New Design for Self-Developing Imaging Systems Based on Thermally Labile Polyformals

Fréchet, Jean M. J.; Willson, C. Grant; Iizawa, Takashi; Nishikubo, Tadatomi; Igarashi, K.; Fahey, James T.

doi:10.1021/bk-1989-0412.ch007

Cited by 15 publications

(7 citation statements)

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“…Polycarbonates, polyesters, and polyethers reported by Frechet et al [19][20][21] are degraded to small molecules by reaction with acids. Their initiation mode may be considered as case 1 but there is no depolymerization step in these systems as opposed to the PPA degradation.…”

Section: Introductionmentioning

confidence: 99%

Chemical amplification based on acid-catalyzed depolymerization.

Itô

England

Ueda

1990

J. Photopol. Sci. Technol.

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The chemical amplification concept proposed in 1982 to support high resolution short wavelength lithographic technologies that demand highly sensitive advanced resist systems is based on acid-catalyzed crosslinking, deprotection, and depolymerization reactions. Each approach has shown a tremendous progress. In this paper is reviewed the depolymerization concept for the design of sensitive positive resist systems formulated with triarylsulfonium salt acid generators.Three modes of the initiation of acid-catalyzed depolymerization are discussed; (1) attack of acids onto backbone oxygens as exemplified by depolymerization of polyphthalaldehyde (PPA), (2) scission of pendant ester groups followed by depolymerization with poly(a-acetoxystyrene ) (PACOST) as an example, and (3) unzipping from the polymer ends as demonstrated by depolymerization of cationically obtained polyp-hydroxy-a-methylstyrene) (pPHOMS). The positive resist systems based on depolymerization of PPA derivatives include a thermally-developable OZ reactive ion etch (RIE) barrier resist for use in the bilayer scheme and the use of PPA as a polymeric dissolution inhibitor for novolac resins. The deesterification of PACOST results in formation of poly(phenylacetylene) (PPA) and simultaneous depolymerization to provide positive images upon development with xylenes, which is briefly discussed. Cationically prepared pPHOMS exhibits 80 % thickness loss at ca. 1 mJ/cm2 upon postbake at 130°C whereas anionic pPHOMS and cationic meta-PHOST are very stable toward acidolysis, indicating that the depolymerization propagates from the termination side of the chain.

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Section: Introductionmentioning

confidence: 99%

Chemical amplification based on acid-catalyzed depolymerization.

Itô

England

Ueda

1990

J. Photopol. Sci. Technol.

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“…The initial work was extended from polycarbonates to polyethers in the following years. [1][2][3][4][5][6][7][8][9] However, last results in this direction were published in 1992 by Yoshiaki Inaki. [ 10] Common chemically amplified DUV photoresists are based on polymers with a backbone consisting of carbon-carbon bonds.…”

Section: Chemically Amplified Main Chain Scission Of Polymersmentioning

confidence: 99%

“…These findings are in good agreement with the results found by the groups of Willson and Frechet. [1][2][3][4][5][6][7][8][9] 3. Line Edge Roughness…”

Section: Chemically Amplified Main Chain Scission Of Polymersmentioning

confidence: 99%

Chemically Amplified Main Chain Scission: New Concept to Reduce Line Edge Roughness and Outgassing.

Eschbaumer

Heusinger

Hohle

et al. 2002

J. Photopol. Sci. Technol.

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“…Incorporation of 70% TMBA afforded an increase in T g from 88 °C to 113 °C. The 1,4-dihydroxy-2-cyclohexenols were prepared under phase-transfer conditions with dibromomethane (23). These polymers were evaluated as self-developable resists.…”

Section: Poly(formal)smentioning

confidence: 99%

A Survey of Some Recent Advances in Step-Growth Polymerization

Labadie

Hedrick

Ueda

1996

Step-Growth Polymers for High-Performance Materials

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The field of step-growth polymers encompasses many polymer structures and polymerization reaction types. This chapter attempts to cover topics in step--growth polymerization outside of the areas reviewed in the other introductory chapters in this book, i.e., poly(aryl ethers), dendritic polymers, high--temperature polymers and transition-metal catalyzed polymerizations. Polyamides, polyesters, polycarbonates, poly(phenylene sulfides) and other important polymer systems are addressed. The chapter is not a comprehensive review but rather an overview of some of the more interesting recent research results reported for these step-growth polymers, including new polymerization chemistries and mechanistic studies. Aromatic PolyamidesAromatic polyamides (aramids) are important in the commercial fibers industry because of their high tensile strength and good flame resistance. The demand for these materials is increasing as new applications are found. One example is their use in composites where high-use temperatures, light weight, chemical resistance, and dimensional stability are crucial.The most widely employed synthetic route to aramids is based on the polycondensation of dicarboxylic acids with diamines in the presence of condensing agents. Good reviews on the synthesis of aramids have recently appeared (1-3). Recently, promising alternative synthetic routes to aramids have been reported and are described herein.These include the polycondensation of N-silylated diamines with diacid chlorides, the addition--elimination reaction of dicarboxylic acids with diisocyanates, and the palladium-catalyzed carbonylation polymerization of aromatic dibromides, aromatic diamines and carbon monoxide.The synthesis of aramids from N-silylated amines has been employed because N-silylated aromatic amines show higher reactivity relative to the parent diamines and the resulting trialkylsilyl halide does not lower the reactivity of unreacted amine functionality as is the case with amine protonation

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New Design for Self-Developing Imaging Systems Based on Thermally Labile Polyformals

Cited by 15 publications

References 0 publications

Chemical amplification based on acid-catalyzed depolymerization.

Chemical amplification based on acid-catalyzed depolymerization.

Chemically Amplified Main Chain Scission: New Concept to Reduce Line Edge Roughness and Outgassing.

A Survey of Some Recent Advances in Step-Growth Polymerization

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