Diazonaphthoquinone

Diazonaphthoquinone

Names
IUPAC name 2-Diazo-2H-naphthalen-1-one
Other names 1,2-Naphthoquinone diazide
Identifiers
CAS Number	879-15-2 Y
3D model (Jmol)	Interactive image
ChemSpider	7991089 N
PubChem	9815339
InChI InChI=1S/C10H6N2O/c11-12-9-6-5-7-3-1-2-4-8(7)10(9)13/h1-6H N Key: URQUNWYOBNUYJQ-UHFFFAOYSA-N 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	170.17 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
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