Synthesis and use of a hyper-connecting cross-linking agent in the hole-transporting layer of perovskite solar cells

Watson, Brian  L.; Rolston, Nicholas; Bush, Kevin A.; Taleghani, Leila; Dauskardt, Reinhold H.

doi:10.1039/c7ta05004f

Title: Synthesis and use of a hyper-connecting cross-linking agent in the hole-transporting layer of perovskite solar cells

Journal Article · 18 August 2017 · Journal of Materials Chemistry. A

DOI: https://doi.org/10.1039/c7ta05004f · OSTI ID:1579847

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^[1]; Bush, Kevin A. ^[1]; Taleghani, Leila ^[1];

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Stanford Univ., Stanford, CA (United States)

Solution-processed organic semiconducting materials feature prominently in modern optoelectronic devices, especially where low-cost and flexibility are specific goals, such as perovskite solar cells. Their intrinsic solubility, poor cohesion and lack of adhesion to underlying substrates, however, curtail their scope of application and durability. To overcome this, a mechanically stiff, light-activated, tetra-azide cross-linking agent, 1,3,5,7-tetrakis-(p-benzylazide)-adamantane (TPBA), has been developed to transform solution processed organic polymers into solvent-resistant and mechanically tough films. The use of 3-azidopropyltrimethoxysilane (AzPTMS) has been developed as a light-activated adhesion promotor, enabling mechanical testing of toughened, cross-linked polymers. Lithium bis(trifluoromethane)sulfonimide (LiTFSI) doped poly[bis(4-phenyl)(2,4,6-trimethylphenyl)amine, poly(triaryl amine) (PTAA), a hole-transporting material used in perovskite solar cells, has been selected as a candidate system for demonstrating the utility of TPBA to transform a fragile and highly-soluble hole-transporting organic semiconductor into a mechanically tough and solvent-resistant semiconducting composite. TPBA enables the solvent resistance and mechanical toughness of PTAA to be tuned without compromising the electronic functionality of the semiconducting material. Here, while increasing the fracture toughness of PTAA by over 300%, TPBA cross-linking also enables fabrication of perovskite solar cells with increased photovoltaic efficiencies in n–i–p and p–i–n geometries, and promotes adhesion of the doped polymer to the perovskite layer, mitigating interfacial device failure.

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Research Organization:: Stanford Univ., CA (United States)

Sponsoring Organization:: USDOE Office of Energy Efficiency and Renewable Energy (EERE), Office of Renewable Energy. Solar Energy Technologies Office

Grant/Contract Number:: EE0004946

OSTI ID:: 1579847

Journal Information:: Journal of Materials Chemistry. A, Vol. 5, Issue 36; ISSN 2050-7488

Publisher:: Royal Society of ChemistryCopyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 37 works

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References (57)

