Dissolution Characteristics of Acidic Groups for 157-nm Resist.

Kishimura, Shinji; Endo, Masayuki; Sasago, Masaru

doi:10.2494/photopolymer.15.625

Cited by 11 publications

(3 citation statements)

References 8 publications

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“…While polystyrene bearing trifluoroisopropanol is insoluble in 0.26 N TMAH, PSTHFA dissolves rapidly at about 6,000 A/sec (close to an average rate of PNBHFA but slower than the rate of 12,000 A/sec reported by the Matsushita group 14 ). What is interesting is that the two NBHFA copolymers containing HFA in every repeat unit dissolve at a much slower rate (13 A/sec) or does not even dissolve in 0.26 N TMAH, while the fastest dissolving HFA polymer is poly(NBHFA sulfone).…”

Section: Dissolution Kinetics Of Pnbhfamentioning

confidence: 75%

Hydrogen bonding and aqueous base dissolution behavior of hexafluoroisopropanol-bearing polymers

Itô

Hinsberg

Rhodes

et al. 2003

Advances in Resist Technology and Processing XX

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The aqueous base dissolution behavior and hydrogen bonding interaction of polymers bearing hexafluoroisopropanol (HFA) as an acid group have been investigated. While pKa of HFA is similar to that of phenol, the dissolution rate of HFA polymers in aqueous base varies from one structure to another. Poly(norbornene hexafluoroisopropanol) (PNBHFA) dissolves in 0.26 tetramethylammonium hydroxide (TMAH) aqueous solution at a rate of 1,500-8,000 A/sec, which is not correlated to the number-average or weight-average molecular weight. Furthermore, PNBHFA exhibits a complex multi-stage dissolution kinetics in 0.21 N TMAH, depending on the molecular weight and molecular weight distribution. Hydrogen bonding of HFA polymers has been investigated using FTIR. Polynorbornene and polystyrene bearing HFA (PNBHFA and PSTHFA) are much less hydrogen-bonded than poly(4-hydroxystyrene) (PHOST). HFAester copolymers tend to have more free OH groups than a HOST/t-butyl acrylate copolymer. The carbonyl bond in 2-trifluoromethylacrylic units is less polarized and therefore less prone to hydrogen bonding with OH than C=O in (meth)acrylate units. The interaction of acid generators with the HFA group can be studied by 19 F NMR. Both ionic iodonium and nonionic imidesulfonate acid generators interact strongly with HFA and inhibit the dissolution of HFA polymers in aqueous base while ionic acid generators are better dissolution inhibitors of phenolic resins.

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Section: Dissolution Kinetics Of Pnbhfamentioning

confidence: 75%

Hydrogen bonding and aqueous base dissolution behavior of hexafluoroisopropanol-bearing polymers

Itô

Hinsberg

Rhodes

et al. 2003

Advances in Resist Technology and Processing XX

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“…The successful polymerization of VBSF with well-retained sulfonyl fluoride groups encouraged us to further explore the PPM of PVBSF based on SuFEx click reactions. − Ideally, PPM of PVBSF by replacement of the fluoride with different nucleophiles could allow a rapid diversification of the polymers. To our delight, the sulfonyl fluoride groups of PVBSF could readily react with various aryl silyl ethers in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) as a catalyst (Figure ).…”

Section: Resultsmentioning

confidence: 99%

“…However, effective and precise PPM normally requires the monomers to possess a modifiable site or functional group with a good balance of stability and reactivity . This consideration led us to the sulfur(VI) fluoride exchange (SuFEx) reaction, which was introduced by Sharpless and co-workers as the new generation of click chemistry. − However, SuFEx remains rarely explored for the synthesis of functional materials through free-radical polymerization, − due to a lack of FSO 2 -containing SuFExable vinyl monomers, even though a number of methods based on SuFEx reactions for the synthesis of polysulfates and polysulfonates via condensation polymerization, − as well as chain-end group transformation have been developed in the past recent years. − On the other hand, the stability of sulfonyl fluoride groups and the high reliability in SuFEx reactions have found applications in chemical biology, − surface functionalization, − as well as the preparation of functional polymers. − …”

Section: Introductionmentioning

confidence: 99%

Atom-Transfer Radical Polymerization of a SuFExable Vinyl Monomer and Polymer Library Construction via SuFEx Click Reaction

Liao

2023

Macromolecules

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The advancement in the synthesis of functional polymeric materials has greatly benefited from the development of functionalized monomers and effective polymerization methods. Here, inspired by the controlled radical polymerization and the new generation of click chemistry, sulfur(VI) fluoride exchange (SuFEx), we introduce a SuFExable vinyl monomer, 4-vinylbenzenesulfonyl fluoride (VBSF), which shows a good balance of stability and reactivity and can readily undergo organocatalytic atom-transfer radical polymerization under visible light with good controls and high end-group fidelity, while retaining the sulfonyl fluoride groups intact. Moreover, poly(VBSF) can be further modified with high efficiency via SuFEx reactions with various aryl silyl ethers, thus allowing a rapid construction of a functional polymer library in a click fashion.

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Fluoropolymers for Proton Exchange Membranes

2014

Polymers for PEM Fuel Cells

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Dissolution Characteristics of Acidic Groups for 157-nm Resist.

Cited by 11 publications

References 8 publications

Hydrogen bonding and aqueous base dissolution behavior of hexafluoroisopropanol-bearing polymers

Hydrogen bonding and aqueous base dissolution behavior of hexafluoroisopropanol-bearing polymers

Atom-Transfer Radical Polymerization of a SuFExable Vinyl Monomer and Polymer Library Construction via SuFEx Click Reaction

Fluoropolymers for Proton Exchange Membranes

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