Dismiss
InnovationQ will be updated on Sunday, Oct. 22, from 10am ET - noon. You may experience brief service interruptions during that time.
Browse Prior Art Database

N-(pentafluorobenzenesulfonoxy)Phthalimide--Synthesis and Characterization as a Non-ionic Photoacid Generator

IP.com Disclosure Number: IPCOM000108401D
Original Publication Date: 1992-May-01
Included in the Prior Art Database: 2005-Mar-22
Document File: 1 page(s) / 40K

Publishing Venue

IBM

Related People

DiPietro, R: AUTHOR [+4]

Abstract

Phthalimido triflate (PIT) can be used as a source of photolytically-generated acid for photoresist applications. However, drawbacks with this compound make desirable the development of alternatives to PIT. The principle focus of this research effort described here was to modify the acid portion of the molecule while retaining the phthalimide. A number of PIT analogs were prepared with this strategy in mind. These analogs included the mesylate, tosylate, brosylate (m- and p-), tresylate (trifluoroethylsulfonate), trifluoroacetate, dinitrophenoxy, and pentafluorobenzenesulfonate (pebsyl). Each of these compounds, with the exception of the pebsyl phthalimide, suffered from some deficiency. The pebsyl phthalimide, however, was found to have a reduction potential (0.

This text was extracted from an ASCII text file.
This is the abbreviated version, containing approximately 100% of the total text.

N-(pentafluorobenzenesulfonoxy)Phthalimide--Synthesis and Characterization as a Non-ionic Photoacid Generator

      Phthalimido triflate (PIT) can be used as a source of
photolytically-generated acid for photoresist applications. However,
drawbacks with this compound make desirable the development of
alternatives to PIT.  The principle focus of this research effort
described here was to modify the acid portion of the molecule while
retaining the phthalimide.  A number of PIT analogs were prepared
with this strategy in mind.  These analogs included the mesylate,
tosylate, brosylate (m- and p-), tresylate (trifluoroethylsulfonate),
trifluoroacetate, dinitrophenoxy, and pentafluorobenzenesulfonate
(pebsyl).  Each of these compounds, with the exception of the pebsyl
phthalimide, suffered from some deficiency.  The pebsyl phthalimide,
however, was found to have a reduction potential (0.93V) and a
preliminary UV lithographic response equivalent to PIT. Pebsyl
phthalimide has also been successfully employed in photoresist
compositions specifically designed for deep-UV microlithography.
Experiments also showed pebsyl phthalimide to be superior to
triphenylsulfonium triflate as a photoacid generator.

      The synthesis of pebsyl phthalimide is straightforward and
results in very pure material in good yield after one
recrystallization.  It is quite amenable to scale-up at its present
stage of development.

      Disclosed anonymously.