DOE PAGES title logo U.S. Department of Energy
Office of Scientific and Technical Information

Title: Structural Characterization of Vapor-Deposited Glasses of an Organic Hole Transport Material with X-ray Scattering

Abstract

Vapor-deposited organic glasses can be produced with enhanced thermal stability and tunable molecular orientation by controlling the substrate temperature during deposition. Recent work has also shown improved charge carrier mobility associated with anisotropic molecular packing in organic electronics. Here grazing-incidence wide-angle X-ray scattering (GIWAXS) is used to characterize the structural anisotropy in glasses of a hole transport material, N,N'-bis(3-methylphenyl)-N,N'-diphenylbenzidine, commonly referred to as TPD. The TPD glasses were prepared by physical vapor deposition at substrate temperatures between 0.79 Tg and 0.98 Tg, where Tg is the glass transition temperature. A GIWAXS-derived orientation order parameter is used to quantify the anisotropy observed in the scattering patterns of the glasses. The GIWAXS-order parameter exhibits both positive and negative values as a function of substrate temperature, indicating either face-on or edge-on packing, and correlates well with a spectroscopic ellipsometry-derived order parameter that is sensitive to molecular orientation. We propose molecular packing arrangements based on the combination of the two order parameters and explore the relationship between kinetic stability and glass structure.

Authors:
 [1];  [2];  [3];  [2];  [1]
  1. Department of Chemistry, University of Wisconsin—Madison, Madison, Wisconsin 53706, United States
  2. Materials Department and Materials Research Laboratory, University of California Santa Barbara, Santa Barbara, California 93117, United States
  3. Stanford Synchrotron Radiation Lightsource, SLAC National Accelerator Laboratory, Menlo Park, California 94025, United States
Publication Date:
Research Org.:
SLAC National Accelerator Lab., Menlo Park, CA (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22). Materials Sciences & Engineering Division
OSTI Identifier:
1413156
Alternate Identifier(s):
OSTI ID: 1261999
Grant/Contract Number:  
AC02-76SF00515; SC0002161; DMR-1121288; DMR-1410438
Resource Type:
Published Article
Journal Name:
Chemistry of Materials
Additional Journal Information:
Journal Name: Chemistry of Materials Journal Volume: 27 Journal Issue: 9; Journal ID: ISSN 0897-4756
Publisher:
American Chemical Society (ACS)
Country of Publication:
United States
Language:
English
Subject:
36 MATERIALS SCIENCE; molecules; scattering; deposition; amorphous materials; order

Citation Formats

Gujral, Ankit, O’Hara, Kathryn A., Toney, Michael F., Chabinyc, Michael L., and Ediger, M. D. Structural Characterization of Vapor-Deposited Glasses of an Organic Hole Transport Material with X-ray Scattering. United States: N. p., 2015. Web. doi:10.1021/acs.chemmater.5b00583.
Gujral, Ankit, O’Hara, Kathryn A., Toney, Michael F., Chabinyc, Michael L., & Ediger, M. D. Structural Characterization of Vapor-Deposited Glasses of an Organic Hole Transport Material with X-ray Scattering. United States. https://doi.org/10.1021/acs.chemmater.5b00583
Gujral, Ankit, O’Hara, Kathryn A., Toney, Michael F., Chabinyc, Michael L., and Ediger, M. D. Tue . "Structural Characterization of Vapor-Deposited Glasses of an Organic Hole Transport Material with X-ray Scattering". United States. https://doi.org/10.1021/acs.chemmater.5b00583.
@article{osti_1413156,
title = {Structural Characterization of Vapor-Deposited Glasses of an Organic Hole Transport Material with X-ray Scattering},
author = {Gujral, Ankit and O’Hara, Kathryn A. and Toney, Michael F. and Chabinyc, Michael L. and Ediger, M. D.},
abstractNote = {Vapor-deposited organic glasses can be produced with enhanced thermal stability and tunable molecular orientation by controlling the substrate temperature during deposition. Recent work has also shown improved charge carrier mobility associated with anisotropic molecular packing in organic electronics. Here grazing-incidence wide-angle X-ray scattering (GIWAXS) is used to characterize the structural anisotropy in glasses of a hole transport material, N,N'-bis(3-methylphenyl)-N,N'-diphenylbenzidine, commonly referred to as TPD. The TPD glasses were prepared by physical vapor deposition at substrate temperatures between 0.79 Tg and 0.98 Tg, where Tg is the glass transition temperature. A GIWAXS-derived orientation order parameter is used to quantify the anisotropy observed in the scattering patterns of the glasses. The GIWAXS-order parameter exhibits both positive and negative values as a function of substrate temperature, indicating either face-on or edge-on packing, and correlates well with a spectroscopic ellipsometry-derived order parameter that is sensitive to molecular orientation. We propose molecular packing arrangements based on the combination of the two order parameters and explore the relationship between kinetic stability and glass structure.},
doi = {10.1021/acs.chemmater.5b00583},
journal = {Chemistry of Materials},
number = 9,
volume = 27,
place = {United States},
year = {Tue Apr 28 00:00:00 EDT 2015},
month = {Tue Apr 28 00:00:00 EDT 2015}
}

Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record
https://doi.org/10.1021/acs.chemmater.5b00583

Citation Metrics:
Cited by: 69 works
Citation information provided by
Web of Science

Save / Share:

Works referenced in this record:

Quantitative Determination of Organic Semiconductor Microstructure from the Molecular to Device Scale
journal, June 2012

  • Rivnay, Jonathan; Mannsfeld, Stefan C. B.; Miller, Chad E.
  • Chemical Reviews, Vol. 112, Issue 10
  • DOI: 10.1021/cr3001109

Quantification of Thin Film Crystallographic Orientation Using X-ray Diffraction with an Area Detector
journal, June 2010

  • Baker, Jessy L.; Jimison, Leslie H.; Mannsfeld, Stefan
  • Langmuir, Vol. 26, Issue 11
  • DOI: 10.1021/la904840q

Surface Self-Diffusion of Organic Glasses
journal, August 2013

  • Brian, Caleb W.; Yu, Lian
  • The Journal of Physical Chemistry A, Vol. 117, Issue 50
  • DOI: 10.1021/jp404944s

Liquid-crystalline semiconducting polymers with high charge-carrier mobility
journal, March 2006

  • McCulloch, Iain; Heeney, Martin; Bailey, Clare
  • Nature Materials, Vol. 5, Issue 4
  • DOI: 10.1038/nmat1612

Essential Differences of Organic Films at the Molecular Level via Vacuum Deposition and Solution Processes for Organic Light-Emitting Diodes
journal, November 2013

  • Xing, Xing; Zhong, Luwei; Zhang, Lipei
  • The Journal of Physical Chemistry C, Vol. 117, Issue 48
  • DOI: 10.1021/jp410547w

Uniaxial Alignment of the Columnar Super-Structure of a Hexa (Alkyl) Hexa- peri -hexabenzocoronene on Untreated Glass by Simple Solution Processing
journal, February 2003

  • Tracz, Adam; Jeszka, Jeremiasz K.; Watson, Mark D.
  • Journal of the American Chemical Society, Vol. 125, Issue 7
  • DOI: 10.1021/ja028945z

Morphology, molecular stacking, dynamics and device performance correlations of vacuum-deposited small-molecule organic solar cells
journal, January 2014

  • Chen, Chang-Wen; Huang, Zheng-Yu; Lin, Yi-Min
  • Phys. Chem. Chem. Phys., Vol. 16, Issue 19
  • DOI: 10.1039/C3CP55385J

Nematic phases of bent-core mesogens
journal, January 2010

  • Keith, Christina; Lehmann, Anne; Baumeister, Ute
  • Soft Matter, Vol. 6, Issue 8
  • DOI: 10.1039/b923262a

Towards high charge-carrier mobilities by rational design of the shape and periphery of discotics
journal, April 2009

  • Feng, Xinliang; Marcon, Valentina; Pisula, Wojciech
  • Nature Materials, Vol. 8, Issue 5
  • DOI: 10.1038/nmat2427

