Abstract
A series of phosphine oxide-functionalized polyfluorene derivatives, PFH-PO-40-1 (P1), PFH-PO-20-1 (P2), PFH-PO-10-1 (P3), and PFH-PO-1-1 (P4), were prepared via a palladium-mediated Suzuki cross-coupling reaction. The structures and purities of all polymers were fully characterized by 1H and 13C NMR, UV-vis and photoluminescent spectroscopy, gel permeation chromatography, and TGA/DSC. Their emission features showed single broad peaks at about 445 nm in film, compared with those in dilute solutions, which might be caused by some degree of aggregation in the excited states of the backbones. The best electroluminescence (EL) performance of these polymers with configuration of ITO/PEDOT:PSS/Polymer/Alq3/LiF/Al was obtained from P1 (current efficiency was 4.2 Cd/A at 6V).
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Braun D, Heeger AJ. Visible light emission from semiconducting polymer diodes. Appl Phys Lett, 1991, 58: 1982–1986
Burns PL, Holmes AB, Kraft A, Bradley DDC, Brown AR, Friend RH, Gywer RW. Chemical tuning of electroluminescent copolymers to improve emission efficiencies and allow patterning. Nature, 1992, 356: 47–49
Pei Q, Yu G, Zhang C, Yang Y, Heeger AJ. Polymer light-emitting electrochemical cells. Science, 1995, 269: 1086–1088
Müller CD, Falcou A, Reckefuss N, Rojahn M, Wiederhirn V, Rudati P, Frohne H, Nuyken O, Becker H, Meerhotz K. Multi-colour organic light-emitting displays by solution processing. Nature, 2003, 421: 829–833
Lovinger AJ, Rothverg LJ. Status of and prospects for organic electroluminescence. J Mater Res, 1996, 11: 3174–3187
Bao Z, Lovinger AJ, Brown J. New air-stable n-channel organic thin film transistors. J Am Chem Soc, 1998, 120: 207–208
Bao Z, Dodabalapur A, Lovinger AJ. Soluble and processable regioregular poly(3-hexylthiophene) for thin film field-effect transistor applications with high mobility. Appl Phys Lett, 1996, 69: 4108–4110
Sirringhaus H, Tessler N, Friend RH. Integrated optoelectronic devices based on conjugated polymers. Science, 1998, 280: 1741–1744
Babel A, Jenekhe SA. Electron transport in thin-film transistor from an n-type conjugated polymer. Adv Mater, 2002, 14: 371–374
Tang CW. Two-layer organic photovoltaic cell. Appl Phys Lett, 1986, 48: 183–185
Wohrle D, Meissner D. Organic solar cell. Adv Mater, 1991, 3: 129–138
Yu G, Heeger AJ. Charge separation and photovoltaic conversion in polymer composites with internal donor/acceptor heterojunctions. J Appl Phys, 1995, 78: 4510–4515
Arias AC, MacKenzie JD, Stevenson R, Halls JJM, Inbasekaran M, Woo EP, Richards D, Friend RH. Photovoltaic performance and morphology of polyfluorene blends: A combined microscopic and photovoltaic investigation. Macromolecules, 2001, 34: 6005–6013
Jenekhe SA, Yi S. Efficient photovoltaic cells from semiconducting polymer heterojunctions. Appl Phys Lett, 2000, 77: 2635–2637
Bernius MT, Inbasekaran M, O’Brien J, Wu WS. Progress with light-emitting polymers. Adv Mater, 2000, 12: 1737–1750
Neher D. Polyfluorene homopolymers: Conjugated liquid-crystalline polymers for bright blue emission and polarized electroluminescence. Macromol Rapid Commun, 2001, 22: 1366–1385
Scherf U, List EJW. Semiconducting polyfluorenes—Towards reliable structure-property relationship. Adv Mater, 2002, 14: 477–487
Klärner G, Lee JK, Davey MH, Miller RD. Exciton migration and trapping in copolymers based on dialkylfluorenes. Adv Mater, 1999, 11: 115–119
Yu WL, Pei J, Huang W, Heeger AJ. Spiro-functionalized polyfluorene derivatives as blue light-emitting materials. Adv Mater, 2000, 12: 828–831
Virgili T, Lidzey DG, Bradley DDC. Efficient energy transfer from blue to red in tetraphenylporphyrin-doped poly (9,9-dioctylfluorene) light-emitting diodes. Adv Mater, 2000, 12: 58–62
Whitehead KS, Grell M, Bradley DDC, Jandke M, Strohriegl P. Highly polarized blue electroluminescence from homogeneously aligned films of poly(9,9-dioctylfluorene). Appl Phys Lett, 2000, 76: 2946–2948
Grell M, Knoll W, Lupo D, Meisel A, Miteva T, Neher D, Nothofer HG, Scherf U, Yasuda A. Blue polarized electroluminescence from a liquid crystalline polyfluorene. Adv Mater, 1999, 11: 671–675
Liu B, Bazan GC. Optimization of the molecular orbital energies of conjugated polymers for optical amplification of fluorescent sen sors. J Am Chem Soc, 2006, 128: 1188–1196
