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Title: Photo‐/Thermal‐Responsive Field‐Effect Transistor upon Blending Polymeric Semiconductor with Hexaarylbiimidazole toward Photonically Programmable and Thermally Erasable Memory Device

Abstract

Abstract It is shown that the semiconducting performance of field‐effect transistors (FETs) with PDPP4T (poly(diketopyrrolopyrrole‐quaterthiophene)) can be reversibly tuned by UV light irradiation and thermal heating after blending with the photochromic hexaarylbiimidazole compound ( p ‐NO 2 ‐HABI). A photo‐/thermal‐responsive FET with a blend thin film of PDPP4T and p ‐NO 2 ‐HABI is successfully fabricated. The transfer characteristics are altered significantly with current enhanced up to 10 6 ‐fold at V G = 0 V after UV light irradiation. However, further heating results in the recovery of the transfer curve. This approach can be extended to other semiconducting polymers such as P3HT (poly(3‐hexyl thiophene)), PBTTT (poly(2,5‐bis(3‐tetradecylthiophen‐2‐yl)thieno[3,2‐b] thiophene)) and PDPPDTT (poly(diketopyrrolopyrrole‐dithienothiophene)). It is hypothesized that TPIRs (2,4,5‐triphenylimidazolyl radicals) formed from p ‐NO 2 ‐HABI after UV light irradiation can interact with charge defects at the gate dielectric–semiconductor interface and those in the semiconducting layer to induce more hole carriers in the semiconducting channel. The application of the blend thin film of PDPP4T and p ‐NO 2 ‐HABI is further demonstrated to fabricate the photonically programmable and thermally erasable FET‐based nonvolatile memory devices that are advantageous in terms of i) high ON/OFF current ratio, ii) nondestructive reading at low electrical bias,more » and iii) reasonably highly stable ON‐state and OFF‐state.« less

Authors:
 [1];  [1];  [1];  [2];  [2];  [1];  [2];  [2];  [2]; ORCiD logo [1]
  1. Beijing National Laboratory for Molecular Sciences CAS Key Laboratory of Organic Solids CAS Center of Excellence in Molecular Sciences Institute of Chemistry Chinese Academy of Sciences Beijing 100190 P. R. China, School of Chemical Science University of Chinese Academy of Sciences Beijing 100049 P. R. China
  2. Beijing National Laboratory for Molecular Sciences CAS Key Laboratory of Organic Solids CAS Center of Excellence in Molecular Sciences Institute of Chemistry Chinese Academy of Sciences Beijing 100190 P. R. China
Publication Date:
Sponsoring Org.:
USDOE
OSTI Identifier:
1562586
Resource Type:
Publisher's Accepted Manuscript
Journal Name:
Advanced Materials
Additional Journal Information:
Journal Name: Advanced Materials Journal Volume: 31 Journal Issue: 44; Journal ID: ISSN 0935-9648
Publisher:
Wiley Blackwell (John Wiley & Sons)
Country of Publication:
Germany
Language:
English

