Synthesis and characterization of poly( p -phenylene vinylene) polymers containing the quinoxaline group

Lee, Bum Hoon; Jaung, Jae Yun; Cho, Jae-whan; Yoon, Kee Jong

doi:10.1007/s00289-003-0142-3

Cited by 16 publications

(9 citation statements)

References 1 publication

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“…One promising approach to improving the external quantum efficiency of OLEDs is to incorporate the functions of hole and electron transport and light emission into a single polymer, thereby creating bipolar (donor/acceptor) emissive polymers. − Rational molecular design of emissive polymers with improved electron affinity and balanced charge transport would allow the fabrication of efficient single-layer OLEDs. One of the challenges of this approach is to improve the charge transport properties while preserving the desired high luminescence quantum yields.…”

Section: Introductionmentioning

confidence: 99%

“…One of the challenges of this approach is to improve the charge transport properties while preserving the desired high luminescence quantum yields. Toward this end, several copolymers have been synthesized based on p-type backbones incorporating an electron-deficient unit such as pyridine, cyano group, oxadiazole, , quinoline, or quinoxalines, − either in the main chain or as pendants to the main chain. Quinoxaline is a useful n-type building block with high electron affinity and good thermal stability.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, Photophysics, and Electroluminescence of New Quinoxaline-Containing Poly(p-phenylenevinylene)s

Karastatiris¹,

Mikroyannidis²,

Spiliopoulos³

et al. 2004

Macromolecules

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Four new soluble poly(p-phenylenevinylene) (PPV) derivatives containing one or two quinoxaline moieties per repeat unit, either in the main chain or as pendants to the main chain, were synthesized, characterized, and explored as emissive and electron transport materials in polymer lightemitting diodes (LEDs). Polymers containing one quinoxaline moiety per repeat unit (QXPV1 and QXPV3) showed low melting transitions (<100 °C), whereas those with two quinoxaline moieties per repeat unit (QXPV2 and QXPV4) had relatively high glass transition temperatures (>140 °C). The polymers emit blue to green light (404-536 nm) in dilute solution and blue-green to yellow light (470-563 nm) in the solid state. The photoluminescence emission was well-described by single-exponential decay with lifetimes ranging from 200 ps to 2.2 ns in both dilute solution and thin film, indicating lack of intermolecular emissive species in the solid state. PPV derivatives with quinoxaline moieties in the main chain (QXPV1 and QXPV2) showed facile reversible electrochemical reductions with electron affinities of 2.63-2.75 eV. As emissive materials in LEDs, greenish-yellow electroluminescence with a brightness of up to 450 cd/m 2 was obtained from single-layer diodes of QXPV1 with aluminum cathode in air.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis, Photophysics, and Electroluminescence of New Quinoxaline-Containing Poly(p-phenylenevinylene)s

Karastatiris¹,

Mikroyannidis²,

Spiliopoulos³

et al. 2004

Macromolecules

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“…The effective mass around the gap remains the same for the LUCO but is 20% larger for the HOCO. Quinoxaline‐containing polymers are reported in the literature 5–8, 54. To the best of our knowledge, the exact polymer we considered here has not yet been synthesized and studied.…”

Section: Resultsmentioning

confidence: 99%

“…Furthermore, the ionization potential (IP) must not increase to a degree that makes hole injection difficult. Substituting electron‐withdrawing cyano groups 1–3 into PPV or replacing the phenyl rings with heterocyclic units such as quinoxaline derivatives 4–8 are promising approaches to increasing electron affinity without destroying mobility or unduly increasing the ionization potential.…”

Section: Introductionmentioning

confidence: 99%

Density functional crystal orbital study of cyano‐substituted poly(para‐phenylene‐vinylene) and poly(quinoxaline‐vinylene)

Bartha

Howard

Geerlings³

et al. 2006

Int J of Quantum Chemistry

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ABSTRACT:We have calculated the optical and electronic properties of several conjugated organic polymers: poly(p-phenylene-vinylene) (PPV) and its derivatives. Cyano substitutions on the phenylene ring: poly(2,5-dicyano-p-phenylene-vinylene) (2,5-DCN-PPV) and on the vinylene linkage: poly(p-phenylene-7(,8)-(di)cyano-vinylene) are considered. In addition, poly(quinoxalinevinylene) (PQV) is studied. The infinite isolated quasi-1D chains are treated with periodic boundary conditions, using atomic basis sets. In a comparative study of PPV, some issues regarding the selection of the functionals and basis sets are discussed and excitation energies derived from time-dependent and from ordinary methods are compared. It is concluded that for these polymers the calculations are informative at the B3LYP/6-31G** density functional theory (DFT) level. The absolute values might change with improved methods, but the similarity of the polymers suggests that the relative characterization is adequate. Band structures are communicated along with characteristics of the highest occupied and the lowest unoccupied crystal orbitals (HOCO and LUCO). Electron affinities, ionization potentials, valence and conduction bandwidths, and effective masses at the bandgap are given.

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“…This property together with their thermal stability makes quinoxalines as an attractive candidate for the synthesis of low band gap polymers [5,24]. Due to their high electron affinities, they are also promising electron transport materials in multilayer organic light emitting devices [26,27] and several copolymers containing quinoxalines either in the main chain or as pendant groups on the main chain has been reported [25][26][27][28][29][30][31]. Quinoxaline containing polymers prepared via condensation reaction were first used as heat and chemical resistant materials and applied later in polymer light emitting devices [32,33].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of a novel fluorescent and ion sensitive monomer bearing quinoxaline moieties and its electropolymerization

Çarbaş

Kıvrak

Zora

et al. 2011

Reactive and Functional Polymers

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Synthesis and characterization of poly( p -phenylene vinylene) polymers containing the quinoxaline group

Cited by 16 publications

References 1 publication

Synthesis, Photophysics, and Electroluminescence of New Quinoxaline-Containing Poly(p-phenylenevinylene)s

Synthesis, Photophysics, and Electroluminescence of New Quinoxaline-Containing Poly(p-phenylenevinylene)s

Density functional crystal orbital study of cyano‐substituted poly(para‐phenylene‐vinylene) and poly(quinoxaline‐vinylene)

Synthesis of a novel fluorescent and ion sensitive monomer bearing quinoxaline moieties and its electropolymerization

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