Degradation of Polymers for Resist Using Microbubbles on Ozonized Water

Matsuura, Kohei; Nishiyama, Takashi; Sato, Eriko; Yamamoto, Masashi; Takahashi, Masayoshi; Koike, Kunihiko; Horibe, Hideo

doi:10.2494/photopolymer.28.299

Cited by 9 publications

(6 citation statements)

References 17 publications

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“…As demonstrated in our earlier work [15,16], which are produced together with H and O radicals [18]. According to some findings [19][20][21][22][23], OH radicals actually have higher reactivity to benzene rings than either H or O radicals. The decrease over 1.5% might be attributable to the decreased production rate of H radicals by the catalytic poisoning of the catalyst surface by O atoms.…”

Section: Resultsmentioning

confidence: 74%

Removal of Polymers for KrF and ArF Photoresist Using Hydrogen Radicals Containing a Small Amount of Oxidizing Radicals

Yamamoto

Taki

Sunada

et al. 2018

J. Photopol. Sci. Technol.

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Photoresist removal method using hydrogen radicals, which are produced on a tungsten hot-wire catalyst, is effective to resolve some environmental and industrial problems in conventional methods for the fabrication of electronic devices. However, its removal rate is not as good as that of the conventional ones. We have previously described that the removal rate of a positive-tone novolac photoresist is enhanced by the addition of a small amount of oxygen gas to the atmosphere, in which hydrogen radicals are produced. Oxidizing radicals, such as OH and O radicals, can be produced together with H radicals. In present study, we examined the effects of oxygen addition on base polymers of KrF and ArF photoresists: the former is poly(vinyl phenol) (PVP), and the latter is poly(methyl methacrylate) (PMMA). Effects of oxygen addition on PVP was confirmed, as was found for the novolac photoresist. On the other hand, the effects on PMMA were different from the cases of the novolac photoresist and PVP. Results were ascribed to the presence or absence of benzene rings, the properties of polymers and the reactivity of oxidizing radicals.

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Section: Resultsmentioning

confidence: 74%

Removal of Polymers for KrF and ArF Photoresist Using Hydrogen Radicals Containing a Small Amount of Oxidizing Radicals

Yamamoto

Taki

Sunada

et al. 2018

J. Photopol. Sci. Technol.

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“…Photoresist removal processes using O [4][5][6][7] and OH radicals [20][21][22][23] have been reported as removal methods using radicals other than H. Although OH radicals are highly reactive, 20,24) only a few studies have been carried out regarding their use for photoresist removal. In these studies, OH radicals are produced using plasma 20,21) or microbubbles in ozonized water.…”

Section: Introductionmentioning

confidence: 99%

Oxygen additive amount dependence of rate of photoresist removal by H radicals generated on a tungsten hot-wire catalyst

Yamamoto

Umemoto

Ohdaira

et al. 2016

Jpn. J. Appl. Phys.

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We examined an environmentally friendly photoresist removal method using radicals produced by decomposing mixtures of hydrogen and oxygen on a hot tungsten catalyst. The photoresist removal rate increased with the oxygen additive amount (the flow rate ratio of oxygen to hydrogen) up to an optimal amount and then decreased gradually. When the catalyst temperature was 1600 °C, the optimal oxygen additive amount was 1.0% and the removal rate was 1.7 times higher than that in the pure hydrogen system. At 2000 °C, the optimal amount increased to 2.5% but the increase ratio decreased by 1.3 times. At high catalyst temperatures, the absolute removal rate as well as the optimal oxygen additive amount is high, but the increase ratio is low. At the optimal oxygen additive amount, H, O, and OH radicals may exert their effects together to decompose photosensitive polymers.

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“…Thus, it has been demonstrated that the two functional repeating units incorporated in the main chain of PMAD, i.e., the anhydride group and the double bond, can be orthogonally used for the crosslinking and de‐crosslinking, respectively. Ozone degradation is one of useful methods for the degradation, surface cleaning, modification, and functionalization of polymers . In this paper, we report the crosslinking reactions of PVA and poly(vinyl acetate) (PVAc) as the precursor of PVA, using the alternating copolymers of MAn and DMPD, i.e., poly(MAn‐ alt ‐DMPD) (PMAD) as the polyfunctional crosslinker (Scheme ).…”

Section: Introductionmentioning

confidence: 99%

Crosslinking of poly(vinyl alcohol) and poly(vinyl acetate) using poly(maleic anhydride‐alt−2,4‐dimethyl‐1,3‐pentadiene) as polyfunctional crosslinker and decrosslinking by ozone degradation

Lou

Okamura

Matsumoto

2016

J of Applied Polymer Sci

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Crosslinking and decrosslinking reactions of poly(vinyl alcohol) (PVA) and poly(vinyl acetate) (PVAc) using an alternating copolymer of maleic anhydride and 2,4‐dimethyl‐1,3‐pentadiene (PMAD) as the polyfunctional crosslinker and subsequent ozone degradation are reported. PVA and PVAc are heated at 200 °C for 0.5 to 3 h in the presence of 5 to 30 wt % of PMAD in the solid state to obtain the corresponding crosslinked polymers. The reactions of a hydroxy group of PVA and an acetate group of PVAc with an anhydride group of PMAD slowly proceed to give insoluble polymers with a loose crosslinking structure. Almost no change in the thermal decomposition temperatures and the IR spectra is observed during the crosslinking reactions. The crosslinked PVA produces hydrogels with a high swelling ratio of 500 to 1700%, which are readily degradable during a reaction with ozone in water at 0 °C. © 2016 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2017, 134, 44229.

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Degradation of Polymers for Resist Using Microbubbles on Ozonized Water

Cited by 9 publications

References 17 publications

Removal of Polymers for KrF and ArF Photoresist Using Hydrogen Radicals Containing a Small Amount of Oxidizing Radicals

Removal of Polymers for KrF and ArF Photoresist Using Hydrogen Radicals Containing a Small Amount of Oxidizing Radicals

Oxygen additive amount dependence of rate of photoresist removal by H radicals generated on a tungsten hot-wire catalyst

Crosslinking of poly(vinyl alcohol) and poly(vinyl acetate) using poly(maleic anhydride‐alt−2,4‐dimethyl‐1,3‐pentadiene) as polyfunctional crosslinker and decrosslinking by ozone degradation

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