Solution-Processed n-Type Graphene Doping for Cathode in Inverted Polymer Light-Emitting Diodes

Kwon, Sung-Joo; Han, Tae-Hee; Kim, Young-Hoon; Ahmed, Towfiq; Seo, Hong-Kyu; Kim, Hobeom; Kim, Dong Jin; Xu, Wentao; Hong, Byung Hee; Zhu, Jian-Xin; Lee, Tae-Woo

doi:10.1021/acsami.7b15307

Title: Solution-Processed n-Type Graphene Doping for Cathode in Inverted Polymer Light-Emitting Diodes

Journal Article · Thu Jan 11 00:00:00 EST 2018 · ACS Applied Materials and Interfaces

DOI:https://doi.org/10.1021/acsami.7b15307· OSTI ID:1418760

Kwon, Sung-Joo ^[1]; Han, Tae-Hee ^[2]; Kim, Young-Hoon ^[3]; Ahmed, Towfiq ^[4]; Seo, Hong-Kyu ^[1]; Kim, Hobeom ^[5]; Kim, Dong Jin ^[6]; Xu, Wentao ^[7];

^[8];

^[4];

^[7]

Pohang Univ. of Science and Technology (POSTECH) (Korea, Republic of). Dept. of Materials Science and Engineering
Seoul National Univ. (Korea, Republic of). Dept. of Materials Science and Engineering; Univ. of California, Los Angeles, CA (United States). Dept. of Materials Science and Engineering; Univ. of California, Los Angeles, CA (United States). California NanoSystems Inst.
Seoul National Univ. (Korea, Republic of). Dept. of Materials Science and Engineering; Seoul National Univ. (Korea, Republic of). Research Inst. of Advanced Materials; Seoul National Univ. (Korea, Republic of). BK21 PLUS SNU Materials Division for Educating Creative Global Leaders
Los Alamos National Lab. (LANL), Los Alamos, NM (United States)
Seoul National Univ. (Korea, Republic of). Dept. of Materials Science and Engineering
Seoul National Univ. (Korea, Republic of). Program in Nano Science and Technology, Graduate School of Convergence Science and Technology
Seoul National Univ. (Korea, Republic of). Dept. of Materials Science and Engineering; Seoul National Univ. (Korea, Republic of). Research Inst. of Advanced Materials
Seoul National Univ. (Korea, Republic of). Program in Nano Science and Technology, Graduate School of Convergence Science and Technology; Seoul National Univ. (Korea, Republic of). Dept. of Chemistry

n-Type doping with (4-(1,3-dimethyl-2,3-dihydro-1H-benzoimidazol-2-yl)phenyl) dimethylamine (N-DMBI) reduces a work function (WF) of graphene by ~0.45 eV without significant reduction of optical transmittance. Solution process of N-DMBI on graphene provides effective n-type doping effect and air-stability at the same time. Although neutral N-DMBI act as an electron receptor leaving the graphene p-doped, radical N-DMBI acts as an electron donator leaving the graphene n-doped, which is demonstrated by density functional theory. We also verify the suitability of N-DMBI-doped n-type graphene for use as a cathode in inverted polymer light-emitting diodes (PLEDs) by using various analytical methods. Inverted PLEDs using a graphene cathode doped with N-DMBI radical showed dramatically improved device efficiency (~13.8 cd/A) than did inverted PLEDs with pristine graphene (~2.74 cd/A). Finally, N-DMBI-doped graphene can provide a practical way to produce graphene cathodes with low WF in various organic optoelectronics.

