Fluorine-contained photoacid generators (PAGs) and corresponding polymer resists

Wang, Mingxing; Yueh, Wang; Gonsalves, Kenneth E.

doi:10.1016/j.jfluchem.2008.04.014

Cited by 9 publications

(3 citation statements)

References 21 publications

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“…There are more possible ways to increase the deprotection activation energy, such as using a secondary cation (i.e. isobornyl groups) 10 or substitute t-BOC carbonate with pendent t-butyl ester 4 . Leaving COOH groups after pending there deprotection also could probably decrease the diffusion, yet more research has to been done in order to figure out the key features of l-PEB resists.…”

Section: Diffusiomentioning

confidence: 99%

Line edge roughness of high deprotection activation energy photoresist by using sub-millisecond post exposure bake

et al. 2013

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The semiconductor industry is facing serious challenges in LWR control at the node of 16nm feature size. One of the reasons that causes LWR is the acid diffusion during post-exposure bake of chemically amplified resists. Laser spike annealing was introduced as a post-exposure bake (PEB) step in order to solve the image blurring problem by rapidly heating up a resist system to hundreds of degrees and completing the PEB in the millisecond time frame. However, lacking detailed knowledge of chemistry and kinetics for laser PEB (l-PEB) becomes an obstacle for resist design. The photoresist we synthesized with high deprotection activation energy and low diffusion activation energy has proved to help reduce LER for l-PEB. This photoresist was compared to another classical DUV model resist in order to analyze the benefits of its chemical structure and reaction kinetics. The interpretation of LER and activation energy will help us to identify better possible resist materials for l-PEB.

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Section: Diffusiomentioning

confidence: 99%

Line edge roughness of high deprotection activation energy photoresist by using sub-millisecond post exposure bake

et al. 2013

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“…Both electron beam lithography (EBL) and extreme ultraviolet lithography (EUVL) are advanced lithography technologies that are capable of achieving high-resolution patterns below 20 nm. , Consequently, steady improvement of resist materials for high-resolution lithography is of paramount importance. − Chemically amplified resists (CARs) have been the primary materials used in the semiconductor industry due to their excellent sensitivity for lithography. ,, In CARs, photoacid generators (PAGs) produce acid after exposure, which catalyzes the deprotection reaction of the acid-sensitive group, resulting in the solubility switch. − However, the poor line-edge roughness (LER) due to the acid diffusion and the uneven distribution of PAGs leads to the resolution limitation . The trade-off relationship among resolution, LER, and sensitivity demonstrates the limitations of CARs. , Researchers have attempted to bind PAG to the skeleton of materials to avoid nonuniform acid distribution and uncontrolled diffusion. − Yamamoto et al reported a series of polymer-bound PAG resists, achieving a 50 nm HP pattern with a line width roughness (LWR) of 3.9 nm. The patterning ability of the resist was significantly improved compared with the polymer-blended PAG resist (75 nm HP and LWR = 6.1 nm) .…”

Section: Introductionmentioning

confidence: 99%

Increasing the Sensitivity of Nonchemically Amplified Resists by Oxime Sulfonate-Functionalized Polystyrene

An,

Chen,

Zeng

et al. 2024

ACS Appl. Polym. Mater.

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Nonchemically amplified resists (n-CARs) based on oxime sulfonate-functionalized polystyrene (PSOS) were designed and prepared. The component ratios of the oxime sulfonate (OS) group in the polymer were well-controlled by changing the molar ratios of monomers, affording PSOS x (x = 100, 90, 60, and 40) polymers with oxime sulfonate ratios of 100, 89, 60, and 40%, respectively. The solubility, thermal stability, and film-forming ability for all of the polymers were evaluated, confirming the feasibility to use them as resist materials. The lithographic performances of PSOS x resists were studied by electron beam lithography (EBL) and extreme ultraviolet lithography (EUVL). PSOS x resists were demonstrated as dual-tone resists by using tetramethylammonium hydroxide (TMAH) as a positive tone developer and n-butyl acetate as a negative tone developer, respectively. Increasing the ratio of oxime sulfonate groups contributes to the negative tone development (NTD) patterns, while decreasing the ratio is conducive to the positive tone development (PTD) patterns. PSOS 100 resists can resolve 20 nm half-pitch (HP) patterns at a dose of 920 μC/cm 2 for NTD, and PSOS 40 resists can resolve 40 nm HP patterns at a dose of 1214 μC/cm 2 for PTD for EBL, respectively. The PSOS 100 resist was further evaluated by EUVL, achieving patterning performance down to 18 nm HP at a dose of 87.1 mJ/cm 2 with an LER of 2.3 nm for NTD. A comprehensive analysis of the patterning mechanism indicates that the decomposition of the oxime sulfonate group into sulfonic acid and other fragments upon exposure plays an important role in the solubility switch.

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“…6 In an attempt to overcome these current limitations, new classes of CARs have been developed. The most notable new classes of materials have been molecular glass photoresists [7][8][9][10][11][12] and polymer-bound photoacid generator (PAG) photoresists [13][14][15][16][17][18] . Molecular glass photoresists were originally introduced because it was thought that the reduction in resist molecule pixel size would improve LER.…”

Section: Introductionmentioning

confidence: 99%

Single-component molecular resists containing bound photoacid generator functionality

Lawson

Tolbert

Henderson

2010

J. Micro/Nanolith. MEMS MOEMS

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A series of single component molecular resists were designed, synthesized, characterized, and patterned using 100 keV e-beam lithography. An onium salt PAG based single component system (referred to here as TAS) which creates a free photoacid upon exposure is shown to produce a low line edge roughness (LER) of 3.9 nm (3σ), but was limited in resolution due to photoacid diffusion. A single component molecular resist with a covalently bound non-ionic photoacid generator (referred to here as NBB), i.e. one in which the photoacid anion is bound to the resist core, was found to exhibit an improved resolution of 40 nm due to reduced photoacid diffusion while maintaining a good LER and line width roughness (LWR) of 3.9 nm and 5.6 nm, respectively. Despite the small size of NBB, it was found to exhibit a glass transition temperature of 82°C. It also showed good adhesion, formed high quality films, and showed no dark erosion during development. These compounds demonstrate that it is possible to form single component molecular resists using both ionic and non-ionic photoacid generators and that such small molecule resists can provide all the basic requirements to serve as functional chemically amplified resists.

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Fluorine-contained photoacid generators (PAGs) and corresponding polymer resists

Cited by 9 publications

References 21 publications

Line edge roughness of high deprotection activation energy photoresist by using sub-millisecond post exposure bake

Line edge roughness of high deprotection activation energy photoresist by using sub-millisecond post exposure bake

Increasing the Sensitivity of Nonchemically Amplified Resists by Oxime Sulfonate-Functionalized Polystyrene

Single-component molecular resists containing bound photoacid generator functionality

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