Citation Formats

Liu, Yidong, Yang, Yizhou, Shi, Dandan, Xiao, Mingchao, Jiang, Lang, Tian, Jianwu, Zhang, Guanxin, Liu, Zitong, Zhang, Xisha, and Zhang, Deqing. Photo‐/Thermal‐Responsive Field‐Effect Transistor upon Blending Polymeric Semiconductor with Hexaarylbiimidazole toward Photonically Programmable and Thermally Erasable Memory Device. Germany: N. p., 2019. Web. doi:10.1002/adma.201902576.
Liu, Yidong, Yang, Yizhou, Shi, Dandan, Xiao, Mingchao, Jiang, Lang, Tian, Jianwu, Zhang, Guanxin, Liu, Zitong, Zhang, Xisha, & Zhang, Deqing. Photo‐/Thermal‐Responsive Field‐Effect Transistor upon Blending Polymeric Semiconductor with Hexaarylbiimidazole toward Photonically Programmable and Thermally Erasable Memory Device. Germany. https://doi.org/10.1002/adma.201902576
Liu, Yidong, Yang, Yizhou, Shi, Dandan, Xiao, Mingchao, Jiang, Lang, Tian, Jianwu, Zhang, Guanxin, Liu, Zitong, Zhang, Xisha, and Zhang, Deqing. Wed . "Photo‐/Thermal‐Responsive Field‐Effect Transistor upon Blending Polymeric Semiconductor with Hexaarylbiimidazole toward Photonically Programmable and Thermally Erasable Memory Device". Germany. https://doi.org/10.1002/adma.201902576.
@article{osti_1562586,
title = {Photo‐/Thermal‐Responsive Field‐Effect Transistor upon Blending Polymeric Semiconductor with Hexaarylbiimidazole toward Photonically Programmable and Thermally Erasable Memory Device},
author = {Liu, Yidong and Yang, Yizhou and Shi, Dandan and Xiao, Mingchao and Jiang, Lang and Tian, Jianwu and Zhang, Guanxin and Liu, Zitong and Zhang, Xisha and Zhang, Deqing},
abstractNote = {Abstract It is shown that the semiconducting performance of field‐effect transistors (FETs) with PDPP4T (poly(diketopyrrolopyrrole‐quaterthiophene)) can be reversibly tuned by UV light irradiation and thermal heating after blending with the photochromic hexaarylbiimidazole compound ( p ‐NO 2 ‐HABI). A photo‐/thermal‐responsive FET with a blend thin film of PDPP4T and p ‐NO 2 ‐HABI is successfully fabricated. The transfer characteristics are altered significantly with current enhanced up to 10 6 ‐fold at V G = 0 V after UV light irradiation. However, further heating results in the recovery of the transfer curve. This approach can be extended to other semiconducting polymers such as P3HT (poly(3‐hexyl thiophene)), PBTTT (poly(2,5‐bis(3‐tetradecylthiophen‐2‐yl)thieno[3,2‐b] thiophene)) and PDPPDTT (poly(diketopyrrolopyrrole‐dithienothiophene)). It is hypothesized that TPIRs (2,4,5‐triphenylimidazolyl radicals) formed from p ‐NO 2 ‐HABI after UV light irradiation can interact with charge defects at the gate dielectric–semiconductor interface and those in the semiconducting layer to induce more hole carriers in the semiconducting channel. The application of the blend thin film of PDPP4T and p ‐NO 2 ‐HABI is further demonstrated to fabricate the photonically programmable and thermally erasable FET‐based nonvolatile memory devices that are advantageous in terms of i) high ON/OFF current ratio, ii) nondestructive reading at low electrical bias, and iii) reasonably highly stable ON‐state and OFF‐state.},
doi = {10.1002/adma.201902576},
journal = {Advanced Materials},
number = 44,
volume = 31,
place = {Germany},
year = {Wed Sep 18 00:00:00 EDT 2019},
month = {Wed Sep 18 00:00:00 EDT 2019}
}

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Works referenced in this record:

Optically Tunable Field Effect Transistors with Conjugated Polymer Entailing Azobenzene Groups in the Side Chains
journal, February 2019

  • Tian, Jianwu; Fu, Lulu; Liu, Zitong
  • Advanced Functional Materials, Vol. 29, Issue 12
  • DOI: 10.1002/adfm.201807176

Trap density of states in small-molecule organic semiconductors: A quantitative comparison of thin-film transistors with single crystals
journal, April 2010


Towards the Development of Flexible Non-Volatile Memories
journal, August 2013


Layer-by-layer assembled charge-trap memory devices with adjustable electronic properties
journal, December 2007

  • Lee, Jang-Sik; Cho, Jinhan; Lee, Chiyoung
  • Nature Nanotechnology, Vol. 2, Issue 12
  • DOI: 10.1038/nnano.2007.380

End‐Capping π‐Conjugated Systems with Medium‐Sized Sulfur‐Containing Rings: A Route Towards Solution‐Processable Air‐Stable Semiconductors
journal, July 2018

  • Fukazawa, Aiko; Toda, Yusuke; Hayakawa, Masahiro
  • Chemistry – A European Journal, Vol. 24, Issue 44
  • DOI: 10.1002/chem.201802656

Flexible Non-Volatile Ferroelectric Polymer Memory with Gate-Controlled Multilevel Operation
journal, August 2012

