Stable Glasses of Organic Semiconductor Resist Crystallization

Bagchi, Kushal; Fiori, Marie E.; Bishop, Camille; Toney, M. F.; Ediger, M. D.

doi:10.1021/acs.jpcb.0c09925

Stable Glasses of Organic Semiconductor Resist Crystallization

Journal Article · Thu Dec 24 00:00:00 EST 2020 · Journal of Physical Chemistry. B, Condensed Matter, Materials, Surfaces, Interfaces and Biophysical Chemistry

DOI:https://doi.org/10.1021/acs.jpcb.0c09925· OSTI ID:1768232

^[1]; Fiori, Marie E. ^[1]; ^[1]; ^[2]; ^[1]

Univ. of Wisconsin, Madison, WI (United States)
SLAC National Accelerator Lab., Menlo Park, CA (United States); Univ. of Colorado, Boulder, CO (United States)

The instability of glassy solids poses a key limitation to their use in several technological applications. Well-packed organic glasses, prepared by physical vapor deposition (PVD), have drawn attention recently because they can exhibit significantly higher thermal and chemical stability than glasses prepared from more traditional routes. We show here that PVD glasses can also show enhanced resistance to crystallization. By controlling the deposition temperature, resistance toward crystallization can be enhanced by at least a factor of ten in PVD glasses of the model organic semiconductor Alq3 (tris(8-hydroxyquinolinato) aluminum). PVD glasses of Alq3 first transform into a supercooled liquid before crystallizing. By controlling the deposition temperature, we increase the glass → liquid transformation time thereby also increasing the overall time for crystallization. Furthermore, we thus demonstrate a new strategy to stabilize glasses of organic semiconductors against crystallization, which is a common failure mechanism in organic light emitting diode devices.

View Accepted Manuscript (DOE)

Research Organization:: SLAC National Accelerator Laboratory (SLAC), Menlo Park, CA (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES). Materials Sciences & Engineering Division

Grant/Contract Number:: AC02-76SF00515; SC0002161

OSTI ID:: 1768232

Journal Information:: Journal of Physical Chemistry. B, Condensed Matter, Materials, Surfaces, Interfaces and Biophysical Chemistry, Journal Name: Journal of Physical Chemistry. B, Condensed Matter, Materials, Surfaces, Interfaces and Biophysical Chemistry Journal Issue: 1 Vol. 125; ISSN 1520-6106

Publisher:: American Chemical SocietyCopyright Statement

Country of Publication:: United States

Language:: English

References (49)

