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Advances in Patterning Materials and Processes XLII

作者： Ku, Yejin Choi, Hyoeun Kim, Gayoung Lee, Jin-Kyun Kim, Jiho Lee, Sangsul Program in Environment and Polymer Engineering Inha University Incheon22212 Korea Republic of Department of Polymer Science and Engineering Inha University Incheon22212 Korea Republic of Program in Semiconductor Convergence Inha University Incheon22212 Korea Republic of Pohang Accelerator Laboratory POSTECH Pohang37673 Korea Republic of

ISBN: (纸本)9781510686427

High-numerical-aperture (NA) extreme ultraviolet lithography (EUVL) is essential for next-generation semiconductor manufacturing, requiring advanced photoresists (PRs) that can function effectively in ultra-thin films. However, ultra-thin PR films-primarily needed to meet stringent depth-of-focus constraints-face several challenges, including low photon absorption and reduced etch resistance. Additionally, as feature sizes shrink, the diminished PR-substrate contact area exacerbates pattern collapse issues in high NA EUVL. To mitigate these challenges, underlayers are increasingly employed to enhance patterning performance. In this study, we propose a supportive underlayer (SUL) to enhance the sensitivity of chemically-amplified photoresists (CARs) and improve adhesion between the CAR film and the SUL. As a preliminary step, we introduced a simple experimental protocol to identify high-absorption elements that could be more effective in the CAR system, exploiting a PR film-overcoat bi-layer structure. Overcoats containing hydrogen (H), iodine (I), and tin (Sn) were readily prepared on top of the CAR film by the help of solvent orthogonality. Our findings revealed that iodine atoms significantly reduced the exposure threshold compared to hydrogen or tin. Based on these results, hydrophobic iodinated materials were selected as SUL candidates, and a few materials were synthesized with different iodine contents. After fabricating the bi-layer stack, we evaluated the solubility changes of PR films under both positive- and negative-tone development (PTD and NTD) conditions. The incorporation of an iodinated SUL beneath the CAR films enhanced both lithographic sensitivity and substrate adhesion, regardless of the development type, with higher iodine content further amplifying these effects. These findings provide a promising pathway for implementing EUV underlayers specifically tailored for high-NA EUVL. © 2025 SPIE.

关键词： Extreme ultraviolet lithography

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Positive-tone Tin-oxo Nanoclusters for Extreme UV lithography 42

Positive-tone Tin-oxo Nanoclusters for Extreme UV lithograph...

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Advances in Patterning Materials and Processes XLII

作者： Kim, Gayoung Ku, Yejin Jeon, Subin Lee, Jin-Kyun Lee, Seohyun Jung, Byung Jun Lee, Sung-Il Ryu, Choonghan Park, Kangho Jung, Yun Lim Jeong, Changyoung Choi, Jin Program in in Environment and Polymer Engineering Inha University Incheon22212 Korea Republic of Program in Semiconductor Convergence Inha University Incheon22212 Korea Republic of Department of Polymer Science and Engineering Inha University Incheon22212 Korea Republic of Department of Materials Science and Engineering University of Seoul Seoul02504 Korea Republic of Samsung Electronics Co. Ltd. Semiconductor R&D Center Suwon18448 Korea Republic of

ISBN: (纸本)9781510686427

In this study, we propose a strategy to achieve positive metal oxide resists (pMORs) based on tin-oxo nanoclusters (TOCs) for extreme ultraviolet (EUV) lithography in high-performance semiconductor integrated circuit manufacturing. TOC possesses Lewis acidic properties and becomes more strongly acidic upon ligand dissociation when exposed to high-energy radiation, such as electron beam (e-beam) and EUV. During the subsequent development process using an aqueous solution of tetramethylammonium hydroxide (TMAH), a Lewis base, the exposed regions undergo Lewis acid-base interactions, leading to increased hydrophilicity. Ultimately, this results in enhanced solubility, enabling the formation of positive-tone patterns. To address the limitations of TOCs, particularly in terms of process margin and chemical stability, we mixed TOCs with small organic molecules containing phenolic hydroxyl groups, which act as Lewis bases. This modification effectively mitigated the shortcomings of TOCs. A TOC formulation containing 10% dendritic polyphenol (DPP) exhibited an improved dissolution contrast while simultaneously enhancing chemical stability. Using this in EUV lithography, we successfully achieved high resolution positive-tone patterns with a line width of 13 nm. © 2025 SPIE.