  • Hwang, Sun Kak; Bae, Insung; Kim, Richard Hahnkee
  • Advanced Materials, Vol. 24, Issue 44
  • DOI: 10.1002/adma.201201831

(Semi)ladder-Type Bithiophene Imide-Based All-Acceptor Semiconductors: Synthesis, Structure–Property Correlations, and Unipolar n-Type Transistor Performance
journal, April 2018

  • Wang, Yingfeng; Guo, Han; Harbuzaru, Alexandra
  • Journal of the American Chemical Society, Vol. 140, Issue 19
  • DOI: 10.1021/jacs.8b02144

Recent Progress in High-Mobility Organic Transistors: A Reality Check
journal, July 2018

  • Paterson, Alexandra F.; Singh, Saumya; Fallon, Kealan J.
  • Advanced Materials, Vol. 30, Issue 36
  • DOI: 10.1002/adma.201801079

Modification of Side Chains of Conjugated Molecules and Polymers for Charge Mobility Enhancement and Sensing Functionality
journal, May 2018


Turn-On Mode Fluorescence Switch by Using Negative Photochromic Imidazole Dimer
journal, March 2019

  • Mutoh, Katsuya; Miyashita, Nanae; Arai, Kaho
  • Journal of the American Chemical Society, Vol. 141, Issue 14
  • DOI: 10.1021/jacs.9b01870

Enhancing polymer thermoelectric performance using radical dopants
journal, December 2017


High mobility diketopyrrolopyrrole (DPP)-based organic semiconductor materials for organic thin film transistors and photovoltaics
journal, January 2013

  • Li, Yuning; Sonar, Prashant; Murphy, Leanne
  • Energy & Environmental Science, Vol. 6, Issue 6
  • DOI: 10.1039/c3ee00015j

Stepwise Two-Photon-Induced Fast Photoswitching via Electron Transfer in Higher Excited States of Photochromic Imidazole Dimer
journal, April 2016

  • Kobayashi, Yoichi; Katayama, Tetsuro; Yamane, Takuya
  • Journal of the American Chemical Society, Vol. 138, Issue 18
  • DOI: 10.1021/jacs.6b01470

Photochromic Phenoxyl-Imidazolyl Radical Complexes with Decoloration Rates from Tens of Nanoseconds to Seconds
journal, April 2015

  • Yamashita, Hiroaki; Ikezawa, Takahiro; Kobayashi, Yoichi
  • Journal of the American Chemical Society, Vol. 137, Issue 15
  • DOI: 10.1021/jacs.5b02353

Printable ion-gel gate dielectrics for low-voltage polymer thin-film transistors on plastic
journal, October 2008

  • Cho, Jeong Ho; Lee, Jiyoul; Xia, Yu
  • Nature Materials, Vol. 7, Issue 11, p. 900-906
  • DOI: 10.1038/nmat2291

Optically switchable organic field-effect transistors based on photoresponsive gold nanoparticles blended with poly(3-hexylthiophene)
journal, July 2012

  • Raimondo, C.; Crivillers, N.; Reinders, F.
  • Proceedings of the National Academy of Sciences, Vol. 109, Issue 31
  • DOI: 10.1073/pnas.1203848109

New Organic Semiconductors with Imide/Amide-Containing Molecular Systems
journal, March 2014


Optical Modulation of the Charge Injection in an Organic Field-Effect Transistor Based on Photochromic Self-Assembled-Monolayer-Functionalized Electrodes
journal, February 2011

  • Crivillers, Núria; Orgiu, Emanuele; Reinders, Federica
  • Advanced Materials, Vol. 23, Issue 12
  • DOI: 10.1002/adma.201003736

Photoresponsive organic field-effect transistors involving photochromic molecules
journal, August 2016


Light-Tunable Nonvolatile Memory Characteristics in Photochromic RRAM
journal, July 2017

  • Ling, Haifeng; Tan, Kangming; Fang, Qiyun
  • Advanced Electronic Materials, Vol. 3, Issue 8
  • DOI: 10.1002/aelm.201600416

Imide- and Amide-Functionalized Polymer Semiconductors
journal, September 2014

  • Guo, Xugang; Facchetti, Antonio; Marks, Tobin J.
  • Chemical Reviews, Vol. 114, Issue 18
  • DOI: 10.1021/cr500225d