Wang S, Gaylord BS, Bazan GC. Fluorescein provides a resonance gate for FRET from conjugated polymers to DNA intercalated dyes. J Am Chem Soc, 2004, 126: 5446–5451
Liu B, Wang S, Bazan GC, Mikhailovsky A. Shape-adaptable water-soluble conjugated polymers. J Am Chem Soc, 2003, 125: 13306–13307
Fan C, Plaxco KW, Heeger AJ, High-efficiency fluorescence quenching of conjugated polymers by proteins. J Am Chem Soc, 2002, 124: 5642–5643
Zhou G, Cheng YX, Wang LX, Jing XB, Wang FS. Novel polyphenylenes containing phenol-substituted oxadiazole moieties as fluorescent chemosensors for fluoride ion. Macromolecules, 2005, 38: 2148–2153
Zhou X, Yan J, Pei J. Exploiting an imidazole-functionalized polyfluorene derivative as a chemosensory material. Macromolecules, 2004, 37: 7078–7080
Zhou G, Qian G, Ma L, Cheng YX, Xie ZY, Wang LX, Jing XB, Wang FS. Polyfluorenes with phosphonate groups in the side chains as chemosensors and electroluminescent materials. Macromolecules, 2005, 38: 5416–5424
Qin CJ, Cheng YX, Wang LX, Jing XB, Wang FS. Phosphonate-functionalized polyfluorene as a highly water-soluble iron(III) chemosensor. Macromolecules, 2008, 41: 7798–7804
Qin CJ, Wu XF, Gao BX, Tong H, Wang LX. Amino acid-functionalized polyfluorene as a water-soluble Hg2+ chemosensor with high solubility and high photoluminescence quantum yield. Macromolecules, 2009, 42: 5427–5433
Wu X, Xu B, Tong H, Wang LX. Phosphonate-functionalized polyfluorene film sensors for sensitive detection of iron(III) in both organic and aqueous media. Macromolecules, 2010, 43: 8917–8921
Huang F, Hou L, Wu H, Wang X, Shen H, Cao W. High-efficiency, environment-friendly electroluminescent polymers with stable high work function metal as a cathode: Green- and yellow-emitting conjugated polyfluorene polyelectrolytes and their neutral precursors. J Am Chem Soc, 2004, 126: 9845–9853
Wu H, Huang F, Mo Y, Yang W, Wang D, Peng J. Efficient electron injection from a bilayer cathode consisting of aluminum and alcohol-/water-soluble conjugated polymers. Adv Mater, 2004, 16: 1826–1830
Yang R, Wu H, Cao Y, Bazan GC. Control of cationic conjugated polymer performance in light emitting diodes by choice of counterion. J Am Chem Soc, 2006, 128: 14422–14423
Peng XG, Schlamp MC, Kadavanich AV, Alivisatos AP. Epitaxial growth of highly luminescent CdSe/CdS core/shell nanocrystals with photostability and electronic accessibility. J Am Chem Soc, 1997, 119: 7019–7029
Skaff H, Sill K, Emrick T. Quantum dots tailored with poly(para-phenylene vinylene). J Am Chem Soc, 2004, 126: 11322–11325
Scherf U, List EJW. Semiconducting polyfluorenes-Towards reliable structure-property relationships. Adv Mater, 2002, 14: 477–487
Gong X, Iyer PK, Moses D, Bazan GC, Heeger AJ, Xiao SS. Stabilized blue emission from polyfluorene-based light-emitting diodes: Elimination of fluorenone defects. Adv Funct Mater, 2003, 13: 325–330
Gong X, Moses D, Heeger AJ. White light electrophosphorescence from polyfluorene-based light-emitting diodes: Utilization of fluorenone defects. J Phys Chem B, 2004, 108: 8601–8605
Brooks AJ, Antonio F, Micheal RW, Tobin JM. Effects of arylene diimide thin film growth conditions on n-channel OFET performance. Adv Funct Mater, 2008, 18: 1329–1339
Chu B, Laser Light Scattering: Basic Principles and Practice. 2nd ed, San Diego: Academic Press, 1991
Hall J, Lehn JM, DeCian A, Fischer J. Synthesis and structure of the copper(II) complex of a chiral bis(dihydrooxazole) ligand. Helv Chim Acta, 1991, 74: 1–6
Yan JC, Chen X, Zhou QL, Pei J. Chiral polyfluorene derivatives: Synthesis, chiroptical properties, and investigation of the structure-property relationships. Macromolecules, 2007, 40: 832–839
Leeuw DM, Simenon MMJ, Brown AR, Einerhand REF. Stability of n-type doped conducting polymers and consequences for polymeric microelectronic devices. Synth Met, 1997, 87: 53–59
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Guo, Z., Liu, D., Wang, C. et al. Phosphine oxide-functionalized polyfluorene derivatives: Synthesis, photophysics, electrochemical properties, and electroluminescence performance. Sci. China Chem. 54, 678–684 (2011). https://doi.org/10.1007/s11426-011-4249-3
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DOI: https://doi.org/10.1007/s11426-011-4249-3