关键词： Extreme ultraviolet lithography

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Approach for enhancing sensitivity of tin-oxo cluster resist for high NA extreme UV lithography 41

Approach for enhancing sensitivity of tin-oxo cluster resist...

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Advances in Patterning Materials and Processes XLI 2024

作者： Ku, Yejin Kim, Gayoung Kim, Min Seung Lee, Jin-Kyun Kim, Jiho Park, Byeong-Gyu Lee, Sangsul Lee, Seohyeon Jung, Byung Jun Lee, Changhyeon Kim, Hyunseok Hur, Su-Mi Koh, Chawon Nishi, Tsunehiro Kim, Hyun-Woo Program in Environment and Polymer Engineering Inha University Incheon22212 Korea Republic of Department of Polymer Science and Engineering Inha University Incheon22212 Korea Republic of Pohang Accelerator Laboratory Postech Pohang37673 Korea Republic of Department of Materials Science and Engineering University of Seoul Seoul02504 Korea Republic of Department of Polymer Engineering Graduate School Chonnam National University Gwangju61186 Korea Republic of School of Polymer Science and Engineering Chonnam National University Gwangju61186 Korea Republic of Department of Materials Science and Engineering Yonsei University Seoul03722 Korea Republic of Samsung Electronics Co. Ltd. Semiconductor R&d Center Gyeonggi-do 18448 Korea Republic of

ISBN: (纸本)9781510672208

High numerical aperture (NA) EUV lithography is considered as the most-promising candidate for next generation lithography protocol that will play a crucial role in meeting the demand on the enhanced semiconductor performance and productivity. While this technology enables the fabrication of sub-10 nm patterns, the increased NA has posed challenges, such as reduced depth of focus and narrower process margins. To overcome these hurdles, it is essential to apply thinner resist films while ensuring that the resulting small patterns maintain sufficient physical and chemical durability. Moreover, considering that thinner films absorb fewer photons, the resist molecular structure should be designed to compensate sensitivity burdens. Here, an approach has been proposed to enhance sensitivity by accelerating the solubility change of a well-known tinbased nanocluster resist. To accomplish this goal, it is important to increase not only the number of secondary electrons but also reaction sites and promote radical-based chemical reactions. We aimed at experimentally validating this concept by utilizing elements with high EUV absorbance and highly reactive functional groups with tin radicals. As a model resist, we chose a tin-oxo cage material consisting of a divalent cation containing 12 tin atoms and two counter anions. Our findings indicate that the introduction of unsaturated groups capable of building bridging bonds with radicals leads to fast solubility change at a lower exposure dose, thus enhancing sensitivity. This research offers a promising direction for the development of resists tailored for High NA EUV lithography. © COPYRIGHT SPIE. Downloading of the abstract is permitted for personal use only.

关键词： Tin

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Sensitivity improvement of fluoroalkylated EUV resist with electron-rich vinyl units 41

Sensitivity improvement of fluoroalkylated EUV resist with e...

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Advances in Patterning Materials and Processes XLI 2024

作者： Kim, Gayoung Ku, Yejin Lee, Jin-Kyun Kim, Jiho Park, Byeong-Gyu Lee, Sangsul Jang, Yu Ha Jung, Byung Jun Koh, Chawon Nishi, Tsunehiro Kim, Hyun-Woo Program in Environment and Polymer Engineering Inha University Incheon22212 Korea Republic of Department of Polymer Science and Engineering Inha University Incheon22212 Korea Republic of Pohang Accelerator Laboratory Postech Pohang37673 Korea Republic of Department of Materials Science and Engineering University of Seoul Seoul02504 Korea Republic of Samsung Electronics Co. Ltd. Semiconductor R&d Center Suwon18448 Korea Republic of Department of Materials Science and Engineering Yonsei University Seoul03722 Korea Republic of

ISBN: (纸本)9781510672208

In this study, we present a method to enhance the sensitivity of fluorinated EUV resists by leveraging the rapid coupling reaction between electrophilic carbon radicals and electron-rich alkenes. To validate the impact of the vinyl groups, DVS-HNF was synthesized by introducing fluorinated alkyl chains and silyl vinyl functional groups into the model compound. Additionally, TMS-HNF and EDMS-HNF, which do not contain a vinyl moiety, were synthesized for comparison. To evaluate the patterning properties of the three materials, e-beam lithography experiments were conducted, resulting in the formation of negative-tone patterns for all three materials. Comparing sensitivities, DVS-HNF with two vinyl moieties exhibited the most excellent sensitivity, confirming the effective collaboration between fluorinated alkyl radicals and vinyl groups. After performing an EUV lithography experiment on DVS-HNF, it was confirmed that a 30 nm negative-tone pattern was successfully formed with excellent sensitivity. These results substantiate the potential of the single-component molecular resist for high performance EUV lithography. © COPYRIGHT SPIE. Downloading of the abstract is permitted for personal use only.

