A Novel Polymer for a 193-nm Resist.

Nozaki, Koji; Watanabe, Keiji; Yano, Ei; Kotachi, Akiko; Takechi, Satoshi; Hanyu, Isamu

doi:10.2494/photopolymer.9.509

Cited by 42 publications

(37 citation statements)

References 5 publications

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“…2-methyl-2-adamantyl methacrylate (MAdMA) was prepared using previously published methods. [3] Methacryloyl chloride was distilled under reduced pressure. Methylene chloride and triethylamine were distilled over CaH2.…”

Section: Experimental 21 Materialsmentioning

confidence: 99%

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New Protective Groups in Alicyclic Methacrylate Polymers for 193-nm Resists.

Nozaki

Yano

1997

J. Photopol. Sci. Technol.

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Section: Experimental 21 Materialsmentioning

confidence: 99%

“…[1][2][3][4] The resist is comprised of a poly (MLMA-co-MAdMA) ( Fig. 1), which contained mevalonic lactone and 2-methyl-2-adamantanol as protective groups for carboxylic acid, and 2 wt% of triphenylsulfonium triflate as a photoacid generator (PAG).…”

Section: Introductionmentioning

confidence: 99%

New Protective Groups in Alicyclic Methacrylate Polymers for 193-nm Resists.

Nozaki

Yano

1997

J. Photopol. Sci. Technol.

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“…[4] In very short order following these three critical findings, several acrylic (or acryliccyclic olefin hybrid) resist approaches have been published which combine imaging performance with plasma etch resistance, most notably from AT&T [5], NEC [6] and Fujitsu. [7] The majority of recently published work on 193nm SLRs involves the design of new etch resistant polymers, focusing on new backbone polymer chemistry, [5,8] alicyclic pendant groups, [6] and acid-labile protecting groups. [7,8] For example, Wallow and coworkers at AT&T have prepared new resist materials from the free radical alternating copolymerization of norbornene and malefic anhydride.…”

Section: Introductionmentioning

confidence: 99%

“…[7] The majority of recently published work on 193nm SLRs involves the design of new etch resistant polymers, focusing on new backbone polymer chemistry, [5,8] alicyclic pendant groups, [6] and acid-labile protecting groups. [7,8] For example, Wallow and coworkers at AT&T have prepared new resist materials from the free radical alternating copolymerization of norbornene and malefic anhydride. [5 ] A joint effort from IBM, University of Texas and BF Goodrich has produced new resists with significantly improved plasma etch resistance from the addition polymerization of norbornene derivitives.…”

Section: Introductionmentioning

confidence: 99%

“…[5 ] A joint effort from IBM, University of Texas and BF Goodrich has produced new resists with significantly improved plasma etch resistance from the addition polymerization of norbornene derivitives. [8, 1 1] Recently, investigations of protecting group chemistry at both IBM [8] and Fujitsu [7] have emphasized the importance of alicyclic protecting groups to provide dualfunction (etch resistance and dissolution switching) in 193nm resists. Workers at NEC have disclosed a variation of this theme, with alicyclic esters bearing deprotectable side groups.…”

Section: Introductionmentioning

confidence: 99%

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The Influence of Photoacid Structure on the Design and Performance of 1 93-nm Resists.

Allen

Opitz

Larson

et al. 1997

J. Photopol. Sci. Technol.

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The impact of photoacid generator (PAG) structure has been largely ignored for 193 nm single layer resists. Most published work to date has involved the use of triflic or metallic (antimonate or arsenate) photoacids. The importance of the PAG structure on the performance of 193nm resists is magnified in comparison to 248nm positve resists in use today, due to the absence of the electron-transfer sensitization pathway in the non-phenolic polymers in use in 193nm resists. Additionally, with the realtively low reactivity (high-bake) protecting groups that we (and others) employ in our resist design, greater control of photoacid evaporation and diffusion are required. In this paper, we document the negative consequences of triflic acid on 193nm resist performance, including data on acid volatility and the impact of apparent diffusion. Model resists based on relatively hydrophobic polymers amplify the impact of triflic acid volatility on the degredation of performance in 193nm resists. Acid generators which combine high reactivity, low photoacid volatility, and improved resolution will be described. The basic chemical skeleton of these improved 193nm photoacid generators is shown in Figure 1. These iodonium sulfonates combine excellent thermal stability, dissolution inhibition, clean synthesis and readily tailorable photoacid size and strength. Most importantly, iodonium sulfonates based on haloalkyl and activated aromatic sulfonic acids efficiently deprotect t-butyl esters and other high activation protecting groups when formulated in 193nm resist materials and exposed to 193nm light.

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4-(tert-Butoxycarbonyloxy)benzylp-toluenesulfonates as acid amplifiers applicable to chemically amplified photoresists

Ito¹,

Ichimura²

2000

Macromol. Chem. Phys.

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A Novel Polymer for a 193-nm Resist.

Cited by 42 publications

References 5 publications

New Protective Groups in Alicyclic Methacrylate Polymers for 193-nm Resists.

New Protective Groups in Alicyclic Methacrylate Polymers for 193-nm Resists.

The Influence of Photoacid Structure on the Design and Performance of 1 93-nm Resists.

4-(tert-Butoxycarbonyloxy)benzylp-toluenesulfonates as acid amplifiers applicable to chemically amplified photoresists

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