Elucidating the patterning mechanism of zirconium-based hybrid photoresists

Abstract. We report a series of studies aimed at shedding more light on the development mechanism of zirconium (Zr)-based extreme-UV hybrid photoresists. In earlier works, our group demonstrated that Zr-based hybrid resists are capable of resolving 30-nm half-pitch features with a very high sensitivity in the range of 1 to 20  mJ/cm2, which renders these materials potential candidates in the area of nonchemically amplified inorganic resists. While attractive because of its high sensitivity, Zr-methacrylic acid suffers from scumming problems. In an effort to better understand what controls sensitivity and scumming phenomena, we employed a combination of analytical techniques (electrospray ionization mass spectrometry, x-ray photoelectron spectroscopy, and Fourier transform infrared spectroscopy) to study the patterning mechanism in detail, to be able to optimize the development process and develop systems with optimal features.

[1]  Markos Trikeriotis,et al.  Development of an inorganic photoresist for DUV, EUV, and electron beam imaging , 2010, Advanced Lithography.

[2]  Li Li,et al.  Studying the Mechanism of Hybrid Nanoparticle Photoresists: Effect of Particle Size on Photopatterning , 2015 .

[3]  Feixiang Luo,et al.  Chemical and structural investigation of high-resolution patterning with HafSO(x). , 2014, ACS applied materials & interfaces.

[4]  Bilge Yildiz,et al.  Non-equilibrium oxidation states of zirconium during early stages of metal oxidation , 2015 .

[5]  Markos Trikeriotis,et al.  A new inorganic EUV resist with high-etch resistance , 2012, Advanced Lithography.

[6]  Christopher K. Ober,et al.  Increasing sensitivity of oxide nanoparticle photoresists , 2014, Advanced Lithography.

[7]  Ulrich S. Schubert,et al.  Can the Clusters Zr6O4(OH)4(OOCR)12 and [Zr6O4(OH)4(OOCR)12]2 Be Converted into Each Other? , 2006 .

[8]  Marie Krysak,et al.  Investigation of novel inorganic resist materials for EUV lithography , 2014, Advanced Lithography.

[9]  Christopher K. Ober,et al.  Non-aqueous negative-tone development of inorganic metal oxide nanoparticle photoresists for next generation lithography , 2013, Advanced Lithography.

[10]  Shengrong Yang,et al.  A simple one-step solution deposition process for constructing high-performance amorphous zirconium oxide thin film , 2014 .

[11]  J. Gaumet,et al.  Electrospray mass spectrometry of , 2000, Journal of the American Society for Mass Spectrometry.

[12]  Shoujun Xu,et al.  Mass Spectrometric and Photoelectron Spectroscopic Studies of Zirconium Oxide Molecular and Cluster Anions , 1999 .

[13]  Olivier Soppera,et al.  Room-temperature preparation of metal-oxide nanostructures by DUV lithography from metal-oxo clusters , 2014 .

[14]  Minoru Toriumi,et al.  Characterization of 'metal resist' for EUV lithography , 2016, SPIE Advanced Lithography.

[15]  Glen B. Deacon,et al.  Relationships between the carbon-oxygen stretching frequencies of carboxylato complexes and the type of carboxylate coordination , 1980 .

[16]  Ulrich S. Schubert,et al.  Oxozirconium Methacrylate Clusters: Zr6(OH)4O4(OMc)12 and Zr4O2(OMc)12 (OMc = Methacrylate) , 1997 .

[17]  Sang Hyun Jung,et al.  Facile size-tunable fabrication of functional tin dioxide nanostructures by multiple size reduction lithography. , 2012, ACS applied materials & interfaces.

[18]  Shibdas Banerjee,et al.  Electrospray Ionization Mass Spectrometry: A Technique to Access the Information beyond the Molecular Weight of the Analyte , 2011, International journal of analytical chemistry.

[19]  Marjorie A. Langell,et al.  XPS analysis of oleylamine/oleic acid capped Fe3O4 nanoparticles as a function of temperature , 2014 .

[20]  Vijayamohanan K. Pillai,et al.  Enhanced nucleation of polypropylene by metal–organic frameworks (MOFs) based on aluminium dicarboxylates: influence of structural features , 2016 .

[21]  Christopher K. Ober,et al.  Nanoparticle photoresist studies for EUV lithography , 2017, Advanced Lithography.

[22]  Mohammad Khaja Nazeeruddin,et al.  Efficient inorganic-organic hybrid perovskite solar cells based on pyrene arylamine derivatives as hole-transporting materials. , 2013, Journal of the American Chemical Society.

[23]  Markos Trikeriotis,et al.  Oxide nanoparticle EUV resists: toward understanding the mechanism of positive and negative tone patterning , 2013, Advanced Lithography.

[24]  Warren Montgomery,et al.  Development of an inorganic nanoparticle photoresist for EUV, e-beam, and 193nm lithography , 2011, Advanced Lithography.

[25]  U. Schubert.  Cluster-based inorganic-organic hybrid materials. , 2011, Chemical Society reviews.

[26]  Markos Trikeriotis,et al.  High refractive index and high transparency HfO2 nanocomposites for next generation lithography , 2010 .

[27]  Hong Yee Low,et al.  Direct patterning of TiO₂ using step-and-flash imprint lithography. , 2012, ACS nano.

[28]  Gérard Férey,et al.  Metal-organic frameworks as efficient materials for drug delivery. , 2006, Angewandte Chemie.

[29]  Markos Trikeriotis,et al.  Nanoparticle photoresists from HfO2 and ZrO2 for EUV patterning , 2012 .

[30]  Jing Jiang,et al.  Metal Oxide Nanoparticle Photoresists for EUV Patterning , 2014 .

[31]  Ulrich S. Schubert,et al.  Variations in capping the Zr6O4(OH)4 cluster core: X-ray structure analyses of [Zr6(OH)4O4(OOC–CHCH2)10]2(μ-OOC–CHCH2)4 and Zr6(OH)4O4(OOCR)12(PrOH) (R = Ph, CMe = CH2) , 1999 .

[32]  Graham A. Bowmaker,et al.  Electrospray mass spectrometry of highly moisture-sensitive metal alkoxides , 1997 .

[33]  J. BrianF.G.Johnson,et al.  Spectroscopic and mass spectrometric methods for the characterisation of metal clusters , 2000 .

[34]  Markos Trikeriotis,et al.  Nanoparticle Photoresists: Ligand Exchange as a New, Sensitive EUV Patterning Mechanism , 2013 .

[35]  M. Popall,et al.  Applications of advanced hybrid organic-inorganic nanomaterials: from laboratory to market. , 2011, Chemical Society reviews.

[36]  Christopher K. Ober,et al.  Recent progress in nanoparticle photoresists development for EUV lithography , 2016, SPIE Advanced Lithography.