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Naphthalene And Perylene Diimides For Organic Transistors.

F. Würthner, M. Stolte
Published 2011 · Medicine, Chemistry

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The development of ambient stable organic n-channel semiconductor molecules for thin-film transistors has experienced a tremendous impetus in the last decade to close the gap in performance in comparison to that of their p-channel counterparts. Especially naphthalene and perylene tetracarboxylic diimides (NDI and PDI) have shown to be the most valuable building blocks to achieve this challenging goal and to gain insight into the molecular structure-transistor performance relationship. Remaining challenges and new emerging research fields for these n-type semiconductors are the optimization of their deposition on flexible substrates, the control of their long term ambient stability and their implementation in complementary transistor circuits, display and sensor devices.
This paper references
10.1002/ADMA.200800629
Solution processed top-gate n-channel transistors and complementary circuits on plastics operating in ambient conditions
He Yan (2008)
10.1021/ja074675e
Organic n-channel transistors based on core-cyanated perylene carboxylic diimide derivatives.
R. Weitz (2008)
10.1016/J.SYNTHMET.2004.08.018
Structure–performance relationship in pentacene/Al2O3 thin-film transistors
W. L. Kalb (2004)
10.1021/JA045124G
Organic thin-film transistors based on carbonyl-functionalized quaterthiophenes: high mobility N-channel semiconductors and ambipolar transport.
M. Yoon (2005)
10.1002/ADMA.19960080312
Evidence for n‐type conduction in a perylene tetracarboxylic diimide derivative
G. Horowitz (1996)
10.1063/1.2803073
Air-stable n-channel organic thin-film transistors with high field-effect mobility based on N,N′-bis(heptafluorobutyl)-3,4:9,10-perylene diimide
J. H. Oh (2007)
10.1002/anie.201003722
A chiral and colorful redox switch: enhanced π acidity in action.
J. Míšek (2010)
10.1021/JO7015357
Core-tetrasubstituted naphthalene diimides: synthesis, optical properties, and redox characteristics.
C. Roeger (2007)
10.1021/OL0613416
Synthesis and optical and electrochemical properties of core-fluorinated perylene bisimides.
F. Würthner (2006)
10.1039/c0cc00078g
Core-substituted naphthalenediimides.
N. Sakai (2010)
10.1063/1.2387892
High performance n-channel organic field-effect transistors and ring oscillators based on C60 fullerene films
Thomas D. Anthopoulos (2006)
10.1021/CM902531D
Interplay between Energetic and Kinetic Factors on the Ambient Stability of n-Channel Organic Transistors Based on Perylene Diimide Derivatives
J. Oh (2009)
10.1063/1.2885712
n-type organic field effect transistors from perylene bisimide block copolymers and homopolymers
S. Huettner (2008)
10.1002/1439-7641(20010316)2:3<167::AID-CPHC167>3.0.CO;2-F
Solid-state structural and electrical characterization of N-benzyl and N-alkyl naphthalene 1,4,5,8-tetracarboxylic diimides.
H. Katz (2001)
10.1039/c0cc00947d
High performance organic semiconductors for field-effect transistors.
H. Dong (2010)
10.1002/1439-7641(20010716)2:7<448::AID-CPHC448>3.0.CO;2-#
Crystal and electronic structure of a fluorescent columnar liquid crystalline electron transport material.
I. Séguy (2001)
10.1002/ADMA.200701478
Core‐Fluorinated Perylene Bisimide Dyes: Air Stable n‐Channel Organic Semiconductors for Thin Film Transistors with Exceptionally High On‐to‐Off Current Ratios
R. Schmidt (2007)
10.1002/ADMA.200802934
Improvements in Stability and Performance of N, N′-Dialkyl Perylene Diimide-Based n-Type Thin-Film Transistors
Yugeng Wen (2009)
10.1021/CR050140X
Charge transport in organic semiconductors.
V. Coropceanu (2007)
10.1021/ja910667y
Core-expanded naphthalene diimides fused with 2-(1,3-dithiol-2-ylidene)malonitrile groups for high-performance, ambient-stable, solution-processed n-channel organic thin film transistors.
X. Gao (2010)
10.1038/nature02987
Low-voltage organic transistors with an amorphous molecular gate dielectric
M. Halik (2004)
10.1021/JP1025625
On the Air Stability of n-Channel Organic Field-Effect Transistors: A Theoretical Study of Adiabatic Electron Affinities of Organic Semiconductors
Y. Chang (2010)
10.1063/1.2953079
Effects of gate dielectrics and metal electrodes on air-stable n-channel perylene tetracarboxylic dianhydride single-crystal field-effect transistors
K. Yamada (2008)
10.1021/JA055686F
n-type organic field-effect transistors with very high electron mobility based on thiazole oligomers with trifluoromethylphenyl groups.
