The present invention relates to novel organic electroluminescent compounds exhibiting high luminous efficiency, and organic electroluminescent devices comprising the same. The organic electroluminescent compounds according to the invention are represented by Chemical Formula (1):

Novel organic electroluminescent compounds and organic electroluminescent device using the same

After an introduction reporting the properties and the applications of fluoropolymers, a first part deals with i) the main routes to produce vinylidene fluoride (VDF) monomer, ii) its homopolymerization, and iii) the advantages and uses of polyvinylidene fluoride (PVDF). In a second section, this review, illustrated by numerous examples, extensively reports the synthesis, properties and applications of the copolymers based on VDF with non-halogenated, fluorinated, commercially available or synthesized comonomers. These comonomers exhibit XYC=CZ-Sp-R structures where X, Y, and Z represent H, F, and CF3 groups, Sp a spacer and R a function such as OH, OAc, SAc, CO2R' (R' being a H atom or an alkyl group), CN, P(O)(OR')2 and SO3H. According to the nature and to the amount of the comonomer, the copolymers can be thermoplastic, elastomeric or thermoplastic elastomers. Introducing reactive R side groups brings complementary properties such as hydrophily, ionic exchange or surface properties, or further crosslinking of the resulting copolymers. Then, the kinetics of radical copolymerization of VDF with M comonomers led to the assessment of the reactivity ratios which are compared. Hence, a reactivity series of these M comonomers with respect to a macroradical terminated by VDF is proposed. Usually, these copolymers exhibit random structures but only three comonomers produced alternating copolymers with VDF: hexafluoroisobutylene, F2C=CFCO2CH3, and H2C=C(CF3)CO2R. The controlled radical copolymerizations of VDF with other comonomers (such as chlorotrifluoroethylene, 3,3,3-trifluoropropene, hexafluoropropylene, perfluoromethyl vinyl ether or-trifluoromethacrylic acid) either in the presence of xanthates, borinates or iodo-compounds are also reported. In addition, new VDF-containing copolymers exhibit well-defined architectures, such as block and graft copolymers. They can be synthesized either by conventional techniques or by controlled radical copolymerization. Chemical modifications of PVDF and poly(VDF-co-monomer) copolymers are also presented. Several properties and applications (such as surfactants, dielectrical polymers, thermoplastic elastomers, fuel cell and ultrafiltration membranes, or polycondensates, the fluorinated segments of which bringing softness and thermal stability) of these VDF-containing copolymers will illustrate this review.

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From vinylidene fluoride (VDF) to the applications of VDF-containing polymers and copolymers: recent developments and future trends.

Polymeric materials as anion-exchange membranes for alkaline fuel cells

The strength of multi-scale modeling to unveil the complexity of radical polymerization

Herein we review the environmentally friendly synthesis of fluorinated polymers in supercritical carbon dioxide (scCO2). Historically, many high-performance fluorinated materials are commercially synthesized in aqueous media using fluorinated surfactants or in non-aqueous conditions using fluorinated solvents. Our group has pioneered both the homogeneous and heterogeneous polymerization of fluorinated monomers in scCO2. This review includes discussions on the synthesis of main-chain and side-chain fluoropolymers conducted via a chain-growth or continuous process. Specific materials consist of acrylate- and styrene-based systems, poly(vinyl ether)s, tetrafluoroethylene- and vinylidenefluoride-based, as well as novel fluorinated elastomers and thermoplastics.

Fluoropolymer synthesis in supercritical carbon dioxide

The heterogeneous polymerization of vinylidene fluoride in supercritical carbon dioxide has been investigated experimentally, and the obtained results have been interpreted through a detailed kinetic model. The comparison between model predictions and experimental data indicates the presence of two reaction loci:  the continuous supercritical phase and the dispersed polymer phase. However, the presence of two reaction loci is not the result of the thermodynamic partitioning between two phases, but rather a kinetic effect. This in fact occurs because part of the radicals generated in the continuous phase, which are driven by thermodynamic equilibrium to diffuse to the dispersed phase, are actually terminated in the former before they can reach the latter. This provides a quantitative explanation for the bimodal molecular weight distributions often measured experimentally for this system.

Modeling of Vinylidene Fluoride Heterogeneous Polymerization in Supercritical Carbon Dioxide

The present invention provides solid alkaline fuel cells comprising anion exchange membranes which comprise diamines or polyamines coupled to a support polymer via a sulfonamide linkage. At least one nitrogen atom of the diamine or polyamine is a quaternized nitrogen atom acting as an anion exchange group. The anion exchange membrane exhibits favourable properties that render it suitable for use in a solid alkaline fuel cell.

Solid alkaline fuel cell comprising ion exchange membrane

Vinylidene difluoride and hexafluoropropene are copolymerized in supercritical carbon dioxide at 280 bar and 50 °C by means of free radical copolymerization, initiated by diethyl peroxydicarbonate. The first stages of the reaction were monitored by turbidity measurements and the time/conversion curve was followed gravimetrically to measure the initial rates of polymerization. The obtained copolymers possessed bimodal molecular weight distributions, their average comonomer composition was well described by the Lewis-Mayo equation with the copolymerization parameters rVDF = 4.8 and rHFP = 0. The glass transition and melting temperatures of the copolymers are similar to that of the materials resulting from aqueous emulsion polymerization. © 2005 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 44: 1299–1316, 2006

Copolymerization of vinylidene difluoride with hexafluoropropene in supercritical carbon dioxide

The present invention relates to a host material comprising a compound having two carbazole moieties which is suitable for blue-emitting OLEDs. Surprisingly, it has been found that when appropriate substituents are present in the carbazole structure, the solubility of the compounds can be improved without any adverse effect on the OLED performance. The present invention further relates to the use of the host materials and to an organic light emitting device comprising the host material.

Host material for light-emitting diodes

The present invention relates to a host material comprising a compound having a carbazole moiety which is suitable for blue-emitting OLEDs. Surprisingly, it has been found that when appropriate substituents are present in the carbazole structure, the solubility of the compounds can be improved without any adverse effect on the OLED performance. The present invention further relates to the use of the host materials and to an organic light emitting device comprising the host material.

Roland Martin

Papers

Modeling of Vinylidene Fluoride Heterogeneous Polymerization in Supercritical Carbon Dioxide

Solid alkaline fuel cell comprising ion exchange membrane

Copolymerization of vinylidene difluoride with hexafluoropropene in supercritical carbon dioxide

Host material for light-emitting diodes

N-Phenyl carbazole-based host material for light-emitting diodes