Novel light emitting and photoconducting polyarylenevinylene derivatives containing phenylene arylamine and phenylene oxide units in the main chain

Rost, H.; Teuschel, A.; Pfeiffer, Steffen; Hörhold, H.‐H.

doi:10.1016/s0379-6779(97)80746-1

Cited by 86 publications

(40 citation statements)

References 7 publications

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“…Furthermore, the Horner reaction is extremely flexible. This means that monomers of a wide variety of arylene units (Ar and Ar9, e. g., m-C 6 H 4 , p-C 6 H 4 , C 6 H 4 1 X1C 6 H 4 ) can be employed 9,10,18) . Thus, alternating copolymers in the PPV family can easily be synthesized when using dialdehyde and bisphosphonate monomers with differently substituted phenylene units (e. g. M3EH-PPV).…”

Section: Introductionmentioning

confidence: 99%

Investigation of poly(arylene vinylene)s, 41. Synthesis of soluble dialkoxy-substituted poly(phenylene alkenylidene)s by applying the Horner-reaction for condensation polymerization

Pfeiffer

Hörhold²

1999

Macromol. Chem. Phys.

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SUMMARY: Soluble poly[2-methoxy-5-(2-ethylhexyloxy)-1,4-phenylene-1,2-ethenylene] (MEH-PPV) and its alternating copolymer poly[2,5-dimethoxy-1,4-phenylene-1,2-ethenylene-2-methoxy-5-(2-ethylhexyloxy)-1,4-phenylene-1,2-ethenylene] (M3EH-PPV) were successfully synthesized by condensation polymerization of substituted terephthalaldehydes with substituted xylylene bisphosphonates via the Horner reaction. This polycondensation method was also applied to the synthesis of the analogous poly[2-methoxy-5-(2-ethylhexyloxy)-1,4-phenylene-1,3-butadiene-1,4-diyl] (MEH-PPB), which contains a 1,3-butadiene instead of a vinylene unit. The optical data of MEH-PPV and M3EH-PPV (solid film, abs. ) and possess all-trans structure. Optical quality solid films are easily prepared from these polymers by solution processing. Blends with phenyl-substituted PPV derivatives can also be prepared in this way. This combination of properties is highly desirable for many light-emitting, nonlinear optical, and photoelectrical applications.

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Section: Introductionmentioning

confidence: 99%

Investigation of poly(arylene vinylene)s, 41. Synthesis of soluble dialkoxy-substituted poly(phenylene alkenylidene)s by applying the Horner-reaction for condensation polymerization

Pfeiffer

Hörhold²

1999

Macromol. Chem. Phys.

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“…12 Two different synthesis reactions have been used with three solvents to give six different synthesis pathways for the polymer. 13 The Horner-Emmons polycondensation reaction 14 in dry toluene was used to synthesize the PmPV for this work. The chemical structure of PmPV is shown in Fig.…”

Section: Materials and Experimental Methodsmentioning

confidence: 99%

Alternating and direct current characterization and photoinduced absorption studies of modified conjugated polymer thin films

Lipson

Coleman

Drury

et al. 2004

Journal of Applied Physics

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Control of interchain separation enables the optical properties of polymer thin films to be altered. We present a thin film preparation technique that increases the free volume fraction in spin coated polymer thin films resulting in reduced interchain interaction. The polaron yield, measured using photoinduced absorption, was significantly reduced as a direct result of the increased interchain separation, leading to a higher value for the measured photoluminescence efficiency. Impedance spectroscopy showed an increase in permittivity, probably due to greater polarizability. Increases approaching one order of magnitude were observed for direct current hole conductivity and mobility values. Space charge limited conduction analysis suggests a narrowing of the highest occupied molecular orbital band tail on treatment resulting in reduced trapping. Single layer light emitting devices prepared using this technique were found to be significantly brighter and to have longer operating lifetimes.

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“…13,14 Metallic sodium (0.23 g, 0.01 mol) was placed into a threenecked round-bottom flask, provided with a dropping funnel, a sealed stirrer, and a reflux condenser closed with a calcium chloride tube; 100 mL dry toluene was placed into the flask, and while the liquid was being gently refluxed with agitation, dibutylphosphite (2 g, 0.01 mol) was added dropwise over 20 -30 min, after which the refluxing and stirring were continued until the sodium was completely dissolved. This reaction generally required 2-3 h. After the solution was cooled to room temperature, 4-4Ј-bis(chloromethyl)biphenyl was added and refluxed for 5 h. Triphenylamine diadehyde (1.5 g, 0.005 mol) was added at room temperature.…”

Section: Polymer Synthesismentioning

confidence: 99%

New light emitting materials: Alternating copolymers with hole transport and emitting chromophores

Zheng

Bai

Zhu

1999

J. Appl. Polym. Sci.

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ABSTRACT:A new type of novel high-efficiency light-emitting nitrogen-containing poly-(phenylene vinylene) (PPV)-related copolymers, which have hole-transfer moieties such as triphenylamine (TPA) and conjugated aromatic units such as 4,4Ј-biphenylene, 1,4-phenylene, 2,5-dimethyl-1,4-phenylene, 1,4-or 1,5-naphthylene, and 9,10-anthrylene, was designed and synthesized by the well-known Wittig-Hornor reaction. The resulting alternating copolymers were highly soluble in common organic solvents. They can spin-cast onto various substrates to give highly transparent homogeneous thin films without heat treatment. The introduction of TPA units in the PPV backbone improved processibility and limited the -conjugation length. Furthermore, the additional -electron delocalization between the lone-paired electron in the nitrogen atom and -electrons in the conjugated units contributed to the improvement of the fluorescence quantum yields of these copolymers. All these alternating copolymers except TPA-PAV have high-efficiency photoluminescence and they are very promising for light-emitting diodes (LEDs). It is very promising that TPA-PAV will emit white light when used in LED device due to the broad emission spectra. The origin of the broad spectrum is contributed by the charge-transfer complex formation, which can be proved by the absorption and emission spectra of TPA-PAV solutions. When the aromatic units were 1,4-phenylene, 1,4-or 1,5-naphthylene, 4,4Ј-biphenylene, and 9,10-anthrylene, respectively, with increase of the capability to accept electrons in aromatic units, the charge transfer from TPA to aromatic units occurred; consequently, the fluorescence quantum yield decreased. The introduction of the alkoxy-substitute group on the aromatic units in the polymer backbone caused the red shift of the absorption and emission spectra of the copolymers due to the stronger delocalization of the -conjugated system.

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Novel light emitting and photoconducting polyarylenevinylene derivatives containing phenylene arylamine and phenylene oxide units in the main chain

Cited by 86 publications

References 7 publications

Investigation of poly(arylene vinylene)s, 41. Synthesis of soluble dialkoxy-substituted poly(phenylene alkenylidene)s by applying the Horner-reaction for condensation polymerization

Investigation of poly(arylene vinylene)s, 41. Synthesis of soluble dialkoxy-substituted poly(phenylene alkenylidene)s by applying the Horner-reaction for condensation polymerization

Alternating and direct current characterization and photoinduced absorption studies of modified conjugated polymer thin films

New light emitting materials: Alternating copolymers with hole transport and emitting chromophores

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