Electrochromic and electroluminescent devices based on a novel branched quasi-dendric fluorene-carbazole-2,5-bis(2-thienyl)-1H-pyrrole system

We report here the synthesis of a novel branched quasi-dendric system, 9,9′-(9,9′-dihexylfluorene-2,7-diyl)bis[3,6-bis(2,5-bis(2-thienyl)pyrrol-1-yl)carbazole], (FCSNS), in four steps, followed by coating onto an ITO-coated glass surface by an electropolymerization process to give a very stable cross-linked polymeric film (poly-FCSNS). The yellowish-green color of this film in its neutral state changed reversibly to black upon oxidation. An electrochromic device, assembled in the sandwich configuration [ITO/anodically coloring polymer (poly-FCSNS)//gel electrolyte//cathodically coloring polymer/(PEDOT)/ITO], exhibited a relatively short response time (about 1 s), a high redox stability, and a high coloration efficiency (1624 cm2C−1). In addition to electrochromic studies, organic light-emitting diode (OLED) work was also carried out using FCSNS. A multilayer OLED having a configuration of ITO/PEDOT:PSS/FCSNS/Alq3/LiF : Al was fabricated, and it showed a turn-on voltage of approximately 6 V and exhibited a bright green emission with a luminance of 3700 cd m−2. The maximum luminous efficiency was found to be 2.0 cd A−1 at 14 V and 11.75 mA cm−2. The emitted light from the OLED device is green, and has the color coordinates of (x, y) (0.33, 0.54) according to CIE. Electrochemical and optical properties were also studied by using cyclic voltammetry, UV-Vis absorption and fluorescence spectroscopy, respectively.

[1]  S. Koyuncu,et al.  A new near-infrared switchable electrochromic polymer and its device application , 2010 .

[2]  Wallace W. H. Wong,et al.  The effect of molecule size and shape on free charge generation, transport and recombination in all-thiophene dendrimer:fullerene bulk heterojunctions , 2010 .

[3]  L. Aras,et al.  Synthesis and electropolymerization of the phthaocyanines with 4-(2,5-di-2-thiophen-2-yl-pyrrol-1-yl) substituents , 2010 .

[4]  J. Reynolds,et al.  Color control in pi-conjugated organic polymers for use in electrochromic devices. , 2010, Chemical reviews.

[5]  Lei Wang,et al.  Highly Efficient and Color‐Stable Deep‐Blue Organic Light‐Emitting Diodes Based on a Solution‐Processible Dendrimer , 2009, Advanced materials.

[6]  W. Kaim,et al.  Spectroelectrochemistry: the best of two worlds. , 2009, Chemical Society reviews.

[7]  S. Icli,et al.  A new conducting polymer of 2,5-bis(2-thienyl)-1H-(pyrrole) (SNS) containing carbazole subunit: Electrochemical, optical and electrochromic properties , 2009 .

[8]  S. Tagawa,et al.  Photovoltaic performance and charge carrier mobility of dendritic oligothiophene bearing perylene bis(dicarboximide) groups , 2009 .

[9]  Ken‐Tsung Wong,et al.  Synthesis and Properties of a Novel Cross-Linked Electroactive Polymer Formed from a Bipolar Starburst Monomer , 2009 .

[10]  A. Cihaner,et al.  Processable electrochromic and fluorescent polymers based on N-substituted thienylpyrrole , 2008 .

[11]  A. Cihaner,et al.  A new conducting polymer bearing 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) subunit: Synthesis and characterization , 2008 .

[12]  Ta-Ya Chu,et al.  A morphologically stable host material for efficient phosphorescent green and red organic light emitting devices , 2008 .

[13]  Ye Tao,et al.  Charge Transport, Photovoltaic, and Thermoelectric Properties of Poly(2,7‐Carbazole) and Poly(Indolo[3,2‐b]Carbazole) Derivatives , 2008 .

[14]  M. Leclerc,et al.  Poly(2,7-carbazole)s: structure-property relationships. , 2008, Accounts of chemical research.

[15]  R. Costa,et al.  Efficient blue emitting organic light emitting diodes based on fluorescent solution processable cyclic phosphazenes , 2008 .

[16]  A. Cihaner,et al.  A processable rainbow mimic fluorescent polymer and its unprecedented coloration efficiency in electrochromic device , 2008 .

[17]  Su Jin Kim,et al.  Fabrication and electrical characteristics of organic thin film transistor using π-conjugated dendrimer , 2008 .

[18]  Mario Leclerc,et al.  A Low‐Bandgap Poly(2,7‐Carbazole) Derivative for Use in High‐Performance Solar Cells , 2007 .

[19]  Andrew J. Steckl,et al.  A comparative study of electrode effects on the electrical and luminescent characteristics of Alq3/TPD OLED: Improvements due to conductive polymer (PEDOT) anode , 2007 .

[20]  J. Pei,et al.  Three-dimensional architectures for highly stable pure blue emission. , 2007, Journal of the American Chemical Society.

[21]  Ken‐Tsung Wong,et al.  A novel electrochromic polymer synthesized through electropolymerization of a new donor-acceptor bipolar system , 2007 .

