A Solution-Processable Donor-Acceptor Compound Containing Boron(III) Centers for Small-Molecule-Based High-Performance Ternary Electronic Memory Devices.

A novel small-molecule boron(III)-containing donor-acceptor compound has been synthesized and employed in the fabrication of solution-processable electronic resistive memory devices. High ternary memory performances with low turn-on (V(Th1)=2.0 V) and distinct threshold voltages (V(Th2)=3.3 V), small reading bias (1.0 V), and long retention time (>10(4) seconds) with a large ON/OFF ratio of each state (current ratio of "OFF", "ON1", and "ON2"=1:10(3):10(6)) have been demonstrated, suggestive of its potential application in high-density data storage. The present design strategy provides new insight in the future design of memory devices with multi-level transition states.

[1]  Yingli Rao,et al.  Four-coordinate organoboron compounds with a π-conjugated chelate ligand for optoelectronic applications. , 2011, Inorganic chemistry.

[2]  Charles R. Szmanda,et al.  Programmable polymer thin film and non-volatile memory device , 2004, Nature materials.

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

[4]  Raymond Ziessel,et al.  Lumineszierende Materialien: Fixierung von π‐konjugierten und heterocyclischen Liganden mit Bor(III) , 2014 .

[5]  B. Dong,et al.  Ion-based materials comprising planar charged species. , 2013, Chemical communications.

[6]  Youyong Li,et al.  Tailoring of Molecular Planarity to Reduce Charge Injection Barrier for High‐Performance Small‐Molecule‐Based Ternary Memory Device with Low Threshold Voltage , 2012, Advanced materials.

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

[8]  Hok-Lai Wong,et al.  A versatile photochromic dithienylethene-containing β-diketonate ligand: near-infrared photochromic behavior and photoswitchable luminescence properties upon incorporation of a boron(III) center. , 2010, Journal of the American Chemical Society.

[9]  Stephen Y. Chou,et al.  A Silicon Single-Electron Transistor Memory Operating at Room Temperature , 1997, Science.

[10]  Todd B. Marder,et al.  Die Borchemie leuchtet: optische Eigenschaften von Molekülen und Polymeren C.D.E. dankt EPSRC und Syngenta für Postgraduiertenstipendien und T.B.M. der University of Durham für Unterstützung sowie Prof. Dr. K. Tamao für einen Vorabdruck von Lit. 32. , 2002 .

[11]  Crystalline amorphous semiconductor superlattice. , 2008, Physical review letters.

[12]  Y. Yamashita,et al.  Synthesis and properties of terthiophene and bithiophene derivatives functionalized by BF2 chelation: a new type of electron acceptor based on quadrupolar structures. , 2010, Chemistry.

[13]  A. Yassar,et al.  Synthesis and optical properties of novel 1,3-propanedione bearing oligothiophene substituents , 2004 .

[14]  J. Campbell Scott,et al.  Is There an Immortal Memory? , 2004, Science.

[15]  S. P. Tiwari,et al.  Benzothiadiazole-Dithienopyrrole Donor–Acceptor–Donor and Acceptor–Donor–Acceptor Triads: Synthesis and Optical, Electrochemical, and Charge-Transport Properties , 2011 .

[16]  Sang-Hyun Hong,et al.  High‐Performance Programmable Memory Devices Based on Hyperbranched Copper Phthalocyanine Polymer Thin Films , 2008 .

[17]  T. Nakanishi,et al.  Aryl-substituted C3-bridged oligopyrroles as anion receptors for formation of supramolecular organogels. , 2007, Journal of the American Chemical Society.

[18]  Seth R. Marder,et al.  Design of Organic Chromophores for All-Optical Signal Processing Applications , 2014 .

[19]  G. Ulrich,et al.  Luminescent materials: locking π-conjugated and heterocyclic ligands with boron(III). , 2014, Angewandte Chemie.

[20]  F. Jäkle.  Advances in the synthesis of organoborane polymers for optical, electronic, and sensory applications. , 2010, Chemical reviews.

