Generic packing motifs in vapor-deposited glasses of organic semiconductors

Bagchi, Kushal; Gujral, Ankit; Toney, M. F.; Ediger, M. D.

doi:10.1039/c9sm01155b

Generic packing motifs in vapor-deposited glasses of organic semiconductors

Journal Article · Fri Aug 23 00:00:00 EDT 2019 · Soft Matter

DOI:https://doi.org/10.1039/c9sm01155b· OSTI ID:1576797

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Univ. of Wisconsin, Madison, WI (United States). Dept. of Chemistry
SLAC National Accelerator Lab., Menlo Park, CA (United States). Stanford Synchrotron Radiation Lightsource (SSRL)

We study the structure of vapor-deposited glasses of five common organic semiconductors as a function of substrate temperature during deposition, using synchrotron X-ray scattering. For deposition at a substrate temperature of ~0.8$$T_g$$ (where $$T_g$$ is the glass transition temperature), we find a generic tendency towards “face-on” packing in glasses of anisotropic molecules. At higher substrate temperature however this generic behavior breaks down; glasses of rod-shaped molecules exhibit a more pronounced tendency for end-on packing. Our study provides guidelines to create face-on and end-on packing motifs in organic glasses, which can promote efficient charge transport in OLED and OFET devices respectively.

View Accepted Manuscript (DOE)

Research Organization:: SLAC National Accelerator Laboratory (SLAC), Menlo Park, CA (United States); Univ. of Wisconsin, Madison, WI (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)

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

OSTI ID:: 1576797

Alternate ID(s):: OSTI ID: 1605680
OSTI ID: 1568933

Journal Information:: Soft Matter, Journal Name: Soft Matter Journal Issue: 38 Vol. 15; ISSN SMOABF; ISSN 1744-683X

Publisher:: Royal Society of ChemistryCopyright Statement

Country of Publication:: United States

Language:: English

References (43)

