Polyarylenesulfonium Salt as a Novel and Versatile Nonchemically Amplified Negative Tone Photoresist for High-Resolution Extreme Ultraviolet Lithography Applications

Reddy, Pulikanti Guruprasad; Pal, Suresh; Kumar, Pawan; Pradeep, Chullikkattil P.; Ghosh, Subrata; Sharma, Satinder K.; Gonsalves, Kenneth E.

doi:10.1021/acsami.6b10384

Cited by 28 publications

(18 citation statements)

References 25 publications

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“…The LER and LWR parameters of ∼15 nm patterns were calculated using industry standard Summit software (Figure S18). The obtained LER and LWR values were found to be ∼1.03 ± 0.07 nm and ∼1.18–1.30 nm, which are very much within the acceptable range. , …”

Section: Resultsmentioning

confidence: 55%

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Organotin in Nonchemically Amplified Polymeric Hybrid Resist Imparts Better Resolution with Sensitivity for Next-Generation Lithography

Peter

Moinuddin

Ghosh

et al. 2020

ACS Appl. Polym. Mater.

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Given the need for a next-generation technology node in the area of integrated circuits (ICs), improvement in the properties of resist materials, particularly sensitivity (E D ), resolution, good etch resistance, and low line edge/width roughness (LER/LWR), has been highly desirable but also extremely challenging. Herein, we report a series of organic− inorganic hybrid nonchemically amplified copolymer resists (n-CARs) bearing radiation-sensitive sulfonium functionality as well as tin metal as an organometallic unit in the structural backbone for low E D and LER/LWR. These resists have been synthesized by the free radical copolymerization of the organic monomer (4-(methacryloyloxy)phenyl)-dimethylsulfoniumtriflate (MAPDST) and acetyldibutylstannyl methacrylate (ADSM) in different feed ratios (97:3, 93:7, 88:12) and characterized using FT-IR, 1 H, 19 F NMR, GPC, XPS, and ICP-OES techniques. These MAPDST-co-ADSM copolymers exhibited molecular weights (M w ) in the range of 10 077−12 187 g mol −1 . Electron beam lithography (EBL) studies revealed that the negative tone n-CARs characteristic with patterning down to sub-15 nm features. The well-developed sub-15 nm nanofeatures showed low LER of ∼1.29 ± 0.07 line patterns (number belongs to feed ratio 93:7). The variable e-beam exposure dose study revealed that the E D of these resists varies with the percentage of incorporated Sn in the polymer matrix. Incorporation of 2.48 wt % Sn (feed ratio 88:12) in the polymer chain led to a significant enhancement in the E D (175 μC/cm 2 ). Furthermore, the mechanistic study of pattern development has been performed with electron beam reactivity analyses using the XPS technique. These investigations substantiate the potential candidature of developed resist formulation for next-generation semiconductor technology applications.

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Section: Resultsmentioning

confidence: 55%

“…The obtained LER and LWR values were found to be ∼1.03 ± 0.07 nm and ∼1.18−1.30 nm, which are very much within the acceptable range. 29,30 3.3. Hybrid n-CARs Dissolution Analysis: Effect of PEB and Developer.…”

Section: High-resolution Pattern Generation From E-beam Lithography (...mentioning

confidence: 99%

Organotin in Nonchemically Amplified Polymeric Hybrid Resist Imparts Better Resolution with Sensitivity for Next-Generation Lithography

Peter

Moinuddin

Ghosh

et al. 2020

ACS Appl. Polym. Mater.

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“…Here we report regioselective C–H sulfanylation of aryl sulfoxides with alkyl aryl sulfides through Pummerer-type activation. This methodology is totally different from the previous Friedel–Crafts-type C–H sulfanylation and enables us to access precisely regiocontrolled 1,4-disulfanylarenes …”

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confidence: 99%

Regioselective C–H Sulfanylation of Aryl Sulfoxides by Means of Pummerer-Type Activation

Kawashima

Yanagi

et al. 2017

Org. Lett.