[22]  C. Tanyeli,et al.  A novel multielectrochromic copolymer based on 1-(4-nitrophenyl)-2,5-di(2-thienyl)-1H-pyrrole and EDOT , 2007 .

[23]  C. Tanyeli,et al.  A soluble conducting polymer of 2,5-di(thiophen-2-yl)-1-p-tolyl-1H-pyrrole and its electrochromic device , 2007 .

[24]  S. Jungsuttiwong,et al.  Synthesis of electrochemically and thermally stable amorphous hole-transporting carbazole dendronized fluorene , 2007 .

[25]  C. Tanyeli,et al.  Synthesis and characterization of a new soluble conducting polymer and its electrochromic device , 2006 .

[26]  T. Masuda,et al.  Synthesis and properties of polyacetylenes carrying N-phenylcarbazole and triphenylamine moieties , 2006 .

[27]  Ken‐Tsung Wong,et al.  Synthesis and Properties of a Novel Electrochromic Polymer Obtained from the Electropolymerization of a 9,9'-Spirobifluorene-Bridged Donor−Acceptor (D−A) Bichromophore System , 2006 .

[28]  M. Leclerc,et al.  Polycarbazoles: 25 Years of Progress , 2005 .

[29]  S. Mashiko,et al.  Amplified spontaneous emission and laser emission from a high optical-gain medium of dye-doped dendrimer , 2005 .

[30]  A. Iraqi,et al.  3,6‐linked 9‐alkyl‐9H‐carbazole main‐chain polymers: Preparation and properties , 2004 .

[31]  F. Wudl,et al.  Organic Polymeric Electrochromic Devices: Polychromism with Very High Coloration Efficiency , 2004 .

[32]  Benjamin D. Reeves,et al.  Electrochromic devices based on soluble and processable dioxythiophene polymersElectronic supplementary information (ESI) available: details of the synthesis of PProDOT(CH2OC18H37)2 and PProDOT(CH2OEtHx)2 and their polymerization. See http://www.rsc.org/suppdata/jm/b3/b306365h/ , 2003 .

[33]  Wen‐Bin Zhang,et al.  Extended π-Conjugated Dendrimers Based on Truxene , 2003 .

[34]  Peter Strohriegl,et al.  Carbazole-containing polymers: synthesis, properties and applications , 2003 .

[35]  I. Samuel,et al.  The Effect of Core Delocalization on Intermolecular Interactions in Conjugated Dendrimers , 2003 .

[36]  P. Somani,et al.  Electrochromic materials and devices: present and future , 2003, Materials Chemistry and Physics.

[37]  P. Lacaze,et al.  Synthesis of 2,5-di(2-thienyl)-1H-pyrrole N-linked with conjugated bridges , 2002 .

[38]  M. Leclerc,et al.  Syntheses of Conjugated Polymers Derived from N-Alkyl-2,7-carbazoles , 2001 .

[39]  R. D. Rauh,et al.  High coloration efficiency electrochromics and their application to multi-color devices , 2001 .

[40]  James J. O'Brien,et al.  Progress with Light‐Emitting Polymers , 2000 .

[41]  Yamamoto Toshihide,et al.  Palladium/P(t-Bu)3-catalyzed synthesis of N-aryl azoles and application to the synthesis of 4,4′,4′′-tris(N-azolyl)triphenylamines , 2000 .

[42]  D. G. Morris,et al.  Strategies towards functionalised electronically conducting organic copolymers , 2000 .

[43]  Claes G. Granqvist,et al.  Progress in electrochromics: tungsten oxide revisited , 1999 .

[44]  A. Natansohn,et al.  Synthesis and Characterization of Novel Carbazole-Containing Soluble Polyimides , 1999 .

[45]  Alan J. Heeger,et al.  New Developments in the Photonic Applications of Conjugated Polymers , 1997 .

[46]  Yang Yang,et al.  MEASUREMENT OF THE ENERGY GAP IN SEMICONDUCTING POLYMERS USING THE LIGHT-EMITTING ELECTROCHEMICAL CELL , 1996 .

[47]  S. Jenekhe.  Excited-state complexes of conjugated polymers† , 1995 .

[48]  D. Rosseinsky,et al.  Studies of tetra-(bipyridilium) salts as possible polyelectrochromic materials , 1994 .

[49]  T. Fujimoto,et al.  Chromic materials. Part 1.—Liquid-crystalline behaviour and electrochromism in bis(octakis-n-alkylphthalocyaninato)lutetium(III) complexes , 1994 .

[50]  Klaus Bange,et al.  Electrochromic Materials for optical switching devices , 1990 .

[51]  J. Ferraris,et al.  Steric effects on the optical and electrochemical properties of N-substituted pyrrole–thiophene monomers and polymers , 1989 .

[52]  Fred Wudl,et al.  Optical properties of conducting polymers , 1988 .

[53]  C. Tang,et al.  Organic Electroluminescent Diodes , 1987 .

[54]  J. Ferraris,et al.  ‘Substitutional alloys’ of organic polymeric conductors , 1987 .

[55]  K. Deuchert,et al.  Multistage Organic Redox Systems—A General Structural Principle , 1978 .