关键词： Extreme ultraviolet lithography

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Photolithography Patterning of Organic Light-Emitting Diodes Using Solvent Resistant Electron Transport Materials

Photolithography Patterning of Organic Light-Emitting Diodes...

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International Symposium, Seminar, and Exhibition, Display Week 2024

作者： Yu, Hyunjin Yeong So, Eun Eun, Kyunghyun Jun Jung, Byung Kim, Myungwoong Lee, Jin-Kyun Yeob Lee, Jun School of Chemical Engineering Sungkyunkwan University 2066 Seobu-ro Jangan-gu Suwon-si Gyeonggi-do16419 Korea Republic of Department of Materials Science and Engineering University of Seoul Seoul02504 Korea Republic of Department of Chemistry and Chemical Engineering Inha University Incheon22212 Korea Republic of Program in Environment and Polymer Engineering Inha University 100 Inha-ro Michuhol-gu Incheon22212 Korea Republic of

In this paper, we develop a novel approach to achieve ultra-high resolution in organic light-emitting diodes (OLEDs) through a photolithography patterning process. It is important to apply a solvent resistant electron transport layer (ETL) in the photolithography pattering of OLED because of solution coating process of photoresist on the ETL. Therefore, a solvent resistant ETL named 2,7-bis(4,6-diphenyl-1,3,5-triazin-2-yl)-9,9′-spirobi[fluorene] (SBF-Trz) was developed and employed as the ETL of OLEDs. The SBF-Trz demonstrated excellent solvent resistance during photolithography process and enabled device performances comparable to those of the conventional OLED without any photolithography process. It was found that the SBF-Trz ETL is appropriate as the ETL of the OLED patterned by photolithography due to good electron transport property, good stability, and good solvent resistance. © 2024, John Wiley and Sons Inc. All rights reserved.

关键词： Reactive ion etching

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Fluoroalkylated tin-oxo nano clusters as resist candidates for extreme UV lithography 40

Fluoroalkylated tin-oxo nano clusters as resist candidates f...

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Advances in Patterning Materials and Processes XL 2023

作者： Ku, Yejin Ahn, Hyungju Lee, Jin-Kyun Kim, Jiho Park, Byeong-Gyu Lee, Sangsul Jang, Yu Ha Jung, Byung Jun Koh, Chawon Nishi, Tsunehiro Kim, Hyun-Woo Program in Environment and Polymer Engineering Inha University Incheon22212 Korea Republic of Department of Polymer Science and Engineering Inha University Incheon22212 Korea Republic of Pohang Accelerator Laboratory Postech Pohang37673 Korea Republic of Department of Materials Science and Engineering University of Seoul Seoul02504 Korea Republic of Samsung Electronics Co. Ltd. Semiconductor R and D Center Gyeonggi-do18448 Korea Republic of

ISBN: (纸本)9781510661035

Extreme UV (EUV) lithography is entering full-scale production of high-end IC chips. This transition gives researchers in academia and industry ample motivation to propose new chemistries that will contribute to alleviating the resolution-line edge roughness-sensitivity trade-off dilemma of EUV lithography. We also have a great interest in the radical chemistry of carbon-fluorine bonds working under EUV and have explored its applicability as a platform for implementing novel EUV resists. While it was checked that the chemical concept is viable by using fluorinated small molecules and polymers, it needed to be upgraded in terms of patterning resolution and sensitivity. Recently, we extended successfully the radical-based strategy to the tin-oxo nano cluster resist concept. Soluble fluorinated tin-oxo clusters could be prepared, and they were cast into thin films from a fluorous solution. When the thin film was exposed to EUV radiation, it lost solubility, resulting in the formation of negative-tone images. Under an EUV lithographic condition, the thin film could be tailored down to 10 nm or smaller sized features. In addition, their unique solubility in chemically orthogonal solvents also enabled the build-up of a bilayer structure composed of a non-fluorinated reactive polymer underlayer without curing. The stacked film structure was found to be helpful for the sensitivity improvement. These results propose another interesting EUV resist candidate possessing unique capabilities in thin film processing. © COPYRIGHT SPIE. Downloading of the abstract is permitted for personal use only.

