Chemistry:Diazonaphthoquinone
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| Preferred IUPAC name
2-Diazonaphthalen-1(2H)-one | |
| Other names
1,2-Naphthoquinone diazide
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| Properties | |
| C10H6N2O | |
| Molar mass | 170.171 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
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Diazonaphthoquinone (DNQ) is a diazo derivative of naphthoquinone. Upon exposure to light, DNQ converts to a derivative that is susceptible to etching. In this way, DNQ has become an important reagent in photoresist technology in the semiconductor industry.[1]
Diazonaphthoquinone sulfonic acid esters are components of common photoresist materials. Such photoresists are used in the manufacture of semiconductors.[2][3][4] In this application DNQs are mixed with Novolac resin, a type of phenolic polymer. The DNQ functions as a dissolution inhibitor. During the masking/patterning process, portions of the photoresist film are exposed to light while others remain unexposed. In the unexposed regions of the resist film, the DNQ acts as a dissolution inhibitor and the resist remains insoluble in the aqueous base developer. In the exposed regions, the DNQ forms a ketene, which, in turn, reacts with ambient water to form a base soluble indene carboxylic acid. The exposed regions of the photoresist film become soluble in aqueous base; thus allowing the formation of a relief image during development.
Chemical reactions
Upon photolysis, DNQ undergoes a Wolff rearrangement to form a ketene. The ketene adds water to form indene-carboxylic acid.[5]
References
- ↑ Dammel, Ralph (1993). Diazonaphthoquinone-based Resists. Int. Soc. Optical Engineering. ISBN 9780819410191.
- ↑ Hinsberg., W. D.; Wallraff, G. M. (2005), "Lithographic Resists", Kirk-Othmer Encyclopedia of Chemical Technology, New York: John Wiley, doi:10.1002/0471238961.1209200808091419.a01.pub2, ISBN 9780471238966, http://onlinelibrary.wiley.com/book/10.1002/0471238961
- ↑ Integrated Laboratory Systems (January 2006). Chemical Information Review Document for Diazonaphthoquinone Derivatives Used in Photoresists (Report). National Toxicology Program. https://ntp.niehs.nih.gov/ntp/htdocs/Chem_Background/ExSumPdf/Photoresists_DNQcmpds2_508.pdf.
- ↑ Henderson, Clifford L.. "Integrated Circuits: A Brief History". Georgia Tech School of Chemical & Biomolecular Engineering. https://henderson.chbe.gatech.edu/Introductions/microlithography%20intro.htm.
- ↑ N. C. de Lucas; J. C. Netto-Ferreira; J. Andraos; J. C. Scaiano (2001). "Nucleophilicity toward Ketenes: Rate Constants for Addition of Amines to Aryl Ketenes in Acetonitrile Solution". J. Org. Chem. 66 (5): 5016–5021. doi:10.1021/jo005752q. PMID 11463250.
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