Side-Chain-Induced Rigid Backbone Organization of Polymer Semiconductors through Semifluoroalkyl Side Chains
journal, January 2016

  • Kang, Boseok; Kim, Ran; Lee, Seon Baek
  • Journal of the American Chemical Society, Vol. 138, Issue 11
  • DOI: 10.1021/jacs.5b10445

Printed, Flexible, Organic Nano-Floating-Gate Memory: Effects of Metal Nanoparticles and Blocking Dielectrics on Memory Characteristics
journal, March 2013

  • Kang, Minji; Baeg, Kang-Jun; Khim, Dongyoon
  • Advanced Functional Materials, Vol. 23, Issue 28
  • DOI: 10.1002/adfm.201203417

Linear Conjugated Polymer Backbones Improve Alignment in Nanogroove-Assisted Organic Field-Effect Transistors
journal, November 2017

  • Wang, Ming; Ford, Michael J.; Zhou, Cheng
  • Journal of the American Chemical Society, Vol. 139, Issue 48
  • DOI: 10.1021/jacs.7b10332

Boron-Stabilized Planar Neutral π-Radicals with Well-Balanced Ambipolar Charge-Transport Properties
journal, October 2017

  • Kushida, Tomokatsu; Shirai, Shusuke; Ando, Naoki
  • Journal of the American Chemical Society, Vol. 139, Issue 41
  • DOI: 10.1021/jacs.7b05471

Nanostructured materials for non-volatile organic transistor memory applications
journal, January 2016

  • Shih, C. -C.; Lee, W. -Y.; Chen, W. -C.
  • Materials Horizons, Vol. 3, Issue 4
  • DOI: 10.1039/C6MH00049E

High-Performance Nonvolatile Organic Transistor Memory Devices Using the Electrets of Semiconducting Blends
journal, July 2014

  • Chiu, Yu-Cheng; Chen, Tzu-Ying; Chen, Yougen
  • ACS Applied Materials & Interfaces, Vol. 6, Issue 15
  • DOI: 10.1021/am502732d

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


Significant Improvement of Semiconducting Performance of the Diketopyrrolopyrrole–Quaterthiophene Conjugated Polymer through Side-Chain Engineering via Hydrogen-Bonding
journal, December 2015

  • Yao, Jingjing; Yu, Chenmin; Liu, Zitong
  • Journal of the American Chemical Society, Vol. 138, Issue 1
  • DOI: 10.1021/jacs.5b09737

Synergistic Photomodulation of Capacitive Coupling and Charge Separation Toward Functional Organic Field-Effect Transistors with High Responsivity
journal, August 2015

  • Zhang, Hongtao; Hui, Jingshu; Chen, Hongliang
  • Advanced Electronic Materials, Vol. 1, Issue 9
  • DOI: 10.1002/aelm.201500159

Light-driven photochromism-induced reversible switching in P3HT–spiropyran hybrid transistors
journal, January 2012

  • Li, Yingruo; Zhang, Hongtao; Qi, Chuanmin
  • J. Mater. Chem., Vol. 22, Issue 10
  • DOI: 10.1039/C1JM14872A

Reliability of Organic Field-Effect Transistors
journal, October 2009


Arylazopyrazoles as Light-Responsive Molecular Switches in Cyclodextrin-Based Supramolecular Systems
journal, March 2016

  • Stricker, Lucas; Fritz, Eva-Corinna; Peterlechner, Martin
  • Journal of the American Chemical Society, Vol. 138, Issue 13
  • DOI: 10.1021/jacs.6b00484

Thermal and Optical Modulation of the Carrier Mobility in OTFTs Based on an Azo-anthracene Liquid Crystal Organic Semiconductor
journal, February 2017

  • Chen, Yantong; Li, Chao; Xu, Xiuru
  • ACS Applied Materials & Interfaces, Vol. 9, Issue 8
  • DOI: 10.1021/acsami.6b13500

Electron and Ambipolar Transport in Organic Field-Effect Transistors
journal, April 2007

  • Zaumseil, Jana; Sirringhaus, Henning
  • Chemical Reviews, Vol. 107, Issue 4, p. 1296-1323
  • DOI: 10.1021/cr0501543