Shinji Ando (2005)
10.1063/1.1467706
N-type organic thin-film transistor with high field-effect mobility based on a N,N′-dialkyl-3,4,9,10-perylene tetracarboxylic diimide derivative
P. Malenfant (2002)
10.1021/CM802281K
Low-Temperature-Processible, Transparent, and Air-Operable n-Channel Fluorinated Phenylethylated Naphthalenetetracarboxylic Diimide Semiconductors Applied to Flexible Transistors
Byung-Jun Jung (2009)
10.1002/adma.201001502
Mixed self-assembled monolayer gate dielectrics for continuous threshold voltage control in organic transistors and circuits.
U. Zschieschang (2010)
10.1021/CM0704579
Cyanonaphthalene diimide semiconductors for air-stable, flexible, and optically transparent n-channel field-effect transistors
Brooks A. Jones (2007)
10.1002/1521-3773(20010316)40:6<1037::AID-ANIE10370>3.0.CO;2-H
Plastic Transistors Reach Maturity for Mass Applications in Microelectronics
F. Würthner (2001)
10.1038/35006603
A soluble and air-stable organic semiconductor with high electron mobility
H. Katz (2000)
10.1063/1.3153510
Electrical stability of inkjet-patterned organic complementary inverters measured in ambient conditions
S. Sambandan (2009)
10.1002/anie.200805228
Heteroanalogues of PCBM: N-bridged imino-PCBMs for organic field-effect transistors.
C. Yang (2009)
10.1002/ANIE.200461324
High-mobility air-stable n-type semiconductors with processing versatility: dicyanoperylene-3,4:9,10-bis(dicarboximides).
Brooks A Jones (2004)
10.1038/nature07727
A high-mobility electron-transporting polymer for printed transistors
H. Yan (2009)
10.1063/1.1949731
Air-stable ambipolar organic thin-film transistors based on an organic homostructure
R. Ye (2005)
10.1039/b909902f
Organic thin-film transistors.
H. Klauk (2010)
10.1063/1.2349290
High mobility n-type thin-film transistors based on N,N′-ditridecyl perylene diimide with thermal treatments
Shuhei Tatemichi (2006)
10.1016/J.TSF.2009.07.019
N-channel thin-film transistors based on 1,4,5,8-naphthalene tetracarboxylic dianhydride with ultrathin polymer gate buffer layer
Shinji Tanida (2009)
10.1021/ja901077a
High-performance air-stable n-channel organic thin film transistors based on halogenated perylene bisimide semiconductors.
R. Schmidt (2009)
10.1002/ADFM.200701045
Effects of Arylene Diimide Thin Film Growth Conditions on n‐Channel OFET Performance
Brooks A. Jones (2008)
10.1021/CM802071W
Thin-Film Morphology Control in Naphthalene-Diimide-Based Semiconductors: High Mobility n-Type Semiconductor for Organic Thin-Film Transistors
D. Shukla (2008)
10.1021/JA071760D
A high-mobility electron-transport polymer with broad absorption and its use in field-effect transistors and all-polymer solar cells.
X. Zhan (2007)
10.1063/1.115503
C60 thin film transistors
R. Haddon (1995)
10.1126/science.269.5230.1560
Organic Heterostructure Field-�ffect Transistors
A. Dodabalapur (1995)
10.1021/JA000870G
Naphthalenetetracarboxylic Diimide-Based n-Channel Transistor Semiconductors: Structural Variation and Thiol-Enhanced Gold Contacts
H. Katz (2000)
10.1063/1.1505746
Passivation effects of alumina insulating layer on C60 thin-film field-effect transistors
K. Horiuchi (2002)
10.1063/1.2907689
Growth and electrical properties of N,N′-bis(n-pentyl)terrylene- 3,4:11,12-tetracarboximide thin films
M. Petit (2008)
10.1002/ADFM.201000425
High‐Performance Air‐Stable n‐Type Organic Transistors Based on Core‐Chlorinated Naphthalene Tetracarboxylic Diimides
J. H. Oh (2010)
10.1021/CR940053X
Chemical Redox Agents for Organometallic Chemistry.
N. G. Connelly (1996)
10.1002/ADMA.200802733
High-Performance Organic Field-Effect Transistors
D. Braga (2009)
10.1039/b615857a
Chemistry of naphthalene diimides.
Sheshanath V. Bhosale (2008)
10.1016/J.ORGEL.2008.12.011
Measurement of the lowest unoccupied molecular orbital energies of molecular organic semiconductors
P. Djurovich (2009)
10.1002/ADFM.201000655
Air-Operable, High-Mobility Organic Transistors with Semifluorinated Side Chains and Unsubstituted Naphthalenetetracarboxylic Diimide Cores: High Mobility and Environmental and Bias Stress Stability from the Perfluorooctylpropyl Side Chain
Byung-Jun Jung (2010)
10.1002/ADMA.200803207
High Electron Mobility and Ambient Stability in Solution‐Processed Perylene‐Based Organic Field‐Effect Transistors
C. Piliego (2009)
10.1021/ja805407g
Naphthalenedicarboximide- vs perylenedicarboximide-based copolymers. Synthesis and semiconducting properties in bottom-gate N-channel organic transistors.
