Synthesis of novel twisted carbazole–quinoxaline derivatives with 1,3,5-benzene core: bipolar molecules as hosts for phosphorescent OLEDs

Abstract A series of carbazole/quinoxaline hybrids have been synthesized by classic Ullmann and Pd/Cu-catalyzed Sonogashira coupling reaction. Their photophysical, thermal, and electrochemical properties were investigated. The introduction of electron rich carbazole and electron deficient quinoxaline on to the 1,3,5-benzene center leads to a twisted structure with good glass forming property and imparts a bipolar character. The triplet energies in the range of 2.34–2.53 eV indicate them as potential host materials in phosphorescent OLEDs.

[1]  S. Jenekhe,et al.  Electrochemical Properties and Electronic Structures of Conjugated Polyquinolines and Polyanthrazolines , 1996 .

[2]  Hartmut Yersin,et al.  Highly efficient OLEDs with phosphorescent materials , 2007 .

[3]  Jiann T. Lin,et al.  Quinoxalines incorporating triarylamines: Potential electroluminescent materials with tunable emission characteristics , 2002 .

[4]  Stephen R. Forrest,et al.  Endothermic energy transfer: A mechanism for generating very efficient high-energy phosphorescent emission in organic materials , 2001 .

[5]  Jiann T. Lin,et al.  Chromophore-labeled quinoxaline derivatives as efficient electroluminescent materials , 2005 .

[6]  Y. Tao,et al.  Doubly ortho-linked quinoxaline/diphenylfluorene hybrids as bipolar, fluorescent chameleons for optoelectronic applications. , 2006, Journal of the American Chemical Society.

[7]  Giovanni Scalmani,et al.  Time-dependent density functional theory investigation of the absorption, fluorescence, and phosphorescence spectra of solvated coumarins. , 2006, The Journal of chemical physics.

[8]  Stephen R. Forrest,et al.  Transient analysis of organic electrophosphorescence. II. Transient analysis of triplet-triplet annihilation , 2000 .

[9]  Chen‐Han Chien,et al.  Phosphine-Oxide-Containing Bipolar Host Material for Blue Electrophosphorescent Devices , 2009 .

[10]  C. Leznoff,et al.  Octaarylethynyl and octaarylbutadiynyl phthalocyanines , 2001 .

[11]  Samson A. Jenekhe,et al.  New Conjugated Polymers with Donor−Acceptor Architectures: Synthesis and Photophysics of Carbazole−Quinoline and Phenothiazine−Quinoline Copolymers and Oligomers Exhibiting Large Intramolecular Charge Transfer , 2001 .

[12]  S. R. Forrest,et al.  High-efficiency fluorescent organic light-emitting devices using a phosphorescent sensitizer , 2000, Nature.

[13]  Peter Strohriegl,et al.  Donor-substituted 1,3,5-triazines as host materials for blue phosphorescent organic light-emitting diodes , 2010 .

[14]  D Murphy,et al.  Highly phosphorescent bis-cyclometalated iridium complexes: synthesis, photophysical characterization, and use in organic light emitting diodes. , 2001, Journal of the American Chemical Society.

[15]  Stephen R. Forrest,et al.  Ultrahigh energy gap hosts in deep blue organic electrophosphorescent devices , 2004 .

[16]  P. Merkel,et al.  A new class of non-conjugated bipolar hybrid hosts for phosphorescent organic light-emitting diodes , 2009 .

[17]  J. Qin,et al.  Novel oligo-9,9'-spirobifluorenes through ortho-linkage as full hydrocarbon host for highly efficient phosphorescent OLEDs. , 2009, Organic letters.

[18]  Peter Strohriegl,et al.  Phenylquinoxaline Polymers and Low Molar Mass Glasses as Electron-Transport Materials in Organic Light-Emitting Diodes , 1998 .

[19]  Pyridoindole Derivative as Electron Transporting Host Material for Efficient Deep‐blue Phosphorescent Organic Light‐emitting Diodes , 2010, Advanced materials.

[20]  Klaus Meerholz,et al.  Highly Efficient Polymeric Electrophosphorescent Diodes , 2006 .

[21]  Joseph Shinar,et al.  Organic Light-Emitting Devices , 2004 .

[22]  S. Jenekhe,et al.  Synthesis, Photophysics, and Electroluminescence of New Quinoxaline-Containing Poly(p-phenylenevinylene)s , 2004 .

