New CF3-substituted PPV-type oligomers and polymers for use as hole blocking layers in LEDs

Lux, Andrea; Holmes, Andrew B.; Cervini, Raoul; Davies, John E.; Moratti, Stephen C.; Grüner, J.; Cacialli, Franco; Friend, Richard H.

doi:10.1016/s0379-6779(97)80757-6

Cited by 57 publications

(53 citation statements)

References 4 publications

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“…Thus, syntheses of new PPV derivatives bearing CF 3 groups at the vinylene linkage (32) have been recently reported (Scheme 5) [82]. Polymer 32 can be obtained by condensation of 2,5-dialkoxy-pxylylene-bis(diethylphosphonates) (31) with appropriate bis(perfluoromethylketones) (30) in refluxing toluene under argon using potassium tert-butoxide as base according to Scheme 5.…”

Section: Modification Of Electronic Properties Of Conjugated Polymersmentioning

confidence: 99%

The chemistry of electroluminescent organic materials

Segura¹

1998

Acta Polym.

287

200

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Electroluminescence has been a subject of interest for several decades because of its many applications in areas such as telecommunications or information displays. Light‐emitting diodes using p‐n junctions of inorganic semiconductors have dominated the field in the last twenty years; however, efficient blue emission has only recently been achieved and inorganic semiconductors are difficult to form over large areas, making the process uneconomic. During the last decade, an explosive growth of activity in the area of organic electroluminescence has occurred in both academia and industry, stimulated by the promise of light‐emitting plastics for the fabrication of large, flexible, inexpensive and efficient screens to be used in different applications. Thus, a substantial amount of research is presently directed towards color control and improvement of manufacturability and reliability of devices in order to make their commercialization viable. A great deal of work has been carried out by physicists and materials scientists concerned with the preparation of different device structures and with the use of different techniques for device manufacture. However, all this work would not be possible without the continuous efforts of synthetic chemists to prepare materials with enhanced luminescent properties and processabilities. This article provides a review of the main types of organic materials that have been used in the fabrica‐tion of light‐emitting diodes either as emitting materials or as charge‐transport layers. Special attention will be paid to the different synthetic strategies that have been followed in order to tune the color of the emission, to increase stability of materials and to enhance their processabilities.

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Section: Modification Of Electronic Properties Of Conjugated Polymersmentioning

confidence: 99%

The chemistry of electroluminescent organic materials

Segura¹

1998

Acta Polym.

287

200

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“…In previous studies, introduction of electron withdrawing substituents onto the vinylene bond has been shown to decrease their rate of oxidation [5,6,7]. Thus, it is implicit that the vinylene units adjacent to anthrylene units are deficient in π electrons, rendering them more stable to attack.…”

Section: Resultsmentioning

confidence: 99%

“…It has been found that substitution with electron donating alkyloxy side chains increases the rate of degradation of the polymer [4], while phenyl or cyano electron withdrawing substituents lead to a decrease in the rate of degradation, particularly if the substituent is placed on the vinylene bonds [5,6]. Trifluoromethyl substituted compounds have been shown to be particularly stable towards photo-oxidation accentuating the benefit of electron deficient vinylene linkages and pointing towards the vulnerability of this moiety to degradation [7].…”

Section: Introductionmentioning

confidence: 99%

Kinetic studies of the photo-degradation of poly(arylene vinylenes)

O’Neill¹,

Lynch²,

McGoldrick

et al. 2012

Journal of Luminescence

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This is a PDF file of an unedited manuscript that has been accepted for publication. As a service to our customers we are providing this early version of the manuscript. The manuscript will undergo copyediting, typesetting, and review of the resulting galley proof before it is published in its final citable form. Please note that during the production process errors may be discovered which could affect the content, and all legal disclaimers that apply to the journal pertain. AbstractThe kinetics of the degradation of a homologous series of Poly phenylene vinylenes in which the phenylene units of the PPV structure are systematically substituted by naphthyl and anthyrl units is presented. Degradation is monitored according to the decay of the long wavelength absorption maximum upon illumination with UV radiation. Compared to Toluene solution, the photo-degradation is seen to be accelerated in Chloroform solution. All decays are fitted with first order kinetics. It is found that all substitutions improve the stability of the vinylene polymers against decay.In particular the highly electro-negative naphthyl group serves to drastically increase the stability due to electron depletion across the vinyl bond. The decay rate is shown to correlate well with the variation of the electronic properties of the backbone and with the reduction of vinylene bond strength as measured using Raman spectroscopy.

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“…This was borne out in reality and such cyano-bearing PPVs boast impressive photoluminescence efficiency (60%) and external efficiency (4%) in a single layer electroluminescence device. 20 There are several PPV derivatives that bear the trifluoromethyl group on the aryl ring of PPV, 21,22 and two reported examples of PPV copolymers bearing a trifluoromethyl group on the ethylene bridge, 23 but the model polymers 3 (Z D CF 3 , H) with trifluoromethyl substitution on the vinylene linkage do not appear in the literature.…”

Section: Introductionmentioning

confidence: 99%

Complete assignment of ¹⁹F, ¹H and ¹³C NMR spectra of monomers and precursors towards bridge trifluoromethylated poly(p‐phenylenevinylene)

Roche

2004

Magnetic Reson in Chemistry

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The complete assignment of 19F, 1H and 13C NMR spectra of 11 trifluoromethylated and four bistrifluoromethylated monomers for bridge trifluoromethylated poly(p-phenylenevinylene) is described. The combination of one-dimensional 19F, 1H and 13C spectra, long-range fluorine couplings and the two-dimensional techniques of direct and long-range HETCOR (J = 140 and 8 Hz) permitted full resonance assignment.

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New CF3-substituted PPV-type oligomers and polymers for use as hole blocking layers in LEDs

Cited by 57 publications

References 4 publications

The chemistry of electroluminescent organic materials

The chemistry of electroluminescent organic materials

Kinetic studies of the photo-degradation of poly(arylene vinylenes)

Complete assignment of ¹⁹F, ¹H and ¹³C NMR spectra of monomers and precursors towards bridge trifluoromethylated poly(p‐phenylenevinylene)

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New CF3-substituted PPV-type oligomers and polymers for use as hole blocking layers in LEDs

Cited by 57 publications

References 4 publications

The chemistry of electroluminescent organic materials

The chemistry of electroluminescent organic materials

Kinetic studies of the photo-degradation of poly(arylene vinylenes)

Complete assignment of 19F, 1H and 13C NMR spectra of monomers and precursors towards bridge trifluoromethylated poly(p‐phenylenevinylene)

Contact Info

Product

Resources

About

Complete assignment of ¹⁹F, ¹H and ¹³C NMR spectra of monomers and precursors towards bridge trifluoromethylated poly(p‐phenylenevinylene)