Preparation of a Photoacid Generating Monomer and Its Application in Lithography

Wu, Huixiang; Gonsalves, Kenneth E.

doi:10.1002/1616-3028(200108)11:4<271::aid-adfm271>3.0.co;2-q

Cited by 58 publications

(36 citation statements)

References 16 publications

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“…17 Triphenylsulfonium salt 4-(methacryloxy)benzenesulfonate (MBS-TPS) was likewise prepared by the method of Gonsalves by reacting sodium 4-phenosulfonate and metharylic acid. 19 Phenyl methacrylate-4-(dimethylsulfonium triflate) (PDMS-Tf) was prepared following the procedure of Gonsalves 17 by condensing phenol with dimethyl sulfoxide in the presence of dry hydrogen chloride to give dimethyl-4-hydroxyarylsulfonium chloride which was converted to the corresponding triflate salt.…”

Section: Methodsmentioning

confidence: 99%

“…An early report of the synthesis and use of cation-bound PAGs showed that both PAG homopolymer and copolymers were capable of being employed in high sensitivity resists with little change in acid generation efficiency. 17 It was later shown that both anion-bound and cation-bound PAGs could be prepared and that cation-bound PAGs had increased sensitivity due to presumably higher rates of acid diffusion. 18 This work also noted that some degree of phase segregation occurred which could be explained by the choice of the more non-polar styrene as the second monomer.…”

Section: Introductionmentioning

confidence: 99%

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PAG segregation during exposure affecting innate material roughness

Fedynyshyn

Astolfi

Cabral

et al. 2009

Advances in Resist Materials and Processing Technology XXVI

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We have developed an improved AFM-based technique to measure intrinsic material roughness (IMR) after base development. We have investigated the contribution of different polymeric PAGs to IMR. These polymeric PAGs include copolymers of several styrenic PAGs with hydroxystyrene. The IMR of these polymer-bound PAGs is reduced relative to that of their nonpolymeric counterparts with DUV exposure. Theses results represent further evidence for PAG segregation during the bake steps as being responsible for increased IMR in exposed resists, presumably by increasing the dissolution rate inhomogeneity on a nano-scale level. The work also shows that the effects of PAG segregation can be mitigated by employing polymer-bound PAGs.

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

PAG segregation during exposure affecting innate material roughness

Fedynyshyn

Astolfi

Cabral

et al. 2009

Advances in Resist Materials and Processing Technology XXVI

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show abstract

“…[13][14][15][16][17][18][19][20] These polymerbound PAGs are designed to improve lithographic performance in two ways:…”

Section: Pag Attachmentmentioning

confidence: 99%

LER Limitations of Resist Thin Films

Cardineau

Early

Fujisawa³

et al. 2012

J. Photopol. Sci. Technol.

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This paper describes fundamental studies of the degradation of LER in EUV resists as a function of film thickness. This research focused on the influence of three variables on this LER film thickness problem:  Substrate interaction (primed silicon vs. organic underlayer)  Changes in optical density (variations in fluorine content)  PAG attachment (bound and unbound)Our experimental approach struck a balance between using resists prepared by commercial resist vendors and using open-source resists with custom-designed polymers to address specific variables listed above. One key feature of this research was our development of a mathematical method for evaluation of the extent of the LER deviation in thin films, called φ LER .Our results showed that the effect of substrate was not significant for two different resists (one commercial and one open source). Additionally, we found that increasing optical density actually made the LER degradation (φ LER ) worse-which was contrary to what was predicted by other researchers. Most significant was our demonstration that PAG attachment plays the most important role in the degradation of LER in thinner resist films; polymer-bound PAGs showed a dramatic 3X improvement in φ LER over a similar blended system.

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“…Many attempts to incorporate acid generators such as ionic and non-ionic PAGs into backbone or pendant groups of polymers have been reported mainly to circumvent the problem related to compatibility of acid generators or to suppress acid diffusion in resist matrices. [16][17][18][19][20][21][22][23][24][25][26][27][28][29][30][31][32][33][34] It is very important to know whether a polymer bound PAG provides a substantial advantage over polymer blended PAG in terms of resolution, sensitivity, LWR tradeoffs. Up to now, it is known that the polarity and hydrophobicity of the polymer were very different from those of the polymer when the acid generators were incorporated into polymers.…”

Section: Introductionmentioning

confidence: 82%

Dissolution Kinetics in Polymer-Bound and Polymer-Blended Photo-Acid Generators

Yamamoto

Kozawa

Tagawa

2012

J. Photopol. Sci. Technol.

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In the fabrication beyond 16 nm node, the uniform distribution of acid generators in resist matrix is a serious concern. Recently, the incorporation of acid generators to polymers via covalent bonds has attracted much attention in order to overcome the compatibility problem of acid generators with polymers and reduce the diffusion lengths of acid, which leads to high resolution and low line edge roughness (LER). However, understanding of the resist dissolution kinetics in polymer-bounded and polymer-blended photo-acid generator (PAG) for extreme ultraviolet (EUV) lithography is insufficient. Therefore, it is significantly important to clarify the effect of binding acid generator with polymer on the dissolution kinetics. In this study, dissolution kinetics in polymer-bound and polymer-blended PAG was investigated to understand inherent EUV resist characteristics. The development rate R(E,Z) at different depth position in resist film was determined in polymer-bounded and polymer-blended PAG using resist development analyzer (RDA-800EUV) measurement system. The difference of R(E,Z) in polymer-bounded and polymer-blended PAG was observed. Also, the preliminary evaluation of resist profile for EUV chemically amplified resists was performed by using PROLITH and parameters obtained with EUV exposure tool. Furthermore, the resist patterns were produced by electron beam and the SEM observation results were compared with the PROLITH simulation results.

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Preparation of a Photoacid Generating Monomer and Its Application in Lithography

Cited by 58 publications

References 16 publications

PAG segregation during exposure affecting innate material roughness

PAG segregation during exposure affecting innate material roughness

LER Limitations of Resist Thin Films

Dissolution Kinetics in Polymer-Bound and Polymer-Blended Photo-Acid Generators

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