Acid catalyzed resist for KrF excimer laser lithography.

Onishi, Yasunobu; Niki, Hirokazu; Kobayashi, Y.; Hayase, Rumiko; Oyasato, Naohiko; Sasaki, Osamu

doi:10.2494/photopolymer.4.337

Cited by 16 publications

(5 citation statements)

References 2 publications

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“…Small molecules that undergo acid-catalyzed deprotection to generate acidic compounds in an acidic or protected polymer matrix have been also employed as a dissolution inhibitor in the design of chemical amplification resists. – Furthermore, the use of small molecules that form amorphous glass (molecular glass), instead of polymers, has attracted a great deal of attention recently as a means to overcome the size-related issues (resolution and LER) in lithography below 30 nm. Polyphenolic compounds – (including calix[4]arenes – ), polyhedral oligomeric silsesquioxane, , cholates, , cyclodextrins, , adamantanes, dendrimers, and fullerenes have been reported as chemically amplified molecular glass resists.…”

Section: Introductionmentioning

confidence: 99%

Characterization and Lithographic Application of Calix[4]resorcinarene Derivatives

et al. 2007

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Calix[4]resorcinarenes were prepared by the condensation of resorcinol and aldehydes (acetaldehyde, benzaldehyde, and 4-isopropylbenzaldehyde), and two isomers, C 4v (ccc) and C 2v (ctt), were separated by fractional crystallization. The products were characterized by NMR and FTIR, and their dissolution rate in aqueous base was measured. The eight hydroxyl groups of the calix[4]resorcinarenes were protected with acid labile t-butoxycarbonyl and t-butoxycarbonylmethyl. The protected calixarenes were thoroughly characterized by differential scanning calorimetry, FTIR, and variable-temperature 1H and 13C NMR. Their interaction with 4-isopropylphenol through hydrogen bonding was investigated by 13C NMR and correlated with their inhibition effect of dissolution of poly(4-hydroxystyrene-co-t-butyl acrylate) in an aqueous base, as studied by quartz crystal microbalance. Finally, the protected calixarenes were employed as a dissolution inhibitor of polyhydroxystyrene-based deep UV and electron beam chemical amplification resists to improve their contrast and performance.

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Section: Introductionmentioning

confidence: 99%

Characterization and Lithographic Application of Calix[4]resorcinarene Derivatives

et al. 2007

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“…The organic soluble TBP becomes aqueous alkali soluble BAP by deprotection of t-BOC to carboxylic acid groups as shown in Scheme 1 and BAP can act as a dissolution promoter. TBP is belong to a compound series of t-Bu esters of aromatic carboxylic acids which have been successfully applied to two-or three-component chemical amplification resist systems [4,6,11,12].…”

Section: Resultsmentioning

confidence: 99%

“…The acid-labile, t-BOC protected dissolution inhibitors in the form of tert-butyl (t-Bu) carbonate or t-Bu ester derived from phenol or benzoic acid functional groups were successfully applied to the three-component positive resist system as follows: t-Bu naphthalene-2-carboxylate and 2-(t-BOC-oxy)naphthalene [8], t-Bu cholate [4], 2,2-bis[4-(t-BOC-oxy)phenyl]propane [9,10], di-t-Bu isophthalate [11], and 2,2-bis[4-(t-BOC-methoxy)phenyl]propane [12]. Other acid-labile compounds such as acetals and prthoesters were also used in the formulations of highly sensitive positive resists [3].…”

Section: Introductionmentioning

confidence: 99%

A new chemical amplification resist system based on novolac and t-BOC protected phosphazene as a dissolution inhibitor.

Ahn

Kang

Kim

et al. 1992

J. Photopol. Sci. Technol.

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t-BOC protected hexakis(4-t-BOC-phenoxy)cyclotriphosphazene, TBP, was synthesized from a semiinorganic phosphazene compound and its acid-catalyzed thermal deprotection was utilized in the design of a three-component positive resist system based on the combined principles of chemical amplification and dissolution inhibition. The new resist system, PTPNS(NRI TBP/PAG), is formulated with novolac resin (NR), TBP and a photoacid generator (PAG). The dissolution characteristics of PTPNS in alkaline development are ideally suited for application to positive type resists which are based on a dissolution inhibition mechanism. The t-BOC protected TBP of the PTPNS resist system effectively acts as an acid-labile dissolution inhibitor of novolac resin when TBP concentration is more than 10 % by weight. As a representative, PTPNS(100/15/5) (by weight parts) exhibited high sensitivity in the range of 20 to 25 mJ/cm2 with contrast of 5 after exposure at 250nm light and PEB treatment at 100 to 130°C. Appropriately formulated PTPNS resist rendered positive-tone patterns down to sub-half micron with high sensitivity when the resist was exposed to KrF excimer laser or electron beam and developed with 2.38 wt% tetramethylamonium hydroxide solution.

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“…Thus, PHOST partially protected with acid-labile groups has become the focal point of the positive resist research (Figure 10) [52][53][54][55]. This approach circumvents some of the above mentioned problems (excess shrinkage, cracking, poor adhesion).…”

Section: Evolution Of Positive Deep Uv Resistsmentioning

confidence: 99%

“…Alternative base soluble resins were sought (such as the ones without tBOC protection in Fig. 9) but PHOST has established its position as a matrix In addition to the two-component resist system composed of a partially protected PHOST and a PAG, a three-component approach involving incorporation of an additional acid-labile small dissolution inhibiting compound ( Figure 12) has been investigated quite extensively, especially in Japan [53,[58][59][60].…”

Section: Evolution Of Positive Deep Uv Resistsmentioning

confidence: 99%

Evolution and Progress of Deep UV Resist Materials.

Itô

1998

J. Photopol. Sci. Technol.

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It has been almost thirty years since the first deep UV exposure was carried out and almost twenty five years since the term "deep UV lithography" was coined. Although resist systems classified as "chemical amplification resists" are the workhorse for the 248 nm deep UV lithography, the resist materials have evolved significantly in the realm of deep UV lithography as well as within the boundary of chemical amplification. This paper describes the evolution and progress of the deep UV (248-193 nm) positive resist materials that have occurred in the last quarter century.

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Acid catalyzed resist for KrF excimer laser lithography.

Cited by 16 publications

References 2 publications

Characterization and Lithographic Application of Calix[4]resorcinarene Derivatives

Characterization and Lithographic Application of Calix[4]resorcinarene Derivatives

A new chemical amplification resist system based on novolac and t-BOC protected phosphazene as a dissolution inhibitor.

Evolution and Progress of Deep UV Resist Materials.

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