Crystallization of amorphous complex oxides: New geometries and new compositions via solid phase epitaxy Evans, Paul G.; Chen, Yajin; Tilka, Jack A. Current Opinion in Solid State and Materials Science, Vol. 22, Issue 6 https://doi.org/10.1016/j.cossms.2018.09.001	journal	December 2018
Highly stable glasses of celecoxib: Influence on thermo-kinetic properties, microstructure and response towards crystal growth Rodríguez-Tinoco, C.; Gonzalez-Silveira, M.; Ràfols-Ribé, J. Journal of Non-Crystalline Solids, Vol. 407 https://doi.org/10.1016/j.jnoncrysol.2014.07.031	journal	January 2015
Amorphous pharmaceutical solids: preparation, characterization and stabilization Yu, Lian Advanced Drug Delivery Reviews, Vol. 48, Issue 1 https://doi.org/10.1016/s0169-409x(01)00098-9	journal	May 2001
The case for bulk metallic glass Telford, Mark Materials Today, Vol. 7, Issue 3 https://doi.org/10.1016/s1369-7021(04)00124-5	journal	March 2004
Crystal Morphology and Growth in Annealed Rubrene Thin Films Fielitz, Thomas R.; Holmes, Russell J. Crystal Growth & Design, Vol. 16, Issue 8 https://doi.org/10.1021/acs.cgd.6b00783	journal	July 2016
Glass Structure Controls Crystal Polymorph Selection in Vapor-Deposited Films of 4,4′-Bis( N -carbazolyl)-1,1′-biphenyl Van den Brande, Niko; Gujral, Ankit; Huang, Chengbin Crystal Growth & Design, Vol. 18, Issue 10 https://doi.org/10.1021/acs.cgd.8b00329	journal	August 2018
Photon Activation of Glassy Dynamics: A Mechanism for Photoinduced Fluidization, Aging, and Information Storage in Amorphous Materials Lubchenko, Vassiliy; Wolynes, Peter G. The Journal of Physical Chemistry B, Vol. 124, Issue 38 https://doi.org/10.1021/acs.jpcb.0c06515	journal	August 2020
Fast Crystal Growth in o -Terphenyl Glasses: A Possible Role for Fracture and Surface Mobility Powell, C. Travis; Xi, Hanmi; Sun, Ye The Journal of Physical Chemistry B, Vol. 119, Issue 31 https://doi.org/10.1021/acs.jpcb.5b05389	journal	July 2015
Ultrastable Amorphous Sb ₂ Se ₃ Film Zhang, Kai; Li, Yang; Huang, Quan The Journal of Physical Chemistry B, Vol. 121, Issue 34 https://doi.org/10.1021/acs.jpcb.7b03408	journal	August 2017
Dense Glass Packing Can Slow Reactions with an Atmospheric Gas Qiu, Yue; Bieser, Michael E.; Ediger, M. D. The Journal of Physical Chemistry B, Vol. 123, Issue 47 https://doi.org/10.1021/acs.jpcb.9b08360	journal	October 2019
Controlling Structure and Properties of Vapor-Deposited Glasses of Organic Semiconductors: Recent Advances and Challenges Bagchi, Kushal; Ediger, M. D. The Journal of Physical Chemistry Letters, Vol. 11, Issue 17 https://doi.org/10.1021/acs.jpclett.0c01682	journal	July 2020
Influence of Molecular Shape on the Thermal Stability and Molecular Orientation of Vapor-Deposited Organic Semiconductors Walters, Diane M.; Antony, Lucas; de Pablo, Juan J. The Journal of Physical Chemistry Letters, Vol. 8, Issue 14, p. 3380-3386 https://doi.org/10.1021/acs.jpclett.7b01097	journal	July 2017
Enhanced Electrical Properties and Air Stability of Amorphous Organic Thin Films by Engineering Film Density Esaki, Yu; Komino, Takeshi; Matsushima, Toshinori The Journal of Physical Chemistry Letters, Vol. 8, Issue 23 https://doi.org/10.1021/acs.jpclett.7b02808	journal	November 2017
Origin of Anisotropic Molecular Packing in Vapor-Deposited Alq3 Glasses Bagchi, Kushal; Jackson, Nicholas E.; Gujral, Ankit The Journal of Physical Chemistry Letters, Vol. 10, Issue 2 https://doi.org/10.1021/acs.jpclett.8b03582	journal	December 2018
Vapor-Deposited Glass Structure Determined by Deposition Rate–Substrate Temperature Superposition Principle Bishop, Camille; Gujral, Ankit; Toney, Michael F. The Journal of Physical Chemistry Letters, Vol. 10, Issue 13 https://doi.org/10.1021/acs.jpclett.9b01377	journal	June 2019
