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

Abstract

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 interfacialmore » device failure.« less

Authors:
ORCiD logo [1]; ORCiD logo [1];  [1];  [1]; ORCiD logo [1]
  1. Stanford Univ., Stanford, CA (United States)
Publication Date:
Research Org.:
Stanford Univ., CA (United States)
Sponsoring Org.:
USDOE Office of Energy Efficiency and Renewable Energy (EERE), Renewable Power Office. Solar Energy Technologies Office
OSTI Identifier:
1579847
Grant/Contract Number:  
EE0004946
Resource Type:
Accepted Manuscript
Journal Name:
Journal of Materials Chemistry. A
Additional Journal Information:
Journal Volume: 5; Journal Issue: 36; Journal ID: ISSN 2050-7488
Publisher:
Royal Society of Chemistry
Country of Publication:
United States
Language:
English
Subject:
36 MATERIALS SCIENCE

Citation Formats

Watson, Brian  L., Rolston, Nicholas, Bush, Kevin A., Taleghani, Leila, and Dauskardt, Reinhold H. Synthesis and use of a hyper-connecting cross-linking agent in the hole-transporting layer of perovskite solar cells. United States: N. p., 2017. Web. doi:10.1039/c7ta05004f.
Watson, Brian  L., Rolston, Nicholas, Bush, Kevin A., Taleghani, Leila, & Dauskardt, Reinhold H. Synthesis and use of a hyper-connecting cross-linking agent in the hole-transporting layer of perovskite solar cells. United States. https://doi.org/10.1039/c7ta05004f
Watson, Brian  L., Rolston, Nicholas, Bush, Kevin A., Taleghani, Leila, and Dauskardt, Reinhold H. Fri . "Synthesis and use of a hyper-connecting cross-linking agent in the hole-transporting layer of perovskite solar cells". United States. https://doi.org/10.1039/c7ta05004f. https://www.osti.gov/servlets/purl/1579847.
@article{osti_1579847,
title = {Synthesis and use of a hyper-connecting cross-linking agent in the hole-transporting layer of perovskite solar cells},
author = {Watson, Brian  L. and Rolston, Nicholas and Bush, Kevin A. and Taleghani, Leila and Dauskardt, Reinhold H.},
abstractNote = {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.},
doi = {10.1039/c7ta05004f},
journal = {Journal of Materials Chemistry. A},
number = 36,
volume = 5,
place = {United States},
year = {2017},
month = {8}
}

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Works referenced in this record:

Click Chemistry: Diverse Chemical Function from a Few Good Reactions
journal, June 2001


Enlightening solutions
journal, September 2005


Stretching and conformal bonding of organic solar cells to hemispherical surfaces
journal, January 2014

  • O'Connor, Timothy F.; Zaretski, Aliaksandr V.; Shiravi, Bijan A.
  • Energy Environ. Sci., Vol. 7, Issue 1
  • DOI: 10.1039/C3EE42898B

Organic Azides: An Exploding Diversity of a Unique Class of Compounds
journal, August 2005

  • Bräse, Stefan; Gil, Carmen; Knepper, Kerstin
  • Angewandte Chemie International Edition, Vol. 44, Issue 33
  • DOI: 10.1002/anie.200400657

Effects of Molecular Configuration on Charge Diffusion Kinetics within Hole-Transporting Materials for Perovskites Solar Cells
journal, April 2015

  • Chi, Wei-Jie; Li, Quan-Song; Li, Ze-Sheng
  • The Journal of Physical Chemistry C, Vol. 119, Issue 16
  • DOI: 10.1021/acs.jpcc.5b02401

Template-Guided Solution-Shearing Method for Enhanced Charge Carrier Mobility in Diketopyrrolopyrrole-Based Polymer Field-Effect Transistors
journal, June 2014

  • Shin, Jicheol; Hong, Tae Ryang; Lee, Tae Wan
  • Advanced Materials, Vol. 26, Issue 34
  • DOI: 10.1002/adma.201401179

Controlling Hierarchy in Solution-processed Polymer Solar Cells Based on Crosslinked P3HT
journal, August 2012

  • Tao, Chen; Aljada, Muhsen; Shaw, Paul E.
  • Advanced Energy Materials, Vol. 3, Issue 1
  • DOI: 10.1002/aenm.201200394