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Research Organization:: Los Alamos National Lab. (LANL), Los Alamos, NM (United States)

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

Grant/Contract Number:: AC52-06NA25396

OSTI ID:: 1418760

Report Number(s):: LA-UR-16-28960

Journal Information:: ACS Applied Materials and Interfaces, Vol. 10, Issue 5; ISSN 1944-8244

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 18 works

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References (58)

Electric Field Effect in Atomically Thin Carbon Films Novoselov, K. S. Science, Vol. 306, Issue 5696, p. 666-669 https://doi.org/10.1126/science.1102896	journal	October 2004
Large-scale pattern growth of graphene films for stretchable transparent electrodes Kim, Keun Soo; Zhao, Yue; Jang, Houk Nature, Vol. 457, Issue 7230 https://doi.org/10.1038/nature07719	journal	January 2009
Roll-to-roll production of 30-inch graphene films for transparent electrodes Bae, Sukang; Kim, Hyeongkeun; Lee, Youngbin Nature Nanotechnology, Vol. 5, Issue 8, p. 574-578 https://doi.org/10.1038/nnano.2010.132	journal	June 2010
The rise of graphene Geim, A. K.; Novoselov, K. S. Nature Materials, Vol. 6, Issue 3, p. 183-191 https://doi.org/10.1038/nmat1849	journal	March 2007
Large-Area Synthesis of High-Quality and Uniform Graphene Films on Copper Foils Li, X.; Cai, W.; An, J. Science, Vol. 324, Issue 5932, p. 1312-1314 https://doi.org/10.1126/science.1171245	journal	May 2009
Improvement of work function and hole injection efficiency of graphene anode using CHF ₃ plasma treatment Cho, Himchan; Dae Kim, Seong; Han, Tae-Hee 2D Materials, Vol. 2, Issue 1 https://doi.org/10.1088/2053-1583/2/1/014002	journal	December 2014
Controlled surface oxidation of multi-layered graphene anode to increase hole injection efficiency in organic electronic devices Han, Tae-Hee; Kwon, Sung-Joo; Seo, Hong-Kyu 2D Materials, Vol. 3, Issue 1 https://doi.org/10.1088/2053-1583/3/1/014003	journal	January 2016
Graphene-based flexible electronic devices Han, Tae-Hee; Kim, Hobeom; Kwon, Sung-Joo Materials Science and Engineering: R: Reports, Vol. 118 https://doi.org/10.1016/j.mser.2017.05.001	journal	August 2017
Extremely efficient flexible organic light-emitting diodes with modified graphene anode Han, Tae-Hee; Lee, Youngbin; Choi, Mi-Ri Nature Photonics, Vol. 6, Issue 2 https://doi.org/10.1038/nphoton.2011.318	journal	January 2012
Efficient and bright organic light-emitting diodes on single-layer graphene electrodes Li, Ning; Oida, Satoshi; Tulevski, George S. Nature Communications, Vol. 4, Issue 1 https://doi.org/10.1038/ncomms3294	journal	August 2013
Work-Function Engineering of Graphene Anode by Bis(trifluoromethanesulfonyl)amide Doping for Efficient Polymer Light-Emitting Diodes Kim, Donghyuk; Lee, Dongchan; Lee, Yonghee Advanced Functional Materials, Vol. 23, Issue 40 https://doi.org/10.1002/adfm201301386	journal	August 2013
Metal Oxide Induced Charge Transfer Doping and Band Alignment of Graphene Electrodes for Efficient Organic Light Emitting Diodes Meyer, Jens; Kidambi, Piran R.; Bayer, Bernhard C. Scientific Reports, Vol. 4, Issue 1 https://doi.org/10.1038/srep05380	journal	June 2014
Engineering high charge transfer n-doping of graphene electrodes and its application to organic electronics Sanders, Simon; Cabrero-Vilatela, Andrea; Kidambi, Piran R. Nanoscale, Vol. 7, Issue 30 https://doi.org/10.1039/C5NR03246F	journal	January 2015