Z. Chen (2009)
10.1021/CM034140U
Cyanated perylene-3,4-dicarboximides and perylene-3,4:9,10-bis(dicarboximide): Facile chromophoric oxidants for organic photonics and electronics
M. Ahrens (2003)
10.1021/JA962461J
n-Channel Organic Transistor Materials Based on Naphthalene Frameworks
J. Laquindanum (1996)
10.1021/CR0501543
Electron and ambipolar transport in organic field-effect transistors.
J. Zaumseil (2007)
10.1021/JP046246Y
Organic Thin Film Transistors Based on N-Alkyl Perylene Diimides: Charge Transport Kinetics as a Function of Gate Voltage and Temperature
R. Chesterfield (2004)
10.1002/adma.200903628
n-Type organic semiconductors in organic electronics.
J. Anthony (2010)
10.1021/CM049391X
Introduction to Organic Thin Film Transistors and Design of n-Channel Organic Semiconductors
C. Newman (2004)
10.1021/JA9727629
New Air-Stable n-Channel Organic Thin Film Transistors
Zhenan Bao (1998)
10.1016/S1369-7021(07)70017-2
Semiconductors for organic transistors
A. Facchetti (2007)
10.1021/ja0371810
High electron mobility in ladder polymer field-effect transistors.
Amit Babel (2003)
10.1021/CR941014O
Ultrathin Organic Films Grown by Organic Molecular Beam Deposition and Related Techniques.
S. Forrest (1997)
10.1021/JA075242E
Tuning orbital energetics in arylene diimide semiconductors. materials design for ambient stability of n-type charge transport.
Brooks A Jones (2007)
10.1021/JA073306F
Anthracenedicarboximides as air-stable N-channel semiconductors for thin-film transistors with remarkable current on-off ratios.
Z. Wang (2007)
10.1002/anie.200904215
A crystal-engineered hydrogen-bonded octachloroperylene diimide with a twisted core: an n-channel organic semiconductor.
Marcel Gsänger (2010)
10.1002/ADFM.200400486
The Effect of Gate‐Dielectric Surface Energy on Pentacene Morphology and Organic Field‐Effect Transistor Characteristics
S. Y. Yang (2005)
10.1002/ADMA.200700064
High-performance solution-deposited n-channel organic transistors and their complementary circuits
B. Yoo (2007)
10.1002/adma.200901454
Recent progress in n-channel organic thin-film transistors.
Yugeng Wen (2010)
10.1021/ja809848y
High electron mobility in vacuum and ambient for PDIF-CN2 single-crystal transistors.
A. Molinari (2009)
10.1039/A605274F
Organic molecular solids as thin film transistor semiconductors
H. Katz (1997)
10.1016/J.ORGEL.2005.01.002
Relationship between the ionization and oxidation potentials of molecular organic semiconductors
B. D’Andrade (2005)
10.1021/CM902925G
High-Performance Solution-Deposited Ambipolar Organic Transistors Based on Terrylene Diimides
Chuan Liu (2010)
10.1002/ADFM.201000383
High Tg Cyclic Olefin Copolymer Gate Dielectrics for N,N'-Ditridecyl Perylene Diimide Based Field-Effect Transistors: Improving Performance and Stability with Thermal Treatment
J. Jang (2010)



This paper is referenced by
10.1021/acs.joc.9b01131
Perylene Bisimide Dyes with up to Five Independently Introduced Substituents: Controlling the Functionalization Pattern and Photophysical Properties Using Regiospecific Bay Substitution
Rajeev K Dubey (2019)
10.1039/c8cc07640e
Naphthalene and perylene diimides - better alternatives to fullerenes for organic electronics?
Agnieszka Nowak-Król (2018)
10.1002/anie.201408067
Ambient stable zwitterionic perylene bisimide-centered radical.
D. Schmidt (2015)
10.1021/ACS.MACROMOL.5B01070
N-Type Hyperbranched Polymers for Supercapacitor Cathodes with Variable Porosity and Excellent Electrochemical Stability
David F Zeigler (2015)
10.1016/J.INOCHE.2019.04.044
Substitution effects on NIR-absorbing Perylene Diimide based on DFT calculation
H. Li (2019)
10.1002/chem.201103158
Tetrachlorinated tetraazaperopyrenes (TAPPs): highly fluorescent dyes and semiconductors for air-stable organic n-channel transistors and complementary circuits.
