Low-LER tin carboxylate photoresists using EUV

Ryan Del Re; Miriam Sortland; James Passarelli; Brian Cardineau; Yasin Ekinci; Michaela Vockenhuber; Mark Neisser; Daniel A. Freedman; Robert L. Brainard

doi:10.1117/12.2086597

Low-LER tin carboxylate photoresists using EUV

Ryan Del Re
, Miriam Sortland
, James Passarelli
, Brian Cardineau
, Yasin Ekinci
, Michaela Vockenhuber
, Mark Neisser
, Daniel A. Freedman
, Robert L. Brainard

Nanoscale Science and Engineering

University at Albany

Research output: Chapter in Book/Report/Conference proceeding › Conference contribution › peer-review

22 Scopus citations

Abstract

Pure thin films of organotin compounds have been lithographically evaluated using extreme ultraviolet lithography (EUVL, 13.5 nm). Twenty-one compounds of the type R₂Sn(O₂CR')₂ were spin-coated from solutions in toluene, exposed to EUV light, and developed in organic solvents. Exposures produced negativetone contrast curves and dense-line patterns using interference lithography. Contrast-curve studies indicated that the E_max values were linearly related to molecular weight when plotted separately depending upon the hydrocarbon group bound directly to tin (R = butyl, phenyl and benzyl). Additionally, E_max was found to be linearly related to free radical stability of the hydrocarbon group bound directly to tin. Dense-line patterning capabilities varied, but two resists in particular show exceptionally good line edge roughness (LER). A resist composed of an amorphous film of (C₆H₅CH₂)₂Sn(O₂CC(CH₃)₃)₂ (13) achieved 1.4 nm LER at 22 nm halfpitch patterning and a resist composed of (C₆H₅CH₂)₂Sn(O₂CC₆H₅)₂ (14) achieved 1.1 nm LER at 35 nm halfpitch at high exposure doses (600 mJ/cm²). Two photoresists that use olefin-based carboxylates, (C₆H₅CH₂)₂Sn(O₂CCH=CH₂)₂ (11) and (C₆H₅CH₂)₂Sn(O₂CC(CH₃)=CH₂)₂ (12), demonstrated much improved photospeeds (5 mJ/cm² and 27 mJ/cm²) but with worse LER.

Original language	English
Title of host publication	Extreme Ultraviolet (EUV) Lithography VI
Editors	Obert R. Wood, Eric M. Panning
Publisher	SPIE
ISBN (Electronic)	9781628415247
DOIs	https://doi.org/10.1117/12.2086597
State	Published - 2015
Event	Extreme Ultraviolet (EUV) Lithography VI Conference - San Jose, United States Duration: Feb 23 2015 → Feb 26 2015

Publication series

Name	Proceedings of SPIE - The International Society for Optical Engineering
Volume	9422

Conference

Conference	Extreme Ultraviolet (EUV) Lithography VI Conference
Country/Territory	United States
City	San Jose
Period	02/23/15 → 02/26/15

Keywords

EUV
LER
LWR
Line Edge Roughness
Line Width Roughness
Organometallic
Photoresist
Resist
Tin

Access to Document

10.1117/12.2086597

Cite this

Del Re, R., Sortland, M., Passarelli, J., Cardineau, B., Ekinci, Y., Vockenhuber, M., Neisser, M., Freedman, D. A., & Brainard, R. L. (2015). Low-LER tin carboxylate photoresists using EUV. In O. R. Wood, & E. M. Panning (Eds.), Extreme Ultraviolet (EUV) Lithography VI Article 942221 (Proceedings of SPIE - The International Society for Optical Engineering; Vol. 9422). SPIE. https://doi.org/10.1117/12.2086597

@inproceedings{826b34b27fe448a19dc649883adb8328,

title = "Low-LER tin carboxylate photoresists using EUV",

abstract = "Pure thin films of organotin compounds have been lithographically evaluated using extreme ultraviolet lithography (EUVL, 13.5 nm). Twenty-one compounds of the type R2Sn(O2CR')2 were spin-coated from solutions in toluene, exposed to EUV light, and developed in organic solvents. Exposures produced negativetone contrast curves and dense-line patterns using interference lithography. Contrast-curve studies indicated that the Emax values were linearly related to molecular weight when plotted separately depending upon the hydrocarbon group bound directly to tin (R = butyl, phenyl and benzyl). Additionally, Emax was found to be linearly related to free radical stability of the hydrocarbon group bound directly to tin. Dense-line patterning capabilities varied, but two resists in particular show exceptionally good line edge roughness (LER). A resist composed of an amorphous film of (C6H5CH2)2Sn(O2CC(CH3)3)2 (13) achieved 1.4 nm LER at 22 nm halfpitch patterning and a resist composed of (C6H5CH2)2Sn(O2CC6H5)2 (14) achieved 1.1 nm LER at 35 nm halfpitch at high exposure doses (600 mJ/cm2). Two photoresists that use olefin-based carboxylates, (C6H5CH2)2Sn(O2CCH=CH2)2 (11) and (C6H5CH2)2Sn(O2CC(CH3)=CH2)2 (12), demonstrated much improved photospeeds (5 mJ/cm2 and 27 mJ/cm2) but with worse LER.",

keywords = "EUV, LER, LWR, Line Edge Roughness, Line Width Roughness, Organometallic, Photoresist, Resist, Tin",

author = "\{Del Re\}, Ryan and Miriam Sortland and James Passarelli and Brian Cardineau and Yasin Ekinci and Michaela Vockenhuber and Mark Neisser and Freedman, \{Daniel A.\} and Brainard, \{Robert L.\}",