Solid-Phase Epitaxy of Perovskite High Dielectric PrAlO ₃ Films Grown by Atomic Layer Deposition for Use in Two-Dimensional Electronics and Memory Devices Waduge, Wathsala L. I.; Chen, Yajin; Zuo, Peng ACS Applied Nano Materials, Vol. 2, Issue 11 https://doi.org/10.1021/acsanm.9b02153	journal	October 2019
Quantitative Determination of Organic Semiconductor Microstructure from the Molecular to Device Scale Rivnay, Jonathan; Mannsfeld, Stefan C. B.; Miller, Chad E. Chemical Reviews, Vol. 112, Issue 10 https://doi.org/10.1021/cr3001109	journal	June 2012
Molecular design for nonpolymeric organic dye glasses with thermal stability: relations between thermodynamic parameters and amorphous properties Naito, Katsuyuki; Miura, Akira The Journal of Physical Chemistry, Vol. 97, Issue 23 https://doi.org/10.1021/j100125a025	journal	June 1993
Tuning Polymorphism and Orientation in Organic Semiconductor Thin Films via Post-deposition Processing Hiszpanski, Anna M.; Baur, Robin M.; Kim, Bumjung Journal of the American Chemical Society, Vol. 136, Issue 44 https://doi.org/10.1021/ja5091035	journal	October 2014
Photostability Can Be Significantly Modulated by Molecular Packing in Glasses Qiu, Yue; Antony, Lucas W.; de Pablo, Juan J. Journal of the American Chemical Society, Vol. 138, Issue 35, p. 11282-11289 https://doi.org/10.1021/jacs.6b06372	journal	August 2016
Anisotropic Structure and Transformation Kinetics of Vapor-Deposited Indomethacin Glasses Dawson, Kevin J.; Zhu, Lei; Yu, Lian The Journal of Physical Chemistry B, Vol. 115, Issue 3 https://doi.org/10.1021/jp1092916	journal	January 2011
Highly Stable Indomethacin Glasses Resist Uptake of Water Vapor Dawson, Kevin J.; Kearns, Kenneth L.; Ediger, M. D. The Journal of Physical Chemistry B, Vol. 113, Issue 8 https://doi.org/10.1021/jp808838t	journal	February 2009
Structural Variations of an Organic Glassformer Vapor-Deposited onto a Temperature Gradient Stage Fakhraai, Zahra; Still, Tim; Fytas, George The Journal of Physical Chemistry Letters, Vol. 2, Issue 5 https://doi.org/10.1021/jz101723d	journal	February 2011
Quantification of Thin Film Crystallographic Orientation Using X-ray Diffraction with an Area Detector Baker, Jessy L.; Jimison, Leslie H.; Mannsfeld, Stefan Langmuir, Vol. 26, Issue 11 https://doi.org/10.1021/la904840q	journal	June 2010
Degradation of Organic Electroluminescent Devices. Evidence for the Occurrence of Spherulitic Crystallization in the Hole Transport Layer Smith, P. F.; Gerroir, P.; Xie, S. Langmuir, Vol. 14, Issue 20 https://doi.org/10.1021/la9709406	journal	September 1998
Molecular Order in High-Efficiency Polymer/Fullerene Bulk Heterojunction Solar Cells Hammond, Matthew R.; Kline, R. Joseph; Herzing, Andrew A. ACS Nano, Vol. 5, Issue 10 https://doi.org/10.1021/nn202951e	journal	September 2011
Supercooled liquids and the glass transition Debenedetti, Pablo G.; Stillinger, Frank H. Nature, Vol. 410, Issue 6825 https://doi.org/10.1038/35065704	journal	March 2001
Laser action in organic semiconductor waveguide and double-heterostructure devices Kozlov, V. G.; Bulović, V.; Burrows, P. E. Nature, Vol. 389, Issue 6649 https://doi.org/10.1038/38693	journal	September 1997
Spin routes in organic semiconductors Dediu, V. Alek; Hueso, Luis E.; Bergenti, Ilaria Nature Materials, Vol. 8, Issue 9 https://doi.org/10.1038/nmat2510	journal	August 2009
Ultrastable metallic glasses formed on cold substrates Luo, P.; Cao, C. R.; Zhu, F. Nature Communications, Vol. 9, Issue 1 https://doi.org/10.1038/s41467-018-03656-4	journal	April 2018
Formation of aligned periodic patterns during the crystallization of organic semiconductor thin films Bangsund, John S.; Fielitz, Thomas R.; Steiner, Trevor J. Nature Materials, Vol. 18, Issue 7 https://doi.org/10.1038/s41563-019-0379-3	journal	June 2019
Ultrastable monodisperse polymer glass formed by physical vapour deposition Raegen, Adam N.; Yin, Junjie; Zhou, Qi Nature Materials, Vol. 19, Issue 10 https://doi.org/10.1038/s41563-020-0723-7	journal	July 2020