Charge Transport in Organic Semiconductors
journal, April 2007

  • Coropceanu, Veaceslav; Cornil, Jérôme; da Silva Filho, Demetrio A.
  • Chemical Reviews, Vol. 107, Issue 4
  • DOI: 10.1021/cr050140x

Measuring the Surface Dynamics of Glassy Polymers
journal, February 2008


Molecular origin of high field-effect mobility in an indacenodithiophene–benzothiadiazole copolymer
journal, July 2013

  • Zhang, Xinran; Bronstein, Hugo; Kronemeijer, Auke J.
  • Nature Communications, Vol. 4, Issue 1
  • DOI: 10.1038/ncomms3238

The Influence of Morphology on High-Performance Polymer Field-Effect Transistors
journal, January 2009

  • Tsao, Hoi Nok; Cho, Don; Andreasen, Jens Wenzel
  • Advanced Materials, Vol. 21, Issue 2
  • DOI: 10.1002/adma.200802032

High Anisotropy of the Field-Effect Transistor Mobility in Magnetically Aligned Discotic Liquid-Crystalline Semiconductors
journal, November 2005

  • Shklyarevskiy, Igor O.; Jonkheijm, Pascal; Stutzmann, Natalie
  • Journal of the American Chemical Society, Vol. 127, Issue 46
  • DOI: 10.1021/ja054694t

White organic light-emitting diodes with fluorescent tube efficiency
journal, May 2009

  • Reineke, Sebastian; Lindner, Frank; Schwartz, Gregor
  • Nature, Vol. 459, Issue 7244
  • DOI: 10.1038/nature08003

Molecular Orientation in Stable Glasses of Indomethacin
journal, April 2012

  • Dalal, Shakeel S.; Ediger, M. D.
  • The Journal of Physical Chemistry Letters, Vol. 3, Issue 10
  • DOI: 10.1021/jz3003266

Solvent-vapor annealing-induced growth, alignment, and patterning of π-conjugated supramolecular nanowires
journal, January 2011

  • Yip, Hin-Lap; Ma, Hong; Tian, Yanqing
  • Journal of Materials Research, Vol. 26, Issue 2
  • DOI: 10.1557/jmr.2010.7

Anisotropic Structure and Transformation Kinetics of Vapor-Deposited Indomethacin Glasses
journal, January 2011

  • Dawson, Kevin J.; Zhu, Lei; Yu, Lian
  • The Journal of Physical Chemistry B, Vol. 115, Issue 3
  • DOI: 10.1021/jp1092916

Organic Glasses with Exceptional Thermodynamic and Kinetic Stability
journal, January 2007


A general relationship between disorder, aggregation and charge transport in conjugated polymers
journal, August 2013

  • Noriega, Rodrigo; Rivnay, Jonathan; Vandewal, Koen
  • Nature Materials, Vol. 12, Issue 11
  • DOI: 10.1038/nmat3722

Electron Transport Materials for Organic Light-Emitting Diodes
journal, November 2004

  • Kulkarni, Abhishek P.; Tonzola, Christopher J.; Babel, Amit
  • Chemistry of Materials, Vol. 16, Issue 23
  • DOI: 10.1021/cm049473l

25th Anniversary Article: A Decade of Organic/Polymeric Photovoltaic Research
journal, September 2013


Tetraaryl biphenyl diamine hole transport materials: a structural study utilizing both single crystal and high resolution powder diffraction
journal, December 2001

  • Kennedy, Alan R.; Smith, W. Ewen; Tackley, Daniel R.
  • Journal of Materials Chemistry, Vol. 12, Issue 2
  • DOI: 10.1039/b107278c

Effects of Thermal Annealing Upon the Morphology of Polymer-Fullerene Blends
journal, August 2010

  • Verploegen, Eric; Mondal, Rajib; Bettinger, Christopher J.
  • Advanced Functional Materials, Vol. 20, Issue 20
  • DOI: 10.1002/adfm.201000975

Density functional theory study of the geometric structure and energetics of triphenylamine-based hole-transporting molecules
journal, September 2000


