[J].Nature Photonics,2007,1:829-831.
[8] Ito T,Okazaki S.Pushing the limits of lithography[J].Nature,2000,406:1027-1031.
[9] Warlaumont J.Pushing the limits[J].Nature Photonics,2010,4:30.
[10] http://www.itrs.net/Links/2010ITRS/2010Update/ToPost/2010_Update_Overview.pdf
[11] Ito H,Willson C G.Chemical amplification in the design of dry developing resist materials[J].Polym.Eng.Sci.,1983,23:1012.
[12] Macdonald S A,Willson C G,Frechet J M J.Chemical amplification in high-resolution imaging systems[J].Accounts of Chemical Research,1994,27:151.
[13] Shirai M,Tsunooka M.Photoacid and photobase generators:chemistry and applications to polymeric materials[J].Prog.Polym.Sci.,1996,21:1.
[14] Sanders D P.Advanced in patterning materials for 193 nm immersion lithography[J].Chem.Rev.,2010,110:321-360.
[15] Diakoumakos C D,Raptis I,Tserepi A,Argitis P.Free-radical synthesis of narrow polydispersed 2-hydroxyethyl methacrylate-based tetrapolymers for dilute aqueous base developable negative photoresists[J].Polymer,2002,43:1103-1113.
[16] Li W,Varanasi P R,Lawson M C,Kwong R W,Chen K J,Ito H,Truong H,Allen R D,Yamamoto M,Kobayashi E,Slezak M.Rational design in cyclic olefin resists for sub-100-nm lithography[J].Proc.SPIE,2003,61:5039.
[17] Ito H.Development of new advanced resist materials for microlithography[J].J.Photopolym.Sci.Technol.,2008,21:475-491.
[18] Sooriyakumaran R,Sanders D P,Truong H,Allen R D,Colburn M E,Mclntyre G R.High refractive index polymer platforms for 193 nm immersion lithography[J].4th International Symposium on Immersion lithography,2007.
[19] Argitis P,Niakoula D,Douvas A M,Gogolides E,Raptis I,Vidali V P,Couladouros E A.Materials for lithography in the nanoscale[J].Int.J.Nanotechnol.,2009,6:71-87.
[20] 中国科学院理化技术研究所.2011年国际光学工程学会先进光刻技术会议在美国召开(会讯).影像科学与光化学,2011,29(3):233.Technical Institute of Physics and Chemistry,CAS.SPIE Advanced Lithography Conference 2011 was held in the United States.Imaging Science and Photochemistry,2011,29(3):233.
[21] Nishikubo T,Kudo H J.Recent development in molecular resists for extreme ultraviolet lithography[J].Photopolym.Sci.Technol.,2011,24:9-18.
[22] Kozawa T,Tagawa S.Radiation chemistry in chemically amplified resists[J].Jpn.J.Appl.Phys.,2010,49:030001
[23] Shirai M,Maki K,Okamura H,Kaneyama K,Itani T.Non-chemically amplified EUV resist based on PHS[J].J.Photopolym.Sci.Technol.,2009,22(1):111-116.
[24] Shirai M,Maki K,Okamura H,Kaneyama K,Itani T.Negative EUV resist based on thiol-ene system[J].J.Photopolym.Sci.Technol.,2010,23(5):687-691.
[25] Cardineau B,Kruger S,Earley W,Higgins C,Revuru S,Georger J,Brainard R.Chain-scission polyesters for EUV lithography[J].J.Photopolym.Sci.Technol.,2010,23(6):665-671.
[26] Lawrie K J,Blakey I,Blinco J P,Cheng H H,Gronheid R,Jack K S,Pollentier I,Leeson M J,Younkin T R,Whittaker A K.Chain scission resists for extreme ultraviolet lithography based on high performance polysulfone-containing polymers[J].J.Mater.Chem.,2011,21:5629-5637.
[27] Blakey I,Yu A-G,Blinco J,Jack K S,Liu H-P,Whittaker A K,Leeson M,Yueh W,Younkin T.Polycarbonate based nonchemically amplified photoresist for extreme ultraviolet lithography[J].Proc.SPIE,2010,7636:763635.
[28] Dai J,Chang S W,Hamad A,Yang D,Felix N,Ober C K.Molecular glass resists for high-resolution patterning[J].Chem.Mater.,2006,18:3404-3411.