Thermodynamic, kinetic, and structural factors in the synthesis of imine-linked dynamic covalent frameworks
journal, January 2012


Application of click chemistry to the production of DNA microarrays
journal, January 2012

  • Uszczyńska, Barbara; Ratajczak, Tomasz; Frydrych, Emilia
  • Lab on a Chip, Vol. 12, Issue 6
  • DOI: 10.1039/c2lc21096g

New Thermally Cross-Linkable Polymer and Its Application as a Hole-Transporting Layer for Solution Processed Multilayer Organic Light Emitting Diodes
journal, September 2007

  • Ma, Biwu; Lauterwasser, Frank; Deng, Lan
  • Chemistry of Materials, Vol. 19, Issue 19
  • DOI: 10.1021/cm0715500

High-performance photovoltaic perovskite layers fabricated through intramolecular exchange
journal, May 2015


Unusually long lifetimes of the singlet nitrenes derived from 4-azido-2,3,5,6-tetrafluorobenzamides
journal, January 1994

  • Marcinek, Andrzej; Platz, Matthew S.; Chan, Stephen Y.
  • The Journal of Physical Chemistry, Vol. 98, Issue 2
  • DOI: 10.1021/j100053a012

Solvent engineering for high-performance inorganic–organic hybrid perovskite solar cells
journal, July 2014

  • Jeon, Nam Joong; Noh, Jun Hong; Kim, Young Chan
  • Nature Materials, Vol. 13, Issue 9, p. 897-903
  • DOI: 10.1038/nmat4014

High-Efficiency and Color Stable Blue-Light-Emitting Polymers and Devices
journal, December 2007

  • Huang, F.; Zhang, Y.; Liu, M. S.
  • Advanced Functional Materials, Vol. 17, Issue 18
  • DOI: 10.1002/adfm.200700752

Mechanical integrity of solution-processed perovskite solar cells
journal, December 2016


High-efficiency solution processable polymer photovoltaic cells by self-organization of polymer blends
journal, October 2005

  • Li, Gang; Shrotriya, Vishal; Huang, Jinsong
  • Nature Materials, Vol. 4, Issue 11, p. 864-868
  • DOI: 10.1038/nmat1500

Theoretical Investigation of Hole Transporter Materials for Energy Devices
journal, October 2015

  • Alberga, Domenico; Mangiatordi, Giuseppe Felice; Labat, Frédéric
  • The Journal of Physical Chemistry C, Vol. 119, Issue 42
  • DOI: 10.1021/acs.jpcc.5b08981

Fabrication and processing of polymer solar cells: A review of printing and coating techniques
journal, April 2009


Decohesion Kinetics in Polymer Organic Solar Cells
journal, November 2014

  • Bruner, Christopher; Novoa, Fernando; Dupont, Stephanie
  • ACS Applied Materials & Interfaces, Vol. 6, Issue 23
  • DOI: 10.1021/am506482q

Light-emitting diodes with variable colours from polymer blends
journal, December 1994

  • Berggren, M.; Inganäs, O.; Gustafsson, G.
  • Nature, Vol. 372, Issue 6505
  • DOI: 10.1038/372444a0

Comment on “The Mechanism of Pyrolysis of Benzyl Azide: Spectroscopic Evidence for Benzenemethanimine Formation”
journal, July 2015


High internal quantum efficiency in fullerene solar cells based on crosslinked polymer donor networks
journal, January 2012

  • Liu, Bo; Png, Rui-Qi; Zhao, Li-Hong
  • Nature Communications, Vol. 3, Issue 1
  • DOI: 10.1038/ncomms2211

The Mechanism of Pyrolysis of Benzyl Azide: Spectroscopic Evidence for Benzenemethanimine Formation
journal, April 2015

  • Pinto, Rui M.; Guerra, Mauro; Copeland, Grant
  • The Journal of Physical Chemistry A, Vol. 119, Issue 18
  • DOI: 10.1021/acs.jpca.5b02453

Solution-Processed Full-Color Polymer Organic Light-Emitting Diode Displays Fabricated by Direct Photolithography
journal, January 2007

  • Gather, M. C.; Köhnen, A.; Falcou, A.
  • Advanced Functional Materials, Vol. 17, Issue 2
  • DOI: 10.1002/adfm.200600651