Workfunction-Tunable, N-Doped Reduced Graphene Transparent Electrodes for High-Performance Polymer Light-Emitting Diodes Hwang, Jin Ok; Park, Ji Sun; Choi, Dong Sung ACS Nano, Vol. 6, Issue 1 https://doi.org/10.1021/nn203176u	journal	December 2011
Versatile p-Type Chemical Doping to Achieve Ideal Flexible Graphene Electrodes Han, Tae-Hee; Kwon, Sung-Joo; Li, Nannan Angewandte Chemie International Edition, Vol. 55, Issue 21 https://doi.org/10.1002/anie.201600414	journal	April 2016
Approaching ultimate flexible organic light-emitting diodes using a graphene anode Han, Tae-Hee; Park, Min-Ho; Kwon, Sung-Joo NPG Asia Materials, Vol. 8, Issue 9 https://doi.org/10.1038/am.2016.108	journal	September 2016
Synergetic electrode architecture for efficient graphene-based flexible organic light-emitting diodes Lee, Jaeho; Han, Tae-Hee; Park, Min-Ho Nature Communications, Vol. 7, Issue 1 https://doi.org/10.1038/ncomms11791	journal	June 2016
Interface Engineering of Layer-by-Layer Stacked Graphene Anodes for High-Performance Organic Solar Cells Wang, Yu; Tong, Shi Wun; Xu, Xiang Fan Advanced Materials, Vol. 23, Issue 13 https://doi.org/10.1002/adma.201003673	journal	January 2011
Organic solar cells using CVD-grown graphene electrodes Kim, Hobeom; Bae, Sang-Hoon; Han, Tae-Hee Nanotechnology, Vol. 25, Issue 1 https://doi.org/10.1088/0957-4484/25/1/014012	journal	December 2013
Ultrathin Organic Solar Cells with Graphene Doped by Ferroelectric Polarization Kim, Keumok; Bae, Sang-Hoon; Toh, Chee Tat ACS Applied Materials & Interfaces, Vol. 6, Issue 5 https://doi.org/10.1021/am405270y	journal	February 2014
On-Fabrication Solid-State N-Doping of Graphene by an Electron-Transporting Metal Oxide Layer for Efficient Inverted Organic Solar Cells Kim, Hobeom; Byun, Jinwoo; Bae, Sang-Hoon Advanced Energy Materials, Vol. 6, Issue 12 https://doi.org/10.1002/aenm.201600172	journal	April 2016
Recent advances in the application of two-dimensional materials as charge transport layers in organic and perovskite solar cells Van Le, Quyet; Choi, Jae-Young; Kim, Soo Young FlatChem, Vol. 2 https://doi.org/10.1016/j.flatc.2017.04.002	journal	April 2017
Work-Function Engineering of Graphene Electrodes by Self-Assembled Monolayers for High-Performance Organic Field-Effect Transistors Park, Jaesung; Lee, Wi Hyoung; Huh, Sung The Journal of Physical Chemistry Letters, Vol. 2, Issue 8 https://doi.org/10.1021/jz200265w	journal	March 2011
Large Scale Pattern Graphene Electrode for High Performance in Transparent Organic Single Crystal Field-Effect Transistors Liu, Wei; Jackson, Biyun Li; Zhu, Jing ACS Nano, Vol. 4, Issue 7 https://doi.org/10.1021/nn100728p	journal	June 2010
Synthesis of N-Doped Graphene by Chemical Vapor Deposition and Its Electrical Properties Wei, Dacheng; Liu, Yunqi; Wang, Yu Nano Letters, Vol. 9, Issue 5 https://doi.org/10.1021/nl803279t	journal	May 2009
Controllable N-Doping of Graphene Guo, Beidou; Liu, Qian; Chen, Erdan Nano Letters, Vol. 10, Issue 12 https://doi.org/10.1021/nl103079j	journal	December 2010
Synthesis, Structure, and Properties of Boron- and Nitrogen-Doped Graphene Panchakarla, L. S.; Subrahmanyam, K. S.; Saha, S. K. Advanced Materials https://doi.org/10.1002/adma.200901285	journal	August 2009
Chemical structures of hydrazine-treated graphene oxide and generation of aromatic nitrogen doping Park, Sungjin; Hu, Yichen; Hwang, Jin Ok Nature Communications, Vol. 3, Issue 1 https://doi.org/10.1038/ncomms1643	journal	January 2012
