A practical route for the preparation of poly(4-hydroxystyrene), a useful photoresist material

Nasrullah, J. Mohammed; Raja, S.; Vijayakumaran, K.; Dhamodharan, R.

doi:10.1002/(sici)1099-0518(20000201)38:3<453::aid-pola9>3.0.co;2-6

Cited by 40 publications

(18 citation statements)

References 26 publications

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“…9,20 Several copolymers, as summarized in Table 1, with varying degrees of acetylation, briefly referred to as ACPS-co-PS, were synthesized by varying the concentration of acetyl chloride. Initially, commercially available polystyrene (PS; Mn = 145,800; PDI = 1.3) was used for the acetylation reaction.…”

Section: Resultsmentioning

confidence: 99%

“…1 H-NMR, 13 C-NMR, and other spectroscopic data characteristic of ACPS were previously reported. 4,9 From the ratio of the integrated areas under the aliphatic protons (six H's) and the aromatic protons (four H's) the extent of acetylation was evaluated. For the quantitatively acetylated PS [ACPS] it was 1.5:1.…”

Section: Resultsmentioning

confidence: 99%

“…The other spectroscopic data of ACPS-co-PS were consistent with those reported earlier for ACPS. 9,20 The synthesis of propionylated, butroylated, and benzoylated PS was also performed according to the methodology used for acetylation. The general synthetic procedure is presented in Scheme 1 and the list of polymers synthesized are given in Table 1.…”

Section: Resultsmentioning

confidence: 99%

“…4,9 Acetylated copolymers of desired extent of acetylation were obtained by varying the amount of acetylating reagent. Similar procedure was adopted for the synthesis of PrPS-co-PS, BuPS-co-PS and BPS-co-PS at desired extent of acylation by varying the amount of different acylating agents were obtained as given in the Scheme 1.…”

Section: Synthesis Of Copolymers Of Acylated Polystyrenesmentioning

confidence: 99%

“…Significant advances have been made by Dhamodharan et al in functionalizing PS at the para position without side reactions as well as crosslinking. [2][3][4][5][6][7][8][9][10] Almost all chemically amplified resists optimized for DUV lithography utilize homo-and co-polymers derived from 4-hydroxystyrene (4-HS) as the materials of choice. [11][12][13][14] Some attempts have also been made for synthesizing non-PHS based polymers for DUV such as poly(4-(1-hydroxy-1-phenylethyl)styrene).…”

Section: Introductionmentioning

confidence: 99%

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Poly(4-(1-hydroxyalkyl)styrene based photoresist materials: design, synthesis, and their lithographic performance

Nasrullah

Dhamodharan

2006

SPIE Proceedings

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Several synthetic approaches are available to make photoresist polymers for deep UV (DUV) lithography. Two approaches were widely used in semiconductor manufacturing: i) direct polymerization of corresponding monomers by (controlled) radical, (living) ionic polymerization ii) thermal or chemical catalyzed deprotection or protection of the macromolecules. The latter approach which is also called polymer modification chemistry (PMC) or polymer analogous chemistry offers several advantageous over the direct polymerization approach. In this presentation, we will provide an overview on the preparation and basic lithographically important characterization of new polymers based on poly(4-(1-hydroxyalkyl)styrene-co-styrene) [Poly(4-HAS-co-S)]. These polymers were synthesized for the first time by PMC and this methodology is an simple alternative for the synthesis of poly(4-HAS-co-S) than conventionally used synthetically challenging free radical or low temperature anionic polymerization of the protected monomer. We have synthesized high and low molecular weight (Mn) polymers with mole fraction of functional group ranging from partial to complete functionalization. Several formulations based on poly(4-HAS-co-S) were developed and tested for negative tone imaging at DUV lithography. Lithographic performance of these polymers at DUV lithography will be compared with their molecular weight and mole fraction of functional groups.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Synthesis Of Copolymers Of Acylated Polystyrenesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Poly(4-(1-hydroxyalkyl)styrene based photoresist materials: design, synthesis, and their lithographic performance

Nasrullah

Dhamodharan

2006

SPIE Proceedings

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Palladium‐Catalyzed Solid‐Phase Synthesis of Allylic Amines

Brown

Fisher

2012

Solid‐Phase Organic Syntheses

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Fluorinated Tetraarylethenes: Universal Tags for the Synthesis of Solid State Luminogens

et al. 2022

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The aggregation-induced emission properties of tetraarylethenes (TAEs) have led to numerous applications in chemistry, biology, and materials science. Herein, we describe two fluorinated tetraarylethenes, which can be employed as universal tags for the synthesis of solid state luminogens. The tags are accessible in one or two steps from commercially available starting materials. Facile coupling reactions with ubiquitous substrates such as thiols, alcohols, amines, phosphines, aldehydes, and enamines allow preparing a wide range of TAE conjugates, including tagged amino acids, peptides, carbohydrates, steroids, and commercial polymers.

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A practical route for the preparation of poly(4-hydroxystyrene), a useful photoresist material

Cited by 40 publications

References 26 publications

Poly(4-(1-hydroxyalkyl)styrene based photoresist materials: design, synthesis, and their lithographic performance

Poly(4-(1-hydroxyalkyl)styrene based photoresist materials: design, synthesis, and their lithographic performance

Palladium‐Catalyzed Solid‐Phase Synthesis of Allylic Amines

Fluorinated Tetraarylethenes: Universal Tags for the Synthesis of Solid State Luminogens

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