IBM 193nm Semiconductor Resist: Material Properties, Resist Characteristics and Lithographic Performance.

Varanasi, Pushkara Rao; Mewherter, Ann Marie; Lawson, Margaret C.; Jordhamo, George M.; Allen, Robert D.; Opitz, Juliann; Ito, Hirokazu; Wallow, Tom; Hofer, Donald C.

doi:10.2494/photopolymer.12.493

Cited by 11 publications

(2 citation statements)

References 4 publications

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“…Finally, it is also possible to polymerize NB maintaining the bicyclic structure, i.e., only opening the double bond, in a typical vinyl polymerization. , This type of poly(norbornene) (PNB) is a special polymer, due to its good mechanical properties, heat resistivity, transparency, high glass transition temperature, and good solubility in polar organic solvents. PNB has been deeply investigated for many optical and microelectronic applications, and its films have excellent optical transparency, heat stability, and good UV resistance; therefore they can be employed as components for condensers or cover layers for liquid-crystal displays. − Moreover, the high optical transparency in the infrared region of the spectrum makes PNBs very promising materials for data storage and telecommunication waveguides …”

Section: Introductionmentioning

confidence: 99%

Vinyl Polymerization of Norbornene by Bis(salicylaldiminate)copper(II)/Methylalumoxane Catalysts

et al. 2006

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The polymerization of norbornene in the presence of different bis(salicylaldiminate)copper(II) complexes and methylalumoxane has been investigated. In all cases a high molecular weight vinyl-type polymer was obtained. The presence of electron-withdrawing nitro groups on the chelate ligand markedly increased the activity of the catalyst. The influence on the catalytic performances and polymer characteristics as a function of reaction parameters, such as temperature, duration, and content of free trimethyl aluminum in the commercial MAO, was studied

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Section: Introductionmentioning

confidence: 99%

Vinyl Polymerization of Norbornene by Bis(salicylaldiminate)copper(II)/Methylalumoxane Catalysts

et al. 2006

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“…In addition, they promised to be highly transparent at 193 nm due to the lack of unsaturation. Much was published regarding the suitability of one type of alicyclic resin for 193 nm application, vinyl addition poly(norbornene), beginning in the late 1990s . For example, unfunctionalized poly(norbornene) exhibited a lower etch rate than novolac under very aggressive chlorine etch conditions while appropriately functionalized poly(norbornene) formulations could print sub‐100 nm contact holes .…”

Section: Introductionmentioning

confidence: 99%

Polymers of norbornenyl‐4‐phenol: Dissolution rate characteristics, positive tone photo‐patterning, and polymer properties

Evans

Brick

Bell

et al. 2017

J of Applied Polymer Sci

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Vinyl addition norbornene polymers with phenol pendent groups are obtained by methanolysis of the 4-acetoxyphenyl norbornene polymer. Thin films of this polymer blended with additives such as norbornene polymers with hexafluoroalcohol pendent groups and diazonaphthoquinone compounds result in linear dissolution in tetramethylammonium hydroxide developer. Good resolution, positive tone patterns are obtained from image-wise exposure of thin films of blends of the diazonaphthoquinone additives with both phenol pendent norbornene homopolymer and with norbornene copolymers with both phenol and hexafluoroalcohol pendent groups. Properties such as transparency, dielectric constant, chemical, and thermal resistance were determined for cured copolymer compositions containing an epoxy crosslinker.

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The Effect of End Group Modification on the Transparency of Vinyl Addition Norbornene Polymers at 193 nm

Chang

Lipian

Barnes

et al. 2005

Macro Chemistry & Physics

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Summary: Homopolymers of a bis‐trifluorocarbinol substituted norbornene (1) (α,α‐bis(trifluoromethyl)bicyclo[2.2.1]hept‐5‐ene‐2‐ethanol or HFANB) and copolymers of 1 with t‐butyl ester of 5‐carboxylic acid (2, t‐BuEsNB) were produced using palladium catalysts and olefinic chain transfer agents such as 1‐hexene and ethylene to control molecular weight. However, these low‐molecular‐weight polymers exhibited relatively low optical transparencies at 193 nm. In fact, the opacity (measured as optical densities in absorbance units per micron) of thin films of these homo‐ and co‐polymers was inversely proportional to their molecular weight. This relationship is consistent with an end group contribution to the film opacity. Spectroscopic analysis of these polymers by 1H NMR and MALDI‐TOF MS confirmed that 1‐hexene and ethylene chain transfer agents generated olefin‐terminated vinyl addition polymers. The olefinic end group contribution to optical density can be eliminated by appropriate chemical modification. Both epoxidation and hydrogenation of the polymer olefinic end groups generated very low optical density materials, independent of molecular weight, that are suitable as 193‐nm photoresist binder resins.End group modification of vinyl and hexenyl‐terminated homopolymers of 1 by epoxidation or hydrogenation.magnified imageEnd group modification of vinyl and hexenyl‐terminated homopolymers of 1 by epoxidation or hydrogenation.

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IBM 193nm Semiconductor Resist: Material Properties, Resist Characteristics and Lithographic Performance.

Abstract: Using substituted poly(norbomenes), we have developed an etch-resistant, high resolution single layer 193nm positive resist. This paper describes the optical absorption properties, oxide-etch characteristics and resolution capabilities of such a first generation IBM resist.

Cited by 11 publications

References 4 publications

Vinyl Polymerization of Norbornene by Bis(salicylaldiminate)copper(II)/Methylalumoxane Catalysts

Vinyl Polymerization of Norbornene by Bis(salicylaldiminate)copper(II)/Methylalumoxane Catalysts

Polymers of norbornenyl‐4‐phenol: Dissolution rate characteristics, positive tone photo‐patterning, and polymer properties

The Effect of End Group Modification on the Transparency of Vinyl Addition Norbornene Polymers at 193 nm

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