关键词： Tin

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P-210: Photolithography Patterning of Organic Light-Emitting Diodes Using Solvent Resistant Electron Transport Materials

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SID Symposium Digest of Technical Papers 2024年第1期55卷 2181-2183页

作者： Hyunjin Yu Eun Yeong So Kyunghyun Eun Byung Jun Jung Myungwoong Kim Jin-Kyun Lee Jun Yeob Lee School of Chemical Engineering Sungkyunkwan University 2066 Seobu-ro Jangan-gu Suwon-si Gyeonggi-do Republic of Korea 16419 Department of Materials Science and Engineering University of Seoul Seoul Republic of Korea 02504 Department of Chemistry and Chemical Engineering Inha University Incheon Republic of Korea 22212 Program in Environment and Polymer Engineering Inha University 100 Inha-ro Michuhol-gu Incheon Republic of Korea 22212

In this paper, we develop a novel approach to achieve ultra-high resolution in organic light-emitting diodes (OLEDs) through a photolithography patterning process. It is important to apply a solvent resistant electron transport layer (ETL) in the photolithography pattering of OLED because of solution coating process of photoresist on the ETL. Therefore, a solvent resistant ETL named 2,7-bis(4,6-diphenyl-1,3,5-triazin-2-yl)-9,9 ′ -spirobi[fluorene] (SBF-Trz) was developed and employed as the ETL of OLEDs. The SBF-Trz demonstrated excellent solvent resistance during photolithography process and enabled device performances comparable to those of the conventional OLED without any photolithography process. It was found that the SBF-Trz ETL is appropriate as the ETL of the OLED patterned by photolithography due to good electron transport property, good stability, and good solvent resistance.

关键词： Organic light-emitting diodes (OLED) Electron Transport Layer (ETL) Photolithography Patterning Reactive Ion Etching (RIE) Micro display Ultra High resolution FMM-Free

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Single Component Hydrophilic Terpolymer Thin Film Systems for Imparting Surface Chemical Versatility on Various Substrates

SSRN

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SSRN 2023年

作者： Kim, Myungwoong Ko, Yun Hee Nguyen, Hai Ha Tran Branstetter, Christopher R. Park, Soeun Lee, Jin-Kyun Yang, Jaesung Jung, Jangwook P. Department of Chemistry and Chemical Engineering Inha University Incheon22212 Korea Republic of Department of Applied Chemistry Reutlingen University Alteburgstraße 150 Reutlingen72762 Germany Department of Biological Engineering Louisiana State University Baton RougeLA70803 United States Program in Environment and Polymer Engineering Inha University Incheon22212 Korea Republic of Department of Polymer Science and Engineering Inha University Incheon22212 Korea Republic of Department of Chemistry Yonsei University Gangwon Wonju26493 Korea Republic of

We demonstrate hydrophilic photocrosslinkable copolymers that can attain single component functional organic coatings on various substrates. The copolymers were designed with a poly(ethylene oxide)-containing monomer, a monomer that can release a primary amine upon UV light illumination, and a monomer with reactive epoxide or cyclic dithiocarbonate with a primary amine. The resulting copolymers were easily adapted in the solution-casting process with polar solvents. Furthermore, the resulting coating was readily stabilized by crosslinking through UV light illumination, which is highly advantageous for achieving surface control of different substrates. The photocrosslinking capability further enables us to photolithographically define stable polymer domains in a desirable region. The resulting copolymer coatings were shown to be chemically versatile in immobilizing complex molecules by (i) post-crosslinking functionalization with the reactive groups on the surface and (ii) the formation of a composite coating by mixing varying amounts of a protein of interest, i.e., fish skin gelatin, which is capable of forming a dual crosslinked network. The number of functionalization sites in a thin film could be controlled by tuning the composition of the copolymers. In the photocrosslinking and subsequent functionalizations, we assessed the reactivity of the epoxide and cyclic dithiocarbonate with the generated primary amine. Moreover, the orthogonality of the possible reactions of the presented reactive functionalities in the crosslinked thin films with complex molecules was also assessed. The resulting copolymer coatings were further utilized to define a hydrophobic surface or an active surface for the adhesion of biological objects. © 2023, The Authors. All rights reserved.