Use of a 1 H -Benzoimidazole Derivative as an n -Type Dopant and To Enable Air-Stable Solution-Processed n -Channel Organic Thin-Film Transistors
journal, July 2010

  • Wei, Peng; Oh, Joon Hak; Dong, Guifang
  • Journal of the American Chemical Society, Vol. 132, Issue 26
  • DOI: 10.1021/ja103173m

Organic small molecule field-effect transistors with Cytop™ gate dielectric: Eliminating gate bias stress effects
journal, February 2007

  • Kalb, W. L.; Mathis, T.; Haas, S.
  • Applied Physics Letters, Vol. 90, Issue 9
  • DOI: 10.1063/1.2709894

Ultrafast Photodissociation Dynamics of a Hexaarylbiimidazole Derivative with Pyrenyl Groups: Dispersive Reaction from Femtosecond to 10 ns Time Regions
journal, June 2009

  • Miyasaka, Hiroshi; Satoh, Yusuke; Ishibashi, Yukihide
  • Journal of the American Chemical Society, Vol. 131, Issue 21
  • DOI: 10.1021/ja809195s

n-Type Doped Conjugated Polymer for Nonvolatile Memory
journal, February 2017


Organic Non-Volatile Memory Based on Pentacene Field-Effect Transistors Using a Polymeric Gate Electret
journal, December 2006


Single-Crystal C 60 Needle/CuPc Nanoparticle Double Floating-Gate for Low-Voltage Organic Transistors Based Non-Volatile Memory Devices
journal, October 2014

  • Chang, Hsuan-Chun; Lu, Chien; Liu, Cheng-Liang
  • Advanced Materials, Vol. 27, Issue 1
  • DOI: 10.1002/adma.201403771

Design, Synthesis, and Structure–Property Relationships of Isoindigo-Based Conjugated Polymers
journal, February 2014

  • Lei, Ting; Wang, Jie-Yu; Pei, Jian
  • Accounts of Chemical Research, Vol. 47, Issue 4
  • DOI: 10.1021/ar400254j

Rapid, Photomediated Healing of Hexaarylbiimidazole-Based Covalently Cross-Linked Gels
journal, August 2017


Organic Semiconductors Based on [1]Benzothieno[3,2- b ][1]benzothiophene Substructure
journal, April 2014

  • Takimiya, Kazuo; Osaka, Itaru; Mori, Takamichi
  • Accounts of Chemical Research, Vol. 47, Issue 5
  • DOI: 10.1021/ar400282g

Flexible non-volatile optical memory thin-film transistor device with over 256 distinct levels based on an organic bicomponent blend
journal, June 2016

  • Leydecker, Tim; Herder, Martin; Pavlica, Egon
  • Nature Nanotechnology, Vol. 11, Issue 9
  • DOI: 10.1038/nnano.2016.87

Non-volatile organic memory with sub-millimetre bending radius
journal, April 2014

  • Kim, Richard Hahnkee; Kim, Hae Jin; Bae, Insung
  • Nature Communications, Vol. 5, Issue 1
  • DOI: 10.1038/ncomms4583

High-Performance Organic Field-Effect Transistors
journal, April 2009


Photoactive Gate Dielectrics
journal, June 2010


High Mobility N-Type Transistors Based on Solution-Sheared Doped 6,13-Bis(triisopropylsilylethynyl)pentacene Thin Films
journal, July 2013

  • Naab, Benjamin D.; Himmelberger, Scott; Diao, Ying
  • Advanced Materials, Vol. 25, Issue 33
  • DOI: 10.1002/adma.201205098

n-Channel Semiconductor Materials Design for Organic Complementary Circuits
journal, July 2011

  • Usta, Hakan; Facchetti, Antonio; Marks, Tobin J.
  • Accounts of Chemical Research, Vol. 44, Issue 7, p. 501-510
  • DOI: 10.1021/ar200006r

Photoswitching of glass transition temperatures of azobenzene-containing polymers induces reversible solid-to-liquid transitions
journal, October 2016

  • Zhou, Hongwei; Xue, Changguo; Weis, Philipp
  • Nature Chemistry, Vol. 9, Issue 2
  • DOI: 10.1038/nchem.2625

