Negative resists for i-line lithography utilizing acid-catalyzed intramolecular dehydration reaction

Ueno, Takashi; Uchino, Shou–ichi; Hattori, Keiko; Onozuka, Toshihiko; Shirai, Shoji; Moriuchi, Noboru; Hashimoto, Michiaki; Koibuchi, Shigeru

doi:10.1117/12.175334

Cited by 8 publications

(4 citation statements)

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“…The resist is composed of novolak, bis(a-hydroxypropyl)benzene and naphthoylmethyltetramethylenesulfonium salt. [ 11 ] The dissolution rate characteristic showed the similar behavior as described for silanol condensation.…”

Section: Chemical Amplification Resistssupporting

confidence: 49%

Chemical amplification resists for future lithography.

Ueno

Shiraishi

Uchino

et al. 1994

J. Photopol. Sci. Technol.

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The technologies for future lithography have been proposed, such as i-line phase-shifting lithography, deep-UV lithography and electron beam lithography. We have proposed several types of chemical amplification resist systems for future lithography. These are based on the change in dissolution rate by acid catalyzed reaction for aqueous development: dissolution inhibitor to dissolution promoter for positive resists and the reverse for negative resist. Deprotection reaction of tetrahydropyranyl protected poly (hydroxystyrene) is used for positive resists. Silanol condensation reaction by acid catalyzed reaction was applied to negative resists. Pinacol rearrangement, etherification and intramolecular dehydration of carbinols can also be used for negative resists.

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Section: Chemical Amplification Resistssupporting

confidence: 49%

Chemical amplification resists for future lithography.

Ueno

Shiraishi

Uchino

et al. 1994

J. Photopol. Sci. Technol.

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“…10. These changes in JR absorbance indicate the formation of p-diisopropenylbenzene (PDIPB) by acid-catalyzed intramolecular dehydration of the 2-hydroxy-isopropyl group of Diol-1 [17]. To clarify the insolubilization mechanism of the Diol-1 resist, we measured the dissolution rates of the PDIPB-doped novolak resin in an aqueous 2.38-wt% tetramethylammonium hydroxide solution.…”

Section: Reaction Mechanismmentioning

confidence: 99%

“…When combined with an appropriate polymer matrix, this resist system can show high sensitivity. We have reported negative-resist systems based on acid-catalyzed polarity-change reactions such as silanol condensation [12,13], pinacol rearrangement [14,15], carbinol etherification [16], and intramolecular dehydration of phenylcarbinol using onium salts as photoacid generators [17]. Ito et al of IBM have independently developed resist systems based on the pinacol and intramolecular dehydration reactions [18,19].…”

Section: Introductionmentioning

confidence: 99%

Negative resists for electron-beam lithography utilizing acid-catalyzed intramolecular dehydration of phenylcarbinol

et al. 1996

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Acid-catalyzed intramolecular dehydration of phenylcarbinol is used to design highly sensitive negative resists for electron beam lithography. Of the phenylcarbinol resists evaluated in this study, the resist composed of 1,3-bis(a-hydroxyisopropyl)benzene (Diol-1), m/p-cresol novolak resin, and diphenyliodonium triflate (DIT) shows the best lithographic performance in terms of sensitivity and resolution. Fine O.25-j.tm line-and-space patterns were formed by using the resist containing Diol-1 with a dose of 3.6 .tC/cm2 in conjunction with a 50 kV electron beam exposure system.

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“…Photoresists using primary phenylcarbinols and their derivatives as latent electrophiles have been investigated in detail by Fréchet et al. − According to their studies, primary phenylcarbinols are converted into benzyl cations, which cross-link the matrix polymer through acid-catalyzed reactions. On the other hand, Ueno et al have examined tertiary phenylcarbinols as a component of highly sensitive and high contrast resist for I-line phase shift photolithography …”

Section: Introductionmentioning

confidence: 99%

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

et al. 1996

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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.

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Negative resists for i-line lithography utilizing acid-catalyzed intramolecular dehydration reaction

Cited by 8 publications

References 0 publications

Chemical amplification resists for future lithography.

Chemical amplification resists for future lithography.

Negative resists for electron-beam lithography utilizing acid-catalyzed intramolecular dehydration of phenylcarbinol

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

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