Chemically Amplified Main Chain Scission: New Concept to Reduce Line Edge Roughness and Outgassing.

Eschbaumer, Christian; Heusinger, Nicole; Hohle, Christoph; Sebald, Michael

doi:10.2494/photopolymer.15.673

Cited by 9 publications

(3 citation statements)

References 11 publications

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“…Polymethyl methacrylate and other methacrylic polymers (ZEP) have been widely used as e-beam resist showing capabilities for structures below 10 nm feature sizes [16,17]. Nevertheless, in the case of the commonly used non-chemically amplified materials of this type issues like sensitivity and poor etch resistance limit their areas of application, whereas inadequate etch resistance and non-satisfactory process reliability are the usual problems encountered in acid catalyzed materials based on main chain scission [18,19].…”

Section: Introductionmentioning

confidence: 99%

Ultra-sensitive EUV resists based on acid-catalyzed polymer backbone breaking

Manouras

Kazazis

Koufakis

et al. 2018

Extreme Ultraviolet (EUV) Lithography IX

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The aim of the current work was to develop new sensitive polymeric materials for lithographic applications, focusing in particular to EUV lithography, where the main polymer chain is cleaved under the influence of photogenerated acid. Resist materials based on the cleavage of polymer main chain are in principle capable to create very small structures, to the dimensions of the monomers that they consist of. Nevertheless, in the case of the commonly used non-chemically amplified materials of this type issues like sensitivity and poor etch resistance limit their areas of application, whereas inadequate etch resistance and unsatisfactory process reliability are the usual problems encountered in acid catalyzed materials based on main chain scission. In our material design, the acid catalyzed chain cleavable polymers contain very sensitive moieties in their backbone while they remain intact in alkaline ambient. These newly synthesized polymers bear in addition suitable functional groups for the achievement of desirable lithographic characteristics (thermal stability, acceptable glass transition temperature, etch resistance, proper dissolution behavior, adhesion to the substrate). Our approach for achieving acceptable etch resistance, a main drawback in other main chain cleavable resists, is based on the introduction of polyaromatic hydrocarbons in the polymeric backbone, whereas the incorporation of an inorganic component further enhances the etch resistance. Single component systems can also be designed following the proposed approach by the incorporation of suitable PAGs and base quencher molecules in the main chain. Resist formulations based on a random copolymer designed according to the described rules evaluated in EUV exhibit ultrahigh sensitivity, capability for high-resolution patterning and overall processing characteristics that make them strong candidates upon further optimization.

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Section: Introductionmentioning

confidence: 99%

Ultra-sensitive EUV resists based on acid-catalyzed polymer backbone breaking

Manouras

Kazazis

Koufakis

et al. 2018

Extreme Ultraviolet (EUV) Lithography IX

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“…To this aim, various materials with the ability to decompose via heat or light have been proposed. [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20] Multi-functional (meth)acrylates with structures such as tertiary ester, 2-7,10-16 acetal, 8,9,[17][18][19] and carbonate, 20 which experience bond cleavage in acid, have been reported. The research group of Osaka Prefecture University has developed a radically curable tri-functional methacrylate resin with a decomposition function.…”

Section: Introductionmentioning

confidence: 99%

Positive‐tone photoresist consisting of a multifunctional acrylate resin that can be patterned after photo‐crosslinking

Sugita

Miyashita

Suzuki

et al. 2017

J of Applied Polymer Sci

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A multifunctional acrylate resin having a tertiary ester structure is synthesized using a thiol‐acrylate Michael addition click reaction. By loading both a photo radical initiator and a photo acid generator into this resin, a positive‐tone photoresist, that can be patterned after photocrosslinking (PPaP), is formulated. After the thin film is irradiated with 365 nm light, radical crosslinking proceeds and a solvent resistant “frozen” film can be obtained. The frozen film works as a positive‐tone photoresist. When the frozen PPaP is irradiated with light containing a wavelength much shorter than 300 nm, the ester structure of the exposed region is decomposed by photo‐chemically generated acid and dissolved in an alkaline solution. Furthermore, a photochemical pattern transfer is achieved using the material. By performing the photo exposure on conventional photoresist patterns on the frozen PPaP underlayer, the photoresist patterns are successfully transferred to the underlayer. © 2017 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2018, 135, 45871.

