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Diazonaphthoquinone

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Diazonaphthoquinone
Names
Preferred IUPAC name 2-Diazonaphthalen-1(2H)-one
Other names 1,2-Naphthoquinone diazide
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C10H6N2O/c11-12-9-6-5-7-3-1-2-4-8(7)10(9)13/h1-6HKey: URQUNWYOBNUYJQ-UHFFFAOYSA-N
  • InChI=1/C10H6N2O/c11-12-9-6-5-7-3-1-2-4-8(7)10(9)13/h1-6HKey: URQUNWYOBNUYJQ-UHFFFAOYAU
SMILES
  • O=C(C(C=C2)==)C1=C2C=CC=C1
Properties
Chemical formula C10H6N2O
Molar mass 170.171 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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.

Diazonaphthoquinone sulfonic acid esters are components of common photoresist materials. Such photoresists are used in the manufacture of semiconductors. 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.

References

  1. Dammel, Ralph (1993). Diazonaphthoquinone-based Resists. Int. Soc. Optical Engineering. ISBN 9780819410191.
  2. 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.
  3. Integrated Laboratory Systems (January 2006). Chemical Information Review Document for Diazonaphthoquinone Derivatives Used in Photoresists (PDF) (Report). National Toxicology Program.
  4. Henderson, Clifford L. "Integrated Circuits: A Brief History". Georgia Tech School of Chemical & Biomolecular Engineering.
  5. 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. S2CID 12123114.
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