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A regioselective C-H sulfanylation of aryl sulfoxides with alkyl aryl sulfides in the presence of acid anhydride was developed, which resulted in the formation of 1,4-disulfanylarenes after dealkylation of initially formed sulfonium salts. The reaction began with Pummerer-type activation of aryl sulfoxides followed by nucleophilic attack of alkyl aryl sulfides. The nucleophilic attack occurred exclusively at the para positions, or at specific positions in case the para position was not available, under perfect control by the dominating sulfoxide directors regardless of any other substituents. The initially formed aryl sulfonium salts were isolable and usefully served as aryl halide surrogates for palladium-catalyzed arylation with sodium tetraarylborates.

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“…In this progress, Nandi et al has produced high-aspect-ratio patterns of 100 nm with an ionic photoacid generator-included Terpolymer photoresist, viz., GBLMA–MAMA–MAPDST . Apart from CARs, hybrid resists are also being considered as emerging candidates for current lithography technology mainly due to their patterning potential for high-resolution features in the absence of PAGs in resist compositions. − Similarly, metal–organic clusters and methacrylate-based materials without any PAG have also been reported with notable sensitivity toward all types of irradiations. − Recently, our group developed nickel-based negative tone resists using EBL/HIBL and showed sub-10 nm line patterning. , Also, the negative tone chromium-containing resists revealed the patterning capability and high-etch resistance to silicon and tungsten at sub-10 nm resolution …”

Section: Introductionmentioning

confidence: 99%

Functionalized Ag Nanoparticles Embedded in Polymer Resists for High-Resolution Lithography

Moinuddin

Kumar

Yogesh

et al. 2020

ACS Appl. Nano Mater.

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Extending the resolution limit of next-generation lithography down to 15 nm or below requires the resist to attain small features, high irradiation sensitivity, and low line edge/width roughness. To meet this prerequisite, an increase of irradiation absorption in resists is an important strategy. A negative tone, deep ultraviolet, electron beam, and helium ion beam active resist formulation has been realized comprising a hydroxystyrene-based polymer tert-butyl 2-ethyl-6-(4-hydroxyphenyl)-4-phenylheptanoate (Terpolymer). Further, the resist performance was enhanced by doping of a microemulsion-based Ag nanoparticle (size distribution ∼2 nm) irradiation sensitizer. As a result, a tenfold decrease in the critical dose (E o ) was observed by increasing Ag nanoparticle contents from 0.1 to 1.0 wt %. The developed resist patterns exhibit significantly higher sensitivities and resolutions of 50 and 34.12 μC/cm 2 and ∼12 and ∼11 nm line patterns, respectively, for e-beam (E e ) and helium ion beam (E He ) irradiations. The line edge/width roughness of well-developed e-beam exposed patterns was found to be 1.5 ± 0.1/2.8 ± 0.3 nm, respectively. These e-beam/resist interactions were modeled by the Monte-Carlo trajectory, and the results were in line with the experimentally observed one. These simulations suggest the enhanced irradiation absorption inside the resist matrix with the addition of a high-electron-density Ag entity. These investigations reveal that one of the best ways to simultaneously improve the sensitivity and resolution of the resist is the optimum incorporation of higher-atomic-number nanoparticles in the polymeric matrix, which enhances the absorption cross section (σ) without altering the resist properties.

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Polyarylenesulfonium Salt as a Novel and Versatile Nonchemically Amplified Negative Tone Photoresist for High-Resolution Extreme Ultraviolet Lithography Applications

Cited by 28 publications

References 25 publications

Organotin in Nonchemically Amplified Polymeric Hybrid Resist Imparts Better Resolution with Sensitivity for Next-Generation Lithography

Organotin in Nonchemically Amplified Polymeric Hybrid Resist Imparts Better Resolution with Sensitivity for Next-Generation Lithography

Regioselective C–H Sulfanylation of Aryl Sulfoxides by Means of Pummerer-Type Activation

Functionalized Ag Nanoparticles Embedded in Polymer Resists for High-Resolution Lithography

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