Orientation Control of Linear-Shaped Molecules in Vacuum-Deposited Organic Amorphous Films and Its Effect on Carrier Mobilities Yokoyama, Daisuke; Setoguchi, Yousuke; Sakaguchi, Akio Advanced Functional Materials, Vol. 20, Issue 3 https://doi.org/10.1002/adfm.200901684	journal	February 2010
Control of Molecular Orientation in Organic Semiconductor Films using Weak Hydrogen Bonds Watanabe, Yuichiro; Yokoyama, Daisuke; Koganezawa, Tomoyuki Advanced Materials, Vol. 31, Issue 18 https://doi.org/10.1002/adma.201808300	journal	March 2019
Controlling Molecular Packing for Charge Transport in Organic Thin Films Li, Liqiang; Hu, Wenping; Fuchs, Harald Advanced Energy Materials, Vol. 1, Issue 2 https://doi.org/10.1002/aenm.201000021	journal	February 2011
Photo- and Electroactive Amorphous Molecular Materials-molecular Design, Syntheses, Reactions, Properties, and Applications Shirota, Yasuhiko ChemInform, Vol. 36, Issue 18 https://doi.org/10.1002/chin.200518291	journal	May 2005
Charge Transport in Organic Semiconductors Coropceanu, Veaceslav; Cornil, Jerome; da Silva Filho, Demetrio A. ChemInform, Vol. 38, Issue 29 https://doi.org/10.1002/chin.200729266	journal	July 2007
Iminodibenzyl-substituted distyrylarylenes as dopants for blue and white organic light-emitting devices Ho, Meng-Huan; Chang, Chia-Ming; Chu, Ta-Ya Organic Electronics, Vol. 9, Issue 1 https://doi.org/10.1016/j.orgel.2007.09.006	journal	February 2008
Investigating the molecular orientation of Ir(ppy)3 and Ir(ppy)2(acac) emitter complexes by X-ray diffraction Murawski, Caroline; Elschner, Chris; Lenk, Simone Organic Electronics, Vol. 53 https://doi.org/10.1016/j.orgel.2017.11.036	journal	February 2018
Anisotropic Vapor-Deposited Glasses: Hybrid Organic Solids Ediger, M. D.; de Pablo, Juan; Yu, Lian Accounts of Chemical Research, Vol. 52, Issue 2 https://doi.org/10.1021/acs.accounts.8b00513	journal	January 2019
Structural Characterization of Vapor-Deposited Glasses of an Organic Hole Transport Material with X-ray Scattering Gujral, Ankit; O’Hara, Kathryn A.; Toney, Michael F. Chemistry of Materials, Vol. 27, Issue 9 https://doi.org/10.1021/acs.chemmater.5b00583	journal	April 2015
Highly Organized Smectic-like Packing in Vapor-Deposited Glasses of a Liquid Crystal Gujral, Ankit; Gómez, Jaritza; Jiang, Jing Chemistry of Materials, Vol. 29, Issue 2 https://doi.org/10.1021/acs.chemmater.6b04877	journal	January 2017
Vapor-Deposited Glasses with Long-Range Columnar Liquid Crystalline Order Gujral, Ankit; Gómez, Jaritza; Ruan, Shigang Chemistry of Materials, Vol. 29, Issue 21 https://doi.org/10.1021/acs.chemmater.7b02852	journal	October 2017
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
Charge Transport in Organic Semiconductors Coropceanu, Veaceslav; Cornil, Jérôme; da Silva Filho, Demetrio A. Chemical Reviews, Vol. 107, Issue 4 https://doi.org/10.1021/cr050140x	journal	April 2007
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
Correlation between Molecular Packing and Optical Properties in Different Crystalline Polymorphs and Amorphous Thin Films of mer -Tris(8-hydroxyquinoline)aluminum(III) Brinkmann, Martin; Gadret, Gregory; Muccini, Michele Journal of the American Chemical Society, Vol. 122, Issue 21 https://doi.org/10.1021/ja993608k	journal	May 2000
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
Character of Devitrification, Viewed from Enthalpic Paths, of the Vapor-Deposited Ethylbenzene Glasses Ramos, Sergio Luis L. M.; Oguni, Masaharu; Ishii, Kikujiro The Journal of Physical Chemistry B, Vol. 115, Issue 49 https://doi.org/10.1021/jp203612s	journal	December 2011
Horizontal Orientation of Disk-like Hole Transport Molecules and Their Application for Organic Light-Emitting Diodes Requiring a Lower Driving Voltage Kim, Jun Y.; Yokoyama, Daisuke; Adachi, Chihaya The Journal of Physical Chemistry C, Vol. 116, Issue 15 https://doi.org/10.1021/jp301650x	journal	April 2012
Surface Self-Diffusion of Organic Glasses Brian, Caleb W.; Yu, Lian The Journal of Physical Chemistry A, Vol. 117, Issue 50 https://doi.org/10.1021/jp404944s	journal	August 2013
High-Throughput Ellipsometric Characterization of Vapor-Deposited Indomethacin Glasses Dalal, Shakeel S.; Fakhraai, Zahra; Ediger, M. D. The Journal of Physical Chemistry B, Vol. 117, Issue 49 https://doi.org/10.1021/jp405005n	journal	August 2013
Essential Differences of Organic Films at the Molecular Level via Vacuum Deposition and Solution Processes for Organic Light-Emitting Diodes Xing, Xing; Zhong, Luwei; Zhang, Lipei The Journal of Physical Chemistry C, Vol. 117, Issue 48 https://doi.org/10.1021/jp410547w	journal	November 2013
