New photoresists for deep ultraviolet (&lt;300 nm) exposure

Chandross, Edwin A.; Reichmanis, Elsa; Wilkins, C. W.; Hartless, R. L.

doi:10.1139/v83-149

Cited by 10 publications

(9 citation statements)

References 1 publication

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“…Thus, such systems have very high sensitivity. This chemical amplification concept has been exploited in the design of a large number of new resist systems. − …”

Section: Introductionmentioning

confidence: 99%

Alicyclic Polymers for 193 nm Resist Applications: Synthesis and Characterization

Okoroanyanwu

Shimokawa

Byers³

et al. 1998

Chem. Mater.

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A series of new alicyclic polymers designed for use as 193 nm photoresist materials has been synthesized and characterized. These resins are based on cycloaliphatic co-and terpolymers of 2-methylpropylbicyclo[2.2.1]hept-5-ene-2-carboxylate (trivial name, carbotert-butoxy norbornene), bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (trivial name, norbornene carboxylic acid), 8-methyl-8-carboxytetracyclo[4,4,0.1, 2,5 1 7,10 ]dodec-3-ene (trivial name, methyl tetracyclododecene carboxylic acid), 5-(hydroxymethyl)-2-norbornene-2-methanol, and maleic anhydride, which were synthesized by free radical, Pd(II)-catalyzed addition, and ringopening metathesis polymerization techniques. The polymers derived from ring-opening metathesis polymerization were hydrogenated to provide another member of this group of materials. The polymers are soluble in common organic solvents and have glass transition temperatures ranging from less than 60°C to higher than 250°C depending on their specific structure and mode of polymerization. The low absorption of these polymers at 193 nm wavelength and their high resistance to reactive ion etching make these attractive candidates for 193 nm resist applications.

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“…Thus, such systems have very high sensitivity. This chemical amplification concept has been exploited in the design of a large number of new resist systems. − …”

Section: Introductionmentioning

confidence: 99%

Alicyclic Polymers for 193 nm Resist Applications: Synthesis and Characterization

Okoroanyanwu

Shimokawa

Byers³

et al. 1998

Chem. Mater.

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“…In order to increase the main chain scission susceptibility of polymethacrylates, various copolymers and analogs were synthesized and evaluated as resist polymers [5][6][7][8][9][10][11][12]. Among the polymethacrylates, poly(fluorobutyl methacrylate), developed for electron beam and x-ray lithography [13], appears to be the most sensitive to deep UV radiation [14].…”

Section: Polymethacrylate Resistsmentioning

confidence: 99%

“…Methacrylate copolymers developed as deep UV resists by AT&T Bell Laboratories are presented in Figure 1 (1, 2) [5][6][7][8][9][10]. Incorporation of select comonomers provided higher deep UV absorptions and alternate degradation pathways for improved sensitivity.…”

Section: Polymethacrylate Resistsmentioning

confidence: 99%

Evolution and Progress of Deep UV Resist Materials.

Itô

1998

J. Photopol. Sci. Technol.

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It has been almost thirty years since the first deep UV exposure was carried out and almost twenty five years since the term "deep UV lithography" was coined. Although resist systems classified as "chemical amplification resists" are the workhorse for the 248 nm deep UV lithography, the resist materials have evolved significantly in the realm of deep UV lithography as well as within the boundary of chemical amplification. This paper describes the evolution and progress of the deep UV (248-193 nm) positive resist materials that have occurred in the last quarter century.

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“…The third is polymerization producing insolubilization, whereby multifunctional monomers are made to polymerize via actinic radiation with/without a photosensitizer/initiator. Chandross et al 1 studied photosensitive bodies sensitive to ultraviolet radiation and exhibiting excellent contrast of images. The images were formed from a base-soluble polymer of poly(methyl methacrylateco-methacrylic acid) mixed with base-insoluble compounds of o,oЈ-dinitrobenzyl esters.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of poly[(methyl methacrylate)‐co‐(methacrylic acid)] for a UV‐sensitive aqueous base developable lithographic plate

Kiatkamjornwong¹,

Tessiri²

2002

J of Applied Polymer Sci

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Syntheses of the copolymers of methyl methacrylate and methacrylic acid were carried out by free radical chain polymerization in the presence of benzoyl peroxide (BPO) as an initiator. The effects of the monomer ratio and polymerization time on the averaged molecular weights, polydispersity index, and glass transition temperature were investigated. FTIR and NMR were used for functional group characterization, GPC for average molecular weights and the distribution, elemental analysis for CHO content, and DSC for the glass transition temperature. The copolymers were mixed with tripropylene glycol diacrylate (TPGDA) and trimethylol propane ethoxylated triacrylate (TMPEOTA), 2-hydroxy-2-methyl-1-phenyl-propan-1-one (Darocur 1173) and benzophenone (Darocur BP) with anthraquinone for visibility of images. The photosensitive coating was spin-coated onto the anodized aluminum plate on which a thin film was formed. The wet film was then coated with PVA solution as an oxygen barrier layer. The plate assembled with a control wedge and a black color separation film was exposed to UV radiation at different exposure times. The plate was developed in a dilute alkaline developer. The resulting plate was evaluated for its reproduction properties in terms of surface properties (hydrophilic/hydrophobicity) by contact angle measurement of image/nonimage areas, resolution by microline, tone reproduction, and adhesion tests. The article describes the results of the syntheses, characterizations, and uses of the copolymer as a binder of a negative, lithographic printing plate. The present lithographic printing plate is good for a medium viscosity printing ink to produce medium printing quality on uncoated paper.

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New photoresists for deep ultraviolet (<300 nm) exposure

Cited by 10 publications

References 1 publication

Alicyclic Polymers for 193 nm Resist Applications: Synthesis and Characterization

Alicyclic Polymers for 193 nm Resist Applications: Synthesis and Characterization

Evolution and Progress of Deep UV Resist Materials.

Synthesis and characterization of poly[(methyl methacrylate)‐co‐(methacrylic acid)] for a UV‐sensitive aqueous base developable lithographic plate

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