Cycloolefin/cyanoacrylate (COCA) copolymers for 193-nm and 157-nm lithography

Dammel, Ralph R.; Sakamuri, Raj; Lee, Sang-Ho; Rahman, Dalil; Kudo, Takanori; Romano, Andrew; Rhodes, Larry F.; Lipian, John-Henry; Hacker, Cheryl; Barnes, Dennis A.

doi:10.1117/12.474196

Cited by 8 publications

(3 citation statements)

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“…Another discovery, that 2‐trifluoromethylacrylic (TFMA) monomers and norbornenes (NBs) can readily undergo radical copolymerization,4–6 whereas they are both extremely sluggish in radical homopolymerization,8 has provided us with a foundation on which to build 157‐nm resist polymers 4–6. Our report on the radical copolymerization of TFMA with NBs has prompted other research groups to explore this chemistry for the preparation of 157‐nm resist polymers 9–12. Furthermore, we have found that vinyl ethers (VEs) can copolymerize with TFMA by radical initiation 13–15.…”

Section: Introductionmentioning

confidence: 99%

Radical copolymerization of 2‐trifluoromethylacrylic monomers. II. Kinetics, monomer reactivities, and penultimate effect in their copolymerization with norbornenes and vinyl ethers

Itô

Okazaki

Miller

2004

J. Polym. Sci. A Polym. Chem.

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Radical copolymerizations of electron-deficient 2-trifluoromethylacrylic (TFMA) monomers, such as 2-trifluoromethylacrylic acid and t-butyl 2-trifluoromethylacrylate (TBTFMA), with electron-rich norbornene derivatives and vinyl ethers with 2,2Ј-azobisisobutyronitrile as the initiator were investigated in detail through the analysis of the kinetics in situ with 1 H NMR and through the determination of the monomer reactivity ratios. The norbornene derivatives used in this study included bicyclo[2.2.1]hept-2-ene (norbornene) and 5-(2-trifluoromethyl-1,1,1-trifluoro-2-hydroxylpropyl)-2-norbornene. The vinyl ether monomers were ethyl vinyl ether, t-butyl vinyl ether, and 3,4-dihydro-2-H-pyran. Vinylene carbonate was found to copolymerize with TBTFMA. Although none of the monomers underwent radical homopolymerization under normal conditions, they copolymerized readily, producing a copolymer containing 60 -70 mol % TFMA. The copolymerization of the TFMA monomer with norbornenes and vinyl ethers deviated from the terminal model and could be described by the penultimate model. The copolymers of TFMA reported in this article were evaluated as chemical amplification resist polymers for the emerging field of 157-nm lithography.

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Section: Introductionmentioning

confidence: 99%

Radical copolymerization of 2‐trifluoromethylacrylic monomers. II. Kinetics, monomer reactivities, and penultimate effect in their copolymerization with norbornenes and vinyl ethers

Itô

Okazaki

Miller

2004

J. Polym. Sci. A Polym. Chem.

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“…Today, their use has spread to the medical, veterinary, and cosmetic fields, where CAs are employed as biocompatible adhesives or sealants for replacing sutures and staples, 3 in dentistry, 4,5 and for gluing fake nails or eyelash extensions. 6 In addition, CAs are currently finding application in other emerging areas, such as in drug-delivery systems, 7,8 3D printing processes, 9,10 high-resolution lithography, 11 and forensic sciences. 12,13 Although free radical initiation has also been described, 14 CA polymerization is normally triggered by anionic or neutral nucleophiles.…”

Section: ■ Introductionmentioning

confidence: 99%

Wavelength-Tunable Light-Induced Polymerization of Cyanoacrylates Using Photogenerated Amines

Faggi

Aguilera²,

Sáez³

et al. 2019

Macromolecules

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Cyanoacrylate photopolymerization has already been described, but it generally requires the use of organometallic photoinitiators and highly reactive monomers, which often leads to photoinitiator−monomer mixtures with limited stability. In this work we report a method to tackle these limitations, which relies on the use of amines bearing photoremovable protecting groups as light-responsive nucleophilic cyanoacrylate initiators. By exploiting the versatility of amine photorelease strategies, we have developed a series of all-organic initiators that (a) enable fast, on demand photocuring of commercial formulations of various cyanoacrylates, including less reactive, biologically relevant long alkyl chain monomers; (b) show wavelength tunability along the UV−vis spectrum and good thermal stability in the dark; and (c) lead to polymeric materials with excellent adhesive behavior. Because of this combination of properties, photogenerated amines appear as ideal candidates to bring cyanoacrylate photopolymerization into real application, especially in the biomedical field.

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“…While the new exposure tools work with shorter wavelength sources, the material area faces the challenge of synthesizing new types of photolithography resists that are needed for more stringent optical absorption criteria. The various types of 193 nm resists [8][9][10][11] synthesized have been a significantly scientific achievement in the semiconductor material technology, since they have successfully met the patterning requirements of the 90 nm technology node.…”

Section: Introductionmentioning

confidence: 99%

193-nm resist shrinkage carryover effect to a post-etch layer due to CD-SEM measurement

Cao

Wheeler

Wong

2004

Metrology, Inspection, and Process Control for Microlithography XVIII

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193 nm resist shrinkage due to critical dimension scanning electron microscope (CD-SEM) measurements is a wellknown but unresolved metrology issue in microlithography. Although there have been numerous studies 1-7 on this subject, there are few publications on the 193 nm resist shrinkage finger-print carried over to etched features, i.e., the CD shrinkage carryover effect. This paper reports the results of our CD-SEM measurement study. We observed that the CD changes due to measurement were still present after etch and were often greater than 15% of the feature size. The shrinkage result implies that the action of CD-SEM measurement is destructive to the patterned circuitry. An improved CD-SEM measurement methodology is required to reduce circuitry damage. The study also revealed that minimal shrinkage carryover (less than 1%) could be obtained when the CD-SEM measurement condition was optimized. These results also indicate that measurement of CD shrinkage on post-etch patterns can offer a very effective method to characterize pre-etch resist shrinkage.

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Cycloolefin/cyanoacrylate (COCA) copolymers for 193-nm and 157-nm lithography

Cited by 8 publications

References 0 publications

Radical copolymerization of 2‐trifluoromethylacrylic monomers. II. Kinetics, monomer reactivities, and penultimate effect in their copolymerization with norbornenes and vinyl ethers

Radical copolymerization of 2‐trifluoromethylacrylic monomers. II. Kinetics, monomer reactivities, and penultimate effect in their copolymerization with norbornenes and vinyl ethers

Wavelength-Tunable Light-Induced Polymerization of Cyanoacrylates Using Photogenerated Amines

193-nm resist shrinkage carryover effect to a post-etch layer due to CD-SEM measurement

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