Fluorinated Chemically Amplified Dissolution Inhibitors for 157 nm Nanolithography

Fresco, Zachary M.; Bensel, Nicolas; Suez, Itai; Backer, Scott A.; Fréchet, Jean M. J.; Conley, Will

doi:10.2494/photopolymer.16.27

Cited by 8 publications

(2 citation statements)

References 22 publications

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“…Chemically amplified 248 nm resists such as those derived from the original t-butyloxycarbonyloxy-styrene system, [2][3][4] while still the workhorse of photolithography, do not have the transparency required to be used with the ArF laser. [8][9][10] The diffraction limit has historically forced a decrease in exposure wavelengths to reduce the critical dimension of new lithographic processes. [8][9][10] The diffraction limit has historically forced a decrease in exposure wavelengths to reduce the critical dimension of new lithographic processes.…”

Section: Introductionmentioning

confidence: 99%

Evaluation of new materials for plasmonic imaging lithography at 476nm using near field scanning optical microscopy

Backer

Suez

Fresco

et al. 2007

Journal of Vacuum Science &Amp; Technology B: Microelectronics and Nanometer Structures Processing, Measurement, and Phenomena

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Articles you may be interested inOptical detection of ultrasound using an apertureless near-field scanning optical microscopy system AIP Conf. Proc. 1511, 360 (2013); 10.1063/1.4789070 Background-free imaging of plasmonic structures with cross-polarized apertureless scanning near-field optical microscopy Rev. Sci. Instrum. 83, 033704 (2012); 10.1063/1.3693346 Plasmonic properties of a nanoporous gold film investigated by far-field and near-field optical techniques Excitation of dielectric-loaded surface plasmon polariton observed by using near-field optical microscopy Appl. Phys. Lett. 93, 073306 (2008); 10.1063/1.2973355Characterization of long-range surface plasmon-polariton in stripe waveguides using scanning near-field optical microscopy A new resist formulation was successfully patterned using near field optical microscopy in order to simulate the conditions prevailing in silver based plasmonic imaging tools. Radiation at 476 nm was transmitted through a near field scanning optical microscopy fiber probe tip to cross-link a film of poly͑4-methacrylmethyl styrene͒ via polymerization of pendant methacryloyl groups using camphorquinone and dimethyl aniline as an initiating system. Patterns were generated by scanning at several speeds in order to moderate the dose while maintaining a constant probe height of about 5 nm above the sample through shear force feedback. After development, lines corresponding to the exposed regions were observed. At a scanning speed of 4 m / s, the observed pattern has a full width at half maximum of 275 nm and a height of ϳ25 nm.

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Section: Introductionmentioning

confidence: 99%

Evaluation of new materials for plasmonic imaging lithography at 476nm using near field scanning optical microscopy

Backer

Suez

Fresco

et al. 2007

Journal of Vacuum Science &Amp; Technology B: Microelectronics and Nanometer Structures Processing, Measurement, and Phenomena

Self Cite

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“…The chemical amplification resist system is one new approach. [42][43][44][45][46] In this system, acid derived from a photo-acid generator promotes removal of the protecting groups, such as tbutyl ester, acetal, trimethylsilyl, and tetrahydropyranyl groups to achieve higher resolution. [47][48][49][50] Recently, many new chemical The n D 's of the calixarene derivative films about 0.1 mm thick, spincoated on a silicon wafer, before and after photo-irradiation were determined by ellipsometry at 632.8 nm.…”

Section: Arf Resist Materials Based On Cyclodex-trinmentioning

confidence: 99%

Development of Novel Photo-Functional Materials Based on Cyclic Oligomers

Kudo

Nishikubo

2009

Polym. J.