Hiking down the Energy Landscape:  Progress Toward the Kauzmann Temperature via Vapor Deposition
journal, April 2008

  • Kearns, Kenneth L.; Swallen, Stephen F.; Ediger, M. D.
  • The Journal of Physical Chemistry B, Vol. 112, Issue 16
  • DOI: 10.1021/jp7113384

Horizontal orientation of linear-shaped organic molecules having bulky substituents in neat and doped vacuum-deposited amorphous films
journal, February 2009


Tuning charge transport in solution-sheared organic semiconductors using lattice strain
journal, December 2011

  • Giri, Gaurav; Verploegen, Eric; Mannsfeld, Stefan C. B.
  • Nature, Vol. 480, Issue 7378, p. 504-508
  • DOI: 10.1038/nature10683

Tunable molecular orientation and elevated thermal stability of vapor-deposited organic semiconductors
journal, March 2015

  • Dalal, Shakeel S.; Walters, Diane M.; Lyubimov, Ivan
  • Proceedings of the National Academy of Sciences, Vol. 112, Issue 14
  • DOI: 10.1073/pnas.1421042112

Molecular Order in High-Efficiency Polymer/Fullerene Bulk Heterojunction Solar Cells
journal, September 2011

  • Hammond, Matthew R.; Kline, R. Joseph; Herzing, Andrew A.
  • ACS Nano, Vol. 5, Issue 10
  • DOI: 10.1021/nn202951e

Liquid Crystals :Experimental Study of Physical Properties and Phase Transitions
journal, December 2001


On-Top π-Stacking of Quasiplanar Molecules in Hole-Transporting Materials: Inducing Anisotropic Carrier Mobility in Amorphous Films
journal, April 2014

  • Wakamiya, Atsushi; Nishimura, Hidetaka; Fukushima, Tatsuya
  • Angewandte Chemie International Edition, Vol. 53, Issue 23
  • DOI: 10.1002/anie.201400068

High-Throughput Ellipsometric Characterization of Vapor-Deposited Indomethacin Glasses
journal, August 2013

  • Dalal, Shakeel S.; Fakhraai, Zahra; Ediger, M. D.
  • The Journal of Physical Chemistry B, Vol. 117, Issue 49
  • DOI: 10.1021/jp405005n

X‐ray Scattering from Films of Semiconducting Polymers
journal, August 2008


Molecular packing in highly stable glasses of vapor-deposited tris-naphthylbenzene isomers
journal, March 2012

  • Dawson, Kevin; Kopff, Laura A.; Zhu, Lei
  • The Journal of Chemical Physics, Vol. 136, Issue 9
  • DOI: 10.1063/1.3686801

Orientation Control of Linear-Shaped Molecules in Vacuum-Deposited Organic Amorphous Films and Its Effect on Carrier Mobilities
journal, February 2010

  • Yokoyama, Daisuke; Setoguchi, Yousuke; Sakaguchi, Akio
  • Advanced Functional Materials, Vol. 20, Issue 3
  • DOI: 10.1002/adfm.200901684

A molecular design principle of lyotropic liquid-crystalline conjugated polymers with directed alignment capability for plastic electronics
journal, March 2013

  • Kim, Bong-Gi; Jeong, Eun Jeong; Chung, Jong Won
  • Nature Materials, Vol. 12, Issue 7
  • DOI: 10.1038/nmat3595

Current Topics in Smectic Liquid Crystal Research
journal, January 2006


25th Anniversary Article: Organic Field-Effect Transistors: The Path Beyond Amorphous Silicon
journal, January 2014


Bulk Heterojunction Solar Cells: Morphology and Performance Relationships
journal, May 2014

  • Huang, Ye; Kramer, Edward J.; Heeger, Alan J.
  • Chemical Reviews, Vol. 114, Issue 14
  • DOI: 10.1021/cr400353v

Order Induced Charge Carrier Mobility Enhancement in Columnar Liquid Crystal Diodes
journal, November 2013

  • Eccher, Juliana; Faria, Gregório C.; Bock, Harald
  • ACS Applied Materials & Interfaces, Vol. 5, Issue 22
  • DOI: 10.1021/am403681q