Ultrasmooth organic–inorganic perovskite thin-film formation and crystallization for efficient planar heterojunction solar cells
journal, January 2015

  • Zhang, Wei; Saliba, Michael; Moore, David T.
  • Nature Communications, Vol. 6, Issue 1
  • DOI: 10.1038/ncomms7142

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

Clickable Periodic Mesoporous Organosilicas: Synthesis, Click Reactions, and Adsorption of Antibiotics
journal, November 2013

  • Gao, Jinsuo; Zhang, Xueying; Xu, Shutao
  • Chemistry - A European Journal, Vol. 20, Issue 7
  • DOI: 10.1002/chem.201303778

One-Step Facile Synthesis of a Simple Hole Transport Material for Efficient Perovskite Solar Cells
journal, April 2016


Understanding mechanical behavior and reliability of organic electronic materials
journal, February 2017

  • Kim, Jae-Han; Lee, Inhwa; Kim, Taek-Soo
  • MRS Bulletin, Vol. 42, Issue 02
  • DOI: 10.1557/mrs.2017.3

Orthogonal Processing: A Novel Photolithographic Patterning Method for Organic Electronics
journal, January 2009

  • Lee, Jin-Kyun; Taylor, Priscillia G.; Zakhidov, Alexander A.
  • Journal of Photopolymer Science and Technology, Vol. 22, Issue 5
  • DOI: 10.2494/photopolymer.22.565

Inkjet printing of organic electronics – comparison of deposition techniques and state-of-the-art developments
journal, January 2013

  • Teichler, Anke; Perelaer, Jolke; Schubert, Ulrich S.
  • Journal of Materials Chemistry C, Vol. 1, Issue 10
  • DOI: 10.1039/c2tc00255h

Polymer and Organic Nonvolatile Memory Devices
journal, February 2011

  • Heremans, Paul; Gelinck, Gerwin H.; Müller, Robert
  • Chemistry of Materials, Vol. 23, Issue 3
  • DOI: 10.1021/cm102006v

Macroscopic Alignment of One-Dimensional Conjugated Polymer Nanocrystallites for High-Mobility Organic Field-Effect Transistors
journal, May 2016

  • Chang, Mincheol; Choi, Dalsu; Egap, Eilaf
  • ACS Applied Materials & Interfaces, Vol. 8, Issue 21
  • DOI: 10.1021/acsami.6b02216

A [2,2]paracyclophane triarylamine-based hole-transporting material for high performance perovskite solar cells
journal, January 2015

  • Park, Sungmin; Heo, Jin Hyuck; Cheon, Cheol Hong
  • Journal of Materials Chemistry A, Vol. 3, Issue 48
  • DOI: 10.1039/C5TA08417B

High speeds complementary integrated circuits fabricated with all-printed polymeric semiconductors
journal, September 2010

  • Baeg, Kang-Jun; Khim, Dongyoon; Kim, Dong-Yu
  • Journal of Polymer Science Part B: Polymer Physics, Vol. 49, Issue 1
  • DOI: 10.1002/polb.22148

High-performance polymer semiconducting heterostructure devices by nitrene-mediated photocrosslinking of alkyl side chains
journal, December 2009

  • Png, Rui-Qi; Chia, Perq-Jon; Tang, Jie-Cong
  • Nature Materials, Vol. 9, Issue 2
  • DOI: 10.1038/nmat2594

Hydrofluoroethers as Orthogonal Solvents for the Chemical Processing of Organic Electronic Materials
journal, July 2008

  • Zakhidov, Alexander A.; Lee, Jin-Kyun; Fong, Hon Hang
  • Advanced Materials, Vol. 20, Issue 18
  • DOI: 10.1002/adma.200800557

Role of Molecular Weight on the Mechanical Device Properties of Organic Polymer Solar Cells
journal, January 2014

  • Bruner, Christopher; Dauskardt, Reinhold
  • Macromolecules, Vol. 47, Issue 3
  • DOI: 10.1021/ma402215j

Cesium-containing triple cation perovskite solar cells: improved stability, reproducibility and high efficiency
journal, January 2016

  • Saliba, Michael; Matsui, Taisuke; Seo, Ji-Youn
  • Energy & Environmental Science, Vol. 9, Issue 6
  • DOI: 10.1039/C5EE03874J

