Abstract

We propose in this paper to use the delayed gel point character of thiol-ene-based resist to reduce the influence of polymerization shrinkage during the replication of micro-optical elements with continuous relief by UV embossing. Experiment results indicate that this resist can be used to bring down the fabrication error to less than 2% in the vertical direction at a proper thickness of the residual resist, which is far less than that of traditional acrylate-based resist. This resist can also be used to transfer continuous relief into a fused silica substrate through reactive ion etching because of its good etching resistance.

© 2011 Optical Society of America

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    [CrossRef] [PubMed]
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    [CrossRef]
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    [CrossRef]
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    [CrossRef]
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    [CrossRef] [PubMed]
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    [CrossRef]
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    [CrossRef] [PubMed]
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    [CrossRef]
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    [CrossRef] [PubMed]
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    [CrossRef]
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    [CrossRef] [PubMed]
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  19. P. J. Flory, “Molecular size distribution in three dimensional polymers. I. gelation,” J. Am. Chem. Soc. 63, 3083–3090(1941).
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    [CrossRef]
  21. J. A. Carioscia, H. Lu, J. W. Stanbury, and C. N. Bowman, “Thiol-ene oligomers as dental restorative materials,” Dent. Mater. 21, 1137–1143 (2005).
    [CrossRef] [PubMed]
  22. H. Lu, J. W. Stansbury, and C. N. Bowman, “Towards the elucidation of shrinkage stress development and relaxation in dental composites,” Dent. Mater. 20, 979–986 (2004).
    [CrossRef] [PubMed]

2010 (3)

C. Pina-Hernandez, L. J. Guo, and P. F. Fu, “High-resolution functional epoxysilsesquioxane-based patterning layers for large-area nanoimprinting,” ACS Nano 4, 4776–4784 (2010).
[CrossRef] [PubMed]

C. E. Hoyle and C. N. Bowman, “Thiol-ene click chemistry,” Angew. Chem. Int. Ed. Engl. 49, 1540–1573 (2010).
[CrossRef] [PubMed]

P. Jin, N. Liu, T. T. Liu, and J. B. Tan, “Replication of micro optical element with continuous relief profile in fused silica using UV-embossing and reactive ion etching,” Microelectron. Eng. 87, 1086–1090 (2010).
[CrossRef]

2009 (1)

E. A. Costner, M. W. Lin, W. L. Jen, and C. G. Willson, “Nanoimprint lithography materials development for semiconductor device fabrication,” Ann. Rev. Mater. Res. 39, 155–180 (2009).
[CrossRef]

2008 (3)

C. N. Bowman and C. J. Kloxin, “Toward an enhanced understanding and implementation of photopolymerization reactions,” AIChE J. 54, 2775–2795 (2008).
[CrossRef]

V. S. Khire, Y. Yi, N. A. Clark, and C. N. Bowman, “Formation and surface modification of nanopatterned thiol-ene substrates using step and flash imprint lithography,” Adv. Mater. 20, 3308–3313 (2008).
[CrossRef]

S. Landis, N. Chaix, C. Gourgon, and T. Leveder, “Quantitative characterizations of a nanopatterned bonded wafer: force determination for nanoimprint lithography stamp removal,” Nanotechnology 19, 125305 (2008).
[CrossRef] [PubMed]

2007 (1)

E. C. Hagberg, M. Malkoch, Y. B. Ling, C. J. Hawker, and K. R. Carter, “Effects of modulus and surface chemistry of thiol-ene photopolymers in nanoimprinting,” Nano Lett. 7, 233–237 (2007).
[CrossRef] [PubMed]

2006 (2)

D. I. Shin, S. H. Kim, H. S. Jeong, S. Lee, Y. Jin, J. Noh, H. Oh, K. Lee, D. H. Shin, and S. H. Song, “Fabrication of phone-camera module using wafer-scale UV embossing process,” Proc. SPIE 6068, 60680Q (2006).
[CrossRef]

Q. D. Wang, Y. G. Duan, B. H. Lu, Y. C. Ding, and Y. P. Tang, “Imprint template fabrication based on glass wet etching using a soft etching mask,” J. Micromech. Microeng. 16, 564–570 (2006).
[CrossRef]

2005 (4)

H. Lu, J. A. Carioscia, J. W. Stansbury, and C. N. Bowman, “Investigations of step-growth thiol-ene polymerizations for novel dental restoratives,” Dent. Mater. 21, 1129–1136(2005).
[CrossRef] [PubMed]

K. Wu, T. C. Bailey, C. G. Willson, and J. G. Ekerdt, “Surface hydration and its effect on fluorinated SAM formation on SiO2 surfaces,” Langmuir 21, 11795–11801 (2005).
[CrossRef] [PubMed]

E. K. Kim, M. D. Stewart, K. Wu, F. L. Palmieri, M. D. Dickey, J. G. Ekerdt, and C. G. Willson, “Vinyl ether formulations for step and flash imprint lithography,” J. Vac. Sci. Technol. B 23, 2967–2971 (2005).
[CrossRef]

J. A. Carioscia, H. Lu, J. W. Stanbury, and C. N. Bowman, “Thiol-ene oligomers as dental restorative materials,” Dent. Mater. 21, 1137–1143 (2005).
[CrossRef] [PubMed]

2004 (2)

H. Lu, J. W. Stansbury, and C. N. Bowman, “Towards the elucidation of shrinkage stress development and relaxation in dental composites,” Dent. Mater. 20, 979–986 (2004).
[CrossRef] [PubMed]