Optically switchable transistors by simple incorporation of photochromic systems into small-molecule semiconducting matrices
journal, March 2015

  • Gemayel, Mirella El; Börjesson, Karl; Herder, Martin
  • Nature Communications, Vol. 6, Issue 1
  • DOI: 10.1038/ncomms7330

Design of a Photoactive Hybrid Bilayer Dielectric for Flexible Nonvolatile Organic Memory Transistors
journal, December 2015


25th Anniversary Article: Recent Advances in n-Type and Ambipolar Organic Field-Effect Transistors
journal, August 2013


Naphthobischalcogenadiazole Conjugated Polymers: Emerging Materials for Organic Electronics
journal, February 2017


Liquid-Crystalline Ordering as a Concept in Materials Science: From Semiconductors to Stimuli-Responsive Devices
journal, July 2013

  • Fleischmann, Eva-Kristina; Zentel, Rudolf
  • Angewandte Chemie International Edition, Vol. 52, Issue 34
  • DOI: 10.1002/anie.201300371

High-performance solution-processed polymer ferroelectric field-effect transistors
journal, February 2005

  • Naber, Ronald C. G.; Tanase, Cristina; Blom, Paul W. M.
  • Nature Materials, Vol. 4, Issue 3
  • DOI: 10.1038/nmat1329

Definitive Evidence for the Contribution of Biradical Character in a Closed-Shell Molecule, Derivative of 1,4-Bis-(4,5-diphenylimidazol-2-ylidene)cyclohexa-2,5-diene
journal, June 2004

  • Kikuchi, Azusa; Iwahori, Fumiyasu; Abe, Jiro
  • Journal of the American Chemical Society, Vol. 126, Issue 21
  • DOI: 10.1021/ja049423h

Enhanced charge mobility in a molecular hole transporter via addition of redox inactive ionic dopant: Implication to dye-sensitized solar cells
journal, December 2006

  • Snaith, Henry J.; Grätzel, Michael
  • Applied Physics Letters, Vol. 89, Issue 26
  • DOI: 10.1063/1.2424552

Optical switching of carrier transport in polymeric transistors with photochromic spiropyran molecules
journal, January 2013

  • Ishiguro, Yasushi; Hayakawa, Ryoma; Chikyow, Toyohiro
  • Journal of Materials Chemistry C, Vol. 1, Issue 17
  • DOI: 10.1039/c3tc30130c

Semiconducting π-Conjugated Systems in Field-Effect Transistors: A Material Odyssey of Organic Electronics
journal, November 2011

  • Wang, Chengliang; Dong, Huanli; Hu, Wenping
  • Chemical Reviews, Vol. 112, Issue 4
  • DOI: 10.1021/cr100380z

Optically switchable transistor via energy-level phototuning in a bicomponent organic semiconductor
journal, June 2012

  • Orgiu, Emanuele; Crivillers, Núria; Herder, Martin
  • Nature Chemistry, Vol. 4, Issue 8
  • DOI: 10.1038/nchem.1384

Ten Years of N-Heteropentacenes as Semiconductors for Organic Thin-Film Transistors
journal, March 2014


Photo-triggered solvent-free metamorphosis of polymeric materials
journal, September 2017


Polymer electronic memories: Materials, devices and mechanisms
journal, October 2008


A Flexible Bimodal Sensor Array for Simultaneous Sensing of Pressure and Temperature
journal, October 2013

  • Tien, Nguyen Thanh; Jeon, Sanghun; Kim, Do-Il
  • Advanced Materials, Vol. 26, Issue 5
  • DOI: 10.1002/adma.201302869

Is a polymer semiconductor having a “perfect” regular structure desirable for organic thin film transistors?
journal, January 2015

  • Hong, Wei; Chen, Shaoyun; Sun, Bin
  • Chemical Science, Vol. 6, Issue 5
  • DOI: 10.1039/C5SC00843C

Toward Printed Integrated Circuits based on Unipolar or Ambipolar Polymer Semiconductors
journal, June 2013

  • Baeg, Kang-Jun; Caironi, Mario; Noh, Yong-Young
  • Advanced Materials, Vol. 25, Issue 31
  • DOI: 10.1002/adma.201205361