Band gap opening of monolayer and bilayer graphene doped with aluminium, silicon, phosphorus, and sulfur Denis, Pablo A. Chemical Physics Letters, Vol. 492, Issue 4-6 https://doi.org/10.1016/j.cplett.2010.04.038	journal	June 2010
Can Commonly Used Hydrazine Produce n-Type Graphene? Some, Surajit; Bhunia, Prasenjit; Hwang, EunHee Chemistry - A European Journal, Vol. 18, Issue 25 https://doi.org/10.1002/chem.201200104	journal	May 2012
N-Doping of Graphene Through Electrothermal Reactions with Ammonia Wang, Xinran; Li, Xiaolin; Zhang, Li Science, Vol. 324, Issue 5928, p. 768-771 https://doi.org/10.1126/science.1170335	journal	May 2009
N-Doped Graphene Field-Effect Transistors with Enhanced Electron Mobility and Air-Stability Xu, Wentao; Lim, Tae-Seok; Seo, Hong-Kyu Small, Vol. 10, Issue 10 https://doi.org/10.1002/smll.201303768	journal	February 2014
Controllable n-Type Doping on CVD-Grown Single- and Double-Layer Graphene Mixture Xu, Wentao; Wang, Lihua; Liu, Yiwen Advanced Materials, Vol. 27, Issue 9 https://doi.org/10.1002/adma.201405353	journal	January 2015
Tuning the Dirac Point in CVD-Grown Graphene through Solution Processed n-Type Doping with 2-(2-Methoxyphenyl)-1,3-dimethyl-2,3-dihydro-1 H -benzoimidazole Wei, Peng; Liu, Nan; Lee, Hye Ryoung Nano Letters, Vol. 13, Issue 5 https://doi.org/10.1021/nl303410g	journal	April 2013
Self-Encapsulated Doping of n-Type Graphene Transistors with Extended Air Stability Ho, Po-Hsun; Yeh, Yun-Chieh; Wang, Di-Yan ACS Nano, Vol. 6, Issue 7 https://doi.org/10.1021/nn301639j	journal	June 2012
25th Anniversary Article: Chemically Modified/Doped Carbon Nanotubes & Graphene for Optimized Nanostructures & Nanodevices Maiti, Uday Narayan; Lee, Won Jun; Lee, Ju Min Advanced Materials, Vol. 26, Issue 1 https://doi.org/10.1002/adma.201303265	journal	October 2013
Nitrogen-doped carbon nanotubes and graphene composite structures for energy and catalytic applications Lee, Won Jun; Maiti, Uday Narayan; Lee, Ju Min Chemical Communications, Vol. 50, Issue 52 https://doi.org/10.1039/c4cc00146j	journal	January 2014
Toward Intrinsic Graphene Surfaces: A Systematic Study on Thermal Annealing and Wet-Chemical Treatment of SiO ₂ -Supported Graphene Devices Cheng, Zengguang; Zhou, Qiaoyu; Wang, Chenxuan Nano Letters, Vol. 11, Issue 2 https://doi.org/10.1021/nl103977d	journal	February 2011
Atmospheric Oxygen Binding and Hole Doping in Deformed Graphene on a SiO₂ Substrate Ryu, Sunmin; Liu, Li; Berciaud, Stephane Nano Letters, Vol. 10, Issue 12, p. 4944-4951 https://doi.org/10.1021/nl1029607	journal	December 2010
The effect of chemical residues on the physical and electrical properties of chemical vapor deposited graphene transferred to SiO ₂ Pirkle, A.; Chan, J.; Venugopal, A. Applied Physics Letters, Vol. 99, Issue 12 https://doi.org/10.1063/1.3643444	journal	September 2011
Nitrogen-doped graphene: beyond single substitution and enhanced molecular sensing Lv, Ruitao; Li, Qing; Botello-Méndez, Andrés R. Scientific Reports, Vol. 2, Issue 1 https://doi.org/10.1038/srep00586	journal	August 2012
Adsorption of ammonia on graphene Romero, Hugo E.; Joshi, Prasoon; Gupta, Awnish K. Nanotechnology, Vol. 20, Issue 24 https://doi.org/10.1088/0957-4484/20/24/245501	journal	May 2009
Polyethylene Imine as an Ideal Interlayer for Highly Efficient Inverted Polymer Light-Emitting Diodes Kim, Young-Hoon; Han, Tae-Hee; Cho, Himchan Advanced Functional Materials, Vol. 24, Issue 24 https://doi.org/10.1002/adfm.201304163	journal	March 2014