关键词： Monomers

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Critical Review on the Abatement Of Endocrine Disrupting Compounds In Iron-Based Materials Catalyzed Persulfate Systems: Reactive Species, Reaction Mechanisms, and Perspectives

SSRN

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SSRN 2024年

作者： Sun, Ye Huang, Ying Zheng, Shujie Chen, Haojia Yang, Yan Ji, Hongbing Han, Changseok School of Chemical Engineering and Light Industry School of Environmental Science and Engineering Guangdong University of Technology Guangzhou510006 China School of Environment Hangzhou Institute for Advanced Study UCAS Hangzhou310024 China School of Chemistry and Chemical Engineering Guangxi Key Laboratory of Petrochemical Resource Processing and Process Intensification Technology Guangxi University Nanning530004 China Synergy Innovation Institute of Guangdong University of Technology Shantou515041 China Department of Environmental Engineering INHA University Incheon22212 Korea Republic of Program in Environmental and Polymer Engineering Graduate School of INHA University Incheon22212 Korea Republic of

Persulfate-based advanced oxidation processes have emerged as promising technologies for mitigating endocrine-disrupting compounds (EDCs) in wastewater treatment. Economically viable Fe-based materials with tailored properties have demonstrated significant efficacy in activating persulfate for the decomposition of EDCs through both radical-routes (•OH, SO4•−, and O2•−) and non-radical routes (1O2, surface activated PS complex, and high-valent Fe species). This review summarized the latest advancements in the persulfate activation mechanisms mediated by Fe-based materials, categorized by Fe valence states and the types of reactive species. Furthermore, it critically assesses the influence of active sites of Fe-based catalysts on persulfate activation pathways and summarizes the selective reaction of reactive species towards EDCs. Despite these advancements, several challenges persist in non-radical route-dominated persulfate activation, particularly regarding the impact of Fe-Fe distance on the reactive species and the catalytic role of Fe-based materials for reactions between inorganic ions and persulfate. This review proposes prospective research directions, provides design strategies, and expands the application of Fe-based materials in PS activation for effective EDC abatement in real situations. © 2024, The Authors. All rights reserved.

关键词： Endocrine disrupters

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Regioisomeric effects regulating the physicochemical properties of complex copolymers in thin films

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European polymer Journal 2025年 234卷

作者： Lee, Hyeji Kim, Seungjun Ko, Yun Hee Park, Juyoung Lee, Dahye Ku, Yejin Ahn, Chanjae Kwak, Yoonhyun Kim, Minsang Lee, Jin-Kyun Kim, Myungwoong Department of Chemistry and Chemical Engineering Inha University Incheon22212 Cuba Program in Environment and Polymer Engineering Inha University Incheon22212 Cuba Department of Polymer Science and Engineering Inha University Incheon22212 Cuba Material Research Center Samsung Advanced Institute of Technology Samsung Electronics Suwon16677 Cuba

We demonstrate that minimal alterations to the chemical structure of a hydroxystyrene (HOST)-containing terpolymer lead to significant changes in its physicochemical properties, which in turn govern photolithographic pattern formation in chemical amplification mechanism. While the structures of the three repeating units, their compositions, and the molecular weight characteristics of the terpolymers were controlled to be similar, the location of the phenolic OH groups was adjusted by copolymerizing o-, m-, and p-acetoxystyrene, subsequently transformed into o-, m-, and p-HOST through deacetylation. In the studies to examine the physicochemical properties of the copolymers, the copolymer with p-HOST showed dissolution rate in n-butyl acetate (nBA) of ≈ 15 nm/s, which was lower than that of copolymer with m-HOST (≈ 18 nm/s) and o-HOST (≈ 27 nm/s), further showing high linear correlation with the Hansen space distance between the copolymers and nBA. Moreover, the acid diffusions in the thin film, which plays a significant role in acid-catalyzed deprotection of the copolymers to solubility modulation, was affected by the location of the phenolic OH: the fastest and slowest acid diffusions were observed in the copolymers of p-HOST and o-HOST, respectively. The regioisomerism further affects the photolithographic performance collectively: (i) in contrast curve, light energy required to change the solubility was in order of p-HOST m-HOST > o-HOST, highlighting the significance of chemical structure design and the fundamental understanding of structure–property relationships. © 2025 Elsevier Ltd

关键词： Physicochemical properties

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