note = "Publisher Copyright: {\textcopyright} 2015 SPIE.; Extreme Ultraviolet (EUV) Lithography VI Conference ; Conference date: 23-02-2015 Through 26-02-2015",

year = "2015",

doi = "10.1117/12.2086597",

language = "English",

series = "Proceedings of SPIE - The International Society for Optical Engineering",

publisher = "SPIE",

editor = "Wood, \{Obert R.\} and Panning, \{Eric M.\}",

booktitle = "Extreme Ultraviolet (EUV) Lithography VI",

}

Del Re, R, Sortland, M, Passarelli, J, Cardineau, B, Ekinci, Y, Vockenhuber, M, Neisser, M, Freedman, DA & Brainard, RL 2015, Low-LER tin carboxylate photoresists using EUV. in OR Wood & EM Panning (eds), Extreme Ultraviolet (EUV) Lithography VI., 942221, Proceedings of SPIE - The International Society for Optical Engineering, vol. 9422, SPIE, Extreme Ultraviolet (EUV) Lithography VI Conference, San Jose, United States, 02/23/15. https://doi.org/10.1117/12.2086597

Low-LER tin carboxylate photoresists using EUV. / Del Re, Ryan; Sortland, Miriam; Passarelli, James et al.
Extreme Ultraviolet (EUV) Lithography VI. ed. / Obert R. Wood; Eric M. Panning. SPIE, 2015. 942221 (Proceedings of SPIE - The International Society for Optical Engineering; Vol. 9422).

Research output: Chapter in Book/Report/Conference proceeding › Conference contribution › peer-review

TY - GEN

T1 - Low-LER tin carboxylate photoresists using EUV

AU - Del Re, Ryan

AU - Sortland, Miriam

AU - Passarelli, James

AU - Cardineau, Brian

AU - Ekinci, Yasin

AU - Vockenhuber, Michaela

AU - Neisser, Mark

AU - Freedman, Daniel A.

AU - Brainard, Robert L.

PY - 2015

Y1 - 2015

N2 - Pure thin films of organotin compounds have been lithographically evaluated using extreme ultraviolet lithography (EUVL, 13.5 nm). Twenty-one compounds of the type R2Sn(O2CR')2 were spin-coated from solutions in toluene, exposed to EUV light, and developed in organic solvents. Exposures produced negativetone contrast curves and dense-line patterns using interference lithography. Contrast-curve studies indicated that the Emax values were linearly related to molecular weight when plotted separately depending upon the hydrocarbon group bound directly to tin (R = butyl, phenyl and benzyl). Additionally, Emax was found to be linearly related to free radical stability of the hydrocarbon group bound directly to tin. Dense-line patterning capabilities varied, but two resists in particular show exceptionally good line edge roughness (LER). A resist composed of an amorphous film of (C6H5CH2)2Sn(O2CC(CH3)3)2 (13) achieved 1.4 nm LER at 22 nm halfpitch patterning and a resist composed of (C6H5CH2)2Sn(O2CC6H5)2 (14) achieved 1.1 nm LER at 35 nm halfpitch at high exposure doses (600 mJ/cm2). Two photoresists that use olefin-based carboxylates, (C6H5CH2)2Sn(O2CCH=CH2)2 (11) and (C6H5CH2)2Sn(O2CC(CH3)=CH2)2 (12), demonstrated much improved photospeeds (5 mJ/cm2 and 27 mJ/cm2) but with worse LER.

AB - Pure thin films of organotin compounds have been lithographically evaluated using extreme ultraviolet lithography (EUVL, 13.5 nm). Twenty-one compounds of the type R2Sn(O2CR')2 were spin-coated from solutions in toluene, exposed to EUV light, and developed in organic solvents. Exposures produced negativetone contrast curves and dense-line patterns using interference lithography. Contrast-curve studies indicated that the Emax values were linearly related to molecular weight when plotted separately depending upon the hydrocarbon group bound directly to tin (R = butyl, phenyl and benzyl). Additionally, Emax was found to be linearly related to free radical stability of the hydrocarbon group bound directly to tin. Dense-line patterning capabilities varied, but two resists in particular show exceptionally good line edge roughness (LER). A resist composed of an amorphous film of (C6H5CH2)2Sn(O2CC(CH3)3)2 (13) achieved 1.4 nm LER at 22 nm halfpitch patterning and a resist composed of (C6H5CH2)2Sn(O2CC6H5)2 (14) achieved 1.1 nm LER at 35 nm halfpitch at high exposure doses (600 mJ/cm2). Two photoresists that use olefin-based carboxylates, (C6H5CH2)2Sn(O2CCH=CH2)2 (11) and (C6H5CH2)2Sn(O2CC(CH3)=CH2)2 (12), demonstrated much improved photospeeds (5 mJ/cm2 and 27 mJ/cm2) but with worse LER.

KW - EUV

KW - LER

KW - LWR

KW - Line Edge Roughness

KW - Line Width Roughness

KW - Organometallic

KW - Photoresist

KW - Resist

KW - Tin

UR - https://www.scopus.com/pages/publications/84931460808

U2 - 10.1117/12.2086597

DO - 10.1117/12.2086597

M3 - Conference contribution

T3 - Proceedings of SPIE - The International Society for Optical Engineering

BT - Extreme Ultraviolet (EUV) Lithography VI

A2 - Wood, Obert R.

A2 - Panning, Eric M.

PB - SPIE

T2 - Extreme Ultraviolet (EUV) Lithography VI Conference

Y2 - 23 February 2015 through 26 February 2015

ER -

Low-LER tin carboxylate photoresists using EUV

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Keywords

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