Main chain copolysiloxanes with terthiophene and perylenediimide units: synthesis, characterization and electrical memory

A main chain donor–acceptor copolysiloxane named poly(N,N′-bis(dimethylsiloxane)propyl tetrachloro perylene tetracarboxylic acid diimide-alt-bis(dimethylsiloxane)-2,2′:5′,2′′-terthiophene) (PBIClSi-alt-PTSi) was successfully synthesized, in which terthiophene donors and perylenediimide acceptors are connected with siloxanes. PBIClSi-alt-PTSi displays high thermal stability, which ensures its long-term stability for device operation. The calculated HOMO and LUMO energy levels of PBIClSi-alt-PTSi are mainly located on terthiophene and perylenediimide moieties, respectively. A fabricated memory device with the configuration of ITO/PBIClSi-alt-PTSi/Au(Al) shows nonvolatile write-once-read many-times (WORM) memory characteristics. Its turn-on threshold voltage is quite low (ca. 1.0 V), meanwhile the on/off current density ratio is around 6 × 103 under ambient atmosphere. As far as we know, this is the first example of a main chain donor–acceptor copolysiloxane used as a memory device. And the low turn-on threshold voltage of 1.0 V may be caused by the high flexibility of Si–O–Si. Furthermore, the progression of the ITO/PBIClSi-alt-PTSi/Au device from a low to high conductivity state is detected by current sensing atomic force microscopy for the first time. At the threshold voltage, the topology of the PBIClSi-alt-PTSi films displays an obvious change due to the arrangement of molecular chains.

[1]  Shouke Yan,et al.  Polysiloxanes for optoelectronic applications , 2016 .

[2]  Dongyun Chen,et al.  Multilevel Conductance Switching of a Memory Device Induced by Enhanced Intermolecular Charge Transfer , 2015, Advanced materials.

[3]  Shouke Yan,et al.  The synthesis and flash memory behavior of alternate copolymer containing carbazole donor and perylenediimide derivatives acceptor by the hybridization of organo-silicon , 2015 .

[4]  Dongyun Chen,et al.  Controlling Crystallite Orientation of Diketopyrrolopyrrole‐Based Small Molecules in Thin Films for Highly Reproducible Multilevel Memory Device: Role of Furan Substitution , 2015 .

[5]  Shouke Yan,et al.  Solution-Processed Blue/Deep Blue and White Phosphorescent Organic Light-Emitting Diodes (PhOLEDs) Hosted by a Polysiloxane Derivative with Pendant mCP (1,3-bis(9-carbazolyl)benzene). , 2015, ACS applied materials & interfaces.

[6]  Yu‐Cheng Chiu,et al.  Non-volatile organic transistor memory devices using the poly(4-vinylpyridine)-based supramolecular electrets. , 2015, Chemical communications.

[7]  Lili Liu,et al.  Synthesis of Alternating Copolysiloxane with Terthiophene and Perylenediimide Derivative Pendants for Involatile WORM Memory Device , 2014 .

[8]  Chengyuan Wang,et al.  Synthesis, characterization, and nonvolatile ternary memory behavior of a larger heteroacene with nine linearly fused rings and two different heteroatoms. , 2013, Journal of the American Chemical Society.

[9]  Chih-Jung Chen,et al.  Linkage and acceptor effects on diverse memory behavior of triphenylamine-based aromatic polymers , 2013 .

[10]  Brett A. Kamino,et al.  The use of siloxanes, silsesquioxanes, and silicones in organic semiconducting materials. , 2013, Chemical Society reviews.

[11]  Cheng-Liang Liu,et al.  Conjugated fluorene based rod-coil block copolymers and their PCBM composites for resistive memory switching devices. , 2011, ACS applied materials & interfaces.

[12]  Wei Li,et al.  Electrochemical Considerations for Determining Absolute Frontier Orbital Energy Levels of Conjugated Polymers for Solar Cell Applications , 2011, Advanced materials.

[13]  Quli Fan,et al.  Flash‐Memory Effect for Polyfluorenes with On‐Chain Iridium(III) Complexes , 2011 .

[14]  R. Hicks Switchable materials: A new spin on bistability. , 2011, Nature chemistry.

[15]  Cheng-Liang Liu,et al.  Synthesis, Morphology, and Properties of Poly(3‐hexylthiophene)‐block‐Poly(vinylphenyl oxadiazole) Donor–Acceptor Rod–Coil Block Copolymers and Their Memory Device Applications , 2010 .

[16]  Koon Gee Neoh,et al.  Nonvolatile Electrical Switching and Write-Once Read-Many-Times Memory Effects in Functional Polyimides Containing Triphenylamine and 1,3,4-Oxadiazole Moieties , 2010 .

[17]  Bin Zhang,et al.  Polyfluorene-Based Push−Pull Type Functional Materials for Write-Once-Read-Many-Times Memory Devices , 2010 .

[18]  Gang Liu,et al.  Conjugated‐Polymer‐Functionalized Graphene Oxide: Synthesis and Nonvolatile Rewritable Memory Effect , 2010, Advanced materials.

[19]  Wen‐Chang Chen,et al.  Non-volatile memory devices based on polystyrene derivatives with electron-donating oligofluorene pendent moieties. , 2009, ACS applied materials & interfaces.

[20]  Changhee Lee,et al.  Surface coatings based on polysilsesquioxanes: solution-processible smooth hole-injection layers for optoelectronic applications. , 2009, Macromolecular rapid communications.

[21]  Dong Min Kim,et al.  Nonvolatile unipolar and bipolar bistable memory characteristics of a high temperature polyimide bearing diphenylaminobenzylidenylimine moieties. , 2009, The journal of physical chemistry. B.

[22]  Cheng-Liang Liu,et al.  Synthesis and Memory Device Characteristics of New Sulfur Donor Containing Polyimides , 2009 .

[23]  Koon Gee Neoh,et al.  Polymer electronic memories: Materials, devices and mechanisms , 2008 .

[24]  Wei Huang,et al.  An effective Friedel-Crafts postfunctionization of poly(N-vinylcarbazole) to tune carrier transportation of supramolecular organic semiconductors based on pi-stacked polymers for nonvolatile flash memory cell. , 2008, Journal of the American Chemical Society.

[25]  Sang-Hyun Hong,et al.  Novel Digital Nonvolatile Memory Devices Based on Semiconducting Polymer Thin Films , 2007 .

[26]  Koon Gee Neoh,et al.  Conformation-Induced Electrical Bistability in Non-conjugated Polymers with Pendant Carbazole Moieties , 2007 .

[27]  Yan Song,et al.  Bistable electrical switching and memory effects in a thin film of copolymer containing electron donor-acceptor moieties and europium complexes. , 2006, The journal of physical chemistry. B.

[28]  Yan Song,et al.  Synthesis and dynamic random access memory behavior of a functional polyimide. , 2006, Journal of the American Chemical Society.

[29]  Chunxiang Zhu,et al.  Non-volatile WORM memory device based on an acrylate polymer with electron donating carbazole pendant groups , 2006 .

[30]  M. Wong,et al.  Full Emission Color Tuning in Bis-Dipolar Diphenylamino-Endcapped Oligoarylfluorenes , 2005 .

[31]  J. Cella,et al.  A New Polycondensation Process for the Preparation of Polysiloxane Copolymers , 2005 .

[32]  R. Muller,et al.  Polymer and Organic Nonvolatile Memory Devices , 2011 .