Tuning the Optoelectronic Properties of Pyridine-Containing Polymers for Light-Emitting Devices

Wang, C.; Kilitziraki, M.; Macbride, J. A. H.; Horsburgh, L. E.; Sheridan, A. K.; Monkman, Andrew P.; Samuel, Ifor D. W.

doi:10.1002/(sici)1521-4095(200002)12:3<217::aid-adma217>3.3.co;2-p

Cited by 24 publications

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“…Among these, nitrogen‐containing conjugated materials have shown considerable promise as an electron transporting layers (ETLs) in OLEDs. They have high electron affinities because they have electron‐deficient heterocycles and can effectively transport electrons from the cathode throughout the ETL materials until they successfully recombine with holes resulting in light emission 2–4. Moreover, it is demonstrated that their light‐emitting properties could be tuned through the protonation of nitrogen heterocycles 2b,c, 3f.…”

Section: Introductionmentioning

confidence: 99%

“…They have high electron affinities because they have electron‐deficient heterocycles and can effectively transport electrons from the cathode throughout the ETL materials until they successfully recombine with holes resulting in light emission 2–4. Moreover, it is demonstrated that their light‐emitting properties could be tuned through the protonation of nitrogen heterocycles 2b,c, 3f. Different heterocyclic moieties, such as oxadiazole,3a azole,3b benzobisazole,3c benzothiadiazole,3d pyridine,3e quinoxaline,3f quinoline,3g and anthrazoline3h were incorporated in both molecular and polymeric materials that were comprehensively reviewed by Jenekhe et al4 The 4‐phenyl‐2,6‐bis(4‐aminophenyl)pyridine, prepared by Chichibabin reaction, and its derivatives were used in the synthesis of various classes of polymers including polyamides, polyimides, poly(amide‐imide)s, and poly(ester‐imides)s 5–7.…”

Section: Introductionmentioning

confidence: 99%

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Solution, thermal and optical properties of novel poly(pyridinium salt)s derived from conjugated pyridine diamines

Nedeltchev

Han

Bhowmik

2010

J. Polym. Sci. A Polym. Chem.

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Several novel poly(pyridinium salt)s with heterocyclic pyridine moieties in their backbones with tosylate and triflimide counterions were prepared by either ring‐transmutation polymerization reaction of phenylated‐bis(pyrylium tosylate) with isomeric pyridine diamines of 4‐phenyl‐2,6‐bis(4‐aminophenyl)pyridine in dimethyl sulfoxide (DMSO) for 48 h at 130–140 °C or by metathesis reaction of the respective tosylate polymers with lithium triflimide in DMSO at about 60 °C. Their chemical structures were characterized by FTIR, 1H, 13C NMR spectroscopy, and elemental analysis. Their number‐average molecular weights (Mn) were in the range of 8,000–51,000 and their polydispersities in the range of 1.18–2.13 as determined by gel permeation chromatography. They had excellent thermal stabilities of 340–458 °C and high glass transition temperatures >200 °C. As they showed good solubilities in common organic solvents, their solution properties were also characterized for their lyotropic liquid‐crystalline properties with polarizing optical microscopy (POM) studies. Their photoluminescent properties were examined by using a spectrofluorometer in both solution and solid states. Their quantum yields were rather low, which were in the range of 1.3–2.0%. Additionally, hand‐drawn fibers from the melts were examined to determine their morphologies with a number of microscopic techniques including POM, scanning electron microscopy, and transmission electron microscopy. © 2010 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2010

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Solution, thermal and optical properties of novel poly(pyridinium salt)s derived from conjugated pyridine diamines

Nedeltchev

Han

Bhowmik

2010

J. Polym. Sci. A Polym. Chem.

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“…Polymer PN is expected to present improved electron‐transport properties in comparison with PC because of the presence of the pyridine ring. It has been established that pyridine is a moderately electron‐deficient π system, and poly(pyridine)s have been used as electron‐injection/hole‐blocking materials for LED fabrication 20–22. Moreover, it has been reported that LEDs with poly(pyridylvinylene) as the emissive material afford improved external quantum efficiency 23.…”

