Diazonaphthoquinone

Diazonaphthoquinone
Names
	IUPAC name 2-Diazo-2H-naphthalen-1-one
	Other names 1,2-Naphthoquinone diazide
Identifiers
CAS Number	879-15-2 ;
3D model (JSmol)	Interactive image;
ChemSpider	7991089 ;
PubChem CID	9815339;
	InChI InChI=1S/C10H6N2O/c11-12-9-6-5-7-3-1-2-4-8(7)10(9)13/h1-6H Key: URQUNWYOBNUYJQ-UHFFFAOYSA-N ; InChI=1/C10H6N2O/c11-12-9-6-5-7-3-1-2-4-8(7)10(9)13/h1-6H Key: URQUNWYOBNUYJQ-UHFFFAOYAU;
	SMILES O=C(C(C=C2)=[N]=[N])C1=C2C=CC=C1;
Properties
Chemical formula	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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	Infobox references

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 indane-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
Integrated Laboratory Systems (January 2006). Chemical Information Review Document for Diazonaphthoquinone Derivatives Used in Photoresists (PDF) (Report). National Toxicology Program.
Integrated Circuits: A Brief History
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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[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] Integrated Circuits: A Brief History

[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.