R. L. Burns, S. C. Johnson, G. M. Schmid, E. K. Kim, M. D. Dickey, J. Meiring, S. D. Burns, N. A. Stacey, C. G. Willson, D. Convey, Y. Wei, P. Fejes, K. Gehoski, D. Mancini, K. Nordquist, W. J. Dauksher, and D. J. Resnick, “Mesoscale modeling for SFIL simulating polymerization kinetics and densification,” Proc. SPIE 5374, 348–360 (2004).
[CrossRef]

2001 (1)

M. Colburn, I. Suez, B. J. Choi, M. Meissl, T. Bailey, S. V. Sreenivasan, J. G. Ekerdt, and C. G. Willson, “Characterization and modeling of volumetric and mechanical properties for step and flash imprint lithography photopolymers,” J. Vac. Sci. Technol. B 19, 2685–2689 (2001).
[CrossRef]

1995 (2)

1945 (1)

C. Walling, “Gel formation in addition polymerization,” J. Am. Chem. Soc. 67, 441–447 (1945).
[CrossRef]

1943 (1)

W. H. Stockmayer and H. Jacobson, “Gel formation in vinyl-divinyl copolymers,” J. Chem. Phys. 11, 393–393 (1943).
[CrossRef]

1941 (1)

P. J. Flory, “Molecular size distribution in three dimensional polymers. I. gelation,” J. Am. Chem. Soc. 63, 3083–3090(1941).
[CrossRef]

Bailey, T.

M. Colburn, I. Suez, B. J. Choi, M. Meissl, T. Bailey, S. V. Sreenivasan, J. G. Ekerdt, and C. G. Willson, “Characterization and modeling of volumetric and mechanical properties for step and flash imprint lithography photopolymers,” J. Vac. Sci. Technol. B 19, 2685–2689 (2001).
[CrossRef]

Bailey, T. C.

K. Wu, T. C. Bailey, C. G. Willson, and J. G. Ekerdt, “Surface hydration and its effect on fluorinated SAM formation on SiO2 surfaces,” Langmuir 21, 11795–11801 (2005).
[CrossRef] [PubMed]

Bowman, C. N.

C. E. Hoyle and C. N. Bowman, “Thiol-ene click chemistry,” Angew. Chem. Int. Ed. Engl. 49, 1540–1573 (2010).
[CrossRef] [PubMed]

C. N. Bowman and C. J. Kloxin, “Toward an enhanced understanding and implementation of photopolymerization reactions,” AIChE J. 54, 2775–2795 (2008).
[CrossRef]

V. S. Khire, Y. Yi, N. A. Clark, and C. N. Bowman, “Formation and surface modification of nanopatterned thiol-ene substrates using step and flash imprint lithography,” Adv. Mater. 20, 3308–3313 (2008).
[CrossRef]

H. Lu, J. A. Carioscia, J. W. Stansbury, and C. N. Bowman, “Investigations of step-growth thiol-ene polymerizations for novel dental restoratives,” Dent. Mater. 21, 1129–1136(2005).
[CrossRef] [PubMed]

J. A. Carioscia, H. Lu, J. W. Stanbury, and C. N. Bowman, “Thiol-ene oligomers as dental restorative materials,” Dent. Mater. 21, 1137–1143 (2005).
[CrossRef] [PubMed]

H. Lu, J. W. Stansbury, and C. N. Bowman, “Towards the elucidation of shrinkage stress development and relaxation in dental composites,” Dent. Mater. 20, 979–986 (2004).
[CrossRef] [PubMed]

Burns, R. L.

R. L. Burns, S. C. Johnson, G. M. Schmid, E. K. Kim, M. D. Dickey, J. Meiring, S. D. Burns, N. A. Stacey, C. G. Willson, D. Convey, Y. Wei, P. Fejes, K. Gehoski, D. Mancini, K. Nordquist, W. J. Dauksher, and D. J. Resnick, “Mesoscale modeling for SFIL simulating polymerization kinetics and densification,” Proc. SPIE 5374, 348–360 (2004).
[CrossRef]

Burns, S. D.

R. L. Burns, S. C. Johnson, G. M. Schmid, E. K. Kim, M. D. Dickey, J. Meiring, S. D. Burns, N. A. Stacey, C. G. Willson, D. Convey, Y. Wei, P. Fejes, K. Gehoski, D. Mancini, K. Nordquist, W. J. Dauksher, and D. J. Resnick, “Mesoscale modeling for SFIL simulating polymerization kinetics and densification,” Proc. SPIE 5374, 348–360 (2004).
[CrossRef]

Carioscia, J. A.

H. Lu, J. A. Carioscia, J. W. Stansbury, and C. N. Bowman, “Investigations of step-growth thiol-ene polymerizations for novel dental restoratives,” Dent. Mater. 21, 1129–1136(2005).
[CrossRef] [PubMed]

J. A. Carioscia, H. Lu, J. W. Stanbury, and C. N. Bowman, “Thiol-ene oligomers as dental restorative materials,” Dent. Mater. 21, 1137–1143 (2005).
[CrossRef] [PubMed]

Carter, K. R.

E. C. Hagberg, M. Malkoch, Y. B. Ling, C. J. Hawker, and K. R. Carter, “Effects of modulus and surface chemistry of thiol-ene photopolymers in nanoimprinting,” Nano Lett. 7, 233–237 (2007).
[CrossRef] [PubMed]

Chaix, N.

S. Landis, N. Chaix, C. Gourgon, and T. Leveder, “Quantitative characterizations of a nanopatterned bonded wafer: force determination for nanoimprint lithography stamp removal,” Nanotechnology 19, 125305 (2008).
[CrossRef] [PubMed]

Choi, B. J.