Section: Introductionmentioning

confidence: 99%

Photophysics, electrochemical properties, and electroluminescence of poly(p‐phenylenevinylene) derivatives with 1,3,5‐triphenylbenzene or 2,4,6‐triphenylpyridine segments along the backbone

Cimrová

Hlídková

Výprachtický

et al. 2005

J Polym Sci B Polym Phys

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The steady-state and time-resolved photoluminescence (PL), electrochemical behavior, and electroluminescence (EL) of didodecyloxy poly(p-phenylenevinylene)based polymers that contained along the backbone structure 1,3,5-triphenylbenzene (PC) or 2,4,6-triphenylpyridine (PN) were studied. An intensive green PL broad-band emission with maxima at 516 and 527 nm was observed from thin films of PC and PN polymers, respectively, redshifted in comparison with the PL emission spectra measured in tetrahydrofuran solutions. The PL decay dynamics revealed the existence of more than one excited species, and the decay curves were best described by three-term exponential functions with a dominant lifetime of about 1 ns. The results of time-resolved PL and steady-state PL studies indicated excimer or aggregate formation. Both polymers oxidized irreversibly. A quasireversible reduction was observed in the PN polymer, whereas the PC polymer reduced irreversibly. For PC, slightly higher values of the ionization potential (E IP ) and electron affinity (E A ) were found (E IP ¼ 5.52 eV, E A ¼ 2.85 eV) than those for PN (E IP ¼ 5.37 eV, E A ¼ 2.77 eV). Light-emitting devices with indium tin oxide hole-injecting and aluminum electroninjecting electrodes were prepared and studied. They emitted green light, and their EL spectra were similar to those of PL thin films. V V C 2005 Wiley Periodicals, Inc. J Polym Sci Part B: Polym Phys 44: 524-533, 2006

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“…Attachment of OEO side chains to PPP rods has already been described in literature, and it has also been shown that SPC tolerates amino groups . The challenge of the present study was ( i ) identification of the PPPs' molecular constitution that ensures solubility in water at vanishing charge density, ( ii ) development of pathways to the required monomers, and ( iii ) identification of appropriate reaction conditions for successful SPC.…”

Section: Introductionmentioning

confidence: 93%

Toward Truly Water‐Soluble Rodlike Polyelectrolytes: Synthesis of Poly(para‐phenylenes) Wrapped in Ethylene Oxideand Amino Side Groups

Wittmeyer

Traser

Sander

et al. 2016

Macro Chemistry & Physics

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cross-coupling protocols are applied to synthesize water-soluble poly(p-phenylene) (PPP) derivatives decorated with oligoethylene oxide (OEO) and tertiary amino side groups. It is shown that constitutionally well-defined PPPs can be obtained having degrees of polycondensation, P n , of 30-60. In some cases, however the heteroatoms in the side chains affect the monomer synthesis and prevent proper chain growth through coordination of metal species present in the reaction medium. It is shown that essentially uncharged but still water-soluble PPPs result if (i) the side groups bear their heteroatoms in the right position, and (ii) if the water-soluble segments of the lateral substituents prevent intermolecular hydrophobic interactions of the apolar main chains reliably. In other words, the lateral substituents have to wrap the PPP core structure tightly in a closed outer shell of water-soluble OEO moieties. These PPPs constitute a valuable new pool of model systems for future polyelectrolyte research, being highly complementary to what has been available so far.

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Tuning the Optoelectronic Properties of Pyridine-Containing Polymers for Light-Emitting Devices

Cited by 24 publications

References 0 publications

Solution, thermal and optical properties of novel poly(pyridinium salt)s derived from conjugated pyridine diamines

Solution, thermal and optical properties of novel poly(pyridinium salt)s derived from conjugated pyridine diamines

Photophysics, electrochemical properties, and electroluminescence of poly(p‐phenylenevinylene) derivatives with 1,3,5‐triphenylbenzene or 2,4,6‐triphenylpyridine segments along the backbone

Toward Truly Water‐Soluble Rodlike Polyelectrolytes: Synthesis of Poly(para‐phenylenes) Wrapped in Ethylene Oxideand Amino Side Groups

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