Negative Resists Using Acid-Catalyzed Dehydration of Phenylcarbinols:  Correlation between Chemical Structure and Resist Sensitivity

Abstract

A series of phenylcarbinols have been evaluated as components of chemically amplified resists used for KrF excimer laser lithography. The character of the carbon atom to which the hydroxyl group is bonded to determines the insolubilization reactions, leading to differences in sensitivity. Resists using tertiary phenylcarbinol, which converts into polymeric compounds, exhibits the highest sensitivity while the resists using primary phenylcarbinol, which cross-links the phenolic resin, has the lowest sensitivity. Properties, such as sensitivity and chemistry, of the resist containing the secondary phenylcarbinol groups lie between those of the primary and tertiary phenylcarbinol containing resists.

Negative Electron Beam Resists Using Ring-Chain Tautomerism of Benzoic Acid Derivatives

“…[4,5,6] In this article we describe a newly developed resist that uses the ring-chain tautomerism of oacetylbenzoic acid. The formulation, lithographic performance, and insolubilization mechanism of the new resist are discussed.…”

Negative EB Resist Materials Using Anisotropic Acid-Diffusion Based on Acid-Catalyzed Dehydration of Phenylcarbinols.

“…We developed negative deep-UV resists based on the polarity change reactions such as pinacol rearrangement, [6,7] phenylcarbinol etherification, [8] and phenylcarbinol dehydration, which have low activation energy compared to acidhardening reactions. [9][10][11] In the course of the development of the deep-UV resists, we found that the resist using phenylcarbinols dehydration exhibited high sensitivity, and small pattern-width dependence on PEB temperature. [ 10] Therefore, we expected that the resist using phenylcarbinols would exhibit a good lithographic performance in terms of sensitivity and CD control.…”

“…[9][10][11] In the course of the development of the deep-UV resists, we found that the resist using phenylcarbinols dehydration exhibited high sensitivity, and small pattern-width dependence on PEB temperature. [ 10] Therefore, we expected that the resist using phenylcarbinols would exhibit a good lithographic performance in terms of sensitivity and CD control.…”

“…were synthesized by Grignard reaction as the same synthetic scheme described in the previous paper. [ 10] The synthesized phenylcarbinols are shown in Table 1…”

Negative electron-beam nanofabrication resist using acid-catalyzed protection of polyphenol provided by phenylcarbinol

“…1 Also we have reported negative resists that use a cross-linking reaction between a bisazide and a phenolic resin for nanofabrication. [7][8][9] We also discuss the formulation, lithographic performance, and insolubilization mechanism of the new resist. However, the sensitivity of the resist ͑150 C/cm 2 at 50 kV͒ is still not sufficient for efficient fabrication of nanostructures.…”