Click Chemistry: Diverse Chemical Function from a Few Good Reactions Kolb, Hartmuth C.; Finn, M. G.; Sharpless, K. Barry Angewandte Chemie International Edition, Vol. 40, Issue 11, p. 2004-2021 https://doi.org/10.1002/1521-3773(20010601)40:11<2004::AID-ANIE2004>3.0.CO;2-5	journal	June 2001
Enlightening solutions Meerholz, Klaus Nature, Vol. 437, Issue 7057 https://doi.org/10.1038/437327a	journal	September 2005
Stretching and conformal bonding of organic solar cells to hemispherical surfaces O'Connor, Timothy F.; Zaretski, Aliaksandr V.; Shiravi, Bijan A. Energy Environ. Sci., Vol. 7, Issue 1 https://doi.org/10.1039/C3EE42898B	journal	January 2014
Organic Azides: An Exploding Diversity of a Unique Class of Compounds Bräse, Stefan; Gil, Carmen; Knepper, Kerstin Angewandte Chemie International Edition, Vol. 44, Issue 33 https://doi.org/10.1002/anie.200400657	journal	August 2005
Effects of Molecular Configuration on Charge Diffusion Kinetics within Hole-Transporting Materials for Perovskites Solar Cells Chi, Wei-Jie; Li, Quan-Song; Li, Ze-Sheng The Journal of Physical Chemistry C, Vol. 119, Issue 16 https://doi.org/10.1021/acs.jpcc.5b02401	journal	April 2015
Template-Guided Solution-Shearing Method for Enhanced Charge Carrier Mobility in Diketopyrrolopyrrole-Based Polymer Field-Effect Transistors Shin, Jicheol; Hong, Tae Ryang; Lee, Tae Wan Advanced Materials, Vol. 26, Issue 34 https://doi.org/10.1002/adma.201401179	journal	June 2014
Controlling Hierarchy in Solution-processed Polymer Solar Cells Based on Crosslinked P3HT Tao, Chen; Aljada, Muhsen; Shaw, Paul E. Advanced Energy Materials, Vol. 3, Issue 1 https://doi.org/10.1002/aenm.201200394	journal	August 2012
Thermodynamic, kinetic, and structural factors in the synthesis of imine-linked dynamic covalent frameworks Duncan, Nathan C.; Hay, Benjamin P.; Hagaman, Edward W. Tetrahedron, Vol. 68, Issue 1 https://doi.org/10.1016/j.tet.2011.10.052	journal	January 2012
Application of click chemistry to the production of DNA microarrays Uszczyńska, Barbara; Ratajczak, Tomasz; Frydrych, Emilia Lab on a Chip, Vol. 12, Issue 6 https://doi.org/10.1039/c2lc21096g	journal	January 2012
New Thermally Cross-Linkable Polymer and Its Application as a Hole-Transporting Layer for Solution Processed Multilayer Organic Light Emitting Diodes Ma, Biwu; Lauterwasser, Frank; Deng, Lan Chemistry of Materials, Vol. 19, Issue 19 https://doi.org/10.1021/cm0715500	journal	September 2007
High-performance photovoltaic perovskite layers fabricated through intramolecular exchange Yang, W. S.; Noh, J. H.; Jeon, N. J. Science, Vol. 348, Issue 6240 https://doi.org/10.1126/science.aaa9272	journal	May 2015
Unusually long lifetimes of the singlet nitrenes derived from 4-azido-2,3,5,6-tetrafluorobenzamides Marcinek, Andrzej; Platz, Matthew S.; Chan, Stephen Y. The Journal of Physical Chemistry, Vol. 98, Issue 2 https://doi.org/10.1021/j100053a012	journal	January 1994
Solvent engineering for high-performance inorganic–organic hybrid perovskite solar cells Jeon, Nam Joong; Noh, Jun Hong; Kim, Young Chan Nature Materials, Vol. 13, Issue 9, p. 897-903 https://doi.org/10.1038/nmat4014	journal	July 2014
High-Efficiency and Color Stable Blue-Light-Emitting Polymers and Devices Huang, F.; Zhang, Y.; Liu, M. S. Advanced Functional Materials, Vol. 17, Issue 18 https://doi.org/10.1002/adfm.200700752	journal	December 2007
Mechanical integrity of solution-processed perovskite solar cells Rolston, Nicholas; Watson, Brian L.; Bailie, Colin D. Extreme Mechanics Letters, Vol. 9 https://doi.org/10.1016/j.eml.2016.06.006	journal	December 2016