[21]  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.

[22]  Guoqing Zhang,et al.  Polymorphism and reversible mechanochromic luminescence for solid-state difluoroboron avobenzone. , 2010, Journal of the American Chemical Society.

[23]  J. Fabian,et al.  1,3,2‐Dioxaborines as potential components in advanced materials—a theoretical study on electron affinity , 2004 .

[24]  M. Dewhirst,et al.  A dual-emissive-materials design concept enables tumour hypoxia imaging. , 2009, Nature materials.

[25]  Kazuo Tanaka,et al.  Facile Modulation of Optical Properties of Diketonate-Containing Polymers by Regulating Complexation Ratios with Boron , 2013 .

[26]  S. J. Payne,et al.  Multi-emissive difluoroboron dibenzoylmethane polylactide exhibiting intense fluorescence and oxygen-sensitive room-temperature phosphorescence. , 2007, Journal of the American Chemical Society.

[27]  Tow Chong Chong,et al.  Phase change random access memory cell with superlattice-like structure , 2006 .

[28]  A. Wakamiya,et al.  Boron as a key component for new π-electron materials , 2006 .

[29]  J Joshua Yang,et al.  Memristive devices for computing. , 2013, Nature nanotechnology.

[30]  H. Maeda,et al.  Dipyrrolyldiketone difluoroboron complexes: novel anion sensors with C-H...X- interactions. , 2005, Chemistry.

[31]  Tadanori Kurosawa,et al.  New Donor–Acceptor Oligoimides for High-Performance Nonvolatile Memory Devices , 2011 .

[32]  J. Dupont,et al.  2,1,3‐Benzothiadiazole and Derivatives: Synthesis, Properties, Reactions, and Applications in Light Technology of Small Molecules , 2013 .

[33]  A. Zanelli,et al.  Thiophene–Benzothiadiazole Co‐Oligomers: Synthesis, Optoelectronic Properties, Electrical Characterization, and Thin‐Film Patterning , 2010 .

[34]  Qiang Zhao,et al.  Single Polymer‐Based Ternary Electronic Memory Material and Device , 2012, Advanced materials.

[35]  M. Halik,et al.  Electron-Transport Properties and Use in Organic Light-Emitting Diodes of a Bis(dioxaborine)fluorene Derivative† , 2004 .

[36]  Stephen Barlow,et al.  Bisdioxaborine polymethines with large third-order nonlinearities for all-optical signal processing. , 2006, Journal of the American Chemical Society.

[37]  R. Dittmann,et al.  Redox‐Based Resistive Switching Memories – Nanoionic Mechanisms, Prospects, and Challenges , 2009, Advanced materials.

[38]  Yang Yang,et al.  Organic Donor–Acceptor System Exhibiting Electrical Bistability for Use in Memory Devices , 2005, Advanced materials.

[39]  V. Yam,et al.  A highly selective bifunctional luminescence probe for potassium and fluoride ions. , 2011, Organic letters.

[40]  T. Michinobu,et al.  Crystalline Thin Film of a Donor‐ Substituted Cyanoethynylethene for Nanoscale Data Recording Through Intermolecular Charge‐Transfer Interactions , 2005 .

[41]  Z. Yin,et al.  Postchemistry of organic particles: when TTF microparticles meet TCNQ microstructures in aqueous solution. , 2010, Journal of the American Chemical Society.

[42]  Hok-Lai Wong,et al.  Photochromic thienylpyridine-bis(alkynyl)borane complexes: toward readily tunable fluorescence dyes and photoswitchable materials. , 2012, Organic letters.

[43]  Christopher D. Entwistle,et al.  Boron chemistry lights the way: optical properties of molecular and polymeric systems. , 2002, Angewandte Chemie.

[44]  Y. Chujo,et al.  Highly intense fluorescent diarylboron diketonate. , 2008, The Journal of organic chemistry.

[45]  B. Cho,et al.  Organic Resistive Memory Devices: Performance Enhancement, Integration, and Advanced Architectures , 2011 .