M. Colburn, I. Suez, B. J. Choi, M. Meissl, T. Bailey, S. V. Sreenivasan, J. G. Ekerdt, and C. G. Willson, “Characterization and modeling of volumetric and mechanical properties for step and flash imprint lithography photopolymers,” J. Vac. Sci. Technol. B 19, 2685–2689 (2001).
[CrossRef]

Clark, N. A.

V. S. Khire, Y. Yi, N. A. Clark, and C. N. Bowman, “Formation and surface modification of nanopatterned thiol-ene substrates using step and flash imprint lithography,” Adv. Mater. 20, 3308–3313 (2008).
[CrossRef]

Colburn, M.

M. Colburn, I. Suez, B. J. Choi, M. Meissl, T. Bailey, S. V. Sreenivasan, J. G. Ekerdt, and C. G. Willson, “Characterization and modeling of volumetric and mechanical properties for step and flash imprint lithography photopolymers,” J. Vac. Sci. Technol. B 19, 2685–2689 (2001).
[CrossRef]

Convey, D.

R. L. Burns, S. C. Johnson, G. M. Schmid, E. K. Kim, M. D. Dickey, J. Meiring, S. D. Burns, N. A. Stacey, C. G. Willson, D. Convey, Y. Wei, P. Fejes, K. Gehoski, D. Mancini, K. Nordquist, W. J. Dauksher, and D. J. Resnick, “Mesoscale modeling for SFIL simulating polymerization kinetics and densification,” Proc. SPIE 5374, 348–360 (2004).
[CrossRef]

Costner, E. A.

E. A. Costner, M. W. Lin, W. L. Jen, and C. G. Willson, “Nanoimprint lithography materials development for semiconductor device fabrication,” Ann. Rev. Mater. Res. 39, 155–180 (2009).
[CrossRef]

Dauksher, W. J.

R. L. Burns, S. C. Johnson, G. M. Schmid, E. K. Kim, M. D. Dickey, J. Meiring, S. D. Burns, N. A. Stacey, C. G. Willson, D. Convey, Y. Wei, P. Fejes, K. Gehoski, D. Mancini, K. Nordquist, W. J. Dauksher, and D. J. Resnick, “Mesoscale modeling for SFIL simulating polymerization kinetics and densification,” Proc. SPIE 5374, 348–360 (2004).
[CrossRef]

Dickey, M. D.

E. K. Kim, M. D. Stewart, K. Wu, F. L. Palmieri, M. D. Dickey, J. G. Ekerdt, and C. G. Willson, “Vinyl ether formulations for step and flash imprint lithography,” J. Vac. Sci. Technol. B 23, 2967–2971 (2005).
[CrossRef]

R. L. Burns, S. C. Johnson, G. M. Schmid, E. K. Kim, M. D. Dickey, J. Meiring, S. D. Burns, N. A. Stacey, C. G. Willson, D. Convey, Y. Wei, P. Fejes, K. Gehoski, D. Mancini, K. Nordquist, W. J. Dauksher, and D. J. Resnick, “Mesoscale modeling for SFIL simulating polymerization kinetics and densification,” Proc. SPIE 5374, 348–360 (2004).
[CrossRef]

Ding, Y. C.

Q. D. Wang, Y. G. Duan, B. H. Lu, Y. C. Ding, and Y. P. Tang, “Imprint template fabrication based on glass wet etching using a soft etching mask,” J. Micromech. Microeng. 16, 564–570 (2006).
[CrossRef]

Dong, B. Z.

Duan, Y. G.

Q. D. Wang, Y. G. Duan, B. H. Lu, Y. C. Ding, and Y. P. Tang, “Imprint template fabrication based on glass wet etching using a soft etching mask,” J. Micromech. Microeng. 16, 564–570 (2006).
[CrossRef]

Ekerdt, J. G.

E. K. Kim, M. D. Stewart, K. Wu, F. L. Palmieri, M. D. Dickey, J. G. Ekerdt, and C. G. Willson, “Vinyl ether formulations for step and flash imprint lithography,” J. Vac. Sci. Technol. B 23, 2967–2971 (2005).
[CrossRef]

K. Wu, T. C. Bailey, C. G. Willson, and J. G. Ekerdt, “Surface hydration and its effect on fluorinated SAM formation on SiO2 surfaces,” Langmuir 21, 11795–11801 (2005).
[CrossRef] [PubMed]

M. Colburn, I. Suez, B. J. Choi, M. Meissl, T. Bailey, S. V. Sreenivasan, J. G. Ekerdt, and C. G. Willson, “Characterization and modeling of volumetric and mechanical properties for step and flash imprint lithography photopolymers,” J. Vac. Sci. Technol. B 19, 2685–2689 (2001).
[CrossRef]

Fejes, P.

R. L. Burns, S. C. Johnson, G. M. Schmid, E. K. Kim, M. D. Dickey, J. Meiring, S. D. Burns, N. A. Stacey, C. G. Willson, D. Convey, Y. Wei, P. Fejes, K. Gehoski, D. Mancini, K. Nordquist, W. J. Dauksher, and D. J. Resnick, “Mesoscale modeling for SFIL simulating polymerization kinetics and densification,” Proc. SPIE 5374, 348–360 (2004).
[CrossRef]

Flory, P. J.

P. J. Flory, “Molecular size distribution in three dimensional polymers. I. gelation,” J. Am. Chem. Soc. 63, 3083–3090(1941).
[CrossRef]

Fu, P. F.

C. Pina-Hernandez, L. J. Guo, and P. F. Fu, “High-resolution functional epoxysilsesquioxane-based patterning layers for large-area nanoimprinting,” ACS Nano 4, 4776–4784 (2010).
[CrossRef] [PubMed]

Gehoski, K.

