Chemically amplified DUV photoresists using a new class of photoacid-generating compounds

Pawlowski, Georg; Dammel, Ralph R.; Lindley, Charlet R.; Merrem, Hans-Joachim; Roeschert, Heinz; Lingnau, J.

doi:10.1117/12.20133

Cited by 18 publications

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“…In fact, product studies we performed on DSD showed that one of the main products formed upon photolysis in acetonitrile/water is the expected sulfonic acid formed via reaction of the sulfene with water (Scheme ). Similar products have been observed in the photolysis of other α-diazosulfones 2 …”

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confidence: 76%

“…α-Diazosulfones are interesting because they are potential precursors of sulfonic acids. For these compounds, the initial formation of the carbene is followed by a sulfo-Wolff rearrangement to give the sulfene which is hydrolyzed in water to yield the sulfonic acid. − While the reactions of α-ketocarbenes to yield ketenes have been the subject of intensive studies (vide infra), the corresponding reactions of α-sulfonylcarbenes and sulfenes have received less attention . These studies have relied predominantly on the analysis of products from solvolysis of reaction intermediates.…”

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Laser Flash Photolysis of Diphenylsulfonyldiazomethane: Detection of the Sulfene and a Sulfene−Pyridine Ylide

et al. 2000

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The photochemistry of diphenylsulfonyldiazomethane (DSD) was studied by means of nanosecond laser flash photolysis. The photochemical behavior of this molecule upon UV irradiation is characterized by sulfene formation, presumed to arise via Wolff rearrangement of a carbene. We were able to detect the sulfene and the sulfene ylide formed upon sulfene trapping by pyridine. Sulfene quenching by nucleophiles was also examined.

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confidence: 76%

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confidence: 99%

Laser Flash Photolysis of Diphenylsulfonyldiazomethane: Detection of the Sulfene and a Sulfene−Pyridine Ylide

et al. 2000

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“…Thus, such systems have very high sensitivity. This chemical amplification concept has been exploited in the design of a large number of new resist systems. − …”

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Alicyclic Polymers for 193 nm Resist Applications: Synthesis and Characterization

Okoroanyanwu

Shimokawa

Byers³

et al. 1998

Chem. Mater.

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A series of new alicyclic polymers designed for use as 193 nm photoresist materials has been synthesized and characterized. These resins are based on cycloaliphatic co-and terpolymers of 2-methylpropylbicyclo[2.2.1]hept-5-ene-2-carboxylate (trivial name, carbotert-butoxy norbornene), bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (trivial name, norbornene carboxylic acid), 8-methyl-8-carboxytetracyclo[4,4,0.1, 2,5 1 7,10 ]dodec-3-ene (trivial name, methyl tetracyclododecene carboxylic acid), 5-(hydroxymethyl)-2-norbornene-2-methanol, and maleic anhydride, which were synthesized by free radical, Pd(II)-catalyzed addition, and ringopening metathesis polymerization techniques. The polymers derived from ring-opening metathesis polymerization were hydrogenated to provide another member of this group of materials. The polymers are soluble in common organic solvents and have glass transition temperatures ranging from less than 60°C to higher than 250°C depending on their specific structure and mode of polymerization. The low absorption of these polymers at 193 nm wavelength and their high resistance to reactive ion etching make these attractive candidates for 193 nm resist applications.

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Photolithography

Leuschner

Pawlowski²

2013

Materials Science and Technology

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The sections in this article are Introduction Exposure Tools Image Formation and Resolution Contact and Proximity Printing Optical Mask Aligner X‐Ray Stepper Projection Printing Near UV Projection Systems Deep UV Projection Systems Nonconventional UV Lithography Post‐Optical Lithography Photoresist Processing Quality Control and Resist Deposition Purity and Storage Stability Resist Coating Resist Exposure and Development Characteristic Curve and Standing Wave Effects Process Latitudes Dissolution Rate and Development Methods Pattern Inspection and Resist Profile Simulation Etching, Resist Stripping and Planarization Photoresists Principles of Photoresist Chemistry Negative‐Tone Resists Photocrossslinking Via Azides Free‐Radical‐Initiated Polymerization Acid‐Catalyzed Crosslinking Positive‐Tone Resists Dissolution Inhibition/Dissolution Promotion Acid‐Catalyzed Deblocking Polymer Degradation Solvents for Photoresists and Main Resist Suppliers Special Photoresist Techniques Nonconventional Diazo Resist Processes Resist Profile Modification and Image Reversal Bilayer Systems for Contrast Enhancement Suppression of Reflections and Standing Wave Effects Dyed Resists Antireflective Layers Silicon‐Containing Multilayer Resists Negative‐Tone Silicon Bilayer Resists Positive‐Tone Silicon Bilayer Resists Top Surface Imaging Gas Phase Silylation Systems Liquid Phase Silylation Systems Trends in Photolithography

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Chemically amplified DUV photoresists using a new class of photoacid-generating compounds

Cited by 18 publications

References 0 publications

Laser Flash Photolysis of Diphenylsulfonyldiazomethane: Detection of the Sulfene and a Sulfene−Pyridine Ylide

Laser Flash Photolysis of Diphenylsulfonyldiazomethane: Detection of the Sulfene and a Sulfene−Pyridine Ylide

Alicyclic Polymers for 193 nm Resist Applications: Synthesis and Characterization

Photolithography

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