Susanne C. Martens (2012)
Strategic Molecular Design to Engineer the Electron Affinity of Self-Assembling Organic Semiconductors
Kelly Nicole Zaugg (2016)
10.1016/J.CCLET.2012.07.005
rac-11-t-Butoxy-1,4-dihydro-1,4-methanoanthracene: A two-dimensional framework structure built from CH⋯O and CH⋯π hydrogen bonds
Hsing Yang Tsai (2012)
10.1039/c5cc09962e
Thionated perylene diimides with intense absorbance in the near-IR.
B. Llewellyn (2016)
10.1016/J.TET.2015.07.032
Synthesis and properties of perylene diimide dyes bearing unsymmetrical and symmetrical phenoxy substituents at bay positions
H. Zhao (2015)
10.1039/c7ob02749d
Perylenediimide-based glycoclusters as high affinity ligands of bacterial lectins: synthesis, binding studies and anti-adhesive properties.
M. Donnier-Maréchal (2017)
10.1039/C8TC05577G
Two isomeric perylenothiophene diimides: physicochemical properties and applications in organic semiconducting devices
M. Nakano (2019)
10.1021/ACS.CHEMMATER.5B01274
Importance of Electron Transport Ability in Naphthalene Diimide-Based Polymer Acceptors for High-Performance, Additive-Free, All-Polymer Solar Cells
Joonhyeong Choi (2015)
10.1002/anie.201207608
Self-assembling decacyclene triimides prepared through a regioselective hextuple Friedel-Crafts carbamylation.
T. V. Pho (2013)
10.1039/c2cs15313k
Small molecule semiconductors for high-efficiency organic photovoltaics.
Yuze Lin (2012)
10.1039/c2cc15733k
Angular-shaped naphthalene tetracarboxylic diimides for n-channel organic transistor semiconductors.
Shuanghong Chen (2012)
10.1002/chem.201801191
Tetrachlorinated Polycyclic Aromatic Dicarboximides: New Electron-Poor π-Scaffolds and NIR Emitters by Palladium-Catalyzed Annulation Reaction.
Magnus Mahl (2018)
10.1016/J.ELECTACTA.2019.04.012
Multi-carbonyl molecules immobilized on high surface area carbon by diazonium chemistry for energy storage applications
N. Delaporte (2019)
10.1088/1361-6463/ab8b04
Experimental Investigation of naphthalene based organic thin-film transistors by combining a polymer dielectric and a carrier injection layer
Atsuro Ohyama (2020)
10.1021/MA5001145
Naphthalene Diimide Copolymers with Oligo(p-phenylenevinylene) and Benzobisoxazole for Balanced Ambipolar Charge Transport
N. B. Kolhe (2014)
10.1021/cr400195e
Functional π-gelators and their applications.
S. S. Babu (2014)
10.1080/21606099.2013.791037
Bis(naphthalene diimide) derivatives with mono- and dicarbonyl-fused tricyclic heterocyclic bridges as electron-transport materials
Yulia A Getmanenko (2013)
10.1039/c1nr10973a
Reorganization of perylene bisimide J-aggregates: from delocalized collective to localized individual excitations.
Yuxi Tian (2012)
10.1021/acsomega.9b02514
Facile Synthesis and Evaluation of Electron Transport and Photophysical Properties of Photoluminescent PDI Derivatives
S. Naqvi (2019)
10.1016/j.nanoen.2020.104718
14.4% efficiency all-polymer solar cell with broad absorption and low energy loss enabled by a novel polymer acceptor
Tao Jia (2020)
10.1039/c7cp04756h
A solution-based single-molecule study of surface-bound PBIs: solvent-mediated environmental effects on molecular flexibility.
J. Lee (2017)
10.1039/C5TC01519G
From non-detectable to decent: replacement of oxygen with sulfur in naphthalene diimide boosts electron transport in organic thin-film transistors (OTFT)
W. Chen (2015)
10.1016/J.MOLCATA.2014.01.014
Electron-deficient naphthalene diimides as efficient planar π-acid organocatalysts for selective oxidative C–C coupling of 2,6-di-tert-butylphenol: A temperature effect
Hua Ke (2014)
10.1002/QUA.25337
On the applicability of time‐dependent density functional theory (TDDFT) and semiempirical methods to the computation of excited‐state potential energy surfaces of perylene‐based dye‐aggregates
C. Walter (2017)
10.1039/c7dt02067h
Electrochemical and structural investigation of the interactions between naphthalene diimides and metal cations.
Benjamin R. Reiner (2017)
10.1021/ja5035107
Homochiral columns constructed by chiral self-sorting during supramolecular helical organization of hat-shaped molecules.
C. Roche (2014)
10.1021/jo402365s
Diindole-annulated naphthalene diimides: synthesis and optical and electronic properties of syn- and anti-isomers.
Sabin-Lucian Suraru (2014)
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