Stability of thin film glasses of toluene and ethylbenzene formed by vapor deposition: an in situ nanocalorimetric study Leon-Gutierrez, Edgar; Sepúlveda, Alfonso; Garcia, Gemma Phys. Chem. Chem. Phys., Vol. 12, Issue 44 https://doi.org/10.1039/c0cp00208a	journal	January 2010
Molecular orientation in small-molecule organic light-emitting diodes Yokoyama, Daisuke Journal of Materials Chemistry, Vol. 21, Issue 48 https://doi.org/10.1039/c1jm13417e	journal	January 2011
Generic packing motifs in vapor-deposited glasses of organic semiconductors Bagchi, Kushal; Gujral, Ankit; Toney, M. F. Soft Matter, Vol. 15, Issue 38 https://doi.org/10.1039/c9sm01155b	journal	January 2019
Humidity-induced crystallization of tris (8-hydroxyquinoline) aluminum layers in organic light-emitting devices Aziz, Hany; Popovic, Zoran; Xie, Shuang Applied Physics Letters, Vol. 72, Issue 7 https://doi.org/10.1063/1.120867	journal	February 1998
Perspective: Supercooled liquids and glasses Ediger, M. D.; Harrowell, Peter The Journal of Chemical Physics, Vol. 137, Issue 8 https://doi.org/10.1063/1.4747326	journal	August 2012
Thermal stability of vapor-deposited stable glasses of an organic semiconductor Walters, Diane M.; Richert, Ranko; Ediger, M. D. The Journal of Chemical Physics, Vol. 142, Issue 13 https://doi.org/10.1063/1.4916649	journal	April 2015
Kinetic stability and heat capacity of vapor-deposited glasses of o -terphenyl Whitaker, Katherine R.; Tylinski, M.; Ahrenberg, Mathias The Journal of Chemical Physics, Vol. 143, Issue 8 https://doi.org/10.1063/1.4929511	journal	August 2015
Influence of amorphous structure on polymorphism in vanadia Stone, Kevin H.; Schelhas, Laura T.; Garten, Lauren M. APL Materials, Vol. 4, Issue 7 https://doi.org/10.1063/1.4958674	journal	July 2016
Perspective: Highly stable vapor-deposited glasses Ediger, M. D. The Journal of Chemical Physics, Vol. 147, Issue 21 https://doi.org/10.1063/1.5006265	journal	December 2017
Tenfold increase in the photostability of an azobenzene guest in vapor-deposited glass mixtures Qiu, Yue; Antony, Lucas W.; Torkelson, John M. The Journal of Chemical Physics, Vol. 149, Issue 20 https://doi.org/10.1063/1.5052003	journal	November 2018
Organic electroluminescent diodes Tang, C. W.; VanSlyke, S. A. Applied Physics Letters, Vol. 51, Issue 12 https://doi.org/10.1063/1.98799	journal	September 1987
Vapor deposition of a nonmesogen prepares highly structured organic glasses Bishop, Camille; Thelen, Jacob L.; Gann, Eliot Proceedings of the National Academy of Sciences, Vol. 116, Issue 43 https://doi.org/10.1073/pnas.1908445116	journal	September 2019
Polyamorphism of vapor-deposited amorphous selenium in response to light Zhang, Aixi; Jin, Yi; Liu, Tianyi Proceedings of the National Academy of Sciences, Vol. 117, Issue 39 https://doi.org/10.1073/pnas.2009852117	journal	September 2020
Growth of AlQ ₃ nanowires directly from amorphous thin film and nanoparticles Cho, Chun-Pei; Tu, Chung-Yi; Perng, Tsong-Pyng Nanotechnology, Vol. 17, Issue 21 https://doi.org/10.1088/0957-4484/17/21/035	journal	October 2006
High-performance organic light-emitting diodes comprising ultrastable glass layers Ràfols-Ribé, Joan; Will, Paul-Anton; Hänisch, Christian Science Advances, Vol. 4, Issue 5 https://doi.org/10.1126/sciadv.aar8332	journal	May 2018
Formation of Glasses from Liquids and Biopolymers Angell, C. A. Science, Vol. 267, Issue 5206 https://doi.org/10.1126/science.267.5206.1924	journal	March 1995
Physical Aging in Polymer Glasses Hodge, I. M. Science, Vol. 267, Issue 5206 https://doi.org/10.1126/science.267.5206.1945	journal	March 1995

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37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
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Stable Glasses of Organic Semiconductor Resist Crystallization

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