R. L. Burns, S. C. Johnson, G. M. Schmid, E. K. Kim, M. D. Dickey, J. Meiring, S. D. Burns, N. A. Stacey, C. G. Willson, D. Convey, Y. Wei, P. Fejes, K. Gehoski, D. Mancini, K. Nordquist, W. J. Dauksher, and D. J. Resnick, “Mesoscale modeling for SFIL simulating polymerization kinetics and densification,” Proc. SPIE 5374, 348–360 (2004).
[CrossRef]

Gourgon, C.

S. Landis, N. Chaix, C. Gourgon, and T. Leveder, “Quantitative characterizations of a nanopatterned bonded wafer: force determination for nanoimprint lithography stamp removal,” Nanotechnology 19, 125305 (2008).
[CrossRef] [PubMed]

Gu, B. Y.

Guo, L. J.

C. Pina-Hernandez, L. J. Guo, and P. F. Fu, “High-resolution functional epoxysilsesquioxane-based patterning layers for large-area nanoimprinting,” ACS Nano 4, 4776–4784 (2010).
[CrossRef] [PubMed]

Hagberg, E. C.

E. C. Hagberg, M. Malkoch, Y. B. Ling, C. J. Hawker, and K. R. Carter, “Effects of modulus and surface chemistry of thiol-ene photopolymers in nanoimprinting,” Nano Lett. 7, 233–237 (2007).
[CrossRef] [PubMed]

Hawker, C. J.

E. C. Hagberg, M. Malkoch, Y. B. Ling, C. J. Hawker, and K. R. Carter, “Effects of modulus and surface chemistry of thiol-ene photopolymers in nanoimprinting,” Nano Lett. 7, 233–237 (2007).
[CrossRef] [PubMed]

Herzig, H. P.

Hoyle, C. E.

C. E. Hoyle and C. N. Bowman, “Thiol-ene click chemistry,” Angew. Chem. Int. Ed. Engl. 49, 1540–1573 (2010).
[CrossRef] [PubMed]

Jacobson, H.

W. H. Stockmayer and H. Jacobson, “Gel formation in vinyl-divinyl copolymers,” J. Chem. Phys. 11, 393–393 (1943).
[CrossRef]

Jen, W. L.

E. A. Costner, M. W. Lin, W. L. Jen, and C. G. Willson, “Nanoimprint lithography materials development for semiconductor device fabrication,” Ann. Rev. Mater. Res. 39, 155–180 (2009).
[CrossRef]

Jeong, H. S.

D. I. Shin, S. H. Kim, H. S. Jeong, S. Lee, Y. Jin, J. Noh, H. Oh, K. Lee, D. H. Shin, and S. H. Song, “Fabrication of phone-camera module using wafer-scale UV embossing process,” Proc. SPIE 6068, 60680Q (2006).
[CrossRef]

Jin, P.

P. Jin, N. Liu, T. T. Liu, and J. B. Tan, “Replication of micro optical element with continuous relief profile in fused silica using UV-embossing and reactive ion etching,” Microelectron. Eng. 87, 1086–1090 (2010).
[CrossRef]

Jin, Y.

D. I. Shin, S. H. Kim, H. S. Jeong, S. Lee, Y. Jin, J. Noh, H. Oh, K. Lee, D. H. Shin, and S. H. Song, “Fabrication of phone-camera module using wafer-scale UV embossing process,” Proc. SPIE 6068, 60680Q (2006).
[CrossRef]

Johnson, S. C.

R. L. Burns, S. C. Johnson, G. M. Schmid, E. K. Kim, M. D. Dickey, J. Meiring, S. D. Burns, N. A. Stacey, C. G. Willson, D. Convey, Y. Wei, P. Fejes, K. Gehoski, D. Mancini, K. Nordquist, W. J. Dauksher, and D. J. Resnick, “Mesoscale modeling for SFIL simulating polymerization kinetics and densification,” Proc. SPIE 5374, 348–360 (2004).
[CrossRef]

Khire, V. S.

V. S. Khire, Y. Yi, N. A. Clark, and C. N. Bowman, “Formation and surface modification of nanopatterned thiol-ene substrates using step and flash imprint lithography,” Adv. Mater. 20, 3308–3313 (2008).
[CrossRef]

Kim, E. K.

E. K. Kim, M. D. Stewart, K. Wu, F. L. Palmieri, M. D. Dickey, J. G. Ekerdt, and C. G. Willson, “Vinyl ether formulations for step and flash imprint lithography,” J. Vac. Sci. Technol. B 23, 2967–2971 (2005).
[CrossRef]

R. L. Burns, S. C. Johnson, G. M. Schmid, E. K. Kim, M. D. Dickey, J. Meiring, S. D. Burns, N. A. Stacey, C. G. Willson, D. Convey, Y. Wei, P. Fejes, K. Gehoski, D. Mancini, K. Nordquist, W. J. Dauksher, and D. J. Resnick, “Mesoscale modeling for SFIL simulating polymerization kinetics and densification,” Proc. SPIE 5374, 348–360 (2004).
[CrossRef]

Kim, S. H.

D. I. Shin, S. H. Kim, H. S. Jeong, S. Lee, Y. Jin, J. Noh, H. Oh, K. Lee, D. H. Shin, and S. H. Song, “Fabrication of phone-camera module using wafer-scale UV embossing process,” Proc. SPIE 6068, 60680Q (2006).
[CrossRef]

Kloxin, C. J.

C. N. Bowman and C. J. Kloxin, “Toward an enhanced understanding and implementation of photopolymerization reactions,” AIChE J. 54, 2775–2795 (2008).
[CrossRef]

Kunz, R. E.

Landis, S.