High-efficiency solution processable polymer photovoltaic cells by self-organization of polymer blends Li, Gang; Shrotriya, Vishal; Huang, Jinsong Nature Materials, Vol. 4, Issue 11, p. 864-868 https://doi.org/10.1038/nmat1500	journal	October 2005
The Organic Power Transistor: Roll-to-Roll Manufacture, Thermal Behavior, and Power Handling When Driving Printed Electronics: The Organic Power Transistor: Roll-to-Roll Manufacture Pastorelli, Francesco; Schmidt, Thomas M.; Hösel, Markus Advanced Engineering Materials, Vol. 18, Issue 1 https://doi.org/10.1002/adem.201500348	journal	August 2015
Theoretical Investigation of Hole Transporter Materials for Energy Devices Alberga, Domenico; Mangiatordi, Giuseppe Felice; Labat, Frédéric The Journal of Physical Chemistry C, Vol. 119, Issue 42 https://doi.org/10.1021/acs.jpcc.5b08981	journal	October 2015
Fabrication and processing of polymer solar cells: A review of printing and coating techniques Krebs, Frederik C. Solar Energy Materials and Solar Cells, Vol. 93, Issue 4, p. 394-412 https://doi.org/10.1016/j.solmat.2008.10.004	journal	April 2009
Decohesion Kinetics in Polymer Organic Solar Cells Bruner, Christopher; Novoa, Fernando; Dupont, Stephanie ACS Applied Materials & Interfaces, Vol. 6, Issue 23 https://doi.org/10.1021/am506482q	journal	November 2014
Light-emitting diodes with variable colours from polymer blends Berggren, M.; Inganäs, O.; Gustafsson, G. Nature, Vol. 372, Issue 6505 https://doi.org/10.1038/372444a0	journal	December 1994
Comment on “The Mechanism of Pyrolysis of Benzyl Azide: Spectroscopic Evidence for Benzenemethanimine Formation” Wentrup, Curt The Journal of Physical Chemistry A, Vol. 119, Issue 29 https://doi.org/10.1021/acs.jpca.5b04198	journal	July 2015
Bright-White Light-Emitting Devices Based on a Single Polymer Exhibiting Simultaneous Blue, Green, and Red Emissions Chuang, Chu-Ying; Shih, Ping-I; Chien, Chen-Han Macromolecules, Vol. 40, Issue 2 https://doi.org/10.1021/ma062192+	journal	December 2006
High internal quantum efficiency in fullerene solar cells based on crosslinked polymer donor networks Liu, Bo; Png, Rui-Qi; Zhao, Li-Hong Nature Communications, Vol. 3, Issue 1 https://doi.org/10.1038/ncomms2211	journal	January 2012
The Mechanism of Pyrolysis of Benzyl Azide: Spectroscopic Evidence for Benzenemethanimine Formation Pinto, Rui M.; Guerra, Mauro; Copeland, Grant The Journal of Physical Chemistry A, Vol. 119, Issue 18 https://doi.org/10.1021/acs.jpca.5b02453	journal	April 2015
Solution-Processed Full-Color Polymer Organic Light-Emitting Diode Displays Fabricated by Direct Photolithography Gather, M. C.; Köhnen, A.; Falcou, A. Advanced Functional Materials, Vol. 17, Issue 2 https://doi.org/10.1002/adfm.200600651	journal	January 2007
Ultrasmooth organic–inorganic perovskite thin-film formation and crystallization for efficient planar heterojunction solar cells Zhang, Wei; Saliba, Michael; Moore, David T. Nature Communications, Vol. 6, Issue 1 https://doi.org/10.1038/ncomms7142	journal	January 2015
Liquid-crystalline semiconducting polymers with high charge-carrier mobility McCulloch, Iain; Heeney, Martin; Bailey, Clare Nature Materials, Vol. 5, Issue 4 https://doi.org/10.1038/nmat1612	journal	March 2006
Clickable Periodic Mesoporous Organosilicas: Synthesis, Click Reactions, and Adsorption of Antibiotics Gao, Jinsuo; Zhang, Xueying; Xu, Shutao Chemistry - A European Journal, Vol. 20, Issue 7 https://doi.org/10.1002/chem.201303778	journal	November 2013