[46]  H. Takezoe,et al.  Oriented salts: dimension-controlled charge-by-charge assemblies from planar receptor-anion complexes. , 2010, Angewandte Chemie.

[47]  M. Rozenberg,et al.  Nonvolatile memory with multilevel switching: a basic model. , 2004, Physical review letters.

[48]  Seth R. Marder,et al.  Bis(dioxaborine) compounds with large two-photon cross sections, and their use in the photodeposition of silver , 2003 .

[49]  ERIC M. VOGEL,et al.  Technology and metrology of new electronic materials and devices. , 2007, Nature nanotechnology.

[50]  Guoqing Zhang,et al.  Emission Color Tuning with Polymer Molecular Weight for Difluoroboron Dibenzoylmethane‐Polylactide , 2008 .

[51]  R. Waser,et al.  Nanoionics-based resistive switching memories. , 2007, Nature materials.

[52]  V. Yam,et al.  Gated photochromism in triarylborane-containing dithienylethenes: a new approach to a "lock-unlock" system. , 2011, Journal of the American Chemical Society.

[53]  Kailash Gopalakrishnan,et al.  Overview of candidate device technologies for storage-class memory , 2008, IBM J. Res. Dev..

[54]  Kazuo Tanaka,et al.  Boron diiminate with aggregation-induced emission and crystallization-induced emission-enhancement characteristics. , 2014, Chemistry.

[55]  Rainer Waser,et al.  Nanoelectronics and Information Technology: Advanced Electronic Materials and Novel Devices , 2003 .

[56]  Daoben Zhu,et al.  A novel air-stable n-type organic semiconductor: 4,4′-bis[(6,6′-diphenyl)-2,2-difluoro-1,3,2-dioxaborine] and its application in organic ambipolar field-effect transistors , 2006 .

[57]  Vonika Ka-Man Au,et al.  Organic memory devices based on a bis-cyclometalated alkynylgold(III) complex. , 2015, Journal of the American Chemical Society.

[58]  S. Möller,et al.  A polymer/semiconductor write-once read-many-times memory , 2003, Nature.

[59]  J. Ouyang,et al.  Electrical Switching and Bistability in Organic/Polymeric Thin Films and Memory Devices , 2006 .

[60]  V. Yam,et al.  Synthesis, photochromic, and computational studies of dithienylethene-containing β-diketonate derivatives and their near-infrared photochromic behavior upon coordination of a boron(III) center. , 2013, Chemistry.

[61]  C. Wade,et al.  Fluoride ion complexation and sensing using organoboron compounds. , 2010, Chemical reviews.

[62]  Se-Ho Lee,et al.  Core-shell heterostructured phase change nanowire multistate memory. , 2008, Nano letters.

[63]  L. Wan,et al.  From a lamellar to hexagonal self-assembly of bis(4,4'-(m,m'-di(dodecyloxy)phenyl)-2,2'-difluoro-1,3,2-dioxaborin) molecules: a trans-to-cis-isomerization-induced structural transition studied with STM. , 2006, Angewandte Chemie.

[64]  V. Yam,et al.  Synthesis and characterization of luminescent rhenium(I) tricarbonyl diimine complexes with a triarylboron moiety and the study of their fluoride ion-binding properties. , 2009, Inorganic chemistry.

[65]  L. Jullien,et al.  Diaroyl(methanato)boron difluoride compounds as medium-sensitive two-photon fluorescent probes. , 2004, Chemistry.

[66]  D. Kwong,et al.  A dynamic random access memory based on a conjugated copolymer containing electron-donor and -acceptor moieties. , 2006, Angewandte Chemie.

[67]  Najun Li,et al.  A small-molecule-based ternary data-storage device. , 2010, Journal of the American Chemical Society.

[68]  M. Lankhorst,et al.  Low-cost and nanoscale non-volatile memory concept for future silicon chips , 2005, Nature materials.

[69]  J. C. Scott,et al.  Nonvolatile Memory Elements Based on Organic Materials , 2007 .