[23]  Yumin Li,et al.  Acridinone/amine(carbazole)-based bipolar molecules: efficient hosts for fluorescent and phosphorescent emitters. , 2009, Organic letters.

[24]  S. Jenekhe,et al.  Quinoxaline-containing polyfluorenes : Synthesis, photophysics, and stable blue electroluminescence , 2005 .

[25]  Tae‐Hyuk Kwon,et al.  A bipolar host containing 1,2,3-triazole for realizing highly efficient phosphorescent organic light-emitting diodes , 2010 .

[26]  David Phillips,et al.  Photophysics of some common fluorescence standards , 1983 .

[27]  Jingui Qin,et al.  Molecular design of host materials based on triphenylamine/oxadiazole hybrids for excellent deep-red phosphorescent organic light-emitting diodes , 2010 .

[28]  Hartmut Yersin,et al.  Triplet emitters for OLED applications. Mechanisms of exciton trapping and control of emission properties , 2004 .

[29]  Donal D. C. Bradley,et al.  Electrochemical determination of the ionization potential and electron affinity of poly(9,9-dioctylfluorene) , 1998 .

[30]  Karsten Walzer,et al.  Triplet-exciton quenching in organic phosphorescent light-emitting diodes with Ir-based emitters , 2007 .

[31]  J. Kido,et al.  m-Terphenyl-modified carbazole host material for highly efficient blue and green PHOLEDS. , 2009, Chemical communications.

[32]  T. Hayakawa,et al.  Novel bipolar bathophenanthroline containing hosts for highly efficient phosphorescent OLEDs. , 2008, Organic letters.

[33]  J. Qin,et al.  Tuning the Optoelectronic Properties of Carbazole/Oxadiazole Hybrids through Linkage Modes: Hosts for Highly Efficient Green Electrophosphorescence , 2010 .

[34]  S. Forrest,et al.  Nearly 100% internal phosphorescence efficiency in an organic light emitting device , 2001 .

[35]  J. Qin,et al.  Highly Efficient Phosphorescent Organic Light-Emitting Diodes Hosted by 1,2,4-Triazole-Cored Triphenylamine Derivatives: Relationship between Structure and Optoelectronic Properties , 2010 .

[36]  J. Mikroyannidis,et al.  Bipolar poly(p-phenylene vinylene)s bearing electron-donating triphenylamine or carbazole and electron-accepting quinoxaline moieties , 2008 .

[37]  Ken‐Tsung Wong,et al.  Triphenylsilyl- and trityl-substituted carbazole-based host materials for blue electrophosphorescence. , 2009, ACS applied materials & interfaces.

[38]  Wai-Yeung Wong,et al.  Triphenylamine-dendronized pure red iridium phosphors with superior OLED efficiency/color purity trade-offs. , 2007, Angewandte Chemie.

[39]  Chung-Chih Wu,et al.  3-(9-Carbazolyl)carbazoles and 3,6-Di(9-carbazolyl)carbazoles as Effective Host Materials for Efficient Blue Organic Electrophosphorescence** , 2007 .

[40]  Ken-Tsung Wong,et al.  Highly Efficient Organic Blue Electrophosphorescent Devices Based on 3,6‐Bis(triphenylsilyl)carbazole as the Host Material , 2006 .

[41]  F. So,et al.  An ambipolar phosphine oxide-based host for high power efficiency blue phosphorescent organic light emitting devices , 2009 .

[42]  J. Kido,et al.  Pyridine-Containing Bipolar Host Materials for Highly Efficient Blue Phosphorescent OLEDs , 2008 .

[43]  Wen‐Chang Chen,et al.  Synthesis and characterization of new fluorene-acceptor alternating and random copolymers for light-emitting applications , 2006 .

[44]  Gregor Schwartz,et al.  White organic light-emitting diodes with fluorescent tube efficiency , 2009, Nature.

[45]  Stephen R. Forrest,et al.  Phosphorescent materials for application to organic light emitting devices , 1999 .

[46]  Stephen R. Forrest,et al.  Blue organic electrophosphorescence using exothermic host–guest energy transfer , 2003 .

[47]  Qiang Wang,et al.  A simple carbazole/oxadiazole hybrid molecule: an excellent bipolar host for green and red phosphorescent OLEDs. , 2008, Angewandte Chemie.