Diazonaphthoquinone
Names | |
---|---|
IUPAC name
2-Diazo-2H-naphthalen-1-one | |
Other names
1,2-Naphthoquinone diazide | |
Identifiers | |
879-15-2 | |
3D model (Jmol) | Interactive image |
ChemSpider | 7991089 |
PubChem | 9815339 |
| |
| |
Properties | |
C10H6N2O | |
Molar mass | 170.17 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
verify (what is ?) | |
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
- ↑ 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.
- ↑ Chemical Information Review Document for Diazonaphthoquinone Derivatives Used in Photoresists, National Toxicology Program, January 2006
- ↑ Integrated Circuits: A Brief History