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Diazonaphthoquinone

Diazonaphthoquinone (DNQ) is a diazo derivative of naphthoquinone. Upon


Diazonaphthoquinone
exposure to light, it undergoes a Wolff rearrangement to form a ketene.[1] This
chemical reaction is exploited with a variety of diazonaphthoquinone derivatives in
the semiconductor industry.

Diazonaphthoquinone sulfonic acid esters are commonly used as components of


photoresist materials for semiconductor manufacturing.[2][3] 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 Names
of the photoresist film are exposed to light while others remain unexposed. In the
IUPAC name
unexposed regions of the resist film, the DNQ acts as a dissolution inhibitor and the
2-Diazo-2H-naphthalen-1-one
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 Other names
soluble indene carboxylic acid. The exposed regions of the photoresist film become 1,2-Naphthoquinone diazide
soluble in aqueous base; thus allowing the formation of a relief image during Identifiers
development. CAS Number 879-15-2

3D model Interactive image


References (JSmol)
ChemSpider 7991089
1. N. C. de Lucas; J. C. Netto-Ferreira; J. Andraos; J. C. Scaiano (2001).
"Nucleophilicity toward Ketenes: Rate Constants for Addition of Amines PubChem 9815339
to Aryl Ketenes in Acetonitrile Solution".J. Org. Chem. 66 (5): 5016– CID
5021. doi:10.1021/jo005752q (https://doi.org/10.1021%2Fjo005752q).
InChI
PMID 11463250 (https://www.ncbi.nlm.nih.gov/pubmed/11463250).
2. Chemical Information Review Document for Diazonaphthoquinone SMILES
Derivatives Used in Photoresists(http://ntp-server.niehs.nih.gov/ntp/htdo Properties
cs/Chem_Background/ExSumPdf/Photoresists_DNQcmpds2_508.pdf) ,
Chemical C10H6N2O
National Toxicology Program, January 2006
formula
3. Integrated Circuits: A Brief History(http://henderson.chbe.gatech.edu/Int
Molar mass 170.17 g·mol−1
roductions/microlithography%20intro.htm)
Except where otherwise noted, data
are given for materials in their
standard state (at 25 °C [77 °F],
100 kPa).
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Infobox references

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This page was last edited on 14 December 2016, at 15:59.

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