One-Step Facile Synthesis of a Simple Hole Transport Material for Efficient Perovskite Solar Cells Chen, Hu; Bryant, Daniel; Troughton, Joel Chemistry of Materials, Vol. 28, Issue 8 https://doi.org/10.1021/acs.chemmater.6b00858	journal	April 2016
Understanding mechanical behavior and reliability of organic electronic materials Kim, Jae-Han; Lee, Inhwa; Kim, Taek-Soo MRS Bulletin, Vol. 42, Issue 02 https://doi.org/10.1557/mrs.2017.3	journal	February 2017
Orthogonal Processing: A Novel Photolithographic Patterning Method for Organic Electronics Lee, Jin-Kyun; Taylor, Priscillia G.; Zakhidov, Alexander A. Journal of Photopolymer Science and Technology, Vol. 22, Issue 5 https://doi.org/10.2494/photopolymer.22.565	journal	January 2009
Inkjet printing of organic electronics – comparison of deposition techniques and state-of-the-art developments Teichler, Anke; Perelaer, Jolke; Schubert, Ulrich S. Journal of Materials Chemistry C, Vol. 1, Issue 10 https://doi.org/10.1039/c2tc00255h	journal	January 2013
Polymer and Organic Nonvolatile Memory Devices ^† Heremans, Paul; Gelinck, Gerwin H.; Müller, Robert Chemistry of Materials, Vol. 23, Issue 3 https://doi.org/10.1021/cm102006v	journal	February 2011
Macroscopic Alignment of One-Dimensional Conjugated Polymer Nanocrystallites for High-Mobility Organic Field-Effect Transistors Chang, Mincheol; Choi, Dalsu; Egap, Eilaf ACS Applied Materials & Interfaces, Vol. 8, Issue 21 https://doi.org/10.1021/acsami.6b02216	journal	May 2016
A [2,2]paracyclophane triarylamine-based hole-transporting material for high performance perovskite solar cells Park, Sungmin; Heo, Jin Hyuck; Cheon, Cheol Hong Journal of Materials Chemistry A, Vol. 3, Issue 48 https://doi.org/10.1039/C5TA08417B	journal	January 2015
High speeds complementary integrated circuits fabricated with all-printed polymeric semiconductors Baeg, Kang-Jun; Khim, Dongyoon; Kim, Dong-Yu Journal of Polymer Science Part B: Polymer Physics, Vol. 49, Issue 1 https://doi.org/10.1002/polb.22148	journal	September 2010
High-performance polymer semiconducting heterostructure devices by nitrene-mediated photocrosslinking of alkyl side chains Png, Rui-Qi; Chia, Perq-Jon; Tang, Jie-Cong Nature Materials, Vol. 9, Issue 2 https://doi.org/10.1038/nmat2594	journal	December 2009
Hydrofluoroethers as Orthogonal Solvents for the Chemical Processing of Organic Electronic Materials Zakhidov, Alexander A.; Lee, Jin-Kyun; Fong, Hon Hang Advanced Materials, Vol. 20, Issue 18 https://doi.org/10.1002/adma.200800557	journal	July 2008
Role of Molecular Weight on the Mechanical Device Properties of Organic Polymer Solar Cells Bruner, Christopher; Dauskardt, Reinhold Macromolecules, Vol. 47, Issue 3 https://doi.org/10.1021/ma402215j	journal	January 2014
Cesium-containing triple cation perovskite solar cells: improved stability, reproducibility and high efficiency Saliba, Michael; Matsui, Taisuke; Seo, Ji-Youn Energy & Environmental Science, Vol. 9, Issue 6 https://doi.org/10.1039/C5EE03874J	journal	January 2016
A solvent additive to enhance the efficiency and the thermal stability of polymer:fullerene solar cells Derue, L.; Lecourtier, C.; Gorisse, T. RSC Advances, Vol. 5, Issue 5 https://doi.org/10.1039/C4RA14139C	journal	January 2015
Synergistic enhancement and mechanism study of mechanical and moisture stability of perovskite solar cells introducing polyethylene-imine into the CH ₃ NH ₃ PbI ₃ /HTM interface Yun, Jae Hoon; Lee, Inhwa; Kim, Taek-Soo Journal of Materials Chemistry A, Vol. 3, Issue 44 https://doi.org/10.1039/C5TA06008G	journal	January 2015