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Novel photo-functional materials, such as refractive-index-changing materials, argon fluoride (ArF) resist materials, and electron beam (EB) resist materials, were designed based on the structures of calixarenes, cyclodextrin, and noria. The synthesis and refractive-index properties of calixarene derivatives containing photo-reactive groups, including azobenzene, norbornadiene, anthracene, cinnamate, and chalcone, were examined, and refractive-index changes (Án D 's) of between 0.007 and 0.061 were observed. The synthesis and patterning properties of a single-layer ArF photoresist system of -CD derivative containing t-butyl ester and fluorine were examined, and a well-resolved 100 nm line and space pattern was obtained on a silicon wafer. A new ladder-like macrocycle, noria (water wheel in Latin), was also synthesized and its application as an EB resist material was examined. The noria derivatives noria-COO t Bu containing t-butyl ester groups, noria-BOC containing t-butyloxycarbonyl group, and noria-acetal containing acetal groups had good physical properties and photo-reactivity. EBresist based on noria-COO t Bu and noria-BOC provided clear line and space patterns at a resolution of 70 and 50 nm, respectively.The development of novel photo-functional materials has contributed substantially to progress in the electronic and optoelectronic industries. Photo-reactive groups, such as radical-or cation-polymerizable groups, photo-isomerizable groups, and photo-removable groups, are useful for obtaining ultraviolet (UV)-cured resins, refractive-index-changing materials, and photo-resist materials, respectively. The physical properties of photo-functional materials, such as film-forming characteristics, thermal stability, mechanical properties, and photo-reactivity, depend primarily on the polymer or oligomer structure. Generally, the photochemical reactivity increases with decreasing glass transition temperature (T g ), due to increase of the molecular motion of polymer chains and functional groups.The photo-chemical reactivity of oligomers is usually greater than that of polymers, due to the lower T g of oligomers compared with polymers. However, the mechanical properties, thermal stability and film-forming properties of oligomer derivatives are inferior to those of polymer derivatives. However, if a linear oligomer is changed to a cyclic oligomer by coupling reaction of the two ends, the physical properties of the resulting cyclic oligomer are expected to be superior to those of the linear oligomer. Therefore, we considered that photofunctional cyclic oligomers might combine the advantages of photo-functional polymers and photo-functional oligomers. That is, photo-functional cyclic oligomers might have both high photo-chemical reactivity and good physical properties.Calixarenes are typical cyclic oligomers containing many hydroxyl groups, and are prepared easily by the reaction of phenols with aldehydes (Scheme 1). 1Although it is well known that calixarenes are attractive materials for use as host molecules in th...

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Syntheses and properties of hyperbranched polybenzoxazole by thermal cyclodehydration of hyperbranched poly[o‐(t‐butoxycarbonyl)amide] via A₂ + B₃ approach

Kudo

Maruyama

Shindo

et al. 2006

J. Polym. Sci. A Polym. Chem.

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The syntheses and properties of hyperbranched poly(o‐hydroxyamide) [poly(HAB‐BCC)‐ABP], poly[o‐(t‐butoxycarbonyl)amide] [poly(HAB‐BCC)‐ABP‐t‐BOC], and polybenzoxazole [poly(HAB‐cycloBCC)] were examined. Poly(HAB‐BCC)‐ABP was obtained from the polycondensation reaction of 3,3‐dihydroxy‐4,4′‐diaminobiphenyl (HAB) as an A2‐monomer and 1,3,5‐benzenetricarboxylchloride (BCC) as a B3‐monomer with 2‐amino‐4‐t‐butylphenol (ABP) in NMP in the presence of pyridine for 24 h. The reaction of poly(HAB‐BCC)‐ABP and di‐t‐buthylcarbonate (DiBOC) was performed to obtain the corresponding poly(HAB‐BCC)‐ABP‐t‐BOC with pendant t‐BOC groups. The thermal cyclodehydration of poly(HAB‐BCC)‐ABP‐t‐BOC was carried out in the film sate at 400 °C, affording the poly(HAB‐cyclo‐BCC) in quantitative yield. Furthermore, the solubilities and thermal properties of these polymers were examined. © 2006 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 44: 3640–3649, 2006

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Fluorinated Chemically Amplified Dissolution Inhibitors for 157 nm Nanolithography

Cited by 8 publications

References 22 publications

Evaluation of new materials for plasmonic imaging lithography at 476nm using near field scanning optical microscopy

Evaluation of new materials for plasmonic imaging lithography at 476nm using near field scanning optical microscopy

Development of Novel Photo-Functional Materials Based on Cyclic Oligomers

Syntheses and properties of hyperbranched polybenzoxazole by thermal cyclodehydration of hyperbranched poly[o‐(t‐butoxycarbonyl)amide] via A₂ + B₃ approach

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Fluorinated Chemically Amplified Dissolution Inhibitors for 157 nm Nanolithography

Cited by 8 publications

References 22 publications

Evaluation of new materials for plasmonic imaging lithography at 476nm using near field scanning optical microscopy

Evaluation of new materials for plasmonic imaging lithography at 476nm using near field scanning optical microscopy

Development of Novel Photo-Functional Materials Based on Cyclic Oligomers

Syntheses and properties of hyperbranched polybenzoxazole by thermal cyclodehydration of hyperbranched poly[o‐(t‐butoxycarbonyl)amide] via A2 + B3 approach

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Syntheses and properties of hyperbranched polybenzoxazole by thermal cyclodehydration of hyperbranched poly[o‐(t‐butoxycarbonyl)amide] via A₂ + B₃ approach