A solvent additive to enhance the efficiency and the thermal stability of polymer:fullerene solar cells
journal, January 2015

  • Derue, L.; Lecourtier, C.; Gorisse, T.
  • RSC Advances, Vol. 5, Issue 5
  • DOI: 10.1039/C4RA14139C

Thermal Stabilisation of Polymer-Fullerene Bulk Heterojunction Morphology for Efficient Photovoltaic Solar Cells
journal, July 2014

  • Derue, Lionel; Dautel, Olivier; Tournebize, Aurélien
  • Advanced Materials, Vol. 26, Issue 33
  • DOI: 10.1002/adma.201401062

Chemistry and kinetics of singlet pentafluorophenylnitrene
journal, June 1992

  • Poe, Russell; Schnapp, Karlyn; Young, Mary J. T.
  • Journal of the American Chemical Society, Vol. 114, Issue 13
  • DOI: 10.1021/ja00039a016

Scaffold-reinforced perovskite compound solar cells
journal, January 2017

  • Watson, Brian L.; Rolston, Nicholas; Printz, Adam D.
  • Energy & Environmental Science, Vol. 10, Issue 12
  • DOI: 10.1039/C7EE02185B

Polymer solar cells
journal, February 2012


Investigating the Role of 4- Tert Butylpyridine in Perovskite Solar Cells
journal, September 2016

  • Habisreutinger, Severin N.; Noel, Nakita K.; Snaith, Henry J.
  • Advanced Energy Materials, Vol. 7, Issue 1
  • DOI: 10.1002/aenm.201601079

Grafting of poly(3-hexylthiophene) brushes on oxides using click chemistry
journal, January 2010

  • Paoprasert, Peerasak; Spalenka, Josef W.; Peterson, Dane L.
  • J. Mater. Chem., Vol. 20, Issue 13
  • DOI: 10.1039/B920233A

Compositional engineering of perovskite materials for high-performance solar cells
journal, January 2015

  • Jeon, Nam Joong; Noh, Jun Hong; Yang, Woon Seok
  • Nature, Vol. 517, Issue 7535
  • DOI: 10.1038/nature14133

π-Conjugated Polymers for Organic Electronics and Photovoltaic Cell Applications
journal, February 2011


Expanded Tetrahedral Molecules from 1,3,5,7-Tetraphenyladamantane
journal, November 1994

  • Reichert, Veronica R.; Mathias, Lon J.
  • Macromolecules, Vol. 27, Issue 24
  • DOI: 10.1021/ma00102a002

Adhesion properties of inverted polymer solarcells: Processing and film structure parameters
journal, May 2013


Perovskite-perovskite tandem photovoltaics with optimized band gaps
journal, October 2016


Reply to “Comment on ‘The Mechanism of Pyrolysis of Benzyl Azide: Spectroscopic Evidence for Benzemethanimine Formation’”
journal, July 2015

  • Pinto, R. M.; Guerra, M.; Costa, M. L.
  • The Journal of Physical Chemistry A, Vol. 119, Issue 29
  • DOI: 10.1021/acs.jpca.5b04334

Minimal Effect of the Hole-Transport Material Ionization Potential on the Open-Circuit Voltage of Perovskite Solar Cells
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
journal, March 2010


Works referencing / citing this record:

Influence of Bulky Organo-Ammonium Halide Additive Choice on the Flexibility and Efficiency of Perovskite Light-Emitting Devices
journal, June 2018

  • Zhao, Lianfeng; Rolston, Nicholas; Lee, Kyung Min
  • Advanced Functional Materials, Vol. 28, Issue 31
  • DOI: 10.1002/adfm.201802060

Toward Perovskite Solar Cell Commercialization: A Perspective and Research Roadmap Based on Interfacial Engineering
journal, June 2018

  • Rajagopal, Adharsh; Yao, Kai; Jen, Alex K. -Y.
  • Advanced Materials, Vol. 30, Issue 32
  • DOI: 10.1002/adma.201800455

Rapid Aqueous Spray Fabrication of Robust NiO x : A Simple and Scalable Platform for Efficient Perovskite Solar Cells
journal, March 2019

  • Scheideler, William J.; Rolston, Nicholas; Zhao, Oliver
  • Advanced Energy Materials, Vol. 9, Issue 19
  • DOI: 10.1002/aenm.201803600