Environmentally friendly natural materials-based photoacid generators for next-generation photolithography

Cho, Youngjin; Ouyang, Can; Krysak, Marie; Sun, Wenjie; Gamez, Victor; Sierra-Álvarez, Reyes; Ober, Christopher K.

doi:10.1117/12.879816

Cited by 3 publications

(3 citation statements)

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“…Reported studies dedicated to the design of PAGs for photochemical applications primarily followed ad hoc approaches based on chemical intuition and design rules (cf. [2,5]) coupled with pre-existing empirical knowledge of environmentally friendly molecular building blocks. Generative modeling of sulfoniums in the sense of contemporary deep learning approaches to small molecule discovery in drug design is yet to become a standard technique among practitioners of the art.…”

Section: Related Workmentioning

confidence: 99%

“…For several decades, performance of semiconductor photolithography has been enabled by technology of chemical amplification [1,2]. The level of regulatory scrutiny of key components of chemical amplification, photo-acid generators, has been steadily increasing [3][4][5]. The consensus across the industry is that accelerated discovery of novel PAGs is the core strategy in meeting growing market demands while further advancing photolithography performance and achieving a high level of sustainability of semiconductor manufacturing.…”

Section: Introductionmentioning

confidence: 99%

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Sample-Efficient Generation of Novel Photo-acid Generator Molecules using a Deep Generative Model

Hoffman¹,

Chenthamarakshan²,

Zubarev³

et al. 2021

Preprint

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Photo-acid generators (PAGs) are compounds that release acids (H + ions) when exposed to light. These compounds are critical components of the photolithography processes that are used in the manufacture of semiconductor logic and memory chips. The exponential increase in the demand for semiconductors has highlighted the need for discovering novel photo-acid generators. While de novo molecule design using deep generative models has been widely employed for drug discovery and material design, its application to the creation of novel photo-acid generators poses several unique challenges, such as lack of property labels. In this paper, we highlight these challenges and propose a generative modeling approach that utilizes conditional generation from a pre-trained deep autoencoder and expert-in-the-loop techniques. The validity of the proposed approach was evaluated with the help of subject matter experts, indicating the promise of such an approach for applications beyond the creation of novel photo-acid generators.Preprint. Under review.

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Section: Related Workmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Sample-Efficient Generation of Novel Photo-acid Generator Molecules using a Deep Generative Model

Hoffman¹,

Chenthamarakshan²,

Zubarev³

et al. 2021

Preprint

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“…Compounds 1 and 2 are likely to liberate the acid of a stable counter-anion, [5][6][7] whereas compounds 3-5 will liberate a sulfonic acid. 3,4,[8][9][10][11] Decreasing feature size is commensurate with the use of higher energy radiation ranging from the ultraviolet (UV; 450-190 nm) down to extreme ultraviolet (EUV) at 7 nm. 3,[12][13][14] Figure 4 shows a possible mechanism for the photochemical fragmentation of a Crivello or triarylsulfonium salt.…”

Section: Introductionmentioning

confidence: 99%

Potential photoacid generators based on oxime sulfonates

Plater

Harrison

Killah

2019

Journal of Chemical Research

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The bis-oxime of acenaphthenequinone and the mono-oxime of benzil have been sulfonated by reaction with 4-methylbenzenesulfonyl chloride and propylsulfonyl chloride. The four sulfonated oximes were characterised by X-ray single-crystal structure determinations. Some photochemical decompositions were studied using a 6-W 254-nm immersion well lamp in dichloromethane. The 4-methylbenzenesulfonate bis-oxime of acenaphthenequinone and the 4-methylbenzenesulfonate mono-oxime of benzil both give 4-methylbenzenesulfonic acid upon irradiation but not 4-methylbenzenesulfinic acid. Fragmentation pathways are discussed. The possible use of these compounds as photoacid generators in polymer resists and the role of secondary reactions to liberate acid is discussed.

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Lithography performance and environmental compatibility of PFOS-free photoacid generators

et al. 2017

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Photoacid generators (PAGs) with environmentally friendly cores and partially fluorinated sulfonate salts have been synthesized and studied. The cores were based on naturally occurring compounds such as cholesterol and glucose and were functionalized with a biodegradable octafluoro-3-oxapentanesulfonate. These PAGs were soluble in common spinning solvents and lithographically characterized with poly(styrene-co-4-hydroxy-styrene-co-tert-butylacetate) photoresist, and they showed higher resolution for photoresist applications than a perfluorooctane sulfonate (PFOS)-based triphenylsulfonium salt PAG, capable of patterning 50 nm dense lines. In addition, microbial bioassays confirmed that the newly developed PAG compounds can be broken down by microorganisms commonly found in conventional wastewater treatment systems. The biodegradation potential of the new PAGs presents a distinct advantage compared to that of PAG perfluorinated structures such as PFOS and perfluorobutane sulfonate, which are highly resistant to biodegradation and difficult to treat by conventional processes. The excellent performance and environmental compatibility of these PAGs make them promising candidates for use in high-resolution lithography systems.

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Environmentally friendly natural materials-based photoacid generators for next-generation photolithography

Cited by 3 publications

References 0 publications

Sample-Efficient Generation of Novel Photo-acid Generator Molecules using a Deep Generative Model

Sample-Efficient Generation of Novel Photo-acid Generator Molecules using a Deep Generative Model

Potential photoacid generators based on oxime sulfonates

Lithography performance and environmental compatibility of PFOS-free photoacid generators

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