S. Landis, N. Chaix, C. Gourgon, and T. Leveder, “Quantitative characterizations of a nanopatterned bonded wafer: force determination for nanoimprint lithography stamp removal,” Nanotechnology 19, 125305 (2008).
[CrossRef] [PubMed]

Lee, K.

D. I. Shin, S. H. Kim, H. S. Jeong, S. Lee, Y. Jin, J. Noh, H. Oh, K. Lee, D. H. Shin, and S. H. Song, “Fabrication of phone-camera module using wafer-scale UV embossing process,” Proc. SPIE 6068, 60680Q (2006).
[CrossRef]

Lee, S.

D. I. Shin, S. H. Kim, H. S. Jeong, S. Lee, Y. Jin, J. Noh, H. Oh, K. Lee, D. H. Shin, and S. H. Song, “Fabrication of phone-camera module using wafer-scale UV embossing process,” Proc. SPIE 6068, 60680Q (2006).
[CrossRef]

Leveder, T.

S. Landis, N. Chaix, C. Gourgon, and T. Leveder, “Quantitative characterizations of a nanopatterned bonded wafer: force determination for nanoimprint lithography stamp removal,” Nanotechnology 19, 125305 (2008).
[CrossRef] [PubMed]

Lin, M. W.

E. A. Costner, M. W. Lin, W. L. Jen, and C. G. Willson, “Nanoimprint lithography materials development for semiconductor device fabrication,” Ann. Rev. Mater. Res. 39, 155–180 (2009).
[CrossRef]

Ling, Y. B.

E. C. Hagberg, M. Malkoch, Y. B. Ling, C. J. Hawker, and K. R. Carter, “Effects of modulus and surface chemistry of thiol-ene photopolymers in nanoimprinting,” Nano Lett. 7, 233–237 (2007).
[CrossRef] [PubMed]

Liu, N.

P. Jin, N. Liu, T. T. Liu, and J. B. Tan, “Replication of micro optical element with continuous relief profile in fused silica using UV-embossing and reactive ion etching,” Microelectron. Eng. 87, 1086–1090 (2010).
[CrossRef]

Liu, T. T.

P. Jin, N. Liu, T. T. Liu, and J. B. Tan, “Replication of micro optical element with continuous relief profile in fused silica using UV-embossing and reactive ion etching,” Microelectron. Eng. 87, 1086–1090 (2010).
[CrossRef]

Lu, B. H.

Q. D. Wang, Y. G. Duan, B. H. Lu, Y. C. Ding, and Y. P. Tang, “Imprint template fabrication based on glass wet etching using a soft etching mask,” J. Micromech. Microeng. 16, 564–570 (2006).
[CrossRef]

Lu, H.

J. A. Carioscia, H. Lu, J. W. Stanbury, and C. N. Bowman, “Thiol-ene oligomers as dental restorative materials,” Dent. Mater. 21, 1137–1143 (2005).
[CrossRef] [PubMed]

H. Lu, J. A. Carioscia, J. W. Stansbury, and C. N. Bowman, “Investigations of step-growth thiol-ene polymerizations for novel dental restoratives,” Dent. Mater. 21, 1129–1136(2005).
[CrossRef] [PubMed]

H. Lu, J. W. Stansbury, and C. N. Bowman, “Towards the elucidation of shrinkage stress development and relaxation in dental composites,” Dent. Mater. 20, 979–986 (2004).
[CrossRef] [PubMed]

Malkoch, M.

E. C. Hagberg, M. Malkoch, Y. B. Ling, C. J. Hawker, and K. R. Carter, “Effects of modulus and surface chemistry of thiol-ene photopolymers in nanoimprinting,” Nano Lett. 7, 233–237 (2007).
[CrossRef] [PubMed]

Mancini, D.

R. L. Burns, S. C. Johnson, G. M. Schmid, E. K. Kim, M. D. Dickey, J. Meiring, S. D. Burns, N. A. Stacey, C. G. Willson, D. Convey, Y. Wei, P. Fejes, K. Gehoski, D. Mancini, K. Nordquist, W. J. Dauksher, and D. J. Resnick, “Mesoscale modeling for SFIL simulating polymerization kinetics and densification,” Proc. SPIE 5374, 348–360 (2004).
[CrossRef]

Meiring, J.

R. L. Burns, S. C. Johnson, G. M. Schmid, E. K. Kim, M. D. Dickey, J. Meiring, S. D. Burns, N. A. Stacey, C. G. Willson, D. Convey, Y. Wei, P. Fejes, K. Gehoski, D. Mancini, K. Nordquist, W. J. Dauksher, and D. J. Resnick, “Mesoscale modeling for SFIL simulating polymerization kinetics and densification,” Proc. SPIE 5374, 348–360 (2004).
[CrossRef]

Meissl, M.

M. Colburn, I. Suez, B. J. Choi, M. Meissl, T. Bailey, S. V. Sreenivasan, J. G. Ekerdt, and C. G. Willson, “Characterization and modeling of volumetric and mechanical properties for step and flash imprint lithography photopolymers,” J. Vac. Sci. Technol. B 19, 2685–2689 (2001).
[CrossRef]

Noh, J.

D. I. Shin, S. H. Kim, H. S. Jeong, S. Lee, Y. Jin, J. Noh, H. Oh, K. Lee, D. H. Shin, and S. H. Song, “Fabrication of phone-camera module using wafer-scale UV embossing process,” Proc. SPIE 6068, 60680Q (2006).
[CrossRef]

Nordquist, K.

