- Introducing Solubility Control for Improved Organic P-Type Dopants
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To overcome the poor solubility of the widely used p-type dopant 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4TCNQ), we have synthesized a series of structure-modified, organic p-type dopants to include alkyl ester groups designed to enable solubility and miscibility control. UV-vis-NIR and cyclic voltammetry measurements show increased solubility of mono- and diester substituted dopants with only modest changes to acceptor strength. Using absorption spectroscopy, photoluminescence, and in-plane conductivity measurements, we demonstrate that the new dopants can successfully p-type dope poly(3-hexylthiophene-2,5-diyl) (P3HT). Monoester substituted dopants are characterized by only slightly reduced electron affinity relative to F4TCNQ, but greater doping effectiveness due to increased miscibility with P3HT. Diester substituted dopants undergo a dimerization reaction before assuming their doped states, which may help anchor dopants into position post deposition, thus decreasing the negative effect of dopant drift and diffusion. We conclude that increased dopant solubility/miscibility increases the overall effectiveness of doping in solution-cast polymer films and that ester modification is a practical approach to achieving solubility/miscibility control in TCNQ-type dopants (Figure Presented).
- Li, Jun,Zhang, Guangwu,Holm, Daniella M.,Jacobs, Ian E.,Yin, Bin,Stroeve, Pieter,Mascal, Mark,Moulé, Adam J.
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- Fluorene derivative and OLED (organic light-emitting diode) with same
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The invention provides a fluorene derivative and an OLED (organic light-emitting diode) with the same, and relates to the technical field of organic optoelectronic materials. The 9-position of a fluorene main structure is connected with a strong electron withdrawing group through double bonds, one side is connected with a phenanthrene fluorene structure to form the fluorene derivative, the fluorene derivative has good electronic transmission capacity and hole transmission capacity, charge carrier injection rate and exciton recombination rate of a luminescent layer can be effectively increased,besides, the fluorene derivative is good in heat stability and film-forming property, is simple and easy to synthesize and can be applied to the OLED as a luminescent layer main body and/or a hole blocking layer, the problems of unbalanced charge carrier transmission, low luminous efficiency, short service life and unstable light color of the OLED can be effectively solved, and the OLED has the advantages of low drive voltage, high luminous efficiency and long service life.
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Paragraph 0090; 0091; 0093
(2019/01/23)
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- The synthesis of 7,8,9,10-Tetrafluoroellipticine
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We have synthesized a novel ellipticine analogue, 7,8,9,10-Tetrafluoroellipticine, in nine steps from hexafluorobenzene and ethyl cyanoacetate, via 1-(phenysulfonyl)-4,5,6,7-Tetrafluoroindole. The key step is lithiation of the indole and subsequent coupling with 3,4-pyridinedicarboxylic acid anhydride to afford a ketolactam. Reaction of the lactam with methyllithium followed by reduction with sodium borohydride yields 7,8,9,10-Tetrafluoroellipticine. formula presented.
- James Gruver,Onyango, Evans O.,Gribble, Gordon W.
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p. 144 - 152
(2018/07/05)
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- Organic semiconductor material and the electronic component
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The invention relates to an organic semiconducting material, comprising at least one matrix material and at least one doping material, wherein the doping material is a 3-radialene compound, and wherein the matrix material is a terphenyl diamine compound, and to an organic component and to a mixture for producing a doped semiconductor layer.
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Paragraph 0075
(2017/01/19)
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- ORGANIC SEMICONDUCTIVE MATERIALS AND ORGANIC COMPONENT
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An organic semiconductive material comprising at least one matrix material and at least one doping material, wherein the doping material is selected from an organic compound and wherein the matrix material is selected from an diamine compound, also an organic component and a mixture for producing a doped semiconductor layer.
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Paragraph 0052
(2017/04/03)
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- Organic Compound having hole injecting characteristic and Organic Light Emitting Device and Display Device using the same
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The present invention relates to an organic compound having hole injecting properties, represented by chemical formula 1, and to an organic light-emitting device and a display device using the same. According to the present invention, the organic compound can reduce the driving voltage of the organic light-emitting device.(110) HIL(Exclusive or doping)COPYRIGHT KIPO 2016
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Paragraph 0081; 0082; 0083
(2016/10/09)
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- Controlling the position of anions relative to a pentafluorophenyl group
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The position of an anion above an electron-deficient arene can be controlled by the geometry of appended directing groups. Here a series of ammonium substituted pentafluorophenyl derivatives is investigated. The presented results are one step on the way to find the ideal structural features for an effective and superior receptor for anion-π studies.
- Giese, Michael,Albrecht, Markus,Wiemer, Katharina,Valkonen, Arto,Rissanen, Kari
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p. 1368 - 1372
(2012/11/07)
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- Carboanion Reactivity: Kinetics of the Reactions of Benzyl Cyanide Anions with Aromatic Nitro-compounds
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Rate and equilibrium measurements are reported for the reactions in methanol of carbanions derived from 12 ring-substituted benzyl cyanides with 1,3,5-trinitrobenzene to give ?-adducts.Some data for reaction of the carbanions with 4-nitrobenzofuroxan were also measured.With increasing carbanion reactivity, rate constants approach a limit of just below 109 dm3 mol-1 s-1.Intrinsic reactivities of carbanions in ?-adduct forming reactions and in proton transfer reactions are compared.
- Atherton, John H.,Crampton, Michael R.,Duffield, Gaynor L.,Stevens, J. Andrew
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p. 443 - 448
(2007/10/02)
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- Color Change of (E)-2,3-Bis(2,3,4,5,6-Pentafluorophenyl)-3-acrylonitrile by the Addition of Amines
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(E)-2,3-Bis(2,3,4,5,6-pentafluorophenyl)-3-acrylonitrile (3E) was synthesized.A benzene solution of 3E turns into a brillant red color by the addition of aliphatic amines.The coloration mechanism is studied by optical absorption, conductivity and product analyses.It has become apparent that ion-pair formations between 3E and the amines by proton transfer reactions are responsible for the coloration.Structural requirements of the amines for the ion-pair formation are discussed.
- Nakayama, Yasuhide,Inukai, Kazuo,Hayashi, Koichiro,Irie, Masahiro
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p. 1226 - 1230
(2007/10/02)
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- Polyfluoroaralkyl amines. Further studies on the reactivity of 4,5,6,7-tetrafluoroindole
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4,5,6,7-tetrafluoroindole 1 undergoes electrophilic formylation and aminoalkylation at C-3 to give compounds that can be readily converted to a variety of products, including the skatole, tryptamine, and tryptophan. 1 reacts with ethyl diazoacetate to yield 4,5,6,7-tetrafluoroethyl-3-indole acetate.The Grignard reagent of 1 offers a direct route to the versatile substituted acetonitrile 10 via C-3 alkylation with chloroacetonitrile.Key words: tetrafluoroindole, tetrafluorotryptamine, tetrafluoroindolyl magnesium bromide, tetrafluorotryptophan.
- Filler, Robert,Woods, Sarah M.,White, William L.
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p. 1837 - 1841
(2007/10/02)
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