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“…Απαναίηδηδ πνμτπυεεζδ είκαζ δ πανμοζία υλζκα δζαζπχιεκςκ μιάδςκ ζηδκ ηονία αθοζίδα ημο πμθοιενμφξ. Σέημζεξ μιάδεξ είκαζ μζ αηεηάθεξ[86][87][88], μζ εζηένεξ[89] ηαζ βεκζηά μιάδεξ πμο πενζέπμοκ ζηδκ ηφνζα αθοζίδα ημοξ δεζιμφξ C-O[90,91]. Σμ θςημπαναβχιεκμ μλφ ηαηαθφεζ αοημφξ ημοξ δεζιμφξ δζαζπχκηαξ έηζζ ημ πμθοιενέξ πμο έπεζ αηηζκμαμθδεεί.…”

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Λιθογραφικά Υλικά Που Βασίζονται Σε Φωτοχημικά Προκαλούμενη Διάσπαση Της Κύριας Αλυσίδας Πολυακεταλών

Manouras¹,

Μανουράς²

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The present dissertation refers to the exploration of novel lithographic materials, based on photodegradable polymers of the polyketal/polyacetal family that undergo main chain scission via photochemically mediated pathways. Suitable synthetic methodologies were developed allowing the incorporation of selected chemical functionalities in the polymers resulted to absorption spectrum tuning for effective photolysis under preferred irradiation conditions either mediated by photoacid generators, or induced by direct polymer group excitation. In addition, the rational chemical design of the polymers, allowed optimization of a range of physicochemical parameters of the developed polymeric materials those were crucial in selective applications.In the quest for the development of materials for standard semiconductor lithography aiming at device fabrication, we achieved the synthesis of polymers with desirable physicochemical properties such as optimum solubility before and after exposure in selective solvents, and lithographic process acceptable glass transition temperatures. Polymeric materials based on photogenerated acid catalyzed degradation of the polymer main chain, produced upon UV exposure (248nm) and contact printing well-defined arbitrary patterns down to 500nm. In addition, it was demonstrated that lithographic materials based on a main chain scission mechanism can provide adequate resistance during standard plasma etching processes.On the other hand, in an effort to exploit possibilities offered by the direct photochemical degradation of the polymers, new processes of interest for biotechnological applications were proposed. It was first demonstrated the possibility of controlling the photolysis process via selecting appropriate chromophores at specific irradiation wavelengths covering the range from 193 to 365nm. Then, using laser exposure a novel process of forming patterns on cultured cells developed on the polymer substrates was introduced. Furthermore, the possibility of effective multiphoton photolysis was achieved by laser irradiation at 512 and 1064 nm through a photomask. Finally, a block copolymer was synthesized based on a photosensitive polyketal block and a polyethylene oxide block which was shown to form polymer micelles that were loaded with bioactive substances and served as a photolabile drug delivery agent against HeLa cancer cells.

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Chemically Amplified Main Chain Scission: New Concept to Reduce Line Edge Roughness and Outgassing.

Cited by 9 publications

References 11 publications

Ultra-sensitive EUV resists based on acid-catalyzed polymer backbone breaking

Ultra-sensitive EUV resists based on acid-catalyzed polymer backbone breaking

Positive‐tone photoresist consisting of a multifunctional acrylate resin that can be patterned after photo‐crosslinking

Λιθογραφικά Υλικά Που Βασίζονται Σε Φωτοχημικά Προκαλούμενη Διάσπαση Της Κύριας Αλυσίδας Πολυακεταλών

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