Air stable hybrid organic-inorganic light emitting diodes using ZnO as the cathode Bolink, Henk J.; Coronado, Eugenio; Repetto, Diego Applied Physics Letters, Vol. 91, Issue 22 https://doi.org/10.1063/1.2809387	journal	November 2007
High Efficiency Composite Metal Oxide-Polymer Electroluminescent Devices: A Morphological and Material Based Investigation Kabra, Dinesh; Song, Myoung Hoon; Wenger, Bernard Advanced Materials, Vol. 20, Issue 18 https://doi.org/10.1002/adma.200800202	journal	July 2008
High performance polymer light-emitting diodes with N-type metal oxide/conjugated polyelectrolyte hybrid charge transport layers Sun Park, Ji; Ram Lee, Bo; Jeong, Eunjae Applied Physics Letters, Vol. 99, Issue 16 https://doi.org/10.1063/1.3653962	journal	October 2011
Highly efficient inverted polymer light-emitting diodes using surface modifications of ZnO layer Lee, Bo Ram; Jung, Eui Dae; Park, Ji Sun Nature Communications, Vol. 5, Issue 1 https://doi.org/10.1038/ncomms5840	journal	September 2014
Efficient iterative schemes for ab initio total-energy calculations using a plane-wave basis set Kresse, G.; Furthmüller, J. Physical Review B, Vol. 54, Issue 16, p. 11169-11186 https://doi.org/10.1103/PhysRevB.54.11169	journal	October 1996
Ab initiomolecular dynamics for liquid metals Kresse, G.; Hafner, J. Physical Review B, Vol. 47, Issue 1, p. 558-561 https://doi.org/10.1103/PhysRevB.47.558	journal	January 1993
Efficiency of ab-initio total energy calculations for metals and semiconductors using a plane-wave basis set Kresse, G.; Furthmüller, J. Computational Materials Science, Vol. 6, Issue 1, p. 15-50 https://doi.org/10.1016/0927-0256(96)00008-0	journal	July 1996
Generalized Gradient Approximation Made Simple Perdew, John P.; Burke, Kieron; Ernzerhof, Matthias Physical Review Letters, Vol. 77, Issue 18, p. 3865-3868 https://doi.org/10.1103/PhysRevLett.77.3865	journal	October 1996
Soft self-consistent pseudopotentials in a generalized eigenvalue formalism Vanderbilt, David Physical Review B, Vol. 41, Issue 11, p. 7892-7895 https://doi.org/10.1103/PhysRevB.41.7892	journal	April 1990
Norm-conserving and ultrasoft pseudopotentials for first-row and transition elements Kresse, G.; Hafner, J. Journal of Physics: Condensed Matter, Vol. 6, Issue 40 https://doi.org/10.1088/0953-8984/6/40/015	journal	October 1994
Van der Waals density functionals applied to solids Klimeš, Jiří; Bowler, David R.; Michaelides, Angelos Physical Review B, Vol. 83, Issue 19 https://doi.org/10.1103/PhysRevB.83.195131	journal	May 2011
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 Wei, Peng; Oh, Joon Hak; Dong, Guifang Journal of the American Chemical Society, Vol. 132, Issue 26 https://doi.org/10.1021/ja103173m	journal	July 2010
Monitoring dopants by Raman scattering in an electrochemically top-gated graphene transistor Das, A.; Pisana, S.; Chakraborty, B. Nature Nanotechnology, Vol. 3, Issue 4 https://doi.org/10.1038/nnano.2008.67	journal	March 2008
Raman Spectrum of Graphene and Graphene Layers Ferrari, A. C.; Meyer, J. C.; Scardaci, V. Physical Review Letters, Vol. 97, Issue 18, Article No. 187401 https://doi.org/10.1103/PhysRevLett.97.187401	journal	October 2006
N-Doped Graphene-SnO2 Sandwich Paper for High-Performance Lithium-Ion Batteries Wang, Xi; Cao, Xinqiang; Bourgeois, Laure Advanced Functional Materials, Vol. 22, Issue 13 https://doi.org/10.1002/adfm.201103110	journal	April 2012

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