R. L. Burns, S. C. Johnson, G. M. Schmid, E. K. Kim, M. D. Dickey, J. Meiring, S. D. Burns, N. A. Stacey, C. G. Willson, D. Convey, Y. Wei, P. Fejes, K. Gehoski, D. Mancini, K. Nordquist, W. J. Dauksher, and D. J. Resnick, “Mesoscale modeling for SFIL simulating polymerization kinetics and densification,” Proc. SPIE 5374, 348–360 (2004).
[CrossRef]

Oh, H.

D. I. Shin, S. H. Kim, H. S. Jeong, S. Lee, Y. Jin, J. Noh, H. Oh, K. Lee, D. H. Shin, and S. H. Song, “Fabrication of phone-camera module using wafer-scale UV embossing process,” Proc. SPIE 6068, 60680Q (2006).
[CrossRef]

Palmieri, F. L.

E. K. Kim, M. D. Stewart, K. Wu, F. L. Palmieri, M. D. Dickey, J. G. Ekerdt, and C. G. Willson, “Vinyl ether formulations for step and flash imprint lithography,” J. Vac. Sci. Technol. B 23, 2967–2971 (2005).
[CrossRef]

Pina-Hernandez, C.

C. Pina-Hernandez, L. J. Guo, and P. F. Fu, “High-resolution functional epoxysilsesquioxane-based patterning layers for large-area nanoimprinting,” ACS Nano 4, 4776–4784 (2010).
[CrossRef] [PubMed]

Resnick, D. J.

R. L. Burns, S. C. Johnson, G. M. Schmid, E. K. Kim, M. D. Dickey, J. Meiring, S. D. Burns, N. A. Stacey, C. G. Willson, D. Convey, Y. Wei, P. Fejes, K. Gehoski, D. Mancini, K. Nordquist, W. J. Dauksher, and D. J. Resnick, “Mesoscale modeling for SFIL simulating polymerization kinetics and densification,” Proc. SPIE 5374, 348–360 (2004).
[CrossRef]

Rossi, M.

Schmid, G. M.

R. L. Burns, S. C. Johnson, G. M. Schmid, E. K. Kim, M. D. Dickey, J. Meiring, S. D. Burns, N. A. Stacey, C. G. Willson, D. Convey, Y. Wei, P. Fejes, K. Gehoski, D. Mancini, K. Nordquist, W. J. Dauksher, and D. J. Resnick, “Mesoscale modeling for SFIL simulating polymerization kinetics and densification,” Proc. SPIE 5374, 348–360 (2004).
[CrossRef]

Shin, D. H.

D. I. Shin, S. H. Kim, H. S. Jeong, S. Lee, Y. Jin, J. Noh, H. Oh, K. Lee, D. H. Shin, and S. H. Song, “Fabrication of phone-camera module using wafer-scale UV embossing process,” Proc. SPIE 6068, 60680Q (2006).
[CrossRef]

Shin, D. I.

D. I. Shin, S. H. Kim, H. S. Jeong, S. Lee, Y. Jin, J. Noh, H. Oh, K. Lee, D. H. Shin, and S. H. Song, “Fabrication of phone-camera module using wafer-scale UV embossing process,” Proc. SPIE 6068, 60680Q (2006).
[CrossRef]

Song, S. H.

D. I. Shin, S. H. Kim, H. S. Jeong, S. Lee, Y. Jin, J. Noh, H. Oh, K. Lee, D. H. Shin, and S. H. Song, “Fabrication of phone-camera module using wafer-scale UV embossing process,” Proc. SPIE 6068, 60680Q (2006).
[CrossRef]

Sreenivasan, S. V.

M. Colburn, I. Suez, B. J. Choi, M. Meissl, T. Bailey, S. V. Sreenivasan, J. G. Ekerdt, and C. G. Willson, “Characterization and modeling of volumetric and mechanical properties for step and flash imprint lithography photopolymers,” J. Vac. Sci. Technol. B 19, 2685–2689 (2001).
[CrossRef]

Stacey, N. A.

R. L. Burns, S. C. Johnson, G. M. Schmid, E. K. Kim, M. D. Dickey, J. Meiring, S. D. Burns, N. A. Stacey, C. G. Willson, D. Convey, Y. Wei, P. Fejes, K. Gehoski, D. Mancini, K. Nordquist, W. J. Dauksher, and D. J. Resnick, “Mesoscale modeling for SFIL simulating polymerization kinetics and densification,” Proc. SPIE 5374, 348–360 (2004).
[CrossRef]

Stanbury, J. W.

J. A. Carioscia, H. Lu, J. W. Stanbury, and C. N. Bowman, “Thiol-ene oligomers as dental restorative materials,” Dent. Mater. 21, 1137–1143 (2005).
[CrossRef] [PubMed]

Stansbury, J. W.

H. Lu, J. A. Carioscia, J. W. Stansbury, and C. N. Bowman, “Investigations of step-growth thiol-ene polymerizations for novel dental restoratives,” Dent. Mater. 21, 1129–1136(2005).
[CrossRef] [PubMed]

H. Lu, J. W. Stansbury, and C. N. Bowman, “Towards the elucidation of shrinkage stress development and relaxation in dental composites,” Dent. Mater. 20, 979–986 (2004).
[CrossRef] [PubMed]

Stewart, M. D.

E. K. Kim, M. D. Stewart, K. Wu, F. L. Palmieri, M. D. Dickey, J. G. Ekerdt, and C. G. Willson, “Vinyl ether formulations for step and flash imprint lithography,” J. Vac. Sci. Technol. B 23, 2967–2971 (2005).
[CrossRef]

Stockmayer, W. H.

W. H. Stockmayer and H. Jacobson, “Gel formation in vinyl-divinyl copolymers,” J. Chem. Phys. 11, 393–393 (1943).
[CrossRef]

Suez, I.