Devitrification Properties of Vapor-Deposited Ethylcyclohexane Glasses and Interpretation of the Molecular Mechanism for Formation of Vapor-Deposited Glasses L. M. Ramos, Sergio Luis; Chigira, Atsuko. K.; Oguni, Masaharu The Journal of Physical Chemistry B, Vol. 119, Issue 10 https://doi.org/10.1021/jp5109174	journal	February 2015
Hiking down the Energy Landscape: Progress Toward the Kauzmann Temperature via Vapor Deposition Kearns, Kenneth L.; Swallen, Stephen F.; Ediger, M. D. The Journal of Physical Chemistry B, Vol. 112, Issue 16 https://doi.org/10.1021/jp7113384	journal	April 2008
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
Emergence of a substrate-temperature-dependent dielectric process in a prototypical vapor deposited hole-transport glass Rodríguez-Tinoco, Cristian; Rams-Baron, Marzena; Rodríguez-Viejo, Javier Scientific Reports, Vol. 8, Issue 1 https://doi.org/10.1038/s41598-018-19604-7	journal	January 2018
Photo- and electroactive amorphous molecular materials—molecular design, syntheses, reactions, properties, and applications Shirota, Yasuhiko J. Mater. Chem., Vol. 15, Issue 1 https://doi.org/10.1039/B413819H	journal	January 2005
Transformation kinetics of vapor-deposited thin film organic glasses: the role of stability and molecular packing anisotropy Rodríguez-Tinoco, Cristian; Gonzalez-Silveira, Marta; Ràfols-Ribé, Joan Physical Chemistry Chemical Physics, Vol. 17, Issue 46 https://doi.org/10.1039/C5CP04692K	journal	January 2015
Advantages and disadvantages of vacuum-deposited and spin-coated amorphous organic semiconductor films for organic light-emitting diodes Shibata, Maki; Sakai, Yoshiya; Yokoyama, Daisuke Journal of Materials Chemistry C, Vol. 3, Issue 42 https://doi.org/10.1039/C5TC01911G	journal	January 2015
All-atom simulation of molecular orientation in vapor-deposited organic light-emitting diodes Youn, Yong; Yoo, Dongsun; Song, Hochul Journal of Materials Chemistry C, Vol. 6, Issue 5 https://doi.org/10.1039/C7TC05278B	journal	January 2018
Tetraaryl biphenyl diamine hole transport materials: a structural study utilizing both single crystal and high resolution powder diffraction Kennedy, Alan R.; Smith, W. Ewen; Tackley, Daniel R. Journal of Materials Chemistry, Vol. 12, Issue 2 https://doi.org/10.1039/b107278c	journal	December 2001
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
Anisotropic optical properties and molecular orientation in vacuum-deposited ter(9,9-diarylfluorene)s thin films using spectroscopic ellipsometry Lin, Hao-Wu; Lin, Chun-Liang; Chang, Hsin-Hua Journal of Applied Physics, Vol. 95, Issue 3 https://doi.org/10.1063/1.1635991	journal	February 2004
A molecular view of vapor deposited glasses Singh, Sadanand; de Pablo, Juan J. The Journal of Chemical Physics, Vol. 134, Issue 19 https://doi.org/10.1063/1.3586805	journal	May 2011
Nematic-like stable glasses without equilibrium liquid crystal phases Gómez, Jaritza; Gujral, Ankit; Huang, Chengbin The Journal of Chemical Physics, Vol. 146, Issue 5 https://doi.org/10.1063/1.4974829	journal	February 2017
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
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
Suppression of tunneling two-level systems in ultrastable glasses of indomethacin Perez-Castaneda, T.; Rodriguez-Tinoco, C.; Rodriguez-Viejo, J. Proceedings of the National Academy of Sciences, Vol. 111, Issue 31 https://doi.org/10.1073/pnas.1405545111	journal	July 2014
Tunable molecular orientation and elevated thermal stability of vapor-deposited organic semiconductors Dalal, Shakeel S.; Walters, Diane M.; Lyubimov, Ivan Proceedings of the National Academy of Sciences, Vol. 112, Issue 14 https://doi.org/10.1073/pnas.1421042112	journal	March 2015
Recent Development of Blue Fluorescent OLED Materials and Devices Wen, S. -W.; Lee, M. -T.; Chen, C. H. Journal of Display Technology, Vol. 1, Issue 1 https://doi.org/10.1109/JDT.2005.852802	journal	September 2005
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
Suppression of tunneling two-level systems in ultrastable glasses of indomethacin Pérez-Castañeda, Tomás; Rodríguez-Tinoco, Cristian; Rodríguez-Viejo, Javier arXiv https://doi.org/10.48550/arxiv.1407.6371	text	January 2014

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Generic packing motifs in vapor-deposited glasses of organic semiconductors

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