[29] Tsuchiya K,Chang S W,Felix N M,Ueda M,Ober C K.Lithography based on molecular glasses[J].J.Photopolym.Sci.Technol.,2005,18(3):431-434.
[30] VanderHart D L,Prabhu V M,Silva A D,Felix N M,Ober C K.Solid state NMR investigation of photoresist molecular glasses including blend behavior with a photoacid generator[J].J.Mater.Chem.,2009,19:2683-2694.
[31] Pfeiffer F,Felix N M,Neuber C,Ober C K,Schmidt H-W.Towards environmentally friendly,dry deposited,water developable molecular glass photoresists[J].Phys.Chem.Chem.Phys.,2008,10:1257-1262.
[32] Yang D,Chang S W,Ober C K.Molecular glass photoresists for advanced lithography[J].J.Mater.Chem.,2006,16:1693-1696.
[33] Silva A D,Lee J-K,Andre X,Felix N M,Cao H B,Deng H,Ober C K.Study of the structure-properties relationship of phenolic molecular glass resists for next generation photolithography[J].Chem.Mater.,2008,20:1606-1613.
[34] Silva A D,Ober C K.Hydroxyphenylbenzene derivatives as glass forming molecules for high resolution photoresists[J].J.Mater.Chem.,2008,18:1903-1910.
[35] Sha J,Lee J-K,Kang S,Prabhu V M,Soles C L,Bonnesen P V,Ober C K.Architectural effects on acid reaction-diffusion kinetics in molecular glass photoresists[J].Chem.Mater.,2010,22:3093-3098.
[36] 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[J].Chem.Mater.,2008,20:7292-7300.
[37] Oizumi H,Tanaka Y,Kumise T,Shiono D,Hirayama T,Hada H,Onodera J,Yamaguchi A,Nishiyama I.Evaluation of new molecular resist for EUV lithography[J].J.Photopolym.Sci.Technol.,2007,20(3):403-410.
[38] Owada T,Yomogita A,Kashiwamura T,Kusaba T,Miyamoto S,Takeya T.Development of novel positivetone resists for EUVL[J].SPIE,2009,7273.
[39] 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].J.Photopolym.Sci.Technol.,2009,22:73-76.
[40] Kudo H,Jinguji M,Nishikubo T,Oizumi H,Itani T.Extreme ultraviolet(EUV)-resist materials of Noria(water wheel-like cyclic oligomer) derivatives containing acetal moieties[J].J.Photopolym.Sci.Technol.,2010,23:657-664.
[41] Niina N,Kudo H,Maruyama K,Kai T,Shimokawa T,Oizumi H,Itani T,Nishikubo T.Multicomponent negative-type photoresist based on Noria analog with 12 etboxy groups[J].Polymer Journal,2011,43:407-413.
[42] Fukushima Y,Watanabe T,Ohnishi R,Kinoshita H,Suzuki S,Yusa S,Endo Y,Hayakawa M,Yamanaka T.PAG study of PAG bonded resist for EUV and EB lithography[J].J.Photopolym.Sci.Technol.,2008,21(4):465-468.
[43] Thackeray J W,Aqad E,Kang S J,Spear-Alfonso K.Design considerations for EUV resist materials[J].J.Photopolym.Sci.Technol.,2009,22(1):65-71.
[44] Thackeray J W,Jain V,Coley S,Christianson M,Arriola D,LaBeaume P,Kang S J,Wagner M,Sung J W,Cameron J.Optimization of polymer-bound PAG(PBP) for 20 nm EUV lithography[J].J.Photopolym.Sci.Technol.,2011,24(2):179-183.
[45] Allen R D,Brock P J,Na Y-H,Sherwood M H,Truong H D,Wallraff G M,Fujiwara M,Maeda K.Investigation of polymer-bound PAGs:Synthesis,characterization and initial structure/property relationships of anionbound resists[J].J.Photopolym.Sci.Technol.,2009,22(1):25-29.
[46] Lawson R A,Lee C T,Yueh W,Tolbert L,Henderson C L.Water-developable negative-tone single-molecule resists:high-sensitivity nonchemically amplified resists[J].Proc.SPIE.,2008,6923