M. Colburn, I. Suez, B. J. Choi, M. Meissl, T. Bailey, S. V. Sreenivasan, J. G. Ekerdt, and C. G. Willson, “Characterization and modeling of volumetric and mechanical properties for step and flash imprint lithography photopolymers,” J. Vac. Sci. Technol. B 19, 2685–2689 (2001).
[CrossRef]

Tan, J. B.

P. Jin, N. Liu, T. T. Liu, and J. B. Tan, “Replication of micro optical element with continuous relief profile in fused silica using UV-embossing and reactive ion etching,” Microelectron. Eng. 87, 1086–1090 (2010).
[CrossRef]

Tan, X.

Tang, Y. P.

Q. D. Wang, Y. G. Duan, B. H. Lu, Y. C. Ding, and Y. P. Tang, “Imprint template fabrication based on glass wet etching using a soft etching mask,” J. Micromech. Microeng. 16, 564–570 (2006).
[CrossRef]

Walling, C.

C. Walling, “Gel formation in addition polymerization,” J. Am. Chem. Soc. 67, 441–447 (1945).
[CrossRef]

Wang, Q. D.

Q. D. Wang, Y. G. Duan, B. H. Lu, Y. C. Ding, and Y. P. Tang, “Imprint template fabrication based on glass wet etching using a soft etching mask,” J. Micromech. Microeng. 16, 564–570 (2006).
[CrossRef]

Wei, Y.

R. L. Burns, S. C. Johnson, G. M. Schmid, E. K. Kim, M. D. Dickey, J. Meiring, S. D. Burns, N. A. Stacey, C. G. Willson, D. Convey, Y. Wei, P. Fejes, K. Gehoski, D. Mancini, K. Nordquist, W. J. Dauksher, and D. J. Resnick, “Mesoscale modeling for SFIL simulating polymerization kinetics and densification,” Proc. SPIE 5374, 348–360 (2004).
[CrossRef]

Willson, C. G.

E. A. Costner, M. W. Lin, W. L. Jen, and C. G. Willson, “Nanoimprint lithography materials development for semiconductor device fabrication,” Ann. Rev. Mater. Res. 39, 155–180 (2009).
[CrossRef]

E. K. Kim, M. D. Stewart, K. Wu, F. L. Palmieri, M. D. Dickey, J. G. Ekerdt, and C. G. Willson, “Vinyl ether formulations for step and flash imprint lithography,” J. Vac. Sci. Technol. B 23, 2967–2971 (2005).
[CrossRef]

K. Wu, T. C. Bailey, C. G. Willson, and J. G. Ekerdt, “Surface hydration and its effect on fluorinated SAM formation on SiO2 surfaces,” Langmuir 21, 11795–11801 (2005).
[CrossRef] [PubMed]

R. L. Burns, S. C. Johnson, G. M. Schmid, E. K. Kim, M. D. Dickey, J. Meiring, S. D. Burns, N. A. Stacey, C. G. Willson, D. Convey, Y. Wei, P. Fejes, K. Gehoski, D. Mancini, K. Nordquist, W. J. Dauksher, and D. J. Resnick, “Mesoscale modeling for SFIL simulating polymerization kinetics and densification,” Proc. SPIE 5374, 348–360 (2004).
[CrossRef]

M. Colburn, I. Suez, B. J. Choi, M. Meissl, T. Bailey, S. V. Sreenivasan, J. G. Ekerdt, and C. G. Willson, “Characterization and modeling of volumetric and mechanical properties for step and flash imprint lithography photopolymers,” J. Vac. Sci. Technol. B 19, 2685–2689 (2001).
[CrossRef]

Wu, K.

K. Wu, T. C. Bailey, C. G. Willson, and J. G. Ekerdt, “Surface hydration and its effect on fluorinated SAM formation on SiO2 surfaces,” Langmuir 21, 11795–11801 (2005).
[CrossRef] [PubMed]

E. K. Kim, M. D. Stewart, K. Wu, F. L. Palmieri, M. D. Dickey, J. G. Ekerdt, and C. G. Willson, “Vinyl ether formulations for step and flash imprint lithography,” J. Vac. Sci. Technol. B 23, 2967–2971 (2005).
[CrossRef]

Yang, G. Z.

Yi, Y.

V. S. Khire, Y. Yi, N. A. Clark, and C. N. Bowman, “Formation and surface modification of nanopatterned thiol-ene substrates using step and flash imprint lithography,” Adv. Mater. 20, 3308–3313 (2008).
[CrossRef]

ACS Nano (1)

C. Pina-Hernandez, L. J. Guo, and P. F. Fu, “High-resolution functional epoxysilsesquioxane-based patterning layers for large-area nanoimprinting,” ACS Nano 4, 4776–4784 (2010).
[CrossRef] [PubMed]

Adv. Mater. (1)

V. S. Khire, Y. Yi, N. A. Clark, and C. N. Bowman, “Formation and surface modification of nanopatterned thiol-ene substrates using step and flash imprint lithography,” Adv. Mater. 20, 3308–3313 (2008).
[CrossRef]

AIChE J. (1)

C. N. Bowman and C. J. Kloxin, “Toward an enhanced understanding and implementation of photopolymerization reactions,” AIChE J. 54, 2775–2795 (2008).
[CrossRef]

Angew. Chem. Int. Ed. Engl. (1)

C. E. Hoyle and C. N. Bowman, “Thiol-ene click chemistry,” Angew. Chem. Int. Ed. Engl. 49, 1540–1573 (2010).
[CrossRef] [PubMed]

Ann. Rev. Mater. Res. (1)

E. A. Costner, M. W. Lin, W. L. Jen, and C. G. Willson, “Nanoimprint lithography materials development for semiconductor device fabrication,” Ann. Rev. Mater. Res. 39, 155–180 (2009).
[CrossRef]

