Diazonaphthoquinone

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Diazonaphthoquinone
Identifiers
CAS number 879-15-2 YesY

Jmol-3D images {{#if:O=C(C(C=C2)=[N]=[N])C1=C2C=CC=C1|Image 1
Properties
Molecular formula C10H6N2O
Molar mass 170.17 g mol−1
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

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


References

  1. N. C. de Lucas, J. C. Netto-Ferreira, J. Andraos, and 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. 
  2. Chemical Information Review Document for Diazonaphthoquinone Derivatives Used in Photoresists, National Toxicology Program, January 2006
  3. Integrated Circuits: A Brief History
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