Thermal Stabilisation of Polymer-Fullerene Bulk Heterojunction Morphology for Efficient Photovoltaic Solar Cells Derue, Lionel; Dautel, Olivier; Tournebize, Aurélien Advanced Materials, Vol. 26, Issue 33 https://doi.org/10.1002/adma.201401062	journal	July 2014
Chemistry and kinetics of singlet pentafluorophenylnitrene Poe, Russell; Schnapp, Karlyn; Young, Mary J. T. Journal of the American Chemical Society, Vol. 114, Issue 13 https://doi.org/10.1021/ja00039a016	journal	June 1992
Polymer solar cells Li, Gang; Zhu, Rui; Yang, Yang Nature Photonics, Vol. 6, Issue 3 https://doi.org/10.1038/nphoton.2012.11	journal	February 2012
Investigating the Role of 4- Tert Butylpyridine in Perovskite Solar Cells Habisreutinger, Severin N.; Noel, Nakita K.; Snaith, Henry J. Advanced Energy Materials, Vol. 7, Issue 1 https://doi.org/10.1002/aenm.201601079	journal	September 2016
Grafting of poly(3-hexylthiophene) brushes on oxides using click chemistry Paoprasert, Peerasak; Spalenka, Josef W.; Peterson, Dane L. J. Mater. Chem., Vol. 20, Issue 13 https://doi.org/10.1039/B920233A	journal	January 2010
Compositional engineering of perovskite materials for high-performance solar cells Jeon, Nam Joong; Noh, Jun Hong; Yang, Woon Seok Nature, Vol. 517, Issue 7535 https://doi.org/10.1038/nature14133	journal	January 2015
π-Conjugated Polymers for Organic Electronics and Photovoltaic Cell Applications ^† Facchetti, Antonio Chemistry of Materials, Vol. 23, Issue 3 https://doi.org/10.1021/cm102419z	journal	February 2011
Expanded Tetrahedral Molecules from 1,3,5,7-Tetraphenyladamantane Reichert, Veronica R.; Mathias, Lon J. Macromolecules, Vol. 27, Issue 24 https://doi.org/10.1021/ma00102a002	journal	November 1994
Adhesion properties of inverted polymer solarcells: Processing and film structure parameters Dupont, Stephanie R.; Voroshazi, Eszter; Heremans, Paul Organic Electronics, Vol. 14, Issue 5 https://doi.org/10.1016/j.orgel.2013.02.022	journal	May 2013
Perovskite-perovskite tandem photovoltaics with optimized band gaps Eperon, Giles E.; Leijtens, Tomas; Bush, Kevin A. Science, Vol. 354, Issue 6314 https://doi.org/10.1126/science.aaf9717	journal	October 2016
Reply to “Comment on ‘The Mechanism of Pyrolysis of Benzyl Azide: Spectroscopic Evidence for Benzemethanimine Formation’” Pinto, R. M.; Guerra, M.; Costa, M. L. The Journal of Physical Chemistry A, Vol. 119, Issue 29 https://doi.org/10.1021/acs.jpca.5b04334	journal	July 2015
Synthesis of a recyclable and efficient Pd( ii ) 4-(2-pyridyl)-1,2,3-triazole complex over a solid periodic mesoporous organosilica support by “click reactions” for the Stille coupling reaction Sharma, Priti; Singh, A. P. RSC Adv., Vol. 4, Issue 81 https://doi.org/10.1039/C4RA06459C	journal	January 2014
Minimal Effect of the Hole-Transport Material Ionization Potential on the Open-Circuit Voltage of Perovskite Solar Cells Belisle, Rebecca A.; Jain, Pratham; Prasanna, Rohit ACS Energy Letters, Vol. 1, Issue 3 https://doi.org/10.1021/acsenergylett.6b00270	journal	August 2016
Step toward robust and reliable amorphous polymer field-effect transistors and logic functions made by the use of roll to roll compatible printing processes Verilhac, Jean-Marie; Benwadih, Mohamed; Seiler, Anne-Laure Organic Electronics, Vol. 11, Issue 3 https://doi.org/10.1016/j.orgel.2009.11.027	journal	March 2010

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