Appl. Opt. (2)

Dent. Mater. (3)

J. A. Carioscia, H. Lu, J. W. Stanbury, and C. N. Bowman, “Thiol-ene oligomers as dental restorative materials,” Dent. Mater. 21, 1137–1143 (2005).
[CrossRef] [PubMed]

H. Lu, J. W. Stansbury, and C. N. Bowman, “Towards the elucidation of shrinkage stress development and relaxation in dental composites,” Dent. Mater. 20, 979–986 (2004).
[CrossRef] [PubMed]

H. Lu, J. A. Carioscia, J. W. Stansbury, and C. N. Bowman, “Investigations of step-growth thiol-ene polymerizations for novel dental restoratives,” Dent. Mater. 21, 1129–1136(2005).
[CrossRef] [PubMed]

J. Am. Chem. Soc. (2)

P. J. Flory, “Molecular size distribution in three dimensional polymers. I. gelation,” J. Am. Chem. Soc. 63, 3083–3090(1941).
[CrossRef]

C. Walling, “Gel formation in addition polymerization,” J. Am. Chem. Soc. 67, 441–447 (1945).
[CrossRef]

J. Chem. Phys. (1)

W. H. Stockmayer and H. Jacobson, “Gel formation in vinyl-divinyl copolymers,” J. Chem. Phys. 11, 393–393 (1943).
[CrossRef]

J. Micromech. Microeng. (1)

Q. D. Wang, Y. G. Duan, B. H. Lu, Y. C. Ding, and Y. P. Tang, “Imprint template fabrication based on glass wet etching using a soft etching mask,” J. Micromech. Microeng. 16, 564–570 (2006).
[CrossRef]

J. Vac. Sci. Technol. B (2)

M. Colburn, I. Suez, B. J. Choi, M. Meissl, T. Bailey, S. V. Sreenivasan, J. G. Ekerdt, and C. G. Willson, “Characterization and modeling of volumetric and mechanical properties for step and flash imprint lithography photopolymers,” J. Vac. Sci. Technol. B 19, 2685–2689 (2001).
[CrossRef]

E. K. Kim, M. D. Stewart, K. Wu, F. L. Palmieri, M. D. Dickey, J. G. Ekerdt, and C. G. Willson, “Vinyl ether formulations for step and flash imprint lithography,” J. Vac. Sci. Technol. B 23, 2967–2971 (2005).
[CrossRef]

Langmuir (1)

K. Wu, T. C. Bailey, C. G. Willson, and J. G. Ekerdt, “Surface hydration and its effect on fluorinated SAM formation on SiO2 surfaces,” Langmuir 21, 11795–11801 (2005).
[CrossRef] [PubMed]

Microelectron. Eng. (1)

P. Jin, N. Liu, T. T. Liu, and J. B. Tan, “Replication of micro optical element with continuous relief profile in fused silica using UV-embossing and reactive ion etching,” Microelectron. Eng. 87, 1086–1090 (2010).
[CrossRef]

Nano Lett. (1)

E. C. Hagberg, M. Malkoch, Y. B. Ling, C. J. Hawker, and K. R. Carter, “Effects of modulus and surface chemistry of thiol-ene photopolymers in nanoimprinting,” Nano Lett. 7, 233–237 (2007).
[CrossRef] [PubMed]

Nanotechnology (1)

S. Landis, N. Chaix, C. Gourgon, and T. Leveder, “Quantitative characterizations of a nanopatterned bonded wafer: force determination for nanoimprint lithography stamp removal,” Nanotechnology 19, 125305 (2008).
[CrossRef] [PubMed]

Proc. SPIE (2)

D. I. Shin, S. H. Kim, H. S. Jeong, S. Lee, Y. Jin, J. Noh, H. Oh, K. Lee, D. H. Shin, and S. H. Song, “Fabrication of phone-camera module using wafer-scale UV embossing process,” Proc. SPIE 6068, 60680Q (2006).
[CrossRef]

R. L. Burns, S. C. Johnson, G. M. Schmid, E. K. Kim, M. D. Dickey, J. Meiring, S. D. Burns, N. A. Stacey, C. G. Willson, D. Convey, Y. Wei, P. Fejes, K. Gehoski, D. Mancini, K. Nordquist, W. J. Dauksher, and D. J. Resnick, “Mesoscale modeling for SFIL simulating polymerization kinetics and densification,” Proc. SPIE 5374, 348–360 (2004).
[CrossRef]

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Figures (7)

Fig. 1
Fig. 1

Monomers and free radical generator used in UV- embossing resist.

Fig. 2
Fig. 2

Microscope image and profile test results after UV embossing with thiol-ene resist at the (a), (c) centers and (b), (d) edges.

Fig. 3
Fig. 3

Comparison of profile tests of stamp and samples at the (a) center region and (b) outer region.

Fig. 4
Fig. 4

Schematics of (a) polymerization shrinkage and (b) relaxed compensation through liquid flowing during fabrication of MOEs by UV embossing.

Fig. 5
Fig. 5

Microscope image and profile test results. Shrinkage relaxing result for (a), (c) thin residual resist and (b), (d) appropriate residual resist.

Fig. 6
Fig. 6

Etching rate ratio of thiol-ene resist.

Fig. 7
Fig. 7

Scanning electron microscope images and profile test results after the RIE process with thiol-ene resist at the (a), (c) centers and (b), (d) edges.

Tables (1)

Tables Icon

Table 1 Comparison of Thiol-ene and Acrylate-Based Resist Used in This Process

Equations (1)

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p c = A 0 + 2 B 0 4 B 0 ( λ 1 ) ,

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